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Crossdressing went wrong…sort of!

Story Info
Dressed up for my girlfriend, didn’t go to plan!
830 words
3.98
22.5k
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When I was in my 20s I made the huge step of telling my girlfriend about my love of crossdressing. We'd played around with me wearing her panties when we've had sex and it progressed to her letting me wear stockings and a suspender belt sometimes when we were intimate but it seemed to stop there.

I'd been crossdressing since as long back as I can remember and I wanted to go so much further.

I'd joked around about me wearing full lingerie rather than just suspenders and stockings and I eventually persuaded her to let me wear a bra sometimes when we made love.

I knew it didn't push her buttons but she loved how turned on it made me so it was a winner!

Eventually I confided in her and told her I'd been dressing for a long time and had some lingerie and clothes of my own that I'd hidden away from her. She was intrigued and said she was curious as to how I'd look when fully dressed up.

Weeks went by until I plucked up the courage to suggest dressing up for her when she came back from work one evening and cook her dinner. When she jokingly agreed, I held her to it!

I reminded her that I'd been doing this sort of thing for a long time and not to be surprised!

We'd arranged it for a Wednesday evening und unbeknown to her I'd taken the day off to prepare.

I took my time making sure every part of me was perfectly shaved and spent the rest of the day applying lashes, perfecting my makeup, attaching French manicure nails and ensuring everything was perfect.

I then tightly laced my corset until my waist was as tiny as I could stand and then carefully put on my lingerie. All matching black lace bra, panties, suspender belt and seamed lace top stockings.

After ensuring everything was perfect I pulled on my black pencil skirt, white blouse and 6 inch patent heels. Lastly I pulled on my bob wig and admired myself in the mirror. I was so pleased, I looked like Vicky Michelle from Allo Allo with perfect sexy black makeup.

I prepared dinner in a very feminine fashion being careful to keep my beautiful nails from being damaged and awaited my girlfriend's return from work. My pulse was racing with excitement as I heard her key turn in the lock.

She came in as relaxed as usual, put her bag down and then froze when she saw me.

Her jaw dropped and she said "oh my God".

I thought it was meant as a compliment but it wasn't, she was horrified!

She was really shocked and didn't expect me to have gone so far and taken so much trouble. I think she was taken back by how often I must've indulged myself to have made such a good job!

I felt like I was being examined, she came closer and asked me to turn around. She lifted my tight skirt and was shocked again that I was wearing suspenders and commented on my high heels.

'Where the Hell did you find those in your size?"

I told her there were lots of places online that sold them.

She then stood back and asked if I was gay. I said no but I had a need to sometimes dress like this and I thought she wanted to see me dressed up?

She was standing with her hands on her hips and a look of disproval and anger.

She then turned around and went into my office, turned on my computer and demanded the password.

I told her and she logged in to my browser history. She then told me to make dinner while she read through it.

I finished dinner and when we sat down she said that she'd seen what arouses me and that she could never compete while looking at me with contempt.

I tried to explain that it was just fantasy but she dismissed it.

I said that this had all gone wrong, that I was sorry and that I should shower and get changed but she insisted that I stay dressed. Once I'd got over her reaction and accepted that I should stay dressed up I relaxed a little but still felt ashamed, silly and humiliated.

Then it hit me. The more she humiliated me, the more I got turned on. From that moment on, every comment, command or observation drove me wild!

Things were never the same between us after that night and we eventually split up but I'll never forget the awakening I felt after being humiliated.

Since then I've only found sexual pleasure in being dominated and humiliated by strong women.

I've had many online strong women who've made me humiliate myself or take risks of being caught and provide pictures to prove that I've completed the tasks and I love it!

This negative turned into a positive!

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7 Comments
4Leather4Leatherabout 1 year ago

Wish I could pull that off. So lovely

AnonymousAnonymousalmost 2 years ago

Reasonable story, horrible ending. Why would he enjoy domination and humiliation from anyone? Why not search for love and acceptance.

LeighhardingLeighhardingabout 2 years agoAuthor

Thank you for your lovely and encouraging comments, I’ll try to write more soon.

X

immoraljaneimmoraljaneabout 2 years ago

Sounds as though you'd like some cock too

AnonymousAnonymousabout 2 years ago

I love how you write. Thank you.

Missy4UMissy4Uabout 2 years ago

It hit home. I love this story

AnonymousAnonymousabout 2 years ago

Her loss.

Once a month I would treat my partner to a full-on lesbian onslaught from her own lingerie-clad personal slut. Culminating in the most wild cunt-ramming sex.

My dream was to visit the local woods , and have her gang-banged as I kept all the cocks hard with my mouth. Then her choosing the cocks that would fuck me too , as she pissed all over us.

I never mentioned my fantasy , but I think she actually might have gone for it on the right day.

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