Cherry was my coworker at a nonprofit office job. (A Part time job for me during college.) She was 39 at the time, white, long black curly hair, very curvy, very thick, sexy tho. Rosie chubby cheeks. She was married but I never met the guy. She seemed happy being married. Her personality is hard to describe, quiet but not shy, not really out going, laid back, go with the flow. She could be a bitch, usually she was nice to me, if I did something to piss her off she would just roll her eyes. I got along good with her but she was never really on my radar. Just seemed too unlikely to consider sleeping with her, me being 19.
I would be resigning soon, as I was leaving for school the next fall, and had already got a new job offer in that town. I could work until classes started up (i was only part time online college at the moment). I would be leaving, and my awesome boss Len was going to throw me a “retirement party”. Two birds one stone because the date of the party would be the 14th of February, Valentine’s day. My manager, Len is truly an awesome boss, short Joe Pesci type guy, very funny. Car Salesman personality. Always on, aggressive type A.
The other key people in the story is my best friend at work Stan and his girlfriend who also works here Brit.
So the party is right in our office. A whole floor that we rent out that is in larger office building. One of a the biggest buildings in my small town. Choclates, flowers, hearts, red everywhere.
Cherry and Brit are work buds, so the four of us hangout for most of the party. Cherry is wearing a black skirt, with a red heart pin on her left breast. Too tight of a top, cleavage showing. Drinks are flowing. Len works us hard but lets us play hard. Cherry is very nice, but usually has a dry demeanor, all business personality. Tonight she’s smiling, and laughing. Her husband is home sick! Most people brought dates but not me or her.
She touches my arm a lot. All my jokes are landing, or at least she seems to be enjoying them. Eventually Stan and Brit go mingle elsewhere.
“I’m really going to miss you” Cherry says.
I reply “really, I thought I drove you crazy”.
“Yeah right! you’re one of the only good people here… and you’re cutest one here”.
Wow, just playful flirting. IDK. I forget how the entire convo goes, but it gets sexual. Booze helps. Some key points are how she had some wild times before her husband, she misses the wild times, the limited wild times of my single life, and how she has a big black toy she likes to get wild with. At one point I make a joke about having a member probably as big as her toy (probably not, i’m thick but average length).
“Really..” she says… “No way, you need to show me”.
“Show you?” i ask… “Really, idk, here or like a picture?”.
“Do you have some on your phone?” she asks.
I say “Hahaha, no but if you want, i’ll take one”.
She replies “Oh my god, really, ok, i wanna see…. uhh, why dont you go down a floor to the other office bathrooms so no one catches you, i’ll watch that no one comes down”.
Ok, not a big deal, me using the bathroom downstairs. Someone would probably just think i’m throwing up if they saw me go down there. Lights are off on this floor. So I go into the stall, take my pants down. I haven’t taken many dick pics. I’m trying to figure out the best angle with my pants and boxers around my ankles, phone out, when I hear the bathroom door open…
(side note if you like this story, pace yourself when beating off, there’s two rounds to this)
I get a little nervous. “What are you doing in the bathroom with a hard dick?” (Girls say weird things sometimes when talking about a penis)
“Cherry?”…
“Yes, are you gonna let me in”?
I unlock the stall. She walks in, looks down at my fully erect cock, smiles. She grab a hold of it, strokes it overhand, while pulling at me to kiss her. We make out while she’s jerking me off. She then flicks her hair back and starts to get down on the ground. Now most stories or pornos the girl drops to her knees, but as I mentioned, Cherry is a bit thicker, less flexible, maybe a little older than in her dick sucking prime, so she sits kind of Indian style(hindsight, her sitting on the oilet seat would’ve made more logistical sense). With her sitting straight up, and me crouching a bit, I can still stick my dick in her mouth. And this is the softest tongue I ever felt. So soft, and warm. She is really good at this, her hands on my ass, while she softly blows me. Her skirt has risen up and I see her fleshy thighs. The hint of red panties.
I press my luck, I’m going to try to fuck her in here. I pull her up. I literally have to help her up by the arm while she stands, and my pants around my ankles. I Kiss her. Then push her out of the stall. I’m a big dude, but i’m not about to lift her on the bathroom sink, i kind of just push her in that direction. She climbs up, hops her ass on it, leans back, lifts her skirt. I pull those Valentine panties off, red thin panties, they rest around her left heel.
I see the heavens. Completely shaved. Most milf porn I was watching had bush (mid 00’s, atleast the milf stuff), but this cougar hadn’t a hair on her. Smooth. Looked tight, and fresh, small lips tucked inside. Puffy bald mound. When lining up we knock over a vase with red flowers in it. The water got on the ass of her skirt, collateral damage. I put my cock in her and fuck her hard on the sink. I could feel the cold water from the spill a couple times on my balls. I’m not going to lie, I was rev’d up, and didn’t last long, She was moaning, and holding my shoulders. I saw myself in the mirror fucking this married milf. Her black curly hair hitting the mirror. Before long i had to pullout and spray all over the sink. We kissed. She thanked me. I dont know if this was a one time thing for her or shes cheated before? She told me to go up, be quiet, and dont say anything. She would be up after.
I get back to the party. What a rush. I try to be cool, but I just completed a major fantasy of mine.
