This is more of an experimental time travel story than it is smut. There is sex mentioned but it isn't as erotic as it could be. The idea was more interesting to me. Enjoy.
Also, this is one interpretation of time travel. Just because you have another one doesn't invalidate the fictional time travel occurring in this fictional story.
Thanks for reading.
*****
Here's the thing about time travel and the Double Time Hook-Up, the strategy is 100%. If you're in the room, you've already verified the MILF is available and up to fuck, because otherwise, you would have left the table. Your past self gives your future self a thumbs-up when you walk in. You already sat through this event and watched yourself score, and if you didn't? Then you wouldn't have come back around to do it again. That would create a paradox. Time will unfuck itself with you in it. Unfucking hurts and is mandatory. There's only one way the event works.
So let me tell it chronologically.
You visit her when she's barely 18, but you're armed with the knowledge that she'll give you at the bar. The little inadequacies that haunted her, and you'll exploit them. You'll be sentimental and sweet. You will fuck her barely eighteen-year-old pussy, and disappear into dust. She'll search for you her whole life. She'll wish you had stayed.
In the future, you walk into the bar, but you're already there. Because time has already happened, all at once, you're just hopping from point to point. If you get a thumbs down, you never met the MILF, you'd never go back in time and fuck her barely eighteen pussy, and you'd never give the thumbs up. So, therefore, the double-pincer move is that you must necessarily have succeeded in order to be there. So you walk in, you meet the MILF. She's older than you, but she missed you. She recognizes you in a way and can't resist you because she's been waiting her whole life for you to come back. The MILF tells you she doesn't often go after younger men. You tell her, "Bullshit."
She's taken aback. Most men in her life probably don't talk to her like that, but you talk to her like that. Because you already know you're going to fuck her. Your future self confirmed it. If you hadn't, you wouldn't be in the room. Therefore the Double Blind Time Hook-Up is a guarantee so long as you follow all the steps correctly.
You knock back several drinks, and she rubs those big fake tits she got when she turned 30. Her husband left her for a younger woman; you'd never do that. You tell her she's beautiful and how you'd like to see yourself between her legs. She tells you you're bold, and she likes that. There's no other way the event could play out.
At bar close, you go back to her house. You disrobe her and motorboat those titties as if the world was ending. You put your dick inside her and pump your cum deep inside her. She's moaning and screaming because this is the best sex she's ever had. You're not good at sex. This is catharsis after you seduced her at eighteen and abandoned her. She's learning to let go while you continue to be the piece of shit that will soon take advantage of her, relatively speaking.