Women I’ve slept with, Pt 8: The best sex I’ve ever had

I have a theory: the best sex you will ever have is the sex you really shouldn’t have. Illicit afairs inherantly have trust at their core, as at least one party has the opportunity to betray and one to be betrayed. If not both parties. And I think with that trust comes the ability to open ourselves to our desires and it empowers us to scream for more more more!

I am not proud of the fact that I have fucked three women I really shouldn’t have, and I shouldn’t have fucked them as all of us were supposed to be fucking someone else at the time. I had awesome sex with all three of them, and the sex I had with Fiona was without doubt the best I’ve ever had. And almost certainly ever will.

Dirty sex is good. And sometimes, the dirtier it is, the better. On the scale of dirty fucks, Fiona was filthy. No, I do her a disservice: she was the most gloriously dirty, fantastically wanton, beautifully insatiable nymphomaniac I have ever knowingly met. She was a primly suited slut and I’m pleased to say she brought out the slut in me. For a couple of years, I was in pussy-juice soaked heaven!

We worked together and got on well, but initially I thought of her as nothing more than a confident, with whom I could share grumbles about managers and a little innocent flirting. When we finally got round to going for an after work drink, as we lived a long way apart, we agreed we would find somewhere near my flat and she would stay over. I never really thought through the implications of who would sleep where and it was certainly not my intention to try to get into her knickers. With hindsight, it’s quite possible Fiona planned to jump my bones all along, but if that were the case, I was blissfully unaware of it.

Fiona was about 8yrs older than me – I was in my late 20s and she was in her mid 30s. Or that’s what she told me and it didn’t occur to me to doubt her. Things she later said made me think she was possibly older still, maybe 12yrs or more. But the adage that older women are great lays is not without foundation.

If I’m honest, although we got on really well as people and colleagues, the keystone for our affair was undoubtably our mutually insatiable desire to fuck. And we fucked a lot. We also sucked a lot. And licked a lot. And fingered. And buggered. And groped. And fondled. And sweated. And we came a lot. And then we got caught and her husband put an end to our dirty little fuck-fest.

I’d like to tell you about all the sex we had. Because it was fucking great! But frankly, there is so much that I remember vividly, and could easily relate here, I doubt there is enough space on WordPress to do our fucking justice. So I’m afraid my best option is just to give you some the Episode titles:

The One Where we went for a drink for the first time, and I have to idea why I thought telling her she wiggled her ass really well was a good idea but it lead to us diving down each other’s throats and groping each other even before we got home to fuck.

The One Where we were in a pub carpark, she leant back against her car, hoisted up her skirt, pulled her panties aside and I pumped her pussy with my fingers till she moaned and her juices dripped down my wrist.

The One Where we played Rummie, but rather than points, we imposed Strip or Confession forfeits, and I learned how her biggest turn on was with a lover that liked her to give him a golden shower, and that the biggest cock she’d had was the 10 inches of her first husband.

The One Where I’d donated her my collection of porn mags, and as we thumbed trough them together on her bed, she quizzed me on which were my favourite models, photosets, poses and confessional stories.

The One Where I shaved her pussy for the first time.

The One Where she shaved my balls.

The One Where I said to her as she sucked me off that I wanted to taste my cum in her mouth, and was then suprised when she gave me a snowball.

The One Where she gave me a blowjob whilst her daughter was in the next room.

The One Where I emptied my balls in her ass, and as she hadn’t cum, I strummed her clit till she orgasmed and as her body tensed, her clenching rectum squeezed out a dribble of my jizz.

The One Where she told me I licked pussy better than anyone else who’d gone down on her. (I had my tongue burried in her cunt at the time.)

The One Where I sprayed her tits with my cum and as we lay against each other, it covered us both, and it felt incredibly intimate and loving. (There were actually a lot of those, but one in particular springs to mind.)

The One Where I knelt to fuck her and held a mirror so she could watch my cock driving into her hole. (Again this was not unique.)

The One Where she rode my shaft with her ass and I buried two fingers in her cunt so I could feel my cock reaming her from inside.

The One Where we went through my flatmates extensive secret porn video collection and fucked doggy style as a scene of MMMF DP / spit roasting was played out on the TV.

