Caution: This Sex Story contains strong sexual content, including Ma/Fa, Teenagers, Consensual, Reluctant, Heterosexual, True Story, First, Pregnancy, .
Desc: Sex Story: Chapter 1 - Remembering sex from the first time on. A candid recounting of various sexual encounters.
My first fuck was when I was 16 years old in 1961. I was in a boy's boarding school, a good one. The pay phone in the dormitory hall rang when I was walking by and I answered it. A girl was on the other end, in fact, there were several girls since I could hear them giggling and whispering in the background. The girl was named Caroline and lived in town. She had gotten the phone number from her sister who had once dated a boy at the school. We laughed and talked and exchanged names. It was the start of two months of phone calls every few nights.
We gradually became incredibly frank with each other. I confessed that I was a virgin but masturbated. She told me that she had "done it" three times with three different boys. She was 18 and had graduated from high school and now worked as a waitress. We described ourselves to each other, and we both, I think, were consumed with curiosity. Once she said that she and some of her friends would drive by the school at 4:00 o'clock. I was to prove to her girl friends that we knew each other by waving. I was dutifully by the road, but it didn't work out. I recognized the car she was in but only as it passed and my wave was late. I could not figure out which girl she was. She saw me, but her girl friends were not sure that I had waved.
After a while the tone of the phone calls changed. More and more of our talk revolved around sex. We finally arranged a date, well sort of. We agreed to meet in the woods behind the school one afternoon. Our talk had been frank enough that I thought there was at least a chance that I might get some sex. I bought a condom from a senior for one dollar, an exorbitant sum, but the condom was also accompanied by a mish mash of advice about sex. I slyly went into the woods several hours before we were to meet and stashed a blanket under a tree.
We did meet and I was both excited and disappointed. She was a girl that I knew had done it, and might, conceivably, do it again. She was heavy set, her face was plain, and she loudly chewed gum while we stood and talked. Her best features were her ample breasts and bright eyes I think she sensed my disappointment, because after a while she stood very closely to me and said "Well, do you like me?".
I said that of course I did.
She asked "Do you want to kiss me?"
As I leaned over to do so, she took her gum out and dropped it on the ground. The kiss was sexy, we tongued each other. She tasted of juicyfruit. She pressed her body against me when we kissed again and I was acutely conscious of her breasts pushing against me.
After we had been kissing for a little while, I stopped and led her over to the place where I had stashed the blanket. Embarassedly, I spread it on the ground. She said nothing, but as soon as it was spread she laid down and extended her arms to me. We started necking, and as we necked my hand moved onto her breast. It was large and soft and immensely exciting. I slid my hand under her sweater and back onto her bra covered breast. We continued necking, and then she stopped and pulled back. I was instantly convinced I had gone too far, but she sat up, reached her hands behind her and unhooked her bra. A moment later we were necking again and my hand was now on the soft flesh of her breast, I could feel her nipple and stroked it with my fingers, now pressing it into her breast and then stroking around it. This was farther than I had ever been with any girl before.
My penis was erecting, uncomfortably pushing against my pants. I reacted with a moment of embarassment when I felt her hand feel at it through my pants. Her hand started rubbing against it and I could feel it swelling. I moved my hand down to her stocking covered leg and then up under her skirt and half slip. She just continued to kiss and rub me, and my hand went further. I could feel the soft skin of her thigh. Her legs moved apart giving me acces to the satin softness of her underpants. I rubbed at her crotch, unsure of how I should do so to arouse her.
Again she moved, breaking our kissing. Her hips lifted up, her hands pulled up her skirt and pushed her panties down. Her legs moved, a foot hooked the underpants, and in a moment they were off. She turned her face back to mine. Her hand reached for mine and pulled it back up under her skirt. As we kissed my hand moved up and felt her pubic hair. Then I was clumsily stroking up and down at her crotch. When I moved my palm so that it pressed at the top of her crotch she murmured and pushed her tongue against me and her hips rose slightly. In a moment I was rythmically rubbing my palm at the top of her crotch, my fingers sliding up and down the soft pubic hair between her legs. Her hips were gently rising and falling in time with my rubbing. My fingers could make out her lips in the pubic hair. My index finger slid between them. I could feel moisture and the lips sliding against the sides of my finger as she pumped her hips.
