I walked into the office a quickly closed the door. My mind just wasn’t into work, nor did I want to see or talk to anyone. All I wanted to do was work my eight hours in solitude, go home, and maybe start looking for a new job. While working on a proposal for a new project, I got lost in thoughts of Tracy wearing her hot pink babydoll. I wasn’t convinced that it was her that I was fantasizing about, but it was me wanting to wear her babydoll so I could feel like a hot sexy woman.
My thoughts were suddenly interrupted by a knock on my office door. I kept ignoring the knocking, but whoever was doing it was very persistent. I finally gave in, walked to the door, and opened it. There stood Sue.
I did a complete double take. Sue normally wears very plain clothes which also hide her figure. On top of that, she rarely wears heels that are higher than two inches. But today was different. She was wearing a red form fitting business suit that accentuated her breasts, waist, and hips. She had on a matching skirt that went down to her mid-thigh, and her legs were encased in a near opaque set of black pantyhose. What really struck me though were her strappy red high heels that had straps around her toes, mid foot, and finally ended with a cute red bow just above her ankles. Not only did those heels look cute on her, but they were a set of five inch heels.
I just stared at her as she walked by me and sat down in my guest chair. After several seconds, I finally shut the door and sat back down in my office chair. Sue leaned over my desk a little, which meant I had a good view of her cleavage.
“Jesse, I need to talk to you about last night.”
Once I heard that, I blurted out, “Look Sue. I was humiliated. I really don’t want to talk to you or anyone else about this. Please leave my office.”
Sue stared at me and then started up again, “No. You are going to hear what I have to say. I really enjoyed last night and felt really bad that Tracy treated you like garbage. You deserve better treatment than what she did to you.”
“Listen Sue, I don’t need anyone’s sympathy.”
“This is not sympathy, Jesse. This is me telling you that you deserve to be treated better than what you were treated last light. I want to make things right between you and me.”
Here it is, another person in the office, looking to set me up, humiliate me, get more laughs, and totally crush any remaining confidence that I still have. I thought about her statement for a couple of seconds 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. Just as promised, Dan shot his first load to the back of my throat, so all I could do was swallow. Several more spurts went into my mouth so I could actually savor his salty yet slightly sweet cum. It tasted really good and I was slightly saddened when I had to swallow what was left in my mouth. Once I cleaned him up, he zipped up his pants and left the restroom. After cleaning my hands and face I left as well. I didn’t see anyone looking toward me so I assumed that I was in the clear.
Friday came, and I was getting excited to meet up with Sue.
Jesse,
As promised, you will have all the copies of the video I made of your performance. There are 12 copies for you to pick up. The only issue is that they are not all at my desk. Happy Hunting!
Dan
I walked out of my office and then toward Dan’s. On the way there, I was stopped by Scott. He handed me a DVD case that had a picture of me in a compromised position with the title “Slave Jessie and her Three Cocks”.
As I grabbed the video while avoiding eye contact, Scott said to me, “Damn Jessie, you are one hot sissy. I couldn’t help but wish that it was me having fun with you in that video. One day.” He winked at me and rubbed my ass as I turned and walked away.
This scene was repeated many times on my walk over to Dan’s office. The word was out throughout the office about my exploits with Dan, Aaron, and Zach. When I finally got to Dan’s office, I saw Tracy there as well. Both of them were laughing at my humiliation. Dan handed me two copies, which made a total of twelve copies.
As I was walking out of his office, Dan commented to me, “After I finished editing that video, I realized how hot it was, so I couldn’t help myself but to share it with my closest co-workers. I know you understand. Don’t forget, I told you that you owed me big time for helping bail you out of that situation three weeks ago. I guess payback was a bitch for you.”
Dan and Tracy were laughing hysterically at me.
I left and walked back to my office. Now, I really didn’t even want to meet up with Sue. I just wanted out of the office and quit my job. However, Sue came in with a big smile on her face, ran over, and gave me a big hug.
“Jesse! I am so looking forward to this evening! Meet me at my cubicle at five o’clock and we’ll go from there. Don’t worry about getting ready ahead of time!” She winked at me and left.
