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Milf and TV Whores with male
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By (user no longer on site) OP
over a year ago
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Jenny (as you probably know) is an old friend of mine who I introduced to the wonderful world of escorting a few years ago.
She is described fully in my my previous story ‘Female friend becomes Transvestite’s Whore’
Again, this is from my escorting days, so there is mention of money etc.
On this particular day Jenny had stayed at my house the night before after a few too many glasses of wine.
Early the next morning I had a text from a regular of mine asking if I was available for sex.
Jenny and I had a cuddle in bed as we started the text tennis. She couldn’t believe it that at 7am a guy wanted sex with an escort. I told her that it takes all sorts, and Russ was a nice (ish) bloke, as long as he wasn’t in one of his nasty moods. She had already met Russ and so knew basically knew what he was like.
I knew if Russ knew jenny was here, he would want us both and so I put this to Jenny.
She was a little reluctant as she didn’t have any sexy clothes to wear and really wanted to look the part. She also had childcare issues as the babysitter was supposed to be leaving her house at 8am.
I messaged Russ back and he said it didn’t matter what she was wearing as he wanted a bit of cheap /rough council housewife look, but he wanted me fully dressed up as normal. He also said he would want it filming.
Jenny said it was odd that he wanted a bit of rough as normally he liked us both dressed to the nines. She asked if she could borrow my make up as she really wanted to make an effort on her face, especially if it was to be filmed. Of course I agreed.
Jenny quickly rearranged the babysitter to be relieved a couple of hours later than planned.
I messaged Russ back and said we would be ready in an hour.
He replied saying he wanted me totally glammed up in stockings suspenders and high heels, but he wanted Jenny to be plain, and especially he wanted her legs to be bare.
I explained to Jenny that it was important to please the guest and do as he instructed.
It is always essential to do as they wish if you can, as it is us that are providing the service.
“I just cannot believe I am agreeing to doing this at bloody 8am!” She laughed.
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By (user no longer on site) OP
over a year ago
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Part 2.
I quickly had a shower, closely followed by Helen. Time was now of the essence as we only had about 50 mins before Russ would be here.
I sat at my dressing table and arranged my make up ready for application.
I smoothed over my foundation and let it dry. Whilst it was drying I did Helens eyes. We opted for purple eye shadow, bright purple on the insides fading into dark purple at the extremities. She went for the dark blusher and very dark purple lip stick. I said she looked very slutty , and she said she felt like she looked like a clown!
Females often have issues with ‘too much’ make up, where as us guys know thee is no such thing, especially when it comes to delivering a sex service.
I powdered my face completely and then I did my usual blue eye shadow, which makes me feel such a slut. I also did the dark blusher but followed this up with red lipstick. I put on my wig and brushed it into shape.
We sat and looked at each other in the mirror and giggled at what absolute whores we looked at 7.30 on a Saturday morning!
Jenny put on a leopardskin bra and matching thong and on top wore a black stretchy pencil skirt and a grey/black satin leopardskin print blouse. As requested she kept her legs bare.
I had my black basque and black thong on, together with my black wonderbra. Obviously I had black sheer stockings and suspenders to complete the look. On top I wore a black very shiny floaty blouse. As it is quite long (mini skirt length) that is all I wore. My 4in hi heels finished off the look.
We had just finished when my phone pinged and Russ was here. It was 7.55.
I got my black pvc clutch bag and went downstairs to meet Russ at the door. He looked his normal self - well kept, clean and presentable, and he smelt lovely in his aftershave, although he had a beard.
I kissed him on the cheek and he gave me a cuddle, saying I looked so sexy. I thanked him for his complement, and lead him into the front room.
He took off his coat and I took that to the utility room and hung it up for him. As I walked I made sure my bum wiggled and walked as feminine as possible in front of him. The sound of my heels on the laminate flooring was just so sexy!
I returned and sat next to Russell on the cream leather sofa. I smiled and thanked him as he counted out the tribute for both Jenny and myself.
I put it in my clutch bag, and zipped it shut.
