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 girl I need to pay to have sex with me. I want it to at least be a girl who likes me, and 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. And so long as I kept my focus on studying, I did just fine being around them, and 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, and 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, sharing the entrance to the stairwell that led to the two floors above us. It was occupied by four women, Colleen, Danielle, Susan and Wendy. All of them had been regular study buddies of mine multiple times over the years, and all four of them were gorgeous. 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. 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, and 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 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 the following 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 blonde hair down to her shoulders, but 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 Danielle, wherever 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, and realized I hadn’t felt her panties. Was she fully nude under the shirt? I slipped a hand under the shirt, and confirmed 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, and her tongue entered it, to play with mine, and I played back. My hands went back to the bottom of the tshirt, and 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. 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, and I tested their weight, as her nipples pressed into my palms. A small moan escaped her lips, as she leaned in to kiss me again, and took 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, and 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, and extended her tongue to lick another droplet of precum off, I had to close my eyes to keep from cumming that very instant, because 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, and 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, and 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, and 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 the 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, and I was beginning to go crazy from being denied, but each time everything got more intense, and 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, and 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 hand slipped between us, and felt her slip my cockhead across her clit, and down to her opening, and 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 insides 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, and 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, and I brought myself to a stop, slipping out, and 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 not?” 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 them, I want one more night with you before finals, and 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.
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, and 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.
It was on my mind again on Tuesday night, when she asked for some help with a math course I had aced the year before. I suspected a ruse, since Wendy had taken the same course, besting my grade by two points, and I was right, as she leaned over to kiss me five minutes after I got into the girls’ apartment, as we studied on their couch. Once again, a suspicious lack of roommates around. She was in a short sleeved grey sweater, and a matching skirt.
I kissed her back, and my hand went to her hip, as we turned our bodies towards each other. I answered her tongue with my own, and she nearly squealed into my mouth. I was giving her more than she expected, and she liked it.
Both of my hands were working their way up her sides, while she was holding the back of my head, pulling us together. I reached the bottom of her sweater-covered breasts, and paused for effect, trying to act more hesitant than I actually felt, before moving my hands over them, to reach the same hard, pointy nipples that had been the feature of a lot of dreams over the past months.
I squeezed each one between thumb and index finger, and pulled them away from her chest, and got a loud moan into my mouth as feedback.
“Oh, wow, Kurt,” she gasped, when we broke from the kiss. “How did you guess my tits are my most sensitive area? You’ve got me so wet, right now.”
“I guessed, that if your nips were going to respond from just a few seconds of cold, that they were extra sensitive. I’m glad I was right.”
She smiled her naughtiest smile. “I want to make you gladder.”
“Are… are you… offering… offering the same… same thing Wendy did, last night?” Even knowing the answer, my tongue still got tied up by the question.
“Yes,” she said, taking my hands in hers. “Do you mind telling me why you turned her down?” Clearly, Wendy had been quizzed, and I wondered whether the girls were coordinating their order of attack, and wondered briefly whether it would be Colleen or Danielle next, before returning my attention to Susan.
“Maybe later,” I answered, before kissing her again. “I want to be thinking about you, right now, don’t you think?”
One of her hands let go of mine, and grabbed my cock through my pants, and I grabbed her breast again in response.
“Let’s go to my bedroom,” she suggested.
Taking her hand, I helped her up, walking into her bedroom, where she draped a sock over the door handle, in the universal “busy here” signal I’d been dealing with from Jasper now and then since Freshman year. As soon as she turned back into the room, I started to undress her. I think my taking charge was surprising her, but so long as I wasn’t trying to talk, I could act bolder than I otherwise might. Being with Wendy had also boosted my confidence, it seemed. I wasn’t as afraid of disappointing Susan as I’d been afraid with Wendy. I was still nervous, but not terrified.
Naked, we got on her bed together, and began kissing again, our hands roaming over each other’s bodies. I pulled back from her mouth, and whispered, “Could… could I lick you?” I’d not gotten a chance to do this with Wendy, and really wanted the experience.
Her eyes widened, but she nodded. I kissed my way down her body, taking about a minute to lick each breast. When I was down between her legs, I looked up at her, and asked, “How do I start?”
Her blush actually made me excited, knowing that I wasn’t the only one with nerves. Wendy’s take-charge attitude had been exciting the night before, but it also felt good to be on a more even footing with Susan.
