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Down The Rabbit Hole - Part Three

"Follow Alex as he finally lives out his feminisation fantasy"

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Monday mornings never got easier. Knowing that you had five difficult days of lectures, coursework, and study ahead of you before the freedom of a weekend presented itself again was always a strain, though today was different. Today was the first day I was going to wear one of my new panties all day, and what made it all the more special was that Sophie had even chosen which pair I was to wear. Her choice had been a sheer, purple set of lace panties that were quite transparent. They felt super comfortable, and the way in which they rubbed against me had already given me an erection. If they continued to make me react this way, I would have to find a reason to hide away in the toilets and allow myself relief.

Sophie had messaged me this morning requesting updates throughout the day, and where possible, she asked that I take a risky shot or two for her amusement. Right now, travelling on the underground, I was tempted to try and get one of those photos, but it was too busy on the train. There would be no way to flash a little of my panties without anyone seeing. I already felt exposed with the knowledge that I was wearing the panties, convinced that the people around me had X-ray vision and were silently judging me, even though there was no way they could possibly know.

Ever since I met Sophie, my life turned upside down, but in a good way. I wondered whether fate had led me to buy those panties on the day of the party. Sure we get on well together, but I don't think the results would have been the same if she hadn't been so turned on by the sight of me wearing panties. When I had left her house yesterday evening after washing off the make-up she had applied to my skin, she had genuinely seemed sad to watch me go.

I arrived at the station closest to my university and headed outside, walking around aimlessly for a while before finding a discreet, dark alley between two quiet shops that weren't open yet.

I vaguely remember using this space before after drinking at a pub after university. I had been so desperate to urinate that I found this place and remember thinking how private an area it was. The loud noise of the city played around me as I fumbled around unzipping my jeans. I looked around the corner to ensure I was alone before dropping my jeans to my ankles. Hastily, I took a couple of pictures whilst I clumsily stuck my ass out, cringing at how flat and unattractive my ass looked in the photos. I may have had a petite frame, but my ass didn't look the slightest bit feminine, and that bothered me for some reason.

Sophie replied instantly, expressing her appreciation for the picture and adding those emojis with the heart eyes and a couple of fire emojis on top. Immediately, she wanted more.

I couldn't help but smile goofily as I read her message. I never imagined I would find someone who would encourage this fantasy of mine the way she did, and then that person would also get off seeing me like this. I promised more pictures for later and then made my way to the first lecture of the day.

I shifted uncomfortably in my chair as the teacher droned on in a monotonous tone. The panties were still causing me some excitement and I felt a need to touch myself, though I couldn't right now in the middle of class. I'm sure that kind of behaviour would be frowned upon. I had made sure I had tucked my shirt into my jeans before sitting down, I didn't want any chance of anyone spotting the panties at all. Despite how nervous it made me, I discovered the risk of wearing the panties was another turn-on. Steve had noticed that I was distracted this morning and he seemed a little concerned. I assured him all was okay, but I knew he worried about me. I didn't have the same social skill or mental strength that he had, and I was sure he was worried about me falling into depression or hurting myself. I wanted to tell him that I was happier than I had been in a while, but that would involve telling him about Sophie and the fact I was wearing panties.

When lunchtime arrived, I sat down alone and rushed eating my sandwich before finding toilets that were out of the way and less likely to be used at this time. Thankfully I didn't have to explain my absence to Steve since he had gone to meet Lily and Sophie for lunch. Both she and Sophie went to a different college not too far from our university and Sophie had messaged earlier that she intended to interrogate Steve to make sure he was good enough for her best friend. I did my bit for Steve, vouching for him that he genuinely was a fantastic guy.

The toilets were thankfully empty as I rushed into one of the empty cubicles. It occurred to me that if I had been desperate to pee, I would have had to come in here as there would be a chance that I would reveal the panties if anyone used a urinal next to me. I sat on the toilet and pulled down my jeans, just as Sophie video called me.

