Cliff and Gillian Ch. 01

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This story is a two chapter spin-off from my series East End Lovers, a mother — son love story. This story is about the son, Cliff, and a relationship he had with an older colleague in the early 1980’s. It’s narrated by Cliff, and set in North London. The second chapter will be narrated chiefly by Gillian. Any constructive comments on possible content are welcomed.

All characters are over 18 years, and all characters and places are fictitious.


In the autumn of 1982 I was 25 years old and had been working for 6 months as an economist in a government office which was overseeing regional regeneration in Britain. It was actually more interesting than perhaps it sounds and I got to travel around the country quite a bit. I was living by myself in Camden Town, though had a regular girlfriend; as anyone who’s read the East End Lovers series will know, I was also having a long term relationship with my mother, though at this time we only got together occasionally.

I was working in central London, in an office with around 30 staff, a mixture of economists and admin people. The senior admin officer was named Gillian, and in those days before personal computers we had a lot of face to face contact and got to know each other quite well. Gillian was around 58; she was a large woman, not so much fat as well built or what we then called stout, with very large pendulous breasts, and shapely legs. She wore glasses and had a round, attractive face — she must have been very pretty in her younger days — and short silvery white hair. Overall I suppose I sort of fancied her, though without wanting to do anything about it, though I did from time to time wonder what it would be like to have those breasts either side of my cock!

I had heard that she had been widowed a year or so before I joined the office. Partly because of this, I didn’t go out of my way to flirt with her. However, after I’d returned from my summer holiday with a nice tan, she made a remark about it suiting me and I began to detect a few looks and smiles coming in my direction. As always I was flattered though again as always I never assumed she actually fancied me.

On Fridays it was customary for the younger members of staff — and some older ones — to go for a drink after work, and Gillian sometimes came along. I noticed she was starting to come more regularly and I put it down to getting over the loss of her husband. I usually left the pub around 7 to meet my girlfriend Jenny, though she also had a job involving travel and around once a month would be away.

On one particular Friday evening in October, when Jenny was not around, I stayed on and found myself chatting to Gillian for much of the evening. It got to 7 pm and most of the others had gone home; there were only four of us left, and one of the other lingerers suggested we go to the India Club along the Strand for a meal, and I was up for it so said yes. I was half expecting Gillian to leave at that point, but she wanted to come along too, so we piled into a taxi for the short ride to the restaurant.

After the meal, the other two dashed off to catch trains from Waterloo, and I was left on the street with Gillian. It was then that she dropped her first surprise—

“Cliff, I was wondering if you might like to come back for a coffee… or maybe a glass of wine? It’s quite early and we don’t have work tomorrow? How about it?”

Of course she might have just meant she wanted to make me a coffee…. But I thought this might well be an offer I couldn’t refuse. I suddenly found that actually I did fancy her quite a bit. Gillian lived in Barnet, a few stops further up the Tube line from Camden Town so getting home would be easy, if I needed to. So of course I agreed and we headed for the Tube.

Back at her house we agreed that wine might be nicer than coffee. I had been drinking beer and was desperate for a pee, so headed to her bathroom — and while there I gave my todger a good wash just in case…

Gillian was sitting on the sofa with two glasses of wine ready and her very shapely legs demurely together. She had put some Ella Fitzgerald on the stereo and there was just one lamp on.

“Well Cliff, here’s to the future, whatever that might hold…”

We chinked our wine glasses, and then she leaned towards me and our lips came together, closed at first and then of course we started tonguing each other and my hand went to her wonderful large tits and I could feel the flesh straining at the thin materials of her bra and blouse. I groaned out loud at the simple pleasure of it all.

“Hmmm, yes, I thought you might fancy me Cliff…. I’ve seen you staring at my tits and I wondered if you might fancy older ladies. I must tell you that I’m a bit rusty on the physical side of things though…”.

She kissed me again and our hands started to roam around each other’s bodies — mine onto her tits and hers on my chest and then down to my erection. She pushed me back on the sofa and I watched her as she güvenilir canlı bahis siteleri undid my belt, unzipped my fly and managed to extract my hard cock so it was sticking straight up, glistening with pre-cum. I was totally taken aback by the speed this had happened, and mesmerised. Gillian stared down at me. She unbuttoned her blouse, removed it and sat there in her plain white bra, nipples already firm and pushing through the cotton.

