Join the best erotica focused adult social network now
Login

Jessie Caught in the Act

"After Jessie and Sue's office interlude, the boss catches them in the act."

17
2 Comments 2
20.4k Views 20.4k
2.2k words 2.2k words
Sue and I were starting to catch our breath from our office session when suddenly someone started 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.

Steve burst through the door and his mouth immediately dropped. After what seemed like eternity, he shouted out, “What the hell is going on? Two of my employees fraternizing on the job, against work policies? Not only that, what is that puddle on the desk? Jessie!!! Sue!!! Did you two have sex on the desk? I can’t believe you came all over the nice office furniture!”

Steve looked at Sue, and then started to turn toward me. Sue smiled as I tried all so feebly to cover the bra and panty set that I was wearing. Once Steve’s shock subsided, he said with a very loud voice, “What the hell are you doing wearing women’s underwear and a bra? No. Wait. Don’t answer that, I really don’t want to know.” After saying that, he tossed my work clothes out into the hallway. “Go show everyone in this office what you really like to wear! Get your clothes and get out of here! Sue, same goes with you!” Steve turned away and mumbled to himself, “My two star employees. Geesh!”

As I walked over to pick up my clothes, a crowd had gathered around all of the commotion. There was no denying it now. My secret was out and there was no stopping the humiliation I was about to endure. Cat calls, co-workers calling me sexy or sissy, some fondling my ass as I walked by, and others were even brazen enough to say they want to bend me over and have their way with me. I was beet red as I walked through the crowd of co-workers. Finally, I walked by Dan and Tracy. Tracy paused for a moment and whispered “You are such a little girly girl. I bet within the month you won’t even touch men’s clothes, and you’ll be begging to have something a little extra.” She had this little evil laugh as she walked away. It was seriously starting to make me wonder if Sue befriended me as one big ploy to thoroughly humiliate and degrade me. I quickly got my clothes back on and started running to the lobby.

Seeing me distraught, Sue started also started to run toward the lobby as she was yelling, “Jessie! Slow down! Let me catch up!”

I slowed enough for her to get within a couple of feet of me, and I turned toward her. I was visibly not happy with what Tracy whispered in my ear. Without thinking, I yelled at Sue, “I can’t believe I thought you were genuinely into me!”

“What is that supposed to mean?” replied Sue.

“Don’t even go there. I know that you are in on this humiliation charade.”

With a questioning look Sue asked, “What are you talking about?”

“Come on. Don’t even go there. I know you, Dan, and Tracy are plotting together to get me out of the office by humiliating me because I happen to like women’s clothes. Tracy herself told me that you’d have me wearing nothing but women’s clothes within the month!”

Sue pleaded, “Jessie, I swear, I have not ever once talked to Dan or Tracy about you. I care too much about you to hurt you. I have never had such quick, strong, and intense feelings toward anybody. I can’t explain it, but I know we were meant to be together for the rest of our lives.”

I replied back, “How do I know that you aren’t just providing lip service?”

“Jessie, hun. It’s called trust. You’ll have to trust me. If we don’t have that now, then it will never work between us. I’ll be devastated.”

Something inside me told me to trust her. So I grabbed her hand, and pulled her close to me. I gave her a soft and quick kiss on her lips, and led her out to the parking lot of our office.

We proceeded to go to her place for the afternoon. While there, we had a very long discussion of our feelings towards each other. Both of us agreed that we had something very special going on. She finally got what she wanted, which was a boyfriend that likes women’s clothes. And I had a girlfriend that encouraged me to explore my feminine side. It was around 3 PM when Sue asked if I would like to go to the mall with her. Of course I said yes to her request and we drove off.

We ended up going back to the department store where we were threatened to have the cops called on us for having sex in the changing room. This time I knew that we would not have an issue. As Sue was looking through some sexy looking black dresses, I saw someone familiar. It was the clerk who threatened to call the cops on us. She quickly helped her customer and came towards us with a big smile on her face. “Sue! Jessie! It’s so nice to see you so soon!”

Sue leaned over and gave the clerk a hug. “Friday was an amazing night. Thank you so much for being a part of something really special. To have my four closest friends present on our memorable first date really means a lot to me.”

The clerk replied, “You better not lose Jessie, girl. Her tongue is so incredibly talented. I’ve never had anyone eat me to a squirting orgasm like she did. I’d take her in a heartbeat if you two don’t stay together.”

“No need to worry about that. Jessie and I have already discussed our future together. We are one, and will always be together.” Sue stated.

The clerk clearly looked saddened by the comment. I was stunned that she really dug me as well.

After seeing her friend’s saddened look, Sue quickly interjected, “I’m not saying that you can’t have a little fun with Jessie.”

I caught Sue’s wink and with that, the clerk took Sue and I around the store.

