Not all my experiences have been good ones. Some have been pretty awful. There was a time I was asked to do anal. And to begin with I didn’t even really want to do it I did it to make the person happy.
Side note: never do anything you are uncomfortable with just to make anyone happy. If they truly care they will not put you in that situation to begin with. Moving on.
I laid on my stomach as lube was placed into my backdoor. He fingered my ass a little to help stretch it out and to help the lube coat the inside as well. He lubed up a small butt plug and stuck it in my ass. I gritted my teeth as he forced it in.
We proceeded to have vaginal sex in doggy position Which was really nice as always. After a bit he took the small butt plug out and then went a Size up. Again teeth gritting pain.
Back to doggy for awhile, I rubbed my clit to get off, which is always a good orgasm. After that he took what was the third butt plug out. My back hole was slightly used to it but still stung with some pain.
He lubed up my ass again and his dick and proceeded to push his cock Into my opening. He had slid his entire dick inside me and proceeded to thrust in and out slowly picking up momentum. A few moments in and he was slamming into my back door.
He would also take it out and shoved it back in over and over again. This was rather painful and I could feel a burning and stinging at the opening because he had tore it abit.
The only way it felt good was when I rubbed my clit as he slammed into me again and again. If I had an orgasm it was slightly less painful.
I didn’t understand how something like this felt good to anyone. By the end of it I was full out crying from the pain. I told him he needed to cum soon because it was getting hard to continue.
He pulled out stroked himself a little and then slid back inside me and after a few thrusts he came into my ass and slowly slid out. I ran to the bathroom and I could feel stinging back there and sure enough I was bleeding.
I did try it again a few times with more lube but it didn’t really help and always left me in pain and bleeding.
When I had told this story to a few anal veterans they were horrified by my experience, and understood why I am so traumatized from the whole experience.
Apparently it’s not like in porn and has to be done a certain way. It should be pleasurable and not cause so much trauma. Unfortunately I don’t think I will ever try this again. It left a really bad mark on me.
To those that find this pleasurable kudos to you I’m glad you did not have the experience I did.
Source: reddit.com/r/eroticliterature/comments/rxv9ot/anal_sex_mf20s
I have only had anal sex with two women in my life. The first woman I had anal sex with was very different from the second. She actually was the woman who took my v card. In fact we both lost our virginities to each other. Yes she took near all my firsts and I took almost as many of her firsts. When I first suggested anal she refused. Made it clear “that is an out hole only”! Over time, and gentle prodding, however she opened up to trying a finger for a bit as she neared orgasm. Which at some point turned into being ok with trying analingus. “Kinda weird. I dunno. Not great but not awful like I thought it would be.” was her review. Several months later (and years into the relationship) she surprised me by handing me a bottle of lube. She said to me that I had been such a good boyfriend to her that she wanted our last day of our trip (we had taken a dirty cheap trip to a different country) to be truly memorable. We talked afterwards in the shower and while she wasn’t a fan at the start, and did not want anal to become common, she admitted to kind of enjoying it by the end once she got into it and started rubbing her clit. At some point down the line she was so comfortable with anal I could switch between holes to her enjoyment and used toys for simulated DP. Some of the anal adventures she started. Jump ahead to the last time we had anal sex and midway through she squirts on my chest as she has an anal orgasm. The look of pleasure on her face, and the clamping down on my cock, made me cum deep into her bowels shortly afterwards.
The second woman was my first wife. Now she is very sexually liberated and was down for anything I suggested. She had many sexual partners prior to meeting me and to say she enjoyed sex would be an understatement. She also has a kink for pain and some times mid anal sex she would intentionally go rougher than she knows she should to tear her asshole intentionally. I kid you not. She had already learned how to enjoy anal in a way that worked for her and she showed me so we could enjoy it together.
Now we jump to today. I find myself slowly going through the same early steps with my second wife as I did with my first lover although with the added baggage of her first husband being just awful to her during anal. With slow prodding she has gotten to the point where a finger enhances her sexual pleasure. Earlier this week I nearly got her to orgasm from fingering with some anal attention added. I am a slow and gentle lover at most times and make an honest, although not always successful, attempt to make sure the woman I am with has an orgasm as well. That doesn’t work for all women. Some want it rough. As my first wife taught me some women want the blood and pain. It is all about finding what works for you. There is no handbook just guesswork and trust. I hope you find a lover that treats you in such a way to find anal enjoyable so you can add it to your drawer of pleasure.