It started off as a stupid joke, one of those things sororities want entering freshmen to do during rush week. All the older sisters in the house I was most interested in voted that all the new freshman pledges would have to try anal sex before the end of the semester. If we wanted to join up, we’d have to take it up — up the ass, that is.
I was pretty eager to get in, so I played along, but already I was trying to figure a way of faking it. I’m no prude, but I wasn’t going to let some stupid frat boy stick it in me — much less in my back door! — just to get some stupid signed certificate.
Well, you know the saying, never say never. Two nights ago I was well into my first semester, doing fine in all my classes, and I decided it was time for some fun. So I called up this dude who had been hanging around with me for a while. He was certainly not the fraternity type, but I like him, and even though he’s not the kind of man I’d ever marry, he’s a lot of fun.
Anyhow, he took me to this pretty good party, and then we made out in his car, as we’d done before. Bobby knows exactly which buttons to push to make a girl happy — at least, this girl — and he was doing a fantastic job of it tonight. I was ready to go all the way right there in the car, but Bobby said a bed would be a lot more comfortable.
“Besides,” he said as he caressed my thighs with one hand while his other brought me to yet another orgasm, “I don’t have a condom with me, and I’m tired of fooling around in this rattletrap. I want to fuck you, I want to fuck you in my bedroom, and if we go there we can do it all night.”
So after getting off again, I was in the elevator going up to Bobby’s off-campus apartment. I must have looked like a tramp, with my hair mussed and my clothes disheveled and my lipstick messed up where it had rubbed off on his shaft while I was going down on him. Not to mention that I was with a man with a huge bulge in his pants. But hey, we were both too horny to slow up. He let me put the condom on him, and then I was on my back in his bed, my ass propped up on a pillow, and he was fucking me.
I came nicely from that too, and with a little party buzz mixing with the afterglow of really great sex, I was totally relaxed as I came down from my first fuck with this man. I stretched out on the bed face down as he massaged my neck and back, doing a superb job of it. Somehow his hands ended up at my ass, spreading my legs a bit and rubbing out any soreness thoroughly. I remembered what he had said about doing it all night, and I knew he had plenty of orgasms in him, so I figured this was just the beginning of round two. I purred, showing him how much I enjoyed the way he was touching me.
His fingers felt so good as they moved on to my pussy. Like I said, Bobby knows me. He brought me up to the edge of what I could tell would be a massive orgasm and held me there, rubbing my clit just irregularly enough that I couldn’t quite get off on it. He held me at plateau, teasing me, his fingers moving from clit to cunt and back again in the most exciting possible way.
Then he did something new. One finger went for the spot between my pussy and my asshole and began to massage it. It felt good, and the more he rubbed that spot, the better it felt. The funny part was that even as that finger touched the outer rim of my asshole, I never gave a moment’s though to that stupid sorority pledge.
Then he was rubbing my asshole itself in exactly the same way, light and slippery and so sexy. Soon the tip of his finger was turning inwards, pressing, popping through the tight ring of my anus. It stuck there one knuckled deep, and it felt so good I never wanted him to stop. I felt lightheaded and horny, and as I felt his cock pressing its hardness against the back of my thighs, all I could think about was the moment.
Bobby pulled his finger out of me and replaced it with his thumb. Then he took a tube of lube from the drawer of his night table and greased up my asshole thoroughly. That was nice, and as his thumb pressed inward, I felt my asshole widening to fully accept the bigger size. He pushed it deeper into me, spreading my asshole with the meaty blade of his upper thumb. Soon I was taking it all, grunting in time with his finger thrusts. My eyes were closed, experiencing all the new sensations and reveling in them.
Somewhere during that thumb-fuck, during one of the times he pulled out to get more lube and my asshole gaped and wondered when the fuck he was coming back to fill it again, he must have made the switch. Because all of a sudden, I realized that he was cupping my tits, one in each hand, while there was still something thrusting itself in and out of my ass. He had switched from his thumb to his cock. I was taking a man’s cock back there, I was doing what my sisters had told me to do, Bobby was fucking me up the ass!
