Giving Mature Ladies Pleasure Ch. 05

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Jack Gets Involved with Other Mature Women.
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Part 5 of the 8 part series

Updated 06/10/2023
Created 08/02/2020
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Jack1107
Jack1107
3,544 Followers

Jack's phone buzzed just after twelve, he thought it was mum, but it was Carol, she wrote, "Jack, Di called me, she loved sucking you off, that was a big thing for her. She was telling me that she can control the Professor, she has evidence of him using University computers for viewing porn. She has challenged him on this and told him that I've to get a First-class Honours and he's not getting a blow job. Di has asked me if after the service tomorrow we could all go back to the apartment, Di wants to watch you fuck me then she will lick my cunt clean. My finals start next week, and my last exam is in four weeks. Will we do it tomorrow or put it off for another day, I think it's best to get it out of the way now as I know that she'll help me with my exams. I loved being with you tonight. Carol."

Jack replied, "We will do her after the service, we can video it, that will ensure that she helps you. I loved being with you too. I'll pick you up after nine-thirty, Jack."

Jack saw that he had a WhatsApp message from Jean, it read, Jack, what a surprise I got when Di showed me the pictures and videos. What a beautiful cock you have, it is impressive. Di has edited the last part of the video into slomo; I get so wet watching your cum dripping from Di's mouth. I hope that you enjoy the edited video. Di is looking forward to seeing you tomorrow and so am I. We should arrange an evening with Di and me though if you want to include Carol, that can be a lot of fun too. Let's keep in touch; I'm sorry that I can't stay longer tomorrow. You now have two goddess's, love Jean."

Jack watched the slomo video; it was impressive. Di was a very sexy woman; Jack knew as he watched it that Di would help Carol with her exams. Jack then replied, "Dear Jean, thanks for the slomo, Di is a very sexy woman, and so are you. Yes, I would love to spend an evening with you and Di. We will arrange something soon. Carol was telling me that you have magnificent tits and a perfect cunt. I would be so interested in seeing them. Do you have any pictures you could send me so I can know what to expect? Love Jack."

When Jack awoke in the morning there were many pictures from Jean, her tits were like Di's, massive and didn't sag. Her cunt pictures were incredible; her vulva was smooth and swollen with thick cunt flaps, she had a very long sex slit just like Di. In other photos, she used her fingers to spread her cunt flaps open. She had an enormous hooded clitoris; it was like a little cock just wanting to be sucked. Jack knew that he would have the two sisters one night soon. He replied to Jean, thanking her for the beautiful pictures.

Jack arrived at the office at ten to seven. Mum's car was in the car park. Mum looked stunning in a very short mini-skirt and heels; Jack had seen the benefit of the heels when he bent her over the desk, her ass was level his cock. Mum was wearing a blouse that looked tailored around her massive tits; they kissed tenderly then went into the office. Mum pointed to the chair that she wanted Jack to sit on. Jack stripped naked, then sat in the chair; his cock was rock hard. Mum took off her blouse and skirt; she was wearing a crotchless bodysuit with no panties. She kept her self-supporting stockings and heels on. She then popped her tits out of the cups; her tits were now so accessible. Mum then squatted over Jack, gripping his cock at the base, she teased her clit with the bulbous head of his cock. Mum said, "I loved the video when I have my period we can still fuck or do you not like to fuck when there is blood around? The warm blood can stimulate your cock when you're inside me. If you don't like that, then I'll give you blow jobs like Di. We should invite Di over then you fuck me, and Di will lick my cunt out after you cum inside me."

"I've never tried that mum; you could lie on top of a towel so your blood will be contained in the one area. I have got a slomo video of Di finishing me off then licking my cock clean; I'll message you it later."

"Do that Jack, I like naughty pictures and videos. Was it taken on an iPhone as I think my iPhone can do that, then we can take pictures when we are fucking."

Mum then started to ride Jack; it was beautiful, she gave him a fantastic ride, they both enjoyed it, mum said, "Jack, that was amazing, we must use the chair again, but I still love it when you fuck me doggy style over the desk."

They showered together then mum made breakfast. They chatted so much. Jack said to mum, "If Carol joins us in the office, then with you, Aunt May and me there's three accountants and a lawyer. We have a private property company. We should develop an Asset Management side to the business; we are qualified to do it, we're doing it ourselves with our own money, why shouldn't we do it with other people's money then we'll earn commission?"

