First sex date

It’s been two weeks since my first date. I’d say I haven’t written because the last two weeks were spent switching jobs and negotiating draconian employment contracts. The real reason is the experience was very different than I expected.

To be fair, the man I met is a great guy. He’s good looking, kind, thoughtful, articulate, muscular, and with a ginormous cock. More on that later… After a week of back and forth establishing who were were and what we were looking for, safe sex boundaries, and logistics I met him at his house for a sex date.

We seemed to get along with an ease and conversation was fluid but brief, mostly because we had done enough talking in the preceding days. There was a definite momentum to his actions as he undressed me and looked me over as if he was preparing to eat his favorite meal. The focus and attention I felt was an aphrodisiac that poured into my body warming me and making me more pliable to his direction. I was locked in my Mature Metal Jailbird device at the time without orgasm for 60-70 ish days so although I was burning with desire I could only be a bottom. The usual dominant male urges seemed to have abated, redirected, or re-wired themselves to enjoy the pleasures of being taken instead of giving.

The sex was hot. I started seeing myself as staring in my own porn flick and captured the images and sensations in my mind as I started finding dialogs and themes that would make the scene white hot. It was in that moment I realized the sex was great, the attention and energy amazing, but psychologically I was searching for stimulus. I NEED to feel mentally engaged. My sexuality is 80% psychological and 20% physical. As the first romp winded down we had a bit of an intermission, mostly for him because I was still completely lit on endorphins from not being able to come. After a few minutes he was back in top form again. For a while there I thought I might be able to orgasm too but the combination of my wiring and inability to access penis proved too high of a hurdle. Maybe he was too big? Perhaps more practice will help me find the right connections to orgasm from penetration. I hope so. What I can say is now I understand when women say sometimes a cock can be too big to be enjoyable. Part of my SPH fetish was crushed when I realized 7″ might be better than 10″. Yup. There was definitely a point where things got a bit eye watering even though I’m proud of my ability to play with some of SquarePeg’s best toys. At least I was feeling secure with my average cock locked away safe from a real comparison.

Damn. I wish my mind was being fucked with as hard as my ass was. I’ve been reading a great book “Enough To Make You Blush –  Exploring Erotic Humiliation” by Princess Kali. Truthfully, I was desperate for context on the psychological deficit I felt and picked up the book on Amazon to fill the void. My expectations were low but I have to say this book is amazing! It is the single best read on BDSM and power dynamic I’ve run across since I’ve been looking. Don’t be misled by the title, the content is written from extraordinary insight and experience. Page after page I find myself saying “wow..that finally makes sense!”.

What I do know is Sex with Cheyenne keeps getting better, more vulnerable and fucking hot. She’s closing ground on me at a furious pace. Her strapon cock puts my dates’ cock to shame. Maybe it’s me that should be blushing? Fuck it. I’m digging my new role.

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1 Response to First sex date

  1. thechastecyclist says:

    Glad you had a great time!

    Liked by 1 person

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