"I've got a few minutes to spare before meeting Lily and Steve and I just wanted to see how you were?"

Sophie's voice soothed me through my wireless headphones. I saw my face at the bottom of the screen smiling goofily, and that was purely the reaction to seeing Sophie.

"Wait, are you on the toilet?"

"I am. Just finishing up."

I smiled sheepishly. I wouldn't have answered, but I didn't want to miss the opportunity to talk to her. Slowly, I shifted the camera to show me sitting on the toilet, my legs spread and my panties around my ankles.

"Oh, I do like the look of those panties around your ankles."

I hoped she was somewhere out of earshot from others when she said that.

"Let us have a little bit of fun, shall we?"

Sophie lowered the camera to her chest and pulled aside the arm strap of her top to reveal that she was braless today. With her free hand, she cupped and massaged her breast. Immediately, my cock reacted to what I was seeing by growing hard.

"Pull those panties up and start stroking that little cocklet for me." Sophie's tone was soft and encouraging. I would be sensitive about having my cock referred to as a 'little cocklet', but she made it sound genuinely affectionate instead of demeaning. I placed the phone down as I pulled up the panties. Moaning, I stroked my cock through my panties, focusing on the feel of the material rubbing against my cock as I watched Sophie play with her breasts and nipples. I longed to be with her, to cup her breasts in my hands as she stroked me, but for now, this would suffice.

"Slow your breathing. Try not to get too excited, sweety," Sophie reminded me as she took in the look of pleasure on my face. She had a point; I'd already cum all too quickly in her presence before, and I could feel that it wouldn't take much more attention before I left a cum stain in my panties. Thinking ahead, I grabbed some tissue to prevent myself from staining my panties.

"Oh, Lily's calling me; I have to go. Can you pull those panties and wait for me to call back later?"

I looked at the screen with an exasperated expression, but I quickly recovered and did as she asked as she kissed the camera on her phone to say goodbye. Blushing, I tried to ignore my cock throbbing for more attention under the panties. It seemed unnatural for me to leave it hard and without climax, but Sophie had asked me to wait until she was able to watch, and I was all too happy to go along with what she said. I'd felt things I thought I'd never feel thanks to her.

The frustration remained as I walked into my next class after an extended lunch break. Steve had returned from lunch with a grin from ear to ear as he said he thought Lily might be the one. For me, it was too early for him to make that statement, but it was clearly the way he felt. He was an all-or-nothing kind of guy; I knew that if things continued to go well with Lily, he would be with her for life.

"I passed Sophie's test; she seemed to like me."

There was no doubt in my mind that Sophie would approve of Steve since he was a likeable person, not to mention one of the most honourable people I knew. I hadn't told him yet of my weekend with Sophie, and Sophie had only sworn Lily to secrecy that we had hooked up at the party and had a picnic date. I wanted to tell Steve but I didn't think it was the right time. I still had a difficult time convincing myself that I wasn't dreaming the entire thing. Listening to him talk about his lunch date was a good distraction from the dull ache from not bringing myself to climax when stroking myself earlier. A part of me wanted to tell Steve everything, including my long-standing fantasy of wearing panties, but I was worried he'd think differently of me. I was always a little different, a little geekier and into things that most others weren't, but this might be too much for him. He already put up with so much from me, and I'm so different to some of our other friends.

That dull ache was still present as I raced back to the underground station to get home, only now there was an increased desperation to touch myself some more, although I wasn't that desperate to try to do it on a crowded train, even if I did attempt to think of ways to do it subtly without getting caught. It was a shame these underground trains didn't have a toilet on them. Things became worse when the memory of how she spoke to me on the phone earlier crossed my mind. I probably should have found the way she addressed me as emasculating, but it seemed to genuinely come from a place of affection. It didn't feel like she was trying to belittle or humiliate me.

