Anal sex

[Loridan]

Before I was married and much younger I had pretty good luck with women. I'm not proud of this now but few were married (and very nasty in bed).
I always attempted anal, some were no way, some were... ok but be careful, some were like go for it.
The best for me was when she groaned just right as I slid in but didn't scream in pain. Then let out those very hot and different moans as I fucked her butt.
One girl, after I'd fucked her butt for maybe 2 minutes then pulled out said something like...that fucking hurt you ass hole. Buzz ...... for sure.
The best was after, when I pulled out she'd say something like...WOW....or that was different...or that was good. Very hot for me.
My wife does this just right when she gets it back there.

 

[spin418]

My wife is something like that when it comes to anal too. It was a progression and i think it’s pretty simple….she has never really had a negative experience. It was only my tongue there up until her freshman year of college, when another guy really claimed her anal virginity…and gave her her first penetrative orgasms in the process.

She’s typically the initiator.

 

[Filipinagrip12]

My wife told me she never did anal

Little did I know hundreds of hours multiple videos, compilations

 

[1sluttywife4you]

I had been with my wife for 7 years and have tried several different times to fuck her ass but she always said it hurt and would make me stop well long short her first black man had the longest and thickest cock I had ever seen (still to this day) stated out giving her a proper anal training by making sure she was permanently resized to accommodate her new role as a BBC slut

 

[Loridan]

Some of my experiences when trying to get girls to take it in the butt...
Girl would say go for it
She'd say no way
Some said I've never done it but go easy....slipped right in. Obviously she'd done it befor but wouldn't admit it.
Some said go slow. I'd get it in, took a min but they were into it.

 

[malky]

Anal sex has never appealed to me , so I wouldn't do it even though my wife enjoyed it. However, a couple of her boyfriend's did enjoy anal and were only too happy to please her.

 

[PaulLani]

When I'm in the mood, I love a cock up my ass.
I love the way it turns men on.
Paul also likes seeing a cock go balls deep in my asshole.

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L P 001

• PaulLani
• Feb 8, 2025
• 4
• anal bare balls deep cuckold amateur

8 inches balls deep in her ass

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L D 002.mp4

• PaulLani
• Feb 7, 2025
• 7
• amateur cuckold anal homemade

Dave cumming in her ass

 

[Geminisyn]

I've butt fucked my wife countless times over 30 years. She absolutely loves it, makes her cum hard every time.

 

[vegeta2025]

I’ve been with my wife for 6 years, she loves when I go down on her and I always make my way up to licking her ass. She allows me to lick it and play with it but she backs away when I try to put my dick in her ass. One of my fantasies to penetrate her ass, one of these days boys it’ll happen.

 

[Spice]

My ex-wife had a beautiful big round ass that was just asking for a cock, I tried constantly to convince her to let me fuck her ass but she would always say no because I was too big and it would hurt too much, I'm around 8 inches and thick when fully erect so I figured my she's right and finally gave up, eventually after 8 years of marriage we grew apart and finally got divorced, I dated a few girls afterwards but never really tried anal sex with any of them mainly because most were one night stands, then one night by chance I met Terry, she was gorgeous and we hit it off instantly, our first time in bed was amazing, it was a Thursday night and we repeated it Friday, Saturday and Sunday,

The following week we were at my place in bed and I was fucking her doggie style, as I was thrusting in and out I was pushing my finger in her ass, then all of a sudden she just yelled out " put your cock in my ass" "please fuck my ass" those words I would never forget, I immediately pulled out aimed my cock in her tight hole and started pushing in, I could hear her groaning and as her tight hole gave way and my cock popped through I heard her give out a loud gasp as I slid all the way in, I started slow moving in and out and as her hole loosen up I increased the speed, I was in heaven fucking my first ass and everytime I would pull out and push back in she would push her ass back to meet me, she was screaming out telling me to fuck her ass and fuck it deep, then all of a sudden she screamed out that she was cumming and told me to cum in her ass, I immediately unloaded my balls deep inside her gorgeous ass, I couldn't believe that for the first time in my life I had found a woman that not only loved getting her ass fucked but also would cum when I fucked her ass,

It was the start of a beautiful relationship, besides being the first woman to let me fuck her ass Terry was also the first woman to give me my first blowjob and swallow all my cum but that's another story.

Here are some pictures of Terry from the first days we met and after we were living together.