Gil's New Butt Adventure

[Wombat23]

45. Back in my first run through university, I had a crisis of identity and was catfished by an older British man posing as someone my own age, and would have killed myself if not for traveling to London/Ipswich to seek the truth. I dropped out of school. It took me almost a decade to get where I could accept who I was. I didn't find my calling (career-wise) until after my mom died, and I am inspired by her and my own sense of justice to return to school, to move on to law school, and to become a public defender/advocate.

I was definitely not relaxed. I couldn't really tell how far it went in, but I don't think it was very much. Certainly not past the bulb part. It wasn't covered in blood or anything, at least.

I might have sex this weekend, btw. And school starts on Monday. Fun times.

Hey trebligon, maybe you can just stick it in. ? My Broke Straight Boys message board status changed from Virgin to Active member - and I didn't feel a thing, ! So press on slowly and don't give up so soon Seriously, bottoming is not for everyone but before you cross it off you menu of pleasure, keep going slowly and be as relaxed as possible as you progress. Good luck. I wonder what your message board status will change to if you become a power bottom overnight ? All the best from down here. W

 

[trebligon]

So it's been a long day and I'm super tired.

I still have not had a penis in my butt. He laid on top of me and humped at me, and started inserting a finger. It was really uncomfortable at first, but he coached me through deep breaths and it became a lot easier. At the end of the session, he said he would prefer not to use his penis because I was so tight that he thought it might turn me off to the whole thing. He said his thrusts would require a lot of force to get through. I went with his advice, but asked him to do some thrusting with his hand so I can at least experience something like being fucked. He complied and that was actually kind of fun. It was like a good pain.

I expected to feel sore or something, but I was just exhausted. He's a really kind guy and I have fallen in love (not literally). He said if I played around with myself I could probably be good in a second session. I look forward to it (though my wallet doesn't).

 

[legend0007]

I have done more pitching than catching and not by choice. I consider myself versatile because I think of man to man sex as where one man gets fucked then fucks during the session. Straight guys usually just get fucked, only the experienced ones will flip you over if they aren't looking for their ass to be filled. There are too many exclusives one way or the other that I looked to toys as an answer. My experience is that hiring a sex worker here in America, or finding someone on a connection site are equally risky. There are catfish in both. I do play with toys and have found that I like those that do the fucking as well as vibrating. One product I liked so much I bought two of them just so I had a back-up in case one broke down. I have heard that diet is important if you are a bottom. Douching and time are the central factors here. Google recomends low fiber and a two hour wait period between meals and sex. I am proudly 70yo. I remember taking part in the sex revolution days before HIV. I got lucky in that I joined the Navy and began playing with virgin straight young men. (Quote: All people start off young but few make it to become old. It is an exclusive club RW)

You're pretty cool aren't you

I don't think there is anything wrong with sex work either; I don't exactly put it in that category but I have seen two guys regularly and got gifts in return, and I have done something with another knowing they would help me with something. But I was still more than happy, and even turned on when doing these things - I hope these guys are getting something like this out of it too?

I was told to douche by my first bf and did it regularly, but have since been told not to, and successfully don't at the moment. I don't want to go into full details Treb (anyone else) but if you dm me I will tell you what i do to limit, well... you know. lol

 

[legend0007]

So it's been a long day and I'm super tired.

I still have not had a penis in my butt. He laid on top of me and humped at me, and started inserting a finger. It was really uncomfortable at first, but he coached me through deep breaths and it became a lot easier. At the end of the session, he said he would prefer not to use his penis because I was so tight that he thought it might turn me off to the whole thing. He said his thrusts would require a lot of force to get through. I went with his advice, but asked him to do some thrusting with his hand so I can at least experience something like being fucked. He complied and that was actually kind of fun. It was like a good pain.

I expected to feel sore or something, but I was just exhausted. He's a really kind guy and I have fallen in love (not literally). He said if I played around with myself I could probably be good in a second session. I look forward to it (though my wallet doesn't).

I'm glad you had an ok experience - I'd had things in me before, but my first time wasn't as gentle or patient. How much did it cost or is that a rude question? Don't answer if it's rude x

edit - comment about my first time sounded misleading - i don't regret what happened or anything like that. It was a cathartic experience x

 

[br6205]

Never regret doing things only not doing them out of fear.

 

[trebligon]

I'm glad you had an ok experience - I'd had things in me before, but my first time wasn't as gentle or patient. How much did it cost or is that a rude question? Don't answer if it's rude x

$300

 

[br6205]

$300

Was it worth it?

 

[mikeyank]

You're pretty cool aren't you

I don't think there is anything wrong with sex work either; I don't exactly put it in that category but I have seen two guys regularly and got gifts in return, and I have done something with another knowing they would help me with something. But I was still more than happy, and even turned on when doing these things - I hope these guys are getting something like this out of it too?

I was told to douche by my first bf and did it regularly, but have since been told not to, and successfully don't at the moment. I don't want to go into full details Treb (anyone else) but if you dm me I will tell you what i do to limit, well... you know. lol

That is very cool and quite natural in the ways of the world Max. A good friend of mine who was in his 20’s at the time, met a man in his fifties who also gave him gifts as they had sex. The older man later mentored my friend in his career and turned out to be one of the most influential people in his life.

As I said it is the “way of the world”, including on Broke Straight Boys, with hot young men being compensated to provide sexual pleasure of mostly older gentlemen, (and some young ones like you Max too, lol). But older guys spend money with young ladies and young men. Always happened, always will.

 

[trebligon]

Was it worth it?

Yes.

 

[br6205]

I am happy for you.