“Goodness Cliff you are a nice hard boy… I do like a good hard set of cock and balls…and you’re big too… that’s just as well ‘cos, well to be totally honest, I do have quite a large fanny too and I’m afraid small cocks never used to make enough impression… I hope this doesn’t all sound too shocking to you? … No, I thought not…. If you want I can tell you more about me a bit later but first I’d like to break the ice…”.

With that she leant towards me and sucked my cock into her mouth. She still had her specs on and even though this had been done to me plenty of times before, I’d never been with anyone as mature as Gillian — she seemed like everyone’s favourite granny. She was as confident and forward as anyone I’ve ever met before or since, and I suspected there might also be something of the Dom about her. She left off sucking me and looked directly into my eyes.

“Right Cliff, I want to freshen up before we go any further. I think you should too… I’ll go and get myself ready for the shower, and if you want to pop into the bathroom now and have a shower then that would be nice…”

We both got up and I went straight to the bathroom, quickly undressed and showered, and just as I finished Gillian walked in wearing a dressing gown. She shooshed me out telling me to get into bed.

Her bedroom was painted a dark red with gold and red curtains. There a large dressing mirror on a moveable stand in one corner. However I didn’t have much time to admire the décor before Gillian came back wearing her gown.

“Now Cliff, it’s our first time together and I hope not our last. I do want to be straight and open with you from the start. You’re a young man and I expect you’ve got lots of spunk in you and expect lots of sex, and that’s very nice for both of us. I have to tell you I’ve not had vaginal sex for a while and I don’t want to end up all sore and not being able to sit down for a week. So what I suggest to keep us both happy is that you can take me once in my vagina, and other than that I’ll suck you, maybe let you cum off between by breasts, and I also like it in my bum… that doesn’t shock you does it, I expect you’ve done it with your girlfriend — though not too rough up there… so you get to cum lots but I don’t get too sore in any one place.. I think that’s a fair offer…”

A fair offer? Goodness, I thought I was one for straight-talking but Gill took the biscuit. She smiled – she knew I wasn’t going to say no. She went to the bedside cabinet drawer and got out a new tube of KY jelly, placing it meaningfully on the top. With that she undid her gown and let it fall to the floor. For the first time I saw her massive pendulous breasts, which at the same time managed to be full and round from the front, while hanging like large oval fruits down towards her waist. As I’ve said she was a big woman but while her stomach was well rounded there were no folds of excess flesh and though her thighs were thick they were also smooth. Her cunt was covered in a mass of hair, a mixture of brown and grey, and while she’d trimmed it around the top of her thighs, she had let it grow in a wide triangle up her stomach. The slit of her cunt was a darker streak in the midst of this mass of pubic hair.

I sat up on the bed and pulled her hips towards me, slipping my fingers between her thighs and feeling the already wet entrance to her sex. I parted her pubic hair and started to run my tongue around her cunt lips, tasting the tangy mix of soap and juices. I thought it would be best if she didn’t have the last word on everything so I asked her to get on the bed on her hands and knees.

“Right Gill, can I have a little look at your arse… yes that’s a good place to start, I think a bit of kissing’s in order don’t you… (at this Gillian shivers with anticipation and groans) hmmm yes you like a bit of arse kissing don’t you…”

I probed her arse with my tongue and licked around the very sensitive area between her arse and her cunt — this was a favourite with my mother and I’d learnt from her the best pressure to use and how to combine using fingers and tongue. Gillian’s cunt was sopping by now, her lips spread — I could see what she had meant by being large. I pushed in 4 fingers and I still felt she could take more.

By this stage I was ready to burst I was so aroused, so I reached for the KY, stuck the nozzle end in her bum and squeezed a really large dollop up her, using my finger to lubricate her rear passage ready for my cock. Before I went in though I asked her for a final suck, and she obligingly turned güvenilir illegal bahis siteleri around, took my penis in her hand and gave a good deep suck for a few seconds before turning back away from me.

