This is a complicated one; Jack had just finished his fourth year at University studying Law. His girlfriend of two months had just ditched him, telling him she liked him as a person, but she wasn't sure if he would be part of her future. His girlfriend was Mags, the daughter of May, Jack's mum's best friend. Jack had been attracted to Mags because she was beautiful, tall and had big tits. Also as being a friend of the family was another factor. For nearly the last three years, Jack had an affair with his Class Lecturer; she was a high-powered businessman's neglected wife. She was fifty-five; Jack had loved the sex; she had taught him so much.
Jack hadn't dated since he left school. He didn't need to; he was getting everything from Jean, his lecturer, whose husband had been promoted, and they moved two hundred miles away. Jack had then started to date Mags; this was another reason he dated Mags as people were curious as to why he wasn't dating anyone. Jack was tall, intelligent and very good looking. However, he had been getting no sex from Mags. Mags was on the pill, but Jack had never penetrated her once as she wasn't comfortable with the size of his cock. When she was sucking him, she would only take his bulbous head in her mouth. The best he got was a hand job; Mags looked bored when she gave him those.
Mags was spoiled, an only child like Jack, her mum gave her everything she wanted. May was an Accountant; she had her own firm and was very successful. Jill, Jack's mum, was a lawyer with her own firm too. Professionally they worked closely together, serving both of their clients. Jack worked at every opportunity for his mum. Every year he was becoming a more significant asset for her. May and Jill were both widowed; their husband had died early from cancer. So Jack was a little surprised when he broke up with Mags, but in no way was he broken-hearted.
The thing that Jack didn't know was that six weeks before the break-up, May had asked Mags how was she getting on with Jack? Mags replied, "Mum, Jack is a gentleman; he's fantastic company. He's tall and very good looking, but there are times I don't feel comfortable with him. It's a strange situation."
"How do you feel uncomfortable with him? What does he do that makes you uncomfortable?"
"Nothing, he is a perfect gentleman. This is difficult for me to explain. I have been on the pill for over three years now. I enjoy sex, but I've never had sex with Jack. It's because I don't feel comfortable with his penis. His penis is the problem."
May was getting worried now if there was something wrong with Jack's penis, May said, "Oh my god, Mags, what's wrong with Jack's penis?"
"Mum, it's massive. It's thick and long with a bulbous head. Once I let his cock inside me, he got only the head in, and I asked him to stop as my pussy felt so stretched. Imagine if I'd let him in, and then it didn't work out. The next guy I would have would be thinking that I have got a very loose pussy. Mum, it's just too big."
"How big is it, Mags? Can you give me a general idea of how big it is?"
"Mum, when I wank him, I can't get my hand around his cock; there's a gap of two inches between my middle finger and my thumb. It's long, at least ten or eleven inches. When you look at it, you think it's beautifully proportioned, but it's just too big for me. Mum, how can I let him down gently? I'm starting a new job at the end of next month; I'll be leaving home then. John, who I used to date, is working for the same company. He has got an apartment, so I'll move in with him; he's got a cock that I can handle."
May was impressed with the size, she had a big cock at University, and she had loved it. Those were the days she had shared the guy with Jill; they had done a threesome with him, they both had loved the sex with him. May then said, "Mags, you must do this nicely; you must think of Jill and Jack. They have been good friends for so long. Don't tell Jack that his cock is big for you. Please don't say anything about the size, or he may think that he's a freak. Cocks come in all sizes; maybe later in life, you'll want a big cock. Start dropping hints that you've got a new job coming up and you're going into an apartment. Let him know nicely; I'm sure that he'll appreciate that."
May was so friendly to Jack for the next few weeks, giving him hugs, pulling him close to her, letting him feel the weight of her massive tits on his chest. May was sure that Jack was responding, but Mags was still around, and May was worried that Mags saw what she was up to. Jack certainly noticed how May was when he was at her house. May had a very sophisticated alarm system in her home. One Saturday night, May had left Jack and Mags in the lounge. The concealed camera was in a mirror facing the door; anyone coming in the door would be captured on film. In its line of view, it took in the couch. Mags was giving Jack a hand job. Jack's cock was massive; she had never seen one as big; Mags was right; it was beautifully proportioned. May then got a big dildo out and started working her very wet pussy with it. Naturally, may wanted Jack's cock.
The break-up came; Mags did it nicely. She had no idea how grateful Jack was that it was over. Jack was more interested in May; he was sad that now he wouldn't see her regularly. He wished that he had sent out some signals to her. He was sure that she would have responded. May had a fuller body than Mags; she had a beautiful smile and honest eyes. Mum was going on Holiday for two weeks to visit her mother, Jack's gran. She would be seventy in two years, but she was still so active. She had an apartment at the coast; it would be good for mum to visit her. Mum had seen gran often but hadn't stayed with her for a long time. Mum was a little concerned about gran as she seemed a little depressed, which was unusual for gran as she was full of life.
Mum was a great cook; she had cooked Jack meals and Vacuum Packed them, and left them in the freezer. So whatever Jack wanted for dinner, he would take it out of the freezer and leave it in the fridge the night before. Jack and also enjoyed wine. Mum was a member of several wine clubs, but they also used a local Wine Merchant, Jack was in there one night after work, and he met May; the hug she gave Jack told Jack that she was delighted to see him. Jack didn't ask anything about Mags. He only asked about what May was doing. Jack told May that mum was visiting gran and he had to look after himself. May then invited him around for a glass of wine tonight at eight. Jack quickly accepted and told May he would bring some wine. Jack was excited; May looked excited too.
May lived a two-minute walk from Jack; Jack was wearing only chinos and a polo shirt, he preferred the casual look, he two bottles of Premier Cru Chablis chilled in a bag. May opened the door, she was casually dressed too, but she looked stunning. She had a tight-fitting top on which showed her massive tits to perfection. She was wearing a pair of tight-fitting leggings, which showed her beautiful Camel's Toe to perfection; Jack was sure that she wasn't wearing any panties as her long sex slit was so well defined. She gave Jack a huge hug, then said, "I've missed you, Jack, I've missed the cuddles you used to give me. I can give you an update on Mags; she's moved in with an old boyfriend; this guy gives me the creeps; I honestly thought that when she had started dating you that she had hit the jackpot. Come on, let's go into the lounge and sit on the couch; I have a selection of cheeses so that we can have a little Cheese and Wine party."
