Down The Rabbit Hole

Part One

London, when the sun was shining was one of my favourite places in the world. The good weather changed the vibe of the city, and although people still kept to themselves, it was clear that everyone just seemed a little bit happier and walked with a little extra spring in their step. Wearing denim shorts sporting a few rips from the wear and tear over the years. and a faded yet treasured Linkin Park tour tee shirt, I enjoyed the feel of the sun on my pale skin as I walked through Hyde Park on my way to meet my best and longest friend Steve. I know that Steve had opted to take the underground, but on a day like today, that seemed like madness. Why travel on a train crammed full of people on a day as nice as today? Sure it was quicker, but leaving earlier sure beat spending a quarter of an hour with my face in someone's sweaty armpit.

In truth, I hadn't wanted to go out today but Steve had insisted he needed me as his wingman. As a self-proclaimed introvert, I was most comfortable at home in front of my computer playing games or listening to music, but there were the odd exceptions that I enjoyed going out, like the Linkin Park concert from a year ago. Steve had a first date today, however, and his date wanted to bring her friend since it made her feel more comfortable. For that reason, Steve had roped me in to join them, and as I approached the coffee shop where he had agreed to meet her, I saw him standing outside waiting for me.

"Alex!" Steve exclaimed and he slapped my hand in welcome. Like me, Steve had long hair for a guy, but he also had a cool beard coming through where I struggled to get mine to grow. He was cooler than me, though he never made me feel that way and he had been a truly great friend throughout our time at secondary school and still now that we were in university together. We both drank alcohol for the first time together, and I was there at the party where he lost his virginity. I was still a virgin, but it didn't bother me. I knew that I was rather average looking, fairly skinny and also quite small in stature compared to most others in their early twenties at just over five foot tall. I wasn't blessed with a large penis either, or the confidence that came with that, and that made me anxious as to how any future sexual partner would react when confronted with my three-inch fully erect penis.

We walked inside the coffee shop which was one of those soulless franchises that had taken over and found a fairly secluded table in the back corner of the coffee shop. The lights were dimmed which gave off a warm and relaxing glow as it softly flickered. Only a few minutes passed from when we sat down until Steve's date and her friend turned up.

"Hi, Lily. This is my friend Alex, Alex, this is Lily." Steve stood and I followed, shaking Lily's hand clumsily. I could see why Steve had wanted this date to go so well, Lily was very attractive. Her face was pretty, and her slender, yet curvy in the right places look was very appealing. Lily smiled warmly at me and introduced her friend Sophie. Sophie was equally as pretty as her friend, though her grin as she shook my hand suggested that she was more mischievous than her polite friend. Everything about her image dared people to confront her and warned them that they'd lose at the same time. The short skirt that showed the thong she wore underneath when she bent over, and her crop top that showed off her perfectly toned midriff yet also was low cut enough to show off her ample breasts. Standing considerably taller than her friend, her inked skin looked remarkable and she had multiple piercings on her ears, nose and lips. The two of them standing together was such a contrast. The modest innocence of Lily who was so polite and softly spoken compared to the loud and much more daring Sophie.

Steve ordered us coffee and the first few minutes were a little nervy, but Lily and Steve hit it off brilliantly. They shared similar interests and had a similar sense of humour, they also managed to keep me and Sophie involved in the conversation so that we didn't feel like a third wheel. I ended up enjoying myself a lot more than I thought I would and was in a good mood when I left the coffee shop over two hours later.

