First time dressed in front of somebody else
out of collage I got a job in a big office, things were awesome. I was making some money, living alone, and heavy in my crossdressing. I was literally dressing every day after work. I keept my legs shaved and my toe nails painted. Sometimes I wore panties to work. I would enjoy talking to the women I worked with knowing I was wearing panties and my toes were painted like theirs.
One day in a meeting I noticed Linda fidgeting around and I realized her tan stocking was falling down and she was discreetly trying to pull them back up. It was so exciting for me to know she was wearing stockings and not pantyhose. I couldn't get enough of looking at her nyloned covered legs so I asked her to lunch pleased to spend the next hour enjoying looking at them. She pleasantly excepted my invitation. At lunch we really hit it off and became good friends. When we were leaving the restaurant I was helping her into the car when I got the best up skirt view. She was wearing black sheer panties with pink trim and the stocking tops. It was so sexy I couldn't wait to get home and dress as closely to what she was wearing as I could.
As time went on we frequently had lunch together, I even admitted to her about the time I got the up the skirt look. She was embarrassed but flattered.
One day during lunch she told me she had to tell me something serious. She was leaving her husband for another guy who worked at our company.
I was shocked to hear this. I had actually thought I had a chance with her so I wasn't painting my toes or shaving as much so I would be ready if she was game.
Even though it was a tough situation with her being married, us being coworkers, and her being 10 years older than me. There was clearly a lot of sexual tension between us.
Over the next couple weeks I dove deep into my crossdressing. Then one day at work she asked me to help her move out of her house. I agreed even though the situation was so messed up. One Saturday when her husband was at work I came over to help her move out. She was mostly packed up and we filled our two cars. Somehow a square cardboard box full of bras and panties was on my passenger seat. As I was following her I fell a car behind purposefully so that I could look through the box of panties. When I look then I found the black sheer panties with the pink trim that I had seen her wearing the first lunch. I've put them in my glove compartment of my car to keep. I figured I deserved some kind of reward for helping her.
She was moving into an apartment in the city that was very small. She asked could she store some stuff in my basement. It was a couple of small pieces of furniture and a few boxes. Mostly the stuff that was in my car already. She promised she would pick it all up in a couple of months. I agreed and headed home. When I got home I unloaded her stuff in my basement. Naturally I looked in the boxes to see what was there. I was pleased to find two of the boxes were full of all kinds of different clothes. Most of the stuff wasn't going to fit me. Lots of fitted stuff. But I found cranberry red minidresses that fit and I add it to my collection. I really enjoyed wearing her mini dress with her panties and then seeing her the next day.
A couple months later she picked up all her stuff, and I don't think she ever suspected anything. We continue to have lunch together often. One day I even had lunch with her while wearing her panties, that was really enjoyable.
I guess things weren't going well with the other coworker because she invited me over on a Friday night to have to have dinner. I think she could tell I had a thing for stockings because when I showed up she was wearing a short skirt with black stockings and a red top. After dinner we were sitting on the couch when she put her hand on my croch. Before I knew it she was pulling my pants down and I was watching her beautiful auburn red hair bob up and down on me. As she continued to pull my pants down I heard her ask do you shave your legs? So I decided to tell her in confidence about my crossdressing. At first she seemed kind of disgusted.
Then she asked me what I thought of the outfit she was wearing. I told her I loved it and thought she was gorgeous. She asked me what I like to try it on?
Of course I was thrilled, this was a fantasy coming true. I strip down naked as she slid her red panties down from under her skirt and handed them to me. She said put these on. I stepped into the panties and slid them up feeling the warmth from her body. Then she rolled down each stocking handing them to me one at a time. I rolled them up my legs like a pro because I love wearing stockings more than anything. She even commented I really must be a cross-dresser after watching me do that. Next she unbuttoned her red top and layed it over the arm of the chair. Then she unclipped heard leopard print bra and put it on my body, hooking the clasp. As I picked up her red blouse and put my arms through it beginning to button it up, She slid down her skirt exposing the perfect square of red pubic hair. I took her skirt and a pulled it up completing the outfit.
There was a combination of things happening, I think she was surprised at how decent I looked in her clothes but at the same time she was kind of grossed out by it. She told me that my best feature was my feminine legs. then as she stood stark naked except for her high-heels, she stepped up to me, reaching under her own skirt to grab my crotch covered in her red thong panties. She pulled the panties down lifting the skirt up, and began deep throating me. After a minute she turned around and bent over and I fucked her as hard as I could while wearing her clothes. The only thing that would've made this more perfect is if I had my wig make up and high-heels. After we finished she told me to take off all of her clothes and give them back to her.
She promised to keep what happened a secret but she thought it was kind of disgusting that I'm a transvestite and didn't want to ever sleep with me again. This was a one time thing just because she had wanted to fuck me. She told me how sick it was that I want to dress as a women. We had lunch much less frequently after this... Then one day she told me she was giving her two weeks notice and moving on to a better job. After she left we didn't keep in contact, only thing I know of her is what I see on Facebook.
