A Deal's A Deal

The weekend had been rather dull; no money, no where to go, just the three of us, stuck indoors watching TV at Ashley's house. We'd decided to get in some beers and a pizza, we also brought out these 2 bottles of whiskey we had left from about two weeks ago, the plan was to take it to a B.Y.O.B. sorta party but the plans fell apart. After we had finished the pizza it was starting to get late, we were all pretty smashed, laughing at the silliest things. Ashley got up and stumbled to his room upstairs to slip into some jogging bottoms, so he was more comfortable to sleep. Nicholas and me were left downstairs, Nicholas decided to change downstairs he had brought something to sleep in with him. He unbuttoned his jeans and took them off, his legs were thick and pale, kinda hairy too. He had on a pair of blue boxer shorts, which he didn't remove he just pulled on his gray jogging bottoms and sat back down to watch TV. I always stay as I am, can't be bothered to get changed. Ashley came back wearing the same shirt he had on before and gray jogging bottoms, he had a poker set with him, it was his dad's.

"Anyone for poker?" he said. Me and Nicholas sat up looked at each other and said, "Yeah, sure."

We pulled out this little foot stool, set the green felt down and dealt the cards. It was tedious, but it passed some time and gave us something to do, being drunk we had a good laugh and a chat.We played for about an half an hour with just the chips, dealing out $100. Then Nicholas said, "Let's make it more interesting. How bout throwing some money into it?" I said I was in, Ashley was some what reluctant but he gave in the end. After 20minutes I was down to about $10 from the $50 I had started with and Nicholas was sitting there holding all the chips, Ashley was down quite a bit as well. Then it finally came what I thought was my big win, I put in everything I had left, Ashley folded. Nicholas raised but I didn't have the extra to put down, but I wasn't going to fold. I put down my gold ring, Nicholas said no. I don't know what he was thinking, it must have been the whiskey, but Ashley sat up and said, "You should dress up like a girl, you can where Gennie's clothes." Gennie was Ashley's girlfriend, she stayed at his house a lot. Nicholas said, "How exactly will that benefit me?"

"How should I know? He'd be dressed as a girl get him to suck your dick." Ashley suggested. I was shocked, I knew I could beat this I had the mother of all good hands. The idea must have piqued Nicholas' interested he put out his hand and said, "How about it?" I was nervous. I shook his hand and said, "You're on."

I put down my cards, I had a big grin on my face, there was no way he could best me now. Nicholas over his cards, he'd beat me he had a Queen and I only had a Jack. I was mortified. They were both laughing at me, Ashley put his hand on my back and said, "Oh well. I'll show you to your dressing room."

The two of us went upstairs, he pulled out some of Gennie's clothes. Some hip hugger type jeans, a pair of panties, a tight white T and a short-bodied hoody. He laughed as he threw her make-up bag on the bed next to bed. He left the room, leaving me to get changed. At this point I figured it was all in good fun and that the next day I could blame it on the whiskey, so i started to get undressed.

I'm a relatively skinny guy, so her clothes fit me, they just felt weird. The panties were kinda nice too. I did the make up the best I could, after all I'd had no previous experience. When I was finished I had a look in the mirror, I thought I looked really fucking sexy. I strutted down the stairs and back into the family room.

They both sat there sort of silent at first, then Ashley burst out laughing, he was pointing at the tent in Nicholas' bottoms.

"You've got wood for our sexy young madame." He chuckled at Nicholas. I was laughing at him as well, I was really playing it up as a girl. Nicholas got frustrated and pulled me onto my knee's, he pulled out his cock, it was already hard and pale like the rest of him about 5inches and thick. "Come on then, a deal's a deal." He said. I was rather horny myself.

I opened my mouth slightly and put my lips over the head, he breathed deep and laid back. I started to use my tongue and swirl it around the head, he pushed his hips upwards and my lips fell passed the head and started to work on the shaft, he grabbed my hand and put it on the shaft after I drew my head back. I started jerking him off and licking around the head, I could taste the precum on my tongue it was salty but it wasn't terrible.

Ashley ran upstairs and came back with a bottle of lotion and a condom. "I know i'll regret this in the morning, but if I'm gonna regret something it might as well be worth while." He said. I felt him pull the jeans and the panties down. Then I felt his finger on my anus, it was cold. He put it in and then I felt him start to push around the edge, i knew what was coming, he was trying to loosen me up. I tried to look behind me, I took my mouth off Nicholas' cock. I turned to look at Ashley, he had his cock out, it was longer than Nicholas' just as thick though. Nicholas' grabbed my head and put it right back on his cock, I continued to suck it, then Ashley entered me from behind it all happened to fast to register the pain or do anything to stop it. My body was trying to push him back out but he kept thrusting slowly.

"Stop, stop, stop!" Nicholas pulled his cock out of my mouth, "I'm gonna cum, gimme a minute." He said, he moved from in front of me and sat down, he took off his shirt, he was sweating. "Come on then." Ashely said as he moved me closer towards the couch, he put my head down so I was bent over the couch properly, then he started to fuck me faster, I could hear my ass slapping his stomach. "I'm not gonna be the only one that doesn't come tonight." I said, I took Ashley's hand and put it on my cock, which was leaking precum all over the floor, there was a small puddle of it. The slowed down so that he could jerk me off as well as continue to fuck me.

Ashley pulled out, "Wanna switch ends?" he said to Nicholas.

"Yeah sure. Let's do it on the floor now." Nicholas said. We moved to the floor, I got on my knee with my ass in the air. Ashley got in front of me, he was still wearing the shitty condom. "No way I'm sucking your cock with that on. And no way are you fucking me without one." I told them both. Ashley hesitated, but he ran upstairs and got another condom for Nicholas. He came back and laid down right in front of me, "Come on, come on before I lose it, I'm close." Ashley told me. I put my mouth over the whole head and began to bob my head up and down, running my tongue over his urethra whenever I came up. Nicholas had unwrapped and lubed up. He didn't have to squeeze my ass was wide open I could feel it, it was all hot from the friction. It was hard to keep a good stroke with on Ashley with Nicholas fucking me so hard, he also didn't touch my cock I had to stroke it all by myself.

Ashley closed his eye's and let loose, as soon as I felt the first shot his the roof of my mouth I wrapped my lips around the head. When I felt it stop, I sucked it, hard, to get everything. It was really salty on my tongue, I didn't think the taste would linger at the back of my throat after I had swallowed though, his cock started to go limp really quickly, he stood up and sat back on the chair he didn't say anything he just watched us.

Nicholas pushed me gently onto my side and rolled me over so I was legs over head, facing him. He started fucking me really quickly, everybody knows thats when a guy is gonna blow. I started stroking my cock faster I wanted to shoot I could feel the tension under my balls. He came inside me, inside the condom of course, he kept thrusting even after he was finished. Before he pulled out I pulled back on my foreskin and let him have it right on his chest. He didn't think it was funny he pulled out and ran to the bathroom to wash it off.

After that there was silence for a while, then for no reason we started laughing, that night we slept naked, separetely but naked anyway. After that night, I discovered my love for cross dressing and I don't mind helping my friends get some release if they ask nicely, but they do always make me dress up for them.