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First time anal

Mollie06 said:
Older man took my anal cherry.
He made sure i had been using plugs for a month or so before hand.
He gave me dildos 2 diff sizes to use and practice on as homework.
Then the night happened. He lubed my asshole up and inserted a good sized plug.
Pushed a vib egg into my pussy then ate me out.
Once i was so horny he pulled the plug out and heard the little pop. pushed his cock head to my asshole. told me to pull my ass apart. (i was on my back with my knees up by me ears) He took his time to get himself into me so my butt was relaxed. he is on the larger side.
Once he was inside me, he would go in a bit, remove his cock. my ass felt empty. then he would push in again.
He done this like 10 odd times. meanwhile he switched the egg on and my eyes roll back in my head.

After popping in and out of my butt he told me to let go of my butt cheeks and hold my ankles.
He turned my egg off and popped out, placed more lube on my hole and pushed in again. Now my hole had relaxed enough i could take him into me so much easier and felt nice.

But then he pushed deeper and deeper. held himself there, pull back and repeat. my heart was racing, my breathing elevated, he told me to relax and embrace my use.

A few times he pushed in and i held his hairy chest and told him it was as deep as it could go, it was becoming sore as pressure inside me built as his cock head explored me.
He pulled all the way out, he added lube, fingered my asshole for a bit, told me my internal sphincter needs to be broken in to take larger cock.
He pushed in and fucked my ass at a fast pace. i held on and grit my teeth. Several min later he slowed down and almost come to a stop. told me turn my egg on. i clicked the remote, and he pushed up again.
he pushed a few times and he seen the discomfort on my face.
He lifted my butt up more so now im looking at my tits and can see my tummy and pussy.

i watch as his cock slides out and pushes in again. I watch as his cock goes into my ass, and watch his shaft get shorter as he goes deeper, then feel his cock head again thump at my internal sphincter.
He said "One of your purposes is to endure right? Here we go," He pushed hard against my insides. I open my eyes and look to what he is doing to me with each push. i see a bulge push up at my belly button.
I look past this bump and he still had 40% of his shaft exposed to get go in me. I kinda started to panic.

He reassured me it will be ok very soon. All i could feel was pressure as i got impaled.
I let out a cry and he grunted as my internal muscle let go and he pushed in with ease.
Told me i was a good girl, as he went balls deep and rested me back down.
Felt like his cock head was up in my tummy. A weird calm and bliss came over me as he lay on me with his cock fully inside.

He started to pull out and could feel my insides become empty. He got to point he was almost out of my asshole and pushed all the way in with one stroke. I remember the look on his face of pure happiness.

My eyes were still wide open and he asked if I was ok and how did I feel. I just said "good now"

He ass fucked me hard, first time i kinda felt like a cock sleeve. Its very different feeling.
After my asshole stayed open for like 30min. eventually it closed up again.
So that was my first time.
Click to expand...
Thats the way to do it, gently.
Done a couple girl friends this way.
We both enjoyed it.
 
I want to preface this by saying that I was stupidly lucky and if anything in sex requires clear communication beforehand it’s anal (bondage is second), and I failed in that respect but it worked out anyway.

The two best things about my wife were first that she was multiorgasmic. Once I figured this out I stopped literally and figuratively bending over backward trying to finish with her. Synchronizing on her second O was so much easier for me and allowed me the space to enjoy (myself and her) instead of perform. And having gotten out of my own head I had the time and the headspace to play.

The second was that she had enough of a surplus of lubrication that I could get my fingers properly wet to try things. I have the brain of a superintelligent raccoon so novelty-seeking is a constant temptation, and when you’re horny there’s a lot of temptation. I started with like caressing her labia with my fingertips during PIV, culminating in exploring her behind with the pad of my thumb during doggy, which she seemed to enjoy. A lot. Over the next month I experimented with rhythm, pressure and timing. I knew what anal beads were and how they were best employed and I did my best to simulate that experience.

We did a lot of doggy during that month. Basted on enthusiasm and volume it was clearly some of my best-reviewed work.

So one day she asked if we should try anal next time. I went slow, lots of stretching and lots of lube. We both supposedly had a good time and finished. I can think of many reasons there wasn’t a repeat, like it was probably still a bit much going from digital to the real thing in a single night. Like the relationship was already in decline. Like we didn’t communicate enough about kinks and expectations. Like that simultaneous stimulation is twice as many nerve endings and it stands to reason that multitasking would feel much, much better than either or.

So the thumb stayed on the greatest hits list but anal was more of a bucket list checkbox that we already checked.
 
