Hi
I will start with an apology for the mistakes that may be in the story below, I am dyslexic, that is why there is such a gap between the stories, both writing and reading is very time consuming for me. But to practice both reading and writing is helping so much and I find that I and making progress.
So I hope you enjoy the read and please feel free to make comments, both negative and positive are greatly received.
It has been 4 days since my weekend with Ruth and tonight is the training session that her son attends so I wait for her arrival. These times are always a bit nerve racking. You really don't know what to expect, having done this before I have some experience in these matters. Now there are a few things that may happen, if she sends the husband with the child then you can be sure that you're not getting a repeat performance, if she attends and blanks you (ignores you) then she most likely didn't enjoy the experience and has written the nights activities off and won't be returning and will keep our relationship as purely professional. All these and other scenarios were going through my head when I saw Ruth and her son approaching.
Now as I explained earlier Ruth is definitely in the 'yummy mommy' category, some like to call them MILFS, either way she's around 5'8" curves, we know from experience that her breasts have been enhanced, she has a slim waist and a peachy bottom, her hair light brown shoulder length and she is beautifully manicured. She always looks her best and wears perfectly fitted skirts and dresses, very rarely trousers, and we also know that she has a liking for expensive lingerie, so in my mind as I watch her walk towards me I can just picture what she has on underneath and I feel a tingling in my loins.
She ushers her son off to the pitches for training with Steve, one of my young assistants, and continues walking in my direction.
"Hi Ruth," I say, wondering what sort of reaction I will receive.
"Hi, glad I caught you alone, we need to talk," she said as she got closer to me.
Well this could be a problem, "we need to talk" is usually not that good. So I brace myself and direct her to the small prefab where I have a desk surrounded by equipment. As we enter I turn and face her as I sit back on the edge of my desk.
"Ok, what's up" I ask, being slightly defensive and preparing for whatever she is about to drop on me.
She looks me right in the eyes and smiles, "Listen, I'm so sorry that I didn't text or call you before this evening things have been a bit crazy, Mark (her husband) got back and I've been too busy. The other night, those things that you did to me, oh my god, I love my husband and we have a good marriage, I just want to make that clear and I won't ever put that in danger, but if there's a way we could have another evening".
"Hold it" I interrupted her. "What you are saying is that you would like us to have another evening together, it must be discreet and no one can find out?"
"Yes please" she said and then continued, "I can't get it out of my head, I haven't been that turn-on for ages, I mean Mark and I have a good love life but for one reason or another we don't get time to do those things, either he's tired, I'm tired, he's away you know"
"Ok, ok, I agree, I am not the sort of person to go bragging about my exploits and I certainly wouldn't wish to create any discord with you and your husband." I say.
She smiles and goes to hug me, she must have been worried the past few days that I'd be spreading the word about what we'd been up to.
"Hold it" I say, holding my hand up before she comes to close. "Best to keep up appearances "
"Oh yes" she says, stopping and putting her hands in her pockets.
"So I'll leave the ball in your court, contact me when you are free and we'll try and get another evening together" I say to her, trying not to betray the excitement inside of me.
She looks down to the ground and says in a very sheepishly voice, "Mark is away this weekend and I could send my son on a sleepover, if you're free"
"Yes of course" I say
"I can't stay the night but we would have more time, what do you think?" she asks.
"Fine around 7.30 good for you" I enquired.
"Yes good" she confirms, showing a little smile and a wink as she leaves the Porto.
As the door closes I smile and can't believe my good fortune, here we have a good looking MILF asking me to fuck her anyway I like with no strings attached. My head is trying to work out what just happened, maybe it's a bit like when a married guy who really loves his wife and the mother of his children but pays a prostitute to do the dark desires that his wife won't do. Well that's enough of the bar-room psychology I thought to myself let's get on with making plans for Saturday evening, I have 4 days to dream up some scenarios that she would be happy to take part in. As I said in the first chapter my ex-wife and I have been into some light bondage, I was never into spanking or inflicting pain (except nipple-clamps which my ex found a turn-on and I thought they looked incredibly sexy) also I don't think Ruth is into pain either, but we may find out differently in the coming weeks.
So the next few days I spent digging out the box of toys that my wife and I used to use, there were restraints, ankle and wrist cuffs, nipple clamps the ones like small G clamps that screw as tight as you or her like with a small chain linking them, a butt plug that I never got to use as my ex was very protective over her asre, and of course the ball-gag. After a few minutes of remembering the times I had my ex secured over the small lounge table while I took my time fucking her mouth and pussy, sometimes I would cum in her mouth apply the ball-gag and leave her tied there with the taste of cum in her mouth and some dribbles on her face while I sat down and recovered sufficiently to fuck her both ends again. Those were the days.
Anyway I decided that Ruth needed spoiling, so tomorrow I would be off to the shop for discerning gentlemen (the sexshop) knowing that Ruth gets off on the whole Christian Grey role play I had to be a subtler with my approach, rather than shackle and fuck her, more of restrain and gently toying with her physical and mentally.
The next day I drove to the 'little house of pleasure" as it's known to purchase some. Playthings. Firstly, the cuffs, I got 4 fur lined buckle-up cuffs each with a "D" ring and 4 lengths of chain with clips. Next ball-gag, maybe not needed this time but definitely for future playdates. Nipple clamps, not needed, riding crops and floggers, don't think so, then I came across dildos, vibes, and butt-plugs, I hadn't necessarily been looking for these items but they did tweak my imagination (and other parts of my body), so into the basket went a modest silicone dildo (lifelike) which had a suction cup on the end so it could be attached to a flat surface, I had some future ideas on how to introduce this item. Lastly one of those small silver butt-plugs, tiny egg shaped end about a 2-inch shaft and then a very pretty little round gem at the end. I thought that the view of that rather than her asshole while I fucked from behind as she was tied over a small table would be very entertaining. I also remembered that anal sex can be a tricky game, trust me guys you can't just go sticking your cock straight in there, it can be a messy affair if you both aren't prepared. So the butt-plug might be a present that I would give to her at the end if she is open the whole anal sex thing. I really don't know what she has in mind, I know from our first encounter that she gets all hot and wet from being handcrafted, she obviously likes it when she feels that she has no control, but how far do I go? Too far, too rough to soon, I think it would be best to take it slow, I have big plans for this MILF.
So Saturday afternoon soon comes around and I am already stiff with anticipation. Knowing that her husband has more than likely left and she'll be on her own or with her son I text her this evening instructions: