Sissy's Decline into a Slut Pt. 01

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A journey into sissy slut play then sissy lifestyle.
6.3k words
4.38
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Part 1 of the 6 part series

Updated 06/08/2023
Created 05/14/2017
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Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy...

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Chapter One: Sissy Crossdressing Play Time.

I'm sitting inside my car, it's late, a faint drizzle falls as the sound of the rain has me fade into a bit of a dream state... My mind is on the type of faggot, sissy slut I truly desire to be. I am in a lucid state of hunger for sissy humiliation and slut duty. It's almost drug like... But a few hours ago I was merely preparing for where I am at this moment...

Earlier tonight my pathetically horny life of crossdressing as either a faggot sissy slut or a prissy sissy maid saw me dressed with full makeup, wig, under garments, black sheer pantyhose and one of my black satin maids dresses with white lace trim a white satin apron, black satin choker and a maids cap on my head. I stepped into a pair of simple, black smooth leather 5 inch spike heel pumps.

I was prancing around my home, feeling all sissy maid girly, playing with myself, wanting to pull my sissy dick until I cream all over my panty but trying not to. It felt so pathetic but exciting as I walked around in my heels, did a few chores. It's like so many hundreds of times in my past exciting like this. I soon sat and looked at online sissy porn and only wish it was me doing that.

My sissy mind wanted to push my limits but for years and years I was too sheepish and never really did. Tonight was different, I finally decided to push through and soon I grabbed my purse and my car keys. It was late oh a little after 11:00pm and I scanned around as I looked outside my front door. My nerves were all wild, my senses were heightened and I said, "Fuck it, get in your car sissy girl." as I scampered my heels were going click, clock, click, clock as I walked to my car, unlocked it and got inside. My heart was pounding and I was panting a bit. I settled down and soon I'm was driving out of my driveway and on the street, fully clothed as a sissy maid. I felt exhilarated as I drove around. I did not see many other cars on the road, mostly a few taxi cabs.

I drove around the town and soon my mind had me thinking about a 'rest area' about 15 minutes outside the town on a local highway. I decided to drive out to see it and whether it had people there or not at this time of night. My excitement was high as I wanted to see if maybe I could mince around the 'rest area' dressed as sissy maid Chantel.

As I arrived and pulled into the rest area off the highway I soon saw it looked empty of cars. I pulled into a parking spot just off the pathway to the large bathrooms. I sat in my car and soaked up all I have done...

Back now to the current moment in time. Yes, it's lightly raining and I am sitting inside my car, all dark and quiet short of the sound of rain falling on my car's roof with light music playing in background on my car stereo. My right hand does begin to fondle my sissy dick while it still rests inside my black satin, padded panty. Pre cum does wet the front area of the panty's crotch. I sniff my fingers and smell the smell of a male getting sexually aroused.

I'm thinking, 'It's so odd at how each step of my journey tonight soon pushes me to another. I mean hours ago, dressing up inside my house was exciting enough, followed by watching sissy porn on my computer. That only set me up to want to get out of my house and get in my car, which I did. Then I started up my car and began to drive around my town dressed as a sissy maid. This all brought me to this 'rest area'. I'm now feeling the urge even with light rain to step out of my car and walk around, maybe even inside the men's bathroom.'

This thought of pushing myself to areas I have yet to do in all my 40 odd years of living is compelling. The fear of being seen and maybe caught by others scares me but also turns me on.

I have been parked here now for about 15 minutes, playing with my sissy dick but not cumming yet is so exciting to me. I think, 'Do I do it? Or Do I not?' I so want to step out from my car. Soon another 10 minutes pass, it's 11:30pm on my car stereo's clock. I've been here near a half hour and no other car has come by. My courage is building. I decide to pop open my driver side door. The rain has now let up and I sit in the driver's seat just letting the cool damp air swirl inside my car. I feel the sensual coolness of this breeze on my black sheer pantyhose clad legs. It feels so fucking great to me. My head is a buzz with nervous excitement. Before I know it, my feet have swung daintily out and my heels plant on the pavement. I stand up and my dress falls nicely in place. I feel the cool breeze on my made up face, the breeze then blows my auburn and blonde hi-lighted, shoulder length with loose wispy curls wig lightly in my face.

I'm standing by my car and it feels so fucking exciting. Before I know it I have the driver side door closed, keys in hand of course and I make my first steps in my high heels. My senses are high and I feel as if each and every click, clock, of my spike heels reverberate all over the city. But step by step I walk further and further away from my car. I feel so excited and so sissyish. My courage slowly builds but I am scanning around myself, eyes darting left and then right and back to left etc.

I rather enjoy this late evening walk around this dimly lit and dead quiet 'rest area'. The continued breeze on my legs and my face feels so comforting. My breathing now normalizes. Soon I'm walking a good 50-60-70 feet away from my car. I see a covered picnic bench another 10-15 feet away. As I step on the wet grass my heels dig in and almost pull my shoes off my pantyhose clad feet. I then carefully walk to the bench and sit on it, looking back to my now car easily 75-80 feet away in the dim light of the rest area's lamps.

I'm thinking, 'If another car was to come now, I could never rush back fast enough in my heels to reach my parked car. I'd have to crouch and hide, hoping whoever it was would only come to use the bathroom and then leave.' This thought and fear only turns me on so much more. I have my right hand down my panty and play more with my stiff sissy dick. A part of me wants to now quickly jerk off and then go home, but another part of me wants to delay this eventual gratification.

It's now about 11:45pm. I've been here for about 45 minutes. My arousal is very high. I decide to walk to the bathroom. Each step of my spike heels gets me closer and closer. The outside door lighting will clearly show the sissy maid I am to any person who could be near by and see. But I am still alone. I am at the men's side outside door and figure if I step inside this brightly lit bathroom I will not be able to see any car that may come. This scares me but fucking turns me on even more.

Before I know it I'm inside, the door closes behind me. Alone my heels with each step, click and echo on the concrete floor. I love the sound. As I walk in the bathroom I soon see the large mirror on the wall above the counter and five sinks. I see my sissy maid reflection in the mirror and smile. I stand back and practice curtsies over and over and over, saying, "Hello Master, sissy Chantel at your service."

I'm so fucking horny right now. I prance around in my heels. I soon stand by the five urinals thinking if I could only hold a man's cock as he pisses in the urinal to then suck him off afterwards. I have no idea if a car has come or not. Some guy or guys could walk in on sissy me, but my arousal is so high it's as if I'm on a drug. I now stare into toilet stalls and think, 'Fuck I wish I was being fucked up my sissy ass in one of these toilet stalls, or sucking cock in one.'

It's now after midnight and I can't contain myself anymore. I walk into one of the five toilet stalls, pull down my pantyhose and my panty. I begin stroking my white six inch, normal girth, uncut sissy dick. At this point it does not take long for me to shoot out a good load of my sissy cum. Drip, dribble it all falls into the toilet bowl. It felt fucking incredible. One of the most aroused masturbation sessions of my life. My head is near delirious as my sissy dick shoots out its load of cum. I excitedly stare at the sissy cum floating in the toilet bowl.

But alas as with most male ejaculation, once you blow your wad, the come back down to reality is often hard and fast. Dressed up as a sissy maid exacerbates this. I am soon just sitting on the toilet. The male err, well wannabe man in me has me feeling like shit. I say to myself, "What the fuck is wrong with me?" "Fucking pathetic, you fucking pathetic faggot sissy." "God dammit what a joke of a man you are." "Fucking look at yourself, maids dress, pantyhose, high heels a wig and makeup."

I sit on the toilet and just sigh. Soon I tuck my sissy dick back in my panty, pull my pantyhose back up, fix my dress and step out of the toilet stall. I walk to the door, peek outside to see if another car has come or not. Thankfully for me, I'm still alone. I quickly scamper in my heels back to my car and am inside on the driver's side. I rest for a minute and start up my engine. As I back out from the parking spot I notice headlights and yes another car is entering the 'rest area'. I am safe as I am now driving away but I think, 'Holy Shit, if I spent two more minutes in the men's bathroom I may have been seen and caught. Fuck imagine what may have come of that?

I laugh out loud about this now and think, 'Huh, maybe I'd be sucking cock right now, or being fucked up my sissy ass if I were still there. But maybe too some guy or guys could be beating the shit out of me.' That last thought scares me but the first two are turning me back on. But it's like 12:15am and I decide to drive back home.

