During a rare quiet time at work I came up with a little scenario that I had never thought of previously. The thought of it caused me to stiffen up quite noticeably at work but I resisted the effort to take care of it in the staff toilets much preferring to save it for later. My remaining time at work was spent with a very clitty stiff in my lacy panties as I refined my idea.
I came home and decided to forgo my tea and instead get straight to work on my fantasy. Into the bath I went topped up with lots of bubble bath and scented oils. I slowly worked the razor over every part of my body - save the small tuft of pubic hair above my clit - making sure I was as smooth as possible. Legs, chest, arms, face and between my legs all felt the regular smooth pull of the razor over it. My legs received extra attention as I love the feel of them when they are recently shaved. When finished my bath I took down the shower hose, removed the head and inserted the water hose carefully inside myself slowly turning on the water. I took as much as I could before releasing the brown liquid into the toilet bowl. I did this four or five times in a row until the water ran clear and I satisfied I was clean inside and outside.
After this, I immediately applied my fragranced moisturising lotion into my baby soft skin before heading for the bedroom where I sat at my dressing table and began work on my face. A layer of foundation went on first followed by black eyeliner and a thick coat of black mascara. Next, came the smokey brown eye shadow applied carefully in a style perfected by years of practice. After this, I slowly traced my lip outline with my red lip pencil taking great care to give myself a fantastic pouting lip shape. It's not very often I wear any other colour on my lips than red and tonight was no exception. Tonight's lipstick of choice was Revlon's "In the Red", one of my favourite brands!
I opened my drawer and chose my underwear for tonight's adventure. It was black and lacy - perfect for a slut such as myself. A perfect 34DDbra coupled with a matching pair of sheer knickers bought just a couple of months ago in La Senza. I had decided earlier in the day that I would wear tights tonight and selected a pair of sheer glossy Pretty Polly's to partner my underwear. I always remember being told by a Master that real women wore tights more often than stockings and that I should emulate this when meeting with him. His words have stayed with me and I often wear tights when out dressed in public.
I slipped on the bra and then had a wicked thought and reached for my special drawer. This contains all of my toys and playthings and the objects I were looking for were near the back. It was my chastity cage and butt plug. The key to putting the cage on was to try and lose all sexual thoughts from my head so my clit is as soft as possible before locking myself in place. This is easier said than done when I'm in the middle of a transformation so I left it at the side and placed the plug on my bed. A small blob of lube helped it's passage up my boy pussy. I've no problems inserting plugs - depending on size - and will occasionally have a quick blast of poppers to help me out if I struggle. I continued dressing stepping into the tights and pulling them up and over my long shapely legs. Next came my sexy panties pulled up high on my body to emphasise my small cute bum.
I then filled a couple of balloons with lukewarm water and popped them inside my bra to give a realistic looking pair of female breasts. I turn the tied end outwards so it gives a nipple effect inside the bra. I've used this method for many year now and love the way they jiggle about when I walk. They feel fantastic when actually walking outside on pavements. I really should invest in a decent pair of breast forms and it is something I did look into a few year back but I've found a cheap pair of balloons gives a very nice effect underneath a blouse or dress - for a fraction of the price.
I chose a smart black skirt and matching blouse from my wardrobe and put them on. I smoothed down my clothing and ensured I was looking my absolute best. Once this was done I pulled down my knickers and tights and reached for my cage placing it over my shrunken clit. I then locked it into place with the small padlock and placed it on the bedside table before pulling my underwear back on again.
I was going to be driving tonight so my choice of footwear was to be a pair of 3 inch heeled black patent shoes. Not too high so they wouldn't interfere with the pedals whilst driving but still a very sexy style of shoe to be wearing. No fuck me pumps for me tonight. They can wait for a home session. The final stage of my transformation is when I apply my wig. It is the last thing I always do and signals that I am happy with how I look. My wigs sit on polystyrene heads inside my wardobe, always washed, brushed and ready to go at short notice. I chose my shoulder length brown bob and pull it across my head. A few goes with a brush and then I cover the lot with hairspray to hold it in place. I look at myself in the mirror and almost immediately feel my clitty strain against it cage. God, I want to fuck myself so bad! I look so fucking good and it feels good to know that I am very passable once all done up. I'm almost ready to go so look out my handbag, fill it with essentials, spray myself liberally with Lacoste's "Love of Pink" perfume and grab my waist length coat from the hook.
