Sissy's Decline into a Slut Pt. 05

We get back home, I am to strip only to my bra, panty and hose as I will spend the rest of the afternoon paint my bedroom barbie pink and dressed as such will make sure I do not get paint to spill to splotch on my maids dress. 


After I get back into my pink maids dress and heels, make dinner and later told to dress as a slut as tonight I will be pimped out on the tranny stroll. I'm so fuckin scared but shower, do my make up and dress up. I put on a black lace bra, some small breast forms, put on a padded black satin panty, a black lace garter belt. I carefully pull on a pair of black sheer back seem stockings. I put on a white long sleeve, satin blouse. and a black faux leather mini skirt. I pull out a pair on red suede 6.5inch spike heel pumps with a 1.5 inch platforms. I put my I.D. perfume and stuff in a shoulder purse and put on a black leather jacket. I look at myself into full length mirror and think, 'Fuck girl, you look fuckin hot, you are a very sexy tranny slut. Masters are going to love your slutty look tonight.'

I walk upstairs and show Masters my look and they fucking love it. I turn them on so much they have me give them each blow jobs before they drive me out to the tranny stroll. I am so fuckin horny too and I suck them off very well as they are in ecstasy. Soon though we are driving out to the part of town where many trannies stroll. It is an area of commercial and industrial buildings. So for most after 6:00pm they are closed and only a few businesses stay open. For instance one is a diner where they accept tranny hookers hanging out on breaks, but mostly it's deserted and only tranny sluts and Johns looking for quick, cheap and dirty tranny sex are out and about.

Of course my nerves are all amok as we drive closer and closer to the stroll. I've never truly prostituted myself and as such for a real pimp master wants me to make him some good money. I am pretty quiet and introspective as Master's Gage and Martin drive me out to the stroll. As we finally get there I see outside the car's windows, tranny prostitutes, I think to myself, 'God, this is it, this is what my life has come too, to be another cheap tranny slut making money for my black pimp master. Knowing the money I will make will be surrendered to him completely. All my fantasies have and will come true.'

Master parks by the curb near an area where working tranny girls congregate and work from.

Master Gage says, "Look Chantel this is your area and given how good you look and your age a good area to work. I want at least $600 tonight, I know it's your first night but you look good and I'm sure enough horny guys looking to fuck some tranny slut ass or have one suck their dicks will hook up with you."

I reply, "Yes.. Yes Master, I'm every scared though."

Master Martin pipe in, "Bitch with them legs, tall heels, short skirt and good slutty look you will be too busy to be scared."

Master Gage adds, "Look it's easy Chantel, flash your body, shake your ass and be upbeat to any dudes who come to you looking for some action. There are fucking and sucking areas all over here, behind garbage dumpsters, under stair cases, by doorway entrances, behind the backs of buildings, parked in cars, lots of places for you to be the whore you want to be Chantel."

I reply, "Oh.. ok, you are both right Masters, I'll be a good girl, I'll work hard to make you the money."

I am instructed to step out of Master Gage's car, which I do, he tells me they will be back at 12:30am, that gives me over 5.5 hours too work it, I curtsey and thank them. They then drive away. I am so nervous, what if there other girls not like me, am I stepping on any other girls area? I begin to walk to where a couple of girls are standing.

First girl, "Hey hun, you look new here."

I sheepishly reply, "Um, yes, it...it's my first night. My pimp master has put me out now to work for him."

Second girl, "Shit you look good girl, love your shoes, they compliment your sexy legs."

I reply, "Thanks."

First girl says, "My name is Tracy, this is Kelly. and your name hun?"

I answer, "My name is Chantel."

Tracy asks, "So you say you are being pimped?"

I reply, "Yes... yes I have always wanted a Master who will pimp me as a prostitute."

Kelly adds, "Well a pimp is a double edge sword, you get acre of knowing you have a pimp who will protect you but you are also under his thumb, but if that's what you like girl, good for you."

Tracy adds, "Yeah, I'd say most trannies like us work freely, I'd say about 30% here are pimped."

I reply, "I've always felt submissive and sissyish so I have wanted live with and hook for a Master. All has recently fallen into place and her I am my first night as a street walker."

We all chat of a few minutes, the girls tell me areas where I can take men for sex. They tell me that most men I will likely do are gonna be between age 30 and 60, ironically most married, some divorced and the rest mostly younger dudes single and fuckin horny for quick tranny sex. It's relatively safe here as most of us girls stay near by, but it can be rough and some dudes want sex but do not think they should pay for a tranny to do it.