On the way back, I headed into Primark to buy some clothes that were sorely needed. When I chose to stay in London for the university as opposed to travel away, it meant I could stay at my parent's house and not have to pay dorm fees. Sure I didn't have as much independence as I would have had if I did choose to travel elsewhere, but it meant I was far less stressed, and much better off financially. The shop was quiet as it was nearing closing time and I rushed around to pick up what I needed, a few t-shirts, some socks and a new pair of jeans. As I walked past the lady's underwear section, I slowed down and cautiously looked around before walking through the section. Feeling ashamed, I lowered my head, but I couldn't help myself. Something kept drawing me to the section, I'd say it was a fascination, but it was nearing an obsession. I wanted to know what it felt like wearing one of those pink lace knickers and I wanted to see how I looked wearing it. There was a feeling deep down that I shouldn't feel this way, that it was wrong, but the idea had excited me for some time now. I picked up the panties like I had so many times before, except this time, instead of discarding them on a shelf before approaching the till I still had them with me as I approached the cashier. I had no idea where this sudden burst of confidence had come from, maybe it was because I'd had such a good afternoon, but all of a sudden that courage disappeared as I faced the cashier, Nervously, I waited for the young lady to question me about them, or to look at me funnily, but she never did. Either she didn't care, or she assumed I was buying them for someone else.

With the lace knickers hidden in the bag, I rushed home feeling eager to try them on. My parents, who were both retired, had gone away for the week somewhere abroad. They did tell me where, but I hadn't been paying attention when they told me. Once inside, I immediately rushed upstairs to my room, taking off my jeans and my t-shirt. I had always hated my body. Skinny with barely any muscles, short and a small penis, I barely even had any body hair. The epitome of masculinity I was not. For years I had wanted to try wearing knickers and had even fantasised about fully dressing up as a girl. I had no idea why but the thought was very arousing to me.

Slowly, I stepped into the knickers, feeling the soft lace travel up my legs until they rested in place around my waist. God, they felt great, and they looked so damn sexy on me. I could feel myself growing hard; I just loved the way it felt when I rubbed myself through the panties. Just doing that alone was almost enough to make me cum, but I stopped myself, I didn't want to blow my load and ruin the panties that quickly. Instead, I stopped touching myself and put my new jeans on over them before starting on some university work and some chores around the house.

By the time evening arrived, I was still wearing the knickers under my jeans as I relaxed in the living room playing some Call Of Duty. The lace knickers still felt amazing. I only wished I had tried this sooner and had more of a selection to wear. I heard a knock on the door and I went to answer it, expecting something my parents ordered to be delivered.

"Alex my man." Steve's face lit up when he saw me. "We have a party to go to."

"We do?" I questioned him, oblivious to this fact.

"Yeah, mate you really need to start looking at your text messages."

"Phone's dead," I replied matter-of-factly, and Steve immediately imitated my voice repeating what I said. Needless to say, I was bad at keeping in touch socially, I often let my phone battery die and did not recharge it straight away. Steve really did put up with a lot from me at times, though he always said that when I did try, I was really great friend. There were not many people that I would go out of the house for, but he was definitely one of them. He said that the date had gone so well that Lily invited him and me to a house party. I was so caught up in Steve's infectious good mood that I left with him right away, completely forgetting to change my underwear before I left.

The party was a twenty-minute trip on the underground in a large apartment close to central London. Clearly, the person hosting the party was well off, or their family was. Aside from a couple of people I recognised from university, I didn't know anyone except for Steve, Lily and Sophie. Aside from that fact, I was really enjoying myself. The conversation came easily and I found myself actually drinking and having fun. Steve and Lily flirted with each more with the more alcohol they consumed, and I could see where this was going before it did. Steve and Lily excused themselves and locked themselves in one of the spare bedrooms in the apartment.

Sophie and I didn't know anyone else so we sat back, enjoyed a few drinks and made light entertainment for ourselves by people-watching and joking amongst ourselves. She was surprisingly easy to talk to and didn't take herself too seriously. I was worried that I may be left on my own when Steve mentioned he was meeting Lily here, but I was glad Sophie had come with her.

