Virgin
2006-04-29
I come like crazy every time I feel his hot jizz shooting into me. Jesse definitely created a monster; being on the pill is fuckin' great! Oh, and he did take my virgin ass on his 18th. He absolutely loved it, which came as no surprise, but what I didn't expect was that after I got adjusted to it I loved it too! Now it's something I save for those special occasions where I wanna give Jesse a real treat. Which brings me around to where we are now. Both of us applied to and were accepted by Colorado State University in Fort Collins. Since men and women can't share a dorm, neither of us wanted a roommate, so we both applied for singles and got them. We somehow wound up with two right next to each other, which tells me we must have done something very good in a past life or something. Oh, and we also share a common bathroom with the entire floor. Hey, it's college. Use your imagination. Jesse is majoring in business right now, but he's not really sure that's what he wants to do. I'm completely undecided. We've kicked around the idea of starting up a bar or nightclub after we get out of college. I absolutely love the idea of being the owner of a swinger's club, but I don't really have any idea what all is involved or how the legality of it works. Not that it matters; we have a couple years at least to figure it out, probably way more since it's sure to take a lot of money. Oh yeah, and Jesse and I have begun talking about getting married.
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Yeah, I know, I know what I said, and in a way nothing's changed. I still love him, but not in that way exactly. I dunno, to be honest I'm not really sure how I feel. He's my best friend. And confidante. And whenever we're horny we fuck. Beyond that. . . well, I really have no clue. What I do know for sure is that at the beginning of the year Jesse hooked up with this girl and I couldn't stand her. All of a sudden Jesse wasn't mine anymore, he was hers. She was talking marriage for awhile, and it freaked him out, which is part of why he eventually dumped her. But it got me to thinking, since I couldn't stand losing my best bud to some other girl, why not just ask him what he thought about us being. .
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. well, an us? So I gave him a couple weeks to get over her and then dropped the bomb on him myself. That really freaked him out and for awhile there I was sure I'd lost him, just like I was always afraid of. But the nice thing about Jesse is that he's always been pretty reasonable and cool-headed, and he literally knows me better than I know myself. So after a truly miserable week of avoiding me, sitting as far away from me as possible in our classes together, and locking himself in his room, he finally broke down and asked me "what in the hell I was thinking. " After a tense couple hours of chatting he and I were pretty much on the same page, which was to say we didn't have a fucking clue how we felt about the whole mess. But we've had a couple very long months to think it over, and I gotta admit that the more I think about it the more I start to like the idea. From what I gather, so does he. No other two people on the planet are as comfortable with each other as we are, so that helps some. And we already have sex every night, so exactly what's missing isn't very clear. I dunno, the more time that passes the more I'm sure we're just destined to be together. This week I finally reached the point where I just decided to start figuring out how I'll propose to him - I'm sure you know by now I'm hardly a traditional girl. Anyhow, that's where we are today. But for now I wanna explain our first party, just like I promised I would. It was 5 years ago, in 8th grade.
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Dad was still a travelling businessman, so he was away as usual. Mom was in bed with a pretty bad head cold, which is probably why we were allowed to have the party in the first place; Mom figured she'd be able to keep an eye on us. That part always makes me laugh. She was absolutely exhausted so she slept during almost all of our party, which turned out to be a really good thing!It was a saturday; I remember that because when I called up Jesse he yelled at me for interrupting X-men during his saturday morning cartoons. "Shaddup Jesse, it's a rerun anyway," I laughed. "Mom said I could have a party, wanna come over?""Sure, as soon as the episode's done. " I rolled my eyes. I liked X-men too, but Jesse's interest bordered on the fanatical. "Cool. Mom said a small quiet party, which I think means six max. Who all do you think should I invite?" I had a fairly big circle of friends, but they weren't that much more than acquaintences really. My only truly close friend was Jesse. "Lessee. . .
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Umm, Gabby, probably. And Jason. And Rick and Tina probably, they hang out together a lot. And you and me obviously, that makes six?" I counted in my head. "Yeah, six," he repeated. "Or did she mean six friends, plus you?"I shrugged. I use a lot of pointless body language while I'm on the phone. "Whatever, that's fine. Do you have the numbers for Rick and Tina? Uh, and Jason too, I have his somewhere but I don't know where I put it. " Rick and Tina were first cousins; Jesse had told me they'd fooled around before but I always figured they were too shy and he was pulling my leg. "Think so. . . Yup, found 'em. Want 'em?""Sure.
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" I scribbled down the numbers he gave me, thanked him, and hung up to call the others. An hour later the six of us were chilling in front of the TV, watching a movie on tape. Jesse caught my attention and quietly asked if I'd go check on my mom. I gave him a funny look but got up to do it anyway. I went upstairs and cracked open her door. She was lying on her side, snoring fitfully. When I headed back downstairs Jesse was pulling a video tape out of the backpack he'd brought. He glanced back at me, and I closed my eyes and dropped my head to one side, pretending to be asleep. Jesse grinned and popped in the tape, turning the volume way down. "Is that. . . ?" I began in a low voice, staring at him. His grin told me everything. "Is that what?" asked Gabby.
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"A porno. Jesse told me he had one and that he'd bring it over sometime. I wanna see!" I bounced eagerly back into my seat, anxious to see this mysterious porno tape. Gabby looked shocked, but Tina was pretty calm and the guys all seemed excited. The tape was cued up to a closeup shot of some guy's cock going into a pussy. Gabby said "gross!" but kept watching intently anyway. Everyone else was sitting in silence gawking at the TV as a large-breasted girl got banged by some sweaty guy with an enormous dick. We watched probably two minutes of hardcore fucking before I broke the spell enough to turn to Jesse, who was grinning at the action on the TV. The fact that he had pitched a pretty decent tent in his pants wasn't lost on me. Perhaps I should pause for a little more background. See, I've known Jesse since before I can remember. We grew up together, him and me; he was the boy next door, both figuratively and literally. We even took baths together when we were toddlers, when I'd play over at his house or he'd play over at mine. I grew up to be a bit of a tomboy, at least until puberty hit. And probably even some after that, actually.
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So we hit it off famously. The first time I remember exploring my sexuality was with Jesse, at age six. It was the typical "If you show me yours I'll show you mine" scenario, and although we touched each other a little bit, nothing really happened. Whenever we put on a movie, whether at his house or mine, it wasn't uncommon for us to snuggle up on the couch under some blankets, which sometimes gave us a good opportunity to play with each other's crotches. But it was never really more than something fun to do with our hands while we watched, that also happened to have the added thrill of being something forbidden. The next major milestone I recall (as far as sex goes) was at age eight, when he actually made me come. We were just fooling around under the blankets like this and it felt good. . . and we kept fooling around and it felt really good. . . and then my sweet precious Jesse gave me my very first orgasm. Good thing his parents didn't hear me come or we'd have been busted for sure. I tried to do the same for him, but although I made him feel really good in return I don't think he ever climaxed.
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At eleven we discovered french kissing - he was my first kiss and I was his - and we made out often whenever we decided to fool around. I guess the association has stuck with both of us even today, because Jesse loves to make out with me while we're fucking, and whenever we kiss I immediately start to get a little wet. That's why we save kissing as a sexual activity only; since then I've come to strongly associate his tongue in my mouth with his cock in my pussy, which has made having quickies a lot easier. Sometimes when I'm really horny a big wet tongue kiss is all the foreplay I want or need!It was also at this point that I really started to discover all those fun words like "fuck" and "pussy" and "cock. " I'd heard the words a couple times before, but I never really used them until now. I used dirty words with Jesse often when we were alone together, talking about every conceivable aspect of sex in gloriously lurid, astonishly explicit detail. I really enjoy talking dirty with him (especially in our classes together!) even to this day. It wasn't until I was thirteen that we started getting serious. At that point I had hit puberty, as had he, and we were exploring our new "adult" bodies together. He had discovered big wet messy orgasms on his own, which he demonstrated to me to my everlasting amusement and intense curiousity. I showed off my newly acquired tits and the golden peach fuzz on my pussy, both of which excited him a lot. When we were alone together we began exploring mutual masturbation to orgasm and a little later, oral sex. Yeah, full-blown oral sex. By fourteen I was a very proficient at giving Jesse blowjobs, and he knew how to tongue me to an orgasm in nothing flat, especially if we were alone and I could moan as loud as I wanted without fear of getting caught. It didn't take long for us to discover sixty-nining, which immediately became our preferred sexual activity for when we got really hot and bothered together.
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Both of us had received "The Talk" and had been through a mandatory sex ed class or two, so we knew a decent amount by this time. While we were extremely curious about "going all the way," we both knew the consequences. The furthest we ever got was rubbing his dick up and down my pussy, which we did when orally pleasuring one another just wasn't enough. I enjoyed watching and feeling him come while he rubbed his cock against my pussy, but I was always concerned about him accidentally squirting some inside me so we didn't do it nearly as often as we'd have liked to. I can't even begin to describe how bad I wanted him inside me though. We both knew we weren't fucking properly and that as nice as this was it was still a poor substitute for the real thing. He must've felt the same way - although he's always been a perfect gentleman he says there were way too many times where he was ready to just say "fuck it" and push his dick all the way inside me, whatever the consequences. I bet I'd have ended up thanking him for doing it if he had. In any case, I pretty much took it for granted that Jesse would be my first; it was only a question of when and under what circumstances. Jesse tells me he "hoped" the same thing, without really "expecting" anything, whatever that means. Sometimes I think that boy must have been thick not to know I was going to go all the way with him sooner or later, what with all the other sex stuff we were already doing together. The final thing you need to know is that half a month prior to this party, I'd discovered a box of condoms in the back of my parent's dresser. In recent years Mom had developed uterine cancer and had beaten it. It ended up taking a hysterectomy, so they had no use for condoms anymore. That's probably why they never even noticed when I took them.
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So with everything I've just told you in mind, you probably have a much better understanding of what was going through my head as I stared at that very familiar bulge in his lap. "Wanna play strip poker?" I asked chipperly. The boys all eagerly agreed, followed by Tina. Gabby looked hesitant, but caved after a moment. I hopped up and got a deck of cards, then recommended we all head up to my room where we could lock the door. But first I had to check in on my Mom to make sure she wasn't going to interrupt us. I peeked my head into her room and noticed she was no longer in her bed. I heard her blowing her nose in her bathroom and slipped into her room as she shuffled back in, dressed in what I'd come to think of as her ratty "I feel like crap so don't bother me" bathrobe. "Hi Ma! How ya feelin'?""Oh, hi Racha. Howible. " She was really congested and looked like she had just gotten up after a long night and hadn't had her coffee yet. "Bummer. Need anything?" I offered, more to keep her out of our hair than out of courtesy or sympathy. "Dot relly. I just need to reth.
Go hab fun wit your fends. " She reclined on the bed with a stuffy groan and grabbed for the covers. "Okay, thanks Ma! Hope you get better!" I bounced out of the room, satisfied she wouldn't be checking up on us anytime soon, and headed back to my own room where the others were waiting for me. I smiled at them as I closed and locked the door behind me, then took my place on the bed with them, sitting crossleged in a tight circle. I pulled out the deck of cards and started shuffling. "Okay, how 'bout this? The winner of each hand collects a piece of clothing from everybody else. No jewelry or watches, socks don't count either. You hold onto the clothes you win and once you don't have any clothes left to bet with you have to start doing stuff for whoever wins instead. ""What do you mean 'doing stuff?'" Tina asked. "You have to do whatever the winner asks. " Gabby immediately protested and shook her head adamantly. "Well, maybe not anything the winner asks. Just like, touching them and stuff, you know? We'll take a vote on whether or not it's too much if somebody asks for something you don't wanna do. "This seemed to put her a little more at ease. "And let's make it okay to raise so we can up the stakes a little!" I grinned impishly at everyone in front of me and started dealing out the cards.
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Everyone fidgeted nervously, but their smiles showed they were eager to start. I dealt out the cards to everybody and looked at my hand, which I recall being absolutely useless. I don't really remember each hand well enough to describe it, which is just as well because the game was going much too slow for me and I was there for it. Let's just say that it took awhile before Jason's stiff little pencil dick was waving in his lap for all to see, and that Gabby and I got to touch it quite a bit since we seemed to be winning more often than anybody else. Eventually Tina got down to just her panties; she was an A-cup but had pointy little nipples that probably stuck out a good inch, and I could tell she was getting pretty hot and bothered. Next to her was her cousin Rick, who was also down to his boxers, with a very obvious erection tenting the thin fabric. Jesse was completely naked, but hadn't been forced to do anything yet. He kept grinning at me when he caught me stealing hungry glances as his erection danced in his lap. The next hand everyone folded but Jesse and me. I kept betting clothes and he kept betting more and more actions he'd have to perform on me should he lose. He was either bluffing to win back some clothes, or he had a hell of a hand. Or he didn't care if he lost and wanted to fool around with me, which I'm sure was the case too. But I had a really good hand, so I just kept going. Once I had bet all of my clothes against basically getting to have my way with him, I got an idea. "Okay Jesse, how 'bout this? If you win you get my entire pile of clothes and everything I'm wearing, and you can do anything you want with me.
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If I win. . . " I paused to smile evilly at him. "I own your cock from now on. " I grinned, daring him to accept. He looked at me curiously. "What do you mean?""Well, you can still use it to pee and stuff. Other than that, it belongs to me. I can do with it as I please, and you have to ask me before you can use it for anything else. " I sat back and smiled a challenge to him as he considered it. Jesse's as big a gambler as I am, and I could practically see the wheels in his head turning. If I win I get all her clothes and she has to do anything I want. And if I don't. .
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. What would she do with it if she won? Would she do nothing just to tease me? Or say I could never play with any other girls since it belongs to her now? Or would she actually. . . ? Hmm. "Deal!" he grinned at me. I grinned back and called him. The hand he put down had four threes and an eight. Very impressive. Mine had four nines and a two though. I swear my grin must've been ear to ear. "Ooh! I wanna play with my new toy!" I squealed, and bent down to take his cock in my mouth. I've always loved giving Jesse blowjobs, but this was the first time I'd ever done anything in front of anybody. Having an audience was only turning me on more!"Ohhh!" he shuddered as he felt my lips wrap around his tool. "Oh shit!" he said, probably realizing that those ifs he was considering a moment ago were now whens.
