Best Friend's Girlfriend [M/F] | 2016

I've been loving Gonewild stories for a long time now and wanted to weigh in with a few of my own adventures over the years. I've had a lot of fun, and though I'm older now and happily married, I still look back on the crazy stuff I did and wonder how I got away with it all. I've been very very lucky.

This happened a long time ago when I was 22 (I'm 49 now, so that should give you a reference point for just how long). In my teens I developed an absolute love of sex and explorations, and was one of those weird kids who really DID read all the stories in Playboy (and Penthouse letters... god how I loved my older brother's collection of Penthouse stuff).

I used to play RPG games, the paper and dice version back before we had broadband and WoW to enjoy. I was seeing someone at the time, and the guy who ran the game was one of my best friends. I met him at college and helped him move his car once when it was stuck, we got to talking and he invited me to join. And since I've long since forgotten that friends name, let's call him Charlie.

Charlie had a girlfriend he had been seeing for a while, a woman named Amanda. Amanda was the model of early geek girl. She loved science fiction and fantasy and always played as part of the group. Charlie was a short, slight guy so she was taller than him but well shorter than me. She wore glasses and kept her blonde hair in a ponytail, so it was hard to say she was really "hot, hot", more of a cutely attractive woman with a nice smile. She wore really baggy clothing all the time and seemed worried about her weight, so we all thought she was a bit chubby, but as it turns out she wasn't fat at all. More on that later.

One Saturday afternoon we got together to game, and had a great time. Things broke up around seven, but I had a few hours to kill before I needed to get home to my own girlfriend and Charlie asked if I wanted to go out with them and get some drinks. I said sure, and a few of us went with Charlie and Amanda to a local bar and started having beers and wine.

I was never much of a drinker, Irish heritage be damned, so one beer was always enough to give me a pleasant little buzz. Amanda had a couple of glasses of wine and was definitely more buzzed than I or the other guys were. Pretty soon it was down to Charlie, Amanda and I as the others left to head home, and I was beginning to think about packing it in myself when Charlie headed to the restroom.

Alone with Amanda we made some jokes and then, really quite accidentally, our hands brushed. You know those moments when you feel that sudden spark with someone, like you just realized "holy shit, this person is so attractive"? Yeah, it was like that, and I could tell she felt it too. And the alcohol really lubricated her tongue.

"I've always found you so hot," she blurted out and blushed. The blushing was cute, I loved that.

"I think you're pretty hot as well," I replied. True enough, at least I had just realized it. I certainly was attracted to her at least, her weight be damned.

"Really? You're attracted to me?"

I nodded in reply. "I would love to sleep with you sometime, if it wasn't for Charlie."

She shrugged and smiled. "We've been fighting a lot and we don't really have much sex these days. I'd be fine with it, but you're seeing someone as well."

Well, for me... the sex was almost as nonexistent, and what sex we had was terrible, and I told her so. She smiled again and said, "Wait, what's happening here?"

"I'd like to come by if you're up for it sometime," I told her.

"Stop by tomorrow," she said quickly, Charlie returning at that point. I made my excuses, thanked him for a great evening and left. The only thing I could think about all the way home was Amanda.

The next day I went to her place. She had a small apartment in the city (small city in the northeast where I lived at the time). She invited me in very shyly and we hugged awkwardly. No, this wasn't the whole "falling into each others arms" thing you expect from these stories, we chatted for a bit and laughed, were both very nervous, touched each others arms and legs and we talked as though to make sure we were each really there, and basically worked up to a moment when both of us had screwed up our nerves to the breaking point.

As we sat next to each other on her couch, I broke through first, leaning in and kissing her. It was a nice kiss, nothing special, and our glasses clicked, which made us laugh. We took them off and returned to making out, and it progressed quite quickly from soft quick kisses to heated necking, wrapping our arms around each other and exploring each others mouths and tongues. I noticed as I held her that she actually had a very small waist, but when he leaned into me she had enormous breasts. Surprise! She wasn't fat at all, she was very height/weight proportionate, she simply had oversized breasts and very wide hips. An hourglass, curvy figure. She could have been a pinup model.

She took my hand and we stood. "Can we take a shower together? It'll help me relax," she asked, and I nodded. We walked into the bathroom, kissing and groping each other on the way. When we closed the bathroom door, I pressed her back against it and we ground against each other as I pulled her shirt up and over her head. She had a heavy, lacy bra on to hold up the biggest breasts I'd ever seen (to that point at least, and still the biggest on a relatively petite woman). She undid the hook and shrugged it off, and my mouth worked immediately down over her chest and found her nipples, my tongue flicking around the tips to get them hard.

