Five Guys And I

Five Guys and I: My First Gangbang

“Where do you want me to cum?” Moaned Stephen, as he fucked my pussy with greater intensity.

I turned my mouth away from the guy who had a really long cock (LC) (it’s a bit silly giving you all the names…you certainly will not remember them all!), removing his cock from my mouth. “In my mouth...shoot it there…” I somehow managed to moan, as LC began to rub my clit with his middle finger…

Stephen began to fuck me harder, incredibly hard, as I turned my attention back to LC’s cock. I was prostrate on a king-size bed. I looked briefly around the hotel suite while beginning to tease his cock with my tongue. I saw my boyfriend John drinking a glass of wine, while vaguely rubbing his cock, as he overlooked the scene, very much, enjoying this all. Near Stephen stood Patrick, jerking himself off, preparing for his turn.

As I was about to cum, Stephen groaned loudly, pulling his thick cock out of my soaked cunt. With a flick of his wrist he removed his condom and moved very quickly to the foot of the bed, where my head lay. I positioned my head so I could suck him off. I began to see to his balls contract when I felt Patrick enter inside of me, returning me to my state of near-orgasm—he placed my left leg over his shoulder, my black heel pointing at the ceiling. He massaged my left tit with his other hand. I moaned loudly as Stephen shot a load all over my cheek. I removed my left hand from LC’s cock and tried to control the aim of Stephen’s shot. I then opened my mouth wider as his second and third shots came in quick succession. They both deflected off my tongue, landing mainly on my cheek and chin, with some in mouth. I tried to lick it but I felt a rush of orgasm.

“Yessssssss.” I screamed as I began to cum violently, cum seeping into my mouth. Stephens flow turned into a trickle, but these events must have been too much for LC, who then positioned his cock over my face, and without saying or muttering anything, began to cum heavily all over my face, with only some landing in mouth.

As I tried to swallow all of the cum that I could, noticing through my squinted, slightly cum covered eyes that guy with small cock (SC) had returned from obtaining ice for the water. I laughed to myself, my orgasm subsiding: “How the hell did this happen!”

One would expect that one would not just fall into a gangbang, so to speak, but that is what occurred. Essentially. My long-term boyfriend John and I attend a fairly elite northeastern university, at which we are both pursuing advanced, post-graduate degrees. We met as undergrads, and we have been dating for over five years. We’ve always been sexually adventurous, even if I was relatively inexperienced when we met. (Drunk frat boys/ high school boys who last 1.25 minutes were not a turn on for me. ) Any way, being secure in our relationship, we eventually decided to place an ad on one of the those internet swinger-sex finder web sites, looking for both couples and single men. While we quickly learned that most couples tend to be very frightening (e.g, out of shape, repulsive looking, older than Methuselah, etc), the sheer number of single men who replied to my ad seeking a guy or two to help John fuck my brains out guaranteed that I was able to find some who were in shape and good looking. We hooked up with a couple of single guys, and I very much enjoyed it. Having two cocks with which to play, being fucked in my ass and cunt at the same time—I was really turned on by it all!

I was also turned for the first time by facials—not the 18 man bukkake films from Kyoto easily available on the net, but, well, more low key ones. For example, we took home one time a very hot, very well endowed, very skilled frat boy (the only one?!?) from a bar one time. I was sucking John off as the frat boy fucked my pussy like a piston. I could tell that he was close to cumming, so I instructed him to cum on my face. Even though I force all guys—save John—to use a rubber, I normally had guys cum on my tits—just in case of any breakage. As John then entered my cunt with a furious thrust, the frat boy began jerking himself off, as I licked the pre-cum from the top of his head. John continued to fuck me furiously, and I approached cumming. Right as it began to shudder through my body, frat boy unleashed a ridiculously huge load over my mouth, cumming in wave after wave. I tried swallowing it all, but decided against it, licking it, smearing it over my face with my tongue. John continued to fuck me, with ravenously erotic look in his eyes. The look of my boyfriend and frat boy, the erotic fascination, the charge I felt, was absolutely priceless.

But I digress!

Any way, we had only done it with one other guy at the same time. The boyfriend, ever the progressive, suggested that we try to include another. I was generally open to that idea, but we never established a firm plan. However, later that night, after some significant drinking, we went back to our apartment, and fucked for a ridiculously long time. We’re not generally dirty-talking people—it sounds so fucking silly when we try it sober—but as he slowly fucked my ass, I moaned how great it would be have a cock in my ass and mouth, as well.

