Shemale Street Hooker

Street Hooker Part 1

After booking in at the hotel in a smart suit and heels, I returned to my car to get my 'things'. My two bags seemed excessive for an overnight stay but this was a stay with a difference. The hotel was perfect. It was just out of the centre of an unfamiliar (to me) town and on the fringe of a rather run down area. I was starting to get that butterfly in the stomach feeling - the buzz of daring adventure and excitement in anticipation of the evening and night to come. Each time I organised these weekend getaways I knew it was going to be a hot time, dressed to kill.

The hotel room belied the hotel's grubby outward appearance and location. It was luxurious - a suite of 3 rooms comprising lounge, dressing room with sunken bath and shower, and a bedroom - and what a bedroom! Decorated and soft furnished in sensual dark colours and a****l prints this was definitely a 'sex-den'. The bed linen was a combination of black and a****l print silk.... so sexy! Much as I would have liked I had no time to sit and admire it for now. I had work to do. I wanted to be eye catching and distinctly fuckable. For the past few years I had begun to expore role-play and over time had become more 'extreme' if that's the right word. I had explored the realm of BDSM. I had long adored the icon of a dominatrix with black leather or latex fetish clothing, high spike heels, striking makeup and hair pulled back tight and high. I'd enjoyed playing the role at a fetish club just 3 weeks previous. However my favourite role had come to be street hooker. The thing is, it was no longer role play. It had become a reality I was addicted to. Cheap slutty clothes, excess makeup, high heels and all that goes with it was my exactly to my liking. The sense of being the 'bad' girl excited me, and the thought of being a sex object and getting paid to do as required by a 'punter' really gave me that 'buzz'. It was certainly making me feel so damn horny tonight, as ever.

I started a bath running and unpacked my bags in the dressing room area, placing all my makeup on the dressing table and hanging my clothes ready for later. I used the shower to wash and condition my hair which I then wrapped in a towel. The bath was luxurious and sensual with the perfumed bubble bath. After a good soak I began my now familiar routine of shaving all over. The only area I could not reach was my back, but I'd had that waxed only 2 days ago along with the back, sack and crack (ouch! - but worth it). By the time I was finished there was not a hair below my eyebrows and I had shaved my light beard twice to be as smooth as possible. I am really lucky in that department as I have very little dark hair so a little more foundation than what women would use would give perfect disguise coverage. Stepping out of the bath I wrapped myself in the softest of towels and sat at the dressing table. 

First were my eyebrows. I'd long been having them threaded but I hate to see stray long eyebrows. With my brow lift they now had an exquisite high arch. I'd been debating having them shaved and tattooed. That was the aim tonight - to get the cash for them. Perfect for distinctive shiny white highlighter. They are now short in length so I can extend them with pencil to different shapes. Tonight they would be long wings. Next was to blow dry my hair after applying relaxing cream. This helps my hair to go straight. Volume mousse on top helps build body to the top of my hair as I blow dry it. I had coloured my hair two days ago and it was a gorgeous platinum white blonde. I was so proud of my hair, which I had been growing for 8 years, sometimes poker straight sometimes soft curls. By the time I had finished my hair was soft and silky and falling well down past my shoulders. Using hair grips I pinned it back away from my face for the next stage - my makeup.

One word - slutty!! I knew how to do slutty (my favourite). First was foundation - I used a theatrical foundation which needed working with a sponge then setting with lots of powder. I took great care to make sure every part was covered and then blended from my neck onto my shoulders/chest. I used an exquisite brush to work in the powder then remove the excess. I created a perfect monotone canvas for the rest of my makeup. Next were contouring powders, light and dark, very contrasting. Blusher along my cheek bone and 'apple'. Much more than day wear, all then blended by brush.

