tagFetishSissy Boy Secretary

Sissy Boy Secretary


As I sit here in the outer office space of the company CO, I look like an ordinary male secretary. On the inside I'm wearing a pair of pink lace panties, at my bosses request. You see I'm really a sissy inside and my boss takes advantage of this at every possible opportunity. I've worked here for 2 years now and it wasn't always this way. My boss, Elaine, a 5'10" fox of a lady, found out about my indiscretion when she checked out the sites I was viewing on the internet. About 6 months after I took the job she asked me to stay after work to discuss a problem she found. I wasn't sure what this problem was so during the rest of the day I checked and re-checked my past work, without finding any problems. Seeing everyone leaving for the day I was getting more nervous.

I timidity knocked at her door and after a couple seconds she asked me to enter. She sat at her desk in her big office chair just staring at me for a minute. Then she asked me to take a seat next to her desk.

"I was checking over the access to the internet from your computer and I found some disturbing things," she told me with a stern look on her face.

I should explain that I had been searching sites about dominant females & how they controlled their men, something I find very exciting. The humiliation factor I found to be very dangerous and sexy, it turned me on quite a bit. I often found that I had a hard-on just from reading and viewing the material.

Turning her computer screen so I could see it too she asked, "Is this what I pay you to do while you work for me?" The picture showed a male secretary in panties at his bosses feet with her holding a riding crop. My penis immediately got hard, something I couldn't control.

"Is this how you think of me? A controlling boss?" she asks. When I didn't answer right away she asked again, "Well??? Is it?," her voice becoming more stern.

"No mam it is not how I think of you." I replied.

"Well is this how you'd like me to be then?" she asks.

"Well it would turn me on. You are so beautiful and command this type of respect mam." I come back with. Watching as she crosses her legs which causes her skirt to move up farther on her thigh.

"Stand up," she orders me to do. My hardness could not be hidden, a fact she noticed right away.

"I see that this turns you on very much by the looks of you crotch." She says while staring at my hard-on.

"You are a very beautiful lady with a great body which is the main reason I took this job mam." I say. "The way you commanded my respect from the interview has always excited me. You are always in control of any situation which I find so sexy."

Let me tell you a little about Elaine before I go on. You see she is a 5'10" blonde with hair down to the hottest ass I've ever seen. Her 34D chest stands firm without the help of a bra, the nipples standing out on quite a few occasions. She always wears skirts that come a couple inches above her knees, showing a little thigh but still very professional. Her blouses are always covered up with a suit jacket that she removes only when alone in the office. At 34 she has kept her body in very good shape.

"So what do you think we should do about your surfing the net on company time? I should just fire you since you do know its against the rules." Elaine asks.

"Could you just give me a warning and I'll never do it again, I promise. I'm sorry that I've broken the rules and know I was wrong." I counter.

"I'm not sure that you would learn a lesson that way though. I think more must be done." She replies.

"I will do anything that you want but I really want to keep this job." I say.

"Anything you say? Do you mean that?" she asks.

"Yes anything, I love this job!" I answer.

She sits and thinks for a minute leaving me to suffer. "Well I think we can work something out and you might even enjoy it." She says. "First off I believe you deserve to be punished for your indiscretion. A spanking might teach you not to do it again, don't you agree?"

I quickly say, "Yes I think I do deserve it. I was wrong in searching the internet during work hours."

"Take off your clothes so I can do it properly!" she demands sternly.

I remove my clothes as fast as I can. I stand there with my raging hard-on naked for her to see.

"I knew you would enjoy this. Now get down on all fours and get my riding crop from the filing cabinet." She says.

I crawl naked to the filing cabinet knowing her eyes are on me as I do it. I open the filing cabinet drawer and place the crop in my mouth and make my way back over to her feet. She takes the crop from my mouth and tells me to place my chair in the middle of the room, staying on my hands and knees. After a couple minutes of struggling I get the chair where requested. She removes her jacket to reveal that her nipples were quite hard. She was enjoying this too it seems. She sits down in the chair and looks at me on all fours in front of her.

When she is comfortable she tells, "Get over my knee now!!!" which I do immediately, my hard-on scrapping her thighs. She starts to caress my ass very gently then without warning I hear the swish of the crop right before I feel the sting.

"Ouch!!!" I respond as it hits.

"I don't believe that is the response I want sissy!! Shouldn't you be counting and thanking me for allowing you to keep your job?" she asks.

"Yes mam, I'm sorry. That's 1 & thank-you for it mam." I say.

"Just how many do you think it will take for you to learn your lesson?" I was asked.

Not wanting to say an actual number I reply, "As many as you think I deserve mam."