“You’d like that?” he responded, thrusting harder into my tight hole.

“Yeah…I’d be a fucking cum slut…” I was laying on my back, legs well behind my head, rubbing my clit furiously.

“You wanna be gang fucked?” he asked, as he fucked me harder and harder.

I through my head back, moaned. “I just want to be used like that… how I want to be used”

This was all too much for him, as he unloaded his cum deep in my ass, collapsing on me. A bit too early for me, but I was still well satisfied.

Later that night, we talked about me being fucked like that, and we agreed that it would be worth trying. Although I had set up all of our previous mee(a)t and greets in the past, I was swamped at school, and John, indifferent as always to his school responsibilities (damn geniuses!) volunteered to set it up. He knows what I look for. I went to sleep that night dreaming of cock…after cock…after cock!

It took him a while to set our evening up, but within a month it was organized. The trouble was not finding guys, but simply coordinating around our schedule—sex is great, but we have a life outside of it! Regardless, John did a very good job of finding four guys with whom to do this. Two of whom we had met before, Patrick and Stephen (the names have been oh-so-cleverly changed, obviously.) He also organised us to have a small suite at a respectable hotel in the heart of downtown. This was a Friday, and I have to admit that I was nervous. And, well, very turned on. ;o). As I thought about my evening ahead, I became extraordinarily wet through the day. Also, I had to rub my clit just to relieve the tension in the women’s bathroom during my lunch break.

Regardless, cum-juice soaked panties aside, I made it through the day, arriving home two hours before we were scheduled to meet the four of them at a pub adjacent to the hotel. I do not dress skankily when going out—that simply is not me. However, I wore garter/stockings/ and ‘special’ pair of black heels, with very large heels. I also wore a reasonably short black skirt. Although it was autumn, and I wore a tight fitting red shirt, with a plunging v-neck, sleeves that barely covered my shoulder, and a taper that barely covered my midrift. Although I’m a wee short and small bones girl, my breasts are amply large and disproportionate, so the shirt was filled out quite nicely . Not the most sensible outfit for late October in New York, but living in the NE for one’s entire life makes one accustomed to this. I looked quite hot, I think, and John agreed. I didn’t look like a tramp—I refuse to make the mistake of confusing “sexy” for “cheap” and “nasty” (although there’s nothing wrong with that if it gets one off…) I just looked, as John said, “sophisticated and delectable.”

We arrived at the hotel shortly thereafter, neither of us really believing what we were about to do. John brought a half case of decent Australian wine, to help things along when we got back to the room, and six plastic cups. (Sometimes class must give way to being pragmatic!). I finished applying my make up, and we left to meet my friends for the evening at the pub…

It was a Friday night, and although the place would not be our ideal hang out, it was nonetheless crowded for only being 7PM. It was not really a hook-up bar—it was more of the kind of place where people meet to talk BEFORE trying to hook up! A bit of bad planning guaranteed that none of the guys knew each other, so it was likely that they all could be there, wandering around like aimless and lost sheep, trying to find us. As the pub also served food, John had the foresight to reserve a table, which we made our way to. I sat one end, John at the other.

Within two minutes, before we could even order our first drink (the outrage!), LC made his appearance. He was medium height, and an Adonis, but certainly in good shape. He also had a super-cute face, which is what I usually look for, and very light black skin. He was a bit sheepish at first.

“Hi, Jen?” he asked, almost apologetically. I beamed back a smile, trying to obfuscate my own nerves.

“That’s right.” He then sat down, and I swear he was already hard. I swear, because the monstrous thing was almost erupting out of his pants. We engaged in some small talk, ordering our first drinks. By the time Stephen had arrived, I had already downed by apple martini. He sat by John—he did not need to introduce himself to me.

