I can’t really remember how we got chatting, he was polite, I remember that, and I was a bit new to it. I’d been through a bad time, my parents were killed while I was at college. They left me with money but with a big hole in my life. I’d had a sheltered life I guess and was desperate for some excitement. All my friends seemed to be having wild times and I’d never done anything. I was a twenty year old virgin. I don’t think I’m shy, I can talk to anyone but I never seemed to have much joy with men. If I threw myself at them it seemed to scare them away, if I played hard to get I didn’t get got. I guess there are lots like me really but that’s not how it felt. I read a couple of newspaper stories about people who met on the Internet and so I got chatting.

All kinds of weirdos tried it on of course but I wasn’t having any of that. I might be lonely and frustrated but I’m not daft. He was different. He seemed to just want to chat, he was a lot older than me and I guess I treated him more like a father or an uncle. It must have been a few months I guess before we talked about sex at all and then what with one thing and another I started to tell him how much I wanted to lose my virginity in a really interesting way, like an orgy or sex in an aeroplane or on the top of a mountain, something memorable. We came back to it now and again and gradually he got interested and I suppose that’s where the offer came from. I offered him my virginity if he could lay on the most memorable ‘event’ anyone could think of.

We talked about a few possibilities but he gradually sold me the idea that it had to be a mystery. I wanted to know what he was going to get out of it and we ended up with a deal. I had to trust him completely, it would be a mystery, I would get deflowered, he would fulfil a fantasy he had. We both got out what we put in and both of us would make it worth remembering. I don’t think I expected it to go anywhere after than, I think we’d planned to just be good friends but at least I would have the virgin thing off my mind and then maybe I could get a man my own age.

I fixed to meet him in London, I knew he didn’t live in London, he already told me he has a place in the county about an hour or so out of town. London seemed the right place, I had a flat there, quite an expensive one, bought with some of the money my parents left me so it was easy for me.

We met in a coffee bar and it was brilliant from the word go. He was easy and relaxed and just like he was to chat to, a bit like Sean Connery only maybe a bit younger, you know what I mean, just enough white hair to make you feel safe and a tan that made him look relaxed. We sat there and talked for an hour I guess until I was feeling up for anything. He was quite clear and firm and I loved it.

“You will do exactly what I tell you; you will have some choices and you can back out right up to the end, you just have to say, are you ready to begin?” Was I just.

“First we have to buy some clothes, let’s go shopping.” Hey wow, I didn’t know he was going to buy me things.

We disappeared into a side street and then into a boutique, I guess he knew where he was going because they seemed to have exactly what he was looking for, I suppose he’d dome some research. He found a lovely lacy white blouse, not see through but holes in the lacework so you could tell what was underneath, very sexy. They had a little table where he sat and had a coffee while I went off with a really nice sales lady, I mean a lady, like she was twice my age but looked really great. She helped me find the right size and I came back out and walked across the store to where he was. The sales lady was standing by my side. He looked at me and then at her.

“What do you think Marion?”

Mmmm he knew her name so he had been here before.

“Maybe without the bra?”

“Yes I think you may be right, shall we try that.” In two seconds I was back in the fitting room and in and out of the blouse minus my bra. I walked out again. I had hardly ever been out of the house without a bra but I do have good tits which are OK on their own, I guess I’ve just been a bit prudish up till now. I felt a bit wild and kinda exposed. The blouse covered everything but there were enough holes in the lace that anyone who wanted to look could see that I was naked under it. I didn’t feel like a hussy because it was such a classy blouse but I did feel different and it must have showed.

“Much better, much better.” His voice filled me with confidence and I felt brilliant.

“Now that skirt I picked out please Marion, no stockings, just those nice white shoes.” Back to the fitting room. It was a little kilt. You know the kind that wraps across the front of you. Marion had a look at my underwear, suspenders and my best panties but she just shook her head and gave me these white lacy briefs with sort of frilly edges, I don’t remember them all that well and I don’t have them any more so I can’t tell you the details but off came my panties and suspenders and stockings and on went the frilly briefs and the kilt with a pair of neat white shoes with three inch heels. The briefs were very light, almost felt like I wasn’t wearing any and my legs being bare emphasised that even more. I was paraded out again and met with total approval, he clapped gently and made me twirl around. He took out a little camera and made me pose at different angles.

