My first ever story here, entirely fictional but based on real (though exaggerated) people and a very vivid series of dreams that I’ve had…
All characters are 18+
—
*boop beep* The discord notification jolted me out of my work trance. A smile crept onto my face when I saw the DM from Jen. “Heyy, how’s your day going?”
I met Jen, her boyfriend Eric, and others though work a few years ago. I was welcomed into the existing friend group and we’d all regularly hang out. I was closest with Eric, but became closer with Jen when the three of us and my girlfriend Ashley started playing online computer games together. Eric wasn’t on too often though. Jen and I got really into the game so we’d message about it a lot. Conversations quickly became more personal and eventually bordering on inappropriate, but we were just joking around… mostly.
My heart started beating faster as I glanced over to Ashley working on her computer at the other side of the living room. I type my reply, “Eh, the usual. Boring work and frustrating personal life. You?”
“Still not having sex?” she was quick to reply.
“Nope, not lately. Even on the rare occasion that we do, I’d honestly rather just jerk off anyway”. After an unstable, dangerous relationship I moved in with an old friend, Ashley. Everybody always wondered why we weren’t dating. We got along and had a strong connection, but she just wasn’t my type. She was sheltered, and didn’t really like to do much. Sure she was cute, but there wasn’t a real sexual attraction. Ashley was a very short Italian brunette girl with small chest and a tiny peach of an ass. The kind of girl who could get away with not wearing a bra, and admitted it would be more comfortable, but still refused to go without.
She was objectively attractive, but I think her “plain Jane” personality was the real buzz kill. She had never been with anybody, and you could just tell she’d be awful in bed. Alas, her emotional stability (dull as it may have been) was incredibly comforting and appealing after what I had previously been through. So we eventually got together.
“Yeah, I know the feeling…” she admitted. I always thought of Jen and Eric as an odd pair. He was tall, but very overweight, conservative, and could generally be a dick. Not an unattractive guy, but definitely not the young and fit soccer player he once was. As could be imagined, his physical condition made sex difficult and unsatisfying. To make it worse, his conservative background made him reluctant in the bedroom.
His 6 year younger counterpart, the 28 year old Jen stood in stark contrast. Barely 5 feet tall, her mesmerizing blue/green eyes jumped out against her pale skin and freckles. Her long red hair draped over her large chest which complimented her thick thighs and soft, squeezable ass. She was a nerd, through and through, and lacked any noticeable confidence. She never really got “dolled up” or showed off her assets, but they were difficult to hide and even harder to ignore.
Their 10 year relationship had been on a decline, emotionally and physically, so we bonded over our mutually boring relationships and awful sex life.
“Are you still thinking about breaking up with Eric?”
“No… yes… I don’t know, it’s tough like we’ve been together so long but I’ve gotten myself together so much recently and he’s let himself go so much we’re not even the same people anymore… I had wanted to marry him but I don’t think I can see myself living this life forever. We’ve talked so much… he just won’t put in the effort.”
“I’m sorry. You guys always seemed like the couple that was totally solid.”
“We were… but not for a while…”
“I think it’s worth holding on to, if you can” I lied. All I could think about was getting her naked on her back and watching her boobs bounce while I gave her exactly what she’s been missing in her relationship.
“I don’t think there’s anything to hold on to. I just want… something else? Idk” She always used text slang when she was nervous, but her reply admittedly made me a little happy.
“Heh, like what? I mean, I do too…” I asked, feeling myself get nervous now. Was she hinting at what I thought? We’ve never said anything out loud, but it always seemed like she was feeling what I was feeling…
*Jen is offline*
“Fuck. I shouldn’t have said that… I hope she’s not mad or grossed out or anything” I silently panicked.
*bzz bzz* My phone lit up with a Snapchat notification.
“Heyy, figured this would be better to continue on snap”
“Why’s that?” I was starting to get excited, but still quite nervous.
“So we don’t leave a record of this… I just… idk I’ve been so done with this relationship for a while and like I’ve gotten to know you over the years and especially the past few months and I just… I have a crush on you ok idk I know it sounds dumb and childish but idk what else to call it I just can’t stop thinking about you and just keep thinking like what if we got together”
I was speechless. Suddenly it was all laid out through her nervous rambling. I wasn’t just imagining things, and it wasn’t just one-sided.
“Honestly, me too. We’ve gotten so close lately and I’ve always thought you were really fun and cool and honestly very attractive. I’ve definitely thought about it, you were just always with Eric and didn’t want to mess any of that up.”
“Really?? Oh god I was so nervous… and you’re with Ashley now”
“Sigh, yeah… we’re both kinda stuck in bad situations. If only things were different”
“Maybe we can hang out some time, just the two of us? And like just hang out and talk lol it doesn’t have to be anything bad. But just see how it is. I could use some advice about Eric anyway..”
“Yeah, of course!. Ashley will be at work tomorrow, but I’m still working from home with the covid restrictions. Come by and I’ll make us some coffee. We’ll commiserate over our lives haha” I don’t know who we were trying to fool…
—-
*ding dong* The doorbell rang and I had a moment of panic. My eyes widened, palms got sweaty, and cock started to stiffen. “Relax” I told myself. “It’s just coffee with a friend.”
