Positive Hook Ups/casual Relationships

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I know many of you on here are either in committed relationships, or positively single, so I’m asking about any previous experiences (or perhaps current) with casual relationships, and whether you were able to master the knack of finding a good fit that added a pleasing dimension to your life? If so, would you share with me, what worked, what didn’t and how you navigated the emotional aspects of intimacy within that casual connection?

I’m trying to figure this out. I’d love to read any advice you’d be willing to offer.
 
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I used to have multiple friends with benefits. It's actually how I started things out with my now sweetie. All my experiences are 8+ years old at this point and from living in a major metropolitan city in the USA. I never used Tinder/etc.

First thing first, I was extremely clear about what I was looking for. If people can't abide by that, move the fuck on. While it's unfair, it's not exactly hard for a woman to have a miles long line of potential partners compared to how some men struggle to find a woman for casual. I told people I had to be able to at least have brief conversations with them without wanting to smack 'em upside the head. They had to share at least some of my preferences for type of sex. They had to abide by safe sex practices. I strongly emphasized that everything was casual and I would sincerely wish them luck if they found someone they wanted to pursue romantically. Being clingy or demanding would get you cut the fuck off.

They had to be able to host on occasion (this is because I want a chance to see their place and make sure it doesn't look like they live with someone). They had to be single or have the permission of their partner or partners to fuck other people. Yes, I would be checking in for the latter. I got bamboozled once and was fucking someone who I later found out had a significant other. Never again. They had to put up with talking just online (maybe by text) for a bit, so I could gauge their patience along with getting a feel for them so I would feel safe allowing them access to my body. They have to be willing to meet at a public place.

I had a sex positive friend I gave a heads up, anytime I was meeting someone new. Let her know the time of day and where I was meeting up, and she would check in with me later to make sure I was ok.

I'm up front with them about seeing other people casually, but it's none of their business how many people or who. I'm perfectly okay with them doing the same. Lying about anything will get you cut the fuck off, with zero regrets. I have to be able to trust the person, and if they're willing to lie to me about something, even something small, they may be willing to lie about much bigger things. So. Any lies = bye!

I never really had any issues "catching feelings" for any of the casual partners I've had. My now sweetie was the exception. He was one of my really good friends for a few years before we started fucking around. Then we ended up living together for a while due to some complicated shit and it ended up turning into a full blown relationship. Anyway, I don't have much advice for that kind of thing, I'm afraid. If someone started having "feelings" towards me, I cut them off and ended contact.

That's all the major stuff that I can think of right now.
 

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It’s been a number of years since I had a FWBs. I found them online. Established that they were looking for the same thing, that they were also single and able to host as I couldn’t. I ensured that they were clean as well. I wanted to know if they had any other FWBs and expected to be informed as it could impact my health.

After texting/emailing several times, we met and it worked out. Both relationships lasted a couple of years. No feelings developed at all. It was just sex. We got along well, but it was nothing more than physical. With one guy, we explored threesomes, etc. Both guys had a great sense of humour, were adventurous and fun. The first guy, it just sort of ended. The second guy fell in love so it ended when he found a girlfriend.
 
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I used to have multiple friends with benefits. It's actually how I started things out with my now sweetie. All my experiences are 8+ years old at this point and from living in a major metropolitan city in the USA. I never used Tinder/etc.

First thing first, I was extremely clear about what I was looking for. If people can't abide by that, move the fuck on. While it's unfair, it's not exactly hard for a woman to have a miles long line of potential partners compared to how some men struggle to find a woman for casual. I told people I had to be able to at least have brief conversations with them without wanting to smack 'em upside the head. They had to share at least some of my preferences for type of sex. They had to abide by safe sex practices. I strongly emphasized that everything was casual and I would sincerely wish them luck if they found someone they wanted to pursue romantically. Being clingy or demanding would get you cut the fuck off.

