Destination Unknown
by Miss K
Jeff slid into the seat on the airplane. He always hated traveling. It
wasn't so much the comfort factor as he was relatively small at only five
foot eight. But nonetheless Jeff always seemed to attract the most
undesirable people on the plane who somehow always had to be sitting next to
him.
To make matter even worse was the fact that he knew just how long this
trip would be. Jeff had recently moved to England from the United States and
the long flight over was still fresh in his mind. And now, only a few months
later, he was on his way back for business. Despite this Jeff was a little
more at ease knowing he would have a week off after all of his meetings to
visit with his family and friends.
As he was settling down for what he knew was going to be a long flight
his eye caught the sight of one of the most beautiful woman he had ever
seen. She had brunette shoulder length hair that framed a face with the most
delicate features he had ever seen. However, what caught his attention the
most was her shapely body. She had an astonishingly small waste that helped
form the perfect hourglass image.
Jeff seemed to loose sense of reality and before he knew it he was
staring as she made her way down the isle and stopped at his row. Still
captivated by her image, he was finally thrust back to life when he heard
her softly say "Excuse me, I need to get past you to my seat."
Jeff did a double take looking at the empty seat next to him before
looking back at the beauty. He couldn't believe his luck. Could he really be
that lucky to sit next to this beauty for the long flight? Jeff immediately
stood up and let her get herself situated in her seat before taking his seat
again.
It wasn't until halfway through the trip before Jeff finally got up the
nerve to talk to her. He had noticed that she was reading an article about
models in her magazine and promptly asked "Sorry for being nosey but I
noticed what you are reading, are you a model?"
"Oh dear no" she giggled, "I was just trying to find something to pass
the time" She replied.
"Oh, well you are definitely beautiful enough to be one" Jeff weakly
stated.
"Well thank you…." She trailed off.
"Oh I am Jeff", he said picking up on her hint.
"Well Jeff, my name is Rebecca and let me tell you this body is the
product of a lot of upkeep."
"Well whatever you are doing keep it up, you look amazing! I hope you
don't think I'm being to forward or anything but you have the perfect body
shape."
She blushed and replied "Well I must confess that I have some help in
that department. You see I wear corsets and that's probably why you find my
body shape in the state it is."
"Really? Wow, I can't say I have ever met anyone who has ever worn a
corset. I have seen them in some movies and all, and I must say they have
always intrigued me, but it seems like most woman don't wear them anymore."
Then with a pause Jeff continued, "I'm sorry you must find this a little
uncomfortable."
"Oh I don't mind really. It's not some secret or anything. I'm
comfortable with myself so I really don't mind."
For the remainder of the flight Rebecca and Jeff chatted back and forth
swapping backgrounds and stories of their personal life. Jeff learned that
she a very successful businesswoman who was going to be staying at her
apartment in the city while doing business the next week or so.
Eventually the plane landed and as Rebecca stood up and began to get her
carry on bag from the overhead storage.
"Well it looks like the end of the road" Jeff said. "I just wanted to let
you know how much I enjoyed your company. It sure made the flight much more
enjoyable."
"It was fun, and a great way to spend the ride over." She paused a bit
and then reached into her purse and pulled out a business card and slipped
it into Jeff's hand and whispered into his ear "don't be a stranger" before
she turned and walked off the plane.
Jeff stood there several seconds before he looked down at the card she
given him to see it had the address of her apartment listed on it. Jeff
smiled to himself before walking off the plane.
…………………………………………………..
Business went well and before Jeff knew it all his meetings were done and
he had a week of vacation to spend however he wanted. Initially he had
planned on spending it catching up with family and friends. However, the
conversation and company of the plane trip kept playing in his mind and it
was only a few hours after his last meeting before Jeff found himself
standing in front of the door to Rebecca's apartment.
Nervously, Jeff knocked on the door not knowing if she really ever
expected him to take her up on her implied invitation.
It was only a few moments before the door opened and Jeff was greeted
with the site of Rebecca looking just as gorgeous as he had remembered.
"I'm so glad you were able to stop by. I was beginning to think you
wouldn't" greeted Rebecca.
"Well how could I say no to such a beautiful woman who made my trip over
so enjoyable" Jeff sheepishly replied.
"Well come in and have a seat. Would you like anything to drink?"
"Thanks, and I will have whatever your having." Jeff replied as he took
in Rebecca marvelous apartment.
