Mum and Sister Mary are Close Ch. 01

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Jack Likes Mature Women.
4.3k words
4.54
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Part 1 of the 2 part series

Updated 06/11/2023
Created 12/25/2021
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Hi, I've disabled comments. This is meant to be fun, and the shitty comments and trolling are tedious, to say the least. I hope that you enjoy it.

Jack had been accepted for an IT course at College; he was over the moon. His mum, Jill was so happy too, he was doing something that he loved. He was eighteen and six months; he had been computer programming since he was thirteen.

He had just sold two Computer games to a reputable Games company. They had given him two thousand pounds for the games plus fifteen per cent on all games sold. Jack knew that he wouldn't have any financial worries at College. Come the end of August, Jack's life will be changing.

Jack lived at home with his mum; she was a single-parent mother. She had told Jack that his father was an intelligent, good-looking man, but mum decided she would be better off bringing Jack up alone. Mum had been a fantastic mum to Jack; Jack loved her. In addition, mum had graduated as a teacher.

She had secured a position in a Catholic Primary school teaching children until they were eleven. The Church owned the school and was run by nuns, but that had changed a few years ago. Although there was only one nun left teaching, Sister Mary, the Church wanted to sell the vast grounds of the Convent and school. Sister Mary was now coming up for sixty, and there was no one to replace her.

The Church had arranged with the local Council years ago that they could use the Convent and school. Then the Church accountants saw the money that was involved in the area was developed for housing. Sister Mary had worked for the Council for nearly thirty years; she was eligible for a State Pension.

The new school was due to open in the first week of January. Mum would be the new headmistress when Sister Mary retired. Mum was a Catholic and took an active part in church life. Jack only went because his mum went.

Mum's best friends were Sister Mary and Father Peter. They were both very close to mum. Father Peter had been the Local Parish Priest for forty years. He was a kind, considerate man liked by all his parishioners. Mum often invited Sister Mary and Father Peter to her house for meals; they were always there for birthdays. Unfortunately, father Peter had a stroke; he was in the hospital with a fifty-fifty chance of recovery.

When he was in there, Jack passed his driving test. Unknown to mum or Jack, Father Peter knew the situation. So he adjusted his will that his five-year-old VW Golf would go to Jack. Jack got the car three weeks later.

Because Jack was going to study IT, Father Peter also left him his nearly new laptop and his iPad Pro. So naturally, Jack was over the moon.

Jack had tears in his eyes at Father Peter's funeral. He had never forgotten Jack's birthday once. He was always chatted freely and openly with Jack. He had also played a big part in the College that Jack had been accepted. It also had close connections with the Church.

The funeral took a lot out of mum, and Sister Mary both looked so upset at the funeral. So mum invited Sister Mary and Jack out for dinner in the evening after the service. They walked to a Hotel with a good restaurant. Mum told Jack that Sister Mary would not wear her habit this evening as she enjoyed a glass of wine with her meal, and she didn't want to be seen drinking wine in her habit. She would also stay the night with mum. She would have to share mum's king-size bed as the spare bedroom was now Jack's study.

Jack got a surprise when he saw Sister Mary dressed. She looked so attractive for a woman close to sixty. Her complexion was so pure, but she was wearing a little makeup this evening. Sister Mary was a voluptuous woman. Although her tits looked massive, she, like mum, was wearing a skirt, blouse and jacket.

Mum had worn black for the funeral, but her outfit was bordering on risqué. They were drinking in the lounge, both mum and Sister Mary were reminiscing about Father Peter. They had been to a Seminar in Rome with Father Peter ten years ago for three days, then four days at Antioch on the Mediterranean. Sister Mary told mum that she had found Father Peter's pictures when sorting his personal things out. She would show them to mum later.

Sister Mary had also brought Father Peter's iPad and laptop, which she gave Jack that evening. Jack was impressed with the power of both of them. Then Sister Mary said, "Jack, would you mind not calling me Sister Mary when we're out this evening, my real name is Diana, but I prefer Di as it could be embarrassing if you asked Sister Mary if she would like another glass of wine. So, in fact, please call me Di anytime that we are alone."

They all laughed at this. It broke the ice as Jack, who had always liked Sister Mary, had always felt affected by her probably because she had been his headmistress for six years. Now, as they drank wine and socialised together, he felt comfortable with her. The same was with mum; they had wine the first time together at Jack's eighteenth birthday.

