The following story evolved from what at first was to become "Adventures of Boygirl." I published this on several adult websites a few years ago, after a particularly nasty breakup with my latest girlfriend. In this revision, I edited much of the previous version and added several new sections. Boygirl needed to bring down the Moon. He needed to go beyond the limitations of the previous boygirl saga. I think you will agree that he pushes the limits.

In "Adventures of Boygirl (2)," the reader may look over my shoulder and take a look at some of the email I actually exchanged with real women who have quite an interest in boygirls. The story concludes with a poem.

Feedback is always appreciated. The story's participants are all adults, not children, and it is intended only for an emotionally stable and discriminating audience over 18 years of age.

The Adventures of Boygirl

by Boygirl

Copyright ©2007 by Boygirl

Part II

(1) Moving On

 

After I moved on from Kara, there were others. It may be instructive for the reader to look over my shoulder, as it were, and take a look at some of the email I exchanged. No real names are given, but this is from real email, and this is what was said:

"I must tell you that your latest e-mail really turned me on, though I can see why some of your former girlfriends might have been put off by your "confession." Sexually speaking the girl (or should I say bitch?) in you is far more powerful than the boy, and the boy desperately needs to be put in his place. He's keeping you from getting what you want.

"I think it would take a special sort of woman who's very confident about her sexuality to appreciate your presentation of yourself as a boygirl. In the back of most women's mind, there's that old question: "What would my friends think of this guy?" Most women get turned on to the sound of rolling thunder. For them to suddenly discover that their boyfriend is a boygirl—well, it doesn't exactly fit their childhood image of a knight in shining armor. They might be initially intrigued, but within a short time, most women would begin to look for a real man. Many would not even admit to those feelings. They might feel guilty or blame you for your lack of trust. But whether they admitted it to themselves or not, most women would start looking elsewhere, and soon. (We worry a LOT about what our girlfriends think, and the pussy in you is not easily hidden!)

"And as far as your lack of trust goes…my guess is that it would be very difficult to trust partners when you secretly have want them to fuck other guys. I bet you've had any number of girlfriends whom you've brought to just to the verge of orgasm, only to leave them longing for a real man. In some cases, I bet you also had secret taboo fantasies of fanning those flames—perhaps orally preparing a favored girlfriend for a hot date or licking her lover's cum from her pussy <<yum>> after she returned home the following morning.

"You're not straight enough to be straight, gay enough to be gay, bi enough to be bi, or trannie enough to call yourself a trannie. Your e-mail tells me that you already know all this and still love women even after all these years. This intrigues me! I can only imagine how a relationship with you might look if it were allowed to run its course. My guess is that it would be monogamous for you, but not for her. Even a bisexual woman would need a real man from time to time, and you'd just have to find a way to live with that…even thrive on it. I think that you already know this but haven't ever been fortunate enough or brave enough to fully explore your potential with a woman who encouraged you in this.

"I'm a different kind of girl from most, and while I'd readily admit that I do need (and already have) a real man in my life, I'm very turned-on with most of the stuff you've told me and I'd like to share my fantasies in e-mail. You don't seem like the kind of person who will hold anything back. I won't hold back either. What do you think?"

(2) The Email Rapidly Progressed

 

"This, then, is our opening fantasy scene, the one that will break the ice and get things rolling. I'm imagining that you're an old boyfriend and we restarted a sexual affair. While you have an absolutely lovely cock, I've always suspected you're a pussy inside. This last Saturday night I was feeling horny. We were going to go dancing (dirty blues has a lot going for it), so I dragged out my shortest leather mini-skirt and a lace, see-through black blouse. You had always been the jealous type and never approved of my sharing my body with strangers when we were together. When you saw me, your eyes nearly popped out of your head with disapproval. You started to complain but I cut you off. You were instantly humbled and apologized profusely, at which point I realized you needed that kind of discipline. I felt empowered and turned on, and really enjoyed the rush I got by putting you in your place. The blues bar was crowded, noisy and fun. You've always been a great dancer, and I was soon buzzing and moving very suggestively and erotically, drawing a lot of attention from both the men and the women. Several men asked me to dance, and I always accepted even though I could plainly see that you were scowling. Around midnight we were resting at our dark little table when a very handsome man came up to me and told me he had been watching me all night; he said that he just had to dance with me. You started to tell him that I was tired but I cut you off in mid-sentence. This guy was really cute and his slacks were thin and draping loosely on his body, clearly revealing a long thick cock through the material. I started flirting with him, ignoring you and telling him I wanted to wait for a nice slow song to come along. The music almost magically changed and he held his hand out to me. I got up and started toward the dance floor, then stopped and went back to the table. It was dark enough that I could quickly reach up under my mini and peel off my little red bikinis. I shoved them into your breast pocket and arranged them like a hankie, slapped your face gently, kissed you on the lips and slipped my tongue into your mouth. 'I'm too hot for these,' I whispered. 'Keep them cool for me.' My new man grinned widely and pulled me quickly to the dance floor, taking me in his arms. I put both my hands around his neck and abandoned my body to his every movement, feeling his swollen cock pressing into me delightfully. When my back was to facing you, he quickly reached under my skirt and took both my naked ass-cheeks in his hands and started kneading them, making sure you were watching and fully aware of what was going on. I had an orgasm right there and just about brought my partner off at the same time. The music changed so we went back to the table and I told you I wanted to leave. I took my panties from your pocket, wrote my phone number on them and handed them to my dance partner. 'Call me in the morning,' I told him. I gave him a very erotic kiss, slid my hand along the huge bulge in his crotch and walked out. You trailed a few feet behind me.

" 'I want you with me in the morning when he calls me, and I want you to prepare me for my date with him. Take me home. Now.' I ordered. You looked mortified, but opened the car door and drove me home."

(3) We Had Our "Morning After'

 

" . . the phone rang early the next morning. I asked you to answer it as I was not yet awake enough. You reached over me to the bedside table and mumbled into the phone---'Hello, hello---anyone there?' You were just about to hang up when it dawned on me that it might be the guy from last night. I had asked him to call me first thing in the morning. I took the receiver and cooed into it, 'Tom, is that you?' He laughed warmly and admitted it was. I snuggled deeper into the bed, cradling the phone on my pillow and giggled suggestively, telling him, 'Yes, we can talk. Michael, go bring me some coffee,' I told you. You looked crestfallen as you obediently left the bed and walked naked into the kitchen. Watching your firm, girlish ass as you walked turned me on.

"I was still talking to Tom, setting up a time for him to pick me up this evening when you came back in carrying the coffee. You held the cup out to me but instead of taking it, I reached out and took your long, flaccid cock in my hand, squeezing and pulling it toward me. I stroked you gently as Tom finished telling me what he hoped to do to me later. With my other hand I pushed the blanket off me and slipped my fingers into my hot, wet quim. 'I'm ready for you right now, Tom,' I whispered into the phone. 'I can hardly wait for tonight! I'll have Michael prepare me for you!'

"I thought you were going to have a heart attack when you heard that, your jealousy was so evident on your flushed face. But your clit didn't lie, and it was throbbing with excitement….I imagined that you were secretly turned-on at the thought of preparing me for Tom. I hung up the phone and took my coffee. 'Draw me a bath, Sweetie, you've got a lot of work to do this morning.'

"While I lay in the tub, enjoying the bubble-bath you had prepared for me, I continued to instruct you. 'Pick out my sexiest garter-belt and nylons, my shortest skirt, thinnest blouse, highest heels and don't bother with a bra or panties. I won't need 'em tonight. There's only one pussy who's going to be wearing panties around here today, and we both know who that is, don't we?'

" . . I left you a note with instructions. You were not to read it until after Tom had picked me up and taken me out for dinner and dancing. You were still wearing my pink panties when we left and could hear Tom laughing when he glanced into the bedroom and saw you standing there, embarrassed and mortified---a large wet stain of pre-cum soaking through the thin material. You had been hard all day, straining for release, but I had forbidden you to touch yourself or cum. You nearly passed out as I spread my legs and ordered you to shave my pussy carefully, shaping the soft hair into a tight little heart shape above my lips. 'A blond Valentine for Tom,' I giggled. 'Put on lots of perfume for him.'

"I slipped into my miniskirt just as the doorbell rang, finishing my dressing for the evening. 'Oh damn, he's early,' I giggled, 'I guess I don't have time to put panties on. Oh well ...' I opened the door and gave Tom a long, wet kiss, knowing you were watching from the other room. I ground my body against his, feeling his erection immediately grow against me. Tom's hands went quickly to my ass and squeezed, his fingers discovering the lack of panties under the thin material. He laughed loudly again as he glanced at Michael, and led me out the door.

"Michael's note was short and sweet. 'Pray that Tom fucks me well, Michael. Or should I say, "Michael-Jane,' since you're clearly a sissy at heart. If I'm excited enough when Tom brings me home, I MAY allow you to lap his cum out of my pussy. Wear clean panties and be on your knees when you hear the front door open. If you can make me cum with your tongue, I may allow you the release you want so badly. Pray that Tom is the best fuck I have ever had, so I'll be ready for a boygirl to clean me out.' "

(4) My Sissyhood Is Confirmed

 

"I am so disappointed in you, you little slut! Can you even begin to imagine how mortified I was to return and find you laying there, your panties soiled in cum? All night long, as Tom and I enjoyed our date, much of my excitement stemmed from the anticipation of bringing him home. Every time he touched me, I felt your soft fingers and I visualized how pretty you had prepared my pussy. Every time I felt his erection strain against me, I remembered how your girlcock looked as you stood in your panties. And as my excited nipples ached, I could feel yours (as hard as small pebbles) against my tongue.

