tagTransgender & CrossdressersRecruiting of a Sissy Maid Ch. 14.5

Recruiting of a Sissy Maid Ch. 14.5


Readers, I am adding another quick short story of tranny girl Bailey hungry for men and cock. Inserting this story between Chapters 14 and 15 of "Recruiting of a Sissy Maid". I hope you all enjoy it.


Title: Another T-girl Bailey out and on the Prowl for Men and Cock Story

Friday night, I've been feeling a desire to dress up as Bailey all fucking day long. I could not get home from work fast enough. The drive home was so miserable as each click of kilometres passing by on my Dodge Durango RT noted to me I'm one more kilometre closer to home and to transform my rather typical 5'10" about 185lb male self to that of Bailey, a sexy, hot transvestite chick. Gawd my mind flows with desire to be so feminine and so sexy and hot. I must say I transform well into a girl, I always have since my first days on full on crossdressing. I'm of good mid 40's fitness, clean shaven, long sexy legs and a nice enough body where en femme I hide my 185lbs well.

By 5:30pm I finally get home into a modest house that I was able to get after my divorce. I get free time to be Bailey and over the years I've gotten good at fashion, makeup and knocking out girly looks and even those hot sexy ass, bitch looks. Since my divorce I've only dabbled in the dating scene with genetic girls, keeping my secret private. I find all too many girls today seem to be well high maintenance, kinda entitled and kinda looking for a wallet. I'm sure not all but being in my mid 40's and at least well off enough to be well ok, not rich, not poor but a decent hard working dude who's been through a lot. I've been there done that with my divorce.

But as time passes and life marches on I have come around to fantasizing and craving relations with men, confident men in recent times, but only when dressed as Bailey. I've only tried being out on the prowl for a man sexually a couple of times and dammit the little horny bitch I can be as Bailey had some hot and sexy times. Cock for a wanting trans girl like Bailey is so intoxicating. Only a couple of times with blow jobs and butt fucks but my memories of each is like it's in Panavision and Technicolor.

Inside my modest little house, I check the mail and grab a beer to sit and relax while I think about becoming Bailey tonight. Smiles of lust for being her is on my face. I finish the bottle of beer and get up to undress from my male life and shower up, making sure to use my feminine body wash. Once done and towelled up it's time for a very close shave.

Ten minutes later shaved and face freshened up with moisturizer it's time to put Bailey's face on. Standard fare concealer, foundation and powder to give my thankfully soft for a male facial skin a nice base. Eyes will be smokey black with lighter bluish gray hi-lites on brow bone and midnight blue for colour. Khol eyeliner to rim Bailey's eyes, curling my long lashes and blue/black mascara and my brows with a clay brown pencil and powder making my well cared for and androgynous brows get a nice feminine arch.

Contouring makes my face more feminine and a deep ruby blush lightly applied along with ruby red lips makes my feminine face pop.

I see Bailey's reflection in the bathroom mirror and I say, "Girl you look great." and blow a kiss to my reflection.

I glide to my bedroom and begin the dressing. I grab a matching black satin and lace bra and lightly padded panty set, pull the panty up my smooth long legs and over my hips. The light padding gives me bit of a shape. I strap on the black satin and lace bra, put my intentionally modest sized breast forms on. I do not want to appear to have huge breasts but tasteful breasts to my nature and style as Bailey. I next put on a pair of black sheer back seem pantyhose. I enjoy garters and stockings too but it's fun and comfy at times to pull on a good pair of silky sheer and in this case black back seem pantyhose too. I love the feeling of pulling them over my hips.

I decide to go with a Royal blue satin blouse and a black leather mini-skirt, so I first put on a black satin camisole with lace décolletage, so the v-neck collar of the blouse shows the lace off. I step into and pull up the black leather mini-skirt and damn it feels so good, so fun, so sexy, my black sheer pantyhose clad legs so long and sexy fill out from this mini-skirt. I walk to my full length mirror and turn look over my shoulder to see my seems and make sure they are run perfectly straight. Once done I'm satisfied. I put on a black 3 inch wide belt with gold buckle to cut through my waistline. I go through my collection of wigs and go with my blonde shoulder length with a few wispy curls, fun wig with cute bangs to frame my made up face. I have all too many wigs and hair colors I feel so blonde tonight.

Gold dangly earrings with zirconia stones hang from my ears, A gold bracelet with zirconia stones is put on my left wrist. I go with a black velvet chocker with a gold decoration in front, spritz on some Estes Lauder perfume and damn I smell fine girl.

