Trudy Ch. 01

Jack was up early; it was a lovely spring morning; it was the second time that he had cut the grass this year. He had now finished cutting the grass and saw his neighbour Trudy in her garden. He went to the fence and wished her a good morning. Trudy said, "Jack, I have a problem with my lawnmower, I can't get it started, both Tina and Helen have tried it too, they couldn't get it to start either. Could you have a look at it?"

"No problem Trudy, I can come now."

"Thanks Jack."

As Jack walked round to Trudie s, he thought that there was something very sexy about Trudy, she was a widow, her husband Tom had died three years ago. Trudy was a tall attractive woman with a full figure. She had come from a farming background. She had inherited two farms, she didn't farm them but rented the land out which gave her a nice income even year. She now lived in her house with her daughter Tina and Tina's daughter Helen. Tina was a single parent. Tina also worked for Jack. Jack's parents had been killed in a tragic road accident. Jack had been in his second year of University at the time. His only other living relative was his Aunt Jo. Jack had gone to live with her; she lived in the house next door to Trudy.

Aunt Jo was Jack's great aunt; she was the sister of Jack's paternal grandfather. Aunt Jo was a spinster; she had never married. She had died two years ago at the age of ninety-five. She had been a lawyer, Jack's grandfather had also been a lawyer as had Jack's father. Aunt Jo and her brother had set up a Law Firm over sixty years ago. Aunt Jo had a law degree but specialised in Asset Management. The firm had grown into an enormous concern. They were today managing trillions. They employed over three thousand people and had offices all over the country.

When Aunt Jo died, Jack had inherited everything; he was a very wealthy man but was quiet about his wealth. Aunt Jo had encouraged Tina to study, but she was unable to get the necessary qualifications for University. Tina, under Aunt Jo's guidance then became a Paralegal, she also became Aunt Jo secretary Tina also became pregnant, she had Helen, who was now finishing her first year of University studying Law. Helen was a brilliant young woman. Aunt Jo had recognised this before she died, she had asked Jack to help Helen in any way he could and when she qualified to offer her a position in the family firm. Jack had helped Helen in every way that he could. Trudy, Tina and Helen were very similar; they were all tall with full figures.

Jack arrived at Trudy's rear door; she was still wearing the short dressing gown that came to the middle of her thighs, Trudy had lovely long legs. Trudy showed Jack the lawnmower, Jack checked it, there was no petrol in the tank. There was a large can of petrol beside it. Jack filled the tank, turned the fuel on, and it started on the first attempt. Trudy said, "Jack, I don't have a mechanical brain, thank you. Please excuse my stupidity."

Jack smiled then said, "The grass is a bit long, if you make me a coffee then I'll cut it for you. It will take me half an hour to cut it for you."

"Jack, thank you, you can have as much coffee as you want."

Jack then started to cut the grass. He was wondering as he cut the grass if Trudy would dress or keep her dressing gown on, Jack was sure that she wasn't wearing anything underneath as when she walked her massive tits swayed. Jack had also noticed that her nipples had been hard as he checked the mower. Jack also remembered the night in Jack's final year at University, it was a Friday night, it was just after ten when Trudy had phoned Aunt Jo, she had asked Aunt Jo if Jack could come and help her get Tom, her husband into bed as he just come home, he had been out with friends and was very drunk.

Jack had gone over. Tom was fast asleep on the sofa. Jack had carried him upstairs to his bedroom. It had surprised Jack that Tom was sleeping in a single bed. Jack was also surprised when he passed Trudy's bedroom; the door was open, the bedside lamp was on. Trudy had a beautiful kingsize bed. Trudy was also wearing a very sexy nightshirt, it showed her curves to perfection. When they went downstairs, Trudy had offered Jack a glass of wine; Jack had refused as he didn't feel comfortable. He left the house with the feeling that Trudy was interested in him. Jack told Aunt Jo about Tom's single bed. Aunt Jo replied, "I think Trudy would like Tom to spend a little more time with her."

Jack had graduated from University he and Aunt Jo spent the next years at the head office. Until Aunt Jo was ninety-three, she was still in the office at least once a week. Her brain was still so sharp. Any new laws that came out she was on top of immediately. Jack worked closely with Tina then, today, Tina is Jack's Personal Assistant. Jack and Tina now basically managed the business. They had other professionals doing different things. Everything was computer-based; they just managed the business. Jack also found Tina attractive, but he had never made any advances towards her.