“You see how there are two sets of lips?” I nodded. Her inner ones protruded slightly, a scarlet color I knew was from them being filled by blood as she got excited, and she clearly was. “At the top of the inner ones is where my clitoris is, surrounded by its hood, like your cock is covered by its foreskin when you’re soft. It’s the most sensitive part of my genitals. Sometimes too sensitive, if you’re too forceful too soon. You need to get the rest of me excited first, so start by kissing and licking my lips, and I’ll tell you when to move on my clit, okay?”
“Okay,” I answered, taking my first hesitant licks. I figured that Susan had probably washed up before I arrived, so her taste was fairly mild, a little bit of musk, a little bit salty. As I licked her, staying away from her clit, I sensed more and more moisture flowing out of her, and her taste got a little stronger, but I liked it, liked exciting her, liked her a lot.
On my own initiative, I licked around her opening, and she cooed, “Yes, like that. Lick my pussy,” A couple minutes later, she told me, “Kurt, push your middle finger inside me, then explore the surfaces towards my tummy. You should find a rough spot inside. That’s called the g-spot. It feels real good if you rub that.” I followed her instruction, and soon found the spot she described.
“Oh, yeah, Kurt. That’s it. Stroke that a little while you start licking towards my clit, really gentle though.” I followed her direction, and her back arched when I ran my tongue across her clit for the first time. “A little softer than that at first, honey, and just a little at a time. Use just the tip of your tongue, and work me up to wanting more.”
I tried just barely making contact, and Susan moaned, letting me know I was doing better. I resumed stroking her g-spot lightly, and thrusting my finger in and out a little.
“Oooh, yeah, I like that,” she said. “A little more time on the clit, but still gentle,” she said.
I complied, doubling the amount of time I spent licking her clit, before circling back to lick the length of her lips and back. When I returned to her clit, she put her hand on the back of my head to let me know not to leave again, then whispered, “A little harder.”
I continued licking around or over her clit, as she asked for increases in intensity or duration several times, as well as asking for a second finger. She was panting, thrusting her hips, and when she screamed and her pussy walls spasmed around the two fingers I had in her, I knew she was cumming. I increased my tongue action, and her orgasm seemed to intensify, her body shaking under me, until she slumped and she pushed my face away, saying, “Sensitive, enough.” I withdrew my fingers, and crawled up beside her.
She kissed me, before I could ask her whether her own flavor bothered her. She pulled back, and looked me in the eyes and asked, “That was really your first time licking pussy?”
I nodded, and asked, “Did… did I do good?”
“Mmmmm, yeah,” she answered. She reached down, and grabbed my dick. “Now for the main event. Are you ready to give me your virginity? I’m on the pill, so don’t worry about a condom.”
“Gawd, yes.” I momentarily felt shame at lying to her, but I couldn’t deny wanting her badly.
“I want to be on top,” she said. “I’ve been told I’m a bit small inside, so I like to control how deep a guy goes the first few times we’re together.” I couldn’t imagine my 6″ dick being too big for her, but she knew her own body best.
“You think… you think I’ll say no?” I got flat on my back, as Susan straddled me. Her hair surrounded my face, as she reached between us to take my cock in hand, and line me up.
She was so much tighter than Wendy! But all of the extra juiciness from my saliva and her own excretions made it fairly easy for me to slide inside, and soon she was pressed against my pubes. She kissed me again, trading tongues, and I supported her upper body by holding onto her breasts, and playing with her nipples, as she began rising and falling onto my cock.
“You can thrust your hips up into me, too,” she suggested. I’d been holding off on doing that, not wanting to seem too experienced, but was soon slamming up into her on each of her downstrokes. I felt her start to shake again, amazed that she’d come again so soon. I was just beginning to feel the beginnings of my orgasm.
“Oh, you’re the perfect length for me,” she said, when she settled down. “Why did we wait so long to do this, again?”
“I was too scared to make a move?” I suggested. “I didn’t know you wanted – ” She cut me off with another kiss.
“I want,” she said. “I want you, to fuck the hell out of me right now.”
I did my best, thrusting into her faster and faster, squeezing her nipples, as we both went into oxygen debt, panting like crazy. Just as I felt myself start to cum, I pulled both of her nipples away from her chest, and squeezed them, probably too hard, and she screamed, but she also came once more, as I shot stream after stream of cum into her.
Gasping for breath, we held each other, as she lay atop me, her thick, curly hair all around us. I ran my hands around her back, as she continued having little shudders from the contact, and my cock slipped out of her.
Confession time. “So, about Wendy?” I began.
