My sexual education started when I was fourteen. I was working as an outside boy at a sporting camp on a large lake in the northeastern US. I carried guests' luggage, cleaned fish, took care of the boats, motors, and gas, did routine maintenance, etc. I was big for my age and had been helping my Dad around the camp for several years.
The camp was run by my grandparents and my Mom. My Dad held down a full-time job, but helped with maintenance in the evenings and on weekends. We served guests three meals a day in a central dining room, and consequently, hired wait staff in addition to housekeeping. There were two dormitories for the staff, one male, one female with separate toilet facilities but only one common shower.
We hired three waitresses that year, Janet, Sharon, and Gail. Janet was 17 and still in high school. Sharon and Gail were college students on summer break and were both around 20. Janet was tiny, only 4' 11" and cute as a button. Sharon was your typical beautiful blonde and about mid-height. Gail was truly "stacked" and had legs that went on forever, if you know what I mean. There was going to be no shortage of loveliness to consider on the sundeck that summer!
As it happened, I had the boy's dorm entirely to myself that year. The dishwasher lived only a short walk away and went home at night. That left me with plenty of time and privacy for my favorite "research" at that age, porn and masturbation. Pictures are nice and I like videos, but I had been an avid reader from a young age and found written porn to be the most stimulating. I had a small collection of "fuck" books that I liked to read at appropriate moments, with all the good parts marked with dog-eared corners. I had learned a great deal about girls in general and sex in particular from those books, but was still a virgin.
The season had started and the girls had been there for about a week when I got sick. I had a summer cold or something and was feeling just bad enough for it to be noticeable, but not bad enough so as to need to take time off from my work. I was sleeping one night when I woke up enough to realize there was someone standing beside my bed in the dark.
"Whaaa?" I mumbled. I was feeling a bit feverish and wondered vaguely what was going on.
A cool hand passed across my brow. "You're sweating. Do you feel all right?"
I realized it was Janet. We had spoken a few times, but there was never any indication that she was interested in anything beyond casual friendliness towards a boy who was three years younger than herself.
"I'm fine, I guess. What's goin' on?"
"I was worried about you. Are you sure that you are all right?" she said softly.
"I'm fine," I said, repeating myself and still wondering why she was in my dorm.
"Would you like me to hold you for a while?" she asked. This was strange, but the thought of holding that small, compact body next to mine was exciting, and I wondered just exactly what she had in mind.
"Do you want to get in with me?" I asked, "I'm not wearing anything."
"No problem," she said, kicking off her slippers. I raised the covers beside me, held out my arm, and she slipped in and laid close beside me, placing an arm across my chest and burying her head into my shoulder. I realized she was wearing a set of what felt like flannel pj's. Her warm length felt wonderful against my side and a small breast was obvious, pressed tight against my side.
I realized I had an erection, and wondered if she would notice and think ill of me. If you haven't figured it out yet, I was still pretty naive at this point. We lay together for a few moments, then she reached up, turned my head towards her, and at the same time slid her leg over my crotch, sliding the soft, warm flannel up the length of my cock. I flinched a bit and was further surprised when she gave me a soft, lingering kiss. This was the first time I had ever kissed a woman other than my mother.
She left her leg pressed against my erection. "Do you like this?" she asked.
I didn't bother answering her. I just pulled her to me again and gave her a kiss of my own. This one lasting even longer while I experimented a bit. Within a few seconds, she parted her lips and thrust her tongue into my mouth. I had read about French kissing, but obviously, had no experience with it. I pulled back a bit, then decided I liked it and went back for more.
While we continued to kiss, she began to softly rub my erection with her leg. This went on for just a few seconds before I pulled back and warned her to stop.
"What's wrong?" she asked.
"If you keep that up, I'm going to cum."
"Wow. That was quick. Have you ever been with a girl before like this?" she asked softly,
"No," I admitted.
"I thought so. I've been watching you, you know."
"You have? Why?" I asked.
"I enjoy watching boys, especially big, handsome ones. Do you think that is strange?"
"Idono," I said a bit breathlessly.
"I like you. I want to teach you some things, and I think it is wonderful that I will be your first." She turned over on to her back, wiggled a bit while doing something with her hands, then turned back and assumed the same position. This time, when her leg slid back over my crotch, it was naked. She had taken her bottoms off and the feel of her warm skin against my cock and my side was like nothing I had ever imagined.
I couldn't take it anymore; I had to feel all of her. I turned onto my side, wrapped both arms around her, and pulled her tight against me. Her hard nipples bored into my chest through her pj top, and her leg came up and over my hip. My incredibly hard erection pressed into her belly and we kissed passionately, my experience at such things growing by leaps and bounds. We writhed against each other, my hips starting to instinctively move in a slight thrusting motion. Not enough to move my cock against her, but providing plenty of stimulation, nevertheless.
I reached down with my left hand and cupped her naked ass cheek, pulling our loins even more tightly together. Her butt was small and firm, hot and wonderful, and the tips of my fingers brushed the bottom of her crease. I realized that the little bump I was touching down there was her asshole, and she moaned into my mouth. I didn't know what I was doing or how wrong it had to be, but I wasn't going to stop now.
I caressed her ass and stroked my finger across her asshole. I could feel that the head of my cock and the skin of her belly were wet with my precum.
She pulled away and turned onto her back. "Get between my legs," she said breathlessly.
I readily complied. She made a warm nest of her legs and I found myself secure between them, with most of my weight on my knees and elbows, my chest on her belly and my head at her breasts. I had only seen naked breasts in pictures and decided right then and there that it was time to see some in the flesh. I reached up and started undoing the buttons on her pj top. I had no experience with undoing buttons on other people, so this took me a few moments. My hard-on was grinding into the sheets at this point and I was very close to cumming.
