Anal Question

I like laying on my back with a pillow under my hips to raise my ass up. I lift my legs and spread them so he can have access to my man pussy.
I love to watch him as he thrust in and out of my ass, then to see the expression on his face when he cums inside of me

You should realize that once you get some dick up your ass, you'll start craving it more and more. I always knew I wanted to try dick just once to see how it felt. So I practiced often with dildos and vibrators until one day on my way home from work I was lucky enough to meet a really shapely sexy horny tranny who stuck her big dick up my ass. It was really good dick and she cam in my ass several times. I was satisfied that my fantasy had finally came true and went on my way. A few days later I started feeling horny and all I could think about was her big dick in my ass again. So I got in touch with her and we had sex again. After that second time her dick was all I could think about. I began wanting it more and more. I went back a third time and we fucked again. But this time she taught me how to be good at sucking dicks. I got horny again and again I went to see her. We fucked again but this time she let me wear her high heels while we fucked. This really excited me because her heels felt so good. I wanted to be like her and get all the dick I wanted. Later I would start visiting her while dressed in a mini-skirt and heels and black stockings and she would undress me and fuck me again. Pretty soon whenever she got horny she would call me and ask me for sex. After a while we were fucking all the time. Now we can't stay away from each other. All I ever think about is having sex with her and all she ever thinks about is fucking me in my ass. She is the best lover I have ever had.

I took anal sex once. At first I thought it would never fit; I didn't have any lube, so use lube.
After a little while of slow going I loosened up and it started going in really easily. It started feeling good to me instead of uncomfortable. I didn't want to seem like I enjoyed it, but I could not help it after a while. My backside just automatically humped backed into the stroke in order to make it hit the spot better. This was decades ago and I was not comfortable admitting that I enjoyed anal sex. But I did.
It doesn't have to take several times, as some people report. Everyone is different of course.

The first penetration should be slow, don't clench which you might do without realising you are use to solids coming out, relax and let it slip in all the way you can take any size

First few times it hurts but only when it first goes in. I've had it done to me while on my hands and knees and also on my back. My lover likes giving it to me in the shower. I bend over and grab some wall and he slides it in. It gets better the more frequently you do it.

I definitely am not a woman but I love receiving anal penetration. It does hurt at first but lots of lube and try to relax your ass muscles completely. The reflex reaction will be to clench so try take some slow deep breaths.

On the gay side of it... A lot of straight men enjoy anal play too but many don't talk about it. Women have a g-spot and men have something similar with prostate stimulation which is most easily achieved through anal penetration.

I use a glass dildo that's in the shape of a pepper. It's narrow at the beginning and gets thicker. Perfect for first time penetration!

That's a hot reply. I, too, think I want to try it. I'm 75, married, and suck a fair amount of cock. I sucked a nice 35-year old grad student's cock this past weekend. He was hard, long, and not too thick --- which might be perfect for my first ass fucking. If I can talk him into it. I also would want to go bareback and have the fellow cum deep in my ass. Want to try it all, I guess. Thanks.

It will be a little painful at first but if you have never done it that is to be expected. Try something small at first. Once you get used to it you will find it to be very pleasurable and highly erotic if you do it right.
You will want to do it often once you experience it. Take your time use lube and just take what is comfortable to you and you will enjoy it. I have quite a few sex toys and my favorite are the suction cup base toys. I like sticking them to something smooth like the end of my bed so I can back up to them and guide them in to my ass then fuck my ass while I jack off and it feels great and I always seem to shoot a much larger load and it just feels so much better with something in my ass.
I was curious as a young boy and started sticking different things in my ass back then and was fortunate enough to have a couple of friends that were horny and very curious that actually liked fucking me in the ass once I talked them in to doing it the first time. We didn`t do it a lot but about once a week or sometimes twice a week. It always felt very good to both of us and after a few times I let them cum in me which really did feel very good.
On weekends we could always find a place and have time to do this and it was mostly outdoors in the woods or in some vacant building or any where no one would catch us doing it. Quite a few times at my house or theirs after school before any one got home. I can remember many times rushing home from school with one of my friends both of us getting out of our clothes pretty fast and me laying on a towel getting my ass fucked good taking my friends cum in the ass then getting dressed before any one got home.
On weekends both of them would spend weekends at my house or we would be at one of their houses and if we were alone we would all three get naked and they would take turns fucking me for as long as we could without getting caught.