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Female prison guard who popped my cherry.

  • Thread startertenn07
  • Start date

tenn07

New around here...
Beloved Member
Aug 11, 2006
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Several years ago when I was younger I worked as a counselor at a womens prison. I was always straight up dealing with that population and professional. However, there was a young female guard whom seemed to have a crush on me when I started work. We became friends and talked when we could, flirted, etc. We would have the usual brushes and hand touches all part of the game. I was pretty shy as she was but she also had been married to an older man and she was lacking a lot in her life.

One Saturday we were both working and like most Saturdays it was pretty slow as visitation was going on. On this day she was working the central control which is basically a very secure area that controls several gates. I decided to pass a little time and go by and visit with her. She allowed me inside and we were just having some casual conversation. I felt very comfortable because I knew no one would interupt us because the only way they could get near was if she allowed them through several gates and there were many cameras too so it was pretty cool.

We kept talking and I could see by her stares she was getting a little randy but she was still being sweet. She was so hot. She was thin, short blond hair, small breasts probably about 34B's maybe. So we were talking "shop" and searches and stuff and she asked if she could pat me down. She did not want to make a bold move but it worked out with the conversation. I said sure. She said ok turn around and put your hands up against that wall. I was not thinking a whole lot really other than she was just being silly.

She started at my ankles and slowly slide her hands up my leg grasping my thighs as she moved up. She stopped just short of hitting my balls then she moved to the other leg and started her way up. At this point I was getting a little excited. She worked her hands up my leg this time slowly making contact with my hanging balls but saying nothing. She stood and began feeling my back, chest, and waist then stopping.

I said that was fun.....is that it for a search? She said well.....not really if it were a real search it is much more through....very through but I don't think you could handle it. Oh yeah? I said. All these thoughts were racing through my mind like what was I doing....what was she going to do....was this for real. So I said I can take it go ahead. Ok she said. Turn around and face me. I turned and she was standing with her hands on her hips....strip she said. I never said anything I just looked at her thinking ok this is what I said I could do. I kicked off my shoes and began unbuttoning my shirt and removing it. All the time she stood and watched my every move.

I removed my belt and stood for a second looking at her only to get a raised eyebrow. If this is for real she said you can do it or I can do it. I removed my pants and stood their in my briefs. Turn around she said and get on the wall as before.

She came up behind me and reached around and run her hands down my chest from behind down to my cock in one smooth motion but she did not play. She stepped back and said now turn around and remove those shorts. I thought, OMG, but it was very exciting and I had gone this far. I pulled them down and stood there as she just gazed at my swelling cock. After a few moments she looked up and said walk over to that counter and lean over grabbing the counter which I did.

She walked up to the counter and pulled some exam gloves out of a container along with an industrial size tube of KY. Not a word was said by either of us now. She stepped back and gently pushed my feet apart with her boots so that I was standing quite a ways apart. She then pushed my head and shoulders down onto the counter. At this point I heard her wheel the office chair over to where I was standing and sit down behind me.

She began rubbing KY inside my ass slowly. Relax she said. It was the first words in several minutes. Slowly she pushed her finger inside me for the first time......by anyone. After a few seconds I felt like this sudden rush or feeling that felt good.....it made my cock rock back and forth. That is your prostate she said. I was so stupid I thought what? to myself.

She continued to work her fingers inside me when she said you have quite the little puddle going there. I looked down and in the floor was a pool of pre-cum and it was still streaming from my cock. OMG I thought. There is going to be a whole lot more shortly she said.

Have you ever cum this way she asked. I said no I have never had a finger up my ass either. You will cum shortly she said which I thought I am not even hard. She began applying more pressure and massaging and stretching my ass further when I heard her say OMG look at yourself......you are dumping a load everywhere. I did not know I was even cumming and it was everywhere all over the floor.

At this point she pulled her fingers out and removed the gloves and while I was bent over she finished milking my cock from behind as she sat in the chair. I felt like some bull being milked in a stall.

Then she rolled back and said a body cavity search was a complete search. As soon as you clean up your mess you can get dressed she said.

OMG, what an experience for our first time.
 

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