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I sucked him off for a few seconds, then stopped and grinned at him as I gathered my long blonde hair back behind my shoulders. "Remember, nothing without my permission, so keep your hands off my pretty new cock!" I taunted. I didn't really have any way of enforcing it, but it didn't much matter. In a sense I owned his dick already anyway; now it was just a little more official. "Wanna play truth or dare now guys?" Everybody smiled and nodded, eager to take things a little further. "I'll go first. Jesse, truth or dare?" He grinned. "Dare!" The others looked at him in surprise, expecting him to ask for a truth, but I knew him too well. I wasn't about to start off that quickly, or it might scare off Gabby and Tina. "Gimme a kiss!"He leaned over and kissed me quickly on the lips, then rocked back onto his seat with a silly grin. I was honestly a little disappointed. "Damn, I shoulda been more specific. Your turn Jess, pick somebody besides me. " He paused for a moment, looking around the group. "Rick, truth or dare?"Rick wasn't quite as ballsy as Jesse was.
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"Truth. ""Have you ever had sex with a girl?" He blushed and shyly answered yes, to just about everybody's surprise. I noticed Tina blush a little too, a detail I think was lost on everybody but me. "Rachel, truth or dare?" I grinned and said, "dare!""Um. . . I dare you. . . to pick one person and make out with them for a full minute!" Rick was a little too timid to ask for any of the stuff I know he really wanted to ask, which was a pity because I'd have gladly done just about anything he could've come up with. I literally grabbed Jesse and held the back of his head in a deathgrip as I kissed him feverishly, my tongue darting in and out of his mouth. I was actually disappointed when Rick called time and I had to return to my seat. My panties were soaked by now and I was looking forward to getting to take them off. "Tina, truth or dare?" She quietly chose the expected "truth," then blanched when I asked her if she was the girl Rick had had sex with. She hesitated, then nodded meekly.
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"Shit, wow! But you're cousins! You seriously fucked?" Jason said, not without a sly little smile. Tina blushed furiously and nodded again. "Your turn to pick somebody, Tina," I reminded her. She lifted her head and smiled before picking Jason, who chose "dare" with a grin. Tina thought for a bit before deciding on daring him to give her a back massage for a minute. I couldn't help but notice that during his massage he happened to graze her tits and stroke her panty-covered ass a lot, and she definitely enjoyed it. Although she seemed shy, I could tell she was getting excited and I figured we needed to start to heat up the game a little. When Jason was done he picked Rick again, who again asked for a truth. Jason grinned and asked him how many times he and Tina had done it. Both of them turned bright crimson and Rick simply said "a lot" before picking Gabby. Gabby surprised me by immediately choosing "dare. " I didn't figure she was the type, but when she was dared to take off all her clothes she did so, eagerly. She was fairly well developed, a little moreso than me, and I had fairly respectable tits at that age. I laughed in excitement and she immediately picked me. So of course I said dare.
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"Let Jason take off your clothes and feel your boobs. In that order. " She quickly added with a grin. My jaw dropped; I'd never have expected for her to push the game this far this fast, but I wasn't complaining. She must've been just as horny as I was. "For how long?""A minute," she replied, grinning. I was more than willing to comply, straddling Jason like I'd done with Jesse and thrusting my chest forward proudly. His hands fumbled with my top and pulled it off, then had some trouble undoing the clasp on my bra before he removed that too. I got up off of him and wiggled my hips to remind him that he had to take off all my clothes. I think he nearly had a heart attack as he pulled down my shorts, then my panties, exposing my little golden patch to everybody. He was so caught up in looking at my pussy that I actually had to remind him that he still needed to feel me up. Once I did, though, his hands zipped instantly to my tits, and judging by the look on his face after the minute was up he was totally walking on air. You'd have thought he'd just gotten laid or something. I sat back down on the bed, horny and rather pleased with myself. "Tina, truth or dare?" She grinned a shy little smile and softly said, "dare.
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""Take off your panties and Rick's boxers, and then let Rick finger you. For a minute. " She blushed, but stood and slid her panties down her legs then stepped out of them. She had little tufts of brown pubic hair above her puffy slit. When Rick rose she knelt and tugged at his boxer shorts, freeing his bouncing cock. She gave it the head a little kiss, which nobody had told her to do, then sat down and leaned back a little. She bit her lip as Rick reached between her legs to stimulate her. Everyone watched Rick pleasure Tina first with one, then two fingers. Her pussy was bright red and really wet, and it made little juicy sounds as she got fingerfucked. He fingered her for a lot longer than a minute before he withdrew his hand, Tina starting to breathe a little heavily. "Tina, pick somebody. " She looked around the circle with a really horny look in her eye. "Jason, I dare you to go down on Gabby. " Nobody complained that he hadn't been given a choice, especially since he probably would've picked dare anyway. Gabby looked really nervous, but I could tell she was eager for this opportunity.
