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Would Not Fit

I am married but very curios about bottoming for another man. I have fantasied about it for a long time now. I had the house to myself last weekend so i decided to try and fuck my own ass with something to see how it felt. What i found out is that my ass is very tight and I could not get anything in it. I tried a cucumber at first, then a carrot. Don't know if I'm just tensing up and that why they wont go in. Does anyone have any suggestions? I feel i need to stretch it out a little before i try the real thing. And yes i tried using lube.

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# 82731 - by Scottr9989 / September 24, 2025
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Comments

Anonymous

by Anonymous on Sep 24, 2025 at 5:40 PM

Probably need to start with something the size of a wiener and some good quality lube. Works lots better when you are very aroused maybe watching some good hot gay or hi sex. I have never been able to enjoy anything real

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Billywatkins1

by Billywatkins1 on Sep 24, 2025 at 6:05 PM

I'm a 58-year-old bi divorced maleI enjoyed anal for a long time. Between my late teens and 30 side periodically had anal and although it was always painful, it was also enjoyable. Then one day I was with this guy and he had some lube on a finger and was working at in my ass which felt awesome. I slowly began to relax (which is an unnatural feeling). And then he had my ankles in his hands and started pushing into me. I managed to stay relaxed and it felt amazing.
You may want to try getting a sec of butt plugs that increase in size. The key though is being able to relax. Once you do it will feel so amazing!

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Anonymous

by Anonymous on Sep 25, 2025 at 6:04 AM

You have to learn to relax and just let it happen. Let's face it your anus is made to expel not to have it pushed on. Once you learn how to relax there's no feeling let it your prostate getting rubbed on with a hard cock.

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Anonymous

by Anonymous on Sep 25, 2025 at 8:46 AM

Lube and stretch with your fingers first. You will feel small creases inside your ass. Massage them to relax your ass. Then you should be able to start using various things in your ass. If you don't have toys, try an English cucumber. They are my favorite to use when travelling. Girth is good, long enough to experiment with how deep you can go, and long enough to have something to easily hang on to while fucking yourself. No matter how good that feels though, you are in for a real treat when you have real cock inside you the first time, and I pretty much guarantee you will love it. Have your ass stretched and lubed before you meet up, many guys don't know how to lube and stretch an ass to make it feel good for the bottom.

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Anonymous

by Anonymous on Sep 25, 2025 at 12:17 PM

Lots of lube really helps. Making out before hand also. I personally like when it hurts going in. Being rocked as the pain turns to pleasure is so erotic.

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Anonymous

by Anonymous on Sep 25, 2025 at 1:47 PM

Absolutely nothing like A real cock fucking your boi c*nt. nothing else feels like it. Bare Back is 1000% better. Best to start with small to average size cock. Go to A nude beach or gym [ you really don't think most of them don't want your cock or ass do you ? ]
Key is tell him go very slow. You will get turned on just knowing that even just a little of his cock is in your boi cu*t . Enjoy the pain of being filled and fuck. Oh boy will you.
PS the easiest way is Sitting on his cock. MMMMMMMMMMMM

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Anonymous

by Anonymous on Sep 26, 2025 at 6:16 AM

It was pretty easy for me my cousin and I were 10 years old and up in the hay lift of our barn he and I started to jack off together and once he grabbed my hard dick and started to jack me off I did the same to him. He said we should get naked so we did.
Both of us just stood there facing one another with our dicks hard as a rock k and he told me we should try to screw. At that point I would have done anything and he got me to lay down in the hay then roll over face down. He used his knees to spread my legs then I felt him holding his dick rubbing it on my ass then touching it to my asdhole telling me he wanted to put it in me. I told him to try it and shortly after that I had his dick in my tight ass and as he laid on top of me working his dick back and forth in my hole he shot his tiny load up my asshole.
He asked me if I was OK and I told him yes and I liked it. He said he wanted to keto going so he did. He screwed me for a very long time with his hands under me playing with my dick and he made me cum just before he came in my ass a second time.
We did it two more times that day in other places and for years he screwed me many times and so did other boys all thru my school years. As an adult I have had anal send with men but not much but I still enjoy it. And after my first divorce I decided to have sex with men again and after having two different men in my ass I decided it was time to try a big one. I bought a couple of sex toys and one was pretty large. Weeks later on Craigslist I found this married Hispanic man with a huge cock. I had him come to my house one Saturday and his dick was extremely thick and over 10” and once I took it all the way he fucked and pounded me until he came deep in my ass twice. He stayed for hours and fucked me several times shooting his big thick load up my ass multiple times. For months after that almost every Saturday he dropped by my house to fuck me and one day he asked if he could bring a friend and I had my first 3 way with two hung Mexican men. They came to my house a few times and I got addicted to two big Mexican cocks and all I wanted was big hard brown dick and taking one up my ass and one in my mouth was really good then one day they worked and worked and finally got both cocks in my ass at the same time and all I could do was yell and scream and beg to be fucked and they both came up my ass at the same time. They did it again later on that day and for some reason they never came back and I moved. I met my wife and we have been married 25 years but early in our relationship we were swapping fantasies and after I knew I could trust her I told her I had been curious about anal sex and had a strap on fantasy and we bought a harness and a few rubber cocks and for years she enjoyed fucking me up the ass but we don’t do it anymore so when I have the time alone I enjoy fucking myself and I guess I always will

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Anonymous

by Anonymous on Sep 30, 2025 at 10:11 AM

Married male, between marriages I got into getting head from men and then into sucking cock myself. I was hooking up with a man in the same neighborhood for a while. The routine was me sucking his cock while I jacked off. He asked it I'd suck another buddy of his, I said yes.
Some I am being the cocksucker for both of them. At one point I am between one guys legs while he laid back on the bed, my ass is up. I feel hands on my ass, then a my hole is being licked, wow!
His hands go to my hips, I feel his cock against my virgin hole. I wanted to say no but I let him slowly penetrate me. I though it would hurt but he worked it in very slowly. He asked "you ready for a fucking"? He pounded my ass until he came balls deep, the other guy blew a big load in my mouth.
I came hard without touching my cock. Most intense sex ever.
I am faithful to my new wife but sometimes JO thinking about taking cock. Go for it.

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