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Lessons from a cosplay boi..How I discovered the pleasure of sex with another man through a cross-dresser and an understanding friend.Me and Pete are partners in a tech start-up firm and were down in San Diego to meet some potential investors. We got separate rooms at the hotel but made sure they had a connecting door so that we could easily get together to put the finishing touches to our presentation. It was a long evening of work but by about 11pm it was done. We figured we’d earned a break and went down to the bar.We’d come down the same week that Comic Con was on and were entertained by all the teens and twenty-somethings walking around in various costumes. Some of the girls there were in very skimpy clothes. I saw several Princess Leias, different shapes and sizes but all quite erotic. There was one outfit that caught my eye. A powder-blue satin get-up. A kind of ‘Supergirl meets WonderWoman’. Tight bustier and micro-skirt barely covering shiny red satin panties. Long slim legs that seemed to go on forever.She had a kind of ‘utility belt’ round the slim waist. Like a real superhero!She walked in past us and headed for the far end of the bar. She dropped something on the floor and, when she bent over to pick it up and I could see that tight sexy ass, I nearly spilled my drink. Pete turned around to see what had caught my eye. And then she looked up and caught us both looking at her. Smiled a little smile and sat down. I kept checking her out over Pete’s shoulder. “I don’t think she is what you expect” Pete told me.I didn’t understand.”Pretty sure that’s a boy you’re leering at””Really?””Yeah, really”Fuck. I was getting hot for a little cross-dressed fanboy. And looking again I realized Pete was right. But she was so sexy. I kept thinking ‘she’, this was strange. I was no less aroused, knowing the truth. “I think I’d still go for it”, I said, only half-joking.”He’s half your age.” was the reply. I thought about that. Pete hadn’t said something like “it’s not a girl”. “So him being male isn’t the issue?” I was teasing him.”Well…” Pete began…. “Ahh you’d be into it as well!!” “Never did before, but that is a very sexy item” Pete had half-turned and was checking ‘her’ out in the mirror behind the bar.She was sitting there all alone in her tiny costume, sipping a coke. Looked up and saw us both ogling her again. Smiled again. We talked more about business, but I was still distracted by what was over Pete’s shoulder.Pete laughed… “Brett, if you can’t concentrate we can do this later. I’m heading up to my room for a nap.”Off he went, leaving me alone at the bar to finish my drink. Every time I tried to take a covert peek at the girl down the other end she caught me. I forced myself to look away and was just leaving a tip for the bartender when I sensed a presence next to me. It was her.”Oh” she sounded disappointed. “Just when I got the nerve to come over, you’re leaving!”I didn’t hesitate….”I could stay. Could I buy you a drink?””I wish, but I’m not old enough to get served a proper drink in here.””A coke, then?” I suggested.”We could explore your mini-bar….”Oh man, she was inviting herself to my room.I’d never done anything like this. But I was highly excited by the prospect of being in my room with her – still thinking ‘her’ – and seeing what might happen.”Let’s go”We headed for the elevator bank. “I’m Jaimie””Brett. Very pleased to meet you, Jaimie.”I could feel my cock hardening, not knowing what might happen, but turned on by being alone in the elevator with this sexy girl…. wanting to touch her.It seemed like forever before we got to my room. Jaimie turned to me at the door and said”I’m not quite what I look like, Brett, did you figure that out?””Yes Jamie, but I think I’d like you to come in, anyway”I opened the door and she went in ahead of me. I couldn’t resist the temptation to reach out and touch her bum.Instead of objecting she turned and looked up at me and I felt her slip her hand down to my crotch. Her hand was rubbing my hardening cock. I looked down at her. Desperate to take her into my arms. But…… “Would you like that drink, then?” out of politeness…. really I just wanted to get over to the bed.”Just some water, Brett, I don’t drink.” So that had merely been her pretext to get up here. She was more in command than me. No surprise, on reflection. She took the bottled water and was looking out of the window, türkçe bahis enjoying the view.I was behind her, enjoying the view as well. Tiny tight ass in shiny material barely covered by the micro skirt. Behind Jaimie’s back, I whipped out my cell and snapped a picture.Then, I couldn’t resist it… sent the photo to Pete’s phone. It was clear evidence that Jaimie was in my room but I wasn’t worried what he would think. I was boasting! Couple of seconds later I heard the faint chime from the adjoining room as it arrived.I told Jaimie that her costume was spectacular. She posed for me. It was impossible to disguise the hard-on in my pants. Jaimie came over to me and took my hand.”I want you to fuck me, Brett. In my girly costume.”She went to the bed and lay face down. I lay along side and my hand was on her ass in an instant. Feeling the smooth fabric under my palm. I traced my fingertips down her thighs and back up and then under the short hem of her skirt. She lifted herself off the bed and began to peel down the satin panties. I took over and slipped them down those long smooth legs and off completely.The rest of the costume stayed on. The skirt was lifted so I could see that super bottom. And I could see ‘her’ balls as well. Reminding me that this was not the kind of girl I was used to. That this was something I had never done before. And the throbbing of my cock told me this was something I had to have.I stood at the end of the bed, still staring at Jamie lying there, and undressed.Jaimie pulled a small bottle from her utility belt and handed it to me. Lubrication.What a well-stocked utility belt. I smiled to myself because it made me think of a very old joke where the answer comes before the question: A/ “Cock Robin”Q/ “What’s that up my ass, Batman?”But I digress…. I rubbed some lube on my cock and dribbled some down onto the wonderful, smooth, tight, tiny, sexy crack of Jaimie’s ass.Jaimie turned her head and looked back at me..”You need to rub it in, Brett. And put some up inside”Jaimie spread her legs and I climbed up onto the bed between them. My hands were on her ass, spreading the lube and then my finger tip touched her anus and I pushed in a little, lubing her insides. And then it was the moment….. Jaimie reached behind and took my erect cock in her fist and guided it to her slippery opening. “Push it in, Brett. Fuck me.”I lowered myself as my cock slipped into Jaimie’s tight, sweet ass. Oh sweet mother of mercy, it felt so good. It might have been the sexiest ass I ever saw…. and I was fucking it. What a dream.”Oh Jaimie…. you’re so exciting!””MMMM Brett, I love feeling your cock inside me”I was on my forearms, leaning down and nuzzling Jaimie’s neck. My cock pounding into that tight ass, over and over. I was in heaven.I knew I wouldn’t last long. Jaimie was just too sexy. The circumstances too new. “Oh Jaimie, I’m sorry…..”She understood…”No, it’s OK….” She started to buck under me, meeting my thrusts. Wanting to feel me cum. And cum was what she felt. I was grinding my cock deep into that little ass and suddenly exploded. What an orgasm. Deep up inside Jaimie’s ass. Spurt after spurt of cum.So good. So good. I told her. “So good”She told me “So good”From behind us….”So good”……It was Pete, he’d come through the connecting door and had watched the whole thing. I didn’t care. My cock was still buried in Jaimie’s ass. I left it there….”Jaimie, this is Pete, my business partner”Pete came forward and said hello.Jaimie was unashamed, said hello back, even while my cock was still deep inside that sweet ass. Finally, I pulled out of Jaimie’s ass and stood. Covering my cock with my hand.”Don’t be shy, Brett. I just watched you fucking Jaimie’s ass. And I enjoyed it…””Do you like my ass, Pete?” Jaimie asked.”It might be the sexiest ass I ever saw, Jaimie.” Pete bent down and caressed it.I went to the bathroom and cleaned up quickly. Brought back a moistened towel for Jaimie…. who was sitting of the edge of the bed….. sucking Pete’s cock!He looked over to me and winked. I was pleased and turned on.And impressed.Pete has a huge cock.Doubly impressed when I looked down and could see the fabric of Jaimie’s skirt lifted well above her lap. She was hard and she was packing, too.Jaimie had Pete’s cock in her mouth and one fist around it. Her other hand was between Pete’s legs and softly fondling his balls.I güvenilir bahis siteleri retreated to the armchair in the corner of the room and enjoyed the show.After a few minutes Jaimie took her mouth off Pete’s cock and looking up into his eyes told him she wanted his cock in her ass.Jaimie lay down on her back and spread her legs. Lifted up her skirt…..This was the first time we had been able to clearly see her cock. It was smooth as the rest of her, but out of proportion to her petite size. Big. Almost as big as Pete. I felt diminshed. Humiliated. My cock isn’t small, but these two both had something to be proud of.But I was actually being turned on watching both these big hard cocks.As Pete climbed up between Jaimie’s legs, I started to harden. As his cock entered Jaimie’s ass and, from behind them, I could watch that sphincter stretch to receive such a huge member, I got fully erect again.I stroked myself as I watched Pete fucking Jaimie. Watched Pete’s ass going up and down. Watched his cock going in and out. Turned on by watching my friend fuck. Turned on by my friend’s ass. By his cock. Most of all, by Jaimie.She was moaning and encouraging. Urging Pete to fuck harder, faster. She looked past Pete to me as I watched.Into my eyes. Smiling. I smiled back, aroused by watching her take such a big cock. Watching her getting fucked.A few minutes was all it took. Jaimie was too sexy for either of us to last. Pete picked up his pace and thrust harder and harder. His ass going up and down. His cock like a piston in and out of Jaimie’s ass.I wanted to touch it. I wanted to feel if it was as hard as it looked. Feel it sliding through the palm of my hand and entering Jaimie’s tight little asshole. I wanted to feel a cock. Someone else’s cock. But I sat there and watched as Pete reached his climax. Pounded himself into Jaimie and I watched as his buttocks clenched as his orgasm overtook him and he dumped his cum into Jaimie’s ass, to join the cum I’d put there a few minutes before.Oh boy. Pete collapsed onto Jaimie. Both of them out of breath and panting. I applauded. Told them both how sexy it was to watch them fucking. Finally Pete pulled out and rolled off Jaimie.My eyes went to Jaimie’s cock. Still hard. Jaimie in her superhero costume. Legs apart on the bed and a superhero proportioned erection… crying out for attention. I got up onto the bed, lying along side her. Now she was between Pete and me.She looked into my eyes and made an encouraging expression. Telling me to take her cock in my hand. And I did. Reached down and grasped that big hard meat.Stroking her. Feeling the weight of her engorged cock in my hand.Stroking. Jamie turned to me.Face to face.Eyes locked on mine as I moved my hand up and down the length of her erect penis.She moved closer. Lips brushing against mine. We kissed. I was kissing a boy dressed like a girl. Stroking her cock. Stroking his cock.Kissing me harder. More urgently.Pete on the other side. Rubbing Jaimie’s ass as I jerked her beautiful penis. Stroking harder. The kisses telling me how she wanted it.Faster.Up and down. Hard meat inside smooth silky skin in my palm. Hard meat as I masturbated this supergirl.Up and down.She tensed. Her hands came up. Holding my face. Holding me tight as she kissed me fervently. Telling me it was close. My tongue found her mouth. Tongue deep in her mouth. Fucking her mouth. Gripping her penis. Jerking faster. Faster. Pete was on his side, tight up against Jaimie’s body. He was humping against her. She held me tighter still, and froze. I felt her cock twitching as the cum shot out between us. Kept stroking up and down. Jaimie moaned. Her mouth still on mine. The cum from her cock on my hand.I stopped moving my hand on her cock, but I didn’t let go. It felt too nice.I wanted to hold onto her cock forever. Big hefty meat in my hand.Pete rolled away and Jaimie rolled onto her back. My cock was hard like iron and she reached down and gave it a little pat.I rolled away onto my back then and all three of us lay on the bed, staring at the ceiling. Jaimie was between Pete and me.Then she sat up and said she was going to take a shower.We watched her go. That sexy costume. That beautiful ass. Knowing without seeing, that big swinging cock in front.Pete looked over to me. Grinning. “That was fantastic” he said.”I know!” “So glad you sent me that picture!””Well I wanted güvenilir canlı bahis siteleri you know!””I never did anything like that””Nor me. I loved watching you fuck her.” I wanted to tell him how much I admired his cock. But even after that, it seemed too personal.”We should go see how she’s