August 5, 2015 – Toronto (Jacqueline)

I am getting ready to leave Detroit and I still haven’t firmed up anything for my next stop, Toronto. Maybe my aggressive and frank approach is too strong for Canadian women?

I had reached out to a sultry brunette, Jacqueline, late last night and she responded this morning. We’re chatting on Tinder as I’m packing up, getting ready to leave the hotel. Mostly small talk. I tell her more about my baseball trip and she’s genuinely interested. It’s cute how she’s a fan of the hapless Blue Jays that haven’t made the playoffs in about 20 years. They’re a half dozen games behind the Yankees at this point.

I also make sure she’s read my profile. She has! We discuss the directness of it and how it’s designed to cut through the “noise” of Tinder. I ask if she’s “intrigued, curious, and/or interested?”

Jacqueline responds:

"You can assume that I'm at least one of those... ;) "

Oh, I like her already!

I’m just about to ask if she’d like to meet up… I’m literally typing the question… But she asks me first in a charmingly polite Canadian way:

"So... at the risk of being a little forward... I'm leaving for vacation on Friday and would like to meet for a drink before I go. Is that a possibility with your schedule?"

Oh, absolutely, yes. Tonight!

I won’t be getting into Toronto until at least 8 or 9pm but she has to work late anyhow. We plan to touch base during the day and firm things up.

But I don’t hear from her for hours. I totally think she’s going to flake on me until she finally reaches out on Tinder. Jacqueline apologizes (of course!). She’s been swamped at work and won’t be able to meet until around 10:30pm. It’ll be late but I’m wide awake now that I know she’ll be headed my way.


We plan to meet at the hotel bar so I position myself in the short distance between the lounge and the big glass sliding doors of the hotel’s main entrance. Apparently it’s a “loose” 10:30 and I’m starting to get that “she’s flaking” feeling again.

But then I see her walking in the door.

And she sees me.

And she nearly gets flattened by a luggage cart.

It’s a near miss so instead of it being a tragic end to our evening it instead breaks the ice a little. She walks up to me and we hug. She’s tall. It’s a delightfully unexpected surprise.

Jacqueline is in her mid 30’s, long, straight, dark brown hair that frames her strong yet soft and feminine, pretty face. She’s on the voluptuous side and carries herself confidently.

We walk into the lounge, choose a low table with big red velvet chairs, and order a couple of glasses of red wine. We talk and laugh. I love her laugh. And I find myself getting lost in her eyes as we discuss myriads of both funny and intellectual topics. I’m unsure where the night is going because I’m not sensing a lot of flirting from either of us. I’m certainly attracted to her but instead of a hook up did I wind up meeting a really great friend for the first time?  I find it’s already midnight and I should probably press the issue.

The waitress has thankfully been leaving us in peace for most of the evening but now that I want to settle up I can’t even locate her. Oh, there she is behind the bar… I wave to get her attention. Nothing. I decide I should go to the bar to settle up. I stand, touch Jacqueline’s arm, tell her I’ll be right back, and go pay the tab.


I lead Jacqueline to the elevators and up to my room. I open the door and gesture for her to enter ahead of me. The lights are off but the streetlights provide plenty of illumination through the sheer curtains.

Jacqueline stops walking and turns around to face me. I reach out for her and pull her close. We kiss. Electricity shoots through me. I think she just melted a little.

We don’t hesitate to climb onto the bed, continuing to kiss. Her lips are soft and knowing. Her tongue seeks out mine. She pulls on my lips with her teeth. She’s driving me nuts.

My fingers trace the curves of her soft body and she presses into me in response. I know she can feel my already-hard cock against her. I want to be even physically closer to her; I feel like I cannot get close enough. Our clothing feels like a barrier. It must be removed. I pull away from her slightly and, apparently sensing my next move, she takes off her shirt. It’s already late so I want to skip the 20-minute “continuing to kiss while we’re in our underwear” phase; I unhook her bra and allow her beautiful orbs to bounce free. They are succulent and round with nicely-sized rosy aureoles. Her nipples quickly respond to my mouth tugging on them in turn. Jacqueline’s moans encourage me to pull and suck on them harder.

Suddenly she separates from me and we begin stripping furiously. I can’t unbutton my dress shirt fast enough! Stupid cuff buttons!

Jacqueline is already naked and she helps me out of my jeans and tight boxer-briefs. It feels so right to be naked with her.

I lay her back down on the bed and smile at her. We both know what’s next.

I spread her legs apart exposing her womanhood.

It is magnificent. Truly. Her clit is over an inch long and is complemented by the meatiest lips I have ever seen in person. She’s turned on; her clit is engorged and jutting out. The lips are elegantly draped down from it.

My overwhelming urge is to put it all in my mouth. And I do. It satisfies something deep inside me.

I lick and suck and pull. She moans. I pull harder. She moans louder.

My tongue works inside her and I get my first full taste of her juices. She’s sweet, a little tangy, and somewhat musky. I still haven’t used my fingers at all. My mouth cannot get enough of her.

I begin working my tongue in circles around her clit. Jacqueline slowly, sensually thrusts her hips toward me, arching her back, getting lost in the sensations. I suck on her clit, letting it slide in and out of my mouth.

She’s getting louder. Her hips thrusting harder. I suck strongly on her clit, taking it deeply into my mouth, rolling my tongue around it forcefully. In just a few seconds she’s cumming and I have to hold on as her body spasms from the pleasure. She pushes me away when she can take no more.

I give her only a couple of minutes to catch her breath. In the meantime my fingers gently explore her pussy lips, eventually finding their way inside her. I find Jacqueline’s g-spot and begin to massage. She definitely approves. My hand works up and down harder and harder, faster and faster; I seem know exactly where and how to touch her. I bring her close to another orgasm but then pull my fingers out and suck on her clit again. This sends her over the edge. Her body bucks. She screams and cums hard. I sense she wants me to keep up the intensity until she reaches her limit so I hang on. After several long seconds she again pushes me away, panting, breathless.

She pulls me up to her and kisses me deeply and passionately, loving tasting her pussy on my mouth. We continue to kiss as I sneak my hand down between her legs once more. My fingers find their way inside her again. I press my mouth hard against hers as I forcefully finger her pussy with my palm rubbing against her clit. Within a few seconds she stops kissing me, gasping now as I bring her to a powerful g-spot orgasm.

She rests for a few minutes then reaches down, grabs my thick, hard cock, strokes me strongly a few times, and asks me to fuck her.

Gladly.

I climb on top of her luscious body and easily slide myself into her sopping wet pussy.

I have never felt anything like it.

The way her pussy lips extend from her body when her long clit is swollen creates suction around my cock that feels like she’s grabbing onto me and won’t let go.

I thrust into her slowly, wanting to feel every sensation. We are completely in sync. Her body moves perfectly with mine and in a few short minutes I feel her trembling beneath me. I bite her neck and she responds by wrapping her legs around me and forcing me all the way into her. She’s controlling my thrusting now with her thighs. The intensity is building. Jacqueline is getting louder; her sensual panting has once again become a vocal gasping which then turns into a low scream. She’s cumming once more. Thankfully her legs are gripping me or she would likely throw me off the bed.  As she orgasms she looks deeply into my eyes, kisses me passionately, and drives her fingernails into my back. The pain is exquisite. I feel my own orgasm quickly build from the base of my cock. Her pussy grips me and I cum hard with a loud moan. Both of us now exhausted, Jacqueline hugs me close as we slowly come down from our ecstasy.

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