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Disclaimer: All of the characters are fictional and over the age of 18.
“Dammit, Kurt, we need to get you laid at least once before we graduate!” said my roommate Dave. Graduation was in about four weeks.
“Mister Tongue-Tied?” asked Tom. “Good luck with that. Have you ever thought about a prostitute? I’ll chip in.”
“So will I.” said Jasper. “What do you think?”
I blushed, even though this wasn’t the first time the subject had come up with my roommates. “C’mon, guys, I don’t want my first time to be with some unknown woman I need to pay to have sex with me. I want it to at least be a girl who likes me, who I like back. But you’re right, I get tongue-tied anytime I make that my goal. That’s the real obstacle. Paying a prostitute isn’t actually going to solve that, even if I managed to go through with it. If anything, it will just make me more convinced that I’m a failure at relationships.”
It was nearly the end of my college life and I was still a virgin. Not because I really wanted to be or was saving myself for my future wife. No, I was one of those poor cases where my brain freezes up around women whenever I was thinking about trying to be romantic with them.
Study buddy? No problem. I was asked to do that a lot, maybe a dozen different girls over the past four years, and agreed because it helped my grades, too. These were usually pretty girls, used to getting guys to help them out. So long as I kept my focus on studying, I did just fine being around them. The fact that I didn’t hit on them only brought more girls to my door.
I really wished, though, that I could turn that kind of relationship into something more, but whenever I thought of it, I couldn’t speak. I just froze up, until I gave up on the idea. For whatever reason, none of the girls were making a move on me, either. I wasn’t even getting close to the “I’m a virgin at 22” speech that I knew I’d have to reveal before changing that status.
To be honest, I had nearly given up hope of ever losing my virginity, finding that I could enjoy myself more at parties if I stopped worrying about trying to flirt or picking someone up, could study better if I was only thinking of a study buddy as a study buddy.
Until one day, about two and a half weeks before finals were going to start…
I was coming back from Friday classes to our first-floor on-campus apartment, when I heard a woman’s voice shout, “You want us to do what?!?” from the apartment next to ours, through an open window I knew was one of the bedrooms.
These were student housing right on campus, cheaply furnished two-bedroom-one-bath apartments housing four students each, with a small kitchenette and a living room. As the best housing option on campus, they were picked by the upperclassmen first. As we were seniors and I had a high GPA to select our apartment for the group, we had picked one of the better locations, closest to where our classes were.
The shout came from the apartment next to ours, across the stairwell that led to the two floors above us. It was occupied by four women, Colleen, Dani (aka Danielle), Susan and Wendy. All of them had been regular study buddies of mine multiple times over the years. We’d even gotten to the point of selecting courses that we could take together, just to be able to study for them together. At least one of them was in every course I had that last semester. All four of them were gorgeous, in their own ways. I would argue that they were the best-looking foursome on campus, maybe even the four most beautiful women I knew.
I crept closer to the open window, when I heard, “We want to get Kurt laid.” That was Jasper’s voice. “And we think you four are all perfect candidates. You’ve been platonic friends of his for a long time, you even chose the apartment next to us just to make it easier to study with him. I know for a fact he thinks all of you are hot. He just has this thing where he can’t make a move on you, because he can’t speak straight when he tries.”
It was Colleen who spoke next, saying, “So you’re offering a $100 prize to whichever of the four of us gets him in bed first? What do you think we are, prostitutes?”
Tom answered, “No, of course not. He’s opposed to going to a prostitute, anyway, wants it to be a girl he likes and who likes him, which fits all four of you. You ought to do it for him out of gratitude for all of the courses he’s helped you out with over the years. We all know you each would not have your current GPAs if not for him. If the money is your only incentive, instead of an added one, don’t bother. Do it because he’s your friend, and he needs this. Consider the $100 a bet that you can actually get him to give in. He’s not to know about the money whatsoever.”
Well, that ship had already sailed. I backed away from the window, just as I heard Wendy say, “Okay, we’ll do it.”
So, what exactly could I do with knowing ahead of time that the girls were coming after me? I sure as shit wasn’t güvenilir canlı bahis siteleri going to play hard to get, unless my shyness itself got in my way, but an idea did occur to me. I turned back around, and headed to the center of campus to get my little plan started.
