Sissy Time!
I met Mark at the pool and he was adorable in his Speedo, his small penis showing through the thin material. You would think he would have worn trunks, but for some reason, he was in that tiny swim suit. My Sissy-dar immediately went up as I watched him pull on a cover-up so he wouldn’t burn.
Sissy?
I sent over a Strawberry Daiquiri and we immediately hit it off, talking like old friends… girlfriends. I offered to have him come over to my house and he eagerly agreed! At my house, we continued chatting, still sitting in our bathing suits. I suggested he take a shower and that I had some clothes for him. (I had plans to make him my crossdressing girlfriend!) “Oh, yes!” and up the stairs he went.
Sissy Clothes
While Mark was in the shower, we kept talking to each other, hollering above the distance and water… and I picked out his perfect outfit. I chose a lovely pair of satin panties with lace on the top… with a pretty bow, too, of course. I chose an adorable sissy dress and knew it would be awesome on him. But something was missing. Oh! Stockings! That would make him the ultimate Panty Boi.
Shocked!
I heard Mark coming out of the shower and went to dry him myself. I then picked out my rose lotion and began slathering it all over his body. He had such a small penis, but I ignored that at the moment. While he seemed to be enjoying the attention, he did keep asking me what I was doing? And why the perfumed lotion? I just laughed and flicked his tiny penis and said I had a surprise for him. We walked to my warm bedroom and laid out on the bed were the underwear and clothes I wanted him to wear. He stood there and blinked, looking at the clothes and then me and then at the clothes again. “This is what you want me to wear?!” Oh, yes, you little Sissy. You’re already my girlfriend, aren’t you?
My Sissy Gets Dressed
Despite protestations, I told Mark to just fucking get dressed already. He knew, as soon as he put on those panties, he had come home. I showed him how to put on stockings without ripping them and then he put on the adorable dress I’d set out for him. I made him stand in front of the mirror and model for me. He prissed up perfectly!!
I had lots of things in mind for my new Sissy friend… I was going to gradually do small penis humiliation, teach him how to put on make-up and maybe even coerce him to go out with me in drag.
What fun we were going to have!
I wish I were Mark, except I wouldn’t protest I’d be thankful, you would see I already knew how to put on my pantyhose!
I love a Sissy who knows how to wear hose. Good girl!
I love it! I absolutely adore men in panties! I can’t even imagine being in a relationship with a man, but I do like to have fun. One cutie pie I met online wanted to come over and I quote, “Give me a good dick down”! I’d never heard that term but knew exactly what he meant. I told him he could come by but the only way he was going to fuck me (I’ve never been with a man, ever! lol) Jeff have to wear panties and a c-ring! He said he didn’t have either so I told him to contact me after he got both and hung up. He never called again and I’m cool with that because there was no emotional attachment. Next!
You are wonderful!!!
I need to know you better!
Oh my Mistress Daphne,
Sounds absolutely fabulous!
I could only hope your disposal of the guys clothes as well.
Could give to charity or burn them?
I’d do as you wished under your authorisation. xx
I always donate them to men who are returning to the workforce (ie homeless men getting a job, men coming out of jail, etc.). Thanks for the reminder to put that in my stories!
So glad to see you here, Krissy. 🙂
This needs to happen to me for real Ms Daphne,
Yes MISTRESS DAPHNE sounds so wonderful so funny sincerly yours beta bottom bitch tedi thankyou
Such a lucky guy. Finding girls to help along the rabbit hole sissy pink brick road is a blessing
I have cherished the items of clothing girls have given
Mistress Daphne as you know i flip flop & at times make room for the girl by giving away clothing a few winters ago i gave away guy clothing warm stuff in our Florida cold. Jeans work shirts flannel & sweat shirts . Anywho i have flipped my switch into fuller sissy mode than ever before .Here in Sarasota they passed an ordinance about giving to homeless can’t give from a motor vechile to a pedestrian so i got around this by parking and giving clothing & food