Dating

Daidraco

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So now that I had the one date with the attractive girl that wants to see me again, I have started thinking real hard about this one. I used to be good at the bedroom side of stuff; but one of the main things that went wrong in my marriage was a lack of intimacy/desire. It hasn't been 2 years for me, but it might have been that long or longer since I felt like she and I are just going through the motions.

I almost want to go find some easy one and get the first strange out of the way to get back into the groove of a female that is excited to be with me. Damn this feels weird to be talking about.
Iirc, you're older than me. This Theoden GIF is the exact representation of what it will feel like when you fuck someone 15+ years younger than you.
 
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KDow

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So now that I had the one date with the attractive girl that wants to see me again, I have started thinking real hard about this one. I used to be good at the bedroom side of stuff; but one of the main things that went wrong in my marriage was a lack of intimacy/desire. It hasn't been 2 years for me, but it might have been that long or longer since I felt like she and I are just going through the motions.

I almost want to go find some easy one and get the first strange out of the way to get back into the groove of a female that is excited to be with me. Damn this feels weird to be talking about.


I did it just to take the pressure off and it worked like a charm. Just having it as a backup let me get out of my own head. And with HIMS being an app, you don't even have to do anything except press some buttons.

I'm sure you'll be fine, I just wanted to take the chance out of the equation.
 
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Sludig

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So now that I had the one date with the attractive girl that wants to see me again, I have started thinking real hard about this one. I used to be good at the bedroom side of stuff; but one of the main things that went wrong in my marriage was a lack of intimacy/desire. It hasn't been 2 years for me, but it might have been that long or longer since I felt like she and I are just going through the motions.

I almost want to go find some easy one and get the first strange out of the way to get back into the groove of a female that is excited to be with me. Damn this feels weird to be talking about.
Dunno, there's something to be said about casual sex and it doing more harm than anything. Like I think if you get with her there's going to be the excitement of someone you date and get it on with and want to do a good job. Vs lets say you go and hit up some high end escorts or something. You just desensitize yourself to the point where oh hey here's a naked lady, and it is kinda as you said going through the motions. When I was younger, was kinda my experience as far as best sex was with someone I'm with ongoing, the one night stands unless it's just a really good steamy drunken meet up maybe. Generally I found the 1-2 timers whern't as great because you don't have the built up knowledge of each others likes and rhythm or however the fuck to say it.

Like too much to unpack with your wife and initmacy but as we ebb and flow up and down ourselves a bit. Even if you dont feel it, she is much more won over and happy when I'm keeping up with doing various dumb small things like the kiss on the forehead, doing all the affirmation bullshit women need. And after bedroom time actually laying there a bit rather than just racing off to clean up/shower/go about your day/night.
 
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KDow

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Iirc, you're older than me. This Theoden GIF is the exact representation of what it will feel like when you fuck someone 15+ years younger than you.


I won't refute this.

So the first woman I wound up having sex with post wife was something else. She was kind of a bigger girl (but not big big, I don't even know if big is the right description), pretty face, big boobs. Outgoing, but super wholesome. She was a big fan of trivia nights and fucking needlepoint. If anything her demeanor reminded me of the secretary in Ferris Bueller's Day Off. She was 35 I think?, has a couple of kids, been divorced 2 years maybe? Texting was fine. We went out and got a drink and then dinner. Conversation is good. She starts getting handsy, and one thing leads to another...

This chick that I thought was straight out of Leave It To Beaver fucked like a demon. She was out of fucking control. She told me to bite her boobs and then she sent me pictures of the bruises the next day. I was un-fucking prepared.

We hooked up a couple of times, but it ended because she came on too strong (I've gone out on dates where I shit you not, when they find out I'm a widower they tell me they want to be a mom to my kids - this has happened at least 3 times on the first date) and it was too soon after Tori passed that in hindsight I wasn't looking to get serious with anyone. Like I mentioned in the other thread - I didn't go out looking to get laid OR to settle down - I was just trying to feel like a human again. Which I was upfront with her about.

The events that really caused it to end was because I was a dumbass in 2 different ways and I deserve to be mocked and judged for both.

The second time we hooked up she told me she had an IUD and my retarded ass came inside her, I immediately freaked the fuck out after she left and could see my wife's life insurance going to the child of a one night stand. I didn't sleep at all that night. Obviously, I dodged that bullet, but I was a fucking idiot.

The second, was a day or so after that, I was itchy and saw some bumps around my junk. I thought to myself, "Oh my god, I've knocked this woman up AND she gave me fucking herpes." Here's the thing though, I've been a boxers guy for a long time, and I heard from some of my female friends, that might not be where it's at. So, I figured, I'd try out some boxer briefs. I did what any guy would do, I bought some cheap ones off of Amazon. Just to try them out. 100% polyester, not breathable, straight suffocation for my boys, and the weather was warm out. I had also thought I'd trim down there and then I just kept clipping and clipping and by the end of it I think I looked like a naked molerat resting on a flesh toned bean bag chair.

Welp, turned out she hadn't given me herpes, I had instead given myself jock itch, but at that point the ship had sailed and my time with her was done.
 
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OU Ariakas

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I won't refute this.

So the first woman I wound up having sex with post wife was something else. She was kind of a bigger girl (but not big big, I don't even know if big is the right description), pretty face, big boobs. Outgoing, but super wholesome. She was a big fan of trivia nights and fucking needlepoint. If anything her demeanor reminded me of the secretary in Ferris Bueller's Day Off. She was 35 I think?, has a couple of kids, been divorced 2 years maybe? Texting was fine. We went out and got a drink and then dinner. Conversation is good. She starts getting handsy, and one thing leads to another...

