Date: Fri, 17 Nov 2023 06:57:10 +0000 (UTC)
From: Jenny Tasting
Subject: A Sissy's Tale
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.
"Yes"?
"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.
"Yes"
"Have you tried them on?"
"Yes."
"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?"
"Yes"
"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."