Surrendering to Darkness Ch. 01

This is a work of fiction. This is a complete fantasy.

I am in my thirties, I have cross dressed for a number of years and with the pandemic I have had the opportunity to dress more often and to express my feminine side. When dressed I am Chloe. I am average looking as a man, slim and toned. I am easily lost in a crowd. My only exceptional features are my blue eyes and recently my long blonde hair which I grew out during the lockdown. I have a professional job in the city working for a large company.

It started in an on line chat room. A user name 'Mistress Understood' sent a personal message using my "password" from my profile.

"Looking for a naughty angel", flashed the message.

Some users in chats do not have detailed profiles, so I was pleasantly surprised to read about this user. I read enough to be intrigued and to understand that they were female, dominant and liked special girls. My profile indicates I am male, but expressing my feminine side and prefer to be submissive.

I replied to the message. We chatted the first time for nearly an hour. I learned my admirer was a business professional who also worked in the city for a large company. She was divorced, no children and had discovered her dominant side. I learned her profile name had a double meaning: as in 'I'm in charge is that understood?' but also 'MissUnderstood'. I shared my love of lingerie, hosiery and heels. We both had a secret side that they couldn't share with the real world.

For several weeks we talked about our secrets, our naughty thoughts and fantasies. We discussed our results from certain on-line tests we had taken.

Our next on line meeting we role played. I was her special secretary working at her company and she 'discovered' my secret. A fear I have that she played on which made the fantasy very exciting. I was virtually dressed in black lingerie, stockings, satin blouse, pencil skirt and heels. She took me to a lift used her executive card locking the lift to the top floor. She 'forced' me to my knees and lifted her skirt. She demanded I please her orally. I did as I was told. It was an escape for both of us. Reality was suspended and it must have been the longest lift journey in history. We laughed about it afterwards. I think we made a real connection. My panties were wet and I retired to bed reflecting upon the encounter.

We had regular chat sessions, role played and generally learned about each other. The weeks passed and both admitted we looked forward to our meetings. We introduced toys to our on line games.

Another week passed and I was back in the chat room. I had chatted with several regular users and was about to close down when I received a message from 'Mistress Understood'. I responded and we expanded on our roles. As we prepared to depart after another naughty role play she asked if I had ever met up with people in real life. I replied I hadn't, but had been out dressed on several occasions. I admitted being outside as Chloe was thrilling, but also quite scary. She asked if I would meet her as she wanted to discuss a proposition. I was somewhat reluctant and afraid of exposure. She explained she had as much to lose. She told me to think about it and we would speak the next day. My dreams were turbulent and my waking thoughts chaotic as I contemplated her suggestion.

We met online the next day and she detailed her plan. We would meet in a public place and we would dress to blend in. We would wear sunglasses and a hat. We would arrive carrying a single red rose. We would share a coffee, go for a walk and she would tell me more. It would be exciting like something out of a spy novel. I finally agreed to meet the following Sunday at a coffee shop outside St Pauls underground station as it was close to the area where we worked in the city.

The week was a blur with work. I met with clients and friends for dinner and drinks. I didn't have much time to think about the meeting until the weekend. Saturday evening I logged into the chat, but her account didn't log in. I was disappointed and anxious. I logged out and went to bed. I had intense dreams of myself in red lingerie held captive by a lady dressed as cat woman. My limbs were tied with red satin ribbons tied into intricate knots.

Finally it was Sunday morning. I woke up very aroused. I was so tempted just to masturbate, but I resisted and took a shower. I wore my black satin panties with matching camisole and black opaque tights. I selected a sky blue man shirt, blue jeans and black training shoes. I drank my coffee and set out. Today I was 'John' and I would be meeting 'Emma'. I put on my hat and sunglasses. I collected the rose that I had purchased the day before and left the apartment. I arrived at the coffee shop with time to spare. I scanned the area looking for possible matches. I saw lots of people with hats and sunglasses, but no rose. My heart rate was higher than normal with the excitement. What was I doing?

I purchased coffee and found a table to wait. I scanned the small crowd while checking my phone. I realised we had no way to contact each other. The planned meeting time passed and I prepared to leave when I saw a lady with a rose at a table outside. I approached her.