"Do you mind accompanying me to the bathroom?" Sophie asked. Like me, she didn't know anyone else here and she didn't feel entirely comfortable walking around the large apartment packed with intoxicated people in their early twenties on her own. I fully understood that, especially with how horrific some men are, even more so when they've been drinking, so I followed her there, prepared to wait outside the door, but she told me to come inside. Like a gentleman, I turned away as she peed and she giggled at my innocence. She washed her hands when she was finished and she walked over to me until she was barely an inch away from my face. There was an excited, yet playful grin on her face as she kissed me. I let her lead and I followed as I kissed her back, aware that I was getting very excited downstairs. This wasn't the first time I had kissed a girl, but I hadn't done it anywhere near enough to be confident with what I was doing. Her hand grabbed my wrist and guided it to her breasts as she lowered the shoulder straps of her top to fully expose her breasts. Her large breasts were firm and perfectly shaped, I felt myself begin to get too excited and I panicked that I was about to blow my load just from the making out and the groping. I tried in desperation to think of random unexciting facts or images to calm myself down but without success. This goddess in front of me was actually making out with me and encouraging me to grope and play with her amazing breasts. I was so carried away, lost in the moment, that I was too late to react when Sophie started to unbutton my jeans.

"What do we have here?" Sophie asked with a huge smile on her face whilst I stood there mortified. Why didn't I ask Steve to wait a few minutes for me to change before leaving earlier? The night had been going so well that I had forgotten I was even wearing the pink panties that I had bought earlier. I couldn't answer Sophie, even though my mind was racing to find an excuse. I'd lost a bet, or it was a dare. Neither of those sounded like they would work. I was shrinking into myself, just waiting for her to open the door and reveal to everyone at the party what I was wearing.

"Hey, they look good!" Sophie said softly, surprising me. "Sexy even." She added as she moved close once again and began kissing me whilst rubbing my hard cock through the panties. I moaned, overcome with the pure arousal I felt at that moment. Sophie stopped kissing me briefly and backed off, slowly stripping off completely. I'd never been one that fantasised over what would happen in this situation, and I'd certainly never dreamed of being with someone like Sophie, nor during that moment would I be fulfilling a completely different fantasy of wearing women's underwear. Suddenly I was hungry with a passion for more, and I explored Sophie's body whilst I put a hand behind her head and pulled her in to make out some more. Sophie responded by grabbing my hands and positioning them so that they were crossed behind my back. I let her take control, kissing me whilst she continued stroking my dick through the panties. It was all too much for me and I closed my eyes as I passed the point of no return and spunked inside my newly bought panties.

"Oh, dear," Sophie exclaimed, giggling to herself. I lowered my head in shame, embarrassed that I'd blown my load from just being stroked through the panties.

"Sorry." I breathed, not thinking of anything else to say or do, but apologise.

"Hey, it's okay," Sophie replied softly, lifting my head by placing a hand on my cheek. She looked into my eyes with genuine warmth and kissed me on the forehead. "You're not like any other man I've been with before, and that's a good thing. Besides, you've had your pleasure, now it's time for mine."

Feeling reassured, I followed her lead as she came to just an inch from my face and started kissing me again. She pulled my free hand towards her and guided it down the front of her skirt, and inside her panties. I could feel her smooth skin as she guided me further down until I reached her soaking-wet pussy. I stroked her softly, letting her show me where her clit was, and she rested her head on my shoulders, enjoying the attention. Her warm breath brushed against my face and I looked at her face as she closed her eyes. This woman was incredibly beautiful, and as much as I had feared her shaming me for wearing panties or for even blowing my load early. It was the first time I had given anyone pleasure like this, and it made me happy to know that I was capable of making her feel this way. That feeling only intensified when her breathing grew heavier against my neck and I brought her to climax as her body shook against mine. She pulled my hand out and sucked one of the fingers clean before guiding my hand in front of my face so I could suck the other finger to taste her.

"That's better." Sophie breathed and she kissed me once again before we left the bathroom together. The people partying outside the bathroom were too absorbed in their conversations and drinking that they didn't notice us leaving the bathroom together. Downstairs, Steve and Lily were cosied up to each other on the sofa.

"So where have you two been then?" Steve asked with his eyebrows raised.

"Oh, I just escorted her to the toilet," I answered, not willing to give away anything other than that.

"How very gentlemanly of you." Lily smiled, giving her friend a funny look as if she could tell more had gone on than what I had just told her. For the rest of the evening, we enjoyed each other's company and drank some more as I tried to forget the fact I had my cum drying inside my new panties. We didn't really interact with anyone else at the party, but still, we had a great time. Sophie kept looking at me with a smile, and as we got ready to leave in the early hours of the morning, I genuinely hoped I'd get to see her again.

