College Days 11, Jenny Explores Her Sexuality

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Works for panties
(Click here for Part 10.)


On a Friday night a few weeks after showing me her BDSM side, for our evening viewing pleasure, Jenny selected girl/girl porn. Jenny used the porn to nervously bring up to me that she had thought about what it would be like to be with another girl, and how just thinking about it gave her a funny feeling deep inside, a little bit wet and her nipples became harder. But she was unsure about it, like she was before being with her first guy, only more so because of how she was raised. Jenny’s curiosity began in high school, but she could never bring herself to explore her sexuality. She had tried to in high school, but she was nervous, didn’t know what to do, dreaded her family finding out, and whenever Jen tried to approach a girl, she chickened out. Afraid the other girl would say no and then Jenny would be outed, or worse, she’d say yes, and once they got together, Jen wouldn’t know what to do. So to help with the latter, Jenny had done lots of research. Mostly watching girl-girl porn and reading girl/girl erotica (which is where she picked up the tricks about humming on clits and breast orgasms she taught me), that became Jenny’s guilty, naughty pleasure for really good masturbatory orgasms. But Jenny also did some research on the internet, not unlike what she had done before we tried anal, to learn about how to please other women, and practiced on herself as best she could. Trying to learn to do it by touch alone, instead of letting the pleasure guide her, because she wouldn’t have that with another girl. So Jenny had learned what she felt like inside, and what motions, pressures, and speeds felt best for her, so she could do it to another girl. She also used her knowledge to become as good at blowjobs as she was, which was very good, and even better once she learned how to massage my prostate. Jenny knew a guy’s penis was basically a bigger version of her clit, so she practiced by pleasing her guy like she would a girl, only she got a creamy reward for a job well done. Since she arrived at college, and since so many explore their sexuality there with no parents around, Jenny thought she’d be able to get past her fears, but couldn’t. She was still afraid she wouldn’t know what she was doing, as she was still a virgin lesbian, despite her practicing on herself.

Jen wanted me to help her explore her sexuality, but I wasn’t sure how I was supposed to help, and Jenny said she wanted to do something similar to when she had fully introduced me to her kinky, BDSM side. Jenny wanted me to go out the next day, find some girl I liked the looks of and who was fully bisexual, and bring her home for them to meet, telling Jenny she was my other girl, who was fully bi. And that if I was to keep Jenny, she’d have to have sex with women so I could have threeways, forcing Jen to explore her curiosity. While I liked the idea of Jenny being bisexual and helping her explore her curiosity for obvious reasons, I was unsure about how she wanted to go about it. I thought it seemed like a bad idea, and must be a better way. One in which I didn’t seem like the bad guy, just in case her first lesbian experience ended badly. Jenny assured me I wouldn’t seem like the bad guy, because she asked me to do it to help her. I agreed to help, making Jenny happy, but I thought she should come with me the next day so we could pick out the girl together, and so she could explain to the other girl what’s going on. Because I knew there was no way she’d believe me, and I’d come across as some asshole. Jen protested, but I told her I’d be there with her to help, but she needed to tell the other girl. To just think of it as me already forcing her to explore her sexuality by talking to another girl. Jenny reluctantly agreed, and with me very aroused at her confession and desire to explore it the next day, I carried her to bed, where I fucked Jenny so hard, telling her I loved how she was going to explore her sexuality with another woman, making her happy. And after giving her many hard orgasms and several squirting ones, she sucked me off for an overflowing mouthful to coat her tits before falling asleep together, spooning.

The next day we went out looking for the woman Jenny would lose her lesbian virginity to, eventually finding a willing girl, excited by the idea of a threeway, and who was actually looking for some action herself. She was a good looking brunette named Emily, who was like 5'8" and had a 36"C-26"-36" figure, showed off well by her short skirt and tank top in the warm, late spring weather, and had gone out without any underwear, so as not to lose them if she happened to get lucky. We returned to our place, where we started it with Jenny ‘at home and waiting for me,’ when I came home with my ‘other girlfriend’ Emily. I did as Jen had asked to force her to explore her sexuality, and we moved to our bedroom, where I had Emily kiss Jen as she caressed and fondled her body through her clothing. When Jenny started nervously responding in kind, I had Emily become more aggressive with her kissing and fondling, turning it into a make-out, feel-up session, that briefly took Jen aback. As Jenny became more confident and comfortable, I took that comfort from her, as I had Emily strip Jenny down, and kiss and caress her newly exposed skin, paying special attention to her fully hard nipples betraying her excitement, as Jenny just stood there in shock at what was happening to her. But like her nipples, Jenny’s cunt was horny and excited with the unknown, already opening and wet enough to make her thong stick to her when Emily lowered it.

