I had the room advertised on many web sites and I had already interviewed 3 females for the room vacancy, but all were not suitable for one reason or another.
I had told them all about my cross dressing, and although this wasn’t so much of an issue, my escorting was. This is understandable I know, but I was certain the right lodger would come along soon enough.
The next applicant was an 18 year old student who was moving out of the campus for some peace and quiet and to get on with her studies in privacy.
The door bell chimed at exactly 3pm, as she had stated on the phone.
“Hi! Im Jezebel! But most call me Jez!”
The girl at my door was an unbelievable sight.
Standing only 5’ 1” tall and a really tiny frame (later confirmed as size 6), with such a cute face, she didn’t look old enough to be at university let aone old enough to have her name on a rent book.
“Come in honey!” I enthusiastically welcomed her.
“I’m Tina, welcome to the home!”
“You look fab Tina!” she smiled, “And the home looks lovely too!”
We both sat down at the dining room table, and I put the kettle on. We chatted for ages, mainly about my transvestism, and my line of work.
She was not shocked at all about the escorting, and said that she knew some of her friends had worked for agencies and done some dirty porn to help with the costs associated with being a student.
She really liked the house and in particular her bedroom as it was he compared to her little room on the campus.
She was amazed when I showed her the room that I use for my entertaining and web camming. It is quite much like a studio or a boudoir as I like to call it.
She was not phased with any of it.
Soon we had agreed the terms of the tenancy and to cut a long story short, she moved in a few days later.
I had an in call booking the same day as she moved in, so after a quick chat and cigarette she made herself sparse and went to her room.
The guy I was seeing was in and gone in about 20 minutes. He had opted for a quick ‘cum n go’. And that is what he had got!
I cleaned my face up and touched up my make up before asking Jez if she wanted to come down stairs again for a chat.
“Jesus! He wasn’t here long?” she laughed.
“No, some don’t want to be!” I replied.
“You can’t of got up to much in that time?” she enquired with a smile on her face.
“You will be surprised!” I laughed in return.
“Be honest, Tina, tell me what you did. I won’t be offended.”
“I led him up the stairs and he sat on the bed. He then paid me. I set the camera to roll aimed at his cock, not his face. I then put on some more lip gloss and then knelt between his legs, and sucked him off. When he was about to cum he stood up and splashed his cum all over my face.
He then smiled and walked out. He comes and does this about once a week”.
“Jesus! And how much did he pay you for that?”
“£40” I replied. I let him have it £40 as he allows me to film it for my web site. No filming and its £50.”
“That is incredible! I work a full day for £50! I’m in the wrong job!” she laughed.
I knew that even on day one she was interested in the lifestyle. Being a hooker is a fantastic way of earning a living, if you can put up with the negative side to the life.
I knew that Jez would be making more enquiries into what goes on as time passed by.
One afternoon she came in from work (she had a part time job in the local Co-Op)
Just as I was saying goodbye to a visitor I had just seen.
“Bloody hell! How old is he?” she laughed.
“He’s 72 Jez. He is actually lovely!”
“Can he get it up?” again she laughed
“You will be surprised what a blue pill can do to these old Grand Dads!” I laughed back.
“Amazing, Tina”
A few weeks passed and Jez took more and more interest into what I was doing.
One night we had decided to have a girly night in and we had some bottles of wine and we had a good chit chat about everything.
She disclosed that she was really thinking about startinbg as an escort, but was worried as she was too skinny, with very little boobs. I told her that if she had the right attitude towards it, and if she was prepared to do some risqué role play, then she would be extremely busy.
She said she was happy with any role play, and actually quite the idea of a much older man having sex with her.
She came over as very business like and that money was the main attraction, and she would do anything to earn it.
“I think, if I am honest Tina, I will do anything they want if the money is right. Is that what you are like?”
“Absolutely Jez! I will do anything – but the price as to be right. Everything and anything has a price.
We retired to our separate beds at about midnight. She said she was going to sleep on it, and let me know in the morning. I told her that it made no difference to me at all what avenue she decided to go down, but I still wanted us to remain friends in any case.
In the morning I was up and making a coffee and having a cigarette when Jez appeared in the kitchen
“Morning hon!......I’ve definitely made my mind up, and I don’t do things by halves Tina. Look at my studies: I always do well, because I throw myself into it, and I intend to do the same in this new exciting line of work”
“That’s great Jez!” I replied, “but it’s not like anything you will have done before, remember that.”
“I want to make lots of money Tina. I want to be popular, and I think you will be able to help me?”
