The easiest £100 I ever made

From the minute I first received a message from a gentleman who wanted me to sleep with his female friend (supposedly very hot, size 6),  I was suspicious. Supposedly she had never been with a woman and wanted to try it. I was certain there would be a catch like he would want to join or watch or film it or something or she’d be really fugly.

I arrived slightly late due to the bus. I was going to offer 10% off but when it was clear that no one cares I didn’t mention it and took the full £100.

“Right, I’ll just make a cuppa and leave you two to to talk.” It felt like being set up on a playdate by an awkward relative. The man was portly with grey hair, to my surprise and to his credit he did in fact just make a cup of tea and sod off into the only other room in the house which was a bathroom where he had set up a chair and a newspaper and closed the door.

The woman was tiny – I wasn’t even sure that a size 6 looked right, her hot pants were clearly baggy around the waist. However, she was attractive with small brown eyes, a thin mouth and very high cheek bones she looked a bit bird like but certainly not fugly. She was nervously looking at the floor, not meeting my eyes.

“Hi, how are you?”

“I’m good, a little nervous. It’s my first time with a woman, I hope you will teach me!” She had an Eastern European lilt and I couldn’t help but wonder if she was mail order, not that it was any of my business.

“That’s OK. I actually Googled how to pleasure a woman the first time I was going to sleep with a girl I was that worried! Like literally read the ‘WikiHow’ on going down on women.”

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She laughed and it turned into nervous laughter, “Oh I get the giggles! I said this would happen to my friend!”

“It’s OK. Is it OK if I remove your shirt?”

She nods. I slide my hands on to her stomach and lift up her top, over her head. Then I straighten her hair, using my fingers to brush it to one side and start slowly rubbing her shoulders. “Is that nice?”

She nods again. I tuck a strand of hair behind her ear.

“Is it OK to kiss you?” She nods again.

I turn her face to meet mine, her mouth is open slightly too wide and her nerves betray her as the first kiss is a little rushed. I slide my fingers through her hair to the back of her head so I have more control and we manage to find a slower rythymn.

She pulls away and leans back on the bed, staring at me. That’s when I realise that I’m on the clock and I’m supposed to be guiding all of this. No amount of sensual kissing would remove the slightly awkward hooker and client wall.

I inch toward her and start caressing her breasts, they’re a decent size but small enough not to have dropped as far as my natural DD’s have. The woman gets a curious look on her face.

“I want to touch yours? Can I? I mean, I guess it’s supposed to be what I want now isn’t it?”

I laugh and take off my top and bra. Her hands are tiny, her slim fingers pluck at my pierced nipples like someone picking berries from undergrowth. Her eyes search my face for a reaction so I close mine and moan softly.

“Yours are much nicer than mine! Much bigger!” It’s always the same with women, there are are million more things we’re worried about when it comes to sex; do I look good? Do I smell bad? Do I tsste weird? Have I missed anywhere shaving? My boobs aren’t as big as yours.

“Don’t be silly! You have a nice handful. I like them!”

She takes off her shorts and gives me that same look as if she’s waiting for me. I kiss down her taut stomach. She’s so tiny that my hands pretty much wrap around her whole waist. Does she have sex with that other guy? Surely she’d bounce off! Concentrate, Alice. I’ve reached her pants. I kiss her lips through the thin black material.

“May I?” I ask, indicating a desire to remove the underwear. She nods but a bit slower, breathing a bit faster.

I remove the pants and slowly kiss up her legs, stroking the inside of her thighs. I start to lick and suck her lips, I can tell she’s still really unsure as her fingers nervously twiddle her own nipples. I stay down there for a while, her moans are so quiet they’re almost inaudible, I’m guessing what feels nice mainly by the tremors in her stomach and the tightening or loosening of her grip on my finger from inside her.

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I know, however that whatever the internal dialogue in her head is, it’s preventing her from completely letting go. She reaches down and gently taps me on the head. I look up which is always an awkward and never sexy angle with pussy juice and saliva running down your chin. I clear my throat and sit up.

“Can I try it?” Her face is excited, even though she’s blushing.

I’m a little surprised, “yeah of course.” I remove my clothes for her and lay on the bed with my legs open. She coaches by my feet with a look as if she were an archaeologist excavating a new dinosaur bone.

“I don’t know what to do!”

“Well, on me it’s really easy because my piercing tells you where my clit is.”

She pokes the metal hoop threaded through the hood over my clit. “There? Ah! I see now!” Like everyone’s first time, her tongue is quite stiff and pointed and initially she kind of jabs in the right area. After a couple go’s, she starts flicking it up and down. It actually feels quite nice and I’m a bit shocked. It’s incredibly light and delicate but definitely enjoyable. “I’d give you some pointers but it’s actually really good. Like I don’t need to.”

Her eyes get wider, “It feels nice? Do you like it?”

“I do. Do you?”

She nods. I sit up and reposition our bodies so that we’re facing and our legs overlap with a clear spread of each other’s genitals.

“So you see,” I say, pointing down at myself, “all women have this hood which covers the clit so you have to aim below that.”

“Oh yeah! Mine has that, too!” Her face lit up in excitement as she poked her own clit hood.

I nod, “Yeah that’s it.” There’s almost a conspiratal moment between us where we both share the anatomical differences and similarities between our vaginas.

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We use our hands to pleasure each other again and I’m shocked again that the woman teaches me a new hand trick that I didn’t know. I realise she watches a lot of porn and had probably run through in her head the things she was most convinced would work.

After a bit, I flip her back onto her back and resume my position between her legs but this time, having tried what she set out to do, the woman was much more relaxed and willing to give over to me.

It took about 10 minutes and when she came, there was no noise but her breathing was deep and rapid, her back arched into a position a yogi would envy and I spied that the gentleman was peeping from the doorway. It was a powerful moment, she had taken what she wanted to try and taken her pleasure into her hands. She had me focused intently on her, the man hiding in the bathroom and whoever she was probably involved with watching this statement of female sexuality and expression. Whoever it was intended for, this Orgasm was a massive fuck you to somebody.

I left 10 minutes later, released into the sunshine. I strolled along the harbour with a wry smile myself.

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