"Jack, that's a great idea, after May and I graduated we both spent time in Asset Management offices, we just need to apply for our Practicing Certificate, and we are in business. I'll talk to May today about it, she's very excited about starting work, don't you forget to feel her pussy before you co, she won't be wearing any panties, and she loves your cock and the videos."

Just before nine May arrived, she looked stunning, her mini-skirt was shorter than mum's, she was wearing a tight-fitting top that showed her tits to perfection, Jack hugged her, and a kiss on the cheek then said, "Aunt May, you look gorgeous, can I start calling you May now?"

"Of course you can Jack, I'm so excited about this, I was bored to tears at home. Give me a few days to find out how everything works; I hope that you haven't a big telephone exchange as I was having nightmares thinking about that."

Mum laughed then said, "Let's have a coffee with Jack; he must leave shortly for the service."

Mum and May were two beautiful women; they were head-turners if you saw them in the street. Jack made three Cappuccinos as mum explained the phone system. Mum phoned from her mobile then when she was on the call to May she asked Jack to call May on the office line. May was excellent; she asked mum to hold then wished Jack a good morning as she took his call. Jack said, "Good morning, do you talk dirty?"

May replied, "I can if you want; I hope this is part of the job."

It had just passed the half-hour, mum purposely left May and Jack alone in mum's office. May came close to Jack then said, "Do you want to check if I'm wearing what I'm supposed to wear?"

Jack took her in his arms and cuddled her; they tongue kissed, May like mum was a lovely kisser. Jack felt both of May's massive tits; they were the same size as mum's. Then he slipped his hand up her skirt, he felt the smoothness off her vulva, he fingered her cunt flaps, he slid two fingers up her very wet cunt then Jack said, "May, don't worry if you make mistakes, you've got the job. You're wearing everything that you need."

They kissed again; May put a lot of affection and tenderness into the kiss. Jack then left, on the way out he passed mum, he put the two fingers that he had in May's cunt close to mum's mouth, mum then licked her sister's juice off his fingers. Mum said, "Will I see you tonight?"

"I'll call you before five mum."

They kissed then Jack left. Once again, Carol was standing outside; she was wearing the same black outfit as yesterday, she was glowing. In the car, Carol said, "I owe you for doing this for me today, the First means a lot to me, I'm doing it for mum. Di didn't mix her words with the Professor, she threatened to make his perverted life public, Di said he was a worried man when she left him last night. She found him in his local pub; he kept telling her to be quiet."

They arrived at the church; Jean was standing outside with Di; they both looked so sexy in black. Di came straight to Jack's car; there was an astonished look on her face, she said, "Carol, you won't believe this but a colleague just phoned me, the Professor's wife went to his bedroom this morning as he hadn't come down for breakfast, it looks like he had a heart attack. The doctor hasn't seen him yet, but that's what his wife thinks. The Chairman of the Law department, has because of my age and experience, promoted me to Professor, I have to take over his classes, your First is now guaranteed."

They hugged and kissed, Carol, said, "Di, I'm so happy, that's a huge relief. I think that I will get drunk tonight."

As they walked to the church, Jean whispered to Jack, "I've sent you a slomo video of me teasing my clit, it shows you how I like it done, at the end watch me squirt. Di told me what's happening today, that excites me, I've asked Di to video you fucking Carol. Could you video Di licking Carol's cunt out? I have several mature ladies that like watching homemade porn."

Jack told her he would do it for her. The church was quiet; there were fewer people than were there the night before. The priest spoke highly of Molly and how proud she would have been in June when Carol graduates. There was only Jack, Carol and Di at the graveyard. The priest did his job with so much respect. Carol asked if anyone was hungry, Di told her she wasn't, and she'd like to go to the apartment as she needed to go back to the University this afternoon.

Within a minute of them entering the apartment, they were all naked. Carol videoed Di sucking Jack's cock; Carol was very wet as Jack was fingering her as Di sucked his cock. Carol was soon ready for Jack; Carol suggested Jack do her doggy style as she wanted him deep. Di loved this idea as she could kneel beside them and get some close-up slomo videos of them fucking. Carol wanted to be done over the kitchen table; she was wearing heels, so everything was okay.