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Even the three supposedly shy people in the circle were anxious to see how far this game would go. Once again, I guess Jesse just had a knack for picking 'em. She shooed the rest of us off the bed and stretched out, cautiously spreading her legs as Jason positioned himself above her pussy. "Till she comes!" I quickly added to Tina's dare, sure that nobody would protest. Nobody did. Jason wasn't that great at giving head, but fortunately after the first couple minutes of uninspired attempts Gabby started giving him subtle direction. He picked up on it and it wasn't long before she was moaning softly and clutching his head between her thighs. She was surprisingly quiet when she came, which was a good thing since my Mom wasn't all that far away. Jason sat up and wiped his chin as Gabby panted quietly, coming down from her high. His eyes immediately settled on me. "Rachel, I dare you to give me a blowjob. Till I come!" he added unnecessarily. I was surprised not only that he'd been so bold in asking me to blow him instead of one of the other two guys, but that he'd crossed over the unspoken divisions between the couples when it came to more serious activities like oral. I didn't really mind, however. I'd blown Jesse before, this'd just be a little extra experience with somebody new.
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He stretched out on the bed, taking Gabby's place as she got up. I propped myself up above his crotch and pulled my hair back, asking Tina to hand me a scrunchie from my dresser so I could put my hair up and keep it out of the way. When I was done I took Jason's thin little dick in my hand and started sucking on it, trying to get him off quickly. It couldn't have taken more than thirty seconds before he groaned and shot his wad into my mouth. I don't mind swallowing when I blow Jesse - I actually kinda enjoy the way his jism tastes - but Jason's spunk tasted strange so I got up to spit it out. "Oh God. . . Thanks Rachel, I had such a bad case of blue balls I thought I was gonna die. " I just nodded and found an empty cup to spit his semen into. I smacked my lips to try to get the taste out of my mouth, then realized it was finally my turn to pick and that everybody was waiting on me. My eyes landed on Jesse and I decided the game'd gone on long enough. I walked to my dresser and pulled out the hidden box of condoms. "Jesse," I said slowly and deliberately. "I dare you to go all the way with me.
"To his credit, he didn't get all wide-eyed like most boys seem to do when they realize they're about to get laid for the first time. His expression didn't even change at all, the only thing he did that told me how nervous he was right then was swallow right after I said that. "Ah, here, in front of. . . ?" he asked cooly. I nodded. "Uhh, Rach, I dunno if. . . I mean, I. . . Umm. .
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. Ahh. . . " That's the only time I can ever recall Jesse being at a complete loss for words. In my experience being told they're about to lose their virginity just does that to boys for some reason. "Look Jesse, I own your cock now," I reminded him. "And right now I wanna know what it feels like to have it inside me. ""It feels really good," Tina interjected bashfully. We all turned to her and she blushed and dropped her gaze back down to her lap. "Well, not at first I mean, but once you get past that part it's great!" She glanced over at Rick with a look of loving gratitude. Jesse glanced at her and then back at me, silent for a very, very long moment. "Okay," he finally said to me in a small, soft voice. "But I get to pick who goes next while we're doing it. Tina, truth or dare?"Tina smiled, a genuinely confident smile.
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"Dare!""I dare you to do it with your cousin while Rachel and I, uh, do it. " As if the dare would've been anything else. "I will if they will. " She turned to Gabby and Jason for their reaction. Gabby bit her lip in hesitation, then reached for a condom from the box. Tina did likewise. Rick just sat patiently and Jason got that same wide-eyed look I was just talking about. You can instantly spot a virgin boy by telling him you're gonna fuck him, I swear. After they'd gotten a condom apiece I read the directions on the box, since I'd never used one before. Tina unwrapped and unrolled hers onto Rick's cock, obviously having had prior experience, but Gabby asked for the directions herself once I finished reading them. I pulled a packet of condoms out of the box and tore one off, then opened it. It felt kinda funny, all rubbery and slimy, but kinda cool too. I looked up at Jesse; to most other people he probably would've looked okay, even a little indifferent, but I could see in his eyes how very anxious he felt. "C'mon Jess, just relax, okay? Please?" I whispered to him as I encircled his cock with my fingers and placed the condom at the tip of his dick. He tensed a bit involuntarily, but then looked at me and nodded, and I did feel him relax a bit.
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I rolled the ring of the condom down his shaft carefully, all the way to the base of his dick. Just then we heard Tina gasp pleasurably, and the four of us turned to watch her. She was laying on her back on the floor next to the bed, with Rick on top of her between her open legs. Her head was thrown back and her eyes were closed, wearing a big radiant smile of obvious pleasure as Rick's ass rose and fell slowly between her spread thighs. Her hands clutched his waist and pulled him gently into her. I really wished I could feel what she was feeling at that moment. She opened her eyes, beaming up at Rick, then her smile softened and her eyes crinkled a bit as she glanced up at the four of us staring at her. "C'mon guys, stop staring, you're embarrassing me!" She shrunk a bit, trying unsuccessfully to hide beneath her naked cousin. "Sorry Tina, you just looked really hot right then," Jason offered. She smiled and seemed to be satisfied with his response, then returned to enjoying Rick's cock buried inside her. I glanced over at Gabby; she had seated Jason in my armless computer chair and was finishing rolling the condom onto him. I turned back and made sure the condom was on Jesse properly, then looked up into his eyes and bit my lip. This was it. I laid down right next to Jesse, spread my legs, and pulled him on top of me. He kissed me softly as the underside of his rubber-coated cock rubbed against my pussy.
