"Friends" with Benefits

"Friends" with Benefits

Author's Note:

This is my second submission to Lit, with at least a few more stories planned. At least for the next few stories, they are all based on real people, and (loosely) based on real events. For example, the Mindy in this story exists, and we had regular Thursday night TV viewings at her apartment, but we never hooked up, much to my dismay.

Depending on what type of feedback I get, and how much time (and ideas) I have, I may add sequels to some stories, or they may all end up as one-offs. That remains to be seen. As always, constructive criticism is always welcome, as well as comments about what you did (or did not) like, so I can keep motivated to continue writing, and develop my craft. Enjoy!

When I was in grad school, I took a few undergrad courses for independent study credit, as I had some open space in my course schedule. Since I was only in the second year of a Masters program, I wasn't that much older than my classmates. In one of the first such classes, we had to do a group project, and somehow I ended up paired with Mindy, who was a senior. Mindy and I had chatted casually before or after class, and we got along pretty well. Since I lived further off campus, she invited me to her apartment to work on the project. While working on the project, we both realized that we watched a lot of the same TV shows, including what was called the "Must See TV" lineup on Thursday night on NBC. Since I lived alone, and my only TV was in my bedroom, we began a regularly scheduled TV night on Thursdays at her apartment. Mindy only had one roommate, who was almost never around on Thursdays, so it was usually just the two of us, and 3 hours of sitcoms, every week. We had been having our usual TV night for a few weeks, when things started to change.

We were sitting on the couch, in the apartment's living room, chatting casually during commercial breaks, when I noticed that Mindy started fidgeting a bit. "Is everything ok over there?" I asked.

"Yes," she replied. Then, hesitantly she continued, "It's just the underwire from my bra is poking me. Would you mind if I took it off?"

"Hey, it's your place. Do whatever makes you most comfortable! Let 'the girls' free if you want, I'm not gonna complain!"

With that, she reached under her sweatshirt, and unclasped her bra, and with some wiggling and squirming (which I tried not to openly stare at, but let's face it, I'm a red-blooded male, so I definitely looked out of the side of my eye a few times), she pulled her bra out from underneath her top, and tossed it on the coffee table. Now, Mindy was definitely very well endowed, at least a double-D cup from what it looked like, and the bras she usually wore were pretty supportive, so her 'girls' were now moving around under her sweatshirt a bit more freely than I had been accustomed to. Especially whenever she laughed at something on the TV, or when she plopped down on the couch after going to the restroom or grabbing us something to drink in the kitchen. It definitely caught my attention, and that increased attention was apparently not unnoticed by her, although I wouldn't find this out for another few weeks.

A few weeks went by, and Mindy became a bit more casual -- most of the time I visited, she had already removed her bra, and if she forgot, or had only just gotten home shortly before I visited, she went through the under-the-shirt shimmy removal routine not long after we sat down. I got used to seeing her braless breasts moving freely under her top - mostly sweatshirts due to the cold weather -- not that I ever grew tired of watching them bounce and sway as she moved about. I also grew used to her casual attitude about it, and about her bras laying around when she removed them while I was there. Usually, she wore a loose sweatshirt and sweatpants, a comfortable lounging-around-the-house outfit.

A few months went by, and spring rolled around, and with spring, warmer weather. One week, when I came over for our regular TV night, she was wearing a t-shirt and shorts. However, the t-shirt was both thinner and tighter than her usual sweatshirts. This not only outlined her breasts more clearly, it also showed their movement a lot more clearly. Something I noticed almost as soon as I walked in the door. Also, the shorts were much tighter than any of the sweatpants she usually wore, and were pretty short, coming to just below her ass cheeks, a fact I noticed when she went into the kitchen to get us something to drink. This was the first time I had seen her bare legs, and I took a moment or two to appreciate the view. I hadn't realized just how attractive she was! Her legs were smooth and well toned, and looked long on her fairly short frame. And, while I knew that she wasn't fat, she also wasn't model thin, but she had very nice curves. Apparently, I looked just a bit too long, because she caught me when she turned to return to the living room, but all she did was give me a mischievous smile.