“I wanted to give you a record of this day, something for you to keep.” I knew I was being led down a road. Here I was for the first time in my life in an expensive boutique being dressed by a woman who obviously knew everything there was to know about being discretely sexy and now posing for pictures feeling slightly naked in my new clothes. I could see in the mirror that I looked stunning. He knew what he was doing. Feeling expensively coquettish was brilliant for my confidence and knowing that he had planned this transformation made me ready to do anything he said.

He let me walk around the shop a bit and practice sitting down and standing up so that I was feeling OK with the length of the skirt and the way the kilt flap behaved. It wasn’t revealing really, I mean if the top flap blew back the one underneath covered everything. I’d have to get hold of the edges of both flaps and pull them back myself if I wanted to show anything, but it looked risky and that was what made it feel so great wearing it. He could have taken me there and then I think and the day would have counted as well done, that gives you an idea of how good the clothes made me feel. When I was ready we ventured out into the street.

I don’t know where we walked but he got me used to being out in those clothes. I’ve never been a flirt but I noticed people looking at me, I kept close to him. I liked the way some guys looked a bit jealous of this older guy with the stunning chic. You could see it in their eyes. I loved it, showed off a bit to make them more green with envy, I liked making him look good because he had made me look gorgeous.

“You get a choice now” he said, “you don’t have to do the next bit but it’s always been a fantasy of mine so please do it if you can.”

“What have I got to do?”

“I’ve always loved those pictures you sometimes see of girls whose knickers have lost their elastic and fall down round their ankles.” He grinned a bit sheepishly.

“ I know it’s silly but you’ll have to cut the elastic and then walk along and wait for them to drop.” I giggled.

“Have you got a pair of scissors?”

“Of course.” He handed them to me.

“You can reach inside the waistband of the kilt and cut the elastic.”

“You do it.” I don’t know what made me say it but I wanted him to touch me, the whole idea seemed wild and wicked and when I looked up and down the street there seemed to be no-one around. The thought popped into my head that he had picked the street specially but that made it all the better. It could have felt like I was being manipulated but it felt like it was planned and therefore safe. He didn’t need any second bidding. I felt him pull the waistband back and then the funniest feeling as he cut the elastic and a bit of the panty down between my buttocks, I could feel them go loose instantly, they weren’t going to stay on long. He walked ahead of me taking out the camera.

“Walk towards me and lets see what happens.”

I walked forward and he walked backwards just in front of me clicking away and I felt the fabric sliding down my legs. I kept looking at him, smiling, pretty much saying take me now as I felt the slight tug of material across my thighs and onto my knees. In another second they were round my ankles.

“Walk past me then step out of them and bend down and pick them up.”

I walked, short little steps with my panties round my ankles, he circled behind me snapping away. I was thinking I hope that’s a digital cam, as I don’t fancy collecting these from the chemist.

As he got in position behind me I stepped out of the pretty lacy cloth and bent down. I knew what he wanted and even as I bent I realised which way the wind was blowing. I let the skirt blow up over my ass and literally posed there showing him everything he could have wanted to see in the middle of the street. I was dreaming slightly, wondering what was happening to me, as his hand brushed my skirt down and gently lifted my shoulder pulling me upright and sweeping me into his arms.

“Beautiful, beautiful” he said. I melted. I felt so sexy it was unbelievable and I was still a virgin, where was it going to end.

We wandered along the street, I think he was giving me time to get used to being naked under such a short skirt. As we passed a waste bin he smiled at me and dropped the panties into the bin. You can tell why I can’t remember much about them. Lace and loose at the leg and no use to anyone now.

That street led out into a much busier road, I should know where it was but I was in a bit of a daze by now and just floating along on his arm.

“Next fantasy.” He said. What was he going to do, strip me in the street?

“We are going to catch a bus,” he said “one of those tour busses where the top deck is open. I want you to go up the stairs ahead of me and I’m going to take pictures up your skirt. I know it’s a cheap little fantasy but I think all men have it and most of them aren’t walking round London with a stunning blond with no knickers on.” Again that sheepish grin.

“How long have you been waiting for this?”

“Since I was about fourteen,” he said. I laughed. I couldn’t wait to get on the bus. I felt so confident with him by now, the way everything had been planned, I just knew that this wasn’t the end of the story, this was just fun bits to get me going, and I was going.

