"Yeah, cum on my face." A few months ago, I'd never have believed I'd hear my best friend say that to me. And yet, there I was, with her boyfriend, getting ready to cover her face.
We'd been friends for years. We met in college, and hung out almost every waking hour. Some people thought we were secretly hooking up, but we never did. Our relationship never swung that way. Sure, she was hot (way hotter than I could ever do), and she did fuel many late-night jack-off sessions, but that wasn't a big deal to me. We were friends; trusted each other, enjoyed each other, and just had fun.
So, what does she look like? A 5'7", long-haired, sometimes brunette, sometimes redheaded, goddess. With beautiful blue eyes that seemed to swing to hazel; a tall, lean, taut body; beautifully small, perfectly rounded breasts; and a curved ass that made men drool; she was a walking wet dream. At times she knew it—her clothing and walk could make sure a man remembered her for the rest of his life. And at times she didn't—she was self-conscious, insecure, and needed people. What a woman. And what a friend.
Me, I'm nothing exciting. A pudgy, tall, dark-haired, brown-eyed, guy. You've seen a million guys like me on the street, and will see at least 10 more by the end of the day.
So, how does this story end? Do we date? Do we fall in love, suddenly, realizing years of mutual attraction? Nope. But this tale does have a very, very happy ending.
We're a few years out of college. We don't live very close to each other, so we don't see each other much, but we're still good friends. Chatting online, emails, infrequent dinners or drinks. It works for us. I knew about her boyfriend. I'd never met him, but she liked him a lot, and he seemed like a good guy. And then one day, our conversation turned to sex.
It seemed her boyfriend had certain fantasies. Dreams of group sex, gang bangs, threesomes. Several men doing her at one time. And let's be honest—who doesn't have those thoughts at some point about the woman they're dating? The difference between this guy and the others: he was ready to make it happen.
Jessica (that's her name) was definitely not that type of girl. Prior to this, she'd been in a long-term, fucked-up relationship. Semi-monogamous on her side, not at all monogamous on his. We (her friends) had warned her many times, but it was a mistake she had to make (and she did). So finally that was over, but she was a girl scorned. Trust wasn't coming easy. But she'd found the perfect guy from her—you know, other than the fact she wasn't ready to be gangbanged.
But Chris (and that's his name) was understanding. A fantasy can just be a fantasy. But that didn't keep him from bringing it up sometimes, in bed or outside of it. And through a little bit of wrangling, I was able to figure it out it turned her on, even if just a bit. Was there a way I could take advantage of this? Perhaps, but it sure wasn't at the forefront of my mind.
Jess gave me more and more information. She's never volunteered much, but she responds quickly to questions, and will quickly follow a conversation path to exactly where I wanted to steer it. And more and more, it came to sex. And Chris's fantasy. And how she could make it come true.
Our conversations got dirtier and dirtier. Well, maybe dirty is not the right word. More descript. More detailed. I found out more about her sex life, what turned her on, what she wanted to do and didn't want to do. I finally convinced her to share a picture or two. And those four pictures were my first glimpse of perfection. I'd always pictured her perfect ass, her tight stomach, her sexy chest; my imagination was nothing compared to actually seeing it. Her beautiful face, her tongue licking up the long, hard, smooth shaft of her boyfriend's cock. Those eyes looking into the camera also made me cum when I first saw them. Another of her riding him, his cock piercing her tight, slightly reddened, obviously well-fucked pussy. And the best of them all, him covering her tits in his cum.
I was turned on. I was aroused. I now had the best fuckin' jerk-off material EVER. So, after spending the next week calling in sick and masturbating (just kidding), I finally made my suggestion to her. Sure, the pictures were good. But they could be better. No one ever made really good porn by themselves. Maybe they needed someone to tape them. Someone with a really nice video camera and digital camera. Someone to guide them into positions that would photograph well. I knew Chris wanted another man, and Jess didn't. Maybe this could be the compromise. I could be the man, but in a non-sexual role (well, as non-sexual as you can get when you're taping two people having sex).
So, I held my breath and suggested this to Jess. She liked the idea. She shared it with Chris. He liked the idea. So, we decided to make it happen.
I was nervous. I hadn't yet met Chris. And I had no clue what to expect. Being ever the optimist, I made sure I was cleaned up all over: clean underwear, a little trim down under, an understated cologne. Then I borrowed my roommate's video camera and digital camera (hey, I only implied I owned one!). Made sure they were fully charged. And got into the car for the long drive to Chris's house.
I sat in the car for a few minutes, thinking this could change our friendship. Or maybe not. Just watching someone have sex doesn't take away from friendship; hell, sleeping with someone doesn't always ruin it. So, I took 10 deep breaths, got out my car, and knocked on his door.
Jess answered the door. She was wearing a white tank top and tight jeans. She hugged me, invited me in, and introduced me to Chris. A little shorter than me, but a little taller than her, he was tall and lean, but in that way that you can see his strength in the way his muscles rolled. Short, cropped brown hair, brown eyes, he was very handsome, and definitely Jess' type. He wore a white tshirt and blue jeans (although a little looser than hers).
"Chris," he said, shaking my hand.
"Tom," I said, as if we could each be any other person. We knew what was going down tonight. Jess offered us beers. We each took one, and sat down in the living room.
"Did you see the O's game?" I asked. Whew, sports. This can kill some awkwardness.
"Nah, I've been following the Nationals," he said.
Ok, I can handle this. Forty minutes of inane conversation followed. But it was ok. It wasn't awkward. It was pleasant. We could handle this. We could be friends. We could chat. Cool.
"You ready to do this?" Jess finally asked.
Oh, lord. I hope so.
"Yeah," my voice squeaked a bit. We all laughed. Ok, tension averted.
I grabbed the bag I'd sat by the front door, and followed them in the bedroom. I set up the video camera on a tripod, as they held hands and watched me. I pulled out my digital camera.
"Ready," I said. They exchanged glances.