She moaned for the first time. To this day, I still can't forget her moans. Her speaking voice was normal, a little nasal, but her moans were high and soft, lilting little gasps that turned me on incredibly. She helped me out of my clothing then and wrapped her hands around my cock.

"So fucking big," she said looking down at it. "Charlie's not even close to this." I kissed her again, still too young and shy to respond to that type of comment (thought later in life I became quite proud and happy to talk about my big prick, and used its size to keep getting women). She reached over and turned on the spray, undid her jeans and slid them off with her panties and we stepped into the warm water.

We soaped each other up, breaking off for kisses from time to time. I almost came twice as she stroked my cock with her soapy fingers, her big breasts pressing against me, the spray from the shower dripping from her hair as she stared down at it. Each time I pulled her hands away and humped the air for a few seconds to gain control, riding the edge of what I needed so I could have what I really wanted.

The second time, once I was back in control, I grabbed her wrists and pressed them back against the wall. I kissed her and worked down her neck and to her breasts again, lightly biting each nipple in turn as she moaned and writhed against me. I finally had to release her wrists as I sank lower, kissing down over her narrow waist and then her mound, letting my lips and tongue find their way through her very light tangle of blonde pubic hair to her perfect little pussy, wet from the shower and wet from her. She had lips that stuck out a little, very pink, parted in arousal, and a tiny little clit that didn't quite stick out from her hood. I buried my face in her perfect cunt and lapped and licked until I felt her stiffening against me, gasping with her first climax as she rode my face. I always remember the first time I go down on someone, it's my second favorite thing to do, right behind burying my cock in them.

I stayed there until she had calmed down a little, then I stood and turned her around, bending her over slightly. Her ass was as sexy as the rest of her, she was a true pawg in that respect by today's terms. I took my hard cock in one hand, holding her left hip with the other to keep her in place, then I stroked the head of my big prick up and down over her sweet little quim as she squirmed back against me. I teased her for a while until she was panting hard, and then I jammed the head into her and held it there for a few moments to let her very tight pussy adjust to the size of it.

"Jesus," she gasped, not moving, her legs shaking beneath her. She was incredibly tight and I had to work slowly to get it in, even as wet as she was. Small strokes, a little more each time, then pulling back a little, then another. Each time deeper, each time further, until that last little bit of resistance melted (you know you can feel it when it does) and I slid balls deep in her amazing pussy.

It was slow after that. No rush. Languidly fucking her in the shower with long, deep strokes I broke up occasionally with short, shallow ones, sometimes bending my knees more so I could thrust UP into her. She was moaning and panting, her breasts swaying beneath her with each thrust, reaching between her legs to feel my balls as they slapped against her clit, and after all the attention she had given me I knew I wouldn't last too terrible long.

I came close once and held off by grabbing her and growling, "don't fucking move," as I stayed still. At 22 it was hard not to come immediately, it took me a number of years to last more than a few minutes, but I managed to get this one to pass and then I started really fucking her, harder and deeper, banging away at that perfect pussy and gorgeous ass. I don't think I had gone more than four strokes when her legs started shaking again as she came once more, and that was really more than I needed myself. A few more strokes, her pussy clamping down on me with her own orgasm, and I felt it ripping through me, a hot climax as my cock throbbed inside her pussy, both of us coming together as I came deep inside her. Yes, I know... no condom. Bad me, bad her, not safe sex. Ah well, as I said at the start, I've been a very lucky man in my life, and not just all the sex I had with all those people. I didn't care, all I knew was at that moment I was coming in the tightest pussy belonging to the hottest girl I'd ever had.

We stood for a while until I softened, then I slipped out of her, some of my cum dripping in gobs down into the bottom of the tub. We cleaned up again, kissing, then climbed out and helped each other dry off. Then we cuddled naked for a while on her bed until it was time, and I left to go home.

Amanda and I saw each other a lot for a few months. Then she and Charlie broke up, Amanda suffered from a nervous breakdown from family issues going on around her, she went on medication for her depression, and well... that was pretty much it for Amanda, she lost interest in anything beyond dealing with own issues, which I understood. But that first time (and one other time outdoors at a swimming hole I used to love to go to, when we almost got caught) was one of those experiences I won't forget, even if all the details aren't perfectly remembered.

But I remember her body, I remember her face... and I remember the way she sounded when she would moan for me. Those are great memories to have.