Bournemouth Street Hooker for a Night

Wednesday June 1^st

Introduction

The phones been quiet for the Mistressing of late, so I decided that today was the day to indulge my favourite fantasy into reality once more. Now for certain I am used to dressing like a total slut for my clients, and have always been happy to indulge in cock sucking and safe anal play.

 There’s no better buzz than being paid for Mistress Session and forcing my slaves to suck my trany cock of. That’s a situation where its incall, and I am in complete control. What happens on this adventure is completely new territory, my intention to be a cheap sluty looking street whore. I am going to pick up some total strangers off the street and get paid the going street rates for sucking off their cocks and having a few cocks in my tranny arse. At least that’s the plan. Believe me girls and boys if this is something you are planning on trying, you’re going to need balls of steel as I was to find out.

Planning

Before leaving home for the two hour drive down to Bournemouth I decide what I am taking and planning to wear. Now I want to pass myself of as best as I can. But want to look as cheap and sluty as I can too. I do after all want to get the attention of the punters ahead of all the regular girls that will be working the streets of Bournemouth’s red light district too. I decide on being brunette for this adventure, and pack my favourite long brunette wig with my makeup. I also pack a skin tight stripy blue and black roll neck top, and denim micro skirt (13” length), suspender belt and 30 denier black stockings. The black PVC jacket and 6 inch high heel platform white knee length boots.

Now to save any procrastination when I arrive i decide this is all I am taking, everything for the transformation from my male self into complete street slut in one bag. This is going to cost me money in travel and hotel; I can’t afford to waste it. I need to follow through on this fantasy adventure and it’s now or never.

A little research  I discover that the mains streets for prostitutes in Bournemouth are in the Boscombe area, specifically Derby Rd, Southcote rd, kynveton Rd, in all about a Kilometre of streets that are all connected and easy for cars to circle round. Now I know which streets to be hanging around looking to pick up punters I decide to find a hotel in that area. Its 1.30 in the afternoon and I am all packed and ready to go. Filled with both excitement and in-trepidation about the adventure ahead of me I set out on the two hour journey to Bournemouth.

The arrival

Its 3:45pm as I arrive in Bournemouth’s notorious red light district and I decide to have a circle around in my car familiarising myself with the area, and looking out for Hotels and B and B’s I can use as a base. Immediately it’s obvious this is not the best side of Bournemouth , but I am not here to check out the living standards of the area. It did look kinda run-down in places, and very seedy in areas. Perfect. As I cruise the area looking for a hotel I notice girls are already out plying their trade on the streets. Most dressed in jeans, and not really wearing any make-up. By now I am starting to have second thoughts as I only packed one outfit for my visit. I am going to stand out amongst the other street workers. I guess I am going to look really obvious compared to these girls, and I am not sure how the police take to working girls (or trannie whores) in this area.

You know they are working girls, they try to get eye contact with you as you drive past, sometimes waving at you just like an old friend they recognise. Sometimes more subtle just a hand on hip stood on the street corner and a wink as you drive past. All the non verbal techniques I shall put into practice when its my turn to ply my trade on the streets tonight.

The first Hotel I come across the Ashleigh Hotel, looked very reasonable from the outside, so I park up in their car park and wander in to check out the room availability. Now this looks like a nice clean respectable place, considering the area and what its well known for. I enter from the car park through the main entrance with blue canopy prominently displaying the hotel name into an open and very well looked after clean and tidy reception. To my right there is an open area with seating, I can’t help but notice a very attractive blonde sat on her own,  white miniskirt, tanned bare legs and white stiletto high heels. She made no attempts at eye contact as I wondered towards the reception desk, so I figure just a pretty lass waiting for her friend, but what do I know?

At the reception I enquire about rooms and am informed that the hotel is full, “what you arrived in Bournemouth without booking ahead, on a school holiday week?” The receptionist exclaimed. Shes in complete surprise at my impulsiveness and lack of planning, and when asked of alternative places to stay just informs me there is nowhere in the local area she could recommend. So I decide to leave there’s plenty of other places to try. As i head towards the exit the girl in the White mini calls over to me “well she might not want to recommend anywhere, but there are other places you can try if you don’t mind lowering your standards a little , you should get a room?”