I now think, 'Hmm...heels...heels...heels. What heels do I wear tonight?'

I find a pair of Royal blue leather lace up ankle booties with 4.5" spike heels, so cute and so sexy I feel. I am pretty well dressed up fully as Bailey and I'm in feminine, tranny Heaven. Looking at my reflection I am rock hard and love seeing cute, tall, girly Bailey before my eyes.

It's now about 6:45pm and I for a while just walk around and lounge around my house. I watch a t.v. show but I'm feeling I must go out tonight. I'm still quite nervous about going out as Bailey, but I love doing it so much. I recall my two previous sexual rendezvous with some hot to my eyes men. I am feeling a want for this and for some cock.

I fill a blue leather over the shoulder purse with some cash, I.D. perfume, makeup and lube, just in case I get some cock tonight. I put on a black leather cropped to my midriff jacket and grab my Durango's keys.

Opening the front door is often the hardest thing for me to do when I decide to go out as Bailey. I look outside, it's evening, just had a fresh rain shower, so it's cool, breezy and damp but I find myself scampering click, clock, click, clock in my spike heels and up inside my white Dodge Durango RT.

Start her up and I say to myself, "Ok Bailey girl, where to, what do you want to do tonight?" I laugh a bit and say to myself, "I so want to seduce a hot guy or guys to get into his or their pants, suck some cock and also have cock fuck my tranny ass."

I begin just driving around town. My desire and sexual heat only rises but I enjoy just driving around as Bailey. By 7:15pm I realize I have not had dinner yet and am a bit hungry. I figure damn girl got to find apace to eat and soak up being sexy and girly in public. Yes, I'm nervous but yes, I pass nicely and even if read I look girly enough anyways. I drive around as I decide where to eat. I decide to stop off at a local Denny's, nothing to fancy, but safe and decent enough food for this girl tonight.

I pull into the Denny's and park my Durango. I open the door and step out my heels click, clock on the damp parking lot, a cool breeze blows up my sexy mini-skirt and I begin to walk. I know I'm too sexily dressed for Denny's but it's a place where it wont matter much. I walk inside and wait to be seated. I young 20 something cute little brunette all 5'4" and maybe 110lbs. of her come up and greets me. Oh she does scan my outfit from head to toe, probably reads me as a tranny but she is polite, smiles and asks. "Hello, is it for one?"

I smile and reply, "Yes darlin, one please a booth by a window if possible please."

As we walk it's not too busy maybe 1/4 to 1/3rd full. She takes me to a booth by a window and introduces herself as Jenny, leaves me a menu and asks if I want something to drink, to which I tell her ice water please.

A few minutes later I give her my order of just a club house sandwich with fries.

Jenny feels a need to tell me, "I think you look great, very sexy, love your boots and your blouse hun." as she winks.

I smile and say, "Thank you Jenny."

By 7:40pm I am enjoying my rather late dinner, being not too busy I am comfortable here as Bailey. I do notice a gentleman got to be 40 something, white, dark hair, clean shaven in a brown leather jacket, over a white shirt, blue jeans and black shoes from time to time eyeing me, he may be wondering if I'm just a sexy genetic gal or am I a tranny. I try not to stare back at him but we do make eye contact from time to time. I see him casually smile and wink at me, I blush, eyes dart down and back up kind of submissively as I play with my blonde hair my ruby red polished nails contrast with my blonde hair. He seems to not be looking at me in a rude or angry way but in a fun and flirty way.

Jenny comes to my table, checks on me and my meal and we chit chat for a moment as she asks where I got my blue leather spike heel ankle booties. I told her I bought them online and gave her the retailer's name.

As she walks away I see this gent who has been eyeing me and flirting with me gets up, grabs his coffee mug and walks towards me.

As he gets to my table he says, "Um, I hope you are not offended but I find you very cute."

I look at him and reply, "Thank you."

He asks, "Would you mind if I sat here with you to finish my coffee?"

I sheepishly play with my hair and say, "Ok, if you like."

He sits down and says, "My name Martin, Marty for short and yes you look very cute."

I reply, "Hi, Marty, my name is Bailey and not to waste time I am a tranny, are you ok with that."

He smiles and says, "I fuckin adore cute trannies. I find them often to be cute, fun and open to things, I enjoy the way many of them dress as girls."

We chat for a while breaking the ice so to speak. I can sense Marty is growing hot for me on this Friday night and yes my tranny balls are beginning to ache as I begin to think about some sex play and I wonder about Marty's cock.