I finally undid the last button and pushed her top open. There was just enough of a glow coming in the windows from the outside lights for me to see. Her breasts were perfect. Small, with extended nipples, they were no more than the perfect handful. I had read a lot about how girls liked having their nipples sucked and I wasted no time, taking her left nipple into my mouth and sucking hard. Her body arched up at me and her legs came up and wrapped around my hips.
"I want you to fuck me," she said simply.
I really didn't know much about the female anatomy, but knew I was in approximately the right position. I raised my body up and tried to find someplace to put my aching cock. I slid the entire length of it up her furrow, and she hissed between her teeth, "Yesss."
Once, twice, three times, I tried to find the right place. I was apparently doing something for her with this, but I wasn't getting to where I wanted to be. "Lower," she breathed.
I slid lower on her body and tried again. My cock slid into something warm and tight and without warning I came, shooting large amounts of my cum all over the crack of her ass! That's right. I had missed my target and my wet cockhead had slipped between the tightly clenched cheeks of her ass. Junior obviously thought that was all she wrote and unloaded. I collapsed on top of her.
"Was I in you?" I asked, already suspecting the answer.
"No," she said, "but it felt good just the same. Your cum is so hot! I love it."
We held each other gently for a while before I realized I was probably too heavy for her.
"I'm sorry. Do you want me to get off?" I asked.
"No," she said. "I love the feel of you on top of me." Her arms and legs were still wrapped around me, and she started to gently lift her hips to me. "Do you think you can go again?" she asked.
My half-hard cock was still firmly snuggled between her ass cheeks, sliding without effort against her ass as she moved under me, my cum providing all the lubrication we could possible want at that point. A few gentle strokes later and I was fully hard again, and started to move with her, sliding out until just the head was in contact with her crotch, then sliding back until it made contact with the very wet bed sheets.
"You're hard again. Lift up."
As I pulled back from her, she reached between us and for the first time, grasped my cock with her small hand. "Wow! I didn't realize how big you are!"
I had no idea how big I was. I had nothing to compare it to. Apparently it was larger than normal. For her, anyway. We measured it later and found that it was about eight and a half inches long and almost a full seven inches in circumference. An adequate tool, apparently. I never had any complaints about it not being big enough and it gained a little in size as I reached my full growth.
She stroked it a couple of times, then pulled it to her. The head entered something that was warm, and very tight. She pulled on me until the head was firmly lodged, then removed her hand.
"Now," she said, "go slow, but push it in all the way." I needed no urging. I sank into her depths, one incredible inch at a time. There was no real resistance, we were both very wet, but she was very tight, and I could feel every nook and cranny as we slid together. I got about halfway in, then felt a strong urge to pull back and thrust again, so I did,
Again she hissed between her teeth as I drove in deeper. I still wasn't all the way in and my cock felt like it was being squeezed to death. She was so hot, so tight. I was in heaven. The hell with masturbation. I wanted this every chance I could get.
I pulled back again and hammered my hips down, driving her into the mattress as my cock bottomed out. I didn't know it, but I was up against her cervix, the head of my cock flattening out at the end of her hot, tight tunnel. I realized there was still an inch or so to go. I ground into her, trying to go deeper and her body writhed beneath me. Her eyes were shut and her mouth twisted in a grimace of pain/intense pleasure. I didn't care which at this point. I pulled back and drove into her again, then again.
"Oh my God," she breathed, "I've never had anything this big and fat before. You're killing me!"
I thrust into her again and held it deep, "Do you want me to stop?" I asked. I didn't want to, of course, but if I was really hurting her...
"No!" she almost screamed, "Fuck me!"
Reassured, I pulled back until just the head was inside, then slowly pushed back in all the way. Her legs pulled my loins into her hard and she shuddered, her depths squeezing my rock hard cock like a milking hand.
"I'm coming! Ohh, I'm cumming."
I held her tight, resting in her warm, tight depths as her spasm passed, then started stroking in and out again. I was getting ready to cum once more and this time I was determined to put it all in the right place, thoughts of possible pregnancy never crossing my mind.
Her legs relaxed a bit, I lowered my head, and with dificulty, bending my body over her, reached and started sucking on her left nipple again. She immediately went into another orgasm. I stretched back on her full length and picked up the pace, the cum starting to boil in my nuts. Pulling back and driving forward, rocking her tiny body, my nuts slapping over and over again against her upturned, wet ass, her hot, hard, little nipples sliding against my chest. I hadn't realized it, but each time I drove back into her, I was going a little deeper. Her warm, tight tunnel was slowly stretching to accommodate my size, her hips jerking off the bed to my every thrust, trying instinctively to get all of me inside.
I pulled back one last time and drove into her again, this time our pubic bones coming together at last, my entire length fully inside, as my cock swelled up even larger and jetted spurt after spurt of hot cum hard onto the entrance to her womb. I gave her three or four more short, hard thrusts, still cumming, her warm cunt squeezing me in continuous contractions. The constricted feeling of my cum rushing the length of my cock with each spasm was incredible.
Once again, I collapsed on top of her, and we held each other tightly for a long time, as my cock slowly softened within her warm, wet embrace. Finally, I rolled us over to our sides and we continued to hold and stroke each other, my cock never quite losing all its hardness, her leg once again over my hip, holding us close. We fell asleep with me still inside of her.
Janet left my bed before first light, but we got together several more times that summer. I was thrilled to be fucking a girl at last, but soon found out that she was doing other boys on the side. I was hurt and stopped making myself available. I found out later that she was fairly well known as the local high school slut, but I will never forget her lessons, and that wild first time.