The Pleasuring of Granny Ch. 02

The Pleasuring of Granny. Part 2. (First-time, Anal, Mature,)

The Diary of a happy Man.

By: djinnrummy (Names have been changed for the usual reasons)

To Recap:

My name is Tim. I am not, nor have I ever been, married. I have never wanted to be married. I know and have known some very special women. They have shown me that there are a large number of women who, through no fault of their own, are stuck in a loveless or at least a sexless life and that they are expected to endure it because of their ages or 'position' in life. Quite a few of them do something about it when the right opportunity arises.

I consider myself to be one of the most fortunate of people on this planet. I was gifted with a six foot tall body, strong, healthy, and "un-ugly." I am also blessed with a 10 inch long, 6 inch girth penis and the stamina and constitution of an Ox to use it. I am well aware that size isn't everything, but, you can learn the rest of the requirements! I am addicted to females, I am besotted with breasts, and vaginas' and I hope that never fades away. There are of course exceptions, but considering the size of the female population, I am happy with the remainder.

For the benefit of those who are easily confused, stamina and constitution have nothing to do with the possession of balls.

Part 2:

Date: 11th December 1965. (A date I shall never forget)

I came home from work to find Granny and my mother, whom I shall refer to as Pat from here on in, setting the table for dinner. This was a surprise as I had no idea that she was even in the country.

After the meal, and usual chit chat that goes with visits, Granny said that she had to get us all 'on the same page', so we settled down in what she liked to call the 'drawing room' and I call a living room, then all was made clear.

"Tim, there has been a lot going on behind your back these last few days and now is the time to get everything out and sorted. I've been thinking for a while now about Jean's situation. You and I rattle around in this huge house, we hardly use any of it and Jean is desperately trying to keep a roof over her and her husband's heads, well I can and will fix that. I'm wealthy, healthy, and you've gone a long way to making me happy. I don't see why we can't use what good fortune we've got to help someone else be happy as well."

"Pat has some news as well and it was her telling me the news which made up my mind for me. I've decided to turn that unused second drawing room into a long-term care room for Jean's husband, and then she can give up renting that hovel they're living in and moves in here with us. It's large enough to put two beds in there as well as all the furniture she'll need. Before any of this can take place the three of us need to talk about our own situation."

Pat then spoke up and told me that she had lost her job suddenly, details would come later, but she had asked Granny if she could come and stay until after Christmas then she could seek another post. Granny picked her up at the station and together they'd sorted out the details of the proposed new arrangements.

Pat then went to Granny and kissed her.

"Granny, I already know you two are screwing each other silly. Thanks to the remote for the drive gates, I actually arrived here one day about an hour before I announced myself, I heard a great deal and I'm green with envy! I never knew he preferred older women. I certainly never knew he could make a grown woman squeal like he did with you. I'm not his real mother, you don't have to explain anything to me, but I give you fair warning, if I can bed him, I will."

"Err, can I say something?"

"What?" "What?" From the two women who have been closest to me in my life.

"I know I'm only a sex object now, but there was a time not all that long ago when I thought of you as my mother and now I find that you are planning to have me in your bed, I'm getting an erection at the thought, I am to say the least, confused, but incredibly aroused."

"Are you embarrassed?"

"No"

"Are you shocked?"

"No, why do you have to be in bed? I'm all for wherever, whenever and I'll certainly encourage your ambitions."

"Is that a promise?"

"Yes Pat, that's a promise and as soon as this pow-wow is over I'll be happy to honour it."

We laughed and relaxed over a glass (or two) of wine and I found out that Pat was indeed going to be living here as she was to be the care assistant for Jean. I also learned that Jean had no inkling of any of this, but, as Granny pointed out Christmas was coming and it would be good to have a full and happy household at this time.

Granny said that tomorrow we had to plan the move of Jean and her husband. She then stood and smiled.

"I do believe I am tired out from such a busy day so if you will forgive me I'll say goodnight and leave you two to talk!"

