“Brian, we’re going pretty fast. Do you even have a condom?”
He pulled his wallet out of his back pocket, then took out a condom. “I’ve got one.”
I bit my lip, aware of both his throbbing erection and the wetness between my legs. Was I really going to have my first kiss and lose my virginity in one night? Stranger things have happened, I guess. Still, I never thought I’d end up here with Brian. I watched as he rolled the condom onto his quivering member. When he finished, he rolled my thong down my legs, taking me in his mouth. As he pushed his tongue deeper inside my sex, I realized how badly I wanted him to put his cock in me.
My squirms told him I was ready. He kissed me, letting me taste my own juices. I sucked on his tongue as he positioned himself. Suddenly, I felt a push. I gasped, a sharp pain erupting across my body. He stopped for a second, then pushed farther in. I tried not to let the pain show. I took a deep breath, letting his girth stretch my virgin sex. After a second, I started to feel the pain lessen. He took himself out, then pushed back in deeper. The pain subsided, but the feeling still brought butterflies to my stomach. I gripped his back as he started his rhythm. I grinded against him, fully losing myself in this new fullness.
Brian grunted and cursed. I kept my pace, but he withdrew. “Stop, I only have one condom.”
“What do you mean? We can’t stop, I was just getting into it.”
He pulled off the condom, knotted the top, and showed it to me. “See? We can’t use this again.”
“I’m on the pill,” I said, ashamed at how badly I wanted him inside me.
“Have you been tested?”
“Brian, you just took my virginity.”
“Oh,” he said, tossing the condom into my garbage can. “I haven’t slept with anyone but my fiancée and we’re both clean.”
“Then will you please fuck me?”
He smiled and did just that. We went at it for another five minutes before he came a second time. I still hadn’t reached an orgasm. I urged him to continue. He said he couldn’t get it up a third time so quickly. I never knew men had to recharge like that. I could have gone on forever. He kissed my forehead, handing me my clothes.
“Here’s your money,” he said, taking out his wallet.
“Could you pay me later?” I said, shimmying back into the tank top. “It would feel weird taking it after we just did that.”
“You more than earned it,” he said, smirking. I crossed my arms over my chest, suddenly feeling embarrassed. He could tell the comment bothered me. “I’m sorry, that was rude.”
“It’s okay,” I said, shrugging.
“I can pay you at the end of the semester instead if it’ll make you feel better.”
I nodded. “That would be great.”
“If I pass with a C or better, I’ll even double it,” he said. “I want to reward my little math scholar for all her hard work.”
“I appreciate it,” I replied, feeling better about myself. A swell of confidence entered my chest. “Maybe if I don’t end up a professor, I can become a different kind of teacher.”
I couldn’t believe I said it, but Brian laughed. “Ah, but, you won’t get to pick your students. You better stick to math.”
Chapter Three
The next few sessions continued like this: study for two hours, have sex for one more. The only problem with the affair was that Brian hadn’t made me cum. He came way too early, then left when he was done. I started feeling more and more like a toy to him. One session, he decided to stay at Yale instead of going to see his fiancée to get in another session. Our final was right around the corner and he still wasn’t where he needed to be. My roommate needed the room to study for a big exam, so Brian invited me to his frat. Initially, I worried that his brothers would think I was only there to have sex. Brian assured me no one would be there on a Saturday afternoon. He picked me up in his sports car and drove me to his frat house. Not a car in the lot. I let out a relieved breath. We got to his room and started studying.
Two hours went by in a flash and Brian and I were fooling around as usual. Even though I had my doubts, I knew Brian wouldn’t let his brothers see us messing around. They had this weird honor code about brothers and the girls they have sex with. He explained, but I didn’t really care. As long as no one saw me naked, I was fine.
He pulled my shirt off, then my bra. I sat on his bed, ready for whatever he had in store. He unzipped his pants, presenting his fully erect member to me. I knew exactly what he wanted. I’d never tasted cock before, but I took his in my mouth hungrily. I wanted him to feel good. I let the tip sit in my mouth as I sucked. The tip was smoother than I thought it would be; it glided around on my tongue. I put him in a little further, tugging on his shaft while I worked my tongue. I felt something warm dribble into my mouth. I assumed it was his precum. I looked up at Brian and smiled, taking him even farther into my throat. I bobbed back and forth. He grabbed the back of my head, pushing me lightly. I was able to get him all the way in my mouth. After a few more bobs, I felt his cock get harder, then it pulsed. Warmth flooded down my throat as his first load shot off. The second and third coated my tongue and cheeks. It burned the back of my throat. For a second, I thought I might choke, but I swallowed, and the feeling went away. I kept sucking, hoping he’d cum more. He pulled himself out of my mouth, saying it was too sensitive to be touched. He sat down next to me and zipped up his pants.
“What about me?”
“There’s no way I can get it back up after that. You sucked me dry, my little math nerd.”
“So I just make you cum and I get nothing?”
“Do you want me to call someone in? I think I heard a brother come home—”
“No! God, Brian. You took my virginity. I get that that might mean nothing to you, but I’ve had to learn a lot in a very short time to keep up with you and I have no orgasms to show for it.”
