Cliff and Gillian Ch. 02

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Tem 24, 2022 // By:analsex // No Comment

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This is the second and final chapter in a story which is a spin-off from the mother–son series “East End Lovers”. It’s mostly narrated by Gillian, though some is told by Gillian’s neighbour Pam (it’s clearly indicated where this happens). For those who have not read chapter one, Cliff is 25, and Gillian is a 58 years old colleague.


When Cliff told me he fancied watching me having sex with someone else, he made it sound like he was half-joking, giving me an out if I didn’t want to pursue it. He also made it clear he had participated in swapping at least one girlfriend before, so he wasn’t new to the idea and could handle it.

I didn’t do anything about it for a few weeks anyway – I wanted to get to know Cliff better and we soon developed a fantastic sex life together. He had a lot to give and I was able to take it – he had me in the kitchen over the sink, on my knees in the bath, on the sofa and on the floor (he liked me to straddle him so he could play with my big breasts) and of course again and again in bed. My cunny had a sort of permanent tingle to it, even though we only actually met up once a week or so.

I know I looked a bit like everyone’s favourite granny with my white hair and specs, and sensible dresses, but as Cliff described in chapter one, I had been round the block a few times and I considered myself quite experienced sexually. Even so, my love life with Cliff continued to take my breath away. He encouraged me to wear very conservative outer clothes, while wearing sexy underwear, and he’d look at me when passing in the office knowing that under my sensible grey woollen dress I was wearing a black lacy bra and matching knickers which – if we were meeting that evening – he’d have off me as soon as we got in the door.

We tried to meet each week, either mid-week or if his girlfriend was away, on the Friday evening. Sometimes Cliff would go back to his flat first and follow on, but mostly he came up with me after work. I remember one particularly passionate night we had early in January of 1983. We were bundled up in winter coats and cold and wet after we’d walked to my house from the Tube.

As soon as we were inside, Cliff made it clear he couldn’t wait to have me. We took off our coats and Cliff told me he’d had a permanent erection all day just thinking about me. He kissed me and I felt his hardness against my stomach – I always loved to feel how turned on I made him, and feeling his penis in this way always quickly brought on my own swelling and lubrication.

“Come on Cliff, let’s go into the living room and have a cuddle (“Cuddle” being my euphemism for sex)… shall I keep my boots on for you, I don’t think we’ve ever done it like that have we?…”

I was wearing the usual winter footwear of black knee-high boots. I took Cliff’s hand and led him through to the living room. I always liked to see him naked so as we kissed and touched each other up, I got off his shoes, jacket and shirt and then his trousers, leaving his long cock sticking out of the top of his pants. I couldn’t help smiling, and he quickly pushed his pants off.

Being winter I was wearing tights. I was aroused and wet from our kissing and touching and I just wanted to feel Cliff inside me. I solved the problem of how to get him there by kneeling in front of the sofa, pulling my dress up to my waist and pushing my tights and knickers down as far as I could – I still of course had my boots on. I know we all have our likes and dislikes, but I don’t know of any man who wouldn’t have been electrified by looking at me in this position – clothed above the waist, then soft smooth bare flesh from my waist to my mid-thighs, my legs just apart enough to see my swollen cunny with its mass of pubic hair surrounding the long wet gash of my sex entrance, then my white knickers taken down as far as they would go on top of my tights and then my black leather boots. If I’d been a man I would have ravished me there and then!

Which fortunately was exactly what Cliff did. “Oh goodness, Gill I just can’t believe what I’m seeing… I’ve just got to fuck you, there let me get at you… ohhhh that feels soooo good, you’re totally fantastic to fuck, here let me get at those big soft tits of yours…”

He unzipped the back of my dress as he pushed in and out, and unclipped my bra, bringing his hands around to my front and massaging my globes and squeezing my nipples until I gasped and told him not to be so rough.

I don’t know when Cliff had last had sex – I assumed he had seen his girlfriend a night or two before – but I hadn’t had sex since having Cliff the previous week, so I was more than ready to climax. I did a fair bit of DIY but I’ve always found that cumming with a man inside made it all more intense and last longer – so as Cliff pushed in and out, I rubbed my clit and carefully paced it so if possible I would cum at the same time as Cliff shot his load.

