At Long Last

"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.

"Ready," she said. I had a feeling she was the only one who wasn't ready, but I knew we all needed her to say she was ready. "I'm ready," she repeated.

I started the video camera, and grabbed my digital camera. We all looked awkwardly at it, until finally Chris smiled. He grabbed Jess, and pulled her into a deep kiss. I started clicking, walking around them, getting the kiss from different angles. He ran his hands up her sides, pulling up her shirt, showing her back and midriff. I made sure to get lots of pictures.

They were fully ignoring me now, and I was ok with that. I just walked and clicked, getting as many pictures as possible.

He kissed her neck, lifting her shirt. That long, beautiful expanse of tanned skin came into view. Slowly, I could see the back of her bra. I circled around, getting pictures from every angle. He pulled off her shirt, then continued to kiss her neck and shoulders, as one hand went to her ass and one to her chest. He fondled her, and she moaned softly as he continued to lick and suck her upper body.

She pulled back a bit, and pulled off his shirt. His tight chest, as tanned as hers, came into view. They kissed deeply, as one her hands started to rub the growing package in his jeans. He grabbed her hair, pulling her head back just a bit, as he roughly kissed her neck. He reached behind her, undoing her bra. I unconsciously held my breath as he let it fall to the floor. Finally, I was seeing those tits I had dreamed about in all their glory. They were beautiful. No larger than a grapefruit, absolutely no sag. My picture taking quickened. So did my breath.

Slowly she pulled back. She looked him in the eye. Something very quick passed between them; I'll never know what it was. But with an almost imperceptible nod, she slowly sank to her knees. With painstaking care, she unbuttoned his jeans. It seemed like it took her five minutes to get his zipper down, but it couldn't have been more than five seconds. She pulled them down to the floor. He was only in boxer shorts, with an obvious bulge in the front. She rubbed the bulge slowly, before putting her hands inside the waistband, and slowly pulling them towards the floor. As she got them below his waist, his cock started to show. As she continued down, it popped up, almost hitting her in the face. She allowed his boxers to fall, and I continued taking pictures. His cock seemed perfect. Tan, like the rest of him, a little over six inches, smooth. It was surrounded by a closely cropped patch of dark hair, a slight fur covering his balls and crotch.

Again, I held my breath as she stuck out her tongue and licked slowly, firmly, one long lick up the length of his shaft. My breathing suddenly matched his, as we both slowly panted, entirely aroused. I suddenly realized just how hard my cock was.

I continued to take pictures, breathing harder, turned on by what was going on in front of me.

I think she knew how much she was turning me on. I could see her smile as she continued to lick up and down his cock, sometimes slowing to tease the top of his balls. I know the sweet agony of a good blowjob, and I knew what was going on in his mind. Imagining it was my dick, I just kept snapping away.

Suddenly, swiftly, she moved her mouth over the head of his penis and covered it. Spending just a moment licking the head, she abruptly took his entire cock in her mouth. He groaned just a bit, as she began to bob up and down. With one hand gripping the bed and the other on top her head, she he was obviously enjoying it. Her technique was spectacular. She would shove the entire length into her mouth, obviously pushing into her throat. She'd pull back, licking the entire way. Sometimes fast, sometimes slow. Her hands roamed his body, sometimes gripping his ass, sometimes fondling his balls, sometimes pinching his nipples.

She pulled all the way of him, looked up into his eyes, and said "you enjoying this, baby?"

Catching his breathe, he sighed and just said "you're the best."

She grabbed him by the hips. I moved in a bit closer, thinking she was ready to deepthroat him again. But she surprised both of us. She roughly pushed him back on the bed, as he fell on his back with his legs on the floor. Still on her knees, she rushed over to him and took his entire cock once again. She jerked his cock, moving her head down and sucking on his balls. She was incredible.

