My Best Friend Jenny [M/F]

Jenny plopped down on the couch beside me and put her beer down on the table. In a well practiced move she handed me my beer while I handed a controller back to her.

“What’s next?” she asked and took a sip from her beer.

I though for a second and said, “Street Fighter? Or Gears maybe?”

“Gears sounds good to me,” was her answer and she put down her beer.

Jenny was short for Jennifer and she had been my closest friend since the first year of high school. We had both been outcasts back then and found each other one day walking home from school. She had been walking in my direction and struck up conversation with me. I was not used to anyone, much less a girl, just randomly talking with me.

We quickly found that it was much easier talking to each other than anyone we knew of our own gender and we rarely spent a day apart after that. Our mothers spent a long time thinking we would be sure to marry each other one day, but they just didn’t understand the kind of friendship we had.

We were both nerds, and back then we were more interested in video games and comic books than clothes, grooming and dating. We spent our days talking about the latest issues and releases.

As the years went by, Jenny grew from being a dorky girl into the hottest woman I knew, but we still remained the same close friends, and to me she was still that dork. I’d be lying if I said I’d never fantasized about her a few times, but I had long since decided that our friendship was one of the most important things in my life, and I didn’t want to chance that by trying for something more that perhaps just lasted a few months.

We were now both 25. She was in med school and I had landed an entry-level job as a programmer at a local business. Both our schedules were tight these days, but our game nights on Fridays were sacred, and today it was my turn to host, so we were hanging out in my apartment.

She had arrived with the beers and some snacks, and I contributed with some food we’d had earlier. We were now deep in a game when she started talking.

“I need to get laid. Last guy was a month ago and I can’t even remember the last time I actually had good sex,” Jenny said matter-of-factly while tossing a grenade in one direction and then turning around to mow down a horde of zombies.

We had always been able to talk about almost everything with each other, and sex was no different. Jenny was the more adventurous of us when it came to sex, often regaling me with her escapades. I was not quite as experienced or adventurous as her, but I was just as good at sharing my tales.

“You’re telling me? I haven’t had sex in months, besides, it’s not like it would be hard for you to solve that issue,” I said.

“What do you mean?”

“Well, I mean, you’re a sexy girl. There’s a ton of dudes waiting to get their chance,” I said.

“Wait, wait, wait,” she exlaimed, putting down her controller and turning to me. “Sexy? Sexy?! I’ve never heard you call me that. Pretty perhaps, some compliments to pick me up. But never sexy. What, you want some of this?” she said with a smile and playfully shook her tits at me.

That’s how Jenny was, she took every chance she could to tease me, but that was our jargon.

I looked her up and down. Jenny had pale skin and curly red hair down to her shoulders. Her face was one of the prettiest I’d ever seen: a pair of green eyes, a thin mouth with one of the greatest smiles I’ve ever seen, and a cute nose. She was fairly small and had killer curves, with fairly big perky breasts that were perfect for her size and an amazing combination of waist, ass and hips that made guys spin around as she walked by. She was wearing a pair of a tight blue jeans and a white tank top with no bra under. She rarely wore a bra, partly because she didn’t need one and partly because she knew the effect it had on men.

Jenny was positively aware of what she had grown into.

I tried to defend myself the best I could, “Come on, it’s not like that, you know that. You’re my closest friend. But that doesn’t mean I’m blind. You cause cars to swerve off the road when you walk down the street. You’re a danger to the public and you should only be allowed near streets covered by a tarp.”

She laughed, leaned back in the sofa and picked up her controller and resumed the zombie slaying.

“Thanks, I’m just fucking with you. Anyway, I don’t think that makes it easier. You need some level of trust to let anyone in, so to speak. It’s hard to know what anyone’s intentions are. In the best case a random hookup ends in a shitty lay with someone who just wants to put his dick in the pretty girl. In the worst case it’s murder/rape. And I’m in no place to try to start an actual relationship anytime soon. I just need a good dicking,” she explained and jokingly jerked her controller towards her groin.

I pondered what she had said for a minute and replied, “Okay, I guess I can see what you mean. I’d always just assumed it was easier for a girl, but I suppose it has different challenges.”

“Yup, of course I’m not saying that there aren’t a lot of good guys out there. But they aren’t that easy to find and taking a chance on someone can lead to bad situations.”

After a few seconds of quiet, she added, “You know what? I bet that if all men were always honest with their intentions, actually wanted sex to be a pleasurable experience for everyone involved and there were no murderers or rapists, there would be so much fucking that society would grind to a halt.”

I laughed at the scenario she was describing, “Yeah, maybe, at least if everyone was as horny as you all the time.”