Jack opened a bottle of the Chablis and asked May to put the other in the fridge; May had left two glasses on the coffee table in front of the couch, there was a selection of Cheddars on little sticks on a plate on the coffee table two. May came into the lounge and sat beside Jack; they toasted each other, then May said, "I'm so happy that you're here, Jack, we must keep in contact. Are you dating anyone at the moment?"
"No, I've too much work, I have the qualifications to be a Paralegal now, so I get a lot to do; it's a wonderful experience for me. What about yourself? You're a beautiful woman?"
"I work hard to Jack; I'm getting older now after my husband died; if it hadn't been for your mum, I would probably have had a breakdown. We supported each other; our husband's died within six months of each other. We mourned, but then we got ourselves active. I believe that we were called the Merry Widows, which was alarming. We weren't out shagging; we were out playing golf and eating in the Club House a lot. Do you miss not seeing Mags?"
"Mags is a beautiful young lady with a wonderful figure; she is growing up; I enjoyed going out with her; when I look at you, I can see where her good looks come from."
"What a beautiful thing to say, thank you, Jack."
"But she didn't get all of them."
Mary leaned over and kissed Jack on the cheek, then said, "A serious question, do you find me attractive, Jack?"
"May, I find you very attractive; I would love to take you out for a meal, spend quality time with you, to get to know you. I think that you're a fascinating woman."
"Thank you, what about the age difference? Does that concern you?"
"No, age is just a number; I was so happy when we met in the Wine Shop and even happier when you invited me over tonight."
"You say the nicest things, a personal question, do you enjoy sex?"
"Yes, but I prefer making love; I love to give my partner pleasure. What do you prefer, having sex or making love?"
"I think the same way as you do, making love for hours, not rushing anything, just being together pleasuring your partner. I must tell you one thing, Jack, I have a powerful libido, I love eroticism, I love passion, I have powerful sexual urges and needs, but I'm loyal and dependable towards my partner. Jack, may I ask you one thing which I've never asked any man in my life before, but I want to ask you, may I kiss you?"
Jack didn't reply. He leaned over their lips met, May's tongue was deep inside Jack's mouth, both their tongues were so active. Their kisses were intimate and tender; Jack's cock was stiffening; he was so attracted to May. His right hand found May's massive left tit. He squeezed and played with it for a couple of minutes as they kissed. Then May said, "Be firm with my girls Jack, you won't break them. They are very sensitive; I can cum if you're firm with them. I want you to make me cum."
May's hand found the bulge of Jack's massive stiff cock; she squeezed and stroked it lovingly for a minute then said, "What a magnificent cock, Mags hasn't thought this through. Can I have all of it, Jack? I'm getting so wet just touching it. Jack, slip your hand inside my leggings and feel my honey pot; no, I'll change that; it's your honey pot now. Jack, this is special for me; I haven't had any cock since my husband died. Can we go to my bedroom? Then we have all night to do it nicely."
Jack slipped his hand inside May's leggings; her stomach was flat, he was right, she wasn't wearing any panties. Her vulva was swollen and smooth; he spread her cunt flaps open, her honey pot was so wet. Jack said, "I want you, May."May led Jack to her bedroom; they both stripped naked, then May took Jack in her arms, they tongue kissed passionately for a couple of minutes. Jack loved how May kissed; it was so much better than Mags; Jack could feel tenderness and affection as May slid her tongue in and out of Jack's mouth. May's tongue wasn't just in Jack's mouth; she also tongued Jack's top and bottom lips. Finally, May said, "We must take our time, please don't rush things, we can take our time. I want us both to have lifelong memories of what we do tonight. I feel so good about you. Your cock is magnificent, just looking at it makes me wet."
They lay on top of the bed, kissing, touching and feeling just like any couple would do in foreplay, but they both could feel that there was no urgency in their actions; they weren't attacking each other; they were pleasuring each other. They were both exploring the other's bodies most intimately with their fingers. As they touched, they both continued to tongue kiss. The touching was letting them get to know the other's body. Though Jack was touching May's massive tits and wet pussy, May concentrated on Jack's huge stiff cock.
Jack was first to break away from the very long kissing session; one by one, he took May's massive tits into his mouth and hands; Mags were smaller and a little firmer, May's were considerably bigger and much fuller. Jack was strong in how he sucked and played with May's girls; May loved it; she was purring with pleasure. May was using both her hands on Jack's cock and balls; there was a little precum on Jack's cock slit, May squeezed his cock slut open with two fingers then used the index finger of her other hand to wipe the precum onto the tip of her finger which she then licked and sucked clean.
Then Jack moved south onto May's beautiful vulva; it was smooth and swollen with thickish cunt lips, her long sex slit was perfect. Jack spread her cunt flaps open, and a lovely big hooded clitoris popped out; it looked so suckable. May had now positioned herself in a position that would allow them to 69, she now had Jack's cock slit pushed open, and her tongue tip was deep as it could go inside his cock slit. Jack thought that May was a very sexy woman; Mags would never have done what May was now doing willingly and gladly to him.
Initially, Jack teased May's big and hard clit with his tongue, May squirmed her hips and pushed her pussy against Jack's mouth when he did this; she also spread her legs, allowing Jack better access to her hungry pussy. Jack then ran his tongue up and down May's very long sex slit; Jack's tongue felt the warmth, wetness and sweet taste of May's cunt juice. Finally, May said, "Jack, that's so beautiful; my clit is so sensitive. If you suck it, then I'll cum very easily. I love what you're doing to me."
May had been licking the head of Jack's bulbous cock and licking up and down his stiff shaft. Then she teased Jack's frenulum, the skin that connects the head of Jack's cock to the shaft, with the tip of her tongue. Jack loved this. Then May said, "Jack, your cock is magnificent, it's so big, I'll try and take as much as I can; I don't think that I'll be able to deep throat you tonight, but I'll take as much as I can. One thing for sure is I'll have to breathe through my nose. Jack, I haven't felt this happy for a very long time."
Jack then started to suck May's clit, he had the nub of her clit between his teeth, and he was sucking hard as he finger fucked initially with two fingers; now he was using three, May loved this. May was now taking two-thirds of Jack's cock in her mouth; it felt so good. Jean, Jack's lecturer, took his full length quickly so he knew that it could be done. May came off Jack's cock and said, "Jack, I will be able to do it with your cock, but I must align my throat to the angle of your beautiful cock; I'm working on it. Jack, I love the three fingers. Could you try four as I love my pussy stretched? What you're doing feels so good."
