tagTranssexuals & CrossdressersLosing My Virginity... Sort Of

Losing My Virginity... Sort Of

byhorneyguy99©

Tonight was going to be the night. In just a few hours, I would no longer be a virgin. The route my girlfriend and I had taken to get there, however, had been somewhat strange. Lets start a while back.

Her name is Kelly, and she's a beautiful girl. 5 foot 3, roughly 100 pounds. Her tits and ass aren't huge, but they fit her small frame well. She's always had long blonde hair, and that's what probably initially hooked me; I have a thing for blonds. We met during our first year of high school and started dating soon after that. When we started dating, all I'd ever done was kiss a girl, nothing else. The same goes for her, she'd never done anything but kiss before either. So we were both on level playing fields, both of us were curious about our bodies but there was little pressure because we were both new to everything. After about a month I got my first hand job. I remember being embarrassed when my dick erupted all over her. I didn't jack off much back then and it literally erupted everywhere. It was probably 2 weeks worth of buildup. It covered her arm, shirt, shorts, everything. But she just laughed it off. From there on out I was always comfortable trying anything with her.

After she made the first move I thought it was time to return the favor. High school girls were so uptight about doing anything with guys, in fear of being called a "slut." But now that she'd made the first move I thought it was time. I was over at her house and the mood seemed right so I went for it. I slowly moved my hand down her stomach as we made out but once I reached her shorts she grabbed my hand and stopped me. I asked her what was wrong and she told me that nothing was wrong, but that she wasn't ready yet. I thought it was a bit strange but decided to give her space. As the months wore on I would occasionally ask her if the time was right.... It never was.

We reached the 6 month point in our relationship and I'd still made no progress. I'd even talked to her best friend to ask if she had any reason why she wouldn't let me do anything to her. She told me that she cared about me a lot, but she just wasn't ready to go that far with a boy yet. We were, after all, still young high school kids, so I decided to leave it at that.

A week or so after our 6 month anniversary I received my first blow job. Of course I didn't know any better, but at the time, I thought it was the greatest moment of my life. I was proud of myself as I managed to last more than a minute. Not too bad for my first BJ I thought to myself. Things continued to go great in our relationship and while I was frustrated, I tried my best not to pressure her into doing anything she wasn't comfortable with.

But as the months wore on it became harder and harder not to say anything to her. And as we approached our one year anniversary I knew I was going to have to say something to her. I just couldn't take it anymore and I thought I'd been more than patient enough with her. It had been almost a year and I still hadn't even reached 2nd base with her.

"Why won't you let me finger you or do anything else to you? It's been almost a year now and I think I've earned the right to know why you don't trust me," I finally said to her.

"It's not that I don't trust you. We're both still young and I just wanted to take my time. But I thank you a lot for trusting me and not pressuring me into doing something I'm not ready for..."

I cut her off, "I know, I know, that's the same stuff I've been listening to for 11 months now."

"You didn't let me finish. I think I'm ready now," she told me with a very serious face.

"So you're going to let me finger you?" I asked with boyish excitement.

"No...." she said. When she said this I thought I was going to shit a brick but she quickly changed my mood. "Lets just skip all that, I want to have sex with you."

I was so confused. I still hadn't even taken her pants off but now she wanted to skip straight to sex. I certainly wasn't complaining, but it was a bit strange.

It was a Wednesday when we had our little chat so you can imagine that waiting until Friday was nearly unbearable. It felt like the slowest week of my life but Friday finally came. School ended and I couldn't wait to head over to her house that night, it would be just me and her.

The light of the day was just about gone as I knocked on her front door that night. She opened the door and was dressed in her normal garb. She always wore a t-shirt and short-shorts when we were staying in for the night. As I followed her back to her room I wasn't sure when I should make my move. Should I just go for it right now or should I wait a few hours till we were relaxed? I decided to wait, but not because I wanted to, but because I was nervous as hell. I'd heard all the horror stories about how the first time almost always sucks. It just hurts like hell for the girl and guys have trouble lasting more than 15 seconds. I think I just wanted to get the first time over with, and I hoped that it would get better after that.

