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Having anal sex with Alan for the first time was an amazing experience, especially since I'd not even masturbated properly until a few weeks earlier! I was quite proud of myself for going so far and having the confidence to try new things and not be embarrassed about it. Alan said that he hadn't done that for a long time and I was really good at being fucked, bearing in mind it was my first time. He told me the fact that I had ejaculated while he was fucking me was a sign that I really enjoyed it, especially as I hadn't actually needed to touch my own penis in order to come.

I cleaned myself up before I left for home but on the way back I could feel Alan's semen running into my underpants, he seemed to have had a really powerful orgasm and had cried out quite loudly when he ejaculated in me and I was sure he had released lots of his seed in me. Sure enough, that night while I was wanking myself to sleep and thinking about Alan's cock slipping in and out of my bottom I put my fingers between my legs and felt the slippery evidence of Alan's orgasm which was soon mixing with my own spunk as I spurted all over my legs and the bed sheets!

I didn't see Alan again for a couple of weeks but then when we did meet round at his house we spent a whole afternoon in his back room masturbating together and having anal sex again. Alan showed me how to make sure I was all clean and open for sex and gave me something which looked like an over sized bottle stopper, it was rounded and narrow and the front and became wider before going narrow again and with a wide base. Alan said this was a plug that if I greased it I could slide it inside and it would help relax me and sex wouldn't be painful. We tried this a few times and I became quite good at slipping it in my bum, I knew that it got painful and then subsided once I was past the wide part. Once inside it felt really nice and made my erections even harder and a couple to times Alan watched me lie back on the sofa with my knees up, showing him the plug in my bottom as I masturbated for him.

One weekend late that summer, Alan asked if I wanted to go out on a day trip to a local museum and I asked my pa***ts and they were completely fine with it. We were going out for the afternoon and planned to get back in the early evening. I went round to Alan's house and before we went he asked if I fancied meeting one of his friends who was a bit lonely and would enjoy seeing me. I thought it sounded ok and although I was still a bit worried about people finding out about what Alan and I did together he reassured me that his friend was very discreet and hardly ever met anyone else. Alan asked if I would clean up and insert the plug as Brian, his friend, might be interested in having anal sex with me if that was alright. I should probably have said no but for some reason the thought made me feel both nervous and excited at the same time. Alan said that if it was ok with me, he would like it if they both did it at the same time and I nodded saying it was ok, although I wasn't sure that kind of thing ever happened. It had never been talked about before.

We drove out in Alan's old Ford Granada with was a big car and I sat in the back seat. After driving for about half an hour we came to a car park near a local beauty spot and Alan said he'd arranged to meet Brian here. Sure enough, a couple of minutes after we pulled up man came over the passenger side and got in, Alan introduced Brian who was about Alan's age, early 60's, a bit thinner and seemed shy but friendly. We then drove for a bit further then pulled off down a country lane and then down a narrow track where there was a parking place that was surrounded by some trees and was pretty secluded. We talked for short while, Alan explaining that we would not be disturbed here and that if it was ok he would be first as I was used to having sex with him. I preferred that and Brian was fine with that arrangement as well. Alan asked me to take off all my clothes and kneel on the back seat facing the rear window, which I did while he got out of the car. It was really warm day and the car windows were closed, it was a bit stuffy so actually being naked was quite comfortable for me. Alan got into the back of the car and started taking off his shoes, trousers and underpants and asked me to open my legs. He then gently pulled out the plug which I had inserted into by bum before leaving Alan's house. It felt a bit sore but not at all painful. Alan got a jar of vaseline out of his trouser pocket and smeared some of it on my pouting anus and then rubbed more on his penis which was already quite hard. There was plenty of room in the back of his car and Alan kneeled on the seat between my legs as I rested my arms on the back of the seat. I could feel him probing for me with his cock in his hand and he found the right place quickly and, after pressing a little he said "Just relax Simon, this will be nice" and I felt him slip inside me in one long go. I gasped but it didn't feel painful at all. Alan rested there for a minute, just pushing gently to make sure he was all the way in, then he withdrew a little and slid back in fully. Alan kept this gentle stroking up for a few minutes and I could see Brian in the reflection in the rear window. He had turned round and was looking at Alan fucking me and I was certain that he had started to masturbate while watching us.