They had to be able to host on occasion (this is because I want a chance to see their place and make sure it doesn't look like they live with someone). They had to be single or have the permission of their partner or partners to fuck other people. Yes, I would be checking in for the latter. I got bamboozled once and was fucking someone who I later found out had a significant other. Never again. They had to put up with talking just online (maybe by text) for a bit, so I could gauge their patience along with getting a feel for them so I would feel safe allowing them access to my body. They have to be willing to meet at a public place.

I had a sex positive friend I gave a heads up, anytime I was meeting someone new. Let her know the time of day and where I was meeting up, and she would check in with me later to make sure I was ok.

I'm up front with them about seeing other people casually, but it's none of their business how many people or who. I'm perfectly okay with them doing the same. Lying about anything will get you cut the fuck off, with zero regrets. I have to be able to trust the person, and if they're willing to lie to me about something, even something small, they may be willing to lie about much bigger things. So. Any lies = bye!

I never really had any issues "catching feelings" for any of the casual partners I've had. My now sweetie was the exception. He was one of my really good friends for a few years before we started fucking around. Then we ended up living together for a while due to some complicated shit and it ended up turning into a full blown relationship. Anyway, I don't have much advice for that kind of thing, I'm afraid. If someone started having "feelings" towards me, I cut them off and ended contact.

That's all the major stuff that I can think of right now.
Thanks for the full response. It sounds to me like you have very clear and healthy boundaries. And I can see how you were able to maintain that for a period of time.

To be a little more specific: I’m trying to figure out how to find the type of guy who is, perhaps similar to me - busy, fairly fine tuned intellectually and emotionally, who would be genuinely be up for an ongoing set up. I don’t know that I want a relationship at the moment, I just really miss having moments of intimacy - something that adds to my life. I hate hook ups because they leave me feeling flat and well, empty and honestly, I would rather spend the evening in, watching Netflix, whilst scratching my dogs butt, than be intimate with a guy I’ve spent a period of time building a rapport with only to never see them again.

How do I get from here to there. That’s what I want to know. What am I missing/doing wrong etc.?
 
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It’s been a number of years since I had a FWBs. I found them online. Established that they were looking for the same thing, that they were also single and able to host as I couldn’t. I ensured that they were clean as well. I wanted to know if they had any other FWBs and expected to be informed as it could impact my health.

After texting/emailing several times, we met and it worked out. Both relationships lasted a couple of years. No feelings developed at all. It was just sex. We got along well, but it was nothing more than physical. With one guy, we explored threesomes, etc. Both guys had a great sense of humour, were adventurous and fun. The first guy, it just sort of ended. The second guy fell in love so it ended when he found a girlfriend.
A lot of what you’ve shared is just really good common sense. Get the basics right - I understand that. Where you actively looking for an ongoing set up? Did your two (relatively( long term casuals just turn into that or did you actively seek them out?

I had an ongoing set up one, a few years ago, that worked really well. Eventually, I grew tired of him and that was that. I thought it would be relatively easy to find something like that again, but wow, it’s really not. And so I’m trying to figure out if there’s a better way of doing this...
 
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I had three different friends with benefits who I enjoyed just hanging out with on occasion/ordering a pizza in, etc. One is my now sweetie, one is the guy I found out had a girlfriend, and the third was someone who lied about something trivial and got cut the fuck off. Otherwise, they were generally short interaction/not much talking and just someone to consistently have sex with when the urge struck.

The one who had the girlfriend, I was so mad. I intensely dislike people who cheat, so being dragged into enabling that pissed me the fuck off. I was also mad because we had a really comfy FWB situation otherwise. We would hang out the occasional evening, eat dinner, and fool around and eventually he would go home. We even went off to a nerdy event for a weekend at one point, but there was never any sense of obligation (other than covering any costs evenly/paying for ourselves).

I found most of my FWB through online personal ads. The one with the girlfriend I found through a particular social circle and it just kinda turned into being FWB. My sweetie I met on here. We both like video games and have similar world outlooks, so we had fun just chatting.