The train stopped at my stop and I ran home and waited for Sophie to call me whilst pacing in the living room. It took every ounce of willpower I had not to touch myself, and although I knew I could touch myself if I really wanted, it mattered more to me that Sophie was a part of this. It meant so much more, even if it was through the phone.

"Hey, beautiful."

Sophie smiled as I answered her video call with a goofy smile. I recognised her room from spending an amazing time there Saturday night. Sophie took her top off and once again cupped her breast with her free hand.

"Now, where were we?"

"I seem to have forgotten," I said with a wry smile.

"Oh really? Well, I seem to remember you were being a good little girly rubbing that cocklet for me. Show me those pretty panties and get stroking, sweety."

Well, that did it; my cock instantly grew hard. I lowered my jeans so that I could start stroking it for Sophie. There was that word 'cocklet' again, and my god, did I respond to it. Hearing her voice urging me on as I stroked my cock through my panties put me in my happy place. It almost felt like I was floating, riding a high of endorphins. I watched Sophie as she played with her nipples for me, asking if I liked what I was seeing. When she saw me getting close, she asked me to hold my free hand behind my back and watch her as she stripped down and headed into the shower. Placing the phone on the side, she angled it so that I could see her whilst she showered. I was allowed to stroke myself again as I watched her tantalisingly lather her beautifully inked body with soap, and I craved to touch her glistening skin. On and off, she encouraged me to stroke myself. Keeping me on the edge of climax and then telling me to stop stroking myself when I was on the brink of release as she teased me by massaging the soap into her skin. I discovered that whilst I was in this sensation of euphoria, I was very compliant. The part of me that yearned for release screamed out in my mind every time I stopped stroking, desperate for that burst of pleasure that came with the climax.

"Keep going there, cutie."

I noticed that she was dressed and outside now. When did that happen? I'd been so lost in that euphoric, floating sensation that I hadn't even realised she had left the shower. Listening to her voice as she instructed me to stroke myself for her had put me in a lustful trance. The desperation for release kept growing whilst Sophie showed no signs of telling me to push myself over the edge as she asked for my address. My cock was so sensitive now that the gaps between touching myself and not touching myself were much more frequent. As Sophie arrived at the street I lived in, I unlocked the front door and left it slightly ajar so she could walk in whilst I continued stroking myself.

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"Well done!" Sophie cheered as she walked in and embraced me. My legs were shaking and my mind felt cloudy, but everything changed as her lips met mine. I could taste her cherry lip balm as I felt her tongue push into my mouth, massaging my own. I did my best to copy her, but I went with her lead, afraid that my lack of experience would be obvious.

"Thank you," I breathed as I felt her soft hand cup my cheek.

I waited there expectantly, breathing deeply as I stood with my jeans around my ankles. Sophie smiled with a mix of playfulness and wickedness and said that maybe I should take a quick shower since we were heading out.

"We're going out?" I asked. This was news to me.

"Yeah, I'm treating you to dinner."

Sophie smiled as she helped me step out of my jeans and panties and followed me to my bathroom. I turned on the shower, surprisingly feeling less and less nervous being naked in Sophie's presence. I quickly washed and dried myself before stepping into another pair of panties that Sophie had brought with her. I recognised them as one of the panties I had worn to model for Sophie on Saturday night. These were silky and much smoother against my skin than the last pair, and the back part was thinner, like a thong that seemed to get between my ass cheeks. Sophie chose a pair of jeans and a smart-casual top from my wardrobe which I got dressed into and then we left.

