Dave Helps Jason become Jenny

My name is Jason, and I suppose it all started when I was 21, in my third year of college. My friends and I were going to a theme party where the girls would dress as guys and the guys as girls. I was studying in a city in California, and it was a warmer than usual May, so we all decided to wear skimpy dresses, wigs and makeup. To avoid an awkward situation, we agreed to go to buy our outfits together; I got a black cocktail dress that went down to my knees with a slit almost up to my waist, and some black lace panties - I don't know why, but I just thought it would be weird to have men's underwear with a dress. My friends were looking at me a bit strangely when they saw I was getting panties as well, but they didn't say anything. In any case, there was supposed to be a prize for best dressed 'girl' and 'guy', and being quite competitive I wanted to be convincing enough to win.

When the night of the party came, I started to get ready at the apartment I shared with a few other guys. I shaved my face to make sure I would be convincing with the makeup - which we had borrowed from some of our female friends - and tried on the dress on top of my boxers (I had second thoughts about the panties, given my friends' reaction). I'm not that tall - only around 5'8" - and weigh about 140 pounds soaking wet, so the dress fit me pretty well, which was a surprise as I just randomly picked one from the rack at the store. I took a second to check myself out in the mirror, and then went to work on the makeup. I had watched some online tutorials, and tried my best to do something classy with the lipstick, foundation, blush, and mascara that I had borrowed. When I put on the wig - I had picked a dark brown one to compliment my pale skin - I was shocked to see a very attractive girl looking back at me in the mirror!

The only thing that didn't really work was that my boxers were visible through the slit in my dress. I didn't have any other types of underwear, so I decided that if I wanted to have any chance of winning the prize, I could either go commando or I would be forced to wear the panties that I bought. I tried commando at first, but if I moved to quickly or danced there was a risk that I would flash my ass (or worse!) to the whole party, and besides it just felt weird to be 'exposed' down there. So I ended up slipping on the panties, which felt oddly both sexy and comfortable at the same time. I finished off my outfit with a pair of white and pink sneakers that I had borrowed from a girl friend.

When I met my roommates in our living room they were pretty shocked to see me. They hadn't put much effort into dressing up, and they basically looked like guys in drag, facial hair and all. One of them, Dave, a tall, hairy, muscular guy - pretty much the exact opposite of my physique - even said that if he didn't know I was a guy he would definitely try to hit on me. They took turns making fun me of me and we all laughed, but I was actually kind of happy about their comments - at the time I just thought it was because I would be a shoo-in to win first prize.

After a bit of pre-gaming, we headed to the party, which was being hosted by some mutual friends at their huge house. I was already pretty tipsy (I was and still am a bit of lightweight), and had stopped being self-conscious about how I was dressed. As Dave and I made our way to the kitchen to get a drink, I couldn't help but notice that some of the guys at the party were looking at me a bit weird; Dave noticed as well, and he gave me a mocking grin. "I think you might be a bit too convincing, Jason, some of these guys look like they want to jump you..." he said.

I just laughed, thinking he was joking. After we got our drinks in the kitchen, we went outside to the backyard. They had done an amazing job setting up for the party, with soft lights everywhere and the pool looking very tempting on a hot night. I was looking around for a girl, Stephanie, who I had been trying to hook up with for a while now. When I saw her with some friends, I left Dave to go chat her up. When she saw me she was impressed and said "Wow Jason, looking very hot!"

I was nervous around her but happy to hear the compliment, so I smiled and said thank you, then mumbled something about the first prize being a new iPhone or something, which I definitely couldn't afford between student loans and my crappy part time job. I told her she was looking pretty convincing as well in a fake beard, a plaid shirt and work boots, and we started talking about our week, the party, our friends, everything really - I felt for the first time that I was actually getting somewhere with her, and was pretty pumped to see where this could go.

We got through a few drinks and by this time I was really starting to feel tipsy, when she looked past me and smiled at someone coming to join us. "Hey Steph, who's your hot friend?" I turned around to see a tall, ripped guy in a bra and a short skirt.