Jeff sat down and waited for Rebecca to return. It was only moments later
before she came into the room and set a glass of wine down for him.
"Thanks, and I just have to say that you look absolutely wonderful
tonight" Jeff said as I took a sip of wine.
"Why thank you" she replied. "However, it probably has more to do with
the stricter corset I'm wearing tonight." She said smiling.
The two continued to chat and have drinks. Eventually the conversation
turned back onto the topic of corsets.
"I find them so interesting. They make the wearer look so sexy, and I
cant help but to wonder just what it would feel like to wear one" Jeff said
without much thought.
Rebecca let a small laugh out at that statement. "Well would you like to
see how it feels to be laced into corset?" grinned Rebecca "I mean, you did
say you always wondered how it would feel…"
"Umm…well it was more an inquisitive remark than anything. Besides it's
not like I could fit into anything you have." Jeff replied hoping to get
himself out of the clear.
"Oh I don't know about that" grinned Rebecca. "You're only slightly
taller than me. Sure you're more muscular and solid, but I'm sure with some
tugging and squeezing I would not only have you in one, but tight-laced as
well!"
After a moment of silence Rebecca continued, "Oh come on it will be fun."
Even though Jeff hadn't verbally agreed he knew there was no getting out
of it.
"I can see you have already made up your mind" Jeff laughed nervously.
"One way or the other you're going to get me into a corset tonight aren't
you?"
"You could say that, and perhaps a little more." Rebecca teasingly
replied as she sauntered down the hallway towards her room.
Jeff stood frozen watching Rebecca's perfect figure walk down the hall,
teasing him to follow. Without much thought to it Jeff began dreamlessly
walking towards her room despite knowing what laid in store.
As Jeff entered, Rebecca stood in the center of the room holding a corset
in each hand. She stared seductively at him as if to say she had him trapped
and she knew it.
"So which one is it going to be?" Rebecca said raising the two corsets
up. In her right hand she held a plain white satin corset, and in her left
hand she dangled a sensuous looking black satin corset. For some reason the
look of the black corset just drew Jeff in and without hesitation he
replied, "I like the black one."
"Great, I was hoping you would choose this one! This corset has so many
possible additional features, and it's just so feminine the way it looks.
You are absolutely going to love this. Now strip everything off and we can
get you into this sexy piece!" She said as she flung the white corset onto
the bed.
"Ummm…Everything?" Jeff asked, a little nervous about getting naked in
front of someone he didn't really know all that well.
"Well we can't very well lace you into a corset with your shirt and jeans
on. And your boxers will definitely ruin the image of the corset." Rebecca
stated. "But if you're going to be so modest then you can wear these." She
said as she walked over to her dresser and tossed Jeff a pair of black satin
panties.
"Listen Rebecca, I don't know if this is such a good idea. I mean the
corset is one thing but these?" Jeff said raising the panties up.
"Oh come on Jeff, please…." She said as she came closer to him; running
her hands over his body. "What's so bad about the panties? Sure they are
more feminine than your boxers, but they will look divine with that corset.
And besides its only me and you here, no one will ever know."
Jeff practically melted as Rebecca ran her hands over him. He couldn't
help but think that she had a point. With that he took the panties and
slipped into them. He was amazed at how wonderful the silky material felt as
they slid up is legs. Enjoying the experience, Jeff couldn't help but think
that perhaps Rebecca was right; they were not that different from his
boxers. Sure they were much more smoother, felt really nice, and were cut
differently, but they were actually quite pleasant to wear.
Jeff's thoughts were quickly interrupted as he felt Rebecca's hand reach
from behind and gently massage his groin through the panties. "I can see
someone is enjoying wearing those panties." She seductively whispered in his
ear.
"Now" she said as she stepped away "lets get you into that corset."
"I think I should be able to get your waste down a good four of five
inches." She stated as she picked up the corset. "Ok, this will work better
if you have something to hold onto. Why don't you go over and hold onto the
top of the door."
Jeff walked over and grabbed onto the top of the door. Within a matter of
seconds Rebecca had wrapped the corset around his waste and started to
thread the laces into the corset. Jeff couldn't help but think as to how odd
it was that the corset had to open from the back and that the laces would
have to be undone in order to remove it. Those thoughts were quickly thrust
out of his mind as Rebecca gave a hard tug on the laces.
