The names of those people and some of the events in the story of been changed to protect several identities.
As we're playing our normal Friday night game, someone suggested that we pull out the alcohol and play some drinking games. It was just me, my roommate Alex, and Sherry so we all agreed and out came the alcohol and the cards. We started by playing Asshole, and wouldn't you know it, I was it for most of the game. When I finally started to win we were all pretty blitzed.
Alex dared Sherry to play strip poker, and she hesitantly agreed. Again luck was not on my side, and I was the first to get totally naked. After that point if I was too loose I was to perform silly actions as dictated by the winner. I was made to do push-ups and chin-ups. Sherry was the next to have to go totally naked, but she wussed out a bit and wrapped herself in a blanket. Alex was upset that she did that, so when he lost he too grabbed his blanket. Unfortunately for me, at one particular moment I got a clear unobstructed view of Alex's short hairy cock. It sent shivers up and down my spine, but not in a good way. Eventually the game fell apart. Drunk and sexually frustrated, Alex went upstairs to bed.
Sherry, who has an olive complexion, dark eyes, and long thick black hair, had curled up on the couch next to me. She was a freshman at the college we were all going too, and she had been a virgin until just recently. She would come over and talk to me about how she just fucked this guy, and how big his cock was. She enjoyed her new found sexual freedom, and spoke of sucking cock like it was an ice cream cone. In fact, since her first time, she had actually had sex with two other guys. She had a nice ass and a good size rack.
As we sat on the couch we started to talk about things, and as such conversations go, it eventually led to sex. Well with my arm wrapped around her neck and shoulder I was able to bring my hand to rest upon her boob. I squeezed it gently and it brought a moan to her lips. She turned her head to face me and we engaged in a soft kiss. As she did that she reached down to rub my cock to hardness. It felt so good to have her hand rub me. She slowly started wanking on my rod, and within seconds she had me going.
She slid off the couch onto her knees, and she eyed my stiffness to see if it was ready to play. She continued to stroke me slowly, but then she stuck her tongue out and licked first the head, then my shaft. She sucked me into her mouth in one wondrous gulp, and proceeded to suck me. She bobbed her head up and down, I was lost in the sensations that she provided me. My cock tingled with ejaculatory anticipation. I grabbed her hair and started thrusting into her mouth. I so needed to cum. There was nothing more that I wanted at that moment then to unleash a monster load into her waiting mouth.
"Argh, ug, ug, hmmmm, so goooood. Suck it please, I'm so close. Oh God, here it cummms." I opened up a huge can of whoop ass, or at least sperm. I thrust deep into her throat and made her swallow every last ounce of my love juice. She kept right on sucking even after I finished spewing to make sure she got every last drop.
After taking a moment to rest, I joined her on the floor, and started to kiss her. I could taste my salty cum on her lips and tongue, but I did not care. Although she had nice size tits, they were a bit on the droopy and wrinkly side, but I sucked on them any way. Her nipples were soft and chewy and I sucked on them a long time. While doing that I started to stroke her pussy and clit with my right hand. She started to moan out her pleasure.
When I knew she was ready for more, I slide down her body. I parted her legs to get a better view of her pussy. Like her tits her labia were wrinkly, but she was wet and pink to dark red. I knew she was excited at that moment. I tasted her with my tongue, and started to slowly push it in and out. She squirmed from my tongue fucking, and she started to secrete white fluid. Now we're playing with fire. I stuck a finger in her pussy, and hooked it upward to stroke her G-spot. This was what she needed. She started to cum into my mouth and when she did she really gushed.
I did not want to miss a golden opportunity. She had previously mentioned that she had used a condom with the other fellows, but I did not have one readily available. With her mind in an altered state, I quickly slide up and mounted her. My cock found her pussy in one stroke. I brought her legs up around my back and locked them there, so she wouldn't think of getting away. Again I needed to dump my cum-load badly, and my fucking showed it. I fucked hard and fast. Since I just made her cum, when I started fucking her it set her off into multiple-orgasmland. "Oh yeah Sherry. Your pussy is so tight. I love how my dick feels inside you. You are so wet and the heat is undeniable. I'm gonna cum soon."
"Evan don't cum inside me, please. I'm not on the pill, and you're not wearing a raincoat."
"Ok, Sherry. I'll pull out before I cum." I in fact had no intention of pulling out. If she was unprotected and possibly fertile then he shoots, he scores. "Ah, ah, oh, oh, grrrrrr...."
Sherry was starting to get lost in her own pleasure, "Fuck me Evan, and Fuck me hard. I need your cock so bad. It fills me up so good. You know how to use it well. I can't stop cumming."
As I felt her go into her third convulsive orgasm, I bust my nuts wide open into her unsuspecting twat. No warning grunt, just a deep bottoming out thrust that hit her cervix and my seed bathed her insides with baby makers. "Evan what are you doing? Quick pull out. I don't want to get pregnant." Since I had locked her legs around my back it made disengaging difficult. When we finally did, I pumped my whole load inside of her. I pulled out and rolled over to catch my breath.
She was upset and started to cry a bit. She got up to get dressed and asked me to drive her home. She did not say anything to me on the way home.
The next day there was a knock at my door. It was Sherry. She wanted to talk about what happened. So we went up to my room to discuss the previous night, because my roommate was in his room. Before she could say anything I kissed her passionately. Before she knew what was happening, I had her undressed, and on all fours in my bed. I was prepared this time around and had put my condom on. Not because I was afraid of catching something or getting her pregnant, but for something else entirely.
From having had long conversations about her new found sex life, she had never had anal sex before. That is before now. As I had her on all fours I lined my rod to her brown rosebud. I pushed the head of my cock through her sphincter. "Oh, Evan, please don't, not there." I didn't hear her, the only thing I heard was the blood rushing through my lust filled brain. I sank another inch into her ass, and she started to cry out. Not to want to be discovered by my roommate I grabbed her panties and shoved them in her mouth to try to keep her quiet.
I could not take the pressure on my cock any longer. I thrust everything I had up her tender ass. She cried out, but her cries were muffled as I had hoped. As I started thrusting harder and faster, I could tell that her pain had went away and she was in fact pushing back onto my cock. Sherry started working her ass muscles massaging my cock. The feeling was so intense. At this point she was pretty well broken in so on one of my backstrokes; I pulled all the way out of her to her displeasure. As I did so I also pulled the condom off. I wanted to ride her sweet ass bareback, and to have her feel my load fill her up.
I fuck her hard for a couple of more strokes and shoot a pint of piping hot fresh sperm up her rear. When she felt her poor battered bowels being flooded she went into her own convulsive orgasm. She shook the bed like a mad woman possessed. She clawed at the bed spread and ripped a hole in it. Sherry's orgasmic spasms caused her to clamp down on my cock. I could not pull out even if I wanted to, and the rhythmic pulsing of her sphincter kept coaxing cum out of my cock for at least a minute. I slowly pulled out, and when I did I saw the copious amount of sperm run out of her stretched hole. I collapsed on top of her, and we drifted off to sleep. When I woke up she was gone, but she had left her panties hanging from my cock. I never saw her again after that day, and was sad to see her go. I wonder what became of her.