I had Emily resume the make-out, feel-up session, adding rubbing Jenny’s pussy, and as I couldn’t stand to just watch and as Emily was supposed to be my other girl, I joined the action, penetrating her wet pussy from behind. I fucked Emily as she made out with Jenny and felt each other up while rubbing Jenny’s pussy, but I paid enough attention to Jenny so that when I saw her nearing her first orgasm given to her by another woman, I had them stop. We moved to the bed, Emily still fully clothed, and I had her resume kissing Jenny as they caressed each other while I had my first taste of Emily’s wet pussy. After I gave Emily an orgasm, I pulled her back so her head was at Jenny’s chest, and had her work Jen’s tits to orgasms as I fucked Emily doggie style to climax. Then I pulled her back to kiss Jenny’s stomach, pubic area, and inner thighs, while I fucked Emily to another orgasm before telling her to give Jenny the best clitoral orgasm from oral she could. Emily smiled sexily deviously at Jenny, and went to work on her clit as I continued to fuck Emily from behind. Emily built Jenny up so high that her hand clawed the bed and the other Emily’s head, she panted hard, her hips were bucking, her shoulders pressed hard into the bed as her head thrashed around, and her body was trembling, needing to cum so badly. Emily finally gave Jenny what her body needed, making her cum harder and longer than I ever had, and after Jenny’s orgasm, I made Emily cum so not to disrupt Jenny’s pleasure to give her a breather to enjoy what just happened to her.

I had Emily continue on through tonguing Jenny’s pussy, fingering her, and fingering her while orally servicing clit to similar results, all while I fucked Emily doggie style. But I took Emily to climax with Jenny when she was only fingering her instead of after Jenny’s orgasm like the other times. I then had Emily give Jenny a fingering to squirting orgasm while orally pleasing her clit, making Jenny cum very hard and ejaculate lots of her cum, before I gave Emily squirting satisfaction of her own. I then had Jenny roll over and get on all fours for Emily to first tease her hungry asshole with her tongue as I did the same to Emily, and with the girls ready, I tongued Emily as she tongued Jenny, taking them both to orgasm, Emily slightly behind to not interfere with Jen’s pleasure. I then had Emily nibble and kiss Jenny’s rump as she fingered her ass, while I butt fucked Emily really good doggie, taking them to simultaneous regular anal orgasms, and then squirting ones with Jenny’s first. Before I let Jenny have her first taste of another woman’s pussy and ass, I had one more thing I wanted Emily to do to her, and had Jenny lie on her back again. I had Emily finger Jenny’s holes for a DP to squirting orgasm while orally pleasing her clit, while I did the same thing to Emily, taking her to orgasm sightly behind Jenny. I had them kiss, Jenny far more confident and very happy from the experience so far, and I then told Jen it was her turn to return the favor, making her nervous and worried. Emily assured Jenny she’d do fine, and that she had already agreed to help Jenny get her technique and locations right, helping to restore some confidence in Jen.

I had Jenny go through everything Emily did to her, her nervousness leaving her and slowly replaced by growing confidence as she realized Emily tasted good, liked everything Jen was doing to her, and with each orgasm she successfully gave Emily. I did everything to Jenny I had done to Emily but harder, while also adding whispering into Jenny’s ear how she had never been more beautiful than with another woman, how much it turned me on, and how much I loved her, also expressed by how I fucked her. All during the sex, Emily did make minor adjustments in technique and location to Jenny’s work, and after their ending squirting orgasms, to thank me for helping her explore her sexuality, Jenny gave me the best overflowing blowjob she ever had, as Emily and I kissed and fondled each other. Jen didn’t swallow any of what I pumped into her mouth, but she held as much as she could, before having Emily clean my cock and them snowballing the massive load back and forth, each getting a mouthful that took several gulps to get down.

After, Emily was very surprised and impressed at how good Jenny was and how close she was for a virgin lesbian. She even asked Jenny if she was sure she had never been with another girl before, and Jenny explained what she had done to prepare herself. We asked Jen how she liked it, and she said that like any first time, she was nervous, but enjoyed it more than enough to want to do it again, loved the way Emily tasted, and loved the taste of my cock coated in both their juices even more, especially with my cum. And that maybe next time, she and Emily would just play together with me watching, if Emily would like to join us again, to which Emily happily agreed.

Emily joined us again the next weekend, Jenny confidently coming onto Emily and leading the entire weekend, half the time lesbian sex for me to masturbate to and get blown or titty-fucked when they finished, the other half threeways. Emily quickly became Jenny’s bisexual lover that she shared with me, coming over Friday night to stay the whole weekend with us, and come over a couple nights a week besides, with Jen even letting me cum in and on Emily a few times. However the good times were short-lived, as Jen loved her BDSM side more than Emily or me, and wanted to go further than I was willing and more often than I was willing. And Emily was completely closed to the idea of BDSM. Because of our unwillingness, Jenny left us before the start of our senior years for a group she found that did it how she liked and as often as she wanted. With Jenny leaving both of us, and Emily and me liking each other and the fun we had together, we decided we’d continue without Jenny. However, we reminded each other of Jenny and what happened as she was the reason we had met, and broke up in October. But in November, I got a lucky break at the coffee shop (the same one where Lisa and Amanda met, and were in line together that chilly morning) to get in line right behind Lisa (who was looking very good in her tight sweater and equally tight jeans with heels), I asked her out, and she said yes. The rest is a story for another time.
 
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