Back to my eyebrows, using a stiff brush sprayed with a squirt of hair laquer I combed and brushed my eyebrows to shape and trimmed them. With a black sharpened pencil I drew very fine lines from the end of my remaining eyebrows round in a high arch to extend my eyesocket area. I then 'filled' in the rest of my eyebrows with colour. Eyeliner next - very thin to the inner eye area then thickening to the outside. A thick line underneath too, smudged to give a smokey look. I curled my lashes and applied a coat of mascara. This acts as a base for my 2 sets of false lashes. First are black and thick. The second set are long and spikey. I am now a dab hand at these using tweezers and an old makeup brush but early days had been difficult. I'd soon learned that long nails were a hindrance at this point! After leaving them for a couple of minutes to set I completed my eyemakeup with a mixture of black, purple and sparkly pink diamond dust. Overlaid was black pencil on my outer corners and on my socket line. I added a touch of stark sparkly white to the centre of my lids and to the inner eye area. Despite the lashes already being thick I added 2 coats of mascara to both upper and lower.... by now the look of a whore was definitely there and I was definitely stirring down below!

The final stage in my makeup was my lips. I used a very dark sharp pencil to draw lines outside my lip line to reshape and enlarge my lips starting from the centre and going out toward the join. The first coat of red lipstick was applied by brush and smudged followed by a second coat. This I dusted with powder and coated once more. Lip fillers was another reason to get some cash. The effect of full red pouty lips was perfected when I added the gloss - lip lacquer by Boots No 7. The 'staying power' was good. I squirmed as I imagined where they would be exploring later..... Always at this point I pause to check everything looks good. Invariably I end up adding more blush, which I did tonight. The result? Whore! I indulged myself with an admiring comment... "You cocksucking whore!" I smiled with pleasure with the knowledge of what I had become.

I removed my plain ear studs and put in the big hooker loops which are at least 4 inches across. In the second holes I added smaller matching hoops. I removed the hair grips and brushed out my hair. I lightly finished my blow dry, continuously lifting my hair with my brush to give volume. Finally I bent forward, back brushed my hair a little and sprayed generously with lacquer to set it. Standing up, I flicked my hair back and used even more hairspray to fix it. There before me in the mirror was a drop-dead gorgeous fuck-doll hooker - my alter ego or perhaps rather my true self. It was my plain day existence which was my alter ego. I knew that this was how I once needed to be and now was. 

Time for a cigarette and to enjoy the erotic sensuality of the moment before dressing. When I had first smoked, it had all seemed so clumsy and deliberate at the time, especially with long nails, but now I was on automatic and it felt natural to flick open the pack and slide out the long white cigarette, place it between my glossed lips and click my silver diamante encrusted lighter, offering its flame and almost in an millisecond taking the smoke deep inside. Sometimes I'm not even conscious of it! I caught my reflection as my cheeks hollowed while I inhaled the welcome creamy smoke. A long deep drag felt so good, hitting the spot, and after I snap inhaled and savoured the feeling, I blew a long stream of smoke upward. I knew some guys (and girls) really liked that and I'd come to use the technique to attract and flirt.

I so enjoyed that first cigarette (since lunch time). Smoking was now a deep rooted part of me. I'd come to be expert in mouth and snap inhales which are now automatic. I chilled as I smoked, looking at my makeup and deciding on one or two things to touch up - more mascara on my lower lashes and a slight lengthening of my eyeliner outward and upward from my eyes.

Inevitably by now I felt sooooo horny! My cock was beginning to throb, and I so wanted to release its juices but I had more to do.

The next stage was to dress. I began by moisturising my body using a combination of Angel body lotion and matching perfume. Next came underwear. My faithfull gel bra lifted and pushed my budding boobs into a sexy cleavage. The effect of estrogen over the last year had been definite C cup breast growth, harder and more sensitive nipples and no adverse effect on my cock. I was clearly a woman from navel up. My fake boob fund also benefited from my new and loved 'profession'. I was due for surgery in 3 months - all booked. I was going to size EE melons!

