Escorting Kinky Escapades

I have previously written about some of my experiences in my early 20s when I worked part time as an escort. Some of you who have been kind enough to leave positive feedback and have encouraged me to write more about what I got up to.

In this 2-part story, I recollect a couple of my kinkier and more unusual experiences.

Chapter 1. "Are you sub?"

I am often whether clients requested Dom/Sub type services.

Now I'm going to be honest. Quite a lot of the guys I saw expressed a desire to explore domination, BDSM or similar. However, most of the time I found their requests a bit a lame and not particularly erotic. I blame Fifty Shades of Grey! After those books and movies came out it seemed like everyone wanted to try BDSM. That could be handcuffing or blindfolding a girl, a bit of spanking, wearing latex, "rough" sex, using abusive language and much more.

However, generally what most guys didn't understand was that the eroticism of a dom/sub relationship is not really about those specific activities. Rather, in my view, 99% of it is mental. The feeling of dominance and control or the feeling of vulnerability and relinquishing control. Just because a girl is wearing a blindfold, and you are occasionally slapping her arse does not turn it into a dom/sub relationship.

In fact, the most erotic dom/sub encounters I've ever experienced didn't involve any equipment or costumes.

For example, I recall one afternoon with a client called Dave.

I should say at this point that everything in this story happened between two consenting adults. While outwardly the scenarios we played out might suggested coercion, ground rules and safe words had been discussed and agreed in advance.

I'd met Dave a couple of times before. He was single, in his late 20s and had previously booked me to accompany him to his work events. Pretending to be his girlfriend and chatting to his colleagues was so much fun, but that's not today's story!

On this occasion, Dave booked me for the weekend to be his plus one at a colleague's wedding.

Dave picked me up in his Audi and, as agreed in advance, we got straight into character,

As it was going to be a traditional church service, I had chosen a fairly conservative navy dress, which had a fitted top half and an A-line skirt that fell just above the knee. Finished with sheer tights and moderate heels.

I greeted him with a kiss on the cheek. He mumbled something back but seemed lost in his own thoughts as we drove off. In my experience, when guys are in that type of mood it's best to let them be. I put the radio on, and we travelled on in silence.

After nearly an hour, Dave's silence was now being interspersed with occasional sighs so I thought I should say something - we couldn't spend all day like this. I put a hand on his thigh and gently asked, "Darling, is something wrong?"

Dave breathed in deeply, stared straight ahead and then said, "I can't believe you're wearing that to the wedding!"

I was completely taken aback. I'd spent ages thinking about what to wear and had ordered an expensive designer dress that I thought he'd love.

Regaining my composure I asked, "What's wrong with this? You told me that I should wear something conservative and classy!"

Dave immediately snapped back, "Exactly! And instead, you've deliberately put on something that makes you look like a tease. Could your top be any tighter? And look how fucking short the skirt is!"

I was genuinely puzzled by his outburst. The top of the dress was fitted, which inevitably meant that it hugged the contours of small boobs, but there was no flesh on display. As for the skirt, it had obviously ridden-up to my mid-thigh when I'd sat down in the car but that was normal for a mid-length dress.

Dave fell back into silence. I was now pissed off with him and was happy not to speak.

As we rounded a narrow country lane, the SatNav showed that we were approaching the small village where the wedding was taking place. However, without warning, Dave abruptly took a right turn onto an even narrower track and pulled up on the grass verge.

I said nothing, I wasn't going to get into an argument with him. He opened his door, got out and walked off into the field while lighting a cigarette. I assumed he was calming down and just needed a short walk and a smoke to regain his composure.

A few minutes later I saw him heading back to the car and he seemed more relaxed.

He made his way to my side of the car and opened the passenger door. I offered him a conciliatory smile, pulling down on the hem of my dress to emphasise that it really wasn't that short at all.

However, in that moment the look of annoyance returned to his face.

Dave tugged my arm and in silence led me to the front of the car. Without warning, I felt him shove my shoulders, pushing me face down over the bonnet. He held me firmly in that bent over position.

My front was squeezed against the bonnet, and I could feel the warmth of the engine through my dress.

Dave lifted the back of my dress and in the same movement I felt his fingers dig into my tights. I heard the sound of the nylon ripping. I tensed as I felt a cool breeze on my skin where the hole in my tights was exposing my bum.

Probably a strange thing to pop into my head at that moment, but I realised I was wearing £200 Bordelle knickers and hoped he didn't tear them too. He didn't but I felt one of his fingers hook the thong back, lift it out of my arse crack and pull it to one side. With his other hand he eased aside the gusset.

Next, I heard him unzip his flies. I looked over my shoulder to see him releasing his cock through the gap in his suit trousers. While I didn't want to break the role play, I did at this point whisper to him, "condom," to remind him that I didn't offer bareback services.

