Feminized By My Mother – Part 1

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My Story of how I was feminized by my mother – Part 1

Charles tells his story about his shemale mom and how she made him a sissy

My name is Charles. Well if you are going to be listening to my thoughts please keep the volume down, I am trying to think. Some things are going on that have got me very mixed up and I have to concentrate. Like most overly complicated things in life, a woman is involved.

I have to admit that I have always been bothered by my penis size. I’ve seen smaller dicks online by typing ‘small penis’ in google but mine is defiantly nothing to boost about at around five inches. I worry that girls are going to laugh at me, which would be mean, or that I just won’t be able to get them off and they won’t be interested in sex with me.

I’ve never actually had sex yet. I just graduated high school a few days ago and I’ve never been a social butterfly. I had some close friends, Thomas for example; Thomas is a good friend of mine. He has short brown hair and a VERY prominent chin. He excels at computer stuff and loves reading. I read as well, but not nearly as much as he does. We play cards and World of Warcraft together all the time. As for females I’ve never had much luck, until recently that is. I’ve been dating this girl, Jennifer, and I think I am going to get lucky with her.

sissy charles photoAbout a month ago she said to me, “Charles, I think that girls should make a boy wait at least six months before they fuck them. My mom told me so. It sure is a rough wait though!”

I blushed like a nervous ninny when she said that, but my dick got hard just from her hand touching my arm and saying that. We had been dating five months and I was sure she was telling me we would have sex soon. Jennifer was a big bookworm, but still popular by virtue of the fact that she was a gorgeous young woman.

So right now, at this moment, we are sitting in my room and it is Saturday night. We are laying side by side on the bed and I’m running my hand through her long dark hair. It’s funny because she is doing the same to mine. I’ve had long hair my whole life. When I was little my mom thought it was cool to have a son with long hair just like hers and she had it cut that way. Since I got old enough to pick my own haircut I just went with it, long brown hair was part of what I saw in the mirror and if I cut it off it would be weird.

It has gotten me picked on some in school though, but I don’t think cutting it would stop that. I get called a fag a lot just cause I’m a bit of a loner and the jock types think I look effeminate. It doesn’t help that my butt is kind of big, which doesn’t make sense to me because I’m skinny overall but fat seems to go to my ass instead of my stomach like most guys. One bully liked to compliment my ass to mock me, it was always, “Man you got a juicy rump,” or “That ass is looking fine Charles!” I’m not gay though just to clear that up. Metallica had long hair, they aren’t gay.

I realized that this was the perfect moment as Jennifer snuggled her face into my neck, she had a long neck, with pale skin, should I start by kissing it? I felt myself getting sissy boy lips imageshort of breath. There were butterflies in my stomach and my legs began to tremble a little. ‘Calm down Charles!’ I thought. I had to act before I lost my nerve.

I shifted myself and lowered Jennifer’s head to the pillow; I propped up on an elbow and looked into her eyes. She smiled at me and my legs quivered. I leaned in to kiss her while my hand squeezed her breast through her shirt. We had made out plenty of times before, and I had fondled her sometimes, so I wanted her to know I was going further than that and give her a chance to tell me no.

I always start out by putting my tongue in her mouth, but somehow she always pushes me back into mine. She likes to bite my lips and hiss at me; sometimes she bites my neck painfully hard. My hand reached her pants and I slowly undid the button. When she didn’t protest I lowered the zipper. Her hands went under my shirt on my back and scratched me hard, her nails digging into my skin as I pulled her pants off.

She had on cotton panties with blue and white stripes, tiny hippos were running along the lines. I rubbed my hand over her crotch, feeling the warmth and the moisture on the fabric. Jennifer pulled her mouth off mine.

“Those come off last bad boy.” She breathed into my ear and then pushed her tongue inside. I giggled as she wiggled her tongue in my ear, it tickled. I got her shirt off, then her bra, and backed off a bit to take off my shirt and pants so that I was left in my boxers. Jennifer spread her legs and grabbed my arms, pulling me into her embrace and clamping her mouth on my neck again. I felt her tits pressed against my chest, the first time I had ever felt bare tits, my dick was hard and I wanted to fuck her bad but I didn’t want to rush this. Jennifer bit me hard making me flinch then she kicked with her legs and rolled me over so she was on top. She sat up and looked at me with a wicked grin, licking her lips.