Finding respectful, single or ethically non-monogamous people takes some digging, that's for damn sure. Finding one offs is easy. Someone you trust for a longer term thing takes a lot more work.
 
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Also booooo at the "oh, gay relationships will never be the same as a hetero one" snobby BS.

For the record, I'm AFAB but gender queer, but due to the fuckery on this site am constrained to just posting in the Women's section out of the Ask a blank. I bet I've spent more time with a daddy, serving as a boy, and in gay leather bars than more than a few of the AMAB men on here, though.

Guess you should have made even more threads, one in Ask a Straight Man and Ask a Bisexual Man so you didn't get anyone's panties in a twist instead of just posting in Ask a Man : unamused:
 
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LaFemme

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A lot of what you’ve shared is just really good common sense. Get the basics right - I understand that. Where you actively looking for an ongoing set up? Did your two (relatively( long term casuals just turn into that or did you actively seek them out?

I had an ongoing set up one, a few years ago, that worked really well. Eventually, I grew tired of him and that was that. I thought it would be relatively easy to find something like that again, but wow, it’s really not. And so I’m trying to figure out if there’s a better way of doing this...
I sought them out online. I used Adult Friend Finder. I knew what I was looking for and did not want a relationship. We really never went out, although we might send out for food. But like I said, I wanted sexual relationships, not someone to see movies with

It’s not easy. I’m glad I’m not interested in doing that anymore. Recently, someone here tempted me, but he turned out to be a total dud. Completely ghosted me. Fortunately, I didn’t invest a lot of emotion into him. But it can be difficult.
 
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I had three different friends with benefits who I enjoyed just hanging out with on occasion/ordering a pizza in, etc. One is my now sweetie, one is the guy I found out had a girlfriend, and the third was someone who lied about something trivial and got cut the fuck off. Otherwise, they were generally short interaction/not much talking and just someone to consistently have sex with when the urge struck.

The one who had the girlfriend, I was so mad. I intensely dislike people who cheat, so being dragged into enabling that pissed me the fuck off. I was also mad because we had a really comfy FWB situation otherwise. We would hang out the occasional evening, eat dinner, and fool around and eventually he would go home. We even went off to a nerdy event for a weekend at one point, but there was never any sense of obligation (other than covering any costs evenly/paying for ourselves).

I found most of my FWB through personal ads. The one with the girlfriend I found through a particular social circle and it just kinda turned into being FWB. My sweetie I met on here. We both like video games and have similar world outlooks, so we had fun just chatting.

Finding respectful, single or ethically non-monogamous people takes some digging, that's for damn sure. Finding one offs is easy. Someone you trust for a longer term thing takes a lot more work.
Yeah... there are so many married men. So many. Man, it’s depressing to learn just how many are quietly open to fucking around behind their wife’s back. It’s not something that interests me. (I can totally understand your frustration with the deception - it’s so gross, not to mention wildly reckless from a health perspective...) Previously, I found men who were academics, rather interesting to deal with - they were always the best experiences. That’s basically my dream demographic.

Maybe it’s that modern tech has wrecked our attention spans and sites like tinder have made it near impossible to stay focused on one thing... Or maybe I’m doing something wrong. That’s entirely possible and, I suppose, what I’m trying to figure out.

Thanks for sharing your experiences
- helps to know that other women have navigated these things with varying success. There must be a winning approach.
 
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I sought them out online. I used Adult Friend Finder. I knew what I was looking for and did not want a relationship. We really never went out, although we might send out for food. But like I said, I wanted sexual relationships, not someone to see movies with

It’s not easy. I’m glad I’m not interested in doing that anymore. Recently, someone here tempted me, but he turned out to be a total dud. Completely ghosted me. Fortunately, I didn’t invest a lot of emotion into him. But it can be difficult.
Yeah... I joined AFF for all of 10mins. Holy hell, it’s rough and ugly, on there. I don’t think this is the site for it, either.

