Party Girls

It's been a while since I posted anything. But this is a story that I've been thinking out for a couple years. Bear with me, as I thought I would fill in the back-story through a series of flash backs. I hope it works, and isn't too confusing...

"Tell me about your first time," she asked.

Julia and I had just finished making love for the first time as a couple. And it was amazing. My whole entire body was tingling. She took my breath away. She had long, wavy brown hair that ended just past her shoulders. Her soft brown eyes were almond shaped, but had a way of seeing right into my soul. She was taller than the average girl at five-ten, but she carried herself with grace and confidence. She was slim and fit. Her breasts weren't big, but she was proud of the fact that they were all natural. Her trim waist gave way to the gentle, sexy swell of her hips. She had an amazing ass atop of long, smooth legs. She was the complete package.

We lay side by side, still naked, our bodies still cooling from our coupling. My cock was just about limp, though when fully erect reached a modest 7 inches. Julia's cock was also limp. Yes, you read that correctly. Julia has a penis. She was born male, but had started transitioning right after she graduated from high school. After four years, her body was beautifully feminine. Except for the obvious. Her cock was also average size, at around 6 inches erect, but looked quite sexy on her smooth, feminine body.

I had moved into my apartment about six months ago. Julia and her two roommates lived in the apartment next door. We shared a landing, and our balconies were separated by only a three-foot high block wall, so we ended up hanging out a lot. Her roommates, Mona and Crystal, were also transsexuals. But all three carried themselves with confidence, and you really couldn't tell unless you spent some time with them. And once you got to know them, you couldn't help but to enjoy their company and their care-free lifestyle.

I too had some quirks, which is probably why we all hit it off so well. I have been what you would call bi-curious for most of my life. Even in high school I was drawn to both guys and girls. But that wasn't something you said anything about when I was growing up. After I graduated high school I started exploring the possibility. I had lost my virginity with a girl in what can only be described as an awkward evening that I think both of us have tried to forget. I also had one encounter with a guy, which I'll tell you about in a moment.

In college I lived by myself in an apartment, so I was able to explore my feminine side. At first it was panties and bras. Then I started experimenting with dresses skirts. I wasn't a full-time crossdresser. But I did enjoy wearing women's clothes when I was alone.

On one of these occasions I had gotten so comfortable that I carelessly went out on the balcony to chat with the girls, still wearing a loose summer dress, bra straps and panty lines on dispay. They seemed a little shocked, and I was a little embarrassed. But it opened up a great conversation that led to a wonderful friendship. Julia and I seemed to hit it off. We spent a few weeks flirting and teasing each other, until one evening I finally found the courage to kiss her.

Which brings us, briefly, back to the present moment. "Tell me about your first time." She was obviously asking about my first time with a guy. It's an awkward story as well, but it would be the experience that would set me on my present course in life. So I told her my story.

I was a sophomore in college. Every year there was always a big party for new-years. Everyone would dress up like it was Halloween. Then usually get drunk and make fools of themselves. But it was fun. Since I had been experimenting with femininity I thought it would be a great opportunity to try dressing in public. Everyone else would be dressed up in some way, so me going in drag wouldn't raise any questions.

I went out shopping the week before to find just the right outfit. I'm pretty slim, but I don't exactly have a feminine figure. I needed an outfit that worked without making me look like a gorilla in a skirt. I eventually settled on a pink and black pleated skirt that went just past my knees, and a white short-sleeved blouse that buttoned up the front. I also picked out some new panties and a matching bra, along with a garter and stockings.

I started prepping for the evening early in the day by taking a long bath, during which I shaved my body completely from the neck down. You have no idea how long that actually takes until you try it. I had to re-fill the tub twice after the water went cold. And once I was done, I finished with a full shower, complete with some strawberry scented body wash.

My whole body tingled as I dried off. It felt absolutely amazing. And I struggled to work around my erection as I got dressed. After rubbing in a coat of lotion, the same scent as the body wash, I slipped on the sexy white nylon thong. Feeling it slide up my smooth legs and nestle between my ass cheeks sent little electric shocks trough my body. Then I slipped into the matching demi-bra, tucking a pair of c-cup breast forms into each cup.

