My First AssbyChimney Sweep©
Carolyn was a slut. I don’t like to use the word, but it fit her perfectly. She had a reputation in high school for giving it up to any guy who wanted it, but as far as I could tell not many guys claimed to have taken her up on it. She had an older sister who had graduated the year before, and the stories about her were even more widespread (pardon the pun) so I suspected that some of it was hand-me-down reputation.
She was a pretty thing, if a bit too rooted in the fashion of the 80’s. I suppose that isn’t fair since it was 1988, but most seniors didn’t bite quite that hard on the fashion hook. She wore the leg warmers, brightly colored tights, the Madonna wannabe uniforms, etc. If you could catch her on a low-makeup day you would see that she had large, pretty eyes and an inviting, thin-lipped smile. Her nose was long and thin and gave her face a sharp look, but I always liked it. I have a thing for noses, I guess. Her body was nice, but nothing outrageous. Puberty had filled her out appropriately but her bra wasn’t bursting and she was a little long and gangly. Her hair was usually platinum blonde but I had known her long enough to remember when it was a more natural honey brown.
I had known her for a few years, though we didn’t move in the same circles. I took advanced classes and she took the easy ones, but we occasionally ran into each other. One semester I made the mistake of taking a geography class after feeling a bit ashamed at not being able to locate the Azores or Lesser Antilles at the urging of my grandfather. It turns out that geography was one of the classes with the lowest expectations in the school. All the idiots took it for an easy grade since the most difficult part of the class was coloring in the lines and making sure Zimbabwe had a different color than Chad and Nigeria.
Carolyn was in the class, and I think it was even a bit below what she expected. She saw me on the first day and took a seat next to me. I smiled politely at her but we didn’t chat much. The teacher was known as a hard ass so we didn’t try his patience.
The subject was mind-numbingly easy. Eventually the monotony got to us and we started passing notes just to pass the time. Most were just conversational or a game of tic-tac-toe, but one day I was encouraged to write something a bit more adult.
Carolyn came in that day with an extremely short skirt and no stockings. She was a long-legged girl and made a bit of a stir as the semi-intelligent animals hooted and whistled at her. Mr. Jameson came over and gave her a little warning about her inappropriate wardrobe that I overheard. We shared a look as he went back to the front and started class, and she mouthed the word “asshole.”
As I tried to stay awake to Mr. Jameson’s droning my eyes kept going to my left and lingering on Carolyn’s nearly naked legs. I’m not partial to any particular part of a woman, but I appreciate a nice set of legs as much as the next guy. I also noticed that Mr. Jameson’s 50-something eyes were constantly flicking over to her exposed flesh, and I decided to have some fun.
I scribbled out a little note and handed it to Carolyn when the teacher turned away. It said, “I think Mr. Jameson likes what he sees.”
She shot me a disgusted look and replied in kind, “Sick old bastard. I didn’t wear this for him to stare at me.”
I replied with another note, “If you wore it for me to stare at you then it’s working.”
Her impish smile told me that I had not aimed too far off the mark. Her reply said, “Maybe I did.”
Unfortunately, I had to find out what her reply was a little later. Mr. Jameson, shooting a glance at her legs again, noticed her trying to pass me the note. We were sent to the principal’s office in a loud and embarrassing manner as he read us the riot act and preached mightily the sins of not paying attention while he wrote out or hall passesm and still he kept stealing glances at her legs. Jackass.
While walking to the Principal’s office she told me what she had written.
“Well, you must have known people would stare. You can’t show off that much leg without drawing some attention.”
“I know. I like the attention.” She walked a little quicker and got out in front of me, intentionally exaggerating her swinging hips, and hiked up her skirt a little more to show off for me. She was wearing a black thong which she quickly covered back up.
I must admit that I was aroused at that point. I knew she had a reputation and I felt she was below me, but when the smaller brain starts talking to the bigger brain, he makes a lot of sense. She kept shooting me those sexy little glances all the way to the front office, strutting like an alley cat in heat, and I was half erect by the time we got there.
She was well known to the disciplinary staff, but I think that was my first trip to the principal’s office in high school. I gave my best reasonable account of the situation and the excuse, and offered up the fact that I know it was wrong but the course was just so far below my abilities that I was bored. I apologized for distracting my classmate and made sure they realized that I started it. Ms. Evans, the vice principal and disciplinarian, was involved in the academic teams of which I was a part and waved it all away as the overreaction of a teacher and an honest apology from a top student. Carolyn didn’t even have to go in to the office.
“What did you tell her?”
“I just said that if I was to have any chance at all of finding out what’s under the rest of that tiny skirt that I would need to get you out of there without even a warning. So she let us go.”
“Bullshit! What did you tell her?” I related the true story on our way back to class, but we took the long route to kill time. When I finished she said, “That was nice of you. Thanks. Evans has been on my ass since I started here. And what makes you think I’ll let you into my panties, even for getting me out of another write-up?”