SC arrived next. He was a short pretty boy, with two earrings, and a very well groomed sartorial sense. He reminded me of John immediately, so I liked him immediately. He was the youngest of our group—only 21 I think—but he was mature and articulate. He kissed on the cheek to greet me, sitting down across from LC, and next to me. We were all discussing politics, off all things, fearing the possibility of another four years of the Bush regime. (Say no to Bush…in the bedroom and in the voting booth!) When we also ordered our second round of drinks. It was actually my third apple martini because, well, I was still nervous! Patrick eventually arrived an dour group was complete. John was discussing something with Patrick and Stephen, while I entertained LC/SC. Our talk was still on non-sexual matters, but, well, I was beginning to make my intent known. I always have a veto over any situation, as any person in a swinging couple should, but I certainly was not going to utilize that privilege tonight! As I talked to LC, SC, under the table, began slowly rubbing my leg. I was already a little bit wet, but this little thing set me off. I smiled at SC, to let him know it was ok. He then moved his hand further up my thigh, until he reached my pussy, and receded.

I turned to him. “Quite the tease, ehh?” LC realised what SC had been doing, and grinned, placing his hand on my thigh, as well. I was quite wet by now. The other three were now paying attention as well.

“How about one more drink and we go?” I asked the group. Strangely, no one objected. We ordered yet another round, and I was beginning to become well, slightly drunk. We had only been there an hour, and four drinks! Luckily, we had eaten before arriving.

As we drank our final round, I had moved my hand to SC’s crotch, rubbing it under the table. LC was not able to do much other than hod my thigh, due to its placement near the table. The other three were well aware of the mutual teasing occurring between me and LC/SC, and the titillation was obviously getting to them. We were just six people, all in college or possessing respectable white collar careers, and we had no intent of signaling to the world that “these five 20 something guys are going to fuck my brains out in an hour.”

We soon reached the hotel, and I quickly signaled my intent. I was the most inebriated, although I was hardly drunk, and although I tend to be shy initially with new people, when we reached the suite, I grabbed John and began kissing him passionately. The door was barely closed. John had mentioned the wine before we made it to the room, and some one went over and began opening the bottle, I think. Stephen stepped up behind me and slowly placed his hands on my tits, gently touching the underside of them, before moving slowly over the outside of my shirt. I turned around and greeted his mouth with another passionate kiss, our tongues lashing each other. John began kissing the side of my neck, which I love, and he slowly moved his face down my shirt, kissing my neck, sliding his tongue down until it was between my tits. I stopped kissing and surveyed the room. Patrick, ever the cool one, was pouring glasses of wine; LC had the largest grin I have ever seen; and SC appeared as if he was about to blow a load. And my clothes were still on!!!

This problem was remedied quickly. Stephen slowly slid my shirt over my head, exposing my bra. I wore a black, almost-faux leather lace bra. Stephen began kissing the back of my neck, as John began to make out with me again. Both of their hands were all over my body. John with a hand on my tit and over my cunt, Stephen on my lean stomach and other tit. They had done this before. They slowly worked me back to the bed where we rather ungracefully fell in a heap.

The situation and the liquor were intoxicating me. “Stand back you, two, give the others a chance to look.” They obliged, leaving me on my back on the bed. I began to rub hands over my breasts, and down my body.”

“God, you’re hot!” exclaimed LC.

I laughed as I eased my back off the bed, unzipping my skirt, sliding it down my legs, exposing my matching black g-string. I kicked the skirt away. I then began to masturbate, slowly rubbing my tits, easing my straps down. LC walked towards the bed.

“Not yet” I softly admonished him. He, still grinning, stopped. I slipped my bra off, exposing my breasts. They are not huge, 36C, but on my frame, they look it. I rubbed my nipples slowly with one hand while the other proceeded to my pussy. Within a minute, I was slowly rubbing my clit from outside of my g-string. All of the guys, save John, who likes to watch initially, began to remove their clothes while still trying to watch me. Within a minute or two, I had four hard or semi-hard cocks staring at me. Five hot guys and me…what a shame!

I stopped rubbing my clit before I orgasmed. “Come here” I whispered, pointing to Stephen. He knew precisely what I wanted. He was between my legs in seconds, slowly pulling my underwear, revealing my cunt. I do not shave it entirely, I am not a 10-year-old girl, but barely any hair remained. He went to work, slowly licking my clit, as it became more engorged.

“May I come over?” LC asked. I laughed at the formality of it. “Of course, “ I responded as Steve began licking me with greater power. “Come up here.” He then walked over to the head of the bed, and placed his beautiful, shaved cock and, yes, very long cock before my mouth. I took it my hand and gently placed it near my clips, licking it, teasing him and, well, every one else.

