Turning Lemons into Lemonade

By Kendra Holliday | November 4, 2017

I was all set to try something new – hire a sex worker for my partner Matthew and me! I’ve been hired countless times myself, but it’s rare I’m on the other side of the equation. Bonus points: My sex worker friend is very different than me. I LOVE contrast! She’s dark, exotic, tall, leggy, busty – and lactates! Mmmm!

I sent her thoughts on what I was envisioning:

90 min session, with about 30 min just talking on the couch connecting, then going to the bedroom and undressing/kissing. You would be center of attention, sweet sensual worship vibe. I’m bi and we’re both very attracted to you. Matthew likes experiencing female energy, exploring a new body, touching and kissing, he loves oral, giving and receiving, but if you don’t want to do oral on him, that’s totally fine. I will definitely go down on him! 🙂 He would like to go down on you if that’s ok. I might sit back and watch, I get great pleasure watching. It would be super hot if he was having sex with me while kissing you. But if we all end up lying around and you being in the middle for a bit, then him being in the middle and us both kissing on him as he gets a handjob…. that is what we are thinking.

She loved the idea!

Photo by Stan Strembicki

We set a date and time. I was so excited to treat her the way I wish to be treated as a sex worker – regard her as an esteemed guest, like a queen, appreciate her rare gifts.

I prepared an envelope with cash – and a tip! – to present her when she arrived, so I wouldn’t forget at the end.

And then, 5 hours before the appointment, she canceled due to illness.

I was SOOOO bummed! Sigh. The more people involved, the harder it is to turn a fantasy into a reality.

But instead of pouting and watching a movie, I came up with Plan B. I was in the mood for something special and super hot!

Sexy mature me

We set up the massage table and played erotic massage parlor. We LOVE this game!

But here was the twist this time – he was blindfolded, and I pretended to be TWO different women!

I put on relaxing music and lit candles. It started out with him face down. I gave him a really nice all over sensual massage with coconut oil, lotsss of warm up and teasing.

Then, he turned over to be face up, still blindfolded, with a sheet draped over him.

At that point, I assumed the role of an older woman. I acted like I called a girl into the room, and informed her I would be teaching her how to pleasure a man.

And then I played both parts!

The woman symbolized mature MILF experienced domme female energy, and the girl represented young teen inexperienced submissive female energy.

Cute innocent me

Those are the two most popular female archetypes in porn!!!!! The top porn search keywords by men who are into women are TEEN and MILF.

I felt like a genius! An artist! A sexually creative maven!

Meanwhile, he felt Ahhh-ma-ZING!

We both got SO into it – we were in The Zone. We weren’t in a living room – we were in a different country…

He is a random horny man with a cock and lust for women. I am a mature, experienced madam, as well as a tentative teen acolyte.

The woman softly commands the girl to disrobe, that the man will want to touch her small breasts and young pussy, and that she should allow it if she wants a tip.

The woman shows the girl how to touch a man. She instructs her on how to make long, sensual strokes, not fast, swiping movements.

The woman teaches the girl how to tease – don’t touch the cock right away. Stroke the thighs, closer and closer…barely graze the straining cock under the sheet.

Then, touch it. Feel how hot it is. Observe the wetness it leaves on the sheet. That is pre-cum.

The woman whispers, you may kiss it. Go ahead.

The girl does, but it’s more like a hurried peck. The woman corrects her and shows her, putting her experienced, languid lips on it, then instructing the girl to try again.

See if you can’t get the head in your mouth, the woman says. Don’t worry, there’s a sheet on it.

Nervously, the girl tries. She’s concentrating on keeping her mouth open, breathing through her nose, this is all so new and strange…

Slowly, the woman moves the girl’s body closer to the table, and places the man’s hand on her thigh. He takes the invitation to touch, and moves between her smooth thighs, his hand creeping up to find her pussy from behind. He gently probes it with his fingers, exploring the lips and seeking the hole…

Meanwhile, the woman is slooowly moving the sheet out of the way, more and more and more, until the cock is exposed, and pops directly into the girl’s warm, wet mouth.

By now, he is raging hard, and the girl is eagerly squirming. Instinct takes over and she greedily sucks his cock, and his fingers are inside her, and they are a circle of hot, erotic energy. So much heavy breathing and groaning…And all the while, the woman is standing over them, observing with stern approval.

It doesn’t take long for the man to cum – the buildup has been massive, and the erotic tension is like a pillar of fire. The woman can sense when his orgasm is imminent – she instructs the girl not to stop, no matter what happens, don’t take your mouth away, just keep sucking and swallowing.

Don’t lose a drop.

Just in case, she places a hand on the back of the girl’s head to steady her, because she knows how surprising it is the first time.

He explodes, filling her mouth, and she lets out muffled whimpers, and the woman coaches, Swallow, keep swallowing, good girl, get it all… 

It was so fun playing like I was inexperienced, being unfamiliar with sensual touch and good oral techniques. That’s the beauty of my craft – an experienced woman can pretend to be inexperienced, but an inexperienced woman can’t pretend to be experienced!

She just needs lots of practice. And a good teacher. 🙂


Kevin Duarte 2017-11-13 09:47:51



John 2017-11-20 10:11:44

I love your sensuality and how you use it to make wonderful things happen. This entire scene, from the early plan of inviting another woman, to dealing with the disappointment, to brilliantly salvaging what must have been a very erotic evening, is one of the coolest things I’ve ever seen a woman do for her man.


    Kendra Holliday 2017-11-20 14:13:50

    Aww thank you so much! I hope others are inspired to incorporate creative roleplay into their sexy time 🙂


Mrs Fever 2017-12-02 17:55:30

I love what you did!

And including that copy of your sex worker communique was a nice touch – educational, sexy, and informative.


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