Jack the Complex Lover 2018


Jack had been dating Kay for eighteen months. Kay was in her final year at University for her teaching degree. From Sunday to Friday she lived in student's accommodation close to the University. She came home at the weekends and stayed with her widowed mother, Joan. Jack stayed every weekend with Kay. He owned every one of her holes. She was his cum bag and slut. Jack was a lawyer, he was twenty-six and recently been offered a partnership in the Law Firm where he worked. He was six foot four tall and had an athletic body. He was also blessed with a massive cock.

Kay loved sex. Every weekend was unbelievable. They would go out for meals then back to Kay's bedroom. John was aware of what was happening. She had told Kay that she and Jack were both adults and knew what they were doing. It suited Jack as he still lived with his widowed mother, Jill, who was very religious and disapproved of any pre-marital sex.

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   He enjoyed staying with Jill during the week as she was an excellent cook and took care of all his laundry. Jack's father was the Senior Partner in the Law firm where Jack worked. Jill owned the property and was a wealthy woman.

Every weekend was a weekend of sex for Kay and Jack. It was constant. Kay had given Jack her virginity on the carpet of Joan's lounge. Joan was a sales representative for a pharmaceutical company. The day after he had taken her cherry Kay told Joan what had happened. Joan realised that Kay was now sexually active put her on the pill immediately. Joan made Jack so welcome in her house. She gave him a key to the house. The day after he had taken Kay's virginity Kay and Jack were sitting on the sofa. Joan came in and sat in an armchair, she said, "Jack, I would like a word with you. Kay told me what happened yesterday. "

Jack said, "Kay, why did you tell her, that was our special thing.

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Joan replied, "Jack, I am not angry about it, in fact, I am happy that it was you who did it. Kay is now on the pill, so you have no worries there. I am happy for both of you. But don't be too noisy, as that would arouse me. "

They then got into a routine. Jack would spend Friday and Saturday nights at Kay's. On Sunday morning he went home. Jill was always at church and would return around one in the afternoon. They would then go to a local hotel that did an excellent Sunday roast. That and going to church were the highlights of Jill's life. It was the least he could do for Jill as she cooked for him for breakfast and dinner every day. Jill would visit the Hospital and the Hospice, to visit parishioners that were there. Jack had bought her a laptop for Christmas, and she spent a lot of time researching things on it. She had even taken evening classes at a local school on computer literacy.


Four months later Jack and Kay had had a very erotic session.

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   Jack needed the bathroom, and as he passed Joan's bedroom door, he heard her sobbing. He went back to Kay's room and said, "I've just heard Joan sobbing. What's the matter with her? Is it because she hears us having sex?"

Kay replied, "She gets depressed, she works so hard. She never socialises. I think that she is missing a man. She is in her late forties now, and she still has her needs and desires. "

Jack said, "Jill does so much for me. Should we stop having sex when she is in the house? I want her to feel happy. "

Kay replied, "She loves being around you. She loves flirting with you. Tomorrow night there's this reception for a Professors retirement. Jill's company is sponsoring it, and I am helping her. I will spend time with her there and when we get home. I will have a real heart to heart with her. It would be better if you were not here as that would give us privacy to speak openly.



Jack agreed to this. Saturday morning and afternoon flew in. They left at six for the reception. Jack hadn't phoned Jill as on Saturday nights she usually watched television. He went to an Italian restaurant for a meal. He arrived home just after eight. He heard the sounds of a film coming from Jill's bedroom. He heard an actor's voice say, "Does mummy wants to be ass fucked?"

Then the actress said, "Fuck mummy's ass hard and deep. "

The bedroom door was open, and Jill was lying on the bed. She was naked, and her body looked excellent. She had a towel under her, and two vibrators were inside her. One in her ass and the other in her cunt. Jack couldn't believe his eyes. He quietly went downstairs. He went to the fridge and poured himself a glass of wine.

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   He then WhatsApped a message to her; it read, "Mum, I have just arrived home. I hear that you're upstairs. I message you to let you know that I am home so that you wouldn't get a shock. I am having a glass of wine if you would like to join me. Your Jack. "

Two minutes later he heard her voice from upstairs; she said, "Darling, I am up here killing time. I have to go to the Hospice at nine as I promised a poor soul that I would visit her tonight. She hasn't long to go. I will have a glass with you when I get back. That's a surprise seeing you on a Saturday night. I will be down in a minute. "

She came down five minutes later wearing her usual twinset with pearls and a skirt. She gave Jack a hug and a kiss on the cheek. She said, "I had better dash. I will be back within an hour, if not then I will message you.