Talk? Ha! It wasn't long before Pat had my jeans open and was hauling my erection out of my boxers.

She stared at what she'd got hold of and then looked me in the eyes and said:

"I knew you were going to be well hung, but I never thought I'd brought a horse up!"

She stood up, and started to remove her dress, revealing what a ripe body she possessed.

"Please, fuck me, now, here."

She would never be able to wear any of those clothes again and once I'd got her breasts out of her bra', I was lost. She really did have beautiful, full, firm breasts. She was obviously ready for sex, but she wasn't ready for ten inches of swollen cock being shoved into her in one thrust and she squealed in much the same way as Granny does, we then settled down to some very enjoyable, inventive and athletic fucking.

After her second climax I confessed that my knees were getting sore and pulled out of her, she sighed and said that that would keep her happy until the morning and stood up. Big mistake, she was on her back on the table before she could blink with my face pressed into her sex. I sat on a dining chair at the end of the table with my arms wrapped around her thighs holding her tightly as I spent a very wet and noisy thirty minutes eating her pussy.

My cock was beginning to throb again so I stood up and inserted it into Pat's soaking sex tunnel then slowly, very slowly, eased it into her until she once again had all of it inside her. I slid gently in and out of her, savouring each fantastic sensation of her vaginal muscles squeezing me as I did so. I could also caress her gorgeous breasts and nip her nipples as well as stroke her tummy.

Eventually the fingers of my right hand wandered down to her clitoris as my left hand continued to tease her erect nipples and soon she was panting and moaning, a glazed look in her eyes as she started to buck uncontrollably before emitting an enormous yell and clamped her legs around me as she climaxed.

I had been surprised by at the eagerness with which Pat got out of her clothes and asked me to please fuck her. I was certainly surprised that I didn't feel at all guilty in doing it.

We called it a day at that point and crawled upstairs to our respective bedrooms, Granny was in mine!

I honestly didn't have the energy to do much, but I needn't have worried, Granny just masturbated me until I was semi-rigid then climbed on top of me, inserted my cock into her very moist sex tunnel, (she must have been diddling herself as she waited for me) and then leant forward to whisper "Isn't Pat a noisy one? I'll always know when you're in her and that's for sure!"

She then forced herself down my shaft and rode me, I really didn't need to move, but the urge is strong and it wasn't long before I was thrusting upwards to meet her coming down until she started moaning, I had to clamp my mouth on hers until she came. As she slowly subsided onto my chest she told me that if she'd met me when she was forty she'd have left her husband and to hell with the money. I think I was asleep when she left my bed.

I slept late the next day and came downstairs to the aroma of bacon and eggs, but said I had to pass as I was late for work. It was Granny's week for surprises, she calmly informed me that she'd already rung in to tell my boss that I was having to take extended leave because of unexpected family problems and wouldn't be returning for some considerable time which is when I found out just how much I was appreciated. Granny was told that if I didn't return to work on the 28th of December, my employment would be terminated.

Before I could react to any of this Granny put a letter in my hand.

"Have your breakfast then go into the study and read that, then we talk!"

I did as she asked but I was not a happy chappy. Then I read the letter.

When Granny set out to surprise people she did not mess about. The letter was written by Granny's solicitor informing me that a trust fund had been set up in my name for the sum of 'One Million Pounds' to be available to me on my 21st birthday. All I had to do was stay with Granny and look after her and the house until that time!

When I'd recovered my composure and went in search if her and found her with Pat on the back porch.

"Granny! What is going on? What's all this about trust funds and a million pounds? What are you up to?"

The story finally emerged. Granny was not rich, she was astronomically wealthy. She had been lonely and alone after her husband died and then Jean, me and then Pat had arrived on the scene and her life started humming again. We never asked anything of her or from her, but we restarted her zest for life and especially in the area of sex. Apparently, she and Gerald had led a very busy sex life which included couples from the upper strata of society occasionally coming to their house for weekend orgies. All that stopped suddenly on Gerald's death. Granny had decided to restart it except that this time the participants would not have to travel anywhere.

