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Dating Disasters
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Straight Male / 39
I Got Cougared With An Audience But The Kitty Wouldn't Purr
Tammy was an older coworker, 30 to my 18, who had made it clear that she was attracted to me from the first time we met. I was flattered, but I not only had a girlfriend at the time, I wasn't really attracted to her. She wasn't ugly. She just also wasn't pretty.
I didn't tell her the second part, of course, but she respected the girlfriend part and everything was cool.
Fast forward a year. I'm 19. She's 31. I am fresh from a breakup. Tammy approaches me and is being very flattering and openly sexual as well as sweet. She is expertly stroking my ego and I don't have a reason to not give her a chance anymore. Not then, anyway. At 19 I was not the type to be able to just say, "Look, your nice. You just don't make my dick want to come out and play."
So, I go out with Tammy. Naive me figures if we go out, she will realize that our age gap is too big and we have nothing in common.
That should have been true. I did not, however, at 19 have a grasp on how little a woman cares about anything when she is horny and has a chance to put the cause of horny inside herself.
So, our date is boring as Hell. It ends and I am shocked when she asks me inside. Again, I don't know how to say no, so I go. I'm confused and not really excited about getting laid for the first time ever, but I was 19. Excited didn't matter I could have fucked extra wet mud and come back for round two.
We get up to her apartment and go in. Inside it reminds me of my grandma's place a little. There were those doily things and candy dishes and stuff. Not exactly a den of erotic pleasure, but whatever.
Tammy takes my jacket and, without pretense, leads me to the bedroom. She opens the bedroom door and inside are shelves and shelves of Doughboys. The laughing ones you poke in the tummy.
There are statues and stuffies and action figures and everything. All sizes of Doughboy. Probably close to 150 or 200 of them. Each and every one positioned facing the bed. Each and every one with that smile.
I tried to ignore it and perform, but it was super weird. No matter where I looked there was a Doughboy looking back and watching me try to fuck this plain looking, no personality having chick.
I'm still not sure how I was doing with my performance that day either. Not really. Like everything else, it was weird.
Tammy has been undressed and we have been playing around for way to long, but for obvious reasons, I'm not fully ready and despite her urgent pant removal and open legs body language, Tammy doesn't seem all fired up either. She isn't really doing much of anything or reacting.
Well, finally, I manage to fantasize my way into being hard and decide to get on with it. I get on top and start. At 19 I wasn't the most experienced, but I had done a few things and had earned some confidence. With Tammy, it all went down the drain.
No matter what I did, all she did was lay there. She didn't make a single sound or move a single muscle except to maintain eye contact which was actually worse. Different speeds, angles, depths, harder, softer. Nothing. And she didn't even feel good. At one point I distinctly remember thinking that I could have jerked off it would have been faster and better.
Eventually, I am able to make myself cum which I'm only happy about because it means its over. I was confused and felt like I failed and just wanted to leave. Which I did soon after, but as I was, Tammy asked with all sincerity if we could do it again soon.
I didn't tell her the second part, of course, but she respected the girlfriend part and everything was cool.
Fast forward a year. I'm 19. She's 31. I am fresh from a breakup. Tammy approaches me and is being very flattering and openly sexual as well as sweet. She is expertly stroking my ego and I don't have a reason to not give her a chance anymore. Not then, anyway. At 19 I was not the type to be able to just say, "Look, your nice. You just don't make my dick want to come out and play."
So, I go out with Tammy. Naive me figures if we go out, she will realize that our age gap is too big and we have nothing in common.
That should have been true. I did not, however, at 19 have a grasp on how little a woman cares about anything when she is horny and has a chance to put the cause of horny inside herself.
So, our date is boring as Hell. It ends and I am shocked when she asks me inside. Again, I don't know how to say no, so I go. I'm confused and not really excited about getting laid for the first time ever, but I was 19. Excited didn't matter I could have fucked extra wet mud and come back for round two.
We get up to her apartment and go in. Inside it reminds me of my grandma's place a little. There were those doily things and candy dishes and stuff. Not exactly a den of erotic pleasure, but whatever.
Tammy takes my jacket and, without pretense, leads me to the bedroom. She opens the bedroom door and inside are shelves and shelves of Doughboys. The laughing ones you poke in the tummy.
There are statues and stuffies and action figures and everything. All sizes of Doughboy. Probably close to 150 or 200 of them. Each and every one positioned facing the bed. Each and every one with that smile.
I tried to ignore it and perform, but it was super weird. No matter where I looked there was a Doughboy looking back and watching me try to fuck this plain looking, no personality having chick.
I'm still not sure how I was doing with my performance that day either. Not really. Like everything else, it was weird.
Tammy has been undressed and we have been playing around for way to long, but for obvious reasons, I'm not fully ready and despite her urgent pant removal and open legs body language, Tammy doesn't seem all fired up either. She isn't really doing much of anything or reacting.
Well, finally, I manage to fantasize my way into being hard and decide to get on with it. I get on top and start. At 19 I wasn't the most experienced, but I had done a few things and had earned some confidence. With Tammy, it all went down the drain.
No matter what I did, all she did was lay there. She didn't make a single sound or move a single muscle except to maintain eye contact which was actually worse. Different speeds, angles, depths, harder, softer. Nothing. And she didn't even feel good. At one point I distinctly remember thinking that I could have jerked off it would have been faster and better.
Eventually, I am able to make myself cum which I'm only happy about because it means its over. I was confused and felt like I failed and just wanted to leave. Which I did soon after, but as I was, Tammy asked with all sincerity if we could do it again soon.
# 75682 - by
LaughingJarl / December 30, 2024