"I was so proud as I bragged about you. Tom was impressed that I was worthy of such worship and subservience. It drove him crazy to know he was getting the best of TWO women that night—me, the most perfect, sexy woman he had ever met, and YOU, my "stand-in" male sissyboy who had prepared me for him.

"Can you even BEGIN to know how turned on I was, knowing that you were kneeling there, focusing all your energy into heightening my arousal for him and his huge, pounding cock? ...knowing that you wanted him to fill me with his manhood in ways your clit could never do? ...knowing that his lips could suck my breasts so passionately that your own nipples would begin to ache with feminine desire....and knowing that if he came 2, 3, even 4 or 5 times deep into my sweet, hot pussy, that you would lick every last drop out with your long, talented tongue and then meekly ask for more.

"His cum was dripping down my legs when he brought me home, both of us totally pumped up with anticipation of watching you in your little panties as you slithered across the floor toward us, begging to be allowed to clean up his slick, thick white cum from my ravaged box, secretly hoping that if you did a good enough job we might reward you with his huge cock being rammed up your little pink rosebud of a cunt to drain the last of his copious flow of cum of the evening. How amusing that would have been to both of us. All this was going through my mind most of the evening, making me as hot and turned on as I have ever been. Finally, I had a sissy who was worthy of my sexuality. I was about to be worshipped in front of the best fuck of a man I had ever known, in a manner that I had looked forward to all my life. I was about to become a fulfilled woman, a sexual goddess, and also the Mistress of the perfect little boygirl. My greatest orgasm was about to overwhelm me ...

"But NO! There you lay, a total failure, an absolute slut, your selfish cum branding you through your disgusting panties as one unworthy of my trust and faith. How embarrassed I was in front of Tom, how hurt I was as he sneered that I needed a real boygirl in the future. He left us there, his greatest load of cum still locked in his huge balls, his cock shriveled with disappointment. I am amazed that I even allowed you to draw me a hot bubble bath before I ordered you out of my house.

"Will I allow you to return? Right now, I honestly don't know. You will definitely have to do some serious begging for forgiveness, and I will have to be extremely impressed with your contrition before I will even consider it. Don't write to me unless you are truly worthy of another chance. My nipples are sore and I have to go rub baby oil into them before I can sleep—another job you should have been able to do, had you any self-control.

"For shame…"

(5) There Were Reconciliations

 

"I awoke with my nipples on fire, my pussy drenched. As I lay there wondering why I was so aroused, My 24/7 boyfriend in real life rolled over and began to softly snore. It was obvious he hadn't any part in my nocturnal arousal, so I snuggled up against him, my ass spooning into his warm but soft crotch, my right hand cupping my pussy and my left on my breast. I lay for a long time, gently pleasuring myself, not seeking orgasm or relief, but merely giving myself up to the sensual joy of physicality.

"Suddenly I knew where all the sexual energy was coming from. I could see you channeling your erotic thoughts to me. As bad of a little slut as you were the other night, you were certainly trying to make up for your transgressions. I hated to admit it, but you are very good doing what you do best---sending and heightening my sensual arousal with your powerful energy. As you tweaked your little nipples, I could feel the electricity sparking into mine, making them pulse and pucker and throb deep into my firm breasts. I found my fingers squeezing in tandem with yours, pulling and stretching, prodding and fucking them delightfully. My clit strained toward my finger and became your ass, involuntarily spasming when you touched it. My pussy became your pussy as I ground back into my SO and began to softly cum. I could feel his cock growing against my ass and realized that you were awakening him, turning him on too. Your finger became his cock. It slipped deeply into me and my orgasm turned from a nice soft gentle cum into a wild thrusting humping cum.

"It was still dark as he collapsed against me, my pussy now full of his hot cum. He was unable to see your face buried in my cunt, your tongue licking and sucking his cum out of me. He was asleep again in moments and missed my last orgasm from your tongue. I fell asleep, satisfied---glad that your erotic warmth came through the airwaves and brought me relief. You had been history when I went to bed last night. If you hadn't sent your energy into my dreams, I probably would never have written back to you again.

"This does not mean that you are totally forgiven. It just means that your role as my boygirl still has some future. How well and how far it goes are up to you, but you still have a chance. Do Not Blow It! The next time I decide to allow you the chance to prepare me for Tom or another boyfriend will determine your future. I can't believe how lucky you are that I didn't cut you totally out of my life..."

(6) And a Second Chance

 

"You were very sweet this morning after I came home from my second date with that marvelous stud, Tom. I attribute this to my special handling of you prior to his arrival last night. I had talked with him on the phone about your transgressions during his first date. I had told you not to play with yourself, yet you did. Moreover, you came in your pretty panties. Tom and I decided that while your job was to prepare me and sooth my pussy with your talented tongue after my dates, my job was to make you prefer to pose in your panties over cumming in them. Even though you have a lovely clit, you wouldn't be feeling hard if you were feeling sufficiently soft. You wouldn't want to cum as a man if I really did my job in turning you into a pussy.

"I loved how you licked all of Tom's cum out of my pussy this morning. I also treasure the memories of your submissive pose at his feet last night, before he whisked me out the door. You sucked his cock slowly and adoringly while I caressed your nipples and reminded you in a soft hypnotic voice what a sweet little cocksucker you were. This is a ritual you will perform many times, not only with me but with every girlfriend whom you will date in the future. The only thing even semi-hard about you will be your girlcock. Secretly, you will long for your women to date "real men" so that you may prepare them and their dates for one another. In this, Michael-Jane, you will learn to excel.

"I put you in your place early yesterday morning and kept you there all day. I loved the way you involuntarily spread your legs when I fucked your nipples with my tongue. You really are a little pussy. Turning you over, I remember humping you slowly, pretending to fuck your smooth girlish ass, teasing your back with my tongue while my fingertips danced over your tits. You mewled in pleasure. Only when you were panting like a girl in heat, however, did I give you what you so desperately needed.

"First, I fingerfucked you, and then I slowly inserted my dildo—which I first made you ritualistically suck—deep inside your well-lubricated ass. The dildo was shaped like a man's penis, though it wasn't as thick or long as Tom's. I strapped it on and then slowly and skillfully fucked you until you were begging for release. I played with your nipples with my fingertips and kept you on edge with my dildo for nearly an hour while I crooned in your ear, hypnotically reminding you what a desirable little pussyboy you were. I reminded you that your "cock" was really an elongated clit, a girlcock, and that you would no longer wish to play with yourself as a male, but as a girl. You would no longer wish to stroke the full length of your shaft (no more 'beating the meat' for you, sweetheart!). You would learn to cum as a girl by rubbing and teasing just the head of your clit, and you would learn to fuck your women with a butt plug or a dildo ensconced deep in your own hot little hole. I also reminded you that your main purpose in life was not only to orally prepare me for my lovers, but also to serve and entertain any man or woman with whom I might choose to share you. I told you that as you became more and more feminized, I'd show you off to my girlfriends, not as my new boyfriend, but as my new boygirl. You had already done that for Kara. Now it was my turn. When you finally came, it wasn't a clitoral orgasm, but a series of multiple "vaginal" orgasms, complete with plateaus and a final blast-off into hyperspace. I felt confident that your pretty little ass would crave that kind of treatment every night.

"That is why you were so meek and mild when you saw Tom come to pick me up last night. Before he even arrived, I had you get me ready for my date by licking my pussy until it was quivering with desire for his cock. You repeatedly brought me just this side of orgasm. Your job was to make me yearn to be fucked by Tom's thick, beautiful shaft, and you did your job very well indeed. When he arrived and his handsome, masculine presence filled the room, you blushed and demurely lowered your eyes. I had shaved your entire body just hours before and dabbed you with a scent that made irresistible. You not only looked vulnerable but you felt that way as well.

"You gracefully dropped to your knees and asked Tom to forgive you for your transgressions on his first date with me. I told him how you had orally prepared me for my date with him this night. He was visibly amused and complimented me on my progress with you. As you sucked his hot male shaft to prepare him for his date with me—your goal was to make him hard for me but not to make him cum—he laughingly told me that you behaved the way a pussyboy should. When we left together, you blushingly admitted that we made a very cute couple.

"As you waited for me to return from my date, it wasn't your cock that needed attention. It was your "cunt." That's exactly where I wanted you to be! That must have been why your panties were so silky clean when I arrived with Tom early this morning! As a reward, I allowed Tom to give you the kind of treatment that I had planned for you after our first date. It's all captured on videotape, which I planned to show to my girlfriends, as you knew.