I had chosen to start with her bum because I knew of course that the first fuck would be the quickest and I didn’t want to make either of us too sore by spending too long in her tightest passage. I’m really a pussy man myself and have always seen bums as the icing on the cake, if you like. Gillian had large smooth buttocks and I knew I wouldn’t have to penetrate her anus too deeply to get the feeling and friction along my cock that I craved.

How right I was. I put some more KY on my penis, spread her buttocks wide and carefully eased the helmet of my cock into her anus, sliding in easily though not deeply. I pushed her buttocks back together so it looked as if the full length of my shaft was penetrating her.

“There Gillian, I’m inside for the first time, goodness what a tight bum you’ve got, I won’t last too long this time, here let me rub your cunt too, ohhhh yes goodness you’re fucking wet and swollen, I can feel your clit nice and hard…”

“Yes please Cliff, lover, fuck, yes rub me while you’re in my arse, you feel so big, haven’t had anyone up my bum for ages, forgotten almost what it feels like, yes, rub hard, come on make me cum, if you like I can fuck you in the bum too, I’ve got a nice big strap-on for boys like you, or maybe you’d like me to bring in another girl and you can fuck me and she can use a strap-on in the same hole….”

As you can imagine I wasn’t really prepared for this side of Gillian — I really had thought of her as a big-bosomed granny rather than a very randy and probably pretty kinky woman — and the words got me ever more aroused and I told her I was about to spurt and I rubbed her really hard and as my cum started to shoot into her bum I told her I was cumming, rubbed her even harder and felt her shiver and spasm too…

“Ohhhh Cliff, yes I’m cumming too, you lovely fucker, oh goodness that’s good, keep rubbing for a second, yes that’s enough, leave off now, ohhhh what a nice cum…”

As soon as I’d shot my full load, I pulled out of Gillian’s bum and we collapsed next to each other on the bed. She took my head in her hands and gave me a long deep kiss. She then put her specs back on, explaining she wanted she see me properly — I found this strangely sexy, having this white haired woman lying next to me wearing only glasses. I decided that when it came to cumming in her mouth, she would definitely be wearing them!

It was still only around 10 pm, and we were both excited with each other and wanted more before we went to sleep. As I recovered I asked her where she’d got all her sexual experience.

“Well, until I was about 50 I was just an ordinary married lady — I loved my husband Dave, and though sex had been going downhill for ages, I didn’t think to do anything about it. We would do it once or twice a month, though he was clearly struggling to keep it up at times — he was a fair bit older than me, either that or he didn’t fancy me much any more – and other than that I used to masturbate occasionally.

“It was my husband who suggested we might like to get other people involved to make it better. We talked about it a lot and I wasn’t really keen. Eventually I agreed to try another couple, and he answered a few of those ads you get in these contact magazines. We got some Polaroids of us with naked but with masks on and sent these with the replies.

“It wasn’t exactly a roaring success. I think we met 3 couples but though we learnt quite a bit about what was going on, we never really clicked with anyone, and never had any sex. Then Dave put our own ad in one of the mags with a photo, and worded it saying we were open to suggestions, but especially welcomed younger couples interested in role play and also single Sub ladies. He said I was bi-curious — which was a cheek really as I hadn’t agreed to that. We got about a dozen replies.

“The first ones we met was a couple in their twenties who had said they wanted to do role play pretending they were our son and daughter. They were nice looking, and after a first meeting in a pub we arranged a second meeting at our house. Well, I think they were as new to this as we were, but I’m quite a good actor, and I did the role play thing right from the start. To cut a long story short, I ended up straddling my “son” on the living room floor while Dave fucked the brains out of his “daughter” right by our side. We used condoms of course. We saw them from time to time for about a year, and did all sorts of stuff — I got screwed by Dave and the other guy at the same time, both in my fanny, Dave had sex with the woman while she sucked her husband off…

By this time I was of course getting aroused again, and Gillian, who had been holding my limp cock, was the first to know. As soon as she felt me start to harden, she started to massage my cock, and güvenilir bahis şirketleri I started on her again, so we were both quickly ready.