She broke the kiss and looked at me. Then she pulled back a bit.
"You can do it to me, if you want to." she said.
"God, yes" I replied.
Her hands were at my belt buckle and then the snap on my pants. I had to stand to pull my pants off. My cock jutted out uder my underwear, and she reached out and touched it through my underwear.
"You've got a really big one." she said, and then her hands were pulling my underpants down.
I was embarassed. My cock was fully erect and she was looking right at it. Then her legs spread apart, her knees lifted, and she pulled up her skirt and slip. For a moment I saw a dense area of dark pubic hair, and then she was pulling me down on top of her.
Suddenly I rembered the condom. I scrambled back and reached for my hastily abandoned pants. I found the little tinfoil wrapper in the rear pocket and pulled it out. She saw what I was doing.
"It's OK. I am safe now." She tugged me back towards her, and I dropped the condom.
My hips fit in between her spread knees and my cock touched her crotch. I pushed forward. Nothing happened. I changed my position slightly and could feel the head between her lips. I pushed again and the head slid up into the top where her lips joined. She gasped. Her hand reached down and clasped my cock and pushed the head much lower than I had had been. Her hips lifted up a little bit and I felt my cock push in. I pressed forward and it slid in several inches.
No male will ever forget that first hot, wet, clasping feel of a vagina around his prick. It was wonderful. She moved slightly back and forth on my cock as if adjusting her position. She pulled at my ass cheeks with her hands and I pushed all the way in until our pubic bones touched. She gasped a little and looked, wide eyed at me, then turned her face a bit to the side and closed her eyes. Her hips moved back a bit, and then pressed forward swallowing my cock.
I started to pump at her. She moved her hips only slightly, but kept her knees wide open, welcoming me into her. I stared, transfixed, at her face as I felt my cock impossibly harden even more. In and out. In and out. Right at the mouth of her tunnel there was a ring of flesh that stroked my cock as it plunged into the softness beyond I could feel the growing pressure at the base of my cock. I started to stroke hard and short, not pulling all the way back, pushing to get deep inside her. As I did so, I moved up a bit higher aginst her, rolling her hips up. Her eyes opened and she looked at me. She was breathing in pants. That did it. I started to convulse. The semen spurted out of me and into her as we stared at each other. Once, twice, three times, a fourth, a final fifth, and I sagged down onto her.
She clasped my head and pulled my lips to hers, and we kissed, a wet soggy kiss with tongues sliding aginst one another. I lifted up and looked at her, then kissed her again. I could feel my no longer urgent cock still inside her. She could too, and I felt her tighten around my cock, almost a friendly gesture like a handshake. we kissed more and I gently moved her hair back from her face and stroked her cheek.
"Did you like it?" she asked.
"I loved it." I replied.
She smiled and we kissed again. Then I kissed her neck, pushed up her sweater, and kissed the nipple on her breast. It was hard and wrinkled and projected out, and I lightly nuzzled it, and then kissed it again. She put her hands on my head and pulled it against her breast. Experimentally, I slightly sucked in her nipple. Her body tightened, her hands pulled at my head, and down below I could feel her vagina clasp at my cock. I continued to play with her nipple with my lips, repeating the sucking that caused her to tighten.
I moved back and forth and little bit with my cock. It was not completely soft and as I moved I could feel it start to harden again. In a few moments we were gently fucking again. This time it felt different. Everything was well lubricated, but things were softer. The inside of her had more definition and I could fell the sides of her tunnel pushing against me as if the walls had expanded into the tunnel. The ring at the start of the tunnel had opened.