She put on a movie and we continued just like it was any other Friday night that we'd spent together over the last 12 months. We talked about the latest high-school gossip. We laughed at the shitty movie we were watching; I felt myself finally starting to relax. A hour passed and it was Kelly that actually made the first move. I was lying on my back in her bed as she started kissing my neck. I let her take over as she slowly let her hand make its way down to my groin. She slipped her hand under my pants and started to grab at my cock. When her hand reached my cock I turned my head towards her and we started to kiss. She didn't waste much time as she quickly broke our kiss and made her way down to my shorts. Just as she finished unbuttoning them she pulled them off and threw them, along with my boxers, to the floor. Before I had any time to react she had wrapped her mouth around my cock. But for some reason, I was having trouble getting it up. This had certainly never happed to me before but I was starting to worry that my nerves would get the best of me tonight. I let her work for about a minute but to no avail. I thought that maybe if I finally got to finger her or something, I could get hard. I didn't know what to do.

I pulled her head up to mine and started kissing her again. I rolled over on top of her and started to make my way down to her groin with my hand. But just as my hand reached her shorts she stopped me again.

"What? I thought this is what you wanted?" I asked. At first I was pissed but then remembered that I was having trouble getting it up, maybe this would be a blessing in disguise.

"Nothing's wrong, let me do it." I wasn't sure what she meant by this but she rolled out of bed and stood up in front of me, just a few feet away. "You love me right?"

"Of course I do," I told her.

She smiled, "You'd never fuck me over would you?"

"Of course not, you mean everything to me. No matter what you ever did, I'd never fuck you over."

"O.K." was all she said. Kelly had a strange nervousness in her voice. She looked me right in the eyes as she reached down and undid the button on her pants. Next she unzipped her little zipper and put her thumbs in the waistline of her tiny shorts. She continued to stare into my eyes as she pulled her shorts down and let them fall to her feet. Hiding underneath her khaki shorts was a small cotton thong. She stood there for a second, with her t-shirt and panties still on. My eyes explored her groin and I noticed that something seemed strange. It almost looked like there was a large bulge in her panties where her pussy would be. I'd never seen a half naked girl in person before so I decided not to say anything. Continuing to stare into my eyes, she reached down to her black thong and slowly started pulling it down. But as she finally got it down to her feet, I realized what the bulge actually was. Where a pussy would normally be, Kelly had a cock.

The second her cock popped out of her panties I saw tears starting to well up in her eyes. Her lip began to quiver and just as quickly as she had undressed, she pulled her panties back up, covering up what she had hidden from me for a year. It was now obvious why she wouldn't let me do anything to her, she was hiding a big secret.

"You think I'm disgusting," she cried as she pulled herself up into the bed and sat next to me.

I was still in complete shock but knew if I didn't manage to comfort her now, I could scar her for life, something I had no intention of doing. "No, not at all. Didn't I just finish telling you that I loved you no matter what?" I asked.

"This is different," she cried. "No guy could love a girl like me, shit, you cant even call me a girl!"

"Kelly, you're the most beautiful GIRL I've ever laid eyes on, and I'll love you no matter what, but you probably should have told me about this."

"I know, I know, but I was so scared that you'd break up with me. Who would want to go out with someone like me?"

"Kelly, there's more to someone than what they have between their legs. All those great times we've shared over the past year aren't changed by this."

I grabbed her and held her in my arms. I rubbed her back and ran my fingers through her hair as she finally started to calm down.

"I've wanted to tell you for a long time," she told me. "I was born like this, and I'm going to get surgery one day, but the doctors said I've got to wait till I'm fully developed before they'll do the surgery. So until then, I'm stuck like this, like a freak."

"Stop it, you're not a freak. I still think you're beautiful, this changes nothing."

For the first time since the breakdown I saw a smile on her face. We continued to talk for a few minutes. She told me about how hard it had been growing up the way she was. She told me how hard she had to work to keep it a secret from everyone. Even her best friends didn't know. I was the only person other than her parents that knew. It actually meant a lot to me that she trusted me more than friends she'd known for over 10 years.