Both tell me they have been assaulted by bad Johns and a few girls have had to go to the hospital. I ask about cops, and the tell me since we are in the commercial/industrial area and if we stay here and away from any residential type areas they don't bother us too much. Once they see you as a new girl they will probably run ya for any arrests and such but mostly leave ya alone. I'm told to not tell cops I have a pimp though. They tell me social workers will probably be by to talk to me about prostitution and such to try and help me, but the know most trainees who prostitute was to do so and enjoy it.

They tell me the diner up the street is where we go to take a break get a load off our heels and to touch base with each other. You will be a part of our group community for safety and support. That makes me feel much better. This said they notice a car pull up and ask if I want to give it a try? I'm so fucking scared but I note to them I will approach the John in this car.

I walk up to the passenger side and the window is down.

I ask, " Hi..hi hun, you looking for a date?"

The guy says, "Maybe... ahh you are a tranny right?"

I reply with a smile, "Yes, hun, you like trannies?"

He says, "I love trannies as I find that they are wanting to really please. "

He asks how much for a date?"

I reply, "$40 darlin, I suck or take fuck for $40."

He pauses and then says, "Ok... ok... that's fine, you got an area you want to do it?"

I look up and see down an alley a few garbage bins and say, "Um.. you good behind a dumpster? If so just park your car over there (as I point to a parking loot) and I'll meet you by that dumpster (as I point to it)."

He nods and drives off to park. I strut in my heels across the street and through the parking lot to stand by the garbage bin. Soon I see the guy park and step out, he's white probably 30 or so about 6 ft. tall and maybe 200lbs, wearing a polo shirt and jeans. He gets to me and asks my name, I tell him it's Chantel and he likes that name a lot, he tells me his name is Gary. He has only been with few tranny working girls as it make him nervous but he loves the way we dress, act and look. He finds sex with us very hot. I tell him that I'm rather new here but eager to please. He pulls out his wallet and grabs 2- $20's and gives the to me. I put them in my bra.

I ask, "So what do ya like Gary?"

He excitedly replies, "I really would like a blowjob."

I reply, "No problem hun, come lean against the wall behind the bin here."

To which he does and just looks at sexy, slutty me.

I get down on my haunches and look up at him, with a big smile, toss back my hair and tell him to relax. I then undo his belt, and pull his jeans down. He is in briefs and I see a stiff bulge in his briefs, I smile and tell him it looks like we both are gonna enjoy this. I soon have his briefs down and before my eyes is 7 inches of nicely thick cut white cock.

I say with a seductive tone, " You have a nice cock."

He smiles and says, "Thanks, please suck it, suck me off."

I grasp his balls with my left hand and stroke his cock with my right, really getting him hard. I look up at him, toss my hair back again and smile as I now move towards his cock and take my tongue to dance around his cock's head. The moans Gary gives are intoxicating and I love it. As I keep doing this Kelly walks by her heels clicking with a rather mature more heavy set man and she says to me, "You go girl, make your man happy."

I stop look over my shoulder at her and say. "Mmm, thanks I will." as I move back to playing wit Gary's stiff cock. I tongue the back of his shaft from his balls forward to the tip and he is pounding the walls with his hands in growing lust.

I now take his 7 inches as best I can in my mouth through my red lipstick colored lips and my tongue working it inside my mouth. I slurp up lots of saliva as we get into some series head bobbing own his cock. The moans and groans the both of us give is so seductively erotic. I enjoy the feeling of Gary's stiff white cock in my mouth and he fucking loves the blowjob he is getting. We keep working with me bobbing and slurping his cock. Gary can't help to not run his hands over my head and through my hair. This excites both of us to get even more and more with it.

I can sense Gary is working up to his eventual prize of a hot orgasm into my sissy, slutty mouth. We keep moaning with mutual lust and joy. I can sense every second that goes by Gary gets closer. I want him to cum in my mouth badly as I bob harder and harder on his cock.

Gary in hard lust says, "Oh shit, I'm so fu...fuckin close..ahhhh...ohhh."

I work it and work it as he comes closer and closer as I feel his firm hands now grab the back of my head and push me on his cock hard.

He is excited and says, "Fuck, ahhh...ohhh.fuck, yeah..ohhhhhh!" as he lets to a thick gooey wad of his hot and sperm filled cum inside my mouth as I swallow every drop and love it.