"Emma?" I queried.

She looked up and noted the rose I was holding.

"John?" she asked with a smile.

"Yes, sorry I thought I had missed you," I replied handing her the rose.

"Me too. I was about to give up. Are you okay for a walk?"

I noted an accent, maybe French, but I wasn't an expert of regional European accents so couldn't be certain.

"Yes, I would like that," I agreed.

She reached out and held my hand and we strolled to a quiet spot. To everyone else we were just a couple having a walk and holding hands. She guided me to a bench and we sat close to each other.

"I guess you want to know more about my proposal?"

"Yes, I'm very interested."

"I thought it best to do this in person so you know I'm real, and I can see you're real. If this was a no show then we would know it wouldn't go further. Our meeting demonstrates our commitment. I also admit it's exciting to meet like this."

"I understand and agree. I am also excited right now."

She outlined her plan. I had been impressed with her intelligence, wit and humour before based upon our many chats, but I was blown away by the detailed plan she had.

"What do you think?" she asked finally.

"I want to do this, but I need time to absorb the plan through. Let me do this in steps and see how we go. At any time either party can call abort," I suggested.

"That's sensible," she agreed.

"So first step is for me to buy a pay as you go phone," I said reviewing the plan in my head.

"Yes, here's the number for mine. Text when you are active. I hope to hear from you soon," she said handing me a printed number.

"It was good to meet you Emma. I hope to see you soon."

She hugged me and then kissed my cheek.

"From now you only refer to me as Mistress naughty Chloe," she whispered in my ear.

I was very aroused. She left me to contemplate the plan. I visited an ATM and withdrew cash. I found a phone store and purchased the cheapest model that had a camera. I returned home and charged it. Later I visited a supermarket nearby and paid for a top-up and completed the setup in the car park. I ensured that the location information was disabled. I added my contact as M and stored the number she had given me. I sent my first message via a messaging application.

>Hello Mistress. My phone is ready. Chloe.

I held it hoping for an immediate response, but nothing. I walked home. I changed into lingerie, a dress and heels. I heard the ping of a message several hours later. I immediately checked my normal phone and found nothing. I remembered the new phone and opened it with trembling hands.

>>Hello Chloe. I hope you are being a good girl. Time for phase 3- cage and plug.

This was really happening. I guess she considered the meeting as phase 1 and the purchase of the phone as phase 2. I retrieved my cage and plug. I took a photo. I locked my cock into my cage and inserted the plug. I took a picture of the cage. I prepared a message.

>Hello Mistress phase 3 completed.

I attached the photographs and hit send. I amended the settings and changed the alert tone so it was different.

>>Good girl. I will send more instructions tomorrow. Sweet dreams.

I had committed to wearing my cage and plug until we met, except for cleaning and I was being trusted not to play with myself.

I had a busy Monday and the day passed quickly. I had worked from home so I had worn a blouse and skirt. It felt strange with the cage. I had become used to tucking. I purchased the special contact lenses she had requested that I would wear and they would arrive by post within 24 hours. The phone pinged.

>>Hello Chloe. Are you dressed nicely?

I took a selfie from the neck down. I wore a red long sleeved satin blouse, black pencil skirt, black sheer stockings and court shoe heels.

>Hello Mistress. I think so. I hope you like this.

I attached the photo and hit send.

>>Good girl. I hope you are enjoying this as much as I am.

>Yes Mistress.

The calls continued in a similar manner each evening until Thursday.

>>Hello Chloe. Are you free this Saturday?

>Yes Mistress.

>>I will book a hotel room. I will send you details once arranged. I want you nice and smooth.

>I am always smooth Mistress.

Later that evening I received the address of the hotel and instructions. I was expected to arrive by one in the afternoon. I would have an hour to prepare myself.

The following morning I showered, completed an enema and applied a little makeup to enhance Chloe. I dressed in lingerie, tights, blouse and trousers. I wore flat boots. I prepared a small overnight bag. I set off hoping I could keep my nerve. I had planned my route and knew where the hotel was. I checked in as Miss Angel as instructed. A new message arrived.

>Chloe I expect you feminised and dressed for when I arrive. Secure your personal items in the safe. Once ready put in your contact lenses and send me a picture.

I found the safe: most hotel rooms have one for passports, money, items of jewellery, etc. I placed my purse with my id, house keys, and my mobile phone into the lock box. I retained Chloe's mobile to complete the instructions. I visited the bathroom and completed my makeup. I changed my underwear for black satin bra, waist clincher and panties, then fastened my black sheer stockings to the suspenders and then wiggled into the black dress. Finally I stepped into my peep toe high heels and secured the straps. I looked at my reflection and was satisfied. I placed my other set of clothes into the overnight bag and placed it in the wardrobe.

"Do you want to go through with this?" I asked the girl in the mirror.

"Yes, we do," she replied.

I sat on the bed with the phone and the contact lenses. This was the point of no return. I unlocked the phone, removed the first lens from the bubble pack. It was completely black and would effectively remove my sight. I have worn contacts before I had my laser surgery, but never like this. it was scary and exciting. I slipped it onto my left eye. I knew what to expect, but was still surprised by the loss of my sight. I realised I couldn't operate the phone if I had both lenses in. I took a photo and sent it to Mistress.

>I am ready for you Mistress.

I attached the photo and hit send. I placed the phone on the bedside table and then opened the second bubble pack. I gently placed the second lens in place. I could no longer see. I am certain my heartrate doubled and my cock was tight in my cage. I waited for Mistress. My mind wandered and I don't know how much time had passed.

I heard the door. What if it was a cleaner or hotel management? My heart raced, adrenaline and endorphins flooded my body. I heard heels approaching.

"Hello Chloe," greeted the familiar accented voice.

"Hello Mistress," I replied relieved it was her.

"Don't you look pretty?"

"Mistress, I wanted to look nice for you."

I felt her hand on my cheek. She caressed me gently.

"Please stand!"

I obeyed. She held me and kissed me gently on the lips. I returned the kiss. We held each other enjoying the gentle exploration of bodies with hands and mouths. She finally pulled away and walked behind me. I tracked her through hearing alone. I felt her arms around my waist and she kissed my neck behind my ear. I love having my neck kissed. She unzipped my dress and let it fall to the floor. I was now in just my lingerie and heels. I felt her warm body pressed against mine.

"Do you think you can undress me?" she asked gently.

"I will try if you want me to."

"I want you to undress me."

I found her waist and unzipped her skirt. I lowered it and stroked her legs. She was wearing sheer silky hold ups and heeled court shoes. I imagined black, but I had no idea. I caressed her legs on the way back up. I traced her thighs and then her hips. I found the blouse and unbuttoned it. I slipped it from her shoulders.

"Hmm, good girl Chloe! Now the bra and then the panties."

She kissed me again as I fumbled with the bra clasp. It was only two hook and eye fastenings, but it felt far more complex. I succeeded and slid the straps along her arms. I found a bracelet on one wrist and a watch on the other. No rings. Her hands were warm and soft with short oval nails. I was astounded by how much information I could detect in the absence of my sight. I reached for her body and found her breasts. I caressed her and then moved my hands to her waist. I could hear and feel her breathing. A hand touched the front of my panties finding my cage. I gasped with surprise.

"It's okay Chloe, I will look after you."

I made a decision and knelt. I slipped my fingers into her waistband of her panties. I slowly liberated them. I kissed her tummy and found her belly button. I was surprised to find a piercing and so I was very gentle. She made several happy sounds as I traced my fingers over her bum. I guided her underwear to her ankles while kissing her thighs. Her pussy was smooth. I imagined her standing in front of me with long golden hair wearing only her holdups and heels. I pictured green eyes and pink lips with minimal makeup.

"You have gentle hands," she observed.

"You have a beautiful body that deserves to be appreciated Mistress."

"Come with me," she instructed.

She took my hand and guided me to the bed. I felt it against my legs.

"Please sit."

I turned, lowered myself and sat on the bed. I heard noises, but couldn't comprehend what was happening.

"Have you been a good girl Chloe?"

"Yes Mistress," I replied to the sound of the voice.

She took my hand and kissed my fingers. She was very close and I could smell her perfume. I wondered what it was.

"Climb onto the bed."

