If anyone had told the way I’d meet my soul mate a few years ago, I never would have believed it. It was my senior year of high school and I had recently gotten out of yet another bad relationship with a girl. Lina had been a pretty, chubby blonde with a nice personality but a nasty temper. We just didn’t click after a while and I was feeling down on myself for not being able to hold onto a girl for very long. My friend Dan took me to a friend’s house where there was a party going on and I went along mostly to distract myself from my thoughts. The place was a dump and most of the people there were boring but there were a few interesting ones and we ended up chilling together in a quiet back room and just smoking cigarettes and talking. The most interesting people in the group were a couple of chicks that seemed to be close friends named Leslie and Sara. Dan and Sara knew each other and had even hooked up before. She was a bubbly, talkative girl with a voluptuous figure and wild curly red hair. She usually wore all black, gothy clothes, tall black leather boots and strange librarian glasses that would have looked terrible on anyone else but were sexy on her. She introduced me to her friend and it was clear to everyone present that a spark passed between us from the first.
Leslie was a tall, slender brunette, the very opposite of what my ex-girlfriend had been. She had a husky, quiet voice, big light brown eyes and a gorgeous smile. She dressed in a carefree hippy-gypsy style that suited her perfectly with a long flowing skirt and peasant blouse. She had a soft, pretty face and long straight brown hair that reached just past her shoulders. Everything about her was exquisitely feminine right down to the swing of her hips when she walked. At the end of the night the four of us ended up hanging out on the edge of the woods behind the party house and Leslie and I wandered off by ourselves. We were really taken with each other and she finally made the first move and asked me if I had a girlfriend. So I told her I didn’t and asked if she had a boyfriend.
She blushed and said “I know it sounds weird at my age but I’ve only ever had one relationship. We broke up last year and I’m really kind of inexperienced and innocent about guys and sex”.
I told her it surprised me because she was so beautiful. She smiled and kind of giggled but didn’t say anything. We started into each others eyes in the light of the full moon and leaned in slowly till our lips touched. I had never felt that way with any other girl and as our tongues intertwined, I knew she was special and she had to be mine.
Over the next few weeks we went on a few dates that went alright but she only really opened up when we were just hanging out at my house or hers. So we started doing that more often. I never met any of her friends except Sara and she rarely mentioned her school. Things moved very slowly sexually, but I didn’t mind because I knew she was a virgin. Her mom was really nice and looked like a very hot older version of her. But for some reason she didn’t ever leave us alone where we could be behind closed doors. So we would wander through the woods behind her house or hang out at my place (where my parents were seldom home) instead. I found we could talk about just about anything and when we were together the world was just right. One time she came over with Sara and we were hanging out in my basement when Sara steered the conversation to the subject of sex.
“Leslie is a VERY sexual person,” she assured me, “She’s just shy about it. But I think you’re the perfect guy to help her express it and let it all out. You guys are really good together.”
As she said this, Sara had come close and put one hand on each of our heads. She then proceeded to push our lips together and encourage us to kiss. She looked at us over those ridiculous glasses that somehow looked good only on her and seemed to get really excited while watching us. But watch was all she did. Leslie and I soon forgot she was there. As I ran my hands through her silky long hair and explored her mouth with mine, she started breathing harder and running her hands all over my chest, stomach and back under my shirt. I tentatively tried the same with her and this time, unlike previous attempts, she let me. Her skin was perfectly smooth and I was surprised to find she wasn’t wearing a bra. I gently stroked her back and she moaned and pressed herself to me. I brought my hands around and caressed her very small, firm breasts and hard nipples. We slipped each other’s shirts off with unspoken perfect timing and the feel of her skin on mine was simply heavenly. I gently lowered her to the floor and admired her half-naked body. Her breasts nearly disappeared when she lay down except for the erect nipples and she arched her back with desire as I took each of them into my mouth. I then kissed her neck as I slipped my hands beneath the knee length skirt she was wearing and ran my fingertips up and down her long, shapely legs. She nervously unbuttoned my jeans and slipped one hand under them to grip and stroke my cock.
