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Girls or boys. Have you ever dressed a guy in girl's underwear or dresses? Was it your idea or his? Was he willing or did you force him? How did it affect you or him? Was it just once, or did it become a "thing"?

2006-10-10 08:55:21 · 9 answers · asked by debbysfemail 3 in Society & Culture Cultures & Groups Lesbian, Gay, Bisexual, and Transgender

9 answers

I caught my younger brother trying on my things one time. My first inclination was to go to our parents and complain about him getting into my stuff. He begged me not to, so I made a deal with him. As I always enjoyed humiliating him, I said that he would have to let me dress him whenever I felt like it -- and have my friends over to join in the fun. During his teenage years when this took place, he was fairly passable, so often we made him run errands for us. While he enjoyed dressing up, the public exposure allowed me to exact my revenge for his original infraction of getting into my clothes.

2006-10-16 04:05:19 · answer #1 · answered by Viki 3 · 3 0

My ex is a transvestite and alot of our sex play was with him dressed, his idea. When I was young I didn't care, when I got into my 30's it just represented his inability to think about anyone but himself. Marriage ended emotionally and physically at year 15.

However I have crossdressed men during BDSM sex play. The idea behind humiliation play (which is the "forced" crossdressing) is to demean the man by making him wear some articles of women's clothing. My preference is for lingerie, stockings, stiletto''s and red lipstick. Other Women I know dress their male submissives completely with the intention of passing. The men I played with were usually conservative christian heterosexual businessmen (stockbrokers are the worst) who had a great degree of self hate, and usually had been crossdressing since puberty so it was all tied up (sorry) with their sexuality. I've actually done this for over 30years, and have "retired" from playing with men.

2006-10-10 16:18:30 · answer #2 · answered by tjnstlouismo 7 · 1 0

I crossdressed a guy about 32 yrs ago, and well Im still crossdressing, so, yea its been more than the one time, It was my idea, and I didnt have to force myself at all, the pantyhose just felt so good, oh and it was lingerie and dresses I have had over the years.

2006-10-14 17:49:15 · answer #3 · answered by Anonymous · 1 0

My sister used to dress me up in her old dresses when I was like 2. Also, I had to cross dress for a play in high school. I don't make a habit of it and I don't know how it affected me, but I am gay so I'll let you do the math.

2006-10-10 09:30:53 · answer #4 · answered by Liir 3 · 0 0

Yes he loss a bet so I made him dress as a female and he look like a cute one

2006-10-18 07:43:23 · answer #5 · answered by Anonymous · 1 0

Ha ha ha - good one...

I dressed my son up as a hooker for Halloween..he was 15, his best friend was his "pimp"...it was hysterical..he hates that I took pictures though...

2006-10-10 08:59:05 · answer #6 · answered by Anonymous · 1 0

i started when i was 13 yrs old wearing a pair of my sisters pantyhose.....and have been doing it ever since, and i love it more each and everyday

2006-10-10 16:11:53 · answer #7 · answered by ph cherrie 3 · 1 0

no

2006-10-10 09:35:30 · answer #8 · answered by st.uncumber 5 · 0 1

That's gross. No, really, it is.

2006-10-10 08:58:30 · answer #9 · answered by 11:11 3 · 0 3

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