My First Time

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Ladyboy

Note: A girlfriend and I were talking about this the other day, and I decided it might be fun to put it down in print for my Literotica readers. I may have taken some liberties with the numbers to keep it ‘legal’, but the story is factual.

*

He pushed my hand away. “Here. Let me,” he whispered. Though we’d been making out for almost an hour, I wasn’t so sure about all this, and my fingers were shaking and tentative. I wanted it, of course. I just needed a gentle shove. I was horny and I was conflicted, my heart was pounding in my ears, and the wetness I felt at my crotch scared and embarrassed me in equal parts. What if I was bleeding?

Thinking back, I’m sure he didn’t care. Bobby was 20, a couple of years older than I, and I knew he was no virgin, but I was madly in love with him. He flipped the buttons on my sweater with practiced ease, and suddenly I was down to my white cotton bra, the thin sweater pushed back over my shoulders. It was cool in my room, and my nipples reacted beneath the multiple layers of padding. They felt like stones inside my bra. I hadn’t developed yet. I was tall and thin, with straight dark hair that flowed down over my back. Coltish, I think, is the word.

It was a gray, drizzly day, and Bobby had been waiting near the bus loading zone when I got out of school. Like most of my friends, I didn’t drive. They all knew I walked home every day, rain or shine. My parents both worked late. Today, Melanie’s parents offered to drop me off at my house, but when I spotted Bobby’s old Buick, I told them I had it covered. The look on Melanie’s face when she saw Bobby was priceless!

“Are you sure?” she asked. She attempted a look of concern, but I saw it for what it really was: a grudging jealousy. I nodded. I’m sure I had a cocky smile on my face, but my tummy was already full of butterflies, and they were swarming.

“Call me later,” she whispered.

I turned and walked to Bobby’s car, then leaned in the window. “Waiting for someone special?” I asked. I was so flirty! He said he was, but he’d let me take her place. Bastard! I laughed, knowing he was teasing me just as I’d teased him, and climbed in. “Come ‘ere, you,” he ordered, pulling me by the arm across the seat until I was practically glued to his side. The heat of his thigh next to mine lit up my senses as he pumped the gas pedal and ground away on the starter. The old Buick wasn’t cooperating, but I didn’t care. I could have sat next to him in the rain for hours, just inhaling the scent of his sweat and cologne.

Finally, the car roared to life, and Bobby burned rubber leaving the gate. I squealed delightedly, sure that my new boyfriend was the coolest guy ever, and he patted my thigh with one hand. That touch started a whole new set of fantasies. Remember when you swore you’d never wash your cheek after your first kiss? I was seriously considering having my leg bronzed, after feeling the heat of his palm on it!

When we got to my house, we sat in the car and talked until he took my chin in his hand and turned my face to his. Bobby’s mouth was soft and warm, and I opened my lips to his tongue after kissing him for just a few seconds. I felt it exploring my mouth while his hands explored my body, covering every inch from my waist to my neckline in long groping strokes. He pressed me backward until I settled onto my back on the seat, with him on top of me, and our kisses turned frantic.

Bobby insinuated casino oyna his knee between my thighs, and I felt the warmth of his leg against my sex. The lust I felt from that touch was doing things to my virginal body that I’d never experienced before. My hormones were in a turmoil. Nerve endings were chaotically sending messages to my brain, but they were being re-routed through my pelvis. My breath was coming in ragged waves as my panties seemed to constrict around me, squeezing the dampness from my pussy.

At last I pushed his hands away. “Bobby,” I gasped. “I can’t do this. Not here.”

He paused abruptly, and I thought he was going to tell me to get out, just leave me standing, clothes and mind askew, on the curb. “Okay,” he said. “Let’s go inside.”

Now it was real. As I led him up the walk, I knew it was finally going to happen. I wanted to call Melanie and tell her what was going on, to beg her between sobs to be there with me, to ask her advice, to rub it in her face. I wanted to run, I wanted to get this over. And I wanted to lie next to Bobby and have him make soft gentle love to me and tell me I was his forever. As he closed the front door behind him, I turned to him. He took me in his arms and walked me backward to the sofa, my mother’s sofa. There he lay me down and began to kiss me again.