He pulls out, we make eye contact and we both smile as he pets my head and tells me that was fucking great. I tell him I am happy that he enjoyed it. I tuck his dick back in his briefs and do up his pants. I get back up off my haunches as he helps me up on my heels and we both walk back to his car and he gets in and says he will see me again soon. I smile and say to him yes we will. He drives off and I walk back to the street corner and talk to Tracy and Kelly as they introduce me to a couple other girls, Jenny and Krissy. All four of them are and to me the new girl. But soon it's back to work as I am offered another car that has pulled up. I am more confident already.

I strut over to this car my red suede 6.5inch spike heel pumps on 1.5inch platform clicking away with each step. I lean into the passenger side window.

I say, "Hi, how are you tonight?"

Driver in car replies, "Fine, nice night and you hun?"

I reply with smile, "I'm good darlin, you looking for a date?"

Driver says, "Um yeah maybe, you are pretty hot, nice legs."

I reply, "Thanks hun, do I really excite you? turn you on? you like chicks like me?"

Driver excitedly says, "Umm yeah, I got a boner in my pants right now, how much?"

I smile, wink, "$40 darlin."

Driver says, "Ok, sounds good, um where do you want to go?"

I say as I look up and down the ally where I was before, I see a gal and a John by the garbage dumpster so I scan to see under a stairway, "Looked like that stairway down the block there can be good. You park and I'll walk there to hook up ok?"

He drives over to park as I begin my strut to the stairway. I get there first and wait for him. He steps out of his car, he's a mature white guy maybe 50, average height and weight, in a business suit, so he is some sort of professional. He calmly walks towards me and stares at my tall, slender body, with my short black skirt, black stockings, red pumps and all.

He speaks, "My name is Ben, you look so hot and new here."

I smile and reply, "Hi Ben, my name is Chantel and thank you, yes I'm new here, it's my first night on the stroll here."

Ben speaks, "Lovely name, can I just look at you for a minute, maybe run my hands up and down your stocking clad legs?"

I reply, "Sure you can Ben, but first I need my donation."

Ben coughs and says, "Jeez sorry hun, I am totally turned on by you and I forgot." he reaches in his wallet and hands me two $20's as I put them in my bra with the other cash I have.

Ben then runs his hands up and down my stocking clad thighs as he pants with desire. He can't help but not to get close and grind on me as his hands go wild on my legs.

Ben all worked up says, "God you are so sexy, I do not care if you are a chick with a dick on the stroll here, I love your look, fuck I'm so damn hard."

I ask, "What do you want to do Ben?"

Ben excitedly replies, "I want up your skirt and in your panty. I'm so fuckin hard I need my cock up your ass girl."

I now proceed to undo Ben's pants and drop them, I feel his bulge in his boxers as I pull them down and both my hands fondle his cock and balls. Ben is hot with delirium and animal drive to want to fuck me. He is 6 maybe 6.5 inches long but nice and thick close to 2 inches and uncut. I reach into my purse and grab some lube as I then rub it over his stiff cock. I then turn around and lean against the wall under there stairway lift up my mini skirt and pull down my panty. I look over my shoulder and hand Ben the tube of lube and ask him to finger my butt hole with lube. He excitedly grabs the lube and soon is fingering my hole working the lube in it. He is sighing with desire and I am moaning with lust at him fingering me. Soon the tube of lube drops to the ground and Ben says he has to fuck me now, fuck me hard. I toss my hair and look over my shoulder bent over, my ass exposed and tell him to go ahead, fuck my tranny ass.

Ben takes his hands and pulls my cheeks apart to open up my tight little hole and he begins to work his stiff cock inside me. I let out a bit of an ouch and such as he stuffs his tool past my sphincter and he is so hot with lust. But he gets inside and works slowly at first as I moan and he groans. His cock is pushing nice and I feel it on my prostrate, if I was not in chastity my sissy dick would be hard. But I coach Ben on to give it to me, I moan and sigh as he gets harder fucking rhythm going. We begin to work in sync as his hands hold my hips and we move back and forth together. Ben tells me how fucking good it feels and how tight I am. I tell him to keep going between my moans.

Ben really gets into a hard pounding ass fuck on me to the point of me almost falling off my 6.5 inch spike heels. His grunts get more animal-like and I am more passive in my moans as his cock invasion of my tight ass gets hotter and harder. It is incredible for both of us and the wild sex I as a sissy slut and rather sexy cute tranny wants and deserves. Ben pounds away relentlessly as we moan in mutual rhythm and soon I sense he will soon let go inside me. I so fucking much want his cum up inside me, I feel like the dirty whore I am and love it.