Mindy came into the living room and handed me my drink before sitting next to me, as usual. She took a sip of her drink, and then leaned forward to rest her glass on the coffee table. In doing so, she went up onto all fours, her knees on the couch, and her hand on the coffee table. This had the effect of causing her t-shirt to drape down in front of her, causing her breasts to sway quite fetchingly, as well as to ride up a bit, revealing a bit of her pale tummy. It also caused her shorts to pull tight across her ass, and I realized that she was wearing a thong, as it was clearly outlined beneath the shorts. In addition, the bottoms of both cheeks were peeking out from under the shorts quite cheekily. She stayed that way for a few seconds before setting the glass down and pushing herself upright, and then plopping back down on the couch, where her breasts bounced and swayed enticingly. I also noticed that her nipples had hardened a bit during that interval; she was at least somewhat aroused. I began to wonder if she was deliberately putting on a bit of a show for me. While we had flirted lightly almost from the start, it had never gone anywhere, and I was now wondering if she was hoping to take things in a new direction.

We settled down to watch TV, and I noticed that she was a little bit more touchy-feely than usual -- she would touch my arm while making a point, or rest her hand on my knee when laughing at something I said. When she got up to get us more drinks, she put her hand on my thigh and used it for leverage to stand up. I wasn't sure, but I think she might even have given me a slight squeeze as she did so. I certainly wasn't opposed to the new attention.

Partway through the first hour, I noticed that Mindy was shifting a bit restlessly, and occasionally grimacing, so I asked her, "Are you ok over there? You're kinda restless tonight."

She replied, "I was on my feet all day today, and I think I might have overdone it a bit on my leg day workout today." She looked over at me for a second, and then asked, "Could you help me out, maybe massage my feet a bit?"

I thought about it for a second -- I don't have a foot fetish, but I'm not grossed out by feet either -- and replied, "Sure. Lemme start with your feet."

Mindy smiled, and turned sideways on the couch, with her back to the arm, and swung her feet up onto my lap. I grabbed the closer foot and started using my thumbs along the underside of the arch, and she let out a soft sigh. I massaged her entire foot, even pulling on her toes a bit to make the joints pop, which elicited a gasp, followed by a groan of pleasure after each one. I rotated her ankle a few times in each direction, and then put her foot down, and picked up the other one, giving it the same careful attention. While I was massaging the second foot, I thought I felt her apply slight pressure to my groin with her other foot a few times, but it was subtle, and I wasn't sure if it was purposeful, or just a reaction to the massage.

When I finished the off-side foot, I started massaging her calves, working my way up the underside of her leg to the knee, and then back down. I looked over and Mindy had her eyes half closed, but her breathing had picked up pace a slight bit, and her nipples were making themselves known under her shirt. I finished that leg, and returned to the near-side leg, again making sure to give it the same attention. While I was working on the second leg, Mindy slid down a slight bit, and her far leg was now angled out a bit at the knee. This had the effect of pushing her shorts up a slight bit in the back, as well as gaping open a bit in the crotch. I realized that I could now see the white lace of her thong, and the sight, along with the smooth satiny feel of her skin under my hand, soon had an effect on me. When Mindy shifted position, it also moved her other foot closer to my groin, and she must have noticed my rising erection because her foot started gently pressing against it, causing it to grow down along my leg.

At this point, Mindy's nipples were clearly visible, poking prominently against her shirt, and her breathing was noticeably faster. She began to gently curl and uncurl her toes against my hard length. I decided to throw caution to the wind and see where this would lead us. I had finished massaging her calf muscles, and now started gently running my hand up along her outer thigh, from her knee to an inch or so short of her shorts. I then ran my hand back down to her knee, and slowly back up along the inside of her thigh. When I got to within an inch of her thong, I again stopped, which elicited a soft groan from her, and I noticed a small wet spot forming on her thong. I massaged her inner thigh gently a few times and started working my way back down to her knee. At this point, I turned a slight bit more towards her, and began running both hands lightly up and down her upper legs, from knee to inner thigh. I noticed goosebumps forming on her skin.

