Advice please... need to take the next step!

[CuriousColorado]

So... I told myself I would make this weekend the most adventurous one I've had and I did pretty well. I got on a couple hookup apps yesterday and by 10 a.m. I was in a stranger's hotel room moaning with my mouth full of his cock. By the time I finished I had a couple messages from another guy nearby and ended up in his garage on my knees with his wife unaware that her husband was pumping my mouth as I kneeled on an old futon mattress.

This morning I was completely cock starved and messaged the hotel guy and he was more than happy to help me out. The thing is, while he was laying in bed and I was doing everything I could to keep his heavy dick deep in my throat I got so into it I did something I've never done before. I realized I wanted to feel him stretch me... I went to stroking him and begging him to fuck me, but almost as soon as I did he started to cum and I got busy licking up his mess.

I think I need to take this step but I'm also really nervous so I don't think I would try unless I was already really into sucking cock... and that took a while weekend to get there. Any advice on how to get myself to push past the nerves and get ready to find someone to take my anal virginity?

 

[el_uno77]

So... I told myself I would make this weekend the most adventurous one I've had and I did pretty well. I got on a couple hookup apps yesterday and by 10 a.m. I was in a stranger's hotel room moaning with my mouth full of his cock. By the time I finished I had a couple messages from another guy nearby and ended up in his garage on my knees with his wife unaware that her husband was pumping my mouth as I kneeled on an old futon mattress.

This morning I was completely cock starved and messaged the hotel guy and he was more than happy to help me out. The thing is, while he was laying in bed and I was doing everything I could to keep his heavy dick deep in my throat I got so into it I did something I've never done before. I realized I wanted to feel him stretch me... I went to stroking him and begging him to fuck me, but almost as soon as I did he started to cum and I got busy licking up his mess.

I think I need to take this step but I'm also really nervous so I don't think I would try unless I was already really into sucking cock... and that took a while weekend to get there. Any advice on how to get myself to push past the nerves and get ready to find someone to take my anal virginity?

oh my....share whatever answers you get. i'm looking for someone to take my anal virginity as well....

 

[Escierto]

Practice with a dildo and lube by yourself first. It takes a little while to get the sphincter muscle accustomed to incoming traffic. Once you can handle that, go for the real thing.

 

[nostuff]

Gawd, you are an inspiration.

I've sucked cock and been sucked, but like you, my ass is still cherry, so I can't really offer much advice. I only hope we both find a way to take that next step.

 

[starfish71]

So... I told myself I would make this weekend the most adventurous one I've had and I did pretty well. I got on a couple hookup apps yesterday and by 10 a.m. I was in a stranger's hotel room moaning with my mouth full of his cock. By the time I finished I had a couple messages from another guy nearby and ended up in his garage on my knees with his wife unaware that her husband was pumping my mouth as I kneeled on an old futon mattress.

This morning I was completely cock starved and messaged the hotel guy and he was more than happy to help me out. The thing is, while he was laying in bed and I was doing everything I could to keep his heavy dick deep in my throat I got so into it I did something I've never done before. I realized I wanted to feel him stretch me... I went to stroking him and begging him to fuck me, but almost as soon as I did he started to cum and I got busy licking up his mess.

I think I need to take this step but I'm also really nervous so I don't think I would try unless I was already really into sucking cock... and that took a while weekend to get there. Any advice on how to get myself to push past the nerves and get ready to find someone to take my anal virginity?

So, your hotel guy... was he open to fucking you? If so, you could just keep sucking until he is hard again, then go from there...

Otherwise, it is just a rip the band aid kinda thing, at least it was for me... was super nervous, and could have backed out half a dozen times... you went so far as to blow two guys in one day, and a repeat the next... which is pretty "adventurous"... do the same thing with a different goal...

 

[cubbyfire04]

So, your hotel guy... was he open to fucking you? If so, you could just keep sucking until he is hard again, then go from there...

Otherwise, it is just a rip the band aid kinda thing, at least it was for me... was super nervous, and could have backed out half a dozen times... you went so far as to blow two guys in one day, and a repeat the next... which is pretty "adventurous"... do the same thing with a different goal...

Yep... Just ask the hotel guy. He knows you want him to fuck you. Why not ask? Make sure he knows it's your first time and take it slow. Even if he's not open to it, I've got a feeling he'll still let you suck his cock.

Oh yeah, and all the prep stuff everyone is talking about... Practice on yourself. Lube, fingers, dildos. Cocks are next level but communicate with him and if he's worth continuing on with, he'll oblige.

 

[JP970]

Adventurous day for sure.

