Trevor to Tracey

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A young man's first time with another man.
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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.

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AnonymousAnonymousover 2 years ago
First Timer

As i finished my hair make up eyes lips and nails it was time to dress.Slipping in to my new corset thong black stocking and red strappy heels.Topped off with a tight short dress now i am ready to met my first date first time.As i knocked on his door i was not sure what i would find or would he like what he was seeing.When the door opened their stood a nice looking middle age man with a very big hard cock showing thru his pants.Once in he was all over me filling me up kissing and licking me.Before long i was down on my knees with the biggest hardest cock deep in my mouth.I spent a very long time in joying sucking his cock.He filled my mouth throat and belly with two monster loads of cum.But he saved the best for last that hard found its way deep in my open ass.He then took me to his bed where he started all over again.

Riki1942Riki1942about 9 years ago
Bareback

I love to cross dress for my Boyfriend when we have sex. I love that feeling when he cums in me and I can feel his cock all wet and slippery in my ass!

Dark_StormDark_Stormabout 9 years ago
A good story, but...

There are these funny little things called quotation marks, ' ' and " " that are used to indicate speech in a written story. You might want to familiarize yourself with them and use them when writing dialogue. Other than those being missing and a few other minor errors, the story was hot enough for a story about a first time encounter.

AnonymousAnonymousover 10 years ago

Great pic, you look hot. I dress but don't look as good as you. You described it well, most women are uncomfortable with anal. Best way is plenty of lube, then one long quick thrust, initial pain, get him to wait, some men cant they just want to fuck, then let them fuck the way they want, fast, slow, it doesn't matter, When they cumm in you, try to make them keep fucking as their warm cumm is a good lubricant and as by this time you are more relaxed, if they can stay hard,young guys usually can, the feeling is really nice and this is when I usually cumm without them touching me.

AnonymousAnonymousabout 15 years ago
trevor to tracey

loved your story it was hot short and to the point. loved your pic. your very hot loved your ass. keep up the stories.

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