A Sissy's Tale

By Jenny Tasting

Published on Nov 18, 2023



A Sissy's Tale By Tasting Jenny

Comments and feedback welcome at tastingjenny@yahoo.com

This story is a work of fiction and contains descriptions of explicit sexual acts between men and women. If this type of content offends you or you are under the age of 18 do not read it.

This story is the property of the author. It can be downloaded for personal reading pleasure or sending to a friend, but if you wish to re-post on another site, please contact the author for permission.

Copyright Nov 2023. All Rights Reserved.

Becoming a sissy MF, bi, cd

Since marrying Kris, we'd settled into a bit of a routine. I'd become much more domestic in cleaning the house, cooking, and doing laundry while she focused on more manly chores of home improvement and landscaping. Kris was more outgoing and social while I was more of a homebody.

That meant on Friday nights I stayed home as Kris either stopped home to change or went straight from work to "Friday Night with the Girls". An early night was midnight but there were lots of times she came home after the bars closed or later. When I suggested that married women might tone it down a little, her tone and words made it clear that she would do as she pleased on Friday nights and I would like it. I struggled with her going out but this was something she'd taken control of. At first I was a bit put off but we were both happier when I followed her lead. We didn't fight and I appreciated her making the bigger decisions.

Each Friday night there were usually 4 women that got together: Dana, Andi, Jill, and Kris. They'd been friends for years. Dana was generally responsible for picking the location and liked to try out different bars and dance clubs. They'd even done a male strip club and when I questioned Kris about this she said it was just harmless fun. You could look but you couldn't touch.

Jill liked to send pics of everyone together and included me on the share. While they all looked sexy, Andi wore the most revealing clothes and seemed to push the others to keep up.

With Andi adding a bit of peer pressure, Kris was stopping home more often. Right now she was in her bathroom getting ready and had said she'd need some help getting dressed.

I loved this because it gave me a preview of the night's look which I almost always liked. I also like the submissiveness of helping her get dressed even if it was just something simple like helping zip her dress, making sure her stockings seams were straight, or being her gopher to tease me as she got ready.

On most Friday Nights, Jill just went crazy in posting pictures so the preview of Kris was followed by a whole collection. She definitely favored quantity over quality apparently thinking "why take one good picture when you can take 5 and pick the best one?". A single Friday Night out could have a hundred shots. .

Jill's pictures were generally of the whole group unless somebody was doing something goofy. Kris was the only one married in the group and when you put four attractive women together, you'll draw attention so sometimes there were also guys in the pictures. Usually they were just part of the background but if you looked closely, and I did, there was more to see than Jill thought when she took the picture.

Over the months they'd been doing Friday Nights there were two pictures that I came to regularly. Literally. The first was simply couples dancing, but if you looked closely Kris was slow dancing and the guy had his hands firmly on her ass at the hem of her mini-skirt. The other was a shot of the back of Kris' head at a Male Revue show. Directly in front of her was an incredibly fit guy with 6 pack abs, a thong and an erect cock. His cock was right in front of her face and had to be just inches away.

Seeing another man touching her, feeling her panties, and grinding his hard cock against her as they danced or rubbing his huge cock all over her face led to all sorts of wonderful thoughts. Is this something she does every Friday night? Is she just teasing or does she let them go further? Of course, she goes further. Does she give them head or let them fuck her? Does Jill have any pictures of that?

"Hey Hun, I need your help now. Can you come into the bedroom?" she called out as she came out of the bathroom.

Once in the bedroom, she handed me a pair of silky transparent panties. "Can you help me with these?"

I knelt in front of her and slowly started to slide the panties over her feet and up her legs. Her pussy was mostly clean shaven except for a little heart as the landing strip. Once in place the panties covered nothing showing off the top of her slit and her pretty heart.

The corset was a lot more challenging as I helped her fasten it and draw the strings to tighten it. Her large breasts were pushed high and the cups barely covered her areola leaving all of the cleavage exposed. Kris added a cover-up over the corset but it really just added to the look vs actually covering anything up.

Back on my knees I helped her with her skirt. I was very short coming just below the curve of her hips.

It occurred to me that the only thing she really needed help with was the corset and the rest was just to tease me.

"You look good enough to eat."

Sitting on the bed Kris reached into her bag and pulled out a yellow bra and panty set.

"Can you explain this? And I know about your collection, so don't bother lying to me."

My first response was panic. I thought I'd done a good job of hiding my stash of women's lingerie. There was no humor on her face as she waited for a response.

"I, uh." All I could do was pause and stutter. No words were coming.


"I saw it on a mannequin at the department store. The yellow was beautiful and it looked so sexy I couldn't help myself."

"So you like wearing women's clothes?" Kris offered.


"Have you tried them on?"


"Put them on for me now. I want to see."

The look on her face was quite direct and expectant and I began to undress.

The panties were easier so I started with them stripping off my jeans and boxer briefs . They were a high cut bikini brief and I tucked my penis flat between my legs as I pulled them into place. Then I stripped off my t-shirt and put the bra around my waist and hooked it. This was way easier than trying to fasten the bra behind my back. It was an A cup but had a little padding in it to give a bit of form to my figure.

"You've done this before. Do you always tuck yourself like that?"

"What do you mean?" I had no idea what she was talking about.

"When you put your panties on, you pushed your little penis, or maybe you call it a clit, between your legs to make yourself flatter. It definitely adds to the look."

"I didn't know I did it but yes. I like the panties to be flat." I blushed slightly at having my penis called a clit because that's how I thought of it. I am quite small and seem even smaller when wearing panties regularly. My clit is less than an inch long when soft.

"Do you masterbate when you dress?"


"Masturbate for me now" as she motioned for me sit or lay on the bed.

I sat on the edge of the bed and put my hand in my panties. I started as the base of my clit pushing it back between my legs as I stroked down on it. This felt a lot more feminine than stroking it like a cock.

"What do you fantasize about when you masturbate?"

"That I want you to make me dress in womens' clothes and have you feminize me. Doing whatever you ask to submit to you and being our sissy is something I fantasize about every day." I was now rock hard and slipped my clit out the leg of the panties to continue stroking it. "I imagine you're hooking up and cuckolding me on your 'Friday Nights with the Girls' putting your lovely cock sucking lips to good use. I want you to make me eat you when you come home as your sissy cuckold."

"You'd eat his cum?"

"I'd do whatever you told me to. So far I've just had my own. I think about being made to eat your cream pie every time we make love."

"Would you suck another man?"

"Yes. I fantasize about that. Getting him ready to fuck you."

"Would you spread your legs for him? Let him have you as a girl?" she said as she ran her hand up my butt cheek and then stroked my balls and clit.

That's all it took and I came in spurts. The first one landed high on my chest and the cum pooled on my belly.

"You have cum on your bra." She then scooped up most of my load and raised it to my mouth. "Swallow it sissy. Suck my fingers like a real cock."

I sucked and licked her hand clean.

She reached into her bag and pulled out a small case. "We're going to give you a little restraint now. Can't have you getting so excited and making such a mess." Unzipping the case was a small chastity cage and she started working it on to me. "You're so small that even this may be too big." It only took her a couple minutes to connect the pieces and lock it in place.

"Now you don't have to fantasize sissy."

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