We made out for the longest time. I thought maybe he was as nervous as I was. But when he cupped my breasts with his hands, he left no doubt that he was in charge. And so…

“Here. Let me.” I raised my hands above my head and surrendered to him. I let him undress me, starting with my sweater. He unbuttoned it and pushed it back on my shoulders, then tackled the snaps of my bra, and when he pushed the loose cups up over my breasts and placed his mouth on my nipple I moaned happily.

Bobby tongued my nipple playfully. “You smell good,” he murmured, as his hand circled my little mound of flesh. I couldn’t speak. “You taste good, too.”

I thrust my chest outward, hoping to make up for what I lacked in size with eagerness. And as he licked and suckled and fondled my erect nipple, I felt a rush between my legs that took the remainder of my breath away.

“Ooooooh, jeeze, Bobby” I breathed. My voice was quavery. I could barely push the words out. The whole of my universe was centered on that place beneath my belly that had only heretofore served as an instrument of frustration, ever since I got my first full period. Now it was causing all kinds of other problems. I hoped I wasn’t bleeding.

When Bobby’s hand went to the snap of my jeans I cringed, but I was too deeply committed to attempt to stop this now. Something inside me was screaming for him to hurry, to rip my clothes off and do whatever it was that turned girls into women. I kicked my legs as he peeled my pants down, and in no time I was almost naked. Only my panties stood between his cock and my pleasure, my white cotton briefs. Thinking back, I wish I could have worn something pretty and lacy and erotic.

It didn’t seem to bother Bobby. His hand slipped behind the waistband and down over my belly, where his fingers encountered my sparse dark little bush. He moaned, happy to be so near his goal, and slid his fingers through the hairs as his other hand tugged at my panties. At the same time I felt him grind his hard cock against my bare thigh. It seemed impossibly big. And then I was naked.

“Tori, take my dick out,” he panted, canlı casino and directed my hand to the mass of meat inside his jeans as he rolled over onto his back. I groped at it, unable to tell exactly what I was holding, but eager to find out. With a shaking hand I unzipped his pants and he unfolded outward onto my hand, like a flower opening in the morning sun. His cock stood erect before I even got his jeans unsnapped, towering atop its denim plain.

Then his fingertip grazed my clit, and a thousand fires glowed inside my belly, each one its own little inferno. My mouth was suddenly dry, and I sucked in a huge lungful of air.

“Bobby!”

I gasped his name between tremors. I felt his finger slip inside me, deeper than I’d ever attempted in my fumbling attempts at chasing the pleasure my friends had said was to be found there. Bobby found that pleasure, claimed it, brought it to my surface. And I craved more.

While he pushed his jeans down his own legs and insinuated himself between my outspread thighs, I waited with my head and shoulders on the sofa cushions, thinking that I was going to hell, and not caring at all. I planted my feet flat on the floor and arched my back, my fingers digging like talons into the corduroy-covered couch as he guided the head of his cock over my skin. His touch was electric. “Please be easy. I’m a virgin,” I whimpered, but I doubt he even heard my voice.

With a groan, he slid his cock between my tender labia, and that’s when the first searing sensation of pain blindsided me. “Owww!” There was something wrong! He edged forward, but he wasn’t going in. Dammit, that hurt! Undaunted, he pulled back, then thrust his hips forward.

“Aaaiiiiiiieeeeeee!!”

I couldn’t help it. I screamed aloud as my hymen tore, and in those long moments between pain and pleasure, two things happened: a boy’s cock breached my vagina for the very first time, and his hand went over my mouth.

My scream of pain muffled, Bobby began thrusting in and out of me. It didn’t hurt for long, perhaps less than a minute. My momentary pain was fast becoming pleasure, but the only thing I understood at the moment was that I couldn’t breathe. In his lustful frenzy, Bobby seemed unaware that he had his hand over both my mouth and nose. My hands flailed uselessly at his strong arms, but they did nothing to stop him, nor even slow him down. He fucked me fast and hard, as young men are prone to do, and just as I was about to pass out he got off inside me.

