The Second Degradation of Alice
Copyright© 2025 by tiffany58
Chapter 10: Paid
Erotica Sex Story: Chapter 10: Paid - A young woman is recovering from years of degradation at the hands of a group of mature men. But an invite to a school reunion triggers emotional flashbacks and leads her towards a second degrading life. How will she survive?
Caution: This Erotica Sex Story contains strong sexual content, including Ma/ft Coercion Consensual BDSM DomSub MaleDom Humiliation Rough Gang Bang Anal Sex Cream Pie Double Penetration Exhibitionism First Fisting Masturbation Oral Sex Squirting Public Sex Teacher/Student Prostitution
I finished my client work in Edinburgh and took an evening flight back to London where I rested and recalled the pleasure my unknown man had given me. I could still picture his beautiful cock hidden under his sagging belly, and how well he used it to touch me inside, in places no man had ever reached so effectively before. I luxuriated in the memories of the mind-blowing orgasms he had given me and could not wait to see the secret film I had made of my debauchery with him.
Saturday afternoon could not come quickly enough, and very soon I found myself standing outside the door to Dylan’s apartment, two floors above his consulting room below. I had worn a simple denim skirt, mid-thigh, a woollen V-neck sweater, with a hint of cleavage, and simple flat-heeled shoes instead of my usual heels. I carried my handbag with the secret camera in my hand. I rang the doorbell and very quickly Dylan opened it and waved me in. He was wearing a simple cotton dressing gown, tied loosely at his bulging midriff, and was obviously naked underneath. He waited before saying anything until I had stripped off my skirt and sweater and stood naked before him, when he simply asked me for the handbag.
Taking the bag, he led me into his bedroom and told me to lay on the huge bed that filled most of the room. He then extracted the camera from the bag and removed the memory card, which he inserted into a laptop below a giant wall-mounted television screen; both machines were already live. He picked up a remote control, came to the bed, throwing his gown onto the floor, and climbed naked onto the bed. He settled himself beside me with an arm round my shoulder, before saying “Right, let me see how well you did. Make me hard while we watch and then suck me until I am ready to fuck you.”
Obediently I took him in my hand and began to gently wank him as he pressed the play button on the remote. The TV screen was instantly filled with a view of me sitting on the hotel sofa, speaking into my phone and clearly could be heard saying I had hooked a fish. As I saw myself lean forward to place the phone in my handbag, I was shocked to see how blatantly I had parted my knees, just the first shock at seeing how sluttish I behaved that night.
The film moved on with him joining me on the sofa, then groping my thigh and eventually my legs falling open to let his hand slide under my skirt to play with my wet pussy – I had not realised I opened my legs so wide or acted so sluttishly, so quickly! Then it was out of the bar, into the elevator and the sordid conversation behind the embarrassed elderly couple.
By now Dylan’s stubby fat cock was rigid in my hand and he pushed my head down to take him into my mouth, my head turned and resting on his big belly, so I could continue to watch my performance on screen while I sucked him. As the film moved into the bedroom and showed me being stripped and then kneeling in front of the man to undress him and take his cock into my mouth, Dylan just pulled me on to his lap, reverse cowgirl so I could continue to watch the screen, and sunk his cock into my sopping wet pussy, where it stayed for the rest of the film. The film ended with the two men smirking at my dishevelled state and a closeup I had forgotten taking, of the big glob of cum that had fallen between my bare feet as I opened my door. At that point Dylan just exploded in me!
Over the next two weeks I repeated my sordid performance in Manchester and Leeds; once again the men were not attractive but at least not sweaty until they had fucked me hard in every orifice. And then on the following Saturdays, Dylan and I reviewed my secret videos.
My fourth man was in a hotel in Nottingham. He was fun, about 45 years old and by my usual standards quite trim and good looking. However, when I showed the video to Dylan on the Saturday afternoon, things were suddenly very different to our previous three viewings.
