Jessie's Office Interlude with Sue - Sex Stories

Jessie's Office Interlude with Sue

I could not believe what a great time I had on my first date with Sue. Her planning was impeccable. From getting caught at the department store, to my new set of lingerie and clothes, and then a feminization session at the salon. Only to wrap this up with a surprise sexual encounter with Sue, her male friend Quenten, and all whom I met at the various retailers. It was a first date that I would never forget. I still was in awe at how Sue was able to plan the entire night, and have it happen all so perfectly. It was a date though that sadly had to end. It was kind of odd how our relationship started. First, I was thoroughly humiliated by my co-worker Dan. Our sexual escapade was a total fluke as he caught me wearing a sexy Red Riding Hood costume when he wanted to celebrate a big project save. Then Dan invited Zach and Aaron over the following week and made me dress in my new Slave Leia costume. That night they made, and had passed out, those dreaded videos of me begging them to fuck and cum inside me. By now, I’m sure the majority of my co-workers knew of my secret life of dressing up as Jessie. To add to my office woes was the complete humiliation by my female co-worker Tracy. After a quick session with Tracy, she berated and humiliated me while Karen was pegging me. After they got bored with me, they went off and made love with each other. Sue was there while I was being humiliated by Tracy, but she did not partake in the shaming I received. Instead, she quietly put on a ...

... strap on and proceeded to fuck both of us to orgasm. I felt a connection with Sue, yet wasn't sure how or why. Only after we conversed at work that I found out how hot it was for both me and Sue. At first, I was totally put off by Sue’s advances as I thought she would further humiliate me at work. I was very guarded until she told me about her love of cross dressing men, and was hopeful to enter into a relationship with one. She eventually convinced me to go on that amazing first date with her. After last night, I was very thankful I took a leap of faith with her. The fact that we connected so fast was amazing. I was falling for her hard and fast. Throughout the weekend, I was praying that Sue was real, and not just another humiliating episode with a co-worker. As seemingly par for the course, it was Monday, and I was scared as hell to go to work. All I was thinking about during my morning commute was every scenario involving Sue shaming me in front of everyone at work, and a movie running in a conference room of me begging Quenten to shoot his load in me and make me pregnant. However, when I walked into the office, I got a couple of stares, but not much for teasing or shaming. But then as I neared Brad’s office, I heard Tracy and Brad’s conversation. Tracy was standing by Brad’s door as I started to walk by his office. “Well, well, Jesse. I couldn’t believe my eyes last Friday.” I stared at him and sternly asked him, “How so?” “Well, I saw Sue walking with another girl to the ...