As the corset continued to tighten Jeff couldn't help but notice how
sensual and erotic the whole experience was. From the firm way it held him,
to the way it started to mold and shape him to its shape. Just when he
thought she had finished lacing Jeff felt her give the laces sharp tugs
before she started to tighten the laces even further. When she was finished
Jeff became aware of how the firmness and pressure the corset restricted his
breathing. He immediately learned that he would have to take short shallow
breaths.
"Ok sweetie, you can let go of the door!" Rebecca stated with a
noticeable hint of glee to it.
As Jeff lowered his arms he felt like the corset grew even tighter. In
shock he let out a tiny little gasp.
"So tell me how does it feel?" Rebecca asked.
"It's like nothing I have ever experienced before. The tightness and
pressure as it molds and shapes me feels so erotic and yet makes me feel so
vulnerable and helpless." Jeff replied.
"Really?" Rebecca said as she moved behind Jeff once again, taking two
small strips that had half of a zipper on each side and attached it to
either side of the corset and zipped the two strips close over the laces
before finishing it with the snick of a lock securing the zipper shut. "And
how does that make you feel?" she laughed.
"What did you do that for? I think this has gone far enough, now unlock
me and let me out of this thing!" Jeff stated franticly.
"Oh come on sweetie. Just a minute ago you couldn't get over how
wonderful it felt, and I just wanted to show you some of the other features
of this particular corset. I'll let you out once were all through having
fun. I promise."
"I don't know Rebecca, I thought this was all we were going to do. What
else could you possibly have in mind?"
"Well, seeing you in my corset and panties really turns me on, and you
look so feminine and adorable. I was thinking that perhaps you would let me
finish off the transformation and see how you looked as a woman." She said
as she sauntered over to Jeff and once again began to gently stroke his
groin through the satin panties. "Please sweetie?"
"I don't know Rebecca…" Jeff didn't know why he just didn't say no, but
as he stood there feeling the erotic pressure of the corset, and the
caressing hand of Rebecca through the panties he couldn't help but utter
"Yea… ok. I guess it could be fun."
"I promise you that you will look amazing! Luckily you don't have much
body hair so we can skip shaving your legs." Rebecca said as she strolled
over to her dresser once more and began to dig around and select things.
"Ok sweetie, why don you take a seat on the edge of the bed and we can
get your legs encased in these sexy stockings I have here."
Jeff nervously made his way over to the bed knowing that once he let her
continue with his transformation that there would be no backing out until
she decided she was completely finished.
Jeff sat down on the bed and tried to calm himself down as Rebecca
started to roll the stockings up his legs. The cool sensation of the silk
stocking being slid up his legs was much more pleasing and enjoyable than
Jeff ever thought it would be. When she finally had them on each leg she
lightly ran her fingers up each of Jeff's legs and thighs before hooking the
stockings to the garter straps hanging from the corset. Jeff didn't know
what struck him as he was consumed in the sensation of soft feminine
lingerie.
After making sure Jeff's stockings were on correct Rebecca stood up and
grabbed the bra she has selected and held it out for him by one strap. She
let it dangle teasingly off of her index finger before saying "I want you to
but this on for me sweetie. I want to see you slide this bra over your
shoulders and strain to hook it."
With a shaking hand Jeff reached out and took it from her. He slowly
slipped his arms through the straps and reached around and grabbed the two
sides and tried to do the clasps in the back. After much fumbling around and
struggling Jeff was finally able to get it hooked.
"Very good, I'm surprised you were able to get that hooked all by
yourself. Are you sure you haven't done this before?" Rebecca winked at
Jeff. "There's still something not quite right about your figure though….. I
know what it is!"
Rebecca walked over to her closet and dug around in the back shelves for
a few minutes before coming out with two boxes. She set them on the bed and
opened them up to reveal two very real looking breasts. "These will give you
just the right shape that every woman should have up top. Now this might be
a little cold at first since I'm using medical adhesive, but this way they
will stay in place. Don't worry though, they should warm up fairly quick!"
She said as she coated a clear liquid on the backs of the breasts. She stuck
them in the cups of Jeff's bra and pressed them up against his chest for a
few minutes before she took her hands away. Jeff could immediately feel the
additional weight of the breasts and was at once glad for the support the
bra provided.
"Ok now lets get you dressed!" Rebecca said as she tossed Jeff a soft
black skirt. He started to step into the skirt and immediately noticed how
soft and intense it felt as it slid up his stocking clad legs. Much to
Jeff's surprise, Rebecca had selected a skirt that was very stylish and yet
still only came to just above his knees.
