Timmy wants to be Timi

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Cross dresser wants to be a Shemale.
2.6k words
4.33
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Part 1 of the 2 part series

Updated 02/14/2024
Created 01/21/2024
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Catcher78
Catcher78
154 Followers

Timmy Wants To Be Timi.

Everyone is eighteen or older in this story.

I was six feet tall and one hundred and sixty pounds. I had red hair and no sideburns and some blond fuzz around my ball sack and my tiny dick (four inches).

I knew I was gay since I was young but never acted on it. I lived with my Aunt Ellen who was my mom's older sister as I had not seen my mom since my dad divorced her for cheating on him, we facetimed some but not much. As near as I could tell from those weird events and what Ellen told me she was an escort in Dubai. I googled Dubai escorts and found her in about two minutes, there were pictures of her fucking black men.

My reaction to it was clinical, she had red hair like Ellen and I did as well and I loved her makeup, incredible eye lashes too, she had light freckles on her face and across her huge tits. God I wished I had her tits and her ass too. I sent the website to Ellen and said I wanted to talk to her about some stuff.

I was at school, freshman year at the University of Washington. I didn't have a class for two hours and I was sitting in a restroom in the basement of Savery Hall. Two months ago, I had started giving men blow jobs in restrooms on campus. There were at least three other buildings on campus plus the grad library that had ten basements filled with books and study carrels.

I looked at gay sex movies on Reddit and there were a bunch of shemale pages that totally blew me away. I learned a phrase one of the individual pages on Reddit that showed this beautiful woman with a huge cock, Daisy Taylor fucking this other female who exclaimed she was "cock drunk". I searched on cock drunk in Reddit and found videos of incredibly beautiful black men with impossibly big, long and curved cocks fucking white, submissive boys. Then I saw this page called Tiny Dick girls and they were getting fucked on their cunts and they'd come hard on the cocks and their Tiny Dicks were spraying cum everywhere.

I was in my second week when I sucked my very first cock. The smell of his crotch was musky and I kissed the head of the beautiful cock. It was six inches and bigger than me and thick and I licked all round the purple head and I'd seen precum on those videos and I immediately licked it and it was both salty and sweet and I loved the way he smelled so much and just like in the videos I started bobbing up and down and the thickness stretched my lips impossibly.

My red hair, which was shoulder length fell over my face, was quickly gathered up and held. Oh my God, I was turning him on so much that he wanted to see me and then he came hard in my mouth and it felt like a lot. O wasn't really sure, but when I swallowed it, some seeped out. I looked up at him and had to be in his mid-forties easily.

He said, "You're such a beautiful girl!"

Impulsively I pulled his cock back into my mouth and furiously sucked him again and he was fine with it and it took another ten minutes or so and he came again. He kneeled down and French kissed me. I was so happy. I left the stall and there were three men waiting and one pinched my ass and I turned around and he took his finger and scooped some cum off my chin and stuck it in my mouth and I slowly bobbed on his finger looking him in his blue eyes. He grabbed my hand and pulled me with him and just down the hall he opened an office door and pulled me in and closed the door and locked it.

He pulled me in and crushed me to his chest and kissed me, forcing his tongue in my mouth and his cock was poking my tummy and I dropped to my knees and loosened his belt and pulled his khaki pants down and he was really big. He said, "I want to fuck you!"

I said, "Not yet baby."

Well it was incredible and I was scared all the same and wanted to be careful too.

My behavior was kind of manic now. I had not missed any classes but I started thinking about nothing else.

I had several dates with girls in high school, I loved dancing with them, we'd talk about her clothes and her perfume and makeup and I'd ask how they would apply and what tricks they'd reveal and I'd even go shopping with them. One girl said she really liked me; I was special she thought and that I got her like no guy ever had and we made love.

I went down on her she said my tongue was magical I was scared to show her my dick embarrassed really. But she persisted and I WAS hard and used her thumb and fore finger with these gorgeous nails to jerk me off and she licked my nuts and she swallowed my dick and my balls and I erupted in her mouth.. Jenny immediately kissed me with my cum in her mouth and we swapped it back and forth, she told me it was snowballing."

Her mom had passed when she was in high school and her dad was a trucker and rarely home. I met him once, and he was quiet and huge. He shook my hand and stared in my eyes and my little dick got hard and he knew it.

Jenny had taken our love to another level. She was in charge and I was so happy. When I stayed over she dressed me in her mom's clothes. I was down to one hundred and forty five pounds. At first Jenny would fuck my ass with her fingers, then an English cucumber with the wax on and I had my first anal orgasm. She called it an analgasm. Whatever the name was it was incredible, my clit shot ropes of cum and they doused her tee shirt and I got her face and hair. I was proud as all get out.

One Saturday morning she had gone on a run and her phone rang in her purse and I was practicing in my new five inch open toe pumps and I made it to her purse and took the phone out, but I saw that she had her cute little birth control dispenser and it was pink and she was taking them regularly.

I opened her phone up, there was no lock on it and read a series of dms, men telling her how she was an incredible cocksucker and how he couldn't wait for them to be married and he agreed that a June wedding was perfect. There were more. She was fucking a couple of guys in her office. I opened up her facebook and looked up James, who she was going to marry in June. He was black and a former NFL player, I've never been into football and I turned her purse upside down and there were separate key rings..

I took her mom's clothes off and I pulled some Levis on and some adidas and an old sweatshirt on and left. I blocked her phone number and instead of going to my apartment which was in the Fremont district. I drove down I-5 to my Aunt Ellen's home. I called her and said I needed to talk and needed some advice.

I was thinking about Jenny and how I had fallen hard in love with her and I always told her that I loved her and she would hug me and say," Thank you baby."

