First time fuck buddy tonight

[curiousgeorge30]

Hey
So my good friend is coming over in an hour and he made it clear we are getting drunk and doing it.
I have shared a girl with him in the past and given him a blow job but never gone the full round.
We r both into shemales,should I just get drunk and put on some shemale porn.
I have a some lube,some suspenders he wants to wear,my cock is thicker than his so any advice on how to not hurt him and him not hurt me lol.
should we wear condoms as I know he is clean as am I but I read its a lot more sensual if he can cum in my ass.
Getting hot thinking about it lol,any advice for a newbie as I am a little anxious.

 

[Bacton1111]

Wow. Sounds so hot. Can't give you any advice but very jealous and would love to hear how it goes

 

[curiousgeorge30]

I ma a bit apprehensive about it at the moment the more I contemplate it.
Someone said it will hurt,we both look good and his cock is a bit pointy but he is crazy for mine and says he will swallow my load and share the cum with me lol.

I guess I will go through with it,the bottle of jack should help ease the ring pain and make me more adventurous.

 

[NCcdgurlfriend]

I ma a bit apprehensive about it at the moment the more I contemplate it.
Someone said it will hurt,we both look good and his cock is a bit pointy but he is crazy for mine and says he will swallow my load and share the cum with me lol.

I guess I will go through with it,the bottle of jack should help ease the ring pain and make me more adventurous.

If you had more time I would suggest you picking up a couple butt plugs for the both of you. Put them in and wear them during dinner and while you're drinking. Then I'd suggest you both wear a pair of sexy panties and start your session with nice, long blow jobs. Once you're both really turned on, take the butt plug out, lube up really well, and take his cock in your ass. Tell him to ease it in very slowly and all the way. He'll need to hold it all the way inside of you for a few seconds before starting to SLOWLY push in and out of your ass. Try being on your back at first. Let me know how it goes. I'm jealous!

 

[johnhobes]

one day.......

I will go after a buddy of mine that adores my cock.. I'd love a nice guys weekend... Oh what I wouldnt explore with his fat cock.. even though he cums very quick, id play all night..

 

[Trap1]

I wish I had friends like that.

 

[curiousgeorge30]

If you had more time I would suggest you picking up a couple butt plugs for the both of you. Put them in and wear them during dinner and while you're drinking. Then I'd suggest you both wear a pair of sexy panties and start your session with nice, long blow jobs. Once you're both really turned on, take the butt plug out, lube up really well, and take his cock in your ass. Tell him to ease it in very slowly and all the way. He'll need to hold it all the way inside of you for a few seconds before starting to SLOWLY push in and out of your ass. Try being on your back at first. Let me know how it goes. I'm jealous!

an update,
well it went better than expected, I think I am a little drunk still and definitely feel it in the ass lol.
He came over with a blonde wigg and his girlfriend s panties, we both got a good buzz on first and started to masturbate to some shemale porn I put on.

He just went down on me and gave me one awesome blowjob, fingering my ass and licking my ass.
I did the same for him and actually liked his precum taste, he got his cock circumcized last yr and its really smooth.
He went first and lubed my ass, it was not slow he just shoved it in and started to fuck me bareback with me facing him and the wigg was a tutn on.
I reciprocated the favour and entered him slowly though, must have fucked him for 30mins and he gave me poppers which, loosened my control and I came so damn hard up his ass, a mazsive orgasm . seriously never came so much, it was dripping out his ass.

he needed to finish and started to fuck me over the bed, the noise we were making, U dont know what area he hit but I really was in ecstasy as he fucked me and my legs were shaking.
The cum just started squirting out of me it would not stop the more he fucked me the more I was cumming until he came in me, which felt awesome.
it was falling out my ass when I went to the toilet, dripping on the floor.

Good night indeed, he left an hour ago and it was not awkward,I gave him a shkrt blow job before he left and he slighlty came in my mouth, I think he was drained.
will do it again, a little sore today but I never had an orgasm like it. lol

 

[Trap1]

So hot! I am so glad it went so well!

 

[Bacton1111]

Amazing
Nice to hear all about it

 

[photobuff56]

full details needed

 

[photobuff56]

Amazing
Nice to hear all about it

wish we could meet up

 

[bottomshooter]

an update,
well it went better than expected, I think I am a little drunk still and definitely feel it in the ass lol.
He came over with a blonde wigg and his girlfriend s panties, we both got a good buzz on first and started to masturbate to some shemale porn I put on.

He just went down on me and gave me one awesome blowjob, fingering my ass and licking my ass.
I did the same for him and actually liked his precum taste, he got his cock circumcized last yr and its really smooth.
He went first and lubed my ass, it was not slow he just shoved it in and started to fuck me bareback with me facing him and the wigg was a tutn on.
I reciprocated the favour and entered him slowly though, must have fucked him for 30mins and he gave me poppers which, loosened my control and I came so damn hard up his ass, a mazsive orgasm . seriously never came so much, it was dripping out his ass.

he needed to finish and started to fuck me over the bed, the noise we were making, U dont know what area he hit but I really was in ecstasy as he fucked me and my legs were shaking.
The cum just started squirting out of me it would not stop the more he fucked me the more I was cumming until he came in me, which felt awesome.
it was falling out my ass when I went to the toilet, dripping on the floor.

Good night indeed, he left an hour ago and it was not awkward,I gave him a shkrt blow job before he left and he slighlty came in my mouth, I think he was drained.
will do it again, a little sore today but I never had an orgasm like it. lol

That is fucking amazing

 

[curiousgeorge30]

Well
Planning round two a little later on,he says he has a twist for me but I am not sure what that could be lol,he can go over the top a bit.I think he wants us to double team a shemale,as he has a fantasy of both our cocks up a hot shemale ass, I was told to bring my own funds so thats what I am thinking,there is one super hot one in our town tonight.
Will update a little later
This time though I am first out the gap,he needs to feel the same orgasm I got as it rocked my ass lol.
Glad you liked my little adventure

 

[curiousgeorge30]

We have both agreed this will be the last time trying it as well,may as well ride it out on a high,than fuck up a friendship lol.

Good to try these things once as they say,will post my last update tomorrow and I intend to get real dirty as am off work for the next 3 days.

 

[biggreg]

Good luck , have fun

 

[curiousgeorge30]

Fun was had,
Sadly all good things must come to an end,time to move back to the females.
It was fun but not much beats a sweet pussy,at least I have dipped and tried.
Good luck

 

[herrdrier]

Fun was had,
Sadly all good things must come to an end,time to move back to the females.
It was fun but not much beats a sweet pussy,at least I have dipped and tried.
Good luck

Sounds nice. What about a MMF? I could never give up on pussy but a nice hard one from time to time would be nice. Both at the same time? Awesome.

 

[HomerSimpson123]

Fun was had,
Sadly all good things must come to an end,time to move back to the females.
It was fun but not much beats a sweet pussy,at least I have dipped and tried.
Good luck

Thanks for sharing.