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 salon. That girl next to Sue was very hot. So hot, that I almost walked up to her and asked her to come to my place for a little fun and action.” With that, Brad chuckled a little. “I swear I had met that girl before, and if memory serves me, she likes to dress up as Red Riding Hood and Princess Leia, and she likes hard man sticks. I believe her name was Jessie.”

I turned beet red and told him to fuck off. Meanwhile, Tracy looked me in the eye, leaned over to me and whispered, “Looks like Sue got her hooks in you. She will transform you beyond your imagination. I can’t wait to see the end result. It is so obvious to us in the office that you’ll become more than a little sissy boy in women’s clothing. Look at you. Your fingernails are still polished and I can smell the scent of Chloe on you.”

Oh shit! I can’t believe I forgot to remove the fingernail polish! This is going to ruin me at work. After realizing my error, I told Tracy and Brad to leave me alone and went to my office. I contemplated what I should do about my nails. There was no way I would be able to sneak out to buy remover and clean them up. I had a meeting with my manager Steve in twenty minutes. I know he wouldn’t think kindly to one of his male employees wearing anything womanly, especially since I was one who interfaced with our customers, but I knew I couldn’t be late to the meeting either.

About ten minutes after getting settled down, Sue walked into my office and shut the door. “Jesse, I have been thinking all weekend long about our date. You were so hot and sexy. Everything you did, I have been replaying in my head. You were such a hot and sexy little sissy boy. When do you suppose we can go out on another date?”

I didn’t respond to Sue. Instead I kissed her passionately on the lips.

I loved the taste of her lips. My cock was swelling, and I had to have her now. We continued kissing for a couple of minutes when I slowly but confidentially lifted Sue’s shirt up to her breasts. She stopped me and stated, “We are at work, are you sure about this?” I went back and lifted her shirt up above her breasts. The threat of being caught was not going to stop me. I was certain my career here was ruined anyways.

After her shirt was removed, I undid her bra and started to suck on her nipples. With her eyes closed, she tilted her head back, placed a hand behind my head, and moaned audibly. She was getting turned on. I continued the treatment on her breasts for a couple of minutes, and then slowly slid a hand over her pubic mound. I could feel the heat emanating from her crotch. As I started to rub her, she started gyrating over my hand to add to her stimulation. It also felt like her crotch was getting increasingly wet.

After a couple of minutes, Sue finally asked for me to take her on my desk. I was floored by her request. She was the one that dominated me, but here she was begging for me to enter her. In our heat of passion, Sue started to take my shirt off. Little did she know of the surprise that she would find. As the shirt came off, she gasped, “Oh my! You really like that bra and panty set from our date.”

Not only was I wearing the matching bra and panty set, but I also had those sexy thigh high lacy pantyhose that Becky gave me before we left the shoe store. Sue continued on, “Looks like my sissy boyfriend would prefer to wear women’s cloths full time. How exciting… And how sexy… Put your sissy clit into my pussy and fill me up.”

I hastily took off her clothes, leaned down and started licking that tasty and succulent pussy of hers. Starting off with a slow lick, followed by a quick nibble on her clit, she started begging me to enter her. But I wanted to taste her for a while. Enough to get her really lubricated, but not too long as to having my door closed where it would arise suspicion of something going on. By a couple of minutes of licks and nibbles, she started moaning and pushing my head deeper into her beautiful tunnel of love.

Finally Sue started shaking and almost yelling, “Oh, Jessie! Oh, Jessie! Your tongue is so talented! Eat me until I soak your face and desk! I can’t take this any…. OOOOO… I’m!!! I’m!!! OOOOHHHH!!! AHHHH!!! YESSSSSSS!!! Oh my god! I need you inside me NOW!!!”

I stood up, my face was drenched in Sue’s nectar, and there was a puddle of her orgasmic juices on my desk. I really didn’t care. I wanted to take care of mine and Sue’s own needs. If I got fired, so be it. I would be saved the agony of working with that ass Dan, or that bitch Tracy.

Sue begged me again to enter her. I slowly slid off my panties and stuck the tip of my man clit to the entrance of her womanhood. As I slowly entered her, Sue moaned, “Ohhhh baby… Put it all the way in and fuck me hard with the clitty of yours. Make me cum again.” I pushed my hardened man clit totally into her and she grunted and moaned. “Oh god Jessie, your man clit feels so good in there. Now Fuck me like you mean it.”

I started thrusting in and out of her slowly, but she wouldn’t relent. “Come on Jessie. I don’t want some nice romantic Fuck. We are in your office, remember? We need a quick release. Now make me your whore!” I sped up my thrusting into Sue. As I was thrusting harder and faster, Sue started talking dirtier and dirtier.

Having sex with the woman of my dreams was pretty hot. Having sex with her while I was in my new lingerie and feeling the sensations of my nylons rubbing my legs made it more intense. But what topped it all was the sensation of the walls of her pussy slowly grasping and releasing my man clit. All of this was getting more and more worked up.

Meanwhile, Sue started moaning more and more loudly. Finally she almost shouted, “Oh God Jessie! Fucking pound my pussy! That’s it! Nice and hard! I want you to make me walk out of your office funny! I want to feel you shoot your load into me! Make me your little slut! That’s it! Oh Shit! I’m going to cum again! Ohhh Jessie, unload your little baby makers into me! I want that sperm of yours to enter my womb! Make me with child! Our child! OOOOOOHHHH! YESSSSSSS!!!”

Her pussy walls squeezed my man clit so hard that I shouted out way too loud, “I’M CUMMINGGGGG!!!” With one final thrust, I unloaded my sperm into her womb. We were starting to catch our breath, and I was still inside her when we suddenly heard the knocking on the door.

“Jesse! You’re late to your meeting with me! What in the hell was all of that noise coming from your office? I sounded like someone was having sex in there!”

Now I knew I was going to get it. That was my manager Steve…