I think he noticed my body becoming limp about the time his cock spewed its first full load into my virgin canal. He let go of my face immediately and grasped me around the waist with both hands, holding me up even as he continued to thrust, until he had emptied himself inside me. I came around slowly, like a diver surfacing from a very deep dive. I was unaware that I had begun to climax, too. I only knew that I was experiencing [i]something[/i] deep inside; that the feelings were confusing and wonderful. The feeling of fullness was something I’d never anticipated. The pain of my recently abused vagina gave way to the awareness of his cock inside me, even as it began to shrivel and withdraw. I loved the primal feel of his skin against mine.

Bobby pulled from me with a groan, and kissed me quickly. I knew he wanted to go, but I locked my arms around his neck and made him tell me it was okay. He mumbled that he loved me, then pushed away kaçak casino and stood up. I pulled my knees together as he redressed, conscious of being naked in front of him, but he wasn’t looking at me. I could feel our combined fluids draining from between my legs, and suddenly all I wanted was for him to go so that I could clean up. I glanced down, and was horrified to see a bloody smear along the top of one thigh, where his cock had dragged over me.

Bobby seemed to understand my embarrassment. He said, “I’d better go, you know,” and stole a quick glance down. He asked if I was okay. I saw his look, and my insides twisted as I muttered, “I’m okay.” He leaned over and kissed me once more, then was gone.

I waited until I heard the click of the door latch, then bolted upright. It was worse than I thought. Both inner thighs were matted with drying blood, and there was a dark red smear across the front of the sofa, my mother’s pride and joy. I ran upstairs naked and retrieved whatever cleaning solutions I could find, then set to work. By the time I had finished, I wasn’t sure if it was better or worse. At any rate, the couch was soaking wet, so I arranged the little pillows to cover it, and hoped it would dry by the time my folks got home. Then I gathered up my clothes and ran upstairs.

I took a quick shower and changed my clothes. Afterwards, I stood in front of the mirror in my room for a long time, analyzing myself. I was sure I looked different somehow. Certainly, I was smiling more. I was practically glowing! I decided I looked experienced, for lack of a better term. I wondered if my parents would notice it, and decided my friends at school certainly would. If not, I’d find a way to let them know what we’d done.

With a coy look, I unbuttoned the blouse I’d changed into and put my hands up under my bra, pushing my breasts up. My nipples began to harden beneath the cups almost immediately. I liked the feeling, and stroked across the fronts with my thumbs, imagining it was Bobby. I could feel the reaction in my pussy. I was a woman now! On a whim, I moved my hands up my chest and onto my neck. There, I encircled my throat with both hands, watching my own face closely in the mirror.

As my fingers tightened, my face began to get red. I wanted to stop, but couldn’t. I was mesmerized, fantasizing about Bobby choking me again, watching me as my eyelids slowly fell, then taking my maidenhead, again and again. Distractedly, I could feel my pussy tingling, and felt the renewal of the wetness that had first scared me so. This time it felt good, and I squeezed harder.

The element of self-preservation must have made me relax my grip, but not before I climaxed again. This time I recognized it for what it was, and embraced it. I lay back on my bed and slid the shorts and panties off my hips, then explored myself with my fingers for the next hour, bringing on two more orgasms before I heard a car pull up in the drive beneath my window.

Shit!

I dressed quickly, then sauntered downstairs, trying to look as casual as I could. My mother came into the kitchen and asked if I had any homework. I lied and told her I’d finished already. Daddy kissed my forehead and headed for the garage.

Once alone, I let loose a long, deep breath, then wandered back up to my room, where I could relive, again and again, the events of that afternoon. Every time I thought about it, though, my mind drifted to that moment when Bobby put his hands around my throat, and that’s when I would become most aroused. I didn’t know it then, but the feeling of being choked would become forever linked to my most memorable moments of sexual ecstacy.

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