Okay, so here's your typical "first story" disclaimer. Yes, this is the true story of how I met a girl named Tracy. Yes, it's been a long time, so I've probably played a little loose with the dialog. And while it's not the incredible "true story" of how I was a virgin until that fateful night when 37 college girls decided to have their way with me in a seven-hour orgy and they all found out that I was a heretofore untapped sex god, yes, this is actually what happened. (and yes, there's more to the story that might come later…)
I was a horny little teenager.
That probably doesn't set me apart from most of the guys writing on this site. What might, though, is the fact that I did very little about it until later in my high school "career." From the time I was 10 and figured out that thinking about the Pretty Blonde Girl in my class would somehow make my penis stand up straight, until I was 15, I hadn't so much as kissed a girl. I *wanted* to, of course. And once I figured out what to do with a hard-on once the effects of thinking about the Pretty Blonde Girl had set in, I became quite the expert at jerking off to fantasies about what I'd do with the PBG…if I could ever talk to her, that is.
But I wasn't the ladies' man I wanted to be. I was painfully shy and certain that, somehow, all the girls knew what a pervert I was for sneaking my dad's Playboys and jerking off almost daily to centerfold pictures of too-large breasts and airbrushed pubic hair. I had crushes on most of the girls in my class, in turns, once the PBG moved away. But I never had the guts to do anything about it. Except to take advantage of the empty house after school before Mom & Dad came home from work, to browse Mr. Hefner's amazing gift to the world. Oh, and jerk off like a madman.
Things started to change the summer I was 16. The day after my birthday in January, I'd gone down to take my driver's test, and with the driver's license came that discovery of freedom that so many people are familiar with. Suddenly I could go where I wanted, more or less when I wanted, and with whom. Friends started asking me to go with them here & there more often, (yes, I knew it was just because I could drive…but that didn't matter), and every now & then I'd even get some attention from girls.
One afternoon when we'd been out of school for a few weeks, I got a call from my best friend, Micah.
"Tom, it's Micah. What's up?"
"Not much," I told him, kind of bored. "What about you?"
"I'm going over to Sandra's house tonight to swim & hang out. She wanted to know if you want to come, too?"
Sandra was the girl Micah had been going out with for most of the past school year. She was a grade behind us in school, but physically she looked a fair bit older. She was taller than most girls in our school, but not quite basketball team material, with long blonde hair, blue eyes, and a figure that featured full, perky breasts and a nice small but round butt. Sandra had given in to Micah's pressuring without too much trouble, and they'd started having sex around Christmastime. Micah kept me informed about all the details of what they did; I think this was partly a best friend sharing information with his horny, still-virgin friend…and partly showing off.
"Sure," I said. "But are you sure you two wouldn't rather be alone?"
"Nah," Micah explained. "Her cousin, Tracy's there, and Sandra thought you two should meet."
I could hear a little bit of a grin in his voice. "What, is she some kind of dog?" I asked.
"Nah, Sandra says she's cute. She just thought you two might hit it off. So whaddaya think? Wanna come?"
"Ok, sure," I said.
"Great! So grab your suit. Can pick me up in about a half hour to go over?"
I told him I'd be over soon and hung up. I was nervous. I didn't really know what Sandra had in mind, or if her cousin was going to want to have anything to do with me. I went into the bathroom to get ready, took off my shirt and started doing some kind of pre-date preparation routine that I made up as I went. I stopped for a minute to look at myself in the mirror and wondered, what kind of girl would really want to have anything to do with me? I wasn't particularly tall, only about 5'10; not particularly muscled and kind of skinny, actually, from running laps in PE; a shaggy mat of curly brown hair that never wanted to be tamed; and green eyes that hid behind glasses. Thinking about the endless possibilities of all the sexual stuff I could end up doing with Sandra's cousin (yeah, right…get real), my cock started to stir in my boxers. I dropped my drawers for a minute and let my cock out. I was going to give it a quick jerk to relieve some tension before I went, but then I stopped and looked at it, too. Nothing impressive about it: not quite seven inches long, and actually kinda think compared to the others I'd seen in the showers after gym class, not narrow & spear-like, like the ones we saw in the porno Micah found in his dad's dresser that one time.
So, hoping for all the best but knowing what worst the night would probably bring, I stopped my impromptu routine and got dressed in a polo shirt and a pair of jeans shorts. Then I grabbed my swim trunks, my keys and my wallet, then headed out to pick up Micah.
Micah was pumped that night. He told me that Sandra's aunt & uncle were visiting for a couple weeks, and Sandra said they'd done nothing but talk about going out for dinner with her mom & dad since they'd got there. Tonight they were going into the city, a good two hour's drive away, for drinks, dinner, and dancing, leaving the two girls alone on a Saturday night.
