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Jamiekent
04-17-2009, 06:29 PM
This is a true story of my first time.

I was recently divorced and was kind of depressed living in a shitty apparement and pretty much broke. I would spend my free time on the net looking at porn and jacking off. Hey.... It was cheaper than drinking :D

Anyways, I stumbled on a t-girl site and I was in awe with all the sexy ladies with something extra fucking and sucking. I foundmyself drawn the them and wanted to be like one. I'd watch the clips and work myself over with my favorite dildo.

One day while in the local adult store while browsing for a new toy, I was looking at some of the lingerie and thought... hmmmmm. So I bought a couple of outfits and raced home. I couldn't get home fast enough.

I picked out a black babydoll nightie with garters & stockings and admired myself in the mirror and imagined what it must feel like to be a woman. For weeks, I would dress up and enjoy the feminine feeling.

So, one day while online I was checking out the t-girls adds on CL and thought, I would post an ad with a sexy pic and see what happened. I was amazed at all the responces I received by horney guys describing what they wanted to do to me. Needless to say I was very turned on. I responded to a few and we corresponded back and forth. One guy in particular caught my eye. He was in his late 30's had a great body and seemed very kind. So, I invited him over.

I was SO nervous waiting for him to show up. Twice I thought about calling him up to cancel our date, but didn't. He knocked on the door and came inside. I offered him a drink and sat down to chat a bit. I explained that this was my first time and that I was EXTREMLY nervous. He said this was his first time with a t-girl and he felt the same way. We had another drink and I asked him if he wanted to meet Jamie. He said HELL yes. I told him to relax and I'd be right back.

I went to the bedroom and started getting dressed. My hands were shaking the whole time. I put on my white corset, white panites, garter & stockings. It took longer to put my make-up on that I thought, but I wanted it to be just right. I looked GOOD!!!

I came out to the living room and apologized for taking so long. He was sitting there in his boxers and just stared at me. I modeles my outfit and and asked him if he liked it. He said HELL YESS!! He stood up and started feeling my body and grinding him self on my ass. I asked if he liked my ass and he said it was firmer than most women.

We sat on the couch and I was rbbing his cock through his boxer and he was rubbing mine. I wpulled his cock out and started to jack him. Man he was hard! I opened his legs and got on my knees in front and started licking his hard cock up and down. The whole time I was thinking "I can't believe I'm doing this" but as loving every second. I started sucking him and rubbing his balls. I asked i f he liked id and he said I was a very good cocksucker. Aww shucks :D

He then pulled me up and I straddled him. I could feel his cock sliding up my crack while he was sucking my nipples. I asked him if he wanted to take me. Without a word, he made me get down on the floor on all fours with my elbows on the couch.
I handed him a condi & lube and was saking my ass while he put it on. I can still remember what it felt like to feel him pull my thong aside and feel him gently push inside me. A little more with each thrust. I hadmy head down and I was thinking I'm finally getting it in my ass.

Once he was all the way in, I made him stop so I could get accustomed to his size. He was 7" and pretty thick, thicker than me. He started to move slowly, the wole time asking if I was OK. How sweet.

He was now pushing it all the way in and pulling it all the way out. It felt so amazing to feel the head of his cock push past my sphincter. I reached underneath me and started playing with his balls. He groaned and said he loved it. He was fucking me pretty good and I wanted more. I reched back and grabbed his ass to pull him deeper inside me. He went nuts and really picked up the pace. I will never forget that wonderful feeling of the pressure.

He was pounding me and forced my head into the back of the couch with each stroke. I grabbed both of my cheeks and spread them as wide as I could to get all of hime inside. It felt like a bolt of lightning went though me and I came like I had never done before. Mt ass clenching around his cock was more than he could take and he moaned he was cumming. I could feel his cock swell and with a few deep strokes, he came.

He stayed inside me for a few minutes and I was griding my ass on his softening cock. He pulled out and I handed him a washcloth to clean up.

He said I was the best fuck he'd ever had. I was flattered and asked if he wanted to see me again.We meet about 15-20 more times and tried all kinds of fun things. Then he took a job in another city.

I will always remember my first!