I know what you mean, the whole casual set up thing has a very limited appeal. Ideally, I would prefer to be in a relationship but, in all seriousness, I cannot tolerate another minute of online dating sites, whilst enduring yet another sexless year... I’m just done with it. There has to be a way to play this where I don’t feel like I’m wasting my (relative) youth waiting for men my age to stop panting after 20 year olds, whilst I dodge 60+ old men who believe they deserve someone younger after “putting up” with their now ex wife... I just want to be able to access an intimate connection, as and when I desire it. And be there for someone else. I have a feeling that the answer is already within me, and I’m just trying to figure this out...
 
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Yeah... I joined AFF for all of 10mins. Holy hell, it’s rough and ugly, on there. I don’t think this is the site for it, either.

I know what you mean, the whole casual set up thing has a very limited appeal. Ideally, I would prefer to be in a relationship but, in all seriousness, I cannot tolerate another minute of online dating sites, whilst enduring yet another sexless year... I’m just done with it. There has to be a way to play this where I don’t feel like I’m wasting my (relative) youth waiting for men my age to stop panting after 20 year olds, whilst I dodge 60+ old men who believe they deserve someone younger after “putting up” with their now ex wife... I just want to be able to access an intimate connection, as and when I desire it. And be there for someone else. I have a feeling that the answer is already within me, and I’m just trying to figure this out...

I wonder if you're somehow giving off the vibe that you're looking for a relationship. Not in an accusatory way, but more a food for though way. I was super duper very much not looking for a relationship when I've had FWBs.
 
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I wonder if you're somehow giving off the vibe that you're looking for a relationship. Not in an accusatory way, but more a food for though way. I was super duper very much not looking for a relationship when I've had FWBs.
You may be right about that... the fact is. I am looking for a relationship, specifically a casual one, but where there’s a strong enough connection that can facilitate the kind of intimate connection I’m after. I just can’t do the mindless fuck exercise - it’s massively uninteresting to me. Especially with my particular sexual interests.

But yes, I can see how that might give off the wrong signals. That’s helpful. Maybe I need to be more casual about it all, and let things develop as they will. But then, am I being true to myself/what I want? I’m pretty straight up and direct in person, and I’m fucking terrible at playing the ‘cool girl’ game. It’s not who I am. I’m an intense person and I love intense sexual experiences. I want someone who’s into that, and gets off on it. What am I missing...?
 
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You may be right about that... the fact is. I am looking for a relationship, specifically a casual one, but where there’s a strong enough connection that can facilitate the kind of intimate connection I’m after. I just can’t do the mindless fuck exercise - it’s massively uninteresting to me. Especially with my particular sexual interests.

But yes, I can see how that might give off the wrong signals. That’s helpful. Maybe I need to be more casual about it all, and let things develop as they will. But then, am I being true to myself/what I want? I’m pretty straight up and direct in person, and I’m fucking terrible at playing the ‘cool girl’ game. It’s not who I am. I’m an intense person and I love intense sexual experiences. I want someone who’s into that, and gets off on it. What am I missing...?

There's nothing wrong with wanting a relationship (just like there's nothing wrong with not wanting relationships), but it might be part of why it's harder for you to find a casual/JUST friend with benefits playmate. I had some very intense sex with friend with benefits don't get me wrong, but it was never with an end goal of "hopefully this will turn into a romantic relationship". I learned how to deep throat with one FWB, I explored how much of a mess I can make with squirting/gushing (I don't like the phrase squirting because it gives a very different idea than what actually happens for me) with another FWB, and the one orgasm from oral sex I've had was with a different FWB.

Not sure what kind of suggestions to make for you, more just general thoughts. If I thought someone was wanting more than I would be willing to give, I would opt to not get involved with them. I don't want to hurt people's feelings or lead them on.
 
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Yeah... I joined AFF for all of 10mins. Holy hell, it’s rough and ugly, on there. I don’t think this is the site for it, either.