I would second the advice of getting yourself a dildo to practice with. If you've gotten to the point that you're craving it, why not indulge? Get something realistic, of a slimmer/average size, and once you've opened yourself up with some lube and your fingers you can explore a little cock in your ass and see if you're ready for the real thing.

I'm generally a total top, but I scratched the itch a while back and got a nice realistic 6"er, two actually, because I was curious and really fantasizing heavily about a twinky three way. Safe and easy intro to anal, and I got to practice my oral on the other one. Super sexy alone time and I realized that I'm definitely verse under the right circumstances.

 

[tristantrotsky]

So... I told myself I would make this weekend the most adventurous one I've had and I did pretty well. I got on a couple hookup apps yesterday and by 10 a.m. I was in a stranger's hotel room moaning with my mouth full of his cock. By the time I finished I had a couple messages from another guy nearby and ended up in his garage on my knees with his wife unaware that her husband was pumping my mouth as I kneeled on an old futon mattress.

This morning I was completely cock starved and messaged the hotel guy and he was more than happy to help me out. The thing is, while he was laying in bed and I was doing everything I could to keep his heavy dick deep in my throat I got so into it I did something I've never done before. I realized I wanted to feel him stretch me... I went to stroking him and begging him to fuck me, but almost as soon as I did he started to cum and I got busy licking up his mess.

I think I need to take this step but I'm also really nervous so I don't think I would try unless I was already really into sucking cock... and that took a while weekend to get there. Any advice on how to get myself to push past the nerves and get ready to find someone to take my anal virginity?

It is a quite normal and natural evolution.
Once you've sucked cock, and enjoyed sucking cock, it's only to be expected that you start into thinking about what other ways it might feel good to experience cock. It's only human to wonder... and then to want to take that step further, and accept a friend's cock up your tight little bum-hole. For me, the decision was taken for me. My friend decided it was time for me to be fucked, and I was in no mood to argue. It was a wonderful experience.
It will be for you too. Don't hesitate too long. Just follow your healthy instinct....

 

[Nicebiguy]

Yep... Just ask the hotel guy. He knows you want him to fuck you. Why not ask? Make sure he knows it's your first time and take it slow. Even if he's not open to it, I've got a feeling he'll still let you suck his cock.

Oh yeah, and all the prep stuff everyone is talking about... Practice on yourself. Lube, fingers, dildos. Cocks are next level but communicate with him and if he's worth continuing on with, he'll oblige.

One other thing,always douche out your boi pussy really well anytime you'll be getting fucked.

 

[MsNatalie99]

You seem to have no problem finding guys, but you finish them off with your mouth. Sucking has it's charm, but if I want to bottom, I only suck till he's hard. Some guys will claim they can come multible times, but most DEs are one pop and off. Give yourself an enema. It'll clean you out, and if your like me, you'll hate the feeling. That'll also be added encouragement not to waste the encounter.

 

[cubbyfire04]

One other thing,always douche out your boi pussy really well anytime you'll be getting fucked.

Also good advice

 

[CuriousColorado]

Well, it's done! I met a guy at home depot today and sucked him off tonight... huge, just really huge cock!! After he came down my throat I was stroking and licking him and he just stayed hard. I got my nerve up and asked him if he would be happier if he could bend me over. He didn't take long to get me over his counter... I was staring out the open kitchen window and squealing as he stretched me out more than I thought I could take!! I've never cum so hard in my life!!! I'm so sore.

 

[saintcero]

Well, it's done! I met a guy at home depot today and sucked him off tonight... huge, just really huge cock!! After he came down my throat I was stroking and licking him and he just stayed hard. I got my nerve up and asked him if he would be happier if he could bend me over. He didn't take long to get me over his counter... I was staring out the open kitchen window and squealing as he stretched me out more than I thought I could take!! I've never cum so hard in my life!!! I'm so sore.

Sounds like a slut has been born. Welcome to your new life bitch. (Yes. I am jealous)

 

[OlderBtm4U]

Thanks for sharing

 

[xdresssissytoes]

Home Depot... huh? Which department? I've got to plan some improvements. Congrats! Find some toys your size and lube to keep that hole loose. You'll be ready next time.

 

[nudeguy76]

Home Depot... huh? Which department? I've got to plan some improvements. Congrats! Find some toys your size and lube to keep that hole loose. You'll be ready next time.

outside behind the sheds for sale

 

[caymancts]

It is a quite normal and natural evolution.
Once you've sucked cock, and enjoyed sucking cock, it's only to be expected that you start into thinking about what other ways it might feel good to experience cock. It's only human to wonder... and then to want to take that step further, and accept a friend's cock up your tight little bum-hole. For me, the decision was taken for me. My friend decided it was time for me to be fucked, and I was in no mood to argue. It was a wonderful experience.
It will be for you too. Don't hesitate too long. Just follow your healthy instinct....