Sister Mary was there too, but she was wearing her habit, but she was drinking wine. Jack was now looking at Sister Mary's massive tits. They jiggled so sexually when she moved. Jack could feel his cock stiffen; Sister Mary was arousing Jack. Then Jack looked at mum, her tits were a similar size to Sister Mary's, but Jack didn't sexually see mum, she was the best mum in the world, and he loved her for that.

Jack liked older women. Five months ago, mum had asked Jack if he could look at Dot's tablet. Dot was a widow and went to the same Church as Jack and mum. Dot was a tall, voluptuous woman. She had a lovely smile, she was maybe five or six years older than Sister Mary, but as Jack looked at Sister Mary tonight in regular clothes, Sister Mary was far more attractive.

Dot's tablet had too many windows open in her browser. She hadn't switched it off for over six weeks; it needed a reset. Jack had checked Dot's browsing history. She looked at a lot of porn, especially younger man older women porn. She was also watching mum son incest which surprised Jack as she only had a daughter.

Jack fixed her tablet; Dot was so happy, they started to flirt in Dot's lounge. One thing led to another, and ten minutes later, Dot was sucking Jack's massive cock. Jack was very well hung. At school sports in the changing rooms, Jack's flaccid cock was bigger than any of the guys if they had a hard-on. Jack was conscious of this, and he tried to keep his cock hidden all the time. When Dot saw Jack's massive stiff cock, she fell in love with it. She wanted it, she needed it, and she got it. A girl had given Jack a hand job. That was the only sex he had in his life apart from when he masturbated in his bedroom until he met Dot.

Dot loved sex; she couldn't get enough of Jack. She taught Jack so much. He could control his orgasms not instead of shooting his load as soon as he got aroused. Dot took it in every hole. She loved oral, anal and being fucked hard and deep. She was also very discreet. She had insisted with Jack that what they did in her bedroom was their secret. Jack had accepted that. He visited Dot three times a week. This kept Dot completely satisfied sexually.

Because of Jack's relationship with Dot, Jack became a very experienced lover. Dot taught him how to give a woman oral; Jack loved to lick and suck pussy. She also taught him how to use his monster of a cock to give a woman maximum pleasure.

Jack also had another older woman lover, but seeing her was difficult as she was married to an older man doing nothing for her sexually. Jack had been playing football three months ago. He had been hit by a football travelling at full force in his groin. The pain was unbelievable. His private parts were bruised and discoloured. A school teacher drove Jack to his doctor, a friend of his mum, she and her husband attended the same Church. May, his doctor, was in her mid-fifties; Jack liked her; she was an excellent doctor. Jack hadn't seen her for years as Jack had a very healthy youth.

Jack arrived at her Clinic. The school had phoned in advance. Jack was still in his football clothes. A nurse took Jack's blood then May came. May recognised Jack immediately and said, "Hi Jack, you have been in the wars. I'll need to have a look, could you please drop your shorts. What type of pain are you having?"

Jack told her that his private parts felt sore. When May saw Jack's flaccid cock she said, "Wow, you should have been wearing a jockstrap, you would have to have it specially made, that's a big boy! Jack, I would like you to pee in this container; please tell me if you have any discomfort when you pee?"

Jack peed in the container May had given him. He knew that he was alright as he peed. He peed normally. He applied pressure to his bladder; his pee came out with a lot of force. He also noticed May's big tits wobbling. They looked good. Jack could feel his cock stiffen. As Jack was peeing, May took his temperature by putting a thermometer under his tongue. As she did this, Jack knew that she was flirting with him when she said, "You have got a lovely big tongue to Jack."

Jack finished his pee, May took the thermometer out of his mouth then said, "Your temperature is normal, your urine is clear and sparkling, you have no blood in your urine. Did you have any pain as you peed?"

Jack told her that he had no pain at all. May then took his heavy balls into her hand and scrutinised them both. Then she took his flaccid cock into her hand and examined every inch of it closely. Jack was so worried in case he got a hard-on. Then May said, "I think it is just bruising. Do you have any pain as I touch your cock and balls?"

"No, May, it feels very good. You have a gentle touch."

