Friend with Benefits

Note: Back when Friends first aired, I was all about Rachel. These days when I watch the reruns, I find that I'm more of a fan of Phoebe. This story was inspired after watching "The One with Joey's Porsche."

It was late afternoon and I was still figuring out what my plan was for that evening when I got a phone call that made that decision much easier. It was my friend Phoebe asking if I would mind if she stopped by. That was a no-brainer, of course, because Phoebe and I were what would be known today as "friends with benefits." This being the late 90s, we referred to ourselves back then as "fuck buddies." Either way, she told me that she'd spent the afternoon babysitting her brother's triplets and now desperately needed to engage in some adults-only activities. She'd figured that, if I wasn't available, she'd probably go with drinking bourbon. When I suggested that we could combine drinking bourbon with what she had in mind she replied that, since combining the two would be more likely to result in even more babies, she thought it best to leave out the bourbon.

I know...there's still the possibility of babies even without the bourbon but the odds would definitely increase with the introduction of alcohol. Interestingly, as I thought about it, our booty calls rarely came after a night of drinking for either of us. I don't think Phoebe really drank much to begin with and, if I was going to be getting naked with Phoebe, I wanted all of my faculties and to be able to remember all of it. She was very at ease sexually and she definitely wasn't kidding when she said that she was "bendy" so we always had, not just highly satisfying sex, but a lot of fun, too. It also didn't hurt that she was fit and cute along with being a bit quirky. Sometimes it seemed like she was the smartest person in the room and sometimes it seemed like she'd just arrived from another planet. When we got together, it was typically because one of us was just horny and the other never hesitated to accommodate, but there were definitely times when we got a bit adventurous, too.

I was a little surprised when I opened the door to let her in because she was wearing jeans. They fit great and she looked fantastic in them but I was so accustomed her wearing flowy skirts and dresses that I was caught off guard. That didn't stop me from staring at her ass as she entered my apartment. Her top was also pretty snug, showing off her perky boobs, and I realized that maybe I was more than just a bit horny. Once the door was locked behind her, we slipped into each other's arms and made out while my hands dropped down to caress her ass through her jeans. I pulled her against me but I didn't think she'd feel my cock stiffening as well as she might have through a filmy skirt. She knew me well enough, though, that I'm sure there was no question as to whether I was ready to go.

We parted and she took my hand, leading me to my bedroom, where we resumed making out beside my bed. She pulled my shirt up and off then cast it aside so I did the same, raising her snug blouse and revealing her bra. Her boobs weren't big but they were really nice and, though I was tempted to just immediately remove her bra, instead I fondled her boobs through it, feeling her hard nipples pressing out. She started to undo my jeans so I kept fondling until she hunkered down to take my jeans down and help me step out of them. She briefly massaged my stiff cock through my briefs before standing again. Rather than resuming the fondling, I got her jeans opened then hunkered down myself to slide them down, revealing her panties. I gave her the once over in just bra and panties before standing and lifting her, carrying her onto my bed. I set her down on her back in the middle of my bed and lay beside her, going back to making out with her and fondling her boobs through her bra.

As I alternated from one boob to the other, I was able to determine that her bra did not have a front clasp. When I slipped my hand around behind her, she rolled toward me slightly to give me better access. I unfastened her bra then slipped my hand under the cups to caress her bare breasts and hard nipples though, to keep things moving along, I soon lowered my head to alternately lick and suck each of her nipples. She shed her bra and tossed it aside, moaning softly, but when I slipped my hand down over her stomach and into her panties, the moaning became louder. I found her pussy practically overflowing with her juices so this confirmed that she was incredibly fired up and I wanted to take some of the edge off. I kissed my way down over her ribs and stomach then started to slide her panties down, revealing her blond bush.

Positioning myself on my stomach between her parted legs, I gazed at her pussy while alternately kissing along each of her soft, smooth inner thighs. Finally, I ran my tongue along her slit, tasting her juices and making her moan even louder. I slurped up her juices a bit before slipping a finger into her while licking and sucking her clit. This immediately had her moaning louder and longer as she reached down to hold onto my head. She was rocking her hips as I devoured her pussy and it seemed like it wouldn't take long to make her cum. Rather than try to draw out the pleasure and hold off her orgasm, I focused instead on making her cum then figured I'd just keep going once she had. It wasn't as much about my technique or my skill as it was about just how worked up she was so I had to think that, once she'd finished babysitting and we'd talked, she must have been focused solely on the impending sex.

