Down The Rabbit Hole Pt. 03

Story Info
Follow Alex as he finally lives out his feminisation fantasy.
3.2k words
4.77
7.4k
11

Part 3 of the 4 part series

Updated 06/16/2023
Created 01/20/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

My first, and only, class today happened to be cancelled due to the teacher being ill. Not wanting to fall behind with my learning, I headed to the library to revise some of the stuff I had already learned. It was quiet in the library, seemingly I was the only one who had thought to use this time to revise instead of enjoy the free time. Despite my good intentions, I could only revise for so long before boredom took over. Instead, I spent my free time browsing the internet on my smartphone. It started innocently enough, catching up on the news and looking into some updates from my favourite bands, but it soon took a turn. I started browsing clothing sites and sending pictures of panties that I liked the look of to Sophie for her opinion. As I browsed, recommendations of full outfits began showing, and I couldn't help but wonder what they would look like on me. Especially now that my body was mostly hairless.

One of the links I clicked on sent me to an adult toy site that sold sexier clothing. I couldn't help but get excited at what I was seeing, just imagining what it would feel like wearing something like the shiny latex dresses, or the babydolls and chemise outfits. And then I saw the corsets. I'd never even thought of wearing one of those before, but suddenly the idea seemed so incredibly appealing. I felt the sudden need to escape somewhere private and I walked quickly to the nearest toilets. My face was flushed and I could feel my hard cocklet pushing against the lace panties, if I reacted this way just from the clothing, I dreaded to think how I would react should I start looking at the toys. Locking the door for the cubicle behind me, I started recording a video on my phone since I knew Sophie was in class as I pulled down my trousers and started stroking myself through the panties. This felt so much better now that I was smooth down there. I imagined myself modelling some of the sexy outfits for Sophie as I stroked, being sure to slow down or stop if I found myself getting too close to climax. It occurred to me how although I found it unnatural to stop myself from cumming, I wanted to do it for Sophie. She hadn't asked me to, but if this could help my stamina during sex, then all the better.

Sophie met me a little later at the nearest underground station. We kissed and she thanked me for the videos saying that they were very sexy. Heading for the Northern Line, Sophie said that we were heading for Camden. I'd never actually been to Camden. A few of my favourite bands have had gigs there but I'd never felt confident enough to go to a gig, even though Steve had invited me before. Since the rush hour had passed, the underground wasn't too busy, and I even managed to flash Sophie my panties since the carriage we were on was empty.

We arrived in Camden a little midday and it was starting to get a little busy. I'd never seen anything quite like this place, it was quirky, to say the least. Everywhere I looked there was something that demanded your attention to appreciate it. From some of the graffitied walls, a couple rumoured to be a 'Banksy' or the stores that were decorated with statues of dragons and angels, the place was certainly unique, but in such a fascinating way. The people walking through the shops and the market stalls were mostly dressed in alternative clothing, a lot of inspiration from punk, and the emo years of the early noughties. There was such an incredible vibe to the place and I wished I'd visited earlier.

The first shop we stopped at sold various band wear and I picked up a top featuring one of my favourite bands, though Sophie suggested I buy the one designed for females stating that she thought it would look sexy on me. I followed her advice, she hadn't been wrong so far, so who was I to doubt her? The theme continued as we went through various market stalls and shops Sophie bought me a few clothes that she'd like to see me in, including some goth dresses, a vintage dress, mini-skirts, and crop tops. I felt spoiled by her buying me the clothes, and I even said I was happy to pay for them, but she was adamant that my wearing the items was more for her. That was something I didn't necessarily agree with, the idea of trying some of these out was making me hard again. At every shop, Sophie gave me her card and told me to go to the counter to pay. She said that I shouldn't feel ashamed of buying these sexy clothes for myself. This was who I was, and she didn't want me to neglect the opportunity to treat myself because I was worried about what others thought.

The last shop we stopped in was different from anything I'd ever seen, Sophie had been saving the best until last. The shop was called Cyberdog and the second you stepped inside you were almost overwhelmed by the colours and the loud electronic music. Down the escalators, a DJ was playing through a set and the shelves and stalls were lined with rave-inspired clothing, some 'glow-in-the-dark', some alternative, and some even with electronic message boards built into the top. This shop was incredible. I was so inspired by some of the choices that I picked up items that I liked the look of myself and asked Sophie's opinion. There was a pink top with a black heart emblazoned in the middle and matching hot pants, and also a couple of dresses that appealed to me that I decided to purchase.

On the next floor down, I found the adult section of the store. I was a little uneasy about going down there, my prudish upbringing showing rearing its face again, but Sophie gently persuaded me. My eyes opened wide as I saw some of the adult toys on the shelf, of course in the loud and colourful style that Cyberdog seemed to specialise in. Sophie picked up a cuff kit, all in pink with a cute pink choker, a pink ballgag, a couple of lengths of rope that had been dyed pink, and a pink blindfold.

"Would you mind too much if I bought us this?" Sophie asked with a wink.

"Err," I replied nervously, instantly reacting in my prudish manner. I stopped myself for a second thought. This last week I've been far more adventurous than I'd ever imagined I would be, and it has paid off massively. I'd got to meet and spend time with Sophie and I'd fulfilled my fantasy of wearing panties which had opened up a bunch of other fantasies I didn't know I had. As much as the look of the gag and the cuffs scared me a little, they also excited me. I had complete trust in Sophie that she wouldn't do anything to harm me, so I nodded and smiled.

"Go for it!"

After shopping, we went for lunch and a couple of drinks by the canal. It was a beautiful day and it was nice just soaking up the sun and the atmosphere whilst eating outside. Feeling somewhat inspired by the happy mood I was in, I asked if Sophie wanted to stay in Camden with me for the night, my treat. Like me, she didn't have any classes at university tomorrow so she agreed. I googled on my phone for the closest hotels and found a nice-looking one just around the corner. It overlooked the canal and offered a balcony that offered a nice view of the London skyline. I booked a room and we both made the short walk there.

Inside our room, I instantly undressed to just my panties. I was becoming used to the feel of them and the comfort they gave me.

"Well, if you're going to strip off, so am I" Sophie grinned and I certainly wasn't going to argue with that logic. We smooched and groped each other on the bed for a little before Sophie told me to stay where I was and she opened the pink bondage kit that she picked up.

"Are you sure you're okay with these?" Sophie asked softly, genuinely concerned. I guessed she was able to read how uneasy my reply to her had been earlier.

"I am," I answered honestly.

As I lay there, Sophie gently put the pink cuffs around my wrists and ankles. She was soothing me the whole way, telling me how good I was as she stroked my cocklet through my panties. With the cuffs secured on me, Sophie asked me to lay spread-eagled on my back and she used the rope to secure the cuffs to the four-poster bed. I was hard instantly, just the thought of being at her mercy was enough to excite me. I could do nothing but lay there and anticipate her touch.

"Oh my god, that looks so pretty on you," Sophie said as she placed the pink choker around my neck and secured it in place. "Not going to lie, that is doing it for me."

I couldn't help but chuckle, even whilst Sophie was still stroking me. I wish I could see how it looked, but whilst being secured to the bed meant I couldn't get up to look in the bathroom mirror. That particular feat was made impossible as Sophie placed the blindfold around my head covering my eyes. Suddenly, my senses seemed heightened and I was more aware of every sound she made and every touch. I breathed deeply as she straddled me, leaning down to kiss. There was something about not being in control of the situation that was beginning to turn me on. I had no idea why I felt this way, but I was going to go with it. As our lips broke contact, I leaned forward, yearning for more. Sophie giggled and she leaned forward and let out lips barely touch, teasing me as I reached for her.

"Such a horny little thing" Sophie teased. "Open your mouth."

I obeyed instantly and felt her place the ball gag in my mouth. It tasted of plastic as expected, but it wasn't as bad as I had been dreading. This feeling of handing over control to Sophie bit by bit felt freeing. She teased my body, tracing her fingers down my chest, lightly tracing her lips against my lips and neck, stroking my nipples between her fingers. The sensations were overwhelming, made all the more intense by the blindfold. I'd never realised just how sensitive my nipples were, and seeing my reaction made Sophie want to play with them more. My whole body felt on edge as she teased me all over, and being unable to see what was coming next added to the anticipation.

Sophie shifted her position on top of me, changing so that she was now straddling my face. I could smell her excitement barely an inch from my face, and as much as I wanted to stick out my tongue and taste her again, the gag prevented me from doing so. It wasn't just her taste that I was craving, I wanted to please her. It caused me pride every time I had made her cum before, and I wanted to give her that sensation again, and again. I felt her wet pussy brush against my nose as she took my cocklet in her mouth. Over and over she teased me until the brink of climax, and then stop contact altogether with her pussy hovering barely an inch above my face. Her scent was intoxicating to me and my mind felt like it was floating as she kept me on edge. It was a high I'd never experienced before, and I didn't want to come back down.

Once more, Sophie brought me to the brink just to stop as she got off of me for a moment to remove my gag. Her lips met mine once again before she put herself in the same position she was before, though this time I could use my tongue. I was instantly rewarded with both her taste and her moan of approval. As I tried to focus entirely on her pleasure, Sophie continued teasing my nipples to the point where they were now so incredibly sensitive. Eventually, she turned her attention back to my cocklet and took it in her mouth again. Within seconds I was on the verge of cumming once more and judging by the growing desperation in Sophie's movement as she pressed down and rubbed her clit against my face and outstretched tongue, she was too. As she frantically rubbed herself to climax against me, she took my cocklet between her fingers and stroked it until I came all over her hand.

"Good work" Sophie enthused. Others may have found it a bit patronising, but I was quickly coming to value any praise from Sophie at all. I felt her hand touch my lips and asked me to clean my cum off of it. I knew what taste to expect since I kissed her cum-filled mouth the night before, and that made it easier to the point that I think I was beginning to enjoy the taste of my cum.