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"Are you sure you really wanna do this Rachel? It's gonna hurt you know," he whispered to me. "And besides, you might want to, you know, give it to somebody else later on. "I snorted. "Yeah, right. Why would I want anybody else to pop my cherry, Jess?" Then I realized maybe he wanted to save his virginity for somebody else. It was an unpleasant thought, but I'd honestly hate to deprive him of the opportunity if it turned out to be what he wanted.
"You know Jesse. . . we don't have to do this if you don't want to. " I whispered to him. This time it was his turn to laugh. "Rachel, we've been fooling around since we were little kids. I've been dying to go all the way with you for years - Hell, you're my best friend! Of course I want to!" He smiled down at me and kissed me as if I was his girlfriend, then put the tip of his cock at the entrance to my pussy. I spread my legs a little wider, waiting for him to push his cock inside of me.
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He seemed very hesitant and I asked him what was wrong. Then Gabby gasped sharply and gave a muffled "Ahh!" of pain as she pushed herself down completely onto Jason's thin cock, tearing her cherry, and I realized that Jesse was so nervous and hesitant simply because he was afraid he'd hurt me. Jason groaned a little too loudly as his cock slid into its first pussy and I frantically shushed him, hoping my mom was fast enough asleep that she hadn't heard. Jason was completely oblivious to everything except the warm, soft, wet tightness now enveloping his dick, though. He groaned again, a little softer this time, as he started bucking his hips up into Gabby trying to fuck her. She was just clutching the back of the chair in agony, however, and staying balls deep on his lap, trying to avoid any additional pain. Gabby grunted painfully from Jason's overeager thrusts into her, and I was a little surprised when Tina quickly jumped up close to the coupling pair, taking Jason's face between her hands none too gently. "Jason, stop!" she stage whispered to him. That evidently got his attention, as he stopped bucking his hips up into Gabby, and she sighed in relief. "You gotta go slow, it usually hurts a girl's first time. Let Gabby set the pace. "Jason apologized to both of them, looking embarrassed and ashamed; while he wasn't always the most considerate of guys, he wasn't really a creep either, just a little more self-absorbed than he should have been. Most guys genuinely can't help it their first time, I think. "You okay?" Tina asked Gabby, sincerely concerned for her friend. "Yeah, just gimme a minute.
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" She looked a little haggard, and I was beginning to have second thoughts about fucking Jesse. He was much more considerate than Jason was, but his cock was bigger than Jason's and I was pretty worried about how much it'd hurt getting all of him in me. "Don't worry, I know it hurts at first but it passes pretty quickly. After the first couple minutes it'll start to feel really good, I promise!" Tina was speaking to Gabby, but it might as well have been intended for me. She returned to Rick's eager embrace, and I considered what she'd just said. I decided I was ready after all, and I nodded to Jesse. He slowly pushed his dick into me. For a moment it felt good, feeling his cock pressing into my slit like always, but then I felt him push against my hymen and it started to hurt a little bit, more uncomfortable pressure then actual pain. He saw me wince a little I think, and pulled back some. "You okay Rachel?""Yeah, I'm okay, try it again. " He gently eased into me again, and again I grimaced a bit as he pushed a little harder against my cherry. When I gasped he withdrew, unwilling to hurt me. We both just lay there for a moment with disappointed looks on our faces. This was ridiculous, no way was this going to stop us from doing it. "Oh fuck it Jesse, just push it all the way in me.
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" He looked very unsure. "Don't worry about me, I'll be fine. " I reassured him. I wish I had had somebody reassuring me, though. I was scared as hell. "I dunno Rach, you sure?" he asked dubiously. "Yeah, just forget about me for a second, please? I only have to go through this once, and then we can fuck like rabbits. " I smiled up at him teasingly. He laughed. "Okay, if you're sure. " I nodded. He blew out a nervous breath, steeling himself up for having to hurt me. Then he shoved his dick all the way into me and I felt something tear inside. It hurt a lot, and I let out a little shriek as he exhaled with a shudder, feeling my pussy twitching involuntarily around his cock for the first time. He immediately held me tight and was looking me in the eyes with a really concerned look.