After about ten minutes Alan's thrusts became more firm and his hips slapped hard against my bottom as he began to fuck me harder and he moved his hands from my hips to the back seat so he could lean the whole of his body weight against me as he fucked me hard. My cock was very stiff and I began wanking myself as I was being pushed against the seat by Alan's thrusts and I moaned out loud with pleasure every time he slapped into me. Alan must have been fucking me for about 20 minutes in total, maybe half an hour, when he said in a breathy voice "You've been a good boy Simon, I'm going to fill you with my spunk." and I moaned "Yes please Alan, come inside me" and a few thrusts later Alan cried out and pushed hard into me and I felt the spasm of his cock then the feeling of warmth as his sperm was released. Alan waited for a few minutes, getting his breath back. The car was foggy and sweaty and smelled strongly of bodies and spunk. Pulling out of me, I felt his fluid dribbling down my legs and I shuffled about, stretching my legs as I'd been in the same position for a while. I was very close to orgasm but had not come yet so I was still incredibly aroused and ready for Brian to have his turn.

Alan got out of the car holding his clothes in his hands and the open door let in some welcome air. Brian got out and came round to the open door and changed places with Alan. Sitting next to me, he didn't take his trousers off, just pulled them down to his ankles along with his underpants. He asked if I was ready and I nodded and turned round again, his cock was thiner and a bit longer than Alan's and the end was less bulbous but bright red instead of the purple colour that I was used to with the head of Alan's cock. Brian got in position kneeling behind me and using his hand to guide himself he found my arsehole straight away and with a very gentle push he slid easily inside me all the way in and I felt his hips push against my bum. With the vaseline and Alan's spunk my hole was open and incredibly slippery, easily accepting of another cock, "Oh god, that feels nice Simon" he said and after a few gentle thrusts began fucking me hard and fast. "Steady on Brian, you'll be done soon!" laughed Alan but Brian kept hammering my arsehole without slowing down and gasped "I can't help it Alan, it feels lovely" and in a couple of minutes Brian moaned that he was going to come soon. By this time I was so excited that I was also working myself quickly to orgasm with my hand and said that I was coming too. I think this must have triggered Brian because he cried out and gave me another couple of hard thrusts then stopped as he ejaculated inside me. After his orgasm subsided he withdrew and I felt loads of semen running out of me and down my legs, the feeling of the cum dribbling down my skin, warm and sticky made me orgasm and I spunked all over the back of the car seat. Brian was sitting next to me, breathing hard, his cock was shiny with vaseline and his bell end looked bright red with a thin stream of spunk dribbling out of it. All three of us were smiling and Brian and Alan thanked me and told me what a good boy I'd been.

We got dressed and I dried myself with a hand towel Alan had put on the back seat. We drove back to the car park where we met Brian and said goodbye, after he thanked us both again. Alan and I stopped to get some sandwiches, crisps and a fizzy drink from the kiosk at the car park which we ate in the car before driving back to his house. I washed myself in the bathroom when we got back and Alan watched me as I lay on the sofa, naked, with my legs open and slowly masturbated as I remembered being fucked by him and Brian earlier that day.

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The Keyholder Pt 4

Ben pushed his face against the locker’s metal grille, desperate to get one last look at Amy as she strode away. She had such a sexy walk with her swinging hips hugged by tight white cotton trousers. He could see the slight bulge of the keys in the back pocket as her body pulled the fabric one way then the other. He watched her dark hair flow behind her, desperately hoping for one last turn of the head and one last smile. Yes, there it was.All too soon though, Amy had disappeared from sight and...

BDSM
3 years ago
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The Fat Older Men Change1

The life is so terribly for Nun, the 29 year old Thai girl who’s living in Great Britain. Last year she worked in a Thai restaurant and met the young black stud who said he loved her with a true heart and promised many things to her. Everything looked so perfect at that time. Now she’s jobless, and that’s not the worst part, when she got back to her BF’s flat from job seeking she found him fucking another girl. He tried to explain but it was too late. She decided to pack her bags and...

2 years ago
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Darnell and Carmela

Chapter One (of two) My name is Darnell Lamm, that's Lamm with two M's. I'm a clerk at Bradley's Super Market downtown, or I was at the time this story begins. This is my incredible story. **** "Okay, Sam, I'm on my way, and I'm walking not driving, so don't worry about me, okay. Sheesh! You're worse than my mother, rest her soul," I said, as I exited the Iron Skillet. Sam watched me go out and smiled; he could smile; he had my back, read looked out for me almost every night. The Skillet...

Love Stories
2 years ago
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Darnell and Carmela

My name is Darnell Lamm, that's Lamm with two M's. I'm a clerk at Bradley's Super Market downtown, or I was at the time this story begins. This is my incredible story. "Okay, Sam, I'm on my way, and I'm walking not driving, so don't worry about me, okay. Sheesh! You're worse than my mother, rest her soul," I said, as I exited the Iron Skillet. Sam watched me go out and smiled; he could smile; he had my back, read looked out for me almost every night. The Skillet was my favorite...

2 years ago
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Fun Time With Menaka

Hello everyone, this is Varun, age 24 athletic body 5’11”. This is my first story in ISS.  I work in an MNC in Bangalore. I met Menaka (age 26, 5’6″, Fig: 32, 28, 32) in this company. Menaka was a senior in my company and she was supposed to my initial trainer. This story took place 2 years Everything was normal during the first week of my training. She had a variety of dressing sense. The first day we wore jeans and tee and the next day she wore salwar and the third day she wore one-piece...

2 years ago
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Clementine in HellChapter 2

"I still can't believe we saw that savage whipping last night. That poor girl - she looked so lovely and delicate. But I suppose she submitted willingly, as James said. Didn't she?" Stella sounded doubtful! Clemmy nodded. "I guess so, Stella. There are certainly twisted people around who love pain. I've even fantasised about it myself before now, though I hope these particular dreams never come true! We just can't get inside their minds to see things their way. But I would rather like...

2 years ago
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Clementine in HellChapter 3

"Nice breakfast, girls?" asked an excited Viola. The four were seated around her dining table on the morning of the Great Fight which was to decide who of two strong and lustful women was to be her mistress - the young and fair Clementine or the mature Rashumba, with her muscular body and excitingly cruel ways. She was clearly looking forward to the coming contest, no matter who won, unlike Estella, who was dreading it, and Clementine, who was beginning to have butterflies in her stomach....

2 years ago
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Clementine in HellChapter 18

"Why have we driven out here, darling" Viola asked Rashumba innocently. Inside her heart was working overtime. Could this be it? She had been here for a week now and Rashumba and James had treated her magnificently. Had she not known of his betrayal of Clementine, Viola would have been happy to meet James again. He had great appeal and was still great to look at. She understood very well how Clemmy had succumbed to his charms. But James was busy today and Viola and Rashumba were alone, and...

4 years ago
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My first experience of older men in panties and st

I'm wearing my new panties that I bought at Target. They're aqua which is a colour a tend towards mostly because Target doesn't have a lot of red panties in Large. My stockings are from Dollarama because I didn't have the nerve to search through other stores. Any way, they're hold-up stockings in a flesh tone and I like them. The self check-out at Target and other stores is a revelation. I could purchase what I wanted without passing through the watchful eyes of some s*******n-year old girl...