"First, I made him hard again by sucking his cock and sweetly teasing it with my tongue. . . .while you were made to play with your exquisitely sensitive nipples and watch how I served a real man. Then my new boyfriend fucked you doggie fashion while I lay there with my legs spread, my pussy just inches from your face. As I teasingly rotated my quim, you rotated your smooth, creamy ass invitingly in tight little circles and rode my lover's hard, throbbing, virile shaft, even as your face contorted with girlish lust. While he fucked your butt, he also fucked your little nipples with his fingertips. In soft, confident, masculine tones, he encouraged you to be his little sissy, and he made you verbally agree that you would service him anytime he wanted you to, and that I could also fuck him anytime I wanted to. While Tom talked to you, I hypnotically repeated my earlier command so that you would always remember that in the future, though you might have many girlfriends, that they would secretly wish to lie in the arms of well-endowed and virile men such as Tom, and that your ultimate thrill was to use that sweet clit of yours to awaken them to that realization. Tom was persistent but very seductive, and his conquest was as sweet as it was complete. There could be no going back. As he erotically branded you, I loved hearing you wantonly encourage him to fuck you even harder. You moaned, making your erotic submission even more complete. You came like a girl, shivering with lust, even as his massive balls pumped their last delicious load of thick white cum deep inside your smooth, firm little ass.

"After Tom left, I continued to videotape your performance as you slavishly lapped his cum out of my ravished pussy while I recounted every detail of my tryst with my handsome boyfriend from the night before. He fucked me almost all night long. It was such a joy to be with a real man. I shared that joy with you by reliving vignette after vignette. You'd make a fantastic housemate! You were so good licking Tom's cum out of my pussy this morning after we returned from our date that it made me want to fuck him every night!"

(7) There Were Further Humiliations

 

"I knew you'd like what happened after that second date with Tom! Do you understand that I couldn't wait to show my girlfriends what I could make you do?! They both asked me about you on our girls night out last Friday. I must confess I told them all the lurid details. As I told them about the last couple of weeks during which we've been "housemates," their eyes widened in growing sexual excitement, and both of them actually blushed.

"One of the things that particularly turned me on about you was that your willingness to serve as my boygirl didn't always last. Soon after I permitted you to ejaculate, which you always did in the most endearingly girlish way, you sometimes became more of a "boy" again, and a very jealous and petulant little boy, indeed.

"A few days ago, I brought home an old boyfriend who knew next to nothing about you prior to his arrival at my house. During the afternoon before the date, I spent the better part of an hour teasing your nipples and ass with my fingertips, and bringing you to a state where you agreed to do anything I wanted when my date arrived. Your role, I explained, was to present yourself as a somewhat jealous ex-boyfriend (which, on some level, you actually were, even if you had a clit instead of a cock), but you were to be low-keyed. Looking deep into your eyes as I slowly finger fucked your delicious little ass, I reminded you that however macho you might wish to present yourself, you couldn't help" but betray yourself as a boygirl. The scene called for you just to be yourself, which meant you were to be a somewhat jealous "ex-boyfriend." My date's role was to "take me away" from you and fuck me in the bedroom while you listened. My role was to pretend to be a young, bright-eyed innocent, and to pretend to be seduced when, after all, it was I who was actually doing the seducing. Our agreement was that you would not be allowed to play with your girlcock at any point if you were to be permitted to lick my pussy out after my date with this stud. If we fucked for half the evening, that was fine, but you were only allowed to play with your tits.

"The cherry on the cake was that I had inserted a butt-plug up your precious little rosebud prior to this boyfriend's arrival, and you were instructed to wear it all night.

"When he showed up, you were absolutely darling! You were just pouty enough to showcase my date's good looks and lean, rugged masculinity. You were so busy overcompensating in trying to play the boy that the girl in you (butt-plug in place) inadvertently managed to reveal herself with every gesture, every word. You didn't need to say you were jealous. You went for understatement, which was precisely what the scene called for. My boyfriend picked up on it and at that point, things began to deviate significantly from the prepared script. Instead of retiring to the bedroom, he staked his claim on me in front of you and began openly flirting with me while we were still seated on the sofa, with you watching. Within a short time, he kissed me and within five minutes, he was fondling my nipples. I melted in his arms. You stared at us utterly fascinated. You could clearly hear my moans and the well-lubricated suction sounds as he slowly and methodically began to finger fuck me while you watched.

"You were powerless to avert it. It was as if the sight hypnotized you, and I took advantage of your moment of weakness and called you over to the couch, saying, 'Watch what I can make him do!' I told you to strip down to your panties, and in sexually graphic language, I then told you to, 'Prepare me for what you know is going to happen, my sweet.' In a trance, you dropped to your knees and with doe eyes, submissively looked up at him and asked whether you might kiss my pussy in order to prepare it for his cock. He unzipped his pants and his shaft sprang forth, waving just a few inches your face. It was beautiful, and my twat throbbed with growing excitement, knowing it would soon be satisfied, literally right under your very nose. Your reward in enduring these humiliations was to be allowed to fondle your nipples while licking 'your woman's' pussy in order to prepare her to be taken by another man.

"As you performed your ultimate act of submission, your tongue seemed to have a life of its own. Soon, however, it was not your tongue that my twat ached for, but the long, thick rod that had sandwiched itself between your ass cheeks (he didn't fuck you, but he was teasing you) even as you did your "job" on me. My boyfriend played with your nipples and in a very seductive voice, called you all kinds of demeaning names. You were like a deer caught in the glare of the headlights…or a small animal hypnotized under the spell of a cobra. You didn't disappoint. You squeezed your butt-plug with mounting desire that paced mine. You were making me connect with the desires that swept over me. You were making my cunt ache for the kind of treatment that you could never give me. Hoarsely, I moaned that I needed to be fucked. I spread my legs wider even as my lover lifted you off of me and gently set you on the floor next to the sofa. Though you were burning with excitement, the hardest thing about you was your nipples. I took this as a very good sign. My boyfriend's cock, however, was something else again. It was a perfect specimen of manhood, it was rock hard, and my pussy ached with desire even as he slowly and skillfully began rubbing just the head against my clit, mercilessly teasing me as he had teased you. What's a girl to do? It was even better than your tongue! I couldn't help it! At that moment, I needed to be fucked by a real man more than anything else in the whole world!

"After teasing the entrance to my waiting hole for what seemed like hours, he smiled down at you and winked just before he let the full length (8 inches) of his hard male shaft slide home, possessing me completely.

"You blushed from head to toe! If you had stomped your foot in a fit of jealous pique, you couldn't have looked more adorable. But you had no will of your own, and even as he slowly fucked me, even as things began building to a thundering crescendo, we ordered you to rotate your ass and spread your girlishly smooth legs while finger fucking your hard little nipples.

"As my lover watched you with visible amusement, he smiled archly and mounted me doggie style pumping in and out with his slick rod of steel, slowly at first and then with faster and more powerful strokes while I rotated my pussy and begged for more. Each time I moaned or cried out, you cried out in sympathy. It was as if you could feel everything I felt, and with that butt-plug in place, you probably could! Later on, I wrapped my legs around his back, while you spread your own legs even wider, moaning with feminine desire, as if in fucking me he was somehow also fucking you as well. I came like an exploding star, my cunt grasping desperately at my lover's cock as it drilled into the center of my soul stroke after satisfying stroke…..

"When he finally unleashed his load of scalding white cum, you moaned out your own sweet obscenities, begging him to, 'Fuck 'my woman, fuck her harder, please…,please give her what she needs, please…..please….'

"I thought it inexcusably presumptuous that you referred to me as 'your woman,' and when my boyfriend and I had finished, I put you in your place by straddling your face while ordering you lick to my lover's hot thick cream from my pussy as it dribbled into your mouth. As you did this, I teased your titties lightly with my fingertips while mentally comparing my boyfriend's massive shaft with your clit. I wasn't cruel, however. I reminded you that it that your tongue was a national treasure and that your future role as my housemate was assured as long as you continued to prepare me for sexual encounters with other men whose virility and skill at fucking would satisfy all of my desires as a woman.

"When you had finished with me, my boyfriend thought it might be fun to see if you could cum as a girl. While he fucked me a second time, we ordered you to masturbate with the training dildo I had bought for you several weeks before….

(8) And Difficult Confessions

 

"At that point, one of my girlfriends raised an eyebrow and interrupted my story. She asked when she'd have a chance to see this tongue in action. She said that she didn't believe any man would voluntarily degrade himself as you have. She didn't realize that you're not a man at all. She insisted that I 'lend' you to her in order that she might verify my story. With my credibility on the line, as you can readily see, I was in no position to refuse….

"One of my girlfriends was strangely silent and flushed when I had finished. After the other one had her say, Carol spoke up. She said that she knew the story was true because she had dated you a few years ago. Seems that she also stumbled on the 'Michael-Jane' part of you fairly early on and it wasn't long before you were 'casting spells' on her cunt with your tongue, much as you do with me now. The difference is that you and Carol didn't talk about your respective fantasies.

"Anyway, one night the two of you got pretty carried away. She had kissed your nipples and you were trembling with excitement, which made you feel even more femmy. As you melted, so did your pretty clit. It simply refused to get more than semi hard. You were finally able to insert it (barely), while Carol continued to tease your nipples with her fingertips. You sensed her frustration, and after you yourself had cum more like a girl than a boy, you helped her out in the only way a boygirl could. That was when you cast your first spell on her waiting cunt….

