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Status: Finished  |  Genre: Literary Fiction  |  House: Booksie Classic

A teenage boy loses his virginity to a prostitute.



‘Plush pushy boysh.’

This is what my friend Lee Hall’s Dad used to say in a lousy Sean Connery accent. Lee’s Dad had made a fortune from a cleaning business and lived in a big house in Heaton Moor.


Lee used to be called goofy at primary school, but by the time he was seventeen his teeth had been fixed and no one called him goofy any more. Lee was a handsome boy now, and his Dad’s famous parties made him (I would suggest) the coolest kid in sixth form.


When Lee passed hid driving test his Dad bought him an MG. He used to drive it to college and we called it the fanny magnet. I’d never seen a fanny at this point, but Lee had seen many.


Lee’s parents were separated and he lived with his Mum. He stayed with his Dad at weekends. Lee’s Dad was not like a normal Dad – he took drugs and threw parties for us and let us drink alcohol.


Lee’s Dad also hired prostitutes.


‘Want some plush pushy boysh? It’s all on me’


We used to spend a lot of time at Lee’s Dad’s house. Malcolm. It was never Mr Hall. Even Lee called his Dad Malcolm. We played Nintendo and smoked pot: it was his Dad who hooked us up. Sometimes we drank vodka and Red Bull, but we mostly just smoked pot and drank litres of fizzy water.


Lee wanted me to take up his Dad’s offer and go with a prostitute.


Lee’s Dad’s house was a lawless place – a paradise for teenage boys – and I loved going there and feeling like I could do whatever I wanted, but the offer of prostitutes was, for me, a step too far. Lee had already been with several prostitutes arranged for by his Dad, and he was urging me to join in, but it made me feel unbelievably self-conscious. Of course I wanted sex (I was seventeen!) – but what I really needed was the validation that sex implied[1]. The booze, drugs and parties were fantastic, but the prostitutes were something that I honestly didn’t want to get involved with.


I remember being in the front room of their house, high from the pot and playing Mario Kart, when Malcolm walked in and fixed himself a gin and tonic. He was wearing a red, silk dressing gown and nothing else. He sat down and I saw a flash of his penis.


A few moments later, a beautiful woman briefly stuck her head through the door and said,


‘Cheerio,’ she said.


She gave a brief wave, took her head away, and shortly thereafter the front door made a closing sound. Malcolm was grinning the grin of all grins,


‘Plush pushy boysh – that’s what the cleaning game gets yer.’


Lee didn’t respond to any of this, he just carried on playing the N64. Malcolm stayed for a while and sipped his drink.


Around this time, I was hopelessly in love with a girl called Anna Antrabus (I know, weird name!). She was in my A-Level English class. It was an unrequited love, of course: one-sided and all in my head: intensely within my own head like all teenage crushes. I don’t think I’d spoken to her more than a handful of times, and none of those times had been what you might call meaningful. I loved her from afar.


She wasn’t one of the ‘hot girls’[2] that all the boys talked about – I don’t think my friends even knew who she was. But I thought she was terrific. And if no one else had the good taste to notice her, then so much the better.


I know it’s not a one-of-the-lads type thing to say, but I had this hope that I might lose my virginity to Anna. And even though it was very far from happening, I kept it in my heart as an ideal. I didn’t like the idea of my first time being with one of Malcolm’s prostitutes.


This was my idealism. But Lee talked me out of it.


Lee saw how I wasn’t getting anywhere with Anna and how I struggled to find ways to talk to her: I was a shy and introverted boy and talking to girls did not come easily to me.  Lee, bless him, had invited Anna to one of his Dad’s parties, but she wasn’t one to go out much and wasn’t part of our friendship group. She was a very well behaved girl.


Lee’s argument was that once I’d lost my virginity I’d be more confident and thus be able to approach dear Anna about the possibility of maybe going on a date some time. He said that they don’t laugh at your wang and even guide it in if you need a bit of help. These were my biggest, secret fears – perhaps he knew me very well or perhaps these are every teenage boy’s fears.


He convinced me.


What I do notice now, looking back, is how all my worries about the size and shape of my dick disappeared. I can’t even remember if I put it in or if she put it in for me. But it happened somehow and then it was done. She seemed quite responsive but that’s probably what she was paid for.


I hurried straight out when it was over. I said a brief thank you to the nameless woman but I didn’t even say goodbye to Lee or Malcolm. I couldn’t face them. It was too much emotion or something. I just wanted to get home where I could feel safe and unexposed.


I was waiting at the bus stop. A few minutes later, she turned up next to me. The woman I’d seen naked. The woman of whom I now had carnal knowledge. There was a brief eye contact and she smiled at me. I smiled back. I wanted to say something but I couldn’t get my tongue to move: the familiar feeling of going into myself and the fear of conversation. She took out her phone and started texting. I pretended to read the timetable.


She didn’t have a Mini Cooper or a Porsche. I’d imagined that the money from prostitution would buy her a certain lifestyle; but maybe not.


She was using public transport. Just two people waiting for a bus. And what had happened between us in Malcolm’s spare bedroom already in the distant past. We politely ignored each other the way that all strangers politely ignore each other during that interminable wait for the bus to arrive. When it did arrive, I rushed onto the top deck and she stayed downstairs. I watched from the window when she got off the bus a few stops later and felt relieved. I watched as she walked away but she never looked back towards the top deck of the bus.


A month later it was the Sixth Form Ball.


I went by myself. By that I mean that I went with a few friends who were also single. Dateless. Me and my dateless mates.  We had pictures taken together on the steps of the venue – wearing our hired suits – like a low budget parody of Eton alumni.


Lee, of course, came to the ball with a date. He never had my problems.


The experiment had failed. My experience with the woman at Malcolm’s house had not changed me. I was still anxious, introverted and socially awkward. It hadn’t given me the confidence to ask Anna to accompany me to the ball. If anything, I felt more ashamed of myself and more pathetic than ever before.


After the meal, there was dancing. I danced in a huddle with my single mates. I looked across the room and saw Anna dancing with her mates: the boys in one corner; the girls in another. I didn’t speak to her once all night – even after drinking several beers. I went home in a taxi by myself.  


Later that year, I moved away from home and went to university. Three years later, I finished my degree and moved back home. My time at Malcolm’s house remained my only sexual experience. I could just never find a way to talk to women. I won’t recount the list of failures here.


After a few months of living back at home, I just could not visualise a future for myself. Life felt like a hopeless endeavour. It was then that I decided to kill myself. And it was a great success. Even now, it’s still the best thing I ever did.






[1]  It needed to be voluntary. I needed someone to choose to sleep with me.

[2]  This is kinda vulgar and sexist and embarrassing but basically true: our understanding of women was basically Pamela Anderson and women in Loaded Magazine and girls in sixth form were basically rated on how closely they resembled these photographed ideals. There were about eight girls that everyone desired because they were close enough and every other girl was basically ignored.

Submitted: December 02, 2020

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