Friends...With Benefits
written by:
nude_in_wpg

"I think we should have sex."

"Uh, what?!"

Ok, so maybe that wasn't the most articulate response ever given to that question, but I suppose I did catch him a little off guard. I mean, really, how often does that question fly out of the mouth of your childhood platonic best friend with no warning?

Tyler and I had been friends since pre-school. We had met at one of the many activities my parents had enrolled me in, and when our mothers learned we lived on the same block, we found ourselves thrown together constantly. We were in many of the same activities, our parents babysat for each other, and then of course we ended up at the same school. We weren't always tight friends, but it seemed that every couple years at least we'd drift back together and hang out a lot. Summers in particular; my mom worked, his didn't, so I would often end up over there during the day. Inside we played dress, up, let's pretend, he'd even play dolls with me when I asked. Outside we'd chase each other, throw or kick various balls back and forth...you know, normal kid stuff for those days. As we got older, video games became our thing.

When I hit my teenage years, and even before, my dad used to tease me about the time we spent together, but the fact was, we never dated. We were just...friends. Even at school, aside from the occasional bit of needling from friends, everyone knew we weren't a couple. But anyway, in spite of other friendships that came and went, when the time came for us to head to college and the question of who to room with arose, we naturally chose to rent an apartment together. As a sign of just how platonic our friendship had always been, neither my parents nor his objected to our co-ed living plans...other than browsing 2-bedroom apartments, of course.

So I guess after all that, it was a bit of a surprise when, about halfway through the year, I sprung that question on him.

"I mean it. You and me."

"You're joking, right?"

Awkwardness got the better of me at that point, and I walked from the kitchen to sit down on the couch as I thought of how to continue. "No...not really...I mean...I keep hearing people on campus talking about it, and I've been curious. I'm just...I haven't found anyone to date, and I don't want to just, like, hook up with some random guy at a party like seems to be the norm here. I just...I want to try it, and I know you're curious, and I trust you. Seems like something we can explore together."

He thought about it for a moment. "I don't know. We've never been like that, not even a little bit. Never kissed or flirted. Damn it, Lisa, you're...you. It would be weird."

"But would it have to be? We do a lot of stuff together, why can't that be just one more thing? Hopefully a fun thing? And then when we actually start dating people, we'll know what we're doing."

He still looked doubtful. "I dunno. I don't know if I could do that. Can we talk about something else?"

I decided to let it drop for the time being. The subject was clearly making him uncomfortable, but I hoped that now that the seed had been planted, he'd think about it on his own time. I had felt the same kind of awkwardness when I first considered asking him to be my "first", and in fact it had taken several weeks before I finally decided and got the nerve to actually ask. I had been telling the truth about my reasons; one of the friends I'd made had been fucking her boyfriend since tenth grade, and she'd occasionally talk about the various creative ways they'd find privacy to do it. Another one was supposedly living in the college dorm, but had met a guy at a party in the first week and moved in with him almost immediately. She'd go on at length and in detail about how they spent their nights. And mornings. And weekends. And in between classes. And while skipping classes. You get the picture. Anyway, it had me curious. I mean, as an 18-year-old girl in modern society, I was already curious, but it got me seriously thinking about giving it a shot. Except...no boyfriend. No one interesting had asked me out. I wasn't a party-goer either, and didn't want just a random hookup like Stephanie had. Which left me at a loss for prospects, until one of the girls saw me hanging out with Tyler between classes and asked about "that yummy guy".

So I decided to let the idea sit with him for a while. Of course, I did what I could to help it along. Our long friendship made my subtle seduction attempts somewhat easier, as it wasn't unusual for us to sit close together while watching TV, or to flit around the apartment half-dressed on occasion, so it wasn't shocking and awkward when I started doing those things more frequently. Head on his shoulder on the couch. Casual conversations in just my underwear. Stuff like that to help keep him thinking about my little proposal. But by mid-February he still hadn't said anything, so I decided to look for an opportunity to bring up the subject again.

A stormy Friday night in early March provided an opening. One of our favourite activities together during bad weather had always been sharing blanket on the couch and watching bad movies all night. Winter was best, because of the added benefit of hot chocolate. We cuddled comfortably through two embarrassingly bad bargain-bin rentals before deciding to call it a night. However, the ill-fitting 1960's-era window in my bedroom and the howling North wind which blew directly on it left my room absolutely frigid, and a sudden idea struck me.

"Can we share your room tonight? I'm going to freeze in mine."