"Man, I really hope you hit it off with Tracy, Tom," he said as we drove on. "I am so horny you wouldn't believe. Okay, maybe I'm complaining to the wrong guy about that, but Mr. Stiffy really needs some alone time with Sandra tonight, know what I mean?"
He didn't wait for me to answer, and I didn't really feel a need to jump in. This was kind of par for the course with Micah these days.
"I mean, Tom, I haven't even seen Sandra in almost a week. And we haven't fucked since the day school got out, ya know?"
I shifted in my seat a little, which apparently wasn't lost on Tom.
"Uh-oh…is all this talk giving you a stiffy too?" Don't worry. Buck up, little camper. Who knows, maybe Tracy will finally be the one…?" He kind of trailed off after that and looked over at me, almost like he expected me to answer for once.
I gave him a quick "yeah, right," and we drove on more or less in silence until I turned onto Sandra's street and pulled up in front of her house.
"Race you to the door," Micah said. "Last one there's a horny sonofabitch!" Almost before he'd finished saying it, he was out of the truck and bounding across the lawn to get to the front door.
I caught up with him right after he rang the doorbell, and he started making stupid kissy faces at me while we waited for the girls to let us in. I stood there nervously, not really sure what I had set myself up for, while Micah's moves became lewder and lewder. I almost busted up when he mocked playing with his breasts and dry-humping my leg, but then we heard the door start to open, and we both snapped to.
"Would you guys rather be alone?" Sandra asked as she opened the door. She was wearing a little blue crop top that stretched tight across her breasts and left a tantalizing gap underneath. Down below, she had on a pair of gym shorts that were about two sizes too small
"Fuck you, babe," Micah shot back as he went into the house and grabbed her.
"Only if you're nice," she said as she wrapped her arms around his neck and spread her legs, pulling him into a long, grinding kiss. "Come on in, Tom," she said, coming up for air.
I stepped into the entry way and squeezed around them. There was plenty of room, but I kicked Micah a little anyway, and they separated a little bit.
"Tracy," Sandra called, "Tom's here! Come on down."
I heard footsteps approaching from upstairs and then coming downstairs. Tracy rounded the landing and came into view. She was cute. She had straight blonde hair that hung down to just above her shoulders and was feathered back to frame her face. Her blue eyes were a hidden a little behind plastic-framed glasses that were just a little too big for her face. She had red lips that, even though she was smiling nervously, somehow managed still to be a little bit pouty. I couldn't tell how big her breasts might be because she wore an oversized t-shirt that she had tucked into a tight-fitting pair of jeans that showed off her skinny legs and a nice little butt.
We exchanged our greetings, and Sandra led us all into the living room. She put a movie into the VCR and climbed into her dad's overstuffed recliner with Micah. Tracy and I sat down on the sofa, close together but not quite on top of each other. We all chatted a little bit while the movie played, none of us really watching it too much. To my surprise, I found it really easy to talk with Tracy. She was pretty & cute, to be sure, but the more we talked, the more I saw that she was funny and sweet, and really seemed to be a nice girl. She admitted to not having been real excited about coming to visit Sandra's family, even though she didn't have a boyfriend at home to miss, until Sandra had told her about Micah's friend & how she thought we might really hit it off.
After a while Sandra stood up and peeled off her shirt, revealing a skimpy little bikini top that barely held in her breasts. "This movie sucks. You guys wanna go swim instead?" She nodded over to Tracy, who also stood up & took off her t-shirt. She was already in her suit, a white-with-blue polka-dots bikini that showed she had a nice set of smallish breasts.
"Sure," Micah said. "But Tom and I need to change."
"You guys can change in my room upstairs. You know the way, don't you?" she said, grinning. "We'll meet you out there." And with that, the girls ran outside.
Micah and I grabbed our towels & swim trunks where we'd dropped them in the entry hall, and he led the way upstairs to Sandra's room. "So," he said as we made our way up, "what do you think? She's cute, yeah?"
"Yeah," I answered, "she's cute. Thanks for making me come."
He turned on the light as I stepped in and closed the door, and we saw the evidence that two teenage girls had been sharing a single room for the past week. The bed was rumpled, and girl stuff was all over: hair brushes, blow driers, curling irons, and clothing of all sorts—including a variety of bras & panties—was strewn everywhere we looked. Micah picked up a bra from where it hung on the footboard of Sandra's bed and threw it to me. "Hey, man, here you go. What do you think of this? It's not Sandra's," he said, grinning. "Can't you just picture the two of them in here, changing together, all naked & stuff?"
"Dude! Cut it out," I said, still holding the bra. "How am I supposed to change into my trunks like this?"
