We met in the Literotica UK chat room. I got talking to Chloe first then Ash, after they had both read my only Literotica Story Submission 'The First Time', my entirely fictitious, first person account of sucking cock for the first time for the benefit of my watching Domme.
They both just got it, that need. The simple, deep desire of a seemingly straight guy who desperately, wantonly wants to feel a cock in his mouth.
We chatted about what we all wanted to get from it. I was open from the get go, explaining that I wanted to explore my bisexuality and that doing it in front, or at the behest of a woman would make it all the more erotic, sensual and arousing.
Chloe asked me if I wanted to maybe try sucking Ash's cock. It didn't take me long to admit that yes, that's exactly what I wanted. She teased and taunted me for weeks, asking if I'd like to wear a pair of her lace panties while I was on my knees with Ash's cock in my mouth. Did I want to be a good sissy cocksucker for her to watch? The more direct Chloe was, the more she got inside my head. She dialled up the humiliating, degrading chat as we talked more, which totally fucked with my brain and left me helpless with needy desire.
Before long it was pretty much all I could think about. Every time we talked the conversation was the same, her cute, well-spoken English-accented voice encouraging me to embrace the woman inside, to be her good subby sissy. To think all the time about how I would feel to be completely submissive in that moment, my own needs put entirely to one side as I worshipped Ash's gorgeous cock.
We talked and talked, making ever more intricate, intimate plans for what Chloe wanted to see and what I would be willing, desperate to do.
FInally, just when I thought that was all it would ever be, a fantasy, Chloe made plans. A simple message arrived on my phone, 'The Dilly Hotel, Wednesday 7:30 sharp. Everything you need will be there. The key will be in reception'. I read it again and again, my head swimming, my cock pulsing with arousal. I had an inkling what 'everything you need' meant and I wasn't about to ruin the vibe by asking. I messaged Ash to ask if Chloe had made plans with him and he simply replied 'See you at 8:15'. Whatever they were planning, I'd have 45 minutes to prepare for it.
The week that followed was excruciating, time seemed to slow the closer it got to that fateful evening until finally, Wednesday arrived. I worked the day in London, struggling as I had for so long to focus on my work and not on the prospect of handling and tasting a throbbing cock! I made my way to Piccadilly Circus for 7:15 and went to the concierge desk when I arrived.
I gave my name and the pretty, young receptionist smiled as she handed the room key to me. 'Room 616, it has a lovely view over London'. As I went to take the room key she held onto it, forcing me to look up again at her smiling face, 'Have a wonderful evening sissy' she breathed at me, smiled widely then turned her back as if nothing had happened. My ears were ringing and my face was beet red, my feet frozen to the spot. Chloe had told her? I realised I hadn't moved when I heard her say 'Off you go now, time to get ready'
I drop my eyes to the floor, turn and make my way to the bank of elevators, calling the 6th floor and desperately trying to compose myself on the way to my room. I swipe the keycard and enter room 616. The room is amazing, large, luxurious but contemporary.
A huge, super-king bed and floor to ceiling windows, which do indeed provide a wonderful view over London, dominate the room. Mindful of what I would be doing later, I grab the remote and wind the curtains all the way shut. Soft lamp light immediately fills the gloom, throwing shadows into the corners of the vast space.
In front of the vast expanse of glass sits a low table and two comfortable looking chairs. On the table stands an ice bucket with a freshly opened bottle of champagne and two flutes. There is also a laptop, powered up with the Windows lock screen showing. In each corner of the room there is a camera mounted on a tripod. Was this what Chloe meant by 'everything you need will be there'?
On the wall next to the bathroom is an enormous flat screen QLED TV, currently displaying the standard guest welcome messages, cycling through the hotel catering offering, spa & massage facilities and some local sights that hotel guests might want to take in on their visit to London. Next to the TV is a full-length mirror.
In the centre of the bed is a small box with a handwritten note on top. I pick up the note first and read 'Good evening Sissy, thank you for coming to worship Ash. As you can see I have made a few arrangements for your evening of debauchery. Be a good girl and get ready for Ash. I will be watching.... Chloe xxx'
I check my watch, 7:25. OK, 50 minutes. I open the box and my heart skips a beat. With shaking hands I slowly take everything out, one item at a time. A pair of white lace panties, brazilian cut and incredibly sheer. A matching size zero bra. The sexiest suspender belt I have ever seen, matching the rest of the underwear with a total of eight clips for the stockings that are next out of the box. Lace topped white nylon. At the bottom of the box are three more items. A pair of pink high-heeled shoes with ankle straps, a tiny chastity cage and a steel, jewelled butt plug along with a bottle of lube. She really had thought of everything.
I check my watch again, 45 minutes. I strip quickly, folding my clothes and putting them all away, not wanting to alter the room in any way. I look at myself in the floor to ceiling mirror, admiring the body Chloe has moulded over the preceding months. To say there has been a change would be an understatement. Long gone was the man I had once been, if not overweight then certainly not the lean, almost feminine body that was looking back at me now. Long gone also was the body hair that had sprouted at adolescence. Months of using hair removal creams and waxing had left me hairless from the neck down. I run my hands down my body, pleased with how I look for Ash this evening, for Chloe.
Making my way to the bathroom, I shave my face, ensuring I am as smooth as I can be before jumping into the shower and scrubbing myself under the hot water. I'm glowing when I finish, my smooth skin pink and soft. I moisturise all over then start to prepare in earnest for Ash's arrival.
Starting with the cock cage, I breathe deeply and focus, allowing my semi-erect cock to go soft and limp before sliding my foreskin back and getting the fixing ring into place, snug around the base of my cock, making the skin around my balls tighten. I insert my cock into the cage and close the padlock, placing the key on the chain around my neck and finally inserting the urethral tube and screwing it into place. I lube up the beautiful, jewelled butt plug and have almost no difficulty sliding it into my ass. The days I have not worn a plug over the past month have been few and far between, and the training has paid off. It has a heft as it settles into place, a weighty presence that I can feel at all times and even more so when I test kneeling on the bathroom floor. The plug exerts a constant, teasing pressure on my prostate, the stainless steel transmitting every single movement, every vibration directly to this intensely sensitive erogenous zone. I smile and my cock pulses in its steel cage.
I apply my feminine deodorant and Jo Malone perfume and leave the bathroom, feeling every inch the submissive sissy I have been working so diligently to embrace since Chloe, Ash and I first started to talk. I admire my partial transformation in the mirror, marvelling at the way my cock looks in its new steel home.