Cliff was usually very good at pacing himself but I guess on this occasion he just couldn’t help himself bonus veren siteler – maybe it was the boots – and he ejaculated his spunk in me quickly, before I had got to a point where I could cum.

“Cliff, just stay in me while I get myself off, love …. Oh you were a good lover, I do love having you up me, you always feel so big and hot, there, I’m getting there, I’m getting there, just a few more rubs, yes, oh yes, oh yesssssss…”

It was a lovely long cum even through Cliff was rapidly softening in my cunny. He slipped out and I quickly pulled up my knickers and tights to hold in his outpouring as I already enough of his cum stains around the house and didn’t want any on my best work dress.

It was wonderful then just to chat as I made a meal for us, and to get a bit tipsy with a couple of glasses of wine. I was very fond of him, and he told me that he was very, very fond of me (though not enough to give up his girlfriend, I thought.)

We had a meal and as usual went to bed soon afterwards. Before we actually got to bed, I made him wash me in the bath – I forbade him actually to get in – well I thought he shouldn’t have everything his own way, but asked him to strip off and wash me as I wallowed in the hot, bubbly water. I made sure he was very thorough around my lower parts!

It was glorious again in bed. Cliff went down on me, gently sucking me and gradually building up and up to a much harder suck where he took my clit right into his mouth, rolling it around and finger fucking me until I climaxed. Then he moved up on top of me, forcing my legs wide apart, and slid his manhood inside in one smooth deep thrust, filling me and making me gasp as I felt the tip touching my womb.

“Gill, oh Gill, I fancy you so much, every time I look at you in the office I just want to undress and fuck you, I really really do like you, of Gill, you’re making me cum, it’s all starting to come out into you, oh Gill I love you…..”

That was all so lovely and sexy and even a bit romantic. Of course I knew he didn’t really love me, and that we just sexually besotted with each other, but I told him I loved him too as his semen spurted into me, and it was a sort of unwritten rule from then on that we’d say I love you at the peak of our lovemaking – but not at other times.


As it happened Cliff’s request to watch me with someone else did raise the possibility of doing something I’d been wanting to do for a while – which was to go to bed with one of my neighbours.

There was some history here. The neighbour in question was Alan, who was married to Pam. I’d known them for a good ten years and when my husband Dave was alive we’d been very friendly. When we’d first met, Alan was around 55 and Pam nearing 60. However, they looked younger, partly I’m sure because they were then both keen cyclists and were very fit and usually sun or wind burnt. To cut a very long story short, we’d introduced them to the Sunniskies Adult Club after they’d complained about lack of excitement in their lives (note – this Club is described in chapter 1 – it was basically a club for couples to go and “swing”).

The first time we took them there, I wasn’t sure if Alan and Pam had in mind to do a swap with myself and Dave, but in the changing room Pam told me she didn’t fancy Dave. It was a bit of a shame as I did fancy Alan. Like us the first time we went, Alan and Pam were very nervous at first, but they were a good looking couple – Alan was lean and tall, with a dark complexion and Pam was also tall, with well-cut short grey hair, small but still quite firm breasts, very shapely legs and a round, very well proportioned bum – and other couples soon took to them.

The first evening we went along with them, I think Alan and Pam must have fucked 3 couples – Alan seemed to be able to recover very quickly, and when erect he looked very well-endowed and handsome and someone very few of the woman at the club would refuse. I certainly wouldn’t have if I had had the chance – but I didn’t.

Since my husband’s death, I’d seen less of them, but Pam sometimes dropped in for a chat. I’d been seeing Cliff for a couple of months when one evening Pam called by. We chatted away and she asked me about the young man she’d seen me with several times. I was open with her and told her about Cliff and how good he was in bed. Her eyes lit up – she clearly found him attractive and it didn’t take us too long to get around to talking about getting together for what we called a “party”. She told me Alan did fancy me and would be only too keen to do a swap, as long as she could have Cliff.

When I next saw Cliff I asked him if he would be interested – I think he was a bit wary because of Pam’s age (she was approaching 70 by this time) but in the end I talked him into it and he agreed.

The “party” was set for a Thursday evening. I made Cliff a meal, and we both showered – of course I put on the most seductive clothes I possessed, including stockings and a low cut blouse bedava bahis which showed off my lacy bra and gave me a really huge deep cleavage.

