Gary's Golf "Outing" Chapter 10 Ladies Golf and Apri Golf

by: Germaine 
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Rating: XXX Add Review    Added: 04/27/2007
Complete: no 
Synopsis:Gary plays golf for the first time in drag. They return to the condo for a pizza party.
Categories: Crossdressing / TV  She Males 
Keywords: Use of Sex Toys 


Gary's Golf "Outing" Chapter 10 - Ladies' Golf

I kissed Bob Goodbye and went out in broad (forgive the pun) daylight for the first time as a broad; it will probably be my last time if this old broad reads me. As I approached the green I recognized my partner. She was the woman who peeped over the stall door last night as I was blowing Christie. She was in her early '50s and built like a fire plug -- about 5'2 and very solid. She greeted me with a strong handshake and a peck on the cheek.

"I hope she doesn't get beard burn," I thought. She seemed very friendly so I relaxed a little.

"What's your name?"

"G-G-Gabrielle." I almost said Gary.

"Do you think we can beat these broads, Gabrielle?"

"I don't know; Kimberly's pretty good."

"I've beaten her before in tournaments. If you can beat her girl friend we should have a good day."

"Hi ladies, my name is Amy; you are?" she asked, extending her hand.

"Kimberly."

"Christie."

They all shook hands. "Gabrielle and I are going to kick your asses. How much can you afford to lose?"

"You have to be kidding," Kimberly said. "I've played with you before. You're a pro. We'd lose all our money."

"Playing for money makes the game more interesting but we don't have to play for money, we could play for something else."

"Like what?" Kimberly asked.

I said, "Yesterday's game was fun and we didn't play for money. Why don't we play for those stakes again?"

Amy pressed us for details but Kimberly just laughed and told her we had played for kinky personal favors. Amy said that sounded like her kind of wager and made this suggestion. "I'm having a luncheon next Saturday for a few girlfriends and I could use some help. I'll play against all of you. If you win, you can come to the party as my guests; if I win, you'll have to come as servants."

"That sounds interesting," Kimberly said. "What will we have to do?"

"Some light cooking, mixing drinks, serving drinks and lunch, cleaning up afterwards. We'll find something for you to do. They're fun people. What do you say?"

"How about it girls? Sounds good to me. Are you two game?" Kimberly asked.

With a bit of apprehension, Christy and I nodded our agreement. We shook hands on it and began playing. Amy immediately began "kicking our asses." Kimberly was right when she said Amy was a pro. She out- drove all of us and her short game and putting were exceptional.

She was a real pro except she wasn't very professional with me when I hit my ball into the woods, as I did quite a few times. She helped me find my ball by patting my ass when nobody was looking. Once when I bent over to pick up my ball she almost found my real balls when she goosed me. She squeezed my tits a couple of times and I told her to fuck off or she'd get something she wasn't looking for. She just laughed and I was tempted to whip out my prick to see what effect it had on her. I thought, Christy and Kimberly have to live here so I better not. She kept rubbing my thigh when we were sitting in the cart and I was afraid she was going to feel how hard I was getting.

We didn't stop for lunch because I was afraid she might read me so we just had a couple of beers and continued playing. I played terribly because of all the attention she was giving me and she really kicked all of our asses.

We were pretty upset when the debauchery was over so we decided on drowning our sorrows in the condo instead of at the bar. Amy gave Kimberly her condo number and told her to stop over and pick up our uniforms. She kissed us all goodbye with a little too much enthusiasm and one last feel of my ass.

"Goddamn, that fucking bitch really did kick our asses," Kimberly growled. We ordered pizza on the cell phone, left one golf cart at the pro shop, picked up the uniforms and drove back to the condo.

The uniforms were French maid dresses, one red, one black and one pink with very short skirts, tons of petticoats, matching long satin gloves, white caps and ruffled white aprons. Our giggles and laughs at our hostess's sartorial taste were interrupted by a knock on the door.

"It's the pizza guy; I don't know what his name is but we call him Luigi," Kimberly said as she picked up her wallet. "He doesn't mind because we tip him generously." Christie laughed and said, "You're our guest so you can tip him first." I guess I looked bewildered because she explained, "We give him blow jobs instead of money. We never get a cold pie and we love the special hot toppings he puts on the pizza, too."

Luigi put the pizza on the kitchen table and shook my hand. I guessed he was about 19 years old and six foot three.

"This is my cousin Gabrielle from Chicago. We've told her all about you and she's a very good tipper." Luigi's eyes lit up and he wasted no time unzipping his fly and exposing his long, thin cock. It was the biggest one I'd ever seen, at least ten inches. I found it hard to believe I was doing this. I took it into my hand and slowly licked the pretty pink head. I sucked the head into my mouth, then slowly let it out; sucked it in and let it out. I sucked in a few more inches each time and swirled my tongue around. It was rewarding to hear him groan. I swallowed a few more inches and repeated the swirling. Then I took his balls in my other hand and gently fondled them. Luigi loved this and pushed his sweet salami a little further into my worshiping mouth. When he hit the back of my mouth I gagged a bit but I wanted to see how much of it I could swallow. So I relaxed my throat muscles and let him slide it in slowly. It slipped down my throat and I had to breathe through my nose like Kimberly taught me. He held the back of my head and started fucking my face while Kimberly and Christie ate pizza, drank beer and laughingly offered words of advice and encouragement. I was afraid Luigi was going to pull my wig off so I stuck my finger up his ass and it produced an immediate response. He filled my mouth with a large hot load of cum. I squeezed his balls and swirled the semen around, savoring the flavor before swallowing his sweet secretion.