I know what you mean, the whole casual set up thing has a very limited appeal. Ideally, I would prefer to be in a relationship but, in all seriousness, I cannot tolerate another minute of online dating sites, whilst enduring yet another sexless year... I’m just done with it. There has to be a way to play this where I don’t feel like I’m wasting my (relative) youth waiting for men my age to stop panting after 20 year olds, whilst I dodge 60+ old men who believe they deserve someone younger after “putting up” with their now ex wife... I just want to be able to access an intimate connection, as and when I desire it. And be there for someone else. I have a feeling that the answer is already within me, and I’m just trying to figure this out...
Men get worse the older you get. Men my age want really young women or are so “traditional” they think they can dictate everything I do, from driving to how to cut a tomato. Young men want sexual lessons. I’m not interested in any of that. I’m completely content on my own.

If you really want a relationship, then stick to your goals. Just a sexual relationship will not satisfy you. It will not work as a stop-gap while you wait for the real thing to come along. Even if you did find someone to satisfy that sexual itch, you would likely find yourself falling for him, and then he’d be confused because you changed the rules on him. You have to be honest with yourself. If love is what you really want, then go for love. You deserve to get what you want. Sex? Well, that’s what vibrators are for. I know you crave intimacy, but you don’t get it by setting up a FWB situation. You’ll only be disappointed.
 

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I wonder if you're somehow giving off the vibe that you're looking for a relationship. Not in an accusatory way, but more a food for though way. I was super duper very much not looking for a relationship when I've had FWBs.
I totally agree. When I was in a FWB situation, I really was NOT looking for relationships. That’s why they worked. I couldn’t care less if I ever saw either guy again. It was just sex.
 
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I totally agree. When I was in a FWB situation, I really was NOT looking for relationships. That’s why they worked. I couldn’t care less if I ever saw either guy again. It was just sex.

Yep! I had a couple of FWB who found a person they wanted to pursue romantically, and I didn't feel bad at all, wishing them luck and never interacting with them ever again. Some, I knew they had other FWB besides me, and I would tell them to have good sex (with the other people).
 
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Yep! I had a couple of FWB who found a person they wanted to pursue romantically, and I didn't feel bad at all, wishing them luck and never interacting with them ever again. Some, I knew they had other FWB besides me, and I would tell them to have good sex (with the other people).
The first guy might have found a girlfriend, I never knew. The second guy, definitely did. He eventually married her. Totally, “good luck!” Second guy and I played with other people. Zero jealousy. But if it was my boyfriend? No way! I would have killed him if he screwed someone else even if he was with me at the time.
 
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Men get worse the older you get. Men my age want really young women or are so “traditional” they think they can dictate everything I do, from driving to how to cut a tomato. Young men want sexual lessons. I’m not interested in any of that. I’m completely content on my own.

If you really want a relationship, then stick to your goals. Just a sexual relationship will not satisfy you. It will not work as a stop-gap while you wait for the real thing to come along. Even if you did find someone to satisfy that sexual itch, you would likely find yourself falling for him, and then he’d be confused because you changed the rules on him. You have to be honest with yourself. If love is what you really want, then go for love. You deserve to get what you want. Sex? Well, that’s what vibrators are for. I know you crave intimacy, but you don’t get it by setting up a FWB situation. You’ll only be disappointed.
Oh god, this is so true... men really do get worse, as they age. I find them grumpy and quick to irritation and that’s massively uninteresting to me. I see why they hanker after much younger women - because they’re, generally speaking, easier. Whilst I love women as we age - I find we get a lot more interesting to spend time with, I can see why there’s an issue. As can every other woman over the age of 35. And yes, young guys in their 20’s are cute and enthusiastic - 29 is the youngest I’ve been able to go, but even that was a challenge.

