The Man Who Stole My Cherry

Literotic asexstories – The Man Who Stole My Cherry by CleoRa,CleoRa
My stories involve events taken, with their permission of course, from my client’s case files as a family sex therapist. Lately, lots of people on this site have been sending me emails asking me to write something about my own personal experiences, an action I have resisted until now. After checking with my husband, who agreed that I should, I will reluctantly share details of my first sexual experience (although I consider it to be quite dull after some of the stuff I hear in my office daily.)

Hubby knew I wasn’t a virgin where he married me, and also knows I haven’t cheated on him since, (although we do “role-play” a lot.) I have shared some of my early adventures with him as part of our role-playing foreplay, to spice things up a bit in our bedroom activities. These stories have always excited him but we have never taken it to the next level and probably never will. We’ve never so much as discussed acting out our roleplaying for real, and the fact that it even seems like there is the possibility we might — keeps things on the edge and exciting.

I have told him this story and it is one of his favorites. After the first time I related it to him, we spent the entire weekend fucking our brains out. I think the idea of sharing me excites him, but he’d never want to do it for real. As for me, I love him so much I’d do whatever he wanted me to do, anytime he wanted it. After nine years, I am still head-over-heels in love with the man.

Bradley was nearly two years my senior. Tall and lean at six-foot-two-inches, he was the school’s star athlete. Blonde and beautiful, blue eyes to kill for and a devastating smile, he was the total package. Just my luck he lived only three houses down the street from me. For two years we saw each other come and go with our tiny circle of friends, but only from afar. I didn’t know at that time he’d enrolled in the local college just as I had.

Around eighteen I blossomed, titties galore, and a butt all my friends said they’d die for. Maybe because of that, I wore lots of jeans to school, and skimpy shorts on the weekends. My friends were all really cute, so we always had a bunch of guys hanging around us.

I attended a local college and in my sophomore year as I was leaving for school one morning, only six blocks away, I encountered Brad walking past. He later confirmed he’d timed it like that. We walked together and by the time we reached school, were smitten. A week later, he kissed me in my backyard, melting my knees. From that day on, I was lost. That doesn’t mean I gave him my cherry that night. That didn’t happen until months later.

I was determined to remain a virgin until I married, but that didn’t mean our petting sessions weren’t pretty intense. We’d meet behind our homes after everyone else had gone to sleep, lie on a blanket and do everything but fuck. The second time we kissed I sneaked over the fence and watched silently as he spread out the blanket. I told him “no sex.” Smiling, he pulled me down against his hard body, kissing me deeply. My heart pounded so loud I was afraid it would awaken the neighbors.

After a few minutes I was trembling and weak, surprised my panties were so wet. I pushed him away, sat up, gasping for breath as he watched me closely.

“I really hurt baby,” he said.

I’d heard how prolonged kissing affected boys, giving them, what we girls laughingly called, “blue-balls.” Maybe it was puppy-love, or simply lust, but I didn’t want him to hurt because of me.

“What can I do,” I finally asked, as he pulled me back down, swallowing my mouth again.

I quickly discovered he’d taken his penis out, only after he took my hand and wrapped it around it. I’d never touched one before. It felt hot — hard but soft, like it was a large piece of marble wrapped inside satin. Although I’d felt it against me when we kissed, it had felt like a piece of wood then and outside his clothing was so much bigger than I’d imagined. I was more determined than ever he’d never get that thing inside me. It’d probably kill me anyway. Still, I was so excited I couldn’t breathe, my heart beating away.

Not knowing what to expect, the size of Bradley’s cock was more than a little terrifying. Now I know that he, like my husband, were much larger in that department than the average male. Back then I thought they were probably all the same. One thing I knew though, it’d never fit inside me. The first cock I’d ever touched seemed so beautiful in the moonlight. I could see veins and ridges running through it, a soft spongy helmet on top, and it moved subtly in my hand, throbbing as I held it.

Anyway, he quickly showed me what he wanted and I eventually got the hang of it, listening to him moan and grunt as I alternated between fast and hard, slow and easy. I soon learned what he liked best and felt that I was about to climax as I watched him throb in the moonlight, the meaty tip glistening with a tiny bubble. Then it broke free, running down my hand in a sticky trail.

“I’m close, Baby,” he groaned through his teeth.

