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Feminized By My Mom – Part 4 – Crossdreser Society | An Online Resource for Crossdressers | Transgender

Feminized By My Mom – Part 4

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This is the last part of my story how my mom feminized me!

Not that I would, I mean if my mom went to prison I’d be on the street and that would be bad. Plus my mom hadn’t really done anything, I figured. It was Dickey’s fault for fucking me when I was clearly too drunk my mom probably thought I was willingly involving myself, I doubt she intended for the night to end like that. She was probably a bit tipsy as well.

Beautiful feminized boy photoAnd if Jennifer found out, the potential for humiliation was limitless. I called Jen up and we talked. She wanted to see me and I was glad to tell her I was free, I left to pick her up (After a bath of course, during which I soaped up my ass really good) and we came back to my wonderfully empty house.

“This is great! Your mom works in the day and you oh, sorry, I guess it isn’t great that you don’t have a father hah, sorry you know.”

I smiled, “If you were going where I think you were going with that then your forgiven.”

“Oh did you think I was gonna say it was great cause you could fuck me all day?” Jen chewed on one of her fingers and looked me up and down.

“Yeah, that is exactly what I was thinking.”

“Ohhhhh, you think I’m some cock hungry slut that just wants to fuck you constantly now that I let you get in my pants huh?”

“Yeah, seems that way.”

“What?” She looked at me with a fake hurt expression, “You’re not supposed to agree you jackass! I’m a lady!”

“Sorry my lady, I’m new to this actually.”

“Oh yeah?” She asked. “Was that… your first time the other day?”

I nodded.

“Ohhh, and you didn’t tell me! That is sweet I popped your little cherry.” She hugged me to her.

“I, ah, don’t have a cherry.” I said. I really don’t want to think about what that brought to mind.

“Oh yes you do! I popped it, don’t steal my thunder.” She rubbed her tits against my chest and stared into my eyes, licking her lips. “We fuck first, and then we go out and have more fun, and come back here and fuck more, sound good?” She asked.

That sounded pretty good I can’t lie.

She stripped fast in front of me and I went down to my briefs. She stood at me with a questioning look.

“What?” I asked.

“Get naked!” She shouted. “I ain’t pulling down those boxers with my teeth EVERY time we do it.”

“Oh yeah.” I said, I had just left them cause I felt better with them on, honestly I might prefer to fuck her with them on…

As we made out I was rubbing her ass cheeks and thought about all the ass fucking I had experienced. Dickey had acted like it was great; I wondered how it felt, maybe…

I slid a finger between her rear cheeks and she moaned approvingly. She was gonna let me! I played with her asshole while I sucked on her tongue, after a minute she pulled back.

“You wanna fuck my ass?” She asked.

“Oh yeah!” I exclaimed.

She grabbed a pillow and held it close, “Get back there then!”

I moved behind her and admired her fantastic butt. I moved forward and rubbed my dick on her buttcheeks. I put my dick between them and squeezed her cheeks together on it. She giggled, “Be naughty…” She purred.

But when I started to push against her sphincter she huffed and shot a killer look back at me. Oops, Of course I was dry. I spat on my hand and rubbed it around my dick. Then I tried again.

“Hold up there lover!” She said, stopping me. “If you’re gonna fuck a girl in a hole you have to show her your appreciation for that hole.”

That didn’t make sense to me, appreciation?

When I stared at her confused she said, “You’ve got to eat it dummy, hah, you were a virgin. It’s okay go ahead and worship my asshole.”

She wanted me to lick her asshole? That was worse than fucking cum! I kissed her pussy from behind and she moaned. While I stared at her asshole and licked her vulva I thought about whether it was worth it. Once her pussy was good and wet I decided to say fuck that. I didn’t need to be humiliated when I was with her too; I got that from my mom apparently.

“Well I guess you’re just not ready for that, maybe later.” She sighed as I pushed into her. I was feeling a little nervous as I slowly moved in and out of her. My legs quivered. Was she liking it? If not she put on a show for me and it was believable. She didn’t thrash about and scream like it was fake but she purred and pushed back, glancing over her shoulder and smiling. She trembled and hung her head after a few minutes.

“That’s good, you’re so sweet.”

I realized when I was close to cumming that I didn’t have a condom on, she hadn’t even said anything about it. I guess I had to take responsibility, so when I was close I pulled out and, just as Dickey had done I moved up her body and pressed my dick against her mouth.

She swallowed my stiff prick and looked up at me for about five strokes, as I grunted and my balls tightened she pulled off, jerking my dick with her hand. I came onto her chest.

I lay on the bed next to her and she kissed me. I didn’t want to bug her, but I remembered her letting me cum in her mouth with no problem the first time.

“How come you pulled it out?” I asked as she wiped it off with a rag.

“Would you kiss me after I did?” She pressed against me and stoked my chest.

“No, that’s gross babe.”

“Well, if you don’t want your cum in your mouth why should I?” She looked into my eyes.

“Well, it doesn’t bother you!”

“Huh, maybe.” She smiled devilishly.

I’m not some chump, I could see what this was. She was trying to pressure me into stuff, the cum, the ass licking. What else would she try to make me do? I’m a man damn it! But then again, it’s better to have a girl who is dirtier than you are maybe.

The day went pleasantly though, my mom gave no indication that anything was amiss when she briefly spoke with Jen. I was beginning to realize that my mom had two sides, the sweet respectable lady, and the wanton tranny slut. It was like some bizarre version of The Hulk.

Or should I say Dr. Jekyll and Ms. Hyde.


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. Michelle  March 29, 2015

    Woof! What a fun story lol. ty for sharing it. Made my boring morning so much better.


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