The Second Degradation of Alice
Copyright© 2025 by tiffany58
Chapter 16: A proposal
Erotica Sex Story: Chapter 16: A proposal - 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
From that Builder’s Birthday Party onwards, the pattern of my new career rapidly took shape. Every three or four weeks I would receive a call from Charlie with instructions on where to be and when, and occasionally what to wear if it was more than just being naked on arrival. He only ever gave me two days’ notice, so there was no time to think about it too much, but I had time to go out in my flimsy dress and buy anything that was specifically needed for that next booking.
Dylan and Uncle John were running the show; Charlie was just their project manager on the job as he described it. They decided I should always have that 3–4-week gap between orgies to allow my body to heal properly and for John to do his STD tests and issue my new health certificate. They also both used me together after each brutal assault on my body so my healing never truly started until I was home alone again. As was now his custom, Charlie would also use me as soon as I arrived at the rendezvous point and then again after I had been ushered unceremoniously from wherever the party was being held. A regular fuck over the hood of my car seemed an appropriate final degradation before driving home naked or with just the coat or dress around my shoulders.
Living naked practically all the time now, Dylan tried to be helpful by regularly placing orders for home deliveries for me: groceries, household goods, and anything I needed for personal hygiene and health. Dylan graciously allowed me a thin, short, cotton kimono in which to answer my door to the delivery guys, although he did not allow me a tie to keep it wrapped around me so every man had a good glimpse of my naked body as I struggled to sign the delivery note or take hold of any smaller packages. Over time, the regular delivery men became familiar to me and they also were very soon familiar with my naked body, so I stopped even trying to hide it from them.
Dr Uncle John would sometimes come to my apartment to treat my wounds and test me for STDs, issuing me with another health certificate ready for the next sordid and savage group onslaught on my fragile small body. My traitorous pussy seemed to always betray me by the way it responded, whatever the treatment it received. Uncle John would stay the night on those occasions and I was surprised myself that I looked forward to those nights, with some gentle romance and old memories.
Then Charlie would suddenly call and give me 24 hours’ notice I was needed again. Each party was attended by a minimum of twenty men, with similar abuse of my body, sometimes more brutal than others, but I always had at least two orgasms as I sank into a state of almost comatose arousal. One memorable occasion saw me walk into a room with around 30 men but this time with more than half with their wives or girlfriends; as the party progressed all the women used me, thrusting into me with large strap-ons and dildos, and demanding that I eat them, another sight for their men to enjoy. One weekend, I was sent to Birmingham again and found myself hired out to Fat Mo for the entire three days to be used by her and her group of lesbian friends. The whole event was filmed and once again I starred on Fat Mo’s own personal website for her subscribers to savour. That was the most brutal of all my orgies.
Within a few months I had finished all my “real” client work and was now just working for Dylan and Charlie, being used by their clients and generating the revenue that they had decided I was now worth for my “specialised group special events.” They now paid all my expenses – food, requested clothes, cosmetics, whatever I needed in fact – and I was now a “kept” whore. Dr John looked after my health, making sure I was both healthy and clean – that I was now a risk of not being clean was probably the most degrading thing that I had to come to terms with – and took his payment in kind on each visit, which I willingly accepted was just what I wanted and needed after a weekend of debauchery.
As the months went by, I tried hard not to think too much about what I was doing and what was being done to me. During my periods of healing between orgies my life passed by with no real focus, just the daily video call from Dylan to check on me, and an occasional video call with him and a new prospective client wanting to see what he was about to buy.
In the first week after each gangbang, I wallowed in shame and disgust with myself – what was I doing? Why was I behaving as I was? Why did I not just say Stop and walk away from it all? And why did my body respond in such a degrading and humiliating manner every time?
The next couple of weeks I settled into that unfocused, dreamlike state: letting delivery men ogle my body; sleeping with Uncle John; being summoned regularly for my revealing walk to Dylan for him to use me and then send me away again. On those occasions I usually walked home, his cum sliding down my thighs, just to free my mind and pretend all was normal with my life.
But suddenly, the call would come from Charlie and my whole demeanour would dramatically change – I was excited to be wanted again. My arousal levels soared, and I was almost continuously wet and on the edge of orgasm but never let myself get too close. I hated to admit it to myself but for that period between Charlie’s phone call and my humiliated, sobbing, drive home after the sex party, I was happy – this was the real me.
It was now almost two years since my school reunion that had been the trigger for my descent into a life of depravity. I was now 28 years old and, unlike at that reunion, I now had no family, no friends, no clients, and no career – I was a kept woman and a full-time whore. All I had were Dylan, Uncle John, and Charlie.
One Friday afternoon I was called to Dylan’s office, which was unusual now as he usually just took me to bed before sending me home again after fucking me, no evening restaurant dinners followed nowadays. I climbed the stairs and walked along the corridor to his office, where I knocked on the door and waited for him to open it for me. He quickly pulled the door open and then stepped out of his office into the corridor, holding his hand out and saying “Give me the dress.”
I looked nervously down the corridor at the various doors that I expected to open at any moment, and then with a resigned sigh, undid the three buttons, slipped the dress off, and handed it to Dylan. Giving me a friendly nod, he waved me into his office, the open door hiding the casual seating area from my view as I stepped in and kicked my shoes off.
As soon as Dylan closed the door, I could suddenly see a man and a woman sitting on the comfortable seats and sofa. My hand shot to my mouth as the shock was even more shattering than when I had seen Uncle John sitting there fifteen months previously. A loud groan emerged from my open mouth and a great sob wracked my body. “Ohhh myyy Goddd – why are you here?” I gasped.
“Hello Alice – what a delightful looking slut you have grown into. I always knew you had much more to offer than those old perverts of yours were willing to explore” smirked Sir Timothy Barlow.
I stared at him in total shock. I had not seen him since I was just twenty-one and my group of old abusers had decided to free me from their lecherous clutches. He was in his mid to late sixties when I last saw him so he must be at least seventy-three by now, if not more, but was still devilishly handsome. He was still a tall, slim, athletic-looking man, with silver-grey hair that was off-set perfectly by his expensive tailored suit.
He had been the most brutal of my gang of four but for some reason I always did exactly what he demanded even when the pain and degradation were at their worse. He could be absolutely charming, especially when he took me to the theatre or to an expensive restaurant, and even seemed to enjoy flaunting his “young floozy” in front of business acquaintances at various drinks events or dinners. However, at other times he could be terrifying and just destroyed me with his abuse of my small body.
“Sit down Alice” he said as he waved a hand at the seat facing him, and Dylan placed his hands on my shoulders and pushed me down onto the seat. “You really have grown into a beautiful woman Alice. The same size everywhere but maturity has given you a feminine softness that is quite alluring. No wonder you have been so successful as a whore!”
He continued “I have really enjoyed watching your performances – I so enjoyed that first video you made of your pick-up of the fat sweaty guy in the hotel – you were so excited and visibly wet as you let your natural slut emerge.”
I was stunned at the thought of him watching that very first video in the hotel, when I had picked up the man in the bar and given myself to him in his hotel room. I simply stuttered “You watched that?” “Of course, my dear. I have watched all your videos – the ones you made and the ones others made of you during your energetic performances over the last two years. Indeed, you have become quite a star in some quarters of the “porn-verse” and a lot of people have enjoyed watching you when I have shared your latest adventures.”