Carol was purring as Jack slipped his cock inside her tight cunt, soon he had a mighty rhythm going, he was going faster and deeper. Carol said, "Baby, you're filling my hungry cunt, you are stretching me, but it feels so comfortable."

Di said, "This looks amazing, Jack, you've got a wonderful athletic movement, this will be an excellent video. I'm getting some terrific close-ups of your cunt flaps as Jack goes in and out. Jean will love these."

Carol was giving Jack a great ride; she was gripping his cock at the base and head of each thrust. Jack was enjoying himself; he knew that Carol loved it too. Di said, "Carol, have you just cum, I can see some cunt juice dripping on to Jack's heavy balls, there must be lots of cock juice in Jack's balls. This video is going to be wonderful."

Two minutes later, Jack shot his load into Carol's cunt; Carol came at the same time as Jack. Jack kept pumping his cock into Carol; Carol loved it. Then Di said, "Jack, just after you pull out I'll give you my phone then could you film me licking your cock clean before I start on Carol's very wet cunt?"

Jack agreed, he got an excellent video of Di licking his cock clean. Di then cum kissed Carol before she went down on her. For the next twenty minutes Di licked Carol's cunt out, the video was terrific. Di then had a quick shower then left for the University telling Carol and Jack that she would send them the edited video, she would also update them on what was happening at the University. They didn't go out for lunch; Carol made them both a delicious omelette. Carol said as she was cooking, "Jack, I love when you fuck me, it feels so good. That's good news for Di; her lectures are excellent, she has a great way of explaining things, she also gives great oral. I think that Jean arranges for Di to visit some of her older patients to give them oral. Di once told me that the number of older women that loved their pussy licked was incredible; she told me she had done women in their eighties."

Jack then told Carol about his idea of setting up an Asset Management Company; Jack was amazed when Carol said, "Jack, I've written a Thesis on the Legal Aspects of Asset Management, I must ask Di about it. I submitted the paper three months ago. Di said at the time that it was excellent and I should get a PHD for it. You should do that; you can make a lot of money. You must be prudent and cautious. That would fly with your mum and Aunt. I have written them both a letter thanking them for the beautiful flowers. I also said that mum was struggling as a single parent. I would love to get to know your mum and Aunt, perhaps one day we will all be friends."

Jack said, "We will do that, you'll have to give me legal advice on the Legal commitments we need to have in place, then we'll have to look for wealthy clients that will invest with us. We have so much in place; it will be easy to start up."

Carol thought for a minute then said, "Jack, Jean has so many older patients with lots of money, when I was writing my Thesis, Di helped me a lot, she told me a lot of Jean's patients were only getting a pittance of a return on their money. I would have a word with Jean and Di, if Di has a Professor title then have her as a Consultant, that would attract a lot of investors. Jean has hundreds of patients; they are mostly women who have difficulty with vaginal dryness. Most are widows, but many have older husband's who have lot's of money, but they have no excitement in their lives. As you build your business it will grow, I would love to be part of it, do you think that your mum would allow that?"

Jack replied, "Mum started working yesterday; she was bored to tears. She was in the office at seven this morning. She is there with her sister today, nobody else, I haven't had any help messages. I think that your letters will help. Mum didn't love my father; she felt betrayed by him. I have never seen my mum as happy in my life. The sex we have has changed everything. In the next days, I'll be seeing Jean and Di, that will be interesting. The night I am with them maybe you should invite mum out for a drink or would you prefer me to ask mum to make contact with you as you have already sent the letter?"

Carol thought for a minute; you could see the concentration on her face, Carol said, "Maybe subconsciously, I put my mobile number on each of the letters. I feel that I have done my bit, she sent the flowers, I acknowledged it, maybe better if you ask her to make contact with me, I want her friendship to last for a long time."

They kissed and hugged then Jack left. It was just after four, he went to the office, when he saw mum and May, he knew that he would have two sisters tonight. They both had had a fantastic day. Mum suggested that they all meet at her apartment at seven; they would order a takeaway. Jack then gave them both Carol's letter; Jack said, "This is important, we have a lot to talk about tonight. Mum, Carol is offering you her hand in friendship, I believe that you should welcome her with open arms."


Jack1107
Jack1107
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