My First Time with a Man

Part of me has always wished I was a girl. My sisters used to dress me up like a girl when I was little. When I was a teenager I would sometimes take my sisters' clothes when I was home alone and try them on. I loved the way the soft and satiny material felt. When I got older I started becoming bi-curious, I would chat with guys online and send pics of myself, often times in my sister's clothes. All the guys loved it and it made me good, being looked at like that. I especially loved when older guys would lake with me. The idea of a guy old enough to be my dad excited me. I started getting a little bit bolder and bought a wig and makeup and even some nail-polish around Halloween, so I could always say it was for a costume. I practiced doing makeup to make myself look more feminine. I went to the store and I got a bra and panties, some thigh-high stockings (which come pretty high on my short legs), a pair of heels and a pretty wrap dress that came right above the knee. I asked for a gift receipt so it made it seem like it was a gift. I'm not a hairy guy so I never had to worry about facial hair, or really body hair for that matter. So much so, that my parents never even noticed the times a shaved my legs, or if they did, they never mentioned it. I loved the responses I was getting and had so many guys wanting to meet up. Finally I decided to just go for it.

I was 22 and in good shape, thin but not muscular. I am only 5'4" with blue eyes and dirty blonde hair. My parents were going away for the weekend and my sisters planned on being with their BFs so I had the place to myself. Having a full weekend to myself I decided to jump on the opportunity. I went to my usual chatrooms and identifying as a CD and posted some of the pictures I had taken. OMG the responses I received. I guess I looked better than I thought. So after chatting with a few guys throughout the day I eventually hit it off with an older guy who lived a few towns over from me. He said he was 46 and he was 6 foot.... and married. He was a big burly buy with a hairy chest and neat beard. I can't explain why but somehow I just felt attracted to him. So we talked and exchanged pics, me dressed up and not dressed up. Finally he asked me if I wanted to come over to his place that night. I was terrified and excited at the sometime, when I wrote back, "Yes." He asked if I was willing to be dressed up when I came over, and again I said, "Yes." Now I had to get to work.

I still had a few hours to get ready so I took my time. I went and took a shower, taking the time to carefully shave my entire body. Going so far as to use my sister's moisturizer so I was soft and smelled nice. Next I painted my nails so that they had time to dry. Since no one was home I decided to live it up and do my makeup and hair at my sister's vanity. It was nice not having to sneakily try do do it in my room. I took my time and was able to do it flawlessly. I was able to style the wig so it wasn't just some mat of hair. It actually looked like it did online, when I bought it. Now time to get dressed. I put on the pushup bra I had bought and put those inserts in it, so it would kind of give me cleavage. The rest I used makeup to give the illusion (you can learn anything from youtube). I put on the panties, tucking my penis down, as I had been practicing, the thigh-highs and my dress. With no one home I could use the full sized mirror in my parents room to finally see me, and not as a crappy selfie. I was shocked. I looked like a girl. From a distance I would probably be confused with one of my sisters. I was counting on that because I now had to leave the house, dressed like this. Thankfully it was winter and got dark early, so if any neighbors saw me, they wouldn't realize it was me. Around 10pm I got the text, "You can come over now." The terror and excitement was back and I replied, "OK."

He texted me his address and some instructions. They consisted of parking at the end of the block and texting when I was there. Then I was to start walking up a few houses and he would signal me. So I drove and parked at the end of the block. It was a dark street. Street lights were overgrown by trees so you couldn't see house numbers. So, I sent my text and started walking. After passing the second house I heard a, "psst" but I couldn't see where it came from. Then he used the flashlight on his phone to get my attention. He was behind the fence on the side of the house. I walked up the dark driveway, and over to him and he let me in through the fence. He greeted me and said we had to be quiet because his wife wasn't home but his kids were sleeping. By this point you could pretty much see my heart beating through my chest. Here I am, at a strange person's home, no one knows I'm here, and I dressed as a woman about to do, who knows what. And yet with all of this... I followed him through the fence, down some steps into what seemed to be the basement.

When we went in and he turned on the lights it looked like an apartment or maybe a mancave. It was too small for a family so I'm guessing that they rent it out and they just didn't have a tenant. He closed the door behind me and came over and said he was glad I came over and put his arms around me and started kissing me. I had never kissed a man before but today was going to be a day of firsts. It also felt nice because it was winter and I was in a thin little dress. He said I looked beautiful and that he loved my outfit. He was in a pair of black sweatpants and a robe that was untied so his chest was out. He said that if he didn't already know he would have sworn I was a woman, which made me happy. I said thank you and that I was glad he liked it, in my best feminine voice, which really is pretty good. Not all nasally like you usually hear. He offered me a drink which I declined, though I should have because my mouth was so dry from nerves I could barely get sounds out. He told me to go and sit down by him on the couch so I did. We sat and talked for a little bit and he kept mentioning how good I looked which just made me feel better and more relaxed each time. "Why don't you come right over here," he said and I smiled and shifted over to him as he put his arm around me. With that he started kissing me again and I kissed him back.

