Anne was someone who had been incorporated into our group by one of our buddies. They started dating early in high school and had an on and off relationship for a few years, and by the time things really broke off for good she was engrained in our group of friends for good. This story is probably her most memorable that I was directly involved in, and took place over the course of a weekend at a friend’s house.

It started out like any other weekend. A bunch of getting together at someone’s place to hang out, chat, play some games/watch movies and have a few drinks. I don’t know why she did it, but for whatever reason, that weekend she decided she’d drink Gin instead of the regular. She’d always been a flirty girl, but she had dated a friend of ours, and consequently for a long time she was just seen as a friend who hung out with the guys, regardless of her undeniable sexuality. But enough time had now passed since their relationship ended (poorly). If she showed skin, I was sure most of the guys would look, and I think she knew that.

As the evening progressed, somehow the conversation got steered towards the ability of the guys in the group to unhook a bra one handed, and innocently enough, Anne let us practice on her. Only a few of us really had any experience, and as it was over the shirt, everyone was laughing and having a good time with it. It was actually Anne who morphed the unhooking the bra challenge to a Truth or Dare game by challenging one of the guys to do or reveal something vaguely sexual. A few more challenges and drinks later and Anne’s turn was up and she was dared to strip down and hang out in her underwear. She was hesitant, but agreed to do it if at least four of the guys got naked and streaked down the street and back. It seemed like a fair tradeoff.

When the guys got back, she followed through on the dare and pulled off her shirt to reveal the Black push-up bra we’d all been unhooking that night. Her jeans came off after, and true to form (she always wore them) she was wearing a very revealing Victoria’s secret thong. We’d all seen her in a bikini before, but this was different and more personal. One of the guys actually went up, and read the tag of her bra to “reveal” her 32B cup size to everyone, but aside from blushing Anne didn’t protest.

A good chunk of the night seemingly passed quickly, with the group of us hanging out and enjoying the sight of our friend in a state of semi-nakedness, and had it just stayed that way it would have been a fun night. Instead, at some point we looked over at the couch to find Anne making out with one of our buddies. A bunch of us gathered around and made a big deal like immature guys do, but she was totally into it and didn’t seem to care. Then our buddy, to much hooting and hollering, drops his hand behind Anne’s back and uses the very skills we’d all been practicing earlier that night. Anne’s bra went slack as he unhooked it, and for a moment we waited, expecting her hands to shoot out lightning quick and press the bra tightly so nothing would show. Instead she just kept going, and as she leaned forward kissing our buddy, her bra slid off her back and shoulders, our friend helping it along the way. And just like that Anne’s bra was off, and she didn’t seem to care that we could all see her tits.

It took a moment for her toplessness to sink in, but when it did the guys went quiet and enjoyed the view before one of my buddies chimed in, asking our friend to “turn her to face us”. Our buddy making out with her was having a good time with it, as if he couldn’t believe what was happening either, and gamely pivoted her so their making out was more awkward, but so that Anne was facing us, her tits completely revealed. The rest of us watched as she let him feel her up, tits first, before sliding a hand down the front of her thong. A few seconds later, and he was leading her to the bedroom, the rest of us in tow.

He got her on the bed, and then pulled her thong off. She was turned away from us, so we got a nice view of her ass before he pushed her onto her back and took position. A moment later we were watching our buddy fuck Anne. She knew we were all watching, but didn’t say a thing. A minute or so in and our friend did everyone a favour and once again turned Anne towards us. On her side, with him holding her leg up, we got to see a full frontal of our female friend. Any thought of her being just “one of the guys” was completely erased at the sight of her pussy taking dick in and out again and again. Our buddy fucked her like that for about 10 minutes, their sex building in intensity before he finally exploded. He came deep inside her, letting his balls empty completely before pulling out to all the guys cheering him on. He was a hero that night. He’d fucked Anne, and had let us watch.

The guys left Anne to clean up, and went back out to the living room to drink some more and talk over what had just happened. Before long a few of the guys left, and the host himself went to bed. We hadn’t seen Anne for a while, and most had assumed she’d fallen asl**p, but I decided to go check on her. I found her in the bed she’d been in and walked over and, after seeing she was awake, asked if she was okay. In response she groped for my cock, telling me she wanted to see it. I laughed, thinking it was a joke, but she was dead serious and made another grab. And then, I don’t know why I said it, but I told her that I only showed a girl my cock if she was going to get it off.

A minute later and Anne’s legs were wrapped around my waist as I eased my stiff cock into her pussy. I couldn’t believe what was happening, how easy this was. It had been a joke a second before, and now I was watching her pussy take in my dick. Just to be sure I asked her if she was sure she wanted to do this. As a response she told me to fuck her. The sex was basic and primal. No sensual kissing, no elaborate positions, her body was something to use and enjoy and I did both.

Up close, she was spectacular. Her tits soft to the touch, nipples that perked up under my fingers, and the tightest and wettest pussy I’d ever been in. As I fucked her, her tits bobbed back and forth seductively and I knew where I wanted to finish. I didn’t bother asking when the time came, I just pulled out, aimed at her breasts and enjoyed the moment. When it was all done, I’d made a mess all over her tits and was feeling very pleased with myself. The sight of your best female friend under you, tits shiny with your cum will do that.

After cleaning herself off, Anne asked for a ride home and I was happy to oblige, and I did the gentlemanly thing and walked her right up to the door. As I gave a prolonged hug goodbye, my hands on her waist started to wander upwards under her shirt, wrapping around to the front so that I’d get a final grope in. Instead, Anne asked me if I wanted to come in, and took me straight up to her bedroom where I fucked her for the 2nd time that night. It was an incredibly satisfying fuck, knowing her protective father was in the next room unaware that his precious daughter was letting me enjoy the pleasures of her body. I had to muffle my climax, but she took everything I had to give deep inside her.

At that point I thought I might spend the night, but Anne shooed me away. I left satisfied, not knowing what would come of all of this, but happy in the knowledge that whatever happened, I’d fucked my best female friend.