She had a strong grip and surprised me with her perfect technique considering she was a virgin. That was then I realized that Sara had hiked up her skirt and was slowly fingering herself with one hand while rubbing her breasts with the other and intently watching us. I was too far along to say anything and she was quite hot herself so I just watched her and slid my hands farther up Leslie’s thighs until I felt her lace panties. She suddenly became nervous and alarmed and tried to stop my hands from moving further. I tried to ask her why but she stopped me instantly by taking my hard cock in her mouth. I gasped in pleasure and pumped my hips into her warm mouth. She sucked and stroked like everything depended on it and moaned like she being fucked. I moaned and bucked my hips into her face while Sara fiercely rubbed her clit watching us. Leslie had one hand under her skirt too and we all came at the same time. My knees went weak and I sank to the floor. Leslie pressed her naked breasts to my chest and kissed me passionately, giving me an unexpected taste of my own come.
“I love you,” I said before I could even think about it.
She jumped a little and her eyes erupted in sudden tears. “I love you too. She said. I love you completely.” She then gathered up her clothes and suddenly ran out of the house crying.
“Wait!” I yelled after her, “Where are you going?” But she was already driving away.
Sara held me back from following. “Don’t,” she said “She just needs some time alone. She’s never felt like this about anyone you know. And she’s really crazy about you. She has some pretty deep secrets and has never opened up to a guy all the way before. Thanks so much for being so sweet to her!”
She then hugged me, her heavy, round tits, still naked, pressed against my bare chest. She then grabbed my cock, now half hard again, and kissed me fiercely, full on the mouth.
“And thanks for the show! That was the hottest thing I’ve ever seen and a fantasy come true.” I was speechless and bewildered as she covered up, got her purse and started to walk out. “And don’t worry;” she said, “Now I know that Leslie will definitely tell you everything soon. Just don’t rush her”.
For the nest week or so, we hardly spoke and I was starting to fear that Leslie was going to leave me. Maybe I’d pushed her too quickly? I was miserable until she finally started seeing me in person again. But she still seemed to have some dark secret that she was afraid to tell me. I asked but she just said she wasn’t ready yet. We kissed and cuddled but she seemed unready for any other intimacy. Then one day she seemed back to her normal self and suggested we go for a walk in the woods behind her house. We walked down the familiar paths to a remote lake where no one ever goes. We had been there twice before to watch the sunset and had made out there in an old empty boathouse. It was a peaceful, pretty place and I could tell she felt at ease there.
“I’ve never felt like this about anyone before,” she told me.
“Neither have I”, I replied, “You really are the perfect girl for me, and I love you.”
“I love you too”, she said, “And that’s why I can’t hide the truth from you anymore. But I’m afraid, Chris. Afraid you won’t love me anymore when I tell you.”
She was exactly the same height as me and we could look each other in the eye perfectly when standing face to face.
“I promise you, Leslie, there is nothing in this world that could make me stop loving you.” I kissed her tenderly and held her for a moment.
“Ok, I think I’m ready”, she said and pulled away with a playful smile. “Today you are going to see what no other guy has ever seen, all of me. And if you still want me, I’ll give myself to you completely.
“Yes, my love, I will let you take my virginity. But first, let me see you.”
I calmly undressed and stood in front of her completely naked and unguarded. It was a strange feeling, being on display like that. I was only 18 and had never undressed for a girl just to look at before. I thought I’d be self-conscious, but with her I wasn’t. And as I thought about our last encounter, all 6 inches of my uncut cock rose to full attention.
She was dressed very differently from her normal style that day. She wore sandals with straps and very short jean shorts that showed her long, beautiful legs and perfect ass. Above it, she had a strapless top that exposed her midriff. She slowly slipped out of the top and showed me her perfect, tiny breasts again. I had learned that she was a 36 A though she rarely wore a bra. Her nipples were already hard as she gave me a look full of lust and stood on display for me. Her body gently curved to a small waist and hips that were not too wide but still full and womanly. Her skin was perfect without the slightest flaw. She slowly turned and unbuttoned her shorts, which she then slipped off to show me the most perfectly shaped ass I had ever seen on any girl. She was wearing a light blue thong that left nothing to the imagination.