When Alan and Pam arrived, and Cliff saw Pam for the first time, I could almost see the sparks fly – he was really taken with her, and I saw at once that they were going to hit it off. Pam looked gorgeous – she had on a tight dark blue skirt with black stockings, and a tight light blue silk blouse which showed off her small tits and nipples very well, giving her a cleavage I wouldn’t have thought possible. She had had her hair cut, and while it was grey, it showed off her pretty features to good effect. Alan had brought wine and what he called an ice-breaker, “Dare U Play?”, an adult board game he claimed never to have played before.

Well, Alan and I sat on one sofa, and Cliff and Pam opposite on the other, and we poured the wine, chatted about not very much, and Alan set up the game. It was one of those games where you throw dice, move along spaces according to what you got, and when you get to a space marked “Take a truth card” or “Take a dare card”, that’s what you did. If you didn’t want to tell the truth or perform the dare, you had to remove an item of clothing. It wasn’t exactly subtle, but it did get things started.

I don’t recall all the details of the game but a couple of items stick in my mind. I had to tell about the last time I had sex, so described meeting Cliff the previous week, when he’d had me over the sink as soon as he’d arrived, both of us fully clothed, and how later I’d taken him up my bum in bed. Pam’s eyes widened when I described the anal act. Pam later had a dare of measuring the erect penises of all men who were playing (the game included a tape measure!); Alan and Cliff were only too happy to get out their dicks, Pam helped them get hard and did a very thorough job of measuring them (I think they were both around 71/2 inches).

By this time we were all well tipsy and Alan and I and Cliff and Pam started to lose interest in the game and instead started to snog and pet. Alan stood up and stripped off his remaining clothes, pulled me up and took off my blouse and skirt, leaving me in my bra, knickers, suspenders and stockings. Cliff and Pam stopped snogging and watched us. Alan was semi-erect, and I kneeled in front of him and sucked him hard. I was wet and ready to be entered, and was very happy when Alan turned me round, slapped my bum and unclipped my bra and pulled down my knickers. He felt my fanny and knew I was ready; I lay down on the sofa, legs open, and within a few seconds Alan was inside me.



When Gillian asked me to write down what went on between me and Cliff at the party, I was unsure if I could do it – I’ve never written anything about sex, and although I’ve always enjoyed sex I thought I was too respectable to write about the things we all did. In particular, I didn’t think I could use some of the words I thing Gill uses. However, having read what Gill wrote, I thought I’d have a go using the sort of words she uses – “fuck”, “cunt” and so on and I’ve found I’ve sort of enjoyed it and that it’s quite liberating. So here goes…

I’d been looking forward to the party a lot. This was partly because my sex life with Alan had gone downhill for some while – I just think we’d got bored with each other. He still fucked me once or twice a month, but I didn’t cum with him. We’d stopped going to Sunniskies after a couple of bad experiences with people who just wouldn’t take no for an answer, and then the Club had actually closed for a while. Instead I’d started to masturbate a lot. Although I was approaching 70, I still had the old feelings about wanting sex, and I had bought a vibrator, which I used whenever I could get a moment to myself. I’d seen Cliff a few times arriving and leaving, and thought he was very good looking, and he was also tall with a good figure (I’m 5’8″ and didn’t like men being shorter than me). I suppose I’d started to fantasise about him a bit, and Gill’s suggestion made me think he might be just the man to get me into sex again.

I’d chosen my clothes carefully. I’d bought some new lingerie, and under my skirt and blouse had on a lovely white lacy bra and panty set with matching suspender belt holding up my stockings. I hoped I would get to go to bed with Cliff, and as my cunny doesn’t always get as wet as it used to I’d smeared on some KY jelly to get me started.

I knew I looked good for my age, but was still concerned Cliff would find me too old and wrinkled. I was nearly 70 after all, and although I was still fit and trim, my hair was grey and I had my fair share of lines around my face. However I realised from the start that he liked me a lot. Alan insisted on bringing along this daft adult game, though I suppose it did get us all going, especially when I got the card telling me to measure the men’s hard cocks. I was delighted that Cliff was as big as my husband!

I thought Gillian deneme bonus had overdone the tight clothes and cleavage thing, but Alan of course loved it and couldn’t wait to get stuck into her – literally. I’d been kissing Cliff and was enjoying feeling my cunny puff up and get wetter, but when Alan stripped Gill and she had sucked him, and then he’d at once started to fuck her on the couch I thought I’d prefer a bit of privacy, so stood up and took Cliff by the hand to Gill’s bedroom.

