A Friend With Benefits

Sabrina and I had a recent weekly tradition. I'd come over on Wednesday night to watch Lost with her and her roommates. We'd drink wine and gossip. Then, after Lost, her roommates would go to bed and Sab and I would go to her room to watch a movie. Deep down, I'd always felt Sabrina would be an easy hook-up. We'd been friends for several years but I'd never made the effort to try and have sex with her. She reputedly had pretty low confidence when it came to guys and was pretty easy. In the looks department, she was nothing to write home about. I figured a low-commitment "date" couldn't hurt suggested that we watch a popular TV show together.

After Lost, we went into her bedroom, turned a movie on, and poured more wine. We drank and chatted through the first ten or fifteen minutes of the movie. Once we quieted down and focused on the movie, we had missed a few things and weren't too sure what was going on. We both grew bored quickly. As my mind wandered I studied her.

Sab looked alright that night. I wasn't sure what had happened; whether Sab had dieted, started doing drugs, or actually started working out, but she looked like she had lost five to eight pounds. In other words, her stomach was decently flat, no noticeable bulge, and her tits looked as good as ever. Sab had a plain face, but smooth skin and pretty eyes. Her teeth were straight and clean. In all, she could have been a lot hotter if she took better care of herself, had more style, and some more confidence. Luckily, she seemed to be coming out of her weird, dark phase as her hair was noticeably lighter. But, she still insisted on styling her with those annoying hipster bangs. She dressed plainly, in jeans and a spaghetti-strap tank top. Sab knew her only strong trait was her chest. She had huge boobs. Sab made no effort to think of a more creative asset to accentuate. Regardless, as we both awkwardly sat semi-prone on her bed, I felt my blood run through my body and being to pool at the tip of my penis.

The pot I had smoked directly prior to getting to the house made me bold and affected my decision making. At a lull in the action of the film, I positioned myself closer to her. She immediately leaned into me. A few minutes later, we were low on wine and had moved even closer. I decided to move things along quickly. I took our wine glasses and set them on the dresser. I immediately leaned in and kissed her mouth. She kissed me back. She was a pretty shy kisser, but the wine she had guzzling made her a bit bolder. Unfortunately, her tongue and lips were clumsy and things got pretty sloppy. I leaned back against the bed and drew her into me. She moved in close and kissed me harder. I began to rub all over her body, but mainly on her tits. Her boobs felt amazing. They were truly huge, but still held tight and firm by her cotton shirt and soft bra. My dick was fully erect, and I began grinding against her, she grinded back. It was all very high school, even though we were each twenty-five.

I pulled her shirt up over her heard. She made no move to stop me. I played with her boobs some more and she put her hands behind her back to unhook her bra. I made no move to help her; she really wanted me to see her boobs. I could tell she was worked up, she wanted something, and she was now acting as the aggressor. By her own lazy logic, she knew showing me her boobs was the best way to ensure I would continue fooling around with her. This was going to be easier than I thought. I made a big deal of marveling over and worshiping her boobs, so she would think I was really into it. I handled their girth in my hands and kneaded them firmly. To be honest, they were a bit of a letdown as their sheer magnitude caused them to spill unflatteringly across her chest. Still, they were nice to toss around.

Before resuming kissing, I took my own shirt off and let her return the favor across my chest. She kept up the act and gave my torso way more physical attention than it deserved. I started to take my pants off. When she helped me with my belt I knew we were in for it. At this point, I was still sitting over her. After I got my pants off I straddled her torso. I placed my dick in between her huge boobs and began to fuck them. She knew the drill as she grabbed the sides of her tits so they would hug my dick. Again, she was not shy when it came to presenting her chest in a flattering light. I only started to tit-fuck her to segue into her sucking my cock, but I had to admit, fucking her tits was pretty nice.