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"Are you okay Rachel?! I didn't hurt you too bad did I?!"I just looked back up at him and breathed out a barely audible, "oww!" His face sank and he hugged me tight. "I'm sorry," he whispered and started to withdraw before I wrapped my legs around him and instantly grabbed his ass to prevent him from pulling back out. Once he realized what I was doing and stopped struggling I hugged him back and waited for the sharp pain in my pussy to stop stinging so bad. I remember thinking that although I was definitely ready for it to stop hurting anytime now, it wasn't quite as bad as I had feared. Not that it was a day at the beach or anything, of course. I could hear Gabby rocking back and forth on Jason's cock; Jason moaning very quietly so as to not wake up my mom, Gabby gasping softly in pleasure or pain, I couldn't tell which. I could hear Rick breathing heavily down below the bed, and Tina gasping out "Oh Rick!" in pleasure as he fucked her. That gave me a little encouragement, knowing this hurt wouldn't last forever. And it definitely sounded like it was worth it. It didn't, and it was. We held each other for a few minutes as the pain began to fade, to be gradually replaced by a gently pleasurable sensation of being filled. Once it got to the point where it started to feel pretty good, I kissed Jesse on the cheek and whispered, "okay, you can fuck me now. " I can't even begin to describe how wonderful it felt to feel his dick slowly pull almost all the way out of my pussy, then come pushing back in until his pubic bone ground against mine. Ooh, it felt great!I cooed to Jesse softly, "Oh my God, you feel so amazing inside me! I can't believe we're finally fucking!""Ohhh! I know, this is so much better than when you're giving me a blowjob even! It feels so good!" he groaned. I savored the luscious feeling of getting fucked by my first cock as he slowly rocked back and forth inside of me.
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It felt so right, feeling Jesse's body against mine, his weight pressing into me, his cock feeling so big and hot inside me as he filled me in a way I'd never imagined possible. I curled my legs around him and placed my hands on the cheeks of his ass as he slowly screwed me. Both of us were moaning and groaning softly into each other's ear as we lustily pleasured each other. When I glanced up into Jesse's face I could see the intoxicated delight in his eyes, and a big silly smile on his lips when he wasn't kissing me. I squeezed his cock as it pushed inside me and giggled as he just groaned with a look of delirious pleasure on his face. I'm sure I looked pretty much the same to him - I was so glad that I was the one giving Jesse's cock its first taste of pussy! And it felt so good inside of me! MMMmmm!When I glanced down between rising hills of my tits I could see his cock emerging from his sparse forest of pubic hair, only to disappear between my open legs below the golden-haired patch on my pussy. I could see his dick gleaming with my wetness when he pulled almost all the way out of me, then watched his pubes meet mine as he plunged back inside me. My Jesse was finally fucking me for real, and it was a glorious sight!I could hear my computer chair sqeaking quickly as Gabby started to really ride Jason's dick, and Rick and Tina were getting louder as they started to fuck a little more vigorously. I pushed and pulled gently on Jesse's ass to prompt him to do the same. The faster and harder he went, the better it got. "Fuck me Jesse! Fuck me harder!" I kept breathing to him, grunting in pleasure as he slammed his hips into mine more and more quickly and with more and more force. I was rocking back and forth on the bed from Jesse's thrusts, my legs spread wide to let him push as deeply into me as he could. I snaked a hand down to my pussy so I could rub my clit as Jesse fucked me, determined to come at least once before he did. I heard a little "Fuck me Rick! It feels so good, I'm gonna come!" from below the bed, followed immediately by a low groan from Rick as he came himself. Tina whimpered softly, and repeated, "Oh, I'm gonna come, I'm gonna come, I'm gonna - UNHHHH, OHHH YESSS!" I was gradually approaching that point myself, and I was sure Jesse wasn't very far behind either.
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I rubbed my clit furiously and closed my eyes, focusing on how good it was finally having Jesse's rock-hard cock filling me, pushing deep inside of me then retreating for another big thrust. We kept at it for quite a little bit before I noticed Rick and Tina standing next to the bed, just watching us fuck. I smiled ecstatically at them and they both grinned back at me, watching as my best friend completely nailed me for the first time. Incidentally, Jesse wasn't particularly big back then, but he wasn't exactly small either. The first time I came with him inside me it felt like I was getting fucked by a telephone pole, it was so good. Ever since then, whenever I felt like stroking his ego, I've whispered that into his ear. It never fails to put a big silly smile on his face. Rick and Tina disappeared completely from my mind as I started to reach my peak. I cried out for Jesse and clutched him to me as fireworks went off in my head and I lost all control over my pussy as it began spasming around Jesse's thrusting cock. Waves of intense pleasure swept through my clenching pussy and out into the rest of my body, and I started moaning really loudly I think. I guess my orgasm must have finally pushed Jesse over the edge too, because he groaned into my ear and pushed his cock deep into me. I could feel it throbbing inside me and squirting come into the thin piece of rubber that separated his body from mine. My fingers dug into his ass like claws and I bucked my hips up towards him as I tried to pull him deeper inside me. I literally couldn't get enough of him inside to satisfy me. When I came down from my climax I found covering his mouth covering mine to keep my mom from hearing my loud moans.