"Hi Mike, this is... Jenny" she said, winking at me. I could tell by the way she was looking at him that she was checking him out, and when I got a better look at Mike I understood why - not only was he in great shape, but he was very handsome as well. I was a bit upset but it was a party and I decided to just play along with the joke for now, so I smiled a bit shyly and introduced myself as 'Jenny'.

Steph took the opportunity to make an exit, saying she needed to run to the bathroom, and Mike and I started chatting. "So, you didn't have time to find a convincing enough outfit?" he said smiling "I mean, I'm not complaining, you look great, I'm glad you didn't try to dress up like a guy." He was leaning close to me, and for the first time since arriving, I started to feel a bit awkward and uncomfortable, very aware of how the dress was clinging to my slim frame, and how the lace panties felt between my legs.

For whatever reason, I just kept pretending to be a girl, and we ended up chatting and 'flirting' for a good half hour. He was really nice and charming, but eventually it all became a bit too awkward, and I started to look around for Dave, Steph, or some of my other friends. Just as I was about to excuse myself, he leaned in, wrapped his arm around my waist, and kissed me. I was shocked, and didn't react, so he pressed himself against me; even more shocking, I could feel his hard cock - much bigger than mine - rub up against my stomach. When he reached around to grab my ass, I finally managed to break away, he could see I was upset and quickly apologized. I told him not to worry, but I didn't at all know how to process this while drunk, so I just ran out of the party like an idiot. We had been talking in a quiet, secluded corner of the backyard, so I was really hoping that no one saw what happened.

I picked up an Uber outside the house and started to make my way home. The driver noticed I was a bit distraught and asked if I was okay; I just smiled at him and said that I had a bit too much to drink but was fine. He smiled back, and I could tell he was checking me out in the mirror, so I pulled out my phone and started looking at videos, hoping he would get the message. When I got home it was early and all my roommates were still at the party, so I rolled a small joint to calm myself down. After I went into my room and turned on some music to relax.

I couldn't get the thought of Mike kissing me out of my head, and was replaying the scene over and over again, feeling his big strong arms wrapped around me. Part of me was still shocked at what had happened, but another part was thinking that it wasn't so bad to feel his hard cock pressed against me and his hands on his ass. I realized then that I still hadn't changed out of the dress and panties. Was I really that convincing as a girl?

I got up from the bed and looked at myself in the mirror. Not only was a convincing as a girl, I had to admit that I was definitely hot, albeit a bit lacking in the chest department. Maybe it was the joint, but I started to get hard, and I began to run my hands all over my body, posing like a girl with my ass sticking out. When I reached down to touch my lace panties, I was shocked to find them wet with precum - I was so hard that my cock was aching. I bent over from my waist, as I imagined a girl would, and slipped off my panties, letting my hard, wet cock pop out. At this point I couldn't control myself, and I started jerking myself off while moaning softly. I sunk down to my knees in front of the mirror, still playing with my cock, running my hands through my shoulder length hair, rocking my hips back and forth. I was surprised to hear my moans become higher pitched, almost like a girl's. I was now almost sitting down, still rocking my hips back and forth, but more like I was riding a horse or a bull. For whatever reason, at that moment, I pictured Mike's cock against me, his hands exploring my tight ass, wondering what would have happened if I hadn't left the party. I could feel a huge orgasm building, and all of sudden I leaned back and exploded all over my dress, my neck and my face, moaning hard, still rocking my hips. I passed out on the floor, covered in my own cum.

The next morning, I woke up very embarrassed, and quickly changed out of my dress and showered. As I was coming out of the shower, I saw Dave sitting on the couch. "Hey man", he said, "Where'd you go last night? I saw you chatting to Steph but then you disappeared. You won first prize, but they ended up giving the iPhone to the second place person because they couldn't find you". I was still feeling really out if it and told him that I got a bit too drunk and decided to head home early. He just nodded, smiling at me a bit weird.

As I was closing the door to my room Dave popped his head in, "Hey, do you have a second? I had an idea I want to run by you" he said. "Listen, I know that you're struggling to make ends meet, so I thought about a way that we could make some extra cash."

"What are you thinking?" I asked. "I already have a part time job, and I don't think I can do much else and still stay on top of school."