It’s not as easy as it sounds walking up the stairs of a bus as it’s moving along and trying to give someone a look at your pussy for long enough for them to take a picture. I was getting a bit bold by now so when I got to the top step and I could see there was no one up there I turned round and looked down the stairs. I could see the camera lens and there was no-one behind him. I flipped up my shirt and let him see my crotch full on. I think he has one of those burst mode things on the camera so it takes loads of pictures very fast. I felt such a slut but it was really fun. I was having the time of my life. None of these things were part of any fantasy of mine but I knew they were his. I was a just a blank sheet of paper ready to be written on.

We sat at the front and watched the buildings go by.

“That was very brave of you, flashing me like that, how did it feel?

“I felt wild” I said.

“Did it turn you on?”

“You bet.” I knew what he was going to say next.

“I’ll do it again if you like.”

He moved back a couple of seat and took out the camera again.

I stood up facing back down the bus. There was no-one on the top deck, I can’t imagine how he could have arranged that, I guess it was just luck but it made it all the better for me, I just felt that I was meant to do this because there was no-one there. I picked up the corner of the kilt with one hand and lifted it across my body, snap snap snap I took hold of the other corner, click click and drew it across the other way and there was my pussy out in the fresh air and straight into the camera. I held it for what seemed like a long time and he just grinned.

“Undo your blouse and let’s see the whole thing.”

The mood I was in by them it’s a wonder I didn’t throw it off the bus. I had the buttons undone in a flash and pulled it open holding it with my arms while I pulled open the kilt again. I don’t know how many pics he took but I loved every second of it.

He sat me down again and handed me a dice.

“Shake the dice onto the floor,” he said “whatever number comes up, that’s how many buttons you can do up on your blouse.”

I looked at the dice in my hand. What if I shook a one, which button would I do up.

“You can back out if you want to, it’s your choice.” Back out, sitting their virtually naked on the top of an open bus - not likely. If it was a one then so be it. I threw the dice on the floor. Two. I laughed out loud.

“Better than a one” he said. I carefully did up two buttons.

He gently kissed the back of my neck.

“Well done. Passed every test, you’re a star.” That’s how I felt. I know I was glowing, I could feel him loving it and I was just giving off heat.

“Time to get off”, he said, getting up and leading me down the bus.

“Mind how you go on the stairs in case someone is coming up.”

“So long as they haven’t got a camera.” I giggled.

Back on the street I was led down a small road and realised that we were getting into Soho.

“You may not have been anywhere like this before, try not to look too surprised and remember you can always say no.” We turned a corner and he led me into a shop that opened my eyes. It was a sex shop I suppose though mostly it sold clothes, not just any old clothes, lots of leather and rubber and stuff like that. He led me over to a rack full of leather cuffs and collars.

“Pick some cuffs that you like.” It felt like a command more than a request and it sent a tingle through me. I reached out and picked up a pair of cuffs and slowly wrapped them round my wrist. It was a deep sensation, I’ve never felt anything like that before. I didn’t know what to think but they were a bit hard. He obviously saw something in my face and reached over to another pair.

“Try these. They’re fur lined.”

I wrapped them on and it was a great sensation. He helped me do up the buckle. It was soft but firm at the same time.

“Those?”

“Mmmm”

He left the one cuff attached to my wrist and picked up a matching set of leg cuffs.

“Try these.” Again the firm tone I lifted up my foot and he knelt down on one knee so that I could rest my foot on it. I knew from there he could see my pussy as he bucked it onto my ankle.

“Other leg” I changed legs and the second cuff was cinched up.

He smiled and stroked my skirt down across my bum.

“You’ll need a collar as well, shall I pick it?”

I nodded and in a moment a collar was being buckled around my neck. Not tight but just enough that I would always know it was there. He picked up my left wrist and buckled on the last cuff.

“There that looks lovely.” He turned to the shop assistant. “We’ll take these. Oh and do you have any of those little buckle locks? Look at yourself in the mirror while I deal with this.”

I turned to the mirror in a trance and saw the most sexy thing I’ve ever seen, me; the little white skirt and lace blouse looked so demure yet provocative at the same time, the cuffs in black leather set it off in a way that I’d never imagined. The collar made my face look twice as interesting. I just felt so sexy I shouldn’t have been allowed out. I thought anyone, just anyone, would want to have me right there. God knows who was going to have my cherry - it might be the next person who walked in the shop the way I looked.

