A Too Trusting Cross Dresser
by Rebecca Knot
Copyright© 2026 by Rebecca Knot
BDSM Story: An over excited cross dresser, fouls fail of a robber.
Tags: CrossDressing Fiction MaleDom
You know what it’s like, I’m sure. You want something so badly, that you check your common sense at the door and dive in head first. The thrill the excitement, it’s finally happening, what you’ve dreamed of for so long. To finally scratch that itch, to fulfill that part of you that you’ve hidden away and buried for some long. Finally, after many false starts, lots of guilt, I start my search again. In search of a playmate, someone that doesn’t mind me dressing up a little. I’m not convincing never will be, but I’m smooth where it counts and I just so badly want to have some fun.
So there I am trolling around the internet again. I’ve checked amazon and they don’t seem to do what I need! I want to get dressed up a little and get tied up. That’s all I want. It isn’t much to ask surely. I’ve done self bondage, but just lacks that, risk, that excitement. Knowing I can get free, takes the edge right off the fun I want.
So there I am, back on the social network for CD’s, TV’s Tgirls, admirers and everyone in between. Chatting to some lovely people but they are all looking for their Top’s and I’m just one of many in the pool, looking for people that know their way around some bondage, want someone that looks like me and wants to play or switch or something.
Then one day as I’m browsing, someone catches my eye. They switch, they love bondage and like me they make an effort but well can’t be as perfect as we’d like to be sadly. But hey birds of a feather as they say.
We chat, lots, first on the website, messages flying back and forth, discussing our love of bondage, gags, being a damsel. Talking about how we’d love to be tied and tied the other, the wonderful mutual fun we could have, two masked damsels each taking our turns to tie and gag the other, bliss. I’d found a friend, who was in the same boat as me, looking to have fun with an understanding soul that wanted to have fun too.
We chat, speak on the phone, we got on really well. Our love for bondage from both sides shines through as we talk. We gag ourselves and ping over voice clips for the others teasing and amusement. It’s going great. We really click and we schedule a time to meet up.
We’re all set, I’m going to meet them at their house. I can get changed there and she’ll tie me up and gag me, I’ll tie her up and gag her and we’ll have a wonderful day, playing damsels. I’m so excited. Up early, shower so I’m nice and fresh, pack a couple of bags. Clothes to change into, heels, tights, bra skirt and a top. Kink kit, Rope, ball gag harness, hoods, tape.
I check my phone to let her know I’m just about ready to leave.
She responds, “Looking forward to seeing you soon. I hope it’s OK, I’ve arranged a surprise? xxx”
My heart pounds in my chest. A surprise, wow. OK. I’m frozen, my mind running a mile a minute. Wondered what on earth the surprise could be. Snapping myself out of my daze I manage to type a response.
“You’ve arranged a surprise sweetie? Do I get a clue?” I wait for the reply,
I don’t have to wait long before I can see she’s typing. Lots of typing. WOW, this is a big surprise and hell she’s building it up!
The message arrives, “You know we talked about both being damsels right? A friend of mine popped in for coffee and asked what I was up to, seeing as I’m dressed so I told him I had a friend coming over and we were going to be playing damsels. So he offered to tie us both up if we wanted. I’ll understand that I’m springing this on you, but if you’re keen, he’s a great guy, we’ve played lots and he knows his way around rope. Want to be a damsel with me? xxx”
I’m once again frozen to the spot. Excitement is flooding my body, I’m almost shaking, I try to type but my hand are near useless. I’m trembling with excitement of what could be! I take a few deep breaths trying to steady myself.
And start typing “That sounds amazing!! YES YES YES. I can’t wait to see you. Leaving now, be there soon!”
I head out the door, almost forgetting to lock it in my excitement. Throw my bags in the car and head on over. I hear my phone buzz as I’m driving, but wait until I arrive to check it.
“Hey, just needed to pop out for something, won’t be long. My friends there, so just ring the door bell, he’ll let you in, brief you on what we’ve planned and go from there? Back in ten xxx” you assure me in the text.
I’m trembling as I sit in the car. I grab my bags and head for the front door. I ring the door bell and the door opens.
“Hey come on in.” Says a friendly sound voice from behind the door.
I squeeze through the half open door and into the hall way. As I turn, I’m taken aback as there is the man attached the voice wearing a ski mask.
“Ooh WOW” I say, slightly in shock.
“Hiya” comes the reply and a bright smile through the mouth of the ski mask, “didn’t mean to scare you, just wanted to be in character from the outset, hope that’s ok? Eer.” He hesitates.
“Louise, please call me Louise” I say so excited I could burst. “And you are?”
“I’m a friend” comes the reply and that bright smile. “I’d rather save names for later, better for the surprise.”
“Ooh yes of course, no, of course that makes perfect sense. Erm what is the role play? I’m mean I’m liking it so far, but do I get a clue or shall I just go with the flow and follow instructions?” I ask not really sure what to do next.
“Of course, we thought a little home invasion/robbery would be the order of the day! Would you like to get a little tied up, gagged and robbed?” he said, the words light and fun.
“Oh my god yes, yes WOW that would be amazing!” I said with far too much excitement,
“Good stuff, so why don’t you pop upstairs and change, shout me when you’re ready, then I will see what goodies you’ve brought with you and we can go from there, sound good?” He asked with a smile.
I take the stairs up and onto the landing, I put my bags down, and change.
Pulling my tights on, falsies into my bra, slipping my skirt and top on and putting my heels ready to step into.
I call down the stairs “Ready.”
I hear him coming up the stair, the mask peeks round the corner first and there’s that bright smile.
“Wow, you look amazing”. His voice full of fun.
I just blush, I’m sure I don’t but how kind of him to say that.
He drops down a bag on to the landing, sweeping my stuff up into it.
“So what supplies did you bring with you?” he asked as he looked around on the landing.
I drop down to my knees and open up my little suit case. The bag full of rope, the head harness gag and of course the hood that only leaves my eyes exposed. In there too is a head bag, which blocks out what little sight I would have left wearing the hood.
“Nice collection you have there” he says admiring what I’ve brought.
I just smile, I’m just too excited to do anything but wait by the case.
“So, a little robbery, shall we? How real would you like to make this?” He asks looking right at me.
“Well, I don’t know, how real can we make this? I mean, do you really want to rob me?” I say with a chuckle.
“Wouldn’t that add to the role play? I could take your bank cards, pull some cash out. It’s just a thought, nothing nasty is going to happen” he says.
I hear what he says, but I hardly take on board what he’s saying, as I stare at the rope in his hand.
“Yeah, yeah sounds good” I mumble out.
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