Caroline's Sexual History

I met her when I was 19 and she was just turning 18. She was my boss’s daughter. I was working at one of those quick oil change/lube places with a small gas shack.

Her name was Caroline and her body was simply a thing of beauty. Tallish, around 5’7″, slender hips with a smaller waist, and leggy. Her ass was like a pair of plumbs, small and round, firm yet jiggly. Her breasts were big and hard with big pink aeriolas and eraser nipples. And she had a lovely face. She was 18 but had a worldly look about her, kinda like a 30 year old, kinda sinister. She was a gymnast, and had perfect control of her athletic body and the stamina of a marathoner.

I gotta tell you with all honesty that I was over-reaching with this girl, way out of my league. A guy knows these things. I was a kind of a mild dork, sort of a misfit, plain. Never had a meaningful kiss before and surely no pussy. And so I was amazed when she began showing an interest in me around work and actually paid notice to and actively talked and seemed to be flirting with me.

I was further floored when her dad, the owner of the place, did not seem to mind (there was a very good reason for him to ‘not mind’ that it was me whom his daughter was showing interest in, but I would not learn this until later). And so from this beginning, I began to date Caroline.

I was still at that point, of course, stuck on my proper upbringing and so proceeded as I thought a decent young man should do: I went slow and easy and with respect. Turns out that this was the wrong approach with this chick.

It took me a good 4 months or so to build the courage to fuck her for the first time even though she had given nothing but strong indications from the start that she was open to anything and everything. I was so embarrassed with my ‘late loss virginity’ (my brothers, even the younger one, had been pounding the puss for years) that I lied and told her that I had done it several times, which I am certain she saw thru with my pitiful fumblings and shyness.

She was patient with me and we finally got it over with. The thing I remember most about the first time was the sweet taste of her hairy pussy, her wide open hole, and her meaty lips. When I finally stuck my smallish (6″) dick in that hole, I sprayed almost immediately. I knew I had not brought her any sort of pleasure at all, so I didn’t even bother to ask if she enjoyed it.

Along the way, I began to learn about Caroline’s past, her sexual history. Although I did not think about it then, this is when I really began to learn about myself as well as learning about her. I found out that for some reason I am turned on by dirty stories (true ones, preferably) and slutty girls.

Anyway, Caroline was an extrovert and could talk to anyone. She was very verbal and talkative, so when my inevitable probing questions and dark curiosity about her experiences (and she was obviously very experienced for a girl her age) began to emerge, she gladly told me anything and everything I wanted to know in minute ‘intimate’ detail, and she had lots of ‘history’ to share.

Her first boyfriend had been a black guy named Maurice. (This is the reason her dad was so open to her dating me, a scrawny white kid, he knew about Maurice and absolutely hated black people.) She told me of how much she was attracted to dark skinned men. Not just black dudes, but Latino, Native American, Indian, Middle Eastern, etc.

She found this Maurice fellow irresistable and told me that the moment she laid eyes on him as a freshman in a mostly white High School, she wanted to fuck him. Within a week or two, she had. She told me of the first time she brought him home for lunch (both parents at work) and he pulled down his pants for her. She described his dick as being huge, a monster.

When I asked her (gulp) how huge is huge, she showed me a Thuringer salami in the fridge. This is a sausage that is nearly as thick as a beer can and around 9-10 inches long. She said as soon as she saw it she just had to put it into her mouth, had to suck it, rolling her lips around the thick head of it. When he had had enough of that, he yanked down her pants, ripping her panties in the process. She begged him to eat her puss instead of fucking her because she was scared. Not afraid of losing her virginity, this was her desire, but of the inevitable pain that would come with him entering her, as she had no idea he was such a huge guy.

He wouldn’t eat her, which he would apparently not do for her for the rest of their relationship (that, later, was my role). I guess black guys (or at least this one) don’t like to eat pussy. Anyway, she described that she sucked him until he couldn’t stand it any longer, then he pulled away from her and tried to push his thick head into her tiny little hole. Of course it didn’t go in but an inch or so, but he shot a huge load of jizz into the opening of her cunt and onto her hairy bush.

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She then cleaned up his knob with her mouth, and later told me that this is when she got ‘hooked’ on black semen. She said that the deep, musky scent and its thick gooey texture was simply ‘yummylicious’ to her. She rubbed the messy cum into her pubic hair and then pulled on her ripped panties and returned to school with him. That was it for her, she has been a thick cock slut ever since.

Of course in short order he had worked her puss well enough to push it in fully and later, by the time I met her, she was loose as a goose. Those lunchtime liaisons became 4-5 times a week. She was a real cum queen and always went bareback. She used no birth control at the time (turned on by the risk?) and in her silly way, always promised each other that he would pull it off at the last minute. Never happened. Why should it? She was just happy as a clam to have that thick black rod pushing creamy juice into her hungry hole on regular basis, and she really lucked out by not getting pregnant.

This went on for a while before her dad finally got wind of it. Can’t remember how he found out, but he hit the ceiling and demanded of her to cease and desist. Perhaps it was around this time that I came on the scene and boy-o-boy was daddy sure glad to pass the baton to me knowing that his precious daughter had been ‘ruined’ by a black dude and needed to redeem herself somehow with a respectable kid (what did he know?).

I honestly believe that she never really did stop seeing Maurice for an occasional lunchtime bump (I went to a High School across town).

