The Pleasuring of Granny Ch. 05

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A new sexual partner and a daughter's holiday.
3.5k words
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Part 5 of the 9 part series

Updated 11/02/2022
Created 11/18/2011
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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.

August 2013

Doreen.

Brenda and I were returning from a supermarket shopping trip, the weather was foul, there was a high wind, and it was pouring with rain. Rounding a bend on the narrow country road we saw a car in the ditch, with a woman standing in the road waving us down. She was soaking wet through, traumatised, but uninjured.

Her name was Doreen; she had been visiting her husband in hospital. He had been admitted a few days previously and had just been diagnosed as having pancreatic cancer. She was distraught because she'd just been advised that her husband's illness was terminally and he was unlikely to be returning home. She was so distracted by events that she'd failed to see the bend until it was too late and into the ditch she went, but at least she hadn't been travelling at high speed so the impact was minimal.

As we drove she chattered, telling us that she was 55, he was 60 yrs. old, they were married when she was 18 and he was 23. They had a married daughter and a 14 yrs. old grand-daughter living in London whom she rarely saw except at Christmas time. Doreen lived in a village, three miles after our track turn off, and as we didn't think she should be on her own in her present state we took her to Brenda's house to dry her clothes. Because of the conditions Brenda said that Doreen should have a shower and a meal and stay overnight. Doreen seemed relieved at this offer so I dropped them off with Brenda's shopping then went on to my place to unpack and store my groceries, have a wash and return to Brenda's cottage for a meal.

When I arrived Doreen had been given a sedative to calm her and was fast asleep. Well, nature being what it is, Brenda and I were downstairs having sex on her sofa bed. I had persuaded Brenda to get on top as I enjoyed her riding me, it meant I could feel her breasts and nibble nipples whilst manipulating any fingers I'd managed to inserted into her anus.

Although it was a very slight noise we both heard it. Doreen, having come downstairs without us hearing her, was watching us and what she saw had aroused her to the point that she'd removed the pyjama's that Brenda had loaned her and begun to rub her clitoris. She looked as though she was still drowsy from the sedative Brenda had given her, but it hadn't dampened her sexual urges. I stood up and went to her, then, putting her hand on my cock, I began fondling a lovely soft, ample, breast and asked if she would like to join us as she was obviously very aroused and we would love to help her relax.

From the way she grasped my cock I didn't think she'd need any convincing, I was right. Both of us fondled her slightly overweight, but very nicely rounded and soft, body. We lay her down on the sofa bed and spread her soft thighs wide apart. Brenda went down on all fours to taste her sex and finger her anus. Doreen tried to sit up and said that she had never had sex with a woman and wasn't happy with the situation. Brenda stopped what she was doing and told Doreen that what she was about to experience didn't hurt, it was fun, and that some women preferred it to having a man and she should be grateful that she had the choice of either sex or both sexes for fun and sexual release.

"I like both options but I have to admit that I've only ever had two men and Tim's the second. Give it a try before you condemn it."

I fondled her breasts and stroked her belly whilst this was going on then reached down to rub her wet, swollen clitoris. She certainly liked the attention her body was receiving and happily lay back as Brenda repositioned herself between her thighs and set about teaching Doreen just what delights could be had from another woman.

I wanted some of this so I moved to get behind Brenda then knelt and slid my cock into her and slowly fucked her as she finger fucked Doreen.

After a while Brenda allowed me to get at Doreen. I told her that I had had a vasectomy many years ago so if she was even remotely able to become pregnant she needn't worry. I instructed her to kneel on the sofa bed and began fondling her big beautiful round backside. She was positioned in such a way that her head was resting on the covers, but as she was kneeling; her backside was high in the air so that I could mount her. It surprised me when my cock slid all the way in without any problem and I was overjoyed when she begged me to fuck her, hard.

Obviously I complied. I slammed my cock up into her soaking, clinging vagina. It was a glorious feeling having the walls of her vagina trying hard to suck my sperm from me and I wasn't about to rush things, I caressed her glorious buttocks and teased her puckered anal entrance then Brenda came with some lubrication and helped me for a few minutes. Eventually I eased my finger into her rectal canal then slowly, very slowly, worked my way into her.

Although Doreen whimpered a little she was certainly not averse to the treatment her body was receiving. Brenda whispered that she thought I should use something larger than my finger, she meant the dildo which she held in readiness so was a little surprised when I pulled out from Doreen's dripping, vagina. She caught on fast, brought a condom and rolled it down my solid cock and placed the head against Doreen's anus and I gently eased it into her. Doreen was full of surprises, and cock! Her anus gradually opened to allow my cock full access, it was a tight fit, but soon I had half my length in her. Holding her breasts tightly I slowly fucked her anus; she grunted and panted and felt for her clitoris and began rubbing it until she squealed in ecstasy and climaxed.

I released my grip on her breasts and allowed her to lie on her back on the sofa bed for a little while just stroking her soaking sex and telling us how wonderful that had been. She said that she hoped that there would be opportunities to repeat the event. We were told that before her husband had been taken ill they'd had a fantastic sex life, but that had been over three years ago and she had missed it desperately.

