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How My Mom Feminized Me – Part 3 – Crossdreser Society | An Online Resource for Crossdressers | Transgender

How My Mom Feminized Me – Part 3

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This is part 3 of my story, how my mom feminized me!

I got back in the shower to rinse off and then we started trying on clothes. My mom pulled out some gel boobs and had me put on a bra.

“I wore these before I got implants.” She said with a smile.

That was a little weird but they puffed out my bra and I shook my chest at the mirror, fascinated by the idea of having tits on me. Fortunately (I guess) my mom was roughly my size. When we started putting on panties I couldn’t help but think about the fact that these had had my mom’s dick in them. We went through a variety of outfits, my mom continuously trying to put less clothing on me while I tried to put on more modest attire. In the end it was somewhat of a compromise, I showed a lot of leg in the dress but at least it wasn’t like many tops she had that showed her whole stomach, though mine would actually be slim enough to pull it off.

“You know what I have always wanted to do?” She asked me.

“Ah, no.” I replied.

femme boy crossdresser image“I’ve always wanted to give my little girl pig tails, is that okay?”

Well that was more gay then okay but at least she was nice about it, so I sat next to her on the bed while she did my hair into pigtails, and explained how I could do it myself later, if I wanted to.

After that we stopped and ate sandwiches, she made them while I sat and read some girl magazine she gave me. I doubt this magazine was very representative of all women though, unless they are secretly far more obsessed with sex then men and have fooled society into thinking otherwise.

After that she put make up on me, fortunately not gaudy amounts and bright coolers like I knew she went out in sometimes but soft pink colors. I looked worriedly at my painted fingers.

“Doesn’t this stuff take a while to come off?” I asked.

“Well that’s what nail polish remover is for silly!”

I didn’t even know about nail polish remover. I had a lot to learn about dressing as a woman.

“Beautiful!” My mother pronounced as she turned me around in my heels. “Your one of the best looking trannies I’ve seen without any surgery or hormones. That bubble butt of yours really helps.”

“I’m not a tranny Mom.” I sighed.

“Oh course honey, cross-dresser I should have said.”

‘I’m not a cross-dresser.’ I thought as I looked at myself in the mirror. ‘That’s a guy in the mirror, that’s me. I am a man.’ Would other people know? I doubted they would know in the dark of a club or if they were drunk. What if guys made a pass at me when we went out?

‘Oh yeah,’ I realized, ‘they’re gone be gay.’ I needed to look as femme as possible.

“Try and speak in a girly voice.” My mom said.

“How… no… How do you do Sir?” I said. My mom laughed.

“You sound like you’re British.”

“Yes mum! I feel pretty. I like Roses.” I practiced slightly different voices while my mom made a phone call. I sat in front of the mirror and actually had some fun making different faces and saying silly things until my mom got back.

David came over at around five and he had a friend with him, somebody I have never met before. ‘What the fuck?’ I wondered. Now some random dude is going to see me all dressed up like this. With David it was cool because I knew he wouldn’t mess with me over it.

But then, I guess David is gay. I kept forgetting and being shocked by the truth about my mom. It was like my mind wanted to slip back to the old reality. Mom is dad was an idea that I had trouble accepting.

David was totally unsurprised to see me dressed up; I guess my mom told him on the phone. “So what’s your girl name?” He asked.

“I thought all trannies had girl names. Let me guess, Charlesielle? That fits easily enough right, or did you get creative?”

There was a guy at my school who made fun of my ass by calling me Charlesielle and saying I had a fine rear so Charlesielle didn’t really appeal to me, but I guessed it didn’t matter. “Charlesielle” works but I hadn’t thought about it, this was kind of sudden.”

“So you found out Rachel was a t-girl last night huh? Man you took it well. When my dad found out my first girlfriend was really my best friend in girl’s clothes he flipped the fuck out. He was all like ‘No queers in this house’ you know?”

I guess mom gave him a white washed version of last night. He thought I was immediately supportive of her and then wanted to go out with her on the town in drag. This made me think about what exactly the fuck I was doing right now. Honestly I didn’t know, I was just doing what my mom said, hoping we’d resume a loving relationship again. I love my mom, I really do. I was still pissed though, about the lies more than the rape, maybe I had that coming, I had hit her and berated her so… I don’t know.

My head hurts from this shit! No one should have to deal with this bullshit!

David introduced his friend, Dickey .

“Is that your real name?” I asked in my British girl voice.

“That’s what everyone asks,” He said, “And it is. It’s my last name and sort of my nick name too.”

Dickey had dark skin and short cut hair, I guessed he was mixed black/white but he could have been African American with very light skin. Heck he could have been Indian I’m not good at such things, he had no accent though his voice was slightly raspy. He was actually very skinny, I wondered if he ever dressed as a girl, he could probably bull it off, but his arms suggested that his body was tight and muscle, just without bulk. Maybe that’s how some trannies are though.

