collection of stories you shouldn't read at work
This is a continuation of my previous story you can find on my profile! Again, this is long so feel free to skip to any of the sexy parts but if you like the slow burn and all the context, please read on! Again, I did fictionalize some of the details and some of the story just to keep it more anonymous but the sexy details and my feelings throughout are what I remember!
**BACKGROUND**
It was the night of my girlfriend at the time’s birthday party. I was working a part time retail gig after school, and had become quite flirty over time with another one of the associates.
On this night my co worker Jane asked me for a ride home, which I was happy to provide. Over the 20 minutes drive we listened to some music, chatted, and flirted some. When I pulled in front of her house we talked for a few minutes before she hopped out, thanking me for the ride. I got around the corner when I noticed that she had left her wallet on the seat.
I rounded the block, pulled out up front again and gave her a call. She came back out, got in the truck and told me to drive. She drove me to a park parking lot with a nice view of the city. She told me to park. We chatted for a few minutes before she grabbed my face and started kissing me. I kissed her back, my hands find their way to her top, pulling her tits out. Cars passed on the road behind us.
So my girlfriend (20) is a pretty modest but incredibly sexy women. Shes 5’7 with DD breasts, thick thighs, phat butt, and the most plump lips ever. She rarely ever shows too much skin and I love that about her because in the bedroom shes the complete opposite, shes kinky and loves getting used. For the longest time though I have been trying to convince her to get a heart tattoo on her ass. I find it so sexy but she wouldn’t budge. I respected this decision because at the end of the day, tattoos are permanent. This past week she has been visiting her bestfriend in another city and they went to a tattoo parlour because her friend wanted to get a tattoo on her forearm. Me knowing my girlfriend knew she wouldnt get one at all so I didnt ask any further questions. Than randomly she texts me “can you facetime quick” . So I immediately facetime her and she picks up smiling, Im looking confused at this point and she pans the phone to her butt in a thong WITH a heart tattoo on her right cheek. I nearly fainted, it was the hottest thing ive ever seen. I had to go after that but since than its the only thing i can think about and how badly i want to fuck her now.
I was in my Junior year of college and had been seeing a girl for a period of a year or so. She was my first “real” girlfriend, I guess you could say. I’ve written about how we met here before and you can find it on my profile. Well, she moved across the state to be with me and being the typical college guy I freaked out and we broke up. She shouldn’t have moved, I should’ve said something to stop her. Again. Young. Dumb. Live and learn.
But this tale takes place about 2 months after the breakup. I’ve moved into a new apartment and have an awful roommate, no furniture, not even a mattress. She has moved down the way, equally depressing circumstances. We’ve been having occasional conversations, usually very dramatic. Neither of knew how to handle the breakup well at all. We’d argue, and then we’d end up fucking, or she’d give me head, which she was so God damn good at that I couldn’t say no. But again, I refused to get back together and I stopped telling her I loved her.
A few years ago I went to a friend’s party. I was a little tipsy, so I took a car home. I felt unusually chatty & so I talked to the driver. I just wanna pause a second & say that Uber drivers tend to be chatty in most of the cities I’ve visited, & that’s not always the case here in NYC. A lot of cabbies here just want to mind their business. But anyway…
The cabbie asked about my girlfriend, & for some reason, even though I usually let random strangers assume what they want, I told him that I’m gay. He opened up & seemed a bit more interested after that, so I also told him I was trans, which is certainly another thing never bring up without purpose, but I had a certain sense about him.
I figured he’d go through the roof & I was, of course, right. He said he’d been looking for a trans guy for a long time. As he spoke it was obvious he conflated being a trans guy with being a bottom, but I was a bottom back then, & more importantly, enjoying a game I’m well practiced in, so I rolled with it.
I had just graduated High school, and was living in a apartment with a roommate. My roommate was out of town and I decide to have a party. There were somewhere around ten and sixteen people over, drinking and having a good time. One of the girls at my party (Sheryl my wife now ), I had dated in high schooI. We had banged a few times, in high school. Sheryl was at the party with her girl friends. Sherl was looking hot with her mini shirt and spaghetti strap tank top, the top fit snug on her, perfect firm “c” cup tits. I wanted to fuck her that night. I reminisced about the first time I fucked Sheryl in my truck. Sheryl is 5’8″, shoulder length brunette hair, perfect real tits, muscular legs, landing strip and razor sharp tan lines. I lasted about ten minutes of fast fucking and came in condom. She was not on the pill and did not want me shooting off in her pussy.
One of Sheryl’s girlfriend Stacey, was at the party.
During the party, Stacey and I went out side. Stacey told me that Sheryl wanted to date me again and hook up.
I came back inside to get beer. I noticed my roommates bed room door was shut and locked. Due to the volume of people at the party I did not know who was missing. I went to the kitchen to get a butter knife to pick the lock.
