An Interlude, Bailey on the Prowl

A little quickie story published between my continuing chapters of Recruiting a Sissy Maid... I hope you all enjoy it and find it, well hot... Characters in it will be new. All names and persons here are fictitious and any resemblance to real persons is coincidence.

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As I sit here at my bedroom's makeup table, freshly showered, shaved, sweet smelling body lotion spread over my rather soft, tall, lanky body I drift into thought...

'I love dressing up as a sexy girl, my whole life has given me these thoughts and when I can, have enjoyed doing exactly that, dressing happily, femininely and sexually as a hot and excited girl.'

Drifting back to my purpose at hand I begin my transition from rather normal, regular Phil, the guy next door, forty something divorced male, to that of cute, feminine, sexy my alter-ego so to speak named Bailey. I begin laying foundation and concealer on my face. My rather clear and soft male skin so well pampered over the years accepts this and it's a nice base for my face feminization through artful makeup. I look at my eye makeup choices and decide to go bluish and black with eye shadows as these will contrast nice with my green eyes. I love doing a smokey eyed effect with bright hi-lite s to make my rather male looking deeper set eyes stand out more. The blending of blues and smokey-grey/black shadows makes my green eyes pierce. The eye liner and mascara only increase this effect. I shape my eye brows next, I as a male keep oh rather neutral so with artful eyebrow pencils and powders can create a gentle arch. Once done I stare into my lighted makeup mirror and love that look. I think...

'Bailey, you sexy little bitch, you little hottie, your eyes kill it. Many men will want you babe...Yeah sure but I never go out on the prowl for men. I just live in my mind this sexual little transvestite vixen.'

Back to my continued face makeup, my lips, lips will be a deep red colour and lip liner trying to make my lips more girlie. Then more contouring of my feminine face with artful and skillful application of powders. I finish off with a deep red blush, tastefully applied to my cheek area. Grab a bottle of new perfume for Bailey, Lancome's La vie est belle and a spritz on my neck, décolletage and wrists and I think...

"Holy cow girl you smell so beautiful, so sexy, so feminine."

I blow a kiss to my feminine face reflection in my make up mirror, stand up wearing only a black lace pushup bra and matching lightly padded black lace panty. I gingerly walk to my closet and thumb through all this girl's feminine wardrobe. I smile, smirk, my right index finger on my lips as I see my closet is about 75% full of girl clothes and only 25% of guy clothes again I drift to thought...

'Bailey, even a trans girl gets caught up in clothes, female clothes are so exciting, cute, sexy, flirty and well just so soft and fun to wear.'

I pull out a short v-neck, shaping black lycra type dress with royal blue cut on a diagonal hash through the bodice part of the dress. I lay it deliciously on my bed as I then go into my dresser and the lingerie drawer to pull out a black satin and lace trimmed camisole. After I put my breast enhancers into my bra I slip this cammy over my head and shoulders, the silky smooth satin feels so good as it drapes over my upper body. I smile at the pleasure.

Back into my dresser and now the drawer full of pantyhose, tights and stockings. I find a black lace garter belt and put it on over my hips. I then find a pair of black sheer stockings with sexy lace tops. I sit on the edge of my bed, it's white satin covered duvet feels so comfy on my panty covered bottom. My toe nails are painted ruby red as I slip the first stocking over my right soft, long, smooth leg. The sight of my ruby red coloured glued on finger nails pulling the stocking up my right leg is so hot to my sexy, girlie mind. Up my thigh and now clasping the garter's clips is so feminine. I follow the same with my left leg and soon I feel so sexy, so womanly, so wanting to be desired by a gentleman.

I get up on my feet all 5'10" of me and look at my reflection in my full length mirror and I feel so good at what I see. I then pick up my dress and put it on fixing it smooth over my long rather thin body. It only goes mid thigh and just covers the lace tops of my stockings as I stand tall. Bend over a tad and the dress hikes up my thighs a bit to reveal these sexy lace stocking tops and garter straps. Again my mind wanders into thought...

'Fuck I feel so good, so sexy, so girlie. I smell great and I so want to masturbate as Bailey is such a hot and sexy transvestite. But I must hold off, the night is still young.'

