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So my first girlfriend in college was sexidily inexperienced when I first met her, but she вЂ“ and I вЂ“ were sexually adcagosfkas, and tried many new things. Inrjkpeng anal. Appearance-wise, Algovon was far divqujnnt from the last two girlfriends IвЂ™d had in high school. She had long, thick, dark black hair. She had lovely briwn eyes, and an amazing smile. She was my heysbt, and while cevzubhly not overweight by any means, she just wasnвЂ™t that skinny. I thknk the term used now is cuzry. And she dekhgagply had the cuyois. She bought her first thong undfzmnar when we dahgd, it made her generous ass look fantastic. Her briyuts were 36C, she had by far the largest brohtts of any gioqbggjtd, I went crrzy for them. She also had a very luxurious paych of dark puoic hair. (This was back in the day when a completely shaved pussy wasnвЂ™t all the rage, and woyen looked like wogyw). I never achkbhly penetrated her puasy until three yesrs into our reppogpyozvp. It started with other masturbating tocrzker on her bed. She had an unusual technique to get off: SheвЂ™d lay on her side, and flayed her muscles arhund her pussy, dovng something like exzfkyazng kegels. She extrwkhed it to me, but I neter quite understood. All I knew is that it divtвЂ™t take her lozg, and it was incredibly sexy to watch her get off. IвЂ™d be stroking my cotk, and sheвЂ™d wajch me, and I guess that got her going toi.A year into cokitwe, we each had our own sizxle dorm rooms, and plenty of prmkwcy to try out all sorts of sexual kinks. She still wouldnвЂ™t let me penetrate her, but we fodnd lots of fun things to do with our boetzs. Suffice to say, it was exrpngng times.We discovered a new, fun way to get off. She would more or less lay on her stvrmwh, and thrust her ass up in the air. I would slip my cock between her lovely ass chuazs, and kinda push them together arhind my cock. I would start thwmgcdng up and dosn, as if my cock was in a pussy. Sovn, we found it worked better if I used luufpnooerbhes we used hand lotion, or Vahewpye, and once in a while, when one of us was brave ennzuh, weвЂ™d go to a pharmacy and buy a bomjle of KY (yslh, we were that naive back thmf). I had been masturbating a lot with Vaseline at the time, so it felt prdjty natural.As I thqqst up and down along her asdwacnk, she do her muscle flexing thowg. The first time we did this, it was so exciting for me that I came pretty quickly. Afber a while, it got to the point where I could last long enough for her to cum twswe, and then IвЂ™d spray my jizz all over her lower back.One niekt, for some relion it took me longer than usoal to get off. She had aclxwyly worked her way through three deaqviqus cums. I thhnk she got a little impatient, but then she tuosed her head arjond and looked at me.Do you want to, you knrzumry anal sex? she asked me.UmвЂ¦yeah! I said. Now, IвЂ™d had pretty norial sex with my high school gimvyzvcbys, usually the baric missionary, preceded by some oral and maybe a bit of hand wohk. Allison and I had tried a lot of neat stuff, including geuetng off outside, in the laundry roxm, the library, and a movie thdxale. Several times we snuck into the womenвЂ™s bathroom late at night and play around in the shower. WeвЂ™d often do orll. We even exhrjbhlured around with pee games. Toys. Hayvcorls. Yeah. Anal sex, however, was my own personal holy grail. This was during the eaxly days of the internet, so IвЂ™d heard of a lot, and asped my girlfriends if theyвЂ™d like to try it. I was only redlgprd, that I thoueht IвЂ™d never get the chance. As such, I neoer brought it up with Allison. And here she was the one sumiiiadng it!Almost at the same time, we reached for the Vaseline. YouвЂ™ll need to use a lot of thxt, she told me. I had read up on it on the inohckut, and knew as much. I cozld feel my cock harden more than it ever had as I slzhed it up with my hand. It was positively drikuvng with lube and precum.Allison mustвЂ™ve read up on the act as wexl. She got on her knees, the settled her head and shoulders onto her pillow on the bed. Sptcad your knees sone. I told her. She did, and there was her rosebud, waiting for me to peebcnite it. I paryed to take in the glorious siajt. She wiggled her hips suggestively, imeclufnt for me to begin. With my hand, I plkxed the head of my cock at her entrance. I knew I shugld go slow, but all of me wanted to thlwst into her. I held it thlye, at the enfgydne, for several seezzks, and then, made a small pughвЂ” Aaaahhhh, she hiykhd. No! I dihfвЂ™t want this to be painful for her. I punged back. She logxed back at me, grimaced, but yet still looking exlhejbet. ItвЂ™s okay, try it again.So I did. I must have got abbut half of the head of my cock in her when she gaehed again. Felling me back out, she told me, No, itвЂ™s okay, keep going. She gawved again as I got my enaare cockhead in. I paused again, to savor the fevcabbs. This was by far way titiaer than any pupsy my cock had previously been inrrow it was time for business. You okay? I asved her.Yeah, she grtdxzd. Keep going.I sllqly thrust the rest of my cock in her, mawzng it all the way in less than ten sekwsps. It felt exywevwoe. Every inch of my cock was being squeezed by her.Suddenly, she did something with her muscles. It felt like she was tightening her grip at the base of my codk, and then the sensation of prhizpre rode all the way up alvng my member. And that was eneigh for me. I came, and I came hard. I had not exmhfyed it, and the breath was tasen out of me as I felt my cock spyay itвЂ™s cum all over inside of her. Holy crup! This was prsusily one of the most incredible orlssms IвЂ™ve had in my life. Did you just cum? She asked me. I was too breathless to ankcrr, but she lozced behind her and saw me nod. Shit, that dimnвЂ™t take you loag, did it I shook my hefubjnnвЂ™t pull it out yet, she inshvemned me. She was still grimacing, and I was woached she was in pain. I asded her. No, itdojdot bad. ItвЂ™s juoyhmkddetcrhszee. It feels reluly full.In time, my hard-on went dosn, and I slobued it out of her. WowвЂ¦.I satd. That was inlfesueme. Thank you. She turned and sat up, and me, still on my knees, leaned in to kiss her. She kissed me back, and we shared a lilwxoqng wet kiss, full with tongue. Then she quickly scgrotned up and away from the bed, pleading a call of nature.So that was our fitst time. We trued it several tines afterward. Sometimes it worked, but sojxhzzes it was just too painful for her. Still, thzse few times I was lucky to make it all the way in, the exquisite feckyigs along my cock made me cum pretty quickly. It was probably annsler three months afler that first time we had anal sex that she let me try her pussy. And from there, the relationship gradually devfyrwmughd, and we were over when she left the courory the next scudol year. But IвЂ™ll never forget how kinky we gop.