I snapped away. Unconsciously, I reached down and rubbed my cock through my pants. I had never been so turned on in my life. I kept taking pictures, as I rubbed my bulge and watched my gorgeous best friend give her boyfriend the best blowjob I'd ever seen.

I stopped taking pictures for a moment, confident the video camera was picking up enough. I just rubbed myself and watched, not quite believing how incredible this was. Chris caught my eye for a moment, and for one, brief second, I had this incredible fear he was going to jump up and throw me out for touching myself. But he smiled, nodded, and put his attention back where it belonged: Jess' bobbing head.

For a few more minutes, he allowed her to wax his pole, before he sat up a bit, grabbed her, and pulled her up to him. He kissed her deeply, one hand holding her against him while the other went between her legs, rubbing her through her underwear. She moaned, deeply. As they continued to kiss, his hand worked at her pussy, rubbing against her underwear, sometimes his finger going just a bit underneath. Keeping her underwear on; that's sexy.

He grabbed her hips and spun her around, so her pussy was in his face. A classic 69 position, with her on top. This was incredible. He knew what to do; he immediately buried his face into her pussy, pulling her underwear aside to allow his tongue access. One hand caressing her ass while the other went to gently tugging and flicking her clit. She, on the other hand, took her time; teasing him, nipping all around the base of his cock, gently licking all over. The whole time, I took some random pictures and continued to rub my cock through my pants.

Suddenly, Jess looked up: "Feeling a little constrained?" she asked.

"A little," I said with a smile.

"Feel free to...you know...make yourself comfortable."

"Are you serious?" I asked.

I needed a little bit of a reality check. Here I am, in a room with the girl I've been lusting after for years, and she's 69ing with her boyfriend, and I'm pretty sure I was just invited to pull out of my cock and jerk off.

"Go for it, dude", Chris said, from underneath her pussy. "Have fun."

Ok, who am I to question fate, the gods, or her boyfriend?

She went back to licking his cock, but her eyes were still on mine. Was I being dared? I didn't know the answer, but it was time. Our eyes locked, that slight smile on her face even as her tongue ran down the length of his shaft, I grabbed the zipper of my shorts and so painfully slowly, still not entirely sure this was a good idea, I pulled it down. My hand went in my pants, and I grabbed my rock hard cock. She smiled and winked. I pulled my whole package out—cock and balls, hanging outside my zipper. She very, very obviously checked it out, and when her eyes returned to mine, I swear her smile was bigger and there was a gleam in her eye that wasn't there before.

Putting the camera down, I stood next to bed and jacked my cock, running my hand up and down while watching a beautiful live porno. They attached each other with gusto, him pulling her ass down to rub her pussy all over his face, while she took his cock deep in her throat. Suddenly, I watched her back tense. She pulled his cock out of her mouth, her hands tightened on his legs. Her breathing quickened. She buried her face into his crotch. I knew she was cumming, quietly, but intensely. And then it seemed to be over. She relaxed a bit. She looked up, her face glistening with the sweat of a great, sexy workout, and said "good job, baby."

Jess seemed to want to relax, but Chris obviously was not done. "Grab your camera, dude," he said, "I need pictures of this!"

Reluctantly letting go of my cock, I grabbed the camera. He flipped her off of him, and turned her so she was laying face down. He grabbed her ass and pulled her to her hands and knees. Grabbing hold of her hair with one hand, he used his other hand to slap her ass with his cock.

"Ready for it, baby?" he asked.

It was obviously a rhetorical question, because he then took shoved the full length of his cock into her pussy. She moaned in pleasure.

He slowly pulled back, before pushing his cock all the way in once more. He worked into a slow rhythm, speeding up just a bit. I circled and took pictures, listening to the smacking of skin each time he pushed all the way in. Sometimes Jess hammed it up for the camera, looking ecstatic. Sometimes she had that beautiful grimace on her face a girl gets when she's being pounded. Chris's look of concentration as he fucked her was incredible. He pulled her hair a bit, so she kept her back arched. Sometimes he smacked her ass.