I needed to research this stuff, I realized, but there was no time before tonight to get away and do so. My mom came out with drinks, including one for me. I can barely stand the taste of alcohol, but these were fruity bitch drinks so I could stomach it. My mom had never had qualms about me drinking and I had never abused her trust, mostly because I can’t stand beer.

We were sitting on the couch drinking and talking, and I learned that Dickey and David had met in the army, at eight we left the house and went to Chili’s for dinner. If the waitress noticed anything strange about us she didn’t show it, but I was very nervous out in public. I realized that this dress, it certain positions, could potentially show very closed to my panties, I kept a hand on my thigh as if to keep a gust of air from blowing up my skirt and showing my panty covered dick to the world.

The main thing that bothered me though was that Dickey drove me while mom drove with David. Then Dickey sat next to me at the restaurant, and as we left for the club I started to wonder what the deal was. Dickey seemed like a cool dude but, well, here I was in woman’s clothes riding alone with a stranger, who I had strong reason to suspect was a homo. Was this guy my date? Maybe mom figured he would keep other people off me and maybe she knew him and that he wouldn’t try any funny business on me.

I was really incredible squeamish as we entered Club Triangle (what a gay fucking name I mean come on) and I saw men dancing with men all around me, as well as women rubbing up on other women… or were they guys too? The lyrics to some band I didn’t know sure didn’t help much as they sang,

“Cause your filthy Oooh, and I’m gorgeous! Your disgusting Oooh, and you’re nasty, and you can grab me oooh, because you’re nasty!”

The club was actually very nice though. My mom took my hand and pulled me to the floor. “I have to teach her how to dance with guys.” She told David and Dickey.

I didn’t dance in my normal life! Now my mom was dragging me out into the middle of a gay bar in drag to dance? This was fucking embarrassing. At first I just stood there while she danced.

“Come on!” She shouted, shaking her hips.

“I don’t know how to dance!” I replied.

“Don’t be silly! Only guys have to know how to dance. We girls can do anything and guys think it’s dancing so long as our ass is moving.”

Well that didn’t encourage me much. Shaking my ass for all these dudes to stare at wasn’t appealing, but I was in disguise wasn’t I? I shook my body some and tried to loosen up. Maybe I could practice and take Jen out. She would be surprised if I could dance. The heels made it harder… high heels are an awful concept entirely.

I actually got into it then and was shaking my ass against my mom some when I noticed Dickey and David cheering us on. That was embarrassing. I tried not to rub up on my mom after that, although that would have been preferable to what happened next.

I felt Dickey’s hands on my hips and suddenly he was dancing behind me. He wasn’t touching me too aggressively, but enough to make me nervous. My mom was dancing with David right in front of me. After we danced for a while we fortunately went over to some pool tables and my mom decided we would play a team game of pool, me and her versus David and Dickey.

Well I sucked at pool and couldn’t get a single ball in, my mom on the other hand destroyed every time she shot and managed to beat David and Dickey despite the handicap of me being on her team. The only unpleasant part of that was when she would lean over and stick her ass out. Every guy nearby checked out the panty shot. When I leaned over the table to shoot in the same way I could feel their eyes on me, happily I don’t think my junk showed in my longer dress.

Dickey brought me some drinks and I nervously drank (being 18 and all). But what could they do other then throw me out anyway? Actually that would have been fine by me; I drank with ease after that realization. On the way home I could feel the world slightly off tilt, I was on a boat but the sea was clam. The alcohol eased my tension around Dickey some, he touched my hand and I didn’t say anything. He moved it.

‘Do wha?’ I internally mumbled, and squeezed with my fingers. What was that? I rubbed around. It was dark and I was somewhat intoxicated so for a moment I didn’t get where my hand was. There was something soft under it, I pawed around, it was soft but there was a lump. It was a bag or something; maybe he wanted me to get him something out while he drove.

I felt about for a button or clasp, found a zipper and pulled down, reaching inside. It was warm, and furry, like there was a fur blanket in there; I wrapped my fingers around something and pulled it out. It was stuck and I tugged it some but it didn’t come out.

“Waz dis?” My fem voice was slurred; the liquor was sneaking up on me.

I squeezed it and ran my fingers up its length until I felt the bulbous head, then it clicked and I pulled my hand away.

“Eh, thas no nice…” I hiccupped. Those were bitch drinks weren’t they? How much alcohol had I had?

“Hey babe I just put your hand on my lap!” Dickey laughed. “It’s okay relax.”

I did that to myself I guessed. “Ohhh, is okay.”

We got home and I fell out the car door. Dickey came around the side and said, “You need some help Charlesielle?”