I started to take off the cuffs when he came up behind me.

“Leave them on, they suit you.” With that he took each cuff and put a tiny padlock though the buckle and clicked it shut. There was no escape. I was cuffed and collared even though my limbs were free to move I felt I could be locked in place anywhere he decided. This really was becoming a day to remember. He led me out of the shop. Well that’s what it felt like although he didn’t actually clip a lead onto my collar until we got to the car park. In that vast underground space where there was hardly a soul around he put a silver chain onto my collar and I fell into step a pace behind him being led along. I knew I was going to do anything he said.

We came to a big silver grey car, I don’t know what it was, I’m no good about cars but it looked expensive and sleek.

“We are going out into the country to my place now, it will take an hour or so depending on the traffic. How are you feeling?”

“Wonderful, very horny, ready for anything, everything.”

“Do you want to travel in the front with me or the traditional way.”

“What’s the traditional way.”

“If you choose that, you’ll find out” he said with a little gleam in his eye.

“Is that another of your fantasies?”

“A little maybe.” I took a deep breath.

“I’ll go the traditional way.”

He reached out and undid my two buttons and turned me around. In one smooth movement he had my blouse off and my hands cuffed behind my back. He knelt down and clipped my ankles together, and as he stood up he slowly reached for the clip on my kilt and whisked it off. I stood there, naked, hands behind my back, ankles cuffed together, unable to move. He flipped the boot open, swept me up, and laid me on a soft blanket. He dropped another blanket over me.

“Try to get some sleep,” he said “you’ve a big day ahead of you still.” The boot closed and there I was, naked, bound, and in the dark. I had no idea where I was going, a full scale abduction, the traditional way. The motor purred into action and I felt the movement of the car. I heard some gentle music in the background and then his voice.

“Are you OK there?”

“Yes.”

“You can call anytime if anything is wrong.”

I relaxed, it was warm snuggled into the blankets and what with the motion of the car and the music I guess I must have fallen asleep because the next thing I knew the car had stopped and I heard his voice.

“I’m going to open the lid. Close your eyes for a moment and let them get used to the light, as it’ll seem a bit bright.” I heard the lid open and felt the light through my closed eyes. I looked up and he was standing over me. He reached down and changed the lock on my ankles putting a short piece of chain between them and then lifted me out. I looked around. The car was parked next to some brick buildings and I was standing on a paved drive, to my left was a neatly cut lawn and a high hedge beyond that. He held my elbow and turned me towards him.

“This is your last choice. You can get dressed and we’ll go indoors and carry on from there, I’ll show you the house, we can have a little to eat and we’ll end up in the bedroom. You can swim in the pool afterwards or have a sauna or whatever you like. Or you can carry on with the adventure but from now on there’s no going back, no stopping, if you carry on now you go all the way.”

The sunshine warmed my skin. Standing there naked was delightful. I took a few steps forward walking across to the grass. I kicked off the shoes and dug my toes into the grass. Even with my wrists cuffed behind my back and my ankles hobbled I felt free and I knew I trusted him. There was something warm and safe about this place. I took a deep breath, felt the fresh air and listened to the birds singing. I didn’t want to just end up in bed, though I just knew it would be a nice bed and probably a romantic bedroom, thoughts of a four poster flashed into my mind. I turned around slowly looking at the garden, wondering where the path led that went behind the building. Not to the house for sure. If I backed out now I’d always wonder what I’d missed.

I turned back and said “Take me all the way.”

“Put the shoes back on and walk over here.” I did as he said and shuffled over to him. I could step about a foot before the chain came tight. I must have looked a little silly because he bent down and freed my legs. My hands were still cuffed behind me. He gently stroked my hair and ran his hands down my sides and round my waist, walking round behind me and running his hands up over my body to gently cup my breasts in his hands. He teased the nipples with his fingers, they were already getting hard, what with being out in the sunshine and my arousal. I wasn’t ready for the next thing. He walked round in front of me and kissed my forehead and then my eyelids, I closed them without thinking enjoying the gentle touch of his lips, feeling his breath close on my face and then a soft blindfold came over my eyes and he knotted it behind my head. I couldn’t see anything. I couldn’t really even open my eyes. He kissed me on the lips as the knot came tight and then his lips lingered teasing me forward trying to stay in contact. I heard the chain click onto my collar.