Dave nodded and immediately went back into character. "Do you think I want to fuck you? You've got to be mad if you think I want to put my cock into your dirty little pussy. I wouldn't even slide it in you arsehole you slutty bitch."

I watched as with one had he started wanking himself, hard and urgent. Pre-cum was already glistening at the tip. He drove his other hand between my legs. Three fingers went straight into my cunt and while he jammed his thumb into my anus. I gasped, I was already soaking wet and could feel the early tremble of an orgasm. I arched my back and involuntarily pushed my bum into his hand so that his fingers and thumb could go deeper.

I heard his breath and the tempo of his masturbation quickening - he was going to cum any second. I was already there. My legs began to shake as an intense orgasm pulsed through my body and juices flowed from my cunt onto his hand.

Dave gave a big sigh as cum exploded from his penis. He aimed it for my bum. I could feel his sperm landing in my arse cheek, gently trickling down my crack and then down the back of my nylon covered thighs.

He pulled his hand from between my legs and used it to reach round to my face which was still pressed onto the bonnet of the car. He prodded his fingers, which were dripping with my juices, into my mouth. Instinctively, I sucked them clean, my tongue savouring the taste of my own cunt.

Dave didn't wait. He pushed his flaccid cock back into his pants and my dress fell back into place as he stood me up and walked me back to the car. The whole thing, from bending me over the car to both of us cumming, had probably lasted 3 minutes.

We sped around the country lanes and ten minutes later were sitting down on the wooden pews of the church. I sat through the entire service feeling the sensation of his cum on my thighs and my knickers and tights soaked with my own juice. As the happy couple exchange vows, my cunt and anus tingled from having been being worked by his fingers and thumb and my mind replayed over and over the punishment I had received while bent over Dave's car.

Chapter 2. "Have you ever..."

In my opinion, there is no time when people are more relaxed with one another than just after sex. All the nervousness, shyness and self-consciousness has gone away, and people can be open and honest.

This story begins in one of those moments.

Ian was someone I was seeing for the first time. I would describe him as just a really nice, normal guy. Like many of my clients, he was someone who seemed completely devoted to his wife and family but who succumbed to an itch that just needed to be scratched. It was his first time seeing an escort - indeed the first time he had done anything behind his wife's back.

At first, he was incredibly nervous. As he opened the door of his hotel room, he wore a guilty guiltily looked surveyed the corridor before letting me in. Then, he nervously sipped his drink before I helped him out of his clothes, and he slid quickly under the covers to hide his nakedness.

A few hours later, we were sitting naked in a bath enjoying a blissful post-coital cigarette, sipping champagne and chatting like old friends.

Feeling the call of nature, I lifted myself out of the water, "sorry I need to pee." Ian looked embarrassed and asked, "Would you like some privacy? I can get out and go to the bedroom."

I laughed and said, "Seriously? Half an hour ago I was sat on your face with your tongue in cunt! I don't think privacy is an issue!"

"Haha that's true," he agreed and watched me cross the room and sit on the toilet. As I started, I smiled at him and jokingly asked, "Does it turn you on watching me pee?"

Ian gave a sheepish grin. "To be honest, I've never seen a girl take a piss before, not even my wife, but there is definitely something sexy about watching you."

He paused and looked at me as if debating whether to continue. "Actually, I've always wanted to try watersports - you know pissing on a girl or being pissed on during sex."

"Have you ever suggested it to your wife," I asked, although I suspected I knew the answer.

Ian replied, "No way, she thinks cowgirl is kinky sex - she won't even suck my dick!"

He paused again before continuing, "Err...just out of interest...err...is it a service you offer?"

I gave an uncertain smile. "In all honesty, I've never done anything like that, not as an escort or in my private life. I guess it's not something I've ever really thought about."

He pressed me for an answer, "But would you? If I were to book you again?"

I thought carefully. As you can imagine I'd had a variety of requests from clients and there were somethings I just wouldn't want to do. However, while the idea of it didn't particularly turn me on, equally I wasn't repulsed by it and couldn't see any harm. I said, "Yeah, I guess I'd be happy to try that. When do you fancy meeting?"

Ian looked like a kid in a sweetshop. "How about tomorrow? I can tell my wife I'm working late book this hotel again."

"I could be free," I replied, "What do you have in mind us doing?"

I could see Ian thinking it over. "Actually, I hadn't thought about the practicalities of it. In my fantasy we'd just be fucking and spontaneously start pissing on each other at some point. But I guess we'd have to move to the bathroom - maybe taking it in turns standing over each other in the bath?"

I've always thought that if you are going to try something new and kinky, you should go all in and make it as exciting as possible. Squatting in a bathtub didn't sound remotely erotic to me.

"I'm sure we can come up with a much naughtier plan. Leave it with me!"

A few days later I was sat on a bench in a park, just around the corner from the hotel Ian had booked. It was a glorious sunny day, and the park was really busy. Close by there were people stretched out on the grass reading, families enjoying picnics and kids noisily kicking balls around. As I waited besides the path that circled the park, I was passed by lots of joggers and cyclists.