Well we got chatting, and she suggested a place just down the road not too far away, it’s very very basic and cheap she informs me, but if you just want somewhere to get your head down after a night out in Bournemouth. It should be OK, and with the money you will save if you’re looking for a little extra fun? She looks me straight in the eye and with a sexy wink she says take my card. Stunned and speechless I look down at the crisp white card she placed in my hand. “Monique, Experienced Massage and tantric sessions, 07768 4…….”. She tells me she’s staying here until Friday and if I want some company her rates are very reasonable starting at £80 for the half hour. “Well you never know, and thanks for the tip on the hotel!”. I head back to the car.

Turning right as I leave the car park I head down Soutcote rd, I see a girl with a guy hand in hand heading to what seemed like into a park area on my right hand side. Curious I decide to park up and check out this part of the area. Sure enough just behind Southcote road there’s a nice leafy area, having a wander around I realise its actually quite secluded and may be a good area for punting. On close inspection as I wander the area I did spot a few used condoms. Excellent I think this is definitely an area for punting. So now in my head I have my perfect spot for plying my trade later this evening. I can be standing out on Soutcote rd where there are plenty of cars circling, other girls are already working the area and can just nip into this park with my punters and do the business.

That sorted in my head I decide to head off to the hotel Monique suggested to me. So I turn around and once again head back up southcote rd and passed the Ashleigh Hotel. I come t a T Junction and notice the Saffron sandwich bar on my right. Feeling peckish I pull over and park up. Whilst ordering a bacon and egg roll I ask the guy about the hotel I was recommended “The Chelsea”, he exclaimed. “Sure you will get a room there as they are never full. Believe me, stay there and that will never be a night to remember. The owner Chrissie, well let’s put it this way, she makes Basil Faulty from Faulty towers look like the perfect hotelier”. So here I am in Bournemouth’s red light district, plenty of action is going on already in the area, and I have been recommended the worst hotel/BB in the area to stay in. And yet I am resolute I will turn myself into the street whore and work the streets of Bournemouth tonight. I finish my sandwich and head for the car to drive over to the Chelsea Hotel which as it happens is also on St Swithuns rd. I did check out “The Lodge” on the way past, but again they to where booked-up. So here I am arrived outside the Chelsea Hotel, parked up on the road as there is no onsite parkin. It seems like a good spot as its in walking distance from the spot where I decided I will be doing my business from. I head in to the Hotel to enquire and book in.

The Hotel

Well I am greeted at the reception; by what I can only describe at this stage by a middle aged and very eccentric lady (middle aged being a little bit kind). And eccentric bordering on crazy. I enquire about a single room for the night. “What do think this is? A hotel? Of course we have rooms”, she barks at me!

Not the warmest of welcomes I have ever had, and to be honest I would not call the place a hotel. Think Pretty Woman and the slum of a room, she climes out of on the back baloney. Indeed I have had warmer welcomes from a cold cup of coffee.

 ” Its £35 for the room and I need a credit card on file, for a £25 key bond, she snaps at me”. OK, and how are you about tgirls staying and using the facilities I enquire? “I don’t care what you hear to sell, she snaps, but the supermarkets already sell that at good prices along with the coffee”.. OK I am seriously wondering about staying here by now, this woman’s several raisins short of a fruit loaf. But time is getting on and its the third place I tried to get a room at for the night.

Money paid and I am handed the front door and room keys.  “Tina”, she calls out looking straight me in the eyes. “no that’s not my…”, “not you, the maid she barks”. Obviously this woman does not use non verbal communication in the way the rest of us do. Tina arrives from a side door by the reception “yes Chrissy”. “Show our new guest to room 14”, she snaps at the maid.

Smiling pleasantly at me and wearing full make-up and Amy Whitehouse hair, a pleasing site to the eyes after the landlady. Tina the maid beckons me to follow her to my room. Making polite conversation on the way up. I enquire about the landlady with Tina, explaining about me being a Tgirl, Tina reassuring me don’t worry its fine. We had a laugh about how Chrissy the landlady thought I was here to sell tea. Of course I am not letting on to the maid what I am really here to sell.

I won’t go into detail about the room, just think of the worst B and B you ever stayed in and then times the state of it by 10. You get the idea, lumpy bed. Not the cleanest of toilets, and the curtains older than me. But for £35 I was not expecting the Ritz.

By now its 6:10pm. My legs already shaved the night before i know I need just an hour to change to my femme self including make-up. I decide I need to be out working on the streets by 9pm. But first I need to eye up the competition and get a little more familiar with the streets that will be my place of work for the rest of this evening. I head out to the car, get my things and put them back in the room. Its up one flight of stairs and the only way in and out of the building is past the reception. I decided to put Chrissy straight on the Tgirl side of things advising I will be dressed as a girl for the evening. “its for a fancy dress party”, I tell her. “But because of the area if I do need to pop back, in the evening, I will always have a guy with me”. She agreed that because of the areas reputation that would be a very safe thing for me to do. “Just don’t make to much noise”, she snaps. And then winks at me.