As much as I liked playing tonsil hockey with him, the burning in my lungs reminded me I needed to breathe, and I broke the kiss to greedily suck in all the air I could. When I had taken a couple deep breaths I gazed up at him intensely and wrapped my arms around his neck. "Oh fuck that was good!" I panted. My face was only inches from his and I kissed him fiercely, pausing every few seconds to draw in a big breath. I could feel his dick softening inside me and I swiveled my hips a bit to tease him. "You're still in her? C'mon big guy, out!" laughed Tina as she slapped Jesse on the ass playfully. He carefully pulled his dick out of me, making sure to keep the condom in place, then got up to throw it away. I made no effort to cover up or even close my legs, thoroughly enjoying the afterglow of my first fuck. Tina blushed slightly and Rick couldn't tear his eyes away from my wet, red, swollen pussy. You could totally tell I'd just gotten fucked and I loved it. "You gotta be careful afterwards or he could spill some in you," Tina told me. I nodded halfheartedly, wanting to just enjoy lying there and not worry about anything. "God, that was way hotter to watch than any porno," Rick commented, and I smiled and closed my eyes, waiting for Jesse to return. "Um, Rachel? Do you mind if we have another condom or two?" I couldn't help but laugh at this, and Tina smiled bashfully as she hugged Rick to her. The box held a dozen condoms and we'd used three of them so far; I had no idea when Gabby and Jason had finished, but they were sitting on the far corner of the bed smiling at me as if to say "us too!""Sure!" I grinned to them, grabbing the box and handing each pair a couple condoms apiece.
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I pulled out two more for Jesse and I as well, saving the last three for some other time. Now that he and I had gone all the way, I realized I'd probably need to find a bunch more condoms since I figured we'd be fucking pretty regularly. I mentioned this to him when he returned. He said he'd try to take care of it, and rolled back on top of me. Feeling his body against mine again was so good!I kissed him quickly and cuddled up with him while we waited for him to get hard again. Rick and Tina immediately went at it again, this time on the far side of the bed we were lying on. Gabby took the opportunity to visit the bathroom, and by the time she got back Jason had gotten it up enough to roll another condom on. She mounted Jason again, on the floor this time, which I thought was a really good idea. Jesse and I were in no particular hurry, however; he came over a lot, or I went over to his place, and we were unsupervised enough that we didn't feel like we had to fool around every opportunity we got. Right now I was a little more concerned with checking in on my Mom, so I pulled on my clothes and tiptoed out the hall to her room. She was still rolled over on her side, snoring fitfully. I smiled and closed the door, then tiptoed back to fuck my best friend again. "Do me again, Jesse!" I grinned as I quickly stripped my clothing back off. He just shrugged, his rubber-covered cock bouncing, and told me it's not like he could refuse, since I owned his cock. I laughed and climbed on top of him.
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To make a long story short, I rode him like there was no tomorrow, coming twice before he finally groaned and shot his load. He and I just watched the others fuck for awhile; Jason thrusting up into Gabby with a grunt before he could get her off (which annoyed her quite a bit), and Rick and Tina taking it easy this time as they gently humped on my bed. Then both Gabby and I got on the bed on our knees so we could get fucked doggystyle. Gabby had a hand between her legs rubbing her clit so she'd come this time, and I just let go and let myself get fucked senseless by Jesse's relentless jackhammering. When he really gets into it, he's awesome at fucking me doggystyle, and I can't get enough of it. Tina was kind enough to wait out by Mom's door to warn us if she heard her get up, since she and Rick decided to save their last condom for another time. Apparently they were kinda hard to come by, at least for them. Once we were done fucking, we all agreed we had to find a way to do this again. We also agreed to keep it a secret, Gabby obtaining a promise from Jason to keep quiet about the whole thing by promising him all the pussy he wanted next time just as long as he never said anything to anybody. You should have seen the grin on that boy's face. So that's basically how all this started. We didn't start swapping partners until the third party, and we didn't start inviting anyone else until the fifth. I let Jesse fuck whoever he wanted, but always reminded him that I still owned his cock and he'd better please me first if he wanted to get to fuck other girls. I finally lost "ownership" of his cock freshman year in a stupid bet I should never have taken, and I've always kinda missed having that control over him. Before 9th grade I'd always just enjoyed fucking for the simple pleasure it gave me, but after I let Jesse come inside me that once I became addicted to it, and a large part of my enjoyment became getting guys off in my pussy.
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Part of it's the sensation of them coming inside me, and part of it's the feeling of control I have over them, I think. Now that I'm on the pill, though. . . watch out!So anyhow, now you know the story of our first party. I've got exams coming up soon, but once I've settled back into my normal routine I'll sit down to write out the story about Sarah and Will like I promised. .