With my bra and panties on I went about painting my nails. I had done it a few times before and was actually getting pretty good at it. And I had been letting my fingernails grow for about a month and a half so they looked pretty natural on their own. I had also been practicing with make-up, following a couple of videos I had found on the internet. I could actually do it without looking like a clown or a cheap whore.

Next came the garter, followed by the nylon stockings. They felt incredible as I slipped them up my legs and attached them to the garter straps. And then finally came the skirt and blouse. Everything fit exactly the way I had hoped. I felt amazing, and so feminine. Looking at myself in the mirror I was quite pleased with the results. The blouse strained a bit with the c-cup breast forms in place. I hadn't factored them in when buying the blouse. But it still worked. And if I unbuttoned the top two buttons, it opened up just enough as to invite a second look, but not so much that you could tell I was wearing falsies.

I felt so good standing there looking at myself that I began to question my own identity. But the party started in just over an hour and I still needed to do my hair. I had let it grow out so that it almost reached my shoulders. And I usually asked for a 'uni-sex' cut whenever I got it cut. The style I chose was fairly easy to do based on the video I was watching. I finished with a few minutes to spare. I touched up my make-up one last time, and made sure I had some basic essentials in a small purse I had picked up. Then I spritzed on some body spray and stepped into the basic black, 2-inch heels I had purchased a few months back. And finally I was ready to go.

I was very self-conscious as I walked out to my car, but nobody was around that I could see. Once I got to campus, however, it was a different story. Because it was a popular party, there were people all over. Most everyone was in costume, so using that to build my own courage I stepped out of the car and started to walk across the quad to the student union where the party was being held.

I had worn a skirt/dress around my apartment on several occasions. But walking outside, in public, feeling the night air flow between my legs, and feeling the weight of my breast forms, I was in another world entirely. I was very nervous, but I was determined to go through with it.

The party was a lot of fun. Several people expressed genuine surprise when I told them I was really a guy dressed as a girl. It felt good to know that I really could pass if I wanted to. Many complimented me, and a couple of guys even playfully squeezed my ass. But after an hour or so, as usually happens, people started to gravitate into their own little groups. I found myself hanging with a group of four guys and two girls that I knew from classes, but not well. I played the part and flirted a bit, and really was starting to enjoy spending the evening as a girl.

Eventually we all decided to head to a house where two of the guys lived. We were all drinking and everyone was more than a bit tipsy. One of the guys, I don't even remember his name, started to flirt pretty hard with me. Felling comfortable in my feminine persona, and having lost some of my inhibitions to the alcohol, I allowed him to, and went with it. And when he tried to kiss me at midnight, I played along, kissing him right back.

We eventually found ourselves alone in one of the bedrooms. He was kissing my neck and letting his hands roam all over my body. The attention felt good, and even though there was a voice in my head that was trying to remind me that I was a guy fooling around with a guy, another part of me wanted to see how it went.

I felt his hand go between my legs. He felt my cock and balls, which surprisingly stayed limp, and he simply grunted. Then he turned me around and bent me over the bed. He held me down with his weight, but I was so shocked by what was happening that I couldn't move anyway. I felt my skirt lift up, and then my panties were pulled down. I heard what sounded like a condom wrapper being torn open. Then I felt a cold, wet pressure on my back door.

It took him a few tries to press himself inside of me, as his cock wasn't all the way hard. But finally with a grunt I felt him slide in. The whole experience was so surreal. It was like it wasn't really me getting fucked like a slut. But after a couple of minutes I found that it was starting to feel pretty good. I'd hate to be his girlfriend, however, as it was over pretty quickly. He grunted a couple of times, them pulled out and passed out on the bed. I was left with my panties down to my knees, my skirt pushed up to my waist, my ass feeling empty and used, and with a feeling of dissatisfaction.