I opened the door and my eyes immediately went to Jen’s chest. She was wearing a spaghetti strap tank top that was struggling to contain her breasts, which were framed on either side by a jacket that couldn’t have been zipped up if she tried. Her red hair was extra curly, glowing like fire in the sunlight. I snapped myself back to reality and welcomed her in. As she walked toward the kitchen table I was again entranced by her ass bouncing in her loose capri pants. She spun around and sat in the chair, flinging her bag onto the table. Her breasts continued to bounce for a few seconds after sitting, and I started to imagine that view without the clothing.
“Coffee?” I asked, hoping the slight nervous crack in my voice wouldn’t betray my thoughts.
“Yes, please.” Her words came out on a breath of frustration. I quickly made two cups in the Keurig, and upon returning was delighted to see she had taken off her jacket. My eyes traced her curves as I caught myself biting my lip. She had a way of holding herself… relaxed and chill, but sexier than she knows. We sat at the table and talked for a time. At first it was awkward small talk with our recent admissions ringing loudly in our heads. We eventually relaxed and were back to normal, talking about life, our computer games, our relationships… all with the usual flirtatious undertones.
I stood and picked up our empty mugs, unnecessarily leaning over the table to look down at her chest and not-so-subtly moving the growing bulge into her line of sight. She quickly averted her eyes, while a touch of red spread through her cheeks. I walked away toward the sink with a smirk, wondering if she was still watching me and what she was thinking. As I started to walk back, she moved to the couch and sat with her head in her hands. I sat next to her, closer than normal but kept a respectful distance.
“What’s wrong?” I asked with a genuine concern.
“You know what.” she shot back.
“Maybe, but I want to hear you say it”. We danced around the subject, the sexual tension rising as we both knew what we wanted but didn’t want to admit. We struggled to find any words to say to each other as we both knew there was nothing more to be spoken, and needed our bodies to do the talking. We were each clearly waiting for the other to make the first move. We sat in silence for a very long few seconds, until Jen got tired of waiting.
“Fuck it.” She tossed out the words along with her inhibitions and before either of us had time to think, she jumped onto my lap, grabbed my face, and unleashed her fiery passion with an intense kiss. I immediately kissed her back, as we began to ravage each other’s body.
She ran her hands around the back of my head toward the top to grab my hair and pulled my head away to look me in the eyes. I gasped from the sudden rush of painful pleasure that ran from my head down my spine ending with a twitch in my cock, pressing up into her as she straddled me. I looked up at her with my mouth hanging open. She stared right into my soul with a burning intensity, her open mouth forming a grin as she felt the effects that her rough play had on me. Still gripping my hair, she pulled me into her, our mouths and tongues in combat with each other. My hands ran up her leg stopping to appreciate her thighs before landing on her big round ass, giving a firm squeeze. She let out a moan as she moved her hands down my face and onto my chest. She pushed off of me and knelt on the couch grabbing at my cock over my shorts. She roughly grabbed it and made a happy groaning noise, giving a few strokes before pulling it out. I happily helped pull my shorts down to open my legs slightly.
Without hesitating, she dropped down and took me in her mouth. I grabbed all her loose hair and held with a tight grip onto the back of her head. I pulled just enough to make her moan, but still let her control her movement. My other hand found it’s way under her body to feel her breasts, hanging their full weight against her straining clothing. She sucked and spit on me, getting nice and wet, then popped it out of her mouth and moved down to my balls. She began licking, kissing, and sucking on them while she stroked me just the way I like it. It was as though she read my mind and gave me exactly what I wanted. I showed my approval by pulling her head into me, which prompted her to just open her mouth and rub her face and tongue all over.
“Oohhhh” The breath escaped my mouth as I moved my hand down to rub and smack her ass.
An exhilarated “Ooh!” popped out of her mouth. She licked long and slow from my balls, up my shaft, to my head, swirled her tongue around it for a bit and then, without warning, plunged down as deep as she could, choking and gagging herself while her hand massaged by balls. I seized the opportunity and took control. With her hair wrapped around my hand, I started forcing her head up and down while I thrusted, shoving myself as deep down her throat as she could take. She had to use both hands to stabilize herself for a proper rough face fucking. I could tell she hit her limit and released my grip so she could come up for air, red faced with saliva dripping down her chin. She put both hands to work while she caught her breath. Long strokes squeezing tighter as she moved up over my head with a twisting motion while her other gentle, but firm, hand cupped and rubbed my balls.
“Nice and rough.. I like that” she winked at me as my hands lifted up her shirt. She released her grip so I could pull her shirt over her head and unclasp her bra. I ran my hands over her shoulders and down her arms, guiding the straps down with me. She brought her arms together as the her bra came off and I got my first glimpse. They were better than I imagined. Her breasts weren’t “saggy”, but they had weight to them and hung in a perfect natural way. They were soft with pale areolas and light pink nipples.
She cupped her breasts and gave her nipples a pinch before leaning in and shoving them in my face.
“Yeah this is what you want, isn’t it” she said with a commanding tone. Although phrased like a question, it was definitely a statement. And she was correct. She pulled my head into her chest, saying “Yeah, that’s it, you like them, don’t you.”
