The Making of Hole
Copyright© 2026 by tiffany58
Chapter 1: meeting Julia
Erotica Sex Story: Chapter 1: meeting Julia - A young woman meets an older Milf and what seems an innocent dinner leads to a sudden descent into a life of abuse.
Caution: This Erotica Sex Story contains strong sexual content, including Fa/Fa Fa Mult Coercion Drunk/Drugged Rape Reluctant Slavery Lesbian Heterosexual Humiliation Gang Bang Anal Sex Analingus Double Penetration Enema Exhibitionism Fisting Oral Sex Squirting Small Breasts ENF Prostitution
Hi there. My name is Sally but nowadays I am more often called “Hole” or even much worse names. This is my story of how I ended up like this.
Let me tell you a little about myself when my story started.
I was 28 years old, divorced, and single for three years. I had a good job running a small online business selling Italian designer clothes to women with rich husbands. I may have been single but I was not celibate, although at that time I had not been with anybody for nearly a year
Physically I am blonde, blue eyes, and 5 feet 2, or 158 cms in metric terms. I am petite, weighing just 8 stone/112lbs or just under 50 kilos. I have small boobs 32A but big nipples out of proportion to the rest of me really and almost always obvious whatever I wear. I am told I have a cute bum. I have a flat stomach, quite wide hips which, with my slim legs, gives me a gap at the top of my thighs.
That gap shows my pussy clearly – my labia are fleshy and my clitoris is large and pops out from its hood when I am aroused. My pubic area is completely bald after I bought myself a course of laser treatment with my divorce settlement, a sort of “fuck you” farewell to my ex, that means I should now be hairless down there for life. With that gap and my large labia, I frequently have an obvious camel-toe if I wear yoga pants or bikini bottoms.
And because it is relevant indirectly to my story, I had an IUD fitted that meant I could have sex without worrying about pregnancy, although, as I said, I had been celibate for nearly a year. So, I am small, pretty I am told, and my nipples and camel-toe often attract admiring looks. And that was me when my story started.
I was at a business conference in London, which had been mind-numbingly boring, and had gone to the post conference drinks as I desperately needed one. I wandered around but did not really know anybody to talk to, and did not want to get hit-on by any sweaty men about to rush home to wifey, so very soon I was on my third glass of warm champagne and thinking about going home.
“God this is awful, isn’t it,” said a voice suddenly beside me. I turned to face an attractive dark-haired woman of about 40, who put her glass down on the pedestal I was leaning against, and held her hand out saying “Hi I am Julia and I see from your badge as she bent forward to look at my chest that you are Sally. How many of this rubbish champagne have you had?”
I giggled and said “Too many!”
“Do you fancy going to the pub next door and having a proper drink”
“Why not” I replied “I am in no rush to get home”
“Oh good” she smirked “neither am I”
It was late Spring and a lovely evening outside. Neither of us had heavy coats, just business-like jackets over tops and skirts. Although I was wearing four-inch heels, she was probably six inches taller than me and her killer heels made her look even taller. Her legs were quite shapely, like the rest of her.
As it was such a pleasant evening, we bought our drinks in the pub and went to sit outside, just round the corner from the pub as there was quite a crowd outside the front. We found a low wall in a surprisingly secluded space, and I followed her example and took my jacket off and folded it to sit on. Both of us had skirts that were mid-thigh length, so as we sat and both crossed our legs, both our skirts rose up our thighs.
I was bare-legged, as I dislike wearing stockings or tights at any time of the year, so as I crossed my legs a big slice of naked thigh was revealed and the hem of the skirt sat precariously close to being interesting for anybody watching us. However, when Julia crossed her legs, I saw she was wearing sheer stockings and, as her skirt rose up like mine, I saw the tan stocking top showing and one of the suspender straps and clip holding the stocking in place.
I was a bit embarrassed and tried not to look too much, but failed I knew. At the same time Julia was being less discrete as she looked brazenly at my small breasts. I was wearing a white sleeveless semi-transparent, cotton shirt. It was collarless and V-necked, with buttons down the front. My small, lacy, unlined, half-cup, white bra, with its front-opening, single hook sitting perfectly between my breasts, was completely visible through the shirt. However, with the jacket on all day, I did not think it was too revealing for a business event.
She was also wearing a white shirt with buttons undone down to nipple level, revealing a spaghetti-strapped white camisole underneath, and two very obviously bra-less breasts moving gently as she moved. While I thought my clothing was fine with a jacket on, I now realised I was showing nearly everything to her, and my nipples, prominent at the best of time, were reacting to the way she was now looking at me, and getting harder the longer she just looked at me. When she finally said “God Sally, you are gorgeous. You must have men after you all the time.”
I blushed and mumbled something unintelligible. I had never been with a woman and had never even thought about it, but for some reason this woman was making me feel quite flustered
“I tell you what” said Julia “Let’s go to a little restaurant I know round the corner from here, have a nice meal and a bottle of good wine and listen to some interesting conversation rather than the boring rubbish we have been listening to all day.”
Before I could speak, Julia had stood up and grabbing my hand said “C-mon gorgeous before some man spots you and entices you off to his man cave.” With that she started to march me off to her restaurant, giving me no time to do anything other than grab my jacket and bag in one hand as she pulled me along by the other hand.