Rebecca smoothed Jeff's skirt out for him and then went back to her
closet and took out a long sleeved burgundy top that had a draping neckline.
As she handed it to him, Jeff couldn't help but notice how soft and light
weight it was. For a moment he thought that it wouldn't fit, but as he began
to put it on he felt it stretch. Needless to say it hugged and accentuated
every feminine curve Rebecca had created.
Jeff couldn't help but catch Rebecca's smile as she took his hand and led
him over to her vanity where she had him sit down in the chair. Then, much
to his surprise Rebecca was straddling his lap and reaching onto the vanity
for her makeup. "Ok sweetie tilt you head back just a bit and let me make
you into the woman of your dreams." She said as she winked at him.
Jeff did as she instructed and tilted his head back and let his eyes
close. It wasn't long before he felt the soft movements of brushes sweeping
across his face, covering it in layers of makeup. Jeff couldn't help but
think of how erotic it felt as Rebecca moved the brushes and pencils along
his face. To further add to his excitement Rebecca would occasionally wiggle
her bottom and press up against Jeff's member or let her soft breasts rub up
against the fake breasts she had attached to him. With all of this
stimulation Jeff sat there extremely turned on unable to hide the fact.
While he knew Rebecca could feel his excitement she never outright
acknowledged it, but seemed to wiggle her bottom in his lap to further
arouse him.
In all of his life Jeff never though that he would be getting excited by
a woman applying makeup to him while wearing a full set of her lingerie and
two large fake breasts. With that thought Jeff felt something slide on top
of his head and the sensation of hair draping over his neck. Wondering what
was going on, Jeff slowly opened his eyes and tilted his head up and looked
into Rebecca's eyes as she adjusted what obviously was a wig.
"Don't move just yet, I still have one more things to do before your all
made up!" With that Rebecca grabbed Jeff's chin and brought her other hand
up holding a tub of dark red lipstick. She moved her face and hand closer to
his mouth and expertly applied a nice coat over his lips. Within a second of
her hand dropping down she embraced Jeff in a deep passionate kiss. He could
hardly contain himself. The feeling of the clothes and the makeup along with
the taste of lipstick intertwining drove Jeff absolutely insane. Rebecca
finally drew away and slowly stood up giving Jeff's panty covered crotch a
squeeze.
"Go ahead sweetie, take a look at yourself while I get a few other small
things." Rebecca said as she walked over to her closet.
Jeff nervously turned to the mirror Rebecca had at her vanity, half
expecting to look like nothing more than a man in drag. Much to his surprise
Jeff looked somewhat convincing. The corset and false breasts did wonders to
shape his body into a female form, and Rebecca had done an amazing job on
his makeup. Combined with the shoulder length brown wig Jeff couldn't help
but admit to himself that Rebecca had done a pretty good job. While he knew
he would never pass for a woman under close scrutiny he couldn't help but
think that he just might get by on a casual glance.
"All right sweetie, just a few more things to finish off your illusion."
Rebecca said as she sauntered back to Jeff, holding a pair of high heels.
"Here slide your feet into these heels." She said holding up a pair of high
heels that must have had at least a five-inch heel! "Now these are a bit
extreme, and are more of a prop than everyday wear, but they were a little
bit to big on me for my Halloween costume but they are the only ones I have
that you will be able to squeeze into."
Jeff slowly rose one of his stocking clad legs and gently began to
squeeze his foot into one of the heels before doing so with the other.
Rebecca was definitely right; they were without doubt a tight fit. However,
just as she said, Jeff would be able to fit in them.
Rebecca promptly kneeled at Jeff's feet and began hooking the straps
around his ankle. Just when he though she was done Jeff once again heard a
couple little
* snicks
* and assumed she had clasped them
shut. However, when he looked down, much to his horror, he found out that
she had instead padlocked the straps shut. Jeff knew right then that there
would be no way he would be able to remove his heels without her key!
"Hey, why did you lock these things on me?" Jeff cried out.
"Oh come on silly. It's just a little bit of fun. Just go with it and
enjoy yourself!" Rebecca said, completely blowing off Jeff's complaints.
"Alright sweetie, give your new shoes a twirl. Lets see how you handle those
new heels!" And with a sharp slap to Jeff's bottom she sent him off around
the room.
