I Let My Boss Try My Pussy

He was in his 50s, very lean build. Abrasive personality but really sweet. I didn’t expect it. He had an incredibly soft touch. He came up behind me and touched my lower back while passing through, just to announce his presence behind me. We were discussing politics when trans people came up. I accidentally slipped out a “we”, which made him ask if I was trans. He had been incredibly accepting about another coworker, so I decided to confide that I was. He congratulated me on how well I passed. A few days later we’re talking about crude things, women and sex. He confesses he’s experimented with men, but was turned off by the mess and prep. I was keeping watch on levels and he got closer, passing behind me and touching my lower back again, but he didn’t continue to pass and kept his hand there. He continued talking about his experience, and I confessed my own. His hand traveled down to my ass and he grabbed it. I was shocked but he was a bit of a work crush so I allowed it. He brought his hand back up to my shoulder and asked I wanted to try something again, I smiled and told him it would be less mess and prep. He called over two workers from the other side of the rig to keep watch on levels while he “taught me how to keep records” in his office.

Immediately we close the door and he starts kissing me and works his way down my neck. He grabs and squeezes my ass, complimenting me. I’m rather small and didn’t expect him to pick me up but he lifted me up and threw me onto his desk. Be both anxiously worked off my pants and he unbuckled his belt and worked out his cock. I pushed him and fell to my knees on the floor and took him inside me mouth. A little above average. I loved feeling him throbbing in my mouth. I crawled back on the desk and spread my legs. He took a good look before inserting himself. I can’t say I didn’t expect him to fuck me so rough, and I can’t say I didn’t enjoy it. He definitely is one of the people who have made me cum the most. I was digging my nails into his back and begging him not to stop. Finally he came inside me. I would have preferred him not to but the chances of me getting knocked up were low anyways.

We both put our pants on and went back to the rig. He kept looking at me slyly knowing that his cum was dripping out of me as we worked. That was our only hook up but damn if it wasn’t good.