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College Days 6, My College Girl Jennifer

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(Click here for Part 5.)


During my time at college, I had about an 18-month relationship with a girl named Jennifer. (Her real name, as she’d recognize the events without her real name anyway, so I might as well.) My college stories involve Jenny as I had the most fun at college with her, aside from that first spring break when I didn’t have a girlfriend, and I was with her the longest. The really good stuff with Lisa worth writing (as it was all very worth doing) happened after college, as my time with Lisa was every bit as good as with Jenny. Only Lisa already knew how to squirt, knew and was confident in her sexuality (I’ll get to that on Jenny later), already did anal (but I was the first to make her squirt through anal sex and to give her breast orgasms, that she then shared with Amanda and their friends, who already knew about humming on clits from their high school days), was sluttier in bed (...and not in bed, but she knew how to act around parents and relatives because of her own who didn’t know what kind of girl they had raised), and liked sex as rough as I did (the extent to which I wrote Brea). Plus it’s already set up with Lisa and Brea (Amanda) at one college and me at another. The only possible exception would be the last college spring break, where Amanda (and the rest of their slut friends, but only as friends, and wanting to spend the last spring break together) sort of went together, stayed at the same hotel and in neighboring rooms, with Amanda in the adjoining room to Lisa’s and mine. Lisa would go out shopping or to have lunch with the girls (devoting all the rest of her time to me, which was more than plenty to keep me happy), but really Lisa and Amanda had their private sexual time together so Lisa could have us both on the trip. Me as her boyfriend, and Amanda ostensibly as her best friend and college roommate, and I only found out the truth later, when they told me after we had graduated. Their sneaking around the only thing really making it worth writing. But that’s for later. Back to Jen and what you need to know about her. The backstory for when I get to the better stuff.

Jenny was a long-haired (shoulder-blade length), naturally flowing, but unnaturally dark-red, redhead (naturally raven), with a nice round butt, and firm, fake double-D tits giving her a good, well-proportioned 32"DD-25"-36" figure, and about 5'7". Her implants were a present for high school graduation, as according to her, she had no tits (I think she said she was a B-cup, and the higher her grade, the bigger implants she could get, so she must’ve done alright to get double-Ds) or ass before the operation, and her hips and bottom filled out on their own after the surgery. Because she didn’t use to have tits, Jen loved using her new tits to give pleasure with titjobs and have them cum all over, and she was very good at it, taking pride in giving pleasure with her new breasts that she was proud of now having. She also loved receiving pleasure to her new breasts, especially in the form of breast orgasms. They were great tits, that also produced those nice stretch marks in the fabric of her tops between her mounds. Her nipples were constantly semi-hard as a consequence of the operation, plenty good enough for poking through her tops (especially since she hardly wore a bra), but her nipples could get harder and swell when she was excited. Jenny hardly wore a bra partially because she never needed one with her real breasts and never got used to wearing one under her tops. Then after the operation, her firm tits supported themselves very nicely, and she didn’t like wearing bras under her tops, so she didn’t except for when she needed to cover her poky nipples (but hated it the entire time, constantly adjusting her breasts and irritating bra) or for lingerie purposes. But she did wear two-piece bikinis, I guess because the top was her top, and not under another garment. Her pubic hair coverage varied with the time of year, with more coverage during colder months, and less during warmer ones. Ranging from almost full coverage to help keep her warm, to completely hairless to keep her cooler, with triangles and landing strips in-between that varied in size as the temperatures changed. But when she did have hair there, she always kept it very short and neatly trimmed to just her pubic mound, never having hair underneath, and used hair products normally used for hair on top of her head to care for her pubic hair. Keeping it very soft, softer than any other I had experienced. And even though I normally prefer fully hairless because of the smoothness and I can see everything, I actually loved her soft hair and would rub my cheek against it as I fingered her. And sometimes when she didn’t want me to cum in her pussy (or I wanted to cum on her), I’d pull out and rub the underside of my cock against it until I came on her. She also liked porn, preferring written erotica over shows or movies, but she liked watching with me, to help get us into the mood and to help us come up with ideas for things to try (or to bring up the subject of something she wanted to try) or remind us something we hadn’t done on a while.