4 years ago
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The United Kingdom of Zoo A fake BBC documentary seriess2e10 Margot 60 retired Police inspector Cardiff

Series 2, Episode 10: Margot Heydon, OBE We’re going from our youngest ever subject, to our oldest... We’re in the kitchen of a neat and tidy little cottage in South Wales. Infront of us, a very respectable looking older lady – shoulder length blonde hair turning to grey, with a few wrinkles around her gleaming blue eyes. She’s in good shape – apparently healthy and not unattractive. Her neatly put together outfit, white blouse tucked into black skirt, suggests that she’s quite trim....

2 years ago
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The United Kingdom of Zoo A fake BBC documentary seriesS10E14 Kia Waheed 21 from Cardiff

We fade in on our regular old set… That dank mattress, lumpy and stained, splitting in places… The iron bedframe, rusty springs looking like they would snap rather than bend. The lighting is harsh, casting shadows from the bed to the concrete floor below. Sleazy is an understatement. Then we hear the familiar clicking of hard heels on the concrete as this week’s guest walks onto the set. There’s a clicking of heels as this week’s guest walks onto the set and we cut to watch her...

1 year ago
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Anne Signs Anullment Papers And Celebrates With Carol

James left me with a smile on my face and wealthy.. I'm Anne and after 2 years of marriage I am going to the attorney's office after work to sign Anullment papers. When I got to the attorney's office I was told James had signed the paper work and checks. His signatures were notarized and he was gone. I looked at the bank statements and investments. Everything was in order. He left me with all of the money in our bank accounts and investments. There is about quarter of a million dollars in all...

Female
3 years ago
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Summer with Carly

The summer after I turned 18 may never be topped. Now in my last year of college, I still find myself daydreaming of that small brown-haired girl who could always make me smile. Before that summer, I felt a little like a battery-operated toy that had yet to be flipped to the "ON' position. Every girl I'll ever be with has Carly to thank for how they are treated and loved by me.Throughout high school, I'd had a few girlfriends but none that went very far. I was a decent looking guy and always...

3 years ago
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Firemens Carnival

"Mark! I'm over here!" I waved my hands wildly, trying to get my husband's attention. It was useless though; he couldn't hear me over the noise of the crowd and he hadn't noticed our booth when he walked past. "Hey, lady. Can we get some pies here or not?" A sweaty, overweight man stood beside three sweaty, underweight kids. Each child clutched a dollar bill in their dirty little fists. I took a last look at Mark's back, disappearing behind the Ferris Wheel. Oh, well, he'd keep...

2 years ago
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Carlotta

Carlotta By Brian Houlihan Copyright @2000 by Brian Houlihan All Rights Reserved "So..what color today?" "What do you mean?" I was sitting across from my future mother-in-law at the apartment I shared with my girlfriend. "Your panties. What color are you wearing today?" I felt like a bomb had just hit my stomach. She was smiling and giggling. Loving the shock of knowing my secret. "Diane told me. You wear panties. That's interesting to me. ...

4 years ago
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Clementine in HellChapter 4

"We've been friends for nearly two years now and in all that time I never knew you could fight, darling! At least not like that - you are something else. Where the hell did you learn? I mean that was just tremendous the way you took all that punishment and still came through it all to win. You must be made of something more than ordinary flesh and blood to have kept going against that woman. Because she was tough too. I should have thought you'd both have been unfit to go on after a couple...

4 years ago
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Clementine in HellChapter 7

"Well, they certainly taught you one hell of a painful lesson" said Olga, the ugly tough who had just whipped her. This seasoned prisoner was sweating from every pore after her exertions, despite the night chill. She was standing over her recent victim and examining her handiwork. The new girl was certainly in a bad way. Clemmy had been warmed up herself, but she was still shivering feverishly from the after effects of the beating, which had brought her out into a cold sweat. "You must...

4 years ago
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Clementine in HellChapter 14

"You still miss her don't you, Viola? Even now, after all this time?" Estella and Jules had flown back from the States, where they had been living since just after their marriage. The couple had brought their two sweet little children with them to start a new life in Estella's native town. Little Estella was getting on for three and already as lovely as her mother. Little Jules was six months old and adorable, smiling delightedly whenever he caught anyone's eye. Estella was clearly...

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