After his parent's death, Jack had a relationship with one of his mum's friends. She was married with two grown-up children. Up until four months ago, when her husband retired, Jack would visit her at least three times a week. The sex was terrific, Kay, taught Jack so much. It was now very sporadic when they saw each other. Jack didn't socialise much, but he was now starting to miss the regular sex.

Jack and Trudy, apart from seeing each other in the garden, had only seen each other at Tom and Aunt Jo's funerals. On both occasions, Trudy had given Jack a big hug and held him close to her. Trudy didn't drive; she relied on Tina and Helen to drive her around. Once Jack had seen Trudy at the bus stop, he had stopped and offered her a lift into town. Trudy accepted and got into the car. She had difficulty with the seat belt; Jack had helped her with it. As he did this, his right hand touched her big tits; Jack secured the belt, Trudy smiled then said, "That felt so good."

Jack finished the lawn, it looked good, even he was impressed with it. He cleaned the lawnmower and put it back in the garden shed. Trudy came out; she was dressed in a beautiful outfit, she was wearing heels, Trudy said, "Jack, the coffee is ready. I just remembered that I have a dental appointment at ten. There's a bus at nine-fifteen, I've made you your coffee, but I now need to run for the bus."

Jack smiled then said, "Trudy, we can have the coffee together, then I'll have a quick shower then drive you to the dentist."

Trudy's face beamed, she took Jack in her arms then said, "Jack, you're a darling."

They finished their coffee. Jack went for a quick shower. He parked his car outside Trudy's house, Trudy came out smiling and sat in the passenger seat, once again she was struggling with the seat belt, Jack said, "Trudy, would you like me to help you the seat belt?"

Trudy glanced down the road then said, "Yes please, but take your time this time. I enjoyed it a lot the last time that you buckled me up."

Jack leaned forward and took the buckle as his hand brushed over Trudy's massive tit. Jack whispered, "How slowly do you like it?"

"Very, my tits are very sensitive. When you play with them, you can make me cum very easily. It may be better if we did it later as I think that we should be discreet, this is a tiny village."

Jack nodded in agreement, Trudy must have been an E cup, he squeezed what he had in his hand, he felt her hard nipple then said, "We will do that Trudy, now what dentist do you want me to take you to?"

Jack knew the dentist, he drove there then said, "I can park here. I'll go for a coffee, how long do you think that you will be?"

"Forty-five minutes, I'm with the hygienist the Dentist checks my mouth."

"Super Trudy, I will be waiting in the car for you. Would you like to go for lunch afterwards?"

"I would love to, but I must wait for an hour after my treatment before I can eat or drink. Jack, when you were playing with my tit, I wanted to kiss you, do you think that I'm naughty?"

"Would you like to be naughty with me?"

"I would love to be very naughty with you. Hopefully, I'll be back in forty-five minutes."

Trudy leaned over, and tongue kissed Jack, she buried her tongue deep inside Jack's mouth. She was a great kisser. Jack then went to a cafe for coffee. Forty minutes later Trudy came out of the dentist, she was happy, her teeth were in good condition. When she got into the car, Trudy said, "Please buckle me up Jack, but please do it slowly and squeeze both of my tits hard."

This time they were kissing as Jack played with Trudy's tits outside her dentist. They sat kissing and touching for fifteen minutes; the kisses were both tender and affectionate. Trudy said, "Jack, there's a new Italian restaurant opened beside the Town Hall. I've heard that it is excellent. It will not open until twelve, would you like to take me there?"

"Trudy, I'll take you anywhere you want to go, you're a fascinating woman. You are a little older than me, are you comfortable with that?"

"I am if you are, Tom was my first love, we were so young, I got pregnant with Tina, we got married, I didn't have a good marriage. When Tom got excited, he was not very big; his cock was tiny. After Tina was born, our lovemaking slowly ended. In the last twenty years of his life, we had separate bedrooms. When Tina got pregnant, I had my reservations about the guy that had made her pregnant. He was older than Tina, he was good looking and intelligent, but he had been married before, and most importantly, he was a heavy drinker. I am secure financially. I pleaded with Tina not to marry him because of the life I have had. Thank goodness, she listened to me. Helen is a wonderful girl. Tina has an excellent job; your Aunt Jo helped her so much. I am older, but I'm still active, am I wrong to have some fun with a younger man while I still can?"

