Conjugal visit [MF] | 2016

A few years ago, I had to do five months of jail time. I was eligible to go on work release after 30 days. I had lost my previous job, and obviously couldn't do interviews from jail, so I needed some outside help. Luckily, a friend of a friend came through for me and offered me a position that I was extremely overqualified for. I didn't care that I was making way less, I just wanted to be out in the world again and not stuck in a cell for 20 hours per day.

I probably had enough work to keep me busy half of the time, so the other half of the time I was just surfing the web. They didn't send me home, I just clocked out when I was done and messed around until my shift that was provided to the officers was over.

Now I was working doing cable tv installations so I had multiple jobsites I had to be at in a given day. Because of this, I was forced to wear a GPS ankle bracelet that would always track my location. I wasn't allowed to go anywhere that wasn't already approved in advance by the State.

Fast forward to where I have about 1 month left of my sentence. It has been at least 6 months since I've had sex and I'm slowly going crazy day by day. I would consider myself a sex addict actually but explaining that would delve way more into my past. I find a website called Badoo that shows girls nearby. I strike up a conversation with some and end up talking in depth to one named Tori.

I'm 25, 5'9", 140 lbs at this time, built pretty skinny but blessed with a nice cock, 8.5" but not super thick. Tori was 18, 5'4", petite but with a really nice ass and probably D cups. Her pictures didn't show much of her besides her face but I was intrigued. I arranged to meet her on a Saturday, when I was supposedly working but in reality no one was in our office. We had a tv and a couch in the front room.

She took a cab over and we made small talk for a while. She apparently had a boyfriend and they were trying the whole long distance thing, but obviously it wasn't working very well. We made out for a while but I wasn't really comfortable escalating for a number of reasons. First, we were in the front room, so if my boss or one of the other employees decided to come in, they could unlock the door and we would have no chance to hide. Second, I wasn't supposed to have any visitors while working so if an officer decided to come check up on me, I would immediately be moved back to the regular part of jail that I hated so much. I didn't want to blow my opportunity to work and the sense of renewed purpose that I had. So, that's all we did and then she left.

Fast forward a couple of weeks - I get a message from her saying her and her bf have officially broken up and she wanted to get together. I told her Saturday was open again if she wanted to come by, but I still had the same reservations as above. When she arrived though, all that flew out the window and I immediately only started thinking with my secondary head.

She was wearing a thin black tank top and short jean shorts. I could see a very revealing bra behind her top, and my dick immediately sprang to life before I could even stop and think. She had piercing blue eyes that I will always remember. We talked for a few minutes and started watching some Ridiculousness before we made that type of eye contact where you just know shit is going to go down.

We started making out again, but this time she got on my lap and just started grinding against my dick through my jeans. I got her top and bra off and get a good first look at her boobs before I start sucking and pinching her nipples while she grinded on me. I couldn't believe how close I felt to cumming already and knew I would have to be a hero to last more than 5 minutes fucking this girl.

While I try to distract myself with other thoughts to prolong myself, she leans in and whispers to me, "What are the chances that anyone else comes in here?" I told her the odds are pretty small and went back to kissing her neck and feeling her up. She leans in again and says "Don't you want to know why I asked you that?" I obviously had not gotten the hint, but the light bulb went off. I was having such an enjoyable time just having her grind on me, on top of trying to not cum from it, that I don't even know how long that went on for but I'm sure she was getting impatient.

I pushed her off me so she was laying on the couch and I unbuttoned her shorts and pulled them off. I also took the liberty of taking off my shirt and jeans. While she was gazing at me, I moved my hand down her panties and started fingering her. She was wet but she was still damn tight. Eventually I was able to get two fingers in while she writhed around on the couch in pleasure.

I could tell she was really close to orgasm, so I stopped. She looked pissed but I smiled and started rubbing the base of my cock around her pussy and clit. She came just from that but before she had much of a chance to recover, I pushed inside.

Like I said, I was 25, so I wasn't used to fucking someone so much younger. She was so tight I could only get halfway in for the longest time. It was actually kind of uncomfortable and even when she opened up a bit more, I could tell she was enjoying it way more than I was. I came pretty quickly inside of her (she was on birth control) but she was so tight that as long as I kept thrusting, my erection was totally sustained. So much for my fear about being done in 5 minutes - well, I was, but I didn't have to stop.

We fucked for about 30 minutes, the whole time me on top of her. At that point I was getting tired and my "shift" was almost over. I asked her if she came and she said she had about 4 times so we were both good.

We met a few more times later (both before and after I was out) but we just really were too far apart in years to have much in common and so it just fizzled out. Thinking back on it, it was a pretty crazy risk - unprotected sex at my workplace, while I was technically in jail. But being tracked by GPS, it was the only place I could feasibly have sex, and no one was the wiser.

I have more if anyone is interested, I know I'm not the best descriptive writer but I do have plenty of stories.