I consider myself a generous lover, but even I'd admit I'm not typically THIS generous.
My typical feelings is that great sexual experiences occur when both people can find the line between being selfLESS and a little selfISH. When both people are concerned about giving the other person pleasure, AND taking over in the moments when they need to in order to get over the top.
During this particular period in my life I was having a LOT of casual sex with various partners, so I was more than happy to sacrifice my own pleasure for this night in order to have a great story for the both of us to share...
But if I'm being completely honest... this wasn't the plan going into the night. It was just something that happened, and it was OH SO MUCH FUN.
I was working regularly in central Florida and discovered a great bar near a convention centre. If I had a Wednesday night where I had nothing else going on, it became a fun place to go. There always seemed to be a conference in town.
On this particular night, the bar was crowded when I arrived with a large group of people surrounding the bar. I ordered my drink and quickly began chatting with a woman that was from out of town. We chatted for a bit before she went to the restroom.
When she left, her space was quickly filled by two other woman, an attractive brunette that immediately got my attention, and her slightly loud friend.
The three of us started talking right away, the brunette sitting beside me, and the friend leaning over everyone to try to put herself in the middle of the conversation. I was now on my second or third beer and they seemed to be in a fun mood, so it wasn't long before the conversation turned more flirty.
I don't remember how it happened, but we somehow began playing "never have I ever" like we were a group of teenagers. I should say, at this point I was 42/43 years old, and I would put them in their early to mid thirties.
I think the questions turned sexual by midway through the first round, and the friend was working very hard to make it clear she was very openminded. The brunette and myself were a little slower to raise the temperature of the game, but the looks we exchanged suggested there was mutual interest.
Around 2am the bar was closing and I offered to give the women a ride back to their hotel. They accepted and as we left together I put my arm around the brunette, she placed her arm around my waist and a hand on my stomach.
We continued to flirt as we drove the short distance back to their hotel, then I walked them inside. No one made any move to stop me from joining them, so I continued to walk with them to the elevator, then got in with them. When we arrived at their shared floor we got out, and the friend awkwardly said goodnight and started to walk away as we arrived at the brunette's door. She opened the door and made her way inside, holding the door in such a way that suggested "well, get in here..." so I followed quickly behind.
We started to kiss immediately.
Now, I should emphasize at this point, I was hoping to fuck this woman. She had long wavy brown hair, was pretty with great eyebrows and smile, and was in very good shape with a nice stomach. If you've read any of my other stories you know I'm a sucker for a nice stomach. Nice stomachs make me want to give oral.
I lay her back on the bed and we continued to make out in missionary position. My hips were grinding against hers, doing my best to tease her with the bulge in my pants.
Slowly different pieces of clothing continued to come off. First our tops, then her pants, then my pants, then her underwear.
I made my way down her stomach, hooking her legs over my shoulders and my tongue teasing all around her pussy without actually touching it.
My mindset is always to make a woman cum from oral first, especially our first time together. It always helps me to relax and enjoy myself when I know that she has had at least one orgasm, and so that is what I set out to do.
I should also mention that there is another moment that going down on a woman seems to create. It usually happens that either after she cums, or after I've gone down on her for a bit, she almost begs to be fucked. It is a moment of PURE ego boost, I'll admit. But isn't that kinda what casual sex is about? And I'll be honest, I was looking forward to that moment...
So as I went down on her, slowly starting to tease her pussy with my tongue, then finding her clit, I also started to enjoy the view. Watching the stomach of a woman move as you go down on her is incredibly sexy. And then listening to her sounds as you give her pleasure is incredibly hot too,
As I slid a finger, then two, inside her I could tell that she wasn't going to take long to orgasm. While she wasn't overly vocal, her body definitely was responding in the most sensual way. I curled my fingers up to massage her g-spot as I licked to clit, and a few moments later I felt her legs squeeze the side of my head slightly, the back arch a little more, and a deep growl escape her lips.
I continued to lick until she reached that moment where she was too sensitive more touch, and pulled away from me. I think kissed back up her stomach and between her legs. The bulge in my underwear pressed up against her wet pussy.
We kissed as I waited for her to ask for my cock. I was sure it would be any moment now.
But she didn't.
Now, I certainly wasn't offended, but it did trigger something competitive in me. I didn't get the ego boost that I wanted so I decided there was only one course of action...
I was going to go down on her again and make her beg. (How typically male, right?)
After a couple of minutes I began to kiss my way back down her stomach half expecting her to stop me and suggest some other naked partner activity. But nothing was said, and her legs spread for me again as I began to tease her pussy for the second time in 15min. Now I was more familiar with what she liked, so I set right to it. My tongue worked her clit as two of my fingers started to slowly fuck her. It was probably about 10min before she came again on my fingers and mouth.
I was certain that NOW she was going to want to be fucked, but I was also set on winning this one-sided battle that I had created. This time I knelt between her legs and lowered my underwear in front of her. She watched while biting her bottom lip, and once fully naked I made my way back between her legs, this time with my bare cock teasing her wet pussy.
I was certain it would only be a moment before she said something about wanting me inside her, or reach down to guide me towards her.
I should also make clear, at this point I was not in any way frustrated. If anything I was enjoying what was happening, and this perceived cat and mouse game.
But when a couple of minutes of making out went by I realized I now had two choices... admit defeat in this ridiculous game id invented in my head, or double down.
And since doubling down was still fun for me, that is what I did. But as I was kissing down her stomach for the 3rd time I made a declaration in my own head. "I'm either going to keep going down on her until she begs to get fucked, or I'm going to keep going down on her until she taps out. I'm leaving this woman with a story to tell her friends later."
This now continued for at least 5 more of her orgasms. I would make her cum, then kiss up her stomach and do my best to tease her, but after a few minutes more, if nothing was said, I would start to find my position between her thighs.
There were 3 occasions where her thighs gripped my head so tightly that I KNOW she came, but my estimation was that she orgasmed about 10 times over the next couple of hours. It became clear that after 5 or so times she probably wasn't going to ask for my cock like my ego had hoped. So instead I readjusted my goal and decided I was going to pay this woman back in this one night for all the times she'd hook up with a guy and NOT cum herself. I was going to be the story that she told over a glass of wine with her friends years from now, the guy that just kept going down on her over and over again until she tapped out.
Finally, after my fingers were curled up inside her and I was fingering her hard as I sucked her clit between my teeth, she came while digging her heels into my back.
I waited until her orgasm passed before removing my fingers. She looked down at me with her legs spread.
"I can't take any more".
I looked over at the clock... it was 5am.
I never did get to fuck this gorgeous woman but a couple of years later I got a random text from her asking if I still worked in that city.
I replied that I didn't but I had fun that night.
"I was surprised you didn't fuck me." she replied "but I was so drunk I couldn't even form words. Certainly was a great experience for me"
I replied that I had a great time too.
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from Gonewild Stories https://www.reddit.com/r/gonewildstories/comments/z6eome/giving_a_woman_i_met_at_a_conference_25_straight/
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