She expertly positioned her mouth in a downward, half-open open position. She did not resist for a second as I moved my cock between her lips and into her mouth. For a minute, she held still and let me fuck her mouth. Then, she took control. At first, she slowly got her head into the rhythm of my hips. After taking a good bit of my dick, she placed her hands on my hips and took control of guiding them forward, while taking my dick in her mouth. It was at this point that I knew I was in the hands of an exquisite cock-sucker.

I reflected on this as just under seven inches of my meat slid into her mouth for the umpteenth time. She must have been sucking my dick dutifully, with no interruption, for over five minutes. At this point, I seriously considered blowing in her mouth or on her face and then recovering later to fuck her. I was getting the vibe the sky was the limit with this chick and that I could essentially set the sexual itinerary. I was so emboldened by the preceding events that I let myself wonder if I wanted to fuck her in the ass and if she would let me.

I let my right hand move to the back of her head. At first, I gently held behind her skull and matched my hand with the movement of her head. Then, I began to hold her head harder and take control of the speed and rhythm of my thrusts. She grabbed my hips harder and opened her mouth wider. By now I had decided to make a statement about the future of the night. I wanted to blow my first load right on her face. I knew that afterwards I could get her to keep blowing me and get me hard again. If I'd even need it. I was pretty worked up today and the sizeable joint I had smoked earlier was making my blood pump quicker. I didn't have any doubts about my ability to recover.

I took my dick out her mouth and moved forward across her face. I rested my balls squarely across her lips. She stuck out her tongue and lapped at my ball sack. I sat up slightly and dropped each ball into her open mouth. She began to suck each of them. She even let out a few moans as she nestled my nuts in her lips. As Sab gave my nuts a few more strong licks, a sudden, jarring thought occurred to me. Was my confidence so high I'd risk trying to get her to lick my asshole? Was she the kind of girl who would do that? Did I want her to do that? Could I envision needing to kiss her later? The hypothetical scenarios ran deviously through my brain. She was making no signs of tiring or growing bored or impatient. I gazed down at her; her eyelids were almost closed tight as she focused on my balls directly over her. She seemed deep in concentration.

I decided to do a sort of test run and moved up an inch on her face. The focus of her oral attention then moved from the middle of my ball sack to the base of my balls. Her tongue rode the edge of my undercarriage. I wasn't sure if she was aware of the implications of my maneuver, but things were going exactly as I had expected. I had her pegged as extremely, almost to a fault, accepting during sex. So far, she had proven my expectations correct. I moved my hips forward once more, another inch. Again, her tongue moved as well, she was now licking my undercarriage. I tightened my grip on the back of her head slightly, and moved her head down even further. She took the hint and let her tongue slide along the edge of my ass. She licked the exterior of my asshole for a few seconds. It seemed clear she would indulge me for the sake of keeping me stimulated but that she was not really into giving me a rim job. I gave her head another little nudge, poking her tongue into the cleft of my ass ever so slightly. I made her give me a few licks for good measure before I moved back down and reinserted my cock into her mouth. She had passed any conceivable test in my book with flying colors.

By now, I didn't need much more stimulation. I had only edged off a tiny bit, to build up more of a load, but I didn't want my first eruption to be so momentous that I was spent for too long afterwards. Once again, I plopped my balls onto her lips and began stroking myself off in front of her face. She knew what was coming and started licking my balls in earnest. I roped off an initial jet of jizz across her face, from three o'clock to ten that landed in her right eye. Sab had both eyes nearly closed so the white rope pooled mainly on her eye-lid. She snapped her eyes shut as her face endured the rest of my load. By the end, she had five strong ropes across her face from the bottom of her chin up across her forehead and in her hair. I gave her a quick peck on her left nipple and left to get her a towel. I was too spent to bother with tissues so I grabbed what was obviously her bath towel off the rack and brought it back to wipe my cum from her face.

She cleaned up pretty quickly, her shy awkwardness was appreciated as I took a few seconds to relax and reflect. What Sab totally lacked in physical beauty, she was doing all she could to make up for in downright charitable foreplay. I didn't try and talk much. She made a brief attempt at trying to show how satisfied and impressed she was with a few, "wows" and "my gosh's". They were quite cute. Luckily, my dick had never fully subsided from its previous erection so I was showing like a motherfucker. I lay down on the bed and she came over to nestle and cuddle for a brief minute.