"So I understand if you never want to have sex with me," she finally said.

"I never said that," I told her. I was still in shock about what she had revealed to me but I did still love her, and I figured we'd find a way to make things work. "If you still want to do it, I'm down."

The biggest smile I'd ever seen crept across her face and she instantly started kissing me as she jumped up into my lap. She was now straddling me as we began kissing more passionately than we ever had before. I know knew why she'd been so protective about me getting anywhere near her groin; as we kissed I felt her cock poking into my stomach. After a minute or so of kissing she once again got off the bed and began to undress in front of me.

"I guess we'll try this again," she said with a grin. Her cock was clearly hard now from the kissing session we just had and was begging to be released from her constricting panties. As she pulled her panties down her cock popped out and I gave it a long look for the first time. It actually looked a lot like my own cock. It was cut, and looked to be about 7 inches long, the same size as my own. I however, was a 5'10 male. A 7 inch cocked looked a lot bigger on a 5'3 female with such a small frame. I still wasn't sure how it made me feel to see a cock where Kelly should have had a pussy. I wasn't mad at her or anything like that, but I was still a bit confused about how to react to it. I didn't know what she wanted me to do. Should I touch it? Should I even look at it? I had no idea what I was doing but like always, Kelly made the first move.

She hopped back up into the bed and started sucking on my flaccid cock again. At this point I'd forgotten about my problems earlier but after about a minute or so it was evident that they hadn't gone away. No matter how long she sucked, my cock just wouldn't budge.

"It's O.K., you can stop," I told her after a couple of minutes, "it just isn't going to happen."

"So you think I'm disgusting and you cant get it up, great," she said with a tone that made it seem that she would start crying again any moment.

"No,no, no, I promise that's not it, in case you didn't notice, I couldn't get it up before you undressed earlier, remember?"

"Yea..... I noticed......"

"This had nothing to do with you," I told her, "I was nervous all day, it was all me."

I could see the relief come across her face. "So, what do you want to do?"

"What do you mean?" I asked.

"Well, I'm hard," she noted with a sly grin on her face. I looked down to her groin and she was right, he cock was rock hard.

"What did you have in mind?"

"Well, I could try doing you." I'd never even thought that was a possibility until she mentioned it. I'd never had anything shoved up my ass before. I figured that one day I might want to fuck a girl anally, I'd seen it a million times before in porn. But I'd certainly never thought the tables would be turned on me.

She noticed that I was thinking hard about it. "You don't have to if you don't want to," she quickly added.

"No, that's not it," I told her, "I just haven't ever thought about it before." She continued to stare at me, waiting for me answer.

I thought about it for a few more seconds then said, "Sure, why not? Let's try it."

"O.K." was all she said. Although I could tell by the giant grin on her face that she was excited. She leaned towards me and started kissing me again.

"So, what do you want me to do?" I asked her, waiting for instructions.

"Um, roll over, I guess," she told me. She seemed just as clueless as I did. I forgot for a second that she'd never done anything like this before either. In fact no one, aside from herself, had even touched her dick before. This would be the first sexual encounter ever for her.

I followed her instructions and rolled over so that I was now in doggy style. I then waited for her to make a move. Just after I onto my knees she hopped off the bed and headed for her dresser. I watched as she opened the top drawer and started rummaging around. She pulled out a pack of Trojan's and showed them to me.

"Do you want me to wear one of these?" She asked.

"Well I don't think I can get pregnant, do you?"

She laughed, "So I guess that's a no?"

"Yea, I don't see the point."

She tossed them back into the dresser and pulled out some KY. As she walked back towards me I saw her cock bounce up and down with each step she took. She still had her t-shirt on and it and it came down just under her belly button, leaving her cock completely exposed. It wasn't until she reached the bed and positioned herself behind me that I realized how big her cock was. Like I said before, I'd never had anything shoved in my ass, but I had a pretty good feeling that it was going to hurt like hell when she put that thing inside me.

"So you're sure you want to do this," she asked one last time as her cock sat only inches from my quivering hole.

"I'm sure," I told her.

