my first time

My mother always said she wanted a daughter….my guy name was Adrian, so you could see where she was going with that. I was also a real sissy as a k**, terrible at sports, threw like a girl, did very few real boy things.

My best friend and I discovered porn and masturbation together. My mom didn’t watch what we were doing too closely, so we used to jerk off down my basement like all the time. We would get a Playboy or some other skin mg and just go to town. He would catch his load in his hand and dump it down the sink (what a waste) but I would usually shoot my load on the floor(another waste) or sometimes accidentally cum in my pants….I guess mom was able to figure out what was going on. We used to dry hump each other a lot while looking at the mags, with one guy topping the other. My mom caught us a couple of times and we gave her some bullshit excuse, but I think she figured out what was going on.
One day he found a big tit porn mag and that really got us hot and bothered. So I went snooping around and found a sex mag at my uncle’s house. The name was Susie’s Six and it was about a babe getting fucked by 6 different guys…..softcore, if I remember properly, with no actual penetration. So we used this mag a lot, getting hot, stroking, and cumming.

One day, we were beating off like we did all the time when I was really taken by a pic of her sucking a cock. I said to my friend that looked so good ….we both had our cocks out…..and I said I’d love to try it….he was feeling hot , held out his cock, and said go for it… I did…….as soon as my lips touched the spongy head, I knew I so wanted this….he got so hard in my mouth so fast….prob came within 30 seconds…shooting his load in Adrian’s mouth. I liked the taste and swallowed my first load that day. After that, I blew him like every day that summer. I think my mom may have seen us but she never said anything.

Mom was feminizing me at an early age….I was walking around the house in her heels at age 5….I wore my aunt’s heels too and they all thought it was so cute!! That must be where my heel obsession comes from. Mom started buying me girl clothes and having me dress up as a girl when I was home….schoolgirl skirts, blouses,panties…bra and heels when I was like 12. I didn’t dress up for my friend though….unfortunately...

I think my mom did see me blowing my friend. Mom had a LOT of male friends….she seemed to see a lot of guys when my dad was at work. And one day, mom wanted to complete the feminization of Adrian into Adrienne. At that time, she was having me dress whenever I was home….girls jeans or skirts, femme tops and heels, all of which she used to shop for. One day, she told me she had bought me a new outfit and wanted me to wear it for a special occasion. I went to a catholic high school where the girls wore these blue and grey plaid skirts and my mom had gotten me one. She also had a black bra and panties and a pair of black 3” heel pumps for me. She didn’t tell me exactly what the occasion was, but that it would be soon and she would help me get ready.

One morning, she told me I was going to be getting a special treat. The first thing she did was give me an enema….she said I had to be cleaned out before I got my surprise. Then, she had me get dressed in the new outfit, had me put on a short brown wig, and did my makeup and nails and then sprayed me with perfume. My lips and nails were both a sexy red. I have to admit that I thought I looked really good.

Then my mother sat down to talk to me…she held my hand and said that there was just one more step in the feminization process to make me a total girl. I was going to have to have sex as a girl in order to be Adrienne. And one of her friends was going to help me with that. One of her friends had something to do with newspaper delivery boys and he was going to come over to help me. I .was okay looking. He smiled when he saw me and came up to give me a kiss…..he took me in his arms and held me close. He said I was so pretty……prettier than he thought I would be……and he was going to help me become a total woman today. I smiled and kissed him. He asked me if I was ready to become Adrienne and I told him I thought I was. Good!!

Mom told us to sit on the couch together and the afternoon of fun began.

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Categories: Shemales
Posted by adrienneheels
2 years ago    Views: 3,885
Comments (26)
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2 months ago
mmmm you had an early start too :)
it's so much better when ur very young n it's all still new.
2 months ago
sucked my best friend's cock at first fucking as Adrienne was at 15...and no turning back after that!!
2 months ago
my step dad made me 'daddy's little whore'
when i was 9
7 months ago
HELL YEA AWESOME SEXY,sweetie love it you lucky slut,wish I could have been this lucky sweetie
9 months ago
Thank you, honey
10 months ago
HOT mom and sexy you! Great story!
11 months ago
Thanks for sharing that. Great post. Not sure about mom pimping you out, but sounds like everything worked out in the end (pun intended)
1 year ago
can't wait to hear what happens next. Lube is ready and cock is hard in anticipation
1 year ago
that's kinda hot in one way ... still wanna feel a spongy head between your lips?
1 year ago
Can't wait to read more. So Beautiful! Thank you!
1 year ago
Please finnish the story it was so hot
1 year ago
Hot indeed, lets hear the rest...
1 year ago
On a side note- when I was around 11 or 12-my sister in law used to live with us. She was a stripper. After she came home and took a shower I would sneak into the bathroom. After soaking up all of the delicious smells in her outfits. I would wear them and jerk off while staring at myself in the mirror. I have been hooked on dressing up ever since.
1 year ago
This seems so wrong but so exciting at the same time. If I would have had a jack off buddy growing up I would have done the same thing! I was very curious very young. I'd play with my ass and think of boys and girls as I would masturbate. I loved the tranny phone sex ads in the porn magazines more than I liked the girls who were featured :-)
1 year ago
wow, this is so hot
2 years ago
VERY hot!
2 years ago
we are meant to play baby girl
2 years ago
This is Awesome please give more
2 years ago
good story ! , i hope you add more !
2 years ago
I was a newspaper delivery boy in my distant youth. I don't remember ever being invited into a house to enjoy someone become a "total" woman. Actually not even becoming, a less than total woman. Thanks for letting me enjoy, through you, what I missed then. I write a bit.

Maybe you would enjoy my stories on my profile page. I'm always looking for comments.
2 years ago
agree more plesase.......
2 years ago
Now you caught my interest lets see the rest of the story
2 years ago
Please, tell us how it went!!!
2 years ago
Great story. Wish there was more and not end like this.
2 years ago
More need more
2 years ago
more plizzzz more plizzzzzzzz