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This is a complicated one; Jack had just finished his fourth year at University studying Law. His girlfriend of two months had just ditched him, telling him she liked him as a person, but she wasn't sure if he would be part of her future. His girlfriend was Mags, the daughter of May, Jack's mum's best friend. Jack had been attracted to Mags because she was beautiful, tall and had big tits. Also as being a friend of the family was another factor. For nearly the last three years, Jack had an affair with his Class Lecturer; she was a high-powered businessman's neglected wife. She was fifty-five; Jack had loved the sex; she had taught him so much.
Jack hadn't dated since he left school. He didn't need to; he was getting everything from Jean, his lecturer, whose husband had been promoted, and they moved two hundred miles away. Jack had then started to date Mags; this was another reason he dated Mags as people were curious as to why he wasn't dating anyone. Jack was tall, intelligent and very good looking. However, he had been getting no sex from Mags. Mags was on the pill, but Jack had never penetrated her once as she wasn't comfortable with the size of his cock. When she was sucking him, she would only take his bulbous head in her mouth. The best he got was a hand job; Mags looked bored when she gave him those.
Mags was spoiled, an only child like Jack, her mum gave her everything she wanted. May was an Accountant; she had her own firm and was very successful. Jill, Jack's mum, was a lawyer with her own firm too. Professionally they worked closely together, serving both of their clients. Jack worked at every opportunity for his mum. Every year he was becoming a more significant asset for her. May and Jill were both widowed; their husband had died early from cancer. So Jack was a little surprised when he broke up with Mags, but in no way was he broken-hearted.
"Mum, it's massive. It's thick and long with a bulbous head. Once I let his cock inside me, he got only the head in, and I asked him to stop as my pussy felt so stretched. Imagine if I'd let him in, and then it didn't work out. The next guy I would have would be thinking that I have got a very loose pussy. Mum, it's just too big."
"Mum, when I wank him, I can't get my hand around his cock; there's a gap of two inches between my middle finger and my thumb. It's long, at least ten or eleven inches. When you look at it, you think it's beautifully proportioned, but it's just too big for me. Mum, how can I let him down gently? I'm starting a new job at the end of next month; I'll be leaving home then. John, who I used to date, is working for the same company. He has got an apartment, so I'll move in with him; he's got a cock that I can handle."
May was impressed with the size, she had a big cock at University, and she had loved it. Those were the days she had shared the guy with Jill; they had done a threesome with him, they both had loved the sex with him. May then said, "Mags, you must do this nicely; you must think of Jill and Jack. They have been good friends for so long. Don't tell Jack that his cock is big for you. Please don't say anything about the size, or he may think that he's a freak. Cocks come in all sizes; maybe later in life, you'll want a big cock. Start dropping hints that you've got a new job coming up and you're going into an apartment. Let him know nicely; I'm sure that he'll appreciate that."
May was so friendly to Jack for the next few weeks, giving him hugs, pulling him close to her, letting him feel the weight of her massive tits on his chest. May was sure that Jack was responding, but Mags was still around, and May was worried that Mags saw what she was up to. Jack certainly noticed how May was when he was at her house. May had a very sophisticated alarm system in her home. One Saturday night, May had left Jack and Mags in the lounge. The concealed camera was in a mirror facing the door; anyone coming in the door would be captured on film. In its line of view, it took in the couch. Mags was giving Jack a hand job. Jack's cock was massive; she had never seen one as big; Mags was right; it was beautifully proportioned. May then got a big dildo out and started working her very wet pussy with it. Naturally, may wanted Jack's cock.
Jack didn't reply. He leaned over their lips met, May's tongue was deep inside Jack's mouth, both their tongues were so active. Their kisses were intimate and tender; Jack's cock was stiffening; he was so attracted to May. His right hand found May's massive left tit. He squeezed and played with it for a couple of minutes as they kissed. Then May said, "Be firm with my girls Jack, you won't break them. They are very sensitive; I can cum if you're firm with them. I want you to make me cum."
May's hand found the bulge of Jack's massive stiff cock; she squeezed and stroked it lovingly for a minute then said, "What a magnificent cock, Mags hasn't thought this through. Can I have all of it, Jack? I'm getting so wet just touching it. Jack, slip your hand inside my leggings and feel my honey pot; no, I'll change that; it's your honey pot now. Jack, this is special for me; I haven't had any cock since my husband died. Can we go to my bedroom? Then we have all night to do it nicely."
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