“Mmmhmm” I mumbled back, with my mouth full of boob.
“Ahh” she said as I licked, and nibbled on one while my hand explored the other,
She reached down and began stroking me again, and in a teasing tone, said “I don’t know how far you want to take this…”.
“Right into the bedroom” I replied.
She giggled, but was uneasy about that, saying “I’m not sure you want to do that”. The reality of the situation set in. We had already crossed the line, and there was no going back. Not only in terms of our friendship, but what we had done to our respective relationships. But that was the farthest thing from her mind.
“Well” she confessed “I meant when I said I didn’t plan on anything like this… I have my period. I mean it’s almost done and not heavy but still. So I can just finish sucking you off if you want.” She said the last part with an evil grin.
“That would be amazing, but how about the shower?” I countered.
Her eyes lit up and she jumped off the couch, nearly skipping to the bathroom. I smiled as I got up to follow, taking off my clothes along the way. She was naked by the time I got to her, sitting on the edge of the counter with one hand pinching her nipple and the other gently rubbing her clit in anticipation. I leaned over to turn the water on and nearly fell over as I got a nice hard slap on the ass.
“hehe, sorry” she smirked, raising her eyebrows.
“Don’t worry, I’ll pay you back” I smiled as I stepped into the shower. She followed and as soon as the curtain was closed, I immediately pinned her to the wall, holding her by the wrists and burying my face in her neck. I teased between her legs, rubbing myself against her lip while I bit her neck. I licked up to her ear, nibbled on her earlobe and said “It’s just too bad I can’t reciprocate with my tongue… I’d love to taste you”.
She buckled at the knees letting out a moan and whispered “Next time, you better.”
I let out a quiet laugh. “Yes ma’am” I agreed, as I kissed back down her neck, over her collar bone with gentle bites, and down her chest to suck on her nipples again.
“So.. how is this going to work?” She asked genuinely. She admitted she had never had sex in the shower before. “Eric is too… we can’t… I usually have to be on top in bed…”
Intrigued by her ability to be so kinky and yet so naive all at once, I instructed her to turn around. I put m arms around her from behind, rubbing my cock against her ass while feeling her breasts. “This will be fun” I whispered as my hand trails down to tease her clit. Her breathing got heavier and gentle moans slipped out each time she exhaled. “Bend over” I commanded.
She obeyed, bending at the waist and bracing both hands against the shower wall. I rubbed my cock against her entrance, teasing her while I replaced the shower water on my cock with her eager juices.
“Fuck me” she begged. And I obliged. I guided my head into her and then grabbed her by the hips, and slowly pushed myself inside. Slow, small thrust to ease her into it and coat my cock with her natural lubrication. Once sufficient, I pushed all the way into her while pulling her hips toward me. “Fuuuuuuck” she exhaled in a moan. I slowly retreat, and just as I’m about to fall out of her pushed myself back in, just as deep, nice and slow. As I built up speed, her moans turned to small yelps with each thrust. I moved my hands up and grabbed her breasts as I continued to get more and more aggressive with my hips. I pinched her nipples hard and she yelled out “Yes! Be rough with me! Harder!”. I gripped both breasts hard and used them as handles to pull her into me with each thrust. “Nnghhh fuck yes keep going!” she cried out. “Fuck my pussy!”
“Yeah, you like it rough you bad girl”
“Yeeessss”
“Mmmm take it” I release one of her breasts and slap her ass, leaving a slight red mark. Her moans tell me she liked it, so I slap the other cheek. After a few thrusts I slap each again before returning my grip to her chest and powering through all my energy to pound her as hard as I can.
“Fuuuuck I’m cumming” she moans “Don’t stop, don’t stop, don’t stop”.
I made every effort to maintain exactly what I’m doing for her, while trying not to slip. “I’m going to be pretty close behind you thanks to this tight wet pussy of yours”.
“Oooohhhh fuuuuuck!” She screamed and nearly dropping to the floor, knees shaking. I slow down, guiding her through the orgasm, catching my breath as the hot steam builds up around us.
“Oooh I’m so close” I said, and she spun around, got to her knees.
“Yeaaahhh cum for me” She hissed with a hungry look in her eye. She grabbed my cock and pointed it towards her face while lightly pulling on my balls. “That’s it, good boy” she said and opened her mouth wide, sticking out her tongue.
“Mmm” I moaned as she begged for my cum.
I moaned loudly as I began to shoot ropes out onto her face and chest. She squealed in delight, content with her reward. Swallowing what landed in her mouth, she finished sucking out what I had left and licked me clean.
“That was incredible” I uttered as I helped her stand up.
“I’ve never been fucked like that before…” she said, still out of breath. “I really liked it.”
We washed up and got dressed, laughing and kissing along the way. Needing to get back to work, I saw her out with a kiss. I stood watching her ass bounce down the sidewalk, wet hair glistening in the sun, wondering “What have I just gotten myself into…”
Source: reddit.com/r/eroticliterature/comments/vt2437/crossing_the_line_part_1_m29f28
!updateme
Subscribeme