Becoming a Sissy Maid & Slut Vol. 10

I ask if she is single or married? She replied, "I was married with no kids, broke up 6 months after I lost my good paying career job. Wife and I now have minimal contact. She found out I strolled as a tranny slut and outed me to all my friends and family. My family has adjusted mostly to my lifestyle. Many of my friends have walked away from me though, a couple of them are ok with it. The rest can go fuck themselves. I'm keeping a roof over my head and am pleasing lonely and horny men. It's my GOD DAMN LIFE! I love being dressed as a girl and used as a slut."

Star asks more about me, I say, "I'm also a divorced male, no kids, ex-wife and I were career types, ya know D.I.N.K.S. We wound up just kind of growing apart with all the career type stuff and stress. We basically lost our passion for each other and felt it was best to move on. Being now in my 40's I figure that my life long obsession with being femme and cd'ing it was time to make my life happier or more exciting for me. I figured that joy for me was becoming a sissy girl." I go on to add, "I took a chance on a dominant male and have been enslaved more or less happily as his sissy maid and slut for about one month full time. So here I am." I add, "It's funny the things that can give one pleasure, acceptance and solace. I love being a sissy maid, wearing women's clothes and enjoy being groomed for slut service."

Jenny says, "Well there is something about many of us cd'ers/trannys and the slut lifestyle. When one free's their mind and follows their cd'ing heart, often slut work is a part of it all. Making some decent cash can only make it better."

I say, "Thanks girls, I feel better and am more excited about being a true slut."

Star says, "Chantel, hun, given your maturity you will likely find yourself servicing 30 to 50 somethings and older, most will be married but loveless or sexless, divorced or lonely and single. That is good as most will want to be discreet and not be much trouble for you, so enjoy them hun, they will likely pay you with no problems.

Jenny adds, "But sugar, if you get roughed up for your money, give it to him. It ain't worth a trip to the hospital or worse. If I had a pimp I'd rather deal with him post being robbed than waking up beaten up in a a hospital bed. Your Master will not want that for you as you in the hospital is not making money for him."

She adds, "If a guy wants freebie, again just shut up and give to him, move on to the next guy. Like Star said, most men you will find will be mature, will act very politely and again not wanting trouble especially with the law. Most are secretive to wives and family over their lust for trannys like us."

I say, "I'm grateful for all your advice ladies. I'm looking forward to being a sexy, street walking slut even more now."

Star looking at a car stopped about 20 feet away says, "I think that guy is eyeing you Chantel, you go girl, make your man some money, have some slutty fun." as she winks at me.

Well here goes as I step in my heels up to the passenger side of the car. Inside is a white, blonde haired male maybe early 30's. I say, "Good evening hun. Are you looking for a date?"

He replies, "Um, maybe yeah," he pauses and then says, "Wait I..I know you. You are the tranny that I fucked in the park a couple of weeks ago. You know at the picnic table with all the other guys," he adds, "You are umm, Chantel, right?"

I reply, "Yes my name is Chantel and yes I remember you now." as I smile.

He says, "So you are now out on the tranny stroll. Good for you, you're pretty hot for a tranny."

I blush and say, "Thank you, shall I get in?"

He says, "Fuck yeah, please do," he adds, "My name is Logan."

I say, "Well it's nice to meet you Logan." I add, "A date though is $40.00."

As he reaches for his wallet, Logan says, "No problem hun. You were fun at the park a couple of weeks ago. I'd like to have some fun with you tonight." and he hands me two $20.00's.

I stuff them into my bra. and say, "Thanks."

He then drives down and into a back parking lot, then parks discreetly behind a coupe of large garbage bins. It's very dimly lit and soon he is popping open his pants and pulls out his ever engorging 6 plus inch, cut cock. He tells me how much he wants to see me gobble it up and play with it in my sissy, slutty mouth.

He fondles it as such. I look at his eyes with my batting mascara covered eyelashes and then my right hand takes over playing with his cock. I then slowly lean over to his crotch and soon slip his hot, hard cock into my wet, slutty mouth. My tongue slurps all over his cock and Logan moans with joy. I suck and slurp, tongue and kiss his engorged cock's head.

Logan is now really into it and it is now my slutty mission to bring his glorious jizz and sperm up from his balls and his prostrate. Mmmm I suck and play and he moans and groans. I can sense the thrill of sexual excitement for Logan is soon to happen. He pets my head as I bob on his tool. He is moments away from the prize he so wants. Logan is moaning and soon lets out an ugh and a panting sigh as a thick jet of his hot cum sprays inside my mouth. I as now standard for me swallow all of it with pride. I pull off his cock, look up at him and smile. He sighs and says, "Fuck, fucking great Chantel," he pants and says, "I fucking love it, just love it girl."

I smile again, "I'm glad you enjoyed it sir. I loved sucking you off and giving you your money's worth."

Soon his pants are done back up and we drive back to my street corner. Logan tells me he wants to hook up with me again sometime. I tell him my Master will likely keep me at this stroll most nights now. Logan loves to hear that as I step out and he then drives off.