“Yeah? About why you turned her down?”
“Not exactly,” I admitted. “It’s about how I didn’t turn her down, but asked her to say I did. And why I’m going to ask you to do the same, for a little while longer. I can even offer $150 as incentive.” I’d taken $300 out at the ATM, thinking I’d need $100 for each of the first three girls to buy their silence until I got to the fourth, but since Wendy had passed on it, I could split it up two ways instead of three.
“You mean, I wasn’t your first after all?” she asked, a little anger to her voice.
“Don’t be mad at me, Susan. I only asked Wendy to be quiet so I’d have a chance to be with you, too, instead of Jasper’s stupid bet being over. I know that if I had to go back to being the one to make the first move, I never would, and I really wanted this with you before we graduated and I might never get another chance. Can you forgive me?”
“And now you want me to be quiet so you get a shot at Dani and Colleen, too?” she asked.
“Yes. Is that so wrong? More wrong than accepting a bet or bribe to take my virginity, something I was always willing, but dumb-fucked unable to do on my own? If I’d just been a normal guy, I bet I would have dated all four of you by now. I’m just trying to get caught up a little.”
She said, “A normal guy wouldn’t have made such a great study buddy, Kurt. So, I’m glad you’re not a normal guy, and could be such a good friend to me, instead. I can accept being your number two, and yes, I’ll keep quiet. On one condition.”
“And what would that be?”
“You can keep the money, but I want a couple more nights with you, after Danielle and Colleen are done with you, one before finals, and one before graduation,”
I could only chuckle, which made her glower at me. “What’s so funny?”
“Wendy asked for the exact same thing. Guess I’m going to be busy between now and Graduation.”
“Oh, she did, did she?” Wendy asked, before pulling her covers over us and snuggling in tight against me, and we soon fell asleep.
I awoke in the morning, when Wendy snuck into the room she shared with Susan to get some clothes, before an 8 AM class. Susan didn’t wake, and I blew Wendy a kiss, which got me a smile. I didn’t know whether Colleen or Danielle knew I was in Susan’s bed. I knew they also had 8 AM classes, so I waited until 8:05 to shake Susan awake so I could give her a proper goodbye, and snuck back to my own apartment.
And ran right into Tom and Dave, who were having cereal for breakfast.
“Where did you spend the night, Kurt?” Tom asked, grinning, clearly expecting any answer but the one I gave him.
“Fell asleep studying with Susan, and she let me sleep in her bed,” Well, it was partly true.
Tom and Dave exchanged the most transparent looks, and I had to force myself not to laugh or smile. As much as I appreciated their concern for me, it served them right for plotting behind my back.
I said, “Got to get ready for my 9:30 class,” and headed for the bathroom to grab a shower.
Colleen and Danielle both asked me to study with them Wednesday night, and I wondered how they were going to peel one of them off so the other could seduce me.
They could nearly have been twins, two brunettes with similarly short hair styles, petite figures both at 5’2″, the distinguishing difference being Colleen’s pixie nose, and a slight elvish look to her left ear, where there was apparently a quirk to the cartilage that made that ear look pointy.
They had started out Freshman year with Colleen as Wendy’s roommate, and Danielle as Susan’s, but they bonded over a history of being football cheerleaders at competing High Schools in our city. The girls swapped roommates the following year, and the four were in the same apartments Junior year and now.
They were also the girls most likely to be caught sneaking out of my roommates’ rooms in the mornings, over the past four years. Why they never seemed to couple up with one of them, I didn’t know.
I shouldn’t have bothered wondering which of them would pursue me next, because the two decided to double-team me from the beginning.
I almost froze when Colleen kissed me on the mouth while Danielle began licking my ear, then I let go and allowed them to take charge, as they both pulled me into their bedroom.
It would have been a tight fit on the bed if we’d tried to lie side by side, but I was soon on my back, with Danielle riding my cock, while Colleen rode my mouth. I was a little surprised that Danielle’s pussy was not quite as tight as Susan’s, even though she was an inch shorter, but I was sure not going to complain about it. I let them give me direction here and there, still trying to not look like I had any experience, instead of just being inexperienced, Colleen’s flavor was a bit tangier than Susan’s was, her clit a little bit harder to find, but her reactions once I did were explosive, coating my face with her cream, and squeezing me between tight thighs.