"May, I'll stretch you later; when I go inside you, I'll do it slowly; if you have any discomfort, then let me know as it may take some time for you to get used to my big boy. Now I'll make your pussy so wet that you'll have so much lubrication that he'll slide up you a lot easier."
May replied, "Jack, you are a darling."
Jack then slid another finger inside May's hungry pussy; he was now drawing May's clit into his mouth as he sucked her huge clit; he was also finger fucking her hard and fast with his four fingers, then May said, "I love it, keep fingering my cunt firmly, I like that, I am close to cuming. I am so close; I'd love to cum in your mouth. Can I cum in your mouth?"
Jack didn't reply; he kept sucking and finger fucking her hard, May's pussy was squelching, then Jack felt the warmth of her creamy spunk flood into his mouth; it tasted sweet and delicious. Jack kept sucking as May trembled with her orgasm. A minute later, May was calm; Jack had a mouthful of her cum in his mouth. He took May in his arms then they cum kissed; the kisses were so intense and affectionate. May was transferring her cum from Jack's mouth into her mouth. They continued kissing for several minutes, then May said, "That was amazing, that was a gorgeous orgasm you gave me. Thank you for doing that for me. It shows me that you aren't selfish, neither am I. Jack, I've been thinking, let me go on top of you cowgirl, then I can control things. I need to get used to your big boy; then, things will get perfect. I want you so much."
Jack lay on top of the bed as May teased her the head of Jack's cock. She then slid it up and down her long sex slit several times; as she pushed her pussy down on Jack's stiff cock she said, "Here goes, I'm so looking forward to this."
Amazingly, May took Jack's entire length on the first push; she gasped with pleasure as Jack felt her thick cunt lips around the base of his stiff cock. Then, very slowly, May started to ride his cock, gradually increasing her rhythm. May said, "I've never felt anything like this in my life, I had a big cock at University, but yours is in a different league. When I do things gently, the head of your cock caresses my cervix; that's a lovely feeling. When I up the tempo, then it stimulates my cervix; those are two wonderful sensations. It feels so good Jack, I'm so happy that I can take it so easily. I feel stretched, but it feels so comfortable; it's a wonderful feeling."
Jack smiled, then said, "I knew that I'd fill you; it feels great for me too; I love how you're gripping me; you grip at exactly the right moment. May, your tits are amazing; I love how they jiggle as you ride me."
May was now arching her back with her downward push; this felt great for Jack, May said, "That's good, once I know what you like, then I'll make it nice and snug for you, do you like a tight ride?"
"I love the sensations that gripping gives; you get a lot of nice thrills. I love how you are riding me this now, May."
"I love the sensations that your magnificent is giving me, Jack. After our husband's died, Jill and I kept our Kegel Exercises going, we were always hopeful that we would find someone nice, but it didn't happen, but now we're together, then things will change. My Kegel Exercises give powerful cunt muscles. Do you like it very tight?"
As May said this, she gave Jack a vice-like grip on his cock; she clamped it, Jack said, "I'd love you to do that when I'm cuming; that could be sensational."
"Jack, we'll have so much variety; we will never be bored. Did you know that I can multitask? This is just for you."
May then, as she was riding, May brought her massive left breast to her mouth and started licking her hard nipple. Then she started sucking it as she squeezed and played with her right tit. She did it also erotically; it looked amazing. May was now beginning to pound Jack's cock; she was riding him harder and faster, then she said, "I'm so close, cum for me Jack, let me feel your cock juice squirt on my cervix. The head of your cock is now hitting my cervix; that's how I like it when I'm cuming. I am going to grip you differently on each squirt you shoot inside me. Then you can tell me which one you enjoyed the most."
May came first, she trembled with her orgasm, seconds later Jack came, remarkably May gripped on the first squirt and the following four squirts with different levels of gripping on each jet. Finally, Jack said, "May, you are amazing, that was wonderful, number two was my favourite, number one was too strong, number two was wonderful."
"Jack, I've never felt anything like that in my life. The pressure of your squirt was fantastic as it hit my cervix, which gave a big thrill. I feel so comfortable, Jack; your cock fits me perfectly; I hope that I've given you a good memory of our first fuck."
"May, it was wonderful; I feel so comfortable with you. However, we must look to the future; I want to see you regularly; how do we manage without mum knowing? For the next ten days, we haven't a problem, but what do we do when she's back home?"
"Jack, I want to see you too. Can you stay tonight with me? I want to wake up with you tomorrow morning? I want you to come for dinner tomorrow night. Can you come?"
"I want that too May, mum's prepared evening meals for me every night; I can't have her coming home, and half the food is not eaten. Can you stay with me some nights, then we can eat the meals she has prepared?"
"We will do that, darling; I'll come to you tomorrow night, then you to me the following night. It's a difficult thing with your mum; Jill's my best friend. But, Jack, I must be honest with you, I must be the one to tell you this, your mum and I are lovers; we have been through thick and thin together. I know her well enough to tell her about us, I know that she will accept this, but I know that she'll still want to see me; there's no one else in her life. So what kind of position does that put your mum and me in?"
"Perhaps the best way forward would be if Jill and I shared you. How do you feel about that? Jill has a huge libido; she loves sex, she needs sex. I know that she would adore your cock. Yes, we can be discreet, but then I'd feel that I'd be letting down your mum. I know that if Jill was in the position that I'm in with you and she had someone like you, she'd want to share him with me. The problem is that you're Jill's son. I know that if Jill found someone like you in real life, then she would be with you. There are many ways we can do this, but I think this is the best way for all of us."
Jack thought for a moment, then said, "May, I agree with you. For years I've found mum attractive. If I was sure that this could happen, then we should do it. You can't say to mum Jack's got a massive cock and gives a great fuck; we have to find a subtler way of doing it. For example, you could say that we met and you invited me over for a meal. We did that then I invited you over for a meal as I had all mum's meals. Then you could say that you wanted to kiss me, then ask mum how she'd feel about that? If she says she's no problem with it, then we move to the next stage. Doing it this way, we're the seeds to mum; how she responds will tell us exactly what we need to know."