“You’re right, Shelley,” he said, rubbing my back. “I’m sorry. Next time I’ll do better.”
We sat in silence.
“Are we still on for tomorrow? The exam is on Monday and I still need a lot of help.”
“Fine, but you’ll need to put in an extra hour if you really want to pass.”
******
The next day was the same. We studied for three hours, then Brian started kissing my neck. “Today’s all about you.”
He meant it. For an hour, he kissed every inch of my body, taking time with each nipple, each thigh, until he finally reached my soaking sex. The more he licked my clit, the louder I moaned. I pulled him up, practically begging him to fuck me. He entered me slowly, finding a rhythm I clearly enjoyed. He went at it until he came close to cumming, then pulled out.
“My little scholar isn’t quite ready yet,” he said, making his way back to my wetness. “I think she needs to go over the material some more.”
He kissed my thighs, nibbling as he got closer to my lips. His tongue found my clit easily, moving in tiny circles while his finger pressed into me. He brought me so close to the edge, but I wanted to feel full of his cock. I whined as he sucked my clit, on the brink of an orgasm. I pulled him up and told him to fuck me. He kissed me, filling my mouth with the taste of my sex.
“I can tell your little pussy liked that extra attention. She’s so wet for me now. You’re a naughty little math slut, aren’t you?”
“Yes, my pussy is so naughty. She’s a bad girl.”
“How naughty does little Shelley think she can be? I think your little pussy can take a lot more, don’t you?”
“Yes, she wants more. She wants more cock, baby.”
Brian pumped into me a few more times before cumming inside me. “After little Shelley gets lubed up with Brian’s cum, I think she can take something this big.”
He pulled out a massive dildo from under his pillow. It had to be a third bigger than Brian, and way thicker.
“That’s way too big.”
“Oh, I don’t think so,” he said, teasing my lips wit
h the tip of the dildo. “I think your little pussy likes to be stretched.”
He pushed it all the way inside me. I thought it would split me in half. It felt so big inside me. I felt so full. He flipped a switch on it, causing it to vibrate while he twisted it. He put my hand on it; it was almost too big for me to properly grip. I managed to slide it in and out of me, letting myself take in more of it as my pussy swelled and ached. Brian smiled as I moaned, arching my back to fit more of it inside me. He traced my lips with his finger; I took it in my mouth, sucking on it. I felt the pressure build until I could feel myself losing control of my muscles. I started twitching and let out a guttural moan. I came hard and long, riding out the vibrations.
“That’s my naughty slut.”
******
Brian got a D on the exam the next day. I got my first B.
Because of the poor test scores, our professor decided to drop our lowest exam grade and upped the percentage of our final. It was now worth half of our grade. I wasn’t too worried; I got one B the whole semester, and that was because I couldn’t sleep Sunday night. I kept reliving my first orgasm. More importantly, though, Brian could end the class with a C if he did well on the final. We crammed the last week before our exam, limiting our sex sessions to really focus on the material. Four days after the exam, the grades were in. I got an A, as expected. I waited eagerly by the phone for a call from Brian. When it rang, I immediately picked up.
“How much do I owe you?”
“Eight hundred and forty.”
“Really?” he said. “Sounds a little low to me. How about one thousand six hundred and eighty?”
“You got a C?”
“Fuck yeah, I did!”
I screamed, scaring the shit out of my roommate, but it was worth it. All his hard work paid off. He passed. He could graduate. “I’m picking you up in five, wear something nice. We’re having a party in your honor!”
I put on a white t-shirt dress and the thong I wore when I lost my virginity. My roommate helped me pick out some lipstick. It felt sticky on my lips, but she said it would dry. I left as soon as Brian pulled up in his car.
I arrived to easily thirty men cheering and singing “She’s a Jolly Good Fellow.” They formed two lines for me to walk through, each holding a bottle of champagne. At the last line of the song, they shook the bottles, blasting me with the champagne. I screamed, my body instantly freezing. I covered my chest with my hands to hide my hard nipples. I completely forgot to put on a bra. Brian apologized, wrapping his arms around me. He took me to his room and gave me a warm robe. He made one of the pledges wash my dress.
“I’m sorry I ruined the party,” I said, sitting on his bed.
“What do you mean? We’re just getting started!”
“But I’m in a robe.”
“That’s okay, no one will care.”
I shifted uncomfortably. I wasn’t sure I was comfortable being the only girl in the house, let alone a girl without any clothes on. Still, Brian’s brothers had always been respectful to women on campus. Out of all the frats, this one was the safest for girls to party at. I got up and let him lead me back down to the festivities.
Everyone apologized while one brother handed me a glass of champagne. We all chatted for a while; Brian told stories about the first two times he took the statistics course. The professor seemed to really have it out for him. As things started winding down, two brothers got up to leave. They kissed my cheeks in thanks for saving Brian from another year of college. The other brothers wanted to thank me, too. One by one, they got up and kissed my cheek. Charlie, Brian’s best friend, went for a kiss on the mouth. I was shocked at first, but quickly came back around. I’d never had this much attention before. I don’t know why, but I found myself enjoying the kisses from these strangers. As the line of men progressed, the kisses became more intense. They ended up turning into full on make-out sessions. I lost myself in each kiss, a wetness growing between my legs. One guy took it upon himself to graze my thigh with his fingertips. To my surprise, my legs spread of their own accord. I found myself needing release. I broke free, making my way to Brian.