"Tim, you are now a man of leisure, with a house and grounds and a Harem to look after. Pat, have you ever slept with a woman?"

"OK, time for secrets to be aired, yes, twice, she blushed, once a long time ago, never to be repeated. Then not until last September, twice a week after that up to last week, always the same person."

"What then?"

"Husband had been trying to get into my knickers, but his wife had beaten him to it by two months. We had regular sessions, Tuesdays and Fridays. It kept us both a little less tense. He used to go riding on those days, but one day he fell off his horse and came home early and caught us in the act. I got my marching orders and I think she got fucked, which is what we'd both been missing. Why?"

"We are going to be living in close company with each other for some time and I really do think we should be open about ourselves, Tim has fucked all three of us and Jean and I have had each other a fair number of times, I was wondering if that would give you any problems."

"Granny, take me to your bedroom and let's see how we get on, Tim fucked me silly yesterday and I'm still a little tender, a woman's gentle ministrations is just what I need right now."

I was left to mull over the days startling events. It was hedonism for me from now on.

Two hours later, sated and showered they returned to the kitchen for coffee and more 'chat' along the line of: 'how fit and gorgeous Granny's body was, how sore their vagina's had been after last night's debauchery' and just how much she hadn't known about having sex with another woman.

"Tim, you've never told me about any of your sexual conquests and I'll bet Granny would like to learn what you got up to."

"I never had any 'conquests', I couldn't afford to take girls out so that possibility never arose."

"You never had any sexual contact with girls?"

"That's right"

"No it isn't! I remember the time I caught Alice giving you a blow job!"

"She wasn't giving me blow-job, she was trying to find out what a boy's cock was like up really close, what it felt like and what happened if you did suck it. I think she was getting ready for a date with some boy from her school; I never got the chance to refuse and never really knew what was going on. I was only eleven!"

It was then that I realised that Pat was blushing again. Things started to drop into place, why I never got into any trouble over the incident, just told to pull my pyjamas up and get to sleep as she ushered Alice out of my bedroom with the promise of a very serious chat tomorrow, which never came.

"Pat! What did you do after you left my bedroom?"

Deep blush, "I took her to my room and got her tell me why she did what she did. She was being pressured by her school mates about discussing sex and experiences and she knew nothing, so she decided to use you to work it all out and you were right, there was a boy she was keen on, I think he'd seen his chance to score and he was leaning on her for a date."

"We talked about sexual feelings and the dangers of unprotected sex and being pressured to 'do it' without a condom. I'm ashamed about what happened next, but there I was in bed with a very soft body along-side me. Even at thirteen she had an amazing figure and I hadn't had any sexual activity for over four months because 'he'd' stopped showing any interest. Of course we know why now."

I started out merely explaining to Alice that it was natural for her to feel the way she did but it would be a lot safer if she found another girl who had a similar situation and maybe they could find out about their sexual needs together. It is quite a common thing these days and could be good fun."

I was guessing as I'd never done it with a woman myself!

Then I blew it, I asked her if she ever played with herself and she started to cry and said she'd tried but didn't really know what to do, so never felt anything. I asked her if she'd like me to show her how it all worked and, if she did find a good girlfriend, what they needed to do. Of course she said yes and all I'm saying now is that she had her first orgasm and I had to stuff my knickers in my mouth to muffle the sound of mine! And before you ask we never had a repeat performance, but I think Alice didn't waste any time finding, if you'll forgive the pun, a bosom friend."

"While were asking questions do you mind telling me why you prefer older women?"

"I don't mind, I don't prefer older women, I like them at all ages, it's just that since I met Granny I've been in the seventh heaven. She likes me, she wanted sex, and I certainly did. It was presented to me on a plate; I certainly wasn't going to turn it down. Granny taught me all I know, she's also been the cause of getting my cock into two more, very desirable, and available, women. Why would I want to go looking for someone younger, even if I did have the stamina I certainly didn't have the time or money."