I was the first to make Jenny squirt and then taught her how to do it herself, and for that, she repaid me by teaching me how to give her breast orgasms. She told me that while tit orgasms aren’t as intense as clitoral or vaginal orgasms, they’re still very nice little orgasms and they’re something different. To do it, basically I just treat her nipple like her clit, but there’s two of them, so I need to give attention to both. Rubbing both with my fingers while kissing her or kissing her breastbone, or use my mouth on one and fingers on the other and go back and forth until she came, or do one and then the other. She told me she loved to masturbate her breasts, and showed me what she was talking about, by masturbating her tits with her fingers and even pulling her breast up to orally play with her teat, giving herself a double breast orgasm before letting me try. So with the instruction and demonstration over and Jenny on her back, I straddled her to treat her left teat like her clit with my mouth as I rubbed the other with my fingers. Jenny moaned and breathed harder as she held my head in her hands, her already hard nipples becoming harder and swollen from the stimulation, and after a few moments, I switched nipples, giving oral pleasure to her right and manual to her left. Jenny moaned more as her breathing became harder, her hands starting to run encouragingly through my hair, and after giving oral pleasure to both nipples, I used my fingers on both nipples so I could kiss her. I broke our kiss to kiss my way down from her mouth to her breastbone, to kiss between her firm, swelling mounds, her breathing becoming harder and faster. Jenny’s tits started trembling around my face between them, and her back arched as her head rocked back into the bed, her eyes closing as she inhaled. Her arching back and inhale making her swollen breasts even fuller, her tits jumped up and down on her chest as her pectoral muscles spasmed and she moaned long and low as she fully exhaled. I continued my actions on Jenny until her breast orgasms ended, her body relaxed as she smiled, and she pulled me up from her chest to kiss me. Jenny broke our kiss to smile, “You just made my tits cum,” making me smile. While that was the first time I gave her breast orgasms, it certainly wasn’t the last, and I’d get better at it with more and more practice.
 

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After we had been together about seven or eight months, and had moved in together after about six, Jenny had chosen an anal porno for us to watch one night before we went to bed, to help her bring up the subject of her wanting to try anal sex, or maybe even have me ask her if she wanted to try. She trusted me and was comfortable with me as we had been together that long, and decided I’d be the one to lose her anal virginity to, but she was still very nervous when she brought it up with me. Jenny had heard good things about anal sex from her friends, wanted to try, and she wanted another way to take my cum during the part of the month she could get pregnant. Even though she was on the pill, she didn’t want to take the chance, and she didn’t like me wearing a condom anymore than I liked it, both of us wanting to feel the other.

Her online research to find out more about anal sex before we just jumped right into it (and before she brought it up with me) had led to how to get her ready and how a guy’s prostate is his G-spot, and how stimulating it can be very pleasurable. So in the process of her trying anal sex, she wanted me to try too, wanting me to try something that could be very pleasurable. Jenny talked me into it by saying she was talking about her, my girlfriend, who loved me and I loved, that wanted to give me pleasure with her body, and that she wasn’t talking about using anything on me that wasn’t a part of her until I was ready or if ever. And that I let her touch me everywhere else, why not there with the possibility of so much pleasure? So over the next few weeks, we helped each other prepare for the big finish, being very loving with each other to make sure we’d enjoy it, leading up to her massaging my prostate for an amazing orgasm and a huge load of my cum that landed in her hair (so I could see how much I would give her) as she sucked my balls and jerked me off the night I got to finger her ass for the first time for orgasms. I should probably tell you that from the start, Jenny’s asshole was hungry, or greedy. Every time it was penetrated, it always came out to take in the penetrating object all the faster. It’s why I’ll refer to her ass as ‘hungry’ or ‘greedy.’

