Down The Rabbit Hole Pt. 04

My heart was pounding as I stepped out of the hotel and walked hand in hand with Sophie back towards Camden Town. The early evening was still warm, and Camden was vibrant. People were out and about, partying, drinking, eating, and getting ready for a long night ahead of them. I gripped Sophie's hand harder as we approached a group of young women dressed in fancy dress outfits, one of them wearing a wife-to-be sash. They were loud and enjoying themselves, and I was afraid they would point me out and laugh, but they said nothing as they passed. One of them even winked at me.

Once we had approached the busier part of Camden by the underground station, I realised that it was unlikely that anyone would say anything about my outfit choice. Everyone here seemed a little different; it seemed such a welcoming place for those who were different.

After a little walk, we found a bar close to Camden Lock. Music filled the air, and the place was heaving with people enjoying a drink or a few this warm evening. I felt a little nervous with so many people around, especially since they had been drinking, but once again, Sophie was my rock. She started chatting to a group of students who studied in Central London. I was quiet at first, but when I contributed more to the conversation, none of them seemed to judge me. Some of the students even admitted that they thought I was a girl. As I grew more comfortable, I felt like a different person, and I acted a little shy and then much more playful and flirty than usual.

We stuck with that same group of people most of the evening as we left the bar to go to a live music venue. It felt great to let myself loose and dance with Sophie and some of the people we had met this evening.

We stumbled back to the hotel at close to four in the morning. This evening had been the least tense I had ever felt on a night out, and it was probably the best night out I'd experienced. A part of me regretted that Steve wasn't here with me; I wasn't sure how he'd react to me like this. I was still finding myself and wasn't quite ready to reveal it to him yet. When we finally returned to our room, I collapsed onto the bed next to Sophie, and we drifted off in each other's arms.

I woke before Sophie did late in the morning, and I couldn't help but stare at her as she slept. She looked peaceful as she slept. I gently stroked her hair as I thought about what she had done for me in a small amount of time.

I stood in front of the tall mirror, admiring my appearance. The make-up had started to run a little, but my hair was still how Sophie had styled it, and I was still wearing the outfit from the night before. It still felt like this was the real me, the version of myself I had been suppressing and too nervous to let out.

I woke Sophie up a little later with a coffee as I thanked her for yesterday evening.

"Thanks to you, I've never felt more comfortable with who I am than I do right now. Sure, there's a way to go, but I wouldn't have got this far without you."

Sophie's face softened as she kissed me tenderly. She looked deep into my eyes and smiled.

"You are a beautiful person, inside and out, Alex. I'm so happy we met on that double date for Steve and Lily. Thanks to you, I'm discovering more about myself and what I enjoy in a healthy environment."

"I want to do something for you, Sophie; what can I do for you?"

Sophie thought briefly before admitting that she liked her feet being touched. She'd discovered it during a massage session, but none of her previous partners had offered to do it to her, and she wasn't going to be the one to bring it up.

"I can do that."

I sat beside Sophie's feet and squeezed a little of her moisturiser into the palm of my hand. Rubbing my hands together before I gently massaged her feet. I heard a sound of contentedness coming from Sophie which spurred me on. Her feet were beautiful; I couldn't help but appreciate them. Getting a little carried away, I rested her foot on my hands and kissed the soles of her feet.

"Oh, keep doing that."

"Yes, Sophie."

I breathed her scent in deeply before gently kissing her soles some more. I started to appreciate how soft her feet felt, the arches and even the long toes. Going one step further, I took one of her toes in my mouth and started sucking it.

"Good girl! I like that. Keep doing that, Alex."

Spurred on by Sophie's praise, I continued attending to her feet with my mouth and hands. It was one thing to discover that I found her feet attractive, but I liked that I was making her feel good and that I was pleasing her in some way more.

"That's a good little foot bitch."

I mumbled a response with my toe in her mouth, instantly reacting to what Sophie said. My cocklet twitched when she called me a bitch, and I regressed more into my submission. This wasn't the first time she had said something humiliating whilst she was feeling turned on, and I had to admit, I liked it.

"You enjoyed that, didn't you slut?"

"Yes, Sophie."

I watched as Sophie got off the bed and stripped down from her outfit from yesterday evening. She motioned for me to kneel by her side as she stroked my hair and had me rub my face on her leg. It felt like home on my knees beside her.

"Stroke your cocklet against my feet, sweety."

Sophie sat at the edge of the bed and held her foot out for me. Lost in the moment, I did as she said without question, holding on to her leg and rubbing my cocklet over her feet. I was already hard long before I started rubbing against her; it didn't take long before I ejaculated over her foot. I'd been unable to control myself and stop.

"Remember, good sluts always clean up."

"Yes, Sophie."

I bent down and started licking my cum off of Sophie's feet, eagerly lapping up every last drop.

Sophie motioned for me to climb onto the bed next to her, and we snuggled up and made out. This had been such a perfect start to the weekend. I had no plans in place, and neither did Sophie, so we decided to go and do some more shopping.

After Sophie had refreshed my make-up, she had me get dressed in one of the vintage dresses she bought me yesterday.

"Oh, those trainers do not go with those shoes."

Sophie nodded her head disapprovingly and led me to one of the shops selling shoes. I'd never been one for appreciating shoes until now, but after this morning's episode with feet: I was suddenly interested. Sophie picked a few pairs of shoes for me to try. A set of boots which would fit in with one of the emo outfits Sophie had bought and some high-heeled shoes.

Walking down the high street, Sophie noticed a DJ was playing electronic dance music this evening at one of the live music venues. She asked if I fancied it, and when I agreed, she ordered us both a ticket.

"We have to get ready for it."

Sophie was suddenly excited and started wandering off to the next shop. There were another ten hours before the gig, so I wasn't sure why we had to get ready now.

"Ooh, this place looks good."

Sophie led us into a hair salon that also offered beauty treatments. She said today wasn't just about the gig this evening but the whole day leading up to it.

The first treatment Sophie booked us for was a manicure and a pedicure. I'd never experienced anything like this before, and I relaxed whilst an employee of the salon started on my feet. She trimmed and buffed my nails and then exfoliated and moisturised my feet. The experience was far less embarrassing than I presumed, and I found the pampering experience very relaxing.

After the foot treatments, Sophie and I enjoyed a lovely couple's massage and then following that, a facial treatment. I'd never thought about having anything like this before, but after experiencing it, I was tempted to make it a regular occurrence. I felt so fresh and invigorated.

To finish our time here, Sophie invited me to join her in having her eyebrows and hair done. I was nervous since I returned to college within a few days, but I was still riding the high of a great time with Sophie. She hadn't guided me wrong yet, so I agreed to sit next to her and have mine done as well.

"What do you think I should go for?"

"Let's go for a raver or festival-inspired look."

Sophie whispered something to the young lady who had come over to my chair to do my hair, and she agreed that it would look great. I watched her work on my long hair, rinsing it first and then adding a temporary dye. My hair turned to a platinum blonde, and she used foil to cover parts of my hair as she created pink and lilac streaks.

As the dye set, the worker had me keep still as she used tweezers and wax to shape and trim my eyebrows. Sophie then suggested we should get our nails done. I was going to have nail varnish on them since it would be easy to remove before college, but then as I watched Sophie have her acrylic put on and painted, I decided to hell with it. I had been holding back this side of myself for too long it was about time I let myself be who I was.

The result of today's work left me admiring my reflection immensely. My face looked fresh and smooth, and that was before Sophie added some more makeup later this evening. My hair, temporarily a platinum blonde with pastel pink and lilac streaks, looked far different, but in a good way. The young lady who had worked on it had also used a grooming tool to straighten and add waves to my locks, making them look much more feminine.

I was buzzing as Sophie and I went for lunch, and my mood was infectious since she seemed to be as well. It was bizarre getting used to my nails which were now longer thanks to the acrylics. I was worried about breaking them so soon, so I ate my burger carefully.

The last stop before returning to the hotel was another trip to Cyberdog. I chose another couple of outfits, including one for this evening: A tight-fitting, pink floral dress. The dress hugged my body all over and had two thin straps that went over my shoulders. I'd have to be careful about it rolling up as it barely covered half of my thighs.

Before leaving Cyberdog, we had a look around the adult-only section downstairs. Feeling less nervous this time, I had a better look at what was on offer. There was a fake pair of breasts which would fit under my dress which I picked up immediately. I loved how I looked when Sophie put the tissue under my top yesterday, so I was dying to see how this looked.

"What's this?"

I turned to Sophie, showing her a pink, plastic item, and she smiled wickedly.

"That is a chastity cage. That ring part fits around the base of your balls, and the other part contains your cocklet. That is then locked in place with a small padlock."

"Oh. So I wouldn't be able to touch myself?"

"Nope."

I paused, deep in thought. Something about the idea of being unable to touch excited me.

"I dare you to wear it for me."

Sophie was teasing me, but I wondered if she could read my thoughts so clearly on my face.

"You're on. For how long?"

"Until the end of next Friday. I wonder how long it will take for you to beg me to take it off."

"As if! What do I get if I last the week?"

"I'll be your naked maid for next weekend. That's if your parents are still away."

"Deal!"

If I thought it was embarrassing buying the outfits yesterday, this was far worse. The cashier barely contained a smirk as she scanned through the pink chastity cage. It got worse when Sophie approached carrying a pink-jewelled, steel butt plug kit with lubricant included and placed it next to the chastity cage at the till.

"Don't forget you wanted to try that."

My cheeks warmed with the humiliation, and I sunk into myself. Unable to look the cashier in her eyes, I hastily paid for the goods and bagged them before leaving the store. Sophie giggled to herself as we left the store and pulled me in for an embrace when we were outside.

"Sorry, the opportunity was too good to resist."

"It's okay."

Camden was busy again as we wandered through the markets and the shops. There was so much going on, and the vibe of the place was infectious. As dinner time approached, I picked up a few snacks for us both and walked towards Primrose Hill. Sophie and I enjoyed a picnic on the hill overlooking the beautiful London skyline. It was effortless being with her. The conversation came naturally. I could let myself loose around her in a way I couldn't with anyone else. Once we had eaten, we returned to the hotel to prepare for the evening, stopping at Boots for a couple of accessories for this evening.

I stripped my clothes as Sophie did the same next to me. Her body was perfect to me, and I imagined what she'd look like in a maid's outfit once I'd made it through her dare. With a wicked smile, Sophie held up the box for the chastity cage and unboxed it. I couldn't help but notice that she picked up the extra-small option, but I suppose I was a little extra-small down there.

"Right, we just have to squeeze these through here."

Sophie explained as she gently pulled one ball after the other through the plastic ring of the device. My cocklet instantly grew hard at the attention, and I couldn't help but think that was counter-productive towards her efforts in getting the cage on.

The plastic part that fits around my cock curved facing downwards, and it took Sophie a few minutes to push my cocklet towards the ring around my balls so that she could attach the plastic cage part to the ring and then thread the padlock through the hole to secure it in place.

"Wow, that's uncomfortable."

Sophie laughed at my comment, but having my erect cocklet confined into a cage barely an inch and a half long was a little painful.

"I bet. Now I'm going to keep this safe right here."

I watched as Sophie attached the key to her necklace before she bent down to inspect the device closer. I moaned as she stroked my balls, causing my cocklet to strain against the cock cage. Maybe this week would be more difficult than I thought it would be.

I waited and watched as Sophie got dressed in a two-piece outfit. Both pieces were glittery pink with sequins that reflected the light. There was a bralette for the top and a mini-skirt for the bottom featuring tassels decorated with sequins to match the top. Completing the set, she wore a pair of slip-ons that matched the outfit. The outfit looked stunning on her.

Now it was my turn. Sophie chose a sparkly pink thong which was riding up my behind the moment I put it on. Next, she placed on the small pair of fake breasts she picked up from Cyberdog. They fit similarly to a bra with a thin strap over the shoulder and a clip at the back. Immediately I was unfamiliar with the extra weight on my front, but when Sophie helped me into the tight-fitting dress, the results spoke for themselves.