“Just wishful thinking, I suppose.” We were walking next to each other, so it was an easy reach for me to bend down just a bit and touch the back of her thigh with my fingertips. I quickly brought them up and brushed them against her thigh and ass, reaching under the skirt a little. “Was I wrong?”
She gave a little shudder from my touch and shot me a lecherous look. “Maybe.”
The bell rang and we had to go our separate ways, so I took a shot. “Meet me at the west entrance after school. I’ll drive you home if you want.”
“I’ll think about it,” she replied, walking away. I watched those long legs swing out of sight around the corner before heading to my locker, an uncomfortable bulge rising in my pants. I spent the rest of the day wondering what I was doing. She was sexy enough, and at 18 I was always ready for a fuck, but I really didn’t want to get mixed up with this girl. I admit I was a bit of a snob, but girls with reputations usually get those reputations for a reason. Then again, if I was willing to fuck her, and she was willing to fuck me, then didn’t that put us both in the same boat? I thought about leaving her high and dry, but the smaller head was very eloquent in his argument to keep my appointment after school.
She was there when I showed up, leaning against the wall with no book bag, effectively expressing her disdain for class work. She smiled when she saw me and perked up a little, perhaps having been worried I wouldn’t show. We walked out to my bright red Triumph Spitfire in the warm afternoon of an early September. I put the ragtop down and then opened the door for her. As I got into the driver’s seat I asked, “Where to?”
“How about your place?”
I pulled out of the parking lot and headed through the sparsely populated almost-farm land around our high school. The school was out in the boonies a little and it took a couple miles to reach civilization. Apparently Carolyn didn’t care that we would actually reach civilization soon, because she was ready to go already.
She reached across the gearshift and started undoing my zipper. I was surprised, but not stupid enough to stop her. I lifted my ass a little to let her have easier access and she quickly had my fly open and was pulling down my pants. I had the presence of mind to take the long way home, sending us out through more farmland. In a car this low, and with the top down, we would be giving a show to the whole world.
My cock was in her hand in a hurry, and she jerked on it for a few moments before she dove down to suck it into her mouth. I had never had a blowjob while driving before, so I was worried about keeping us alive. She sucked hard at my half-erect dick, working it quickly up to full mast.
She was aggressive about it and it was not one of the better blowjobs I’ve had, but it is a rare blowjob, in my experience, that one can truly call “bad.” It was a bit awkward for her to really get in there and take care of business, so she was jerking me off fast and hard while sucking on the head. I reached my right hand up her shirt and got a handful of tit to play with while she worked. I got a little moaning for my attention as I fingered her hard nipple. I would have slipped a finger up her pussy but I couldn’t reach her from that position. Plus, I had to save some attention for the road.
She was a little rough, but before long I started to thrust up into her face as my orgasm approached. I put both hands on the wheel, planted my left foot hard into the floorboard and made sure we were safe as the first glob of my sperm hit her mouth. The sensation was intense, doubly so because I had to pour so much attention into driving. She sucked it up quickly and increased her pace with her hand, jacking me off like it was a race. She continued to pump me and lick up my load until I finally relaxed, spent for the moment. I had to flex my white-knuckled fingers from gripping the steering wheel so hard.
Carolyn sat up, leaving my wet cock dangling in my lap with my pants around my knees. She leaned out over the passenger side and spat a few times, then sat back down in the seat. She flashed me a wonderful smile as she wiped off her chin. God damn this bitch knew how to make it hot and sloppy. I was looking forward to fucking her brains out now, but I wasn’t sure if that was in the cards.
“Damn. That was intense. You trying to get us killed?”
“Great way to die, huh?”
“I guess! Holy shit that was hot.”
“Nice cock. Can I get more of that at your house?”
“Yes you can.” I pulled over at the side of a cornfield to pull up my pants, then spun around in a U-turn to head back to my house. Our detour had taken us far out of the way and I was eager to get home to give the nice lady more of the nice cock she wanted.
She put one leg up on the dash, spreading her legs open wide and pushing the skirt out of the way. She put a hand down by her crotch and started playing with the hem of the fabric, looking at me to make sure I was watching. I put a hand on her thigh and started rubbing her through the fabric of the panties. She was very wet and the panties were soaked quickly. Every shift of the gears wiped more of her scent on the gearshift, a smell that would linger for weeks in the car.
I fingered her as best I could while driving like a mad man to my house. Once there I shut the car off and we finally kissed, a passionate, needful kiss full of pushing tongues and nipping teeth. I had softened a bit after the blowjob but my 18-year old body had quickly recharged, and as I leapt from the low convertible I did so with a nearly full erection straining to get free.
Carolyn followed closely and pressed herself hard against my back, reaching around to tug at my denim-encased cock as I fumbled with the keys at the door. After what seemed like a dozen attempts I finally shoved the key home and we tumbled into the house. I didn’t think I would have that much trouble getting my cock into her sopping wet hole. We went up the stairs in a tangle of clothing and tongues, grasping hands and probing fingers.