I'm home by 12:30am and quickly scamper in my heels back inside my house. Tonight was some of the most exciting stuff I have ever done crossdressed and as a sissy maid. I sit down and relive the night in my mind and soon am playing with my sissy dick again. But I am imagining being caught by some guy or guys from that car that came as I was a leaving. My mind was thinking, 'Fuck that could have been exciting and life changing. I mean what if it was a guy or guys who'd have gotten off on seeing a faggot sissy girl like me. Imagine if I would have for the first time in my sissy life sucked cock or was fucked up my sissy ass by hard cock. DAMMIT! DAMMIT! DAMMIT! I wish I was caught now.'

Yes, I'm horny again and feel the arousal of what could have been. My right hand is stroking my hard sissy dick inside my panty and soon I shoot my night capper wad of sissy cum all over my satiny panty. Another little treat for myself. I am back melted down to feeling blah again.

I get up and go to my bedroom remove my sissy clothes and go to the bathroom and wash the makeup off my face. It's now 1:00am. and I am in bed. My mind wanders I know this, I'm going to do that again, I just know it. Sooner than later I'm going to dress up as a sissy maid or as a sissy slut and late in the night go back out to that 'rest area.' I smile as I drift to sleep wearing a white full slip over a white bra and panty and a pair of white tights that I sleep in.

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Chapter Two: It is Off to Another Play Night at The Rest Area and More.

Well a few days have passed since my first outdoor foray dressed as sissy Chantel, mincing and prancing around the local area rest area. I've been recollecting about that night every day since then. The thrill of it all is very powerful and I know that I'm going to do such stuff again. As I sit with a cup of coffee after dinner I begin getting hot for dressing up again and venturing out to that rest area again. I thought tonight I'm, going to dress up more as a sissy slut.

I took a nice hot shower and once dry I put lotion all over my body. A very close shave and then it's on to my make up. I have become a crossdresser who has been able to do very good makeup applications. I'm lucky being at 5'11" and about 185lbs. I look tall and slim. My face does feminize nicely. I really am a hot looking crossdresser/sissy.

As to clothes I put on a black satin bra and then slip in my breast forms, a matching black satin padded panty gets me going well. Tonight I'm going to pull on a pair of black silky sheer pantyhose and a black denim mini-skirt. A white satin long sleeve blouse finishes off my slutty outfit.

I relax dressed as such until about 10:45pm. Once it is 10:45pm I put on a cropped black, faux leather jacket, put my belongings into a black purse and I slip on my black velvet 5 inch spike heel pumps with cute ankle straps.

My nerves are heightened as I know I plan to venture out and to the rest area again. So as I click clock in my heels to my front door and first sheepishly peek outside to see if any people are around to see femmy me strut to my car. I am satisfied I shall be not seen. I scamper in my heels and soon sit in the driver's seat of my car. Start up the engine, rest and ponder things for a minute, 'Do I want to do this again? What if I get seen, get harassed or worse beat up? But I will have electrifying fun too. Driving to that rest area again will be so intoxicatingly fun.'

Soon I find myself out and about driving in my car. My mind melts into my feminine style and sexy feeling. Being a manual transmission car my mind wanders to my sexy fun high heeled feet manipulating the peddles as I change gears, brake, apply gas and change more gears.

It's cloudy but cool tonight so the rest area short of its few parking lot lamps and security lights outside the bathroom building will be privately dark for me when outside. If or when I walk inside the men's bathroom though it will be brightly lit. I keep on driving towards the rest area.

As I pull into the parking lot off the roadway I soon see two cars parked. My nerves really go wild. I at first park in a space further away from the two cars which are parked near the walkway to the bathroom. I'm scared but excited, I sit in my car and wait for a minute to see if people are coming or going to or from each car. It's too dark for me to see if any person sits inside either car. As I wait I can't help but find my right hand feel my crotch and my hard sissy dick. I feel the silky texture of the black pantyhose and it turns me on. I keep my eyes on the bathroom area.

A couple of minutes pass and I soon see one guy walk out and back down the walkway. I'm sure he does not see or notice me. He is focused on his car and soon he gets inside it and then drives off.