"Jack, what a fantastic idea; this is the best way for us to go. I know Jill so well. If we do this, I know that she'll be phoning me to find out how I got on the night before. Now love me again; your magnificent cock is still hard; it takes you minutes to recover. I hope that this works out for all of us.
The next morning they had a fantastic session just before seven in the morning. May was glowing as she made breakfast, they had showered together, but Jack needed to change his clothes. So they agreed that May would come to Jack's house at six this evening, she would bring clothes for the following evening. May was also going to phone mum to explain that May had met Jack and invited him for dinner. They kissed lovingly before Jack left; as Jack walked home, he looked forward to seeing May tonight.
Jack had worked hard; he had a message from May saying the seeds had been sown and how much she was looking forward to seeing him tonight. Just after three, Jack had just finished with a client; he received a message from mum, it read, "Jack, I'm so proud of you, I tried to call you, but you were with a client. I spoke with Angela; she told me how you were doing. She said that you were faster and did more work than three Paralegals; you have no idea how pleased I was when she told me that. Gran is amazing; she has me swimming two kilometres and riding a bike for ten kilometres every day. We do this in a Spa Hotel ten minutes from grans house. I am feeling the benefit of all this exercise."
"Gran was depressed, she had a boyfriend, and he died a couple of weeks ago. I think that she misses him. She's bored to tears down here. She has wonderful sea views but nothing to do and no places to socialise. She's been talking about renewing her Practising Certificate and coming back to work part-time in the office. Gran was a first-class lawyer in her day. She would be an asset to the practice, but nothing is definite yet. She would stay with us during the week and go to her house at the weekend. I think it's a good idea."
"I had a call from May, she said that she had met you shopping and had invited you for dinner, that was so nice of her. She thinks you're a perfect gentleman, so polite and courteous; I'm proud of you. She told me that you had invited her tonight for a meal that I've cooked, that was kind of you, Jack. Don't be mean with the wine; in fact, offer her some Champagne; there's a couple of cases in the cellar. Gran's had her hair highlighted and styled; she's asking kindly for you. A lady at the pool took a couple of pictures of Gran and me on my smartphone today; I will send them when I figure out how to attach them; my new phone is so sophisticated. If I don't manage it, then I'll ask Gran to do it. Keep up the good work. Love mum xx."
Jack got a message from reception that his mum had phoned, but he was with a client. Angela had taken the call. Jack left the office just before five; he had left two portions of goulash out this morning, they were defrosted. Jack then took three bottles of Champagne from the cellar; he took two fast chill sleeves from the freezer and put them around two bottles; they would be chilled in twenty minutes. He put the three bottles of Champagne into the fridge and went to change.
May arrived just before six; she was carrying a small suitcase, she was also wearing a light raincoat which Jack found strange as it was a beautiful day. When May stepped into the house, Jack closed the door; May took off the coat; she wore a stunning red crotchless Basque, self-supporting stockings and three-inch heels. She looked gorgeous. They kissed and touched for a couple of minutes, then May said, "Let's have a quickie before we eat, I want to have you in a chair, and I know the chair that I want you in."
May led Jack into the lounge; there were two wooden with upholstered cloth seats; she took one and asked Jack to strip naked and sit on the chair. Jack stripped naked, and his cock was rock hard; it looked so impressive. May said, "I was hoping that you'd be a little flaccid, then I could have licked and sucked you, but I see you're ready for me. I am ready for you; I'm so wet, Jack. I have been thinking of your cock all day. Can I take a couple of pictures of it later then tomorrow? So I can look at them. That will make me horny when you come to me."
Jack told her she could take them later. May kissed Jack passionately then said, "After our quickie, I'll lick and suck your cock clean, then we can have a protein kiss, and that will be our starter for our meal."
Jack sat on the chair, May guided Jack's cock to her pussy lips then pushed down; she took his full length quickly. Then May popped her massive tits out of her Basque and rode Jack as he sat on the chair. May said, "I've thought of your cock all day; I was even thinking of it when I spoke with Jill; I will tell you what's happening there when we cook dinner. It feels so good when I slow down; then, I'm just stimulating my cervix with the head of your cock. When I do it like this, then I'm pounding my cervix, I'll do that when I'm cuming, but that won't be for a few minutes."
May was so relaxed; it was apparent that she was calm and comfortable with Jack. Jack was now fingering May's clit; she loved that. May was giving Jack long strokes; Jack could see seven to eight inches of his shaft when May gripped him at the head of his stiff cock. Jack's shaft was glistening with May's cunt juice. Then Jack lubed his middle finger with May's pussy juice; he slowly slid it up May's tight ass. May gasped with pleasure, then said, "I love that Jack, give me another finger, and that'll make me cum."
Jack gave her another finger; May was now pounding Jack's cock and the two fingers that Jack was finger fucking her ass with; Jack was good; he was finger fucking her ass at the rhythm as May was pounding his cock. A minute later, May had a mind-blowing orgasm, Jack, faked an orgasm as he had nothing to eat since breakfast and was very hungry. May's face was glowing as she leaned down and kissed Jack. They kissed for a minute, then May said, "I love you, and I love your cock, Jack. That was gorgeous; everything happens so naturally with you. Now, you sit comfortably in this chair as I have a little job to do."
May was gripping Jack's cock at the base as she raised herself up, still maintaining pressure on Jack's cock with her cunt muscles. She slowly came off Jack's stiff cock; there was a blob of cum on the bulbous head of Jack's cock. May then went down and licked and sucked Jack's cock clean. When she had finished, she came up and opened her mouth in front of Jack. The blob of cum was now on May's tongue. She then cum kissed Jack lovingly and tenderly for several minutes. Both their tongues were busily transferring the cum into Jack's mouth.
They then went into the kitchen, May took the goulash out of the two Vacuum Packs and put it into a pot to heat it. It was simple as mum already had cooked the potatoes, and they were with the goulash. Jack got the Champagne; May said, "That's nice; if you pamper me with Champagne, I'll pamper you in bed later."
They sat at the kitchen table sipping the Champagne, then May said, "I've sown the seeds; I was truthful with Jill as that's the best way. I told her that we had met at the wine shop. I had invited you to come over for a glass of wine that evening. I told her that we had talked about Mags. I said that you were comfortable with that. To cut a long story short, I said that I was attracted to you. I felt so comfortable being with you. I told her that I wanted to kiss you but didn't because I was thinking of her; Jill told me I should have kissed you if that's how you felt. She said that we were both adults, and that was a natural thing to do. Of course, there's an age difference, but that doesn't matter if your both attracted to each other."