AntonellaReed
Online Now!
Lush Cams
AntonellaReed

While listening to Sue, I learned that the clerk’s real name was Abby. She was really pleasant and helpful. Not only did she help find some killer fitting dresses for Sue, but she also found some really sexy things for me to wear as well. Abby ushered all three of us into a large dressing room so she could verify the fit of the clothes on myself and Sue. The dresses that Sue picked out for her were absolutely stunning. They accentuated the curves of her figure, and gave her a sex appeal that was beyond imagination.

When it came to be my time to try on the dresses, nothing seemed to look good on me. They were either too baggy around the breasts, or did nothing to create a figure for me. Abby wasn’t one to give up. She left for several minutes which gave Sue and I several minutes to start making out. She was fondling my sissy boy clitty when suddenly Abby caught her red handed. As she handed me several short length dresses, Abby stated, “I also found these items for you Jessie. I think these will really help you out.” I looked at the other items that Abby handed me. One was a nice white colored corset that looked like the waist was 3 inches too small for me, and the others were silicone breast forms. I was wondering how she obtained the breast forms as I knew the store didn’t sell them.

Abby helped me get into the corset, and she made sure to tug on the laces so the corset was really tight on me. “I want you to wear this every day that you wear women’s clothes. Sue should periodically tighten the lacing as you body starts to get used to the shape. Eventually, you will end up going a size smaller.”

The corset was pretty tight on me. One would say it was uncomfortably tight as I had to work a little harder to breathe, but for some reason it also felt really good. After getting on the corset, Abby handed me the breast forms to insert into a new bra. I quickly put the bra on and quickly looked in the mirror. I have to say I was quite stunned at the womanly figure I had suddenly “developed”. Sue and Abby also commented how sexy my body looked and that I would make a lot of ladies jealous. I was smiling inside, yet a tear slowly made its way down my face. Sue quickly took notice and asked, “Why the tear? Are you sad?”

“No Sue, I am so incredibly happy right now! I have never been so happy! I have you in my life, and now a figure that I have always wanted. Everything seems so… Perfect right now.”

Sue came to me and wrapped her arms around me. I felt protected and secure. My feeling of security wasn’t so much about one being protected by their mother, but more of a man protecting his woman. Yet Sue didn’t act manly by any means. She was all woman, so I guess it was me acting super feminine and vulnerable which was quite a first for me. I literally wanted to go home with her and nestle into her and rest my head on her chest while she had her arms wrapped around me.

Abby interrupted my thoughts when she stated, “I think Jessie has finally found some inner peace.”

Abby was right. I had found some inner peace. I realized today that nothing would be better for me than to be ultra comfortable in women’s clothes and with Sue.

I walked out of the department store wearing new high heels, a beautiful black dress that stopped mid thigh, and my new corset and breast forms. I was glowing and walking with a confidence that I had never had. In the changing room, I was so focused on my revelation, that I never really realized how real my breasts looked. Each step I took, I could feel the slight lifting and falling sensation that I knew a woman would feel with real ones. I just loved how they jiggled and moved. If only they were real.

We got back to Sue’s place and she realized there was a message on her cell phone. She listened to her message only to give a scowl at the phone and yell “Jerk!” I asked what was going on, and she quickly replied, “Our boss left a message that me and my cross-dressing boyfriend are on unpaid leave for a month.”

“What? He can’t do that! I don’t have the money to survive a month of lost wages!” I stated in a defeated tone.

“Well, he can. And he did.” Sue replied back. “There is nothing we can do now, so let’s grab some Merlot, have a couple of glasses and enjoy each other’s company.”

As the evening progressed, we lit a fire in her fireplace, and I learned a lot about about Sue. I learned about her favorite hobbies, her life growing up, the trials and tribulations during her teens and college years, and finally her discovery of getting hot and bothered by submissive men wearing women’s clothes. I clung to every word, and realized she truly was a treasure to behold. She was my soul mate. What left me totally awestruck that she hadn’t had a boyfriend for over three years. I was amazed as she was the perfect woman for any man.

As the fire was dying out, I leaned over to kiss her. We started with a slow series of passionate kisses. None of which were hurried or lustful. They were full of passion and love toward each other. Every time our lips touched, I felt little jolts of electricity between us. As we continued to kiss, my job worries slowly faded away. Both of us were feeling a connection that neither of us had experienced before.

When all that was left were glowing red embers, we looked into each other’s eyes. The love our eyes showed was very evident to each other. I gave her one final passionate kiss and wrapped myself around her, taking the submissive role of placing my head on her chest. Her arm wrapped around me in a protective and loving way. As I started to drift off to sleep with Sue, I felt the weight of my breast forms and my new corset. It suddenly came to me what true happiness would be for me. I fell asleep with the thought that our month away from work would be a month like no other.

Published 
Written by JessieCD
Loved the story?
Show your appreciation by tipping the author!

Get Free access to these great features

  • Create your own custom Profile
  • Share your erotic stories with the community
  • Curate your own reading list and follow authors
  • Enter exclusive competitions
  • Chat with like minded people
  • Tip your favourite authors

Comments