When and how did you realize that free sex is over ?

[+ Eric Hassan]

I work in a courthouse and am required to wear a jacket and tie to work. Sometimes I use an elevator in a secured area which is used by many of the judges as well as deputy sheriffs.

 

Occasionally a deputy who doesn't know me will see an older man wearing a jacket and tie and greet me with a "Good Morning Judge". My response: "Actually, I'm not a judge, but you may address me as Judge. I like role play."

 

And Eric, even though I am much older than you, I would love to have you be my Daddy!

 

Maybe we can both put on suits, hit the town, then go home for some dad and son time?!

[LivingnLA]

Free sex is never over if you ignore the time and energy put into cruising/dating/etc.

 

The reality is more simple: everything involving another human being requires effort. Sometimes, effort is just a bit of time on a hookup app and sometimes that effort is a grand for a few hours with a pro.

 

I was a horndog growing up because my mother--a feminist and a doctor--insisted on giving me the knowledge early to practice safer sex and about actually doing it well. No, it wasn't pervy. Like many topics in my household, it was along the lines of, "if you're going to do something, DO IT WELL!" I lost my "straight virginity" at 13 to my babysitter and developed a reputation as "The Guy" to go to in HS if a girl wanted a great first experience.

 

My college frat experience expanded my mind and led to the beginning of my personal journey to accept my bisexuality. I didn't sleep around with guys the way I had girls, but I had a few experiences here and there.

 

I'm lucky in that over more than 30 years, I've only caught 2 STIs, both easily treated, and they hammered home my personal responsibility for myself and those I'm intimate with. Those who've avoided all STDs and STIs--even nearly ubiquitous ones--while having many sexual experiences blow my mind.

 

Now, as I embrace my "middle age," I've found it's still easy to get sex when I want--and not just from my wife--because of the "DILF thing." The number of times I'm flirted with by people of various ages and orientations, especially when I'm with my youngest son or daughter. I wonder how it will change over the next three to four decades? I am assuming there will come a time when it's "fuck off" not "hey daddy" to my smile.

[danncyC]

I am curious to know how you realized, accepted and adjusted to that fact. Was it at a particular age, some specific event that happened - like someone making a comment or such ? How did you handle it - Was it actually liberating to realize that you are out of the dating, cruising game ? Did your sex life improve or did you get depressed, detached, spiteful ?

 

For me it came with the diagnosis of autism when I was 28. I always felt out of place or weird, certainly because I was gay, but more so because I didn't make friends or feel like I made friends the same way that others did. Dating, even approaching someone to chat, is very tricky when you find it difficult to make eye contact when having a conversation. I never want to be the one to make initial contact in person or online not because of fear of rejection but because my brain is not wired that way, and when I compel myself to think about doing it, my brain questions nonstop whether it would be the right thing to do at that time.

 

I never thought I would be in the place to use an escort, but by my 30s I had existed so much in my own head that I had reached a state of loneliness that is hard to express. I would find myself at home on the weekends and realize on Sunday evening that I had not spoken one word aloud since Friday night.

 

At the time, I was seeing a massage therapist for actual massage therapy, but then he moved away and recommended someone else. The someone else turned out to give a very good massage and then when it was over, finished me off. It wasn't something I asked for or discussed in advance, but it did satisfy, somewhat, the need for touch and connection that was difficult to come by. I was seeing him for massage et al for a couple of years, but then he too moved away last year. So now I'm on the hunt finding someone else for that level of intimacy and connection. I have played the field quite a bit at home and when I travel, but it's difficult.

 

I've had experiences with escorts where the connection is just so superficial and you feel more empty when it's over. I've tried to be open and upfront with the fact that I am on the spectrum and have a stutter when I first meet someone. I would say, about 75% of the time, when I am upfront, appointments get cancelled. I've also once had an escort call me on the phone after meeting and imitate my stutter while laughing.

 

I still hook up on my own. I'm in my mid-30s, fit, have my own special skills and have some regular buddies. But when I get that text "What's up" or that Scruff woof, I'm just not mentally there for it. And when I am mentally there, the timing on there end doesn't work. It's something that I just can't juggle. But I can, when the feeling is right log on to Rentmen and see what's out there.