“I bet you that a lot of them are, they just have to be careful because of all the idiots out there.”

By now the zombie horde had overwhelmed us and our beers were empty. It was my turn to get our refills so I trotted to the kitchen and got two more. When I got back to the sofa Jenny had a sly smile. That usually meant she was going to tease me.

“So you think I’m <i>sexy</i>, huh?” she asked and reached for her beer and took a sip.

“Oh, come on, we’ve handled that already. I’m not blind, that’s it. It’s not like you don’t know it as well.”

“Does that mean you’ve fantasized about me? I mean sexually?”

I froze. I really didn’t want to go there. I was a bit ashamed of thinking of my friend that way.

She saw my hesitation, “Dude, it’s okay. I’ve had fantasies about you a few times. You’re a cute guy, you’re a good guy and you’re my best friend. It doesn’t have to be weirder than that.”

“Yeah, okay, sure, a few times,” I admitted.

“See? That wasn’t so hard, now was it. Now, what do you say we give those zombies another try?”

“Sure!” I replied, happy to escape any follow up questions, and got comfortable in the couch again. I was surprised at how quickly she had stopped teasing me. She usually kept it up for hours when she found something good to tease me about.

We spent the next bottle of beer trying to unsuccessfully stem the tide of zombies, with no conversation except for call outs and the occasional swearing.

Jenny was next in moving the conversation forward, as she usually was.

“Last guy I was with couldn’t even find my clit, and he spent almost half an hour doing his best. And when it was time for penetration he got halfway in before he came. I mean, what do you do in that situation?” she asked.

“Fuck if I know, sounds beyond help. Last girl I was with thought that blowjobs was dragging your teeth along a dick and when it was time for sex she just laid there, like a starfish, waiting for it to happen.”

“Beth?! My friend that I set you up with?!” Jenny exlaimed.

“Yeah, sorry, but she was lousy.”

“I wouldn’t have guessed that, she talks a big game. She told me that she had blown you away.”

Jenny got us two more beers from the kitchen and we started a new attempt against the undead.

Out of the blue she suddenly said, “So, do you think we could fuck each other and still be friends?”

I choked on my beer, and my player character was immediately overrun by the horde from my inaction.

“W- what?” I stammered.

“Come on dude, I’m just asking. Let’s say that we hypothetically hooked up, just to help each other out. Do you think that we would be the same afterwards?”

I was confused. What was she trying to say? Was she just toying around? Was it just hypothetical?

“I don’t know. How would that work?”

She looked at me with a serious face and said, “Let me refer back to our previous conversation. We both need to get laid, you apparently think I’m sexy and I think you’re cute, we’re close friends, we trust each other and we’ve both fantasized about each other. It seems to me pretty obvious that we could help each other out with this just as we help each other with other things. I’m just wondering if it would be weird afterwards.”

I stared at her blankly for almost a full minute. It was crazy, but the annoying thing was that she was making sense. I hadn’t gotten any in months. She was eye-blisteringly hot, and while I had discarded the idea of us as a couple, I hadn’t really thought about just sex, as friends. The longer I thought about it the more I actually believed we could have sex and keep our friendship as it was.

“Uh, yeah, I hadn’t really thought about it like that. I guess I think we could handle it. We know each other as well as anyone, and we know what our intentions would,” I finally said.

“Right, just some sex, between friends, nothing more.”

“Right,” I concurred.

“Right.”

“Right.”

We started at each other for a few seconds, unsure about where to take it from here.

I caved first and asked, “So, what now?”

“I think we should start easy, see how it feels,” she said, and casually added, “Want me to suck your dick?”

I didn’t have a response to that.

“Y- yes,” was all that I managed to say while probably looking scared to death.

“Alright, let’s do some testing, take of your pants,” she commanded while putting a pillow on the floor between my knees.

I fumbled with my belt buckle and jeans and finally got them off as she got in position between my legs.

She looked at me and said, “Hey, if you don’t want to do this it’s fine. I don’t want to jeopardize our friendship either, but I think it will be fine.”

“It’s okay, I want it too, just a bit of nerves,” I managed to say with a smile.

“Alright then, but I can’t suck your dick through your underwear, stupid.”

“Right,” I said and slid my boxers down.

She quickly grabbed my half-erect cock.

“That’s a nice cock,” she said while staring at it.

I’d never been ashamed of it in any way, it was perfectly average, but I couldn’t remember anytime anyone ever calling it nice. Her hand on my dick felt amazing as she slowly stroked it and I let out a short groan. She seemed intent on inspecting it closely before moving on and I had no complaints.

