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Hello again, I feel a bit embarrassed that it's been such a long time since I last posted on this wonderful forum. My apologies, Mistress Watchful (although…

member_fe4f74e910 28 Aug 2026 #1

Hello again,

I feel a bit embarrassed that it’s been such a long time since I last posted on this wonderful forum. My apologies, Mistress Watchful (although it is lovely to see the place growing and thriving). However, I believe I have something worth sharing beyond just my fantasies about my Goddess Bitch Manager.

I actually decided to take some practical steps toward finding a Mistress/Keyholder/Cuckoldress. To that end, I’ve spent considerable time scanning the Dating Columns of various publications and internet sites, going on dinner dates, and trying to spot hints of a dominant personality or more than just an interest in vanilla relationships. It has been interesting and enjoyable, sometimes downright terrifying, but the woman of my (admittedly submissive) dreams remained elusive until last week.

I responded to an advert that seemed to have a nice assertive tone, though I didn’t hold out much hope since I was well outside her age bracket by several years. However, Carol, who is in her late 20s, told me later after the drinks had flowed that I had a pleasant voice and who would turn down the chance of a night out at a top restaurant?

Carol was far from shy or inhibited. After a fantastic meal, lots of wine, and more drinks, she made it clear she had no intention of sleeping with me if that’s what I expected, although she did admit to using dating networks to enjoy good living and a very energetic sex life without strings attached with people who caught her fancy.

In fact, she went on to flirt and tease me with graphic descriptions of her most memorable conquests (not just men, might I add). By this time, as you can imagine, I was beside myself. The conversation turned to my reasons for being there, and since Carol had been so candid, I decided nothing ventured, nothing gained. Hesitantly, I started describing my interest in dominant women who control a man by keeping him submissive in a Chastity device.

Carol actually shut up for the first time as I bumbled through my whispered confession with downcast eyes. As I finished my tale, I waited for her to laugh bitterly or leave the table in outrage/disgust, but it never came. Instead, Carol just stared hard at me. After what seemed an eternity filled only by my dry mouth and pounding heart, she started to grin and held my gaze as she questioned me further.

To cut a long story short, Carol was fascinated (and still is), and we agreed to meet again the next night.

I booked another table for dinner, got a room, and after another evening of food and drink—lots of it in my case—we went up. There my dream came true: a vivacious woman clicked the padlock shut, sealing me in chastity. As I stood before her naked and vulnerable, the keys vanished into her purse.

Carol spent considerable time examining her property afterward, taking obvious delight in her new role and the inescapable nature of my submission. However, for her, the night was still young; she rang for a taxi to meet some friends at a local club, leaving me alone to contemplate my newfound, very real state of chastity.

My only link with Carol is via mobile phone; I have to wait for her to contact me sometime next weekend to arrange another date. My friends in the community will keep you posted. milton

member_a75d26c9f5 29 Aug 2026 #2

Congratulations Milton, I hope it works out for you.

member_fe4f74e910 30 Aug 2026 #3

Thank you PT109. A quick update: I have received a text message from Carol. It seems she is out for a night on the town and fully expects to get 'a right good seeing too'. She hopes I will be thinking of her... interestingly, she has been 'dripping' since our last meeting knowing that I am locked up. milton

member_988a8a5ecc 2 Sept 2026 #4

Lucky man - looks like you're in for a ride now - congratulations.

member_fe4f74e910 2 Sept 2026 #5

About 3:30 am my already restless sleep (just how many erections is it possible to have in one night?) was broken by my mobile ringing and ringing. Answering it, a breathless female voice whispered in my ear... no prizes for guessing who... a very satisfied Carol... Her 'stud' had gone to get some drinks, and she thought she'd better quickly tell me that she'd just cum for the second time; his 'juicy fat fucking cock' hit all the right spots, and she'll be 'fucking crawling home at this rate'. Before I could stutter a reply, Carol whispered he was on his way back and laughing wished 'Milty' goodnight. Staring at my mobile in disbelief with my imagination running riot, I became very aware of my imprisoned cock trying to achieve an erection and the biting discomfort on my balls. I reached down and felt the hard plastic sheath its lock...... chastity indeed. Needless to say, it was a long time (and a cool bath later) before I finally managed to get some sleep. I think Carol is going to be a very enthusiastic keyholder....... and I am so grateful to her.... actually very, very grateful. milton

member_fe4f74e910 4 Sept 2026 #6

Knightservant and sensual slave thank you both for your good wishes. milton

member_e55fab181a 6 Sept 2026 #7

Milton I'm so happy for you! I'm even happier that you have chosen to come here and share the adventure with us all.:love0059: I look forward to reading how this all turns out.:animal0008:

member_61bffea921 7 Sept 2026 #8

Absolutely brilliant.:-)

member_fe4f74e910 9 Sept 2026 #9

Thank You Mistress Watchful for Your gracious reply. I will gladly share what I suspect... well... know is going to be a real dose of reality..... happy days indeed! milton