I jump in my car throwing the bag on the seat next to me. Starting the car I glance all round to see if any neighbours are going about, but the coast is clear so I head off. My journey takes around fifteen minutes and all the way there my heart is beating in my chest so fast. This scenario will be a first for me and I love the thrill and uncertainty of what will soon happen. It's been a while since I've tried something as wild as this and so have a bit of apprehension as to the possibilities. Soon I am at my destination though and start going up and down the darkened streets looking for someone suitable. It's nearly nine at night so the streets have more than a few candidates although not all of them are what I am after. I am a fussy fucker and know the look I want. Then I spot her and know this is the one. She's wearing a short miniskirt, a short furry jacket along with knee high spikey heeled boots that show off her long thin legs perfectly. I can't tell if she's wearing tights, stockings or has bare legs though? She looks to be around mid 20's, around the same height as myself, has long dark hair and has a thin frame to her. She looks perfect. Just what I want.
I grab my bag from the passenger seat and pull up next to her causing her to step forward and open the door. I can immediately tell she's confused. What does this woman want with me she must be thinking? I open my mouth and tell her I'm looking for some fun. The penny drops as she hears my natural voice and her mouth follows soon after. A second or two later her brain kicks in and it's business as usual. She jumps in and tells me to drive. As she directs me to a more secluded spot we start to discuss the transaction. I tell her I want a blow job and she starts at a laughable fifty quid! I plead poverty and tell her I only have twenty in my purse and she jumps at the price eager for easy money without spreading her legs. I watch her eyes as we talk seeing her looking me up and down. What is going on in her head. She knows I'm a man now but she was definitely confused earlier. She'll know I'm no threat dressed like I am. Fantastic. This is pretty much going according to plan and in the words of Hannibal Smith, "I love it when a plan comes together".
We park up in secluded car park a mile or so away from the pick up point and I pass her the note. It's dimly lit but I can make out that she's late teens - younger than I expected but I'm not changing my mind now. She is a good looking girl. I tell her I want a blow job but that when I cum I want the condom contents poured into my mouth. She smiles at my request but nods approvingly. I wonder if this is the first time she's been asked for this particular fetish? She rummages in her jacket pocket and pulls a condom out waving it at me and introducing herself as Mandy. You can call me Fiona I reply and she laughs.
"Really!?!?"
"Yes, really....." I say revelling in my her unwitting humiliation of me.
"Are you a tranny".
"Kind of... I call myself a sissy though. I love to dress as a woman and I like women as well as men"
She cracks a hesitant smile so I then recline the car seat and teasingly lift my skirt up above my waist eager for her to see what I am wearing underneath it. My clitty swells with the change in her expression. I'm watching her intently as my knickers come slowly into view and I distinctly see her eyebrows raise as she struggles to comprehend what is in front of her before she realises exactly what I'm wearing down the front of my sexy underwear.
"I'll need to take my knickers off, okay" I whisper softly to her, not taking my eyes from her face.
She nods, but remains motionless her eyes fixed on my nether regions as I lift my long nyloned legs and bum up slowly peeling my knickers off exposing my caged and swollen chastised clit within my glossy tights.
"My boyfriend makes me wear it when he's away" I explain almost apologetically.
"Does he..." comes the reply. Slow and monotone. Almost in automatic. She's stunned.
".... but I have the key" and I giggle pulling the key from my bag. I deserve an Oscar for this performance.
I start to pull the waistband of my tights down but do it clumsily and slowly before telling her it's not comfy and rip a big hole in the material letting her see my caged clit properly. I then reach down and make to open the padlock. I deliberately struggle to unlock it. The next step of my plan is in operation.
"I'm sorry... my fingers are trembling... could you.... possibly.... help" I stammer and hand her the key.
I flick on the interior light for a better view as she reaches over and takes the cage firmly in one hand squinting down and examining its shaped construction. Her other hand feels for the attached padlock - her fingers soon holding it tight - and she eventually slips the key home and frees me from my plastic prison.
"Thanks" I sigh.....
"No problem.... Fiona. Here...." and she hands me the cage and padlock back which I place on the dashboard. She's watching my clit slowly unfurl from its confines. Red and marked from the plastic it soon fills with blood and begins swelling up nicely.