Steve was building me up now.

“That feels so good, Jen, oh year.” LC moaned.

I approached cumming. I grabbed hold of Steve’s hair and held his face down in position. He licked me furiously. The sensation built up in me and I gasped softly as I came.

“Fuck me, now.” I said to Steve

Steve then slowed down, and, in reaction, I placed LC’s cock in my mouth and began to suck him furiously. Steve stood up, went to the bureau, and picked up a rubber. LC placed his hand all over my tits, softly, with a lot of skill, keeping me sensations at a peak. As I sucked LC off, I noticed Patrick approaching me from the other side of the bed. Steve also approached, condom in hand. He kneeled before my cunt, placing it on his cock. Patrick meanwhile placed his cock near my mouth.

Stephen slowly entered me. I moaned as his cock slid into my very well lubed cunt. With all the dexterity I could muster, I began to rub awkwardly Pat’s cock.

“Oh, you feel great.” Groaned Steve. I, having a mouth full of cock, could only moan in reply. He began to pick up the tempo. I had to moan again, pulling away from LC’s cock.

“God” I muttered as Steve continued to fuck me in this modified missionary position which I presume not many missionaries used.

I decided to give Pat some attention, but before doing so, I licked away some pre-cum that was flowing from LC. Like every guy, he tasted different from any one else. I moved my head away from LC, the miniscule thread of cum attached from my lips as I attacked Pat’s cock with a passionate fury. LC began to jerk off furiously. I suspected that he was not going to participate much longer in this session.

Steve was not going to last much I longer, either. He always finished early in the first session. His face was highly contorted..

“I’m gonna cum soon.” He sighed.

“Oh, yeah, so am I” said LC.

I looked up at Pat, to the best of my ability, as I was rocked with greater intensity against the pillow.

“Fuck me…” I said loudly, almost screaming.

“I’m gonna get a condom.” Pat said, as I then turned my attention to my new friend LC. I devoured his long cock in one gulp…He sighed appreciatively.

“Where do you want me to cum?” Moaned Stephen, as he fucked my cunt with greater intensity…

So, that is the historical development.

LC was still cumming…the guy must not have fucked or jerked off for a week before this. Cum was sliding down my cheeks, down my chin, into my mouth….I could tell from his cum that he was obviously a vegetarian. (straight boys who have never tasted cum: ask your girlfriends about this…)

“You like that?” Pat muttered, as he quickly fucked my cunt.

“Fuck me, God, fuck me!” I curtly said as he continued to fuck me. LC presented his cock in front of my mouth—the head of his cock was seemingly encased in cum. I adjusted my head so I could place it in my mouth and suck the last drops out of it. I looked up at him, he and he stared down, very appreciative of my work.

I held my hand up to Pat’s chest, indicating that I wanted him to slowdown. He did, and LC removed his cock from my mouth.

“Do me from behind.” I directed. I could feel the cum that I had missed with my tongue begin to harden on my face, chin and neck which is just—well—an odd feeling, if slightly arousing feeling. However, no time for that—I got on my hands and knees, facing the headboard, leaving enough room for someone else to fit in for a roasting. I motioned to SC, who had been waiting oh-so-patiently. Pat waited for him to get into position, and I put SC’s firm cock in my mouth. I suspected that he would not last so when Pat started fucking me again, brutally hard, which is how I often like it. To prevent SC from cumming too quickly, I just teased him with my tongue, really. As any one who has been roasted will attest, however, it is very difficult to control what precisely the mouth does.

Pat continued to drive his cock deep into my cunt, and I could feel my ass tingling—it usually takes me a few orgasms before I feel ready for anal, and I was beginning to feel ready. Just as I was ready to direct Pat to fuck my ass, he removed his hands from my ass, which ha had alternately slapped lightly and held onto, and he placed his hands on my should as he began to bore into me with increasingly alacrity.

“I’m almost there…” Pat moaned.

As I was about to tell him where to put it, I felt his midsection contract violently. I knew that he had just shot a load into the condom. He drove at me a few more desultory times before holding still.

After he pulled out, I took and opportunity to get some wine and clean myself up slightly. LC and Stephen were not quite ready yet, John was not undressed and semi-hard, waiting his turn. SC sat on the bed, still hard.