I checked my watch and then glanced down the path. Right on cue, in the distance I made out the figure of Ian making his way towards me. He was dressed in blue shorts and a baggy green t-shirt and looked like all the other middle-aged dads who were out for an afternoon run.

As he came near, I stood up, flexing my legs behind my things - just another runner warming up. I was wearing my cute black gym leggings and a fitted vest top. I saw him ravenously surveying my thin layers of Lycra, his eyes darting from my small breasts to my tight arse, before coming to rest at the triangle of light between my thighs.

We did not greet one another. Nothing needed to be said - we had exchanged texts and we both knew the plan.

I set off on a gentle jog and looked back to see he was following a few metres behind. Two random strangers out for a run.

Ian was in reasonably good shape, but it was a very warm day, and I could hear his breathing getting heavier. As we completed our first lap, I turned to see his face was glowing red and patches of sweat were forming on his t-shirt. I too could see small beads of sweat glistening on my skin.

Halfway through our second circuit, I veered off the path and beckoned Ian to follow. I headed across the grass towards a gap in the tall trees and continued down a dusty trail.

As we entered the woods, it immediately became darker and cooler. Although we were only metres from the busy park, it felt quiet and secluded. A minute later we reached the small clearing that I'd scoped out earlier.

By then we were both incredibly horny. I threw myself into his arms and locked my lips over his. Our tongues met and we desperately explored each other's mouths in a lengthy French kiss.

His hands reached round and groped by arse, digging his nails in as he pulled me tight against his body. I could feel his rock-hard cock pressing against my Lycra clad leg.

Ian's hands reached for the waistband of my leggings. He was in a hurry to get me naked. However, I gently pushed his hands away. "Not yet, I need you to lie down on the ground for me."

He obediently sank down and got himself comfortable on the leafy floor of the clearing.

I moved to stand over him, planting my feet either side of his shoulders. My eyes fixed on his as I moved my hand between my legs and gently rubbed myself over the thin material of my leggings. It felt amazing. My leggings were already warm and damp with sweat from our run and it wasn't long before the juices from my pussy were adding to that wetness. My fingers pressed against the Lycra so that the shape of my cameltoe would be visible to Ian, who had one hand inside his shorts as he watched from below.

Soon the crotch of my leggings was soaking wet. I lowered myself into a squat, coming to a rest a few millimetres from Ian's face so that he could smell intoxicating of my sweat and my sex.

Ian reached up and gripped my hips, pulling me tight against his face. His mouth kissed and nuzzled my cunt through the material of my leggings while his tongue licked and tasted my wetness. I rocked gently back and forth on his face.

Feeling the first spasms of an orgasm, I leant back slightly and, without warning, started peeing.

In preparation, I'd drunk a lot of water and now my clear piss was gushing out from between my legs and through my leggings. I watched as it ran down Ian's face, into his mouth and down his chin.

Ian's hand disappeared back down his shorts and he started to furiously masturbate. He opened his mouth wide and lapped up my piss with his tongue, gulping it down. I ground my cunt harder against his nose and mouth, bringing myself to a shuddering climax.

But we were not done. I rolled off Ian and lay beside him trying to catch my breath. "Your turn," I gasped.

Ian didn't need a second invitation. He sprang to his feet and pulled off his shorts in one movement. At the same time, as I lay on the ground, I pulled down my leggings and panties to reveal my trimmed pussy and also lifted my top to expose my 32b breasts.

I looked up to see Ian holding his penis, the tip glistening with pre-cum.

It took a bit of time for Ian to get going. At first, he couldn't decide where to aim, and then he found that his erect cock was stopping his flow of piss. Eventually the tap did open. A small trickle at first that gave way to a full-on shower.

First, he expertly aimed for my exposed cunt before working his way upwards and soaking my bare breasts. His warm pee felt fantastic against my skin and prompted me to insert four fingers into my cunt for a frenetic wank.

Ian continued. As his pee reached my neck, I closed my eyes and opened my mouth in anticipation.

The torrent of piss reached my face. To be honest the taste was fucking disgusting. However, as the warm liquid entered my mouth I didn't care. Lying in a public park in full daylight, semi-naked and being pissed on by a respectable man twice my age made me feel like a dirty whore. My state of arousal was of the charts. I swallowed every drop while fisting myself to a second powerful orgasm.

I knew Ian also needed to cum. "Fuck my mouth!" I demanded.

Like a possessed animal, Ian dropped to his knees and drove his cock down my throat, making me gag. He pumped his penis in and out of my mouth as my tongue thrashed against his shaft.

His cocked tensed and started to pulse before he filled my mouth with a stream of warm cum. Holding it in my mouth, I pulled him towards me and we passionately French kissed, swapping his cum between our mouths before swallowing it. Exhausted, we collapsed on the ground side by side.