doing. I need a shower now, too”And we got up, both naked, and went to the bathroom.Jaimie’s costume was on the floor and she was in the shower already. No wig. That long blond hair was natural. We watched through the frosted glass. Watched the shadows as she stood under the flowing water. Pete was first to open the shower door and step inside. I followed.Now we took turns washing Jaimie’s petite, smooth body. Touching every inch of her. The soap making our hands slide effortlessly up and down her delicate frame. We all three became hard again. As I took my turn with Jaimie, Pete began to add soap to my skin and I felt his manly hands on me. He went up and down my legs, over my back. From behind me he rubbed my chest. I was being held in his hands and his cock was rubbing against my ass.Such a big cock. I reached behind and stroked him briefly. Then returned to Jaimie.Pete’s hands began soaping my ass. I felt him separate the cheeks and slide against my anus. His finger lingered over my asshole and he pushed a tip into me, briefly. It felt so good. His other hand reached around me and gripped my cock. Jaimie pressed herself against me from the front and I was sandwiched between them both as Pete’s finger explored further up into my ass.As much as I was enjoying it, I wasn’t ready for this and squirmed away from them. “Get you next time, Brett.” Pete told me. And he was probably right. We were in new territory, but I wasn’t against further exploration. We finished up our shower. It was late. Neither Pete nor I wanted this adventure to end, so I asked Jaimie to stay the night. “OK, but now I’m out of my costume you should call me Jimmy” he told us.And so it was Jimmy that joined us in my bed.Jimmie that lay between us. A male. We were three males in bed together.And it was Jimmy, we discovered, that couldn’t get enough cock.He loved it.Pete and I took turns fucking him.His smooth tight ass was filled twice more that night by each of us. First Pete climbed up on him from behind and drilled him. Then it was my turn. Jimmy lay on his back, as he had for Pete the first time. I fucked him in the missionary position. Our lips locked together. Pete’s hand caressing my ass as I humped up and down into Jimmy. Encouraging me with his words and then exciting me by slipping a finger into my own ass again, like in the shower. It was an exceptional orgasm when I shot into Jimmy once more… feeling my own ass being stretched and tickled by Pete’s finger. Then later, Pete and Jimmy spooning. Jimmy facing me as he took Pete’s big cock for the third time. Longer and slower this time. More loving, gentle, sensual.As Pete fucked him that time I moved down the bed and took Jimmy’s big hard cock into my mouth. It seemed so natural. It felt so perfect.I sucked Jimmy’s cock as Pete fucked him and he came in my mouth while Pete’s cum filled his ass again. I didn’t swallow. Instead, I moved up and put my lips on Jimmy’s. Sharing his cum with him. Pete leaned in and all three of us were kissing simultaneously. Each taking a taste of Jimmy’s cum. And that brought me erect again and I was not to be denied. I rolled onto my back and pulled Jimmy onto me. I slipped easily into his ass, stretched as it was by recently accommodating Pete’s big cock. I felt Pete’s cum coating my cock. Felt it leaking slightly from Jimmy’s ass and trickling down onto my ball sack.Jimmy moved up and down my hard cock. Looking into my eyes. Telling me how much he liked it. Pete cleaned himself off and came and stood by my side of the bed. Not quite hard again, but not soft… He fed his cock into my mouth as Jimmy rode me. A cock in my mouth and my cock in this beautiful boy’s ass…. I was in a heaven I hadn’t imagined. I came again. Bucking my hips up into Jimmy. Shooting the last of my cum into him. We rearranged ourselves. Jimmy lay beside me. Pete got back in bed on the other side. And, full of blissful exhaustion, we drifted off. In the morning, it was Jaimie again when she dressed. She thanked us for a great night and went to enjoy ComicCon.Pete and I made our presentation. Our teamwork never seemed so perfect as that morning after. And it continued. We had discovered a new bond. Jaimie had been the catalyst… now we were on our own. And when the day came that Pete stopped using his finger and started using his cock to excite my ass….. it was the best day of my life.

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