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She then left. Jack sipped his wine then went upstairs to Jill's bedroom. He looked in her bedside cabinets. Both had vibrators, dildos and lube oil. He then opened her laptop; her favourite porn was incest. He checked her photos; she had lots of her posing in risqué lingerie. In every picture, she was wearing a masquerade mask. She had a private email address. Which she used to communicate with guys that she had met online. Then he found a roleplay site where big breasted mature, with an open mind and a creative imagination, was looking for a younger man that she could mother; he should be well endowed, intelligent and exciting. For online fun.

He saw that she had been doing this for over two years. He had only given her the laptop four months ago. Then he remembered her old iPad. He went to his computer and created an account using the nom de plume 'Horny Graduate' looking for a mature, intelligent woman to have fun with.

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   Kay had taken some cock pictures which were impressive. He attached three pictures and wrote, "Hi big breasted mature; I love your profile pictures. I am twenty-six years old and am looking for a mature woman who enjoys younger men. I am fortunate that I am well endowed as the attached pictures will show. I am an accountant with my first foot on my ladder of life. I am honest. Look forward to hearing from you. Bob, aka 'Horny Graduate'. "

He then put everything back where he had found it. He found a picture folder named 'Cocks', there must have been over fifty different cocks there, but none came anywhere close to his. He then went downstairs to the lounge. He put the roleplay site on his smartphone though he didn't expect to have a reply anytime soon. Jill hadn't been away for thirty minutes. He went to the kitchen and poured another glass of wine. He was trying to work this out in his head.

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   Why was Jill doing so much charity work and having another life on the Internet?

His phone beeped, he had a message from Big Breasted Mature, it read, "Hi Bob, so happy to read your message. Wow, you are well endowed, that beauty looks massive. I am widowed for over six years. I have not dated a man in this time. I went online just over two years ago after a woman in my church told me about the roleplay site. I have a son the same age as you. He lives with me, apart from the weekends which he spends with his girlfriend. I do a lot of charity work for the church during the day. At night I enjoy the roleplay site. "

"I have never met anyone that I write with though I am tempted with you. I have my fun online. I do peep shows; I love to see a man masturbate then squirt his spunk. If you are on Skype, then we can Skype. I have attached some pictures that I took last night. My son is home this evening, this is unusual, as he is normally with his girlfriend.

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   I am going to have a glass of wine with him when I get home. I am looking forward to that. If you don't hear from me later, then I will try and get back to you tomorrow. Looking forward to hearing from you Jill aka Big Breasted Mature. "

Jack replied, "Thanks Jill, I like what I read. I am not on Skype but will look into getting it. Tell me what you enjoy most, your charity work or your roleplay life? Have you ever thought of having fun with your son? Don't worry about when you reply. I am doing a lot of research work this weekend. Thanks for the pictures, you have a beautiful cunt, smooth, swollen with a perfect slit. Your tits are stunning. Look forward to hearing from you. Bob. "

Jill replied, "Bob, what interesting questions and thanks for the compliments. I enjoy my church work as I can help and give comfort to people. I love it when I am in roleplay mode.

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   I get very aroused when I am on camera doing it. I love to orgasm, though there are not many men that turn me on. In regards to my son, I have fantasies about him. He is tall and athletic. He is intelligent. A while ago he used to wank into a hand towel. I would find it in the laundry basket. It was still wet with his spunk. I never said anything to him about it. I was tempted to wash it and leave it on his bedside table so it would have been within reach for the next time. I would be scared that I could lose him. Write when you can Jill. "

Jack was surprised by this as he had wanked into a hand towel. He replied, "Jill, I love your honesty. Do you get jealous when he is with his girlfriend? Do you ever flirt with him? Tonight when you have your glass of wine, relax with him.


   Wear something sexy. You have fantastic lingerie. Tell him that you are both adults who have needs and desires. Talk with him about both of your lives and how you can make your lives better. I think that you could find that maybe he wants to fuck you. I wish you luck but be honest with him. Bob. "

Jill read it with interest. The lady that she was visiting was now asleep. Jill wanted to stay until ten with her. She then messaged Jack; it read, "Darling, I will be home soon. The lady is asleep; it's doubtful she will be here in the morning. The good thing is she recognised that I had kept my word and visited her tonight. I am looking forward to having wine with you. When I arrive then pour me a glass and I will take it to the shower with me.