This chick that I thought was straight out of Leave It To Beaver fucked like a demon. She was out of fucking control. She told me to bite her boobs and then she sent me pictures of the bruises the next day. I was un-fucking prepared.

We hooked up a couple of times, but it ended because she came on too strong (I've gone out on dates where I shit you not, when they find out I'm a widower they tell me they want to be a mom to my kids - this has happened at least 3 times on the first date) and it was too soon after Tori passed that in hindsight I wasn't looking to get serious with anyone. Like I mentioned in the other thread - I didn't go out looking to get laid OR to settle down - I was just trying to feel like a human again. Which I was upfront with her about.

The events that really caused it to end was because I was a dumbass in 2 different ways and I deserve to be mocked and judged for both.

The second time we hooked up she told me she had an IUD and my retarded ass came inside her, I immediately freaked the fuck out after she left and could see my wife's life insurance going to the child of a one night stand. I didn't sleep at all that night. Obviously, I dodged that bullet, but I was a fucking idiot.

The second, was a day or so after that, I was itchy and saw some bumps around my junk. I thought to myself, "Oh my god, I've knocked this woman up AND she gave me fucking herpes." Here's the thing though, I've been a boxers guy for a long time, and I heard from some of my female friends, that might not be where it's at. So, I figured, I'd try out some boxer briefs. I did what any guy would do, I bought some cheap ones off of Amazon. Just to try them out. 100% polyester, not breathable, straight suffocation for my boys, and the weather was warm out. I had also thought I'd trim down there and then I just kept clipping and clipping and by the end of it I think I looked like a naked molerat resting on a flesh toned bean bag chair.

Welp, turned out she hadn't given me herpes, I had instead given myself jock itch, but at that point the ship had sailed and my time with her was done.
I love it, dude. I promise I will be back with my stories to contribute.

I already fucked up one of your rules, but I hadn't read it yet. I didn't think that I would get a ton of matches and now I have like 5 I'm talking to casually.

The one I went on the date with I have already planned another one on Saturday night. She seems great and is really attractive.

I have another one that I can only describe as a casual date, but she was the first one to match me and I talked to her before any other one.

Another hot one I feel like I want to see has all the signs of a trust fund baby. She has 4 kids, no job, plays tennis, and told me about the three different vacation spots they go to every year. I don't known if my growing-up-poor ass could even date her.

Finally, there is a 33 year old hottie that seems cool, but...... it feels weird even though 33 isnt a kid. I don't know if I can her language? She is the most intimidating, if that makes sense.
 

Kithani

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Another hot one I feel like I want to see has all the signs of a trust fund baby. She has 4 kids, no job, plays tennis, and told me about the three different vacation spots they go to every year. I don't known if my growing-up-poor ass could even date her.
Dude, you’re dating a neurosurgeon’s wife.

Don’t worry they’ll be too busy to hunt you down anyway.
 
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Izo

Tranny Chaser
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I won't refute this.

So the first woman I wound up having sex with post wife was something else. She was kind of a bigger girl (but not big big, I don't even know if big is the right description), pretty face, big boobs. Outgoing, but super wholesome. She was a big fan of trivia nights and fucking needlepoint. If anything her demeanor reminded me of the secretary in Ferris Bueller's Day Off. She was 35 I think?, has a couple of kids, been divorced 2 years maybe? Texting was fine. We went out and got a drink and then dinner. Conversation is good. She starts getting handsy, and one thing leads to another...

This chick that I thought was straight out of Leave It To Beaver fucked like a demon. She was out of fucking control. She told me to bite her boobs and then she sent me pictures of the bruises the next day. I was un-fucking prepared.

We hooked up a couple of times, but it ended because she came on too strong (I've gone out on dates where I shit you not, when they find out I'm a widower they tell me they want to be a mom to my kids - this has happened at least 3 times on the first date) and it was too soon after Tori passed that in hindsight I wasn't looking to get serious with anyone. Like I mentioned in the other thread - I didn't go out looking to get laid OR to settle down - I was just trying to feel like a human again. Which I was upfront with her about.

The events that really caused it to end was because I was a dumbass in 2 different ways and I deserve to be mocked and judged for both.

The second time we hooked up she told me she had an IUD and my retarded ass came inside her, I immediately freaked the fuck out after she left and could see my wife's life insurance going to the child of a one night stand. I didn't sleep at all that night. Obviously, I dodged that bullet, but I was a fucking idiot.

The second, was a day or so after that, I was itchy and saw some bumps around my junk. I thought to myself, "Oh my god, I've knocked this woman up AND she gave me fucking herpes." Here's the thing though, I've been a boxers guy for a long time, and I heard from some of my female friends, that might not be where it's at. So, I figured, I'd try out some boxer briefs. I did what any guy would do, I bought some cheap ones off of Amazon. Just to try them out. 100% polyester, not breathable, straight suffocation for my boys, and the weather was warm out. I had also thought I'd trim down there and then I just kept clipping and clipping and by the end of it I think I looked like a naked molerat resting on a flesh toned bean bag chair.

Welp, turned out she hadn't given me herpes, I had instead given myself jock itch, but at that point the ship had sailed and my time with her was done.
I feel like we should see the bruised titty. Or titties. Yeah.
 
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