May said, "I told your mum that I had invited you for dinner the following night. You were happy about this, and you said that you would bring some wine. I told you that I had plenty and you didn't need to. Then I said that as you were leaving, you cuddled me, the next thing we were tongue kissing and you were a beautiful kisser, both our tongues were deep in the each other's mouths. I told Jill that it felt so good that I didn't want to stop."
"Then I told her that you had put your hand under my top and were squeezing and playing with one of my girls. I told her that you unhooked my bra and raised my bra over my tits so you could play with both of them. I told her that I didn't want you to stop, but I thought we should stop before we went too far. I told her that I could feel your stiff cock pressing against my leg; it felt enormous. I told her I wanted to feel it. I then told her it was easily the biggest cock I had ever felt; it was thick and long. I then told her that we should stop now. It would be better if we both wanted to do this then; we must both be sure. I told her that Jack could still come for dinner the following night."
"Jill said that I had done the right thing. She asked me a lot about the size of your cock. I told her that I hadn't seen it; I had only felt it and felt massive. I told her that I was so excited all day about you coming to dinner. I told her that we had a wonderful night; everything was relaxed. Then I told her that we kissed and touched that you played with my girls. You made me cum as you played with them. I told her that we wouldn't have full sex tonight as we both must be sure. I told her that I felt sorry for you as that was two nights running that I'd given you a hard-on, so I took your cock out and sucked you off. I told her that your cock was beautifully proportioned. It was long and thick. I told her I could only take two-thirds of it in my mouth as it was so big. Jill then told me to angle my throat then I could deep throat you."
"Jack, I think that Jill would like to be with us. She has no problem with me doing it with you. She said if we were both sure, then we should do it. I didn't tell that we had done it, and you gave me the best fuck of my life. There's another important thing; your Gran was having an affair with an old Pharmacist, he was a bit older than your Gran. He was a widower with no children or family. He had six Pharmacies which he sold for several million. Jill found a cupboard in Gran's house filled with boxes of Viagra; Jill is sure that Gran shagged him to death. Gran knows that she is the beneficiary of his will as Gran went to his lawyers when he signed it. This is one reason why Gran wants to come back here as it's so quiet there, and tongues would be wagging."
"When Jill spoke with Angela today, Angela told her that morning she had received a letter saying that Gran was the only benefactor of her friend's will. So mum and Gran may be returning faster than we expected, Jack. I am sure Jill will be on the phone with me tomorrow morning to see if we did it tonight. I will tell her we did and again in the morning. I am sure that she'll be interested; I wonder how she'll play it."
The goulash was excellent, they then went to Jack's bedroom, May went into mum's bedroom and found some lube. May then got Jack to pose with his massive hard-on; she took four excellent pictures of it. His cock looked so impressive. They had a fantastic night; Jack ass fucked May; she loved it. He gave her three vaginal orgasms anally, with the head of his cock stimulating May's G-spot, then he did her dripping pussy doggy style. May was a satisfied woman when she fell asleep. They both were pleased. Both were thinking if Jill would get involved with them.The next morning May wanted anal first; Jack gave her two orgasms, then did her pussy doggy style. May loved how deep he could go when he did her pussy doggy style. May made the breakfast; she had an early appointment, so she was in a bit of a rush. Jack told her that he'd be at her house tonight at six. May said, "Jill was very interested yesterday in the size of your cock. I have been thinking about it; the pictures that I took are for my enjoyment. Would you mind if I shared two of them with Jill? If she's interested, then she'll start to flit with you. I'll attach them with a message; I can handle it, do you want it to? He goes so deep in every hole. My appointment is at eight o'clock; I will send it before then, so any messages you get after that, you'll know that Jill has seen it."
They kissed lovingly but hurriedly; then May left with her suitcase. Jack got to his office at eight-thirty, he made a coffee then checked his messages, he had one from mum sent at twelve last night with two pictures attached. The message read, "Gran, helped me send these, she's so good with computers and phones. I hope that you looked after May last night. I think that she likes you a lot. I think that Gran and I could be with you soon. Gran can sleep in one of the spare bedrooms. Gran applied for her Practising Certificate online yesterday; she has a meeting with the Local Law Society on Friday, so that we may be home on Thursday night. I am missing you. Love mum xx."
Jack was amazed by the two pictures mum had sent with her and Gran. They both looked gorgeous. One was head on the other was at an angle of twenty-five degrees; this picture showed their massive tits, flat stomachs and beautiful figures to perfection. Gran looked stunning, and so did mum. Mum was wearing a red one-piece bathing costume. Gran was wearing the same in pink. The tops were cut low and showed a lot of cleavage. Jack felt his cock stiffen as he looked at that picture.
Then he looked at the head-on picture; mum's camera was HD and very powerful. Jack used his fingers to enlarge the tit area for both of them; their tits looked amazing. Jack then enlarged the vulva area. Both the costumes were very tight fitting. Jack then saw two of the best Camel's Toes he had seen in his life. They were so similar that you could say that they were identical. Both had very long sex slits; both had perfect cunt lips. Both of them looked so fuckable. Jack studied them in detail for several minutes. He liked what he saw. Jack knew that both of them knew what they were showing in the pictures. Their beautiful big tits and both their amazing Camel's Toes, mum had sent it; Gran had helped her. So it wasn't just mum that was flirting; Gran was in it too.
Jack replied, "Dear mum, thanks for the beautiful pictures of you and Gran. You both look gorgeous, and you both look so young. To look at the pictures, you would never think it was of a mother and daughter. You would think it was two sisters with a couple of years between them. I had a lovely night with May last night. We drank two bottles of Champagne. We are so relaxed when we're together. I am missing you, mum, but May has invited me for dinner tonight. May looks after me well. I love you mum, Jack xx."
Jack checked the time; it was nine-fifty. Jack then got started on his work. He had six files to get through. He enjoyed this work; he would carry out Legal and factual research on these files. The more he did, the faster he was getting through them. Jack had no idea that just after eight mum had tried to phone May, May was at her early meeting, her mobile was on voice mail, mum hung up then sent May this message, "Thanks May, what a cock, I couldn't believe the size of it, it's enormous. It's bigger than that guy; I can't remember his name at University that we had threesomes with. I want Jack's cock, I know incest happens a lot more than people are aware of, but I want to love and have that cock. The other problem is I showed mum the pictures; she wants him to. She's deadly serious; she wants Jack's cock too."