“You are so hot Jen!” I said, gazing at her round boobs. She looked down at them and pressed them together, then pushed them to my face.

“I know you want to worship my tits Charles.” She said in a sultry voice.

“Oh yeah…” I gasped, running my lips along the lower curve of her tits, licking at her fingers as her hands squeezed her breast and shook them right in my face. The soft bouncy jugs drove me wild, I slurped loudly on her nipples which she offered me for a few seconds at a time, then moved her tits so I had to catch them. She slapped me with them a few times actually, not sure if that was intentional.

“Bite them.” She whispered.

I took her nipples in my teeth and flicked my tongue over them.

“Harder!” she demanded.

I bit her with about half my strength and she moaned.

“Chew on my tits Charles! Hurt me!”

I left marks around her breast, they were covered in spit when I was done and had bruises from when I got really excited and she screamed at me,


Finally she pushed me down her strong hands on my shoulders. She lowered her face to my chest and proceeded to give my chest the same treatment. It felt great at first, her tongue electrified my nipples and it was like there was a straight connection from them to my dick, I was afraid I would soot in my briefs, but then she started biting the crap out of me and I whimpered. When I tried to push her back she slapped my hand away. I was afraid to turn her off, so I took it as best I could, emitting a combination of sighs when she licked gently around my chest, moans when she swirled her tongue around my nipples, and shrieks of pain when she sank her teeth into my flesh like she was going to tear out a chunk.

I was laughing as she licked the sides of my stomach on her way down, I was very sensitive there. Then the anxiety was back all of a sudden when I realized she was about to see my dick. What would she think? I looked down at her and tried not to show the worry on my face as she put her fingers into the waistband of my boxers and pulled. My five inch hard penis sprung free, and without batting an eyelash, she engulfed it with her mouth.

“Uhhhh!” I groaned and reached down to stroke the back of her head. The feeling was amazing, unlike anything I’d felt before. It was her breath and her tongue I think that really did it. I’d had wet towels before with hot water, and an awesome pocket pussy that was super soft… but they weren’t alive like her mouth. Her nose let hot air flow out onto my crotch and goose bumps went down my legs, her tongue wiggled on the underside of my cock. She looked up at me as she bobbed her head on my dick, I felt my balls tightening up and the pleasure intensified. ‘No not so soon!’ I thought.

“Jennifer,” I said, “I’m gonna, uhhh gonna, you know…”

She didn’t stop or slow down; she just pumped my dick in and out of her mouth, staring up at me. I squeaked embarrassingly and came. My dick twitched in her mouth and poured cum onto her tongue. She held me in her mouth as I deflated. She kept a seal over my dick as she let it slide out her mouth, the wet head falling back onto my balls, and then she crawled up my body.


She opened her mouth and showed me then cum on her tongue, a grin on the corners of her mouth. I was horrified as she leaned in and stuck out her tongue. I turned my head away quickly. She closed her mouth and smiled then gulped audibly. She looked a little disappointed which I was sad about but seriously, what can a girl expect? I am not kissing her when her mouth is full of my cum. She lay next to me and started kissing my neck.

“My turn now!” She whispered in my ear, and flicked her tongue across it. I felt her hips wiggling next to mine as she pulled off her panties.

Jennifer sat up and crawled forward. She yanked the pillow from under my head and put a knee on either side of my head. I inhaled her scent and looked at her pussy. It was my first real look at one and I stared transfixed as she pushed it forward. She had shaved it to a landing strip over her clit. It was sexy as hell. My willing lips parted and I began to kiss around the lips of her juicy cunt. The taste was sweet and tangy, like a green apple, slick fluid filled my mouth.

“Oh yeah, eat me.” Jennifer mumbled.

I did the best I could, probing her feminine parts with my tongue, exploring to see what made her respond. I pushed in as deep as I could, and lapped at the skin around the lips. I kissed her protruding slit and sucked on it, making it puff out a little more. Her fingers curled in my hair pulling my mouth tight against her. I loved her shoving my face into her wet slit, making it hard for me to catch my breath. My dick was standing up again.

“Do you like it?” Jennifer asked. I mumble my agreement as she shook, grinding her pussy over my mouth and nose. Her cunt-lips and pubic hair filled my vision. “Ohhh, suck my clit, suck my clit, suck it hard!” she squealed. I sucked her clit into my mouth and worked it with my tongue as she came.