She had a pretty hot temper on her and although we dated for about two years, there were many many break up/make up sessions, too many to count. I think this was a way for her to somehow convince herself (or her friends) that she was not a cheating slut because she always quickly found another ‘boyfriend’, usually black, to keep her company (read: service her pussy) when we were apart. Sometimes we would break up only for a half a day, sometimes for a week or more. She would always come back and tell me some sordid story of her ‘mistakes’. I was embarrassed, of course, as she would always explain it as an ‘I was just missing you and felt lonely’ episode, but we both knew the truth. She was a tramp.

I don’t think she ever really knew how much I came to actually look forward to our break-ups. I grew to anticipate the long wait for the phone to ring, looking forward to the moment it would finally ring and she would say she was sorry for her anger and the things she said, begging me to come over to visit her and make up.

I would arrive to inevitably find a tired looking girlfriend with a red, swollen, well-fucked pussy waiting for me. Sometimes she would wash it up, others I would find a dirty smelly musky hole and loaded, and sometimes crusty, panties waiting for me. We both knew the drill by then. She would squeeze out a tear or two, beg for forgiveness, and I would quietly pull her pants down and begin to inhale the stench of forbidden and dirty sex from a black stranger. My tongue gently cleaned the dried jelly of another man from her hairy vulva. I would dance around her hole with the tip of my tongue, patiently cleaning, probing, and teasing, running it gently up and down her meaty lips.

Then, after the hole was nice and clean again, and she was quivering in eager anticipation, I would go to work on her clit. All the while she would tell me the dirtiest details of how she had met him (at the mall, hitchhiking, at a party, or thru some of her other ‘bad white-girl’ buddies), what they had done together, how she had been distraught over our break up or had simply drank too much. She would then detail where, when, and how she had fucked him. She would always describe how big his cock was, what it was shaped like, cut or uncut, and what it tasted like.

She clearly preferred to have sex with strangers and tended not to see them again unless they had a truly remarkable organ. Often, as she would tell me of her dirty exploits, I would cum before I ever even touched her puss with my dick. Sometimes I would take her dirty used panties with me to enjoy later. I would always wash them and bring them to her for re-use later.

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Once, and only once, I actually caught Caroline in the act with another guy. My parents had gone to Europe for a couple of weeks and left us young men in charge of the house in their absence, making a big deal out of the trust they given us and the great responsibility of ‘running the house’. Big Mistake.

First chance we got, my brothers and I organized a kegger. It was a hell of a party and of course my darling Caroline was the bubbly life of the party. At some point, maybe 2 in the morning, Caroline and I finally went to bed as the party slowly wound down. I had drunk a shitload of beer and so had she, so we were both out like a light (or so it seemed).

I awoke maybe an hour and a half later with a full beer bladder and staggered, bleary eyed, to the john to take a leak. Then it occurred to me that Caroline had been beside me when we went to bed, but was gone now. I quietly wandered around the house looking for her. I found her downstairs on the pool table, every light in the room blazing bright. She was on top of this Italian guy named John Benedetti that had played football with my older brothers. This guy had a long thick rod and was lying on his back in the middle of the pool table. She was squatting on top of him, bare feet on the green felt, and very slowly sliding up and down on his pole. She was pretty tipsy still, and he was steadying her with his arms as she pushed him in and out of her. It was a thing of beauty. I was standing behind the door and peeking around it watching them for a good 5 or 10 minutes when I finally decided not to risk being caught. I quietly returned to my room and waited for her.

Drunk as I was, my dick was hard as a rock and I did not dare touch it for fear of spontaneously erupting. Around 20 minutes later, I heard her coming down the hall and pretended that I was still sleeping when she came back into the room. I lay on my back and she entered quietly, closed and latched the door. In total darkness, I could hear her moving clumsily around the room and hop on the bed. She did not even remove her panties, just straddled my face and leaned in and whispered to me to wake up, that she had brought me a present.

She slipped aside the gusset of her panties and pushed her sloppy, cum filled pussy onto my mouth. No attempt at teasing or foreplay, she just gave me a mouthful of Benedetti’s cum. She then began rubbing her gaping hole round and round on my tongue, nose, and mouth, grinding her sloppy hole into my face. This was how she liked to finish her night. Sharing her huge hairy sloppy hole with the man she loved. This was her fetish, and mine.

It was in this way that I found my true talent: eating pussy. And she showed me how. To this very day, 30 years later, I get way more pleasure from eating a woman and bringing her to orgasm than I do from coming myself. And to this day, I have my best orgasms when I think of the woman I’m with (generally my wife) getting fucked by a big huge black cock and bringing home a present for me to enjoy afterwards. This has become a recurring theme in my life.

Years later I would run into Caroline at an airport between flights. I asked her if she ever thought of those 2 crazy years we spent together as kids. She confided that it was me, our relationship, that taught her who she really was. I was stunned, as this is exactly precisely how I remember her. Not in a bad way, but in the truest sense, it was she who brought me to know who I really am sexually, and it was I who clarified for her that having a big thick cock was not enough, she wanted (needed) to share her sloppy seconds with another understanding and appreciative man before her night was thru.

This is a true story, and is accurate as best as I can recall it. I have dozens of other exploits I have experienced in the 3 decades since. I would be happy to write and share more of them if any body would care to read. Feedback is appreciated, good or bad, especially from any ladies who would care to comment.

Updated: December 20, 2016 — 7:00 PM

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