My one hand had slid behind his back on the couch and my other had was on his chest. I loved the feel of his chest hair and kept rubbing my hands over it. Then it happened. He took my hand from his chest and moved it to his crotch. I could feel his hard cock through the pants (yet another first for me). He took his had away and I continued rubbing it. After a minute or two he stopped kissing me and leaned back in order to pull his pants down. Without missing a beat my hand was back on it stroking it. This was my first time touching one that wasn't mine, but I'd seen a lot of porn up to that point so I knew what to do. With his one hand he managed to undo the tie in the front of my dress. I lifted myself off of the couch so that he could pull it open. There I was... in an open dress, in a bra and panties, in front of a man whose cock was in my hand. "Fuck you're so sexy" he said to me, while pulling the dress down, off my arms to the floor. When my hand was free, he pulled me on top of him and started kissing me harder. At this point I knew what I was going to do.

I stopped kissing him and started kissing him down his neck...then down his chest... to his stomach and then to... it. In this age of the internet, and having been on the receiving end a few times (by girls) I reached into all of my knowledge and did what I came there to do. It started by kissing up the shaft and then up to the head. This giving my time to build up some saliva. With that accomplished, I switched to licking around the tip. Then up and down a few times until wrapping my whole mouth around it. It was so warm and hard in my mouth. A little bigger than average sized, definitely not porn star size. Up and down. You'd think I had done this a million times before but this was my first time giving a blowjob. And from his reaction he was enjoying it. I imagined him being married and his wife not doing this. I imagined him desperate to find someone who would do it and be excited about it. And it was me that was doing it. He would put his hand behind my head to push me down further onto it, which I surprisingly was able to do, and alternating between rubbing my back. Even going so far as to unhook my bra with one hand (very impressive). My alternating was between sucking his cock or jerking it while I licked and sucked on his balls. Finally, he said the words I was worried about... "You're gonna make me cum." What do I do? I have a few seconds to decide how this is going to end. Do I stop and he cums on me? Do I let him cum in my mouth and I spit it out? Or... do I swallow? It was a decision my brain had to make but I wasn't stopping. I doubled-down and was stroking him as I sucked. This was apparently more affective and within a few groans it happened. His body froze meanwhile I could feel his cock pulsating in my mouth. I could feel it filling my mouth with each pulse. What did I do? I swallowed it.

I think he was as shocked as I was, but I tried to play it cool. I climbed back up and straddled his lap. He was a very happy man. Apparently, I have a skill. We went back to kissing and now that my bra was off, he proceeded to now kiss and my body. The little cleavage I had disappeared with the bra but he went ahead licking and sucking my nipples, which I loved by the way. He rubbed his hands all over me, grabbing and squeezing my butt. Then he turned me around on his lap (reverse cowgirl style) and had me lay with my back on his chest while he kissed me. His hands rubbing all over my chest, down to my panties where my cock was no longer tucked, and had been hard for some time now. I don't know why but I stopped him. I think that maybe acknowledging my cock would somehow break the illusion of me being a girl. He took the hint and went back to kissing me. He told me to stand and lean over the coffee table, which I did. He stood behind me and pulled the panties down but I stopped him and told him I didn't want to do that. He understood so he said, "Don't worry, I won't." Then he took his cock which was getting hard again and starting rubbing it between my ass cheeks. Up and down just grinding it in between. He pulled out some lube and put on his cock while sliding it. It felt warm and nice but I still didn't want that, and again, he didn't try. So I started rocking and grinding on his cock between by cheeks. He put his hand on my shoulder and pulled me up so I wasn't leaning on the table. Pressed hard against his body I could feel lit sliding up and down, nervous and maybe starting to get a little open to the idea of it going inside me. He says the words again, "You're gonna make me cum again." He stops griding and turns me around and drops me to my knees. I wrap my hand around his cock and within a few stokes he is coming again. Not nearly as much as the last time but he managed to get one load onto my chest.

With that last ounce of his energy, he was done. He sat back onto the couch, exhausted. I climbed back on next to him and we just sat there snuggling, with the occasional kiss and my grabbing of his dick which was now red and worn out. Too much excitement for one day. The same for me. After a few minutes all of the events of the day & night had come back to me and I was starting to freak out. I told him that I needed to go and he understood. He helped me get my dress back on and my shoes. I didn't bother with the bra at that point. He gave me a kiss at the door before I left which for me felt as awkward as the first one. The "spell" that had come over me had worn off and now I'm thinking about what I had done. I then started what I imagine would be the walk of shame, back down to my car. I was freaked and then just as I opened the car door and the light came on. I went home and threw away everything, so afraid anyone would find it, as if they did, they would somehow know.

I shied away from it for many years and only recently decided to try again. Now being much older, I wondered who would ever be interested in me. It turns out guys are still interested... but that's a story for another time.