On the walk back to mine, Steve left out no detail as he talked about his night with Lily. The two of them had sex when they disappeared, which was no surprise really. Steve had always been better with the ladies than me. There was no way in a million years that he would be the one walking home at three in the morning wearing lace panties with his own cum drying inside of them from when he blew his load too early, that was for sure. Ever the good friend though, Steve ensured I got home and inside my house safely before he went off home himself. We didn't live too far from each other, but he always made sure that I got in before he did. When I got inside, I went straight for a shower, taking off the panties that were beginning to stick to my body. Once I'd turned off the water, I quickly towelled myself dry and then collapsed into bed.

Good Morning. I hope you don't mind me messaging here, I looked you up on Facebook when I woke up. How are you feeling this morning, not too hungover I hope. Are you up to much today?

I woke up to find the message from Sophie on my phone and it made me smile. Accepting her friend request, I then replied to say that I surprisingly felt fine and that I had no plans at all. She asked me if I wanted to meet up for lunch and I agreed. I quickly got dressed, feeling a little bit gutted that I didn't throw the panties in for a wash before I went to sleep last night.

I met Sophie close to lunchtime in Hyde Park by the Serpentine lake. On her way to the park, she had bought sandwiches, crisps and some chocolate so that we could have a little picnic in the park. Being the middle of spring, it was pleasantly warm and not swelteringly hot so we picked out a quiet spot on the grass and sat down.

"Are you wearing your panties again today?" Sophie asked after a little bit of small talk as we both talked about what we were studying at university and a few of our interests and hobbies.

"I'm not," I said with genuine disappointment. "By the time I got in the cum in them was sticking to my skin and I was too tired and a little too intoxicated to remember to put them in the washing."

"Oh, dear." Sophie laughed, grimacing at the thought of the cum sticking to my skin. "Do you mind if I ask how long you've been wearing panties like that?"

"Yesterday was the first day, I'd only bought them four hours or so before the party"

"No way?!"

"Yeah, caught wearing them on the first day I tried them on. Just my luck. Still, it's something I've wanted to do for so long, I don't know why. I'm glad I tried though, I love how they feel against my skin, and you were right last night, I feel sexy wearing them."

It was nice to have someone I could talk to about my fantasies of wearing panties. I was too embarrassed by the fantasy to bring it up with Steve, or god forbid, my family. Steve may understand, but he was the only close friend I had, and I didn't want to risk losing him as a friend, even if that risk was only minuscule. My family were very traditional; they would never understand. Sophie didn't seem to judge as she asked about my fantasy of wearing women's underwear which made it so much easier for me to open up to her. If anything she only seemed more intrigued by the matter.

After a perfectly lovely picnic in the park, Sophie asked me if I wanted to join her shopping. We went into Primark and she headed straight for the women's underwear section. She gave me one look up and down before picking a selection of panties in various colours and then had me follow her to the dressing room. The assistant looked at us dubiously but still allowed us through. I know some places didn't like couples going through to the rooms together.

"Try these on," Sophie said as she passed me a purple lace pair of knickers first. The pattern on these was more risque since they were a little transparent. Nervously, I took off my jeans, looking at the locked door every time I heard someone pass to go into another dressing area. Whether it was because of the risk of being caught, or the fact that I was wearing panties again, I had grown hard once again. Sophie noticed and smiled at me with a wink. She started stroking me but stopped abruptly.

"We wouldn't want to hand these to the cashier covered in cum now, wouldn't we? Not when they look so good on you." My face grew red at her playful, taunting words, but my cock remained rock hard. I tried on every one of the panties Sophie picked up, and in the end, she decided they all looked good. As we left the changing rooms, I was back in my boxer shorts, but I was still very hard. Because I wasn't that very well endowed, however, it didn't look too obvious. As we approached the till Sophie handed the panties to the cashier and paid for them to my surprise.