Our usual weekend activities unfolded, a lot of it spent with the girls as a group together with my roommates, and I never had an opportunity to be alone with one of them without the guys around.
I studied with Colleen and Susan in their apartment for the last history exam before finals that Sunday night, with nothing happening. There wasn’t even a hint that they were thinking of seducing me. Or maybe I didn’t see a sign that would have been more obvious to a more experienced guy.
It was the next night, when I was studying with Wendy for both of the classes we had together, with the first hints of finals preparation, that everything started. My roommates were conspicuously absent, so we were spread out on the sofa and coffee table in the living room, rather than trying to study on the ridiculously small kitchen table the college provided, or trying to fit at the one desk I shared with Jasper in our bedroom.
An hour in, she excused herself to go to the bathroom. I was beginning to wonder whether the girls had backed out of the agreement they made, when Wendy came back, her jeans and shoes gone, and it took little time to see that she’d also relieved herself of the bra she had on, as her big tits were wobbling all around underneath the remaining tshirt the whole walk back from the bathroom. The tshirt covered her privates, barely.
Wendy was about 5’7″, three inches below my 5’10” height, although she often wore heels that put us eye to eye when standing. She had straight, sandy blond hair down to her shoulders. She was really smart, contrary to the cliche. She was my favorite study partner, because she helped me at least as much as I helped her. Because we were both pursuing the same double major with a minimal number of electives, we wound up in a lot of the same tough classes, and had started studying together Freshman year, when we were all in the dorms. Her roommates became my study pals because of her, Susan first, then Colleen and Dani, whenever we were all in the same courses, later without Wendy involved.
With a big bust and a curvy butt turned into an hourglass shape by a well-exercised abdomen and a narrow back, she was also the girl most likely to give me an erection during a study session, which I always hoped she wasn’t noticing. She’d never said anything but you never know. She did not have a reputation as a tease but I would have made an easy target. If I had wished for any of these four girls to be my first, it was her. Although I hadn’t admitted it even to myself, I was in love with her. I just didn’t know what to do about how she made me feel. She was about to teach me.
When she immediately straddled me on the couch, there was zero chance of her not noticing the erection I’d sprung from watching her jiggling towards me. After a brief look into my eyes for approval, she kissed me full on the mouth. Out of instinct more than anything else, I wrapped my arms around her, and pulled her boobs into my chest. Oh, they were so soft, pressed against me, and my dick got even harder, causing her to squirm her hips as she recognized what was growing stiffer under her.
I slid my hands down her back to grab her ass, realizing I hadn’t felt her panties. Was she fully nude under the shirt? I slipped a hand under the shirt, confirming nothing but bare skin.
She pulled away from the kiss and, looking at me again, said, “Well, your hands are certainly not shy.”
I nearly stuttered, “N-no. My… my prob… my problem’s… always been with… talking,” I managed to get out.
Wendy softly asked, “If I lead, and tell you what to do, can you follow?”
I could only nod.
“Kiss me, Kurt.”
I did. It might not have been the most impressive kiss in the history of kisses, but it was the first romantic kiss I had ever initiated in my life, a milestone kiss for me, the one I would always remember. Wendy’s lips were soft against mine, at first, but she pressed against mine in a way that made them firmer, her breath against my face as we breathed through our noses was warm, and I smelled her sweet, musky perfume as I inhaled.
She ran her tongue against my lips for a few seconds, before she pulled back, saying, “That tongue is a signal to open your lips, Kurt,” before she kissed me again, and this time I opened my mouth. Her tongue entered it, to play with mine. I played back. My hands went back to the bottom of the tshirt. I ran my hands over her buttocks, eliciting a small moan from Wendy, which only encouraged me to squeeze her butt a little more.
Wendy slid off of me, down onto her knees between my legs. “Take off your shirt,” she said, as she pulled my sneakers and socks off, then reached for the belt to my pants. güvenilir illegal bahis siteleri It soon joined my shirt and shoes in a pile next to the couch.
“Has a woman ever given you a blowjob before, Kurt?”
“N-No, never,” I answered.