“This way.” I was drawn forward, had no choice. We must have walked round the corner of the building, down the path I had seen earlier round a corner and into what felt like a big space. I was hypersensitive I think, like a blind person, I could tell the way the sound of our footsteps changed, there was no echo off the walls. We crossed the space and then the air stilled and I realised we must be in a building, a barn or something big. I could smell leather and other things that I couldn’t make sense of, country smells I guess. I stood still feeling him move around me.

“I’m going to change your shoes, boots, pick up your right foot.” I felt his body next to me, letting me lean on him a bit so I wouldn’t fall over. He eased my shoe off and then guided my toes into a boot pressing the heel in and then zipping up the boot. All the way up to my thigh. He ran his hand up my leg smoothing the leather into place, the back of one of his hands ending up pressing gently against my pussy. His hand moved slowly forwards, an even pressure massaging my labia and then sliding away. He must have heard me catch my breath. The other boot went on in the same way and again I was massaged. This time I knew he was standing in front of me. Both his hands ran down over my belly and down there again. Slowly very patiently he teased my labia apart opening my pussy so that I could feel the air, cool on the wet bits inside. I read about girls getting wet and always wondered if someone could do it to me. I was praying I wasn’t too sticky or disgusting. I guess not because he kissed me again. As his lips held me I felt him wrap a thick fitted belt around me and fasten it in the front. I don’t know how wide the belt was, well I do now but I didn’t then. It felt like about six inches with a curve to it almost like a waist type of corset. The buckle must have been huge, I could feel it flattening my tummy. He smoothed that around me, or felt it because he liked it, I don’t know which. And then his finger ran through my pussy again. I was just shuddering every time he touched me by then. There was a pause as he moved away and I heard strange sounds, little bells ringing, I had no idea what he was going to do until he held my nipple in his fingers. He twiddled it a bit and then I jumped as some sort of clamp grabbed and then I knew there was a bell attached to my nipple. I was more ready for the second one but it still made me jump.

His hands cupped my breasts and shook them slightly. I felt the drag on the nipple clamps as I heard the bells ring.

“You’ll stop feeling the clamps in a minute or two.”

He stepped away from me again and came back with some sort of leather straps that went over my head. I had no idea what it was. He kissed me again.

“Open your mouth.” I obeyed and then felt some metal right across my mouth. There was a jingling sort of sound alongside my cheeks and then I knew I was wearing a bit, like a horse, except it was curved so it fitted under my tongue. Suddenly it was making sense, I’d seen pictures of pony girls on the web, always thought they looked sexy even if kind of kinky.

He drew me forward a little and then started moving something behind me. I felt him attach something to my belt then he undid my hands and clipped them to the shafts that were attached to my belt. He ran his hands over my head harness adjusting something then took off the blindfold. My eyes adjusted to the light and I tried to look around me. I couldn’t see anything to my sides, I was wearing blinkers. As I stood there he brought up the lights and I saw myself in a couple of huge mirrors. They were right in front of me facing inwards at a slight angle so I saw myself about a quarter on from both sides. As my eyes adjusted I could see another mirror behind me and there I was connected to a little cart. Like a pony and trap. There was a seat on it and I knew who was going to sit there. At the side of the trap ready to use was a long whip. I shuddered slightly as I saw it, it was bound to get used. I gazed at my lovely virgin ass and wondered what it might end up looking like. And then I remember the other thing about ponygirls. They have tails and I knew where they went. Would he do that to me?

“You look wonderful, every inch the part. How does it feel?”

Of course I could not talk, but offered him my rump, as if to say “I’ve seen pictures like this but being the real thing is out of this world.”

“Ah. I see you know what’s missing.”

His hand came into view holding a long blond tail that exactly matched my hair. He trailed it across my face. It was smooth and silky, it must have been real hair, ponygirl hair not horse hair. Then I saw the plug on the end of it. I’ve never seen a butt plug for real, pictures yes, but not this sleek black monster at the top of the tail.

“I know it looks big but we’ll take our time. Bend forward.”

