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I'd have to say the most taboo, for want of a better word, sexual experience I've had happened when I was 29. It was part of a double header (quite literally) one summer weekend in 2010.

I use the word taboo because the first part of this double header involves a woman that was not only 26 years older than me, but we were also related. In a way.

To be clear, she was not a blood relative or anything. Nothing that took place was i****tuous or i*****l. But it was definitely irregular and I'm pretty sure that if anyone in my family had found out, it would not have gone down well! Unlike her...

Her name was Helen and she was 55. And I'm using the past tense because, sadly, Helen is no longer with us. How we were related is complicated and involves second marriages and separate connections to both of my parents. I'm not even sure exactly what relation she was because it was quite a unique and obscure situation, but the relationship was always a kind of auntie / nephew one - even though that isn't strictly accurate.

She liked the atmosphere and people in my local pub and used to come over every couple of months for a night out, and would often spend the night at my place. Nothing remotely intimate had ever happened before, and the thought of it had never crossed my mind. Why would it? She was my (not) auntie!

Then one night that all changed. We were back at my place after closing time, having a few nightcaps, and for the first time ever I also asked her if she wanted to join me in a smoke. I knew she was a bit of a hippy back in the 70's and would probably be up for it. Which she was. I suppose Helen was quite attractive and looked good for her age. She was quite fashionable, looked after herself, and had long blonde hair and decent looking figure, although she was probably a bit too thin if anything.

It must have been the combination of alcohol and weed that turned the conversation sexual, and she was quizzing me about why I didn't have a serious girlfriend and wasn't I fed up of 'playing the field'. "Doesn't a nice looking young man like you want to settle down" etc. etc. Then she got a bit more full on and starting asking me about how many women I'd been with and what sort of experiences I had had. I told her about a few of them, including the one almost 2 years before with Tracey over the road, who was 17 years older than me (see 'The Older Women Experience' story for further details!).

This one in particular seemed to pique her interest and she asked me if I had a thing for older women, and if a 17 year gap wasn't an issue for me, how much more of a gap would be too much? I now had the feeling this was going somewhere a bit weird, but that alcohol and weed combination was blocking any normal impulse to resist. And when she put her arm around me and pulled me in to kiss me, I didn't pull away.

I remember feeling really nervous, and actually saying out loud "Should we be doing this", to which she replied "Probably not, but it's not like we're properly related or anything is it?!". That kind of made me feel better. And when she ran her hand down my chest and started undoing my belt and jeans, I began feeling A LOT better.

Once my already hard cock was free she wasted no time in bending over and taking me in her mouth. I sat back and watched her head bobbing up and down as she licked and sucked expertly on my big purple helmet and took all of my dick in her mouth so that her face was pressed right up against my body. She carried on pleasuring me for around 10 minutes while her hands stroked my chest, and my thighs, and my balls.

Then she brought herself back up and while wanking me slowly, started kissing me again, as I took off her blouse, undid her trousers and pulled them off. Maybe naively, I was a bit apprehensive of what her 55 year old naked body would look like, but as mentioned earlier, she looked after herself and looked a lot better than I probably would have imagined.

Something was still holding me back just a little bit though. My first instinct with a naked women in front of me is more often than not to lead with my tongue and go for the pussy, but I didn't feel entirely comfortable with it so I just used my fingers to rub her wet cunt, caressing her clit and inserting first one, and then two fingers inside her, while all the time we carried on kissing, with me paying special attention to her neck, which she told me was really turning her on. And the wetness between her legs and all over my hand said she was telling the truth.

"Do you want to fuck me" she whispered after a while, and I nodded. Bringing my hand up from her pussy, my fingers were soaking wet and I could smell her scent on them as I put my hand on the side of her face. Realising I'd gone from her pussy to her face, and not knowing how she might feel about that, I quickly pulled my hand away and stuck two fingers in my mouth, sucking off her juices with a deliberate show of satisfaction!