A black suspender belt next. This had no less than 12 suspenders which ensured my stockings were held up perfectly all round and very taut. They contrasted wonderfully with my skin. My stockings were 10 denier fully fashioned nylons with cuban heels. They were expensive but so so worth it with that wonderful feeling as they are drawn up my smooth moisturised legs. I'd long learned the knack of getting straight seams sat facing a mirror and lifting my leg so I see the backs. Top next - a white blouse with three quarter length sleeves and a lace up front. My black bra was clear to see underneath where the lacing was deliberately loose but I like that. Taking the two front sections of the blouse I knotted them together tight under my boobs, exposing my flat stomach perfectly. This left my tummy piercings clearly on display. One above and one below. I took out the plain bars and put in a bar with large pink crystal that nestled in my belly button then on the lower piercing pushed in the bar with diamante stone above and three 2 inches long dangling strings of diamante below. Then my skirt - if thats what this 6 inch deep band of vinyl can be called! It barely clung to my hips and there was no way it would cover my stocking tops... but then thats what a hooker would wear and somehow it felt just right... It also barely covered my erect 7" cock! A black thong finished the dressing to help hold me in!

Heels next. I had decided on white overknee high vinyl boots with buckles and chains and silver spike heels. 2 inch platforms and 7 inch heels. The only problem with a small foot size was that I had a small arch so this meant that the 5 inch difference made me almost walk on my toes. Short steps were vital and I adored the feeling of 'constraint' it gave me. I soon adapted to that now so familiar sexy feel and enjoyed mincing around the room. White is a street hookers pre-requisite as it stands out in headlights.

And so to the finishing touches. Earlier, I'd been to my favourite nail bar for a full set. But instead of cutting the tips back after gluing I'd just had them shaped then the acrylic. Long red nails that looked like talons. I finished with a black vinyl choker, 6 rings and lots and lots of jangly hoop bracelets! The sound of them was so slutty but for me erotic and sensuous. It was time to admire my efforts. I could not believe the horny hooker that looked back at me in the full length mirror, so obviously a working girl up to attract punters to make money. I had once thought that if I had been born a girl there would have been no doubt what I would have done for a career. I looked like a perfect cock-sucking street whore and was so turned on. The thing was... It WAS me... I AM now that hooker.

I admired my skills in transformation, dreaming of the hot night ahead of me.

I put on my leather coat. In my white vinyl bag I put lipstick and compact for touching up, cigarettes and lighter, gum to freshen my mouth, car keys, room key and condoms.

When first plied my trade I was in two minds at this point - prepped up. Excitement and apprehension. Thoughts of attracting the wrong type, or the police, had been through my mind. But now it was different. This was a buzz I craved. I had to admit inside me I felt an incredible excitement.... as my hard proud cock revealed! I had to do it. Just the thought of mincing in heels down the street looking as the prostitute I had become was almost too much for me. I could have cum just thinking about it! I simply had to do it to get my fix.

Gathering my thoughts to the task in mind I tied up my coat. It came down to above my knees so whilst it covered most, my legs were still revealed as I walked. I spritzed myself with a heavy dose of Angel and I slipped out of the room. The lift was at least 40 yards along the corridor and I was praying that nobody came out of another room. When I arrived at the lift I was relieved to say that no-one had appeared but when the lift arrived it opened to reveal two guys... Their eyes fell on me and their mouths opened... I strode in, turned and showed my long nails as I pressed the 'G' button. Mirrors in the lift gave me and them full views and I could see their hungry eyes looking at all of me. I returned a demur smile and sideways glance. God this was fun. I could not help but notice that one guy was clearly 'tenting' his trousers! I made a point of looking then looking into his eyes. The other had tight jeans on but even there I could see a bit of a lunch box. I was glad that there were two guys, maybe if it had been just one I'd be at risk... but then maybe that would have been a bit of fun. I so enjoyed flirting!

'DING' the bell chimed at ground floor. I minced out leaving the guys looking on in wonder. I'd have loved to hear their conversation after! The reception area was reasonably clear. A few guests were grouped around the reception desk and that kept most eyes off me as I stepped across the hallway. My spike heels clicked on the marble floor, attracting the gaze of the 'kinky' ones who knew. One was an older guy and the other a sexy looking woman dressed in a black suit. I could not help but notice her looking at me and her black patent mules were at least as high as mine. As I passed by I caught her eyes and smiled. Did she 'spot' me.... who knows and I didn't care. I was enjoying this now. She returned with a knowing look.