I walk back to the sidewalk and Jenny is still there, Star is with a date now too.


Jenny with a sassy tone says, "Mmm girl, you had some fun?" and asks, "How did it go for you hun?"

I smile and say, "Jenny I actually sort a knew the guy, we hooked up a couple weeks back at a park when he among a group of men fucked my ass," I go on, "Yeah, his name is Logan and loved to have me suck him off tonight as my first paying client."

Jenny says, "Ya see Chantel, being a street walker can be lots of fun, lots of guys are just horny and are into getting it on with us. Most men really do love to be kinky at times, we tranny sluts know this and have fun with it."

Soon Jenny gets a date and is on her way inside a car. I'm standing around and waiting. Star is still out on a date. I notice a minivan drive slowly by me and then drive off. I strut in my heels back and forth a few feet at a time and wait for another hopeful date. I see the minivan drive by again, slow and about 30 feet up the street then stop. I begin to walk up to it, approach on the passenger side. I look inside and the side window rolls down. Inside is an older white guy, average looks and graying hair, a bit tubby in his gut. I ask, "Hi hun, you looking for some company tonight?"

He replies, "Umm, maybe, I'm kinda new to this," he asks, "Sorry but take no offense, but you are a chick with a dick right?"

I smile, and say, "Are you looking for a chick with a dick?"

He answers, "Yeah..yeah I am, I've been curious about this," he asks, "How much for a date?"

I answer, "Um, Forty hun... You can play most anything you want with me then."

He replies, "Oh ok, come on in."

I step inside his mini van on the front passenger side.

He tells me, "My name is Gerald, and yours?"

I reply, "Chantel, nice to meet your Gerald."

Gerald then hands me $40.00 and says he knows a place up the road where we can go for some privacy. I tell him ok and soon he drives into the empty park's, back lot and backs in to a spot to see the street from his windshield.

He says, "Are you ok if we just talk for a while Chantel?"

I reply, "Of course Gerald, no problems to chat if you like."

Gerald goes on to tell me about himself, he's a 66 years old retired widow with 2 grown kids. His wife passed away a year ago. It's been tough and he has fought loneliness as he really does not want to find another longterm relationship. He does enjoy exciting company and has come to meet with working girls like me. He says as odd as it is for him to be with trannys, that the few he has shared time with have been polite, super ladylike and sexually stimulating. He tells me though that he is still nervous about hooking up with working girls such as me.

I politely tell him that wish to please him and if I can fill in some of that loneliness for a while, then I'd be happy too. I feel for the loss of his wife and hope he can move on as he still has life to live. I say to him I'd like to give him back his $40.00 but my Master is counting on me making a quota.

Gerald interjects, "Oh no please I do not want a freebie sympathy moments with you Chantel. I know you have a job to do, I just want an ear to bend first and then play a little bit with you."

I reply, "No problem sir. I hope to be an ear for you and to give you some pleasure tonight."

We chat for a couple more minutes to break the nervous tension for Gerald.

Gerald then says, "I'd like you Chantel, if you can please now undo my pants for me?"

I say, "Mmm, sure Gerald let me get to it?"

I then unzip his pants and help pull them open to then fish though his boxers his enlarged 7 inch, nicely thick, uncut cock. I then begin playing with it as he leans back in his seat and tells me softly how good it feels. I then move onto his stiff shaft parting my red lipstick covered lips and sliding his now hard rod into my wet mouth. My tongue caresses his cock as Gerald moans. I start my slutty head bob and Gerald pets my hair. We both moan in lust and I can feel his cock work a wad of soon to be hot goo up through the hard cock.

He moans, I slurp and he holds my head on his shaft as he lets out a grunt and a sigh, with a " Oh my God, oh my God, Chantel." as he shoots a thick, yummy wad of his semen into my sissy slut mouth. I lick him clean and he loves seeing my red lipstick on his shaft. Soon all tucked back in and driving me back to my street corner, Gerald tells me he enjoyed me tonight. I told him I enjoyed servicing him. As I step outside and plant my heels on the ground, Gerald tells me I'm a hotty. I wink and thank him as he then drives off.

I see Star and Jenny are back at the corner as I step in my heels back to the same corner. Star actually hands me a bottle of water with a here you girl. I smile and say, "Thank you."

She adds, "I figure you may need a bit of water to wash the cum down your throat." and she giggles. Jenny and I both giggle too as it's true, I luv cum but it does need to be washed down at times. :-)

We all talk a bit about the men we have serviced tonight. I tell them it's off to a nice start for me. We all get it, tranny sluts like us are in our own element as street walkers. Well soon the both are off on other dates. I wait in hopes of another guy who is looking for some fun.

Soon a guy in a nice BMW 3 series soon drives by me slowly, he stares and we both make eye contact and he smiles. He also stops about 30 feet up the street. I'm thinking, well here goes girl. Click, clock in my heels and I'm soon at his passenger side door. Window is down and he whistles a cat calling way. I smile and say, "Hello."

He says, "You are new here."