Our appreciative audience applauded approvingly and Christie pushed me out of the way and aggressively took my place. I enjoyed the show along with my pizza and beer. Christie gave him a royal blow job and sucked his balls for good measure. That caused him to shoot his load all over her forehead and face. Kimberly immediately licked her face clean before proceeding with the blow job hat trick. Luigi thanked us profusely and we had to remind him to zip up his fly as he returned to reality through the front door.

Christie put my clothes into the dryer and she and Kimberly took a shower together (with much giggling and a few screams). While I waited for them to complete their ablutions (and whatever else they were doing) and for my clothes to dry, I called Kay to see how her "date" with Heather went. It went so well that she said she was thinking of staying in Chicago for another week. That was good news because I was looking forward to attending that party on Saturday. I told her I was getting ready to leave and I would call her when I got home. She was okay with that because she had some things to do before she went home to her mother's. She didn't say what the nature of the "things" was, but I heard giggling in the background.

Kimberly and Christie emerged from the bath room with two raging hard- ons and enquired about my phone call. When I told them who it was they had all kinds of sexy things to say about Kay's lesbian liaison. I told them both to go fuck themselves as I made a bee-line for the bathroom to end the conversation. A chorus of derisive laughter hastened my retreat.

When I finished my SSS (shit, shower and shave) I dried on the fluffy towels and wrapped it around me to retrieve my male attire from the dryer. When I returned to the bedroom, Kimberly and Christie were lying on the bed head to toe, back to back, with their bubble butts pressed firmly together and erotic looks on their faces.

"What are you two up to now," I asked.

"You told us to go fuck ourselves so that's what we're doing," Christie said. They had bent their cocks back and were fucking each other's ass-pussies. I had never seen anything like it before. Their bodies were dry but their toes looked wet so I assumed they were sucking each other's toes while fucking each other. My cock immediately tented my protective towel. Kimberly noticed right away and offered to relieve it for me. I just had to participate in this tableau, so I lay down next to her, facing her crotch and enjoyed another fantastic blowjob, while I watched their cocks moving in and out of their pussies. We all climaxed almost simultaneously to end the most fantastic weekend I had ever experienced.

As I started to put on my shorts, Christie gave me a pair of red satin bikini panties and told me to put them on instead. "Something to remember us by," she said.

"How could I forget you two. I had a wonderful weekend and I can hardly wait until next weekend."

Kimberly said, "Here's something else to remember us by," as she handed me the vibrating dildo that had been a source of so much of my pleasure last night. Kimberly slipped it into my pussy and turned it on, then quickly pulled up the panties to hold the dildo in place. "Now don't take it out until you get home," she admonished.

"What makes you think I would ever take it out?"

They both laughed and Kimberly said, "Be sure it's in there when Gary sucks his first cock." I had almost forgotten she had said I had to suck a cock as a guy to be a boney-fied cock sucker. I promised I would, and after tongue-sucking kisses all around, I reluctantly started for home. The vibrator kept my cock standing at attention and all I could think about all the way home was the wonderful weekend I just experienced and who's cock I would suck to earn my cock sucker membership card.



I called Kay's cell phone as soon as I got home without even thinking to remove the vibrating butt plug. It vibrated all during our conversation and kept my big boy up, especially when she told me what she and Heather did after the reunion.

"I called my mother and told her I was staying over at Kay's because I had too much to drink to drive home. Then a group of us hung around and talked more about old times. Eventually Heather, Vicky, Dawn and I were the only ones left so we all went up to Heather's room, which is in the hotel where the reunion was held. We had a little pajama party like we did in high school and I'm still here. The room has two queen sized beds and Vicky and Dawn, who have been a couple since college, are putting on a show for us in the other bed."

"What kind of a show?" I asked.

"Vicky is naked and Dawn is just wearing a purple garter belt and stockings. They are joined at the crotch like two wishbones rubbing their pussies together and sucking each other's toes. It looks like fun and - wait a second - Heather is getting into position to try it with me. I'll let you how I like it when I call you later."

She told me she was definitely going to spend another week with Heather, or until she was sure her mother was going to be okay. Imagining what they were going to do relieved any guilt I felt about my weekend with Kimberly and Christie. I told her to take all the time she wanted, that she deserved a vacation, even though I would miss her. She said, "I'll make it up to you when I come home." We "kissed" goodbye and I removed my clothes, except for the panties, lay down and fell asleep to the gentle whirring of the butt plug still vibrating in my pussy. I dreamt of Kay, Heather, Vicky and Dawn, Kimberly, Christie and Bob and the coming weekend party at Amy's place.