I know what you’re saying about being clear on what I want and to not try to mix and match, but the fact is, I’ve thought this through and I just feel bad about how little sex I’ve had, in absolute years. It’s actually scares me. I figured that, if I really wanted to be in a relationship, I would be. And part of why I haven’t felt like dating (at all), is because I’ve felt so disconnected from my body, sexually speaking. Joining this site, back in June, taking images of myself, chatting with men and writing erotica, did exactly what I’d hoped it would: it woke me up. I spend a lot of time running a business, meanwhile, time is ticking on. I would settled for an intensely pleasurable sexual relationship. I would love that. I love my single life, and whilst I hope I won’t be single forever, right now, I really just want to be fucked and, well, dealt with in away that makes me feel alive. Because, you know, modern life can really suck the life out of you, if you don’t book this stuff in... holiday, books, sex etc. That’s where I am.

And thank you for taking the time to talk this through with me. The only friend of mine I chat to about this - she’s explores her sexuality in similar ways, lives in Sydney and she’s currently on a long trip around South America.... (Having an amazing time!)

I actually feel better. That last paragraph where I wrote about what I want, feels right to me. Maybe it’s just a case of being super clear on these things...
 
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Oh god, this is so true... men really do get worse, as they age. I find them grumpy and quick to irritation and that’s massively uninteresting to me. I see why they hanker after much younger women - because they’re, generally speaking, easier. Whilst I love women as we age - I find we get a lot more interesting to spend time with, I can see why there’s an issue. As can every other woman over the age of 35. And yes, young guys in their 20’s are cute and enthusiastic - 29 is the youngest I’ve been able to go, but even that was a challenge.

I know what you’re saying about being clear on what I want and to not try to mix and match, but the fact is, I’ve thought this through and I just feel bad about how little sex I’ve had, in absolute years. It’s actually scares me. I figured that, if I really wanted to be in a relationship, I would be. And part of why I haven’t felt like dating (at all), is because I’ve felt so disconnected from my body, sexually speaking. Joining this site, back in June, taking images of myself, chatting with men and writing erotica, did exactly what I’d hoped it would: it woke me up. I spend a lot of time running a business, meanwhile, time is ticking on. I would settled for an intensely pleasurable sexual relationship. I would love that. I love my single life, and whilst I hope I won’t be single forever, right now, I really just want to be fucked and, well, dealt with in away that makes me feel alive. Because, you know, modern life can really suck the life out of you, if you don’t book this stuff in... holiday, books, sex etc. That’s where I am.

And thank you for taking the time to talk this through with me. The only friend of mine I chat to about this - she’s explores her sexuality in similar ways, lives in Sydney and she’s currently on a long trip around South America.... (Having an amazing time!)

I actually feel better. That last paragraph where I wrote about what I want, feels right to me. Maybe it’s just a case of being super clear on these things...
No problem. I just want you to be able to get exactly what you want out of life. Personally, I’ve explored my sexual being in every way I’ve felt I needed to. Relationship-wise, not so much. But it is what it is. When I was ripe and ready for it, it didn’t happen, now I’m past it. And I’m fine with it. I’m settled in my career, financially, and with my friends and family. I’m at peace with myself. I wrote in another thread that it would have to be an extraordinarily special person to change my relationship status for me. I’m not looking for it. Kind of avoiding it actually.

But if this discussion helped you pinpoint what you want, I’m glad. I hope you achieve that. You absolutely deserve that. I do believe women get more interesting as we age. Sexually riper, more rounded as human beings. Don’t waste yourself on just anyone.
 
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I don't have a lot to add because I'm only interested in monogamy. That said, I did have a semi-successful casual relationship a few years back. This guy was pretty much perfect for me... funny, smart, successful, kind, easy on the eyes, TONS in common... except he was averse to monogamy. At the time, I was interested in an exclusive FWB/casual monogamy situation. He wasn't. We gave it a shot anyway, but when I found my feelings didn't change about what I was looking for, we ended it. That sucked because we were compatible in the bedroom... same things were on the "oh, hell no" list, GGG, he was fairly girthy but not too big for oral, and was just plain fun in the sack.

We kept in touch sporadically, mostly networking, sharing jokes, news on our similar hobbies and the occasional life update. Now that I'm single, and he's not in the same headspace, he wants to date. He's been married twice and cheated both times, so I know I would never trust him... so I'm not very interested.
 
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