The more I talk with the landlady the more I am convinced she’s a few pence short of a pound.

I head out on to the streets to do some market research in male mode.

Checking out the competition

Out on foot I decide to check out the area and the girls. Not taking the car as I don’t want to get clocked for kerb crawling. I turn right from outside the Chelsea and head towards the junction of Southcote rd. Initially I decide to go straight passed the junction and find up on the right hand side a lap dancing club. Closed as its only 6:30pm by now, but it does set the tone for the area. And with a name like Peaches I am sure its the sort of establishment where there will be lots of semi naked pole dancers, but I am not here for that.

I turn around and head back to the junction; turning left I am now on Southcote rd. I head down the road ahead of my. Taking a casual stroll to my pace, knowing when I make this journey later I will be in six inch high heel white kneel length boots a micro mini, stockings and a PVC jacket. I intend to look the slut I intend to be this evening.

Less than 5 minutes into my journey I spot a girl hanging around a car service shop on the left hand side. Shes wearing small heel ankle boots, jeans jacket and not much make-up. Not the sort of girl I would go for, but given her body language definitely looking for business. She’s paying more attention to the passing traffic as I approach. Spotting me she calls out, “looking for business honey?”. Well she’s obviously up to providing a service, just not an MOT LOL. Just for the hell I enquire what’s on offer (remember I am going to be in competition with the likes of her later). “£20 for hand relief, £30 for O with, £40 for o without and £60 for the full service”.  I declined her offer, “I prefer Blondes” as my excuse and I move on. Heading further down Soutcote Rd i spot a much better place to ply my trade. Southcote rd apartments. A dilapidate 70’s type build of flats. Anopen garage entrance to my left, centre stairway (to hide in when the plod circle round) and another road garage entrance a little further down. Perfect I thought. Hopefully none of the other girls have the same idea.

I wondered the area a little more, and its a real mix of private housing, council housing, and industrial units. Its easy to see why this area is so good for working girls with plenty of car parks. Alleyways and parks for the girls to ply their trade.

Having chatted to a few more of the girls round the area I get the idea that the average going rate is about £60 for a full service, but one of the girls did mention that she adjusts her prices according to the type of car the punter is driving. “yeagh, if they have a well posh car like a recent BMW or Audi, you can get away with asking a bit more”, she tells me.

Well now familiar with the area and some of the girls I head back to the Chelsea. Firmly n my mind the layout and where I plan to go for my evening as a Bournemouth Street Prostitute. I just hope the punters don’t mind that I am a T girl whore. Then maybe some won’t care, maybe some won’t work it out.

Its 7:30 now, back at the Hotel and I finally get down to preparing for my change from boy into T girl slut whore. The hardest thing is going to have the confidence to wander out of the Hotel onto the streets and for the first time, ply my trade as a TV street prostitute.

Getting Ready for work as a street prostiitute

Unpacking my bags and sorting out my inventory of clothes make-up wig and accessories for the night’s work I ensure I got everything I will need for my adventure on the streets of Bournemouth.

The big (and I mean big) handbag for some things I need to take out with me. Couple of tubes of Anal Lube (£1 a tube from pound stretcher), BJ Condoms (special deal from Tesco’s right now, 12 ultra thin sensation for £3.69, while stocks last), Anal Condoms (The safer thicker variety, no deals to mention off), and my butt plug.

I lay out my make-up, false nails and clothes, stockings suspenders and boots (white 6 inch platforms), ultra tight size 8 mini-skirt and sexy shiny PVC Jacket. 

Yes everything I need to look and be the part of a street whore.  Actually thinking about it, the cost of all this gear must be heading towards about £100, blimey its expensive looking this cheap.

I head to the en-suite bathroom in my room; well actually it’s the size of mini box room, no bath, shower bowl, dripping taps and no light over the cracked mirror. I decide after my wash I need some good light for doing my make-up.

The prepared Girl I am, I place my own mirror in front of the bedroom window, and sat on the edge of the bed, I start preparing my face after first putting on my Bra, inserting my fish fillets (tits) and putting on my blue stripy roll neck top (£1 Matalan clearance, last year’s sales).