As we rounded the corner, we had to squeeze through the big group of office workers all standing outside the pub. I was acutely conscious of my aroused nipples poking through my transparent shirt and bra, and saw a few male eyes looking at me as we shuffled through the crowd. Julia, as the older woman, was sort of shepherding me and protecting me as she led me down the street, still holding my hand, but telling me about the place we were going to.
When we entered the Italian restaurant, a smarmy older man greeted us at the door, giving Julia a kiss on each cheek, asking her who her delightful companion was. She laughed and introduced me as her new friend, Sally. She told him we had only met today and we had been bored to death by a bunch of talking men and needed a decent bottle of Barolo and a nice dinner to help us recover from the trauma.
He also laughed and said did she want her usual table to which she replied “Of course. Piero, thank you.” He led us towards the back of the Restaurant to a small secluded alcove with a table for two. Without asking, he took our two jackets from us, and when Julia asked him to take our bags too and keep everything safe for us, he quickly whisked those away as well.
We both slid onto the cushioned bench seat and, as we waited for the menus, I felt our knees touching under the table. I was not sure what was happening, but assumed it was an accidental touch caused by the small table. I had never been intimate with a woman, so I had no experience of being with a woman in circumstances like this.
Before I could move my knee, Piero returned with two menus and a bottle of Barolo red Italian wine. Julia tasted the wine, and then handed the menus back to Piero saying “Why don’t you just bring us two of my usual veal specials – that will be OK with you Sally? It is delicious and we do not want to eat too much, do we?”
We sat quietly tasting the wine, which was delicious, and talking about the conference and our various businesses, although all the time I was very aware of her knee pressed against mine. Although she did nothing more and the conversation was harmless, my tension never eased and my nipples stayed just as hard and rigid as they had been since she first stared at them.
When Piero arrived with our meals, which looked and tasted amazing, she leaned closer to me, placed her hand on mine, and said “You will enjoy this.” As Piero left us, he pulled a free-standing folding screen across in front of us, hiding us from the rest of the customers. She was still holding my hand which she now squeezed, telling me to relax and enjoy the food, patting my hand as she let go and sat back.
I began to relax, the food and wine were delicious as she had said it would be, the conversation was enjoyable, especially when we compared notes on useless husbands and messy divorces, and we were close to clearing our plates when I felt her foot slide forward, and the knee that had been pressing against mine all the time moved to push between my own knees. The foot and the knee were now stopping me from closing my legs and the bench seat gave no room for me to ease back.
With three glasses of champagne at the conference, a large gin and tonic at the pub, and now most of the bottle of powerful Italian wine, as she had given me much more than she drank herself, I was beginning to feel decidedly tipsy.
Piero came to clear the plates away, and when he asked if we wanted deserts, Julia said no but two Amaretto on ice would be welcome with our coffee. Once he had left us, Julia leaned across the table and whispered “You have the most amazing blue eyes – I have been entranced by them all night – and your nipples look quite delicious.”
She slid round the bench seat so she was close to me, her knee and foot pushing further between my own as she moved. I was blushing and unsure what to do or say, but she simply lifted her hand and brushed a lock of hair behind my ear, leaving her arm resting on the back of the seat behind me as she lowered it.
With the angle she was sitting to push her foot and knee between my opening legs, my knees probably six inches apart by now, meant that her other leg and hip was pressing against my thigh and hip now, and her breast was resting against my bare arm. At that point Piero arrived with the two coffees and two large balloon glasses of Amaretto. At that moment, the arm resting behind me came up to lay across my shoulders and the hand rested on my other bare arm pulled me towards her.
Piero placed the cups and glasses on the table and smiled at Julia and said “Enjoy,” to which Julia whispered “Oh we will” right into my ear. As a grinning Piero turned to leave, she moved her lips closer and her tongue flicked out to lick my ear before a kiss landed on my neck behind my ear. He smiled at us again and left us, this time moving the screen closer to our table.
I was dumb struck and terrified, but could not deny the evidence of my rock-hard nipples and the dampness I was feeling between my legs, I was aroused and excited by what was happening, so did what came naturally and turned my head towards her to accept the kiss I knew was waiting for me.
We kissed long and slow for ages, her tongue invading my mouth, mine becoming awake to this new sensation and entwining with hers. Her hand came up and held my breast, gently squeezing and massaging it, until through the shirt and bra she found my erect nipple and firmly pinched it, making me gasp into her mouth as the kiss continued.
In a panic, I suddenly blurted out “I need to go to the loo” and smiling Julia said “Yes, you probably do. Be quick or the ice will melt and your coffee get cold, and you are the one I want to melt.”
I untangled my legs from hers, escaped from the arm that was cuddling me and caressing my arm, staggered to my feet and slid past the screen. Piero pointed me towards the Ladies toilet, and I wobbled into it. I was panting and had no idea what I should do, but when I pulled down my tiny white lacy thong, the match to my bra, it was soaking wet. I was astonished at how wet my pussy was and how excited I felt.
I looked in the mirror and was surprised that two buttons of my shirt were undone and the clasp of my bra was quite visible. I went to do them up but paused, realised Julia must have popped them open while massaging my breast, and simply pulled the edges of the shirt together as much as I could. With a deep breath I left the toilet and walked back to our screened-off table, Piero watching me with a smile all the way. I squeezed past the screen and my shirt fell open again revealing my bra edges. She was now sitting so that we could be close together and held her arm open for me to slide back into her embrace. My arm went around her waist and the other one just hung uselessly at my side.
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