In hindsight I found out what a messed one she really was aside from what she did to me ( not that I'm complaining ) and all the men she slept with in our company, all of which I found out after the fact. The latest thing I heard, was she had set her sights on a married man. Good luck to him. I'll just continue to enjoy dressing myself up as a woman.
One day in a meeting I noticed Linda fidgeting around and I realized her tan stocking was falling down and she was discreetly trying to pull them back up. It was so exciting for me to know she was wearing stockings and not pantyhose. I couldn't get enough of looking at her nyloned covered legs so I asked her to lunch pleased to spend the next hour enjoying looking at them. She pleasantly excepted my invitation. At lunch we really hit it off and became good friends. When we were leaving the restaurant I was helping her into the car when I got the best up skirt view. She was wearing black sheer panties with pink trim and the stocking tops. It was so sexy I couldn't wait to get home and dress as closely to what she was wearing as I could.
As time went on we frequently had lunch together, I even admitted to her about the time I got the up the skirt look. She was embarrassed but flattered.
One day during lunch she told me she had to tell me something serious. She was leaving her husband for another guy who worked at our company.
I was shocked to hear this. I had actually thought I had a chance with her so I wasn't painting my toes or shaving as much so I would be ready if she was game.
Even though it was a tough situation with her being married, us being coworkers, and her being 10 years older than me. There was clearly a lot of sexual tension between us.
Over the next couple weeks I dove deep into my crossdressing. Then one day at work she asked me to help her move out of her house. I agreed even though the situation was so messed up. One Saturday when her husband was at work I came over to help her move out. She was mostly packed up and we filled our two cars. Somehow a square cardboard box full of bras and panties was on my passenger seat. As I was following her I fell a car behind purposefully so that I could look through the box of panties. When I look then I found the black sheer panties with the pink trim that I had seen her wearing the first lunch. I've put them in my glove compartment of my car to keep. I figured I deserved some kind of reward for helping her.
She was moving into an apartment in the city that was very small. She asked could she store some stuff in my basement. It was a couple of small pieces of furniture and a few boxes. Mostly the stuff that was in my car already. She promised she would pick it all up in a couple of months. I agreed and headed home. When I got home I unloaded her stuff in my basement. Naturally I looked in the boxes to see what was there. I was pleased to find two of the boxes were full of all kinds of different clothes. Most of the stuff wasn't going to fit me. Lots of fitted stuff. But I found cranberry red minidresses that fit and I add it to my collection. I really enjoyed wearing her mini dress with her panties and then seeing her the next day.
A couple months later she picked up all her stuff, and I don't think she ever suspected anything. We continue to have lunch together often. One day I even had lunch with her while wearing her panties, that was really enjoyable.
I guess things weren't going well with the other coworker because she invited me over on a Friday night to have to have dinner. I think she could tell I had a thing for stockings because when I showed up she was wearing a short skirt with black stockings and a red top. After dinner we were sitting on the couch when she put her hand on my croch. Before I knew it she was pulling my pants down and I was watching her beautiful auburn red hair bob up and down on me. As she continued to pull my pants down I heard her ask do you shave your legs? So I decided to tell her in confidence about my crossdressing. At first she seemed kind of disgusted.
Then she asked me what I thought of the outfit she was wearing. I told her I loved it and thought she was gorgeous. She asked me what I like to try it on?
Of course I was thrilled, this was a fantasy coming true. I strip down naked as she slid her red panties down from under her skirt and handed them to me. She said put these on. I stepped into the panties and slid them up feeling the warmth from her body. Then she rolled down each stocking handing them to me one at a time. I rolled them up my legs like a pro because I love wearing stockings more than anything. She even commented I really must be a cross-dresser after watching me do that. Next she unbuttoned her red top and layed it over the arm of the chair. Then she unclipped heard leopard print bra and put it on my body, hooking the clasp. As I picked up her red blouse and put my arms through it beginning to button it up, She slid down her skirt exposing the perfect square of red pubic hair. I took her skirt and a pulled it up completing the outfit.
There was a combination of things happening, I think she was surprised at how decent I looked in her clothes but at the same time she was kind of grossed out by it. She told me that my best feature was my feminine legs. then as she stood stark naked except for her high-heels, she stepped up to me, reaching under her own skirt to grab my crotch covered in her red thong panties. She pulled the panties down lifting the skirt up, and began deep throating me. After a minute she turned around and bent over and I fucked her as hard as I could while wearing her clothes. The only thing that would've made this more perfect is if I had my wig make up and high-heels. After we finished she told me to take off all of her clothes and give them back to her.
She promised to keep what happened a secret but she thought it was kind of disgusting that I'm a transvestite and didn't want to ever sleep with me again. This was a one time thing just because she had wanted to fuck me. She told me how sick it was that I want to dress as a women. We had lunch much less frequently after this... Then one day she told me she was giving her two weeks notice and moving on to a better job. After she left we didn't keep in contact, only thing I know of her is what I see on Facebook.
In hindsight I found out what a messed one she really was aside from what she did to me ( not that I'm complaining ) and all the men she slept with in our company, all of which I found out after the fact. The latest thing I heard, was she had set her sights on a married man. Good luck to him. I'll just continue to enjoy dressing myself up as a woman.
7 jaar geleden