“You know, when I’ve fantasized about you I’ve tried to imagine your cock, but this is nothing like it. Not in a bad way, but it’s hard to imagine something you’ve never seen.”

Then she held it in place and slowly licked the tip while staring me in my eyes. The view was too much and I groaned louder and tipped my head back in the sofa.

She seemed to enjoy that and let her tounge play all around the tip while stroking the shaft.

“Jesus, that feels good,” I managed to utter.

Suddenly I felt her hand slide down and the warmth and smoothness of her mouth replacing it. I looked down again and saw my cock halfway into the cute mouth of my friend, and her green eyes smiling back at me. It seemed like she was loving this just as much as me.

She started sucking up and down while stroking the shaft with her hand, making sure everything was slick and lubricated.

“Oh, fuck. That’s amazing,” I moaned.

She picked up the pace and moved her hand to caress my balls. After a while she switched it around and took one of my balls in her mouth, sucking on it, and stroked my cock with her hand.

“Fuck you’re good at this,” I exclaimed and I started having trouble sitting still.

“Well thanks buddy!” she said cheerily and dove back down, engulfing my dick with her mouth once again.

I could feel myself creeping closer to the edge as she picked up the tempo, bobbing up and down faster and faster and helping along with her hands.

Suddenly she withdrew her mouth, still stroking with her hands, and said, “Fuuuck, I’m so horny. I’m sorry, I need to come. Could you give me head instead? I promise I’ll finish this afterwards, you can finish in my mouth if you want.”

I gasped for air and managed to say, “Sure, let’s switch positions.”

She finally let go of me and jumped onto the sofa and slid off her jeans in one fluid motion. She laid down along the sofa on her back, her legs slightly apart. She was wearing a pair of red thongs and they had a big dark spot around her pussy. I reached out a hand and slowly stroked her smooth skin on her leg, towards her pussy. When I got there I stroked it slowly through the fabric, feeling how wet she wad. She moaned and writhed slowly and I finally slid her underwear down and off her legs.

Her pussy was just as beautiful as she was. Perfectly shaven except for a tuft of red hair above her slit, and bright pink lips poking out contrasting with her pale skin.

I laid down on my stomach between her legs and spread them. I kissed and licked hungrily around her pussy, taking my time to cover every inch around her sex. Looking up I could see her chest heaving with her deep breaths, her amazing tits forming two mountain peaks in her top.

The smell of sex was wonderfully overwhelming and I just needed to taste her so I started licking slowly around her lips and folds, making sure no part got left out. I explored every part of her over and over again until I finally sought out her clitoris and started teasing it slowly with the tip of my tongue.

“Oh god, that feels so good, I want you to make me come,” she wimpered.

She seemed to respond much more as soon as I reached her clitoris, so I put my focus there and switched between gently sucking and flicking my tongue across it, only moving away to tease the rest of her pussy now and then.

“Oh, fuck, fuck, fuck,” she moaned.

Her breathing was now quick and shallow, and her back was arched and she bucked and writhed. I had to grab her thighs to keep my mouth planted on her sex.

Just as I was doing a quick rhythm up and down over her clitoris, she yelled, “Fuck yes, just like that, don’t stop, I’m going to come.”

I focused all I had to keep the rhythm up and to not move an inch. Suddenly, she stopped breathing and her whole body tensed up for a few seconds.

“Fuuuuuuck,” she finally screamed, her whole body quivering as she came.

As her shaking slowly faded away and her body relaxed I kept slowly licking her pussy and only stopped once it seemed like her orgasm was over.

“God damn, that was good, thank you,” she said between deep breaths after a while.

“My pleasure,” I responded with a smile. I’d always enjoyed giving pleasure, and it was always the most fun when the reaction was loud and clear.

“Let’s see if we can’t help you out now.”

I sat back up in the sofa and she got back on the pillow between my legs. My cock was still as hard as it could be and was aching for release.

She didn’t waste any time and dove down immediately, sucking and stroking as fast as she could. She only gave pause for a few seconds to say, “Please come for me.”

I was gasping for air and barely manage to utter, “Oh god, I’m close.” between breaths.

My reaction from her earlier treatment of my cock hadn’t subsided completely so her warm mouth sliding up and down my shaft was making me race towards the edge at an incredible speed.

“I’m going to come, I’m coming,” I yelled and she kept sucking as hard as she could while I felt my balls tightening and my cock beginning to pump my cum into her mouth. It felt like my whole body exploded and she kept sucking, gently, until I was done.

When it was done she stood up and grabbed her beer, took a large sip and swallowed it all. Then she sat down next to me and let out a deep breath.