When I quickly pushed the door open there was my future wife, naked on her back spread wide, on the bed. One of my older brothers friends, Bruce, was getting up off of her. His face looked like a glazed donut, he was naked. He must have ate her pussy, prior to fucking her. I was super jealous. Sheryl’s pussy looked perfect. Her dark landing strip and puffy swollen pussy lips were exposed. I stared at her sweet little cum covered pussy.
This was some time ago, cuckolding was not even a thing. I wanted to kick Bruce’s ass! I was pissed and jealous. I told Sheryl and Bruce to leave, and I shut the party down. I thought I would be the one screwing her that nite.
Four months went by and Sheryl and I hooked up again. She was just a fuck to me now. I was screwing other girls too. I did hookup with a few of her friends during this time. Fucking her girl friends and other girls , during this time is what made her lust for me again.
I screwed her for a long time before, I took our relationship serious again. She was giving her self exclusively to me during this time.
We have talked about that night. She told me Bruce and her were drunk , and they did fuck and she sucked his cock in the bed room. They hooked up a few more times and then broke up. I don’t believe her, when she said they broke up because Bruce has the smallest dick she has ever sucked and she could not cum when they screwed.
I still run into Bruce around town. He is a much smaller build than me. I know the situation makes him uncomfortable. I am not going to stomp a mud hole in his ass. I can’t blame him, if I was in his shoes, I would had fucked her too.
I have been married to Sheryl now for 12 years. She keeps telling me she wants to see me fuck another girl. I keep thinking about our past, and don’t feel like it’s a good i idea. I cant help but feel if we do a three some with another girl, she will then resent me and think anything go’s, like I di
*Staring this story: Sophia, a 5’ 4” blonde of athletic build, D-Cup; Maya, a 5’7” brunette with curly hair of athletic build; both at the age of 20; Me, John, a 21-year-old guy more athletic than the average person, photographer who just got into fitness*
Last time I’ve heard from the two, they promised to hit me up for a photo session at a location I may choose for us. Since then, about a month has passed already. Just moved into a new flat after resigning my job at a big local employer to start my own business as fulltime photographer for local news and bookable photoshoots as well as event-shootings, I still have some spare days of paid time off as well as overtime. Enjoying having no responsibilities, I leave my mobile phone unattended for most of the day, only checking it once or twice a day. All of the sudden, a feeling overcomes me to check it for some messages. The notification-LED blinks in bright yellow, reserved for people I trust with my personal number who are close friends, but not family!
A few years ago I was heading to the Vegas area for work.
Like all good deviants, I put a Reddit post in the Vegas Boards, said I was looking for a local girl that wants to be stuffed and filled with cum.
A couple days went by and I didn’t hear anything…no big deal, its the internet, plenty of flakes and fakes out there.
I took my flight to Vegas, made a pass through the strip, went to my hotel and then looked at my phone messages. Sure enough I had a message from a guy telling me how he would love if I would fuck his girlfriend raw and fill her with cum.
Seemed like a crazy message, so I figured why not, and reached back to the guy.
We worked it out where his girl would drive to my hotel, right off the strip, and meet me in the lobby. We’d use made up names to introduce ourselves and If we both liked each other, we’d go upstairs, if not, then we would just go our separate ways.
Last weekend I hung out with one of my friends snd and his girlfriend. We decided to go to the bar and hang out. I dont know if it was the drinks but I swear she was all over me. Being flirty and touching me, asking me if her outfit was too slutty (which it was). She was hot btw, nice tits and an ass, I had to catch myself from doing anything stupid. As the night went on she continued when he wasent around. I kept playing it off but a part of me was thinking she was coming on too me. When we left I said good bye to them and she looks at me saying hopefully Ill see you again licking her lips. On Monday I get a surprise while working. Somehow she got my number, probably from my friends phone and started sending me pics of her. Not gonna lie she make it really hard to ignore them. We started taking and apparently shes likes black guys and thought I was cute. She keeps wanting to hang out, but im torn. I don’t want to do that to a friend, but my horny side is telling me to do it. What should I do. I have pics of her for you guys to help me decide.
It was my first year as a real professor. Not an assistant, not a temp, but my own classes with my own schedule. I’m not sure, but I may have been the youngest full-time professor at the entire university: 26 years old. Who knows? I never checked. But I’ll never forget that first semester.
During the first week of classes all I kept saying to myself is, “Don’t fuck the students. Don’t fuck the students. For fuck’s sake Avery, do not fuck the students.” It worked. For a month anyway. That’s when a student of mine, a shy, timid student of mine came to me for help. For the most part, his grades were good, low A’s and B’s until the last one. A D for dismal. He was distraught, and just couldn’t understand what happened. My office hours were always posted in my class and of course on the syllabus handed out on the very first day, but who keeps those. And, as always, an outside hours appointment is always possible. Curly, that’s what I will call him as to not giveaway his true identity, didn’t make an appointment. He knew his class was my last of the day and that my office hours were from the end of that class until 90 minutes later: 330pm to be exact.