First time anal

[UtilityCurve]

Tonnes of times

That answers both questions! Glad for you (and for the guy or guys).

 

[Mollie06]

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.

 

[Samantha47]

I was young, in my early 20s. I was always curious about anal sex but all the girls I was with over time said the same thing. No! It hurts, it does not feel good and girls only do it in porn.

I’m into enthusiasm, if a girl is not into it things are hard to enjoy so I don’t push it.

But I was curious if they were telling the truth. Being an adventurous person i decided to see what it felt like. So I got a small candle and lay on the couch, then I used the same lube I was stroking with to ease the candle in my virgin ass.

It felt exotic and amazing. It did not hurt, it did not take long before I had an explosive orgasm that was easily double the power of the average orgasm. I was mind blown.

I couldn’t believe it, so I waited and tried again later using only the candle. That’s when I became addicted, the candle alone made me cum. Hard.

Now my girl at the time would have reacted poorly to my discovery so I kept it to myself for a long time. Keeping it hidden is how it became a full blown fetish. I can’t get enough.

I have come a long way from a candle since the early nineties. Now my all time favorite toy is a 17” tentacle that I can take to the base. It is an otherworldly pleasure that only experience can describe. The best part is, my wife is totally cool with it.

My most favorite toy ever! 17” long with a base that is 3.75” wide.

Love that toy

 

[BiBoiSub]

I was young, in my early 20s. I was always curious about anal sex but all the girls I was with over time said the same thing. No! It hurts, it does not feel good and girls only do it in porn.

I’m into enthusiasm, if a girl is not into it things are hard to enjoy so I don’t push it.

But I was curious if they were telling the truth. Being an adventurous person i decided to see what it felt like. So I got a small candle and lay on the couch, then I used the same lube I was stroking with to ease the candle in my virgin ass.

It felt exotic and amazing. It did not hurt, it did not take long before I had an explosive orgasm that was easily double the power of the average orgasm. I was mind blown.

I couldn’t believe it, so I waited and tried again later using only the candle. That’s when I became addicted, the candle alone made me cum. Hard.

Now my girl at the time would have reacted poorly to my discovery so I kept it to myself for a long time. Keeping it hidden is how it became a full blown fetish. I can’t get enough.

I have come a long way from a candle since the early nineties. Now my all time favorite toy is a 17” tentacle that I can take to the base. It is an otherworldly pleasure that only experience can describe. The best part is, my wife is totally cool with it.

My most favorite toy ever! 17” long with a base that is 3.75” wide.

That’s a great looking toy!!

 

[Samantha47]

That’s a great looking toy!!

Would feel so good

 

[BiBoiSub]

Would feel so good

Would feel so good

Yes it would.

 

[Samantha47]

Yes it would.

Love to enjoy with you