Hi, my name is George and at the time this story occurred (not long ago), I was 21 and home for college during the summer. I am white, 5'11, and a little over 200 pounds (not small at all, but far from being fat). Though I definitely think I am more straight than gay, particularly in the last few years, I have gotten more and more gay urges. I have been dressing up in women's underwear for many years and have even developed a stash of my own. I've only actually had one gay experience (see my other story "Adult Theater Fun" [though admittedly, only part of that is true]), but ever since then, I've just wanted to do it again.
Overall, I am a very calm person and generally do not do anything like have sex with random guys (or generally with ANY guys), so at home, I wasn't sure what to do. I was paranoid about being found out, but even more so, I was paranoid I would catch some STD (even just herpes through kissing or oral), so I felt stuck. I just didn't have the nerve to do anything. I would watch gay and shemale porn, dress up and go on webcam chat sites, and I would play with my dildo. It satisfied me for a bit, but I just wanted to do more.
I tried to think more and more about what to do and my head just kept going to one thing...Aaron. Aaron had been my best friend for about 10 years. We didn't go to the same college, but we were still close. He had no idea of my gay side and I was pretty confident he didn't have one. Aaron isn't the sexiest guy out there, but he was pretty good looking. He has short dark, hair, is about 6 feet tall, weighs about 180 and is pretty fit. I knew he had had sex with only one girl (once) and she was a virgin, so I figured a. he was clean and b. he was probably pretty horny. I knew trying to do anything with him was just a horrible idea, because it would probably ruin our friendship, but I couldn't get the thought out of my brain. It festered there for about a month.
One night, we were up in my room getting drunk. Not super drunk. Just enough to lower inhibitions and make us a bit worse at Xbox. Eventually we got bored of playing and just sat there talking. My mind just kept wandering to one thing. I'd try to tear it away, but it would just go right back. Eventually I said "Aaron, can I tell you something I've never told anyone before and will you promise to never to tell anyone either?" He said "Of course man, what is it?" "I'm bisexual," I replied. He briefly look surprised, but didn't say anything. I went on to explain the feelings I had, but left out the crossdressing. I just wanted to have sex with men, not relationships. I was hoping he would tell me he felt the same way and we would go from there, but he eventually just said "I had no idea man."
We awkwardly sat in silence for a couple minutes. Eventually, I said "Aaron, you are my best friend and are the one person I know I can really trust. I've just been dying to do certain things and I am afraid I'll do something stupid and end up doing something with a random guy. I would completely understand if you don't want to, but would you consider letting me give you a blowjob?" He just sat there with a dumbfounded look on his face. Eventually he said "George man, you are my best friend too, but I'm just not into that." I had promised myself I would just end it there, but I just couldn't do that. "It's not like you are giving ME a blowjob. Hell, just pretend I am a girl. Receiving a blowjob doesn't make YOU gay," I replied. He thought for a second and said "I don't know. It's not like you look like a girl or anything. I would just feel weird." I stopped and thought about the situation. I didn't want to tell him about the crossdressing. He was freaked out enough. I eventually came up with a solution; "Okay, well I have a wig that I used at Halloween one year. It's pretty realistic. If I wore that, would you let me?" What Aaron didn't know is that though yes, I had worn it for Halloween, I wore it all the time while dressed up in lingerie. He still didn't seem quite convinced. "Aaron, I know you are horny. Don't lie. You know you would enjoy a blowjob and it would really help me out." He finally relented and said "Okay, but you have to promise to never tell a soul." "I promise."
I walked over to my closet and pulled the wig out of the bag where I keep my lingerie, careful not to make it obvious what else was in the bag. I put the wig on and walked over to Aaron. I knelt down on the floor and undid his belt. I then carefully unbuttoned and unzipped his pants. With his help, I pulled off his pants and boxers. His cock was completely flaccid, but the first glance of it made me excited. It wasn't huge, but wasn't small. I predicted that when it was hard it would be 6 or 7 inches. Aaron closed his eyes and I moved forward and engulfed his cock with my mouth. I slowed bobbed back and forward, massaging it with my tongue and in no time at all, his cock sprang to life.
I pulled back and looked at it, admiring it in all its glory. There it was, about 7 inches long with an average thickness. His cock was cut, giving it those glorious two colors that accompany circumcision scars. It was rock hard, slightly bobbing up and down on its own. The head pulsed and I could tell Aaron wanted some more attention, but I left him with another moment of anticipation. I loved the way the veins showed on his rock hard cock and how my saliva made it glisten in the artificial lights. It curved ever so slightly to his left, giving it a little extra character. Looking at his beautiful member made me crazy. I leaned in and put as much of it in my mouth as I could. Aaron moaned and I started bobbing my head. My hands took turns massaging his balls and rubbing his cock below where my mouth would go. Periodically, I would go down and lick his balls or put them in my mouth and then lick his cock from base to head.