"We can't just say to him, Jack, we would love you to fuck us, let's do it. May you must have an idea of how Jack thinks sexually? What makes him tick? We must try and think of a way to send signals to him that we're interested in him. I can flirt with him easily, but how can mum? I sent Jack a couple of pictures late last night of mum and me in tight-fitting bathing costumes; he could see a lot of our tits, believe me, they looked good. He could also see both our Camel's Toes; the costumes were so tight down there that they showed our long sex slits beautifully. He hasn't replied yet, so I've no idea what he thinks of them. If you have any ideas, then let me know. Mum wants to know if Jack gives good anal? To be honest, I Iike it myself. I can call you if you want, but if you're stuck for time, then please WhatsApp me. Love Jill."
May was between clients, she replied to Jill, "Jill, Jack is amazing; he's a gentleman. He is very caring and attentive. He doesn't rush anything, his foreplay is phenomenal, he gives the best oral that I've ever had from a man, you are fantastic too, but Jack is incredible. I can only suggest that you flirt with him and send out signals; I'm sure he'll respond. How your mum can flirt with him, I've no idea, but I know that he likes you both. His anal is out of this world; his cock is so long that the head of his cock stimulates my G-spot; this gives you vaginal orgasms that are so strong and powerful. I'm with Jack because of Mags; she didn't feel comfortable with his big cock. When I saw his magnificent cock, I wanted it. I am sure one day Mags will regret her decision. Jack's giving me the best fucks of my life. If you have any other questions, then please ask. Love May."
Mum showed Gran May's message; this excited Gran more then Gran said, "Jill, I've pulled a lot of men in my life; I'm sure with a little thought I'll be able to pull Jack. But, of course, it will all be down to flirting with him, two sisters, what a lovely compliment, please give me his mobile number, I need to thank him for those nice words."
Mum gave Gran Jack's mobile number then started to think about how she could reply to Jack with a subtle flirt. Gran was already typing on her smartphone; she wrote, "Dear Jack, Jill gave me your number as I wanted to thank you personally for that lovely two sisters compliment. That was so nice of you. Thank you. I don't know if you know that the partner that I had in a relationship sadly passed away. That's me on the market again, but it's so quiet here that I've decided to come out of retirement and work part-time with Jill. I've suggested that I use one of the Consulting rooms as my office. I would like you to share that office with me as I would like to work closely with you. I have a wealth of experience in every aspect of Law. I have kept myself up to date in every change in the Law since I retired. I have also suggested to Jill that I will do the Saturday morning Court work. You can assist me. By my doing this will relieve Jill and Angela from doing it. I am keeping your mum fit at the Spa; I know of two in your area, so I must check them out. My dear Jack, you will find that I'm excellent at a quick sprint, but I'm also excellent at distance events. I look forward to hearing your comments. Love gran xx."
Jack was impressed with the ambiguity and suggestiveness of Gran's reply; she was quite a woman. Jack thought for a moment, then replied, "Dear Gran, I'm so happy to hear from you with your so kind words. The photos mum sent showed you both in such an appealing and tempting way. I am so sorry to hear about your late partner; I'm sure with your pretty face and exciting features you will soon find someone who will look after your every need. I am so looking forward to working with you; that's so kind of you the offer you to share your office with me. I am sure your experience and my curiosity and eagerness to assist could be an exciting opportunity for both of us in every way. Are you looking forward to your next adventure in life? Love Jack xx."
Jack wondered how she would reply; he was sure that Gran would flirt in her reply. He didn't have to wait long; five minutes later, Gran replied. "Dear Jack, thanks for your interesting reply, you're going to be a great lawyer, as well as Law, I can give you the experience of life, but in that area, we both use a lot of discretion. I am happy that the photographs tempt you; my body and mind are still in excellent condition. Would you be the one to be able to look after my every need? I believe that it would be nice if you were interested. Don't worry about my partner, he was not that good, and laterally he was not much use at all. I have a powerful libido, and hopefully, that's in your blood too. Jill and I will be home on Thursday evening; if an opportunity for us to be alone, then we possibly could have a little sprint. If not on Saturday you could come with me back here to help me bring more of my clothes, we could have a distance event. I am now thinking a lot about you. Are you happy with my suggestions? Love gran xx."
Just after Jack had read Gran's message, he had a message from mum which read, "Dear Jack, what a nice thing to say about Gran and me, I never thought of two sisters but when I looked at the pictures again then yes it would be possible to think that. That sounds lovely spending time with May; I'd love to drink wine and relax with you. I'm sure that we could be very comfortable together. The house is going to be a bit crowded from Thursday with Gran coming back with me. So, I'll come to the point, would you be interested in spending, as they say, quality time with me? I would love to know what you think. I love you, Jack, love mum xx."
Jack then knew that Gran and mum wanted him; he wanted them too, along with May. Jack thought to himself, what a lovely and exciting situation I've got myself into. Jack then replied to Gran; he wrote, "Dear Gran, I am more than interested in your suggestions, but I must be honest with you, I'm having an intimate sexual relationship with May at the moment. I look at the pictures of you and mum; I get aroused and excited about having the same intimate sexual relationship with both you and mum as well as May. I am young enough and have the libido to satisfy all three of you. May has no problem with sharing me with you and mum. If we are all comfortable with this, then we don't have any problems. I hope that this is acceptable to you? I love you Gran, love Jack xx."
Jack then wrote a similar message to mum, saying that he wanted to spend quality time with mum, Gran and May. Jack hadn't heard anything from May all day. He knew that she was having a busy day. Jack arrived at May's just before six; he was happy to see her car in the driveway. He let himself into May's house; she had given him a key. May was in the kitchen; they kissed lovingly and tenderly for several minutes, then May said, "I've had a busy day, and so have you, Jack. Jill phoned me, she's going to have a chat with her mum, Jill wants what you offered, and she's sure her mum will want the same. I want fucked as much as we can between now and Thursday; then I'll have a night off so you, your mum and Gran can get to know each other on Thursday night, then we can all get together on Friday night. I'm happy the way things are working out."