“Cliff I really think it’s time for you to make love to my pussy… it’s probably going to work better if I put a pillow under my bum — I know I’m big and this helps me to feel you — is that OK? Of course it is — and the other thing is that it helps me to cum if you talk to me — you can be as dirty as you like, I love hearing all your filthy thoughts… and one final thing, you can be a bit rough too, don’t hurt me of course but you can hold me down and things like that…”

I asked her to keep her specs on, arranged her across the bed with a pillow under her hips, and legs wide apart, and knelt in front of her showing her my hard cock….

“There that’s what you do to me Gill, this is all down to you, flaunting your tits at me in the office, crossing your legs so I just get a glimpse of your knickers, now I’ve fucked your bum, and now you’re going to have to take it right up your hairy old cunt, look I’m slipping it in now…. Ohhhh fucking bollocks, Gill, you’ve got the wettest cunt in London, I think you need two cocks in you to fill you right up, yes look at me pushing it in and pulling it out — shall I take it right out for a moment — look at my cock, how wet and red you’ve made it — now it’s going back in again, yes now a nice regular fuck up your cunt, yes in and out, I bet there’ve been lots of cocks in there before me, you must have made loads of men spunk up you, I bet you’ve had them queuing up taking their turn…”

Whilst when I had sex with my mother we would always talk dirty to some extent, I never felt before like I did with Gillian — that I really could say anything I liked and she would get turned on by it and never think I was over the top. Her cunt was big and after a few minutes I pushed her legs together and put my legs on the outside so she held me tightly. She was groaning with my thrusts and saying fuck oh fuck me; while it only seemed like a few minutes, we must have fucked for over half an hour, when I got to the point when I knew I had to cum, so I pushed her legs open and asked her to wrap her legs around me. At that moment I thought I was in Heaven — we kissed deeply, I seemed to fill her deep cunt completely and as I started to spurt in her I said –

“Oh Gill, yes you’re making me spurt my sticky spunk right inside you, I’ll push down on your clit, can you feel me on your clit, there, hard on your clit, come on Gill, I’m cumming, you cum too, yes it’s spurting out now, again and again…”

Gillian screamed softly and I felt her shudder and her skin seemed to glow hot for a moment, and she told me she had cum too.


I had no intentions of going home and Gillian clearly wanted me to stay. After we had had intercourse, we must have fallen asleep without much further conversation, as I don’t remember anything until the next morning.

I can’t say I felt great when I woke up on that Saturday morning — I had had one glass too many. Gillian seemed to be still asleep so I went to bathroom and had a shower and cleaned my teeth. As I was going back to the bedroom Gillian was coming out and she told me to go back to bed and she would bring up some breakfast.

I dozed off again as the next thing I knew, Gillian was sitting beside me in her dressing gown with a plate of scrambled eggs, toast and tea. She had had a shower, and looked refreshed and older — older I guess because she had no make-up on. I found this incredibly sexy, and she let her gown fall off when she got back into bed.

“Let me tell you a bit more about what happened to our sex life after Dave placed that advert. As well as that young couple who pretended to be our son and daughter, we got replies from quite a few single men and 3 or 4 young women. Dave was very keen to meet the girls — the randy old sod. We met a couple of these but frankly I don’t think they fancied Dave. Anyway, when we agreed to meet a third woman, I went along at first by myself, and we got on famously — I think she saw me as a mother figure. She had a boyfriend but was just as keen on girls and had some experience. We agreed she should visit and that we would play around with each other and Dave could watch but do nothing more unless invited.

“Stella was a lovely girl — about 28, quite plump but very pretty and intelligent. I wasn’t sure what to do really, but when she arrived we had a couple of drinks and a kiss and cuddle on the couch and then went to bed. She had brought along some vibrators — I’d seen these before but never had one — and she used one on my pussy and I did the same. She also had a strap-on dildo which she said she’d never used. We were both quite tipsy and quite aroused by then — though in some ways I was still glad Dave was around.

“Anyway Stella managed to fix this dildo on herself and she stood by the side of the bed while I lay down with my legs hanging over the side either side of her. She used a vibrator on my pussy and then eased the dildo up me and started to fuck me. It was amazing… I came again and again. Afterwards I pulled her down on the bed and went down on her like nobodies’ business – I wanted to repay the compliment and made sure she came properly too.

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