Secretary Caught Me!

Our office is small just 4 people. My secretary and myself are very close, she knew i was an avid crossdresser but had never saw me and had never said she wanted to. One Sunday I was behind on some work, it was a holiday weekend and i thought everyone was out of town. So me being me, I decided to go in a more feminine look but I brought some other clothes just in case. After about three hours I figured no one was going to show up so I relaxed a bit and got to some serious work. I had to make some copies of an invoice, so i walked to the copying machine, which is in another room. As i was making copies I started looking out the window and never heard the door or the person say "OH MY" when I turned around there was Karen my secretary standing there looking and smiling. I guess I should have just died right there, but I didn't. I just turned and said "Hey girl what are you doing here? I thought I had the office to myself." "I guess you did." she said. We both walked back to my office and I could tell she was looking me over pretty well, and I was enjoying it. We sat and talked for about two hours she was asking questions as fast as I could answer them. She told me how attractive I looked several times and that I could easily pass as female. She finally said she had to run and that I needed to get back to work, so after she locked the door that is just what I did. It was almost dark by now so I was trying to finish up and get home to enjoy a little bit of my holiday weekend. I was sitting at my desk when my door squeaked and Karen was standing there looking at me she was wearing a shirt and tie and khakis, she said in a deep voice,"Hey beautiful about finished" yes I said why? "Because I have always wanted to **** in the office, especially another woman." I was shocked and aroused at the same time, I had never thought of Karen in that way, even though she was a beautiful woman. She walked in the office and came over to my chair and pulled up my skirt and began sucking my ****, it did not take long and I was about to ***. She must have knew because she stopped abruptly,and said "Stand up and bend over the desk." Of course I did as I was told and bent over the desk as i was i could here Karen unzip her pants. When I looked behind me she was sporting a "*****" about 8 inches long. I said "Oh my God what are you going to do with that?" Karen said "You are going to remember this desk and this office for the rest of your life." She lubed my *** and her **** and began to **** me slow at first then she really started to enjoy her self. And so was I, in a few minutes I was ******* all over my desk and Karen started ******* to it was running down my *** and my legs. Karen was a squirter and could she ever!! We both just dropped to the floor and laid there for a while kissing and smiling at each other.After a while we got up got dressed and ordered some chinese we stayed at the office til after midnite. Today Karen and I are closer than ever, **** buddies, and I have never looked at my office the same!!!!!!! If these walls could talk!!!!!
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25 Responses Oct 16, 2011

wow you are so lucky

Oh my you are sooo lucky . I wish I was the one ,to be taken like that!

i want this the same as you did

All I can say is WOW!

I've been in positions at places of work were I've been able to dress and have similar and less then similar experiences. Not with co workers but I did carry on a liaison with an associates that I have confided in and met me at the office one Saturday afternoon ;). Throughout my work history, I have had co workers (male and female) who knew, appreciated and understood, but nothing of the sexual kind as they were all good friends and supporters. I just wanted to share, as your story is hot and obviously a fantasy come true. I hope the situations in your life and relationships are endless.

Wow, and I'm not sure if I could ever go into the office even in a skirt. But it's awesome that you were able to, and and it turned out so well!

It's great when people can be open and discover new things about themselves and others, and and of course have things turn out so well.

Love this story! It is a dream fantasy of mine for something like that to happen.

Great had a nice physical effect on me :)

Dam thats hot I need a secretary like that!!

MMMM I can only wish that would ever happen to me.

I wish tht wld happen to me

What a happy ending to a very scary situation - loved it.

That's a GREAT story, so hot that she came back and ****** you good. Would love to have that happen to me.

Oh you lucky *****!!

Holy WOW! that is every crossdresser's fantasy right there!!

That is HOT!

you are very lucky i dream one day like yours!

Excellent! Aren't you the lucky one!

Wow, I would love to meet her. Maybe I should invite her to my office for some late night work sessions

Just read your fascinating story. Now retired for almost 10 years, by force not choice, I often think back on my customer service career of over 37 years. I wonder if any of the customers I did presentations to or consulted with over the last 15 of those years ever realized that under my male shirt and pants I was femininely dressed. Customarily I simply wore satin panties and in colder weather a plain satin tank top type camisole (from Sears "Meant to be Seen" collection) or 1 one of my short lacy satin slips as those would be all I'd have time for at home. When on the road overnights I spent a lot more time dressing in my hotel room before leaving for customer meetings. Usually I'd add either an open bottom girdle or lacy satin garter belt to hold up my silky nylon stockings and a satin sleep bra (so no strap lines would be visible). My shoes on these trips were customarily a black pair of women's flats that appeared to be men's. (Thank you Payless!) These were easily slipped on and off so I could wear my 2.5 inch pumps for the drive to and from my hotel. <br />
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I've also wondered if the lovely female co-worker I was on a project with noticed my pink satin and lace slip the day we were working together in my office cubicle. After she returned to her desk I discovered that my shirt had unbuttoned (most over-sized males know about this) and my slip had partially puckered out through the opening. She never said anything but seemed a lot more fun to work with after this incident!

I wish I was in your position

Surprise, surprise! :)

That is very hot! You are real lucky!

great story

I do believe she was right. Did you have to change out the desk to keep from being distracted? Of course the obvious question, do you girls ever work together? (as opposed to play) Do you think the other two in the office know, or might be interested?