Jessie and Sue - Sex Stories

Jessie and Sue

... and finally decided to hear her out some more. “I want to tell you a little secret about me. I come across as very shy and submissive. However, in bed, I like to be the aggressor. Until last night with you, I had never been with a guy that liked dressing up in a woman’s clothes and enjoyed getting pegged.” I had to admit, she had me intrigued by her statements, although I still was very unsure where this was going. I prompted her by asking her to further explain. “Ever since I was a freshman in college, I had a secret obsession with men who were highly in touch with their feminine side. I would go to those night clubs that tended to cater to cross dressers and transgender. I made a couple of real good friends there, however nothing sexual ever came from it as they were all interested in other cross dressers. Something last night reignited my thoughts of wanting to be with a guy who enjoys the pleasures of being a woman.” She now totally had me in her grasp. I knew that this could either be a very good thing for me, or a complete disaster. I decided to ask her what her intentions were. “Well Jesse, I want to hang out with you and see what may be in store for us. I think we would have a lot of fun together.” She had me on the hook and was reeling me in. I told her I was game, and we set up a date for Friday. The rest of the week was surprisingly quiet, much to my relief. On Thursday, I went to use the restroom, and Dan happened to be in there. I was pretty gruff with my “Hi”, ...

... and Dan asked what was wrong. I decided to confront him. “Dan, quite frankly, you have flipped my life upside down. I am terrified that you, Aaron, and Zach will torment me at work or spread that video you have of me. In fact, I was thinking about quitting and getting out of this situation, especially after what happened last..” “Night when Tracy and Karen humiliated you,” Dan finished. Holy crap! He knew about that as well? Damn. Tracy was right. Nothing got past her and Dan. I really needed to get out of here. “Jesse, let me offer this. I’ll give you all of the copies of your video, and will stop tormenting you.” “OK Dan, you never get something for nothing. What do you want?” “Simple. I want for you to give me head right now.” With that, Dan whipped out his beautiful cock and pushed my head toward his crotch. I hesitantly placed my lips around the head of his perfectly shaped manhood. I started going back and forth, pausing to lick his shaft and suck on his balls occasionally. After several minutes of licking his balls, shaft, and taking him in my mouth, he finally grew impatient with me and started thrusting in and out of my mouth while holding my head in place. Dan was effectively fucking my mouth and enjoying every minute of it, as was I. Eventually, I got him to the point that he was ready for release. He loudly yelled, “Oh god Jesse! I am going to cum and cum deep into your throat so you’ll have to swallow my load!” That had to have been heard by half of the office. ...