I had long had a fetish with body swapping. I.E. trying to experience totally what a women feels like having anal sex. I wanted to take pegging to a new level with a FWB that I met on rare occasions that was similarly wired. Cross dressing was well practiced. She would often shop for me at lingerie sales and surprise me with new items.
I recall one of the few forays into makeup play. You had shown up
with a new bra and several new panties, but was most unsettling was a small, gold cardboard box that had some jewelry, and lipstick in it that you brought along.
What was particularly disturbing about it was that it wasn’t simply
items that you had picked up on sale at a CVS or other discount
place, but rather things you had obviously worn or used yourself
that you were going to put on me. Even though I knew they were
castoffs of yours, it somehow felt too intimate that you were going
to see me wearing them. It also flew through my mind that each
time before I fucked you, you always took off all of your jewelry.
Watch, earrings, all came off. But….I was going to be dressed up
before you inevitably fucked me with the strap on.
I recall touching each piece, and then diverting your attention to
the clothing. We selected what I would be wearing, and began the
process of dressing me. Always starting with rolling on the
stockings first, then the garter belt, then the bra with the tits,
and finally selecting a panty to pull over the top of the garter
belt. You remained dressed which which felt awkward and exciting.
You very matter of factly told me to come over to the desk, and
brought the lamp forward, gathering up not only the cosmetics in
the gold box, but also pulling out some small items from your
purse. I don’t know if you remember that part. You had eyeliner
and mascara in your purse, lipsticks and such in the box with the
jewelry.
It was disturbing to have you touch my chin, to adjust my face
upwards and feel you start to brush on the eyeliner to my closed
eyes. I felt more vulnerable than when being penetrated by you.
You moved with purpose, like you had done this before, but then I
realized you did it every morning to your own face. You seemed
happy with the eyes and then took the lipsticks out, and opened two of them asking me which color I liked. I felt again totally out of my element and told you to choose.
You leaned close to my face with your face, and applied it,
unconsciously making your lips tight as if it was going on you, and
I mimicked you. You leaned back and told me to blot them, first
scrubbing the two lips together, and then being handed a tissue.
You did a bit of touch up, and even lightly applied a foundation
with a soft foam rubber pad. You leaned back happy with the
result, reached into the box and handed me a pair of clip on
earrings that were large, and somewhat heavy. You sprung them
open, and watched me put them on, again with a look of curiosity
and almost appraising me on your face.
You told me to stand up and look at myself in the mirror. You
stood behind me, looking over my shoulder, and I saw myself. You
went heavy on the eyeliner, and the lipstick was a deep red shade
that I wondered immediately where you had worn it previously.
The earrings felt odd, moving and pulling as I moved my head, brushing my neck. I had trouble processing the change in my face more so than I did seeing myself in the bra, panties, stockings, tits and garter belt. It felt like an almost unrecoverable step towards feminization.
I remember you reached around me, rubbed my cock through the
panties until it started bulging outwards, and asked me if I wanted
you to fuck me. I saw the expanding dot of pre-cum forming on the champagne colored panties. Of course I agreed, and you undressed in front of me, totally unconcerned. I felt like you were acting like you would undressing in front of another woman.
I helped you into the black strap on, getting the excess ends of
the belts tucked neatly away. You had me lean over a low dresser
with a large mirror over it, head up, watching you lube up the
dildo and my anus.
My last memory was you pushing into me, me leaning forward
spreading my cheeks to give you access to my man cunt, and you told me “Look into the mirror, see my tits on your back?”
And there you were, pushed all the way into me, tits flattened down on my back, while my discarded panties lay on the floor, I saw my bright red lips, and heavily made up eyes looking back. At that moment I felt incredibly vulnerable but also felt I finally had come as close as possible to feeling what you must feel, when I grab your hips and force my cock deep into your slick rectum.
Source: reddit.com/r/gonewildstories/comments/5ksg3a/fm_kink_body_swapping
sounds nice! Any pics of you dressing up?