"You ate her out for a long, long time, licking your cum out of her insatiable pussy, and while no words to this effect were actually exchanged, she told us that she felt as if your tongue was imbuing her pussy with an almost magical power to attract men—handsome men at that, with hard, virile cocks—who would find her irresistibly attractive and want to fuck her. Her fantasy was that as they looked at her, she'd find herself…looking back. Any resistance or pangs of conscience that she might have felt arise in her was immediately quelled by the magic of your own persuasive tongue, which brought her to a greater peak of excitement than she had ever known with you before.

"As it happened, Carol had a plane to catch the next day. She didn't talk to you about at happened, but she told us. When she boarded the airplane, she found herself seated to a very handsome stranger whom, as luck would have it, she spent the weekend with. They couldn't get enough of each other, and when she flew back home, her pussy was still slick with his cum. Carol reports that you were very attentive when she returned….You licked and kissed her sex almost slavishly, bringing her to a thundering orgasm. You seemed to sense something had happened, but she never admitted the truth to you because she didn't want to hurt you.

"She didn't know how to handle you as I do, plus she really didn't appreciate the depths to which a sissy would sink. Because she felt guilty about lying to you and because she couldn't quite fit you into her picture of the way "things ought to be" between boyfriend and girlfriend—she found herself 'looking back' at a lot of other men during that period. Carol dumped you a month or so after.

"You should take some consolation in the fact that after telling her my story, she said she regrets the dump. She now knows that she could have molded you in ways that would have pleased you both, and that there was never any cause for shame or guilt. She knows that if she had just been a bit more honest and a little more daring, she might have been able to have her cake….and have it eaten too."

(9) It Included Arduous Assignments

 

Your e-mail really turned me on. I didn't realize there had been a Carol in your life or how close I had come to the truth. You (and the women in your life) need to fully accept the fact that you really ARE a little sissy! If the "man" in you hadn't been so jealous, Carol could have used you in some delightful ways!

"I want you to do something for me and for my girlfriends as well. I want you to imagine these scenes that I've described, and masturbate with them in mind. I don't want you to cum as a man. I want you to tease your titties and spread your legs, playing with your breasts on a daily basis, while fucking yourself with a dildo and learning to cum as a girl. I also want you to imagine that each of your previous girlfriends encouraged the girl in you, even if it humiliated the boy. I want you to imagine them with real men. Imagine yourself in a totally subservient role. Imagine what they say to you, how they put you in your place, the things they do to you and what they make you do.

"In a few weeks (I need to be away awhile), we will have a party. My girlfriends will be there. Carol will be there with her lover. You'll also be there, perfumed and pantied. It will be at the party in which Carol, your former girlfriend, will tell you and everyone else in the room exactly what happened after you saw her off at the airport on that day so long ago.

"Carol's boyfriend, you'll be interested to know, is bi and very handsome. You will demonstrate to my girlfriends what a passionate cocksucker you can be, if properly inspired. You will suck him off, and if Carol times this right, he'll explode in your mouth at the same time she finishes her story. Remember to do your homework while I'm gone, boygirl."

(10) And Risqué Parties

 

"You remember that my girlfriends and I decided that you would be the guest of honor at a party we were throwing?

"Well, instead of staging our own party, in which the outcome would be known from the beginning, we decided to bring you along as my "date" to that swinger's club that I told you about. My three girlfriends would be there with their guys, and you would come pretending to be mine. We wouldn't bring you dressed in panties, but after we got finished with you, it was a sure bet that you'd leave in them!

"We realized that it would take some time and preparation for the other people at this party, even though they were pretty open-minded, to get used to the notion of someone like you. We thought the most erotic move would be for Monique, who is even prettier than her name, to "out you" in a room full of other people while I was being laid. The goal wasn't to just get you aroused (that's hardly a challenge), but also to get the rest of the people aroused as well. Everything depended on our presentation.

"On the night of the party, we decided that you would be initially presented very much as you were in that scene before. You would appear to be my 'boyfriend' but before the night was over, everyone at the party would know you for what you were. They'd want to use you too, as a willing and winsome little boygirl.

"By the time Monique got to you, you had already made an impression on some of the guests. We were all naked, of course. The babes weren't very shy about checking out how well endowed the guys were. When I asked you to eat me out before slow dancing with an exceptionally well-hung and handsome suitor, you did as you were told. Your ass was high in the air and your butt-plug (!) was clearly visible to all present. Several people laughingly commended you on your technique. By the time my partner took my hand and led me to the dance floor, I was literally dripping with excitement. It wasn't long before the full length of his enormous dick was ensconced in my tight little hole. While he danced with me, my cunt spasmodically clasped his shaft in rhythmic contractions. I wrapped my legs around his waist as he slowly fucked me in time to the music.

"Seeing that you were beginning to flush with jealousy, Monique took your hand and led you off to another corner of the darkened room. She told you she had seen the video I made of our threesome with Tom. It wasn't long before she began to play with your sexy nipples, first with her fingers and then with her tongue. You moaned and began to spread your legs, panting like the pussy whom you actually are. She whispered in your ear that even though your girlcock wasn't exactly stud material at a party like this, there were other ways in which you could please the women there.

"She flipped you over, still teasing the little points of your nipples until they burned with girlish passion and desire. She positioned you so that your head rested low on a pillow, while your smooth, creamy ass, which was supported on several pillows, was raised high in the air, making it am inviting erotic target. Your pose made a very pretty picture indeed! With that butt plug in place, you could not have looked more submissive! She began to pretend to fuck you doggie style, and, in her seductive French accent, she began to tell the other people in the room how things were for you.

"The little minx seemed to take inordinately perverse pleasure telling everyone in the most explicit language about you. 'See!' she continued, as if she were referring to a pet. 'He can't help it!' With her free hand, she held an index finger out for you and coyly told you to suck it like the sissyboy you were. Without missing a beat, you shamelessly began sucking her finger as if it were a cock.

"While all of this was going on, my legs were wrapped around the kind of drop-dead gorgeous hunk every girl at one time or another dreams about fucking. I heard your moans from the other side of the room, and answered them with my own, even as my lover's lovely cock pistoned in and out of me. I felt that my pussy belonged to him and him alone! As he teased the entrance to my honeyed hole with the head of his shaft, Monique stabbed your nipples with her fingertips, causing you to howl at the moon. By this time, our room was packed with spectators, and the sexual heat was incandescent.

"While Monique pretended to fuck you from behind, Carol began to sensuously rotate her well-trimmed box in tight little circles in time to BB King's 'The Thrill is Gone.' She had been well-fucked by her boyfriend earlier in the evening, and her cunny was still sticky with his cum. She whispered huskily, 'I'm not interested in your clit, boygirl, but I know you give good head. Eat me!

"You didn't need a lot of extra encouragement. You leaned forward while on your hands and knees, licked her clit, and then, deciding you definitely liked the taste, you methodically cleaned her sex with your tongue as if it were a long prehensile serpent, fucking her, arousing her to the point where her pussy seemed to glow in the dark and she began to whimper. My own girlish moans blended with Carol's. I could hear her struggling to maintain control while she complimented you on being so good with your tongue…just moments before a series of multiple orgasms sent her cascading over the edge.

"Monique used that opportunity to hold up the same harness and dildo I had been using to train you with over the past few of weeks. God knows how she managed to smuggle it into a roomful of naked bodies! She strapped it on, took the butt plug out, and lubed both the dildo and your sweet rosebud hole….and slowly and sensuously began fucking you in earnest! As you began to moan with pleasure at being thrilled and filled with something more substantial than a butt-plug, she told everyone within earshot that as the party's mascot, your "job" was to remind every woman there that what she really needed in a man was something that no boygirl could ever give her...but that as a cheerleader in their mating ritual with real men, as an "oral facilitator" who had a talent to make their sex burn for something hard and real and satisfying, a sissy like you definitely had his uses. Your own ecstatic cries of agreement as she sensuously skewered you with the dildo were enough to send me over the edge!

"Everyone in the room heard me cry out, as the truth of Monique's words seared my soul and penetrated even more deeply than my lover's dick, 'God yes, "I need a REAL man!! Yes!! I do!! Ohhhhhhhhhhhhhhhhhh! YES! A big…long…thick cock… like YOURS!! Please! Please! Give it to me!! Nail me to the wall! Please fuck me NOW! I need a cock between my legs! Your COCK!! YOUR cock!! YOUR COCK!!! Oh God…Oh my God… Please Fuck me!! I'm Cumming…..Oh God...Oh God…!! I'm cummmmmmmmmmmmming!! Ohhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhh!!!'

"Carol's handsome lover stepped forward at the precise moment that my first orgasm swept over me. He began to tease your nipples with his fingertips. In the next moment, with your ass still raised high in the air while Monique continued to fuck you, you struck yet another pose of ultimate submission as he encouraged you to show everyone at the party what a sweet little cocksucker you were!