"That's a good answer my sissy. I believe 20 should be a good start." She responds.

Smack!!! Goes the 2nd hit, "2 & thank-you mam," I say.

This continues until all 20 hits are finished with her calling me sissy the whole time, which only adds to my excitement. She is so much in control of me at this point and she knows it. She rubs my very red ass at this point, "Gee that looks so red and it looks like it hurt. Do you think you learned you learned your lesson my sissy boy?"

"Yes mam, I will never surf the internet again on work time!" I respond.

"Good, now to continue your punishment," she says.

I thought my punishment was complete but she had other ideas. She has me stand in front of her while she teases my cock with the riding crop. "You did seem to enjoy that as much as I did, didn't you?"

My cock throbbing now as she teased it, "It was what I deserved mam."

"Now since you are going to be my sissy I think you should dress like one. A nice pair of panties would be a good start. Get on your knees!!!" she orders.

Having no idea what she was thinking I sank to my knees in front of her. She slowly moved her thighs apart revealing a frilly lace pair of thong panties. They looked to be a wet spot in the center of them.

Standing up she tells me, "Remove my panties sissy boy!" A nickname that thrilled me, especially coming from such a dominant women.

I reach up under her skirt and grab the top of the panties to pull them down her sexy legs. As I thought the panties were indeed quite wet.

Stepping out of them she commands, "Now put them on sissy boy!" I pull the panties on over my hard-on, the lace pushed out in front.

"Turn around and let me see how they look on you sissy boy!!" I do just that and she comments, "Now you look like the sissy boy you are! Your red ass matches the color of the panties sissy boy."

"As you can tell this has got me quite excited too. Now what do you think we can do about that sissy boy?" she asks. My hard-on feeling the wetness of her panties. She moves around me letting her hands roam over my body, slapping my ass a couple of times as she does. "Would you like to see how excited sissy boy?"

Of course I said, "I would like to very much!!!"

"Would you like to please me my little pet?" she asks as she caresses my red ass. Slowly she starts to unbutton her blouse, revealing 2 very obviously hard nipples. "Would you like to suck my nipples sissy boy? I think that would feel good to me."

I practically drool as I respond, "I would love too mam!!! Any thing to please you my boss."

"OK then you may suck on them but do not use your hands!!!" she says. I begin with the left sticking my tongue out to gently lick it before putting it all in my mouth. Then I move to the other repeating the same process as she leans her head back and moans. "That feels so good. I guess being a sissy boy you do know how to satisfy a lady."

After a few minutes of this, switching back and forth between nipples, she pushes my head away. "Now sissy boy I have another task for you. It seems I've become very wet and I don't want to stain this skirt. You may now remove it but again, no hands." She commands. I get down on my knees and use my mouth to pull the zipper down. Watching me fumble with the zipper makes her giggle a little, "Good sissy boy."

Her skirt finally falls to the floor. She steps out of it and moves back a little, her hand going to her pussy. "Would you like to lick it sissy boy?" She moves away to sit at her chair.

"OH YES!!! I would love to lick it boss!" I say from my knees.

"OK then crawl over here between my legs and beg for it sissy boy!" she says. I think she enjoys watching me crawling on the floor over to her as I watch her play with herself.

I ask, "May I please lick your pussy boss and give you all the pleasure that you deserve?"

As she holds her lips apart, "You may lick me now but no hands sissy boy and you had better do a good job!" I reach out with my tongue licking her from the bottom to the top of her pussy. I pay special attention to her clit as she moans with pleasure, using her hands on the back of my head to pull me in more, securing my head in place. My head is held in place tight as she experiences an explosive orgasm, covering my face in her juices.

"Now clean up the mess sissy boy!!" she demands. I lick every inch of her thighs and pussy until she is completely clean. "Get my clothes now!!"

I do as ordered on my hands and knees of course. I watch her get dressed from my knees. She then grabs my clothes going to her door. "That will be all for today sissy boy!" throwing my clothes out to my desk. "Now crawl out of here and get dressed. Tomorrow I expect your panties to be clean and that you will be wearing them!"

I crawl out of the office hoping that the night guard is not making his rounds. She stands in the doorway laughing and saying, "That's my sissy boy, I have more plans for you tomorrow. Good night!"

I get dressed thinking about what will be in store for me now. I have never been this excited in my life and hope this is only the beginning.

To be continued...

Report Story

byHotenuf4u© 9 comments/ 232603 views/ 39 favorites
1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartOmegaMaximum, raz0132 and 37 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous03/21/18

Lovely Start

Hoping to find a boss like this

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 9 User Comments  or
Click here to leave your own comment on this submission!

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: