My name is Erin, and I’m going to tell you about my first anal experience – well, actually my first four anal experiences! It happened last year after had just turned 18 and was a junior in high school and dating a guy named Kevin.
It all started on the bus rides home from our volleyball games. We girls would get to talking and eventually the conversation would always turn to sex.
Over the years we had talked about all our experiences, sharing from our first kiss to our first time going all the way. There was a group of six of us that were very close and we pretty much conformed to the group’s idea of what was acceptable at that time. For instance, when Kim admitted to letting John take her virginity after one of our school dances, within three months the rest of us had followed suit and ‘done the deed.’
At the time of my story the group had progressed to anal sex, with Kim again being the first to try it and Angie being the first to admit she liked it better with a dick in her ass rather than her pussy. Within a month the whole group had also had anal sex, except me. They kept one me, telling me how much I would enjoy it once I got over the initial pain, how it was better than vaginal, how you didn’t have to use a condom because as Janet said, “No one ever got pregnant from butt fucking.” A month stretched to two and then to three – after four months the ribbing was so constant that I figured I would let my current boyfriend Kevin in my ass and get it over with.
Before I go any further I’ll describe myself to you so you’ll know how to picture me in your mind. I’m just a bit over five feet tall any my build would be considered athletic from the sports I played. My legs and ass are particularly tight and seem to get a lot of attention from guys. My breasts are small but perky and very sensitive and I love to have them sucked on. My hair is brown and cut shoulder length, though most of the time I have it pulled into a pony tail and my eyes are also brown. I have a cute face, not strikingly beautiful but nothing that I’m unhappy with. There, now you know what I look like – now let me tell you about that Saturday when I let not only my boyfriend fuck my ass, but three of his friends as well.
It was a July afternoon, a Saturday and I was out behind my house shooting hoops at the rim on our garage. Kevin’s car pulled up and he and his friends hopped out. At that point I had been dating him for about six months and fucking him for five of those. The sex was good and he had a decent sized cock – not too big to be uncomfortable but not too small that it failed to adequately do its job.
With Kevin that day was Jimmy, Andy and Rob. They were all athletes like Kevin and some of them had dated some of the girls in my click – I think that Rob had even spent a few evenings fucking Kim (but come to think of it, it was almost easier to name who hadn’t nailed her yet.)
They joined me shooting hoops and things started to get competitive with the boys shoving and taunting each other as boys do when they get their testosterone flowing. I wasn’t about to be left out and joined in, bumping and jostling them and they did the same to me. They knew I was a ‘tough girl’ and that I wasn’t about to back down from them just because they all had a hundred pounds on me.
Andy and Rob were two starters for our basketball team and both very good, soon they had challenged Kevin, Jimmy and me to a game of three on two. “What are the stakes,” someone asked.
“Well,” Rob said. “If you win we’ll pay for you the next wing night.”
“And if you win,” Kevin asked.
Andy and Rob exchanged a sly smile. “Then we all get to fuck your girl.”
Kevin laughed and thought they were kidding. “I don’t think that’s a bet that I can make, just because she’s my girl friend doesn’t mean that I can wager with her pussy.”
“Then why don’t we ask her?”
Suddenly all eyes were on me. The idea of fucking all these guys was kinda exciting, actually. “Well,” I said looking at Kevin and Jimmy. “Do you plan on losing to these two?”
“Hell no,” they said in unison.
“Then fine, you beat the three of us and I’ll fuck you all.”
I never thought in a million years that we would lose, or that they would stick to the wager – I was wrong on both accounts. In fact, the game wasn’t even close and it was essentially over before it began. When it was over the usual trash talk ensued with Andy and Rob really rubbing it in.
“Now we get to fuck your girl!” they laughed and prodded Kevin.
“When do you want to pay up?” Andy asked me.
My parents weren’t home and wouldn’t be until tomorrow, they were off visiting my brother at college.
“How about we go inside and get a drink,” I suggested. “Then we’ll see.”
We were all seated in the living room, enjoying a glass of cold lemonade and cooling down from our game. When I had been getting drinks for everyone Kevin cornered me in the kitchen.
“You’re not really going to go through with this,” he asked.
“A bets a bet, babe. Unless you object I’m inclined to see where this goes.”
“Well, if you don’t have a problem then I’m game. But if you start to feel uncomfortable just say the word and I’ll get them out of here.”
I agreed and we kissed. Kevin slipped a hand up my shorts and rubbed my pussy which was wet with anticipation. I think that I wanted to fuck these guys more than I had realized.
We were sitting around, sipping our drinks making small talk and then Andy asked the question that had been on everyone’s mind.
“So, are you going to pay up or what?”
They all turned to look at me, all trying to guess exactly what my answer would be.
“Depends,” I said
“If you guys are willing to fuck me in the ass.”
They were so surprised they almost spit out their drinks. I’m not sure if they were really expecting me to honor the payoff but I was sure that they weren’t expecting me to ask them to pop my anal cherry. The only stipulation I made was that when we got to that point that Kevin would be the first in my ass – other than that they were free to decide how they wanted the wage paid.
Of course they all agreed to my terms and in seconds I had the hands of four horny guys groping and caressing me. My cloths came off in record time and I stood before then naked, turning to show off my assets to the group of them. They pushed me down on a chair and leaned me back. Kevin began to kiss me while his friends attended to my other treasures.
I wasn’t sure who was doing what, I think that it was Jimmy and Andy who were sucking my nipples and Rob who took up position between my legs, all I knew was that I was the center of attention and loving it.
Whoever was between my legs began licking me and what they lacked in technique they made up for in enthusiasm. I could feel a tongue pushed deep inside of me, licking and caressing the soft folds of my pussy. I reached my hands out and found a cock with each, one was Jimmy’s I think and the others was Kevin’s. I rubbed both through their shorts and felt them reach full erection.
Kevin was the first one out of his shorts, he dropped them on the floor and moved his hard cock within reach of my mouth. I opened wide and received his advances as he slid inside my mouth. In the position I was in I couldn’t really perform on him and so he did the work for me, slowly fucking my face with as much of his cock as he could fit.
My pussy was still being worked on by Rob or whoever and now I felt myself being penetrated, not by a cock yet but by fingers. I pulled the cock from my mouth and could see that not only was Rob between my legs but Andy was as well and they both had their fingers inside me. Being fingered by two guys at the same time was a new experience for me and one that I enjoyed – I felt myself growing wetter at their touch.
Jimmy stopped sucking on my tits and took off his shorts. He moved to the other side of my head and tapped on my cheek to let me know his cock was there. I turned my head to that side and slid him between my lips. Jimmy’s cock was long, probably over seven inches but it was very thin and I was able to slide him deep in my throat without triggering my gag reflex. I lay there dividing my attention between him and Kevin while the other two continued to work my pussy into a sloppy mess.
I needed a cock and I needed it now. I sat up and pushed the cocks out of my face. “Who’s first?” I asked. Kevin tried to assert his right to be the first in my pussy, but his friends rebuffed him saying that it only applied to my ass. Kevin looked to me to support his claim on my cunt and all I could tell the group was that I didn’t really care who fucked me, but that one of them better do it soon.
Jimmy took the initiative and beat the other three to the punch, pushing me down on all fours and sliding his cock into me. Rob and Andy still had their shorts on and they both quickly remedied that. Rob slid into the chair in front of me and pushed my mouth onto his hardening cock. Jimmy wasn’t exactly stretching me out with his slim cock but he was putting a good fucking on me, holding onto my hips and thrusting all he had inside me. I’m not a very tall girl and his seven inches were hitting bottom with each stroke.
I slid Rob’s cock into the back of my throat and felt his organ fill completely with blood. It was thicker than I expected and I chocked on its girth. It was about average length and proved a very nice size to suck on; with a little effort I could shove all of him in my mouth burying my nose in his wiry pubic hair. He moaned with approval and told Kevin how lucky he was to have such a good little cock sucker at his disposal.
Kevin had had enough watching Jimmy fuck me and he called ‘switch’ and his cock replaced Jimmy’s inside me. Kevin knows how I like to be fucked and he arranged himself under me so that his cock ran into me over my clit. It took only a few second in my heightened sexual state for my first orgasm of the day to overtake me. I jammed my mouth down on Rob and felt his hips rise – I could tell that he was about to cum and didn’t want to. I released him from my mouth as my orgasm subsided and Andy moved in to take his place.
In all that was going on I hadn’t bothered to look at any cock that wasn’t being offered to my mouth but now I got a good look at Andy’s meat, and there is only one way to describe his weapon; enormous. It must have been ten inches long and so thick I couldn’t get my mouth past the huge mushroom head. It looked like something out of the porno’s that the girls and I would sometimes rent and watch at our sleepovers.
Kevin pulled out of my pussy and he and Rob rolled me over on my back. Andy repositioned himself, straddling my chest and letting his cock fall in my mouth. I worked with all my might on the head, that being about the only way I could perform on his massive tool. Rob slid his cock inside me and it felt snug in my tight pussy. It had been a while since I’d been stretched, having been used to Kevin’s rather average cock by then.
Rob was a good fuck; I had heard that from Kim back when they were screwing. He really knew how to please a woman, driving his cock into my wetness and using his thumb to stimulate my clit at the same time. He brought me to my second orgasm not long after he started fucking me and by the time he finished I had had my third as well.
When he pulled out I knew that it was time for Andy to fuck me and I was excited and nervous as hell all at the same time. I had offered my virgin ass to these guys and here I was worried about just getting this cock inside my pussy. I asked Kevin to run up to my room and bring down the lube that I kept in my dresser drawer. He left to retrieve it for me and Rob went back to work with his mouth on my pussy, trying to do his part in lubing me up for the coming attraction.
Kevin returned with the lube and handed the bottle to me. I took a large handful and spread it on Andy’s huge cock, then spread some on my pussy for good measure. No one moved to put their dick in my mouth, they all knelt on the floor around me and prepared for the show.
Andy positioned himself at the entrance to my pussy and pushed. I felt my self being torn in two, I had never even imagined that something could rip me open like his cock. The lube helped and he slid inside me some more. I spread my legs as far as I could trying desperately to make some more room for him. I felt some more push inside me and was thankful that Andy was being gentle about things – he could really do some damage if he hadn’t been.
A few pushes later and I felt him hit bottom I was entirely full, every available inch of my womb was filled with his amazing cock. I put my hand between my legs and touched the part of his cock that wouldn’t fit inside my pussy; he still had at least four inches that weren’t going to end up inside me. He seemed satisfied with what he was able to get inside me however and began to slowly, gently fuck me.
I couldn’t cum, couldn’t think of pleasure just survival. He would shove inside me until he hit bottom and then would withdraw slowly and I imagined that this was a preview of what it would be like to give birth. Once he got inside me and started getting into rhythm the other guys took up positions around me. I had Rob in my mouth and was using my hands on Jimmy and Kevin, who in turn used their mouths on my nipples.
Andy only fucked me for probably ten minutes but it felt like hours and when he withdrew I let out a sigh of relieve that he hadn’t killed me with that thing. I’m not sure who said it, but someone suggested that now that they had all had my pussy it was time to get to work on my ass. They all seemed to agree and seconds later they had me face down on the floor with a pillow placed under my hips to put my ass up in the air.
Kevin got the lube and began to coat my asshole with it, pouring dabs of it on my virgin ass and using his fingers to coat the inside of my sphincter. Several times when he was taking me from behind Kevin had slid his finger in my ass and it had felt good, but I had resisted taking his cock up there out of fear – now here I was having my ass lubed up for not just him but three of his friends.
Soon he had what he thought to be a good amount applied and I felt him reposition himself behind me in order to being. “Be gentle,” I told him and he assured me he would be. I felt the head of his cock press against my hole and he applied pressure until my muscles relaxed and I felt the head of his cock pop inside my ass. I reached behind me with my hands and spread my ass for him, giving him full access to my ass.
I knew that Kevin had wanted this for a long time and his passion soon took over his reserve and he began to fuck me with more fervor. From what I could tell he was able to get about half of his cock in my ass and he was running it in and out of me much the way he fucked my pussy. The feeling wasn’t unpleasurable for me and after I relaxed and settled in it actually started to feel quite good. I looked around the room and saw the other three guys sitting on various pieces of furniture around the room, lazily stroking their cocks and anxiously awaiting their turn.
Behind me Kevin’s breath became short and I knew that he was about to cum, I reminded him that the other three guys still hadn’t had their turn and that cuming in me before they got to ass fuck me would be rude. Reluctantly he withdrew and sat on the couch in the spot that Rob vacated when he came to me to be the next in my ass.
Rob didn’t bother with the lube and he didn’t bother being gentle either, he just aimed and pushed. I guess that was ok, he was treating me like a whore and I wasn’t exactly in a position to demand to be treated lady-like. Rob pushed my legs further apart and pressed his body against my back, using my shoulders to pull me to him and increase the strength of each push.
Again I felt pain but also an underlying pleasure. Rob’s cock was thicker than Kevin’s and he was stretching me as well as getting deeper into my ass than Kevin had – not because he was longer but because he seemed bound and determined to get all of his cock inside me hole. I think he actually managed to do just that before the feeling almost over took him and he withdrew.
I was thankful when Jimmy took next on my ass, I didn’t think that I would be able to survive Andy and I didn’t want anyone left out. Jimmy’s long, thin cock slid in my ass easily and his entire length fit easily inside me. His balls were banging against my clit with each stroke and there as no pain of being torn apart, only the pleasure. It didn’t take long and Jimmy had me cuming, my first anal orgasm! It was awesome and just as the girls had said it would be, all together different than a vaginal orgasm but somehow still the same.
