Caught Crossdresser

This story contains accounts of bondage, crossdressing and humiliation. If this offends you please read no further.

First let me explain that I am a hetro crossdresser. I am also into bondage and DS play thou I rarely get the chance to do bondage and DS as partners are hard to find.

This story takes place as I am a senior in HS. My Mom and I live in a modest two-story house with a basement. It's a really nice neighbourhood, nice yards, not rich but not poor.

Thanks to the Internet I have met people who share my interests in crossdressing and bondage. After a few months I met Master Rick in a chat room and we agreed to do email domination and that I would take pictures and email them to him. He would have me paddle my bottom to a bright red, take a pic and send it to him. Sometimes he'd make me do one outdoors while dressed as a hooker and of course the red butt. All of this I kept from my mother, who would have put me in a home if she knew.

Things had been going great, Master Rick had introduced me to some bondage. He told me how to do it and made it very safe. I would use plastic soda bottles filled with water and a small cable wound inside and frozen, just one end and D ring outside the bottle. He had me bore two holes in a four-foot piece of wood big enough for the cable but not the bottle, the board was clamped to an old wooden table in the basement. I was made to get on all fours, Doggy style as Master Rick calls it, secure my knees with rope to the edge of the table then both hands cuffed to the frozen bottles. This resulted in my head down and my shaved bottom pointing up for all to see.

Sometimes it would be two hours for the ice to melt enough for escape. All the while bound I would fantasize about being caught by a repair man or and intruder and what they would make a boy dressed like a slut do, my lipstick would surely get smeared and my posterior used and made to wiggle.

It was going to be the perfect nite. Master Rick had sent me a hot email and Mom was to be out of town for a meeting. I would be all-alone for the whole afternoon and evening.

Master Rick’s instructions were devious. First I was to paint my finger and toe nails with black polish, I knew it would really take some work to get the polish off before school the next day. I was to put on a red wig, shoulder length and pin it to my own hair. Next came the black fishnet thigh highs, and my moms red knee boots with the three-inch heel. I took a few pics Master Rick had requested, He has had me completely shaven crack, legs, pubic since we started emailing. Mostly he wants cheesecake poses with spanks in between, gradually my bottom gets an angry red. The last article of clothing is a fuzzy purple and red bustier, it doesn't come down to my belly button and I get hard just thinking of wearing it.

It is now time for the bondage part. I set up the timer on the camera and bend over and give my poor bottom another volley from the ping-pong paddle, my ass is on fire but I want it really red for the pic. Master Rick will be so proud, and hard! I crawl up on the table and wiggle my roasted rump, pretending I'm teasing the construction workers across the street. I place my knees spread wide and tie first one, then the other. My heart is beating as I bend forward and arrange the TV mags and Master Ricks Emails on the chairs around the table, this way I'll be hard for the entire hour or so of being bound. I am also to leave my jelly dildo and a jar of Vaseline between my legs on the table for the upcoming pic. I get to use them after my wrists are free but before my legs are released. The left wrist is fastened easy because I can use both hands, the right wrist takes a couple tries but the spring loaded D ring finally catches. Now I'm caught the board is clamped to the legs of the table to my head can only get about an inch off the table, my knees are close enough that my defenceless ass is sticking lewdly in the air, shaven and very red.

I'm waiting for the timer to go off and flash the pic for my Master, I know it will happen in just a few seconds and I'm so hard that it hurts! FLASH... I give a jerk and have an uncontrollable urge to get off but there is no friction for my swollen member. I think of what this pic must look like and how Master Rick is going to share it with his friends for their amusement.

It's only been a couple of minutes when suddenly the door to the basement flies open and I hear someone coming down the steps, It’s a female and she is humming. A million things go thru my mind, Mom is in Portland, it can't be.... oh no. The humming continues until she is almost right beside me. Then I hear:

"Oh My God, who did this to..... you" Our next door neighbor and mom's best friend, Laura. She's mid thirties, a little overweight, but very cute. She's wearing cut offs and a sports shirt her brunette hair is almost down to her shoulders.

All I can think of to say is, "Please don't tell Mom, Pease?" I now realize that my face is as red as my bottom sticking up in the air.

