August 2, 2015 – Detroit (Margaret)

I drive east from Chicago slicing through all of Michigan today to get to my hotel in the northern suburbs of Detroit. I had canceled my Airbnb room and booked a hotel to ensure I would have a place to play, thereby increasing my chances of having an encounter.

Though I’m staying in a hotel, tonight I have plans to meet Margaret at her home. We had matched on Tinder and, since most of the women in my age range are looking for their soulmates (on Tinder! WTF?), I made sure to ask if she had read my profile. She hadn’t, then came back to the chat saying:

OMG! I have now! OMG!

She was shocked at my frankness. Usually this reaction results in the conversation’s swift end. I recognize the pattern so I tell Margaret I understand what I’m offering isn’t everyone’s cup of tea and begin to wish her well.

She re-engages, telling me this is something she just might be interested in. She’s been exploring her sexuality and, if my skills are as good as I say they are, she’d like to experience them herself.

We meet at her home that night. She greets me at the door, blush wine in her hand, her little dog yapping at my heels. Margaret smiles at me sweetly but nervously. She obligatorily says she doesn’t usually invite guys over like this.

Margaret is in her late 40’s, maybe 5’4″ with mid-length brown hair. She seems very reserved, much more than I anticipated. I’m deeply concerned that the night might be very flat.

She’s drinking the last of her wine as we sit on the couch and make small talk. Very. Small. Talk. I’m starting to wonder if coming over was a bad idea.

It’s now or never.

I lean in and kiss her. Her lips taste sweet. I’m guessing she’s drinking Moscato. Margaret moves closer and puts her hand on my leg, squeezing. Her kisses are warm and passionate; they bely her modest appearance. Margaret pulls on my lips with her teeth. My moaning encourages her to press her mouth hard against mine and explore with her tongue.

My hands reach out to touch her body but she’s already getting up off the couch and inviting me into the bedroom. With only a sliver of street light illuminating the room we move toward the bed. Standing next to it we hold one another while continuing to kiss. I run my hands down Margaret’s body, feeling her curves. She presses into me softy. My lips kiss across her cheek and down her neck. I bite gently and she approves with a slight shiver. I believe I also hear a slight growl.


There is a hunger.

Margaret moves back slightly and is now unfastening my belt. And unbuttoning my pants. And pulling down my zipper. Her hand quickly finds its way to my cock, still covered by my underwear. My manhood aches to be released but she treats it like her toy; her fingers run up and down the length of it, only occasionally giving it a satisfying squeeze.

I remind her that the night is supposed to be about her. She chuckles, giving my cock one final squeeze before stepping back to unfasten her dress and letting it fall to the floor. My eyes have adjusted to the darkness and I can see her dark, silky bra and panties contrasting with her light skin.

She helps me off with my button up shirt, making sure to undo the buttons at the cuffs. It falls to the floor. My pants, already undone, are quick to follow.

Margaret climbs on the bed. She adjusts the pillows and lays flat on her back in the center of the bed. I join her, straddling her body, and bending over to kiss her lips. My mouth trails off to her neck. I nibble, kiss, and suck slowly, tantalizingly down the center of her chest to her stomach. I shift my body toward the foot of the bed and continue moving my mouth down. My hands gently spread her legs. I lean over and let my warm breath caress her inner thighs. Her eyes close and her back arches up. It’s an invitation for me to remove her panties to expose her womanhood. I gladly accept.

Once bared I lower my mouth onto her pussy. She’s shocked by the suddenness of it which is precisely the effect I was hoping for after all the teasing. Her lips are soft and delicate and deliciously wet. My tongue separates them and begins working up and down her slit. Her hips subtly mimic my motion. Margaret’s breathing is becoming more labored. She’s moaning under her breath. Louder with each moment. My mouth focuses only on her engorged clit, sucking with my lips while swirling my tongue around it in snug circles. I slide a finger inside her. She’s blazing hot. I add another finger and her moaning becomes unabashed screaming as she begins to cum. Her body is bucking. Margaret thrashes on the bed. I hold on tightly making sure to keep my mouth pressed to her clit and my fingers deep inside her so that I don’t suddenly abandon her during this powerful orgasm.

Her climax lasts for well-over 30 seconds but then for minutes afterward she enjoys its aftershocks; several times she tries to catch her breath, smiling, then suddenly closes her eyes, shivers, bucks.

During one of these moments I kneel next to her and forcefully slide two fingers inside her to stroke her g-spot. Within a few seconds I give her another full-on orgasm. More uncontrolled screaming. Thrashing.

I let her calm down briefly then begin to work my mouth over her pussy once again. She hasn’t had any squirting orgasms tonight but has gotten extremely wet. My face is covered with her copious juices.

I kneel upright but slide my 2 fingers back inside her. I slip my other hand underneath her bra to feel her ample breasts. Margaret reaches behind her to unlatch the garment and remove it. Her nipples are large and erect. I pinch them lightly and she implores me to do it harder. I comply and she enjoys that small bit of pain mixed with the pleasure my fingers are providing in her pussy. My fingers tap on her g-spot briefly before moving in a come-hither motion. Margaret’s moans are building again. My fingers grab onto her g-spot and begin finger fucking her with determined movement. The pleasure is building inside her. She can only stand this for a few seconds before she is again in the throes of a violently loud orgasm.

I allow her only few moments to relish the sensations. Before it winds down however, I begin sucking and licking her clit. Margaret lets out a gasp, her hands clench at the bed sheets, she thrashes, literally thrashes, and has a clitoral orgasm on top of the g-spot orgasm she was already experiencing. Her pussy clenches my fingers tightly for several long seconds then releases with a flood of juices.

Margaret is laying there on the bed in front of me, exposed and beautiful and glowing. Her breathing is hard and she’s slowly calming though, for minutes afterward, aftershocks repeatedly disrupt her serenity.

I hear her whisper intently, “I want to feel you inside of me.” She rolls over and, with her head on the pillow, gets on her knees. Margaret raises her ass up to me. Half asking, half-demanding, “Fuck me, James?”

My cock has been rock hard while I have enjoyed pleasuring her. I kneel behind her and tease her pussy lips with my head. My teasing doesn’t last long. Margaret rocks trying to capture me inside her. With one perfectly timed thrust backward she has my cock deep in her soaking wet sex.

I push forward and I’m even deeper, pressed into her up to the hilt. My thick cock stretches her. She consents with a guttural moan.

Margaret works her hips in circles as I kneel without moving. She’s looking back at me over her shoulder and smiling mischievously. Her tight pussy is expertly milking my cock. My pleasure is building. I suddenly have a base urge to be animalistic with her. I push all my weight on top of her, forcing her flat on the bed.

I lock my legs with hers, grab both her wrists above her head, completely pinning her down. My cock is throbbing, aching, as I pound into her. I want to cum but I hold back and continue to take her powerfully. My cock is hammering her, filling her, dominating her. Our sweaty bodies are dripping. Margaret’s body stiffens, her moans of pleasure once again become screams, and I increase my pace to ride her through her climax. She writhes and I hold on. Her pussy grabs at my cock and I can no longer contain my orgasm. From my head to my toes I feel intense pleasure encompass my body. I slow my pace as my orgasm continues, then subsides to a low hum of full-body tingling.

Margaret and I release from our locked embrace. I roll off and lay on my back almost panting. She moves close to me, her warm body almost too hot right now. Margaret strokes my chest as we lay there in the dark completely spent and satisfied.


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