The Best Worst Situation For A Str8

I’m straight but have crossdressed since around 12, and has experimented anal since much younger. This experience was around 10 years ago, I was living with my then GF and she went to visit her family for a couple of weeks, so I spent all my free time crossdressing and wearing a lot of her clothes… I was so horny and needing some rushing experiences that I went out dressed a few nights. It was very fun and exciting… one of those nights I was walking in a lone section of the city trying to get seen and boom, police came around, I hide a little but got caught anyway and was took over their patrol car… they asked why I was doing that and if I was gay, told them that I was not gay and I just liked to dress and wanted to be seen a little… so they took me for a small ride, to a loner and more private street to say so, and proposed me to give them money and service them as the slut I wanted to be, I had some money purposely just in case and gave it to them, and let them fuck me both, ended up all trashed with my clothes totally screwed and all my lingerie showing off more that I was originally dressed for, with my ass dripping cum and scared as f**k but at the same time safe and feeling more girl than ever after feeling 2 cocks f**k me and their strong hands touching me for 20 some minutes… I was shaking at the end but went home and masturbated like crazy that night.

That's Juicy! 12
Remove It! 1

# 73397 - by MexTv / September 8, 2024

by Anonymous on Sep 30, 2024 at 4:23 AM

I was 13 when my Mom told me she was going away for the weekend and that I was going to be alone from seven Friday morning until ten Monday night so a long weekend. That was the very first time I was ever alone. I had been fantasizing about cross dressing since I was around seven when I got to see how much fun my cousin had when she dressed up in pretty clothes. In fact it was that very desire that was the reason I insisted on growing my hair as long as Mom would let me. So by the time I was 13 my hair was long enough to sit on. On many occasions I stood in front of my mirror brushing my long hair and posing as femininely as possible wishing I had something pretty to wear. But all I ever got were some hair elastics to put my hair up in pigtails.

So Friday morning as soon as I heard the news that I was going to be alone I waited in anticipation of Mom's departure helping her carry her bags to the car, telling her I would wash the breakfast dishes and she should not be late for her trip.

Then she was gone.

I ran upstairs and made a b-line for her room. What I found shocked me. How the FUCK did she know? Laid out on her bed were several outfits including underwear and lingerie. Each with a note pinned to it suggesting accessories and instructions on how to put them on and what day to wear each thing. There were dresses and skirts and bikinis and bras and panties and garter belts and stockings and hair accessories and j*welry and shoes. I turned to her vanity and found more things. There was a basic beginner make-up set and a DVD titled "Beginner Make-Up Lessons For Young Girls." She had the DVD player plugged into her bedside TV so I watched. There were instructions as well on her Vanity. On the make-up kit and all the clothes there were notes indicating that these were all things for me to keep. She even left me some perfume in little sample packets.

I spent the next four days exploring. What I did not know is she had six video cameras set up in her bedroom and was watching me the whole time from the comfort of a hotel room via the internet.

When Monday night was approaching I gathered up all her g*fts and neatly put them away in my one newly emptied drawer in my dresser and cleaned up her bedroom as neatly as possible and took the DVD with me as well. When she got home I was dressed as I normally dressed, I.E. as the boy I was but boy did I enjoy that four days.

When she got back she told me she had been watching the whole time. I am so glad I did not desecrate her room with cum. I did all my jerking off in my own room where she had NOT set up cameras. But she saw every pose and every change of clothes and my attempts at make-up and doing my nails and she complimented me telling me that I did better than she did when she was my age. She told me that on my birthday she was going to take me out for a girl's weekend. It was going to be four days again only it would include going to a spa, having my nails done professionally and getting a pedicure and facial and massage (to die for! -her words) and then I was going to have professional make-up lessons to perfect my look as well as having my hair done. I was a natural blond but it was a dark sandy blond and I was going to have some lighter blond highlights added. More clothes and shoes shopping and she was going to have my ears pierced and get some additional j*welry for me to wear including something made with real gold. The only price had to pay for all this is I had to let her photograph me like I was her model. I was in heaven. I could not believe Mom was so OK about my cross dressing. She told me that I had unconsciously dropped hints for years starting with every excuse in the book to avoid a hair cut. Talking about how I wanted my ears pierced like several other boys I knew. And how I frequently made wardrobe suggestions to her made her think I wanted to cross dress. She said that had I never sneaked into her bedroom that Friday morning I would never have found the g*fts and she would then have found out she was wrong about me. But she wasn't.

Mom has encouraged my cross dressing ever since. We still go on spa days together. We go shopping together though I know buy my own things. Puberty was not fun and involved a lot of waxing. For my 17th birthday she took me to a place for electrolysis and that was very expensive but now I have no body or facial hair. She asked me around that time if I wanted to transition to female and I said no. I told her that I am not and cannot be a female but I do want to be as feminine as possible so I maintain a very slender figure. I don't over indulge in muscle building exercises. I keep my hair long and I never leave the house without some make-up. But I identify as a femboy not a girl. Mom is good with that. She did secretly confide in me when I was 18 that she had wished I was born a girl but is happy that she got me. Also, I am bi and I have dated both girls and boys and I am currently in a three way relationship with a man and a woman who I adore. Mom is OK with that too. I met the man first, he is ten years older than me then we were in a club, me cross dressed and he in a suit and a woman in her late twenties approached us and introduced herself and she gave me a funny look when she heard my deep voice then she was really into it and that night we spent the night at his place and we've been together ever since.

All thanks to Mom.

(0) (0)

Over 75,650 Adult Confessions Shared!

The Best Worst Situation For A Str8

Comments

by Anonymous on Sep 9, 2024 at 11:06 AM

by Anonymous on Sep 30, 2024 at 4:23 AM

Comment this

Top Sex Confessions

Popular Confessions