"You dirty little bastard" she said with a laugh. "Now fuck me". So I did. Right there on the sofa, I laid her length-ways and shoved my cock straight in to her waiting pussy and fucked her hard and fast with no let up. She was crying out in pleasure as I pounded away and before too long I felt the tell tale sign of impending ejaculation, so I slowed down and pulled out. "Cum here" she said through ragged breaths, pointing to her mouth, so I shifted up her body so my cock was right in her face and she took me in her mouth again. Clearly I needn't have worried about my pussy stained fingers being on her face earlier because she had no problem taking my pussy stained cock straight in her mouth.

Within seconds I came hard, shooting my spunk straight in her mouth, where some went straight down her throat and the rest remained in there for a few seconds, some of it dribbling on her chin as I pulled my spent dick out and climbed off her.

It was quite an experience! It felt, and still feels, a bit wrong even though technically there was nothing wrong at all. Although for obvious reasons, not another living soul knows about what went on between us that night. We never talked about it, not the next day, or ever again. It was one night of intimate secrecy, never to be repeated.

I spent most of the next day, Sunday, back down the pub. Around 10pm, a woman I was friendly with asked me if I would walk her home, which I (and a few other guys) would do if a woman was by herself. I trotted back to the pub afterwards and there was another woman that I knew, and who had been in the pub for several hours, sitting on one of the benches out front. I didn't know her all that well but stopped to say hi as I was finishing my cigarette.

She'd clearly had quite a bit to drink and started being very flirty. I knew her name was Jo and she was quite a big, bubbly woman, a fair bit older than me (for a change!), but I'd never really even had a proper conversation with her, until now. Out of the blue, she said she'd finished with her man earlier that afternoon and was determined to get pissed and have fun. "Fair play to you" I said. And then she says "Is your dick clean?"

Fucking hell! Where did that come from?

I've said that all stories I post are true, so I will stick with the truth. I hadn't showered since the previous night with Helen. I'd got up and gone straight down the pub. So the honest answer there would probably have been, no, not exactly. But, I'm hardly going to say no it's not, so I said "Of course it is! Why?"

"Get it out and let me see it. I'm feeling really horny!".

I said "I'm not going to just whip out my dick right here where the whole pub can see, and on the main road!". So we walked around the corner in to the car park where it was a bit more private, and she sat down on another bench while I proceeded to pull my cock out through my flies in its "semi" state.

And she grabbed hold of it and wrapped her lips straight around it and started sucking me off! It didn't take too long for me to go from semi to full on hard, and Jo kept sucking like she meant business. I was relieved to note that she didn't seem to have picked up on any 55 year old pussy taste on my cock! It seemed to take quite a while with her sucking hard and fast, and wanking me off in between while taking a breather, but eventually, and without much of a warning, I shot my hot cum in to her mouth as her lips were wrapped tightly around my length.

Afterwards, she just got up, fetched a tissue from her bag, wiped her face a bit, and with barely another word just fucked off back in to the pub!

I found out a few days later that Jo was 45. So in the space of 24 hours that weekend I came in the mouths of two women with a combined age of 100. Happy days.

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Clare - The love trianglePart 2, the week afterHow my loving relationship turned into a love triangleI woke early the next day, well before my alarm went off. I still couldn’t believe my luck. I had a big smile on my face and why shouldn’t I? I got a fantastic blowjob of Clare last night but I couldn’t figure out what she meant when she said “I’ve wanted this for a very long time.” Did she really fancy me or was I just a notch on her bedpost? I’m a decent looking guy, even back then, at 35 I...

3 years ago
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Clare Continued

Clare:What a wonderful day it had been and I felt completely fulfilled and I felt like a young teenager who had just had her first date. I waved to Peter as he drove off and then returned home to get down to the more mundane part of my life to prepare a meal for my hubby.Before I did I sent of an email to Peter to let him know I was going to Cornwall and would be staying a night or two and possibly be out of email contact. My husband arrived home from work and we had a meal together and he...

3 years ago
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Clare Continued 2

Please read the story Clare first or this will make no sense to you.Peter:I emailed Clare to explain that maybe we should cool off a little, neither of us wanted to get caught and we might get careless if we carried on as we were. We had done so much over the last few days that if we carried on there would be no surprises left! Our fantasy world stopped for a short time. A couple of days later I was on my way back from a customer in Swindon, as I was nearing Salisbury my wife called and asked...

4 years ago
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Caregiver in Love continuing the Caregiver Saga

Caregiver in Love (the continuing saga of the Caregiver) Part 1 Caregiver Saga Part II: Caregiver in Love. Shawn's older sister continues to dominate him. Shawn rejects and resists her efforts to feminize him. Meanwhile, he is thrilled by a budding romance with his beautiful cooking teacher, Jacqueline. He only hopes that his smooth legs, and his complete lack of any experience with sports or other manly attributes do not turn her off. He hopes that she can forget his shameful...

3 years ago
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My Minotaur Part IX

Without Valsivale, our journey had grown much more dire. We were forced to march long hours during the day, and barely slept at night. As we traveled North the weather grew cold and my flesh felt somehow too thin to protect me any longer. But Oluth was a beast possessed! He set a fast stride and at night fucked one or more of us to sleep with a newfound vigor. It was a good thing we moved quickly, I hated to admit. There were days when we could hear the great mob in pursuit of us, the legion...

2 years ago
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My Minotaur Part IX

Without Valsivale, our journey had grown much more dire. We were forced to march long hours during the day, and barely slept at night. As we traveled North the weather grew cold and my flesh felt somehow too thin to protect me any longer. But Oluth was a beast possessed! He set a fast stride and at night fucked one or more of us to sleep with a newfound vigor. It was a good thing we moved quickly, I hated to admit. There were days when we could hear the great mob in pursuit of us, the legion...

Supernatural
2 years ago
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The Bank Notary

I got out of my Jeep and headed inside. The marine layer was still thick this morning, clinging onto that June Gloom mantra. I stepped inside and was greeted by a young gentleman. I let him know I needed the services of a notary. "No problem sir, our notary is with another customer at the moment. You can just have a seat here. Can I get you a bottle of water?" He asked. I accepted and took a seat in one of the awkwardly uncomfortable chairs. He soon returned with the water as I...

4 years ago
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Tupperware Meeting

Tupperware Meeting By Gini Lane Shortly after our little tryst on the hallway floor, I found myself again in the kitchen making tea for Bobby. As I stood at the counter, waiting for the kettle to boil, it was difficult not to look at him. He made such a pretty picture, really very cute. I had to resist the urge to cast more than the most discrete of glances. Each time I dared, Bobby appeared the same; so much so that the pretty image remains with me: Bobby at the table in his lovely...

3 years ago
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Jared

It was a regular day for the morbidly obese Jared, all except for the fact that he had received a knock at the door. Jared normally received his disability checks from the vocational department at this time of the month, but he always had to make the arduous journey across the parking lot to get his mail. Maybe they stopped being so lazy, Jared thought. He opened the door looking around only to find a box of chocolates at his feet. Without a second thought the fat man shut the door...

1 year ago
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Jared and Andrea

Jared and Andrea ? by: Ashley Shine Jared loved these times. He was alone in the house, free to explore his stepsister's room. The parents were down in Florida vacationing for three weeks, and Andrea was away at college. Fortunately for Jared, Andrea kept almost a full wardrobe back home. Jared had always been attracted to frilly clothes. He loved the taboo nature of dressing up in girl's clothing it was exhilarating. Access to Andrea's clothes was a big bonus when his mom...

3 years ago
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Clare

Clare is married to Scott, my best friend. We’ve known each other since we were teenagers. My story takes place in the late seventies. It was March, you know that time of year when spring isn’t here yet; you’re sick of winter and just getting over the February blahs. My wife had left the previous December and taken our son with her. Something about needing to find herself, and oh “Merry Christmas dear!” Bah Humbug! Scott and Clare knew I was feeling low so they organized a party at my place....