We put the sofa bed back into sofa mode then had a couple of drinks, Doreen and Brenda taking it in turns to suck or masturbate me. I spent time fondling Doreen's tits, stroking her belly then down to her hairy vulva so it wasn't long before she had her thighs wide open again. I stood on the couch and offered my cock to her mouth which she sucked, and at the same time rubbed her fingers around my anus. The back of the sofa bed was speedily readjusted to bed mode and Doreen found herself once again on her back. Her feet were now high in the air and Brenda's 10inch vibrating dildo entered her oiled anus. Doreen gasped then reached down to hold it in place as I dropped to my knees, replaced my cock in her mouth and joyfully fucked it whilst Brenda sucked her labia and clitoris, she then pleasured her own anus with the dildo as my cock slid in and out of her mouth.

We took another rest with a couple of drinks and lots of fondling. Doreen gave Brenda a lot of attention and asked if she can eat her sex, obviously Brenda's ministrations had gained another fan, of course she can, so upstairs to Brenda's comfy bed, Brenda lay down on her back and Doreen got into the 69 position and they start to drive each other wild. Doreen moaning and slurping on Brenda's smooth labial lips and saying how fantastically erotic that is.

I stroked myself to another hard erection and entered Doreen as Brenda adjusted her position to allow me the space I needed whilst keeping her tongue on Doreen's clitoris. Doreen grunted and thrust herself backwards to get as much of me inside her as she could. Once everyone was comfortably positioned we concentrated on enjoying ourselves until, eventually: we climaxed, subsided into a sweaty heap, and fell asleep.

Morning arrived all too soon We showered, breakfasted and dressed, telephoned local garage (10 miles away) to have the car towed for inspection. We phoned Doreen's insurance company, and as she talked to her insurers I stood behind her fondling her buttocks then reaching round to fondle her breasts, I felt her nipples stiffen, so I lowered my hands down to her pubic area, she's lost! She ended the conversation as quickly as she decently could; went to the couch removing her dress as she did so, stretched herself out, and asks me to fuck her again, and told us that she wants us to use her until she can't take any more. We do!

At one point I was sitting on a chair with Doreen straddling me. My cock was buried deep inside her vagina when I saw Brenda putting on her latest toy. This was a 10inch dildo attached to strapping so that she could take a male role. She got behind Doreen and gently pressed her forward thus giving me chance to hold two lovely soft, bouncing, breasts against my face, and to enable Brenda to access her anus . With one finger she was applying lubrication to Doreen's anus and with the other hand she was guiding the head of her dildo to the puckered ring, Quickly she prised Doreen's buttocks apart and then eased her groin forward and inserted at least half of her protrusion into Doreen who immediately tensed, uttered a long, low moan which grew louder as she quickened the speed with which she rode my cock.

Doreen was panting and moaning and thrusting herself rapidly down my shaft and each time she got all of me in her, Brenda rammed her strap-on dildo up into her rectum. I was in heaven; my rigid cock was being massaged inside a vaginal sheath whilst I was being fucked by a sex starved dynamo.

Doreen did very well. She managed to ride me for at least 30 minutes before she climaxed, which was fine by me as I was pumping what little semen I had left into her love tube at the same time. Her vaginal muscles are incredibly strong, I'm pleased to say!

Much later we took Doreen to her house. We have exchanged telephone numbers and, arranged to come and collect her for a rerun in a couple of days' time. She says that she is more than willing, but wants Brenda to depilate her.

It did occur to me that it didn't matter where you were in the country, there was always an opportunity to pleasure a granny.

Carol's Holiday Part 1 (Lust, Arousal, First Time, Lesbian)

September 2013

I heard the car door slam and went to see who was there. A vision of pure beauty stood at the fence and all manner of lustful, erotic thoughts chased themselves around my head, but I managed a civilised greeting;

"Hello, I'm Tim. I think you must be Carol, your mom has spent days telling me how gorgeous you are, but she never came close to the actuality. She also told me to behave myself so I'll try, but it will be hard. Brenda has gone for swim as she doesn't expect you until this evening."

"Hi Tim, mom said you had a silver tongue, but thank you for the compliment."

"Oh come on, are going to tell me that you don't know the effect you must have on anything that breaths?"

Carol was around 5' 10". Very shapely figure, bottom half wearing jeans so could only see that her legs were long. Top half was a T-shirt trying desperately to cover a pair of exquisite breasts and succeeding in merely emphasising the fact that she had them.

"I do, but I'm not used to people I've just met admitting that I'm having an effect."

"I'm not shy, if I think something is worth saying and is unlikely to upset anyone then I'll say it, come in and I'll make you something to eat."

Brenda arrived shortly afterwards and after all the kissing and cuddling of greetings, immediately asked Carol if I'd been behaving myself, on being told that I had been a perfect gentleman Brenda told her to remember the occasion because it was unlikely to happen again. They left soon after that and I didn't see them for two days, I could certainly guess why but thinking about that merely made me sweat so I tried not to.