He gets around to asking, "Are you into play? I love hooking up with t-girls."

I reply, "What do you want to do Marty?"

He smiles and says, "I'm hot with feeling up your body and well [as he whispers] having you suck my cock...I really would like that Bailey."

I smile and say, "Umm, sounds good Marty, lets finish up and well go."

We both get up, Marty grasps my right hand as I get up on my heels and we both pay up and walk out. Marty asks if it's ok with we just hook up in his truck? I see he has a rather new Ford F150 extended cab and I figure it's probably good enough to get some action for each of us.

Marty helps me up in the passenger side of his truck and gets around to the driver's side as he gets in. I can smell his cologne and well he is quite hot for me now.

He says, "You ok if we drive to a bit of a more private place Bailey?"

I look at Marty and say, "Sounds good Marty." as I place my left hand on his crotch and feel his hard bulge in his pants, I sigh and tells him it feels nice as he looks at me, licks his lips and smiles back. We drive off a few minutes to a back parking lot of a large outlet mall, should be private enough for some play being it's after 8:00pm and another light rain shower falls, the pinging of raindrop on his truck almost enhances what will soon happen. I ask him to put his stereo on lightly to a classic rock station. I then lean over towards him as we both kiss and feel each other up. Marty's hands are all over my pantyhose clad legs and up my skirt, it's a turn for both of us.

Marty is in full heat and says, "Bailey...I...I need you now...I need my cock in your sexy tranny mouth now."

I begin to help him undo his pants and ease the down along with his boxers. I smile at his nicely endowed cut white cock. He asks if I like it and I look at him and smile as I reply. "Oh yes...nice...very nice Marty."

He now leans back in his seat his cock is fully erect and on display for me. I lean forward and my ruby red lips kiss his cock's bulging head as he sighs with desire. I then let it slide past my lips and glide over my wet tongue. My tongue dances with his cock as I suck it and my saliva flows making it all so hot and wild.

Marty begins to moan which I as Bailey love to hear as I'm doing well then. My sucking of his nice cock and his moans and groans works us both to a hot, horny fever pitch. Marty begins to stroke my hair as he tells me I'm doing so well and he is loving it, my cock sucking.

We work well and I bob and slurp on his rock hard cock, I can sense Marty is moving closer and closer to what he wants and that is to cum, cum inside my mouth. I work it more and more intently and I sense he is getting so close. His petting of my hair and his moans grow more intence and I work him right up to his grateful groan and then a blast of his hot cum fills my mouth, pulse after pulse of cum sprays from Marty's cock and I swallow it all up. I love that feeling of a guy blowing his load of hot semen inside my wanting tranny mouth, the taste of a man when I am dressed as Bailey is so hot.

We finish up, he does his pants up and he drives me back to my Durango, thanks me for the good time and I see him drive off as I get back inside my car. I'm even more in heat now I am looking for more hot guys and cock. Bailey wants to be a sexy bitch. tonight but where and how?

I drive and find an all night adult video/book/sex shop and figure hey first time for me I'm sure guys will lust for sexy bitch Bailey. I park and step out the wet sidewalk my heels click clock and the echoes bounce off buildings and windows. I walk inside the front of the sex shop, it's full of all merchandize one would see in said shop. A 30 something pudgy dude, dark hair, with a beard and a Cold Play black t-shirt on looks up from the computer till and scans me, smile at me and says hello. I reply with a hello too.

I walk around the shop my heels click as I step, a few other guys are about and all scan me, they thumb through magazines and a few some videos. I see a few take some videos, pay the dude at the till and walk in back behind a black curtain. I figure this is where guys can get a private space, watch some porn and jerk off to it all. Places like this are not unknown to have some sex going on. I walk up to the curtain and step behind it to see a bright red lit hall and booths with curtains, some drawn closed as I hear guys watching porn and sounds of guys jerking off to it. My lust and desire to hook up is high. My heels click as I walk down the hall. I see guys here and there open up their booths curtain and the pop heads out to see me.

One dude chimes out, "Fucking yeah, great fucking legs girl, you looking for fun?"

I stop turn around and look at him as I reply, "Fuck Yeah! I want...no need cock...I want cock up my sexy tranny ass, you want to give me some darlin?"

He coughs pauses and says, "Fuck yeah, I love tranny ass."

