Giving Mature Ladies Pleasure Ch. 07

The next morning was excellent; Jack told them he had a meeting at eleven with Jean, who appeared to have a lot of potential customers. Both mum and May were excited that Carol was coming. Jack was sure that this mornings meeting would clear the air between them. It was all business chat; last night had been exceptional; he had done them both again after the meal. May loved the anal; she had three intense orgasms. Carol had messaged mum saying this morning she wanted to set up the procedures for smaller investors and she would bring all the paperwork with her. She had sent this at five this morning. Mum had replied at six.

Carol arrived at ten-thirty, she looked gorgeous in her mini-skirt and heels. Mum and May made her welcome; they had given her a coffee and were now sitting in Jack's office with a bundle of paperwork.

Jack arrived at Jean's house just before eleven. Jean opened the door; she was wearing a red silk dressing gown. Things happened very quickly after that. Next thing Jack was lying on top of Jean's bed with Jean on top of him in the cowgirl position, pounding his cock like nothing else mattered in life. Jack was stroking her big clit; this accelerated her first orgasm. Her second and much stronger orgasm came ten minutes later as Jack fucked her doggy style on top of her bed. They then lay on top of the bed; Jean was cuddling and touching Jack, Jean was glowing, she said, "I needed that, your cock is wonderful. I felt filled."

Jack told her that he enjoyed it too. Jean said, "Jack, it's difficult for me to explain this but here goes, I have a patient, she's in her early sixties, she's married, her husband is in her eighties, he has been in a care home for over four years. He has dementia, he doesn't even recognise him when she visits, but she still visits him every day. She would be an excellent investor for your new business. This is where it gets difficult. She is a very wealthy woman; there's serious money there. She is still sexually active with toys, and Di gives her oral once a week. She's seen pictures of your cock and the video of you fucking Carol. She likes what she saw; she would like to meet you. Would you be interested in meeting her?"

Jack replied, "Jean, I'm an accountant, I'm not a gigolo, I need investors, but there must be an attraction for me to have sex with a woman. I do not stray outside our group; that way, everyone stays clean."

Jean kissed Jack then said, "This lady is clean. I'm her doctor; I will not recommend any dodgy women to you. The lady that I'm talking about is very distinguished looking; she's tall with a voluptuous body, she oozes class. She has a lot of discretion. She asked for a picture of you; I told her that I would have to ask you; first, she respected that. I told her that you were setting up an Asset Management company, Di would be a consultant for you. Jack, may I give her your mobile number then she can contact you directly. I'll ask her to attach a photograph. If you are interested, then you can reply. Her name is Connie Watson. She will only have your mobile number and know that your name is Jack. Can I give her your mobile number? I believe that she can invest millions with you."

Jack nodded in agreement, then said, "I wouldn't normally do this, Jean, but I'll do it for you."

They showered together, then they both left. Jack went to a small Italian restaurant for lunch; he wanted to give Carol time with his mum and May. He was drinking a coffee when his phone beeped, Connie had messaged him, she had attached three pictures, she was a beautiful woman with a gorgeous smile and honesty in her eyes. She was so distinguished-looking, her figure was full of gorgeous curves. Jack liked what he saw. Her message read, "Hi Jack, I'm so glad that you allowed Jean to give me your number, I can appreciate your apprehension, believe me, I have a little doubt myself. If you like my pictures, then please send me a couple of yourself then I will know if I wish to continue. Kind regards, Connie."

Jack took three selfies which he attached to his reply to Connie, he liked the selfies, he looked very natural, there was also honesty in his eyes. He wrote, Dear Connie, you are a beautiful woman. I hope that you like my pictures. I am available to meet you this afternoon if this is convenient for you, then please suggest a place where we can meet for a coffee. Kind regards, Jack."

Two minutes later a reply came, it read, "Thank you Jack, the Bistro at the Hilton on George Street in twenty minutes, I'm wearing the same clothes as I was wearing in the selfie that I sent you. I have butterflies in my tummy, and I feel happy. Regards, Connie."

Jack arrived at the Hilton ten minutes later; the Bistro was quiet; he ordered a cappuccino and waited for Connie. She came five minutes later; she was tall and attractive; she was wearing a three-stone diamond brooch on her Jacket lapel, there were a lot of carats there. Jack stood up, extending his hand. Connie shook it warmly then sat opposite Jack. Jack said, "I'm a little nervous too, what would you like to drink?"

"May I have a cappuccino too?"

Jack ordered two as he had finished the one he was drinking. Jack then said, "Will I go first and tell you about myself? If I start to bore you, then please tell me, and I'll stop."

Connie laughed then said, "Please start; I have all day to listen."

Jack then told her about the family business, which was a property rental company. He said to her that he was single. He told her about Carol and Di and the help that they were giving in setting up the Asset Management company. Connie listened intently when he had finished. Connie said, "I have a sizeable property portfolio, maybe a start would be you looking after that for me. May I ask how your debt is structured?"

Jack replied, "We are debt-free, we have a sizeable war chest, we have no liquidity problems. We are working on a marketing strategy at the moment."

