Surrendering to Darkness Ch. 03

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Darkest fantasies explored and a happy ending?
11.5k words
4.83
3.3k
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Part 3 of the 3 part series

Updated 06/11/2023
Created 04/06/2022
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Submission. Domination. Crossdressing. Feminisation. Bdsm. Lingerie. Latex. Pegging. Oral. Anal. Sensory deprivation.

Several months passed. I regularly spent the weekend with Katrina at her 'little place in the country'. It wasn't every weekend, but it allowed Chloe 'out'. The legal people had written us an agreement protecting us both. We had both promised with pinky oaths we would keep each other's secret, but the agreement gave us an assurance just in case. It was something that we didn't need to 'worry about'. It allowed us to explore our kinks. We had lots of play times involving bondage with Katrina dominating me, but for the last few visits I had just been Chloe. I wore skirts, dresses, satin lingerie, hosiery and heels. We had talked a lot about our life journeys. Katrina liked that I was feminised. I was comfortable as Chloe.

We were sat resting in the lounge on a cold wet Sunday morning. I was dressed in a wine wiggle dress with matching lingerie, pale sheer silky stockings and black patent heels. Katrina was wearing navy trousers and a cream satin blouse. We were sat side by side drinking tea. We were still tired having too little sleep after a long night of sex.

I think we had covered most of the things we liked in our session. It had started with Katrina sucking my cock, something she said she wasn't fond of, but she was very enthusiastic and it was over quite quickly. Her lovely lips and tongue teased and tantalised my cock and balls. I returned the favour laying her on the bed kneeling between her legs. She rested her legs on my shoulders while I nibbled, licked and sucked her. She held my head gently, stroking my hair, making little sexy noises as I slowly pleased her. I took her to the edge twice, I had hoped for three, but the combination of my eagerness and her passion she couldn't hold on. I licked her post orgasm until she begged me to stop.

After a period of cuddles and kisses she retrieved her cock. Oh, how I have come to love her cock. She made me watch as she slipped it in place. She sighed and smiled once it was how she wanted it. The best thing was we could both achieve multiple orgasms. We completed our love fest with Katrina on top. My cock enveloped and massaged by her beautiful pussy. She 'tortured' me, knowing just when to squeeze and delay my climax. I caressed her amazing body.

When I was close for the fourth time, I knew I would have to focus on her nipples, I knew she was planning on edging me again, we both knew when I was close, she smiled and I knew she wanted to suspend my climax. I pinched her nipples and turned them between my finger and thumb. Any thoughts of control fled and I came very hard, seconds later so did Katrina. She collapsed on top of me.

"Naughty Chloe," she breathed in my ear.

"Bad Katrina," I responded kissing her and running my hands through her lovely hair.

*

The next morning my little bum hole was sensitive after the night of passion, but I was so happy.

"Chloe, do you think you'll ever step into the real world?" she asked.

"I don't think I can. My family wouldn't understand. My work place definitely wouldn't: they are super old fashioned. They talk a lot about diversity and inclusion, but I don't see much of it in practise. You should have seen their faces when I appeared on a video call with my longer hair. Can you imagine what they would say about my painted nails, makeup, and earrings? If I wore a skirt to the office they would need a row of ambulances to deal with the heart attacks."

I shook my head sadly.

"Would you consider a step into the real world, at a place where no-one would know you?"

"What do you mean?"

"A dinner date in a restaurant far from the office and home," she suggested.

"That does sound exciting, but also super scary."

"It was just a thought. It's an opportunity to expand your horizons as Chloe. You know I would never make you do anything you're not comfortable with."

"I'll think about it. Do you ever step into the real world as your alter ego?"

"Yes, I visit a few clubs now and then, but it's easier for me. I can wear a mask. I can fit in and it preserves my identity."

I nodded.

"What's your darkest fantasy?" she asked.

"I'm not sure I can tell you that, even though we have known each other for a while. You'll think me strange. Do you have a dark fantasy?"

"Yes. We've shared a lot. I mean you know more about the real me than anyone. I've never shared my dark thoughts with anyone."

"I understand. For me it's like my user name: the angel part is me exploring my feminine side. The love of lingerie, hosiery, satin, heels and trying to be the best 'girl' I can be, the dark part... It's that part of me that likes to submit and be restrained. That part of me is like my naughty shadow. It's always with me."

She squeezed my hand. She kissed it. We spent the day together. I changed back into my male clothes and I was driven home by Phil.

*

Another week passed. It was Friday night. We had eaten Chinese food. We were sat cuddling in the lounge.