It IS quite normal and natural. Men are supposed to have dicks inside them on a frequent basis. Once you start.........no going back, that's for sure!

 

[Oshkosh60]

So how did you approach him behind the sheds? how did that conversation begin....? That led you to getting fucked in the ass not much later? (Asking for a friend)

 

[nudeguy76]

So how did you approach him behind the sheds? how did that conversation begin....? That led you to getting fucked in the ass not much later? (Asking for a friend)

ive done it a couple times. found guys on an app that wanted to meet there

 

[nassauguy_2001]

So... I told myself I would make this weekend the most adventurous one I've had and I did pretty well. I got on a couple hookup apps yesterday and by 10 a.m. I was in a stranger's hotel room moaning with my mouth full of his cock. By the time I finished I had a couple messages from another guy nearby and ended up in his garage on my knees with his wife unaware that her husband was pumping my mouth as I kneeled on an old futon mattress.

This morning I was completely cock starved and messaged the hotel guy and he was more than happy to help me out. The thing is, while he was laying in bed and I was doing everything I could to keep his heavy dick deep in my throat I got so into it I did something I've never done before. I realized I wanted to feel him stretch me... I went to stroking him and begging him to fuck me, but almost as soon as I did he started to cum and I got busy licking up his mess.

I think I need to take this step but I'm also really nervous so I don't think I would try unless I was already really into sucking cock... and that took a while weekend to get there. Any advice on how to get myself to push past the nerves and get ready to find someone to take my anal virginity?

It's like the old joke, "How do I get to Carnegie Hall?"
Practice, practice, practice!

Lots of lube and take your time to allow your body to adjust to whatever toy you decide to start with. Personally I recommend starting with a slim vibrator and working your way up to a good sized dildo.

Good luck and have fun!

 

[Analsexlover]

So... I told myself I would make this weekend the most adventurous one I've had and I did pretty well. I got on a couple hookup apps yesterday and by 10 a.m. I was in a stranger's hotel room moaning with my mouth full of his cock. By the time I finished I had a couple messages from another guy nearby and ended up in his garage on my knees with his wife unaware that her husband was pumping my mouth as I kneeled on an old futon mattress.

This morning I was completely cock starved and messaged the hotel guy and he was more than happy to help me out. The thing is, while he was laying in bed and I was doing everything I could to keep his heavy dick deep in my throat I got so into it I did something I've never done before. I realized I wanted to feel him stretch me... I went to stroking him and begging him to fuck me, but almost as soon as I did he started to cum and I got busy licking up his mess.

I think I need to take this step but I'm also really nervous so I don't think I would try unless I was already really into sucking cock... and that took a while weekend to get there. Any advice on how to get myself to push past the nerves and get ready to find someone to take my anal virginity?

Just know that nothing feels better than anal sex and thats all your gonna want from now on.

 

[Busy54]

Just know that nothing feels better than anal sex and thats all your gonna want from now on.

Agreed, there is nothing more fulfilling (pun intended) or satisfying than having a strong masculine man on you, pressing into you, grabbing your hips, and fucking you like a whore. You cannot feel the cum, but you can feel his cock pulsing in you. When he does begin to pulse, you will instinctively, contract your pussy in an attempt to hold him inside as long as you can. You won’t want him to soften and pull out. But when he does, his seed running down your thighs will feel so good and satisfying. You’ll be long for the next time immediately, even though you pussy is still stretched and sore. Most glorious feeling.

 

[Illinoisguy1980]

The garage bit sounded hot

 

[johnnyampleed]

Agreed, there is nothing more fulfilling (pun intended) or satisfying than having a strong masculine man on you, pressing into you, grabbing your hips, and fucking you like a whore. You cannot feel the cum, but you can feel his cock pulsing in you. When he does begin to pulse, you will instinctively, contract your pussy in an attempt to hold him inside as long as you can. You won’t want him to soften and pull out. But when he does, his seed running down your thighs will feel so good and satisfying. You’ll be long for the next time immediately, even though you pussy is still stretched and sore. Most glorious feeling.

You have so many lovely, sexy thoughts.

 

[Hardupdad]

Reading all these posts has me craving cock, or even better, cocks to suck. I'm ready to take the next step. Anyone from alberta Canada here?