Connie said, "It sounds so exciting, I have a law and accountancy degrees myself. I was the Managing Director of a large private company; we were in the construction industry; we were a national company which was owned totally by my husband. My husband is over twenty years older than me. We had a son; he was my life and joy. I was old when I had him, thirty-seven. He was at University studying law. For his twenty-first, I bought him a sports car for his birthday. Two days later, he was involved in a horrendous car crash; he died instantaneously. I was heartbroken. My husband doesn't even know that he is dead. My life changed completely the day he died; his name was Jack too."

Jack said, "Connie, that's so sad, life can be so hard at times, don't blame yourself for buying him the car, he was twenty-one, at University, I am sure that the accident wasn't his fault. It must have been tough coming through all that alone?"

Connie said, "You are right, a drunk driver hit him head-on in a country lane, the driver of the other car was doing over one hundred miles per hour, it was tough for me, but I'm still here today."

Jack felt for Connie; he said, "Connie, what are you looking for from me?"

Connie said, "Jack, I'll be honest with you, I love sex, I need sex, the last time that I had penetrative sex with a man was thirteen years ago with my husband. When Jean showed me your cock pictures, it made me wet. When I watched you fucking the girl that Di licked out afterwards I came as I watched it. When Di licked your cock clean I wanted to help her. What do I want? I would like us to come to an arrangement that I see you at least twice a week with a proviso that I can call you for an additional meeting if my needs required that. I love sex as long as it is consensual, if you don't like anal, for example, I will respect that, and I love anal. What would you get in return? I could be one of your biggest investors, I'm not looking for a crazy return but a small percentage to support a charitable fund that I've set up. I believe that I can trust you; I wouldn't be offering this to anyone."

Jack looked at Connie's big tits; she had a gorgeous face and figure. Jack thought, Connie is a nice woman, he thought why not. Jack said, "Connie, I don't have a problem with what you suggest. I'm sure we both will have a lot of fun. When would you like to start?"

Connie smiled then leant over the table; they tongue kissed, Connie was a lovely kisser. Then Connie said, "Would you like to come home with me now? Jack, I don't have a problem if you see other women; in fact, I would like to join you anytime that you want with that. I have one last thing to ask you; this is very important to me. I have a little fantasy, when we are socialising, please call me Connie, when we are alone, when we are having sex, I would like you to call me mummy or mum, the question is now would you like to take mummy home and give mummy the good fucking she needs so much?"

Jack leaned across the table; they kissed tenderly with affection then Jack said, "Mum's going to have to suck Jack's big cock to make him hard then mummy will get a fantastic fuck. Has mummy any lube at home or will I have to use mummy's cunt juice as lube when I ass fuck her?"

Connie had excitement on her face when she said, "Mummy will take her baby's cock in every one of her holes; let's get home now."

Connie was driving a beautiful Mercedes SL; it was an expensive car. Connie lived in a very exclusive area of town. The house was impressive, Connie wasn't wasting any time, she took Jack straight to her bedroom, they were both naked in under a minute, Jack then saw Connie's lovely body, for her age it was gorgeous. Jack loved big tits, Connie's were huge, her vulva was smooth and swollen, she had a long sex slit. Jack liked her body. Connie was stroking Jack's massive cock, she knelt in front of him and started to suck him, she took his full length on the first attempt. She was good her tongue was teasing all around Jack's cock, Connie said, "Baby, I need it so bad, lay me on the bed then go on top of me then fuck mummy until mummy cums, I need to cum so bad, we'll take our time with our next fuck but just fuck mummy now."

Connie lay on top of the bed; she had spread her legs wide open for Jack, Connie had slid three fingers inside her wet cunt as she fingered herself Jack could hear a squelching sound, Connie said, "Baby, fuck mummy hard and deep, you can give mummy a rough fuck if you want, I need you to fuck mummy now."

Jack centred his cock in the middle of Connie's sex slit; Jack then moved the head of his massive cock inside Connie's cunt flaps to lubricate the head of cock with her cunt juice. With a gentle push, he was home; it felt tight and warm. Jack soon had a smooth rhythm going, Connie said, "Baby, it feels so good, you're filling mummy's hungry cunt with your big cock, I've wanted your cock for years, now I have you, fuck mummy baby, make mummy cum. "

Connie now was pushing her pussy against Jack's penetrating cock; her legs were wrapped around Jack's hips, she was gripping Jack's cock with her strong cunt muscles, Jack said, "Mummy, it feels right, mummy has got a very tight cunt, does mummy like her baby's big cock?"

"I love it to bits; I've been dreaming about this for so long, mummy loves having your big cock inside her, is mummy giving you a good fuck?"

"Mummy, we are both working together to give each other great fucks, mummy cum for me, mummy let me feel your cunt juice on my cock, mummy CUM for me."

Connie then had a body-shaking orgasm, Jack still kept pounding into her, hoping that he too would cum but that didn't happen, he knew that he would shoot inside her later. Connie continued to shake for a couple of minutes. When she composed herself, she pulled Jack close to her, she kissed him so affectionately, Connie's urgency was gone, she had needed to cum, and she had. Connie said, "Thank you, Jack, I needed that, it was wonderful, can you stay with me today as I want to get to know you?"