It took Jeff awhile, but after getting accustomed to the feeling of
heels, and a few shaky laps around Rebecca's bedroom, Jeff began to feel
like he was walking like a pro. However, Jeff's pleasure was short lived as
Rebecca stopped him and told him "You have your balance down, but your still
not walking like a woman. Swing your hips and give yourself a sway. That's
the only way you will look like a woman in heels instead of a man."
Jeff took her suggestions and tried to sway his hips but it wasn't to
long before Rebecca stopped him and said "Your just not getting it. Your
movements are either way over the top or just look forced or unnatural. Now
I could have you prance around this room all night before you got it down,
but I think I know something that will give you that natural sway. Now I
don't think its necessary…" she said as she reached into her nightstand
drawer "but it will most definitely get the job done. Now come and lay
across my lap."
Jeff did as she asked. It was only a matter of seconds before he felt her
hand slowly make its way up his stocking clad leg and raise the hem of his
skirt. "Ok sweetie, I'm going to need you to be nice and still and try and
remain relaxed." Rebecca said as she lowered his panties. "Now this may be a
bit uncomfortable at first be let me assure you that it will eventually feel
wonderful." With that Jeff felt something cold and slimy, yet firm, begin to
spread his butt cheeks and slide into his bottom. Despite Rebecca's words,
Jeff couldn't help but to start squirming around from the discomfort as the
object stretched his hole. However, a sharp slap on his bottom from Rebecca
put him back in place. Fearing another spanking, all Jeff could do was moan
as Rebecca continued to apply pressure as she slid the object further into
him until suddenly when Jeff thought he was about to be split in two the
remaining part of the object easily slid in. Rebecca then promptly raised
Jeff's panties back up and lowered his skirt back into place before giving
him a firm pat on his now full bottom.
Jeff quickly stumbled off of Rebecca's lap and in a panic reached back
and tried to feel what was now unfamiliarly stretching his butt. Unable to
reach he looked up into Rebecca devilish stare and asked, "What did you
stick up there?"
"*giggle* Silly it's a butt plug. I know it feels strange and weird right
now but once you get used to it you wont feel right without one. And once
you start walking around again on your heels you will see exactly why I
thought a butt plug would be a good idea for you."
Not the least bit happy Jeff immediately started to walk around the room
again hoping that the sooner she was happy with him, the sooner he could get
out of this. Much to his embarrassment Jeff could feel the plug shift and
move inside his bottom causing him to tighten up his sphincter muscle in
order to hold it in place. Much to Jeff's surprise this caused him to add a
little wiggle and sway to his walk.
"See, now your walking much more womanly and all because of the little
friend I stuck up there." smirked Rebecca. Jeff started to blush at the
comments and from the erotic feeling of the plug caused.
"Alright, what now?" Jeff asked hoping she was done with him.
"Well silly, I didn't get you all dressed up and train you to walk like a
girl for nothing." She said as she walked out of the room and into her
kitchen. When Jeff finally made his way into the kitchen Rebecca handed him
a sealed addressed envelope and stated "Since you look so adorable why don't
you head out and mail this envelope for me. There's a mailbox about two
blocks down. Just walk down there drop it in and come back and I will have a
special surprise for you."
She led Jeff to the door, opened it and pointed him to the direction of
the mailbox, turned around walked back inside and shut the door leaving Jeff
alone on her front steps.
Jeff had never felt more vulnerable and exposed than he was now as he
stood outside her door dressed as woman with a butt plug buried deep in her
bottom. Jeff stood on the steps for a few minutes before he finally mustered
up the courage to begin his journey to the mailbox. Jeff couldn't help but
feel so self-conscious as he began the 2-block trek to the mailbox. As Jeff
began walking he experienced the most foreign sensations. The cool evening
air never let him forget that his legs were encased in stockings while the
light wind blowing his skirt bottom made him even more aware of what he was
wearing. With each step Jeff took he could feel the slight jiggle of the
large breasts and hear the seemingly loud click of his heels as the sound
pierced into the silent evening. All while the unfamiliar sensation of the
plug brought him to a new level of excitement. Thankfully for Jeff Rebecca
had insisted he tuck his male member between his legs, otherwise the smooth
front of his skirt would most definitely have an obtrusion.
After what seemed like hours to Jeff he finally arrived at the mailbox
and dropped the envelope into the mail and turned around to head back to
Rebecca's. On his way back the sensations and feelings soon turned to a deep
pleasure. Taken by this intense pleasure Jeff slowed his walk in order to
relish every moment of the sensations before he would be back in the safety
of Rebecca's apartment.