On my next pass up her legs, when I got to her upper thighs, I kept going, up along the outside of her legs, along her hips to her waist. When I got to the waistband of her shorts, I hooked them with my fingers and paused, looking directly at her. She looked back at me for a few seconds, clearly thinking if she wanted to take this further, then bit her lip and nodded. I started gently inching her shorts down, staring in her eyes the whole time. When I got to the top of her thighs, she lifted up off the couch, and I slid the shorts over her hips and ass, then slowly pulled them down her legs and off. All she was wearing on her bottom half was the white lace thong, and I stopped for a second to admire the sight. Long, smooth, lightly tanned thighs bracketed a small, lacy, white thong with a noticeable wet spot down below a thatch of dark hair. I licked my lips in anticipation, but I wasn't going to rush this. No, the first time would be a slow buildup, a tease.

I took her legs and put one on each side of me, and turned the rest of the way towards her, kneeling on the couch between her thighs. I leaned forward, and using my right hand, tucked a wayward curl behind her ear, just barely brushing her earlobe in the process. She closed her eyes and shuddered slightly at the touch. I ran my hand down behind her ear, to cup the nape of her neck, and as I was doing that I was also leaning forward, and I brought my lips down to place a soft kiss on her forehead, and her nose, before touching my lips to hers.

I kissed her a second time, with slightly more pressure, followed by a brief flick of the tongue. I kissed her again, with a bit more pressure, and I heard her sigh and lean into the kiss. After a few more kisses, I swiped my tongue across her lips again, and felt hers open a bit to allow it entry. I turned my head to allow more contact and deepened the kiss as she opened to me. Soon, we were dueling with our tongues, and I felt her raise one hand to rest on the back of my neck and pull me closer. I pulled back just a bit and nipped lightly at her lower lip. Then I began kissing my way along her jawline to her ear. I nipped lightly at her earlobe, and then kissed down into the hollow behind her ear, which elicited a soft sigh, and she turned her head to give me better access.

I began to trail kisses down the column of her throat, and at the same time I removed my hand from behind her head and placed it at her waist, gliding it slowly up along her side. As my lips reached the neckline of her t-shirt, and the line of her clavicle, my hand also reached the bottom hem. I slid my hand slowly inside her t-shirt as I began kissing along her clavicle towards the hollow of her throat. My thumb brushed against the outer edge of her breast, which brought a short inhale, followed by a sigh as I slid my hand up to cup her breast. Her hand at the back of my neck threaded itself into my hair. I began to kiss my way back up the other side of her neck, as I gently cupped and molded her ample breast. I softly molded her breast in my hand, and then slid up and inward until I caught her nipple between my thumb and index finger, lightly pinching and rolling the nipple between my fingers until it was firmly peaked, and Mindy let out a low moan. I kissed her again, firmly and we began dueling tongues again for a few minutes before I nipped her lower lip again and pulled back slightly.

As I leaned back slightly, I brought my free hand to the hem of her t-shirt, reluctantly released her nipple, and brought that hand out from under her t-shirt and began sliding her shirt up and over the soft swell of her breasts. When her breasts came into view, I stopped for a moment and just took in their magnificence: they were large, each way more than a handful, yet still fairly firm, each topped by a large, fully erect nipple, surrounded by large, dark areolas. I gave a low whistle, and Mindy blushed lightly, and smiled at me. I reached forward and grabbed a breast in each hand and began gently kneading them, and then brought my hands up and began lightly pinching both nipples, and alternated pinching and rolling them.

Mindy let out a low moan, and looked up at me and said, "You have way too many clothes on. We should do something about that!" With that, she reached down and grabbed the hem of my t-shirt, and as I reluctantly released her breasts, I leaned forward so she could pull it up and over my head, tossing it on the floor to join her clothing. She reached up for me, and I bent back down and tasted her lips, kissing her long and deep.

After a few minutes of deep kisses, she put a hand on my chest and pushed me back a bit and reached down with the other hand to undo my belt, pop the button free, and with a mischievous grin grabbed the zipper and slowly pulled it down. She grabbed the waistband of my jeans on either side and began pushing them down over my hips. I knelt upright so she could push them over my hips and down my thighs. Lifting one leg at a time, I pushed my jeans the rest of the way off and added them to the pile on the floor.

