about 8 years ago I was 100% top. I had tried being bottom a couple of times. Once whilst on holiday 25 years ago in Gran Canaria I was fucked by a guy i meT on the gay nude part of the beach. It was incredibly painful and from then I shield away from guys wanting to penetrate me. I started trying bottom again whilst during one of my frequent trips to Pattaya when during a massage the boy partially inserted his cock in me. I didn’t let him carry one but in retrospect I found the experience erotic so later I invited an off boy with a slim dick to top me. I persevered with moderate pain and enjoyed it when he came. From then on I was Regularly bottom but in the early days of my trips I have to try and get boys to penetrate me very slowly using plenty of KY.

1 hour ago, AlexThompson said:

 

.  I revealed the box of condoms and he looked surprised and then smiled. maybe I do have some regrets about not going for it? 

 

A box of condoms? Now you were really prepared for an evening of fun/pain. 

9 hours ago, AlexThompson said:

.  So maybe therapy, PreP or a combination of the two?  And PRACTICE!  Definitely practice.

 

try shot of gin before practice , should work

11 hours ago, AlexThompson said:

Thanks so much, @DrimVoiz and others for your continued insights.  I am definitely intrigued....

This past summer, I spent two weeks in Phuket.  I met a great 27 year-old local guy on Grindr on my first night and he slept over every night from that point on.  Handsome, fit, smart, big dick.  After a few days, I was surprised that he didn't initiate anal so i asked him about it and he said, "Oh, I just thought you weren't into that."  I was determined to prove him wrong, so I bought condoms and lube...

I was staying in a gorgeous, secluded house in the hills...it was pouring rain outside....the bed was amazing...we had been making out for hours...it was all so incredibly romantic.  I revealed the box of condoms and he looked surprised and then smiled.  He asked if I wanted to top or bottom, and I said bottom.  He slipped it on.  We were hot and ready  He made it to the entrance...

....and then I panicked and stopped.

Thankfully, it didn't matter to him and the rest of our time together was perfect.  But maybe I do have some regrets about not going for it? For me, it truly wasn't about the possibility of physical pain.  I think I just have this leftover fear from the 1980's.  So maybe therapy, PreP or a combination of the two?  And PRACTICE!  Definitely practice.

 

I think you need more 4play, more kissing, more sucking, more romance so u will get relax...tbh with u, my 1st time was sooo romantic that I agreed 2 pop my cherry, lol...also its all in the mind, just clear your thought, expect it will hurt but try 2 relax, let him in slowly, practice with your finger, lol...just do it when ur ready, but my advice 2 u, make it sooner bcoz u already got a perfect partner, ur losing time whereas u should really enjoying it by now, the more you keep it longer, the lesser time u'll enjoy it with ur perfect partner, so make the most while ur still together, good luck!!! Its only my opinion, the decision is still yours...

11 hours ago, AlexThompson said:

I think I just have this leftover fear from the 1980's.  So maybe therapy, PreP or a combination of the two?  And PRACTICE!  Definitely practice.

Seriously, that leftover fear from the 80s is so incredibly outdated. I understand it may sit deep because back then an hiv infection was a near-certain death sentence. Nowadays, in the INCREDIBLY unlikely event that you should catch hiv despite being on PrEP AND condoms (virtually impossible to get it really) it is also a certain sentence - to take a pill a day until you die a peaceful death of old age. Nothing much wrong with that, because millions upon millions of people, including I bet a sizable percentage of forum members, take one or more pills every day for all sorts of ailments like high blood pressure or whatever else. Big fucking deal (as it were).

40 minutes ago, DrimVoiz said:

also its all in the mind, 

couldn't agree more. 

So go see a therapist, let him get you out of the old 80s anxiety and then go and ENJOY  

10 hours ago, kokopelli said:

A box of condoms? Now you were really prepared for an evening of fun/pain. 

A typical box of condoms sold at 7/11 contains about 2-3 condoms, some brands maybe even a whopping single condom.

Last night, I made the craziest purchase of my life and thought of you gents the whole time -- a butt plug trainer kit.  I have never put anything up there in my life.  You'll be pleasantly surprised and/or horrified to learn that I graduated to the biggest of three within ten minutes.    (Maybe I was born a bottom after all?)  I relaxed, put some porn on, and really enjoyed the experience.  Afterward I was blushing and laughing to myself like a teenager who had  just lost their virginity.  

I couldn't have done it without your encouragement.  Looking forward to continuing the practice and overcoming the mental hurdles.

20 minutes ago, AlexThompson said:

I graduated to the biggest of three within ten minutes

And in a more serious manner, congratulations! 

Wow! I wonder what kept you all this time from trying the sex toys? Surely not fear of HIV? Hehehe. Kidding aside, i think you are ready lol

1 hour ago, anddy said:

A typical box of condoms sold at 7/11 contains about 2-3 condoms, some brands maybe even a whopping single condom.

Guess I was thinking of the 36 condoms/box which I purchase. 

1 hour ago, AlexThompson said:

  Afterward I was blushing and laughing to myself like a teenager who had  just lost their virginity.  

 

enjoy while it lasts, it never hurts to feel young again

5 hours ago, AlexThompson said:

Last night, I made the craziest purchase of my life and thought of you gents the whole time -- a butt plug trainer kit.  I have never put anything up there in my life.  You'll be pleasantly surprised and/or horrified to learn that I graduated to the biggest of three within ten minutes.    (Maybe I was born a bottom after all?)  I relaxed, put some porn on, and really enjoyed the experience.  Afterward I was blushing and laughing to myself like a teenager who had  just lost their virginity.  

I couldn't have done it without your encouragement.  Looking forward to continuing the practice and overcoming the mental hurdles.

Nice, very nice start Alex!!! But you'll definitely enjoy the real m*nh**d with your perfect partner, lol. It makes me wonder how many inches u used, haa haa  

One of the best threads I've ever read! Congratulations Alex. Brought a smile to my face as no doubt it did to yours...