This is a loose sequel to my debut 3 part story: An Observed Threesome. If you want to know what changed Mrs Shepherd, you'll need to read this. If you are not bothered about the backstory just read this one. Everyone in the story is over 21 and it is entirely fictional. It's set in the UK about 2010.
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Chapter 1 - An Unexpected Opportunity
Since observing Mr. Paul and his former students cavorting in the most depraved way, Mrs. Shepherd had herself undergone a transformation. She had hired a personal trainer to get her fifty something body, which was in admittedly good shape anyway, even more toned. She'd been to the beauty salon and had her vaginal area waxed within an inch of its life. She purchased a vibrator online and now most of her nights were spent furiously masturbating to pornography on the internet, in her large, but sadly empty house.
After watching the scenes of debauchery she alternated between wanting to be dominated and to dominate herself. Mr Paul, the teacher she had observed was very much her target for the man she was going to dominate. Unbeknownst to him she had a copy of the filmed footage that had been made of his exploits. Whilst he and those two sluts had been showering together after their night and morning of fucking, it had been child's play to quickly sneak into the hotel room (using the adjoining door between the rooms) take the camera, download its contents and then place it back on the dressing table. However, she lacked the confidence to take Mr. Paul to task just yet. After rediscovering her sex drive she was at a loss at how to proceed next. The answer came, indirectly, from an unexpected quarter.
Mrs. Shepherd was at an Old Girls and Parents get together for the school for which she was headmistress. Normally she would enjoy these social gatherings, but she was now so addicted to spend her evenings masturbating that all she could think of was being at home watching porn and playing with herself. She'd got rather addicted to MILF porn where women of her age would find themselves being fucked by multiple partners much younger than themselves self. The thought of their hard bodies, erect penises and (most forbidden of all) erect penises ejaculating on her face and breasts made her feel so hot. Her much missed deceased husband had been a wonderful partner, but upon reflection, their sex life had been rather straight laced.
It was with this in mind when she found herself talking to a rather tearful parent, a Mrs. Grisham, whom she see wanted her counsel. Mrs. Grisham's daughter Jill, must be thirty by now, and was happily married to a young doctor in Yorkshire when last she'd heard. What could possibly be the matter? Mrs. Shepherd reflected how many parents whose children had long left school would still seek her advice
"Mrs. Grisham, whatever is upsetting you?" She asked drawing her to a quiet corner.
"I recognize that look from when we had all those problems with your Jill coming to terms with her dyslexia, gosh! And many how many years ago was that?"
"Oh Mrs. Shepherd. Such kind words, such a calm voice in a crisis, that's what I used to say to my husband, but oh I'm at my wits end. I knew I was right to see you! I just don't have the experience of dealing with such appalling behavior and well, I know there isn't much you've not dealt with. My husband won't let me talk to anyone in case it gets out you know. I mean we're both strict church goers!"
Mrs. Shepherd stared over to Mr Grisham who was staring at his wife and Mrs. Shepherd with a quiet determination. Puzzled Mrs. Shepherd asked whatever had happened. The problem it seemed was Jack, the youngest of her children. He was twenty-five and had always been something of a problem. Going to the best schools couldn't make him academic, and unlike his sister, who'd grafted her way through school and university, he'd always been a bit wild. Asked to leave school in his final year he'd drifted from one thing to another until he'd finally set up - with his parents' financial support - a photography business. All had been fine before the recession, his father's contacts had got him some good deals taking pictures for prospectuses and brochures for businesses and schools and he'd also done a lot of wedding pictures as well. Things had dropped off with the slump and he'd taken to doing something that was so horrifying Mrs. Grisham took some moments to even describe it.
"Whatever has he done?" Mrs. Shepherd asked all of agog.
"I can hardly say. I'm so so so ashamed, but he can't carry on. I mean if people
were to find out!" Mrs. Grisham hissed desperately.
"Please tell me, I've had a lot of experience with silliness in my time and I guarantee I'll sort this out. It's not drugs again is it, because -"
"No no it's something far worse." Mrs. Grisham drew Mrs. Shepherd to the quietest part of the room and looked like a frightened mouse as the women happily chatting with each other over a buffet and glass of wine.
"Two months ago, Jack came over for Sunday lunch. He was really happy and apparently business was booming. Him and his father went down the pub before lunch and I mean I'd pretty much finished dinner so when I saw Jack's MacBook in his bag I just thought, ooh, I'll have a look at some of his photos. I was shocked!"
"What did you see?" Mrs. Shepherd asked.
"Women, naked women! When the business started to slide, he'd decided to do what they call Boudoir photos. Kind of glamour pictures. From speaking to him afterwards that's how it started."
"What do you mean?"
"Well most of these women were just having pictures done where they might be naked but it was all tastefully done, you know it was all hinted at. A bit like that film 'Calendar Girls'. They were just women like us really, most of them it seemed just wanted to feel attractive, I've done some research and it's quite an innocent practice."
"Well whatever is wrong with that? I mean it's perhaps not something to talk about at the church social, but it's nothing to be ashamed about. It's good that -" Mrs. Shepherd exclaimed.