He didn't seem to see where I was going. Maybe my prior suggestion wasn't at the front of his brain, in spite of my subtle efforts to keep it there. "Um...are you sure? That wouldn't be..."

"Oh come on, Tyler, it's not like it would be the first time we've shared a bed."

"Yeah, but when was the last time, what, 10 years ago? Things have changed a bit since then."

"When did you become such a prude? We've been cuddled up on the couch all evening...under a blanket...is it really that much different? Go check my room, you'll understand why I'm asking."

He wandered down the hall to my door, and the look on his face when he opened it showed he was convinced. He didn't say a word, just walked into my room, grabbed my pillow, and headed down to the end of the hall. I quickly got changed for bed (tonight's choice was an oversized T-shirt that nearly reached my knees...and nothing underneath) grabbed the box on condoms I'd purchased just in case the moment ever arrived, and followed him. He was already in bed by the time I got there...right in the middle of course, so I had to scoot him over one side so I could slide in beside him. I discreetly dropped the little box beside the bed and snuggled up beside him, soaking up the warmth from his bare chest, thinking only about how much nicer it would feel if it was bare skin-to-skin, but I was nervous about springing sudden nakedness on him. Instead, I propped myself up on one elbow to look him in the eye.

"So...have you thought about it?"

"Huh? About what?"

"About that thing I asked you a few weeks ago. A certain...suggestion I made."

He still seemed to have no clue. "Ummm."

Alright then, so much for subtlety. I lifted my hips slightly to slide the shirt hem out from underneath, sat up, and peeled the shirt over my head, revealing my naked torso to him for the first time. "This, stupid. Now do you remember? I want this. Tonight, if possible." To my embarrassment, my eyes were moist from frustration. I had always been insecure about my body and the few extra pounds I carried, not counting the extra "few extra" that had settled in since starting college, and a truly ugly thought suddenly occurred to me. "Do you really consider me that un-fuckable that I can crawl in to bed with you and you still don't get it?"

"No...no...I..." he stammered. At least he was clearly distracted by the first naked breasts he'd seen in person hanging just inches away. That was a start. "You didn't say anything after that first time, I thought it was just, like, a one-time offer thing, and then we were back to being, you know, us."

"Well, it wasn't a one-time thing. The offer is still there. And before you wonder, nothing else has changed. I'm not looking for domestic bliss here, I just want to try something new. See what all the fuss is about. Touching myself is one thing, I'm pretty sure the real thing is a lot different. And I honestly can't think of a better first time candidate than you. As long as you promise not to be weird about it." I pushed the blanket down off my hip despite the cool air, exposing my entire naked body to his sight, then took his hand and placed it gently on my thigh. Our eyes locked as he considered it, and when his had started gently sliding upward, along my hip to curl around my waist, I knew he'd decided, possibly without realizing it. I slid back down, resting my head on the pillow beside him, and began running my hand across his shoulder and down his back. His lips curled into a sheepish smile as I moved my face closer to his, and finally our mouths met as we shared our first kiss in nearly fifteen years of friendship.

Once the ice was broken, he got more bold, and the next few minutes were filled with giggles and awkward groping as we started exploring the parts of each other's bodies we'd never previously discovered. I ran my fingers through his chest hair, then reached down to cup my hand over his surprisingly firm butt. He rolled me onto my back to fumble at my ample boobs (the unspoken blessing of the Freshman Ten I'd gained) before sliding his hand downward, shyly skirting my most private area on the way down, and caressing my thigh and butt on the way back up. I leaned in again, kissing him more fiercely than before, and threw caution to the wind, pushing insistently downward on his boxers. They refused to come off, and it was only when he winced and grabbed my wrist than I realized what they were caught on. A quick twitch of his hand pushed the waistband past his erection, and now it was my turn to take in the naked body of my best friend.

I had seen pictures of naked men, of course, even caught the odd unintentional glimpse of Tyler during the time we'd been living together, but this was different. This was up close and personal; a real, live, cock right in front of me expressly and exclusively for me. My fingers closed around the shaft and I stroked gently, completely in the dark about how to proceed. After a wince and a twitch told me I'd done something wrong, I regretfully let go for the time being. "Show me," I said softly.

He seemed reluctant to stop his slow exploration of my own body, he nodded and rolled onto his back, where I had a clear view. Gently cupping his balls with the palm of his left hand, he made a circle around the base of the shaft with his thumb and forefinger. "Squeezing gently down here helps keep me fully hard," he said, as if thinking through for what he was doing and why for the first time, which perhaps he was. "Also keeps my nuts from flopping around and hurting themselves," he added with a grin. Clearly he was getting comfortable with the situation. He carefully pulled the foreskin back off the head of his cock, then made a fist around the shaft with his right hand. "Gently at first," he told me. "Squeeze too hard and it gets uncomfortable. Focus toward the tip, so I squeeze a bit with the top of my fist, so when I stroke, the pressure moves from here to here." He indicated one spot about an inch below the head, and another near the tip. "I don't know how circumcised guys do it, but I let the foreskin slide up and back; that way I don't actually get any friction against the skin, I just let the pressure do the work." He demonstrated a few strokes. "You want to try?"

I was still worried about hurting something, but I replaced his hand with mine, doing my best to mimic the motion he'd shown me. Twice he asked me to slow down, seeming to prefer a slow, steady stroke to the frantic jerking I'd always pictured. At his urging, I gradually increased the pace, but by the time he started lifting his hips off the bed, my wrist was getting tired. No problem, he took over again and I watched in amazement as his face contorted, his pelvis angled up higher and higher, and his hand became a blur until he finally made a weird sound in his throat and twitched his hips violently as a sudden spurt of milky goo erupted from the tip of his dick and splattered all over his chest. He continued to twitch for several seconds after the first eruption, gradually settling down and releasing his grip. His sheepish grin returned as he caught his breath. "Sorry about that," he panted at me. Not used to stopping once I get to a certain point."

I laughed at that. "That's ok. It was fun to see that. I probably couldn't have brought you off like that, even with your guidance. As long as you're good to do more tonight." I had heard that some men were "one and done" when it came to ejaculating, and was hoping desperately that the display I'd just witnessed didn't mean I'd lost out on getting my first fuck tonight.

"I don't think you have to worry about that," he assured me. "I should be hard again in a few minutes. And I once jerked off four times in one night...it gets harder to cum each time, but I can do it." He carefully wiped the mess of his chest and then looked me over again. "Your turn to show me?" I hesitated for a second, and he gave me a look of mock sternness. "And don't try to pretend you don't do it. Not only have a heard you moaning and groaning on more than one occasion - you're not as quiet as you seem to think you are - you just told me a before we started that you touch yourself but you want the real thing." His smile came back again, as open and genuine as ever. A finger of his left hand gently circled one of my nipples, and I clenched my thighs in anticipation as his hand slid lower, gently gliding across my mound. "Show me what you like, so I'm not just blundering around down there."

I laid back on the bad and took a couple long slow breaths, trying not to think about my best friend staring at me while I attempted to masturbate. My nervousness began to settle, and I slowly began to run my hands over my body. I squeezed my tits together a couple times, pulling gently on the nipples, clenching my thighs together as I felt tingles starting again in my pussy. Following Tyler's example, I started to talk through what I was doing.

"You can't just, you know, jump right in. It takes time to get things started. I'm pretty much good to go now though...anticipation has me warmed up already." I opened my legs enough to slide my hand down in between, and sure enough there was some moisture leaking out between my lower lips. I slid my palm over my mound a few times. "Gentle pressure on the outside is great. The inside is very sensitive at first; I'll be able to handle direct stimulation a bit later. I'm starting to get wet though. Check it out." I took his hand and ran his fingertips over my slit so he could feel the wetness seeping out. I winced slightly as his finger tangles in my pubic hair. I'd heard that a lot of women shaved down there, but I'd never seen the point. "When I'm ready, it almost opens up on its own; a finger just kinda slides right in between." To demonstrate my point, I guided his finger inside; my slick wetness allowed my lips to part easily to allow the intrusion. A gasp left my lips; touching myself usually took quite a bit of build up, but wow was it different when it was someone else's hand doing the work. I slid his hand away for the next lesson.

"Look here," I told him, and he leaned in closer as I spread my lips wide, exposing my innermost secrets to his gaze. "Wetting my finger here helps it glide easily up here, where all the good stuff happens." I ran two fingers up, gently flicking my clit before dipping back inside. My fingers circled the sensitive button, spreading my wetness all around, and this time my gasp became a soft moan. "Gentle is still the main idea. Too much, and it just gets irritating," I warned him. "You can get more aggressive as I get more turned on, but for now, slowly and carefully." I demonstrated the various ways he could stimulate my clit; gentle pressure below, tickling from underneath, flicking it from any direction. Side to side was doing the trick that night, and my hips twitched upward as a quick spasm ran through my body. Tyler rolled his body against me, kissing me fiercely as one hand began massaging my breasts. I moaned into his mouth, my hands moving more fiercely over my clit. I usually got myself off just by rubbing my clit, but I felt...hungrier that night. Keeping one hand busy on my engorged nub, I plunged two fingers of the other hand deep inside, letting out a groan from the sensation. I couldn't wait to have something else spreading me open and filling me up.