I felt completely emptied. We were sitting there in the sofa, both naked from the waist down, relaxed and breathing slowly. And curiously enough it felt completely natural. Just two friends hanging out.

“So, how do you feel?” she asked and poked my lifeless body.

I came back to reality and said, “Like I just had the greatest orgasm ever.”

“Well that much was obvious, and me too by the way, but I meant about us.”

I thought for a second and said, “Well, you’re still you, and I’m still me, and we’re still the same friends. I think I feel fine.”

“Good, me too. That was great, I really needed that.”

“Yeah, me too. So, how does this work from now? If you still want to do this?” I asked.

“So, what I was thinking is that friends help friends..” she said trailing off, looking into the distance.

“Yes?”

“Well, I mean, it doesn’t have to be complicated. We keep hanging out as we do, and we fuck each other when we want to.”

“That does sound pretty simple.”

“Right, I think so too.”

My head was still spinning from the blowjob and the new arrangements was causing the spin to gain speed. It also caused my cock to harden a bit. We spent a few minutes just sitting there, breathing slowly.

“So, I feel a bit done with the gaming. Want to watch something?” I asked.

She turned on the TV and we soon agreed to a comedy movie just to have something to watch. She laid down in the sofa. I snuggled up to her, spooning her from behind. My naked semi-hard cock nuzzled between her ass cheeks.

We laid there for a while, just relaxing and watching the movie, before Jenny piped up, “So, have you been tested since Beth?”

“Yeah, as soon as we were done I got myself tested.”

“Okay, I’m tested as well, and I’m on the pill, just so you know,” she informed me in an official manner.

We continued watching the movie, my hand resting in her stomach, her amazing ass tight against my groin. Now and then she was almost imperceptibly grinding against my dick, and I was no better, doing the smallest thrusts, pushing my cock into her crack. We were both aiming for something more before the night was over and both playing it like nothing was happening.

After a while she pushed her ass back hard against me and readjusted her body a bit while stretching her legs. Like magic my dick ended up between her thighs, barely rubbing against her pussy.

We kept watching the movie and not saying anything. The almost imperceptible thrusts and grinds continued, now with my dick sliding between her thighs and against her pussy. Both of us had started breathing a bit heavier and I don’t think either of us gave a shit about the movie anymore, but it was fun to pretend like nothing was happening.

Feeling a bit bold I reached down to my cock and moved it a bit so that suddenly the tip was grinding on her opening instead. She was slick with juices and her body shivered slightly. I took aim and slowly pushed inside while we both let out a deep sigh. She was tight and warm and my brain was malfunctioning as I reached the bottom and her ass pressed against my groin.

We stayed like that for a while, me just staying inside her, her amazing pussy hugging my dick from all sides.

After a while I started to slowly fuck her from behind while we kept pretending to watch the movie. My hand slowly roaming over her body, finding its way under her top, caressing and gently squeezing her breasts, moving down between her legs to slowly massage her clitoris.

We kept it up for a while, softly moaning in unison as I slid in and out and kept caressing her body. I was so hard that my dick felt ready to explode, and she was so wet that I felt her juices running down my legs.

After a while she pulled away from me and said, “Sit up, I want to ride you.”

I sat up and took off my t-shirt that had stayed on and she tore off her top. For the first time she was standing completely nude in front of me. I drank in the sight of her. Her hips, her thin waist, her perky breasts with bright red areolas and the hungry smile that was on her lips.

She climbed up in the sofa, straddling my hips, her hands planted on my shoulders and sank down onto my cock. Slowly she rose again until I was almost fully outside of her and then slowly came back down.

“God, your pussy feels amazing,” I moaned.

Putting my hands on her hips we started to build up a rhythm, her breasts bouncing up and down with each stroke.

She threw her head back and let out a long sigh, “Fuck, I can get used to this cock.”

By now we were both hungry and in a hurry, so after a short while the rhythm had become fast, her pounding into me while I fucked her back, hard, from below.

“I’m getting close, please come with me,” she said between breaths.

I grabbed her tits with my hands and did my best to fuck her as hard as I could. The feeling was overwhelming and I had to concentrate to last until she was done.

Suddenly she tensed up and froze once again for a few seconds, her pussy spasming around my cock as I kept thrusting into her as fast as I could. She let out an incoherent scream just as I came inside her, filling her completely.

She collapsed onto me and we stayed like that for a while, my dick completely spent, slowly going soft inside her.

“I think we have a good plan,” she spoke into my ear.

“Yeah, I can get used to this,” I replied and laughed softly.

Source: reddit.com/r/eroticliterature/comments/fzk5yf/my_best_friend_jenny_mf