I start chatting with Len. This is the part of the party where just the hard drinkers stick around. Maybe 6-7 people left. I see Cherry sneak back in.
Len asks if I wanna have a cigarette outside, as we walk he invites Cherry “you still smoke occasionally right?’. She comes too.
We are outside winter cold. Len is lit. Drunker than me. He is a HR nightmare but everyone has fun. He tells a dirty joke about a blowjob. Then he tells me the best blowjob he has ever gotten was from Cherry, with Cherry standing right there. We all laugh, I say congrats. But #1 this tells me she has cheated before, because she was married before starting to work here.
We go in. Things get fuzzy for me. It’s my understanding, I’m openly flirting with Cherry. She likes the public attention but also, probably wants me to cool it. Brit gives us a dirty look. The story from Cherry is everyone eventually left, Len was last, in a cab, and Cherry promised to get me home.
We stay in the office, make out more, end up by the bathrooms on our floor where there’s a couch. We kiss, and makeout, and before you know it, she’s blowing me again with that silk tongue. I have her skirt up, throw her panties by the trash, she’s lying on the couch, i’m standing at side of the couch.
I tell her to get rough with me (i like to be bossed around, it comes out when drunk). She holds my nuts, firm and hard, squeezes, and tells me to eat her out. I lick her cunt sideways. She’s lying spread eagle still on the couch, skirt up, shirt still on(she never actually took her top off), shaved bald milf wet pussy, juicy and creamy, i’m on the side of the couch, licking her box, my testicles in her palm. I love this taste, pure sex.
I get a naughty idea. I start licking her ass while rubbing her clit, then rub my index finger on her butthole, i spit and work my finger in to the first knuckle. She winces but doesnt stop me, then…ok i know this is bad, not sanitary, but I was drunk and she didnt stop me: I go back in forth from fingering her pussy, lubricating my fingers with her pussy juices, and inserting my fingers in her ass. Ass to pussy to ass to pussy to ass. I get my index finger in all the way. I finger her ass in and out, it’s like a wet pussy now, spit and pussy juice, while I lick her clit and lips. All while she’s holding my nuts FIRMLY, and or stroking my shaft. I finger her ass hard a few times and she jumps. She squeezes when she jumps. I like it rough tho. Cherry says she’s never done that, no ones ever fingered her like that. (sorry i dont fuck her ass, fingers is one thing without proper lube).
We kiss some more. Then I mount her. I fuck her again, no condom. I rail her out on the company break room couch by the vending machines and rest rooms. I don’t think my dick got bigger, maybe harder, but she was pushing her head back with every thrust like I was doing damage. I stop, stay inside her, slowly in and out while on my knees, about an inch in and out. Then i take my hand down to her ass, spread her fat cheeks, and finger her ass again. My finger goes in easier now, she’s loose and lubed, but this angle it’s tough to keep fucking her. I do this a few more thrusts, stick my finger completely up her butt, she jumps again. I pull my finger out then lay on her, and fuck her hard full force again. I am eventually close and pull out, and jerk myself off to finish, erupting a few more ropes from round 2, cum on the couch.
We sit, panting, catch our breath. I get my clothes on, kiss her, she pulls her skirt down, fixes her hair, i hand her her panties, she puts them on, then goes to the bathroom.
While i’m getting dressed, I hear the water running, and what I assume her looking at herself in the mirror and i hear “What the fuck am I doing, fuck, damn it, you idiot” and water splash. “Shit, fuck”. Then she comes out like she saw a ghost, reality sinking in. She makes me swear up and down not to tell. I won’t (other than 10ish year later on reddit), i’m cool. She drives me home drunk. I don’t think I even washed my hands.
The aftermath:
Here’s the kicker… there’s a camera in the hallway that picks up part of the couch. Brit reviewed the tapes. She couldn’t see anything good, just two bodies fumbling around. She gave Cherry major shit, erased the tape so she could keep her job but threatened to tell her husband. She encouraged Cherry to tell him first. Brit’s old school, that’s why I assume she’s a faithful wife to Stan. However, Cherry talked her down. IDK how much Brit could see, but Cherry went with the story that I was just really drunk and we made out and did hand stuff. It worked, but things were awkward for them.
Cherry also kept contacting me to stick to the story if it comes up with Stan/Brit and not say a word to anyone. She made me promise like 5 times over two weeks. It got annoying and kind of rude. However, during those exchanges she did mention how it was obvious I liked a dominant woman, she liked it too, wanted to do it again sometime (never did), I was one of only two guys she’s been with that has “hammer” like dickhead which is her favorite, and no one has ever fingered her booty before.
Years later i live back here after college, buddies with Stan. I was in his wedding to Brit. Cherry was there. We’ve seen eachother at bars and like gender reveal parties. Everything’s groooooovy. But every 14th of February i’m reminded of what went down that drunken cold winter night…
So if you read my previous story, I peaked at 19… two milfs, then the rest of my experiences are dating/marriage sex stories, boring, vanilla.
Happy Valentine’s day!
*edit spelling
Source: reddit.com/r/gonewildstories/comments/f3spag/i_hook_up_with_a_thiccc_married_milf_at_an_office
Great story. Cherry sounds hot AF.