I cleaned myself up as best as I could, then left to find my car. It took about five minutes for me to walk back to my car, and the whole time my mind was buzzing over what just happened. When I got back to my apartment, I pulled down my panties and stroked myself until I exploded with the largest orgasm I had ever had. Then I passed out on the bed, still dressed as a girl.

"That was almost two years ago, now," I added, as I wrapped up my story. "I haven't been with anyone else since then...until now."

"So what you're saying is that this was the first time you actually made love to anybody?" She asked, the pleasure obvious in her voice.

"Pretty much." I replied. "I've never really felt comfortable with anyone until now. Asking out a girl, when I wear women's clothes half the time, felt weird. And I can't say I have ever felt a strong attraction to a guy. You're the first person I've ever really wanted to be with."

I could see her eyes were a bit watery. "That's so sweet," she said quietly. "I got to be your first time, and your first love."

I hadn't thought if it that way, but she was right. "Pretty much," was all I could say. It had been an amazing evening already. But that I did love her made the evening that much more special.

The night has been nothing short of a dream date. We had gone out a few times as a couple and had gotten to feel very comfortable with each other. I had never thought of her as a transsexual. She had always been a girl to me. And the fact that she had a penis didn't bother me a bit. If fact, it made things that much better in my opinion.

We had gone to dinner earlier in the evening, then returned to my apartment where we spent a good hour on the couch, kissing and cuddling, and teasing each other in a suggestive way. And then she made the first move.

Julia got up from the couch and knelt in front of me. I was wearing a pair of cargo shorts and a t-shirt. She unbuttoned my shorts and slipped them off of me. Underneath I was wearing a pair of light blue hi-cut bikini panties. She began stroking my cock through the microfiber material. It didn't take more than a few seconds before my member was straining against my panties. She toyed with me for another minute or so, then pulled the front of my panties down to free my cock.

After teasing the head of my cock for a few seconds she reached around me to pull my panties off. I helped by raising my hips to allow her access. She then began to tenderly kiss and lick the tip. The feeling of her lips and tongue on my flesh was hypnotic. I was almost in a trance as she worked my shaft with tender loving care. She began to take more and more of me into her mouth. Then she would back off to just the tip while she stroked my shaft, using her saliva as a lubricant.

She continued stroking with her hand, but moved her lips down until she could take my balls in her mouth. She lovingly sucked each one like a succulent morsel before moving back up to take me into her mouth again.

It was honestly the first blow job I had ever received. But it as more amazing that I had ever thought it could be. Somehow she could sense when I was nearing climax because she would back off every few minutes, making it last as long as she could. But finally I hit the point of no return.

"Oh, shit, baby. I'm cumming," I warned her. She looked up at me and held my gaze as I started shooting my cum into her mouth. She held my cock between her lips until the last bit of semen had been pumped out. Then lifting her head, she showed me her mouth full of my cum. I don't know where the thought came from, but I knew I had to kiss her. And before she could swallow, I locked my lips onto hers, tasting my own cum as our tongues danced together. Finally we broke the kiss, and both swallowed half of my cum.

I had never tasted cum before. It was a bit on the bitter side. But not bad at all. And I knew I had to have more. Only this time it would be her cum.

I managed to get myself off of the couch and onto my knees. She was still kneeling in front of me. I reached around and unzipped the short zipper in the back of her dress. And in one quick motion she lifted it up over her head. She was wearing a lacy red thong and a matching bra underneath. The red lingerie looked amazing against her pale skin. I almost hated to take it off. But I had to see her body. Had to feel her, had to taste her.

She kissed my neck as I reached around her to unfasten her bra. With the clasp undone she easily shook loose of the straps, tossing the garment to the side. Her breasts were soft and round. I knew that, even though she was not a natural woman, her breasts were not implants. The had grown 'naturally' through the use of hormones. And even though they were not huge, they were absolutely beautiful to behold.

She leaned back against the couch as I took one of her nipples into my mouth. It was instantly hard, and I sucked at it like a hungry child. She moaned in pleasure, her nipples being one of her more prominent erogenous areas of her body. I moved to her other nipple, cupping both breasts in my hands.