I next go through my jewelry box and find a pair of sexy silver drop earrings with little hoops over opal drops, clip them on my ears. I find a heavy silver box chain for around my neck and a set of three silver bangles for my right wrist and a silver strapped delicate ladies watch for my left wrist. I now go through all of my wigs, my male hair is kept short as I live most of my life as regular looking Phil, but I find a fun wig I like that is shoulder length, wispy with cute bangs, most trannies will look better with bangs and it's light auburn with platinum blond hi-lights. On my head it sits great, is long enough to be very femme and frames my face well.

Almost done I now walk in my stocking feet to my shoe closet and wow does this girl have a lot of women's shoes and boots. I lightly bite my right index finger nail taking care not to chip the polish as I decide on my foot wear for tonight. Then I see them almost calling out for me tonight my new black leather Pleaser branded over the knee boots. Yummy I feel as I grab them and unzip the side zipper. Back sitting on my bed I put my right foot and leg into the right boot, the black stockings disappear into its shaft but a few inches and the lace tops stay exposed. I zip the boot up and repeat with my left foot and leg into the left boot. These sexy 4 odd inch spike heel boots are quite comfy. I stand up on these heels and walk to my full length mirror and see my feminine reflection, my girlie cock is stiff but tucked down ok for now.

Enjoying what I see I then walk out from my bedroom and to my kitchen, my heels click loudly on my kitchen floor and I love that sound as I make myself a coffee. Once done I take it and walk to my living room, putting the coffee mug on my coffee table. I walk to my record collection and decide to listen to some music as it's only 8:05pm. I find Stevie Nicks, Belladonna and place it on the record player. I love how feminine she has always been and I then sit on my sofa dressed so fun, so cute, so girly and so sexy, listening to the album as I sip my coffee. My mind then drifts from the music to thoughts of my femme self, yes I want to masturbate and once cumming would be sort of done with the heat of it all, but I do not want to well kill this night off so soon. I enjoy the music and feeling so sexy as Bailey.

By about 9:00pm I am really wishing I had the gumption to go out as I do not do that much as Bailey but my God I'm feeling as if I want to go on the prowl for a man who'd be into a girl like me. I've yet to be with a man with me dressed as a girl named Bailey.

For the next 20 minutes or so I struggle with these thoughts and I then get up and then turn off my stereo and go to my closet, pull out a black faux fur shrug and put it on over my dress. I grab a small black leather purse, put my I.d., some cash, lipstick, pressed powder, mascara and yes I have had in my company a small tube of lube for if/when I ever decide I may finally get on with a man. I now think...

'Well girl you are dressed and ready to go, step outside, get in your white Dodge Durango R/T and just go for a girlie drive...Maybe tonight will be the night to prowl for a guy. God I want to do it, but I am so nervous...Dammit girl you look so fucking good just go, get in your car.'

Like a puppet on a string I am now walking out too and into my Durango, my dress hikes up my thighs as I step up into my Durango R/T. It's cool but a dry cloudy Friday night with no rain though. My high heeled feet get on the peddles as I start my car up and soon I am backing out my drive way and I just driving off. I have no plan to where to go but I just drive. It feels so good to be doing this, my right heeled foot feels good working the gas and brake. I drive around almost aimlessly as I soak up the night. I have not too loudly a classic rock station on the FM dial as it soothes my nerves.

By about 9:55pm I want more. I look at my gas gauge and see my Durango could use a fuel up. I've only done this en femme once before and it was scary fun. I pull into a gas station that is empty of other cars. The first time I did this I used my debit card and paid at the pump. I want more this time. As I sit in my car I feel a need for a soft drink and I figure I will walk inside the store area, pick up a bottle of Coke and pay cash at the till with an attendant serving me. It is so scary but so exciting. I look at my vanity mirror and see a sexy and pretty passable t-girl. Besides the staff do not know me so why not? I open my driver's door and swing my thigh booted feet out and plant them on the asphalt. I begin to walk, click, clock my heels sound to the store and like that I'm inside. A young lady and man both about 20 or so inside and they look at me, scanning me, well I am sexily dressed and the boots speak for themselves.

The young lady from the cash register area says, "Hello, ma'am."

I instantly feel great being called a ma'am. The young man is mopping the floor and nods at me.

I smile and reply in a meh pretty good femme voice, "Hello." as I go to the cooler and pull a bottle of Coke from it then click, clock my heels sound as I walk to the cashier and with my red coloured nailed hand place the bottle on the counter.

I say with a smile, "I'll take the Coke and um $40.00 for gas on pump number 7 please."

She smiles and replies, "Ok, no problem dear, you look very nice tonight...I like your boots and your little jacket too."

