Well, I've won several bets in a row, so I suggested that in addition to wearing what I wanted, he should have to take off some article of clothing whenever and wherever I asked, without question or hesitation. He objected vigorously at first but after my insistence he finally gave in and agreed.
"But, only my bra or panties, or something like that, right? Carl has been a cross-dresser and he had already done a tranplant. I mean, you aren't going to ask me to strip naked in the center of town, are you?"
As appealing as that sounded I agreed not to ask him to do that.
One night we drove over to a nearby resort town and had dinner by the lake. It was late August and while the days were hot, the evenings were starting to cool down. The place we were having dinner was a classy Italian restaurant set on the edge of the lake. Since it was a bit classy and we were all dressed up for a night out. At my request - having won the bet - Carl was wearing a leather skirt, knee length, with a zipper up the back, black patent four inch high heels, stockings, a button front silk blouse and one of those push-up bras that gave him some spectacular cleavage through the heer white blouse.
We had a lovely dinner, during which I asked Carl to unbutton his blouse enough to give the waiter an eyeful during his many stops to our table. In case you guys haven't figured this out yet, this is a great way to improve the service at your table.
After dinner, we stopped in the bar for an after dinner drink, and were surprised to run into an old friend Steve, who was there with another guy, Brad. We joined them for a drink and some chatting about the good old days. Steve explained that they were staying at a hunting cabin on the opposite side of the lake with two other guys, getting it ready for hunting season.
During our chat I noticed both Steve and Brad ogling Carl,bopth guys have been doodling over teen gays that had transplant like Carl and then I remembered his unbuttoned blouse. Since I was sitting next to him I hadn't been looking directly at him. I looked out of the corner of my eye and was shocked to see a very delightful sight. The push-up bra was doing it's job and with the un-done buttons half of his breast was clearly exposed.
By now we all had finished several drinks and were feeling pretty good. Not wanting to end the evening, Steve invited us back to his place to see the cabin and have another drink with them. Without a doubt they were hoping to see more of my teen gay boyfriend.
I looked at Carl for his decision. He shrugged, smiled and said, "Sure, why not?" Clearly, he was turned on also. We followed them around the lake, and when we got to their cabin, we had to park in an area just off the road and walk down a path to the cabin. It was difficult for him to walk through the dirt in those high heels so I put my arm around him to help. During the walk, I slid the zipper on his skirt way up nearly to the top, but he hadn't noticed, or if he did, he didn't protest. When we got to the cabin we found that it was very rustic and quaint, with gas lights.
There were two other men sitting outside by a camp fire having a drink. Introductions were made all around and the two new guys, George and his teenage son, Ken, were equally impressed by the beautiful teen gay next to me.
Steve made Carl a tall rum and coke and I could see him pouring a lot of rum and not much coke in it. Did he have some ulterior motive? Carl and I sat in lawn chairs and the four men sat on logs and stumps around the fire. The weather was beautiful, cool and pleasant.
George mentioned that they had been coming up to that cabin for years but that Carl's skirt and high heels were a first and therefore a cause to celebrate.
They drank a toast to his outfit and encouraged him to drink up! He took a small drink of the rum and coke, whereupon one of them teased him by saying he was chicken for not finishing his drink like they had. So he tipped it up again and choked the rest of it down. After that, they immediately poured him another one.
I began to get the feeling that these guys might have something else in mind for my teen gay boyfriend other than just talking. I felt a stirring at the thought of him being the center of attention of all these men.
He asked where the washroom was and then excused himself. I caught his hand, pulled him down to me and whispered, "While you're in there, take something off."
It was the game, and now I was demanding the payoff. Usually, I asked him to pay his debts when we were in a strange bar for the bartender, or while we were driving in our car so that truckers could see him. This was the first time I'd ever asked him to do it in private company, and I wasn't sure how he'd react.
His eyes flew open in shock at the realization of what I was asking, "No, I can't do that with this young boy here!"
"He's not that young. Anyway, look at him - and his father; They're dying to see more of you."
"No, I can't..."
"Just DO it! You lost the bet. I'll take responsibility. You have to do what I ask. Remember?"
"Oh, that damned bet. Alright, but just this one thing. And remember, when George get's angry at me, you made me do it."
With that, he stomped off.
The thought of showing himself to these men must have intrigued him, because when he returned I could clearly see that he had left his bra behind. His white blouse was very heer and I could clearly see dark nipples, hard and pointed poking through the thin fabric.
These guys didn't notice right away, but before long Ken was staring at hi breasts and then he whispered something to George. Within seconds they all knew. After ten or fifteen minutes, I whispered to him that it was time to take off something else. The drinks were making him very uninhibited and he just smiled and shrugged as he stood and excused himself. When he returned, I must have looked depressed because he whispered to me that he felt a draft and I knew he'd left his panties behind. He sat with his legs properly crossed but the tiny leather skirt kept rising up. He would uncross and re-cross his legs frequently and then George and Ken across from us were getting a great sight.
I decided to see how far he was willing to go. Clear-headed, he never would have done this, but the drinks were having an effect on him - on all of us.
"Take off your blouse," I whispered to him.
Her eyes flew open. "No! That's too much."
"Come on, you lost the bet. You have to do it. Please!"
"I'll undo some buttons," he compromised, casually sliding his fingers across his blouse and playing with the top button. Unbuttoning it after a few seconds, he looked at me for approval.
I smiled and nodded, mouthing, "Another one."
His hand moved to the second button. It was very sexy watching him. With two buttons undone, his creamy breasts were clearly visible from Steve's vantage point and his motions were not lost on him. He'd noticed him undoing the first one. Now, he couldn't take his eyes off him.