"Your lips were soon molded prettily around his long, sculpted tool, your face flushed with sexual excitement as your head bobbed dreamily up and down. Carol came to your side, and she began telling the whole room the story of her sexual dalliances after you dropped her off at the airport so long ago. This was the first time you had heard it, of course, and out of consideration for you, she held back none of the erotic details. The stranger on the plane had indeed looked at her, and she looked back, and what ensued was a torrid weekend affair.

"Then there was the other guy with that lovely cock two weeks later! She told us that you displayed so much humility in cleaning her box whenever she returned from her trysts that she failed to give you any credit for the magical chemistry between herself and her lovers. She simply didn't know what a boygirl could do, or what to do with one at that time. She didn't know that you were only doing your job—and, she added, doing it very well indeed.

"And so she dumped you, she let you go. At that point, she leaned forward and tenderly—almost wistfully—kissed your breasts, while Monique continued to fuck you with the dildo. As Carol lightly fucked your hard little nipples with her tongue, your legs parted ever so slightly and, shivering with lust, you sucked her handsome partner's hard, virile shaft until his massive balls rewarded you by giving up their hot sweet seed, which you gratefully swallowed without a moment's hesitation.

"Moments later, Monique produced a pair of sexy lace boyshorts and in full view of everyone, she made you wiggle into them and pose. She let people know that your new party name from this time forth would be Michael-Jane. Several of the women giggled while the men looked on with amused interest. Monique described the boyshorts as a symbol of your subservient erotic status, having just come out as the party's "mascot."

Then Monique asked for volunteers to "finish you off!" The 2 guys who volunteered to fuck you managed to keep you on edge for half an hour, during which time your cute, tight, girlish ass moved in inviting erotic circles as if it were plugged into a perpetual motion machine. You sucked their cocks to make sure that each man was "ready" when he got to the front of the queue and slipped it in from behind. You also were required to performed cunnilingus on several beautiful women who invited you to clean out their sex with your tongue. You were used as a sissy all night and came en femme several times. Word was getting around regarding your many unusual talents! Needless to say, my girlfriends and I were very proud of you, boygirl!

(11) There Were Times When the Email Turned Reflective.

 

"Maybe I'm not as kinky as I think I am. Or I'm mentally kinky, and not into the physical posturing and props. Playing dress up occasionally is fun, in private, but I'm not really much of an exhibitionist. hmmmm.....although I did just think of something else fun to do with you...

"Imagine this: You are kneeling in a quiet and darkened room with just enough candlelight for me to see you by. But you don't know about the candles, because you are blindfolded. You are deliciously naked, your arms tied over your head, maybe attached to a loop on a wall or ceiling.

"And I am quietly, sensuously, kissing you over your entire body, licking your titties, fondling your clit, tasting your lips. Since you are in the center of the room, I can hold you from front or back, and I enjoy spending time caressing your smooth ass cheeks, they're so round and nice.

"You can't tell where the next kiss or lick will land, you are blindfolded, and so you must wait, your skin tingling, for my next touch. Suddenly my hands stop touching you, and you wonder, what is she doing? And my mouth suddenly engulfs your cock, not touching any other part of your body. The lack of sensation from the rest of your body makes you focus intensely on the pleasure in your cock, and as it slides deeply down my throat you can feel my tongue delicately licking it's base. Still helplessly tied, you succumb to a draining orgasm, your semen filling my mouth. As you sigh with pleasure and relief, I move upwards, holding your head, and as I kiss you, transfer your tasty cum into your mouth. Yum!

"Or imagine you and I in a partial state of undress, you with your shirt off, your trousers unzipped, passionately kissing. My hand in your pants, holding and stroking your girlcock. My mouth drops to your exposed nipples, at first softly kissing each one, and then more firmly. Your knees buckle with desire, falling backwards onto the bed, my mouth following you down. I slowly fuck each nipple with my tongue, insistently probing and biting, and your legs spread underneath me, your mouth softly opened, panting...

"My warm mouth descends lower, kissing my way towards your throbbing clit, but only lingering for a moment on it's swollen head, teasing you, before I continue my downwards travel. I pause, kissing each testicle, laving them with my flat and wide tongue gently and then I slowly lick the skin between your legs, where your pussy is, hearing your groans of passion, your head thrown back. I lick you like you were a woman, softly and wetly, and when you raise your knees, lick downwards toward your secret place of passion, eliciting even more sounds of pleasure from you. I gently roll you over on your stomach, kissing your rounded and girlishly smooth ass checks.

"When you are unable to move away from my mouth, your pretty butt high in the air, legs spread, I slowly slide a finger into your well-lubricated ass. Your honeyed hole is warm and tight, and after introducing another finger, I start to slowly fuck you in and out until it's time for something a little larger. I get out a harness, and fasten into it a two headed dildo. One end is going to satisfy my dripping pussy, and the other end is for you. I need you to lubricate the end destined for me, and so while you are kneeling so prettily on the bed, I ask you to you lick and suck the cock intended for me, in order to be sure it is ready for my hot cunt.

"You watch as I don the harness in front of you, being sure you have a good view as the thick dildo that spreads my pussy widely, my face contorting in pleasure. You are glad the other end of the dildo meant for you is a slimmer version of the one impaling my swollen cunt. I move behind you, and give your 'pussy' a last wet finger-fuck to be sure you are ready.

"Restraining my lust, I press the head of the dildo into your ass slowly and gently, although my instincts are to thrust deeply, desiring the reciprocal thrust into my box. At last it is completely enclosed in your sweet hole, and I bend forwards, my body in complete contact with yours, slowly thrusting, my fingers reaching around the front of you to teasingly touch your fiery nipples.

"As you moan in anticipation, I whisper in your ear what a good little whore you are, and how much pleasure you give me.

Each time I impale you on my cock, the double dildo thrusts deeply into me. Our boundaries blur as our sexual tension increases, each of us fucking and being fucked, penetrated and being penetrated. My hand slips down to your semi-hard clit (sometimes it's hard to be a girl and a boy at the same time), stroking you in time with my thrusts into your pussy. The dildo stretching my cunt causes me to begin to orgasm, and as I cum, I helplessly thrust deep and hard inside you, triggering your own orgasm, your cum spurting through my caressing fingers, and we collapse into a sweaty, smiling pile of humanity.

(12) There Were Times When It Turned Serious.

 

"Subject: What a Woman Really Wants (part 1)

". . . oh, you silver-tongued devil, you! Thank you, thank you!

"Linda Lovelace may have had her clit in her throat, but mine is definitely higher and deeper—right between my ears. No, Sweetie, don't try to hit it with your schlong. That may have worked for her but it isn't gonna make me see the stars. Fucking my face just isn't ever gonna get me off. +++But can you ever deep-throat me with that silver tongue of yours+++WOW (!)


"My significant other is the best man in my life at playing my body to it's full erotic potential, but you are definitely the best I've ever known when it comes to fucking my mind. In so many ways you give me more powerful, exciting and satisfying climaxes than my SO and his awesome command between my legs. Yours are the ones that stay with me all day, that I flash on as I reach for the Cheerios or cross my legs in my mini, or glance at my reflection in the store window.


"Fucking my mind gets so much closer the dirty little core of what really makes me cum—it "gets to" the real slut in me. I've been physically-fucked by a master—a man who could keep it up for hours and hit every square centimeter of my inner pleasure palace, but who couldn't deliver me even the tiniest orgasm. He was just totally unaware of my brain's clit. While my SO knows it's there and can play around with it, and often gets it nice and juicy, it's still very much a mystery to him. And for some reason he doesn't seem interested in getting to know it to its full potential.


"You have come the closest to understanding it and possessing it and making it your own. Perhaps because I've loosened up and allowed you free reign, perhaps because of the "safety" of our physical distance, perhaps because your feminine side is so much stronger and fine-tuned than most men—I don't know. But you seem to know that girls can get as down and dirty and nasty as guys can. This is a first for me and I love it! Thank you again!

 

 

"Subject: What a Woman Really Wants in a Man (part 2)

"Reading about your lust and need to prepare me for my significant other and your girlfriend is so Totally Hot. I closed my eyes and could almost taste his cum on your tongue. I love the idea of slurping a woman's pussy while getting fucked doggie-style, and having you there facilitating all the action is a fantasy that has incredible erotic power for me. That's the glory of fantasy. I know it would never happen as intensely as you made it sound, but I can let myself go and revel in my inner slut until I dissolve into the blessed relief of orgasm. Yummy!

"….Bringing us to your real question—what does a woman really want in a man? That one will take lots of time to answer definitively. Suffice it to say for now, I believe a woman wants a man who recognizes her mind and body as being an intertwined unit, and respects and accepts and honors them both equally. As you have learned to fuck my mind, to stroke my inner slut, you have come closer to being what I want in a man than I could have imagined. You have the confidence to admit a sissy lives within you and is as real and important as my inner-slut is to me. You have shown that you crave the same acceptance and respect that I do. And your obvious ability to play with these inner-souls of ours makes you fit my compatibility needs like a glove. Take care Sweetie. Thanks for sending me your sexy vibes. I'll enjoy being there for you when you girl-cum with your nipple-play.

"Subject: What YOUR Women Will Want in a Man….