Brenda and Carol arrived in Brenda's car which I thought was strange until she told me that Doreen had rung her saying that she was feeling strange and could Brenda come to see her as she didn't like to be alone when she felt 'funny'. She thought that Carol and I would be able to amuse each other until she returned. Then off she sped.

Carol sat down and giggled, which was a lovely sound.

"Do you think you could decipher that?"

"Has your mom told you anything about Doreen?"

"No, she's never mentioned her."

"Doreen is a lady we found after she crashed her car during a heavy rain storm, she wasn't injured, just scared. We brought her to your mom's place as she was soaked to the skin and really upset. We cheered her up, warmed her up looked after her needs and became almost instant friends. Now she wants Brenda to go to her house and be extremely friendly with her and Brenda is quite happy to oblige."

"Oh my mother is such a kind person, how friendly is extremely friendly?"

"Very, very, friendly."

"She's very friendly with both of you? That is friendly!"

"Yes, Doreen seems to like us both."

"I should also say that I believe there to be a sub-text in your mother's message along the lines of" while I'm away doing my good works, you two should get to know each other!"

"Well she has told me a great deal about you two getting it together and I'm not so ecstatic about events."

"Assuming Brenda has told you all, why are you upset?"

"I'm not really upset it's just that I know my mom hadn't had a man since dad died, I know you know we're lovers, but has she told you about our little group?"

"Yes, I almost salivate at the thought."

"We have been a group for 19 years, just mom, me, Pauline, and her mom Jean, that way we don't hurt or get hurt. We look after each other's needs and the sex is always fantastic because we really do love each other. Now you've become a major player in her life and I worry about the effect you could have."

"I can see your mother hasn't told you quite everything about me so now I'm going to try and put your mind at rest. Has she told you about the erotic stories website?"

"Yes, but I haven't seen it."

"I think you should read the story I wrote, I have it on my laptop so read it before we go any further and while you're doing that I'll make us a drink."

She did as I suggested and then came the question I was expecting.

"Is this really true? You had all those women anytime you wanted and you had group sex with them?"

"Yes it is true, the opening tells you what I am, and I've not changed."

"Aren't you even a little bit ashamed of your behaviour?"

"Why should I be ashamed? All the people involved were there because they wanted to be. Granny seduced me and I'll be forever grateful, after that, each and every person made their own choices, and I haven't changed. I just want to have as much sex as I can get. I would never, ever, force any woman to do anything she did not want to do and I would never do anything to hurt a woman. Your mom knows this and she and I just use each other for our pleasure. It isn't love and it's more than just lust, but believe me it is fantastic. I'm not going to take your mom away from you, I am certainly not going to try and persuade you that following your mom's example might give you a very pleasant surprise."

"That is just as well, I'm a virgin. I'm 35, I've seen a man's cock but I've never touched one, mom says that she thinks you'd be the ideal man to take my cherry, but I don't feel happy about losing it just because it might be good."

"I know, and I know why. I'm not like that. Obviously what you and Pauline saw would affect you, but why allow what happened to spoil your life? Anyway, it's your choice. Would you care for more coffee?"

"Yes please, what is the name of the website?"

"I told her and explained how to navigate through the site then left her to it."

When I came back into the room Carol was standing by the table. She took our drinks and placed them on the table and asked me to sit down on the chair she'd been using, her face was pink, and she was sweating and looked very nervous.

"Don't say anything please, just do as I ask. Take your trousers and pants off then sit down."

"Ermm."

"Do it."

"OK."

I did as she asked and also removed my shirt, oh boy was going to enjoy, this I hoped.

Carol knelt before me and stared at my cock which even as she watched grew harder and longer until it was fully erect. Gingerly she put out a hand and touched my penis, and when it didn't bite her she put her hand around it and then looked up at me and said:

"This is solid, and I couldn't get that in my mouth never mind in my vagina."

"It wouldn't go in anywhere if it wasn't stiff so moving on to the next part of that sentence, you've read the story, you know your mother has no trouble with my penis, why do think you are any different to anyone else?"

As I was speaking she had begun to slowly slide her hand up and down my now aching shaft, so I abandoned my attempt to get her to rationalize her feelings and instead concentrated on not coming in her face. She squeezed my cock a little harder and asked me if that hurt me, I said no so she kept that pressure and began masturbating me until she achieved her goal and I pushed her away from the firing line as a stream of semen spurted into the air and slopped over the carpet where, moments before, she had been.

"Well that was a sight to brighten a girls day, said Brenda from the doorway, Can I take it that you two are having fun?"

"I was, but I think Carol is still unconvinced."

"Mom have you been taking all that up both tunnels?"

"Oh yes my love and boy I would miss it if I had to stop, I did tell you he is really well hung and a so gentle with it. He really is a wonderful lover. You wouldn't believe the stamina he's got. I just know your going to have a wonderful time with him, and me!"

"There is no way I'm letting that monstrosity inside me, I'll masturbate him, I may try and fellate him, but I will not fuck him, I think I'll keep my hymen intact thank you."

"Ah well, we have 10 days to sort that out."

To be continued in Part 6

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