Jack got a message first from then mum, both accepting that they would share Jack with May. Then Jack went to May's house, where May told Jack that Jill and Gran were so excited about it. They were both wondering how to break the ice on Thursday night. Then Jack had an idea, he set up a Group on WhatsApp, he called it Family and Friends, he included himself, mum, gran May in the Group. Little did Jack know that this Group would become so busily used until Thursday and most certainly did break the ice.
Jack was writing the first message to the Group, it read, "Hi all, I'm so happy that all of you have agreed to share me. I must tell you that I'm so excited about this. May has told me that mum and Gran were wondering how we could all get comfortable on Thursday night; maybe we could use this Group to get to know each other likes and dislikes. May won't be with us on Thursday night but will be with us on Friday night. So having all three of you on Friday night is exciting me a lot."
"Mum and Gran, maybe we could have a little game on Thursday night? The two of you play with each other in front of me, and the first one to cum will get my cock first. I have spoken with May, now we have had a lot of sex together, I know what she enjoys, and she knows what I enjoy. Perhaps we all write about it here, so we are all in the loop, then we should all have a good idea of what everybody likes by Thursday and Friday night. May loves making me hard first; she loves it when my cock is very stiff. This is how she does it. So enjoy and don't be scared to ask any questions, no matter how intimate they are. I love you all. Love Jack xx."
Jack attached an HD video of May sucking and licking Jack's massive stiff cock; it looked so impressive, especially when you noticed May's smallish hands wrapped around Jack's cock. Gran was the first to reply; she wrote, "Jack, what a wonderful idea; I love how you think. We should all throw our likes and dislikes into the pot; my only dislike is pain. Your cock looks magnificent; a question for May, how difficult is it too deep throat? The video made me so wet; Jill needed to help me out; here's a little video of Jill sucking my clit; I know that Jill, May and myself all love having our clits sucked. We all love to cum in the other's mouth. I hope that you enjoy sucking clit to Jack; I'm so looking forward to this. Love Jo xx."
The video was first-class; Jack was sure that it was the same smartphone that had taken mum and Gran's bathing costume pictures. Jack felt his cock stiffen as he watched it. Then Jack got a surprise, May had replied to Gran's question about Jack liking sucking clit. May was in the kitchen preparing dinner, but her reply was great; it read, "Hi guys, this is a great idea, ask the questions, and you'll get the answers. First, you need to get your throat angled with Jack's cock then it's so easy to deep throat him. Regarding clit sucking, Jack gives the best oral that I've ever had in my life. Jack's not a swallower; he's a sharer. He gives wonderful cum kisses. I am so looking forward to Friday. Love May xx."
Then mum sent a message; it read, "Hi Jack, I want you to know that I'm so looking forward to Thursday night. I am very nervous about it, but I want you so much. Would you please not think of me as a woman that you're having sex with? Would you please think of me as a woman who loves you, a woman with urges and needs? I am also a woman that will do anything that you want to give you pleasure. I'm also your mum; I don't want to affect any things we do together. I love you. Love mum xx."
Jack replied, "Mum, thanks for the beautiful words. I feel the same way as you do, and I feel the same way about Gran. This is going to be wonderful. We all feel the same way. Thursday can't come soon enough. Here is a great way for you and Gran to let me know what you enjoy. What gets your pussies wet? Knowing this can make all the difference. Lots of hot kisses wherever you want them. Love Jack xx."
Gran then replied, "Jack, this is a great idea, Jill and my pussies are always wet. We both love everything. Would you like to 69 with Gran? Then I'd take your big stiff cock into my mouth and make it stiffer, and then you could spread my cheeks and tongue gran's ass as she sucked your cock for you. Then you could slip a finger up Gran's tight ass and tongue her hot cunt. I want to take your cock deep; I'll soon work out the angle my throat should be. I will take it down to your balls then make you beg to cum in my mouth. Jack, would you like it when I've got all of you in my mouth that I slip my tongue out and lick your balls? On Thursday night, Jill can lick your balls as I'm blowing you. Jack, Thursday night can't come quick enough for me two. I can't wait to feel you shoot your creamy spunk deep inside Gran's hungry cunt. Your Gran loves you. Kisses everywhere for you. Love gran xx."
Jack replied, Gran's honesty had touched him and openness, he wrote, "Gran, I love you too, I will fuck you and mum hard the way that I think you both need it. I also want to hold, kiss and cuddle you both and be so nice and loving to you both in every way. I love you both, and Thursday night will be special. All my love, Jack xx."
Late afternoon on Thursday, Jack was driving home; both mum and Gran's cars were in the driveway. Jack was a little nervous as he got out of the car; he loved mum and Gran with all his heart. May had brought them all together. They had both fallen in love with Jack's magnificent cock; they hadn't seen it as yet buy in the modern digital age, a picture said a thousand words. Jack opened the front door; he heard mum and Gran in the lounge. They were laughing and sounded happy.
Jack went into the lounge. Mum and Gran were both in crotchless bodysuits and self-supporting stockings; they looked gorgeous. However, Gran's figure looked a little fuller than mums, but they both looked terrific; Jack said, "You both look gorgeous, thank you for dressing like that, you have broken the ice nicely, would you like me to get a little more comfortable?"
Mum got off the couch; she hugged Jack pulling him closer to her as their lips met. They tongue kissed for a couple of minutes, then mum said, "Jack, I'm not forward, but Gran and I would love to see your cock. Before you arrived, we were both looking at the pictures of it; we are both very wet and excited."
Jack stripped naked; his cock was so stiff; Gran started to stroke it then said, "It's beautiful, it has perfect proportions, Jack, your balls look so heavy, I thought May would have emptied them, but there's still some left for us."
Then mum cupped Jack's heavy balls and said, they feel lovely. I'm sure that there will be no shortage of Jack's spunk."
Then Gran said, "I'm sure of it too, now Jack, we have to put on a little show for you, first to cum gets your magnificent cock first, now the big question, what would you like us to be, two sisters or mum and daughter? We can be anything that you'd like us to be."
Jack laughed then said, "I love your imagination, gran, be what you want to be, both of you look fantastic, I'm a little nervous, but I'm sure that I'll relax as I watch the show."
Gran said, "Don't know about relaxed, but I'm sure that your cock will get very stiff when you watch our little show. So, Jill, let's pop our tits out, then we can get comfortable on the carpet."
