The Origins of Pippa

This story is the mostly true tale of how I discovered my kinks, including crossdressing and bdsm elements. Any resemblance to anyone of any place real is entirely coincidental.

This is also my first story so any and all feedback is welcome as I would love to improve my stroytelling.

I was 18, single and horny. Always so horny! I'm sure you all remember what it's like at that age as a horny male virgin, if left to my own devices I would have done nothing but masturbate all day, sleep then repeat!

As I lived in a VERY rural area with no real night life or anything resembling excitement for miles around the internet became my way of living out some of my fantasies and exploring my sexuality.

For a long time I'd been gradually exploring more and more away from the standard, hetero vanilla porn categories of amateur, hardcore, milf type stuff. I had really got into bi stuff, bdsm and even some gay porn. All this exploration led me to a website for dominant and submissive guys to find each other for talking, advice and to the lucky few meeting up and acting out some fantasies.

I'd been on the website a few months taking part in chats on the forums and asking for advice for someone who was curious but had no experience with men at all. Then I got a message one day from a guy in Birmingham (at least 50 miles away from where I lived at the time) saying that he would like to get to know me a little more with a few to meeting and training me up as a submissive. We spent the next few months chatting regularly in the evenings, even building up to some webcam chats and exchanging of numbers.

I'd been incredibly honest with him, giving my real name, sharing my pictures with him and he knew pretty much what I did most weeks, all I knew about him was he was called Chris, was in his mid 50s and lived in Birmingham. Yet, despite this I trusted him so much, I knew he wouldn't push me, wouldn't reveal any of the secrets I'd told him and wouldn't do anything with me I wasn't comfortable with.

One weekend in October I was planning on visiting a friend in Birmingham who had not long moved there for uni, with the plan to get very drunk with a few friends from college and some of their new mates from uni. I told Chris this one evening before but let him know that as I was with friends it was unlikely that I'd have time to meet up even for a drink or a chat. He was fine with this but said that he'd be free most of the weekend and reminded he that I had his number if anything changed.

So Saturday rolls round, we go out around Birmingham and get very drunk quite early on and this causes my teenage libido to go into overdrive. So I texted Chris:

'Good evening Sir, hope you're well and this isn't too late. I want to meet you. I can sneak off early in the morning. Is this OK?'

I sent the text and felt my heart rate increase, was I really going to do this? Meet someone who was a relative stranger in matter of hours, leave my friends to fulfill my deepest, darkest and most deprived desires? As I was thinking my phone buzzed:

'Good boy, I will text you the address in the morning when I'm ready. I will assume you won't be able to shower in the morning so you will do that here. Understood?'

'Yes Sir.'

No turning back now. I looked at the time, it was around 12:30, still several hours of drinking and making a fool of myself to go before we were heading back to my friends halls.

Those hours passed and we went to bed, I had set my alarm for half past six the following morning. I woke and snook out, texting the others saying I needed to go back and was getting an early coach back northwards.

Really, I had snook out and headed to the train station around the corner, knowing that there would be taxis there and somewhere I could get a drink and a bite to eat as I had no idea what the rest of the day would entail.

Around an hour later I was sat in a coffee shop waiting with my phone in hand, anxious as to when I'd be allowed to finally meet Chris. Moments later, my phone buzzed and I had a text from him with nothing but the address and the word 'Now!'

I hurried to the taxi rank and got in the first one I saw asking if he could take me to the address I'd been given, he nodded and I got in.

15 minutes later the cab stopped on a normal looking residential street, terraced house slightly set back from the street with a small front yard stood on both sides of the street and I looked for the number I needed. 16. I don't know what I expected, a neon sign pointing me toward it but I felt so stupid as I walked around looking intently at the front doors of every house instead of just counting my way to the right one.

Eventually I found it, composed myself and knocked gently, hoping beyond hope that this wasn't just some elaborate trick or prank on some naive teenager.

As the door opened I got my first glimpse of Chris in the flesh. He was wearing a dressing gown that covered his ample frame but still let me know he was a large man.

"Come in boi," he ordered in a soft voice.

I obliged and went in, shutting the door behind me and standing there waiting, unsure what I should do or how this would work.

"Clothes off, put them in your bag and leave the bag by the door then come in here," he said as he walked to a room just off the hall to the right. I did as I was told, got completely naked, exposing my shaved genitals (I always kept them completely hairless) to the cold air in the entrance hall. I tentatively stepped into the room which was obviously his living room, a sofa, a coffee table, TV, a couple of lamps. Nothing out of the ordinary.

"Stand there boi. I need to inspect you, see if you need a wash. Arms by your sides for now and don't move a muscle."

This last command sounded infinitely more menacing than anything else he had said to me so far, I could tell I shouldn't disobey him and would have to follow every instruction.

As I stood there he walked around me very slowly, looking at every inch of my body, sizing me up. He lifted my arms and looked at my armpits. He told me to bend over and he inspected my arse hole, the first time anyone else had ever even touched it. When I stood back up he took my balls in his hands and seemed to be weighing them. Then he took my cock and pulled the foreskin back as far as he could. This caused me to shift a little uncomfortably. He paused. Moved his hand back to my balls and stood up, facing me. Then he squeezed gently and said, "If you disobey me, there are consequences, slut!" On the last word he gave a much harder squeeze.

"Are you ready boi?" To potentially do everything we talked about?"

"Yes Sir."

"Remind me of your safeword"

"Pippa"

"Good boi, hands behind your back." As he said this I saw he had a few things in his hand, the first was obviously a hood as he pushed it over my head, plunging me into darkness. Luckily it had a mouthhole so my breathing wasn't restricted. He then placed something round my neck, a collar surely and some velcro cuffs on my hands leaving me pretty much helpless as he tugged on the collar and led me back into the hall and upstairs...