Eventually, he slowed. He worked into a very steady, slow cadence, sinking his cock all the way in her beautiful pussy, before pulling all the way out. He still hadn't removed her underwear, so I zoomed in with the camera to watch his cock sawing past the small piece of fabric that used to run under her crotch. I alternated between quick strokes of my cock and taking pictures.

"You like the view, Tom?" Jess asked.

"Fuck yeah," I replied enthusiastically.

"You think he's really enjoying it, baby?" she asked her boyfriend.

"His hard cock makes me think he is," Chris replied.

"You know, hon," she said to me, "it doesn't quite seem fair. Here we are getting off together, and you're just sitting there, jerking off. You could be doing that at home."

Could this be going where I hoped it was going? No, no way. That's not how we did things.

"Yeah," I replied, "but the live show is so much better."

"You want more than a live show?" she asked.

Fuck, one of my closest friends was getting pounded by her boyfriend and I'm pretty sure was offering me some type of sex at the same time. Was this a good idea? Does it matter if it's a good idea? My rock hard cock was thinking for me now.

"Of course," I smiled. I figured if I was interpreting it wrong, I could always pretend I was joking.

"Then come here," she said with a smile and a wink. Shit, I think I got it right.

I put down the camera and walked over, my dick waggling out of my pants. She looked up at me, our eyes locking, as her boyfriend continued his steady, deep rhythm. We continued to look at each other as she reached up and wrapped her hand around my thick, 7" cock. She slowly stroked up and down, matching Chris's beat in her pussy.

"Did you ever think I'd be doing this?" she asked.

These people must love their rhetorical questions, because she immediately craned her neck up just a bit, and ran her tongue from the top of my tongue all the way down to my balls, making every thought escape from my mind.

"Oh, baby," I groaned.

My hand immediately went into her hair. I loved the feeling of it; my cock was getting worked over, and I was able to run my hands through her beautiful, full hair. She licked up and down my cock. I got harder and harder.

She licked down to my smooth balls. The moment she took my left nut in her mouth, I forgot everything else, including the fact her boyfriend was fucking her pussy even as she was licking my nuts. She buried her face in my testicles, as she stroked my cock, rubbing it all over her face. This was better than anything I'd ever imagined.

After a few minutes of this, as Chris continued to fuck her young pussy and I got entirely too close to cumming, she took my entire cock in her mouth. I could feel it bumping slightly into her closed throat, as she pushed it in. She proceeded to work over my cock, sometimes shoving it deep in her mouth, sometimes pulling it out and jacking it a bit, sometimes licking up and down. At one point I pushed her into my balls, pushing down on the back of her head and making her lick and suck them. I used my other hand to jerk off, rubbing my cock all over her face. It was risky; some girls wouldn't appreciate it. But she looked up with her smiling, beautiful face; god, it was enough to almost make cum.

Suddenly, she stopped. What the fuck, I thought. Then I realized Chris had stopped fucking her, and had stepped off the bed. I stepped back, too. He took her by the hand, and stood her up, next to the bed. Then he pushed her down slowly, gently, so she was again on her knees in front of him. His thick cock was glistening with pussy juice. She smiled up at him, before taking his cock in her mouth. She used her tongue to clean off every drop of her own juice.

"Come on over here," Chris said.

He stood there naked, and I stood next to him, our cocks jutting out. She pulled down my shorts and boxers, leaving me in a shirt, shorts, and my pants and boxers around my ankles. She licked my cock, still stroking Chris'. Then she licked his, still stroking mine. On her knees, in front of us, she presented quite a picture, licking our dicks. She took me all the way down her throat, still stroking him. She allowed me to put my hand on her head, and fuck her mouth, gently, softly, but deeply. She did this for about 45 seconds, before switching to Chris and doing the same thing. She used every technique in the book, and she made sure we were each treated equally. She licked our cocks, she sucked our balls. It was incredible.