Colleague [20f] would grope me [18m] and made me her cuckold [real]

I’m typically just a lurker in this subreddit, but I frequent it a lot, I love these stories so much. It was when I was reading one from a while back about someone and a colleague at work that I realised one of my first cuckold/sph experiences was quite similar; not entirely eventful but enough that this post made me think people might be interested / be turned on like I am when I remember my own experiences.

So one of my early jobs I had as a teenager was in a small convenience store in the very small town I lived in. It was typically only two people who were needed to be in the store on the weekday evenings, and this was a post-college job for me, so I would almost exclusively do these shifts.

Normally I’d be paired with the same girl; she was older than me by a few years, 5”5’-ish, cute face, really nice figure, and an incredible ass - and she was flirtatious as fuck from very early on.

I was never particularly shy with girls - I’m a decent height, nice build, no inherent facial flaws (not trying to brag, just context!), quite open with my sexuality with friends etc, so I think that helped; I’d be approached in my single days and beyond, and I knew how to talk to and treat women properly (it’s almost like they’re humans); so this definitely helped me flirt back with her…

It started off with her just “jokingly” bending over in front of me and saying “oops” or she’d say silly things like “enjoying the view?”, and because I’d always respond positively it eventually turned into her brushing up against me to get past despite plenty of room, and pausing as she does so to rub her ass or her front against my cock.

Gradually it evolved further into me slapping and grabbing her ass and her with mine, then time goes on and it would be me cupping her pussy and pushing my fingers against it as she stands next to me, or her grabbing my cock and balls through my trousers - and these trousers didn’t leave much to the imagination, they were basically cheap suit pants… So you could feel each other fairly well, and my cock was pretty visible when erect… But we’d grope each other and play with each other around the store when we were bored or passing by to go somewhere, or quite frequently when I was serving a customer, she’d pretend to reach for something and just get a handful of my package - more than a dozen times she was pretending to be organising below the counter, but in reality she was groping my cock and making it hard to try and distract me from serving - thankfully the counter was fairly high so they’d have to be pretty tall to see what she was doing! I loved our dynamic tbh, it made the shift fly by, and most nights I'd have to masturbate the moment I got home...

She had a boyfriend through all of this, but didn’t seem to care and continued regardless - he came in a few times and he was so hot, certainly my type now… taller than me by a good few inches, dark skin, really handsome, really nice figure… but as she and I got familiar enough with each other to cause a HR nightmare, she would openly talk about their sex life pretty much every shift.

She would talk about how big he is, how she can’t wait to finish so she can get a good fuck from him, how she wants to be filled with his cum etc, just as dirty as she’d like. My favourite was she would jokingly say “if only I had a nice cock to suck right now” and would flash me a look - with the power of hindsight and the confidence of an adult, if it was now I would have responded with something like “well I’m not as big as ___ but you’re welcome to suck mine”, but teenagers are dumb - hints are smashing you on the head but I would respond with “not long to go and you can choke on ____’s cock”. I’m fairly certain if I had offered her mine, that she probably would have dropped to her knees…

She'd also be showing me pictures of his dick, and making comments like “I bet you’d like to suck it” and we’d joke about the two of us going to town on it together - I definitely would have, it looked fucking huge and like I say, he was super hot - the guy was hung like a horse, she would say about being sore some days and I don’t blame her. There were pictures of it erect, and then a few of him doing a mirror pose with his flaccid cock, which was still about 4x the size of my hard cock...

The one time I’ll never forget was when she showed me a video of her sucking it - we had closed up the store, and were in the back room finishing up for the night; she just said “look at this”, handed me her phone, and hugged me shyly from the side as I watched - it was from his perspective and she was taking so much of his cock down her throat. I just said “oh shit that’s so hot”, and that was basically all she needed to hear to start groping my cock with her left hand, and after a bit my ass with her right hand. I became rock hard, and she started to caress the length of my dick (which is about 2 inches hard), and she giggled - at the time I just thought it was the situation that made her laugh, but her saying “it’s made your little man so hard”, I like to think she was laughing at the size of my cock - not that it was a secret, as she’d already groped me for the longest time around the store, so she knew my cock was tiny already!

I was enjoying it so much I joked “I’ll have to watch it again to get a good look” so it played over, and she continued to stroke my dick the whole time - my arm around her shoulder, us both watching, and her gripping my little cock. She said “little (my name) better not cum, I’m not cleaning that up” - I remember I left that evening so goddamn horny, and thank the lord she sent me it, knowing full well I would masturbate to the video - and I did, I came twice that night watching it.

These sort of interactions would continue while I worked there, I would continue to listen to her talk about getting fucked good and filled with cum, I’d jokingly offer to eat it out of her, she’d say how she’d love to dress me in lingerie and get him to fuck me whilst she watched and played with her pussy - all kinds of kinky scenarios we’d talk back and forth about, the dirtier the better; we’d message each other outside of work as well, I’d tell her about the girls I’d hook up with and she’d say things like if “they want something bigger get them to message me for a threesome”; I didn’t know I was into sph at the time but holy shit did it turn me on - in hindsight, I was basically her cuck in this scenario (or like a reverse cuck..? Her bf was hung and her friend/coworker she cucks…)

I would always feed into it, she was so into making me her little toy, asking for videos of me jerking my cock and replying things like "omg so small", and she’d send me the occasional pic of her tits, a pussy pic or once a video of her rubbing her pussy. She’d call my dick cute, always refer to it as “your little man” or “little [my name]”, and tell me how much she loves big cock. This whole friendship really turned me on, despite not actually getting to do anything other than touch her through her work clothes or her touching me, or seeing her naked irl, just what she sent me.

Eventually after a while, one night I got sent two videos of her boyfriend fucking her, and I was in heaven that day - both were from his perspective, the first from behind doing doggystyle, she was moaning and her voice was quivering like crazy, she sounded so vulnerable compared to how confident she was with me - it was amazing, I could even see her asshole which was probably the only part of her I hadn’t seen yet… it’s a weird admission to be that excited but honestly her ass was her best feature, this was the ultimate milestone for our friendship.

The second video was even better, her lay on her back completely naked, bare pussy visible, and he enters his huge cock into her slowly and she moans so cutely - she starts saying “fuck me daddy” and he picks up the pace; it was about 30 seconds long total but honestly that was more than enough time for me to cum to that.

I eventually changed jobs, we fell out of touch, and a huge regret is the phone with all those videos and pictures on broke, and I didn't have cloud backup then... I still have it in a box somewhere just in case I decide to get it fixed / salvage what was on there.

I hope this was interesting enough, and apologies if it’s a bit long winded - as I said up top, I read about a colleague doing sph to someone else and it made me think “if people like that, they might enjoy what me and ____ used to get up to…”

Peace 💜