As Jeff neared Rebecca's place he noticed she was leaning against the
doorframe of her open door with a look of amusement on her face. "I see that
you enjoyed yourself darling, perhaps a little to much…" Rebecca said as she
reached under Jeff's skirt and began to massage his panty-covered crotch.
With glowing smile Rebecca led Jeff back to her bedroom and flung him
onto her bed. "Now for that surprise I told you about." She said as she
began to kiss him deeply while continuing to rub his panty-clad crotch. Just
when Jeff thought he was going to go over the edge Rebecca stopped rubbing
him and scooted herself up and straddled his face. Without any hesitation
Jeff stuck his tongue out and began to orally please Rebecca. Jeff expertly
worked her to several orgasms before slowing down and teasing her eventually
sending her to an earth shattering orgasm.
After awhile Rebecca slid off Jeff and worked her way down to his skirt
and flipped it up. She then pulled his panties to one side freeing his
member. Without hesitation she took it into her mouth. After all the events
of the evening it wasn't long before Jeff was on the edge of an orgasm.
Suddenly the sensation of the weight of the breasts, the clothes, the
makeup, and the way his butt now clenched tightly down on the plug caused
Jeff to burst into what was easily the best orgasm he had ever experienced.
As Jeff lay there in post orgasmic bliss he could feel Rebecca continue to
play with his member as she worked it into what felt like a plastic tube
before he eventually heard a little snick and she pulled his panties back up
and gave Jeff a deep kiss that had the lingering taste of cum.
Jeff lay there admiring Rebecca's firm curvy figure clad only in her
lingerie as she walked to her dresser and removed a red silk chemise and
brought it back to the bed with her. She immediately got to work carefully
removing Jeff's top so as not to disturb his makeup and wig. After that she
removed his skirt. As Rebecca was removing his top and skirt Jeff couldn't
help but think that perhaps his experience was coming to an end. That,
however, was until she once again surprised him and had him slip on the
chemise. Rebecca then slid into the bed next to Jeff and cuddled right up
against his back and whispered into his ear "Good night sweetie!" After all
the events of the evening Jeff drifted off to sleep.
…………………………………………………
Jeff woke up groggily, stretching out in a vain attempt to wake himself
up. It didn't take him long to realize that he wasn't in his hotel room and
that he felt different. Jeff lay there for a while with his eyes closed
trying to remember everything from the previous night. All he could seem to
remember was that he had worked up the courage to visit the stunning woman
at her house for a few drinks. It was obvious from the strange feelings and
his lack of memory that those few drinks had turned into more than a few.
Jeff stretched his hands out to either side of himself to feel if Rebecca
was still here. She wasn't in bed so he assumed that she had gotten up
already. It was at that point that Jeff's senses really started to alert him
that something was different. For starters Jeff felt like he was engulfed in
soft satin. He just shrugged that off as not being accustomed to the sheets
Rebecca had on her bed. But not so easily explained was the weird weight he
felt on his chest, the odd feeling of being full in his butt, why his waist
felt stiff and constricted, and the fact that his morning hard on seemed to
be obstructed and unable to get fully erect.
Jeff slowly ran his hands up to his chest and was shocked when his hands
brushed the fake breast. His eyes opened up abruptly and he threw the covers
off and jumped out of bed. It wasn't until then that the previous nights
events started to filter back into his head.
Jeff looked into the mirror and suddenly started to grasp just how far
everything went. The wigs hair was somewhat messed up but the makeup was
still as expertly done as last night. He was still wearing the chemise,
heels, corset, and the other lingerie from the previous night. Jeff
nervously reached behind himself and felt the firm base of the plug
confirming the reality of the still hazy evening. Jeff then began to
investigate what was restraining his morning erection and placed his hands
inside his panties and found that is member was encased in a small plastic
shell. It was at that moment that Jeff realized that Rebecca had placed him
in a chastity belt! Jeff couldn't think of when she locked that on him but
slightly remembered hearing the familiar snick of a padlock closing during
his post orgasm heaven when he had thought Rebecca had still been playing
with him.
Jeff couldn't believe this and knew he had to get out of this stuff. He
practically tore off the chemise and grasped to rip the corset off but
couldn't find the laces; instead just a smooth surface and two padlocks at
the top and bottom. In his frustration he lost his balance in the heels and
fell back onto the bed. Jeff immediately went to slip them off when he
remembered that they too were padlocked on. He sat there with his head in
his hands wondering why he hadn't put up more of a fight when she was
locking all of that on. Now there was no way for him to get out of this
mess. He slipped his chemise back on taking some comfort in the fact that it
covered the lingerie that now adorned his body.