As my brain was filled up with this realization, my body was responding perfectly. I liked the new thrills the spike in my asshole was giving me. No, not really. I loved them. I loved the way his cock filled me to the max, the overstuffed way it was making me feel. I loved that feeling I got every time Bobby stuffed his prick up me, and the other feeling I got every time he came so close, so very close to pulling it out. There was no need for more lube now, which was a good thing, because I don’t think I could have stood it if I had lost his prick again.
As you may have been able to guess by now, Bobby isn’t exactly porn-star material. In fact his cock isn’t that long, and it’s pretty thin, too. But in my ass it was completely satisfying. So he stoked me nicely until I came yet again, with a little help from my own fingers. It was only when I felt his jism rushing up inside me, then spreading out in a pool of warmth, that I realized he had been barebacking me. What the hell.
So we did end up doing it all night, and Bobby signed the certificate, which I have a sneaking suspicion he knew about all along, and I got to be a full member of the sorority and everything. I wonder how many of the other girls submitted phony evidence, anyhow? I guess I’ll never know.
But there’s just one thing left over. Now that I’ve tried anal sex with Bobby, I’m dying to try it again, with another guy. You know, someone just a little bit — larger? It might not fit with the image of a woman attending a small elite liberal arts college, but there are some things in life that a girl just has to face up to, and this is one of them.
I admit it. I’m looking for a man with a big dick, I mean a really big one — and when I find him, I want him to fuck me up the ass.
##### ##### #####
A Dish Best Served Cold
When I was just eighteen, I fell in love with a girl named Jodi. She was the sweetest girl I’d ever known, and she told me that she loved me too. She was also the first to suck my cock, the first pussy I ever tasted, and the first woman I ever fucked. I was convinced that after college she was the woman I was going to marry, and we’d live happily ever after. Of course, that was before I came home one night and found her in my parents’ living room on her hands and knees while my older brother Dennis rammed his cock in and out of Jodi’s ass.
Pissed off doesn’t even begin to describe how I felt. I screamed at them until Dennis retreated to his room and Jodi ran out the door without even putting her underwear back on. I cried myself to sleep with the pain of Jodi’s betrayal, and the next day I told Dennis, “Some day you’re going to get married, and then I’m going to fuck your wife.” He just laughed at me, and told me Jodi was nothing but a slut and I was better off without her. I never saw her or heard from her again.
Well, that was a long time ago. I did go to college, but I didn’t get married. When I came back to my home town for good, though, Dennis had gotten married. Laura was new in town since I left, so we hadn’t grown up with her, but I could see what Dennis saw in her — she was not only a looker but she shared some of his interests and even a few of mine, so she was easy to talk to.
Dennis works as a traveling salesman, although what he sells is extremely high-priced computer software, not vacuum cleaners or hairbrushes. It’s the kind of thing that you can’t just download from the Internet — his company never gives anyone a copy without a signed contract and a hefty down payment in hand. I don’t know all that much about it. Anyway, it means a lot of travel for him, not only in this country but all over the world, but he doesn’t seem to mind that.
On the occasion I’m going to tell you about, Dennis was going to be gone for a full six weeks installing and training for his company’s latest extremely hush-hush product. So he asked me to stop in on Laura from time to time, say on my way back from work, which wouldn’t be too inconvenient for me. So I waited for a week, and then I went to check on her. When she answered the door, it was obvious that she’d just been in the pool — she was dripping wet and wearing a bikini that left little to the imagination.
She smiled when she saw me, invited me in, and offered me a beer. I followed her into the kitchen, where she poured an imported beer into an icy-cold mug, and then accidentally dropped the empty bottle. When she bent down to pick it up, the crotch of her swimsuit was pulled so tightly against her body that I could see her pussy lips under it. Ohh, they looked so sweet, I just wanted to lick them and suck them. My mouth went dry, and I downed the beer in one long pull as she stood up. Her eyebrows climbed halfway to the ceiling, but she didn’t say anything.
The next two beers she kept up with me drink for drink. After those, our eyes met and locked together until I pulled my gaze away from hers and let it travel downward, roaming over her big beautiful tits, her flat stomach, and the small purple patch covering her mound. Then I met her eyes again and licked my lips. All of a sudden she was in my arms.
We kissed feverishly, our tongues meeting like old friends inside her mouth. I brought my hand up to caress one economy-sized breast, pulling her tight against me with the other so that she could feel my hard-on against her stomach. When she was rubbing herself against it with no help needed from me, I brought both hands up behind her back and untied her bikini top, and then pulled it off her and tossed it to the floor.