“Not drunk!” I said, “I walk fine.” When I lay there unmoving her picked me up and carried me inside. He was skinny but strong.

“You strong…” I muttered.

He took me up to my mom’s room and laid me on her bed, I guess he didn’t know where my room was.

“Do you want something to drink?” he asked.

“Yes, you a gentlemen you are go. Go bring drink.” Some water would be good, or soda.

In a few minutes he put a glass in my hand and I started gulping it down. It was like a slushy or something. Wait no…

“Dis not wata.” I said.

“Haha, no you didn’t say water, sorry. It’s your mom’s strawberry daiquiri. Are you doing okay?”

Ugh, alcohol. That wasn’t good. “Oh I fine! Just lost my balance.” I hiccupped.

My mom lay in the bed next to me, David was on top of her and they were making out.

“Get a room lease!” I said, falling back onto the pillow. I didn’t remember my mom having a ceiling fan.

Dickey was taking off my heels. That was good, they hurt like the devil, and then his fingers rubbed my feet.

I sighed, “You gentleman…” I told him.

I wondered how many calories all these fruit drinks were. ‘They are going to go straight to my ass.’ I thought. I had never been this drunk before. In my head I felt fine, I didn’t feel inhibited, but it was like my thoughts weren’t getting to my body right. Dickey’s hands were messaging my legs that was nice of him, but gay, so I tried to tell him to stop. I succeeded in making a girlish mumbling but the words were just noise.

“Oh, David!”

I looked over at my mom, her top was hiked up and David had one of her nipples in his mouth. That was good, I thought, he could keep her off me. He was pulling down his pants; it looked like he might be in too much of a hurry to undress. That was good too, I didn’t want to see him fucking her naked.

Wait… “Sow don.” I said. I needed to think, this was off.

“Of course, just relax.” Dickey said.

‘I wasn’t talking to you.’ I thought.

I felt a breeze on my balls and shivered. Someone sucked on my inner thigh. I looked down and saw Dickey naked. I had been right; he was muscular but skinny, like spider man. I saw him licking up toward my dick.

‘Stop.’ I thought, “Stop.” I said.

Dickey nodded, like he understood, but he just kept on. He was licking my balls then and I gasped. I felt my mom squeeze my hand and looked at her. She had a big grin on her face and was being shafted by David.

“Fuck my little girl good Dickey!” She yelled.

Dickey had a bottle of lube in his hand and pushed it against my asshole.

‘Stop, I thought. “STOP” I said.

I trembled as cold fluid squirted into my rectum. This was fucked up, I needed to get the message across, and this guy was dense!

Dickey was moving up my body, kissing my stomach. I had to do something, but my arms only failed around like somebody had inverted the controller and my mom held my right hand tightly.

‘I’m not gay, I like girls.’ I thought. “I ike gahs.” I said.

Dickey laughed at me. “God you’re so drunk.” His hands were rubbing up and down my bare chest. When did he get me naked? Had I just blacked out for a second? I didn’t know, maybe he took it off while I was thinking about something else.

“Hot drunk.” I said. Somehow I couldn’t believe I was this far gone. If I could just collect myself, but I had never been drunk like this.

Then I felt his dick at the entrance to my pussy, ass I mean, I’m a guy…

“Uggh!” I grunted as he pushed forward.

“Hurt.” I breathed.

“Shhh.” Dickey shh’d me.

“Uh… uh… wha… ah…” I clinched my mother’s hand tighter as I was penetrated. I couldn’t see his member but it felt large, bigger then my mom.

A bizarre thought popped into my head. ‘I’m small, my mom’s average, this guy is big… it’s a circle… what about David?’

‘You don’t care about David’s cock!’ I yelled at myself in my head.

“Your ass feels so good Charlesielle.” Dickey said in my ear.

“Hanks.” I said drunkenly. “But I a gah. Uhhh, not gah. Top fuck my.” I was shaking under him, this horribly shaking just seemed to take over when I was nervous and sexually excited.

‘Oh shit,’ I realized, ‘I’m excited.’ Just like with my mom my dick was hard on Dickey’s stomach as he rode my ass. I could feel his pubic hair tickling my balls and it was not unpleasant, physically. Emotionally it was awful; I suddenly understood why they say drunken people can’t give consent. I was fucking out of it, only present enough in my body to watch horrified at my date rape, but I couldn’t act to stop it.

Dickey moved me around, I gave up resisting, I tried to go somewhere in my head to wait this out. I was flat on my stomach and my legs were spread, my mom had my left hand now, and her other hand was pumping David’s dick with the head in her mouth, but her eyes were on me.

Dickey entered me again and it thankfully wasn’t very painful. My ass was lubed and warmed up for him, and he pressed himself to my puffy rump as he fucked me.