May smiled then said, "I can be rougher too, but I don't know how bad your bruising is. I would like you to get some Baking Soda. You get it in every supermarket. Run a hot bath and then put half a cupful into the bath, then soak in the bath for thirty minutes. You have a beautiful bulbous head on your cock. Pull your foreskin back and let your cock soak in the bath too. If you continue with your football, then buy a jockstrap as it would be a pity if anything happened to that beautiful monster of a cock you have. I will call round to your house around seven, and I'll recheck you. Soaking in the bath with Baking Soda is important."

Jack went back to school, changed, then went home but bought three packets of Baking Soda. He went home and soaked in the bath for forty minutes. When he got out, he could feel the benefit. He had no pain whatsoever. His cock felt amazing. There was no discomfort at all.

He heard mum coming home. He put a towelling dressing gown on then went and told mum about his accident and how the school had insisted that he went to be checked at Dr May's. He told her about soaking in a Baking Soda bath for half an hour. He also told her that Dr May would call at seven this evening to recheck him. Mum said, "I have Baking Soda in the house. That will do you good. I soak in the bath at least twice a week with it."

Jack opened the door for May just after seven. He was still only wearing the towelling dressing gown. May was showing a lot of cleavage. She had done this on purpose as two more buttons buttoned on her blouse would have been normal. Mum was in the bathroom. Jack led May into his bedroom, which he had tidied just for her visit. May closed the door then said, "Have you had a long soak in the bath and were you a good boy and did you do everything that I asked you to do?"

Jack told her he had done everything that she had suggested he do. May then said, "Good, now lie on top of your bed and take your dressing gown off; I hope that you are naked underneath. Please leave me some room so that I can sit on the side of the bed with you."

Jack's cock was flaccid when he lay on top of the bed, but it still looked so impressive. May then put her hand on Jack's chest. First, she squeezed and felt his tight muscles, then her hand moved over his hard stomach, May said, "I have surgical gloves in my pocket, but I think that you enjoy skin against skin. Am I right in thinking this?"

"I love how you touch me. Skin against skin is much more personal."

"I agree with you Jack, is Jill at home?"

"Yes, I think that she's having a shower."

Then I'll have a quick look now. When are you home tomorrow?"

"I'm here all day. The school gave me the day off to rest. However, I will do some work at home because the exams start next week."

May then gave Jack her mobile phone and said, "Jack, in my Contacts, put your name and mobile number in so I can message you a time tomorrow morning. Very few people have my mobile number."

As Jack entered her number May started to examine Jack's cock and balls. She pulled his foreskin back and closely looked at the bulbous head of his soft cock. Her touch was incredible. Jack was sure that his cock would soon stiffen. But May was in control. She knew what she was doing.

She then felt both of Jack's balls. Jack could feel his cock starting to stiffen. May said, "The Baking Soda has worked. There's no bruising on the crown of your cock. Your balls have no swelling from an injury. They are heavy and full of lovely testosterone. I believe that you need to relieve yourself of some of this. I wouldn't do it today. Tomorrow morning early have another Baking Soda bath. Tomorrow, when I visit, would you like me to give you some relief?"

"I would like that a lot, and I'm looking forward to it. We must both be so discreet. What happens with us stays with us. Are you happy with that?"

"I'm delighted with that. We must be so discreet. I love a big cock, I love my cunt stretched, and your monster will stretch me. My husband is older than I am. He's also very possessive. He likes to know my every movement. I haven't had a cock for eight years. Just looking at your monster makes me wet. Jack, I would like you now, but it's risky as Jill is in the house, and I can be very noisy when you fuck me. Tomorrow will be special. Thanks for your number, everything is good with you. I will say hello to Jill if I see her. I'm looking forward to tomorrow."

May then tongue kissed Jack and left his bedroom. Jack put on his dressing gown and opened his bedroom door. He heard May say, "Hi Jill, Jack got a nasty one, but it's only bruising, another couple of Baking Soda baths, and he will be fine. However, you should think about getting him a jockstrap if he's going to continue playing sports. You will need to order a special one as he is very well endowed. He is like a stallion, I've never seen one as big, and it's beautifully proportioned. Are you looking forward to your new school? I hear that you'll take over when Sister Mary retires?"

"May, I had no idea about Jack. I will tell him to order one online then he can get the appropriate size. Yes, the new school will have so many new facilities, it's very exciting. Sister Mary will work for a year and then retire. She's been offered a position on the School Education Committee Quango. She'll be an asset to that Committee."