I was happy that it appeared as though she'd be cumming quickly because it took a little pressure off of both of us. Not that sex with her was ever stressful but sometimes we just put that pressure on ourselves; me to make her cum and her just to not feel like it was too much effort for me. I enjoyed being down there between her thighs, eating her pussy, and I'd told her many times that I didn't care how long it took. In reality, it had never taken very long any time we'd been together but I guess it can be difficult to shed insecurities. I could feel her pussy becoming even wetter and more engorged the longer I was eating her so I knew fucking her was going to feel great, just as it always did. Between this and her louder, longer moans, it was obvious that she was almost there. I just kept up what I was doing even as she started to tense up and hold onto my head even tighter.

She went briefly still and silent then let out a loud and passionate cry as her body started shaking. I had no doubt that her cry could be heard through the walls of my apartment but I had no issue if my neighbors knew I was not only having sex but was also providing a high level of pleasure to my partner. Phoebe tended to be loud in general but during sex I was definitely less concerned about her volume disturbing my neighbors. I continued to devour her pussy as she was cumming and her orgasm appeared to be both long and highly pleasurable, which was not unusual for her. As it tapered off, I kept up what I was doing and she made no indication that she'd prefer that I stop. She seemed to relax for a bit but it wasn't long before she was clearly starting to build toward another orgasm. This time I made more of an effort to draw out the pleasure rather than focusing on making her cum.

Her moaning was building in duration and volume as the level of pleasure was obviously also building. We had nowhere else to be and, as far as I knew, no other plans for the night aside from pleasuring each other so I was definitely enjoying being where I was and doing what I was doing. Glancing up, it was pretty clear based on her expression that she was enjoying it, too, as if I couldn't already tell that from the moaning. The longer I was eating her, the wetter and more engorged her pussy was becoming which was making me even more eager to slip my cock into her but, again, we had the whole night ahead of us.

Her grip on my head had relaxed when she'd cum but, as she was getting closer to her second orgasm, she was holding me tighter and humping her pussy subtly toward my face. She was also beginning to tense up though she appeared to be trying to remain relaxed each time she realized that she was arching her back. Finally, she briefly went still and silent again then let out a loud and passionate cry as her body started shaking. I continued to devour her as she was cumming and, no surprise, it was another long and clearly highly pleasurable orgasm. I was still enjoying myself so I just kept going through this orgasm then through a couple more before finally stopping. I kissed my way up over her abdomen and ribs to her tits, licked and sucked each of her nipples then lay beside her as she was recovering.

"You're so good to me," she said, turning and kissing me, "Hey, I taste delicious. No wonder you spent so much time down there."

"I keep telling you that," I reminded her, "Beautiful blond bush, tasty pussy...you're lucky I don't just set up permanent residence."

She kissed me some more while reaching down to massage the bulge in my briefs, which I was still wearing. She slipped her hand inside and briefly stroked my stiff cock before getting up on her knees and sliding my briefs down and off. I was just ogling her naked body as she was moving around then as she straddled me. She guided my stiff cock toward her blond bush then lowered herself onto it, causing both of us to moan. She briefly just sat on my cock, feeling it inside her, before slowly beginning to move up and down. I reached up and fondled her tits, feeling the soft, smooth flesh and her hard nipples. Her pussy felt amazing as it slid up and down my tool, so wet and so snug that I'm surprised I didn't shoot off immediately.

Since Phoebe never seemed to have any issues with cumming, I wasn't expecting it to take long before she had another orgasm and, since she'd already had several, that usually made having each subsequent one even easier to achieve. She was way too free-spirited to ever consider it but I'd have married her just because it was so easy to make her cum. I was certainly happy with our current situation, though, and would have no issues if we were never more than "fuck buddies."

As she gradually picked up her pace so that she was riding me harder and faster, her boobs were bouncing so I moved my hands away from them to watch. As I gazed at her bouncing boobs, I ran my hands down over her ribs and waist and around to her ass. I was not only caressing the soft, smooth flesh but also holding it so that, each time she dropped down, I could push up into her, giving her my full length. Her pussy was becoming even hotter and wetter the longer she was riding me so I could feel the first stirrings of my orgasm. I still wasn't sure how I'd lasted as long as I had up to this point but it was obviously no problem since I certainly wanted to continue having her ride me for as long as possible. I really was thoroughly enjoying feeling her pussy sliding up and down my tool while watching her tits bouncing.