I stepped into the high-heeled shoes that Sophie had bought me earlier and couldn't believe how much taller they made me feel. I did a couple of practice laps in the hotel room for Sophie, and she giggled as I stumbled a few times. These were going to take some getting used to.

I looked incredible with the dress hugging my slim torso and the fake breasts. With the chastity device tucked between my legs, there was no evidence of that on show. The final part for this evening was the make-up, and Sophie went to town using some new glittery body paint she picked up from Boots earlier. She made a rainbow effect using pastel colours to decorate my cheeks and also painted some small, glittery gold stars to go with it. She continued the pastel-colour theme with my eyelids, blush, and lipstick.

Standing beside Sophie in front of the mirror, I couldn't believe the transformation Sophie had overseen. We both looked like a couple of hot girls ready to go out for a night out on the town or to a music festival. I felt attractive; that was the first time I'd ever thought that. Hell, I would do me. With our arms linked, we left the hotel together for the music venue.

It was muggy outside after another sunny day in the city, and Camden was buzzing with energy as people prepared for their night of partying ahead. There was no queue when we arrived at the Electric Ballroom close to the underground station, but then we were early, and the doors wouldn't open for another quarter of an hour. As we waited, I received my first wolf whistle from a group of drunk football fans walking by. I didn't know how I felt about that. I was a little flattered, but I'd never felt so objectified.

The doors opened a little later than the tickets said they would, but when they did, Sophie and I made a beeline for the bar. The modern music played on the speaker system as we stood by the bar drinking a cocktail and waiting for the first DJ to come onto the stage.

Halfway through the first act, we recognised a few girls we met yesterday evening and joined dancing with them. At every opportunity, Sophie made sure that she rubbed herself against my groin area, teasing my locked-up cocklet. After a while, it became unbearable and I even felt like I would end up dry-humping something.

Aside from the frustration, it felt good to be treated like 'one of the girls'. My voice alone made it clear that I was born male, and although Sophie had done a fantastic job of transforming me, I was still able to see my male self through reflection, and I guessed others did too. The group we had met had followed Sophie's cues and didn't treat me any differently from how they would treat one of their friends.

By the time the main act came onto the stage, I was so desperate to be touched. Sophie had encouraged some of the other girls to dance up close as a group and I was having my body rubbed by other bodies all over.

It was close to three in the morning when we left the music venue, and my cocklet was twitched for release. To my relief, Sophie had promised she would give me a chance to cum when we got back to the hotel. I wasn't sure I felt too optimistic about the way she said it was a chance instead of allowing me completely. I did like the way that it wasn't my choice though. Well, sure I could forfeit her dare, but I was no quitter.

Once we made it into the room, Sophie told me to strip out of the dress and put on the fluffy cardigan she bought for me earlier.

Wearing just the cardigan and the chastity cage, Sophie led me to kneel with my legs spread facing the mirror and to place my hands down on the floor on either side of my cocklet and she handcuffed my wrists with the pink, fluffy handcuffs. The second she unlocked my chastity cage, my cocklet sprung to life, fully erect.

"You have one minute to get yourself off, sweety. Are you sure you still want to go stick it through with this dare?"

For a moment, I was confused about what Sophie wanted me to do. It dawned on me that she wanted me to try and fuck the gap in between my wrists that were covered in the fluffy cardigan. I stared at her, mouth agape.

"I'd get starting now, as your minute starts in three, two, one. Go."

Realising that Sophie wasn't joking, I got to it. On my knees, with my hands resting on the floor just in front of me, I started thrusting and fucking the gap between my wrists. It was incredibly awkward, especially since I was a little drunk; I struggled to find a rhythm. Still, I was already on edge from the constant teasing at the rave earlier, but as soon as I found a rhythm, I only had fifteen seconds left. Desperately, I started fucking between my wrists much quicker as Sophie giggled.

"And, three, two, one. Time up. Stop."

It took all I had to stop thrusting as my cocklet twitched and throbbed for more since it was so close to release. I looked up at Sophie as she approached and pouted at her, almost begging her to let me continue.

"You know, I quite like you begging like this. I'm afraid a dare is a dare, and you've had your minute. You'll have to wait for the next attempt."