About a month ago, I had sex with my first man. It has been a long time coming but I am so glad I did it.

I have been crossdressing for a while. I started going out in public just to see if I could get away with it. I am only a little effeminate, 5'7" with a toned swimmers build, about 115 pounds, I even grew my hair out to get a crop cut.

So I finally decided I would take it to the next level. I posted ads on craigslist, and after about a week of posting everyday I finally found the guy I wanted. He was a tall, muscular, white guy with a bit of an Italian look, with almost no body hair.

I met him at a starbucks. I was of course subtlety crossdressed in the jeans that show off my ass the best and a striped blouse with a black leather jacket and some flats; I put on some cute black panties and bra (I have a toned enough chest to wear a AA cup bra). He seemed like a decent guy so I talked to him for a minute and got him to come back to my place.

We got to my house and we sat down on my sofa we made out for a little bit. Compared to me he had huge hands. I straddled him and he put one of his hands on my lower back and one on my ass. I could feel his cock on my leg. I rubbed it a little through his jeans; he squeezed my ass really hard when I did. I got off of him and got down on my knees. I played with his cock more through his jeans. I unzipped his pants and he relaxed a bit. I pulled out his cock. It was everything I hoped it would be. His email said he was 9 inches and he was. His cock was almost as long as my forearm. He wasn't too thick though, I put him in my mouth. He put his hand on the back of my head and softly pushed my head down. I gagged before I could go all the way down. I sucked his cock for a few minutes before I got up.

I asked him if he wanted a drink, then I poured us a few shots of whiskey. We made out some more while we were drinking. At one point he pinned me against the wall and grabbed my crotch. He could feel my cock even though I am only 4 inches. After I had about three or four shots I excused myself to go change. I went to my room and put on my white thigh-highs with little pink bows to the top, matching white teddy, gloves and garter belt. I put on my 4 inch heels and a soft pink lipstick and mascara. I put on a my robe so that I could surprise him when I was ready.

I went back to my living room and offered him another drink. I led him back to my room. I put my hands on is sides and felt up muscular body. I went the rest of the way up and took off his shirt. Then I ran my hands down his body as I got on my knees and I took off his pants and briefs. I led him to my bed and sat him down and pushed him back on his back. Dropped my robe and watched his cock come to life. I got down and started sucking his cock (I can suck a lot deeper when I have had a few drinks), after a few minutes he sat up and picked me up and laid me on the bed where my head was hanging off. He walked around to where he was standing over me. He put his hand on the back of my neck put his cock up to my lips. I opened my mouth and he pushed his cock in deep. He went all the way in until my chin hit his body. He left it there for a second and he touched the front of my neck and he felt of his cock inside my throat. Then he started thrusting back and forth. After a few times my eyes where watering. He kept going and it got hard to breath. He started going a little faster and I tried to slow him down. He grabbed my hands and held one of my arms by the wrist and put his foot on my other arm. So now my arms were stretched out and he was still fucking my face. He started going a little faster and not as deep. I started tasting a little cum, then it really started going. My mouth filled with cum and he was still thrusting and still hard.

He pulled out of my mouth and I had a little cum running up my face almost into my eye and a little went up my nose. He told me to stand up and I did, he grabbed my jaw and opened my mouth, then he told me to swallow. After I swallowed he grabbed my hips and picked me up and threw me on the bed. He got on top of me and rubbed his cock on mine through my lingerie. Then he put his cock between my ass. I could feel the head of his cock passing by my asshole. After all of this foreplay I was extremely horny. I pushed him up and reached over to my nightstand and got my lube. He went to his jeans and got a condom. He put his condom on and I got on all fours, moved the thong of my teddy aside and before I had a chance to use it he grabbed the lube from me.

I felt him doing something and I looked over my shoulder and he was licking my ass. He stuck one of his fingers in my ass and it around in a circle, just inside my ass. Then he worked another finger in and I could feel him stretching my ass just a little. Then I felt him use the lube. He got up behind me and he put his cock under me and I reached down and felt of his cock and it went to my belly button. I wanted to revel in this for a second but he pulled back. I could feel the head of his cock move up to my ass.

I asked him if he wanted to take the condom off. He took it off and put his hand between my shoulders and pushed my chest down to the bed. He grabbed one of my hips and I felt him working his cock into my ass. Once he got the head in, he grabbed both of my hips and thrust all the way down really hard. It hurt a little and it was so deep that i made it hard for me to breathe. He stayed there for a second then started fucking me slowly. He felt all over my body, ran his hands through my hair, grabbed my thighs. He started going faster and got up over me and started fucking downward. I hear him cumming and I could feel it wetting the lube and making things a little more slippery. I knew he came but he didn't stop, he just slapped my ass. Then he rolled me over pulled off my teddy and left me in just my thigh-highs and gloves.

He pressed his body down on me. I wrapped his legs around him. He started fucking me again. He grabbed my neck and squeezed enough to give me a bit of a head rush. Then picked me up, while still inside me he got up on his knees. My shoulders were still on the bed and I was looking up at him. I still had my legs wrapped around him. He was holding me by my hips and I used his arms to pull myself up to where he is holding me. I wrap my arms around his neck and bite his lip. I let go and fall back on the bed and then get him to lie down. I crawl over on top of him and put my head on his chest for a few seconds. Then I mounted up on his cock. I moved up and down slowly for a second then he starts moving and going faster and deeper than I could. I leaned back and just took it.

I could feel him hitting my prostate and for the first time I became aware that I had a cock too. He kept going harder and harder and my cock started dripping a little bit on his belly and finally a lot of thin cum came out and covered him and I could see it in his face that he was cumming again too. I tried to roll over but he caught me and he spun me around into a 69 position and he started sucking on my balls and licking my ass. I had my face right over where I came. I licked and sucked up all of the cum and kept it in my mouth. I thought me might want to see me swallow it. Then he pushed me upright so I was basically sitting on his face. Then I felt him suck the cum out of my ass (which felt more amazing than I could have imagined). He threw me off and started to kiss me. He moved his mouthful of cum into my mouth and then sucked all of it back into his mouth. Then I told him I wanted to swallow it. I laid back on my back and opened my mouth he leaned over me and let it all run into my mouth. I could see it running off of his tongue then it dripped into my mouth. I showed him my mouthful and I swallowed it with him running his hand over my head.

I was expecting this to be a NSA experience, that is what I advertised. I am glad he stuck around all night. He laid and talked with me in the dark for about an hour. Then I got dressed in a tshirt and some cute boyshorts. We ordered a pizza and got drunk.

He really surprised me I was really thinking it would maybe turn into a regular thing but we are now actually dating now and so far things are going well. He has been over to my house now 3 or 4 times and the sex is amazing. We have even taken showers together and he just makes me feel like real girl.

The way he makes me feel is so great that I am now a girl all the time unless I am at work and I may be finding a new job just so I can go full time CD.