Kerry

Everybody remembers their first time. Losing one's virginity is a milestone in anyone's life. Sometimes the memory is pleasant, and sometimes not so much. Either way, it isn't likely to be forgotten. I won't say I remember my first time like it was yesterday, because, frankly, many of the details have faded over time, but I do, however, remember enough of it to smile warmly when it comes to mind.

I've been telling the story of my first time around campfires and drunken parties for years. Well, when the conversation turns to sex, that is. I don't just jump in with, "Hey, everybody! Want to hear how I lost my virginity?" I usually wait till other people have lied or exaggerated first about their own sexual experiments and experiences.

Unlike a lot of my friends, I didn't have sex until after I'd graduated from high school. Doesn't mean I didn't try. I just didn't manage it till after graduation. I was always envious of my friends who were "getting some" in school. Had I known then what I was missing, I probably would have tried harder to get laid. My best friend, Eddie was getting it on a regular basis from his girlfriend when he was a senior. He almost always got laid on Sunday afternoons, and sometimes even through the week, after school. Just depended on what his girlfriend's plans were.

The three of us; Eddie, Marie, and me, spent a lot of time with each other, and there were many times when Eddi and Marie would make out in front of me, making me wonder if maybe they were budding exhibitionists. I remember one time when Eddie grabbed a handful of breast when they were making out on my couch, and he asked me, "Doesn't Marie have the best tits you've ever seen?" True, they were nice , probably D cups, but I never did get to see them uncovered. Not only did Eddie have no qualms about fondling Marie in front of me, but he confessed later that he'd tried many times to talk her into having a threesome with me. It never happened, but she DID tease him sometimes about the possibility of doing me without him. Eddie didn't like that idea. She never did try to seduce me, though. I think Eddie didn't like her teasing him about doing me, because he knew I probably would have taken her up on her offer. She WAS cute. In fact, she and I even went out a couple of times after they'd stopped dating, but nothing ever happened between us. We were never anything more than friends.

I did have a casual girlfriend part of my senior year, and for a short while after graduation, but we really didn't see much of each other. Kerry was the athletic type, very into her softball team, and just didn't make much time for dating. I often wondered if maybe she was a closet lesbian, and only kept me around to throw off suspicions of her preferred sexual desires. I didn't care that she might "play for the other team." I often fantasized about her when I masturbated. I thought about her showering with her teammates, soaping each others breasts, stealing kisses when the coach wasn't around, and just reveling in being naked with the other girls . What I wouldn't have given to have showered with her and her teammates. I'd have been more than willing to soap their backs, their fronts, wash their hair, finger their pussies, and even towel them dry when they were ready to get out of the shower. There were also many other things I thought about doing with all of them in the showers, but I don't have that kind of time or space in this story.

My relationship with Kerry started when she invited me to the Sadie Hawkins dance our senior year. In case you've never heard of Sadie Hawkins, it's a dance where the girls take the initiative, and ask the guys to be their dates. The Sadie Hawkins dance can trace its origins back to the 1930s, and the L'il Abner comic strip. The mayor of Dogpatch had a daughter he didn't think was ever going to leave home because she was homely, wasn't married, and wasn't very likely to ever be so. He decreed a footrace between the unmarried guys and gals, with the end result being matrimony. The comic was so popular that it took only a few short years for a variation of the concept to be adopted by high schools and colleges across the country. It's been more than 20 years since I was in high school, so I'm not sure if the Sadie Hawkins traditions are still practiced or not.