We arrived at one of the more popular gastro-pubs in East London. It was busy inside so we were lucky to have got a table without booking and even luckier to get a table that was fairly secluded from anyone else. I ordered a chicken with cheese and barbecue sauce dish which came with homemade chips, and she had a burger. The food was absolutely delicious; I could see why this place had become so popular. Over dinner, we spent time getting to know each other a little more, and it amazed me how much we had in common. I was a little geeky; I loved things like Marvel films, anime and gaming and she did too! We had a lot of music that we liked that overlapped as well, which was always good as I was a little fussy with my music taste and wasn't too tolerant of the stuff I didn't like. She asked me about my history with girls, and I admitted I'd not got far, just to kissing, though that was before the other night at the party. I was still a virgin, of course, though I very almost lost my virginity with Sophie at that party if only I hadn't been so excitable and came a little prematurely.

Sophie explained how she usually went for the bad guy, the hot guy that would cause her anguish at some point. The sex was usually good, but she was left wanting romantically and ended up being hurt. She admitted that she had never thought about a man wearing panties before, but seeing me that night of the part changed all of that and it seemed to have awakened a part of her that she didn't know existed.

"I've never felt as close to anyone as I do to you right now, you're definitely not like the other guys I've been with, and believe me, that is a good thing. If it's okay with you, I'd like to be with you; to make this official. That is if you want me too."

"I'd love to," I answered softly, amazed by how vulnerable Sophie seemed as she asked the question. She genuinely wanted to be with me. I wondered how badly her partners had hurt her in the past; was her confident demeanour just a facade?

"That's great," Sophie beamed at me before she leaned over the table to kiss me. We continued talking but the mood changed when Sophie started rubbing her foot between my legs. Thankfully, the tablecloth covered the view of what was happening, but that dull ache of being teased without release all day had returned a hundred-fold. Her grinning face told me that she was enjoying my anguish. She got up and I followed her out, my cheeks warm and looking down to the floor, avoiding anyone's gaze as we left for Sophie's place.

The second Sophie's door closed behind her, she locked it, turned on some soft, sensual music, and then pounced on me, pushing me softly onto the bed as she straddled and kissed me. There was a passion inside of me that I had never experienced before, and all I wanted to do was to have her lips against mine. Her fiery passion matched mine as we made out and explored each other's bodies. I let Sophie take the lead as she unbuttoned my jeans and started kissing the inside of my leg. I don't know why I felt so sensitive, but it felt so good as her lips made contact with the inside of my thigh. My penis stood to attention as Sophie lowered my panties and took it in her mouth. She shifted her gaze to meet mine and I nearly came right there and then. I was instantly on the edge as she slowly took my cock in her mouth, and slowly came back up. My abs and legs were shaking, but Sophie was going just about slow enough to push me over the edge.

As she straddled me, she removed her top and pulled down her panties. I was completely frozen as she positioned herself over my rock-hard cock, and guided it with her hand as she lowered herself onto me. It was, of course, my first time and the first thing that struck me was how warm and soft it was inside her. She kept the rhythm slow as she rode me, keeping eye contact as I couldn't look away from her. She completely mesmerised me as her body moved to the slow rhythm of the song on top of me. It was all too much and I closed my eyes as I felt myself getting close to climax like I had so many times already today. Sophie saw it too and she changed her position so that her glistening-wet pussy was directly over my face. I didn't need her to tell me what she wanted and I started softly licking her clit. I felt her take my cock into her mouth again, slowly teasing it as I tried listening to her contented moans as to what worked for her with my tongue. She started rubbing her pussy over my face slowly as I licked, and I felt her legs convulse on either side of my head as she got close. Her desire for climax grew as I felt her smother me with her sex as she started bobbing her head faster and rougher on my cock. All the pressure that had built throughout the day of being denied release erupted in an exposure of pleasure that made me feel light-headed. I was barely aware of Sophie's cries of pleasure as I moaned in pure ecstasy. Sophie straddled me again and leaned down to kiss me with my cum in her mouth. I felt her push the cum with her tongue, sharing it with me. There was a small part in the back of my mind that thought that having my own cum in my mouth was wrong, but it seemed so right at this moment. Sophie and I had just shared this incredible experience, and this was just a part of that experience.

