First Time With A Man While Crossdressed

This isnt about how I started or why. This is just about the first time I was with another man. I had met this guy in the chatroom. He was in the next city over, a couple years older than me and similiarly inexperienced. He was fit and decent looking so we made a plan to meet up. I was very nervous about this, but excited as well. I was just doing this for fun and to try something new. I am not really attracted to guys, but wondered what it would be like to be with one as well as the role-reversal aspect. He was in the next town over, but would come to meet me so I rented a hotel room one day and spent the next couple hours getting ready. I had slowly accumulated some clothes, makeup, and a wig. (again, another story) I used nair for my hair and I think i burned my skin in a few spots as it became red and tender. I shaved off whatever the nair didnt get completely. It felt great to be hairless below my neck. After applying some feminine smelling lotion my skin felt fantastic. The air felt different when it hit my skin. It felt more raw, more sensitive. I wore a black teddy with garter straps and sheer black thigh highs (my favorite part), a short denim skirt, 4" leopard print ankle strap heels, and a white tank top.I also had a wig I purchased and some basic makeup and a nice smelling perfume. Looking in the mirror when completed I was looking pretty damn sexy if I say so myself (in a white trash hooker kind of way of course). I was 24, 6'0 tall, and about 145#. My face wasnt very passable, but my body was looking good. I do have very soft and full lips though, which men and women seem to like. Especially when covered in lipstick. He didnt show up at 7 like we had discussed and I was unable to contact him by email or the chatroom. By 8 I was very frustrated and began looking for someone else to come over. After all I spent the money and was all dolled up. I come from a smaller town so it wasnt easy to find someone else. Around 8:30 I heard from him and he sounded nervous, but said he still wanted to see me. (especially when I described how I looked). It took him about a half hour to get to me and I was scared and nervous the whole time. When he knocked at the door, my stomach jumped into my mouth. I didnt know what to do. art of me screamed to ignore him, the other half screamed to let him in. I peeked through the shades and saw it was him, and figured that this is what i spent the money and time to do so just go for it. I opened the door wide with a flourish and struck a pose in front of him. I was scared, nervous, thrilled, and excited all in one. At once his smile helped put me at ease. I welcomed him into the room and gave him a little kiss as he walked in. When I closed the door I leaned against it and continued to try and show off my body. He just kept smiling and looking me up and down. That was the first time I experienced the raw lust that a man can have. Women dont do the same thing. A man looks at you and there is no doubt about whats on their minds and that turns me on incredibly. I asked what he thought and he said I looked fantastic. I walked up to him slowly, pressed my body against him and slowly kissed him. As he wrapped his arms around me I made sure to be soft and passive. He pulled me closer and kissed me with passion and vigor. His tongue pushed past my lips and explored my mouth. Right away I felt the power of a man and what it was like to be passive and used. I adored this feeling. I loved being this object that drove him crazy with lust. His hands explored my body while his tongue explored my mouth. He was a couple inches shorter than me in my heels, but was larger and in good shape, latin, about the same age, and medium skin tone. He picked me up and laid me on the bed. I loved the way his body felt on top of me as we made out. I wrapped my legs around him and he dry rubbed his c*** on me. Telling me how hot I looked and how badly he wanted me. I began to stroke his hard c*** in his pants and he rolled over so I could get better access to it. I wanted it bad so I wasted no time in going down and unbuttoning his pants. I pulled off his pants while he took off his shirt. There was this nice hard c***, about 7 inches long and thicker than mine. I looked at it a moment then looked up at him and smiled he just nodded and said go ahead. I then began to lick, kiss, and savor this nice piece of meat. Not saying Im the best at sucking c*** since I'm inexperienced, but I think my enthusiasm made up for it. He continually told me what a good c*** sucker I was and how great it felt. I kept thinking about getting f***** by him, but I was too scared to say that. I had never done it before and was too nervous. I sucked him for a good 20 minutes (he later told me he jacked off before coming over) before he told me he was going to c**. I told him to c** in my mouth because I wanted to taste him real bad. He held my head and pushed himself about halfway into my mouth and I could feel him tense up just before my mouth became real salty and I felt his c** in my mouth. I sucked and stroked him while he came, but didnt swallow yet. When he was done he let go of my head and I could feel his body relaxed. I sat up in the bed and opened my mouth to show him I still had his c** on my tongue. All he said was d*** your a naughty b**** and smiled. I smiled at him and he told me to spit it out on his c*** and then lick it all up. I did just like he asked, letting it run out of my mouth onto his now flaccid c*** then licked it all back up and swallowed every drop. I looked up at him as I did it and said thank you for letting me suck your c***. Then I placed my head on his stomach and continued to gently suck his soft c***. There was more I wanted to do with him, but was still a little nervous and scared. We really didnt have much to talk about and I realized how little I know about him and suddenly realized he could steal my laptop that I was playing music on while I slept. He told me he wanted to see me stroke myself. I had done that before he came over but I was very hard while servicing him. I laid on my back and pulled my gurl c*** out and stroked it while he watched. When I was getting close to c****** he told me he wanted to see me swallow it. So I c*** in my hand and swallowed it. I laid my head on his chest and we just lay there in silence. I wanted him to f*** me but was scared to try. He ended up leaving shortly after that and we never met again, though we did chat a few times. I ended up using a ***** on myself in bed and stroking again.
edgarallanho edgarallanho
36-40, M
4 Responses Jan 11, 2013

Very nice story. By thw way, I love your profile picture. Very sexy.

thanks all. was a wild night.

Fabulous sweetie

Wow! Great story. I'm hard as a rock now.