Jessie and the Office Girls - Sex Stories

Jessie and the Office Girls

... bed and started to take off my shirt. I really wanted to pinch myself as I could not believe my fantasy was coming true. Tracy took off all of my clothes and commented how smooth I felt. She suddenly stopped and went into the bathroom. She returned with my slave Leia costume and heels. I was now on edge as I know for a fact they were not left at Dan’s or my car. Somehow she got into my house. I quickly started to relax once she secured the bra around my chest and helped me put on my heels. “I have always wanted to make love with a cross dresser, especially one so in touch with his femininity.” So here I was, wearing my costume with the office woman of my dreams. Tracy started stroking my cock through the slave skirt. After a couple of minutes, she shifted her body so her crotch was over my face. “Jessie, I really want to make love with a cross dresser tonight. I want you to get me ready for a night with a cross dressing sissy.” As my tongue came in contact with the outer lips of her pussy, she moaned and then said, “My, my. I know why you aren’t talking. My cat definitely got your tongue, and it feels so good!” I stuck my tongue deeper into her pussy and occasionally licked her clit. She was really starting to get into the gentle and sensual licking that I was doing to her. After a couple of minutes, I felt a slight shift of weight on the bed. I figured Tracy was just getting into what I was doing to her. That all changed when I felt two hands push my legs toward my chest. ...

... Tracy held onto my legs so they wouldn’t fall back to the bed. I felt my slave panties get pushed to the side, and something started working its way into my ass. “Tracy. Dan, Aaron, and Zach were right. This sissy’s ass is prime territory to please any guy.” I immediately recognized that voice. It was Karen. What was she doing though? I couldn’t see her as Tracy was still sitting on me and I was still enjoying her female juices. I felt more pressure on my ass, and then suddenly my sphincter gave way and something slid deep into my ass. It felt similar to a cock, but I knew it wasn’t. I felt it start to slide out until it was almost out, and then it slid back in. It was feeling really good, whatever it was. “Man this sissy’s ass sure loves to be penetrated. Tracy, look at Jessie’s cock. It is swelling from what I am doing to her.” Her. Great. Karen referred to me as a she. Of course I was a female, well, kind of. I was dressed up as one, felt like one, and was sensitive to another woman’s needs like one. Tracy got off of me and that is when I saw that Karen was wearing a strap on and was using it on me. I was starting to moan from all of the stimulation I was receiving. Tracy straddled my cock and slowly lowered herself onto me. I felt the warm and cozy feeling of her pussy surrounding my cock. Tracy slid up and down a couple of times. Between Karen fucking my ass, and Tracy’s warm pussy on my cock, the stimulation was way too much. I moaned really loud and told Tracy I was ...