 

[entonces65]

You're pretty cool aren't you

I don't think there is anything wrong with sex work either; I don't exactly put it in that category but I have seen two guys regularly and got gifts in return, and I have done something with another knowing they would help me with something. But I was still more than happy, and even turned on when doing these things - I hope these guys are getting something like this out of it too?

I was told to douche by my first bf and did it regularly, but have since been told not to, and successfully don't at the moment. I don't want to go into full details Treb (anyone else) but if you dm me I will tell you what i do to limit, well... you know. lol

You're pretty cool aren't you

I don't think there is anything wrong with sex work either; I don't exactly put it in that category but I have seen two guys regularly and got gifts in return, and I have done something with another knowing they would help me with something. But I was still more than happy, and even turned on when doing these things - I hope these guys are getting something like this out of it too?

I was told to douche by my first bf and did it regularly, but have since been told not to, and successfully don't at the moment. I don't want to go into full details Treb (anyone else) but if you dm me I will tell you what i do to limit, well... you know. lol

During the confused days of just coming out at age 20, I had no one to show me the ropes as it were. I had not yet learned of gay bars either. The only people I knew that made gay sex were the boys that stood on a corner in Detroit. So, much of my first sex experiences I paid for. I was a hit with the guys because I was young. This led me to never avoid the option of sex workers and I treat them as humans. Hiring a sex worker is comparable to daiting in cost. I also found that plenty of the men would do what is called bait and switch, or back in the days of Backpages they would catfish. These were disapointing. The best places to find sex workers is overseas. As a tourist, never expect to have sex and not pay for it. Most countries do not prohibit sex work. In Asia you have to be careful and ask for age, because many underage children sex work there. It is still against the law to have sex with an underage person in America no matter where you are. My peronal preference are Latinos, Colombia leads the pack, with Brazilians a close runner up. Anthony Bourdan once said that Brazilians look like they are going to have sex or just got done having sex. They simply carry themselves as sexy. Mexico is easy to get to just watch your wallet while having fun. Sex workers are fun, they rarely have diseases and they make the best tour guides overseas.

 

[trebligon]

During the confused days of just coming out at age 20, I had no one to show me the ropes as it were. I had not yet learned of gay bars either. The only people I knew that made gay sex were the boys that stood on a corner in Detroit. So, much of my first sex experiences I paid for. I was a hit with the guys because I was young. This led me to never avoid the option of sex workers and I treat them as humans. Hiring a sex worker is comparable to daiting in cost. I also found that plenty of the men would do what is called bait and switch, or back in the days of Backpages they would catfish. These were disapointing. The best places to find sex workers is overseas. As a tourist, never expect to have sex and not pay for it. Most countries do not prohibit sex work. In Asia you have to be careful and ask for age, because many underage children sex work there. It is still against the law to have sex with an underage person in America no matter where you are. My peronal preference are Latinos, Colombia leads the pack, with Brazilians a close runner up. Anthony Bourdan once said that Brazilians look like they are going to have sex or just got done having sex. They simply carry themselves as sexy. Mexico is easy to get to just watch your wallet while having fun. Sex workers are fun, they rarely have diseases and they make the best tour guides overseas.

What's wrong with Puerto Ricans?! Too American for you?! Oh right...

I'm in college (second semester starts tomorrow! Eep!) and with all the lovely young men around, I am terrified I'm going to be appreciating a 17-year-old. Luckily (?) no one has hit on me in a way I was aware.

 

[br6205]

What's wrong with Puerto Ricans?! Too American for you?! Oh right...

I'm in college (second semester starts tomorrow! Eep!) and with all the lovely young men around, I am terrified I'm going to be appreciating a 17-year-old. Luckily (?) no one has hit on me in a way I was aware.

The way you are thinking indicates you are serious and cautious, those are good treats to have. But don't be afraid to experient. I wish I had been that way back then. You might be lucky and find a mentor to help guide and advise you

 

[entonces65]

What's wrong with Puerto Ricans?! Too American for you?! Oh right...

I'm in college (second semester starts tomorrow! Eep!) and with all the lovely young men around, I am terrified I'm going to be appreciating a 17-year-old. Luckily (?) no one has hit on me in a way I was aware.

I love Puertorriqueños and Cubanos Et. al. Latinos. I live in a Latin neighborhood. Can't understand a word of Chilian Spanish but I had a great time there too.

 

[trebligon]

I love Puertorriqueños and Cubanos Et. al. Latinos. I live in a Latin neighborhood. Can't understand a word of Chilian Spanish but I had a great time there too.

I was just being silly because I am Puerto Rican.

 

[Burgess23]

Wow, just catching up on all things forum related after a mini holiday. I am glad that the experience was okay for you @trebligon. Hiring someone in my opinion is totally fine. I had done the Grindr experience and on the whole people say who they are but I have been catfished twice. One was a really creepy individual who lied about everything best said about that the better!

 

[mikeyank]

Wow, just catching up on all things forum related after a mini holiday. I am glad that the experience was okay for you @trebligon. Hiring someone in my opinion is totally fine. I had done the Grindr experience and on the whole people say who they are but I have been catfished twice. One was a really creepy individual who lied about everything best said about that the better!

I love when members of the forum share some of our previous real life experiences, both good and bad. I hope you had a wonderful mini-holiday, Burgess. Welcome back.

 

[trebligon]

It's hard to find time to stretch my anus. The Daodejing is a mood-killer.

 

[br6205]

It's hard to find time to stretch my anus. The Daodejing is a mood-killer.

What do you mean by The Daodejing?

 

[trebligon]

What do you mean by The Daodejing?

We're reading it and having to do lots of discussion (online and in-person). I am not a fan. Its message of being content and don't make waves feels like a slap in the face of those who strive for a better life and a better world.