We were both down to just our underwear, and I lay down between Mindy's thighs and brought our lips together again. We kissed long and slow, chasing tongues back and forth from one mouth to the other, trading breath back and forth, her breasts pressed against my chest, her hard nipples pressing against me, as my erection pressed against her belly. As good as the kisses were, I soon began to become aware of the feel of her soft belly against my erection, of myself throbbing in time to the beat of my heart. I began gently pressing myself into her, lightly grinding against the wet spot on her panties with the base of my erection. Mindy moaned and began pressing back, grinding us together harder. After a couple minutes of this, I broke off from the kiss and knelt upright. I hooked my fingers into the sides of her thong, and began sliding it down, watching as first her thick thatch of curly pubic hair was revealed, matted with her juices just above her opening, where her inner lips protruded slightly, slick with her juices and engorged with blood, flushed a dark pink. Then, as her thong finally peeled free from between her legs, she lifted her ass off the couch so I could slide it down her legs and off. I looked back up at Mindy as I reached for the waistband of my boxers, and as my eyes met hers, she nodded once, and I slowly slid my boxers down, until they were caught on my length. Her eyes darted down as I pulled the waistband out, and as my erection popped free I saw her smile slightly. I quickly pulled my boxers the rest of the way off and added them to the pile of clothes next to the couch.

We both paused for a second to gaze at one another, finally naked for each other for the first time. Although I hated the thought of possibly breaking the mood, I stopped to ask her, "Are you sure you want to take this further? I don't want to ruin things between us, if you're not sure."

She responded, "See, that's exactly why I want to take things further: you asked, you get it, you care! Most guys my age would've been all over me within the first week or two of watching TV here. Definitely they would've jumped me the first time I took my bra off because the underwire was poking me. You don't see me as just a conquest."

She got a mischievous look in her eyes and said, "So, are you just gonna stare and point that thing at me, nodding at my erection, or are you gonna use it?"

Always one to rise to a challenge, I grabbed my cock, leaned forward, and began slowly sliding the head up and down her pussy lips, spreading the glistening juices around the head. At the first contact between my cock and her pussy, she let out a gasp, and as I continued to slide the head up and down her opening, she sighed and laid back, grabbing her breasts and massaging them. On the next pass, when I hit the bottom of her opening, I angled my head a slight bit, and dipped the tip of the head into her, going about half the head in before continuing to tease her by sliding up and down her length.

A few passes later, and I slid just the head in, pausing for a second, before continuing the slow tease. She gasped as the head entered her, and growled as I went back to teasing her opening. I chuckled and kept teasing her. Then I changed tactics, and instead of entering her, I slid my entire length along her slick lips, making sure to pass over her clit, causing her to shudder. I ran my length up and down a few times before going back to circling her opening with just the tip. After another minute of this, I angled myself down, and slid the top of my shaft down along her opening, pressing against her taint and spreading some more of her wetness over the top of my shaft. I repeated this a few times, then went back to teasing her opening again.

Mindy practically growled, "Are you just gonna tease me all night, or are you gonna use that thing?"

Honestly, I was rock hard and throbbing from the slow buildup, and I was fairly well lubricated from all the teasing, so on the next pass, I put the head in, and paused for a second, but then I kept going, sliding my whole length slowly into her. When I had paused, she drew in air like she was getting ready to complain again, but that turned into a hiss as I sank my length into her, and finally a groan as I bottomed out inside her, and then rotated my hips a bit to make sure to press my pubic bone against her clit.

I pulled all the way out, paused with my tip barely in her entrance for a second, and then sank all the way in with one long stroke. I paused at the bottom, ground against her clit, and then slowly pulled out. This became the pattern, sinking in faster on each in stroke, and pulling out slower on each out stroke, teasing us both with the delicious friction. After a few minutes of this, I grabbed her legs and put them up over my shoulders, and began stroking faster, still going balls-deep on each downstroke. Mindy began moaning, her hands which had been stroking her breasts began squeezing them, pinching her nipples. I began stroking into her faster, harder, and her moans became more urgent, rising in pitch. I began to feel myself getting close, the urge to come building in my balls, but I wanted to make her come for me first. I could feel her legs starting to tremble where they were pressed against my chest, so I asked her, "Are you going to come for me Mindy? Are you going to come on my hard cock pounding into your wet pussy? Are you going to come all over me?"