After several minutes of sitting there in complete shock Jeff noticed a
folded piece of paper on the bedside table. He took it and opened it up
wondering what Rebecca had left to say to him.
Jessica,
I hope you like the name I gave you. I just didn't think Jeff would be
appropriate in your current state. I'm sure by now you have discovered
everything that remains from last night. I cannot tell you how much I
enjoyed all of it. While I know that you had several drinks and probably
don't remember a lot of last night, I still never thought you would go along
with what I had planned, or for the matter as far as things went. I want you
to know you make such a sexy little sissy. While I do not know if this is
what you truly wanted, I do know that a small part of you couldn't say no to
this experience. I am sure you are wondering about the situation I left you
in. While I know you can, and probably have, removed butt plug and whatever
clothes you could, there is still the matter of the other items that you do
not have the keys for. I am sure by now you have realized exactly what the
locks on the corset and heels mean. I'm sure you also found the chastity
belt I placed you in. I'm sure this came as a surprise to you as I sort of
snuck it on you. You see when you came in and I saw you enjoyed your little
stroll I couldn't believe what a sissy you were. I was quite unable to
accept this and thought of it as a little revenge for enjoying what was
supposed to be slightly frightening for you. Additionally, incase you
haven't noticed last night I used long lasting makeup products on you. Your
makeup shouldn't run or fade for at least four or more days and wont be
completely gone for about another week. Now I, on no certain terms, plan to
keep you captive within these items; however, I do have a choice for you to
make. You may or may not remember last night I said I was leaving town for
business today (Friday) and would not be returning till Monday evening.
Should you want to see where this relationship takes us and decide to stick
around I will coming straight home on Monday and we can continue where
things left off. However, if you wish to stay there are several rules you
must abide by. You will keep your buttplug in at all times, and you will
continue to dress in a dress or skirt and blouse at all times. Additionally,
I request that you take it upon yourself to maintain the upkeep of my
apartment in the meantime. If you however wish to leave, which I wont old
against you, you can leave at any time. While I have disposed of the male
clothes you came here in, I'm sure you can find a pair of jeans or something
less feminine to wear on your way out. I however cannot give you freedom
from those things locked on you so you will have to leave wearing them. You
see that envelope you mailed last night was an envelope containing the keys
to the padlocks on your corset, heels, and chastity belt. I made the
envelope out to the address that was on your driver's license. Since the
mail wouldn't be collected until sometime this afternoon I doubt the keys
will be sent out to your address until Monday and will take at least a
little over a week to reach your home in England. Although I assure you that
all the keys are in that envelope and you will have your release when they
arrive. Whatever you decide I wish you the best of luck, and want you to
know how much I love my sweet little sissy girl.
Love,
Rebecca
Jeff couldn't believe what he was reading. How could she have done this
and made it sound like it was no big deal, let alone ask if he wanted to see
where a relationship with her would go.
Jeff slipped off into a dazed state letting the letter drop out of his
hands. It wasn't long before the unfamiliar weight of the breasts tugging on
his body, and the excruciating tightness of the corset brought him back to
earth.
Jeff wondered how he had allowed himself to get into this situation? All
he knew was that he had to get out of here. Rebecca was insane to think that
he wanted this. He couldn't actually believe that anyone would actually want
this?
However, as Jeff reached underneath his chemise to take out the buttplug,
he had still yet to remove, his hand lingered on the satin material of his
panties and his mind drifted back to the enchanting words left in the note
and the captivating woman who had put him in panties. Perhaps something deep
down in him really did crave and want this.
Jeff couldn't believe himself. He didn't actually like the way these
things felt and he didn't crave this did he? Confused and emotionally
drained from all the events of the past day Jeff sat down on the wooden
stool at the counter. He was immediately reminded of the buttplug, he had
yet again forgotten to remove, as it was crammed even further up his already
unfamiliarly stretched bottom. Jeff pushed the discomfort to the back of his
mind and began to think about the decision he had to make. A decision he
found harder to make than he ever thought it would be.
I hope you all enjoyed this story. It is my first that I have written and
I would love to hear from all of you on what you thought. I am always open
to ideas, comments, and constructive criticism. Please send any of the above
to
katied29@gmail.com
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