By tambor333

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Tags: Trans, Crossdressing, Anal, Oral, Group, Caught

Added: 16 Jun 2010 Views: 22857 Avg Score: 4.89

An introduction to a new side of my roomate

It had been a hell of a year with a divorce, a new job that had me traveling more and having to move into shared housing because my ex was sucking my bank account dry. Carl, my roommate, was a decent enough guy. I found the room on and we seemed to be compatible. He was neat without being compulsive about it, was a working student and was not inclined to throw wild parties.

I had not been dating thanks to the bad break up, but in the two months I had been living there I had to admit I was feeling the lack of companionship and was rather horny.

I returned a day early from a business trip to Austin and arrived on a late evening flight. I drove home and went into the house, interesting that the lights were dim instead of off and in the living room I saw two woman engaged in oral sex. A brunette sat in one of our easy chairs with a red head kneeling in front of her with her head buried in the brunette's lap. Both were dressed in lingerie, the brunette in a blue brocaded corset, black stockings and patent high heels pumps with shoulder length hair slightly tussled from their activities, the red head with a page boy cut had on a white chemise and garters with stockings with white strap sandal heels. Porn played on the big screen where a couple were fucking reverse cowgirl and really going to town.

I was taken aback, as were the girls, although the red head looked a hell of a lot like Carl! I said "Excuse me, I did not wish in interrupt your fun," and quickly made my way into my room, slightly embarrassed by the situation. I heard muffled conversation from the front room, with snippets including, "He was supposed to be home tomorrow," and "He seemed ok with us playing," then a "I don't know, I'll ask him if you want me too." A few moments later I heard a tap at my door and a sexy ladylike voice asked if they could come in.

I opened the door and the red head stood in my door way of my room with a white satin robe covering her lingerie. It was Carl dressed and made up like a sexy red head. I said "Hello, we don't know each other but I am Carl's roommate Mark, and you are?"

"Linda" , she responded.

"Charmed," I said, taking her hand and kissing it, capturing a whiff of a floral perfume. I stammered "Sorry for interrupting your evening, I can just relax in here this evening to give you run of the house, by the way did Carl say when he would be home?"

"Tomorrow morning" said Linda "but you can get a hold of him by cell if need be."

"No, that's allright Linda, it can wait till later," I stated.

"Um," Linda started, "look, this is sort of weird but, my friend found you sort of attractive... and was wondering if you wanted to join us to play this evening?" She went on, "I know this scene might not be your cup of tea, but you are welcome to join us should you wish too."

I stood there for a moment, wondering if Linda / Carl had found out my secret that I actually fancied crossdressers and T-girls or was this just a unconscious stroke of synchronicity that I just happened to pick a roommate that was a crossdresser! I pondered for a moment the implications of having sex with my roommate and her friend and gave into temptation, throwing caution to the wind. "Linda," I said "I would be happy to join you, please let me grab a quick shower." She smiled, her eyes lighting up and she said "Great, don't linger too long, we're riled up and ready to go!"

I grabbed a towel and headed to the bathroom, showered quickly dried off and threw on a comfy shirt and boxer briefs and padded out into the living room. Linda had freshened up and touched her makeup up as had her friend. Linda introduced me to her playmate Nell.

Nell melted into my arms and kissed me with her crimson painted lips, her French manicured hands rubbed my chest, and she smelled faintly of jasmin blossoms, it was a powerful sensation to say the least and my erection swelled. Nell removed my shirt and knelt before me. Linda took Nell's place and kissed me passionately, our tongues entwining. Nell grabbed the waistband of my boxer briefs and pulled them down exposing my hard cock. She took the tip of my penis in her mouth and slowly slid it into her moist mouth, swelled with the feeling of it an a little pre-cum oozed from the tip. I ran my hands over Linda's hot sexy body as I felt Nell slide something around my shaft and tuck my balls through something cold and metallic. I broke away from my passionate kissing with Linda to see what it was. Nell had fitted a cock ring on me and I was now rock hard and staying that way for the time being.

