Indiscretions of [m]y youth: Her best [f]riend

As with some of my prior tales of my youth I'll give you a quick heads up about me. At this point in my life I was twenty, I was in college, things were looking good, and generally, I was pretty happy. I was working and had a pretty decent paying job (for that time), school was a little jumbled, but I was getting through it, and on the sex side of things, I was doing pretty damn well.

I got into a relationship with a co-worker. It started off with just sex, as per usual drunk sex, but it developed into a relationship later on. During the first month or so of relations, something odd happened…

The beginning…

My new relationship was just about the sex. I fucked this girl I had been working with for the first time in an open bar (only about 3 people in the place, including the bartender). I fucked her again in her car in a park that same night. From that point on we had office sex, sex in clubs, sex in cars, and pretty much any place we thought we wouldn't get caught. On that point, the sex was pretty fantastic. The girl I was seeing had medium length brunette hair, glasses, was a little – a little- curvy (but not in the right places exactly). Considering my prior recent exploits, Jennifer wasn't physically my norm. However, her appetite for sex and her absolutely awesome personality just drew me in. As we progressed along we started having sex at her place pretty frequently. After the third time there, I met her roommates. Steven and Amy.

Steven and Amy were a couple. The consequently also worked at the same place, some small chain steakhouse, and they were some wild people. The little trailer they were all living in was a den of beer and weed. It was a like a little commune of hippies. Everyone chipped in (except for me and weed, I don't smoke) for everything. It was odd, but I really kind of enjoyed it.

Due to the confined living quarters, there were some awkward moments. The occasional catching someone or someones coming out of the shower, or coming in the door and not everyone was completely decent. Yet, for the most part, I never really looked at Amy during those compromising times.

Amy was tall, at about 5'8, with exquisitely long legs. Her butt was small and tight. Her waist was a size two. As for her breasts, well I did see her bras a few times and out of curiosity took a peek…learning that they were D-cups (she would later tell me that she fit more comfortably in DD). The thing that I had the most trouble with and the reason I rarely looked at her in the "compromising" situations was her eyes and lips. She had the sexiest and almost persistent "fuck me" eyes. They were dark brown and matched her Mediterranean skin and hair color. Her lips were thin, but the smile this girl put off made me understand how the Trojan War started. Because she was dating another person in the place and I was fucking her best friend, I did my best to never really look at her in this light. However, one night things changed.

Everyone was drinking and/or smoking, and we had chilled out watching movies. As my now (at that point) girlfriend and her other roommate had to work they decided they were going to hit the bed. Neither Amy nor I had to work the next day and we were in the middle of drinking and watching some action flick. We said we'd head back to our respective beds after the movie was over. As we sat on the couch, drinking and bs'ing during the movie, she casually sparked up a tiny bong. She egged me on to smoke with her, which I reluctantly agreed. As I said above, I don't smoke, so this kinda hit me hard.

I don't remember falling asleep, but I awoke to being cuddled up with Amy on the couch. The movie had cycled back through and was playing again. What ultimately caught my attention was that my hand was cupping one of her full, firm breasts and I had a raging hard-on that was pressing into her, only thin materials separating us. The second thing that caught my attention was that we apparently had both woken up at about the same time. As I was just taking stock of the situation, I looked up at her and Amy turned her face and looked at me. Damn those seductive eyes drew me in. I leaned in and kissed her. It was slow, but intense, and my cock felt like rebar by the time we separated. Then reality struck us both. This was wrong, we shouldn't be doing this. We both needed to go to our respective bedrooms. Needless to say, I woke my girlfriend up and fucked her brains out.

Fast forward about 6 months…

Amy and Steven had broken up, and Amy had moved out and started renting a nice townhouse in an upscale part of the town. I hadn't been by to see the place, but I knew where it was. I decided one day after work to go see her and see how she was doing. When I arrived at her new place, I was bombarded at the door by her son (a hell of a kid). I played around with her kid and some of the neighborhood children for what seemed to be about 20 or 30 minutes, all the while Amy was cleaning her place up.