Russ asked where the video camera was ( I had forgot about it), and I went and got it from the conservatory. It was already on the tripod and fully charged. I put it on the floor on the tripod in front of him. “You know what you are doing with that!” I giggled as Russ had filmed be dozens of times before - by myself, with men, women and other transvestites. He didn’t need instructions on setting the camera up. As my most loyal ‘regular’ I let him be my cameraman when the need had arose, and indeed, he loved being filmed with me when we were on a ‘booking date’ and said it turned him on knowing people were wanking watching him with me on my website.
“Jenny is ready?” he asked.
“Yes, she looks so sexy!” I replied.
“Bare legs and bare feet please” he requested.
“Bare feet too?” I questioned this very odd request, as he had never ever asked for that of me.
“Yes, I want her a bit plain. A contrast to you sweetheart” he replied.
I told him we had done her make up quite heavy, and in dark purple! He shuffled in his seat, smiled and said “no problem, lets go. I want a good lesbian show to start .”
“So do we!” I laughed. I grabbed my clutch bag and smiled at him before I made my way upstairs to ‘collect’ Jenny. |
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By (user no longer on site) OP
over a year ago
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Part 4
Jenny was sat on the bed looking quite nervous. I sat next to her and stroked her leg and told her she would be fine. She said she felt undressed without stockings or tights on. I told her again that its all about providing a service, and not to question, but to do. She shrugged her shoulders and said “I suppose.”
I put the clutch bag on my knee, unzipped it and removed the tribute. I counted out her share (which was the greater proportion) and put it in her hands.
“There you go Jenny. When he says bare legs, he gets bare legs!” I laughed.
“It takes me a week cleaning to earn that” she quietly exclaimed.
“Exactly!” I quickly replied. “It’s a lot of money, and so he deserves a good service doesn’t he?”
“The best!” she enthusiastically replied, “I’m so wet already!”
I let my hand explore her, and she was right, she was soaking!
“Let’s be real slags for him honey” I whispered.
“Anal slags!” she whispered back, “Saturday morning Bareback Anal Slags!” she giggled.
She was now ‘in the zone’ and I knew this was going to be a good meet.
“The camera will be rolling as soon as we enter the front room Jenny, so be your best!”
“That’s cool” she said as she got to her feet. “Where are my stilettos?” she asked.
“You don’t need them hon, he’s asked for bare feet too!” I confirmed with her.
She looked at me almost bewildered, shook her head in disbelief and said “Whatever!”
We both stood side by side. I was towering above her in my heels and I leaned forward and kissed her on the forehead, “Let’s go saucy!” I smiled.
She smiled back at me and I lead her by the hand down the stairs to the front room door which was shut.
I put my head around the door and Russ was sat patiently behind the camera which was perfectly placed aimed at the large three seater leather sofa directly opposite him.
“We are ready honey!” I said plainly to him. “Please come in!” He requested, “I’m aching to see you both!”
I turned around and looked at Jenny, she smiled confidently and almost mocking the way I sometimes talk said “let’s earn our money!” Bless her!
I opened the door fully and walked in with Jenny in my trail, hand in hand. |
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By (user no longer on site) OP
over a year ago
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Part 5
As I still have access to the film, from now on I will paint the picture completely from the film, so I don’t have to go from memory. I will not add anything for artistic licence - it is exactly as the film shows. Also, the dialogue is totally verbatim from the film.
“Russ this is Jenny” I say as we enter the room.
“Hello!” replies Russ.
Jenny replies with a really well spoken “Hello!”
We walk to the sofa hand in hand. As I am walking you see my stocking tops as my shiny mini dress is so short.
We sit down and immediately start French kissing, and my right hand is straight onto her ample boobs. The kissing is very heavy, we are whispering things (that cannot be made out) but you clearly hear Jenny say ‘yes’.
Her hands are now all over my tits as my hand goes between her legs. She makes it easier for me to get access to her cunt by placing one leg up on the sofa, and her legs naturally open.
We have only been in action 20 seconds and already she is gushing!
As I finger her she buries her head into my cleavage, fighting to get my tits out to suck on.
My mini dress is very awkward to release my breasts and she lays back again and we continue to kiss.
I turn around and beckon Russ to come closer with the camera, and I actually say “Russ come closer!” and he does so shuffling the camera and tripod into position above our heads as we continue to French kiss. Jenny’s tongue is deep in my open mouth, and my fingers are deep in her wet, hairy cunt.