“Do you want this, lover?” she asked as she bent over and tempted me with her ass. All I could do was nod as I started massaging my throbbing cock.
Leslie then walked seductively towards an old chair; her long chestnut colored hair shimmering in the light, and then sat down across from me to take off her sandals. I could hardly stand the longing for her when she finally slipped off the thong and sat with her legs together, her bush shaved only to the bikini line. And that was when I got the surprise of my life. She stood up and showed herself to me, naked and unguarded.
Beneath her bush, where I expected to see a pussy, was an erect cock and balls.
I was shocked but not in the way I would have thought. Her penis was small, probably 5 inches at most, uncut, and much thinner than mine. Somehow it looked right on her slender form and she was still the most gorgeous creature I’d ever seen. Despite my lifelong prejudices, my cock remained rock hard.
“So now you know the truth. I’m not really a girl. I’m a boy and I still have to live as one sometimes. No one at my school knows about this except Sara.”
“But didn’t you say you were in a relationship before?” I asked
“Yes,” she said, “With Sara. She was my girlfriend until she encouraged me to try to find a guy. She knows the truth and that’s why it turned her on so much to watch us. She has a whole collection of gay and transsexual porn. She loves it. So, do you still want me even though I’m a guy?” she asked.
“Leslie, you are the most beautiful thing I have ever seen and in my eyes you’re just a different type of girl that I’ve never had before. Of course I still want you.”
I pulled her towards me and kissing her full on the mouth while our cocks rubbed together. It was a completely new sensation for me and I found that it really turned me on as my hands caressed her ass. We kissed and groped while our dicks dripped with pre-cum and our desire grew. We went to the mattress we had dragged in there on a previous visit and she started sucking me again. I maneuvered myself into a position where I could reciprocate. Her skin smelled like strawberry body spray as I licked her scrotum and shaft and made her moan. I slowly took her cock in my mouth and licked the head as I pulled back the foreskin. We fucked each other’s mouths slowly and my fingers started to caress her opening. The pleasure built until I made her stop for fear of coming too soon. Instead, she got a tube of lube out of her bag and applied it to both my cock and her ass. She then got on her hands and knees in front of me. Her hot, heart-shaped ass was open before me and made my cock throb in anticipation.
“Please be gentle”, she said as she looked at me with longing over her shoulder. I slowly worked first one finger, then two into her tight little ass. She moaned and touched herself while rocking back and forth on my fingers. I then took my naked cock and pressed it gently to her opening. I then told her to push back on my dick and I slowly penetrated her. She gasped in pain and pleasure as I slowly pushed my shaft all the way in. The feeling was amazing. It was tighter than any pussy I’d ever had. I had tried anal sex with girls before and always liked it but this was another level. As I slowly fucked her I was in ecstasy. As I pushed all the way in, my balls touched hers and I nearly came too soon from the sensation. I reached around to caress her dick and move the foreskin back and forth. My thrusts increased in strength and speed. Before long she screamed in pleasure and her cock shot come all over my hand. As she came, her ass squeezed my dick many times in quick succession and she bucked her hips just like a real girl. I couldn’t hold back anymore and I came, filling her ass with my juices.
I withdrew from her ass and held her as we kissed and caressed each other. I explained to her that one of my problems with past girlfriends was that, while I enjoyed fingering and licking pussy, I never particularly enjoyed penetrating a girl’s pussy anywhere near as much as I enjoyed ass. One of the reasons Lina had left me was that I wanted anal every time and she didn’t enjoy it as much. Now I had found the perfect girl for me. One who had the same tastes and enjoyed it when I made love to her in the way I most enjoyed. Every time. And just as importantly, one with whom I’d found love. Our small towns would never understand, but we were 18 and would be out of high school in less than a month. We could go somewhere where no one knew or cared. She mentioned that Sara would want to join us and maybe even share our bed. I told her it was an adventure I looked forward to. I made her come three more times that day. And as we lay in each other’s arms, covered in each other’s come, we sat naked on the dock and watched the sunset and I knew that a completely new aspect of my sexuality had been pleasantly awakened.