"Oh, wow! Your story about your affair with Beverly was too much! Here you were, fucking someone else's wife…while she was getting off dropping hints to you about cheating on both of you with a third guy. I can just imagine that conversation she had with you in the coffee shop while she was fondling your nipples while telling you about this guy who was trying to get into her pants…whom she was encouraging! And then there was Diane, who diddled herself with a dildo after you came—if she even allowed you to cum—while she verbally fantasized being with another man! You need to know that girls don't just do that sort of thing, boygirl. Clearly, they had a strong need to go elsewhere to satisfy their need for cock! You should learn from this sort of thing, Michael-Jane! When women go out with you, they're still going to need real men, and you're just going to have to get used to it!

"Beverly may have turned her husband into a cuckold without his knowing it, but she turned you into a pussyboy and rubbed your nose in it. The same was true of your other girlfriends. I think you must like this sort of thing! You've just got to find some way of letting your women know what you're about without turning them off. I want you to ponder this question. Remember that timing is everything. I will not allow you to cum until these women, in your imagination, look you in the eye and laughingly (but gently) call you 'little bitch.'

"I came while masturbating, imagining your licking Beverly's hot little hole while she told you about her affair. My, but it's clear that you need to be put in your place!"

(13) With Seriousness Came Affection

 

"I was a good girl last night and joyfully did my homework as requested. At some points I imagined my significant other was you, boygirl, and the way you licked my pussy was so delightful...you have such a gentle touch...I was licking you at the same time, but it was so hard to concentrate with waves of pleasure emanating from between my legs. Did you like how my pussy is so closely trimmed? I like it that way, because I can feel your tongue on everything, including my pussy lips. They are so sensitive...

"After I was satisfied, I turned around and climbed on top of you, teasing you with just the head of your cock inside of my tight hole. I think your moaning is soooo sexy...I slowly, slowly, teasingly sat down on your thick, throbbing rod, and once it was inside, squeezed slowly with the muscles that line my cunt, pressing my clit down on yours, rotating my hips. The wetness started to pour down your hard girlcock, making me sigh...

"Groaning, you put your arms around me, holding me tight, and somehow managed to turn me over, you on top, never breaking our delicious connection...I like how I feel with your weight on top of me, and I like how you kiss me, now with unbridled passion... As your penis slides slowly and gently back and forth, you moved yourself upwards, so that your nipples were -conveniently!- just above my mouth. Ah, how you moaned, and your girlcock throbbed, when I alternated teasing them with my tongue and fingers. As you climbed that helpless peak leading to ton petit mort, I lightly pinched your nipples, lightly, and then, harder and harder....until you succumbed.

"I called you a sissy again and again as your body cleaved as closely and deeply into mine as it would go, caught in that irreversible tide sweeping you out of this world and into that other...

Afterwards, I thanked you for sharing with me about feminine half, your alter ego, Michael-Jane." I guessed as much. I've had my own fantasy about being with a.sissy Yep, it's tacky for me to think about a pussy when I make love with my man, but it turns me on. I must be careful not to moan, 'Oh boygirl' out loud, yes?

"As I read your mail from yesterday, it drives me crazy to think about you kissing gently between my legs. Please let me cum eventually, it is so cruel to make me wait! And I WOULD beg aloud, asking you to please not stop, please....I'm so close, just a little more. Kiss my pussy lips like you kiss my other lips, and oh please, kiss me deeply and slowly.

"But you stop, my hips writhing on the bed as you hold my hands above my head, while you insist that I kiss and lick your hard little nipples... I would do anything for you at this point...I raise my head and tease one nipple with the tip of my tongue, just as you are teasing my wet cunt with the tip of your clit. I move from one nipple to the other, licking and sucking, sometimes gently, sometimes a little roughly. As only the head of your clit enters my pussy, sliding back and forth a little, I begin to learn my lesson: I must please you first before you will give me what I need, and it pleases you that I lick your little titties.

"The more I kiss and tease, sometimes kissing your neck and ears, the more of your shaft enters me. I desperately want to kiss your lips, and as you lower your head towards mine, I open my mouth to meet you. I suck on your offered tongue, and it penetrates me in time with the penetration below. I can't help it, and I begin moaning as your mouth begins to consume me.

"I spend ¾ of my time wanting to be at someone's feet, and the other quarter wanting to order a slave around. Go figure. GOD I wish I didn't have this pesky conscience, the things I would like to do with you, the things I would like you to do to me. Don't think your letters to me are falling into a black hole, it's just that I'm uncertain what to do with them, with my feelings, with my cunt. I want to taste you, I know that you taste sweet, I want to SEE you melt when I touch your nipples, not just read about it. I want to wrap my legs around your back, I want my collar around your throat, I want you to service my girlfriends, too. I want to hear your moans, feel your girlcock, smell your sweat. If you asked me at this very moment, if I were looking deeply into your eyes, I would kiss you softly, slowly, my tongue lightly darting between your lips.

"You are like a fast flowing river. I fear to take a first step, that I might be carried away."

(14) With Affection Came Humor

 

"Subject: Putting You in Your Place

"I had a lovely fantasy, about shaving your legs. I seem to be going through a phase of thinking about smooth assholes, and the thrill of penetrating them. Not mine, yours! Since you've been freshly shaved, your skin must be very sensitive. And I did it the old fashioned way, with shaving foam and a razor, so you're very very smooth. I hope you don't mind, but I've got you turned on your stomach, the lights down low, and I'm enjoying slowly smoothing lotion on your back, your legs, your ass, and the sensitive shaved places between them. As I slick the lotion over your balls, my hand between your legs, I slide upwards, and my finger gently penetrates your tight hole. You moan with pleasure, having been totally relaxed by the body rub you've gotten. Gradually, I ease a second finger into your asshole, slowly finger fucking you, like a pussy, leaning over you and simultaneously kissing and licking your neck and shoulders. You begin to raise your buttocks a little, meeting each thrust, impaling yourself on my fingers.

"And I reach under the covers, and get the smooth dildo I've been saving for you, and hold it up to your lips for you to suck. And you willingly, slavishly suck it, drawing it deep into your mouth, as I continue to relax your sweet ass with my fingers. You are so beautiful, and so willing...your legs slightly spread, your hard cock pressed underneath you. I withdraw the dildo from your mouth, and slowly slide it into your tight hole, a little at a time. As its thickness enters your body, your clit jumps a little, and a small trickle of pre-cum drips down it's head. After the dildo is all the way inside, I stand up, and look at you lying there. I can't resist, I lean down, holding your head, kissing you...thrusting my tongue in your mouth...and the doorbell rings.

"I instruct you to stay right there...don't move, I have a nice surprise for you...and go to the door and let in my friend Bobbi. She is a VERY cute woman, model material actually, petite with pixielike short black hair, mysteriously androgynous and very bi as well, and I've told her about you, and the magic your tongue can perform on my pussy.

"As you lay on the bed, the dildo protruding from your asshole, she and I begin to kiss passionately, and our fingers begin caressing each other's pussies, mine already wet from the treatment I've given you. I whisper into her ear, and she nods, and lies down on the bed beside you, face down also. Now it's your turn, and with the dildo still inside of you, you have to kiss and lick her neck and back, and slowly work your way down to her sweet little pussy. She moans and wriggles in pleasure as you stick your tongue up her pussy, sliding it in and out, preparing her for what is to come. You finger fuck her tight ass and lubricate it with her juices.

"At the same time, my mouth has found its way to your hard girlcock, slowly sucking its swollen head, licking up and down the shaft. The dildo in your ass excites you, and you thrust your hips toward my face, your cock sinking deep into my throat. It swells even more, but I don't want you to cum quite yet, and I stop my caresses. You are so sweet and so willing, and so you don't hesitate a moment when I tell you to please sink your rod up to the hilt in her waiting ass. She wants it bad, my dear.

"As the head of your cock passes her tight sphincter, the two of you cry out in unison, in profound pleasure. She arches her back, begging for more of your shaft, and you gladly give it to her. The dildo in your ass, and the tightness of her hole is nearly more than you can stand...and I start slowly fucking your asshole with the dildo, as you're fucking her...as you back out of her, you impale yourself on the thick cock in your ass, as you move forward, you fill her with deep pleasure...her hand creeps beneath her body, her fingers stroking her pussy lips and firm clit, and she begins to cum, crying out. Her asshole begins to rhythmically open and close on your sweet girlcock, and you drive as deeply inside her as you can, the dildo buried deep inside of you, your hot semen pumping, filling her body...

"And I realize that I have not had an orgasm, and my pussy is throbbing and wet...and you may be tired, but you are going to have to do something about this, right now!

 

"Subject: Bobbi & Boygirl (continued)

"Your cock slowly enters my upturned pussy, delving into the warm wetness as my lips lower themselves towards Bobbi's eager cunt. I know her sweet taste well, and her head drops back on the bed, and she begins to moan and rotate her hips. The pleasure of your penetration has me moaning as well, and the vibration of my voice adds to her sensations. Somehow our roles have changed, the thrust of your pelvis against my ass makes me feel submissive, and I revel in the knowledge that you will not stop fucking me until I have cum, Bobbi has cum, and you can't stand the pressure of another impending orgasm.

