When I first signed up to AdultWork, all I did was read reverse bookings and fantasize about filling them. There was one – I always think of it – by a guy who wanted someone to come over, show him her tits, then bend over the table and lift up her skirt to let him fuck her up the ass, all within 45 seconds of the knock on the door, and with no words exchanged. Not bad, eh?
Cucumber Man’s reverse booking instantly caught my eye. It was for a date in August when I was sure to be in London, in the middle of the afternoon, and not too far from me. And he wanted, specifically, a submissive escort. I checked his profile, he had listed BDSM as one of his interests and he had over 1000 good ratings. I put in my bid, and I won.
We entered into a lengthy correspondence, during which Cucumber Man helpfully sent me lots of safety information and tips on how to get more clients, both of which I naturally ignored. I was more interested to hear about the trials and tribulations he had to endure as a single dad, and how he dealt with his ex who was still in love with him. For some reason, though, he kept bringing the conversation back to how he would humiliate and degrade me and teach me why I “was born with 3 holes”.
As our date approached, he wrote to me to tell me what he wanted me to wear and asked me whether I would need an introductory 5-minute chat or if he could just start fucking me the instant I walked in. You can guess which option I chose.
I knew he wouldn’t really – it never happens like that (except once when I was really, really horny and the guy was just so hot). Instead, he led me first to the sofa, where the used panties I had sent him lay draped over the back.
“Look familiar?” he chuckled. Then he gave me the money, a box of chocolates and a big bag of arts and crafts supplies for my son. How charming! Then, he asked me to take off my dress.
“Mmmm,” he said, stroking my bottom admiringly. “Who gave you these marks?”
“A – a friend,” I stammered.
“Am I a friend?” he asked, speculatively.
He lifted me up, carried me into the bedroom squealing in protest, and threw me onto the bed. Then he paused, his cock hovering right in front of my unprotected pussy.
“Cucumber Man!” I gasped, as he entered me. “Not… without… a condom!!”
He seemed to be mulling this over in his head as he fucked me. Finally he objected: “But you didn’t say that was one of your limits.”
“I thought that went without saying!”
“Nothing goes without saying.”
“Listen, Cucumber Man,” I went on, desperately. “I can’t afford to have another child…”
“You don’t look to me like a woman afraid of getting pregnant,” he countered, cheekily.
“…and you can’t either.”
He pulled out then.
“I’m going to make you suffer for this,” he said, taking down a box of condoms.
Actually, he didn’t really say that. But I felt like I spent the better part of the afternoon screaming, “no! stop!” and being completely ignored. At some point, I just had to… block everything out, and enter a strange, dream-like state. No wonder he later said that I was “the most submissive escort” he’d ever met.
So I don’t remember it all, but I remember that he asked me to put on a schoolgirl costume – it was so bizarre, not like anything a real schoolgirl would ever wear – and I remember him fucking me in the ass, cruelly, withdrawing all the way and then re-entering me, every time, so that each stroke hurt like hell, and this seemed to go on for hours, wordlessly… I just lay there, with tears in my eyes, wishing I were anywhere else in the world but there. I can’t even remember how it ended – perhaps he came, perhaps not. Then he took out various implements to see what else he could use on me. He decided against the nipple clamps, saying they were too painful. Instead he handcuffed my wrists to the bed-posts and began to rub my pussy with a Hitachi wand. He kept turned it higher and higher while I screamed and begged him to stop. All of a sudden, he switched it off.
“You squirted,” he said, holding up the dripping wand.
“What??” I craned my neck, in disbelief, to see that the sheets were soaking wet beneath me. I lay back and closed my eyes in shame and horror.
I can’t remember exactly what happened next, but at some point he went into the kitchen to fetch some ice-cubes, then turned me over on my stomach and inserted one of them into my already abused ass.
“Oh no, please don’t!” I cried, but he began to fuck me, pausing every now and then to insert another ice-cube while I begged and pleaded with him to stop. Finally he ran out of ice-cubes, but he kept fucking me in the ass, and then all of a sudden he wrapped a muscular arm around my neck, drawing me up towards him and tightening his hold on me until I felt like I was about to pass out. Everything went kind of white and I could hear the sound of birds outside the window gradually fading away, and part of me just wanted to fade away too, to let the pain just fade away with me. And in fact, the pain did seem to be fading away. I could still feel him fucking me in the ass, somewhere far, far away from the rest of me. But what if I were to die here, in this horrible place? I gritted my teeth and struggled to stay conscious. He loosened his grip – “You don’t want to pass out?” “No!!” “You should try it. An ex of mine really loved it.”
