What Was Your Worst Date/best Date?

Derringer

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Subject Hijacked from "Ask a Woman" forum because guys aren't allowed to post there.
There are all too many candidates to choose from as my worst date so I will first post what I consider my best.
My best one on one hookup didn't happen until about a decade or so after one of my worst.
I was in dire need of a temporary place to stay after returning from a long time travelling.
My sister offered me her couch until I could sort out a place of my own. She had a flatmate (Janis) whom I had met a few times who was apparently ok with the arrangement. Little did I know she had a thing for me until the first night in the flat.
My sister and Janis had retired to their rooms and I was just preparing to crash on the couch. Janis crept into the room and asked me point blank if I want to share her bed. I was surprised but readily agreed to join her.
Before I give the basic details I need to point out that prior to this I previously had never managed to give any woman much pleasure let alone an orgasm with my penis action. I have a tiny cock and unreliable stamina. I am pretty adept at foreplay though and have managed the deed with fingers and tongue before and/or after my disappointing cockmanship.
She seemed to be a bit dismayed when she saw my little dick but that is a common reaction and has only very rarely been a showstopper (the greater disappointment comes later)
I did my best to extend the foreplay long enough to get her off but she wanted to get to the fucking. She was warmed up for sure but I was certain my poor little dick would fail to raise the bar.
Something very rare happened as my usual 'Gone in 15 seconds' performance level extended to an unprecedented length of time. I wasn't clock watching but I slow grooved her for a record time. That was amazing enough but she actually had a genuine orgasm. I have given more than a few definite fake ones but this was the real McCoy. She was very grateful and thanked me for giving her 7 Orgasms! (I have often thought it would have been better for those women before and after this girl if I didn't use up all my power in one go)
That was the only time I managed to give Janis another O with my cock even though we actually coupled up for about 6 months. (I found out it lasted that long partly because our non sexual relationship was good and partly because she was fucking other guys)
 

Derringer

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Haven't concluded which one was my worst date but here is a shortlist of contenders. I will expand on the winner(s) after I mull them over and compare the disaster level.
In no particular order :
- First (all the way) experience
- Holiday hook up
- failed MFF
- camping trip in/out emasculation
- club pick up jumps over
- I'll judged skinny dip
- designated revenge sex participant
- motel hell
( so many to choose from already and I have plenty more possible )
 

Tight_End_SC

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I will keep this at a high level description and not get down into all of the details.

My worst was a date (aka proposed hookup) was with a fellow who must have been strung out on something. He was so paranoid that he kept looking in the closet and under the bed to see if people were there. He asked me if he could 'hit the pipe a little bit'... NO you can't... as I escorted that worthless sack of &*(^% out of my home. He was yelling and screaming at me to such a degree that I though maybe I would end up having to use force. He left on his own however.

My best (so far) was with an amazing person who suggested we take a late night walk on the beach. It was simple and nothing extravagant, and looking up at the stars, talking, and just being together in a wonderful vibe made it all just perfect.


With women the worst was at a time in my life where we can't discuss here. My best was with a great woman who is 9 years older than I am. She and I screwed in the hot tub, pool, on the patio, on the den floor, couch, steps, then ultimately in the bed while the headboard was knocking against the wall so hard that stuff was falling off the shelf and onto us. What a night!!!