Laura fumbles an apology "William, our washer is broken and your mom is letting me borrow hers, I'm so sorry." 

Some of the intial shock has gone from her voice. "Can I help you get loose?" as soon as she asks she lets out a muffled giggle and says, "Oh, I guess that's not why you did this."

Again she giggles and heads for the washing machine and loads some clothes in. Laura must have forgotten the soap because she walks behind me to get it from a shelf.

Again I have become aware of how hard my cock is and she must be staring at it and my red rear. So again I say, "Please Laura, don't tell mom."

She lets out another giggle, this time almost laughing and says, "God, I haven't even thought of what to do. Did you know I almost sent Carl over to do this load?" she does laugh aloud now, "I think he would have fallen in love with that cute bottom. He loves a red butt to play with."

The thought of Carl, a large burley man in his mid forties finding me like this makes my face flush some more and I just groan.

Laura is walking around the table really soaking in the spectacle, giggling and telling me how cute I am. She picks up a magazine and some of my pics from previous escapades. Now her face is getting flush and red. She says, "Hey, that’s my black bra in this picture!" I had stolen it from her clothesline a month ago. She goes to the washer and puts the soap in and says, "I'll be back to get my clothes in about a half hour. Have fun hon." this time it's laughter as she goes up the stairs.

I've had the ice melt enough in a half hour to get free but usually it is at least an hour. I know Laura is coming back, suddenly I wonder if she'll send Carl or if she'll tell him I stole her black bra. Now panic is setting in, I struggle but it's no use. The washer is on the final spin cycle and I hear someone coming down the stairs.

Laura speaks, and I am so relieved, "I guess I can't call you Prince William anymore, huh!" followed by a huge burst of laughter, "Maybe Princess Billy!" again she almost splits a gut. Somehow I don't see much humour in it.

"I see by these emails you call yourself Amber. That's a cute name." Laura says in her most feminine southern voice. "I won't tell your mother if you agree to tell me when Master Rick is going to have you do another session and let me watch the rest of this session. I won't interfere but I would love to watch Amber turn her bottom pink and use that dildo you’re so fond of."

"Ohhh.. Nooo" I moan, she found the pic where I'm using a jelly dong on my just paddled bottom, my knees are tied to the table spread wide. "Please don't make me do that."

"YES, YES" she's laughing, "I have got to see this show! Besides I see your still , AHEM... really excited about it."

I am shamed to realize she is right, I'm so hard it hurts. She picks up some short rope pieces and starts to tie each ankle as well and turn the knots down.

Laura steps back and admires her handiwork, "There, this way when your hands get loose you won't get away in a hurry".

Right about this time my wrist pulls the cable thru the softening ice and I have a hand free to let my left one off the clip. I almost dread this as Laura lets out a squeal.

"Come on Amber, lets get your little sex show on the road." she has a tint of lust in her voice. "We wouldn't want Carl looking for me? Or maybe you would?"

I know I have no choice so I reach for the dildo and then reach for the Vaseline and start to put a coat on it. Just then I see a flash. Laura has taken a pic with her digital camera. I am shocked and start to utter a protest but she cuts me off.

"I just want a little memento and besides I'll sent them to your email address, or... maybe your masters" she is really getting into being in charge.

I bring the dildo to my bottom, it's been there before but never for an audience. Laura stops this too when she says, "Not so fast, Amber, tease yourself for a while, run it up and down your crack and then beg for it."

I did as Laura commanded and she was quiet as I slowly inserted it to its base. As I did so I slowly went back to the doggy style and started to get lost in my own lust. She had me take it all the way out and then all the way in. My eyes were shut and I was working my cock with my other hand. Finally I could hold out no longer and started to shoot what I thought was about a quart of white goo all over my hand.

When I turned to catch Laura's reaction I was stunned to see she had left. I didn't know when or how many pics she had taken.

I was exhausted and untied myself as quickly as possible and rushed upstairs to change.

I didn't see Laura again until a week later when she was at our house-visiting mom. They were looking at a ‘Victoria Secret’ catalogue and she asked how I liked a pink bustier on one page, I could feel myself blush and she giggled but hasn't yet told her about my hobbies.

26/10/01