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swjg
Over 90 days ago
Bi-curious Male, 59
0 miles · Tiverton
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swjg
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Cheating - by most social standards - yes.

If all parties are aware of the situation - then it is between you.
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swjg
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Offered to do it for my G/F. She isn't into the idea so:

No.
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swjg
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A combination of:

On my back
One girl with strap on (or functional TG) deep fucking me in the ass (still to do)
One girl sitting on my face sealing me in some breath play with her pussy and ass (done this before)
Both girls are facing each other and kissing while jacking me off between them (still to do)
If we could get the timing right and all came together - the one on my face would pee over me as we finished (still to do).

Maybe that is a fantasy rather than a bucket list......
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swjg
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Well - I just flew back across the Atlantic - UK to USA. Couple of days after Xmas. In a 747. I was seated back in the cattle class and was in the middle row of four. Lady to the left of me - so in the aisle seat - was reading a fairly steamy pot boiler on her Kindle - from what I could tell by a brief glance over the screen. In her late 30's I would have placed her. In due course she put her blanket over herself - I thought to sleep. But she seemed a bit restless and as I caught a whiff of her - I figured she was taking care of herself under the blanket. A gentle shudder and then probably real sleep confirmed my suspicions. To be quite honest - I was surprised that I didn't find it at least a little bit hot. It was just a touch too public where she was seated - and I had a better book - well I thought - about flying!
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swjg
Active Ink Slinger
On my back
One girl with strap on (or functional TG) deep fucking me in the ass
One girl sitting on my face sealing me in some breath play with her pussy and ass
Both girls are facing each other and kissing while jacking me off between them
If we could get the timing right and all came together - the one on my face would pee over me as we finished.

Maybe that is a fantasy rather than a bucket list......
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swjg
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+1

My first wife use to time our joint orgasms with that trick. Just as she came she would stroke my ass hole and I would trigger into her.
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swjg
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At least once. But more likely 2-3. Even in an active relationship. As I age I might not get so hard - but it is supposed to also be good for prostate health (seriously).
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swjg
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Climbing a rope in the gym. With the rope pressed on top of my cock as I levered my way up with my legs (and down and up and down and....)
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swjg
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Well as a way of trying something that you are not going to run into mainstream or fulfilling a fantasy - sure - why not? About the only way I have been able to cum up with to have an experience with a shemale or just some completely uncomplicated relief in a fantasy. Take your time, book at least two hours, go with workers with good reviews and decent histories. They have reputations to protect!

Avoid very young, inexperienced and those who are there because they are desperate.
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swjg
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My ex used to do this to make us cum together. I would hold off while thrusting into her. As she started to cum she would reach around and finger my ass and it was like a trigger - setting me of finto her and she clamped on me.
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swjg
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Used to have a gf who liked putting me in her silk French Knickers and rubbing me though them. When my pre-cum started to wet them she would sit on my face and get very wet and excited. I used to love the feeling of the silk.
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swjg
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As I get older and the clear lines of "straight" blur towards nuances of different experiences with others who are not necessarily "straight" - there are some things you just can't do with your partner of the opposite sex - like trying with another guy or a transgendered person. Is it cheating to try? You only live once. Would I regret if I didn't try? Would my partner understand me trying? Too much of a wimp to risk exploring this boundary with her. I paid for the experiences.
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swjg
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Few of us were having to share a floor on camp rolls while working on a volunteer project one weekend. Hooked up with a gorgeous willowy redhead. We lay together while everyone else fell asleep - then we started to touch each other. We had to be silent so as not to wake the others. I slid down and started to lick her perfect pussy - red tuft of hair and tasted of cinnamon and strawberries. I kept going while she gripped my head and tried to remain silent while she came. I slid up and when she touched me I came across her belly. We rearranged the sheets and fell asleep - hoping no one heard us.......
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swjg
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I did once have a girl insist that I keep trying when it just was not going to happen. (I'm not THAT big!). She was completely turned on and kept trying to take me from all sorts of angles. It was quite painful for me and in the end she hurt herself with some tearing. :-( Not a good outcome for either of us
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swjg
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Consider myself straight but love it if it is the right guy and cock. A little bit of feeling the power of the cock in my mouth and a little bit of submission on my part.
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