I now take hold of my calves and lift and spread my legs for her deliberately exposing my plugged arse for her. She hadn't noticed this at first but once she does her eyes do a double take. She purposefully leans forward for a better look. I'm in humiliation heaven.
"That's my plug. I like to wear it most nights" I explain.
"OK.... do you not get... sore"?
"No, I'm used to it now. It was at first but not now. I love wearing it."
By now I'm very hard. The sexy chat coupled with the look on her face has worked wonders. She has pulled quite the trick tonight with me! I'm absolutely loving it. I take the condom and roll it down and over my stiff member. She's still staring at the display in front of her. A stiff rubbered sissies cock with a tight fitting butt plug jammed in an arsehole to top it off. Mmmmm. She looks up at me one more time and I smile across at her eager for her slutty mouth to start its work.
Her head goes down, her mouth closing around my cock and I relax and let her head bob up and down slowly at first. I moan and tell her she's good which causes her to speed up a bit. She wants me to cum. This eager slut is taking me closer and closer to orgasm with every movement of her head. This girl has definitely sucked cock before.... plenty times. She works it hard eager to make me cum and get back on the street for her next punter and more easy cash. I try to think of something else to extend my session and softly ask her to smack my plug. She stops her motions, lifts her lips from my clit, and softly taps against my plug with her fingers.
"Harder Mandy" I ask lifting my legs up and she does it again with more force using her full hand this time. I groan and she is not sure whether this is pleasure or pain?
"Again Mandy. Harder", and once more she slaps her hand against it causing me to moan in ecstasy.
"Thanks Mandy" and I put one of my hands down underneath my body and towards my plugged arse.
I push her head back down with my other one and she goes back to work while I manipulate and pull at the plug stretching my filled boy pussy as best I can. I feel the pressure build up within me and tell her that she's doing it good. She can sense it's nearly over and continues to build up speed. One hand holds my clitty secure whilst her other is resting on my glossy tights covered leg. I love the feel of it resting there against the silky smooth material. I bet she enjoys this more than sucking on some hairy legged smelly bastard's cock? A shaved and perfumed sissies body must be a treat for someone like her. By fuck, she;s good at sucking cock though.
"That's it Mandy... that's it... you're so good..... my boyfriend would be so mad if he knew.... fuck him.... keep going baby.... keep going.... you're the best.... better than him.... oh yes.... fuck him.... oh yes.... oh yes.... fuuuuuuuccccckkkkk"
Her head was almost a blur as I came. My salty load spurted out thick and fast easily filling the rubber condom. Her head kept going extracting every drop from my balls. I was so excited with this perfectly staged illegal dalliance. At the same time my sphincter repeatedly squeezed hard on the plug, tightening spasmodically as the waves of passion ran through me. It felt so good. So good. So naughty, and so very good....
After I was totally spent, I opened my eyes to see Mandy staring at my splayed legs and spent softening clit. I nodded at my clit and she followed her cue. Her long fingers peel the rubber off and I smiled to myself as she holds the bag between her fingers displaying the warm gooey contents. I sit up, look in the mirror and straighten my wig and tell her to hold on as I pull my knickers back on, smoothing my skirt down from round my waist. She hands the condom to me and I tip my head back, open my lips and pour my own jizz straight over my red painted lips and into my waiting sissy mouth. Dear Lord, I'm loving this performance....
Mandy looks at me with a mixture of amazement, amusement, disgust, and disbelief at what has just happened in front of her. I sexily lick my lips and thank her for her efforts. She asks to be dropped off at the same place and after checking my appearance once more we head off. She is more conversational now and tells me that she has a mobile number if I want to meet up again? I tell her that's a great idea and make a note of her number in my diary. We pull up just up from the original meeting point and I thanks her once again before she jumps out. I watch her wiggle off into the distance and smile at the thought of having had my cock insde such a good looking girl. Once she is gone from view I rip the page from the book and throw it from my car. That was a great night - better than great actually - but it depended upon the girl not knowing I was male to start with and seeing the look on her face when my cage and plug came into view. Going with Mandy again wouldn't be the same now she knew what to expect from me. The thrill comes in exposing myself slowly and precisely as a femmed up sissy to some unwitting girl. Mandy was good, but only for one meeting.
Til the next time people.
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