Trevor to TraceybyTraceytrans©
A few years ago I was living in a large rooming house in upstate NY. I am 35 year old, 5'8 with a slim build and get propositioned regularly by both men and women so I guess I am reasonably attractive.
One of the other roomers was an ex-military guy (Jim) who had done his hitch and was now attempting to adapt to civilian life. He had broken his ankle playing on his friend's 4-wheeler and consequently lost his job- so he spent a lot of time drinking and looking for people to fight with.
On Tuesday night I was watching TV in the living room when Jim came in and sat down. He had been drinking and was quite argumentative. I managed to deflect his barbs with relative ease and at length he relaxed and invited me down to his room for some beers. I didn't really want to go but I didn't want to get him wound up again either so I tagged along with him.
Once we had cracked a few beers I was feeling more at ease- we were sitting on his bed-we talked some sports and then moved onto some gossip of the girls we knew.
Jim said that a lot of the girls were really into anal sex- and he really enjoyed giving it to them. I was a little surprised and said Jeez- you must have a small dick - chicks don't like big cocks in their ass.
Jim whipped off his sweat pants and his cock was a good 8" long and rapidly hardening.
Show me yours he said. I reluctantly lowered my pants and quick as a flash he pushed me onto my back and started sucking my cock. I was shocked but it felt so good I didn't try to stop him.
His hard prick was oozing precum and dangling just inches in front of my face so I put my lips around it- I licked the head and tried to get as much as I could in my mouth-Jim immediately started fucking my mouth- I was doing my best to lick and suck - it felt so good sucking his shaft while he sucked mine. I was ready to blow my load when Jim pushed me away and handed me a plastic bag- go put these on he said.
I went into the bathroom and opened the bag. Inside was a black miniskirt, white thigh-high
stockings, a white lacy bra with breast forms, a frilly white blouse and a blonde shoulder-length wig. I was shaking as I dressed and I had a hardon like I had never had before. My reflection in the mirror was so hot- I was a hot chick!
Jim whistled when I came back into the room WOW- Baby- his cock was all shiny looking and he must have greased it up because he pushed me onto the bed and shoved his cock right up my ass in one quick thrust. I yelped with the pain but his mouth was on mine - shoving his tongue into my mouth he tongue-fucked me as his wonderful thick cock plowed my tight ass. He put his hands under my bra and kept pinching and tweaking my nipples.
Yeah that's it baby- take it all- take every inch of my cock you bitch- Your ass is made for cock you little slut. My cock was rubbing against his stomach as he fucked me harder and harder. I could feel his balls slap my cheeks as he buried his cock. He was grunting with pleasure. I was moaning and thrusting back - his cock felt so good in my ass-I was hoping he would never stop as he stroked slowly then faster and faster until he let out a roar and I could feel his cum blasting my ass. He shot and shot load after load until I could feel his cum all around his cock. I grabbed my cock and pumped furiously until I shot all over his chest. He grabbed my head and made me lick it all up. Amazingly I could feel his cock hardening again. He flipped me onto my stomach and fucked me again- slower this time- spanking my ass every time he shoved his cock in- making me jump and jerk on his cock. Again he shot a huge load deep in my ass.
He stayed on top of me until his cock grew soft.
When I got up off the bed my ass was leaking cum. Thanks Tracey- that was great - I'll have some more beers for you tomorrow he said.