I bent and he helped me. Actually with the belt round my waist held in the shafts which were supported by something, it was easy, almost relaxing. I’ve never had anyone touch me there, my pussy isn’t the only bit that’s virgin. I had no idea what was really going on, maybe his finger went in first. Oh gee! His finger up my bum, but he was so gentle. He put something on, cool and slippery, and something slid into me, in and out. Oh what a feeling, and then I knew it was the plug, slowly pressing forward gently, rotating a little this way, a little that, but always getting bigger and bigger. I held my breath, tried to run away from it a bit, but there was nowhere to run. I couldn’t move forward because I was clamped to the cart. I must have been squirming around because the bells on my tits were ringing a lot. The more he pressed and I couldn’t get away from it, the more I wanted it. But at the same time it was getting more and more uncomfortable, painful. As the pain rose I reflexively pressed backwards, ramming myself back onto it to get it over with. And he pushed hard in return and then plop it was all over. I felt my sphincter clamp round it and the pain went away. He eased me back upright and there I was in the mirror, the most amazing blond tail swinging between my legs. I almost came on the spot.

I watched in the mirror as he sat in the cart and picked up the reins. The whip was in the other hand. I watched as the whip came out horizontally and switched me on the ass. I was mesmerised by it and stood still until it hit me. I could have moved but once we started moving I couldn’t see behind me because of the blinkers. The reins pulled my head around to the right and I turned right. There were a few more switches so I picked up the pace jogging along as well as I could in the boots. We ran out along a path past the barn and I came to a gate that was closed. I stopped and felt him get off the cart. He came into view in front of me opened the gate and led me through. It was a chance to get my breath back. I heard the gate close behind us and the weight changed on the shafts as he sat down again. I could have started but I was getting used to the switches on my ass. Whack and off we went again. Whack, a bit faster. There was only one path and it took us around a small field with a lake in the middle. It was an idyllic setting. I could see why he wanted to bring me here, even without the pony play it would have been lovely. Whack, a bit faster still. I was jogging along quite quickly now and realised that the track went right round the field. There might be no end to this. I’m pretty fit but in strange boots and with a butt plug in my ass it was a strain pulling a grown man in a cart. The stinging whacks on my ass didn’t give me much choice and I knew I was enjoying being worked. He was right about the bells on my tits, I couldn’t feel the clamps at all but I could hear them ringing.

We did a whole lap and as we came round again I could see that the only tracks on the ground were two wheels and hoof marks. No wonder the boots felt a bit strange, I was wearing thigh-high hooves. As we went round the second lap we came towards a point where there was another path leading towards the middle of the field. The reins pulled my head around and I trotted down it. In front of me was a slight incline, well when I hit it more than a slight incline, quite a little hill. I could see that it was a small mound raised up to give a better view over the lake but pulling the cart up it was no fun. Half way up I was struggling and the whip was hitting both sides of my ass one after the other. I just knew he was enjoying beating me and it was fun. Sweating up that hill with my ass on fire I was in a different world. By the time I got the cart to the little plateau at the top I was breathing hard, sweating and feeling like a pony through and through. The reins both pulled at once, which had to mean stop and I felt the brake come on the cart. We were in a little flat spot on top of the hill surrounded by low bushes with lovely flowers. The scent of them was trapped in the clearing. There was a blanket on the ground, he must have put it here before he set off this morning.

I was unclipped and drawn over to the blanket. I did exactly what he made me do, I was breathing too hard to resist and I was a pony. He laid me on the blanket and spread my legs. There were rings on the back of the boots and they were clipped to something I couldn’t see. I knew what was coming. He took my hands and spread them above my head and attached them in the same way. I was spread wide in the sunshine. With the blinkers on all I could see was sky. The air was full of the perfume of the shrubs around us. As my breathing calmed he began to stroke me, still wearing the softest kid gloves. Every touch was like warm electricity. I don’t know how he undressed while still giving me total attention but I gradually became aware of his skin touching me. He began to kiss me all over; the tops of my legs above the boots and then right on my pussy and up over my stomach and tits and then my neck. I was flying as his lips came onto mine and his weight gradually came onto me. He kissed me again.

“Are you ready?”

“Yes” I nodded.

“If you get taken like this, you know you’ll always be a pony girl.” He breathed.

Nothing seemed more obvious and nothing felt better.

“Yes” I nodded. “Oh yes!”