Down The Rabbit Hole Pt. 02

Monday mornings never got easier. Just knowing that you had five days ahead of you where you had work to do before you had a day of freedom once more was always a strain, but today was different. Today was the first day that I was going to wear my new panties all day, and what made it all the more special was that Sophie had asked me to, and had even chosen which pair I was to wear. Under my jeans today I wore a sheer purple set of lace panties, that were fairly transparent. They felt super comfortable, and just the way they rubbed against me was already causing me to get hard. If it continued in this way, I was going to have to excuse myself when on a break to give myself some relief.

Sophie had messaged me first thing this morning asking for updates throughout the day, including a risky shot or two where possible. I debated doing the first of those risky shots now whilst I was on the underground, but it was far too busy. I felt on edge with the knowledge of what I was wearing under my jeans alone, trying to flash here without being caught would be impossible. Not to mention it already felt like everyone had x-ray vision and was silently judging me, even though there was no way they would know. That didn't stop me from shifting around to try and distract myself though.

Ever since I had met Sophie, my life had been turned upside down, and not in a bad way. I wondered if it was fate that led me to buy those panties the day of the party because if the same events had unfolded the way they had and I wasn't wearing the panties, I wasn't sure the results would have been the same. Sure we get on well, but she would have been disappointed with my tiny penis and lack of experience. Maybe I would have lost my virginity that night, but I don't think I would have made such an impression on Sophie. I could tell that she genuinely wanted to spend time with me, and she was sad to see me go on Sunday morning but she had breakfast arranged with Lily.

I arrived at the station closest to my university and I headed outside to wander before I found a dark alley between two shops. I'd used this space once before to urinate when I had been desperate, and I knew that it was rare that anyone came around here. Still, my heart was beating fast as I unzipped my jeans and lowered them slightly, leaning forward to push out my ass and take a quick picture for Sophie. The picture was a little rushed, but it came out better than I anticipated, at least I didn't have to do it again. I cringed at how flat and unattractive my ass looked in the picture. I may have had a petite frame, but my ass didn't look feminine at all. I wasn't sure why, but I was starting to crave that my figure was a little more feminine. Sophie replied within seconds of the picture being sent with one of those emojis with the heart eyes and a couple of fire emojis, saying that she wanted more. I couldn't help but smile to myself, never did I imagine that I would find someone who would encourage this fantasy of mine the way she did, and that person would also get off on seeing me like this. It had taken me a long time to convince myself to buy the panties to wear for myself, if I had been doing it for someone else for the reaction I was getting from Sophie, I probably would have done this much earlier.

The first couple of lectures of the day seemed to drag on a little, though being able to feel the panties and the reaction they caused whilst being surrounded by other students was proving a turn-on. I made sure I tucked my t-shirt in under my hoody so that there was no chance the panties were visible to those sitting behind me. The risk of wearing the panties was another turn-on, but I really didn't want anyone to see them. Steve noticed I was otherwise distracted this morning and asked how I was, he didn't seem to buy my answer that everything was okay and he gave me a concerned look. I wanted to tell him he really didn't have to worry about me, I felt far better than I had for a while, but that would involve telling him about Sophie and the fact I was wearing panties. He would be sceptical about my sudden mood change, he had known me for too long.

When lunchtime arrived, I rushed through my sandwich before rushing off to the toilets. 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 free cubicles. It occurred to me that if I had been desperate to pee, I would have had to come in here anyway otherwise there was a chance that I would reveal the panties if anyone used a urinal next to me. I sat down 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 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. Normally, 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" Sophie exclaimed, and I hoped that she was somewhere out of earshot from others. "Let us have a little 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 and it grew hard.

"Pull those panties up and start stroking that little cocklet for me." Sophie's tone was soft and encouraging. Normally 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 of the panties 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.

"Try not to get too excited beautiful" Sophie reminded me as she took in the look of pleasure on my face. She had a point though, I'd already cum all too quickly in her presence before, and I could feel that it wasn't going to 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 precious. Can you pull those panties and wait for me to call back later sweety?" I looked at the screen with an exasperated expression on my face, 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 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 feeling of frustration remained as I walked into my next class after an extended lunch break. Steve had returned from lunch with a grin on his face and he mentioned to me that 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 and 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," Steve exclaimed, and I smiled. There was no doubt in my mind that Sophie would approve of Steve, he was a likeable person, not to mention one of the most honourable people that 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 just yet. I still had a hard 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 I felt 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 puts 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, though 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 in a subtle way 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 they seemed to genuinely come from a place of affection. It didn't feel like she was trying to belittle me 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 girl and rubbing that cocklet for me. Show me those pretty panties and get stroking sweety."

Well, that did it. I felt my cock instantly grow hard and 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 where she angled the phone on the side so that I could see her. I was allowed to stroke myself again as I watched her tantalisingly lather her beautiful inked body with soap, craving 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 touching 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" Sophie enthused and I noticed that she was outside now. When did that happen? I'd been so lost in that euphoric, floating sensation that I hadn't even realised she was dressed and outside. Just listening to her voice as she instructed me to stroke myself for her had put me in a lustful trance. The desperation for release just kept growing and Sophie was showing no signs of telling me to push myself over the edge as she asked for my address. My cock was feeling so sensitive now that the gaps between touching myself and not touching myself were much quicker. As Sophie arrived at the street I lived in, I unlocked the front door and left it slightly ajar so that she could walk in whilst I continued stroking myself.

"Well done!" Sophie cheered as she walked in and embraced me. My legs had been shaking and my mind felt cloudy, but everything changed as her lips met mine. I could taste her cherry lip balm and 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. For a moment, I waited there expectantly, breathing heavily as I stood with my jeans around my ankles. Sophie just smiled with a mix of playfulness and wickedness and said that maybe I should take a quick shower since we were going to go 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 which 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

Sophie took me to one of the more popular gastro-pubs in East London. It was busy inside and 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 and 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 really 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 normally went for the bad guy, the hot guy that she knew would cause her anguish at some point. The sex was usually good, but she was left wanting romantically and ended up hurt. She admitted that she had never even 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," Sophie admitted. "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 to."

"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 and it showed in the way she asked. I wondered how badly her partners had hurt her in the past, was her confident demeanour just a facade that she put on?

"That's great" Sophie beamed and she leaned over the table to kiss me. We continued to talk, but the mood changed as 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 and she got up and I followed her out, my cheeks warm and looking down to the floor avoiding anyone's gaze as we left.

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 me 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 own cum still in my mouth. My body was slightly shaking as I recovered from that moment of pure bliss that 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 and I squeezed in facing her, enjoying the softness of the water changed by the bath bomb.

"Have you ever thought about shaving?" Sophie asked.