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   I always feel better when I shower after visiting these places. Be with you soon, Jill. "

Jack was pleased when he read the message. She had never called herself Jill to him before. He topped up his glass, and he had a message from the roleplay site, it read, "Bob, thank you for making me realise so much that I was doing wrong tonight. Yes, I am jealous of his girlfriend, as I could give him so much pleasure. I have never flirted with him in my life. Though he gave me so many orgasms when I breastfeed him. I will wear something sexy tonight for him. I will talk to him about the things that you have suggested. If things turn out the way that I want, then he will sleep in my bed tonight. Thank you for your good advice. Jill. "

Bob replied, "Good Luck. "

Jill arrived five minutes later.

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   He gave her the glass of wine. He said, "If you need more then call me, and I will bring it up to you. "

She smiled and leaned forward and kissed his cheek then said, "You are a darling, I may just do that. "

Jack knew then that tonight would be good. Ten minutes later she shouted, "Darling, I need another glass. I am in the bedroom applying my war paint. I am only wearing underwear so don't be surprised. "

He took his glass and the bottle upstairs. Jill was sitting at her dressing table. She was wearing a red crotchless bodysuit which pushed her massive tits up. She had a red thong, which fitted her tightly, showing her swollen slit to perfection. He topped her glass up and sat on an armchair facing her. He said, "Cheers, you look fabulous, I am so glad that I came home tonight. Jill, I wish we had done this after dad died. I worried about you for so long.

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She replied, "Darling, I would have loved that. We haven't spent enough time together. I am your mother, and I love you with all my heart. I have done everything that I possibly could for you. We should have spent more evenings like this, drinking wine together, talking about things that are important to us. Since your father died, I have never been out with another man. I have needs and desires, the ten years before your father died I didn't have sex with him once. I haven't had sex with a man for over sixteen years. That's a long time. "

"I have my toys and fingers, but that's not the same as a hard cock. I have met men online, and we have had online sex which I enjoy. I suppose that nowadays that's the safest way to have sex. I want us to spend time together. Perhaps even taking a holiday together, so we get to know each other. How do you feel about that?"

He replied, "Jill, I would love that.


   I appreciate everything that you have done for me. I love sex too. I need sex. I function better when I have sex on a regular basis. I wish we had spoken like this before. Let's go to the lounge so we can kiss and touch on the sofa or would you like to go to bed?"

She put her glass on the coffee table near to where Jack was sitting. She then undid his belt and removed his trousers and boxer shorts. He pulled off his polo shirt and socks. He was now naked. Jill said, "Sit in the armchair and leave the rest to me. But first, let me make this beauty, big and hard. "

She removed her thong and popped both her tits out of the bodysuit. They looked wonderful. She then knelt down in front of him, her tongue teasing his cock. He had a little pre-cum in his slit.

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   She squeezed his slit open, then with a flick of her tongue the pre-cum was gone. She soon was taking his full length in her mouth. He was quickly rock hard. She then squatted over him. Using her index and middle fingers, she spread her cunt lips open. Out popped her massive clit. It was enormous. She then teased her clit as she stroked it with his bulbous tip. She was good.

She centred his tip in the middle of her swollen vulva then pushed down on his cock. Two-thirds of his cock vanished inside her cunt. With up and down and circular movements she started to ride him. She was gripping his cock at the base and the crown. Her tits were wobbling beautifully. He was rubbing her clit with two fingers as she rode him.

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   She was getting very wet. There was a constant stream of her cunt juice coming out of her hot cunt. Jack was using this to lube her ass. He was fingering her ass with three fingers. Jill loved it. She was moaning with pleasure.

Ten minutes later he raised her up then holding his cock at the base guided it to the centre of her ass, and she pushed down on it, and the full length slid inside her. She said, "That feels fucking wonderful. This is the first cock that's ever been in my ass in my life. I have had a few vibrators but it feels so good. Jack, you have taken my ass virginity from me tonight. "

She then started going up and down with a circular motion. She was beginning to pound her ass with his cock. He knew that the way she was moving she was stimulating her G-spot with the bulbous tip of his cock. Five minutes later she had a massive vaginal orgasm.

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   She was shaking with it. He told her to keep going. Ten minutes later she had another vaginal orgasm. This one was more intense. She was trembling now. He said, "Darling, that was good now put me back in your cunt and fuck me until I cum. "

She did that, and thirty-five minutes later they both climaxed simultaneously. Jill sat on his cock gripping it tightly, holding him inside her. He pulled her forward, and they kissed tenderly and affectionately. It was also the first time in their lives that their tongues had been in each other's mouths. Jill said, "That was, without a doubt, the best fuck that I have ever had in my life. You are something else. I had two massive vaginal orgasms within minutes. We must do that again. I will go downstairs and get another bottle of wine.

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   I won't go to church tomorrow as I want to spend the morning with you in bed. "

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