She never ever said she loved me. She did fuck my brains out and I was such a fool. I thought to myself, fool me once.

Aunt Ellen was my mom's sister. She lived in Tacoma and was a lesbian and had a series of partners, and was a stunningly beautiful woman. When I presented made up with Jenny's mom's clothes on I aspired to look like her. She had a huge house in Tacoma by the Ruston district.

My mom and dad had been divorced since I was five. I had seen my dad once since the divorce I was in high school and he said, "You look like a faggot. Are you a faggot?"

I balled up my fists and started walking towards him and faked with my left right hand hit him as hard as I could with left hand and knocked him on his ass. He looked up at me shocked and said, "Maybe you are my son after all."

I looked at him and said, "No you're right, I absolutely love to such cock, but this faggot kicked your ass."

Ellen laughed her ass off and told my dad to go fuck himself and get the hell out of her house. I had not talked to him since then.

My mom was a slut and caused the divorce by fucking around on my dad. Ellen raised me and I went to a Catholic school in Tacoma and then on to the University of Washington, where I got my degree in fashion design.

I'd get a call on my birthday from my mom and sometimes Christmas. Somewhere along the line she had become a porn star and had won some AVN awards for MILF of the year or some such shit and I didn't know if I hated her or my dad more.

Her and Ellen's parents had left me a lot of money in a trust fund and I came into it at different stages, twenty one, twenty five, thirty etc. until I was forty when I would get the bulk of the money which at initial stages was five hundred million dollars, but since Ellen was the trustee had grown a lot. Ellen had always asked if I wanted to know more about it and where the money was invested. I always said, "I am doing fine and have plenty. I'd hug her and tell her I loved her.

When I went to Seattle to go to the University of Washington, she made my favorite dinner which was her spaghetti with some sauteed asparagus and lemon sherbet. I helped her wash off the dishes and loaded the dishwasher. I tapped her shoulder and she turned to me and I hugged her hard and said, "Mom, thank you for being the best mom a boy could have."

She burst out crying and squeezed me so hard. I said, "I am so sorry, I should have said this years ago, I love you so much and I will do anything for you."

We cried a bunch. I parked in her driveway next to her Porshe SUV and I came up through the front door, still had a key and I saw her and her mouth was open in a big round quiet oh and then she said, "You're stunningly beautiful Timi." I had left my hair in a ponytail and my make up on and still had my pumps on and so I did sexy strut over to her showed her my nails and kissed her on her cheek leaving my lipstick there.

She said, "If you were not my son I'd say you were a hot chick and ask you to fuck."

I blushed and said, "I always saw me as your daughter."

I told her about Jenny and that I thought somehow she knew about the trust but I go to where my heart was and that Jenny fucked my brains out with a strap on.

"Mom, I said, "I am a woman with a little dick, it's tiny, almost like a big clitoris. I want tits and a great big ass. I have sucked a lot of cock and I've been fucked by men. I am gay, but I want to be a woman to attract straight men and gay men too. I want to keep little dick. It's never been mean to me."

We both laughed and she said, "Well Timi, I do know a little bit, because in high school, you I mean, I thought this was where we were going. You're Miss America beautiful now, Sports Illustrated cover beautiful, just startlingly gorgeous."

"You could be a sissy. Sissies present as women, even get fake tits and even marry. Drag Queens are performers, sissies by definition are shamed as wimpy males and though beautiful often they love the humiliation.

"Then there are shemales, who go through HRT which hormone replacement therapy and some have surgery to augment the size of their penis. It is also not uncommon to have breast enhancement surgery and also to make their ass look like they can attract black men. But then I went on Reddit and discovered a page called "Small Dick Girls" and they're all so fucking beautiful Timi. I knew this was your kind of girl. So Timi, what do you want?"

"I am tall mom; I want really big tits, jiggly and I want to be able to do titty fucks for my men. I do want a nice ass, but I'm almost there, don't you think," I twirled around and stuck my ass out, and said, "you should it with my pink yoga tights."

Ellen said, "There is more, Laser work to remove hair on your face and genitals. Surgery to soften your jaw and Adam's apple.

"Shemale please," I said, "I'm so excited my little clit is as hard as a diamond."

"I have plenty of gay friends, I can someone for you," said Mom.

Always a perfect mom for a gay son and soon to be a shemale, "Umm do you know any black guys?"

"Guys"

"Two or three, please! Then I laughed out very loud, Mom just a guy that will rock me all night long."

"Ok, when?

I said, "Eight or nine is perfect."

I had some pink chinos that made my ass look spectacular. I had to work hard to pull them and I had really cute thong too, almost kept my balls in. A sleeveless pink skintight tee that was sheer and would show off my nipples..

I raced upstairs to my room and painted my nail pink, and laid out my clothes and my pink stilettos. "Mom I yelled with my girl voice, I need some help," I was wearing my thong, only. I held my nails out to her as I turned around and she took in my barely encased clit and balls in the thong, "Do you have some lipstick that will match?"

I bent over the bed showing off my nice ass and my pink little rosebud and turned with the tee held against my chest and said, "I have big nipples and I want him to kiss and play with them, should cut holes for them?"

Ellen said, "No, I have a completely sheer white top, that will show you off. Rub some ice over them just before he gets here, or wait upstairs and then pull the top on. You need big hoop earrings to turn him on when you're blowing him."

She ran to her room and came back with the top, lipstick and the earrings. She did my lips and my hair was in a top ponytail. It was five to nine and Ellen ran downstairs. I was rubbing my nipples and the doorbell rang. I pulled the top on and sprayed some more perfume on my neck and on my ass, a girl's got to make her man want her.

Catcher78
Catcher78
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AnonymousAnonymous3 months ago

I want the black guy to fuck his sissy ass.

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