"Each thrust of your hips pressed my mouth against her wet slit, and as she begins to cum on my face, I slide as many fingers will fit into her hot cunt. She cries out, loudly, and begs me to please fuck her, and I oblige with my tongue and slick fingers, pumping them into her swollen hole, slowly but a little roughly—I know

she likes it that way. And my pussy is responding as well to the delicious feel of your thick shaft, tightening with desire and my approaching orgasm. Your girlcock glistens as you withdraw it completely from my now desperate cunt, and you begin to insistently press it into my asshole, as a recovering Bobbi kneels by your side.

"As your uncomfortably thick shaft eases it's way into my ass, her fingers find their way into my grasping cunt - both my holes are filled, and I am swept into a frenzy of desire, uncontrollably moaning and thrusting myself on your throbbing cock, cumming again and again. My legs are spread as wide as they can go, and you impale me over and over again, as her fingers begin rubbing my overly sensitive clit, and as my asshole quivers in yet another orgasm, you fall forward on top of me. Your cock jammed in as deeply as it can go, your orgasm overwhelming your body, and your sweet girlcum spurting inside of me, you hold me tight and kiss my opened mouth, telling me what a sweet little cunt I am.

 

"Subject: Alternate Ending (Bobbi and Boygirl, part 3)

"Ok...the plot so far...

"I believe that after kissing and fondling Bobbi, I asked you if you would fuck her asshole, since she likes that sort of thing. And while your thick cock was buried deep inside of her, she was finger fucking herself and licking my pussy...

"But this time you don't get to cum...at my request, you have to hold back, making your penis available to her, thrust deep in her ass, so she can have a spectacular orgasm. And she does, humping against her own fingers...her tongue lashing my clit. You have to stay inside of her, throbbingly close to your own orgasm, while she finishes me off. She does a nice job, my hands holding her head, my fingers laced in her hair...I love the way she kisses my pussy as if it were my mouth, kissing over and over, her tongue delving inside of me.

"After I have cum, you are allowed to pull out of her ass. Bobbi rests on the bed while I take you to the shower to quickly clean up. You stand meekly in the shower while I lather you with soap, paying attention to your smooth balls and ass, and being sure to get your still hard cock really clean. I tease you with my soapy hands, playing with you, stroking your shaft but not letting you cum. You are getting frustrated, and it's not going to get better any time soon.

"After you get out of the shower, I towel you off, and reach into the cupboard and produce a length of soft, skinny, rolled leather...like a piece of spaghetti or shoe string, but smoothly finished all around. To your surprise I begin to gently lace up your still erect penis, sort of Roman-sandal style, crisscrossing, and tying the ends at the base. It's not painful to you, but somewhat restrictive, and you wonder what I'm up to. I lead you back out to the bedroom, where Bobbi sees your cock and smiles with delight. She knows what is going to happen, and she is excited. She crawls to the edge of the bed, her mouth at your crotch level, and begins licking your cock. As she sucks it's head, you feel exquisite pleasure as it swells like a tasty plum. I tell her to make you cum.

"She begins to suck you off with serious intent, and it doesn't take long before you thrust yourself into her mouth, you've been waiting so long. But while your cock trembles with the pleasure of an orgasm, the lacing doesn't allow your semen to exit, and your cock remains erect and sensitive, and you feel a pressure in your balls that you would dearly like to relieve.

"Bobbi lays back on the bed, beckoning you to fill her pussy with your now cock. You plunge into her, wanting to cum, to fill her cunt, to pay her back for the frustration you are feeling - and she loves every second of it. The sensation of this ridged cock makes her scream in pleasure, her legs wrapped around your back, her hips thrusting upwards, her mouth biting and sucking at yours. My arms are wrapped around you, alternately teasing her nipples and yours as well. She is cumming over and over again, her heels on your ass drumming you deeper and deeper inside of her. You have another pleasurable but frustrating orgasm, your cock still annoyingly erect, your balls painfully engorged...Finally, Bobbi has had enough, and you pull your beautiful, thick, pulsing cock out of her slit, dripping with her wetness, and you look at me with complete frustration...

"I roll her over, and she complies willingly, tiredly, and I reach for the laces around your cock. I carefully untie them, releasing your rod, stroking the shaft, and lightly licking it's head. You throw your head back in pleasure, and I turn you towards Bobbi's relaxed asshole, helping you slide your swollen cock inside of her.

"The sensations for you are unbelievable, you have waited for so long for an orgasm, it only takes a few thrusts in her tight ass, and you release the pent up sperm you've so wanted to fill her with. You can hear her muffled groans of delight, feeling the quantity and heat of your cum..."

(15) With Humor Came Tenderness and Curiosity

 

"I would like to say that you are responsible for me not being worth anything at work these days! I can't stop thinking about our conversations, and my pussy is constantly aching. I have had more orgasms this last month than in all of last year! I'm Gonna Explode if I don't fuck you soon! I thought of you and your sweet mouth yesterday. This warm weather does something to me, every hot afternoon I get languidly aroused and have to do something about it. When I lay in the sun it's even worse. When my sister and I went to Alki, I thought about how nice it would be if you were lying next to me, and I could see the bulge from your clit. Alki was magically a secluded private beach, so I could reach over while you were drowsing in the sun on your back, and lightly trace its outlines through your bathing suit. You moaned in your sleep, enjoying the increasing pressure of my fingers. I gently slid your suit down your body, freeing your girlcock, and leaned over and took it's head in my mouth, licking and kissing it. Hmmm...are you still sleeping or just pretending to sleep, lying completely still and quiet? I inch upwards, taking time to lick your salty nipples, biting them gently, sucking on them like small breasts. And then back down to your girlcock, smelling of warm sweat and sun, and of the salt water of the Pacific. I continue gently sucking on its head, licking up and down the shaft, not wanting to wake you. I see it swelling, your orgasm approaching. At the last moment, my tongue still delicately flicking, teasing, I take as much of your shaft into my mouth as I can hold. Your hips rise off the blanket, your hands instinctively clutching my head, as you pump warm jets of cum down my throat, a groan escaping your lips. You sneaky boygirl, you were awake all along!

"What we have is good. At least for me. It makes me feel good even though I don't necessarily understand it. Even when I'm not trying to just get "high" by reading your inner workings or sharing my own, it feels good. That you can make me cum with just your words, totally liberate me with your imagination and validate my own history with your confessionals has been so empowering I can't believe it. I think the term you used in a recent letter about turning your women on to their "raw female sexuality really sums it up for me. I'm starting to understand that that's what I love most about you and what you've brought to our relationship. Not only is your acceptance of my inner needs important but your nurturing of them even more important. My significant other 'accepts' the fact that I have them, but it's kind of like Clinton's "don't ask, don't tell" policy. Just accepting them isn't the same as honoring, encouraging and even loving them. You do this for me, boygirl. You prepare my soil, plant the seeds, water and weed them, and—most of all—heap the fertilizer on so lovingly that I can't help but grow and blossom for us both! I hope you enjoy the aroma of my flowering as much as I love having you put your nose so deeply into me that you can inhale all my inner essence.


"I've never met a man with nipple-sensitivity it (the NS factor) like you have, but mine are the same, and men absolutely love them. Many have commented on how jealous they are. I have the capacity of orgasm from nipple stimulation only and have heard of very few women who can brag of that.

 

"I do love knowing that I have the power to turn you into a boycunt, and when you talked about laying in the next room listening to me make love, you really hit my turn-on button. I've always really gotten off making love in motels where I knew we could be easily overheard. I'm always much more vocal, make more sexual sounds, bang the bed against the wall and talk way dirtier than at home. 'Oh yes, lick it, (pant, pant,) oh yes, yes, (snort, snort,) fuck me, fuck me now, stick it in, (gasp, Gasp!) now, NOW, yes, yes, oh Yes YES, Oh fuck, I'm cumming, Oh fuck! Oh GOD oh Fuck, Harder, Faster, oh Fuck FUCK!!!' I heard a woman doing exactly that many years ago, and I actually came when she did—just listening to them. Ever since, I've enjoyed trying to return the favor whenever possible! :-)

"Toni—boy, do I want to hear more about her! I really love sharing real experiences and people. Fantasies are a special turn-on, of course, but sharing real-life seems to get me wetter, quicker. Toni pushed a special button with me. The modeling/ studio/fucking, and especially the telling you about it later scene—all this cries out to me for more detail. I could really get into that, having been in front of a camera on occasion in my past, and knowing the exhibitionist-rush it gave me.

"If Toni had been able to bring out the sissy in you when you were twenty-two, your life would have changed forever! I picture her teasing your nipples and fucking you with a strap-on dildo before the swingers parties, leaving you in a state of arousal and frustration, and then going with you to a party where she gets all her needs satisfied by beautiful studs with toned, muscular bodies! Wow! Then she takes you back to her apartment and lets you clean out her pussy with your nimble tongue. Yes! I want you to play with yourself over the next few days with that image in your head and a butt plug in your ass!

"It's still gray outside. I just slipped my fingers inside my robe and discovered that my nipples are now nice and hard and pouting---just the way I love them. Writing to you seems to have pleased my body, and for that I thank you. I'm considering the idea of picking up the phone and calling Tom---I wonder if he'd be interested in another date.