I reply, "Yes sir, my name is Chantel, would you like some company?"

He says, "My name is Miguel, sure, step inside."

Miguel is a 40 something, Latino male of average heigh and weight, pretty good looking and wearing a smart black button down shirt and black jeans.

I get in, and ask, "Anything specifically you looking for Miguel?"

Miguel says, "Hmm not sure yet, how much do ya need for a date hun?"

I politely say, "$40.00 Miguel."

Miguel says, "No problem Chantel." as he pulls $40.00 from his wallet and hands it to me. I stuff it in my bra.

He then drives off and soon down a back lot parking lot and stops near a outdoor garbage bin. He asks if I'm ok talking for a bit first? I agree. It seems Miguel is married for 18 years and has two teen age kids. He tells me he and his wife love each other and the kids but no longer are in passionate love with each other. I listen attentively as he goes on telling me that his wife has turned 'bi' but he thinks she is really now a lesbian.

She and he have agreed to do their own things sexually. He tells me he is not wanting a secret mistress nor a divorce. The kids are too important to each of them. So she finds other like minded chicks for her to date and play lesbian games with. He is into playing the field of prostitutes, real girls and chicks with dicks. He does seem bothered at the thought of that though. Saying he finds it a zesty fun thing to do to hook up with trannies but afterwards he feels sorta bad. He tells me his lifestyle growing up has not always been so positive to gays and trannies. He often feels bad about hooking up with chicks with dicks as he feels gay and he is not into gay men.

I interject and say, "Hun, I'm no gay man, I'm carrying on as a chick, I feel like one, I act like one, I dress like one. I like being chick but one with a dick, slut." I go onto to ease his mind and say "Growing up male I think I know what men like in sexy girls. Genetic girls obviously have it all naturally and some really can flaunt it well in life and for some as street walkers. But trannies like me do have it all passionately. I and we luv it, we try harder, we crave being like slutty girls to please real men. I hope that helps you Miguel?"

He then adds that yes he likes vag. but is also really into tranny mouth and ass. I keep listening, it's fascinating to hear normal men who are doing diverse things. I am impressed that Miguel and his wife have enough decency to stay together and just be friends to keep a stable life for their teenage kids.

Miguel says, "Are you now ok with stepping out by the big garbage bin there and having me fuck you up your ass?"

I reply, "Of course Miguel, let's have some fun.

We both step out of the car. I plant my heels down and fix my leather, mini skirt. Miguel walks around to my side of his car. He extends his right hand and I take it with my left, as I see my fingers with long acrylic nails with their bright red polish fall into his hand. We walk up towards the garbage bin. I then bend over, but reach in my purse first and pull out a small tube off KY and Miguel asks me to hand it to him. I then pull up my mini skirt and pull down my back seem, pantyhose and panty.

Miguel takes some lube and begins to finger my butthole as I bend over and place my hands on the side of the garbage bin. I say, "Mmm feels good." as he fingers me. Soon though his jeans and briefs are down to his ankles and he takes his 7 inch cut, latino cock and begins to push it up inside my rectum.

"Ahh, oohh, ahh." I say as he is now inside.

Miguel says, "Mmm nice Chantel, your ass is nice and tight." as he begins to pound it, but pounds it harder and harder. We both groan and moan I pant and ask him to pound me harder. Lots of ughs and ohhs by both of us. Miguel pants as he pounds me harder and harder, I feel as if he wants to fuck me off my high heels. "Mmmm... mmmm... ahhh," I say.

Miguel says with passion, "Umm, Ch...Chantel... I..I'm almost there, ahhh ugh." and he lets out a groan and from the bulbous head of his cock inside my butthole a blast of his sperm filled cum shoots out in all its thick, gooeyness. He sighs, I sigh, he leans over his firm hands grasp my chest, I hold on to the garbage bin and I feel his heart pound on my body. We pant and breathe and soon he pulls out. I turn and drop to my knees and I lick his used, wet, dick clean.

I look up at him and we both smile as I tuck his cock back into his briefs, do up his pants, fix my panty, pantyhose and skirt. We get back to his car and he drives me back to my street corner. We both say good bye and hope that we will meet up again.

Me and the girls talk and through the rest of the night I do enough men to make $320.00. Master George comes at 12:30am to pick me up and loves the $320.00 I earned for him. He is proud of me as we drive home. I am now a TRUE CASH EARNING SLUT!

At home and ready for bed, I have had a busy day and a busy night but I will drift to sleep in bliss. Before so, Master told me I will get most of Sunday off because I was a damn good girl this past week. But he noted later on in the afternoon I will have to dress in the following outfit, a pink satin maids dress, white tights, white 5 inch high heel pumps, of course my wig and make up. He tells me a very interesting and exciting Sunday afternoon and evening is planned. I find another exciting surprise for me before I go to bed. Master has replaced all my panties with new ones, black, white, beige, and pink satin panties with each having some modest butt and hip pads in place. These are just enough to help give my bottom a more feminine look but not bulky with massive padding. I LUV THEM!