“Your cunt’s all wet!” I laugh.
“It always is!” She sluttily replied.
I sit upright and pull my huge tits out of the top of my dress for her to feast on.
“Kiss them honey!” I say “Lick and kiss my tits”
I look at Russ and ask him if he likes it “I love it!” is his reply.
“Do you like us being sluts together?” I knowingly ask him, “Yes, and Helen looks gorgeous!” was his complimentary reply.
“She is fucking gorgeous!” I say whilst still kissing her.
Jenny sort of mumbles in gratification.
We are continually kissing but I manage to undo her blouse and expose her leopardskin bra and start to fondle her gorgeous tits.
Jenny’s hands are rubbing the tops of my stockings and my suspender clips.
(A long time after we filmed this Jenny admitted she loved feeling my suspenders and it made her feel so lesbian doing so!???!! I know in the other films we have done, she does spend a lot of time feeling them.)
Unannounced, I lay back on the sofa and pull out my hard cock from my panties.
Jenny takes no time in going straight down on my.
“Suck my girl cock!” I exclaim.
Jenny is so hungery for cock, she starts the oral assault fast and hard.
“Nice and Slow!” I ask.
She conforms and reduces the intensity into a nice slow, methodical rhythm.
As she is doing so I look at Russ and ask him if he’s enjoying it to which of course he says yes.
“Jenny is a real slut isn’t she?” I ask him.
“Yes she is” he replies - “Just like you.”
“We are sluts together Jenny aren’t we?”
“Mmmmmmm” she said, without taking my cock from her mouth.
Her head bobbing oral continues for a few moments more, before she sits back on the sofa.
She looks absolutely ‘pure filth’. Saturday morning, about 8.15 am and being a whore like this, all on film. It is tremendous!
“Tell Russ what it is you are looking forward to today the most Jenny” I ask her directly.
“The cum over my face!” she smiled.
“There will be lots of that!” replied Russ.
Russ is an exceptional cum machine, always delivering a huge load. Jenny always looked forward to his sperm, as I did.
“Are we going to share it?”
“mmmmm” she smiled back.
“Is there anything else you are looking forward to?” I ask her again,
“The anal!” she smiled at me whilst replying.
“Are you?”
“Yes! Bareback!” she laughed. “From both of you”.
This was from a woman who literally only a few weeks ago grimaced at the thought of anal sex. She really was so into her new role. |
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By (user no longer on site) OP
over a year ago
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Part 6
I wanted her verbal confirmation - “You are going to be a true anal slut today then Jenny?”
“Yep” she replied, before quickly going down and taking my cock in her mouth once again.
Russ moves around with the camera and you get to see her enjoying my hardness in her mouth in all its glory. Slowly she goes up and down on it, right to the girth.
“You love my girly cock Jenny” I stated the obvious.
I look at Russ and ask “She’s a good girl isn’t she Russ?”
“Very!” he replies. “Amazing.”
Jenny continues her slow methodical head bobbing oral on me for a few moments, before I get to my feet.
“I’ve got something else for you!” I say as I stand and turn away from her and bend over, exposing my arse in front of her face.
“Tongue my arse Jenny - Good girl”
She needs no prompting as I hold my arse cheeks apart for her, her tongue goes straight inside me.
Russ misses nothing, his camera work is sublime.
Jenny’s eyes are closed as she savours the taste from my brown honey pot.
“She is so clever!” says Russ, and he wasn’t wrong.
“Finger me honey” I ask, and she immediately pulls her head away and starts to finger my arse as requested.
I have to say at this point her head is bowed down, and I really do think at this moment in time she was having a guilt trip. She could have been thinking anything - her previous life at the church, her work friends who were also finbding it hard to make ends meet, but not lowering herself to this to make money. Maybe her family? Her children at home with a bay sitter, whist Mum was here with a transvestite and a paying male client. I don’t know, but it certainly is a mood I captured from this moment in the film.
The moment didn’t last long as soon I have turned around again to face her. She looks up at me with those doey eyes, and smiles before taking me in her mouth once again.
“She is unbelievably gorgeous!” says Russ, and I have to agree, on the film she does look gorgeous.
I beckon Jenny to get on all fours on the sofa, facing the wall, with her arse on display.
