Author's note: the following story is purely a work of fiction and any resemblance to real people or events is purely coincidental. The author wishes to express his gratitude to Copperbutterfly for her editing to make this a better story.
I'm not bragging when I say I enjoyed my share of pussy during my high school years. I mean, you've got to be pretty backward these days not to "get some on you," even without trying. By far the majority of the girls in high school have given up their virginity by the time they graduate, a lot of them many times over.
When I went to college, it was really my first extended time away from home and my parents, so I was looking forward to some "variety" in life, meaning that I wanted to try a lot more of the girls than I had the chance to in high school. By then, I had worked enough to purchase my first car, a very nice two year old sporty coupe, good enough to let me get around the large campus and the fairly spread out town that hosted our school.
The town was large enough that it operated four large high schools and some of my new friends taught me about the local hangouts for each of the schools and that those hangouts always were filled with sweet young things that were quite willing to share their treasures with a college man; it made them feel sophisticated to be bedded by an "older" male.
That first semester, my schedule left me with light work on Thursdays and Saturdays, so Wednesday and Friday afternoons found me making the rounds of the high school places, checking out the girls, talking to whoever showed interest, and usually escorting one to my car for a ride out to a secluded area and a quick romp in the hay. Well, some of them weren't so quick, but that was alright. If it was quick enough, I might have time to pick up another sweet thing and go for round two; if it wasn't quick, my round two was with the same pretty pussy. Either way, I thought it was a win-win situation.
By the start of the spring semester, I was getting a little itchy to try moving up in class a little. I wanted to sample some of the college girls. Lord knows a school of over 67,000 enrolled students has enough of them. There were short girls, tall girls, heavy girls, thin girls, round girls, voluptuous girls, girls with big tops, girls with even bigger tops, girls with nothing on top, girls with skinny-minnie asses, girls with basketball-shaped asses, and girls with everything in between. I think the main reason I had stayed with the high school girls at first was that I was a little intimidated by girls who could make better grades in major college lines of study than I could.
I finally reasoned that, if they were smarter than me, that was just another way of being sexy, it didn't detract from their attractiveness. Oh, I got turned down a few times by girls that obviously looked down at me, but that didn't deter me. I found myself soon getting dates with college women — note that I had subconsciously changed from thinking of them as girls to women — and even found it surprisingly easy to get laid. In fact, many of the college women required less persuasion than the high school girls did.
Dorm life was somewhat restrictive for me, even though it was a highrise coed dorm. The building I was in was eight stories tall and the only restrictions were that roommates had to be of the same gender. Well, that and that the bathrooms were reserved for one gender or the other and no mixing was allowed. Side by side rooms frequently were occupied by members of the opposite sex. The dining hall and other common grounds were intended for use by all residents. There was no restriction on being in your room at any particular hour, such as a curfew I had heard some schools used to impose, particularly on the females. Nevertheless the dining hall was only open certain hours and the front doors were locked from 1:00 AM until 6:00 AM every day. I also decided that I could save money by doing some things for myself.
Before the end of that first spring semester, I searched the town for available housing for the following fall, finally finding one nice three-bedroom apartment that would be available when the current occupants graduated in the spring. The house had originally been something of a mansion for a single family but was broken up into apartments, one on each of the three floors. The one I signed up for was on the second floor. All I had to do was find some roommates to share the cost and I would be doing good.
I bought an ad in the weekly college newspaper, advertising for roommates for the fall semester. I was amazed at how quickly the calls started coming in the afternoon the ad first appeared. The first two callers decided that it was too far from campus and they wanted to find something else.
The third caller was Lindsey, who asked if she could meet me. I invited her to my dorm room to discuss the apartment. Twenty minutes later, a pretty brunette was sitting across my study desk, looking at the layout of the apartment that I had showed her.
"So you're taking this bedroom, right?" she pointed to the master bedroom.
"And either of these two is still available?"
"Good. That kitchen looks good sized. Nice living room."
"Yeah, and the owner will repaint this summer."
She looked up at me, her expression very serious. "Are you gay?"
"No — happy but not gay."
She laughed. "Girlfriend?"
"Nope. No one special."
"Okay, if you'll give me one of these rooms, I'll pay one third of the rent and expenses and give you fringe benefits."
"What... kind of fringe benefits?"
"You like sex, right?"
"Do you like... ass?"
"You know... doing it in back door."
"I don't know."
"Never tried it."
She raised her eyebrows. "You've never had a piece of ass?"
"Ohmigawd! You don't know what you're missing."
"Yes, really. For me, it is the greatest thing... since sliced bread. Gawd, I love it."
"Wanna try it?"
"Sure... if you want to."
She jumped up and began to shed her tank top and jeans, kicking her shoes into a corner while I stripped. She finished first and reached into her little purse, extracting a tub of K-Y lubricant. Dropping to her knees in front of me, she gave my cock a few quick licks and sucks to help it grow stiffer and then smeared it liberally with the lubricant. When I indicated which bed was mine, she climbed on, raised her legs up beside her and used one hand to dribble out the lube while the other coated her valley and then worked fingers inside.
With her upper arms resting on the backs of her thighs just above her knees, her ass was raised in the air so magnificently for my assault. I got on my knees just below her and advanced toward her puckered opening.
"Give me a few seconds," she said, just before I pushed inside.
As I watched, it was like seeing a therapist work the tension from muscles, except for Lindsey it was a mental thing instead of physical. She relaxed her muscles, including the sphincter holding her anus closed. It actually began to open before my eyes. She grinned at me and gave a nod for me to continue.
I had expected her to be tight, and she was. I had expected it to cause us both some pain, but it didn't; at least, it didn't hurt me and from her expression it didn't seem to hurt her. I stopped pushing a couple of times, but she urged me on, until I pressed against her buttocks. I couldn't believe how loudly she sighed. I backed out until I could feel the rim of my mushroom head against her ring of muscle, then pushed back into her. She kept her legs propped back with her elbows, while her left hand played with her clit and the fingertips of her right hand barely scraped my shaft as it stroked in and out of her opening.
Lindsey had a nice pair of tits, probably about 36C, perhaps 36D. I would have loved to bend down and suck on them but with her legs and arms as they were, it just wasn't possible. However I planned to sample those jewels when the opportunity arose. Meanwhile I gradually picked up speed, stroking in and out of her anus. She lasted maybe two or three minutes before she started yelling through clenched teeth that she was cumming. Suddenly she got tight, as her sphincter tightened around my shaft and I was forced to stop moving until she loosened up again. Then I resumed stroking her ass.
She was noticeably looser by then. If I had enjoyed stroking her ass before, now I absolutely loved it. Pussy is nice but, if all asses felt as great as Lindsey's did, I couldn't believe the population explosion wouldn't have died a natural death. After pumping her ass for a couple of minutes, Lindsey gingerly moved her arms, releasing her legs for an instant until she could grab her ankles with each hand. Her bottom was not quite so high but it left her other treasures available to me. I started by leaning over her and locking lips with her in a long sensuous kiss, still stroking my prong in and out of her anus.
The change in position seemed to do something to her because just a few minutes later, Lindsey was talking loudly, "Ohmigawd, ohmigawd, ohmigawd, baby, fuck my ass, honey, fuck my ass, oh, yeah, baby, cream my ass, honey, ram that big cock into my butt, sugar..."
.... There is more of this story ...