I am a 25yo male. I have a fuck buddy from a couple years ago that I stay in touch with as friends. She is a traveling sales rep, and is always on the road.

We havent hung out in a while and we finally got together for dinner last weekend. She looked so sexy in these tight white pants, high heels with her long sexy legs up to her beautiful ass, and low cut shirt showing off her tits. We had a few drinks and we fucked, I fisted her, and she gave me an amazing massage until I fell asleep.

I woke up with her straddling my face and I eagerly started to lick her pussy and she leaned down to start sucking my cock. She stopped after getting me really hard and wanted to cuff me down to the bed. We have had kinky sex before so I was game for it. She had the cuffs already attached to the bed and had me cuffed spread eagle really quick.

She went back to grinding her pussy on my face and sucking my cock. I was soon cumming her in mouth and she squirted all over my face. She moaned and asked me if that was a great blowjob. I said of course it was...

She then got up, opened the drawer next to the bed, and pulled out a chastity cage. She gave me this sexy but evil glare and locked up my cock. I thought it was a joke.

She climbed on top of me and rubbed my locked cock against her pussy. She told me that she missed my cock and wanted to keep it for herself. I instantly lost the smile on my face and asked if she was serious.

She put the keys around her neck on a necklace and said that she will be back in town on Friday. She got up, let me up, made me get dressed and sent me on my way.

At first I thought it was kind of a hot game, it wont be too bad. I have been extremely horny all week and she just told me today that she will only unlock my cock if I cum from her fucking me with a strapon tomorrow. Im so desperate to cum I would beg for her to fuck me. I will keep you posted on what happens.

When I was in college I got hooked up with a Gentleman by a friend of mine who was a drug rep. The Gentleman was a specialist surgeon who came to visit the local hospital every other Monday when he would do cases. He had to stay in town overnight in case there was a complication, so he got a hotel room. Every other Monday, I went and stayed with him in his room. He was very generous. He always treated me nicely and respectfully. Hit fetish was having me sit on his face although we did most everything else as well. I would let him lick me silly from front to back, then we would usually finish by me riding his cock as he lay on his back. This went on for two years until his arrangement with the hospital ended.

My Gentleman was 50 years old, married and had three kids, but we never talked much about his wife. I was 20 when it started.

I came to depend on the income. It really helped a lot and I would have had much bigger student loans without it. I never considered myself a prostitute, but I now know that I was. I went on to work in pharmaceutical sales, and into sales management from there. The only person who ever knew about this was my best friend and room mate in college.

Not only do I not regret it. It was great. I would do it all over again in a heart beat.

I had a couple of sales reps from out of town today. When we were done the assholes wanted to go to Hooters. What a bunch of hicks. It was a late lunch and the place was not very busy. Our server was so stupid. She screwed up the order and the bill and the change. But she had a decent face and big tits. My company makes me pay for my own meals and when the girl saw I had a bunch of C-notes she got really friendly. She sits dawn and starts to chat and next thing she is giving me her phone number and tells me she is off in 2 hours. I went over to her place and fucked her. Half way thru this 4 or 5 yo girl runs in saying mommy, mommy and then the Hooters mom comes walking thru the bedroom door. It was so fucking funny. I stood up, my cock still hard and the little girl is saying look mommy while pointing at my dick and the mother is standing there shocked. The stupid Hooters girl is just laying there with her legs wide open like a total whore.