Weekend CD slave - Part 1

My name is Anthony and I’m a 28-year-old closeted, married, crossdresser. My wife and I have been together for around 6 years now and she knows nothing of my dressing up, I usually keep my kink very limited and usually only throw on a pair of her knickers before masturbating to sissy porn. The post-nut clarity hits me pretty hard every time and has been the reason I’ve never gone further with it. Lately though, the fantasy of fucking a sissy with us both dressed in sexy lingerie has been consuming me. My wife travels a bit for work which is usually when I get the time to dress up. During her last work trip, I was browsing through an online crossdressing community when I came across a post by a crossdresser calling herself Amy. It read, "Hey gurls, I'm looking for other crossdressers/sissies to join me to explore various kinks. Let me know if you're interested." Intrigued, I messaged her, and soon we were exchanging pictures and flirtatious messages. Amy suggested we meet up at a hotel for an entire weekend. I thought about my wife finding out but the thrill of it all was too much to resist. I told Amy I was happy to meet however we would have to wait for my wife’s next work trip which was 2 weeks away. Amy accepted this and in the meantime, we continued with our steamy conversations, the anticipation building as we discussed our fantasies and plans for our secret getaway.

Due to having to hide my ever-growing alter ego, I only had limited lingerie and female clothing so I decided it was time to start preparing for the big night by buying a new sexy outfit. After work, I headed straight to a lingerie store that catered to people like us – those who enjoyed crossing gender lines. As I entered the dimly lit store, my heart raced. The sweet scent of vanilla filled the air as I perused the racks, searching for the perfect outfit to wear for the special occasion.

I finally settled on a sexy black skirt that hugged my figure and clung to my skin like a second layer, It was short with a slit on the left side revealing just enough thigh to be provocative. I matched the skirt with a white blouse with intricate lace details and delicate fabric. I picked out a black lace bra and panty set, complete with a garter belt and sheer stockings. Moving further into the store, I found a wig section and picked a long, flowing blonde one that would complement the outfit nicely. Next, I made my way to the makeup counter, where I found the perfect shades of lipstick, eye shadow, and foundation. Satisfied with my selections, I proceeded to the register, feeling giddy and excited about my upcoming adventure.

On my way home, I stopped by an adult store to pick up some essentials – a butt plug and a chastity cage. The thought of trying these toys with another person sent shivers down my spine. The days leading up to our meeting were agonizingly slow. Each hour seemed to drag on forever, yet I couldn't help but feel a sense of nervous excitement. I got home from work at least an hour before my wife each day so I spent my late afternoons practicing my makeup skills then jumping in the shower to wash it all off just before she got home from work. A week before my rendezvous with Amy I waxed my entire body, I have often shaved my body so it’s not something that my wife would notice but if she did I could just play it off as something I wanted to try rather than shaving so much. I slipped on my new lingerie and send some pictures of me to Amy.

Finally, Friday rolled around and my wife had left for her work trip giving me all weekend to have the much-anticipated adventure with Amy. I got home from work in the afternoon and started to get ready, I headed to the bathroom and took off the work clothes I’d been wearing revealing my smooth hairless body, I just needed some small areas touched up to make sure I was completely smooth. I entered the shower and lathered my body, as I rubbed the soap into my skin, I couldn't help but imagine the touch of another person's hands exploring my body. I grabbed my razor and began gliding it over my skin in long smooth strokes, making sure not to miss any spots. I felt a surge of excitement course through my veins. This wasn't just any ordinary night; this was the night I had been waiting for. The night I would finally be able to express my true identity. After finishing shaving any stray hairs from my body that may have been left over after waxing I turned my attention to my facial hair. I used the razor in all possible directions to make sure my face was smooth and ready for my makeup.

Once I was finished in the shower, I stepped out and dried myself off before applying a generous amount of lotion to my skin ensuring I was soft and smooth from head to toe. The scent of the lotion filled the room, a mix of vanilla and jasmine that was both sensual and inviting. A little extra lotion was applied around my back door and just worked the tip of a finger inside before grabbing my new plug and positioning it at the entrance to my hole, the lotion was all the lubrication I needed to push it inside me. A heart-shaped purple jewel was now all that was visible from the plug. With the plug positioned firmly, I moved on to my chastity cage, my goodness it was uncomfortable, I’ve never really been into the chastity side of things, I just thought some of the cages looked really cute and I wanted to make a good impression for Amy. I tried to brush the discomfort aside and forget about it for now as I planned on taking it off once I was at the hotel with Amy anyway. I moved on with applying my make-up just as I had been practising all this week, Contouring used to appear as feminine as possible, my lips painted a deep red and sultry dramatic eye shadow completed the look. I slipped my new lace front wig on and wiggled it into place, the long blonde perfectly styled waves falling around my shoulders. I smiled at my reflection, feeling more confident than ever before. It was now time to go, I threw my makeup, mobile phone and some other supplies in a bag I had borrowed from my wife and slipped on some open-toe heels also borrowed then made my way downstairs and opened the front door, took a deep breath and stepped outside, ready to embrace whatever the night had in store for me.