Her body quivered as she came down off her orgasm and I licked her cunt-lips gently until she moved back off my face. She scooted back until she was astride me and lowered her pussy to my dick. I sighed as she took hold of my penis and lined it up with her vagina, lowering herself onto me easily. I shouldn’t have been surprised that she wasn’t a virgin, but part of me had hoped she was.

Her nails found my nipples and pinched me as she started to bounce on my dick. “You ate me good.” She said, looking down at me. I tried to sit up but she pushed me back down. “You’re going to learn to do it even better.” She licked her lips; I rubbed her thighs as her hot pussy gripped my dick with each stroke, her pussy juice splatting onto my balls and crotch.

“You feel so good!” I said.

“Don’t you dare cum in me!” she shouted.

I managed to last a while that time, having just cum. Jennifer’s tits were dripping sweet and she was breathing heavy when I finally announced I was close. Once I did she pulled off me and grabbed my dick. She jerked me hard and I spurted onto my stomach. Jennifer cooed and curled up next to me, putting her lips to mine. I could taste the saltiness of my cum on her lips, but I thought better then to refuse to kiss her now. She wrapped her arms around me and I just thought about how incredibly lucky I was.

My mom likes to stay out late. I had taken Jennifer home and kissed her goodnight, and was sitting in front of the computer wasting time browsing when her and her date stumbled in. I love my mom, and I don’t mean to sound judgmental of her, but she is a bit ah… loose? Is that the word? I don’t know I don’t mean to say she is a slut she doesn’t bang a bunch of guys and sleep around… but she always has a boyfriend and they never last more than six months. Although her current boyfriend breaks that trend actually, they have been dating for almost a year, his name is David and he is a pretty cool guy. He is laid back and has a twisted sense of humor.


Oh I don’t know if I mentioned it but my mother raised me alone, my father ran off when I was little and my mom never heard from him again. I didn’t have any issues with my mom’s boyfriends about replacing my dad or anything, he was a prick, and my mom deserved to be happy. The only thing about the men she brought home that I didn’t like, don’t tell anybody this, was that I was jealous. My mom is really hot and sometimes I think about, you know. I’ve looked in her draws and sniffed her panties occasionally, which would get me hard instantly, especially the ones she left on the bathroom floor.


She didn’t smell anything like Jennifer though, now that I thought about it. But I guess all women smell different. Anyway my mom has fantastic tits, bigger then Jen’s. I heard music coming from my mom’s room. She plays music to cover the sounds of her and her boyfriend’s fucking; I figured that one out by like eleven. Sometimes I would creep up to the door and listen to the sounds under the music. I could hear slapping frequently, and that put dirty thoughts in my head of my mom being spanked.


In the morning I was sitting at the kitchen table when my mom came in and sat next to me. I was still waking up early because that’s what I was used to from school. Soon I’ll be sleeping until noon though. I was in my underwear. I walk around the house in my briefs all the time. My mom favors modest dresses at home, although I’ve seen her change into some revealing outfits to go out in. I was busy dwelling on the size of my dick. Did Jen like it well enough? She looked like she enjoyed riding me, but if she came it wasn’t near as explosive as when I ate her.

“Are you okay honey?” My mom asked.

“Yeah…” I said.

“Is everything okay between you and Jen? I saw she wasn’t here when I got home.”

“Mom you got home at like midnight!” I told her.

“So? Your girlfriend can spend the night you know.” She said, putting some breakfast bars and a magazine on the table.

“I don’t think her parents would feel the same way.” I said.

“Well you graduated high school you can do what you want. They can’t keep her from growing up.”

“Mom,” I said hesitantly, “How big of like, dicks you think girls my age like?” I felt dumb for asking immediately

My mom laughed and I looked down. “Oh I’m not laughing at you honey it’s just that was out of nowhere. Really I don’t know I only know what kinds of cocks I like, do you want to know about some of the best ones I’ve had?”

“No! Never mind mom that was a bad idea forget I said it.” I had terribly embarrassed myself, why couldn’t I just keep that to myself?

“It’s okay honey. Are you worried you won’t satisfy her?”

“Yeah.” I admitted

“Well, let me see it.” She said.

“What? N-no way!”

“Don’t be a baby you walk around me in your boxers all the time and I saw you naked all the time when you were younger it’s okay.”

I shouldn’t have, but I shouldn’t have brought it up. At this point I figured I might as well. So I slowly pulled down my boxers and show myself to my mom.