I definitely didn't want the night progressing to this kind of behavior already so I made a move for her crotch. I began to grind her jeans-covered crotch with my hand. At this point, I had to tread delicately. My dick needed another minute or two of rest before action. I wanted to make sure she was warmed up again, but I didn't want to commit myself to something that would either kill my mood or that I would regret later. Namely, I didn't want to get stuck licking her pussy, fingering her pussy, or even kissing her for any extended period. She moved her face up toward mine and I gave her the neck maneuver as I buried her face between my shoulder and shin. She took this as a sign of passions and willfully went to town on my neck, coating it with a bit too much of her saliva.

I swung across her shins and started to pull down her pants from her hips. She helped me, and pulled the panties-at-the-same-time-as-the-pants maneuver. This was another good sign. She was in a hurry to get naked. Again, I moved across her stomach and fucked her tits. Then, I moved my dick back into her mouth. To her credit, she took my dick with just as much enthusiasm the second time around. I was quickly hard again.

I moved down her body and positioned myself between her thighs, opening them further in the process. I grinded my package against the inside of her thighs. I wanted to give her an indication as to where I was to about to take this. She grinded against me in return. Her hands moved across my back and ass. She wanted it really bad. I moved my cock between the wet lips of her pussy. She was noticeably wet, but no overly slick. She was close to perfect. My cock moved into her easily, but with a healthy, natural resistance. It felt pretty amazing. She moved her legs up nice and high. She settled into my rhythm quickly. She really knew how to take a cock.

I quickly built momentum; I wasn't going to break this girl easily. I knew I could basically give her all I could and that she would take it just fine. I was eternally grateful that I had already busted once. I already knew my stamina would be much better this time around. I really set into motion as I thrust away on top of her. Her tits swung beautifully as I railed into her. In the middle of our hard fucking, I moved her hips up and gave her my full length, as deeply as I could. As well as she was taking the majority of my cock, I didn't think an extra half-inch would matter too much, but she let out a few deep moans and I broke new ground in her pussy. I briefly wondered if her roommates were still awake to hear us. To Sab's credit, she was able to recover well enough as her moans subsided to whines.

I moved off of her. As she sat up, I stood up on the bed and grabbed her by the head. I shoved my cock between her lips, not gently, and began to fuck her mouth. I was pretty worked up. Then I laid down across the bed and grabbed her by the thighs, forcing her to straddle me. I guided my dick into her pussy and put my hands on the back of her ass. She posted her hands up on my chest, stuck her butt out, and went to town on my post. It was truly a sight. Her out-stretched arms, resting on my chest, created the perfect perch for her fat tits. They swayed and bounced with her gyrations. Her pussy felt amazing. She was methodical and determined. I was content to let her use me like a dildo on a skate board for several minutes.

As I grew board, I once again grew bold. I moved my hands down across her ass cheeks. I pulled her butt cheeks apart softly at first, but then harder. I nestled my pointing finger into her crack. I stuck my fingertip in her ass and matched the movement of her hips for a few seconds. Then I began to finger-fuck her ass. At this point, I hadn't decided if I wanted to fuck her ass or not but I knew I shouldn't squander this opportunity to let her know where the night might lead.

I moved her off me by the hips and positioned her for doggy style. Luckily, she had a vanity mirror on a wall across from her bed. So, by positioning her body a certain way, I was able to get a terrific reflective view of her face as I fucked her from behind. I immediately set about penetrating her as deeply as I could. Sab had a big, white ass but it was smooth and it felt amazing to stick my rigid dick deep in between her thighs. Again, she cried out in suppressed pleasure for the first few initial thrusts, before calming herself. I grabbed her by the hair and pulled her head up, so that I could see her face in the mirror. She didn't seem to want to make eye contact, she seemed pretty self-conscious in front of the mirror, but her shyness only turned me on. I made her make eye contact with me a few times but she always glanced away after a few moments.