Something about Sue invigorated me and made me want to stay at the office. Five o’clock finally came, and I walked over to Sue’s cubicle. She saw me and an immediate smile came across her face. “Let’s get out of here, Jesse!”
She grabbed my hand and dragged me to her car. I got into the passenger seat and off we went. She drove to the local shopping mall and parked the car. I asked what we were doing at the shopping mall, and all she did was smile, grab my hand, and walk into one of the anchor stores. Once we got in there she led me to the lingerie area and started looking at matching bra and panty sets. I thought this was really odd for our first date, but I went along with what she wanted to do.
Sue settled on a sexy hot pink satin bra and panty set. A look of approval came over her face, and she walked toward a changing room. I followed her and stopped at the entrance. She looked back and forth and saw that the clerk had turned to help another customer. Sue then grabbed my hand and said, “Come on!”
I followed her into one of the larger changing rooms.
Sue started taking her clothes off in front of me and I just stared at her beautiful form. Earlier this week, I didn’t really notice how attractive she was when she was sliding that dildo in and out of me. I had been too absorbed in the rejection and humiliation from Tracy. But now here was Sue, totally naked in front of me, and I was learning that I was really attracted to her. She put on the hot pink satin bra and panties.
Sue finally interrupted my thoughts, “Jesse, what do you think?”
“You are absolutely beautiful, Sue.”
“Well, what are you waiting for?”
“What do you mean?” I replied.
Sue displayed the same set of panties and bra, only slightly larger than what she had on. “Come on Jesse, I think you know. Put these on and model them for me.”
As I took off my clothes, we heard the store clerk walk to our changing room. “Is there anything I can assist you with?”
Sue calmly stated, “No, we’re good.”
I looked at so funny and mouthed, “We’re?”
The clerk started to walk away and said, “Let me know if there is anything you need.”
Sue giggled and told me to put on the bra and panties. I did as she asked and Sue loudly told me how pretty I looked wearing the lingerie. She started rubbing my crotch and I was getting harder than I ever had in my life.
“You sure are a sexy looking girl, Jesse. You will even look more hot and sexy once I am done with you.”
My cock grew to the point that the head was now visible. Sue seductively looked at me with her beautiful green eyes, licked her lips, and moaned a little. “I think I need to take a taste of this wonderful girl clitty.”
Sue knelt down and slowly licked my shaft. A drop of pre-cum came out of the tip. Sue licked it up and moaned. Finally she started giving me a nice sensual blow job. After a couple of minutes, I started moaning. I guess I was moaning louder than I thought as the clerk came back.
“Are you alright, Miss?”
“Yes ma’am! The fabric is really soft. I’ve never felt anything so good on my body.”
“Okay, Miss.”
After a minute, Sue replied, “Damn Jesse, you are loud. Maybe we need to do something a little different. Sue grabbed my head and forced it to her crotch. “You can pleasure me for a while, I won’t be as loud.”
I started licking the folds of her womanhood through the pink satin panties. Sue then moved the panties to the side so my tongue could come in contact with her labia. “Mmmm, yeah Jesse. Keep doing that, it feels so good.”
I kept licking her folds and occasionally licked her clit. I was going back and forth between sticking my tongue inside of her and tonguing her clit. Sue was more quiet than I was, but soon the pleasure I was giving her was making her moan louder and louder. Eventually her legs started shaking and Sue started gasping for air. “Oh my God! I am cumming! I am cumming! OHHH!”
Her nectar came flooding out of her pussy and all over my mouth. Her juices were unlike anything I had ever tasted. She had came so hard that it was all over my face, dripping down my neck, and onto the nice hot pink bra I was wearing. As her orgasm subsided, she was panting hard.
Then I looked up and there was the clerk. She was staring at us with her mouth wide open. Finally she composed herself and told us to leave before she called the police.
Sue and I quickly got dressed. As we were still wearing our bra and panty sets, Sue gave the clerk a hundred dollar bill. With that, we ran out of the store and into the mall.
It was going to be a great night.