When we finally came back in the townhouse, Amy had changed clothes and was wearing some Victoria's Secret sweat pants, the kind that hug the hips low and show off the curve of a woman's ass so nicely. While Amy didn't have much by the way of ass, she made up for in the litheness of her stomach, which was exposed by the cropped shirt she had paired with it. The cropped shirt only helped to outline the stark difference between her flat, toned stomach and her voluptuous, full breasts.

The show starts…

Amy's son was milling about in the townhouse and eventually settled on playing a videogame. At that point, I asked Amy to show me around. We went through all of the rooms finally ending with the display of her bedroom. Literally, there was nothing in there other than the bed, and that was on the floor. I made a few jokes regarding the bedroom setup to which she pushed me and told me to shut up. Amy and I had a history of wrestling playfully, she was feisty and very flexible, but most importantly, she like the aggressiveness, even if playing around.

So after she had pushed me, I jokingly told her to watch herself because that's how people get hurt. The game was on, she full on pushed me and said what you going to do about it. I dove in and grabber her by the waist and took her down onto the bed. We were wrestling about and it was all in fun, but something changed. She was intentionally backing off, making it easy. That's when I felt her hand on my crotch. Apparently, I had gotten rather turned on by this mini bout, and she felt my firmness as I had been between her legs.

Things moved rather quickly as she looked at me with those damnably sexy eyes. We were kissing frantically, our tongues probing and interlocking and swirling around. My hands immediately moved back to her breasts and I came to realize that she wasn't wearing a bra. Her breasts were so firm and perky and her dark nipples were rigid against my finger tips.

I was quickly moving down her neck, kissing down her body, and then coming back up to the swell of the underside of her breasts. With both hands I raised her cropped shirt as my tongue traced up her sternum; taking one breast in hand and kissing and licking my way to the other breast and her puffy, erect nipple. I swirled my tongue around the nipple and alternated by flicking my tongue up and down it – eliciting moans.

I went back to my earlier pursuit of kissing down her fit stomach. Then kissing lower to her hip bones. My fingers hooked into the tops of the VS sweatpants and into the top of her underwear, and I swiftly pulled both down …my tongue trailing down her pelvis. Her bald pubic area had been freshly shaven and was smooth to the touch. Her vaginal lips were prominent and begged to be sucked on, licked. I obliged, quite willingly. I spread her lips open and flattened my tongue taking long licks, stopping at her clitoral hood to flick my tongue across it. My fingers splaying her open were slick with her wetness and I could hear her gasp every few moments as I would come to the little pearl of her clit. I used my other hand to pull the clitoral hood back and began licking and sucking her clit in earnest. She began trembling and moaning out. Her hips were writhing and crushing her wet pussy into my mouth, grinding out her soon to be climax on my face. She was getting so close, I could feel the heat and wetness building. I slid two fingers into her and began curling them in. She wrapped both legs around my head and began squeezing. Her orgasm wracked her body …and nearly suffocated me. She was shuddering and whimpering as I gave one final lick.

I sat up on my knees and quickly undid my jeans. Fishing my raging hard-on out. I stroked it for a few moments until she was somewhat composed and then I flipped her over. She went face down and arched her back. She used one of her hands to spread her ass open to me. It was one of the most delicious views I have ever seen. Her small little rosebud was so tight, and it looked inviting, but I wasn't sure this was her kind of thing yet, so I slid my cock up and down into the canal of her vaginal lips and then after her wetness had coated me, I plunged my throbbing cock into her. I was so worked up the only thing I could think about was climaxing. I was jack-hammering my dick into Amy, grabbing her hips to thrust harder into her. As I started to feel the cum boiling up, I let her know I was close. I already knew that she had her tubes tied, but I wanted to hear her say it. I leaned forward a bit and whispered, "Can I cum in you, I'm soo fucking close?" She replied back, "Yes, yes, cum in meee!" Hearing those words, her desperate plea for me to unleash in her, I came. I filled her wet, hard-fucked pussy with my sperm; splashing four or five ropes of hot cum in her.

I was sweating and panting and fell onto the bed beside her. After the sex crazed parts of our brains had shut down, we realized that this was bad, and that it couldn't happen again. It did, many times over.

Source: reddit.com/r/gonewildstories/comments/3zwpe9/indiscretions_of_my_youth_her_best_friend