"Right, Time for lunch, we've got to get going if we want to go to Jean's house and tell her what we want to do."

"She already knows what I want to do!"

"Behave and set the table."

We spent nearly three hours convincing Jean that her problems regarding her husbands care and well-being were over and that she would be amongst friends who would look after them both.

Granny had one final item to attend to; she told Jean that she didn't want her to have any misunderstandings about moving in with us.

"I'm probably looking at ten to fifteen years of being fit and healthy, then things will start to deteriorate. I intend to see that I enjoy every minute of that time so that means a lot of sex. I know Tim will fuck me silly any chance he gets, but I've also enjoyed you and want to keep on doing so, I reckon Tim will be close behind me, if not in front, and believe me when I tell you that Pat can hold her own, or anybody else's, when given the chance."

"So, bottom line Jean. Are you prepared to come into a house of love and debauchery, there will be no half measures, sex on demand and you of course will be able to do your own demanding."

We moved Jean and her husband in over the next few days and guess who got her in bed first, not me, Pat.

So I spent the night pleasuring Granny.

Date: March 1972

Jeans husband died following another stroke so the mood of the house was pretty low for two or three days. Things got back to normal when Jean came into the kitchen one morning in the nude and asked who would be first, I was, and she never did get breakfast, or lunch.

We had an idyllic life. All the sex and love you could handle, and although we were always together we never argued over anything.

We took holidays to warm countries in winter and loafed about our own house and grounds in summer especially round the pool, although the rule was still no sex outside the house, you never knew who might be watching.

Jean turned out to be a real sex fiend once she had no worries. One of her inventions was to conspire with Pat to put me through a bondage session every so often. The one I liked the most involved strapping me to a chair and then taking it in turns to arouse me, then mount me and ride me until I almost came, but then stop for a short while, before repeating the process until either they became so sore that they could no longer take my cock or I was unable to produce any more cum juice. Mind you, with all the fun I was having with soft bouncy breasts and erect nipples I wasn't about to complain at the treatment I was receiving.

After they'd done that I was invited to take retribution, if I had the strength!

One day I had and I did and Jean learned all about anal sex. It took the whole of the day for her to experience a large chunk of me inside her anal canal, but I had been in no rush, I wanted her to really enjoy the experience and be amenable to more of the same. It became obvious that she most definitely was.

Another reason for the length of time was that I kept getting distracted by other bits of her body. I learned later that Granny had warned Jean that I would probably have her backside fairly soon because she was asking me not to do it to her as often anymore and she knew I'd got a taste for it now and I'd already said I couldn't contemplate trying Pat in that way.

Date: June 1978

Granny and I did have sex almost every day, until she passed away at the far too early age of 73, after a heart attack following a fall from a bicycle. She had obviously loved me more than a little. She left the whole of her estate to me, her house alone was worth over six million on the open market, and there was a great deal of money plus other financial arrangements. I was a seriously wealthy man.

I would much rather that Granny was around, even if we'd never had another sexual encounter. She was the most wonderful person I ever knew and did more to shape me as a person than anyone else.

I moved into Granny's bedroom and talked Pat into moving in with me. I was tired of having to go visiting either her or Jean whenever I felt in need of sex during the night, mind you, in view of the amount I got during the day it didn't happen all that often. The end result was that Jean sometimes came and visited us.

When Pat moved in with Granny and me she'd written to Alice and made sure that she knew her new address, so she was beside herself with joy when she got a letter telling her that she was now living in Australia, was married, and had just given birth to a daughter, so Pat was now a grandmother.

The letter contained Alice's telephone number. Pat rang Alice immediately and it took a long time to prise them apart. (The bill for that call was astronomical but it was worth every penny just to see the happy smile and gleam in her eyes). I knew that it would be no more than a few days before she was telling us that she wanted to go and see her daughter and grand-daughter. To celebrate the news, Jean and I took our new Granny to bed, so I am still happily pleasuring Granny.