[MikeyGMin]

I've had experiences with escorts where the connection is just so superficial and you feel more empty when it's over.

We all have, bud. We all have. Please don't think you are alone on this one. With or without the challenges of autism, it takes a very very thick skin to never feel like that. Hang in there.

[BabyBoomer]

I've also once had an escort call me on the phone after meeting and imitate my stutter while laughing.

 

 

That's despicable.

 

~Boomer ~

[+ FreshFluff]

Confession-- in college and even high school, before I met my wife, I was a bit of a dog, and slept around a lot, trying to prove to myself that I was straight.

 

It's always hard to disentangle true desire for a person from desire to prop up our own self-image. But do you think you truly desired sex with those women at the time?

[LookingAround]

Its debuncture and derision in the counseling and psych community is a standing joke.

 

Your point?

That's not true.

[BasketBaller]

It's always hard to disentangle true desire for a person from desire to prop up our own self-image. But do you think you truly desired sex with those women at the time?

Well, yes, I did, and I enjoyed it, and I hope they did too. But looking back on it I think it had a lot to do with wanting to be as straight as possible, and in my adolescent mind that meant sex with lots of women.

[AdamSmith]

That's not true.

Beg pardon! Posting while sleepy -- I was thinking of the MMPI.

[Rudynate]

That's been my experience, too.

 

 

Same here. I get way more free sex than paid sex.

[Rudynate]

I don't know if I could still get free sex or not--I simply stopped looking for it when I hit middle age. It was so much more convenient to just hire and get exactly what I wanted when I wanted it. Then when I retired to Palm Springs in my early 60s, I decided one night to see what the bars were like, and was surprised to be picked up and taken home in his Mercedes convertible by a really hot-looking guy of about 40. The sex all night long was fabulous, but I realized it was probably a fluke, and if I expected the experience to be repeated regularly, I was bound to be disappointed. So I stopped looking again.

 

I was talking about PS with a friend just last night. I've never been there - thinking seriously about a visit in the next month. The cold, wet weather in the Bay area has aggravated my asthma symptoms so much that I feel like I need to look for a place to winter over. I was discussing this with a friend just last night. He told me about a friend of his who visited PS for a weekend, stayed at a gay resort and had non-stop sex the entire weekend, and decided to move there, based on that. He lives there now and complains about it non-stop.

[Rudynate]

Well, yes, I did, and I enjoyed it, and I hope they did too. But looking back on it I think it had a lot to do with wanting to be as straight as possible, and in my adolescent mind that meant sex with women.

 

Isn't that generally what being straight means - sex with the opposite sex?

[BasketBaller]

Isn't that generally what being straight means - sex with the opposite sex?

True, LOL. I mean that as a young man in denial about having any interest in men, I tried to prove to myself that I was straight by having sex with as many women as possible. It wasn't completely dishonest, I was attracted to women too and enjoyed the sex. But that didn't mean I was completely straight, as it turned out.

[Rudynate]

I guess I've never been in denial about the fact that I would some day get old. So, now that I'm old, it doesn't surprise me that young men treat me like an older man. Playing in the sexual marketplace is definitely different but no less fun. Younger men call me, "Daddy," or "Boss" or "Sir." They hold doors for me and are generally deferential. It's a different kind of attention, sure. But I like it - I'll take it.

[Rudynate]

True, LOL. I mean that as a young man in denial about having any interest in men, I tried to prove to myself that I was straight by having sex with as many women as possible. It wasn't completely dishonest, I was attracted to women too and enjoyed the sex. But that didn't mean I was completely straight, as it turned out.

 

 

When I was in my late 'teens, I told myself that my same-sex attraction was just a phase - that I would get it out of my system and find a nice girl, settle down, have kids, get a house in the suburbs. When I faced the fact that I wasn't "getting it out of my system," I realized I had to recalibrate - I do remember it was a very sobering realization, that most of the things I expected out of life might not happen.