"Katrina?"

"Chloe," she responded with her beautiful accent and a smile.

"About that dinner at a restaurant?"

"Sorry, remind me? Which dinner? What restaurant? When?"

"You asked me a few weeks ago about going in the real world, about going out as Chloe."

"Yes, I remember the conversation. What about it?" she asked.

"Would you like to go out to a restaurant with me?"

She stood and knelt in front of me holding my hands.

"I would really like that, but only if you want to. Have you been thinking about that all this time?"

"On and off, and yes I want to do this" I admitted.

"Where would you like to go?"

"I hadn't thought that far ahead. I came to a decision in the week. I wanted to tell you. Is there somewhere you know that we could go?"

"There is a little village pub a couple of miles away that has really good food. When would you like to go?"

"This weekend is probably a bit late notice, so next time?"

"Let me see what I can do. Shall I ask Phil to drive us, or would a taxi be better for you?"

"Well Phil knows I'm Chloe, but he's never seen me like that."

"I've known Phil for a long time. I really trust him. He has been a good friend too. He has driven me around when I have dressed in my latex. He has his own non-disclosure agreement."

"Okay. I trust you and I trust Phil."

She kissed me. She went to make arrangements.

"Dinner at seven tomorrow?" she asked while on her mobile.

"Oh, yes please."

The booking was confirmed.

"All done, but you don't look happy. Have I talked you into something you don't want to do?"

"No, it's just..."

"I've gone too quickly. You haven't had time to process it? I can cancel. I'll arrange for another time?"

"No, I really want to. I just didn't bring anything special to wear."

"You look amazing as you are, but if you want to dress up there is the blue satin dress still in your wardrobe. You still haven't taken it home."

"Will it be too fancy for the pub?"

"I don't think so. I will wear the red one if you want me to."

"Okay I will wear the blue dress. What would you like to wear?"

"I'll wear the red dress."

"Katrina, that didn't answer my question. What would you like to wear?"

"My latex cat-suit?" she tested with a laugh.

She shook her head and thought for a moment.

"No, I'll keep that for later. I'd like to wear a navy trouser suit. Would that be okay?"

"Yes, of course. You need to be comfortable too. I appreciate the offer of you wearing the dress."

We retired to my room. We started slowly, just kissing, holding hands, but it didn't take long for Katrina to take the lead. Layers of clothing were discarded. I wore a black satin corset, thong panties and sheer stockings. My heels were still buckled to my feet. Katrina was in dark red panties and matching bra with nude holdups.

"May I love you?" she asked.

I nodded and smiled. I watched as she prepared her cock. Katrina knew how to push my buttons. We spent a lot of time kissing and cuddling, before she finally penetrated me. I love to feel her body against me and her cock deep inside. She is gentle, but very dominant. She loved me for what felt like ages before we both climaxed loudly. We cuddled for a long time after before discarding the remainder of our clothes. Our smooth warm bodies pressed together. We fell asleep together as a tangle of arms and legs.

*

Mid-afternoon we took a walk through the gardens enjoying the warmth of the sunshine. I felt the breeze circling my ankles and lower legs like a friendly cat. My heels sounded loud on the paving stones. I was happy here; I wished I could stay here. It was the normal things we did together while being Chloe that I also enjoyed so much as well as the kinky things.

"Phil will be here at 6:40. It's a twenty minute drive," explained Katrina reaching for my hand.

"I'm really looking forward to this."

"Me too, thank you for trusting me.

*

It was 5pm: I heard the chimes from the clock in the hall.

"I'm going to get dressed for dinner," I reported kissing Katrina.

"Are you really that high maintenance," she teased.

"It takes a lot of work to look this okay."

"I don't believe you, but go, do what you need to do," she said patting my bottom.

I ascended to 'my' room. I sat on the bed. I removed my heels. I wanted to look my best. I had been out a few times solo, but this was different. I removed my jewellery, cleaned my makeup then undressed. I washed my face and brushed my hair. I opted for a pony tail while I prepared. I laid out the lingerie, the dress, with the shoes. Talking to many people on-line that cross dress: the preparation, the anticipation is at least half of the buzz. Dressing for me is a thrill in itself- silky soft clothing gliding over smooth skin. I painted my toes and finger nails a dark glossy blue that matched the dress. I glued my breast forms in place. I blended special make up to hide the edges. Bra, suspender belt, sheer black silky stockings then my panties. I tucked. It is a huge turn on for me to be tucked, I don't get hard, but I have an intense warm tingly feeling. I looked in the wardrobe mirror. From the neck down I looked like Chloe. I visited the bathroom. I applied my makeup. I smiled as Chloe looked back at me.