Generally I take about an hour applying my make-up and tonight is no exception. I pay the same attention to detail, as I do any other time, for a punter when mistressing or a photo shoot or a night out. Today I put in just the same effort. After all, I need to achieve a few things, pass as a girl, looking good for the punter (so I don’t have to spend too much time getting them off), and feeling good and convincing for myself.

Make-up done suspenders and stockings on, I place a condom on my but-plug, lubricate my arse with lube and insert it. Now the reality is kicking in what’s going to happen on this night. Turned on by my own look;  as I see the reflection of this sluty TV whore in the mirror. The sensation of the but-plug in my arse, my cock is getting hard and I really feel the need to have a good wank while the but-plug, which could as easy be any strangers cock is comfortably warm and wet in my tranny arse.

It’s getting towards 9pm now and there I am have dressed as a street whore in a dingy B and B room two hours drive from home. Still plunging the but plug n and out of my arse, wanking of my rock hard tranny cock I fantasise about the events to come this night. I continue to please myself as I slip into a fantasy of being the TV street whore. In my fantasy I see myself from a third perspective as I am engulfed in the pleasure of my Anus and Cock stimulation.

I continue the physical play with myself and close my eyes, look for the moment of visual stimulation to accompany.

The Fantasy

She’s dressed in a tight PVC dress, my gaze draws down towards her slim sexy legs covered in fishnet stockings and black PVC 5 inch high heels. Confidently walking the streets of her beat, click click click, as each step of heels makes contact with the pavement as she strolls looking for her punter.

The night is dark and the traffic is busy, toots of horns as passing drivers, raise there awareness to the whore on the streets looking for business. The police turning a blind eye, as streetwalking is accepted on the streets of Paris. She’s looking good in full make-up, walking confidently, her warm blonde hair glistening in the air of the busy suburbs of Paris.

A gentleman passes her by as she struts her way up the street, caught by the allure of her expensive perfume he turns towards the beauty that just passed her. His eyes drawn to her cute arse encased in tight shiny black PVC, his eyes wandering down her Shapley legs covered in seamed fishnet stockings and finally to the alluring look of her very sexy very high heel shoes as they click click click on the pavement as this alluring streetwalker heads away from him.

Immediately he turns towards her and quickens his pace, she sensing the approaching stranger who just passed her by, turns towards him and smile. “Looking for business”, she enquires.

Almost lost for speech and in total awe of the very sexy hooker in front of him, he just about squirms, “yes, how much?”. They discuss and agree on the services to be offered as she walks him up the street towards an off street enclosed car parking facility. She drags him into a quiet but will lit area of the car park next to the bins.

Her hand reaches out towards him, encased in the same black shiny PVC gloves that match her dress; she demands the cash upfront for her services. Placing it between her warm breasts and the tight clinging of the material of her PVC dress; “Mmm, and now we can have fun”, she exclaims as her hands reach down towards the throbbing hard cock in his trousers.

The sounds of cars arriving and slight echo’s of voices in the background, bring a slightly open ambience of the car park as the whore gets down to work. Unzipping his trousers she pulls his throbbing cock into full view, and just a slight distance from her now open and hungry mouth.

She takes the cock enthusiastically into her wet waiting mouth, tightening her lips firmly around his hard shaft, swallowing deeply down to the back of her throat. Thinking of the money she’s earning for her sordid acts, she works his cock with vigour in and out of her wet hungry mouth.

To the point where she senses he is close to Cumming, a technique endowed with experienced women, she pulls off, stopping the pleasure for a moment as she reaches into her handbag for a condom.

Opening the wrapper of the condom, whose packet reads “instant anal pleasure condom, self lubricating technology”, she takes it out places it into her mouth, and expertly applies it orally onto her punters throbbing dick.

Assured the condoms applied fully, she turns, stands and hitches up her PVC dress revealing her purt cute ass,  like a lighthouse bulb, bright in the reflection of the ca park lights, between the blackness of her now hitched up PVC dress and her black stockings.

She pulls her cheeks apart revealing her waiting anus for her punter to fill.

Back at the Room

The beds bouncing, headboard knocking the wall, I am still doing my arse with the but plug and wanking almost to the point of ejaculation, my “fantasy” in my minds eyes. I stop completely. Take a deep breath and hold my orgasm inwards. I need to contain my sexual urges and let them drive me to the next stage.

I complete my dressing and ensure I have everything I need, I think to myself “Time to be a real TV street prostitute”

Its 9.30 Wednesday June 1^st, and now its my turn to live out my fantasy for real

To be continued