“Pants off, honey.” she ordered. I unsnapped and unzipped, pulling pants and briefs down my legs together, where Wendy helped pull them off of my feet. She leaned towards me, and said, “Take my shirt off,” and raised her arms. I leaned towards her, grabbed the bottom of the shirt, and pulled it over her head, and tossed it towards my clothes.
She was breathtaking. Her breasts, which I would later learn were 36DDs, were magnets to my hands. I tested their weight, as her hard nipples centered in broad aereola pressed into my palms. A small moan escaped her lips, as she leaned in to kiss me again, taking my cock in her hand, stroking slowly.
She began kissing down my jaw, to my neck, swirled her tongue around each of my nipples, causing my cock to spasm, as I saw some precum leak out, which Wendy spread across my glans. Soon, she was kissing and licking my navel, just inches from my cock.
When she kissed the head, softly, then extended her tongue to lick another droplet of precum off, I had to close my eyes to keep from cumming that very instant. I knew that if I watched her take me into her mouth, I would have lost it immediately.
Instead, she kissed and licked her way down the shaft. I opened my eyes when she gripped the base hard, to stop me from shooting off the moment she sucked one of my balls into her mouth.
“Gawd, Wendy!” I got out, feeling overwhelmed by the sensation of her warm mouth, her tongue sliding around my testicle. She repeated the same on the other nut, maintaining that grip on my cock until my need to cum receded a bit, then she began stroking up and down again.
Looking down at her, her mouth beginning to work its way back up my shaft, her tits pressing between my legs, the ends of her hair tickling my left knee and her naked back and ass the rest I could see of her, I said a small prayer that I wouldn’t wind up disappointing her, this goddess in the process of answering so many of my other prayers.
I didn’t care that she was doing this because my roommates had asked her to. I didn’t care that she was going to get $100 for it. I only cared that it was one of my best female friends I was going to give my virginity to, very soon.
Wendy’s mouth had reached the top of my cock. She repeated the grasp around my base at the same moment she swirled around the glans with her tongue for the first time. I arched my back, anyway. Her grasp tightened even more, as I felt my balls tighten up. She looked up at me, and said, “You’re not going to cum until I say so, baby, so relax a little and enjoy this.”
“I… I’ll try.”
The sensation of her mouth taking my head inside was unlike anything I had imagined it would be. I hadn’t imagined the warmth, hadn’t imagined the texture of her tongue sliding across my nerve endings, hadn’t imagined the suction. I sure hadn’t imagined also sliding across the roof of her mouth, to bump against the beginning of her throat, before she slurped back up to the head.
My brain surrendered to the experience, feeling instead of thinking, my fears of disappointing her, of being rejected by her, fading away, as I let myself be just my cock for a while, as she made love to it, as I let her love me.
She’d repeat that grasp around my cock several times, as she sensed I was getting close again. I was beginning to go crazy from being denied, but each time everything got more intense. I really thought my balls were going to explode if she didn’t let me cum soon.
“Please,” was the only word I could get out.
She must have taken pity on me, because the next time I peaked, she let my cum burst forth, deep in her mouth, where I could feel her swallowing as I pumped shot after shot of my seed. I think I blacked out, because the next thing I could remember was Wendy standing in front of me, pulling on my arm, saying, “Let’s get in bed, Kurt.”
I stood, still feeling a bit groggy, and let her pull me to my bedroom. She managed to roll herself onto her back on my bed and simultaneously pull me on top of her. My cock was just beginning to recover. Being pressed against her pubic hair, while she started to kiss me and I felt her nipples, I was soon rock hard again.
“Do… do I need a condom?” I asked, knowing Jasper kept some in his desk.
“No, baby, I’m on the pill,” she answered. “Are you ready for the next step, to stop being a virgin?”
“What do I do?” I asked, feeling stupid as I did.
“First, put your hands on the mattress by my sides, so you can take some of your weight off of me.” I did this, which pressed our groins together more tightly. “Get your knees onto the mattress between my legs, and I’ll guide you inside me, okay?” She spread her legs, as I shifted more weight onto my knees.
Wendy’s güvenilir bahis şirketleri hand slipped between us, I felt her slip my cockhead across her clit and down to her opening, then her other hand went behind my ass, and pulled me into her a couple of inches. “Now, it’s just a matter of pushing in and pulling out with your hips. Not too fast to start, I’ll let you know when to go faster or harder, okay, baby?”