"You don't understand. After looking at these pictures, well I wasn't happy but as I tried to log out I saw another file. It was called X rated!" Mrs. Grisham was having trouble not sobbing.
Mrs. Shepherd felt her vagina moisten and she asked in a voice that she hoped was not too husky, "Did you look in the file?"
"Yes Mrs. Shepherd."
"And what did you see?"
Mrs. Grisham shut her eyes as she spoke as if trying to block out the memory. "It transpires that when these photographs are taken some of the women become rather aroused and find themselves wanting more. There were pictures of women that were topless, which was bad but there were pictures of women that were far worst. But but..."
"Yes Mrs. Grisham."
"There were pictures of women masturbating and finally there were pictures of Jack having." She paused and then whispered. "It seemed that he'd asked a couple of his friends along to some of these photo shoots and there were pictures of him and his friends, well, well, copulating!" the whisper almost became a harsh scream, "worst of all there were photographs of the foulest kind, where Jack and his friends, well, they ejaculated on these poor women's faces! I say poor women!" and Mrs. Grisham hissed like an Old Testament preacher, "Those sluts seemed to be enjoying every moment of their depravity!"
"I see Mrs. Grisham." Mrs. Shepherd struggled to keep her voice steady. "Did you confront Jack about this, this, lewdness!"
"Indeed I did. There was a huge scene. He was furious that I'd invaded his privacy. It turns out that it had happened the first time as an accident when one of the women had got carried away and well, so did he. But then he said that he realized that's what many of his clients wanted. And for these hardcore pictures he could charge top dollar as it were."
"But what of his friends getting involved! It's disgusting!" Mrs. Shepherd found herself trying to not drift off into a reverie.
"It appears that one of his clients had suggested it and well, it's quite popular now. I mean the shame of it! The shame of it! He says he won't stop! But if word were to get out! I'm at my wits end!"
"Leave it with me Mrs. Grisham, leave it with me."
"There is one thing, Mrs. Shepherd, one of the pictures, there was someone I knew in it. Someone you knew!" she nodded over to Mrs. Grace, the wife of one of the richest parents at Mrs. Shepherd's school. "Her face Mrs. Shepherd, her face was covered in semen!"
Chapter 2: Two is Company and Three
is a Crowd.
Mrs. Shepherd had spent sometime looking at the Jack Grisham's photographic website and the Boudoir section looked incredibly tame on first inspection. She'd never met Jack, but the picture on the website showed a handsome twenty five year old who looked like he played rugby. She decided to ring up and dip a toe in.
"Mr. Grisham?"
"It is indeed, how I can help you?" a voice, warm and confident rang back.
"I was wondering if I might book a Boudoir Photography session?" she felt her voice tremble as she said it. "My name is Mrs. Savage" she felt herself blushing as she lied, "and I'm friends with a Mrs. Grace. She highly recommended you and your team of photographers."
"She does, does she?" Mrs. Shepherd could almost visualize him smiling.
"Please don't tell her I've called I'm rather shy, but er, I was hoping I might get the same experience that she got. If that's OK?" Mrs. Shepherd found herself stuttering out.
"Well," she could definitely hear him smiling down the phone now, "I'm guessing if I were to ask Mrs. Grace she wouldn't know who you are, as that's not your real name is it?"
"How can you tell that Mr. Grisham!" she squeaked as if she'd been goosed.
"Just a hunch, I'm sure Mrs. Grace told you of the confidentiality of our service."
"Indeed she did. You use digital cameras I believe?"
"I think everyone does these days"
"Well if I were to download the pictures from you camera's straightaway that really would guarantee confidentially would it not? Your service doesn't come cheap I believe?" Mrs. Shepherd couldn't believe that she was committing herself so quickly. She'd only meant to sound him out.
"It'll be a thousand pounds per hour, I can provide clothing, but I'm guessing you're the kind of girl that will want to bring her own? Am I right?"
"You are indeed. I'll see you on Friday." Mrs. Shepherd found herself agreeing.
"Ok, we'll start off with just the initial Boudoir session and see if you want to take it further, that'll be an extra two hundred, does that seem agreeable? It's best to meet in person before you decide whether you want to go for the full service."
"I'll see you on Friday then. Can I just ask how many of your er, assistant photographers will be there?" she found herself asking.
"I thought one should be enough"
"Could I request two please?
He really was grinning now, "Two it is, but it'll cost you twenty percent more. With me that will be three. You are a greedy girl aren't you Mrs. Savage?"
"I am indeed Mr. Grisham and it's been so long since I have eaten if you know what I mean?
She slammed the phone down and rushed to the bedroom with an insatiable need to climax.
Chapter 3: Mrs Shepherd finally gets fucked
Mrs Shepherd was standing in a bright green summer dress that was fashionable rather than sexy and the only thing that gave a clue to her intent were the matching dark green high heels that were just that little bit too high.
Jack Grisham grinned. He'd suggested a Boudoir session as a preliminary just incase she was the size of a bus or was ugly, but this was prime Milf. He'd got a real taste for fucking these sluts and to get paid for it was even better.