Out the reception and turn right to the car park. Reaching my car, I shed my coat and donned the red pvc biker jacket I'd left there earlier. Thank goodness for the dark - it was just past eight o'clock. At least I would not be quite so conspicuous, I reasoned. However my white boots were definitely something of a giveaway as they were so visible in car headlights. Now quite comfortable in my heels I walked sexily toward my chosen location - Andrews Street, where I knew from the internet street local whores worked. After 200 yards the street lights became fewer. I started to relish the sensuality of my situation. The sound of my clicking heels, the tautness of the stockings, the cool air on my legs, belly and under my skirt, the subtle taste of my lip gloss. I stopped to open my bag, took out the pack of cigarettes (VS120's from my last trip to the States) and lit up. I inhaled the warm smoke... heaven knows what I looked like but I think I knew full well - a street hooker! I loved it. Already, cars were flashing lights but this wasn't the right place to pick up.

But where was Andrews Street? I must have walked for at least half a mile before I came to a cross roads. Relieved I looked up to the wall and found the nameplate. This must be it. But as I looked around there was nobody else here. Maybe a little early I reasoned. I noticed a few cars passing during this time. They were clearly slowing down to look at me. I was certainly very very turned on! Maybe it's the exhibitionist in me.

I hung around on the corner like the hooker I had become, smoking and flashing my white boots in the headlights. 

Was this just roleplay? Not now, though the buzz was still there as intense as ever. What I did know was that I had incredible feelings of on the one hand fear but on the other a sense of being alive, as the true me, and at the same time as horny as hell! 

Pulling my knotted blouse tighter so my boobs rose, and then straightening my skirt, I strutted right over to the corner of the junction. I stood and fished out my ciggies once more. Lighting one I happened to glance over the street at a shop window. There stood a woman, slim body with boobs prominent. Perched on sexy high heels, light reflecting off her diamante belly button piercing, hair as white as her boots, full heavy makeup and holding a long white cigarette, her looks were screaming out "FUCK ME!" It was me. It was my reflection in the window. A street whore and fuck-doll all rolled into one.

After 3 minutes a van stopped and out came another hooker. She stood just 20 yards from me and smiled. I smiled back. It was the right time for the earlies, on there way back home. I was really feeling the part and wanted some business bad. I swung my hips sexily taking long strides. As cars came near I looked directly in, willing the john to stop. I didn't have long to wait.

As I was lighting another cigarette, my legs apart and facing the oncoming traffic, a red BMW pulled over... "mmmmmm, classy" I thought. I stepped over and leaned into the opened window giving the punter a full view of my cleavage. The guy simply asked "How much?"

"25 for hand, 40 for BJ, 60 for a fuck" I replied.

"Sounds good to me you are a hot babe, get in sweetheart and lets do business"

After taking a long deep double pump, I dropped my cigarette and slid into the leather seat of the warm BMW. Now I could get a good view of my punter. Neatly dressed, suit and tie, greying hair and slightly expanded round the waistline, he was pretty good looking - much to my relief. Forty'ish. He also smelt nice (I didn't like horrible smelling punters that were just plain dirty but knew it was something that had to be tolerated).

"Business before pleasure darling, so lets have your cash" Even the process of asking for my payment was exciting.

"Here's the forty" he added "when I park up I want a nice slow blow job, OK?"

I didn't need prompting! "Of course! Thats what you are gonna get". I could not believe the natural and easy way I had come to respond. I took his money and quickly stuffed it away in my bag . What I wanted was to feel his cock and as soon as possible.

As he drove, my arm reached across and I felt his expanding package between his legs. My long nails caressed his hardening firmness. It felt good and I knew it was going to be big when fully hard. My mouth was watering already.

"Slow down, sweetheart, I like to savour this and I don't want to come too quick"

"But I am so hungry for your cock, I replied" Whilst I wanted to give a good service, I knew it would be better to be quick so I could move onto the next trick. Besides I felt so horny!