I smile feeling like I'm on cloud nine say, "Thank you very much."

I pay up and say good night as I walk out, the young man holds the door open for me saying, "Good night ma'am." I can see and sense him looking at me as he does this from my heels up to my face and I feel he enjoys my look.

I get to my Durango R/T, put the bottle of Coke in a cup holder and the get to pumping $40.00 worth of gas. The light cool breeze feels good as it whips up under my short, tight dress.

As I am filing up, a car, one that looks like late model Camaro pulls up by me on the other side of the pumps, two oh 20 to 25 y.o. males inside. They both eye me and they both get out and walk towards the store staring at me as they pass near by. I sense they enjoy what they see as they both almost walk into the store's doors. I hide my giggles but love the feeling of male gaze attention. I think...

'Fuck what gal would not enjoy such simple visual attention by men?"

I'm finishing up putting my Durango's gas cap back on as these boys walk back past me. One whistles at me, the other chimes, "Nice boots."

I look at both wink and say, "Thank you."

They get a tease of my hiked up skirt and my stocking tops as I step back up into my Durango. Soon though I'm back on my way. I'm thinking...

'Damn girl that was fun, the looks especially of the men and the small talk was so exciting. Girl you pass well enough that men and women do not care much.'

Driving more around the city my lust for feminine life is high. I want to be on the prowl but am scared and nervous. My girlie balls are beginning to ache as my sexual heat is growing. I will need to jerk off soon be it parked in private or getting back home. I'm thinking...

'Fuck I want to experience a sexual rendezvous with a willing man. I'm near in my mid forties and I am scared like a child of my most feminine primeval feelings. I'm a fucking a grown adult why am I so scared?'

I am driving down a street and pass by a lighted bus stop bench, I see a lone male sitting staring at his phone, in my glance I see an oh regular fit looking white male in a black leather jacket, black jeans and black shoes on. I decide to make a few rights and circle back around. He is still looking at his phone as I drive by and this time slow down. I see he has brown hair, nicely kept. I see a large silver watch sticking from under his coat sleeve. He looks pretty good for maybe 30 something. I drive around again and pass by again, this time he does look up and see me pass by. I'm so fucking nervous but I'm so hot with aching t-girl balls. I find a pull out up the street about a 100ft. or so from the bus stop. I sit and look back through my mirror at this guy. I'm thinking...

'Shit I want this, but who knows if this guy is wants a hook up with a sexy tranny? He may tell me to fuck off, he may want to hurt me, but what if he is turned on by me and wants to take me up on a hook up? I better hurry if this guy is waiting for a bus.'

My nerves are a mess but I am opening up my driver's side door and bingo my heels are on the ground as I begin to casually walk towards this guy. My heels are clicking away. I'm in sexual heat but also almost ready to puke in fear. Each step draws me closer to this guy and just like that me in my 6'2" in my heels 185lb. stature am at the bus stop bench. He looks up at me and scans me head to toe says, "Hello."

I sheepishly reply, "Hello. "As I sit on the bench. I add, "Cool but nice night."

He looks at me, smiles and says, "Yes ma'am nice night."

Silence speaks loudly and I figure I better cut to the point or just get up and go back to my car. I can't believe what is now flowing from my mouth...

"Do you like my outfit? My boots? My look?"

He sits up, looks at me and says, "Fuck yeah, you look great, love your fuckin boots."

I say in heat, "I'm a hot and horny tranny...I've never done this before...but I fucking want you...I've never given head before but I so want to suck you off...I'm sorry if you are not into it and if not please just tell me so and I will go."

He stares at me, looking at my boots, my dress, black faux shrug, my face and hair. [pauses] and says, "You a hooker?"

I smile and giggle as I says, "Um no, just a hopefully desirable transvestite who now wants to be with a man."

He looks at me and says, "You are very sexy...umm my name is Mark what's yours?"

I smile and reply, "Bailey, how are you Mark." as I extend my right hand into his.

Mark answers, "Great Bailey, cute name." he adds, "Um I'd like to hook up with you. Where should we go?" as he looks around.

I tell him I have my white Durango up the street why not inside it?"

He looks up the street and says, "Ahh, I saw you go around in circles...You certainly locked onto me girl. Ok, lets go to your Durango."

We both walk up to my car and he actually holds my right hand as we walk, he says, " You smell pretty Bailey."

I say, "Thank you Mark."

