Come Monday, my ass was still sore from what Dan, Aaron, and Zach did to me, so I walked into the office as normal as possible and sat in my office. There were a couple of instances that I had to get up to walk to the finance department. I thought I was pulling this off when Tracy commented to me, “Why are you walking funny? Someone had a little too much fun on Friday?”
I paused, and tried to hide my mortified look. Did she know? I finished off my business with Tracy and walked to my office.
About a half hour later, Tracy came into my office and shut the door. “Can I help you Tracy?”
“Well, Jesse, I was wondering if you were okay.”
“What do you mean?” I replied.
“Well, you were walking funny, kind of like when someone had anal sex for the first time.”
“Excuse me?”
“I’m sorry, Jesse, I didn’t mean to be so direct. But I do know when someone had a lot of backdoor fun. So tell me all about what happened.”
Tracy was being way too direct with me. I had to find a way out of this, but how? I thought for a couple of seconds. “I was playing tennis, and…”
“Alright, Jesse. Tell me the truth,” she interrupted. “I know everything that happens in this office, you can’t hide it. I know you secretly like to cross-dress and have some fun on the side.”
“I am telling you that I was playing tennis, and…”
“Alright Jesse. Let me lay it on the line, and if I am wrong, you can do whatever you want with me. You went over to Dan’s house, Zach and Aaron were there. They made you dress up as Slave Liea, and had their way with you all night long, including videoing your performance and making you walk to your car down the block while still dressed up in your slave costume.”
My jaw and eyes betrayed me. My reaction let on that she was dead on.
“The reason why I know, is that I live in Dan’s neighborhood, and I have seen what the three of them do when they have a party. I saw you walking funny in your costume to your car on Saturday morning. It was around 8:15 Saturday morning if I remember. I know about the camera system, because Dan did this to me as well. I have to admit, he knows how to treat a woman. I’m sure he would know how to please a sissy boy as well.”
“Oh man. My career here is going to come to an end.”
“I wouldn’t say that, Jesse. It will end, but not as you expect. I think you need some womanly attention. Why don’t you come over tonight after work, and you and I can enjoy the evening.”
I quickly replied, “Alright. I’ll meet you after work.” I was actually excited for the day to be over as I was going to spend time with the one woman I wanted to have an office affair with.
Just prior to the end of the day, I was cornered by Dan and Aaron. Dan had pushed me down to his crotch level, and placed his pants covered crotch at my mouth, while Aaron went behind me, grabbed my hips and mock-thrusted into me from behind. I was quite embarrassed as Dan and Aaron were making a lot of noise and jokingly commented about the weekend slut. I was red with embarrassment and quickly slunk away hoping no one saw my humiliation happen.
The rest of Monday was uneventful, and I met Tracy at her office.
“Dan and Aaron sure did a number on you this afternoon. Don’t worry, only myself, Karen, and Sue saw what happened. I feel bad that you were humiliated at work. Let’s go out and try to forget about what happened.”
I felt re-assured as I walked out with Tracy hand in hand. We hopped into her car and drove to a local dive bar that was known for their burgers, fries, and tap beer selection. When we walked into the dive bar, Tracy got a smile on her face and yelled out, “Karen! Sue! Glad to see here! Mind if Jesse and I join you?”
“Sure!” Karen replied.
Tracy grabbed my arm and dragged me to where Karen and Sue were sitting. I was really unsure of this. It seemed too coincidental, almost like a set-up. I played along as I really wanted to see if anything would happen between me and Tracy.
The time at the dive bar was a lot of fun, there was no mention of what happened at the office. I was totally relaxed and had enjoyed the evening so far. Tracy finally told the girls that it was time to go. I got up and followed Tracy to her car, fully expecting the night to be over. Instead of going to the office to get my car, I noticed a very familiar area, and realized that we were in Dan’s neighborhood. I started to become uneasy when Tracy seemed to read my mind.
“Jesse, I’m sorry if this is making you uncomfortable, I am not ready for the evening to end quite yet. I just want to have a nightcap with you.”
We got to Tracy’s house and went inside. Tracy excused herself while I sat down on the couch in her living room. After several minutes, Tracy walked out and I really thought I was having a dream. She was wearing a sexy pink babydoll that barely covered her crotch area. I was rendered speechless by the sexiness of her body. After a couple of moments of silence, Tracy finally said, “Kitty got your tongue?”
I was still speechless because I was entranced by her pink babydoll and how it hugged her curves.
“After the weekend you had, I think you deserve the attention of a hot and sexy accountant who has been the subject of many of your office affair fantasies.”
Just then, she came up to me and gave me a kiss.
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 going to cum.
Tracy laughed as I shot my cum deep inside of her. “You really are a sissy girl that craves a nice cock in your ass. You can’t even last two minutes inside a pussy while getting fucked by a strap-on.”
I was humiliated.
Tracy got off me and then sat on my face. “Clean me up! You are a worthless sissy that can’t even please a woman.”
While Karen kept fucking me, I cleaned Tracy’s pussy of our combined juices. Finally Karen got bored with me and removed the strap-on from her waist. I felt more movement as Sue got into position with the strap on and started fucking me with it again. While Sue was fucking me, I noticed that Karen and Tracy were going at it with each other and eating themselves from one orgasm to another. It was something that I couldn’t deliver to Tracy.
As Sue kept ramming that silicone dildo in and out of my ass, I became totally lost in deep thought of what was happening. I had my office affair with the beautiful Tracy, although I was ashamed that I didn’t last with her. I realized that my highlight was letting Karen and Sue have their way with my boy pussy. Ironically, Sue rammed the dildo deep into me and I started to cum all over myself just as she was having an orgasm from the stimulation she received by ramming that dildo into my ass. I was spent.
After tonight, I knew I would never be the same. I was well on my way to being a complete sissy girl who would never be able to fully satisfy another woman again. Instead, I was the woman, and either others would satisfy me, or I would satisfy the males. When the night ended, Tracy drove me back to the office. As I exited her car, Tracy called out, “Jessie, Dan is right. You do make a great woman and you have an ass that would satisfy any man, but you are really lousy with satisfying a real woman’s needs.”
With that, she left me at the work parking lot. I got into my car, drove off to home wondering what else would be in store with me.