Jimmy fucked me for a few minutes longer after my orgasm and then he was done and it was Andy’s turn. He moved behind me with that huge cock of his and asked me if I wanted to skip this, and his sweetness moved me to the point where I relented and told him that I wanted him to at least try and get in my ass. He lubed himself up good and then poured some more in my now gaping hole. He pressed the head of his cock against me and I gripped the carpet with both hands, holding on for dear life.
It felt like I was being torn in two, like someone had lit a fire in my asshole. I screamed but it was too late, Andy cock had started its descent down my dark hole. Like Rob he grabbed my shoulders to help him pull himself inside me. My hole felt like it would tear at any second and the feeling was so intense that I actually came again. I was being filled in a way that I never knew existed and it felt amazing. And it just kept going, Andy just kept pushing more and more of his cock inside me until I felt the most amazing thing, his balls slapped against my ass cheeks – his entire ten inches was in my ass.
He groaned in pleasure, I don’t think that very often the entirety of that huge organ gets inside anything fully. He asked me if I was ok and I assured him that I was, but that I was going to be sore as hell tomorrow. He started to really fuck me then, going slow but not showing my ass any mercy. Again and again I felt him slap against me, filling my ass totally and completely.
I started to feel his rhythm and started to move in sync with him; I was now fucking him as much as he was fucking me. I was totally oblivious to the other guys in the room – my attention devoted totally to the monster cock that was buried in my ass. Andy leaned in close to my ear and told me that he wasn’t going to be able to hold back much longer and asked what I wanted him to do. “Cum in my ass,” I told him without hesitation. “I want to feel your cum in my ass.”
The other three were so into the show that they didn’t even object and after a few more deep thrusts I felt Andy go tense. A shiver seemed to quake through his cock and it seemed to grow even bigger and stiffer inside me. He moaned loudly and I could feel his sperm shoot out of his cock deep inside my ass. Again and again I felt it flex and could feel his liquid filling my insides. He pushed one last time and then he was done, totally spent. He pulled out of me carefully and collapse against the couch.
When I had caught my breath I looked at Kevin, Jimmy and Rob. “You guys can cum however you want, but if you want to use my pussy than you have to use a condom. I’m not on the pill or anything. There are some in the dresser drawer…” I noticed that Kevin was holding some packets in his hand. “Ah, seems as if Kevin was prepared. Who’s first?”
Rob and Jimmy played rock-scissors-paper to see who went next and Rob won. “What do you want,” I asked him.
“Suck me off,” he ordered.
I got onto my knees and took him into my mouth. I used my mouth and my hands, sucking and tugging on him in long strokes and soon his hands were on the back of my head, holding me in place as he deposited his load on my tongue.
Jimmy was next and he wanted to cum in my ass, too. I was a sloppy mess down there and Andy’s cum had started to leak out of my hole and run down my thighs by then but Jimmy didn’t seem to mind. He shoved himself in me completely and fucked me fast and hard. He made me cum again and then his load joined Andy’s, deposited deep inside my ass.
Kevin was last and as he got up off the chair I could see that his cock was wrapped in a condom – I knew that he would choose my pussy, he always did. I rolled onto my back and spread my legs wide for him. He positioned himself and placed one of my legs on each of his shoulders. He entered me in a rush and I could see the lust in his eyes. I was quite proud of him actually, not many guys could handle watching their girl fuck three other guys right there in front of him. I decided that when my ass healed I would let him have a private evening with it as a reward.
He fucked me hard, the way that he does when he’s on a mission to cum. I felt him stiffen and could feel the heat of his spunk inside the condom. Eventually I got around to getting on the pill and we no longer had to mess around with those damn things but that day, it was a necessary evil.
Kevin pulled out of me and sat back on the floor. I looked around all saw that they were all sprawled out on the rug or on furniture, wearing that sly smile that men who are completely satisfied do.
I must have fallen asleep because when I awoke the last streams of sunlight were streaming in the windows. I was lying in Kevin’s arms and he felt me stir.
“Everyone leave?” I asked.
“Yeah, we all fell asleep and when they woke up they didn’t want to disturb you. They told me to make sure to tell you ‘thanks.’ I think you shocked them with your sexual prowess but even more so because they never expected you to honor the wager.”
“A bet’s a bet. I had to pay up.”
“I’d say you paid us all in full. More, I think actually. I think we owe you.”
“Oh, you’ll get your chance to pay up… the girls are never going to believe this and its going to take all four of you telling them what happened before they are ever going to believe me.”
“I think we can handle that,” he said and kissed my neck. “C’mon, let’s get in the shower and go get a bite to eat – you may have had all the meat you could take but I haven’t eaten since breakfast.”
“Haven’t eaten anything other than me, you mean?”
He laughed. “Right, nothing other than you.”