I wanted to say, “Thank you,” but knew it would sound trite. Besides, it ought to be saved until after we were done. I began pumping into her, adjusting to the sensation of her flesh both sliding by and gripping me as I moved through them, every nerve ending tingling. I was glad for the first orgasm, as I knew I wouldn’t have lasted long without it.
I watched Wendy’s tits wobbling on her chest as I fucked her, and I leaned down to grab one of her nipples in my mouth, causing Wendy to moan, “Suck me, fuck me, Kurt. Oh, gawd, I’m gonna cum! Oh, baby, just like that! Fuck! Cumming!!”
Feeling her start to shake under me, squeezing around my cock, was marvelous I’d made a woman cum. Me, the last person I knew who was still a virgin, had not only stopped being one, I’d just achieved another dream as well. I kept sucking on her nipple and thrust harder with my hips, feeling my own intensity rising and rising.
“Oh, baby, so good,” Wendy said, breathlessly, when she stopped shaking. “Faster now, baby. Get yourself off in me. I want to feel you splash inside me.”
I released her breast and started slamming into her faster and faster, our pelvises slapping against each other, feeling my orgasm racing towards me. I screamed, “Wendy!” when I started to cum. And cum. And cum. I managed to not black out this time, and kept thrusting into her, hoping to get Wendy off a second time, but my cock softened against my will. I brought myself to a stop, slipping out, then rolled to my left, between Wendy and the wall my bed was against. I reached my hand over to rub her clit, only to find that her hand was already there, working furiously.
I leaned over to kiss her, one hand groping her closer breast, as I watched her get herself off next to me. She shuddered again, moaning into my mouth.
Once she was done, she turned her back to me, then snuggled her ass back into my hips, pulling my right arm over her, and under her breasts.
Cuddled behind her, I whispered, “So, I guess you won.”
“Won what, baby?” she asked.
“The $100,” I said, feeling her stiffen in reaction.
She rolled back over to face me, putting her left hand on my cheek. “You knew? It wasn’t about that for me, Kurt, you have to believe me.”
“I know, Wendy,” I said, taking her hand and kissing the back of it. “I overheard at the window the day Jasper and Tom arranged everything. Even if I hadn’t heard you girls raise your objections, that’s never been the kind of girl you are. Besides, I don’t really care if it had been the reason. However it happened, tonight is going to be a glorious memory for me, forever, when I got to make love with the woman who’s been closest to me these four years. Thank you so much. But I… I have to ask you something.”
“Anything, Kurt,” she responded.
“Can I… Can I buy your silence, for another $100? Don’t tell anybody that you succeeded tonight, until I’m ready to tell everyone myself? Tell them that we kissed a lot, but we didn’t go all the way, that I got scared.”
“Why?” she asked. “I would think you’d be happy to let your best friends know you weren’t a virgin any more.”
“Normally, I might,” I said. “But this bet changes things. What happens if you go back to your roommates and mine and announce that you won? That would be it, it would be over. And any shot I have at being with the other three girls goes away with it. I would rather they still thought they have a shot at winning, if you don’t mind.”
Wendy giggled. “Oh, you do have a naughty mind, under that shy exterior. Okay, I’ll keep quiet, but I want something else instead of the $100.”
She kissed me quickly before saying, “After you manage to get with all three of my roomies, I want one more night with you before finals, then another before graduation. Deal?”
We snuggled for a little while longer, before she got up and got dressed, then slipped out of the apartment to get back to hers, about half an hour later. I picked up my own clothes and was asleep before my roommates returned.
Susan – always Susan and never Sue or Suzy – was a 5’3″ black-haired beauty of Jewish heritage, although she herself claimed to be agnostic. Her curly hair was down to her mid-back, slender everywhere but her C-cup tits, which she tended to leave braless all the time. The closest I ever came to flirting with her was one day during the preceding winter when she came into our apartment looking for Jasper. Her nipples were very prominently popping out against her grey sweater. She hadn’t bothered putting a jacket on, that’s how close the two apartment doors were. I asked, “Cold out?” while looking right at her chest. Her answer was a swat on my arm, and a blush of her pale skin, while she tried to cover up with the other arm. The image is burned into my brain forever, though.
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