[+ Charlie]

When I was in my late 'teens, I told myself that my same-sex attraction was just a phase - that I would get it out of my system and find a nice girl, settle down, have kids, get a house in the suburbs. When I faced the fact that I wasn't "getting it out of my system," I realized I had to recalibrate - I do remember it was a very sobering realization, that most of the things I expected out of life might not happen.

+1 My experience was exactly the same.

[Jbdesc]

I don't think there is such a thing as free sex. If we're speaking strictly monetary then sure. I feel every experience gives and takes something from you. Enough with the philosophical discussion though.

 

Even though it's not over I figured I would share my experience.. 'Free' sex is not over. I, however have trust issues with many people - and I tend to be rather shy. Apps tend to lead to hookups or flakes with the occasional silver lining. Hookups are fleeting and don't carry much weight in terms of experience. In fact there have been some where I regret having done anything. I'm yet to have that experience hiring.

 

I have an open relationship with my SO and we have some great fwb arrangements. While we have some great fwb arrangements we've also had a couple that were less than satisfying for me. I guess I hire because I have some form of self esteem issues. I'm a bigger guy (active and losing a lot tho ), my SO however is not. He is about 150lbs, and younger than I. We've had a couple experiences where it was not so much about us, but more about him - and this lead to some discussions about concerns, feelings, and all that mushy stuff.

 

I found hiring has helped my confidence. Even if it's a performance, it has helped me pick my head up a little bit more. And for that I am grateful.

 

Cheers!

[caliguy]

If your ideal man is limited to say a twenty something and you're say a fifty something yep the feebies are over. That or you just let yourself go which I guess could supersede any kind of situation.

[+ quoththeraven]

That's despicable.

 

~Boomer ~

Some people find it acceptable. I can't be more specific without crossing the line into political discourse.

[Zman]

I was talking about PS with a friend just last night. I've never been there - thinking seriously about a visit in the next month. The cold, wet weather in the Bay area has aggravated my asthma symptoms so much that I feel like I need to look for a place to winter over. I was discussing this with a friend just last night. He told me about a friend of his who visited PS for a weekend, stayed at a gay resort and had non-stop sex the entire weekend, and decided to move there, based on that. He lives there now and complains about it non-stop.

 

Is he complaining nonstop about the nonstop sex? I'm sure you are like, "Yah. Bummer dude."

[Rudynate]

Is he complaining nonstop about the nonstop sex? I'm sure you are like, "Yah. Bummer dude."

 

 

Maybe the non-stop sex was an atypical event. It seems like everybody in San Francisco, when they hit 45 or so, retires to PS, where they get lots of tattoos, work out a lot, lay in the sun and have lots of kinky sex. Sounds like a nice life. I'm told Ft. Lauderdale is a similar scene.

[Zman]

Maybe the non-stop sex was an atypical event. It seems like everybody in San Francisco, when they hit 45 or so, retires to PS, where they get lots of tattoos, work out a lot, lay in the sun and have lots of kinky sex. Sounds like a nice life. I'm told Ft. Lauderdale is a similar scene.

Well at least everybody rich enough.

[pubic_assistance]

I get plenty of freebies. Especially the Latin and Asian boys LOVE daddy. I like to hire because, I enjoy massage and you rarely find a random cutie who's a trained masseur ...and I am very American in my love of the power of Capitalism. Find what I want, decide when I want it, how I want it and how much I want to pay. Such a turn on right there. LoL

[handiacefailure]

I can still have free sex but was my early 40s when I realized if I wanted it with guys in their 20s that I find hot to plan on paying for it sometimes. I also have a fairly kinky side so that limits my sex partners as well. I am lucky to find some young guys that like older guys (I'm 50 and in decent shape for my age)

[handiacefailure]

I get plenty of freebies. Especially the Latin and Asian boys LOVE daddy. I like to hire because, I enjoy massage and you rarely find a random cutie who's a trained masseur ...and I am very American in my love of the power of Capitalism. Find what I want, decide when I want it, how I want it and how much I want to pay. Such a turn on right there. LoL

 

Fortunately I am attracted to Asians and find a lot of Asian's like older white guys. Unfortunately though there aren't many Asians in my area