And then we were in my bedroom, behind the closed door, completely naked and making out so hard it was almost like a fight. Her body was harder than I thought it would be and her flesh was cool to the touch. She continued to shove her tongue at me like a weapon, and I answered every thrust with one of my own. Her hands roamed me quickly, as if she couldn’t touch enough of me at once, while I had one hand full of ass cheek and the other full of tit. She was a firecracker! I broke our embrace and pushed her down on the bed, moving in for the kill.
“Hold on,” she said, getting up and grabbing for her denim jacket which lay on the floor in a heap. She dug into a pocket and retrieved a couple of items. One was a rubber, and I was glad she had her own because mine were a little old. The other I didn’t quite see. She crawled back to me on hands and knees, then sat up in front of me and grabbed my cock with both hands, dropping her items on the floor. He repeated her frantic blowjob technique on me for a few moments while her eyes bored into mine. I was about to take a handful of her hair when she popped my cock out of her mouth and reached for the rubber. She put it on quickly and expertly, then got up off the floor and faced me for a moment.
“Look, you need to know something. Don’t fuck my pussy. I’m a virgin and I want to stay that way, so keep that thing out of my pussy, got it?”
I must have looked like a dumbstruck ox because she laughed at me and laid a cool hand on my chest. She held up the other item in front of our faces. It was a small tube of lubricant. She pushed it into my hand and crawled onto the bed, ass in the air and pointed at me.
“Lube up that fat cock and shove it up my ass, stud.”
I had never fucked a girl in the ass before and I was stunned. I thought girls hated that. I had joked around with other girls about it and they had all reacted as if it were something disgusting and degrading, but here was this hot little bitch begging for it. I was stunned, but not stupid.
I popped open the tube and lubed up the already slimy condom, making sure I had the entire shaft coated. Carolyn was wiggling her ass back and forth at me, looking back over her shoulder with an anticipatory grin. “Hurry up, damn it!”
I got up behind her put my slimy cock on her puckered little asshole. She pushed back against me and my dick deflected away but I quickly grabbed it and pushed it hard into her ass. It went in deep with the first push and she let out a bellow, a deep grunt as I entered her. She pushed back into me and stuck the rest of my shaft inside her. She was wonderfully tight at the entrance and intriguingly gentle beyond that.
She had no time for intrigue. She was humping back and forth on me before I could grab her hips and take control. She seemed to want it hard and I was eager to oblige. I pulled out almost to the tip and rammed it back in as hard as I could, holding her ass to me for a moment as I enjoyed the sensation of being all the way inside. Again she gave that shouting grunt, that low yell as if she had been punched in the belly. She dropped to her face to the comforter and put her hands back to grasp and scratch at me as I pulled back for another thrust, and another. I fucked her as hard as I could, blasting away at her tender innards just like she wanted. She kept barking like a dog as I fucked her ass for all I was worth.
After a while I was getting a little tired of the position, so I pulled out and slid back to get my feet on the floor. She was an animal now, and the look she shot me was one of confusion mixed with base lust and fury. I grabbed her ankle and dragged her down to the corner of the bed. I had no footboard so there was nothing in the way as I set her belly down on the corner, legs dangling down and ass bared. I squatted a bit to get into position and then swiftly invaded her ass again to the sound of her lovely voice bellowing out her lust.
From this angle I could more easily access the rest of her and I grabbed two fistfuls of her false blonde hair. I pulled her head back and she snarled at me, still scratching and clawing back at me. I was able to throw all my weight down onto her asshole from here and I did so, repeatedly. I rode her like that for quite a while, but never did she give me any impression other than that she was in complete heaven. I felt like I had a tiger by the tail and dared not let go.
It was hard to tell what was an orgasm with her with all that yelling and grunting, but after a while I could hold back no longer. I released her hair and grabbed her hips again, pulling her up into me. As the orgasm drew near I picked her up and twisted her on the bed so I was coming in at an angle, and from here I could penetrate even more deeply. I pushed in and held her tightly to me as the first contraction neared. I held myself still, driven fully inside her as the first spasm started filling the condom. A quick thrust and again I was pulling her onto me as hard as I could. Again and again I held her entire body up and fucked as hard as I could into it. Her sphincter gripped the base of my cock hard, making me spasm even more. The feeling was fantastic, very fulfilling and deep, unlike the sharp, almost painful orgasm she had given me in the car.
I kept thrusting until the wave passed. My energy disappeared and I fell to the bed like a marionette with its strings cut. I slid out of Carolyn’s ass with an ugly sound, but I certainly didn’t care. She rolled over and cuddled up next to me. She played with the hair on my chest and I ran my fingers along her shoulder and back, her skin still cool and smooth on my fingertips.
We relaxed for a while and talked a little bit in quiet voices. I asked if she really enjoyed that and she replied very strongly in the positive. She said she couldn’t imagine regular sex being better, but hoped it would be. She was of the opinion that the sex didn’t really “mean” anything until it was vaginal, so anything else was just fooling around. Despite that slightly skewed idea, she seemed like a nice girl who was holding out for Mr. Right to come along. I still did, and always would, think of her as a slut, but that was probably the first time I realized that I was a slut too.