I didn’t know what that meant exactly, but I leaned closer to watch the first male climax I’d ever seen. I wanted to touch my wet panties, feel some of what he was experiencing, but I wasn’t that brave yet. Then his body went rigid as he groaned aloud, my face suddenly sprayed with his explosion. Startled, I tried to withdraw my hand but he clasped his around it and kept it working, as he thrust upward over-and-over. After a while, he lay back, breathing hard. I had goop all over my hand, and some on my chin.

“Jeez, what a mess,” I whispered.

Strangely, I wasn’t all that repulsed by its stickiness. In the darkness I saw him handing me something white – his handkerchief. I cleaned up a bit with it and he drew me down to kiss me again.

“I love you, Cleo.”

No one had ever told me that before and my heart simply melted. I felt him guiding my hand back to encircle his deflated cock, now feeling soft and satisfied, like me, content. I did it again for him before I went back home that night. I could have done it all night. In fact, I did it every night we could get together after that. Soon though, it wasn’t enough. After the first week, he was also touching me through my panties, as I did him.

The first time it happened, I felt his fingers slide inside my loose-legged shorts, touching my damp Venus Mound. I started to pull away but suddenly just pushed myself back against his fingers. A few minutes later he forced the elastic band of my panties aside and slipped the tip of one finger inside my virgin opening, the first to ever do that, other than my own. Heaven soon followed. I came like I was dying. Now I knew what he was feeling.

We kissed every time we got together, there was deep soul kissing, lots of tongue, our hearts pounding, hands touching each other through our clothing, leaving us gasping for breath.

“God, I’m dying,” he’d gasp. “Let me make love to you, Cleo. I love you. It’s okay.”

I admit I was a real tease though. I’d wear short-shorts, mini-skirts and soft sweaters, anything I knew that would drive him wild. I’d let him touch me almost anytime, anyplace, sucking his tongue, sliding my fingers over the bulge in his taunt blue jeans. My hormones were raging, making me reckless. Everyone in school knew we were an item, and suspected we were having sex. I did nothing to dispel those rumors. He was the school star athlete, and I was his girlfriend. I drove him crazy — and that drove me crazy.

One night as I stroked him slowly into delirium in his back yard, he wrapped his fingers in my hair and forcibly pulled my face down until the tip of his wet penis touched my lips. All the girls had talked about this stuff enough that I knew what he wanted. I’d even considered doing it for him, but just wasn’t brave enough to initiate it. It took little urging but I finally licked it, and then slid my mouth over the head, nearly swooning with pleasure. It was like nothing I’d ever experienced before.

It slid over my tongue, banging against the soft sides of my mouth as I licked and gently sucked it, sensing that he wanted me to take it even deeper. I let my tongue slide around the soft helmet, tasting his fluid as he grew more excited. Later he’d explain what that was, but all I knew at the moment was, it was delicious.

I made it last a long time, stopping each time he was about to shoot. I wasn’t ready to let him go off inside my mouth. I didn’t think I could handle that. I sucked his thick meaty penis with love, licking all the way down and back up, learning that he enjoyed having me kiss and suck his balls. I learned how to swallow nearly all of its length, breathing through my nose to keep from gagging. Feeling it enter the opening of my throat was one of the most enjoyable things I’d ever imagined. I quietly came on my fingers as I did that but never stopped fingering myself, as I waited to do it again and again. I was in heaven.

As it was, he came in my mouth anyway. Totally unexpectedly, thrusting upward, holding my face close, emptying himself inside my mouth and throat. It wasn’t bad. Okay, I loved it. I told myself it was because I loved him so much. I sucked him dry again before I left that night, wanting to do it more but he was finished. I was thinking; God, what a rush!

All I could think about the next day was letting him do that to me again. I saw him standing with his teammates after school, and walked toward them. They saw me coming, whispering among themselves, nudging each other and winking as I arrived. I felt they all knew, and that Brad had told them. Well, I thought. Fuck them. I was his. Who cared if they knew?

Because of football practice, it was two nights before we got together behind his house again. I couldn’t even wait until he’d spread the blanket, just dropping to my knees, unzipping his pants, and taking his swelling cock inside my hungry mouth.

“God, you must’ve missed that,” he groaned, clutching my hair.