“Oh, gawd, Kurt, I think I love your tongue,” Colleen said. “You get a bit more experience, and you could have any woman on campus.” I just continued licking, adding a finger into her when she asked, as I felt my orgasm getting closer, and focussed on thrusting up into Dani as she began moaning louder and louder. I grabbed onto her hips, and upped my pace as I lost control and came into her, just as her own orgasm started, and I kept thrusting as long as I could, as she screamed and jerked over me.
She fell to my side, and Colleen hopped off of me, to get into a 69, while I watched, my erection returning in record time. Colleen looked up, licking some of my come off of her lips, and said, “Would you like to learn doggy style, Kurt? Get behind me, and put that cock to good use.”
I knelt behind her, and was tempted to just watch Danielle’s tongue dance across Colleen’s pussy, wanting to learn more, when Colleen wiggled her hips at me. I fumbled a bit trying to line myself up with Colleen’s opening, and Danielle helped me, then licked at my underside as I slid into my last pussy of the four.
The sensation of having a tongue and pussy caressing my cock at the same time was yet another new one, and I really didn’t last as long as I had hoped to. The girls didn’t seem to mind, as Danielle burrowed her tongue into Colleen as soon as I withdrew. I just continued to watch, in awe at the Sapphic display in front of me.
They orgasmed simultaneously, then came after me one more time, kissing me, and giving me plenty of compliments, before we lay down together on the bed, pretty much covering every inch.
“Time for us all to come clean, ladies,” I said, as Colleen cuddled behind me, and Danielle in front of me.
“About what?” Danielle asked.
“I’ve known about the bet since the beginning. I overheard the whole thing through Wendy’s window the day it began.”
They started laughing. “What’s so funny?” I asked.
Colleen pinched my earlobe, then said, “That wasn’t the real beginning, Kurt, and you were meant to hear what you did. We were waiting until we saw you walking up the path, before we all went into our act.”
She said, “This was all Wendy’s idea, from the beginning, to take you to bed as a thank you for helping her so much these last four years. She’s the one who wanted to make sure you didn’t leave college a virgin, so she arranged the whole thing. From your roommates suggesting that you get a prostitute, knowing you’d say no, to letting you overhear about the fake bet. She thought that if she tried to approach you normally, that you’d get scared off. But if you thought it was all a secret plan to get you laid arranged by your roommates, you’d have some time to adjust to the idea, and let her take the lead. The whole idea was for her to win the bet. And it worked, too, didn’t it? Of course, she didn’t expect you to then want all of us, but she realized when you asked her to be quiet about it that we all had just as much to thank you for as she did, if not more. You kept me from failing two courses that I know of, and Danielle another, not just getting me to a D, but to a B and C. Susan has wanted you from the first day we met you as Freshmen, but she’s a lot more like you than you realize, unable to take the initiative with a guy. She’s better when she’s pursued, but you were always the one she wanted to do it, and you didn’t.”
“I wish I could have…” I said.
“It’s okay, Kurt, we love you anyway,” she said, tousling my hair.
Colleen leaned away from me as Danielle picked up the thread, “So, when Wendy told us that you were expecting us all to make our move with you, it took us each only ten seconds to agree to it. We let Susan go next, and I’ll tell you it was only finding out from Wendy that you wanted her too that let her play her part. She would have been too scared, otherwise. She also had a hard time pretending to be mad at you when you revealed that you’d had sex with Wendy first, since she already knew it. Colleen and I decided to do you together since we couldn’t decide between us who should go actually go last, and thought it might be easier to get you to go along with a threesome if you had Wendy and Susan before us. Besides, that let us be another first for you, your first threesome. Susan got to be the first pussy you licked, so I think it worked out well for all of us.”
At that moment, the door to their bedroom opened. In walked Wendy and Susan, in rather sheer nightgowns, and they sat down on the other bed. “Hey, boyfriend,” Wendy said. “Colleen sent us the all clear.”
Colleen waved the cell phone that had apparently been on the window sill next to the bed.
“Are you mad at us? At me?” Wendy asked, looking scared for my answer.
“Why would you think that?” I reassured her, pushing myself up on one elbow so I could see over Danielle. Somehow, being naked actually helped me keep my guard down. “These last few nights have… have fulfilled every fantasy I ever had about the four of you since we first met, but could never make come true on my own. If I had graduated and only made love with one of you, it still would have been more than I expected to happen. Somehow the four of you agree amongst yourselves to share me for a few days while letting me think it was somehow all my idea, and I’m supposed to be mad?”