"Dude!" he said, "don't worry about Mr. Stiffy. Just put on your suit & hold a towel in front of you until we get in the water. That's what I'm gonna do." Then he turned around, pulled off his shorts and pulled up his swim trunks. He adjusted himself as best he could, then picked up his towel and held it in front of his still-obvious hard-on, then looked at me with raised eyebrows as if to say, "See?"
I sighed and did the same. We looked like a couple of idiots standing there with towels held in front of our cocks, but we were horny and there were two girls out in the backyard, splashing around in the pool waiting for us, so downstairs we went. When we got outside, the girls were already in the water. They were splashing around but stopped when we came out, and swam over to the side of the pool together to meet us.
"Well," Sandra started, "are you gonna put down your towels & come in? The water's nice & warm."
When I hesitated a minute, Micah grabbed my towel and threw both of them aside. Then he peeled off his shirt and jumped over the girls' heads and into the water, making a huge splash. Sandra swam over to where he surfaced, and the two of them swam over to one of the built-in benches in the irregularly shaped pool, pawing at each other as they went. I just stood there at the side of the pool, not sure what to do. I just about died when I saw Tracy looking up at my hard-on pushing against my swim trunks.
After what seemed like an eternity but was probably only a minute or so, Tracy pulled herself up out of the water to stand next to me, dripping wet. I could see her nipples stiffen and strain against the fabric of her bikini top, and then she reached up on her tiptoes and whispered in my ear, "It's okay, I don't mind. Come on in." Then she jumped back into the water and swam off.
Figuring anything would be better than standing there with my dick on display, I took off my shirt, tossed it over by my towel, and jumped into the water. When I came up, I looked around to find Tracy. She was over on the other side of the pool sitting in a little alcove near the egress to the hot tub. I swam over to where she sat, and slid up onto the seat next to her.
"Are you okay?" she asked.
"Yeah, I guess," I mumbled.
"We don't have to swim if you don't want. We could go back inside"
"Nah," I said, "it's okay. You're— um, this is nice."
Tracy smiled. We heard water splashing & dripping from the other side of the pool, and I turned to see Micah & Sandra scrambling up out of the water and over to a couple towels she'd set out on the lawn on the far side of the pool. They laid down and started kissing.
Tracy reached up and gently stroked from the hair behind my ear, down along my jaw, turning my gaze back to her as she did so. "You know why Sandra invited you guys over here tonight, right?"
"Well, yeah," I said, "so she & Micah could…" I trailed off.
Tracy stopped me. "A little, I guess. But it was for us, too." I just looked at her, a little puzzled. She went on, "Sandra said you're hot. And she said thought we'd have a good time together if we could meet and you could just relax."
She moved a little closer in toward me. "I think she's right." Then she shifted up in the water and kissed me lightly on the cheek. "What do you say? Wanna go lay down & relax?"
"Um, ok," was all I could think to say. Tracy slid down off the bench seat and into the water, then started swimming for the shallow end of the pool. She moved slowly, with long, relaxed, lazy strokes, and I just watched her for a minute. When she got to the shallower water, she stood up and turned toward where I was still sitting. She smiled at me, made a "come here" gesture with her finger, and turned and started walking up out of the pool. I slipped into the water and started out after her.
By the time I made it up out of the water, I looked around and saw Tracy sitting on a big beach blanket in the farthest corner of the lawn. It was getting dark in the back yard, so it was hard to see her clearly, but it was still a warm night, so I walked over to where she was. I sat down next to her and said the suavest, most sophisticated thing I could think of.
I sounded like a complete idiot, a total dork. And Tracy couldn't help herself. She broke out laughing. But for some reason, rather than being horrified at my own stupidity, I started laughing, too. We laughed together for a couple minutes, and when it started to die down, Tracy looked over at me and said, in her own mockingly suave tone, "Hi." That started us going all over again. We couldn't look at one another without busting up. It was stupid, sure, but it helped, somehow. This time, as our laughter subsided, I reached up, put my hand on the back of Tracy's neck, and leaned in and kissed her.
And, of course, I botched the job. I bumped her nose with mine, pulled back suddenly, forgetting that I still had my hand on the back of her neck, and pulled her over onto her side.
"Oh, God. Tracy, I'm sorry…" I started.
"Tom," she said, "it's okay. Just relax for a minute." She pulled herself up and kissed me lightly on the lips.
"I want to kiss you." She kissed me again.
"I wanted to kiss you when you first got here." And again.
"I like you, Tom." And again. She shifted around with her hand on my neck now, and started to lay back down on the blanket, pulling me with her. "And I want you to kiss me."
I leaned down over her on one elbow, bent my head down, and kissed her, more slowly this time. She opened her lips a little and flicked her tongue across my lips while we kissed. I opened my mouth and pushed my tongue between her lips, and she started running her hand up and down my back. I finally started to relax a little, and we just kept kissing.
