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.