[M] Hooking up with my Lesbian co-worker

I was 20 when I met K. I’d taken a seasonal gig at some shitty big box store over the holidays in a pinch. After sweating through my first couple days, she’d spotted me and been more or less the only one who backed me up when I inevitably needed help. We were fast friends and she ended up introducing me to some other people she hung out with from the store, namely her girlfriend G and their other friend, A. Despite being a shamelessly horny 20 year old, finding out that K was a Lesbian instantly shut my mind off to the possibility of trying to sleep with her. I’d never knowingly met anyone who was gay to that point, but in my mind a relationship was a relationship. And seeing as I wasn’t attracted to A, we instead formed a neat little friend group.

Most days were spent slinging knickknacks and overpriced wine to housewives who were flattered when I had to ID them at my register. At the time I was your classic skinny white boy with long skater hair and a good jaw line. So every once in a while, this flattery led to a flirty “you’re sweet” followed by a touch on the arm that went on just a second longer than it probably should have. Had I been less shy, I almost certainly would have tried to parlay it into something. Instead I just basked in the attention, something K, G, and A all loved to remind me of when we hung out after work. They were all a few years older than me, all more experienced and established in the world. Usually we’d all end up at K & G’s apartment, smoke a bowl or three, watch something, or play a game. K had an old, fluffy dog I used to play with til he passed out. G & A would usually knock out early in the night, leaving K & I as the night owls. More often than not, the nights would close with K and I alone on her love seat passing a blunt back and forth while we shot the breeze til we either went to sleep or she decided to drive me home.

Over time, it evolved into cuddling and watching a movie til we both passed out. Given her sexuality and relationship status, I didn’t think anything of it when she put her head on my shoulder or asked to lay on my chest. Sometimes I’d look down at her- a shock of shoulder length box-dyed orange hair framing her white face, bow like pink lips, middle nose piercing, and light blue eyes- and think about doing more. I’d done my best not to check her out too much, but I was, at the end of the day, still a horny 20 year old man. Watching her lithe figure move through the kitchen pulled my eyes away from whatever I was doing more often than not. Her spaghetti strap top- usually green, sometimes pink- clinging to her pert bralessness. Too big sweatpants rolled down to her hips. For a petite woman, the curvature of her hips seemed impossibly accentuated. Yet even with these facts, I also didn’t want to be “that guy”. The one that came on their Lesbian friend. I liked the group of friends I had. The job sucked, and I was alway embarrassed when K would bring up the older women, but things were good. I tried to put it out of my mind.

As the season wore on and the hangouts continued, I became privy to some (really basic) lesbian experiences- namely that of the Gold Star Lesbian. Its merits were occasionally the subject of “debates” (however jokingly) in K & G’s household. K had her gold star, while G preferred to label her experiences with men as “dalliances.” She wasn’t ashamed, and she owned her prior curiosity. But she was firm that it was in the past for her. Late one night after one of these debates, I used the opportunity to interrupt our by-now routine of cuddling, smoking, and watching a movie to ask a “dumb straight person question” about K’s Gold Star. Without missing a beat, she rattled off her explanation: she’d always been attracted to women, she never felt a desire or curiosity about dating or sleeping with men. I didn’t question it. We went back to cuddling and eventually, sleep.

I woke up around 3 or 4 still stoned and a little disoriented. K and I had fallen asleep spooning and as I attempted to sit up, she asked me what was going on. I grumbled some half-asleep answer and was met with her laughter. I looked down at her-“What’s up…?” She let out another chuckle. “You’re….” She trailed off. Looking down, I realized I was hard as a rock, my cock pressed right against her ass. “Oh my god- I’m so sorry” I blurted out, frantically trying to rearrange my body position. She stopped me.
“It’s alright. You don’t have to move. I’m warm anyways.” “Are you sure?” I asked, my nerves peaking. “Yes.” She patted me on the shoulder as though trying to flag me back down into our previous sleeping position. My cock was throbbing against her. I could feel the precum leaking out, dampening my boxers, seeping through my pants. Trying to shift my body back into our previous sleeping position, my hips couldn’t stop from grazing hers. Each minor shift only seemed to radiate small rings of pleasure through my waist and up my spine. With the head of my cock becoming more sensitive by the second. If she was wearing underwear- panties, a thong, anything- I would have felt it. For what seemed like hours, I bit my lip and tried to think of anything else to get my hard on to go away. Suddenly she shifted- already asleep again. She pushed her ass into me even more. Cuddling in even tighter.