I walk to his booth as he sits back on the chair, a hardcore tranny BDSM video is playing on his monitor, his cock is out and in his hands. He's a 20 something, white dude, straight blonde hair a tad long, light framed eye glasses, a check shirt and his black Dickies dropped to his knees as his briefs are too and black and white Nike's on.

I enter and my right hand replaces his on his cock, he gulps as he stares at sexy tranny me, he wiffs my perfume and sighs as he says, "Fuckin sexy tranny bitch, right?"

I look into his eyes, smile and say, "Yes I am and I want you to fuck me, right here, right fucking now." I add, "My tranny balls ache I want a hard butt fuck and I hope you get me to blow a prostate load of cum as you fuck my ass hard."

He gets up from the chair and I move towards it, I bend over and brace myself on the

chair's arms. He tells me his name is Rick, as he scans my backside, my black leather mini-skirt and the hot back seems of my pantyhose right down to my blue spike heel ankle boots. I tell him my name is Bailey, as I look back over my shoulder at him.

Rick lifts up my mini-skirt, runs his hands over my pantyhose clad ass and then pulls my pantyhose down to my knees, then my black panty too. I reach into my purse and grab my lube, hand it to him and he opens it and dollups a finger load to then begin fingering my butt hole. He sighs and licks his lips as he fingers me and then massages my butt cheeks, his uncut modest white cock is ready for fucking.

Rick takes his hand and begins to feed his cock up my butt hole, I grunt and groan as he pushes carefully past my sphincter. We both grunt as he gets inside me, it feels so intense as Rick slowly works himself into a gentle rhythm as I moan and he groans. The lube works up well and soon Rick is thrusting harder and deeper and I feel his cock get onto my prostate and it feels so fucking good for both of us. I tell him I love being a cum slut and he loves hearing those words.

We work well together, me bent over the chair, ass out, Rick's hands on my hips as he fucks me harder and harder. Our lustful groans can be heard outside the video booth, surely other horny dudes may want a piece of my tranny ass too. But for now Rick and I are all hot for this butt fucking. He is fucking me so hard his eye glasses are fogging up but he is in auto mode as he wants to cum so bad.

Rick moans and groans as he thrusts and I take it like the tranny bitch I am and then he tells me he is about to cum and just like that he grunts and thrusts as his hot gooey cum fills my butt hole. I can't hold back my prostate orgasm as my right hand on my hard cock finally helps me stroke out my ejaculation and my tranny balls feel their relief. The two of us cum intensely together, Rick up my ass and me spilling my seed on to the floor.

Once we are both done, Rick pulls put, backs off, does his briefs and pants back up and I stand up, some of Rick's cum spurts from my butt hole as I pull my panty and pantyhose back up, fix my mini-skirt and stand up on my heels feeling tall and refreshed from my butt fuck and own ejaculation.

Rick tells me how good it felt for him and I replied the same as I then walked out from his booth. I'm spent now it's about 9:30pm and I feel like driving home now but a few other guys want me too. I do no feel like much more but between three other customers at the moment and the dude behind the cash register they all plead for some action so I relent and for the next half hour or so I suck two of the men off, and enjoy swallowing their cum. I then arrange to have one guy and the cash register dude to have one fuck me as I suck the other guy off. Two 30 something regular looking dudes get it on with me. They are quick to get going. The cashier dude gets bent over and into fucking me first as the other dude sitting gets his cock in my mouth. The first time for me to have a guy fuck my ass as I suck a guy off as Bailey. It's really intense. The sound of men moaning, groaning, and fucking me together as I slurp on hard cock is wild. Cashier dude sloppily fucks me and soon blows his load up my ass and then slaps my ass as he pulls out, cum still streaming from the head of his cock. The other guy holds my head firmly with his hands as he pounds my mouth with his cut white cock and bam, jizz fills my tranny mouth and I dutifully swallow up every drop of his cum. He pulls out my red lipstick is smeared all over his cock's shaft as he does up his briefs and pants.

The two thank me for the good time as I walk out and back to my Durango and now fully spent as well as filled I drive home, satisfied as a sexy, hot tranny girl. Bailey gets to have lots of t-girl fun.

At home, undressed, showered up I think about tonight and sigh with joy as I drift to sleep in my black bra, panty and camisole.


I hope you all enjoyed this little and new short story of sexy little tranny girl Bailey and her feminine and horny wilds. I kind of enjoy putting out quick little one offs. I like making Bailey into some hot little, sex pot, horny tranny girl. I hope my readers enjoy her ventures too.

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bySissy_Chantel© 0 comments/ 2957 views/ 4 favorites
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