The Second Degradation of Alice
Copyright© 2025 by tiffany58
Chapter 6: Session 4: Sir Tim Barlow
Erotica Sex Story: Chapter 6: Session 4: Sir Tim Barlow - 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
In my final video session with Dylan Jones, we moved on to the story of Sir Tim Barlow, the fourth of my users and abusers. In his own way he was by far the worst of the four, at least the others were nice to me when they were not using me for their own pleasure. This is what I told Dylan in that session.
When I had returned from my two nudist holidays with Uncle John and Mr Green, The Professor proudly announced that he had the best holiday of them all lined up for all four of us, and told us to pack for warm weather, although I did not need to pack anything, not even toiletries and cosmetics this time.
On the appointed day, we all met at the Professor’s house where an executive car picked us up and drove us to Biggin Hill airport, the centre for private jets flights from London, and after passing through security and passport control, we were guided to a gleaming private jet sitting on the tarmac. As we climbed the steps, my little white skirt flapping up in the breeze to reveal my all-over tanned bottom, we were greeted by a smiling stewardess who welcomed us aboard.
Inside there was a stunning cabin with white leather seats and sofas, around small coffee tables. The stewardess then showed us through to a private salon at the rear of the cabin where there was a plush double bed, and beyond that a washroom and toilet. As we took our seats in the main cabin and buckled our seat belts the stewardess gave us each a glass of champagne, before telling us that our flight would take about seven hours, so to sit back and enjoy the flight.
About an hour into our flight the Professor said, loud enough for the stewardess to hear, that he had always wanted to join the mile high club before adding “Come on Alice, let’s get that little ass of yours lubed up ready for me.”
Twenty minute later, he walked me naked back into the main salon, and told the others that he was now officially a member of the club, and asked the stewardess to give us more champagne to celebrate. As the stewardess handed me my glass, she smiled at me and whispered “Ok?” and I nodded and smiled back at her, although Mr Green grabbing my hand and pulling me towards the bedroom brought that moment of gentleness to an abrupt halt. When Mr Green left me Uncle John came straight in and fucked me without even saying a word to me.
Within the first two hours of the flight all three men had joined the mile high club, and were all laughing and joking about it. The stewardess took my hand and led me through to the washroom where she gently and tenderly cleaned me up, then put me to bed to sleep for an hour or so, before all three men took me once again, this time in the main cabin in a team fuck, before repeating the abuse when the stewardess announced that we were an hour from touchdown. Once again, she took me to the washroom and cleaned me up, this time even using an enema kit to wash me out in both holes. She then kissed me softly and told me to go put my clothes on ready for landing.
The pilot announced, as we hit the tarmac, that we had just arrived in Tortola in the British Virgin Islands, and that a car was waiting for us the other side of Customs and Passport Control. As I stepped out on to the steps that had been pushed up to the plane, a hot Caribbean wind blew my tiny skirt up to my navel, revealing my smooth and tanned pussy to the airport workers standing around below, who simply laughed and pointed at my nakedness. A hint of what was to follow later.
After passports and customs, we left the airport buildings and climbed into a waiting blacked out people carrier, which took us a on a short trip to a marina where an expensive-looking motor vessel was waiting. After just a 45-minute journey, we arrived at a small island with a massive villa perched on the top of it. Standing on the small harbour deck stood a tall, slim, grey-haired man, in his mid to late sixties. Professor Aronson ran forward to shake the man’s hand and then turned to us all and told us this was our host for the next two weeks, the billionaire Sir Timothy Barlow, his great friend and sponsor of several of the university’s most important projects.
This was the first sight I had of the man who would become my main abuser for the next two years and by far the most brutal.
Sir Timothy led us all to his mansion, past a handful of gardeners, and in to the cool interior, where several maids welcomed us and took our bags to our allocated rooms, well not mine as I did not have one obviously, and Sir Tim looked at me and said you do not have a room as I am told you will sleep where needed.
Humiliated and degraded after just a few minutes on the island, my degradation continued as Professor Aronson said “Sir Tim is to become the latest member of our little group with your welfare and career at heart. He is the lead sponsor on several of the University’s key projects and needs a student liaison to look after all his needs when at the university, or elsewhere, as and when he needs support. That liaison is you from this moment onwards. So, Alice, as is good manners when you meet a new master, strip and show Sir Tim how you always greet a new owner.”
There in the hallway of the villa, surrounded by maids and with the gardeners looking through the windows and open doors, I pulled my thin T-shirt off my body and dropped my skirt to the floor as I kicked off my sandals. Now naked I walked slowly to Sir Timothy and knelt before him, pulling his beach shorts down and revealing a beautiful long, thick, and very straight erection. I took him in my hand, stroked him, and then sucked him into my waiting lips, before doing my best to deep throat this gorgeous cock, the biggest I had ever enjoyed.
He never touched me, just let me work on his magnificent tool, until as I felt his muscles tighten and his hips begin to thrust into my open throat, he suddenly grabbed my head, and with a roar pushed as deep as he could down my throat and shot what seemed like gallons of his cum inside me, As he did so his gardeners all cheered and the maids smiled and clapped their hands – apparently not the first time they had seen their billionaire boss unload in some unsuspecting girl’s mouth.
As I knelt there in front of him, drool, and spit, with a little coughed up cum, dripped on to my breasts, he told three of the maids to take the gentlemen to their rooms, and told the men when they were settled in, they could come back and join him on his play terrace.
Turning to the one who seemed the most senior maid, he told her to take my pile of clothes and get rid of them as I would not be needing them for the next two weeks. As she picked them up, he leaned forward and grabbed my arm just above the elbow and said “You come with me.”
He led me from the entrance hall towards the back of the villa and then opened a heavy padded door at the end of a corridor with dining rooms and lounges leading off it. Opening the door, he pulled me into a large room built on a wooden terrace, with wooden walls on three sides and an open wall with glass doors folded right back, giving a panoramic open view of the ocean in front of us.
I stood gaping at the room which was full of strange equipment – metal frames and tables, a wooden chair with a rigid back and arms but no seat, another similar one but this time with a central spar running from side to side with a very large wooden phallic dildo standing erect in the middle of the seat. On the walls were various chains, cuffs, tools, weapons and numerous whips and things for obviously beating someone – me most probably!
He pulled me round to face a table with an assortment of leather straps and things on it, and grabbing each wrist in turn fixed and locked a leather cuff with rings on it in place, a task he then repeated with my ankles, before completing the ensemble with a deep leather collar that sat around my throat, again with rings attached to it. “You will keep these on at all times while you are on the island unless I decide to remove them for some reason – do you understand?” I was speechless and could do nothing other than nod my head as much as the collar would let me.
He walked me across the room to a large metal frame standing in front of the open window, and, taking one wrist at a time, fixed me to the top corners of the frame, my arms spread wide above my head. He then did the same to my ankles so I was spread-eagled on the frame with my toes only just touching the floor. A touch of a button and a motor quietly whirred, and the frame suddenly tilted to the horizontal so I was hanging by my wrists and ankles, with pain shooting through my shoulders and hips as my weight fell onto my unprepared joints.
As I hung there getting my breath back from the shock of the sudden movement and pain, he pulled up a stool on wheels and sat in front of my drooping head. Grabbing my hair by my pony tail he lifted my head so I was looking straight at his cruel eyes.
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