I made my way to the hotel and found a spot to park my car, I got out with my heart racing as I crossed the parking lot to the designated room. With a shaky hand, I knocked on the door. The door opened, revealing not the woman he had been expecting, but a balding, grey-haired, moustached man with a beer belly and broad shoulders. I froze for a moment before I could get any words out. “I must have the wrong room, sorry,” I said as I turned to walk away. In an instant, he grabbed my wrist yanking me past the doorframe and into the hotel room. “You’re not going anywhere” he sneered as he slammed the door behind us. I started to scream at him “Let me go” as I struggled towards the door. He picked me up, my handbag falling to the floor and in one swift movement he slammed me onto the bed pinning me down, I screamed as loud as I could but only for a second before he covered my mouth with his hand, he took a stray sock that had been laying on the bed and shoved it into my mouth. I had one free hand which I used to hit him which had little effect, he was so much bigger than me and quickly adjusted himself so that his body weight did most of the restraining, his hands now pinning my wrists down to the mattress.

I thrashed underneath him as I tried to scream through the sock stuffed in my mouth effectively muffling my cries. He let me squirm and struggle for a while longer but you would be surprised how quickly you can tire yourself out fighting to free yourself from being pinned down and after a minute or so my thrashing became feeble attempts at resisting against my attacker. I struggled to breathe past the sock and began to feel a little lightheaded, my squirming stopped as I submitted to his grip. “You done now slut? ‘Cause I can do this all night” he said looming over me, his sharp piercing eyes staring into my soul. I didn’t respond, I could not face my captor and I turned my head to look away closing my eyes, trying to wish my way out of this situation. Tears began to flow from my eyes as I pictured my situation and what I believed this man planned on doing to me. He noticed the tears and started to laugh “You sissies are so easy to break, I probably don’t even have to blackmail you do I, Anthony?” Wait! Anthony? How does he know my real name? This quickly gained my attention and I turned my head back to look at him, his eyes lit up as he watched the realisation hit my face. “Oh yes, I know a lot about you Anthony. I'm somewhat of a hacker and I've been able to learn all I need to about you, I know your wife’s name and contact details most importantly but I’ve also got your employment details from which I was then able to get your bosses and colleagues' contact details. I have your social media accounts and have copies of all your friends lists”.

My mind was reeling, my heart was pounding out of my chest, and complete shock fear took hold of me. This man whom I’d never met before had just used my real name, not that of a cross-dressed alter ego but rather my real identity, an identity that I would do anything to protect. “I’m going to let go of you now but before I do I need you to agree to be a good girl,” he said with his full weight still on top of me “No screaming or scratching okay? You don’t want me sending all those pictures you sent me to your wife right?” I nodded in agreement “You understand I will destroy your life if you are naughty yes?” Again I nodded meekly and with that, he released his iron grip and got up off the bed. I sat up and pulled the sock out of my mouth. I swallowed hard, trying to maintain my composure.

“Why are you doing this? What do you want from me?” I asked meekly, his gaze fixed on me, his lips curving into a dangerous predatory smile. “I want you to be my slave for the weekend, you are free to go right now if you want but you should know if you leave I will be sending all of the pictures of you and screenshots of messages to your wife, coworkers and everyone on your social media friends list and did I mention the videos? Oh yes! He said excitedly, you should really strengthen your cybersecurity. I have hacked your computer, it’s how I got all of your information. Remember the email you opened from me with what you thought was a ‘broken link’ attached? Well, It gave me access to your laptop and I accessed your webcam. Now I have multiple clips of you dressed in your wife’s lingerie sitting in front of your laptop masturbating and parading around the room trying to look sexy. If you decide to stay and serve me as my slave then those videos will never see the light of day but you will do exactly as I say and obey every command, any disobedient actions on your part over the course of this weekend will be met with a video, photo or set of messages being released, His threat hung heavy in the air as I struggled to find the words to respond, I was unsure of what to do.

Would he let me go right now if I said I didn’t care if he sent them? Should I tell him to go ahead and send it to everyone? At least then I could go to the police. Complying with his demands meant putting myself at his mercy and who knows what he was going to do to me but the thought of my wife finding out was more than I could bear. Fear was coursing through my veins as I weighed my options, I couldn’t help but notice the way he looked at me – with a mix of hunger and contempt. It sent a shiver through me that I couldn’t quite explain. He must have noticed my hesitation because he leaned closer to me, his breath smelling of cheap beer, his eyes darkening. “You should know that I won’t hesitate to release those photos, videos and messages if you don’t cooperate”. As I wrestled with my conscience, I couldn’t help but wonder what kind of twisted things he had in mind for me, I love my wife and her seeing those photos and proof of my plans to cheat on her would destroy her, let alone all of my colleagues seeing and laughing over my compromising photos. I couldn’t allow this man to ruin my life and humiliate me in front of everyone that I know. I reasoned to myself that it’s just 48 hours, make him happy and he might leave me alone, it’s the best chance that I’ve got, and the only option I could see was to comply with his demands. I will stay for the weekend to save my marriage. “Okay I will stay” I said meekly. “Good girl, I knew you would make the right decision” My heart sank at the sight of this man smirking at me, how could I have been so foolish? I was so caught up in the fantasy of meeting another crossdresser that I hadn't considered the risks, now I’m stuck being this man's plaything for a weekend.

Continued in Part 2….