The “debates” over being a gold star lesbian seemed to happen more frequently after that. They always started as friendly conversations and would inevitably become about the integrity of being a lesbian vs. what it meant to satisfy a curiosity. Whether having that curiosity at all compromised someone’s ability to “be a lesbian” in the first place. I had no business in the arguments unless they turned (as they sometimes would) toward the differences between having sex with men and having sex with women. My limited experience had been employed for these debates all winter in service of both arguments. At best, I was the “expert” brought in for the trial since I was the only man able to speak about having sex with women. They would ask what the sex was like. How it felt to as a man. How the women responded to what I did. Often the latter point was a jumping off point for K to talk about her ability to make women cum “better than any man.” I was in no position to argue, especially given that she’d nearly done the same for me without even trying. Soon the debates became frank discussions of sex. I’d never talked with anyone about sex who wasn’t a therapist or a sex ed teacher. So the discussions doubled as a sort of crash course in how to ~actually~ please a woman. Or at least some women.

These conversations continued on with K & I, where we’d talk about the people we slept with, the best hookups, our sexual preferences. By this time, G going to sleep usually meant K would flirt with me shamelessly. At first I’d tried to stop myself- I knew what was happening wouldn’t lead anywhere good for K’s relationship. But I also knew that it was almost Christmas and I had no intention of staying on at this job after the season. I’d saved my pennies all season and was hoping to strike out on my own somewhere else once I was gone. Whatever K’s flirting meant, I decided I needed to find out. The thought of potentially being the first man K had sex with had become too intoxicating. It helped that her nightly teasing about the wine moms had started to take on a different tone. It wasn’t just making fun of me for liking the attention. Now she’d ask me which ones I thought were hot. What I thought was hot about them. What I imagined doing to them. She told me that she could tell which ones hadn’t fucked their husbands in a long time by how much they flirted with me at the register.

Occasionally one of her spaghetti straps would slip down her shoulder and she’d leave it there. I could see her pierced, taunt nipples bristling under the fabric of her top. In my mind, I abandoned all pretense of not thinking about her naked. Now I could picture her clear as day while she talked to me: her pale, slender frame, perky pierced B cups, a carefully cropped bush. Mid conversation, my mind would wander to the times I’d masturbated thinking about her. I pictured her leaning back, her pussy dripping wet, leaving strands hanging between her thighs for me to hungrily lap up with my tongue. I saw myself plunging my tongue deep inside her holes, listening as she moaned for me. Circulating my tongue between them and her soaked, throbbing clit begging for my attention. I wanted to push my cock inside her as deep as it could possibly go. I wanted to feel her stretch around a man’s cock for the very first time.

The holidays came and went. I put in my notice. K, G, and A expressed their sadness but wished me luck. We agreed to have one final hang before I moved on- a big blowout to celebrate our time together. We drank, we smoked, we laughed. It was a good night. When G & A passed out, K and I returned to our old routine. By this point, it was simply an unspoken fact that I would be hard at varying times while we cuddled. She would ever so slightly push her ass against my cock and gently, carefully grind against me. When my breathing gave away that I was close, she would stop or I’d make an excuse to get up. The deal seemed to be that as long as she didn’t actually make me cum, she could still call herself a gold star lesbian. The logic held I suppose. But given that it was my last night in town, I wanted to know if it was going to stay that way. Relationships be damned.

I was hard the moment we started spooning and true to form, she started to grind against my bulge right away. Her usual gentleness and care were on display but as I got closer and closer, I leaned in close. I wanted her to hear how much she was turning me on. The grinding grew in intensity. Her hand traveled up from her chest toward the back of my head, pulling me in toward her. A moan escaped her lips. I couldn’t help myself. “Gold star eh?”. “Shut up” she smirked. “You’ve been teasing me for months.”. “I teased you??” She shushed me- serious.

“If we do this, we have to be quiet.”
“Do what?” I asked, unable to conceal my burgeoning ego.
“Don’t be a fucking asshole.”