They chatted for ten minutes, then May left. Jack noticed that May made no mention of her coming to visit Jack tomorrow morning. Jack did his studying then went into the lounge. Jack liked to watch television. Mum would sit on an armchair and surf the Internet on her iPad. She always wore a pair of earphones when she did this. Jack had bought her a pair of earbuds, but mum preferred her cable and headphones. That night mum seemed happy that Jack was in the room with her.

The next morning, Jack soaked in the bath for thirty minutes. He felt great. It was now ten past nine. He had breakfast with mum before she left at twenty past eight. She gave him a hug and a kiss on the cheek; he felt the weight of her tits on his chest. They felt full and meaty. She had never done that before. Jack's phone beeped, he had a message from May, it read, "Hope you're good, I'll be with you in five minutes, I've got to be back by eleven-thirty. I wish it were longer, but there will be other days. See you soon, May."

May arrived when she had said Jack was wearing only his towelling bathrobe. Instead, May was wearing a jacket, skirt and blouse. She looked good. Jack led her to his bedroom; May asked, "Would you like me naked then you can explore my body as I do nice things to you?"

"I would love that, May. Your body looks so good."

May was only wearing a bra and a thong when he took off his bathrobe. He was hard when he opened the door for May when he saw her take off her bra and thong. His cock now had a massive hard-on. May's was beautiful; for her age, she was terrific. Her tits sagged a little. They were enormous and still looked amazing. Her stomach was flat. Her vulva was smooth and swollen. Her cunt flaps were thick. Her sex slit was long and perfectly formed.

May then saw Jack's massive hard-on. In her life, she had seen many erections, but this one was in a league of its own. May then thought that being naked had given Jack this massive hard-on. She felt good when she felt that.

May then sat naked on the bed beside Jack, Jack pulled her close, and they tongue kissed for a couple of minutes, then Jack said, "May, I find you very attractive, I love how you kiss. You have given me this massive stiff cock this morning. It's not just a fuck that I want. I want to make love to you."

May had been holding one of Jack's testicles as they kissed. She was still massaging it gently. She then wrapped her thumb and middle finger around Jack's thick cock. There was a gap of at least two inches between her thumb and finger. This cock was going to stretch her pussy. It was so long and thick.

May said, "Jack, I've never in my life seen such a big cock. I want to make you cum with my hand and mouth. Your blood and urine test are good. You can cum in my mouth if you want. I want you to cum then we will make love. I orgasm a lot when I suck cock. I think it happens instinctively as my brain is telling my pussy to get wet as I will get fucked hard and deep soon. I will be very wet for you soon. I want you to cum in my mouth."

There was some precum on the slit on the bulbous head of Jack's stiff cock. She used her tongue very gently to lick it away. May then thought that she would do this slowly for Jack. She took the bulbous head of his cock in her mouth. She teased his frenulum with her tongue, Jack's cock jerked with pleasure. May said, "Does it feel good?"

Then she put his cock back into her mouth but took more of his cock. May knew that she must angle her throat correctly, then she would deep throat him. When she knew the angle, then she would let Jack give her a mouth fuck. Jack replied, "May, you're so good at that. I love what you're doing to me."

May continued to suck him, taking a little more as her head started to bob up and down. Then she guided one of Jack's hands onto her massive tits. May said, "If you play with my tits, that will help you cum."

May sensed that Jack was so close, then Jack said, "I'm going to cum."

May then slid a finger up her dripping pussy then slipped the finger up Jack's tight ass hole. Seconds later, Jack shot his load into May's mouth and throat. A massive spurt of creamy spunk hit the back of her throat. May then sucked every drop of his cum into her mouth; her lips were clamped around the bulbous head of his cock. When she had the last drop in her mouth May came off his cock.

She shut her mouth. She didn't swallow. She took Jack in her arms, their lips met. Jack was trying to get his tongue inside her mouth. May opened her mouth. They cum kissed lovingly and passionately for several minutes. May said, "I enjoyed that. It was something exceptional for both of us. Jack, I'm so wet for you. Take me now. Your cock is still hard."

May pulled Jack's tongue into her mouth. The taste of her cum was still there. Jack then went on top of May. He ran the head of his cock up and down the length of her long sex slit several times. Finally, he placed it in the middle of her long sex slit. Just as he was about to slip it up her May said, "Put it in now, Jack, I'm ready, I'm so wet, but do it slowly and gently, to begin with, I haven't had a cock inside me for years, never mind one the size of your monster."

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