"Your turn," I gasped, guiding Tyler's fingers inside me. In a matter of seconds he'd picked up the proper motion, and he kept up a steady plunge and withdraw as I worked my clit furiously. My orgasm hit me with very little warning, and I yelled out loud as I lifted my hips clear of the bed, forcing his fingers as deep inside me as I could reach. I came back down to Earth to see Tyler grinning at me, but unlike the relaxed mood that seemed to take him after he came the first time, I was on fire, hungry for more. I rolled over, grabbing the box from beside the bed, and handed it to him. Well, actually, I was a bit over-eager and succeeded in smacking him in the face with it, but aside from a wince and a chuckle, it hardly broke the mood, until he realized what I'd hit him with.

"Where did these come from?" he asked.

"I bought them around the time I first made the suggestion," I admitted. "I wanted to be prepared just in case you accepted on the spot." He nodded, and got to the serious business of getting the box open. Giggles from me and frustration from him followed as we struggled to apply what seemed to be a hopelessly complex device under the circumstances. We managed to break two of them trying to put them on him, and wasted another when we realized we were trying to roll it on inside-out. Finally, he was sheathed and ready. I was more than ready to feel him inside me, and I rolled onto my back, spreading my legs as far open as I could. "Come on," I urged. "Let's do this!"

He carefully took position on top of me, and as he lined himself up, I spread my lips for him, making sure the area was as wet and slick as possible, and then guided him in. It was a tighter fit than I'd expected, and I had to stop him from plunging in hard on the first stroke. "Careful," I urged him. "Nothing that size has been in there before, let me adjust." His face was tight with anticipation, but he complied, and after a few careful short strokes, he finally sank his cock into me right to the hilt.

"Oh, yes," we gasped in unison as our bodies bumped together for the first time. We held the position, enjoying the newness of it for a minute. "So different than my hand," he confessed sheepishly. "Wasn't really sure what to expect. Had no idea it could be this warm and soft." All I could do was nod, and begin shifting my hips, sliding him slightly in and out. He got the hint, pulling back almost reluctantly before thrusting back in, and soon we'd found a nice, steady rhythm. Oh. My. God. Like Tyler, I had really had no idea what to expect, but this sudden glorious assault on my senses was certainly beyond what I could have imagined. It was like he could reach every nerve in my body from inside me, and I could hear myself getting louder and louder as he picked up the pace. I felt the familiar rush approaching, and I threw my arms around his shoulders, crushing his body against mine as I came with a vengeance. Dimly, I heard him make some sort of painful exclamation as my fingernails dug into his back and my teeth clamped down onto his neck, but he neither slowed nor stopped. My orgasm finally subsided as he continued to plow into me, grunting with the effort as his pace increased faster than I'd ever seen him move. Suddenly he froze, buried almost painfully deep inside me, whimpered slightly, and then his body convulsed. I felt a rush of warmth inside me as he filled the condom, triggering an aftershock to accompany his release. He collapsed on top of me with a groan, and I wrapped my arms and legs tightly around him to prolong the amazingly deep physical contact we were sharing. Finally, I released him and headed to the bathroom while he removed the soiled condom and cleaned himself up. He was back under the covers when I returned, and without a word we settled into a comfortable "spoons" position, where I drifted lazily on a cloud of euphoria before drifting off to sleep.

I woke up alone in the bed with the sun streaming in through the open curtains. I stretched luxuriously smiling from ear to ear at the memory of the night before, until Tyler's absence began to worry me. How was he feeling about it? Did I disappoint him? Would he be weird about it now?

I found him in the kitchen making ham and eggs, and he smiled at me as I entered the room. "Sleep well?" he asked, grinning at the cheesyness of the question.

"Fine," I said. After a nervous pause, I continued, "How are you feeling? Please don't tell me things are going to be weird now."

"That depends," he said as he dropped the plates on the table and took me in his arms. "Is it weird that I want to do that again?"