Kerry and I went to the dance, held hands, danced really close, kissed a few times on the gymnasium dance floor, and were told more than once what a cute couple we were. Really, I think we WERE a cute couple. We're both short, only about 5'5", and lean of build. Of the two of us, Kerry was definitely the more attractive. The dance was a casual affair, with a hint of hillbilly, so we were both decked out in jeans and flannel shirts. Kerry was also wearing cowboy boots and straw hat. Her flannel shirt was just the right kind of tight to accentuate her firm breasts, and was unbuttoned far enough to show a very tantalizing hint of cleavage. Her jeans were form fitting, and hugged a very nice little ass. I tried fondling her ass during some of the slow dances, like I saw some other guys doing to their dates, but she wasn't having any of that. She reached around to grab my wrists, pulling them up a more modest height on her waist. Hindsight being what it is, I don't really blame her. Getting all worked with up your date is one thing, but looking like you need to get a cheap hotel room is something else entirely. She made a good call, considering where we were. We had a good time at the dance, working our teenaged hormones into a frenzy, and I began to wish for the dance to end so we could go someplace private. She must have read my mind, because she asked if we could leave early. At first I was worried that she wanted me to take her home, but she held onto my hand as we went to get our coats. I took that as a good sign. We climbed into my old Mustang, and she leaned into my shoulder. I would have loved to hold her hand, but the transmission was a manual, and I had to shift gears. I held her hand as much as I was able while driving.

As we left the school parking lot, I asked if she wanted me take her home. She looked at me and smiled. She also reached over to plant a very warm and sensual kiss on my ear. I took that to mean that she didn't want me to take her home right away. We drove outside of town to find ourselves on a country road I knew, and found a deserted area to park. We sat and talked for a little while, reminiscing about the dance, and who did or said this and that, when it began to rain. We weren't bothered by the rain though, because we were in my warm and dry car. Unlike a lot of older cars, my Mustang had cloth instead of vinyl seats, and was quite comfortable. There are times when I really miss that car.

This was the first time I'd ever been alone with Kerry, and my cock was hard from the close dancing, holding her close, kissing, and the possibilities of what might happen while we parked. I'd never had a girl touch my cock before, and didn't know if it was going to happen this evening or not, but I certainly hoped it might. I could wish for it, but wouldn't be too disappointed if it didn't.

We weren't in the most comfortable car for necking, since there was a stick shift between the seats, but we made the most of it. We kissed, held each other close, and she let me put my hand inside her shirt. I reached around to unfasten her bra, and heard her laugh. I wasn't sure what was so funny. She moved my hands away, and leaned in for another lingering kiss. She told me her bra fastened in the front. I'd never heard of such a thing. How convenient!! She unhooked her bra, and pulled the cups away from her firm young breasts. I'd felt girls up before, but this was the first time I'd ever actually seen real bare tits. All my previous sexual fumblings had been in situations where it was too dark to see anything. I thought I was going to cum in my pants. I played with her tits, sucked on her nipples, and had a great time. She rubbed my cock through my pants a few times, but never made a move to undo my belt or zipper. I didn't push the matter. I was happy enough, just to be rubbed through my jeans. I was really hard, and I knew the end of my cock was wet with precum, but there wasn't much I could do about it. I never got my hands inside her pants, but she let me rub between her legs. I could feel her heat through her denim pants. I was stunned at the heat.

We kissed and felt each other up for what seemed like hours. I was still pretty inexperienced at the time, but I think she came when I was rubbing the warm spot in her pants. Her breathing quickened, she stopped moaning, and actually shook for a moment. I thought maybe she was cumming, but I wasn't sure. When she finally pulled my hand away, she increased the urgency of our kissing. She rubbed my cock harder and faster through my pants. Instinct must have kicked in, because my hips started rocking back and forth. If she'd had my bare cock in her hand, I'm sure I would have sprayed both of us with thick ropes of hot cum. As it was, I didn't climax, but the end of my dick was leaking, causing a wet spot in my underwear. I was so close to an orgasm, but I'm glad I didn't. It would have been an uncomfortable ride home with an underwear load full of cum.

I have to laugh, because I remember getting the Mustang stuck in the mud when we tried to leave our parking spot. Remember that it had been raining. It never occurred to me that the rain would complicate matters. I put the car in gear, pushed on the gas pedal, let out the clutch, and heard the drive tire spin in place. I pushed harder on the gas, and felt both tires spin. This wasn't good. Cell phones weren't part of our daily lives in the early 80s, and it was a LONG way to the nearest pay phone. Kerry jumped out of the car to push. I tried to get her to stay in the car and let me push instead, but she didn't know how to drive a stick shift. She told me she wasn't a sissy, and wasn't afraid to get out and push. I didn't want to ruin a fun night by arguing with her, so I gave her my shoes, and let her get out to push. I was careful not to press on the gas too hard, so the second tire wouldn't spin, covering her in flying mud. I wondered if anybody else's date was ending like ours was that evening. She impressed me by actually helping me get the car unstuck. I'm just glad she didn't get muddy doing it. I only just got her home early enough to keep her out of trouble with her mother.