He was looking a bit embarrassed which got my attention, and he finally said "Look, you were super convincing as a girl last night. To be honest, you were the hottest 'girl' there." He was looking at the ground, maybe a bit worried about how I would react to what he was about to say. "I think we should try to set you up as a cam girl crossdresser" he finally blurted out.

This caught me completely off guard, and I didn't know what to say. Finally, I managed to tell him that I wasn't gay, and definitely did not want guys looking at me like that.

"I've already thought about that" he said "We'll only broadcast to cities on the East coast, and besides, no one will recognize you with your make up on and a wig." He could see that I was looking a bit skeptical, so he added "And don't worry I know you're not gay man, it's just about making some solid money on the side. Honestly from what I read you can make up to $1,500 a week, just by doing one hour sessions every night."

I was about to tell him absolutely not, but hearing how much money I could make was definitely making me reconsider. "What would I have to do...?" I asked, surprised I was even considering this.

"It's easy" said Dave, "You just have to wear sexy outfits and dance around a little, maybe show a little skin, that's it."

"Okay, I guess that's not so bad..." I said. Was I really going to do this? If he was right, I could stop working AND start to save up to pay off my student loans, maybe even graduating debt free.

"Great!" he said smiling, "The first show will be tonight. The other guys will be out so we'll have some privacy."

--------------

I knocked on Dave's door at 7pm, carrying my cocktail dress, the lace panties, and my wig. "Oh don't worry about those" he said, "I've got something else for you to wear. You can keep the wig though, it looks great on you." He handed me a bag with some clothes in it, and told me to go to the bathroom and shave the hair off my body, take a shower, and get dressed and come out.

"I am definitely not shaving" I told him, starting to regret this decision.

"Honestly Jason, I don't think it's going to work if you don't" he said "I know you're already naturally pretty smooth, but we need you perfect for this first session, otherwise we won't get any followers and we won't make any money. You can use the electric razor to shave around your dick, but use the normal one for your legs and arm pits." Not knowing what else to say, I grabbed the bag from him with a death stare and went to the bathroom.

First I found the razor and shaving cream, and somehow managed to shave my legs without any issues. It was definitely harder than shaving my face! Then I took the electric razor and trimmed all around my cock and balls, and took a shower. It was definitely weird feeling so smooth everywhere, but I would be lying if I said I wasn't excited about it as well - it made me feel more feminine and, well, vulnerable.

Oh well, time to get dressed, I thought. When I saw the outfit, I swore under my breath. Inside the bag was a black thong, stockings, and a sheer nightie. That was it. "Are you serious?" I said to Dave through the bathroom door "There's no way I can wear this!"

"Just try it on" he said "Trust me this will work!"

Grudgingly I pulled on the stockings and the nightie, then slipped into the thong. I'm not going to lie, it was hot feeling my ass exposed in the thong through the sheer nightie. I did my make up like the night before and put on the wig. When I saw myself in the mirror, I didn't recognize the person staring back at me. I wasn't Jason anymore; I was a hot girl dressed in sexy lingerie.

When I opened the door and walked back in the room Dave looked at me but didn't say anything. He just sat down quickly behind his computer and webcam and started to set up the session. "Well, how do I look?" I asked.

He looked up, and I could see his face was red. "You look good..." he said sheepishly "Now sit down on the bed, but in a girly way."

I got onto the bed and sat down, tucked my legs around to the side and started unconsciously playing with my hair. I don't think I had ever been this nervous before.

"Okay" said Dave, "Are you ready?"

"As ready as I'll ever be" I said, trying to keep my legs together and cover myself as best I could.

"Okay, here we go. Aaaand we're live!"

As soon as he said that I froze, realizing that this was actually happening. I must have been so red.

"Jason, you need to move a bit" said Dave "Some guys have already joined based on your profile, and they're saying that you're really hot."

For some reason, hearing that other guys thought I was hot made me a bit less nervous, and I started to shift on the bed and play with my hair, then waved at the camera and smiled.

"That's perfect" said Dave "Now we're going to start taking requests."

I looked at him a bit shocked - I thought I was going to be in control of this session!

"Okay, this guy wants you to spread your legs a bit. Do you think you'd be comfortable doing that? He says he'll tip you $15."