I positioned myself so my head was on a pillow, but somewhere close to the centre of the bed and my legs close together.

"No need to hide my pretty Chloe."

She crawled from the bottom of the bed spreading my legs as she moved upwards. I felt her body weight press on my chest. I gasped in surprise.

"It's okay my pretty girl, I'm going to love you. I have a special girl cock. I think you will like it."

I felt something against my leg, but couldn't identify it. I felt her tug on my plug and then it was removed leaving me feeling empty. I had been plugged for the last five days 99 percent of the time. She kissed me again. I felt something cool and wet against my hole.

"How many people have loved your boi pussy Chloe?"

"No-one Mistress, but I've plugged for a while and I've used a toy."

"I want to love you. Do you consent?"

"Yes Mistress."

She positioned herself between my legs. I felt a phallus against my hole and so the moment I had dreamed of for so long had finally arrived. I moved my hands to her hips expecting to find a harness, but found nothing. I was confused and it must have shown on my face.

"It's a special cock for my special Chloe," she whispered.

She was gentle and took her time stretching me. I gasped as she finally squeezed through my barrier. My body submitted to the remainder of her cock. She slowly pulled back before penetrating me again. I surrendered to her as she loved me. She liked to kiss me and was very much in control. Her body felt athletic, her skin was warm and soft and it wasn't long before I was begging to climax. Weirdly my cock was no longer hard and demanding attention, instead it was replaced by something much deeper.

I had no idea of time. My rectal muscles were focused on squeezing her cock. Mistress moaned several times before she called out as she reached her orgasm, something warm and wet squirted inside me. The pulse triggered me and I cried out in surprise and then immediately climaxed. I was surprised by my reaction, but also overjoyed at the feelings, the sensations, and my body responses to her.

"I am really liking spending time with you Chloe. Did you like it?" she asked.

"Yes Mistress. I have never orgasmed like that before. It was amazing."

"Would you like to play some more?"

"Yes, you want to go again?"

"You want to take this a little further?" she asked.

"What do you mean?"

"Submit a little more? I would like to put you into cuffs and a collar. Would you like that?"

"That does excite me, but I'm also a little scared."

"I promise I won't hurt you, humiliate or expose you. I know it's a lot to ask for after such a short time. Do you think you could trust me?"

"Okay. I would like to, but please no locks. That would be too much."

"Okay I promise no locks. I have some cuffs."

She wrapped a leather cuff around my wrist and then she buckled it. She repeated with the other wrist. She ran her nails down my legs which made me gasp in ecstasy. Another cuff was secured at my left ankle followed by the right. She kissed me again.

"I don't want my pretty Chloe running away. Will you submit to me?" she asked in a whisper to my left ear.

I swallowed. My adrenaline was coursing through my veins and I could hear my heart beat in my ears.

"I submit," I said simply.

"Good girl."

Those two words have a profound effect on me. A leather collar was placed around my neck and she began to buckle it in place. I reached out and my hands found her thighs sheathed in her soft nylons. She moaned as I caressed her legs. I found a phallus erect at her groin, but couldn't determine how it was attached.

"I hold it inside me," she explained perhaps in response to my confused expression.

She stroked my face and kissed me again.

"I didn't give you permission to touch me did I?" she admonished me.

"Sorry Mistress."

I felt her teeth nibble on my earlobe.

"Why don't you get comfortable on the bed."

I wriggled so I lay in the middle of the bed. A pillow was positioned at my lower back to raise my bottom. My legs were positioned leaving me exposed and vulnerable with my bum and caged cock on display. I felt her body as she climbed on top.

She slowly and gently penetrated me for a second time. She was as gentle the second time as the first, but with the thrill of feeling tight cuffs on my limbs. We were both vocal and the second time was better than the first as we discovered each other's pleasure points. She held the rings on the wrist cuffs effectively holding me down. I loved the feeling of helplessness. I heard her cry out and I felt a surge of wetness deep inside me. I felt my insides spasm and I climaxed a moment later.

She withdrew her cock and slid down my body. I was left to recover my breath. She unbuckled and removed the cuffs and collar. We lay together side by side gently caressing each other with our hands. Our stockings whispered together conspiring against me.