They both popped their tits out of their bodysuits, then they hugged and tongue kissed. It was such a hot kiss, filled with affection; Jack could feel the love between Gran and her daughter. Jack knew that this would be quite a show. They both positioned themselves on the carpet in a way that would allow them to 69, then Gran said, "Jill, your honey pot is so wet, I need a taste."
That's when they both went down on each other; then Gran was running her tongue through the folds of mum's dripping pussy. Next, Gran was running her tongue up and down mum's long sex slit, teasing mum's clit when she got to the top of her stroke. Gran was totally in control, what Gran was doing to mum; mum loved it. The gasps of pleasure coming from mum were noisy and sensual. As Gran started to suck mum's hard clit, she was now thrusting two fingers in and out of mum's wet pussy; mum had spread her legs wide open for Gran; it was an incredible sight. Both mum and Gran individually were cock stiffeners. Seeing them do this was making Jack's cock very stiff.
Gran was now sucking mum's big clit fast and hard, still finger fucking her with two fingers. Then Gran used a finger from her other hand and slid it up mum's tight ass hole. Then mum flooded Gran's mouth with her creamy spunk. Gran held a lot of it in her mouth as mum cried out, "I've won, I came first, I will get my baby's big cock first."
Jack notice the glint in Gran's eyes; he was sure that Gran had planned it this way. Then gran cum kissed mum; they kissed lovingly for a minute, then Gran said, "Jack, would you like to taste your mum's cum? I've saved some for you; it's so sweet and delicious."
Gran then cum kissed Jack, her tongue deep inside Jack's mouth; Jack tasted mum's cum. It was delicious. Jack also loved the way Gran kissed; Gran was a very sexy woman. Mum was now lying on top of the carpet in the missionary position; her legs were spread wide, mum was finger fucking herself with three fingers, her other hand was rubbing her huge nub of a clit with a circular motion, mum said, "Come on top Jack, mum's ready for your big cock."
Jack then straddled mum, gripping his stiff shaft at the base; he ran the bulbous head up and down mum's very wet long sex slit several times. Then he placed it in the middle of her long sex slit and pushed; mum gasped with pleasure as she took Jack's full length quickly. Mum said as Jack started to ride her, "It feels wonderful, my pussy feels stretched, but it feels so comfortable. Baby, I want you to cum inside mummy's pussy. Let me feel you squirt your creamy spunk inside me. You are hitting my cervix with the head of your cock; I've never had that before."
Jack had built up a powerful rhythm; Jack loved how mum gripped his cock with her powerful cunt muscles. Mum was working her hips in rhythm with Jack's pounding hips; this was thrusting Jack deeper inside mum's hungry cunt. Then mum said, "Fuck me harder, Jack, nice and deep, give all of it to me, I can take it."
Jack loved fucking mum; they were both giving it their best shot, then mum cried out, "Rub my clit Jack as you fuck mummy's pussy, rub it hard, mummy's going to cum for you."
Jack was now slamming into mum's squelching pussy as his thumb pressed harder on mum's huge nub of a clit. Mum's hips were pushing harder against Jack's pounding cock as mum's strong cunt muscles contracted against Jack's massive cock as Jack slammed his stiff cock up her quivering pussy relentlessly. Then mum slumped on the carpet and said, "I haven't cum this hard for years. Did you feel mummy's cum on your cock, darling?"
Jack leaned down, and they kissed tenderly and lovingly for a couple of minutes, then mum said, "You fucked your mum the way that she needs it, now fuck your gran, believe me, gran needs your cock."
Jack had noticed that Gran, who had been sitting on the couch watching them, had been lubing her ass; Jack was curious as to why she was doing this but didn't say a word. Gran looked terrific as she came over to Jack; Gran said, "Jack, you have a beautiful athletic movement as you were riding Jill; the way that you were slamming into her was incredible to watch. You have excited and aroused your Gran now."
Then Gran stroked Jack's stiff cock then said, "Jack, you're so hard, is all that big boy for gran, I want to feel him everywhere."
"Gran, you can have all of him wherever you want."
"Jack, I'd love you to suck Gran's clit. My clit is my starter button."
"That's it, Jack, just like that, it feels so good. But, my god Jack, your cock is so stiff; I want him inside me now."
Gran then straddled Jack, she leaned over she tongue kissed Jack, Jack could feel the heat of her pussy on his stomach as Gran swayed her hips, as Gran kissed Jack, he felt Gran's cunt juice dripping onto his stomach. Jack's body tensed as Gran teased her pussy with the bulbous head of Jack's cock; Gran said, "Jack, tell gran what you'd like gran to next for you?"
Jack knew where this was going; Jack replied, "Gran, I want you to fuck me."
"Super Jack, we're both starting to think the same way."
Gran then placed the head of Jack's cock inside her dripping cunt lips and pushed down firmly. Gran was in control; she had leaned over, her massive tits were resting on Jack's chest, she was kissing him lovingly. Her hips were doing all the work as she lifted and pushed down her hips. Jack's cock was sliding in and out of her. Gran then upped the tempo, faster and harder she was going, then Gran said, "I'm so close Jack, slip a finger up my dirty hole, I've lubed it for you; it'll slip up me easily."
Jack did as he was told; thirty seconds later, Gran had a mind-blowing orgasm; Gran continued to pound Jack's cock throughout her orgasm, then Gran said, "Jack, your cock is magnificent, we can all have a lot of pleasure from it. It fills me beautifully. Could you stay in this position? I want now to take your gorgeous cock in my dirty hole. What would Jack like Gran to do now with Jack's big cock?"
"Gran, I want you to put my cock up your tight ass then fuck me in the cowgirl position?"
As Gran pushed her ass down on Jack's cock, she said, "It feels amazing, Jack, the head of your cock just hit my G-spot, it feels so good, I want more of this."
Gran soon was hammering Jack's cock; she was gasping with pleasure as she raised and lowered her hips on Jack's cock. Her massive tits were jiggling beautifully outside her bodysuit. Then out of nowhere, Gran had a vaginal orgasm from ass fucking Jack's enormous cock. Jack was fingering Gran's clit as she climaxed. Again, he felt her creamy spunk on his fingers. This time Gran came to a standstill on Jack's cock. She was still trembling a minute later, then Gran said, "That was the orgasm of my life. I've never cum so hard in all my life. Jack, we are all going to have so much fun now."