Then I held her at arm’s length so I could get a good look. I knew how big they were, but I hadn’t truly appreciated them until I could get a good look at them bobbing, all pale white with dark rose nipples that were pure candy to me. I leaned forward and sucked one hard point into my mouth while my fingers tweaked the other over and over. She moaned, and then to my delight she was deftly slipping one hand into my shorts and squeezed my hard cock over and over until I could feel my own pre-come dripping from the tip.
I could have stood there all day sucking on Laura’s tits, but I wanted to slip a finger or two into her pussy, which I knew was wet from top to bottom. So I let my hand snake slowly down her belly until it could find its way into her groove, then ran it up and down the outside of her until I could part her pussy lips and deal her my middle finger straight up her cunt. She shuddered and shook all over as she felt my finger ram home.
Then I was on my knees pulling off the rest of her bikini. She stepped out of it quickly, eagerly. My thumbs parted her pussy lips and I gave her a long lick. Laura shuddered again, and I glanced upward to see the look on her face. Unfortunately, her big boobs were in the way.
I licked her thoroughly, and before long she was groaning rhythmically and pushing her mound into my face. When she began to lose her balance, I eased her to the floor and onto her back. Then I regrouped, giving her long licks from her asshole all the way to her clit. As her pleasure rose to its peak, I let my tongue circle around her sensitive button and finally sucked it straight into my mouth. She cried out and exploded, her love juices gushing all over my face.
As she quivered and twitched her way down from the orgasm, I was on my feet again and stripping my clothes off. A second later, I crawled onto her body, my cock pressing into her pussy. She reached down and grabbed me with her hand again and guided me till I was lined up just right, and then I pushed. Once the head was secure, the shaft followed, and I sank into Laura up to my balls.
I screwed her slowly and carefully, knowing I needed to get her motor running again. Sure enough, very soon after that her heels were kicking at my ass as she screamed “Harder! Faster! Deeper!” They were almost the first words she had spoken since offering me that first beer. But within a few more minutes she was babbling with her frustrated desire, and I knew I had to deliver. So I slammed it to her again and again, and suddenly all my memories of Jodi were jarred loose. I grinned fiercely as I pounded Laura’s pussy with my prick.
I put it to her with everything I had, pulling my cock all the way out until only the head kept it inside her, then using my feet for leverage to ram home deep into her cunt. My cock was a jackhammer and Laura was the virgin pavement I was trying to break open for good and all. Her moans rose in intensity and she humped up against me faster and faster, finally screaming out my name and “I’m coming, I’m coming”.
So was I. At that very moment when I felt her pussy throbbing and pulsing around me, I lost it, spurting my jism straight up my sister-in-law’s cunt and leaving it deep in her belly. When I pulled out to drip the last of my load on her thighs, I was amazed to find out I was still hard. So I pulled and pushed until Laura was on her hands and knees, and then I pushed my boner straight into her beautiful big butt.
She screamed and screamed, first in shock, then in pain, and finally in joy. My cock filled her completely, stretching her asshole wide, an asshole that I was sure had never taken any cock before. I gave her an ass-fucking she’d never be able to forget, and soon the screaming was replaced by whimpering and begging, first for me to take it out, and then for me to bang her harder and deeper. I did. I rode her for a long, long time, using my hands to hang on to her tits, before I let loose and blasted a hot load of come into her bowels to keep the first load company.
When I pulled out again, she had tears in her eyes, but I could tell from the way she was trying to talk that they were tears of overwhelming pleasure. Her ass had reduced my cock to a limp noodle, but I knew the cure for that. Within a minute she was back on her back and I was licking her cunt for a second time in the sixty-nine position. It took her a while to accept my cock in her mouth, but I just kept teasing her lips with it while I teased her clit with my own lips until she finally gave way. Once I was in, she sucked me like a pro, and by the time she had come for me twice, I was halfway down her throat and shooting my last load of the day.
As I dressed myself and got ready to leave Laura found her voice again, as she tried to make me feel guilty about fucking my own brother’s wife. But I just remembered Jodi and gave Laura a big smile and a sweet little kiss goodbye, tasting my own come in her swollen mouth. I told her I would be back the next day to fuck her ass all over again.