Mollie06 said:
Older man took my anal cherry.
He made sure i had been using plugs for a month or so before hand.
He gave me dildos 2 diff sizes to use and practice on as homework.
Then the night happened. He lubed my asshole up and inserted a good sized plug.
Pushed a vib egg into my pussy then ate me out.
Once i was so horny he pulled the plug out and heard the little pop. pushed his cock head to my asshole. told me to pull my ass apart. (i was on my back with my knees up by me ears) He took his time to get himself into me so my butt was relaxed. he is on the larger side.
Once he was inside me, he would go in a bit, remove his cock. my ass felt empty. then he would push in again.
He done this like 10 odd times. meanwhile he switched the egg on and my eyes roll back in my head.

After popping in and out of my butt he told me to let go of my butt cheeks and hold my ankles.
He turned my egg off and popped out, placed more lube on my hole and pushed in again. Now my hole had relaxed enough i could take him into me so much easier and felt nice.

But then he pushed deeper and deeper. held himself there, pull back and repeat. my heart was racing, my breathing elevated, he told me to relax and embrace my use.

A few times he pushed in and i held his hairy chest and told him it was as deep as it could go, it was becoming sore as pressure inside me built as his cock head explored me.
He pulled all the way out, he added lube, fingered my asshole for a bit, told me my internal sphincter needs to be broken in to take larger cock.
He pushed in and fucked my ass at a fast pace. i held on and grit my teeth. Several min later he slowed down and almost come to a stop. told me turn my egg on. i clicked the remote, and he pushed up again.
he pushed a few times and he seen the discomfort on my face.
He lifted my butt up more so now im looking at my tits and can see my tummy and pussy.

i watch as his cock slides out and pushes in again. I watch as his cock goes into my ass, and watch his shaft get shorter as he goes deeper, then feel his cock head again thump at my internal sphincter.
He said "One of your purposes is to endure right? Here we go," He pushed hard against my insides. I open my eyes and look to what he is doing to me with each push. i see a bulge push up at my belly button.
I look past this bump and he still had 40% of his shaft exposed to get go in me. I kinda started to panic.

He reassured me it will be ok very soon. All i could feel was pressure as i got impaled.
I let out a cry and he grunted as my internal muscle let go and he pushed in with ease.
Told me i was a good girl, as he went balls deep and rested me back down.
Felt like his cock head was up in my tummy. A weird calm and bliss came over me as he lay on me with his cock fully inside.

He started to pull out and could feel my insides become empty. He got to point he was almost out of my asshole and pushed all the way in with one stroke. I remember the look on his face of pure happiness.

My eyes were still wide open and he asked if I was ok and how did I feel. I just said "good now"

He ass fucked me hard, first time i kinda felt like a cock sleeve. Its very different feeling.
After my asshole stayed open for like 30min. eventually it closed up again.
So that was my first time.
Click to expand...
Wonderful recounting, hard now and waiting for company to leave
 
liliput1 said:
I want to preface this by saying that I was stupidly lucky and if anything in sex requires clear communication beforehand it’s anal (bondage is second), and I failed in that respect but it worked out anyway.

The two best things about my wife were first that she was multiorgasmic. Once I figured this out I stopped literally and figuratively bending over backward trying to finish with her. Synchronizing on her second O was so much easier for me and allowed me the space to enjoy (myself and her) instead of perform. And having gotten out of my own head I had the time and the headspace to play.

The second was that she had enough of a surplus of lubrication that I could get my fingers properly wet to try things. I have the brain of a superintelligent raccoon so novelty-seeking is a constant temptation, and when you’re horny there’s a lot of temptation. I started with like caressing her labia with my fingertips during PIV, culminating in exploring her behind with the pad of my thumb during doggy, which she seemed to enjoy. A lot. Over the next month I experimented with rhythm, pressure and timing. I knew what anal beads were and how they were best employed and I did my best to simulate that experience.

We did a lot of doggy during that month. Basted on enthusiasm and volume it was clearly some of my best-reviewed work.

So one day she asked if we should try anal next time. I went slow, lots of stretching and lots of lube. We both supposedly had a good time and finished. I can think of many reasons there wasn’t a repeat, like it was probably still a bit much going from digital to the real thing in a single night. Like the relationship was already in decline. Like we didn’t communicate enough about kinks and expectations. Like that simultaneous stimulation is twice as many nerve endings and it stands to reason that multitasking would feel much, much better than either or.

So the thumb stayed on the greatest hits list but anal was more of a bucket list checkbox that we already checked.
Click to expand...
Awsome account
 
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