She stretched her legs out in front of her as I began to move my kisses lower down her chest and belly, licking her navel and toying at her belly-button piercing with my tongue. When I reached the top of her panties, I hooked my fingers under the waist band and slid them down her smooth legs. Her cock sprang out immediately to it's full 6-inch length and begged for attention. I had never sucked a cock before. I had never even touched one other than my own. But as I wrapped my fingers around her throbbing shaft it felt completely natural.

I began just as she had, kissing and licking the tip, tasting her pre-cum. Then, again doing as she had done, I began to take her deeper into my mouth, working up and down her shaft with my lips and hand. I took her smooth balls into my mouth and sucked each one while stroking her. Then I took her shaft back into my mouth.

It took me a few minutes to get a rhythm going. I had to figure out what to do, or not do, with my teeth, how to use my tongue, how hard or soft to suck, how much or how little to take in, and so on. But based on her moaning I was getting the hang of it. And the payoff came soon after. She ran her fingers through my hair and then said, "Baby, I'm gonna come. Are you ready?"

We locked eyes, and all I could do was keep going. Then I felt her shaft pulse, and globs of her cum coating the inside of my mouth and throat. "Don't swallow yet," she warned. "You have to share like I did with yours." I was happy to oblige, and as soon as I felt her orgasm was over, I kissed her, sharing her load of cum as she had shared mine.

It was an amazing beginning to the evening. We moved from there to my bedroom. Both completely naked at that point we held each other and kissed. No body part was ignored. Whether we were caressing or kissing, we explored each other's bodies, getting to know each other in the most intimate way.

After a while we found ourselves laying on our sides, facing each other. We were close enough that our cocks were touching, and it was very erotic to feel them slowly get hard at the same time. We did some light dry humping, grinding our cocks together as we kissed. Then she pulled back, looked into my eyes, and asked, "Do want to keep going? Or should we stop for the night? I know this is new to you."

I was touched that she showed such loving concern. But I wanted her. "Why stop. This feels amazing. I want you so badly I can hardly breathe."

She nodded, then got up from the bed and went into the other room. I was puzzled as to what she was doing, but loved watching her perfect ass as she walked away. She returned a few seconds later with her purse. Opening it, she took out a box of condoms. She offered one to me, but I declined. "No, baby. I want you to go first," I said. "I want to feel you inside me." Honestly, I wanted her example to follow, as I really was new to this.

She nodded. Removing the condom from the wrapper she rolled it onto her now rigid member. "We'll use these until you're used to it. It's safer that way," she explained. "We won't have to use them all the time if you don't want to."

At this point I wasn't sure what to expect or to do. But she could obviously sense my uncertainty. "Why don't you lay back on your back," she directed. "We'll go slow. Tell me if I'm going too fast, or if it hurts."

"Okay," was all I could respond, and I did as she directed. She took one of my pillows and placed it under my ass, just below the small of my back. Then she took some lube from her purse and squirted some onto her fingers. She gently worked it into my hole, massaging lightly before slipping a finger inside me. In and out a few times, then she applied a little more lube.

"How does that feel?" she asked.

"So far it feels pretty good." It sounded lame as I said it. But she nodded and continued, this time with two fingers. I could tell she was trying to loosen my up for what was to come, which was far more considerate than what's-his-name was when he took my anal virginity.

Finally I saw her apply some lube to her cock, then stroke herself a bit. And then I felt the tip of her cock pressing into my hole. She was still kneeling between my legs, her knees on either side of my ass. She pressed gently for a minute or so until she started to slide more easily inside me. Once past that initial point of entry she leaned forward so that she was now over me.

We held each other's gaze as she continued to press farther inside me. Then she would pull back and start pressing in again. Eventually she started to fuck me slowly and steadily. Her breasts swayed as she rocked back and forth. I was mesmerized by them. But my concentration was mainly on the sensation I was feeling below. It had hurt at first, but that pain was gone now. The feeling of her sliding in and out of my boy-pussy was unlike anything I had ever felt before.