I apologized. She got up and looked around. The apartment was quiet. The only light was the nature doc on the TV. She turned to face me. “Take off your pants” she whispered. I did as told. I gestured toward my shirt. “Leave it on. Incase we get caught.” I nodded. My cock lightly bounced against the sheer of my boxer briefs. She watched it fascinated as she stripped off her top and sweatpants. My jaw hit the floor as I struggled to stifle a moan. She was everything I pictured and more, with a big circular tattoo decorating her left thigh. She climbed on top of me, softly gripping my cock in the palm of her hand. “It’s much different than I expected” She said. “What were you expecting?” “I dunno. Just different.” “Do you have any… y’know…” I asked. “I’m on birth control. And y’know, I’ve been in a monogamous relationship with a woman for six years so…” I nodded. I looked her in the eyes.

“Tell me you want this.”
“I want this.”

She leaned in close and kissed me. I felt all my shyness melting away as she guided the head of my cock toward her pussy. “Oh fuck.” I felt her whole body tremble as my cock slid into her with ease. She was absolutely soaked. She shifted her weight, wrapping her arms around my neck and pulling herself into me. I looked down at my crotch, now shiny and slick from her being on top of me. I could see strands of groom glimmering in the light as she began to make little movements back and forth with her hips. I placed on hand on her waist and guided the movement while the other firmly clasped her ass. I pressed myself to her, my mouth moving instinctively to her nipples. My tongue softly traced her piercings while my lips kissed and sucked. I tried to log every second in my memory.

“You feel so fucking good on my cock right now” I whispered to her. She raised her head and looked at me. Steadying herself with her hands on my shoulders. Her grinding increased in intensity, a hunger burning in her eyes. “Say it again.” “You feel so fucking good on my cock right now.” Again the intensity increased. The tension in her body building. She lowered her head again, but I could see her eyes open. Watching herself be filled up with my cock.

“Say it again”
“You feel so fucking good on my cock right now.”

I could hear her somehow getting wetter. I was sure that we were going to be caught, that G or A would wake up and demand answers. But I was too far gone. I could feel my orgasm building, my cum demanding to be released. The combination of the situation and how turned on she was, how extremely tight she was- was going to send me over the edge. “I’m gonna cum” I said, struggling to hold back my moans. This seemed to send her to another plane. She started to writhe against me furiously, leaning into me again. She’d abandoned any hope of being quiet or subtle and started to bounce her dripping went cunt up and down on top of me. “I want you to cum inside me” she whispered breathlessly. “I want you to cum inside me and tell me how good I feel.”

I was barely able to make it through her sentence. I pushed myself all the way into her, as deep as I could possibly go. Painting her insides with rope after rope of my cum. She trembled, mouth open- a mix of shock and utter delight. I kissed her nipples again, sucking and biting, somehow even more turned on than I had been previously. She lifted my head and kissed me. It was a sweet kiss that turned into something hungrier and more needy. Already my cum was seeping out of her but my hard cock never left her pussy. She continued to slowly grind herself into me, this time accompanied by the completely un-subtle sounds of her wet cunt being filled repeatedly. She didn’t care anymore. Even if they’d caught us I don’t know that we would have stopped.

We fucked like that for hours. Months worth of teasing and flirting culminating in a night spent making each other cum our brains out. Either she’d cum or I’d cum and we’d take a slight reprieve to check in before eagerly tearing into each others bodies. The gold star lesbian who demanded to be filled with cock. Go figure.

The morning arrived and she offered to drop me off at home before G & A woke up. I was exhausted, and we’d left her living room a disaster of cushions, blankets, and miserable attempts at hiding fluids. As she drove me home, I slipped my hand under her sweatpants and gently fingered her still-wet pussy. She placed her hand on my cock and ran her hand over it. I could have fucked her all day long. She dropped me at home with a kiss and a thank you. “Let me know if you’re ever in town.” She said.

We did reunite eventually, which is a story for another time. She and G eventually split, though I’m not sure of the circumstances. But I think of K fondly and often. We still talk from time to time, usually on responding to something on social media. Every once in a while I’ll see a selfie and remember those months we spent, and that one amazing evening.

DM’s open.

Source: reddit.com/r/gonewildstories/comments/104h5r2/m_hooking_up_with_my_lesbian_coworker