“Can we go somewhere else?” I said, hoping we could have a private moment.
“The party isn’t over yet.”
“Please either take me upstairs or take me home.”
“Okay,” he said. “Let’s go upstairs.”
He took me to a room with mirrors for walls. It looked like a gym. Wrestling mats covered the floor. I glanced up. The ceiling was a mirror, too.
“Why are we in here?”
“Well, this is the party room! We’re still having a party, aren’t we?”
I smiled, telling him to lock the door. My wetness dripped down my thighs. I needed him in me. We started fooling around and he started talking dirty to me. He told me that my naughty little pussy was so wet and ready to be fucked. I moaned as he entered me.
“Oh, yes, she’s so naughty. She needs your cock.”
He started pounding me hard, asking me if I wanted a bigger, thicker cock to fuck me when he was finished. I didn’t see him bring the dildo in, but I assumed he had it hidden like last time.
“Yeah, baby, I want your cum to lube me up and then I want a huge cock in me, fucking me raw.”
“Boys, we’ve got ourselves a party!”
The door burst open and the rest of the brothers came flooding in. Brian fucked me for a moment longer, then came into me. His hot cum trickled down my legs as Charlie tried to put himself in me.
“Wait! I don’t know if you’ve all been tested.”
Brian pulled Charlie away from me. “Guys, wrap it up. If you don’t have a condom, leave the party room. Slutty Shelley wants you to wear a condom.”
I heard the rustling of condom wrappers. Suddenly, I was surrounded by about ten hard cocks in condoms.
“Is this what you want?” I asked, turning to Brian.
He smiled. “It’s not important what I want. It’s what you want that matters.”
The room quieted. I looked at each of the men. They waited for my decision. Was I really about to be such a dirty slut? My pussy ached for another cock. I pulled Charlie down to me. My heart beat so fast I thought I’d have a heart attack. I realized after this, I’d never be the same.
Charlie slid into me easily. He filled me more than Brian did, and seemed to know what he was doing. He started slow, building me up with hard thrusts. I reached the edge of my orgasm, in disbelief that I was about to cum from my first real cock. He stopped moving in me and asked if I was close.
“Yes, don’t stop,” I said. The others started protesting. They wanted a turn, too. The full scope of the situation hit me. Just the thought of all these men fucking me brought me to my first orgasm. Charlie kept pounding me as I rode out my orgasm. I felt his member harden and he grunted. I felt him leave me, my pussy twitching, and another cock immediately replaced his. The next few men were average in size, but I slowly reached my second orgasm. I expected another average penis but was surprised to feel a thick one push into me. I looked up to see a guy I’d known since high school. I had a crush on him as a teenager.
“Who would have thought? Shelley the nerd turned into such a little slut.”
A surge of shame waved through me. I couldn’t believe how much I loved being the sex toy of all these men. He started pounding me. Brian moved to my face, asking me if I enjoyed being everyone’s slut. Then he put his cock in my mouth. I moaned, wetter knowing I took two cocks at once. I spotted myself in the mirrors with one cock fucking my pussy and another in my mouth. The sight brought me to my third orgasm. I shook as Brian let off his load in my mouth. I swallowed every drop.
They went on like this for a while until Leroy, the full back of the football team, brought his cock to my pussy lips. Immediately, I knew he was too big for me. I apologized, saying he’d surely hurt me. He said he’d let me set my own pace, and that I could lower myself onto him. I straddled him, nervous and excited to take on such a l
arge cock. I lowered myself down, bracing myself on his knees. His tip barely fit; it must have been the size of a tennis ball. It stretched me more than I thought possible. Slowly, I tried to lower myself further. It felt like a balloon inflated inside me, pushing my walls as far as they could go. I lost my breath.
“It’s too big,” I said through gasps. Still, I found myself trying to take more of it. Two guys brought their cocks to my mouth. I spent time licking each of them as I tried bouncing a little on Leroy. The two brothers removed my hands from Leroy’s knees and guided them to their hard members. Without the support, I slid all the way onto Leroy’s dick. The rest of the men beat their cocks furiously, in awe of how much my little pussy could take. I moved myself back up to the tip, then lowered myself down again. After three or four more slow bounces, I relaxed, enjoying the stretching in my hot sex. I went faster and faster, putting both cocks in my mouth. They came instantly at the sight. Their cum shot in my throat and onto my face. I tried to swallow it all, but there was too much. I let it drip down my chin as I felt my next orgasm build in my stomach. I looked down to see the tip of Leroy’s cock pushing out my stomach. He grabbed my hips and started fucking me hard. I came, then felt hot liquid in my wetness. He hadn’t worn a condom.
Gay Dads- All His Son's Friends Page 42