After nearly driving Sab off the bed a few times, I flipped her over again and moved between her thighs. I fucked her harder than before, getting her legs up closer to my shoulders. At this point I decided to make my mark on the evening. I asked her with a whisper, "are you on the pill?" She gave me the one word answer I was hoping for, "yes" she whispered back. I didn't say anything in return but settled into another pattern of vigorous thrusting. After several more minutes, I quietly but forcefully jammed my cock deep into her pussy and blasted a load of semen inside her. I made a big production of thrusting into her and climaxing like a rock star. She totally got off on it. After I was spent, I rolled off of her.

Before she could make a move to cuddle, I not-so-subtly hinted, "its ok, go ahead and clean up in the bathroom." Whether she understood the exact specifications of that hint I can't say but she acquiesced and moved into the bathroom. After the obligatory toilet and sink noises she came back out. Of course, when she came back her hands were freezing from the cold water she had used to wash her hands.

At this point I was content to let her snuggle me to prove that it was ok that she had just gotten gut-fucked by a dude who was not her boyfriend. Being the semi-lazy nerd girl that she was, and completely incapable of making any kind of small talk, she quickly agreed to turning on the tv. She even had the previous week's The Office and 30 Rock on her DVR. She had already seen them but I asked if I could watch them. She agreed to let me watch them.

During The Office, I could tell she was a bit bored from having already seen the episode. I began to tease her a little bit. She performed all the requisite giggles and gasps to let me know my efforts were appreciated. Again, I didn't want to get into any foreplay commitments that I didn't want to keep. Luckily, I was inspired by an ad for the upcoming episode of 30 Rock. I expressed my love for Tina Fey. Sab quickly agreed. I even recall Sab describing Tina as her "lesbian-crush". Again, I let my inebriation affect my choice and words and I proposed that Sab suck my dick while I watched 30 Rock and fantasized about Tina Fey. To illustrate my point, I pulled the sheet from off of me and exposed my nearly erect penis. Sab seemed to honestly marvel at its rapid ascension back to erectness. Also, the TV light was casting it in some pretty legit lighting that gave it a huge shadow.

Sab sat still for a moment and feigned shock and surprise. She looked at my semi-rigid penis and then back at me. Sab let out a half-hearted scoff, but then simply giggled and moved down to engulf my cock. I watched the entire episode of 30 Rock (which was delightful) as she bobbed up and down on my dick. During the mid show commercial break, she tried to pull the kiss-your-way-up-the-chest maneuver but just as she reached my nipples the show started again. I pushed her head back down to my dick and muttered, "after the show . . ." It was pretty awesome.

As a man of my word, after the show ended and she had been sucking hard on my dick for at least twenty-two minutes, I flipped her over, stuck my dick back in her sodden pussy, and gave her an immediate jack hammer session. This part of the fuck was pretty much for her benefit as I could have come at any point. I was edging off to try and give her some more enjoyment. I wanted her to feel rewarded for all her hard work. I let her ride me for a few minutes but I wasn't going to hold out forever. I flipped her back over and fucked her missionary for just a few seconds. I quickly moved over her mouth and dropped my load over her waiting tongue. My load didn't project as far this time but the quantity I was still able to produce impressed me. I completely covered her lips. My cum ran down her neck.

I flopped onto the bed while she went to the bathroom. After more water noises, she brushed her teeth. She went to her closet, put on some boxers and her tank top and asked if I wanted anything to sleep in. I declined and she came back to bed. I let her snuggle me pretty close and we drifted off to sleep. In the morning, she woke up around 7:30 and spent some time getting ready while I slept in. Before she left for work, she came over to say goodbye. I didn't hear or listen much to the praise she lavished upon for the night before. As she sat on the edge of bed, I started to play with her tits through the blouse she had put on for work. She moved to get up but I held her to the bed. I made her give me a quickie blowjob before she left for work. She went work with the taste of my cum in her mouth. I probably made her late.