"I love you," she said.

"I love you too," I replied.

Some shitty movie was still playing in the background and she began to cover her bare cock in lube. I tried to listen to the dialogue in the movie, trying to distract myself from the impending pain. It didn't work well. I heard her place the cap back onto the bottle and I soon felt the tip of her cock press up against my hole. I was starting to think that maybe she should have started smaller, like with fingers or something, before jumping up to her big dick. But at this point there was no going back. I figured I just might as well go ahead with it, "how bad could it be?" I asked myself.

When her cock began pressing up against my hole I thought it would be too big to fit. It felt like the head of her cock was covering every inch of my asshole, and then some. She started to push her groin forward and I felt the pressure against my hole beginning to increase. But so far, nothing was happening.

"Try to relax," she instructed. Easy for her to say, I thought to myself. She wasn't about to have 7 inches of meat shoved into her ass for the first time. Once again she pressed her cock against my hole and began to apply pressure. I tried my best to listen to what she said and did my best to relax all the muscle in my body. It worked. Without any warning her cock finally broke past my sphincter and 3 inches of her cock plunged into my virgin ass. I instantly let out a loud grunt as every muscle in my body tightened. It felt like someone had just exploded a grenade in my ass.

Kelly noticed the pain I was in, "Are you O.K.? Do you want me to take it out?" she quickly asked.

"No, no.... just give me a second." I told her. I had no idea what it was supposed to feel like to be fucked in the ass. I figured it would hurt but I didn't think it would be as bad as it was. We sat there motionless, me on my knees with Kelly's cock buried in my ass for a minute or so. But just as I was about to give up and tell her to stop, the pain began to subside. My fists began to unclench and my muscles finally started to relax. "O.K.," I said as the pain finally began to pass, "I think I'm fine now."

With that she slowly started to push he groin forward. I could feel my insides stretch as this new intruder made its way deeper and deeper inside me. For the first time I felt a strange mix of pain and pleasure as she continued to push inch after inch inside me. Just as I felt like I couldn't possibly take any more of her meat inside me, I felt her balls push up against my ass. I finally had all 7 inches of her dick inside me. With her entire length inside me she leaned forward and started kissing my back and shoulders as she allowed me to become accustomed to her cock. After about a minute passed she straightened back up and started to pull her cock out of my ass. Just as her head was about to pop out she plunged her entire length back into me. I let out a loud moan as she did this.

"How does it feel?" She asked.

"Fucking great," I replied.

She let out a soft giggle but I heard it. And I wasn't lying, it did feel incredible. But it was a different kind of feeling. It wasn't comparable at all to anything I'd ever felt before. There was still some light pain but I almost enjoyed it. It was a good kind of pain. I also think there was something about being dominated that I enjoyed. It was nice to just sit there and let Kelly do all the work. She continued to slowly stroke her cock in and out of my ass. Each time she plunged her dick back into my hole I let out a load moan.

After about a minute or so of slowly pumping me she began to increase her speed. Even though this was her first time ever, I thought to myself that she was doing a damn good job. But just as I said this to myself her moaning began to increase. I could feel her grip tightening around my waist and her breathing quickened with each stroke. Her once fluid pumping had now become erratic as her cock just seemed to be vibrating around inside my ass now. And just as I thought she couldn't moan any louder, she pulled her cock from my ass with one hand and erupted all over my ass and back. I didn't really know what to do so I just sat there and let her finish. Her breathing was heavy as she continued to stroke her big dick until the last of her juices had emptied onto my ass. I looked over my shoulder and we made eye contact. She smiled and I smiled right back.

"Sorry about the mess," she said after she had finally stopped cumming.

I laughed, "don't worry about it, I've given you some pretty massive loads as well." Although I'd certainly never had one this big. Almost my entire ass, and a good amount of my lower back was covered in her sticky cum.

"Wait here," she told me. She hopped out of bed and ran across the room. She returned with a towel and began to clean me up a bit. I started to get aroused again as she ran the towel up and down the crack of my ass. But once she had cleaned me up I rolled over onto my back and she laid down next to me in bed.

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