Wendy and Susan both relaxed, and Wendy asked, “I don’t want to put you on the spot, but if you had only been allowed to have one of us, who would you have wanted it to be?”
I knew the right answer immediately. “You, Wendy. It’s always been you. I… I love you.” Why did it still have to be so hard to say? “I think I always have, and needed this experience to show me that.”
“I love you too, Kurt,” Wendy said, a tear sliding down her cheek into the corner of her mouth, where she instinctively licked it away. “You do still have promises to keep, you know. You promised Susan and I both two more nights before we graduate,” Wendy said, and when I looked over to Susan, she was trembling.
I hopped right over Danielle, not caring that I was still nude, and sat beside Susan on the empty space on the bed, with Wendy on her other side. “What’s wrong, Susan?”
She turned and buried her face in my shoulder, sobbing. I looked over her to Wendy, who mouthed the words, “She loves you, too, dummy.” Oh, gawd. I had just professed my love to Wendy in front of Susan, having learned mere minutes before that she had harbored an attraction for me since we were Freshmen. Damn, I can be dense sometimes.
I slid my right hand under her chin, and lifted her head up until I was looking directly into her bright green eyes, noses nearly touching, and wiped some of her tears away with my left thumb. “Honey, I have more than enough love in my heart for both of you, for all four of you, for that matter.. I may… may have fallen in love with Wendy first, but I love you, too, Susan.. I’m just now admitting that to myself, because I hadn’t let myself feel those things, in order to not lock myself up. That seems not to be as much of a problem right now, thankfully. I can’t pinpoint when it happened, maybe that cold day you walked in with your high beams on, and you looked so vulnerable when you realized it,” which earned me a chuckle around the room – apparently the story of that one-minute encounter was legend now, “but I am in love with you. I chose being your friend over taking the risk of being more, with either of you, but I don’t want to make that choice any more. I can’t really imagine my life without you… without the four of you in it, either as friends or… girlfriends.” I emphasized the plural, and Susan’s eyes went wide, just before I kissed her, and she hugged me tight.
“You… you want both of us?” Susan asked, and kissed me again when I nodded.
When we parted, Wendy leaned over for a brief kiss of her own. I said, “I’m so glad we’ve all found jobs here in the area, even if all I was anticipating was that we’d stay friends after college. I don’t really know where we go from here, but I want it to be together, wherever it is.” I looked around for validation.
Colleen coughed, to get my attention. “You do realize I just inherited my grandmother’s house, on the other side of the city, don’t you? Five bedrooms, three baths, more than enough room for the eight of us.”
“Eight? You mean Jasper, Tom and Dave, too?” I asked.
She chuckled, before saying, “He’s catching on, girls. Kurt, Danielle and I have had a pretty regular thing going with all three of your roommates starting Freshman year, pretty much every combination possible from twosomes all the way to all five of us at once. We were never quite sure who would wind up with who in the end, until we finally said, ‘Fuck it,’ and decided that we both love all three of them, and they love us, and that works for us. They avoided making any moves with Wendy and Susan, because everyone other than the three of you could see that you were the one they both really wanted, even when you all wouldn’t admit it to yourselves, and they hooked up with other guys here and there instead, but I’m sure you must have noticed they never lasted very long, always coming back to being your study buddies and waiting for you to do something. Also, the guys haven’t flaunted their relationship with us in front of you, knowing that you weren’t getting any and they didn’t want you to feel bad, so we mainly got together at our dorm rooms or apartments, rather than yours. Or did you really think that studying with you was the only reason we chose the apartment next to yours?”
“Are they going to be mad you were with me?” I asked.
Danielle answered, “No, we got their permission for us to be with you tonight first, and I don’t think that has to end with tonight, either. They’re as ready to share with you as they do with each other. Nor do I think they’d object if Wendy or Susan wound up in any of their beds some night, if you’re willing to share, too. Just because they backed off for you doesn’t mean there’s no attraction there. I know this might be moving really quickly for you, Kurt, but do you think we could all live and love together, all eight of us, perhaps as two polyamorous marriages that sometimes swap with each other?”
My head was swirling, but my heart and the looks of approval on Wendy and Susan’s faces answered for me. “I wouldn’t have it any other way.”
Author’s note: I took a slightly different approach, writing everything but the sex scenes first, about 5000 words in 5 hours, then went back and filled in the sex, and then proofread and polished the whole. What do you think? Constructive feedback is how I learn what you liked and didn’t, so I can decide what I need to do better in my next work. Thank you in advance for your comments and votes.