Ben with a panting breath says, "Fu...fuck... ohh Chantel. ahhhhh gawd yes... so fucking close... oh you lil bitch, you got me so hot...ahhh...ohhhh, yeah .. all...almost their...ughhhh yeah, yeah, fuck yeah, I'm coming up your lil ass." as Ben fills my rectum with that awesome cum juice, one of the best things a real man can give.

Ben slows down, panting and thanking me for such a great fuck. He is so enamored with me he leans forward and kisses the back of my neck, telling me I am the perfect tranny slut. He pulls out and I turn and drop to my haunches as I grasp his softening cock and lick him clean. He loves it.

I sigh and say, "Ben you are a good fucker, I loved your way up my butt hole, I'm glad you are so happy."

I tuck his now soft cock in his boxers and pull up his pants as he pets my head and tells me he definitely wants more sex with me in future. I agree and soon he walks away. Before I put myself together I grab some tissue from my purse and wipe my butt hole of lube an some of Ben's cum that back flows. I discard the balled up tissue, fix my panty and skirt and walk back to the street corner.

Tracy an Kelly are also back and ask me how did things go? I say they went great. As we all stand in our heels strutting like there sluts we are I get a few more dudes for dates, three more blowjobs and two more butt fucks. I'm doing well for my first night.

By 10:00pm the girls ask if I want to get a coffee at the diner. I agree and the three of us walk to the diner, we get some coffees to go and Tracy was kind enough to pay for mine as. We sit at an outside table, take off our high heels and rub our feet. I love my heels but they can be hard on one's feet. I find Tracy is 35 and has been working for 7 years after her divorce and needing money to survive. She still keeps a bit of a day time life but mostly she lives enfeme and prostituting has paid her bills. She has been robbed a number of times and beat up a few times, it happens she says. I ask her if she plans on quitting. She says not any time soon. it makes her more money than her day time work does.

Kelly is 42 has been a tranny hooker for 12 years. She too is divorced with kids but they do not know she is a tranny slut. She has come to accept this lifestyle and loves the clothes and the sex so she is able to buy a lot of clothes with this lifestyle. She tells me getting robbed happens but not so much on this stroll. In another city she once worked it was bad for tyrannies. She was once beaten up badly and she was in hospital for a week. Some 250lb. dude just went ape shit on her after he had her suck him off. He gave her two black eyes, bruised cheeks and cut her lip as well as twisted her right arm. It was bad, but she says it comes with the job. She is much more careful today. It is safer to be a tranny slut here.

Soon we are back on our corner and I am told to go onto a new parked car. I walk up to the passenger side and see two men inside. As I peek inside I see two young dudes who are twins. They tell me it's their 30th birthdays and they both want to get on with a tranny working girl. I am intrigued at this and tell them ok. They ask me how much for a date. I tell them $40 for each of you.

Driver says, "Come on, it's our birthday, how about a discount?"

I smile and reply, 'Hmmm ok hun, you two boys can get a date for $30 each."

The look at each other and back at me and agree. They ask where?

I look around and see it's busy with other girls in our area I see a parking lot and say park in back in the dark. We can use you car as a place to get it on. They agree and I tell them I'll walk over there and the can park. They drive off and I strut in my heels.

They park first and both step outside and wait for me. They are two 30 year old white males about 6'2" and 220 lbs each, blondes, tanned in good shape, one in a blue button down shirt with black jeans on the other in a white button down shirt and blue jeans on.

As I get to them they introduce themselves, "Hi I am Jordon and the is my brother Tate."

I smile and say, "My name is Chantel, nice to meet the both of you."

Jordon hands me $60 and I stuff it in my bra as I ask, "So men what do you all want tonight?"

Tate says, "Well Chantel, we figured one of us gets sucked off by you as the other fucks you, are you ok with that?"

I think, "Nice a suck and fuck.' as I say, "No problem boys, why not just have one of you sit on the hood of your car so I can bend over and give head while my ass is ready for the other to fuck, you all like that?"

They nod and agree. Jordon undoes his pants and briefs as he then sits on his car hood, he is maybe 7 inches and average in girth, as well as cut. I see Tate drop his pants and briefs and his cock is the same. I hand a tube of lube to Tate as I bend over and lift my skirt and pull my panty down, "Lube my ass Tate."