I lift her skirt up exposing her tiny leopardskin thong which is dwarfed by her lovely round white arse.
“Look at that Russ!” I exclaim.
“Wonderful!” he replied.
I pull her thong down and pull her cheeks apart, before I start to rim her enthusiastically.
Russ moves in close with the camera and you can clearly see me French kissing her dark and musky hole.
I lick and finger her arse, and kiss both her arse cheeks. Both kisses leave a complete red ‘kiss mark’ from my lipstick.
“You like that Jenny?” I ask as I finger her arse.
“Its lovely!” she giggled back.
“Take it like a good girl!” I say.
“I am!” she again giggles “I love it.” |
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By (user no longer on site) OP
over a year ago
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Part 7
I goed her once more - “You’re an anal slut aren’t you Jenny?”
“Yes!” she exclaimed.
My hand moves down from her arse to her fanny.
“Her cunt is all wet!” I laugh “It’s gushing!”
“No wonder!” Jenny replied in gratification.
Without a word spoken Russ passes me my hollow strap on. This toy is white, thick (To accommodate a hard cock), with very heavy veins and it’s about 9 inches long. I often wear this when fucking men and females myself. It makes me feel so feminine to be wearing a strap on, and I think it looks so sexy in the various films I have done with me wearing it.
Firstly I open up her lips and expose her very wet cunt. I rub the head of the toy up and down her crack. Jenny is moaning throughout the evolution.
I then line it up to enter her, and Jenny takes hold of it from behind to get the right comfortable angle of insertion. “Go on babe” I encourage her.
The toy is inserted and I ask Russ to back away with the camera to get the whole picture.
It really is a sight to see Jenny on all fours facing the wall with her bum in the air, with her thong pulled down around her thighs, with me pushing this huge toy in and out of her soaking wet vag.
Jenny is moaning loudly as her cunt is getting battered. Russ cheekily passes her another dildo (this one a normal dildo of similar dimensions to the strap on) and I say “suck on that!”.
Russ moves round with the camera and we see Jenny going up and down on the dildo on the dildo in her mouth. She is moaning throughout, and clearly enjoying this.
“You have a hole free Jennny!” I say suggestively “I think we had better sort that out” I continue.
Jenny moans loudly in acceptance of her fate, but concentrates on the amount of pleasure the plastic double ending is giving her. Her eyes are closed a she quietly moans, whilst concentrating on giving good head to the toy.
“You want it don’t you Jenny?” I ask.
“Yes!” she eagerly replied.
“Say it!” I beckon her - “say I want cock in my arse!”
Jenny stops sucking on the toy, looks to the camera and says “I want cock in my arse!”
“All in good time” I promise her.
The double ending continues a while with Jenny moaning loudly continually.
I slowly remove the strap on from her juicy fanny and immediately start sucking it. Russ captures this so well on the film. I lick and suck off her juices from the soiled toy, and sit back in a normal position on the sofa and ask Jenny to turn around and sit next to me.
The camera is again repositioned so you can see both us girls sat next to each other.
Russ appears in front of us both and Jenny smiles as she leans forward and takes his hard cock in her mouth.
I rub Russ’s balls as Jenny goes down to his girth “Good girl!” I say.
Her eyes are closed and she looks so sexy in her heavy make up as she takes his cock to the back of her throat and not wincing in nay way, but completely enjoying it.
I lean forward and we share his hardness. Both sucking it a few seconds before passing it to the other.
Jenny sucks his bell end and I lick along the length of his very hard cock.
Russ puts his hand on my shoulder and you can see his watch. It is 8.15am! I think this makes the scenario even more sexy and seedy.
Russ starts to feel Jennys boobs as she pleasures him and she responds by sitting back and removing her blouse and popping her tits out over the top of the leopardskin bra. She smiles before leaning forward more and taking him orally once again.
I then stand up and she is then presented with two cocks to suck.
I hold the camera down from my chest and film her taking us both in her mouth one at a time.
“I Fucking LOVE this!” she exclaims out of the blue.
“You are such a busy girl aren’t you?” I comment.
“Mmmmmmm” is her reply with my cock in her mouth.
She takes us both one at a time for a few moments and savours every suck, every lick. Sucking one whilst wanking the other, and repeat. |
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