The other car is still parked, again it's too dark for me to see if it's empty or not. A part of me wants to step outside my car and tempt fate if a person or persons are in the bathroom. I think, 'If a guy or guys are still inside the bathroom, I could get out of my car and in the dark quickly scamper towards the bathroom, but off the walkway, staying on the grassy area of the rest area and hide from sight near the bathroom to be turned on by fear of being seen as I wait in hiding to see a guy or guys walk out and back to the car to then leave. I would need to be quick and discrete.'

I am close to popping open my door to do this when I see not the men's bathroom door open but the ladies. I see two ladies walk together down the walk way to the car. I so want to show them femmy me but I just meekly sit in my car. One gal gets in the left back door and the other gal gets in the right front side. I think, 'Shit it's a good thing I did not get out of my car as there was one person in the driver's side of the car.' Soon it too drives off, I am alone at a fun play place for a wannabe sissy slut tonight.

My car clock now shows 11:30pm. I now work the courage to step outside my car. Door open, high heeled feet planted on the pavement and standing feeling so horny and yes sexy, slutty. I close my car door and again I begin to walk. Again like my first time my high heels click clock seemingly so loud in the now still night air. I feel my heart pounding as I make my steps in my heels. The adrenaline rushes through my girly looking body.

The bathroom is about 60-70 feet away and I soon decide to move onto the grassy area and walk not to the bathroom entrance but to the back side of the building away from direct street lights. I lean against the back side wall and gaze at the entrance of the rest area. Soon I reach into my purse and grab my cell phone and set it up in video mode. I turn on the LED video light and start a video of me. I am so excited at this and make sure my selfie video shows my made up face, wig and clothes including my spike heels.

I narrate to my video, " Hi all who may see this video, this is sissy Chantel, out at the rest area off 'Apple Grove Road'. I'm here dressed as a sissy slut, enjoying being in a public place. I'm so nervous but so excited and horny."

I can't help but to touch my crotch. I now add to my video, "Two cars with people were here using the bathroom mere minutes ago. I hid in my car until they left, even though the sissy faggot in me so wanted to show myself to them. So I'm going to stand here in the dark for a bit but then walk into the men's bathroom to play some more."

I let the video run but after I turn off the LED light to help keep me in the dark. It was a good thing as soon a car pulls into the rest area and parks not 40 feet away from me but in front of the bathroom's walk way. I carefully back away and around the corner now behind the back wall. I can now hear the guy walking up the path as he horks out a lugi. I can't see him nor he see me. I hear him walk inside the bathroom. It's so exciting to know a man is so close but so far from sissy slut me. I want to run inside and show him faggot, sissy me, but I'm too scared. I just stand and play with my crotch area. A couple minutes later he steps back out and walks back to his car. Once inside I hear him start it, back up. I so wanted him to find me and fuck me.

He is now gone and I'm so fucking horny now I almost wildly walk up and inside the men's bathroom. my video is running. The heels click loudly on the bathroom's concrete floor. Bright fluorescent lighting shows my sissy slut outfit, my make up and wig as well. Right now a guy or guys could walk in on me and it would be scary.

My video running I narrate, "Here is sissy faggot Chantel and here are the toilet stalls, fuck would it not be a blast to suck cock inside one or Mmmm get my sissy ass fucked bent over the toilet?" I make clear with the camera of the toilet I'd either sit on to suck a guy off or be bent over to be fucked for first time in my pathetic sissy life up my sissy slutty ass.

As I keep video running I pull up my skirt with my right hand, pull down my pantyhose and panty. My six odd inch dick is at attention as my right hand begins to stroke it. I am so horny right now I begin to seriously jerk off standing at the counter and a sink. I hold my phone and video myself, my reflection in the mirror. I start to call myself a slut, a sissy, a sissy slut, a fucking faggot whore over and over as my arousal to cum is so high. Soon I moan and groan as I pant and sigh and just like that my sissy dick shoots out a volley of my sissy jizz into the bowl of the sink. OH MY GOD WHAT A FEELING!

I slow down and come back down. Like most or all guys who cum, I get lost in my declining mood. I say to myself, "Fuck, fuck, fuck, why the fuck do I do this? I feel like shit now, so pathetic."

I stop my video and tuck my dick in my pantyhose and fix my hose and skirt. I now just walk out of bathroom and quickly get back to my car. The drive back home is quiet and melancholic. Once at home I sit for a few minutes dressed en femme and soon then strip off my clothes, wash my face and put on a bra, panty and slip to go to bed.

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