That Saturday Dylan wanted to start with his cock already buried in me so I was sitting on him watching the film. As we watched, the man came over to me with a glass of wine in his hand for me and sat down beside me. After a few polite exchanges, he asked me if I was working tonight, and was I free or waiting for a client. At first, I did not understand and simply said no I am not waiting for a client as I had finished that afternoon. At which point he asked if I was free now and how much I charged. I suddenly realised what he was asking and burst out giggling, and said “No I am not like that I am just looking for some fun and company tonight - if you want to join me that would be nice.”
At that, Dylan suddenly shouted “You stupid girl” and threw me off his cock onto the bed. I sat up on the edge of the bed while Dylan stopped the film, and as he turned back to me, he viciously smacked my left breast with his right hand, and immediately did the same to my right breast with his left hand – I screamed with pain and shock and grabbed my throbbing breasts, each with a blazing red hand print clearly visible. Before I could ask what was wrong, he grabbed, pinched, and twisted both nipples with his hands.
As the pain rushed through me, he yelled in my face “You stupid little bitch – he wanted a whore and you gave him a free slut - that was your chance to become a real whore and you wasted it. Now get on your knees and spread your legs.” I thought he was going to fuck my ass but he had other plans first, as ten viciously hard slaps descended on each buttock in turn. My ass became bright red and hurt like crazy, with his finger prints all reaching into my crack and hitting my anus on each spank, a couple also smacking my pussy hard at the same time. I cried in pain and humiliation as he climbed back on the bed and, with no foreplay or lube, forced his fat cock into my anus and fucked me as hard as he could until he dumped a first load of the day into my bowels.
Once he had stopped panting from his exertions, he started the film again, and pulled me into a gentle cuddle on the bed as if the violence and pain had not happened. A long slow fuck followed at the end of the film, and eventually I fell asleep resting my head on his belly and with one leg thrown across his.
We both woke up when it was getting dark outside, and without letting me clean up, he told me to get dressed, before taking me to his favourite local restaurant for dinner. All through dinner I was twitching and fidgeting on my seat as my still-inflamed bottom was too sore to sit still for more than a few minutes, and under my sweater my breasts still had the finger prints of his brutal slaps.
They gave us a small table in the corner near the kitchen as it was a busy Saturday night but Dylan was a regular client and knew the owner. As we sat there eating, Dylan had his fingers almost constantly on or in my pussy under the table cloth, keeping me gently aroused and taking my mind off my sore behind. It was also an ideal place for the conversation that now took priority in my mind.
Dylan leaned towards me and said “I hope you understand why I punished you for your stupidity – you are a whore and it is time you started acting like one. You have had a bit of practice at just being a free-use slut but from now on you will behave as a true whore and only fuck men who pay for you. You can carry on picking up men in hotels and bars but no more freebies. Do you understand?”
Close to tears, I told him I understood, but he had hurt me and I was still sore, although he just ignored that. He started to tell me how much to charge and how to phrase things so that I was clearly a prostitute looking for a customer. Strangely my arousal levels began to soar as he continued to finger my pussy while teaching me how to present myself as a woman “on the game.” We agreed I would charge an hourly rate but with full service included so no hidden extras, and that really did mean anything the client wanted was included.
By the time we left the restaurant to walk the short distance back to Dylan’s apartment my inner thighs were sticky with my juices that flowed continuously from my sopping vagina. The discussion about my becoming a paid-for whore obviously had the same effect on Dylan as, once inside the apartment, and I was immediately naked as the rules demanded, he wasted no time in throwing me on the bed and fucking me vigorously for the rest of the evening.
We slept well and by the time we woke it was nearly noon. Over a light brunch I told him my next hotel stay could be on the coming Thursday in Southampton. I did not really need to stay there as it was only an hour or two from London but Dylan wanted me to whore myself out before our next rendezvous. He also gave me a “burner phone” and told me to try to get my clients phone numbers and location so I could let them know when I would be in their areas and available to meet them again if they wanted to. He put his own number in the contacts to start me off.
So, that Thursday evening, I checked into a hotel in Southampton I had never stayed in before. It was a low-rise hotel, with rooms on just two floors. A corridor with rooms on both sides ran from the reception area, with a small bar and dining room off the other side. So that was my reconnaissance of the hotel complete within minutes of checking in – I was getting quite experienced at checking out the best pick-up points. My own room was on the upper floor near the stairs and the elevator.