A Sissy Training Experience

I had an experience with a younger woman where I worked I'll call Sue, she was tall, true blond, legs forever.  I don't know why but she got a crush on me, she would have some computer problem and call, I'd go down there, she seldom wore a bra, her nipples stood out, she'd stand behind me to see how'd I fix her problem and brush my neck with them.  Her older sister was a manager in another department, I worked with her frequently also, and one day she invited me to dinner at her and her boyfriends house.   Sue was there, dressed in heels and a slit skirt, awesome, she sat next to me, would brush her foot along my leg from time to time, I spent the night there talking with Sue, fondling, but not going all the way.  We met a few times, then finally I spent the night with her in her apartment.  She was such a tease, she'd stop me before she would ****** and before I would, denying me any type of satisfaction.  Then finally, when she wanted, she'd push me on my back and get on top, riding me and controlling when I could finally ***.  After the 2nd night while I was in the shower she came in with me but instead of playing she started to shave me, telling me smooth men excited her so of course I allowed her.  When we got out she put on a long sheer black night gown and gave me a pink baby doll to wear.  She teased me for hours, she'd stand behind me, our silky bodies rubbing as she'd reach around and rub me thru the panties.  Eventually, as we were standing in front of her vanity mirror she made me *** in my panties as we watched in the mirror.  I couldn't believe the intensity of the ******, I just about fell over.   Then I satisfied her orally.  After that I always had to keep shaved, still do to this day, and she would pick out things for me to wear.  I would serve her, sit at her feet b her chair, I'd wear a collar and sometimes she'd hook a leash to it and put her end under the chair leg so I couldn't stand up, she'd rub my pantied crotch with her high heeled foot and tease me to no end, if I displeased her shw would make me bend over her knees and she would spank me, I loved it all.  Then one evening as I was in a little pink nightie with pink stockings and heels, my leash hooked under the foot of her chair as she sat on it, the door opened and in walked her sister and her boyfriend.  I was panicked, fear and embarassment rushed over me, I couldn't hide, I was there, a shaved sissy at her feet.  Her sister stood there looking at me and said she couldn't believe she had really done this to me.  I worked with this woman regularly, she knew and I hadn't known it, but now it was out and I'd have to see her almost daily knowing she knew this about me.  Sue unhooked me and told me to get her sister and boyfriend something to drink, and I was a good maid all evening while they talked about me, Sue telling them about how she controlled me sexually, makingme bring out some of the things she had me wear, telling them that I was wearing panties and stockings to work ever day, one time the boyfriend came into the kitchen while I was there making snacks and began to rub my *** thru my panties, then turned me around and rubbed my excited ****, telling me he was going to make me his ***** one day, it was one of the most humiliating experiences in my life, but the experience left me so excited I begged Sue to let me ***, so she had me hump her stocking leg like a dog until I came in my panties.  At work the next afternoon I had to see her sister, who had me close her office door, made me walk over to her desk, drop my pants so she could see that I was wearing panties and stockings, fondled me a bit to make me horny and uncomfortable while she told me Sue had called and told her about my being so horny from the evening I humped her leg like a dog, told me that if I didn't come to her immediately whenever she called she would make me *** in my pants and walk around like that the rest of the day and how would I explain the big wet spot, and she'd start telling all the other women about me.  About 6 months later I was transferred to another location 650 miles away though and it all ended, the boyfrined never did get the opportunity to make me his *****, but I wouldn't mind going thru it all over again.   

SissyDenise SissyDenise
56-60, M
18 Responses Mar 5, 2009

Love your story ! Wish some of the women in my office would do that to me !

A really nice story about a great experience. Thank you for sharing.

Denise I love your story. WIsh our office manager would do this to me!

oh Sister Sis lovely story we all live for times like that. too bad the boyfriend never lived up to hid word

nice,did all the women at your job start using and teasing you too?

I love women who realize their power...

me too,i have a supervisor that is a high school senior that knows her power and runs me around like a chicken and she knows im scared to death of her boyfriend and tells me she is gonna tell hinm i grabbed her ***,im almost crying while i beg her not to,i do all her work and pick up and pay for her lunch

Wow, I"m rock hard in my pantyhose just reading this and thinking about being in your place.

Fabulous sweetie<br />
Hugs<br />

Good slave Denise. Like the bit about her leg.

Wow! Just wow!

what a wonderful experience, thank you for sharing it

I wish I could meet them

Are they hiring?

my panties are stretched here at work wishing I had someone at work to make me feel like a sissy ****

great story `s` thank you for sharing it

very hot! a dream come true for me

very hot! a dream come true for me

You are a good story teller,and She sure turned you into who you really are very fast, did she not? Have you started to service the pleasure of men yet? Even though you are a straight male, as a sissy, one of your duties is to learn to suck off men and swallow their gift to you. Or did you not know that, little girl?