"Good sluts always clean up" Sophie laughed jokingly, but hearing her call me a slut pushed me deeper into my newly-found submission. I guess I was becoming a slut, at least for her, and that didn't bother me in the slightest. Sophie kissed me once again before she untied the cuffs and removed the blindfold. Before we showered, she wanted me to see my reflection in the bathroom. She was right, the choker around my neck looked brilliant.

"You should have seen yourself with the full kit on, you looked incredible. I would have taken a photo but I didn't know how you'd feel about that and I didn't want to ruin the moment." Sophie smiled. It was moments like that which made me trust her more. She could have easily taken a photo and I wouldn't have known about it, even if it was just for her collection.

"I think I would like to see that. Next time, you can take a photo, I trust you." I said as I removed the choker, getting ready for a post-sex shower.

Once washed and dressed in what I was wearing earlier, we went down for an amazing meal in the hotel. It wasn't too busy at this time and we had time to talk some more without being overheard. Sophie said that she was still finding out more about herself and how much she enjoyed this, so if she overstepped, she wanted me to say. The truth was, I was very much in the same boat and discovering more and more about what I liked as well. I was completely comfortable with everything, and how she had done it so far.

After dinner, we returned to the room to try out one or two of my new outfits. Sophie wanted to see me in one of the emo-inspired sets that she bought me, so she helped me dress. The first couple of items that Sophie helped me with was a new matching black lingerie set. The panties had a strap design which went up to just above my waist, and the bra had a matching pentagram design with the straps which also fitted to a black choker around my neck which had a metal ring at the front.

I stood there motionless, nervous as I let Sophie dress me. I was nervous as to how I would look, hoping that my image would live up to what she had imagined when she had picked out the clothes. Next, I lifted my arms as she fitted the crop top on me. It seemed so thin and I was worried I'd break it or stretch it when it was fitted, but I didn't. I suppose that said a lot about my actual frame, perhaps I should start working out. With the top on, Sophie carefully showed me how to roll on the tights so as not to damage them, something that was especially important for these that had been designed with holes in them. They felt so delicate, that they would break at the slightest pull. I couldn't help but stroke my legs to see how they felt against my skin. It was such an incredible sensation. The final piece of clothing for this outfit was a pleated, black mini-skirt which had some small chains around the waist. I stepped into it, and then with Sophie's help, put on the boots to match the outfit.

"Can I look now?" I asked, unable to hide my excitement and Sophie giggled.

"Not yet. I want to add make-up." She said with a grin and I sat on the floor facing her as she retrieved the make-up kit she had brought. As she applied the makeup. she spoke about her class on beauty. She had always been interested in how much makeup could change your appearance and she had spent years working on her face to teach herself and try out different designs. I felt at peace just listening to her and keeping still as she worked on my face, I would have to volunteer my face to her more often for this.

"Can I look now?" I asked again when she had finished applying the makeup, the anticipation of seeing what I looked like was too much.

"I'm not finished yet, I've still got your hair to do."

I sighed, impatient to see what Sophie had done to my image. I'd never had anyone do my hair before, and it was quite a nice feeling just talking to her naturally as she did it. There were so many things that men missed out on like this because they clung to their fragile masculinity.

"Voila" Sophie said and she helped me up and led me to the bathroom mirror.

"Wow!" I exclaimed, barely able to recognise my face. The outfit was comfortable, but what amazed me most was just how feminine I looked. Sophie had added some subtle eye shadow and mascara on top of a pale foundation which accentuated the emo look. dark brown hair had been braided on both sides and the bottom of that tied off to make 'pigtails'. Sophie informed me this style was called the 'double dutch pigtails'. I was lost for words and felt like crying because of how happy I felt. This was the first time I had looked in the mirror and felt fully comfortable with how I looked like it was the first time I had seen myself look how I thought I should look.

"Oh, one more thing," Sophie said as she just had an idea and she pulled off a bunch of tissue paper and shoved it down my top into both sides of my bra to give off the impression I had breasts. I looked incredible, and because of that I felt my confidence more than I had ever felt before, and Sophie was to thank for this. I'd have to figure out a way to show her exactly how much I appreciated everything she had done for me and how much it meant to me. For now, though, I said something to her that I thought I'd never do whilst dressed like this.

"Fancy going out for an evening walk?"

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
darthnader19darthnader19about 1 year ago

Loving it so far 🥰

AnonymousAnonymousabout 1 year ago

aw!!!! cute little lesbians

Share this Story

Similar Stories

Lacy Cream Ch. 01 A young man’s journey to become the hottest tranny porn star.in Transgender & Crossdressers
A Bad Bet with a Playful T-girl Will he lose and be feminized by his fun sexy T-girl friend?in Transgender & Crossdressers
Camming Down the Rabbit Hole Ch. 01 This is the story of how I became a camera gurl.in Transgender & Crossdressers
Creating Ginger Ch. 01 A wife decides her cross dressing hubby needs to go further.in Transgender & Crossdressers
The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
More Stories