$15 just for spreading my legs? Not a problem. I slowly opened up my now smooth legs, exposing the black thong underneath that was struggling to hide my cock.

"Great Jason, he says you're super hot. Now this other guy wants you to dance a bit."

I got up off the bed and started dancing awkwardly, not really knowing what to do. "No no" said Dave "You have to move your hips and shake your ass a bit, like a stripper."

I started moving like he wanted me to, swinging my hips and showing off my ass. I don't know why, but knowing that I was turning on all these anonymous guys was a huge turn on for me. I kept dancing for a few minutes, feeling sexier and sexier.

"Uh, Jason..." said Dave, smiling, "I think someone is saying hello..."

I looked down and sure enough, my hard cock was sticking out of the thong! I was mortified, and covered myself up quickly with my hands, jumping back onto the bed. Dave was just staring at me and smiling.

I heard a dinging noise from the computer. "Wow, so this guy just offered you $100 to jerk off live on camera" said Dave.

This was going way too fast, and I didn't have time to think about what I was doing. All I knew was that I was incredibly turned on, and I didn't want to disappoint my viewers. I stood up, bent over with my ass facing the camera, and slowly pulled down my thong. Out of the corner of my eye I could see Dave swallow and look away.

I climbed back onto the bed, and slowly started playing with myself. Soon enough I was moaning like last night, and I was leaking precum all over my hand. Dave was watching but he didn't say anything. I kept going faster and faster, staring into the camera, feeling exposed and vulnerable and sexy all at once, struggling to not moan like a girl. It was useless. The closer I got to cumming, the more my moans became high pitched. Dave was staring at me now without blinking, and I noticed that there was a huge bulge in his pants. Was I turning him on as well? This pushed me over the edge and I just started cumming everywhere, moaning loudly with pleasure. When I finally stopped I felt ashamed but also happy in a weird way, and I licked my now cum-stained fingers and blew a kiss to the camera.

This seemed to snap Dave out of his trance and he shut off the session. "Wow" he said "I think that worked. You've just gained more than 150 followers!" He got up slowly, trying to hide the massive bulge in his pants, and left me in the room to clean up.

--------------

This went on for about 2-3 weeks. Each time I wore a skimpy outfit, did a sexy dance, and ended up jerking off on the bed. The only thing that changed was that I was getting more and more comfortable exposing myself, and was posing in sexier ways.

I was just starting to get into a rhythm when Dave said that he wanted to talk about going to the next level. His brilliant idea was that I should use a toy to play with myself - he said we would do an offline practice session on one of my nights off to test it out. I came to his room as usual when the other guys were out, and he had me put on a thong bikini with my wig. Then he pulled out the toy, which I was shocked to see was a pretty large dildo!

"What the fuck is this, Dave?" I asked "When you said a 'toy' I thought you mean a pocket pussy or something. There is absolutely no way I'm using that, I told you I wasn't gay!"

"Dude, lots of straight guys use dildos and prostate massagers and what not, it's perfectly normal and doesn't at all mean that you're gay. You'll go from 1,000 followers to 10,000 if you do this, I promise. Here let me help you out, just lie down on the bed."

I was really upset but the idea of getting 10x more followers was definitely tempting. And I remembered Steph telling me that she had an ex - as straight as they come - who liked her to use a strap on every once in a while. "Oh well" I thought, "might as well give it a shot!"

I laid down on the bed, breathing heavily, as nervous as I was the first time, even though it was only Dave who could see me. He poured some lube onto his finger, moved aside the bikini, and slowly started opening me up. At first it was weird, but even at the beginning it was turning me on; something about it just felt so transgressive. He was very gentle, and one finger slowly became two, and he was massaging my smooth legs, stomach, and ass with his other hand. Once he could fit both fingers in comfortably, he started making a slow motion with his fingers. Eventually, he hit something inside my ass that sent shivers all through my body, and I moaned a bit without even realizing it.

"Ah, I see you're starting to enjoy it" said Dave, smiling. I was so embarrassed that I just covered my face and my eyes with my hands, not knowing what to say, feeling completely at the mercy of this big, strong man. "Okay, now I'm going to use the dildo. I'll be gentle, I promise."