When she finally dropped down on my cock and just sat there with her eyes closed and her mouth open, I still somehow wasn't too close to cumming myself so I figured we'd be switching things up once she'd finished. Since they were no longer bouncing, I brought my hands back around and resumed fondling her titties. I doubt this helped with the pleasure she was feeling but it didn't sound as though she needed any help anyway. Her orgasm was clearly another long and highly pleasurable one and, as she was cumming, my orgasm was even backing off a little so I was happy that I'd be able to enjoy more pleasure for longer once she'd finished and we'd figured out what we were doing next.

It turned out that she apparently already knew what she wanted to do next because, when she finally finished cumming and had taken a moment to recover, she climbed off of my cock but remained on her knees beside me. When she leaned forward so that she was on all-fours with her ass up in the air, I got up and knelt behind her then guided my stiff cock into her, easily slipping all the way in until my hips were pressed against her ass. Holding her waist, I started to slowly slide my cock in and out, relishing the pleasure that I was feeling as a result. I was looking down, gazing at her sweet ass, which would jiggle each time my hips tapped against it. Once I had a good rhythm going, though, I slid my hands forward over her ribs until I was cupping her boobs. As I felt the soft, smooth flesh in my hands and her hard nipples against my palms, my cock was becoming even harder, which I wouldn't even have thought possible. She clearly felt it as well because I don't believe me fondling her boobs would have had her moaning louder and longer.

She had reached under herself when I'd slipped into her so I assumed she was caressing her clit while I fucked her. I was always glad when she was being proactive about her own pleasure and I definitely wasn't taking it personally that she was helping herself along. My orgasm resumed building up, nice and slow despite how incredible her snug, slippery pussy felt gripping my cock and how much I was enjoying fondling her tits. When it sounded like she was getting closer to cumming again, though, I did release her tits and straightened up, holding her waist. This way I could make sure she was getting the full length of my cock with each thrust. Because she had her head down and was reaching under herself, she wasn't pushing back so I figured it was on me to make sure she was getting as much penetration as possible.

I was gradually picking up the pace, fucking her harder and faster, her ass jiggling and I'm sure her tits were swinging like crazy. Her moaning was getting louder and longer which was helping to give me a sense of how close she was getting to cumming. Her pussy was also becoming even slicker than it already had been, so the pleasure I was experiencing was increasing as well. When she finally cried out and started shaking, I continued to fuck her but it wasn't as hard and fast. I switched to long, slow strokes which I was really hoping were helping with her orgasm because they sure felt incredible to me. Whether it helped or not, her orgasm was long and appeared to be pretty pleasurable for her, which was no surprise. I didn't stop fucking her even once she'd gone still and had let out a sigh.

I was getting closer to cumming by then but, once she'd apparently recovered enough, she moved forward so that my cock slipped out of her. Straightening up on her knees, she turned toward me and we kissed as I fondled her boobs some more and she briefly stroked my cock. She ended up maneuvering me around and having me lie on my back then moved backward down the bed, kissing her way down to my stiff cock. As she lay between my spread legs, she gripped my stiff tool, pumped it a couple of times, then engulfed it in her hot mouth. I was immediately moaning as her mouth moved up and down my shaft while she gently pumped the base. I pulled my pillows over to prop up my head so that I could watch and watching her suck my cock was even hotter than just feeling it.

She had my orgasm building up again from the moment she started sucking my cock but she also somehow managed to draw out the pleasure she was providing, allowing me to enjoy her cocksucking for longer. I would have been more than happy to continue enjoying it through the entire night but, even though she was able to draw out the pleasure, there was only so much she could do when it felt so fucking incredible. Gradually my orgasm was building despite her efforts to prolong this blowjob though, even as my cock began to swell a bit more, she was unfazed and maintained her efforts. She did wind up adjusting her technique slightly to get me the rest of the way there rather than continue trying to draw out the pleasure when she knew I was getting close to cumming.

When I finally exploded into her mouth, the pleasure was intense and seemed to go on and on. Still unfazed, she swallowed my load while continuing to skillfully suck me off. Only when I was fully spent did she release my cock from her mouth then smile when she saw the look on my face. She crawled up to lie beside me, her naked body pressed against my naked body. This was just the beginning, though, and we cycled through fucking and recovering until we were exhausted. Actually, we did take a break to order out some food, then resumed our activities after eating. There were also never any regrets when we woke up together the next morning, usually because we started fucking again. There had been a few times late on a Sunday night, however, when I'd contemplated calling out from work the next day to stay in bed with Phoebe...and a few times I'd actually done it.