Cheating
4 years ago
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Jared gets Caught

Oh what a day from hell. Or should I say week. I have been sick for almost 2 weeks and finally broke down and went to the doctor, only to get news I wasn’t expecting. Then I came back to my boss getting on my ass for a file she couldn’t find, and too top it off I haven’t hardly seen Jared my boyfriend all week. So I was looking forward to seeing Jared after work, and I so need to tell him our news. Even though I knew he wouldn’t be happy about the news. I had tried a couple times that day to...

Group Sex
4 years ago
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The Hypnotist

I had known this amazing hypnotist for years. In fact, I am 46 and have moved 46 times. Every town I moved to, he was the Hypnotist when there was going to be that kind of show at one of the clubs or the bars. We had become pretty good friends and I say he was amazing because I have a Bachelor Degree of Science in Mental Health and while training,Hypnotism was a much debated topic in almost every class and I had learned quite a bit of it. I will call this guy Newton. Newton to my...

2 years ago
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Jared And The Reluctant Groupie Part 3

Kareena was scrambling inside before he’d finished speaking. She made a grab for the phone, but he held it away from her and let it drop, bouncing across the seat. “Give it here!” she yelled, but he grappled her by the waist as she grabbed for it, the six-pack of beers tumbling to the cab’s floor.She ended up lying across him with her breasts bouncing as she struggled for the cell. His cock—she realised with a shock to her heart—was thickening again under her belly.“Think you can get it?”...

Group Sex
2 years ago
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Jared and Jennifer Part 2

My mind was racing. Did that really happen? Did Jared really kiss me? Why would he do that? And why did I kiss him back so passionately? I wasn’t falling for this kid was I? I was. As I drove home I started to put things together in my head. When we had our first tutoring session, I was in a bad place. My life was falling apart and I didn’t even want to be a teacher anymore. Jared brought something out of me. I could tell he truly cared about me and was also glad I was helping him pass his...

4 years ago
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Jared and Jennifer Part 2

My mind was racing. Did that really happen? Did Jared really kiss me? Why would he do that? And why did I kiss him back so passionately? I wasn't falling for this kid was I? I was. As I drove home I started to put things together in my head. When we had our first tutoring session, I was in a bad place. My life was falling apart and I didn't even want to be a teacher anymore. Jared brought something out of me. I could tell he truly cared about me and was also glad I was helping him pass his...

Mature
3 years ago
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Clare

I shouldn’t have tested her. Or, maybe I should have. I’m not sure anymore. I’m not sure which emotions are mine. I’m in a happy relationship. I think. My name is Clare. Now… Anyway. Sorry, I realize how confusing this is. Let me attempt to make sense out of it. My name is John. Or, my name used to be John. My best friend is named Hunter. We did everything together. Now we do everything to each other. You see, Clare was dating Hunter. I didn’t know her last name, whether or not she had a...

3 years ago
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Clare

I shouldn't have tested her. Or, maybe I should have. I'm not sure anymore. I'm not sure which emotions are mine. I'm in a happy relationship. I think. My name is Clare. Now... Anyway. Sorry, I realize how confusing this is. Let me attempt to make sense out of it. My name is John. Or, my name used to be John. My best friend is named Hunter. We did everything together. Now we do everything to each other. You see, Clare was dating Hunter. I didn't know her last name, whether or not she had a...

4 years ago
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Clare

ClareLet me introduce you to Clare, I met Clare on xHamster and wrote her a short story just for her entertainment, to my surprise she wrote back with a continuation of that story. This has been going on for some time now and with Clare's full consent we would like to share this fascinating journey with you.Neither Clare nor I are professional writers as we are sure you will see, but if you can excuse the appalling grammar you may enjoy the concept of a story written by two people one male, one...

4 years ago
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Jared and Amanda Naked in SchoolPart 5 Thursday Daytime

Jared I woke up the next morning, threw on some clothes, and went downstairs, still rather delirious. "Hey, little brother." Tina greeted me. Mom and Dad were there, too. "Hiya, Jared," Mom said, "want some breakfast?" "Love some." I sat down and Mom started spooning out some bacon and eggs. "So, how are you today?" Dad asked me. "Just fine." "I'll just bet," Tina butted in. "So, how long are you going to tease me about this?" I asked her. "As long as I can get away...

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