We kissed back and forth for a few minutes, me running my tongue over Tracy's teeth and darting in to feel for her tongue, and then he pushing me out and chasing my tongue with her own. After a little while, and feeling a little bolder based on how eager Tracy was, I started to rub my free hand around on her stomach and side. I kept getting closer and closer to her left breast, but was still scared to go for it.
Then Tracy kind of half pulled back, half pushed me away, from our kiss. She looked up at me, reached for my hand, moved it up to her breast, and smiled at me. I couldn't believe what I was feeling! Her breast was soft, and a little squishy, but firm at the same time. I rubbed it through her bikini top, and we went back to our kissing. I branched out a little and kissed from her lips, down to her chin, then up along her jaw line to her ear. After nuzzling her ear for a moment, I started kissing down her neck, still rubbing her breast with one hand.
When my lips moved from Tracy's neck to the top of her chest, I stopped, and looked up at her. She smiled, shifted around a little bit, and untied the top strap of her bikini top. Then she pulled the material down & out of the way, uncovering her breast and exposing her nipples for me to see. Even in the dim light, I almost came at the sight. She had beautiful little pink nipples, centered in somewhat darker pink areolae, and I sat staring, transfixed, at the sight. I reached out a hand and cupped one of her breasts in the palm of my hand and felt the warmth of her skin and the soft hardness of her nipple in my hand. I leaned down to kiss her again, and after our lips parted, Tracy put both her hands on the top of my head and guided me down to her chest.
I gingerly kissed the skin on the rise of her breast, then flicked my tongue right up to the edge of her areola. Tracy, her hands still on my head, pulled me over a little bit until my lips grazed across her nipple. She shuddered a little, and raised her chest up to meet me. Not quite believing what was happening, but not wanting to move and break the spell, I continued sucking at her breast. I rolled my tongue over her nipple and felt it move between my lips. I sneaked my left hand up her side and rubbed her right breast under my palm. I couldn't believe what I was doing. This beautiful, sweet, sexy girl was letting me suck on her tits! Right there in Sandra's back yard!
Reluctantly, I paused for a moment to take a breath, and picked my head up. I heard a noise, and looked over to the side of the lawn where Micah and Sandra had gone. It looked like Sandra was sitting on top of Micah, rocking back and forth. I couldn't tell in the dim light, but it almost looked like Sandra wasn't wearing her bikini any more.
I looked back down into Tracy's eyes and saw her smile. Then her smile changed to a grin, and while I bent down to kiss her again, I was surprised by the sensation of her hand tugging at my swim trunks. Before I knew what was happening, I felt Tracy's hand slip down my side and under the elastic of my waist band; then her fingers wriggled lower and found their way through my pubic hair, and I felt her fingers wrap around my cock.
Then she squeezed. Not hard, just a little bit. But it was the most exquisite feeling I'd ever felt. I saw stars in front of my eyes, and I must have got a funny look on my face, because Tracy stopped, sat up, and asked, "Tom, are you okay?"
I just smiled at her and said, "Yeah," after which she started to reach back in to grab my cock again. I leaned in, kissed her, and ran my hands down over her breasts to find the top of her bikini bottom. I hooked a finger under the fabric and started to rub back and forth, when Tracy stopped this time. She sat up, gently grabbed my wrist and pulled my hand away.
"Not tonight," she whispered into my ear. Then she reached into my swim trunks again and found my raging hard-on. She sort of half-squeezed, half-rubbed up and down the shaft with one hand, while at the same time laying back down and pulling me back down with the other to nuzzle, lick and suck her beautiful little tits. We stayed like that for a few minutes, until I jerked a little and sat up. Tracy saw the panicked look in my face and said, "It's okay," then she sat up on her knees and knelt over me with her little tits hanging down. She kept rubbing my cock, moving a little faster, and with her other hand, pulled my swim trunks down to let me free.
By the time she had my cock completely free and was openly stroking it up and down, I couldn't contain myself any longer, and with a grunt I stiffened and shot my load all. The first jet actually shot up and hit right between her breasts, but the others landed a little closer to home, sliding down the side of my cock and over her hand. Tracy grinned but kept pumping my cock, until there was nothing left.
After a minute, she wiped her hand on the blanket next to me, then tucked my cock away in my swim trunks again, and laid down next to me with her breasts, still uncovered, resting on my chest. We stayed like that for the longest time, sometimes kissing, sometimes stroking each other here or there, but mostly just lying next to each other, until the sound of Micah clearing his throat from a little way off brought us back to reality.
I looked up. Micah & Sandra were standing just a little bit off our blanket. They were both wrapped in towels and were holding their swim suits in their hands. They were both grinning from ear to ear as they watched us.
"Looks like you two hit it off, after all," Micah said. "It's getting kinda late. We need to get inside & get cleaned up before the girls' folks get home."