I whimpered my agreement as I slobbered on his leaking penis, wanting him to cum quickly, hungry for it. He forcibly pushed me away as I protested weakly, quickly spreading the blanket and pulling me down on it. Before I could object, he had my sweater off, and was pushing my shorts down as he nibbled my breasts. I couldn’t object, I couldn’t breathe, I couldn’t even think, clutching his head tighter against my tits. It was the first time we’d both been completely naked. His lean body felt wonderful against mine. I felt so small.

His hot mouth trailed down my electrified body, licking and nibbling everywhere maddeningly, driving me crazy, until I felt his breath against my wet vagina. I almost screamed with pleasure and surprise as his tongue entered me. I came so hard I nearly blacked out, and the first thing I was aware of was him pushing his hard cock against my tiny opening.

“No . . .” I muttered.

“I gotta. Can’t stop.”

Stretching and burning my small vagina like fire, he finally managed to get the crown inside, then the fire increased as he buried himself deeper, where nothing had ever been. A sharp pain snapped deep inside my vagina walls, but it wasn’t nearly as bad I’d heard it’d be. The he effortlessly bottomed out against something deep inside me.

I remember thinking, “I’m a woman now. Brad’s woman.”

After a moment, he started slowly moving. I waited attentively to see if it’d hurt again, but within moments I was moving with him, helping him – urgently seeking that place where all things exploded into the universe. When I came it was like nothing I’d ever imagined. Indescribably delicious. Life-changing. Painfully exquisite. He didn’t stop, even then, just kept hammering me harder, no longer making love — fucking me now – like he was some animal and I was his mate. I came again as I felt him spurting deep inside my core. It was even better than the first time.

I think we both slept for a short time, and then I felt him stir, touching my breast with his fingertips. I covered his hand lovingly with my own, smiling, just letting him feel my slowing heartbeat. I was in love. He lowered his head and I opened my mouth, accepting his tongue, slow, sensuous and dancing against mine. His hand found my pussy again, a finger slipping inside, then two more. I lifted, helping him, feeling him pinch my nipples, his cock hard, pushing insistently against my thigh.

I leaned over him and took it in my mouth, tasting our love juices, relishing it because I knew we’d made them together. His cock quickly throbbed to life as I swallowed it, feeling the pleasure of it pushing my throat apart, into my gullet, deeper than ever before. I wanted to taste him, let him empty inside my mouth, but he had other plans. He suddenly hovered over me, fumbling to find my opening again as he inserted his cockhead inside me. Then he pushed all the way in.

How could this have been better than before? I don’t know, but it was. I was out of my mind with forbidden pleasure, letting him roughly use my body as he wanted, loving it, needing it as I thrust upward to meet his hammering. I cried and whimpered into his open mouth, clawed his bare back, clamping his hips with my thighs so hard they hurt. His cock felt like a light post sliding into me, pulling my vagina walls out and then forcing them back inside savagely. It should’ve hurt. It didn’t. If both our parents had walked up at that moment, if the whole world came by, it wouldn’t have mattered. All that mattered was the pressure I felt building inside my loins.

He leaned upward, bracing himself on locked elbows, slowing his thrusts as he gazed down at me frantically clutching his hips to pull him deeper.

“What . . .?

He smiled at my shenanigans, as though amused. Puzzled, I squirmed around, seeking his meaty length again.

“Please,” I muttered.

“Like that?” he said.

“Please, brad, I need it. Please?”

“I like it when a girl begs for my cock,” he said as he savagely drove it into me, finally giving me what I wanted.

I came, sobbing and climbing his body, feeling him release his sperm inside me a moment later. It was so intense I blacked out for a moment. When I came around I leaned down and tenderly cleaned his wet cock with my tongue, loving every minute of it. He was my man now. I’d do anything for him.

I guess it was just blind good luck that I didn’t get knocked-up during all this. My best friend Carrie, realizing what was going on, gave me a lecture about birth control and provided pills. Her mother no longer needed birth control because she’d had an operation, but continued getting them for her daughter. Carrie had so many she gave me some and instructed me how to use them.

Fucking Brad was on my mind constantly those days. I couldn’t get enough of him. He’d do me any place we took the urge, and I’d let him. Blow-jobs in the gym, on the bus, the park’s men’s room, anywhere we took the urge. He got a lot more oral sex than I got fucked, so by the time we finally found a place to do it I was usually climbing the walls! Sometimes we didn’t even talk. I’d just walk up, take his cock out, pull him down and mount him. It’s a wonder we didn’t get into all kinds of trouble. He got a car that summer and that made it easier to find a place. Glad a cop didn’t see us.