Nell stood and led us into Linda / Carl's room where we made for the bed. Linda laid down on her back and opened her mouth excepting my hard cock. She slowly worked the shaft with her tongue working its 7 inches deeper and deeper till my balls rested on her nose. Nell, from behind me knelt and started to work her tongue over my ass spreading my cheeks and rimming my twitching hole. I was ecstatic! The waves of pleasure built and I could feel myself moving towards climax. "I'm so close to cumming!" I breathlessly gasped. Nell shoved her tongue deep int my ass and pushed me deeper in to Linda's mouth. I exploded in orgasm spurting into Linda's throat, feeling that tingly feeling down to my toes. "Wow!" I exclaimed, "that was amazing!" The cock ring did not allow me to get soft. I leaned down and kissed Linda tasting my juices on her lips. I got Nell and Linda up on to the bed kneeling with their shapely asses pointed towards me.

I let my hands roam over their panty clad asses caressing them. I eased Nell's panties off her and then Linda's, seeing their clities for the first time. Linda's was slightly curved upwards, cut and about 5 inches long, Nell's was nearly as long as mine but slimmer and not circumcised. Both were just adorable and both were sporting cock rings as well. I positioned myself behind Linda and began to rim her sweet ass, while reaching between Nell's legs and stroked her hard clit. I switched off and then tongued Nell while stroking Linda. Both squirming with delight and kissing each other. I turned Linda over on to her back and began sucking her sweet cock, and Nell squatted over Linda's face for Linda to rim her. I felt Linda's excitement growing her moans became more passionate as she came while I was sucking her. I swallowed as much as I could then started to lick her clean, her body twitching as I touched her cock with my tongue.

I kissed Nell sharing Linda's cum with her, then turned my attention to Nell's sweet clit, and moments later with Linda and I switching off Nell to came in Linda's mouth. I was so hot by then I moved them back to their knees on the bed and returned to rimming their asses switching off every 30 seconds or so. I spotted some lube and condoms on Linda's side table. Grabbing them I wrapped my rock hard cock and lube both my cock and their sweet holes.

I positioned my cock head in Nell's sweet ass and she breathed out relaxing as I eased the tip inside of her. I held the tip inside her feeling her relax and then slide deep till my pubic bone ground against her ass then slid it out. watching her ass close I repeated the slow insertion over and over till when I pulled out she had a bit of a gape with her ass, then I turned my attention to Linda and did the same with her, penetrating her over and over with my rock hard dick. Finally I started to switch off between my hot tranny cock monsters relishing the power and exhilaration of fucking two hot t-girls. Finally I rolled Linda to her back and and began to fuck her hard, deep and fast, stroking her slick clitty-cock and moving her towards climax. She spurted cum high in the air as I fucked her and milked her hard clit. Then I moved back to Nell much the same way, looking deep into her eyes, telling her how hot she was and how much I liked slamming her hot pussy ass with my hard cock. As she approached her own orgasm I could feel my own building up as well. I grabbed Linda and forced her mouth down on Nell's cock making Linda take it all of it as deep as she could while I pounded Nell's sweet ass. Nell exploded in Linda's mouth and I let go filling my condom with my love juices.

I sat back exhausted and spent. I carefully removed my condom as to not spill it, held it up and asked who wanted it. Nell opened her mouth and held out her tongue so I held it high over her mouth and pored it in. Linda then kissed Nell and my cum mixed in their hot mouths.

I was spent from the long trip and the awesome love play. I lay down on Linda's bed and laid them next to me one on each side. Nell removed the ring from my well used cock and snuggled next to me with Linda on the other side. I fell asleep basking in the afterglow of our lovemaking and enjoying the intimacy that had not been in my life for sometime, thinking to myself how lucky I felt at the moment and how I wanted more in the morning.