I slipped into the beautiful satin dress, shivering as the layers of soft, cool satin enveloped my body. I signed with pleasure at the sensations. I really loved this dress: adding my earrings, a bracelet and my necklace. I checked my ladies watch- it was already after six, so much time had passed. I spritzed my favourite perfume to my neck and wrists. Lifting my dress, I spritzed my thighs. I smiled, it felt naughty doing that, but I hoped Katrina would appreciate it when we returned. Guiding my feet into the black patent four inch peep toe shoes securing the ankle strap- it's another crazy quirk I'm sure, but I don't feel complete without my heels.

I released my hair from the pony tail, brushing it allowing it to glide over my shoulders. I took a final look in the mirror. I was ready. Descended the stairs as I had many times now, but wearing this dress it felt different somehow. I checked the lounge, but no Katrina, moving to the dining room then the kitchen, but she wasn't there. She must still be dressing I concluded, so I returned to the lounge to look out of the impressive windows.

I heard footsteps; I turned to find Katrina in a pale blue satin blouse, navy trousers and jacket with high heeled ankle boots. Her long hair was tied up in a bun.

"Hello beautiful," she greeted.

"Does this look okay?" I asked.

"You're kidding me, right?" she asked kissing my hand.

She shook her head. She held me close.

"You look amazing. Honest! Shall we have a little dance while we wait," she suggested.

We danced for a few minutes including a few twirls for good measure. We laughed.

The pub was far off the beaten track, the few locals from the village were in the bar, leaving the restaurant to just Katrina and I. We had a lovely meal, drank wine, we enjoyed each other's conversation. Phil is a gentleman: he complimented me which triggered another one of my terrible blush moments. The evening was lovely. I enjoyed the experience.

We were back at the house, alone once more: I was on a high- no drugs required. Katrina embraced me from behind and kissed my neck. I don't know why, but when I'm feminised I just love being held and kissed this way.

"I like that perfume, it always reminds me of you," she whispered in my ear.

"It's Coco Mademoiselle. Someone walked past me in the office one day. I asked her what it was. I then bought a bottle for myself. It's my favourite."

She kissed me hard, leading me to the bedroom. I expected it would be another night without much sleep. We were soon down to our lingerie. Katrina played with me. We made love, first Katrina penetrating me and then me inside Katrina, but both times she was on top. I love the gentle rocking back and forth pleasing each other. Katrina tried a butt plug and inserted her cock so she was double penetrated. She climaxed loudly. She held her cock deep inside me as I rode my own wave of joy. It was another night I would remember with great fondness.

*

I had another week of drab torment, but looked forward to a weekend of adventure. It was Saturday afternoon. Katrina and I had been for a drive in the country. I had ventured out again as Chloe in an apricot dress with nude high heels and matching lingerie- of course. Katrina had driven me around in her little red sports car. It felt good to be in the real world. We returned to the house happy. We made tea and nibbled on afternoon cake. I had baked gingerbread. Katrina teased me that I was a lovely little housewife.

I noticed that she had a thoughtful expression: it was serious, but also anxious.

"What's wrong?" I asked.

"You asked me about my dark fantasy?"

"We talked about it briefly. Did I say something to upset you?"

"No, gentle Chloe: the exact opposite! You have trusted me to take you out of your comfort zone twice now. Thank you for your trust. I'm torn. I want to tell you, but I don't want to scare you."

"Please tell me. The worst that can happen is I say it's not my thing."

"But you'll look at me differently. I would be a monster."

I held her close, hugging her.

"Katrina you'll never be a monster," I assured her.

"What if I said... I want to lead you around blindfolded and have sex outside?"

"I would say that sounds exciting. I would prefer to wear the blackout lenses rather than a hood. Do I need to change clothes?"

"What if... I wanted to restrain you?"

"You have restrained me lots of times, as long as you didn't leave me I think I would like that- I trust you."

"Really?"

"If it's in a safe place: where no-one will see us. In a place that doesn't involve breaking into private land or anything, I'm up for it. I don't want police helicopters searching for us or security guards chasing us. I can't run in heels," I said with a laugh.

"Will you..."

There was a pause.

"There's more?" I prompted taking her hand and kissing it.

"Would you be Alice for me?"

"If calling me Alice does it for you, then I'll be Alice not Chloe for a while."

She shook her head.

"I have a thing for the Alice in Wonderland dress," she revealed.

"You want me to dress as Alice?"

"Yes, I knew I would creep you out."

"Katrina, keeper of my secrets, I love the Alice dress too. I've thought about buying one for a while, but I could never justify the cost for a whim."

"You're not just saying that?"

"Honest!" I said putting her hand on my heart and covering it with my own.

"Do you need time to think about this?" she asked.

"No, you want to do it now?" I asked excitedly.

"Oh, yes. If I bring you the outfit, can I leave you to dress?"

"Yes, shall I wait for you in the bedroom or the lounge?"

"I'll come to you. I'll find you in the bedroom," she said kissing me hard.

We were both excited. We rushed up the stairs. We stopped at the top. We kissed again.

"I'll be with you in a few minutes," she promised.

I watched as she skipped towards her room. I walked back to my room. I'm not sure when it became 'my' room. From the first time when I stayed over, I dressed in my room and we slept together in my room. I slipped off my heels. I set them to one side. I removed my watch and jewellery placing them on the dressing table for safe keeping. I would hate to lose them in the deep dark woods.

I think five minutes had ticked by when Katrina appeared in the doorway. She laid a garment bag on the bed, a holdall and a shoe box.

"You have a lot of these garment bags you know?" I observed.

"Yes, I bought a job lot on-line. I thought I ordered three items, but received three boxes. They have come in handy mind you. I have a lot of my clothes in these bags."

The garment bag was unzipped to reveal the Alice dress in pale blue and white satin.

"Wait, that's not any high street dress," I said.

"No, I had it made for another party I went to. The lucky thing is as we have proven many times is we are nearly the same size and can share clothes. I think my hips are a bit bigger, and maybe your shoulders are slightly wider."

She opened the shoe box to reveal black patent Mary Jane high heels. The holdall revealed white satin lingerie: bra, panties, suspender belt with white lace topped stockings and a satin petticoat.

"Right, I'll leave you to get ready. Back soon."

I removed my cobalt blue dress I had been wearing, my lingerie and stockings replacing them with the set provided. I glided into the luxurious Alice dress. It was a lovely fit, a little loose around the hips, but I was in heaven. I discovered it had a series of petticoats that made the skirts whistle if I twisted back and forth at the waist. The apron was made from the same high quality satin. It felt so soft when I rested my hands in my lap. I was now concerned that the dress would be damaged if I was laid on the rough grounds. I slipped my feet into the shoes and buckled them. I inserted my blackout lenses. I then knelt down on the floor arranging my dress around me. I waited for Katrina to return.

"Well don't you look special?" she said from the doorway.

I think, I blushed a little, but I was getting better with compliments. She took my hand, I found latex covered fingers- she helped me to my feet and led me from the room. We descended the stairs, went outside, and walked the patio. I was led slowly. I felt the wind against my legs. I don't know what route I took, or where I went. It was exciting and had total trust in Katrina. I was helped into the car and driven for about ten minutes. I was helped from the car at the destination. I think I walked on concrete, gravel, grass, wooden flooring, more concrete and then more grass. Katrina 'forced' me to my knees. It felt like grass with something silky on top, like a satin sheet. Katrina lifted my chin and kissed me. She left me kneeling for a few minutes- I think she was watching me. I heard wind in the trees, bird song and may be even a woodpecker tapping out on a nearby tree. With my sight gone I was more aware of sound. I was very aroused deep inside. I know she was close by, but the feeling of being abandoned without sight in an undisclosed location was very exciting.

I felt a wide leather collar encircle my throat. It was buckled in place and I heard the resolute click of a lock. I was directed by touch alone. Leather cuffs were secured to my wrists, upper arms, wrists and thighs. I was helped to lay face down.

My legs cuffs were roped and then pulled apart. My wrists were then tied until I was spread eagled on the ground. The ropes were tied slightly higher than my body position given me the impression I looked like a sky diver. More ropes were secured to the upper arm cuffs and thighs. I wriggled and found little movement. I loved it. The ropes supported me, making staying in the one position easy. Hands stroked my hair and gently pulled it lifting my head. A ball gag was pushed into my mouth and buckled. This felt amazing. I lay there and happily surrendered to my captivity. Hands caressed my legs and I felt my dress being lifted. Warm latex covered fingers tickled my exposed bum cheeks. Oh sweet torture. I think Katrina kissed my bum cheeks. She lay on top of me for a while. I think she was wearing her full latex body suit. I felt her cock slowly glide into me. I relaxed, allowing my body to swallow her lovely shaft.