I didn't have to wait long, We drew into a smaller backstreet and parked up in darkness. I had been feeling his cock all the time he was driving but now I could get full access. He set the seat backwards and relaxed ready for me to get to work. I fumbled a bit with his belt, button and fly but my skills with long nails were good and he was soon fully accessible. I reached into his silk boxers and wrapped my hand around his cock. I pulled it out, setting it free. I was right, his cock was a good 8 inches and a nice diameter - not too thick for my mouth to take but then not thin either. I leant over kissing the tip of his cock. Already the tip was oozing pre-cum. I took one long lick at his tip and scoooped up his juice. It tasted good - a little salty, but nice. For a few moments I admired his cock - and told him how gorgeous it was. All good whores do that, but in this case it was very true. Without hesitation I took his phallus in my right hand and began to wank him slowly. My left hand started to tease his balls with my fingernails. My mouth had already been salivating for several minutes and I drizzled some spit from my mouth onto his member. The skin to his cock head was getting lubricated and it slid back to reveal all of my target. Slowly I brought my tongue to the side of his cock and licked my way to the tip then underneath on that special sensitive spot. He was already throbbing and I hadn't even got to the best bit. Meanwhile, his exploring hand was inside my thong and a finger easing into me.

Opening my mouth, I slowly slid my lips over the head, sucking gently as I did so. I slowly pushed my head down into his lap so he could feel his cock pushing deeper into me. I stopped half way and then sucked as I withdrew completely, making that 'plop' sound as he left my wetness. I went down again, working him with my hand and sucking. Up and down my head started to bob. I am a cock-sucking whore and I love it! Twisting my head as I went down whilst wanking him with my hand, sucking harder as I withdrew, exploring his head and underside with my tongue I was starting to work up a rythmn. I was fucking his cock with my mouth. His pleasure was obvious. I could hear his moans clearly, then he spoke "Thats right, whore, suck me good. You are a fucking brilliant cock-sucking whore.....mmmmm thats so good....." I was in heaven - my vocation fulfilled.

Eventually I had his full length inside me, leaving it there, sucking with my throat for a few seconds before raising my head. I started to feel his balls tighten... not long now and I would get my reward. "Get ready babe, its on its way" 

"Give me your spunk" I responded eagerly. I was desperate. "Fill my mouth. Shoot your gorgeous cum in my throat" I implored.

Quickly I sunk down on him again, sucking, to be rewarded by his cock throbbing hard and his warm sweet cum shooting into me. "Mmmmmmmmmm!" I murmered with pleasure through his orgasm, as his juices filled my mouth and started to seep out at the sides..... I sucked and swallowed as much as I could but he was a deliciously heavy cummer. Feeling him slowly deflate I sucked the very last drop out of him, I withdrew him and started to lick him clean. I'd loved the taste of his cum and wanted it all!

"God, that was good. You are a fucking good cock sucker and I want more of you. Here's my mobile. Ring me next wednesday evening. I am in town and we could do some more and unfinished business at the hotel I am staying at."

"It would be my pleasure" I replied, "I will look forward to it very much. Glad to be of service tonight. Next week would have to be enough to cover my street earnings for an evening, ok?"

"As long as you look like you do, sure!"

He tidied himself, and as he did so I turned on the vanity light and refreshed my lipstick using the compact mirror.

"You know, you look fucking incredible" he said, "I can't wait to give that whore face another good fucking"

"I hope that won't be all that gets a good fucking, darling" I replied, "I will look forward to it too. Lets go, I have more work to do..."

He drove me back to my pick-up point and dropped me off. "Don't forget. Next wednesday" he reminded.

I smiled, reached for his cock and gave it a squeezed, then slid sexily out of the car. I strode over to the shop doorway to have some gum to freshen my mouth for a minute before lighting a cigarette and hooking my next john. I felt good but needed more... More cock and more cum... This hooker felt insatiable in her addiction!

100% (27/0)
Categories: Shemales
Posted by MelissaKandy
1 year ago    Views: 2,775
Comments (9)
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6 months ago
so hot!
11 months ago
Stunning detail and so descriptive!
11 months ago
well written and exciting !
1 year ago
So sexy and well written. Made my panties soaking wet baby! Hope to read more soon.
1 year ago
Wow, what a story! Cant wait for part 2! x
1 year ago
I loved it. I want more. Xxxxx
1 year ago
a very hot story and tyvm for the make up tips included!
1 year ago
Very hot xxx
1 year ago
wow what a fantastic experience have never hooked but that was excitting