“I am certain you will be extremely busy Jez, as long as you are prepared to work hard to please.”
“That sounds great. Just great Tina”
We then went on to discuss the types of men she would have to see (if she wanted to make big money she should not turn anyone down).
“I don’t want to say no to anyone and any of their requests – Like you don’t!” She laughed.
She knew I advertised myself as ‘the girl who does not say no,’ she had seen it on my web site. “I want to be just the same. I want the men to know that ANYTHING is on the menu”
“That is incredible Jez!” I stuttered, “but a tall order”
I looked at her ever so slight figure – I have to stress she was just SO tiny! I just could not stop thinking of her dressed as a schoolgirl – she would look amazing.
Her slender white soft legs and her thin hairless arms were just incredible and I knew it wouldn’t be long before I woud be seeing her naked torso, and for that I couldn’t wait.
“Are you happy about role play Jez?”
“Totally. I know what these men want. I am happy to be dressed as schooly, I have no issues with fantasy role play. The more I have thought about it the more I find it very sexy. I’m also happy to dress in sexy stockings and heels etc. I’d like to get some PVC and maybe wear heavy make up. It’s a real fantasy trip for me to! I can’t wait!
“Would you like to do porn as well?” I asked
“Ive been watching a lot of porn, and the answer is yes - I will do anything to make money, but I won’t be looking to get ripped off”
“Jezebel l am not in the habit of ripping anyone off.”
“I know that, Tina”.
The next few days we did nothing but talk about different scenarios I expect she would be asked to undertake, and I have to admit, she did not flinch at anything. She was addressing this in a very business minded and mature way. It was just theatre.
We went out and got some sexy outfits for her, as well as ordering some PVC mini dresses, ‘pole dancer’ shoes and ‘fuck me’ knee and thigh boots on line.
We were in Primark in Portsmouth and we were looking at the childrens clothes as they fit her perfectly. She picked up a full school uniform, with pinafore dress, satin blouse for less than £10! She also picked up some very sexy mini skirts, hot pants and sassy tops from there as well.
She looked at ‘wonderbras’ but I said her almost flat chest would be an asset to her work, and she should not try to inflate the size of her tiny A cup boobs. She agreed. She agreed with everything I had to say, and was always very positive.
When we got home that day from the shopping trip, we took some photos of her in her new outfits. She just looked amazing. With her hair in pony tails with pink flowery bunches and her new school uniform (complete with white knee socks and ‘Mary Jane’ flat ‘T’ bar shoes, she looked incredible.
She said she felt sexy and I told her how amazing she looked.
A quick change, and her hair was pinned up and she had red lipstick and bright pink blusher, with blue eye shadow. Her tight micro-mini skirt and tight crop top looked fantastic, especially with her tiny waist on show. With her pink high heels she looked like a right slut, and I told her so.
“If it sells, I will wear it!” she exclaimed.
I knew this young, pretty girl was going to be extremely popular.
The next thing was to set her up a page on a well known escort’s web site. This I had done in a matter of minutes and I put my phone number down as a contact for ‘Sasha’ the stage name we had chosen for her.
Within in 20 minutes of the page going live, she had received 10 email enquiries. Within the first hour she had received 3 telephone bookings for the following week.
“I told you you would be busy Sasha!” I laughed.
Jez had said that until she found her feet she would like me to be around, as a safety net. We told all the men who made enquiries this and most accepted it as a pre requisite. Some, on the other hand were not interested.
Jez had stipulated that she thought it a good idea if her first client was an old man, as old as possible, so that she knew if she could do it with an old man, she could do it with anyone.
I told an old man I know very well, Russ, who is a regular client of mine, about Jez, and he immediately wanted to book her.
I explained to Jez that he was 67, and he simply loved schoolgirl role play, and could easily get carried away.
Enthusiastically, she agreed to see him, and the booking was done for the next day.
I had told Russ that Jez wanted me to film it, but I wasn’t to take any physical part in the meeting other than a bit of directing, when maybe he had run out of ideas.
When I run the filming idea by Jez, she was more than happy. “I think you will be surprised by my performance” she gloated.
The next day I was in the kitchen when ‘Sasha’ appeared. In her full school outfit she looked incredible, and I knew Russ was going to love the sight of her.
We went upstairs to the bedroom and I set up the video camera on the tripod facing the king sized bed. Jez had already made the bed up with bright pink satin bottom sheet, and removed the duvet. As Russ was due any minute, she said that she would wait and I should call down ‘Sasha’ when he was comfortable.
