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Taking sister-in-law's anal cherry (part 1 of 2)

"A chance situation leads to an unforgettable night with my sister-in-law"

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My 50 year old sister in law’s naked slender body was draped across mine. Her head resting on my chest, her leg across mine. I could feel my cum dripping from her pussy onto my thigh. She seemed to be almost purring as we rested. The cat that really did get the cream. After a few minutes of post-coital bliss, we were startled by her phone ringing. ‘oh shit, that was Donna’ (her wife), ‘I’d better call her back, give her an update’. ‘you might not want to update her on everything!’ I said. ‘no, of course not!’ she said and she planted another kiss on my chest. ‘I’ll make myself scarce’ I told her. I got dressed, tidied the hotel room a little and went out in search of alcohol.

How had we got here? My sister-in-law is a lovely, but shy and nervous woman. For as long as I’d known her she was in a relationship with a woman called Donna. It always seemed a little incongruous to me, and I could see that Donna was the dominant partner in the marriage. Fiona is my wife’s younger sister. I’d always fancied her but never really got close to her but that began to change a year or so ago when I helped her elderly parents out in a few emergency health situations. She seemed to appreciate that, and ‘becoming quite the hero’ was how she described me at the time. This day had been another cris de coeur as her and Donna’s adopted son (Tom) had injured himself playing sport at university some 150 miles from home. Donna was working away and had taken their car, so I answered the call to help. Thankfully Tom was OK but was being kept in hospital overnight for observation, so I helped Fiona find a nearby hotel room and got her settled in. ‘Settling her in’ somehow turned into sex. As I drove to a local supermarket it occurred to me that the journey up and the hour or so in the hotel is probably the only time we’ve been alone together for any length of time, ever.

I got back to the hotel armed with a chilled bottle of champers and gently knocked on the door. ‘How was Donna? I brought a bottle of something’ I said. ‘She's fine, driving over tomorrow. You staying here tonight then?’ she asked. ‘Only if I’m invited’ I said. ‘Well, I’d appreciate the company’ she said. ‘Just company?’ I asked. She just smiled and walked through to the bathroom. Then my phone rang – my wife! I stepped into the corridor to take it. All was fine. I gave her the update about Tom, told her I was helping Fiona settle in and would drive home later that evening, Donna was planning to drive up tomorrow. Luckily for me, my wife was on a walking holiday with mates in Spain – the perfect situation. I knocked on the hotel room door to be greeted by Fiona in a gown. ‘Just hopping in the bath’ she said, ‘come and talk to me’. I grabbed the bottle and two glasses, stripped off and joined her.

After a quick chat about Tom, Donna and my wife, the conversation turned to the situation we now found ourselves. Thankfully, I didn’t detect remorse on her part – here we were in the bath together, her leaning back onto me, drinking champagne and enjoying the moment. I gently caressed her and she willingly let me stroke her pussy. ‘So, when did last have a cock in here?’ I asked. ‘that’s a bit personal isn’t it? Maybe I could ask you when you last shagged someone other than my sister’ she replied. ‘Maybe you should – about fifteen years would be the answer’ ‘really?’ she asked, ‘how come?’ ‘It happened with a colleague. Induced by stress I think. Just one of those things.’ I was lying of course, in truth I’d been a serial shagger, but I’m sure she didn’t need to hear that. Nor was it credible that I’d never strayed, so admitting to one affair seemed the best response. ‘OK,’ she said, ‘I guess we’re all entitled to the odd indiscretion. Thirty years is the answer to your question’. ‘Thirty years? Have you missed it? Being with a man I mean’. ‘I didn’t think so’ she said ‘I’ve been very happy with my relationship with Donna. It took me by surprise at the time as I’d only had boyfriends before her, and sex with them was average to say the least. I guess they were inexperienced.’ ‘Did you enjoy our encounter?’ I probed. ‘Yes, very much so. Couldn’t you tell?’ she asked. ‘Well, yes, but I didn’t want to presume.’ I replied tactfully. ‘Did you enjoy it? She asked. ‘Very much so,’ I said, ‘it was very lovely. You’re very lovely’ was my response. She turned around a little and kissed me.

‘I’d forgotten how intense penetrative sex is, and oh my god, how hot a man’s cum is. I wasn’t ready for that!’ She said, making me laugh. ‘I should have asked you before, but you have had the snip haven’t you?’ ‘Yes,’ I said, ‘you don’t need to worry about that. I could cum in you all night and not make you pregnant. In fact I might just do that.’ ‘All night?’ She asked, ‘I like the sound of that’. ‘Where would you like me to cum next time?’ I ventured. ‘Anywhere’ she answered. ‘Anywhere?’ I asked. ‘Everywhere. Anywhere and everywhere. Surprise me!’

I let the thought settle. I wondered whether her idea of ‘anywhere’ matched mine. With a whole night ahead of us, I thought I’d take the opportunity to find out. But more on that next time.

Published 
Written by Jack T

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