“Well you gotta get hard honey. There is a big difference between hard and soft.”

“Ehhh,” I blushed, “I don’t think I can do that right now…”

Then I gasped as my mother reached over and touched my dick, she squeezed the base with her fingers and tugged on me. I was like a deer in the headlights but my mom just smiled at me casually. Slowly my dick came to life and stood out.

“Oh, that’s not bad.” My mom said. “It might be a little below average but so what. You think every girl needs ten inches to get off? You’ve been watching too much internet porn baby. Besides some woman is gonna love you just the way you are. You’re a sweet young man now forget about that.” She went back to her magazine and chewed on a fiber bar.

I was freaked out, but maybe a little relieved that I had told my mom about my fears. I was a little horny now too. I called Jennifer.

“Hey Jen, you ah, want to go out to the pool today.”

“That sounds great… bring condoms.”

‘This is so awesome!’ I thought as I got ready.

“Are you going out?” My mom yelled. “Yes.” I replied.  “Okay don’t get her pregnant.”

I’m too nervous to get condoms from the grocery so I stopped at the gas station and used the machine in the restroom. Jennifer came out of her house in her swimsuit and I watched her ass as she walked around to the passenger side and got in. When she sat down she put her hand in my lap and said, “Don’t drive too close to any other cars.”

I was super nervous as I drove, but I couldn’t bring myself to push her head out my lap. It was the middle of the day and she was slurping on my cock as we drove down the highway. This girl had been waiting to open the floodgates!

That night when I got home David’s car was in the driveway and I heard the bed creaking from my mom’s room. I walked down the hall to my room and saw her door was cracked open. ‘Holy cow.’ I thought. ‘You’d think she thought she lived alone!’

As I quietly crept past her door I couldn’t help but look in. I saw my mom dressed like some cheap prostitute with bright red lips, a miniskirt, a strapless top that just covered her boobs, and thigh high pantyhose. David was naked and pulling her hair as he fucked her from behind. I even overheard them talking dirty.


“Uugh, fuck that hits the spot!” My mom said.

“You have such a tight asshole Rachel!” David hissed.

My mom was taking it in the ass! If Jennifer had not made me cum twice already, I would have pulled it out and started beating it. Fortunately I was sexually sated and so my higher thought processes weren’t that impeded. I did stare for a long while though.

What I saw the next morning would change my life though

As I walked past her room the door was wide open and I looked in. David was gone, and my mother was asleep on top the covers, naked. I peeked my head in and my eyes traveled down her body. ‘Such nice tits! Even a hot belly button… wow she has a big bush… wait…’ My mind failed to process for a moment. I imagine it was something like discovering you’re in the matrix, the whole world didn’t make sense! This was impossible! This was my mom, my mother, the women who gave birth to me, and she, how could she….

My mind reeled as I gazed at my mother’s soft cock.

This couldn’t be! She was a man, a man! My whole life she had lied to me! Her whole character took on a different light. All her boyfriends; I realized they were all fucking her in her ass! They were gay or just plain weird! My mom was a fucking fag!

I wanted to puke, I went in my room and closed the door, burying my face in the pillows and sobbing. I was sickened on so many levels, especially when I thought about all the sexual things that I myself had thought about her, those thoughts had been about a guy! My head was in pure turmoil, I must have lain there for hours by the time my mom came in.

“Son, baby? What’s wrong?” She asked. She put a hand on my shoulder.

“Don’t fucking touch me!” I screamed.

“Honey…” She tried to slip next to me on the bed.

“Don’t get near me! You fucking faggot!” I screamed.

“Oh. Oh God Charles, I’m so sorry….” She tried to reach for me again.

“I said don’t touch me you damn cock sucking sissy!” I was just so overcome with anger. I slapped her and shoved her off the bed. She looked up from the floor shocked and I glared at her. Tears started to well up in her eyes and she turned away. “We’ll talk later…” She said slinking away.

I lay back on the bed and breathed out a sigh. I just couldn’t believe it. I just wanted to avoid the issue. Jennifer would be with her family at her grandparent’s today, so I called Thomas.

He showed up about thirty minutes later with some playing cards and we sat on my floor playing games. I tried to take my mind off my mom but it was hard, especially when Tomas made a comment, “So, your mom is she single right now?”


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. Avatar
    GS test  March 31, 2013

    How i was Feminized By My Mother | Crossdresser Society


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