We both get to my car and decide the second row seat will be best. He sees my dress hike up a I step up inside and he loves it as he licks his lips. He gets in after me. His hands immediately run over my stocking thighs up my dress and into my panty, feeling my hard t-girl cock. I run my hands over his crotch, he is rock hard in his pants. We then immediately kiss, with tongue and panting in sighs as we run our hands over each other's body's. I have never felt this way, being only having heterosexual boy on girl sex in my life to now be the femme with a guy is so hot and I'm so horny, my girlie balls are so aching.

We keep kissing and soon I get in words saying, "I want to suck your cock Mark, SO BAD! SO FUCKING BAD! I NEED IT MARK, NOW!"

He sighs and replies, "Do it girl, do it you sexy bitch."

My hands now undo his pants and helps him pull them down, next I pull his briefs down and before my horny eyes lays his big but not too big or thick, cut white cock, a nice size that a rookie t-girl to suck off. I like a moth to a flame am drawn to his manhood and I feel my red coloured lips kiss his cock's head. I then part my lips and let his cock slip into my wet mouth. I feel lust as it glides over my willing tongue. Mark sighs and pets my hair as I begin to suck on his cock, moving my head back and forth over this hard cock. I'm thinking...

'God this is it, 40 plus years and finally this sexy tranny bitch is giving head and it feels so fucking good.'

I suck on his cock, lots of slurping and saliva coats his manhood. I hear with pride Mark groan in joy, utter joy as he watches this sexy tranny suck him off. His petting of my hair turns me on more. I suck with intent and passion. I wonder if I'm going to spit or swallow once he cums...I KNOW THAT I WANT TO SWALLOW! All hot girls want to please their men by swallowing.

Mark moans and I can sense he is getting closer to ejaculating. It makes me want to work harder to bring him to cum.

Mark sighs and says, "Fuck girl, yes, fuck feels so good...ahhh...ahhhh...ohhh... fuck Bailey...oh fuck soon...ohhh man...so soon."

I work more and more forcefully to bring him to cum. I want him to cum. He is so hot with heat and the ejaculate gets closer to shooting from his stiff cock. I work on it and bang just like that I feel him cum and hot gooey liquid fills my mouth. Momentarily I feel repulsed, but seconds later I feel joy and desire and I swallow his semen and I love it. I love having his seed slide down my throat and into my stomach. Mark sighs and I slow up as my mouth slides off his cock. I look up a him doey eyed and smile as he pets me saying he loved it. His cock is smeared with my red lipstick then he tucks it back in his briefs as such, pulls up his pants as I sit up grab my lipstick from my purse and fix my lips.

He says, "That was great... you are a first timer? I can't believe it Bailey."

I reply, "Yes Mark but thank you for the compliment."

Mark says, "I missed my bus but it was fucking worth it."

I tell him, "I can drive you home."

Mark tells me he recently wreaked his car and it's being fixed so the bus it is for him for now. Him and I move to the front seats as I begin to drive him home. About 10 minutes later we park in his driveway. We talk about tonight and the joy we each had. Up comes it not having to end, Mark asks if I have ever been fucked up my ass. I tell him no, my mind thinks...

'Wow a blow job and now maybe a good butt fuck, what a night.'

Soon we are in his house, a normal looking home as he enjoys the sight of sexy me. He helps me take off my shrug and we sit on his sofa, he makes me a drink, a rye and Coke and he has the same. We talk about me being a tranny and how I finally decided to have sex with a man. This talk and a drink builds up curiosity and heat. Mark told me he has done anal on regular cis girlfriends in his past, so he is akin to it, but he is excited in taking my anal cherry as a t-girl to fuck. I'm nervous but willingly hot as we move to the act. We both decide to just do it down and dirty over his dining table. He helps me up on my heels and we walk to the table. The sexual heat is wild and we both sense this act of soon to be sex.

Marks says, "It's ok Bailey, don't be nervous, you will enjoy it."

I sigh and reply, "Thank you Mark, I'll try not to be nervous, I have lube in my purse let me get it."

I give Mark the tube of lube as I now bend over his dining table, smile and wait as he said he will do all the rest. I can feel my heart pounding in my chest and my breathing against the table top. Mark's hands now touch my back side, slip up my thighs, over my stocking tops, he sighs as he feels the lace tops and garters. He eases up my short tight dress, revealing my black satin and lace panty clad ass. My sighs and breaths grow more passionately with desires but also a bit of nerves.