Her macho attitude through getting my car unstuck only reinforced my beliefs that she might be a closet lesbian, but like I said, I didn't care about that. It intrigued me to think she might be getting it on with her teammates. I thought again of her showering naked with the other girls after practice. Strange that a young man would keep fantasizing about naked girls, huh?

We never did more than heavy petting whenever we went parking after that, but at least it was sexual activity, and I DID become very familiar with her breasts. She wasn't bashful about letting me play with them. I remember how I'd suck on one nipple, fondle the other, and hear her moan with pleasure while I had my way with her breasts. I remember the first time she unsnapped her jeans so I could get a hand down her panties. I was amazed at how HOT and wet her pussy was. I could feel the heat emanating from it before I even touched her. It seemed like she was always wet when she let me finger her.

Kerry was fond of giving me hickeys. I have to admit that they felt good while she was giving them to me, but we fought more than once because I didn't want her to give me hickeys where they would be visible. I had a job that required me to deal with the public on a daily basis, and hickeys have always struck me as somewhat low brow, and not very conducive to a professional appearance.

It was a few weeks after graduation, and deep into the summer months when Kerry, my best friend Eddie, his girlfriend Marie, and I were partying at my house while my folks were vacationing in Las Vegas. My parents had what at the time was one of the coolest bedrooms I could imagine. Along with a big waterbed, real wood paneling, and exposed timber beams in the ceiling, there was also a refrigerated 16 gallon beer cooler. Not having yet developed a discriminating beer pallette, I was more than happy to drink whatever beer my parents had on tap. My parents went for quantity over quality, and the tap was usually filled with cheap beer. On the upside, the beer was cold and available. I had three older brothers, and a fraternal twin, but they were all long gone by this time.

We were partying in the living room, which was separated from the master bedroom by a simple hollow core door, but the bed in the next room was very much in my mind while Kerry I were sitting next to each other on the couch. We'd had only a couple of beers each before Eddie and Marie excused themselves to my bedroom. Kerry and I exchanged awkward glances, and wished them well. I was going to tell Eddie and Marie not to get my sheets dirty, but thought better of it at the last possible moment. When we were finally alone Kerry leaned into me for a serious lip lock. I really enjoyed kissing her. Kerry had such sweet breath, and she was a great kisser. She licked tentatively at my lips, and I eagerly accepted her tongue. She must have been hornier than I thought, because she began groping my growing cock. I'd been down this road with her in the past, and didn't really expect anything more than blue balls at the end of the evening.

Being a young man, it took almost no time for my cock to reach full, straining hardness. I wasn't as open to being an exhibitionist as Eddie and Marie, even though they had already excused themselves from our presence, so I asked Kerry if she'd like to move our play into my parents' room. She answered by standing, pulling me up, and leading me to the next room. I was looking forward to some more kissing and less hurried groping. This was going to be our first real chance to get truly comfortable while we gave in to our teenage urges. It was nice to finally lie down with Kerry someplace other than the back seat of a car. We kissed and hugged for a few minutes, then I started to get paranoid about getting caught. I thought it might be a good idea to lock the front door, and maybe use the bathroom while I was at it. I knocked on my bedroom door after I'd locked the front door, just to check and make sure everything was okay, and was none too politely told by Eddie to fuck off, that he and Marie were busy. I laughed and headed back to my parents' room. I was completely unprepared for what I found when I got there. I walked in to find that Kerry had removed all her clothes, thrown them into a pile on the floor and was waiting for me under the covers. She patted the bed and asked if I was going to join her. I didn't need to be asked twice.

I shed my clothes, but tried to appear like I wasn't in the biggest hurry of my life. I was finally going to be naked with a beautiful young woman. What I failed to take into account was that Kerry still lived with her folks, and they insisted she still abide by a curfew while living under their roof. She had to be home by 10:30, since she hadn't made prior arrangements to stay out later. Crap. I saw by the bedside clock that I'd have to get her home in just a little over an hour. So much for some less hurried groping.