"That was intense." My voice was weak as I tried to catch my breath, the sweet, yet salty taste of my cum still in my mouth. My body was slightly shaking as I recovered from that moment of pure bliss I would never forget.

Sophie kissed me and asked if I'd like to join her for a bath. I stood leaning against the wall as she ran the bath and threw in a lavender-scented bath bomb that turned the water a lilac shade of purple. Her bath wasn't the biggest; I squeezed in, facing her, enjoying the softness of the water changed by the bath bomb.

"Have you ever thought about shaving?"

"I do." I smiled, rubbing my chin.

"I meant your body, silly."

Sophie grinned. I told her that it hadn't occurred to me, but now that she had mentioned it, I found the thought appealing. I mean I didn't have the hairiest of bodies in the first place, but I told her that it was something I'd probably do.

"Can I do it? I promise I'll be gentle," Sophie smiled, and I could see how excited she was to shave me. How could I say no to her now? I think she would genuinely pout if I did.

"Go for it!"

Sophie celebrated as she got one of her disposable razors and a tube of shaving cream. I lifted my leg and rested it gently on Sophie's shoulder as she massaged the shaving cream onto my legs. Delicately, she shaved my leg, keeping her promise of being gentle. Once again, I felt myself getting hard as I watched Sophie shave me. When she saw that I was hard, she giggled lightly and continued until she couldn't see any body hair on my legs, face, chest, and back.

My pubes were a little longer; she had me stand as she used scissors to trim them down before continuing her work with the razor. I was still so sensitive there from earlier and so turned on from being shaved that just a little bit more stimulation would have probably made me cum again. I had to admit, my body looked good and smooth, and I even looked a bit bigger down there.

"You have such great skin for a man, though you really should start a skincare routine to maintain and improve it further."

Sophie wiped off the last of the shaving cream and rubbed a moisturising cream into my skin before passing me the product to massage into her body. I took care to massage it in all over, making sure I didn't miss a spot as I admired her body. How had I got so lucky?

After the bath, I lay at her side on the bed with my smooth skin touching hers. I felt her drift in my arms whilst I stroked her hair, and I drifted off within a few minutes.

I met Steve early in the morning for coffee. I would have loved to spend more time with Sophie, but we both had classes. We travelled into central London together before kissing as we went our separate ways. Sophie had asked if it was okay for her to tell Lily about us, and I said it was fine, and asked her about telling Steve. She had promised to leave out the part about the panties before I had the chance to ask, and I thanked her for that. I may have been comfortable with Sophie, but I wasn't ready to let Steve, my closest friend, know about it, let alone Lily. She seemed like a lovely girl, and Steve definitely raved about her, but I didn't know her that well.

"Good morning, my man, how are we doing?"

Steve was in his usual upbeat mood this morning. It was usually quite hard to handle at this time in the morning, but I was in a good mood after last night. As we drank our coffee, I filled Steve in on my new relationship with Sophie, leaving out the bit about the panties, including the pink ones Sophie had chosen for me to wear this morning. I had to admit, they felt so much better against my smooth skin.

"My dude, really?"

I watched his facial expressions switch from shock to pure delight and he embraced me before offering his hand for a high five. He wanted to hear everything I had to say on the matter; he was absolutely thrilled.

"I was worried that I'd be spending less time with you because of spending more time with Lily, but it seems you have someone else to spend time with now! Lily speaks very highly of Sophie, and Sophie certainly is protective of Lily; you should have seen the way she interrogated me, pal. I think you've got a good one there!"

Steve offered a wink before we finished our coffee and made our way to class.

On the way to class, I had a message from Sophie saying that Lily approved of me. She also expected another video call to play when I was free after the first class. In another message sent straight after, she said she finished at lunchtime today and asked if I wanted to join her shopping if I was free. I agreed to both the video call and the shopping trip and all of a sudden I couldn't wait for the first lesson to come to an end.

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Written by elementsoflife
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