As soon as we were alone, Cliff told me how much he fancied and wanted me. He really was lovely in what he said about my looks and how aroused I made him feel – it’s very rare at my age to be so flattered, and I think he meant it too. He took all his clothes off there and then, leaving me still fully clothed; he did look gorgeous, a nice sleek body with little body hair, a good strong cock and well-filled balls, full of nice sticky spunk – I couldn’t help but imagine the semen spurting out from the tip of his cock into Gillian!. I sat on the bed and he knelt next to me. From what Gill had told me about their love-making I knew they did a lot of sucking and licking, so I carefully took hold of Cliff’s cock, drew back his foreskin and took the head into my mouth, gently squeezing his balls with my other hand.

“Oh Pam, oh yes that’s so good, don’t make me cum though, I want to save that for your cunt, oh you’re so sexy, I just love your body, I’ll suck and fuck you all night…”.

I wasn’t really used to the very explicit language – some men I’d been with at the Club used the words, but not in the way Cliff did – but I found it turned me on.

“Come on Pam, I need to see what you’ve got, let me take off that skirt, yes, oh what nice knickers, now let me undo your blouse… wow you look incredible, just let me have a look at you…”

Cliff stepped back and stood admiring me – of course I admired him too, his hard cock now fully upright, moisture oozing from the tip. I turned around a couple of times, as I knew I still had a nice tight bum. I’d trimmed my pubic hair until it was just a small dark triangle pointing to where my cunny lay.

“Pam, could you just take off your bra please… yes oh you’ve got lovely tits… now please turn around and take down your knickers and bend forward with your legs open..”

I wasn’t sure exactly what Cliff had in mind, but turned my back to him, slowly lowered my white panties and kicked them away, then opened my legs and touched my toes – not bad for a 70 year old! I knew he could see my fanny and bumhole too, and wondered exactly what he was going to do.

The next thing I knew I was feeling Cliff’s mouth and tongue on my bottom and cunny – he was kneeling behind me, had pushed the cheeks of my bum open and was licking my anus and fanny. Goodness he was good… I had never had my bottom licked and tongued before and the whole experience was very exciting, if a bit nerve wracking too. Cliff then pulled me upright and pushed me face up onto the bed, and then went down on my cunt again, very hard, sticking a finger of one hand in my anus and two fingers from the other into my fanny.

I would like to have cum, but I was too nervous and excited at the thought of being entered by this gorgeous young man. I pulled his face off my cunny and asked him to make love to me, and he looked up, smiled, and with what seemed like one single motion, moved his body onto top of mine and entered me with his lovely hard cock.

I can’t tell you how good that fuck was – it made me feel like I was a young bride again, except Cliff was much better at it than Alan had been on our honeymoon. He kept going for as long as I wanted, and rubbed my clit with one hand while massaging and finger fucking my bum with his other hand. We talked to each other as he pushed his cock in me and then slid back, and then pushed in again –

“Oh Cliff, what a good lover you are, no wonder Gill is all over you, I bet she can’t get enough… you like older ladies do you… I’m old enough to be your gran, does that get you going, does it get you hard and excited?… yes I thought it does… I expect you’d like Gill and I together in the same bed wouldn’t you…. That’s such a naughty thought, you having two old ladies to pleasure with your big cock, what would you do? I expect you’d bend us over and fuck us for five minutes each in turn… but we’d make sure you made us cum before we let you take us…”

“Yes Pam, you and Gill together, yes please, you’re much tighter than Gill you know, she’s got a really big fanny and even with my big cock sometimes she doesn’t feel me properly…but you’re much tighter, I’m sure you can feel this and this and this….”

By this point, Cliff had raised my legs so they were sticking in the air, meaning he could penetrate me even deeper, and I felt the tip of his cock pressing against my womb. He was rubbing my clit hard with his hand, and I was close to cumming but didn’t quite make it – Cliff just couldn’t hold out any longer and I felt his cock spasm inside me and felt his hot spunk pouring out deep in me. When he had finished cumming I asked him to pull out so I could finish myself off; he pulled out but stayed on top, taking his weight on his arms and legs, and he watched as I rubbed myself to a quick and very noisy climax.

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