Jack kissed her again, then Jack said, "Trudy, I don't have a problem with this, I find you so attractive, let's do it, but we must be discreet, remember that I am Tina's boss and I will also be Helen's boss. We can't have tongues wagging."

They were both so relaxed over lunch, Trudy was an intelligent, witty and interesting woman. She was so knowledgeable about so many different things. After lunch, when they got into the car, Jack said, "Your place or mine?"

"Jack, can we make it your place? I would be so nervous if Tina or Helen came home early. I enjoyed lunch so much. It has been a long time since I was last out. I can't believe how relaxed I am with you if you had told me at eight this morning that I would have lunch with you today and I was excited about the prospect of going back to your house for sex, then I wouldn't have believed you. I am so happy that it is happening."

They arrived at Jack's house; he had a large double garage beside Trudy's driveway. There was no fence there; Jack opened the garage door with his zapper. He then gave Trudy the four number code to open it from the keypad on the wall. They went straight to Jack's bedroom; Jack hadn't made his bed this morning, they were both naked in seconds, Trudy was nude first, for her age, her body was superb. Her tits were massive with big hard nipples. Her stomach was flat with a beautifully smooth and swollen vulva; her sex slit was long; she looked gorgeous. When Jack took off his boxers, Trudy gasped then said, "That's massive, I have never seen one as big. Jack, I had Tina by caesarean section, yes she came out of the sunroof. My pussy is still very tight. I don't have a problem with vaginal dryness; in fact, I can get very wet. Maybe it would be better if I went on top then I would be able to control how much of that beauty that I take but first let me make him hard."

"Trudy, I would love you to do that, but let me make you wet before we do it."

They then started to 69; Jack was impressed with what Trudy's tongue and lips were doing to his cock; she was massaging Jack's heavy balls as she sucked on his stiff cock. Very quickly, Trudy was taking Jack's full length; she was deep throating him, the bulbous head of his cock hitting the walls of her throat. Jack was sucking on Trudy's big hard clit; it was like a little cock. Trudy loved it; her legs were spread wide open, giving Jack easy access to her pussy. Trudy was pushing her wet pussy against Jack's mouth. Five minutes later, Jack felt the warmth of her cum as she flooded his mouth with her spunk. Jack held it in his mouth; he brought Trudy close to him, then they kissed, Trudy then realised that they were cum kissing, her tongue went deep into his mouth, transferring her cum back into her mouth. A few minutes later, Trudy said, "I have never done that before, I thought that you would have swallowed my cum, we must do this again; I enjoyed doing it."

Jack lay on top of his bed, Trudy was squatting over him, teasing her hard clit with the head of his cock, then she placed the bulbous head in the middle of her long sex slit and pushed her pussy down on Jack's stiff shaft. She took half of his length then raised herself then pushed down again. She did this several times; then Jack felt her thick cunt lips around the base of his cock. Trudy soon had a steady rhythm going; it felt good for Jack and Trudy was purring with pleasure. Trudy said, "Jack, it feels wonderful, I feel stretched, but it's so comfortable, I feel filled, the head of your beautiful cock I'd hitting my cervix, that will make me cum. How's it for you? Can I do anything to make it better for you?"

Jack replied, "Trudy, it feels wonderful for me; your pussy is so tight. I love how you're gripping me at the base and head of each thrust. You are giving me a great ride, just take your time, let us both enjoy it. Don't worry about cuming; I want to feel your warm cunt juice on my cock."

Jack was stroking Trudy's hard clit as she rode him, she loved that. Jack loved looking at Trudy's massive tits as they swayed, then Trudy started to pound Jack's cock, she was going so much faster and harder now, it felt so good for both of them. Jack felt his cock tingle; he knew that he was close. A minute later they both climaxed simultaneously; Jack emptied his balls inside Trudy's pussy, Trudy's cunt juice flowed down Jack's cock and onto his balls. Trudy held Jack's cock inside her then leaned down, and they kissed lovingly and tenderly for several minutes. Trudy said, "I loved that Jack, when can I see you again?"

"How's tomorrow for you?"

Trudy's face beamed then said, "I can come over just after seven when the girls leave. You stay in bed, and I will join you. I will not forget the four access numbers."