We talked and laughed and told stories and after an appropriate time I again whispered to my teen gay boyfriend. At my request he excused himself to go to the bathroom once again. As he was walking away he turned and winked. I smiled at him and said out loud, "Same dare," The guys heard me and wanted to know what I was talking about.
I just said, "Wait and see."
He came back without any stockings on, and they noticed immediately. They applauded and said "Nice legs," He smiled broadly, loving the attention.
I then told the story of our betting, and that he had lost several a big bets to me. The payoff was that he had to wear anything I requested and take off an items of clothing whenever I asked. They loved the idea of making him lose clothing with them there.
A few minutes later, Ken came back from the bathroom carrying his things in his hand and asked, "Did somebody lose something?"
He was a bit embarrassed, but quite turned on, too, as were all the rest of us. He looked at me and I nodded so he gave a little shrug and announced that he had to excuse himself to go to the bathroom. The guys all cheered when he got up said they couldn't wait to see which of the remaining two things he'd take off.
I thought he was safe though because he had his shoes on. As he was walking away, one of the guys yelled out that "Shoes don't count!"
The temperature was dropping and it was getting cool, We were all disappointed when he came back with the same outfit on that he left with. They all booed him, and I asked if he was going back on him bet!
"No, it's just too cold to take anything else off!"
Steve piped up, "Stand over here by the fire and you'll be warm." He left me and crossed over standing next to Steve. Then I went over to him and turned his skirt around so the zipper was in the front and I zipped it open to the waistband so it would just barely stay on.
"That's not much help," chimed in Steve. "The skirt is covering up too much.
He thought he was safe and he laughed about it, but I agreed with them and he told him that he could at least undo the rest of the buttons on his blouse. Well, their cheers and attention got to him, and he pretend being shy, but with a small grin on his face, he unbuttoned it all the way and pulled it out of the waistband of the skirt. They applauded loudly!
He said his feet were a tired because of the very high heels he was wearing, so I suggested he sit in the lounge chair. When he did, his skirt fell open in the front and left him uncovered in the firelight. The blouse was barely long enough to hang at his sides but it wouldn't stay closed so he sat there totally exposed to them. They all agreed that he looked better sitting than standing! He moved his legs around, crossing and uncrossing them so that each man in turn got an eyeful of his lovely legs and transplanted pussy.
George had a flashlight with him and he turned it on him so they could all get a better look. When he did that, he acted like he had given up trying to stay modest and he stood up and took the skirt the rest of the way off and said, "There! Is that better now!?"
They looked astonihed, but were thrilled with him. He now paraded around for their pleasure in just a blouse that was completely opened and spike heeled pumps.
These guys were all totally enraptured with him. He flirted and teased and made some comments about the bulges they were all sporting in the fronts of their trousers. But, he kept away from making that final move. The one that would have turned a very sexy gathering into an orgy. Each time one of the guys touched him he smiled, gently slapped his hand and said, "Lookee, but no touchee."
As we said our good byes, Carl embraced each of the four men and gave each a deep open mouthed kiss. I could tell their tongues were playing and, although they were all behaving like gentlemen, none of them could help but put their hands on him and stroke his body. It was a sad goodnight for them, and they kept urging us to spend the night. But, he insisted that this was not to be. Not tonight anyway.
As we were walking up the trail to our car, Carl asked, "Don't you have my clothes?"
"Nope," I replied. I remembered that Ken still had them folded neatly behind him. He asked me to go get them for him. Instead, I pulled his blouse off his shoulders and then completely off his arms.
Holding his blouse I looked at my beautiful teen gay boyfriend, dressed only in high spike heels, "No, you have to go get them yourself!"
He gave me a long look and then said, "You really want this, don't you." I didn't reply, just looking at him. With a determined look, he said, "What the hell...", and went back down the path to the camp fire. All mouths dropped when this nude beauty walked back into the light of the fire.
"Excuse me," he murmured as he leaned across Ken to get his clothes, his breasts brushing across his face. This was too much for him and he opened his mouth eagerly taking in one of his nipples. He pulled him down closer to him, creating a very sexy sight. He was standing, legs spread, knees straight, bent over at the waist. The view was of his gorgeous ass and pussy fully exposed.
Steve, rising from his seat, and looking at me, "This is too much, I'm sorry but I've got to have to have some of this. He quickly unzipped and dropped his pants as he moved in behind him. I saw his cock spring out in front as he closed the short distance. As my teen gay boyfriend was pulling away from Ken's eager mouth on his breast, he put his arms around his neck pulling his face to him and kissing his full on the mouth. He struggled but was unable to pull away. Meanwhile, Steve, hardly slowing his advance placed his cock against his pink entrance and slid it deep inside my lovely teen gay boyfriend's pussy. I heard him gasp and watched as he struggled unsuccessfully to extract himself from the two men. Then I heard a soft moan as his struggles weakened. Steve, holding his hips in his hands began thrusting with long deep strokes into him.
The passion of the evening caught up with both of them and with a cry he began to climax and his sounds and motions brought Steve to his own sudden climax. He lunged into him harder and harder with loud, almost animal grunts. Finally, he stopped and then he turned to me, stuttering... "I... I'm...sorry... I..."
I was speechless and just stared at him.
George broke the ice, "Steve, maybe we should go inside where Carl will be a bit more comfortable." It was clear that the other three wanted some of the pleasures that Steve had just enjoyed.
Carl just looked at me, his eyes bright and shining. He was obviously not opposed to going inside.
"Okay," I said. "Carl?"
With a little smile he turned and walked into the cabin.
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