I was not so self absorbed with my own feeling as I had been the first time, and I as I looked down at her I watched her face. I noticed that when I rode up higher she gasped slightly and her hips pushed more strongly. In a moment I had shifted position. I was much higher on her body, my prick much more vertical into her, rubbing against the vee at the top of her lips. Her knees were lifted up and her hips were moving against me. With each movement she gasped a little but and I could feel the muscles tighten in her legs as they grasped at me. We fucked like that for several minutes as she grew more and more excited. Her eyes no longer looked at me, but were tightly squeezed shut. A flush started to spread over her neck and the top of her chest that I could see above the neckline of her sweater. Her arousal excited me, and I sawed into her faster.
"Unh, unh, unh" she gasped and her hands gripped me, stopping my plunging while her lower body rose up and down on my cock pushing against it, closing over it, and then drawing down against it. Her chest had a dark red flush on it, she gasped, all her muscles straining and poised at the top of one her heaves. Her eyes were tightly squeezed shut. She slid down, and pumped again, rubbing my cock against her as it went in. She jerked and and then relaxed. I knew she had come. It aroused me.
"God, a boy has never done that to me before" she said, looking up at me.
I started to move again, but she stopped me.
"Wait just a minute" she said, and pulled my mouth down to hers and kissed me. Obediently, I waited, kissing her, my rock hard cock well up in her, but my pubic bone not pressing against her.
Then her hands urged me and I started plunging in and out of her again. This time her eyes were looking at me, and I could see concentration on her face as her hips moved, timing their movements to mine. I started the short hard strokes and her hands pulled at me. I pushed into her as hard as I could and could feel my the base of my cock pulsate as I came. I pushed again and again, each push timed with a pulsation, intensely aroused at the thought that I was coiming into her. It was almost painful, but I spasmed several more times, then leaned down and kissed her.
We fucked twice more that afternoon, and agreed to meet the next Saturday when she dressed to go home.
As the Spring advanced we kept meeting in the woods. Most of the five or six meetings were similar -- little conversation and much fucking. One meeting she told me that she "wasn't safe". That afternoon I learned the most about sex. She showed me how to best excite her with my hand. I looked for the first time in detail at a cunt, saw her clitoris, and watched it enlarge as I moved the skin around it... We each masturbated the other several times and she was fascinated to watch my cock ejaculate as she stroked it with her hand, and even, most memorably, lightly kissed it a couple of times. She explained how when I sucked rhymically on her nipples she felt it down in her pussy, and what a female orgasm felt like.
I think for Caroline our affair was partially a prestige thing... she obviously was glad to tell her girl friends about the fact that she was doing it with a boy in prep school. The sex was not a big deal to her, but the affection and fondling was... She told me that she liked the most the time right after I had come in her, when she knew that she had given pleasure and I was soft and tender with her. It was obvious that she had had sex more than the three times she had said. Her father was a French-Canadian and had left her mother when she was ten. She first had sex when she was 12, and from what she said I gathered it had been with her mother's live in boyfriend and her mother had known that he was fucking her daughter. One time when she had undressed I could see a bruise on her cheek and on the side of her breast, but she had refused to talk about it.
For me the affair was about sex -- few things are as important to a 16 year old boy as sex. It also built my ego, a fragile thing in a 16 year old. I knew from the shower room that my cock was longer than most of my classmates, but it was immesely gratifying for a girl to tell me it was a "really big one". Moreover being told that you were the first one that had made her come by fucking her was a real ego booster. I did not love Caroline, and perhaps wasn't even fond of her -- I felt a bit guilty about what we were doing. But I loved the sex.
We lost touch that summer, except that almost a year later she sent me a birthday card on my birthday. I tried to call her then, but her phone number was disconnected. When I looked closely I noticed the postmark on the envelope was from another town forty miles away.
I was not to fuck again until after I had graduated. I had girlfriends, and one intense necking session that caused me to ejaculate in my underwear, but Caroline remained the only girl I had fucked until the summer after my senior year. I had became wrapped up in sports, particularly rowing. My physique was unusual for a Jew. When I graduated I was 6' 2", weighed 194, and had the long torso and arms that were needed for crew. My coach had told me that if I were able to keep rowing over the summer, he thought I would have a good chance at making college varsity my freshman year.
I suppose that my desire to row through the summer is what led to my next sex.