Originally, Jenny either jerked me off for a fountain of sperm to splatter down into her hair as she sucked my balls (and sometimes onto her tits that she loved to get creamed) or blowing me for an overflowing mouthful that ran down her body, especially when the overflow coated her tits. The overflowing blowjob quickly became her new favorite way to get me off outside her pussy or ass with me cuming in her, surpassing her original favorite of titjobs which became a very close second. That is until she figured out how to use her tits and work my prostate at the same time, becoming her ultimate favorite as she got a huge load all over her big, beautiful new tits while also using her tits on me and not just jerking me off onto them. While Jen continued on to beads and a butt plug to get ready for my cock, I wasn’t willing to move on to toys, only wanting the pleasing finger or tongue of my loving girlfriend inside me. While she was disappointed I didn’t want to go further, she was happy I had tried with her and that far, and liked what she did enough to want her to keep doing it. And Jenny was very happy I only wanted her inside me giving me that pleasure, knowing that her toys were good, but she still greatly preferred me pleasuring her with my body because it was me. So she told me that if I changed my mind later and wanted to continued into toys, she’d be willing to help. And as we continued to prepare her for full anal sex, she got better and better with her finger working my prostate.

Her research had also revealed how to make her squirt through anal sex, and how the continued internal stimulation along with the normal clit rubbing would make the already amazing orgasm truly spectacular. So the night she fully lost her anal virginity to my cock, Jenny rode me some first to test the anal waters and her anal boundaries, and make sure it was all good. After cuming from just mounting me, amazing her, Jenny started slow and easy in reverse cowgirl so I’d have a good view as she slowly rode me harder and faster with each rewarding anal orgasm bolstering her confidence and growing in intensity with the increased stimulation. Jenny ended her riding hard and fast in crab from cowgirl, giving me an even better view of her hungry asshole taking me in and out as her vaginal secretions ran down to coat my impaling dick, really slamming herself down onto me, pounding me into the bed, and making herself squirt for the first time through anal sex. Only her orgasm prevented her from continuing the ride, the head of my cock still inside her to act as a butt plug as her legs lifted her, and I rubbed her clit, not getting the full effect. It didn’t occur to me at the moment to thrust up into her to make it better. I was too busy enjoying the show, and it only barely occurred to me that I should rub her clit.

Then it was my turn to fuck her ass as hard as I wanted (as she had determined she could take it through her riding, but she was too tired to keep riding me), and make her squirt through anal sex and keep fucking her ass through the orgasm while also rubbing her clit for the full effect. She also wanted me to shove my cock into her hard and fast, with one swift motion, telling me she could take it, and she did, making her cum again from just shoving myself inside her. As I fucked her hungry ass really good doggie to really pound her ass and be able to reach her clit, Jenny came so hard, screamed so loud and hard, and squirted so much that I thought I was going to break her as hard as her body shook under me, her voice would give out (and in the end, her voice was going), and that the cops would be called with a neighbor thinking I was killing her. And she ejaculated so much, soaking the bed so thoroughly, that we couldn’t sleep on it that night. When her voice started to go, I decided she probably didn’t need to keep going, even though I’m sure she would have disagreed if I had asked her. And since she wanted her first anal sex to end with me cuming in her butt for the full experience, I gave her one more squirting anal orgasm and blew my load in her ass as she came, making her very happy as her screams turned to squeals of pleasure with a little bit of giddy giggling in her exhaustion. Her tired arms and legs gave way, collapsing us, I rolled off of her, and with a big but tired and sweaty smile, Jenny tenderly sucked my cock to clean me, get the last of my sperm that had stuck, and to taste herself, already knowing she liked the taste on her toys and fingers, but loved it even more on me and with some of my semen. Then after drinking lots of water to rehydrate herself, we slept on the couch, spooning, waking the next morning with my morning wood buried in her hungry ass for us to go again. We repeated the events of the night before, but with Jenny fully confident in her riding from the start. This time me having the presence of mind to thrust up into her when her squirting anal orgasm prevented her continued riding, and we soaked the couch in her juices when I fucked her. Then a few days later, to repay me for teaching her to squirt and helping her lose her anal virginity, she taught me how to make oral clit play better by humming. How she learned about breast orgasms and humming on clits, I’ll get to later.
 
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