He told me to go to bathroom and clean myself up, as the ice-cubes had all melted and were dripping out of my ass. I staggered into the bathroom, my head spinning, and he followed me, saying he liked to watch. Then he told me to go back to the bed, get on all fours, and close my eyes – he had a surprise for me. “Oh, God, no,” I was thinking, and then let out a shriek as something huge and cold was rammed into my pussy.
“What is that thing??” I screeched in dismay.
“A cucumber,” he answered mildly. “There’s one for your ass, too.”
“Noo!” I screamed, struggling to get away from this new violation. “No, please, really – DON’T!!”
“I can’t – there’s not enough room in there,” he said, disappointedly, taking the cucumber out and replacing it with his cock. “Sure opened you up, though.”
“What – really?” I asked in horror.
“Yes, you feel all loose now.”
Oh God, I thought to myself, this guy is killing me! Finally he lay back and asked me to ride him. I climbed up onto him, happy to oblige. He commended me on my enthusiasm, then asked if it was true that I was lactating.
“It is,” I assured him.
“I want to taste it,” he said, so I obliging squirted some at him.
“Not like that!!” he cried, incredulously. “Like this,” and he pulled me down towards him. I watched as his lips enveloped my left breast and he began to suck… harder and harder. Waves of pain shot through my breast, which felt like it was caught in a slowly tightening metal clamp. I cried, literally sobbing with pain. Finally he released my breast, which emerged, grossly misshapen, from his mouth.
“It’s been years since I tasted breast milk,” he murmured appreciatively, turning towards my right breast.
“No!!” I screamed, but he drew it into his mouth, only not quite as viciously, and sucked it dry too.
“See?” he told me. “I was gentle that time.”
I collapsed beside him in bed, completely worn out.
“You did really well,” he said. “But you should specify no bareback in your profile. You can’t blame me for trying to see if you’d accept it.”
“Do most escorts accept it?” I shot back at him.
“No,” he admitted. “Hardly any.”
I was a little peeved, because the last person who had asked about my limits had laughed dismissively when I added, “no bareback”, saying that he wouldn’t even have contacted me if he thought I offered bareback. I was also quite upset to see that I had stayed half an hour over time. I could have put an end to this torture much earlier! As it was, I got home an hour late and had to endure a lengthy interrogation by the Albatross which extended well into the night. I hid the chocolates away – I couldn’t bear to eat them or even to look at them.
The next day, I found that Cucumber Man had left me a good rating and asked me to do the same for him. He had helpfully dictated what he wanted me to write, but I couldn’t help changing it slightly, to make it sound a little less crude, and then, just to lighten things up a bit, I added something about never being able to look at a cucumber again without shaking in fear.
Well! I was never to hear the end of that! For the next month, people were writing to me saying things like, “I’d like to make a booking – just need to stop by the green-grocer’s first!” And I was partly laughing, and partly dying a little inside. But mostly laughing.
And then, to top it all off, he wrote me a field report! And sent me a message explaining how to display a link to it on my profile. Though the field report was actually quite flattering, it wasn’t really something I wanted to advertise on my profile, so I decided not to display the link. Nevertheless, the very next day, people were literally calling me up to determine the veracity of this field report. I was teased about it by both Cherry Popper and the Anal Rapist. The Anal Rapist was particularly aghast by the crude and vulgar language of the report, which, he warned me, would “attract all the wrong sorts”. He then made me promise never to see Cucumber Man again. (I was touched, at the time, by his apparent concern for my safety!)
Cucumber Man sent me quite a few emails after that, asking when I’d be back, passing on details of venues where I could make a lot of money doing gang-bangs, and commending me for being the “most submissive escort” he’d ever met. Inexplicably, I didn’t write back to any of them. I was really proud to be called the most submissive escort he’d ever met, and really turned on by the gang-bang idea, but – I don’t know why – I just couldn’t bring myself to write even two words to him. Until yesterday…
“Hi Cucumber Man! Thanks for your message(s)! Sorry it’s taken me so long to get back to you… had hoped to be in the UK for the October school holidays but looks like I won’t be able to. What about Xmas holidays, though?”
He replied: “Christmas is good for me. I will be dropping my son to his Grans and then have the place to myself while I do overtime at work. Cant wait to teach your holes an other lesson.”
I felt my blood run cold when I read that. The afternoon I spent with him was one of the most physically traumatic experiences of my life.
So why the hell would I want to go back?