“Your ass is beautiful.” He complimented me.

If my mom saw my horrified expression she didn’t acknowledge it, she just kept blowing David’s dick. Dickey was touching something in me that got my dick really hard, this position felt better than the other ones even. I realized if he lasted long enough I would cum again, cum from getting fucked by a guy. But what’s it matter, I was already fucked. I started to have some of the same thoughts I had last night, that when this was over I’d just pretend it didn’t happen, ugh but thinking was getting harder, I’d think later.

I heard myself moaning but didn’t care anymore, this was going to happen, had already happened.

“Gaw… tha… hot…” I didn’t even know what I was saying, I started grinding my ass back into Dickey as he humped my fat ass. The grinding rubbed my dick on the sheets too, that felt nice. “Iz ice…” I humped back harder.

“Tell him where you want his load!” My mom shouted at me. I saw she was jerking David’s dick hard with both hands, it was big, so the circle was top heavy… it was clear where she wanted David’s cum before she said it.

“Cum on my face David!”

I didn’t want Dickey cumming on my face! Something about not getting it in my mouth was important. That consideration was forgotten however as I felt an orgasm building.

“I’m gonna cum!” Dickey panted.

“Put it in her mouth!” My mom suggested.

No… not that! “Ugh… ass, cum Dick…” I pleaded. It was too soft, he didn’t hear. Dickey pulled out and pushed me onto my back. No fucking way he was going to…

He did, he shoved his dirty cock into my mouth and I choked, with a few thrust he was deep and both his hands held my head as he fucked my face. I was surprised though, his dick didn’t taste too soiled it was just salty and… What? What the fuck am I thinking? I felt fingers on my cock, my mother’s I thought, jerking me.

Dickey moaned and a shot of jizz hit the back of my throat. I shut my eyes and tried to shake my head but dickey held me in a death grip and another shot coated my tongue and then another. I gagged as he pushed deep and his cock pulsed a few more times, feeding me his seed. My lips were tight around his tool and I had no choice as cum slid towards my tonsils I had to swallow or choke on it. The big wad of cum went down my gullet. He pulled out and I coughed.

I heard my mom cheering as she pumped my dick with her hand. “That was so hot you did great Charlesielle.”

She slide over me as Dickey sat back, recovering. Her lips touched mine and I tasted David’s cum on her tongue as she probed for Dickey’s from mine. Her head pulled back and lowered to my cock, I inhaled sharply when she took me in her mouth and sucked hard. It was no time before I squeaked and erupted in my mom’s mouth.

She brought her head up to mine and forced her tongue back into my mouth, it was covered with my spunk, she hadn’t swallowed a drop. I was helpless as she force fed me my cum, She wasn’t drunk at all and I couldn’t move my head when she pulled on my hair and held me there. I surrendered and drank my own cum.

She pulled back after giving me a loving peck on each cheek and I lay down, mentally and physically exhausted. Dickey came over and hugged me, sleep came blessedly quick.

Dickey and David were gone long before I got up, as was my mom, there was a note on the kitchen table.

“What the fuck?” I said, rubbing my throbbing head. There was a picture of me with Dickey’s cock in my mouth; my mom’s hand was jerking my dick, though you couldn’t tell it was her in the picture. My eyes were staring up at Dickey. David must have taken it. The note said,

“Had a great time last night! Got some souvenirs from your mom, don’t worry I know your closeted nobody is going to find out from me!” It was signed Dickey.

I didn’t fully recall the specifics of the night before, you probably know more than me if you were listening in. I know I got too drunk and got tapped like a slut by a friend of my mom’s. I knew this picture made it look consensual, and they probably had more, it would be my word versus the three of theirs if I said otherwise.


About the Author:

Hi, I’m Marcy Simpson, the founder and creator of Crossdresser Society. I have been a crossdresser for over 25 years and I am also an author, photographer, entrepreneur, and admirer of the feminine realm. I currently work and live in Los Angeles, California.


  1. jesse  December 15, 2013

    wow you write very erotic stories

  2. Deepthi philip  December 28, 2013

    Hi Marcy !! Ur story was awesome !!! I live in Bangalore,India. I am a 15 year old male crossdresser. Please help me if u can. If ur interested in helping me please mail me at : amalbarca777@gmail.com. I realy like 2 b a girl.

  3. Kary desuja  April 6, 2014

    Hi deepti , I m also cross dresser , I m also live in India in Delhi , can u help me in Chang my all life firemd pl send me mail , karydesuja@yahoo.com

  4. tiamarie512  June 19, 2015

    Love the story about charlisse me I am a Crossdresser to LOVE BEING FEM I LIVE FOR IT I DRESS 24. 7 FEEL WONDERFUL FAV.3SAYINGS SILK LACE SATIN


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