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Tomboy coworker

I had a career change a few years back. After I passed training I had a trainer I was traveling the state with. She was ten years older and a cute blonde with glasses. After meeting her she explained we would be spending quite a lot of time on the road and staying in hotels for the first few weeks. She was pretty upfront on things and she quickly explained that she was married. So if I had to fart while in the car she understood and she would too if I didn't mind. I said no it didn't and was curious when it would happen. On day three she was the first and said she felt like she had to break the ice and it was fine. Everyone does it. I got a little turned on and later that day I let one go. She gave me a hell yeah and high five. Nothing else happened for a bit till the second week she was asleep after shift. She started grunting and heard a muffled moan. Looking over she was still out when her hand went down between her legs. Focusing on the road her other hand grabbed her breast. Hearing another moan I got hard and looked at her. Sweating now her face was red when she let out a loud grunt and woke up. Startled I asked if she was okay. She said she was and drank some water before asking if she was doing stuff in her sleep. I said no and she said that sometimes she masturbates in her sleep and being away from her husband wasn't helping. So she apologized if she was and would try not to do it again. I said hey everyone does it so. She laughed and said if you need to I understand. Pulling over I asked are you sure? She said yeah I could go another round and it's five hours to the hotel. Watching she undid her jeans and stuck her hand down them. Undoing mine I pulled down my boxers and my cock popped out. Hearing a gasp she said sorry for looking. I said I watched her so only fair she sees me. Handing me some napkins we went at it. It wasn't long till she pulled her shirt and bra down. Seeing her ivory tits with pink nipples she pinched them and moaned hard. Shooting my load we came together. Panting she said we should get back to driving. She took my napkins and gave them a smell. She said she missed the smell of cum and put it in the trash. The next morning she explained what happened yesterday wasn't against the rules but not talked about a lot. So if it was to happen again it would be okay with both of us. I said yes. Our next time didn't happen for a bit since it was longer days and shorter drives. We had switched and had six hours to our base to restock with stuff. Half way in I got bored and asked if it was okay to jerk off. She said go ahead. Grabbing the napkins I quickly got out my cock and went to town. Getting wet my strokes filled the car. Feeling my balls getting tight I blasted out a huge load. Getting some on the dash I cleaned up before she asked for my napkins again. Handing them to her she put them open to her nose. Getting my cum on her she licked it before moaning and realized what she did. She threw it away and said that she crossed the line and wasn't going to let that happen. Before training came to the end we had one last trip together. Everything was going good when we stopped for dinner and hit the road again. She said she needed a second and asked me to pull off the road. Pulling over she said she needed some time to her self and I could join. She got her purse and pulled out a toy. Seeing it I got hard as she pulled down her leggings. Looking at her smooth wet pussy she spread her legs and put the toy against her swollen clit. Getting my cock out I started slowly jerking watching her. Opening her shirt she took off her bra and played with her tits watching me. Giggling she asked if I liked her body. Saying yes she said I had a fat cock for my age. Putting her head back she got into it. Watching her breasts and between her legs she came to orgasm. Holding mine back she came down and kept doing. Putting her legs on the dash I got the full view of her lips and tight brown ass hole. Stroking faster she again came to orgasm. Smelling her juices she said she was horny tonight and couldn't wait for her room. She admitted that she liked our time doing it together. Getting close to cumming she got up over the console and took my tip in her mouth. Blowing my load she swallowed it all. Taking my cock in her hands she pumped me a few times before cleaning my tip. Grabbing her breasts they were firm and perfect. Laughing she said let's get to the hotel.

Jul 15

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      • I, male, had a tomboy friend growing up. She could pee standing up.

      • I had a tomboy coworker once upon a time. I fucked her rotten, cumming in her every time. She never complained, just hovered over the toilet after each load I pumped into her, and tried to squeeze it all out. She was so tough.

      • So did you fuck at the hotel?

      • We did in a later trip. She came knocking and wanted to have a play together like old times. She came and wanted my dick so got to fuck her pussy and ass. Came in both and she loved it.

      • Yes, we gave in to our base animalistic desires, and we fucked. Mo condoms in sight. I hope she's on the pill.

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