The One Where she drove 100 miles for 2hrs of mid morning sex … and then went home.

The One Where I drove 100 miles for 2hrs of late night sex … and then went home.

The One Where 6 fingers in 1 pussy didn’t seem at all excessive.

The One Where we went to the cinema together and, all through the movie and the journey back to her house (and although we didn’t mention it days later) I knew she was thinking about fucking as I could smell her juiced up pussy … and it was great.

The One Where she introduced me to being rimmed.

The One Where she shoved a finger up my ass for the first time.

The One Where we fucked for so long, I was so tired we both fell asleep with my fingers in her cunt.

The One Where we sat down to to watch a video and had to stop it twice to fuck. (It wasn’t a sexy film.)

The One Where I drank wine from her pussy.

The One Where we fucked five times in a night and never really got any sleep.

The One Where Geri asked if I fancied Fiona, which I denied, and the same night I fucked Fiona in a cheap hotel.

The One Where I sent a no-holes barred how I want to fuck you email, which was discovered by her husband.

The One Where (after our affair had been discovered) I knew she wasn’t getting laid so I posted her a Rampant Rabbit with a faked covering letter of gratitude for customer loyalty from a fictitious mail-order sex toy shop and I later learned that she’d opened the anonymous brown paper packaging in front of a couple of female friends. (For the record, the anonymity was noble – so there was no risk her asexual husband would realise it was from the man he knew had been fucking his wife.) (And she guessed it was from me.)

The One Where we met in a pub a year or two after we’d been stopped from seeing each other and she told me all about the new affair she was having and how amazing the anal was, and how she’d had sex with a female collegue, and then she went to the toilet with my camera-phone to give me a photo of her newly tattooed mons, and I groped her through her jeans before we parted. (This was the last time I saw her.)

Despite the fact that Fiona and I got caught by her husband, and were to some degree suspected by Geri, I should add that neither of us were gettting what we needed at home. Fiona’s marriage was sexless – I got the impression that either her husband was incapable of having sex for some reason or, as Fiona wondered, that he might be gay. And by this stage, my relationship with Geri had started to come apart at the seams. I know Fiona had had affairs both before and after we stopped fucking, and I think she may have been fucking at least one sugar-daddy whislt she was fucking me. And that just covers the simple stuff in her life – eating disorders, a messy end to her previous marriage, a child that was psychologically manipulated by its father. use of prescription antidepresants … the list goes on. I’m sure her need for almost daily sex and all this were tied up together, but I was far too young, dumn and interested in filling her with cum to really take the interest in her as a person that she probably needed from someone. I probably wasn’t just filling her holes – by doing so I was probably filling an emotional hole too. Not that I didn’t care for her!

Paradoxically, Fiona described herself as monogamous. Her get out clause for fucking men other than her husband was that she also regarded herself as polyamorous and as such she made no demands on the fidelity of her bed mates. She and I both knew the rules and when she moved several hundred miles away, and our fucks became infrequent, she wanted to know all the sticky details of the sex I was having with Sarah and Tania. Indeed, at one point, I fucked all three of them within a month, they all knew it, were all ok with it, and all should have been fucking someone else.

I owe a great debt to Fiona for what she taught me. About sex. About sexuality. About me. About women. About what I like. About how to pleasure a woman. About experimenting with sex and a partner. And about trust. She taught me more about sex than any other woman has. And I owe her a great deal of thanks for the best sex I will ever have. I hope her life is a little more settled these days.

2 Responses to “Women I’ve slept with, Pt 8: The best sex I’ve ever had”

  1. sexuallifeofawife Says:

    Wow! Sounds like you had ALOT of fun…
    I kind of disagree with your theory – but then again maybe it does have some truth…
    The best sex I’ve ever had has def been with my husband – so no illicitness there – but then again the best times have always held feeling which for some would be classed as not normal – maybe feelings I ‘shouldn’t’ have been having…

    • Thanks. It was A LOT of fun. If I could have a fraction of that now I would be happy.
      I guess if you can avoid things like monotony, complacency and boredom in a long term relationship, then you’re probably right, and my theory falls apart. But divorce statistics suggest to me that that is not the norm.

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