As sports started up again we got to see less of each other, or at least I thought that was it. I only got to meet him once or twice a week, and for a girl who was used to playing with her new toy nearly every night I was in misery. After five days of excuses, I finally saw him near the school entrance, talking with a pretty brunette I didn’t recognize. I walked up, glaring at her until she stammered something and walked off.

“Busy?” I asked sarcastically.

“Look Baby, don’t go getting an attitude on me! Okay? You want to get together tonight to fuck?”

“Well, since you asked so eloquently . . .”

I suddenly choked up, fighting back tears. “Brad, what’s going on between us? Did I do something wrong?”

He wrapped his arms around me in a tight hug. “Everything’s cool Babe. Just been busy with practice and studying for exams. Want to go to a party this weekend?”

I wiped my forming tears away, sniffing. “Sure, if my parents let me.”

“Oh yeah. Forgot, you’re younger than most of us.”

Ouch. I almost spit at him, but I calmed down, saying, “I probably can. I’ll tell them I’m staying with Carrie so I can be out late. And, I’m not that young. I’m a woman now. Remember?” I tried smiling seductively at him. “Tonight around midnight behind your house, then?”

“Yes. I’m gonna fuck you to death.”

“Big talk,” I said as I walked away laughing.

We met later and he did nearly “fuck me to death.” But the real story is what happened that weekend, as I told my parents I was staying with my best friend for the night. I hated deceiving them, but I was in love. The party was at one of his team mate’s house, whose parents were out of town. His whole team was there, as were a lot of girls, to include the new girl I’d seen him with. Her name was Samantha, called Sam for short.

We had the entire house to ourselves, and by midnight most of the crowd was drunk, many slipping off in pairs to fool around, maybe have sex. Brad insisted I drink the drinks he brought me. “Act like an adult.” I guess you’d say I was really getting fucked up. Several times I couldn’t find Brad and would look for him, finding him talking with Sam. I got pissed and wanted to leave, but couldn’t find my jacket and my mind was so foggy I didn’t remember what I was looking for five minutes later.

Someone had me by the wrist, leading me somewhere. It was Brad. I smiled at him and he smiled back. We were in a master bedroom, and the bed was mussed like it’d recently been used. He pushed me back on it, pulling off my pants and sweater as I giggled.

“Nasty boy,” I remember saying.

He knelt between my sprawled legs, and I felt his tongue lathing my crouch. Groaning, I pulled him tighter, humping upward. Just before I came, he dragged me roughly into the middle of the bed and started unbuckling his belt. I closed my eyes, felt his weight on the bed over me, and his wonderful hot cock against my wet opening.

He thrust hard to enter me, and I gasped loudly and he lowered himself and started fucking me wildly. I went in and out of consciousness, but came almost at once, and then he did also, spurting over and over inside me. I blacked out a bit but he was still there humping against me when I drifted back.

He kissed me as I opened my mouth for him, then he leaned back. I wasn’t Brad! In fact, there were several people in the room, his teammates! The guy groaned loudly as he came inside me, and rolled off, replaced by Alan, the Black running back on Brad’s team. I tried pushing him off but my hands didn’t want to work. Alan grinned down at me.

“After you get this black cock you won’t want anything else,” he said maliciously, thrusting against me hard.

Even as wet as I must have been with several men’s cum in me, it still hung up, burning, stretching, and hurting me. I cried, tears running down my face, but he just kept pushing harder as I blacked out again. I came back to life to find my legs over his shoulders and him fucking me like an animal. It no longer hurt. In fact, it felt good. I

n my drunken state I didn’t consider the consequences as I started to move with him. He let me lower my legs to grip his sides, and increased the pace of his rhythm, seeking my mouth with his. I took his tongue, followed it back inside his mouth with my own, moaning and thrashing, seeking his cock. Lost in my induced fog I fucked him back as he stretched my pussy with his huge cock like Brad had never done.

I came hard, and he also came but never stopped fucking me until he flipped me over on my knees and entered doggie style. I wanted to cum again, but after he’d fucked me for a while he suddenly stopped, crawled around in front of me and shoved it down my throat, cumming instantly. His sour sperm coating my tongue and the roof of my mouth as it slid down my working throat, I felt someone else as he knelt behind me, shoving a smaller cock inside me. But I drifted away again and didn’t wake up again until morning.