I crawled into bed with Kerry , feeling electric tingles where my flesh touched hers. I leaned in for another kiss, thinking I'd be cool and act like I wasn't rushed for time with her. She was having none of that! She again probed her tongue into my mouth, much more urgently than she had on the couch, then reached down to pull my hips toward hers. I felt my cock brush against her pubic hair, and I thought I would come right then and there. If I hadn't spent so much time jacking off, I probably would have cum as soon as my cock touched her.

She'd rubbed my hardness through my pants many times, but had never actually touched my cock in any of our previous encounters. I reached for her right nipple, and caressed it with my fingers. She loved it when I played with her nipples. Before I knew it, she'd taken command of the situation, and worked us into a perfect 69 position, with her on top and me on my back. I could have died with pleasure when I felt her tongue lick the base of my cock, and work its way to the head. Again, I almost came when she took my cock head into her mouth. I felt it only fair to return the favor, and took my first tentative lick of pussy. I'd read lot of porn stories, and was expecting her pussy juices to be salty or bitter, reminscent of other, less sexy, bodily fluids. I was pleasantly surprised to find that her pussy, like her breath, tasted great! I stuck my tongue in as far as it would go, bringing my nose into contact with her anus. Kerry was a tiny girl, so I was able to lift her just a bit to give me better access to her clitoris. She must have been masturbating while she was waiting on me earlier, because an orgasm gripped her as soon as my tongue touched her clit. I didn't give her time to simply cum. I put my whole mouth into it,sucked her clit for all I was worth, and used my tongue to lash it while she writhed in her climax.

When she finally came down from her sexual frenzy, she climbed off, lay down beside me, looked me in the eye, and told me to fuck her. I answered by pulling her in close for another deep tongue kiss, then reached down with my free hand to feel how wet she was. I scooped some of her slick wetness onto my middle finger and rubbed it gently on her clit. She squealed and pulled me on top of her. Having no experience, it took me just a moment or two to get properly aligned and work my cock inside of her. In the heat of the moment, and not realizing this was going to happen, I'd made no provisions for birth control. I had my cock about halfway in when I told her maybe we shouldn't be doing it without a condom. She told me to relax because she was on the pill. She explained that she'd had some medical problems, and being on the the pill helped regulate her hormones. That was all I needed to hear. I sank my cock in to the base, and just stayed there, enjoying this new sensation. Her pussy was warm, wet, and comfortably tight. I was in as deep as I could go, and just lay there for a moment, amazed at how good it felt to finally have my cock buried in a hot, wet pussy.

I'm not hung like a porn star, but it didn't seem to matter to Kerry. Her face flushed, and the rosy glow spread down her torso, making it appear like she was standing too close to a campfire or woodstove. I must have stayed buried to the hilt for too long, because she reached up with both hands, pulled me tighter, and began rocking her hips back and forth. This was incredible. Now I knew why Eddie and Marie fucked every chance they got. I could get used to this! We fucked, kissed, fondled, and enjoyed each other's company for the longest time. I glanced at the bedside clock again to find that she was going to be late getting home if we didn't stop what we were doing. I tried pumping faster, hoping I could cum before we had to stop, but it just wasn't going to happen. I couldn't believe it. The first time I get a girl naked and willing to fuck, and I can't even cum. I was bummed, but didn't have time to dwell on it.

Kerry saw the clock, and immediately started reaching for her clothes. She apologized for not being able to finish, but really had to be home on time. Her mother was a tyrant when she was late. Apparently her mother didn't relish the fact that her daughter was on the pill, and only agreed becuase it was a medical necessity. Her mother would kill her if she knew Kerry was taking advantage of the pill's contracetive benefits. Now she tells me... In Kerry's haste to get naked earlier, she'd misplaced her underwear. Of all the places to lose undergarments, it would have to be in my parents' waterbed. We looked, but didn't find them. She finished getting dressed, and went to wait for me by the front door. I knocked again on my own bedroom door, and told Eddie I was taking Kerry home. He again told me to fuck off, that he was busy. I thought to myself that I should make the two of them change my sheets, but once again kept my thoughts to myself.