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B_J_Frontenac
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07 Nov 2024 5:12PM
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See, here’s the thing. I have a choice. I have an old jerking buddy who’s going to be in town this weekend and I have a chance to get off with him. More than jerking, he’s one of the ones I can suck and 69 with. We’ve done it every couple of years for a few years now.

On the other hand, there’s a GILF who comes into my place of work. Tiny thing. 70+. 5 foot. Maybe 110 pounds. Great taste in clothes. Former New York party girl circa 1970. I complimented her shoes yesterday, these great patent leather and calf loafers. Black. High dollar. Bright socks. She told me about them. I told her I thought they were kinky and she said, “Kinky, huh?” and then she asked me out for a drink.

The problem is that my buddy will be here for just a few hours on Saturday evening on his way through. Not even for overnight like he usualloy is. My GILF friend asked me out specifically for the same few hours. I can either risk turning her down and go for a sure thing and cum with someone who knows how to get me off OR I can hope to get to strip my little gremlin granny down to her loafers and get kinky. Hinted at but not a sure thing. Something I’ve been wanting to do for a while now. 75 or no, she’s fit and tight. I’d like to see just how tight.

I confession that I can’t decide. Cock or cunt. I haven’t had this problem since I was a lad, banging a brother and a sister (No, not and never at the same time).

Buffalo Jose Frontenac
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Youknowwhoiam
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07 Nov 2024 5:27PM

gotta go for the old pussy, jerking bud will be back, may even understand if you explain. if shes as bad as your saying id personally try and bag the old lady

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B_J_Frontenac
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07 Nov 2024 5:36PM

I think you’re probably right. My buddy’s around my age and we get along great, but while he’s well hung, he’s kinda quick on the draw and a little on the non-adventurous side. We like the same porn and he’s fun to get off with but does he look hot in skinny jeans, tight sweaters, and $1000 loafers? No.

Sure, I might get out for drinks and find out that she has no intention of letting me see her wearing just those loafers and only those loafers, but then I’d know. On the other hand, those shoes and those those painted nails might end up wrapped around my back and that bright lipstick might end up at the base of my cock. So I’m leaning in the direction of agreeing with your opinion.

Thanks for chiming in.

Buffalo Jose Frontenac
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Youknowwhoiam
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07 Nov 2024 5:39PM

she asked you out to drinks after you said part of her outfit was “kinky” i think theres a more than 0% chance she is down to clown

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B_J_Frontenac
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07 Nov 2024 5:48PM

Which is why the decision is difficult at all. Pretty sure I’ll see some action, she did respond to ‘kinky’ but being pretty sure and 100% are two different things. I do hope she is kinky though. I’m a foot taller than she is and not quite twice her size. Wouldn’t mind seeing how kinky we could get. And as far as it goes, as fun as the occasional cock is, I do prefer the pussy.

Buffalo Jose Frontenac
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Youknowwhoiam
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08 Nov 2024 5:46PM

so update? i see you decided to go for gran puss, when are yall getting drinks? hope youre able to snap some pics, if not anything crazy just some to show off her tight ol body

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07 Nov 2024 9:18PM

I fully understand this…I like pussy and have been married for years. I’m not ready to be full time gay but it’s very hot to suck another man off sometimes.

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B_J_Frontenac
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08 Nov 2024 12:00AM

100%. If I never helped get another guy off, I’d be satisfied with just pussy. But I’d miss those occasional cocks.

Buffalo Jose Frontenac
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B_J_Frontenac
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20 Nov 2024 7:18PM

UPDATE:

Finally got together with my GILF last weekend AND my buddy. Talk about good timing.

I went out with my lady friend for dinner on Friday and I was NOT mistaken. She wasn’t shy about what she wanted. She wore a different set of shoes, a nice pair of patent leather Mary Janes with white ankle socks. A mid-calf black wool skirt, a white silk blouse with a tab collar, and a black sheep-s wool coat. Talk about lovely. 70+ or no, she pulls off hot very well.

After dinner we went to her place and while I was taking off my coat, she was sparking up a joint. I had no idea. I don’t smoke much and didn’t then, but took a couple of hits to be polite. She asked if I would like a glass of wine and I said sure. When she came back from the kitchen with the wine, she had her hair pulled back in ponytail, still had on her Mary Janes and those cute socks, and that was it. I don’t remember if we even touched the wine.

For a woman of her age, she’s still put together nicely. Sure, there’s a little sag here and there and the wrinkles you’d expect but her breasts were surprisingly perky. And the carpets matched the drapes. I’d always assumed her hair was dyed but she had a lovely little black bush and it was exactly the same shade. Also, one of the bigger clits I’ve ever encountered. I wish I’d seen her in her panties as I’m sure it would have been obvious. As it was, the hood stood up out of her bush prominently and I had no trouble finding it.

We did all the good things. Mutual masturbation (she fingered her own ass but that was as close as I got to it), 69, and a half-dozen positions before I came up into her while I was flat on my back and she was riding. At one point I got to feel those little feet wrapped around me and the heels of those shoes digging into my back and it felt as good as I thought it would. We’re going to get together again soon. She asked what kind of shoes she should have next time and I said cowgirl boots. She asked, “Spurs and chaps?”. I said, “Surprise me.”. I hope she does.

She was tight, uninhibited, and enthusiastic. I couldn’t have asked for a better evening.

My buddy’s trip was delayed and he spent overnight in Denver on Sunday to Monday. I had enough time to get to his hotel and tell him the story while he went down on me. Then we took a shower and I took my turn. The story had turned him on in a big way and the load he dropped was hot, thick, and plentiful. Then we went out and grabbed a bite at a Waffle House. As we left, the hostess, asked us if we had any plans for the rest of the night. My buddy said, “Oh, you know. Suckin’, fuckin’, 69. The usual.”. She coughed, blushed, and I’m pretty sure I won’t be going back to that Waffle House.

We did all of those things. We’d never fucked before and I was a little hesitant but his isn’t the biggest cock and he came pretty quickly. I was on my back and it felt good when he went deep. I’ll let him do it again if we ever have the chance. It’s not something I crave but he felt good. After that, he gave me world-class head, swallowed, and I left after another shower. I’ll probably see him again in another year or two.

If my GILF does show up with chaps and boots, I’ll let you know.

Buffalo Jose Frontenac
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