Rm 209: First Sex as a Crossdresser

This is a TRUE STORY.

I've been crossdressing for much of my life, as far back as I can remember. I would even go to sleep as a kid and pray that I would wake up in a girl's body. In the last few years, now that I live by myself, I spent about $1,000 on a whole wardrobe of women's clothes for myself - bras, thongs, dresses, tops, stockings, lingerie, make-up, perfume, etc... I have also been overweight for some time so I have breasts. As a man, I have to minimize them all the time. As a women, I can flaunt them! One day a few months ago I decided that I've had enough of merely wondering about my real sexual orientation. I've always liked girls but I also have had a secret craving for cocks. I decided before my 20's were over, I had to know the truth.

I had been chatting with a guy who answered a craigslist ad I had posted, his name was Dave. I had been crossdressing and masturbating to his pictures almost every night. Finally, I had enough. It was time. I booked a hotel room in the city and told him I would give him the room number when I checked in.

I checked into the hotel about 4pm and was supposed to meet him at about 8pm. I had already gone to have my chest, back and bottom waxed that morning, so I was on my way to feeling "girly." I asked Dave what he wanted me to wear and he told me he loved this red dress I had worn in some pictures I had sent him. The first thing I did after checking in was take a shower. I had bought some women's deodorant, soap and a few other things, figuring that if I'm going to do this, I'm going to go all out. By 6pm, I was basically done. Then came a question I had not thought about... What do I do now?

I had about two more hours until Dave was going to come, yet I was basically ready. I was so concerned about him getting there before I was ready that I finished two hours early! So I laid down and watched some Keeping Up With the Kardashians, a show I never watch. I figured if I'm going to be a girl, I'm going to do what girls do. I paid attention to how they were dressed, how their make-up was done, and how they spoke. I quickly smoked a joint to relax and then started to play with myself. I grabbed a dildo I brought with me and started to loosen myself up. In and out, in and out. This helped. Suddenly, I was in the mood again.

It was now almost 8pm and I texted Dave to see where he was. He answered: "Leaving now babe." Now I was getting a little annoyed. He lived about 45 minutes away from the hotel and hadn't even left yet! So, I had to kill even more time. After another 45 minutes of watching the Keeping Up With the Kardashians marathon, I had lost some of that horniness that had me playing with myself just an hour earlier. Then I got a text - he's parking! I immediately ran into the bathroom and did a quick touch-up.

*Knock! Knock!* Oh my God, he's here! My heart started to beat so fast, I almost couldn't contain myself. All of these years of crossdressing in secret and finally the time has come to take a chance. I took a deep breath and opened the door. There was Dave, a good looking black man in his early 50's, wearing a white sweater and scarf. I remember thinking how are we going to say hello? Kiss? Hug? Nothing? Well, it turned out to be nothing. I opened the door, invited him in, and he followed. We then sat on the couch in the small living room. He offered me wine, to which I passed.

Honestly, I did not want to engage in small talk. I was paranoid about my voice sounding girly enough, plus I wasn't looking for any type of relationship. I just wanted sex! But I followed his lead and chit chatted a bit. As we were talking I noticed him looking me up and down. My sexy red dress, my red stockings, my brown wig, my natural breasts being pushed up by my bra to flaunt my ample cleavage. We had been talking for about five or ten minutes when I couldn't take it anymore. I looked down, touched his cock through his jeans and asked if I can finally see why we're here. Dave obliged and took of his jeans. He was wearing white briefs which looked like they were about to explode with his big black cock poking through.

My first thought was 'Oh my God, this is it!' I pulled his cock out of his underwear and started stroking it. Dave then leaned over and started to kiss me. Suddenly, I no longer felt my bra, my thong, or my dress. All of the sensations that had made me feel so alive were not giving me the rush. My bra and my thong were now just a part of me. The sensation was him. His lips were so big and wet that I felt like I was being swallowed every time he kissed me. Part of this was due to me still being tentative considering it was the first time I had ever even kissed a man. We french kissed for a few minutes, rubbing tongues and feeling each other's bodies. Finally, I led him to the bedroom.

As soon as Dave took off his clothes and laid on the bed, I couldn't believe how incredible his body was. He was very muscular with no body fat, and his cock almost looked fake, that's just how beautiful it was. Like Dave, I too was shaven down there but mine was being hidden by a red thong under my red dress. As soon as he laid on the bed, I laid on my stomach between his legs and started sucking his long black cock.

I can't explain how amazing it was. Until now, all I had ever sucked was dildos, which actually turned out to be pretty helpful. I was licking his 8 inch shaft over and over like a lollipop, while also playing with his balls at the same time. I tried to deep throat him a few times which got easier the more I did it. This was as close to euphoria as I've ever been. My natural breasts looked like they were jumping out of my dress, especially because of the position I was in. I could see my cleavage while I was sucking the most beautiful cock I had ever seen. The only problem was my hair kept falling front of my face, but Dave helped out and kept trying to hold my hair.

After about ten minutes of sucking him off, Dave stood me up on my knees and began sucking on my tits. It felt incredible. These breasts that I have spent so many days being ashamed of were now allowing me to feel like a real woman. I kept moaning, "suck them Daddy." At first the feeling of having my tits sucked was a little weird, but once I fully embraced the fact I was now a woman and my man was sucking on his women's tits, it felt exhilarating.

Five minutes later, Dave slid off of the bed and walked to the edge. I inched myself over and grabbed his cock, I simply could not control myself. It was so beautiful and was basically staring me right in the face. I remember thinking I could play with this all day. He bent down and kissed me on top of my head and then started making out with me again. I was a little overwhelmed by how aggressive he was kissing me, but it also felt good to be wanted by someone like that.

Dave then stood on the bed and began to slide his cock in and out of my mouth, to the point that I started to gag a little bit. I told him let's go slow, which he was okay with. It seemed like an awkward position to give a blow job but I went along with it. After another five minutes, I rolled over to the other side of the bed and spread my legs. Truth be told, this is the position I was most excited about. I wanted to spread my legs wide with his cock between my thighs. Dave got down on his stomach, slid on top of me with his rock hard 8 inch shaft rubbing my thong and back pussy, and we began making out again.

This was the first moment when I stopped being nervous and began to fully embrace everything. I stuck my tongue right back in his mouth and began passionately kissing him back as he kept thrusting between my thighs. He was not inside of me yet, but it was almost even more exciting to feel him rubbing against me. Dave then pulled my dress down a bit to reveal my breasts and continued to suck on them. I then saw Dave do what I had been waiting for... He pulled off of me and grabbed the lube.

After making a joke about the lube being water-based, he put a Magnum condom on his big and perfect chocolate cock and covered it with the lube. He decided it'd be easier to get it in if we did it doggy-style so I bent over and stuck my ass out, feeling completely vulnerable but incredibly excited. He pulled off my red thong and began to rub the head of his cock on my back pussy. I had fucked myself with some rather large dildos so I knew I'd be able to take his cock, but I didn't know how a real cock would feel. Well, it was time to find out.

Dave put it inside of me and pulled out a few times as my hole was loosening. Finally, he put the whole cock in and I felt a beautiful but noticeable pressure inside of my back pussy. It was official, I was being fucked by a man. Not just any man, but a black man with a big, gorgeous cock. He began to thrust in and out, in and out, in and out.

Even though I had fucked myself with dildos, I had only been able to do so in a few positions, such as the cow girl or the traditional missionary bottom. This was my first time feeling a cock penetrate me from behind and it was interesting. There was really no work to be done on my part, I just bent over and let Dave do everything.

Every minute or so he would pick up the pace until we were both thrusting into other aggressively. By now, I stopped being passive and was really slamming my ass into his cock. This is amazing, I kept thinking to myself. We fucked doggy-style for about ten to fifteen minutes until Dave turned me around and began to make love to me missionary style, with my legs spread wide and him in between. Eventually he placed my legs on his shoulders as he was sliding his cock in and out.

We kept going back and forth with these two positions for about a half hour. At this point, I decided that I wanted to try something else that I had been dying to do - 69. I asked Dave and he said, "Yea baby." I laid on my back as Dave slid on top of me and placed his tight, muscular ass right on my face. I began sucking his cock again, but this time he was also sucking mine. My little cock was just that, little. Only about 5 inches and skinny when rock hard, I feel like my cock was made to be hidden under women's underwear. But right now, Dave was sucking it like a vacuum cleaner. It felt amazing. I kept thinking that I could stay in this position forever.

After about ten minutes of that, he started to fuck me again. This time he laid me flat on the bed and put a pillow under me which propped by ass up. He buried my face in another pillow and began to fuck me harder and faster than before. It even felt like he was deeper inside of me than before. It didn't hurt, but the pressure was much more intense now. I could hear the sound of his body smacking my ass with every thrust, over, over, over again.

We then began to 69 again, with him on top of me like he was earlier. I remember laying there sucking his cock and thinking that this is the real me. I just love sucking cock. We kept this up for another fifteen minutes or so before we laid side-by-side stroking each other. Eventually, I came, but he wasn't. He was rock hard, but not cumming. Finally, Dave said to me, "Baby, I have trouble cumming. I don't think it's going to happen tonight." I didn't care. I kept stroking his beautiful chocolate cock for no reason other than I loved touching it.

Imagine I got to play with his cock whenever I wanted. Imagine this was my man, my boyfriend. Imagine I was his girlfriend, and just like I could play with his cock whenever he wanted, he could play with my tits whenever he wanted. With those thoughts running through my mind, I finally gave up on getting Dave to cum. We kissed and he got up to shower.

A little while later Dave got dressed and was ready to leave. I was kinda sweaty from the past hour and a half, but didn't want to shower until he left. Before he left he gave me a few more kisses and a hug. He said, "Bye baby," and I closed the door.

I looked in the mirror and saw a woman who had just experienced an intense love-making session. I didn't notice my bra, my stockings, my dress, my wig, my make-up or my earrings until I looked in the mirror. These things had always been what got me off - just feeling like a girl. Well, not anymore. I had become a girl. I had made love to a man for more than an hour. The one question I was not prepared for was, What do I do now?