After a while, I noticed Aaron thrusting up a little to meet my mouth (well as much as you can sitting in a chair), so I played around with him, only sometimes giving him what he wanted and sometimes slowing down, leaving him dying for more. The brown-haired wig I was wearing made the job infinitely more difficult because hair kept getting in the way. It made me feel for girls who have to deal with it all the time. However, unlike girls, I didn't have a hair band around to put it up, so I just dealt with it and kept moving to the side. I hoped Aaron would help keep it out of my face, but I think he was a little too distracted to do that. Eventually he reached his hand out and I got hopeful, but instead, he just helped push my head down onto his cock, making me briefly gag. However, I recovered and got used to it.
I was getting so excited that I couldn't help from touching myself. One of my hands reached down and rubbed my cock through my pants as I went. I must have only lasted 5 minutes before I came, leaving a huge wet spot in the front of my pants.
I kept going and his moans started getting louder and more stuttered. I knew he was getting close. I kept going, trying to read exactly what he wanted. He got louder and louder and pushed my head down a few times and I felt cum start to fill my mouth. I swallowed as much as I could, but a bunch leaked out onto his cock. His cum tasted amazing (well at least as far as semen goes) and I licked the remaining cum off of his cock.
Aaron sat there, spent. He eventually said "That was amazing...but we can't do that again." But even at that point, I knew I could probably change his mind.
For the next week or so, we pretended nothing happened. We hung out a couple times (and with other friends), but neither of us spoke a word about it. I couldn't get it out of my mind and must have masturbated thinking about it every day. I kept thinking of how to convince him to do it again and finally came up with a plan of sorts.
One day, I knew Aaron was going to come over later and hang out and I just prayed he wouldn't try to invite anyone else. I spent the afternoon carefully shaving my legs, chest and armpits. A few hours before he came over, I put on my favorite and sexiest lingerie. It's a sexy pink bustier with matching string bikini panties. It has garters that attach to a pair of sexy stockings I own. I then put on jeans, a t-shirt, and socks to cover it all up. Unfortunately, it was still obvious I was wearing the bustier, so I put on a zip-up hoodie over the t-shirt and had to put the AC on high (thankfully my parents weren't home that night).
Aaron hadn't invited anyone else, so it was all good. He wanted to go out for a bit, but knowing it would be extremely odd to have a sweatshirt on outside, I convinced him to stay him. He asked why it was so cold and I told him that the AC was messed up and it was either super hot or super cold so we chose cold.
The night progressed pretty normally and as usual, we drank some. We watched some random movie on Netflix and I noticed that Aaron seemed particularly fixed on a sex scene in it. I knew that was my cue and excused myself for the bathroom. I quickly stripped off my clothes and put in two breast forms I had stashed in there. I then carefully put on the small amount of makeup I had stored in the bathroom and put on the wig, which I had put below the sink earlier that day.
I looked at myself in the mirror. I was far from looking like a real girl. I was too big and didn't have hips. My makeup was good, but it was clear I hadn't been putting it on my whole life. Overall, I thought I looked pretty damn good...But I wasn't the person I needed to impress.
I walked back into my room and Aaron stopped watching the movie and just stared at me. He stuttered "George, what the fuck?" I said "You said I didn't look enough like a girl, so I thought I'd change that. You know you enjoyed last week. Let me do it again." He started to say no but then looked me up and down and said "Alright, yeah that was amazing. You can do it again." I switched off the tv and went over to Aaron and started to repeat the events of the night a week before. The big difference is that this time, he barely closed his eyes and he just kept watching me. As we started to get into it, he surprised me by saying "Oh yeah. Suck it you slut. You know you love daddy's cock." This made me happy. I knew I had him hooked. He periodically kept saying things like that and kept calling me his girl and a slut.
Eventually, he told me to lie down on the bed. For a split second, I thought he was going to suck my cock, but then figured that probably wasn't going to happen. To my huge surprise, he leaned forward and stuck his tongue in my mouth. We passionately made out and he fondled my (fake) breasts. After maybe 5 or 10 minutes, he climbed on top of me and started fucking my mouth. For a while, he didn't go in too far, so I was enjoying myself. After a bit though, he really started fucking my mouth and made me gag. I pushed him up a bit and he eased up. He started fucking harder and harder until I could barely take it anymore and he shot his load. It seemed like he came for 2 straight minutes. I swallowed what I could, but a huge amount of cum spilled out all over my face.
Aaron lay down next to me, spent. He said "Fuck. No real girl would let me do that. Geez George, if you want to be a girl for me that bad, I guess I'll just have to let you. What can I call you?" "I like `Jessica'" I responded. He said "Okay, Jessica, I like that, now go to the bathroom and get cleaned up."
I went to the bathroom and when I looked in the mirror, I was shocked. For one, I was covered in cum. It was all over my face, my chest, and even in my wig. My wig was disheveled and it pretty much looked exactly like you'd expect a girl's hair to look after being face-fucked. Lastly, my make-up was smeared EVERYWHERE. I looked horrible. I also understood why Aaron had called me a slut. That's exactly what I looked like.
There's more to come. If anyone really likes this or has any comments, please feel free to e-mail me at George3130@gmail.com.