"Kisses to your little titties, Michael-Jane. Hope they are as perky as mine are right now and you squeeze them lovingly for me. Remember to think of me. And don't forget to think of your other former (and future) girlfriends too…all doing you as I do!

"You really ARE a good little cocksucker, Michael-Jane! Now that you mention those boyshorts from the party, you might look nice in thigh-high stockings too. I've always had this urge, when I see one of those Victoria's Secret models, to slide my hand up her nyloned thighs, slowly, her head resting on my shoulder as we stand in the middle of the room...slowly, teasingly, until my fingers reach the treasure hidden under her panties...and fondle her through the silk until she is helpless....open...I could do the same thing to you, too.

"And after your knees weakened from the effect of my fingers, I would lay you gently down on the bed, on your back, and lay on top of you, my weight pressing you down...softly, insistently, licking your nipples, while at the same time rubbing my dampening pussy on the clit imprisoned in the silk panties... ahhh, you are so hard, it feels so good on my clit, I bite down gently on your stiff nipples and circle them with my tongue...

"I want to lick you all over. Did you remember that my significant other was standing behind me, stroking his lengthening shaft? Maybe this time I will make HIM watch, as I make love to you as I would to a woman, gently, slowly, as he can never do...kissing, our tongues clashing...I work my way down your chest, nibbling, one hand holding each breast, as I playfully tug your boyshorts down with my teeth...freed, you spread your legs for me as I lick between them, with long slow strokes. I slide upwards and turn around, simultaneously lowering my pussy to your face and my mouth onto your shaft. Your girlcock fills my mouth, I love that feeling and the taste of you...Your tongue is working magic on my clit...I can't help it, my hips move slowly and sensuously over your lips, fucking your face. You wrap your arms around me strongly, tightly, and you gently roll us over so that you are on top, and you are fucking my mouth.

"You are so good at this, boygirl! Your tongue starts licking and kissing me and I hold your head, directing where I receive the pleasure of your mouth. I can feel my first orgasm building. I look down between my legs, enjoying the view of my hands holding your head between them and I arch my back in a thrilling orgasm, impaling myself on your tongue, squeezing your head between my thighs.

"But we are not alone and you are very much the sissyboy today. Remember that your firm, girlish ass faces my significant other and his now-raging hard-on...."

 

(16) In the End, I was Reminded that I was a Lucky Little Bottom

 

"I'm in a very aggressive mood and I think you have been getting away easy for far too long.

"I had been out shopping all day, and was tired and my feet ached. I was glad to see that you were home when I arrived, and you knew by the look in my eye that I needed some attention. Some of the things in my shopping bags were for you, from a special store I visited today.

"Don't talk, just do what I say", I murmured into your ear, my arms around your shoulders. I started removing your clothing, and after you were naked, I went around the house being sure the blinds were closed. I returned to stand in front of you, and ordered you to kneel in front of me, as I began to remove my clothing. I was wearing very high heels, stockings, crotchless panties, and a leather corset cinched tight around my waist. From a shopping bag I pulled out few leather straps and cords, and a small leather riding crop with a suspiciously thick handle.

"By this time you knew what was in store for you, and your hands were caressing my thighs spread in front of your face, my pussy at eye level. Pulling you into a standing position, one hand holding both your wrists behind your back, I kissed you, at first gently, and as I became more aroused, harder, my tongue invading your sweet mouth, my hand at the small of your back pressing you hard against me. The high heels made me the same height as you, and my insistent kissing made your knees bend, and your head tilted back, your mouth opening wide to receive my tongue.

"With my mouth, I pressed you slowly backwards to the floor, where at last you lay helplessly beneath me. I buckled a leather belt around your waist, which had two convenient loops at the small of your back, the perfect size with which to enclose your wrists. Your clit was fully hard, and as I reached up to slip a silk blindfold around your eyes, it seemed to swell even more. I couldn't resist giving it a kiss, and the salty taste of it made me lick it a little, teasingly, enjoying it's hardness and the way you squirmed, trying to get me to suck on it...but not yet, my dear.

"Your arms were uncomfortable behind your back, lying on the floor like that, so I tugged you to your feet, and led you to the bedroom, where I had you kneel on your hands and knees. Your smooth ass was sticking so nicely up in the air, I thought it might need a little attention...you started when I put my hands on your cheeks, and spread them a little, but then moaned deeply when you felt my finger slowly insinuate its way up the pink crack of your ass.

"I grabbed the riding crop with the suspicious handle, and began flicking your tender ass with it, as you yelped in surprise. Not too hard, oh no, just a little bit, to counteract the sweetness of my fingertips on you, it wouldn't do for me to be too nice and I moved around to where your head was resting on the bed, your mouth open in surprise and desire, and asked you to suck on the thick head of the crop, to suck on it like you were sucking on a thick cock.

"I know you're such a good cocksucker...I pushed it slowly deeper and deeper into your mouth, in and out, your tongue swirling, as I position my hot and wet cunt in front of your face. As I pull off your blindfold so that you can see again, I slide the still wet handle into my aching pussy, masturbating slowly, just a few inches from your yearning mouth.

"Ahhh, it feels so good, you can see the lips of my pussy clinging to the sides of the thick black crop as I slowly pull it out, and then spreading as it plunges back in. I need your tongue on my clit, and as I pull the handle out of my pussy, I reach for your head and pull you forward, pressing your mouth where I need it."

"Given my recent fantasies as YOUR submissive, I had almost forgotten how much I love having you as you as a submissive to feed my sexual appetite. It's definitely been too long since you assisted other men in their attempts to satisfy my needs. What a rush knowing you get off by being totally devoted to me and my every whim. Your reward (allowing you the pleasure of slurping the cum of other lovers out of my pussy) seems like the least I can do after the way you heightened my orgasms by your service.

"However, after reading your email this morning, I fear I may be granting you too much too soon. You sounded like you got way too much satisfaction. I want you climbing the walls each and every day. I want you to know that your reason for existence is to turn me on.

"You are definitely on the right track, but we need to fine-tune your role. I want you to feel constantly feminized, your girlcock interfering with all the rest of your daily activities. Allowing you to cum at will as a male is sure to take away some of your need and, more importantly, adversely affect the quality of your service. Since that reduces your effectiveness as my submissive, in the future you will be allowed to cum only en femme and only when I specifically give you permission.

"I am completely aware that you receive a great deal of pleasure when I allow you to be butt-fucked or slurp my pussy. However, since I, too get off on seeing this, I guess I'll just have to allow it. When you are able to prove to me that it is YOU that heighten my orgasms above and beyond anything I have ever known, I will reconsider allowing you the release you crave."

(17) Things Change, However. Sweet Partings, and All That Jazz.

 

Take care of yourself, sweetie, and be proud of who and what you are. You are so interesting, you truly are a mixture of masculine and feminine. Part caveman and part slut. :) You're more than just okay—take it from me. I hope you find a woman (and/or a man) who will honor your boygirl and bring much happiness and sexual fulfillment to your life(s). She is out there somewhere for you—keep looking. Even if you don't find her, I hope you will find peace and contentment and have a very good life. Thank you for letting me be part of it, and for lubricating mine in such a special way. I've loved what we had between us and will think of you often—and I certainly will every time I masturbate! Enjoy the sunshine! I can feel myself blossom and gain strength as it soaks into my naked body here for the last time, and am ready to head out into whatever comes for me. Goodbye, and thank you so much for our time together!

"I have one final request that I am asking of you before I fade out. Do you remember my foxy friend with the name that also begins with an 'M' ('M' for mischievous, 'M' for mons, 'M' for Monique)? Well, I want you to look within yourself and listen for her voice. I can no longer be with you, but she's agreed to take over. You will find her inside yourself. Trust her and promise me that in the future, you will do as she requests!

"You are my private little sissy. I remain your very special little slut!"

 

Part III

All of the above, of course, suggests that my soul had, as it were, a certain erotic trajectory. After the previous correspondence, I wrote a poem.


 

"Priestess of Cybele"


You are an exponent
Of the dark and beautiful goddess
With whom I have had
A long-standing connection.
I am a waterfall in the Garden of Cybele.
Yours is the reminder that my job


Is to make you long for satisfaction,
Prepare others for love in your name.

My assignment is to please
Those whom you have chosen
With my smooth, submissive ass,
My eager mouth—


Symbols of my erotic status
As a boygirl in your stable.
You have also changed me
Into something

Soft and sweet and willing,
And, let us not forget essentials


Something aching to be used!
Teach me too the elements of patience.
As you pour the waters
From the soul of my sex
Back out upon the land,
I feel my cock transformed


Into a candied clit
Whose purpose it is
To cast a spell on your cunt,
To make your love light burn
Throughout the world,
So that the kind of men


Whom you desire
Will know that you're available!

When you touch my nipples,

You have my full attention!

My girlish ass, rotating ever so sweetly,

Makes infinity signs in the air!

 

Use whatever terms of endearment you will,
But in this life, I can no longer answer to "Sir!"
When you touched my tits,
I felt bolt of electricity shoot through me!
See! Even now, I spread my legs for you!

Even now, I serve as a bridge to the abyss!

  

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