“I’m so nervous! I’m shaking!” she laughed as she disappeared up the stairs.
Russ arrived dead on time as always. A kiss on the cheek was the welcome I gave him and he sat down at the kitchen table and instantly produced his ‘tribute’. I quickly counted it and put it in my black patent PVC hand bag.
“SASHA!” I shouted, and a few seconds later I heard her coming down the stairs.
Russ’s face was a picture as she stood in the doorway between hall and kitchen.
“Well hello little one!” he smiled
“Hi!” replied Sasha in a timid way, “I’m extremely grateful you have come to visit me, sir” she said and kissed him on the cheek, whilst sitting on his knee.
“I want you to enjoy yourself so much today Russ” she said confidently “I don’t want you leaving here wishing you had tried something, I promise I am here to make you happy, and I will do anything you ask.”
“Oh you are making me so happy little princess - indeed you are”
With that Sasha got to her feet and lead Russ up the stairs to the bedroom. Flicking her pony tails, she sort of skipped up the stairs, with him struggling to keep up on his frail legs.
I followed behind and walked in the bedroom behind them. Sasha was French kissing the old man, and his hands were in her bra and all over her tiny little tits.
She was feeling his now hard cock in his trousers as the kissing continued.
Russ struggled in opening the straps on her pinafore dress, and Sasha knelt up next to him and aided him in undoing the big buttons.
Her dress dropped down, and she was soon out of and now down to her white satin blouse, white satin panties and white knee socks with her flat black Mary Jane shoes still in place.
“How do you feel Sasha?” I asked her as his hands were once again all over her tiny titties.
“I feel sexy, wanted, and very very vulnerable!” she laughed.
“Why vulnerable Sasha?” I questioned.
“ Because I know I’m so wet and turned on, I am almost certain going to end up being so bad.”
“You are being very good little Sasha, a very good girl” Interrupted Russ, his hands desperately trying to unbutton her blouse.
“Let me help you” she said, and put a few feet between them both as she almost did a strip show out of her blouse.
He lay back and just watched the show. He was already down to just his horrible grey underpants, the rest of his clothes thrown in a pile in the corner of the room.
He was rubbing at his rock hard bulge and I filmed that in close up briefly as Sasha was now down to her tiny white padded bra, panties, socks and shoes.
His hands then grabbed at her tiny titties and he tried to make a cleavage out of them by forcing the together, but it was simply not possible as they were just almost non existent.
“I’m sorry I have no boobies Russ. It’s a price I pay for being so skinny”
“You are divine Sasha: My perfect little angel.”
Her hands went behind her back and immediately his head plunged into her almost flat chest.
She slowly removed her bra and again he sat back.
“My oh! My! Look at you!” he exclaimed.
I knew Sasha was really enjoying this, she could not been more receptive to the situation if she tried.
She lay back and pushed her tiny pelvis upwards which displayed her tight white panties against her pussy lips, and it could be clearly seen she was sexually turned on by the proceedings as her gusset was absolutely soaking.
“Oh look how wet I am sir!” she spoke softly in a real wicked voice.
I was amazed at how she had taken the lead in the role play. I knew Russ would go there eventually, but for Jez to have initiated it was really unbelievable.
“Come and rub my pussy, sir” was her next ‘come on’ to the old man.
He didn’t need telling twice!
His frail and veiny hands were into her panties like a shot.
He was busy fingering her lovely bald pussy as he French kissed her. His long grey beard hairs were smothering her tiny mouth as their tongues lashed at each other.
Sasha was soon out of her panties and the sight of her completely bald pussy was just wonderful.
He asked me to take some shots of her for his future use, and she posed naked (apart from knee socks and shoes) on the bed.
She KNEW how to pose!
One shot after the other was taken, in all positions. She looked (and acted) like a professional model.
She decided when enough was enough and lay on her side and patted the bed in assign to him to join her once more.
“Come on sir, I want to give you a special cuddle” she provocatively put to him.
He lay down next to her, still in his dirty underpants, with quite a huge bulge showing in them. He put his arms out to embrace her, but she put her head on his hairy belly and started to play with the hard bulge over his underpants.
“Sir, I really want to be your special girl?”
“I want that so much Sasha” he replied softly.
“I want to be the girl that makes you the happiest old man in the whole world.”
As she spoke she was taking a real interested in rubbing his hardness through the dark stained grey cotton, whilst licking her lips.
She leaned forward and pulled the cotton underpants over the top of his hard cock and then pulled them down completely to his ankles.
He lay back as he felt her warm breath on his bell end as she took position………
TBC
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