My First Time Anal Fisting!

By Kendra Holliday | October 26, 2012

You know, I never thought I’d get the chance to anally fist someone. Who does?! I haven’t even vaginally fisted anyone yet, although I’ve been fisted thrice, and it was nice!

Anyway, I found out that a friend of mine is into anal fisting, so I asked him if he would let me put my hand up his ass.

He said sure. He gave me this mini-tutorial:

The rectum is much like the vagina, only with more defined muscle groups.  those groups need to be slowly stretched at first.

Because I am male, this may take some effort, but that is part of the fun.  You will worry about hurting me, don’t worry.  Use lots of lube, start with one, then two fingers and keep adding more and more.  Be sure to pull all of the way out from time to time so the muscles will relax.

Each new insertion will be easier than the previous. After some time you will notice a sexy type of looseness that is different than anything you have ever felt.  When you hand is finally in, go very slow at first, this gives the muscles time to relax even more.  This is not the time to hurry, just get used to the tightness and warmth.

On the next insertion you will go in much easier and it is then that I will let you play any way you want.  I will be in heaven at that point and will want you to take full advantage of your new experience.

You would never guess by looking at him that he was into this kind of thing. He’s very manly, brawny. I asked him how he got into such extreme penetration, and he told me it all started when he was 12 years old and his 19 year old, well-hung brother raped him.

Seriously.

He told me all the details over hash browns at the Waffle House. He said that right as he had his first orgasm, his brother rammed his entire cock right up his ass ala Vlad the Impaler. It hurt like a bitch, but to this day he still associates that very full feeling with pleasure, and he loves sharing that intimacy with a woman. He has no desire to be with a man, and was very happy to meet me.

I told him I’d be honored if he allowed me firsthand experience into the world of extreme penetration. He has a HUGE strapon dildo.

He came over, and brought towels, latex gloves, and some Boy Butter.

“I’ve always wanted to try Boy Butter!” I exclaimed. I love how the tub resembles the stuff you find at the grocery store. Also, I hear it’s better than Crisco for anal fisting.

We stripped, he put on his three cock rings, and laid back on the bed.

I gloved up, dipped my left hand into the Boy Butter, and peered intently at his asshole. I was so curious to see what it would look like after all those years of intense anal play. Guess what? It looked perfectly normal. He was very shaved and clean down there.

I started with one finger, then he told me to add two. Right there was more than I’ve ever done before.

Then three.

Four.

Finally, the moment of truth: how in the world was I gonna fit my thumb in?! Well, I just did it. We went slow, but honestly, he made it seem easy.

My whole hand slipped in his rectum. It was an amazing sensation – he gripped me tight. It felt very warm, snug, muscular. I removed my hand and reinserted it a few times to help him relax. He remained very clean.

I was in up to my wrist when he looked at me and said, “Now it’s time for you to be mean to me.”

He jerked off as I moved my fist back and forth inside him. He urged me to fuck him harder. He held his knees up to give me even deeper access. He wanted me to POUND him.

I murmured filthy insults at him – “Look at you, you fucking little sissy slut. Don’t you make a good hole. I want to do this to you while my girlfriend sits on your face. I’ll watch her juices run down your neck as I ram your ass raw!”

“Right now my ass belongs to you!” he gasped.

“It sure does,” I agreed. “I’ve got you right where I want you, fuck toy!”

I was into it – I enjoyed it even more than I thought I would. I marveled the entire time. I hit a wall of muscle inside him. I wondered what his prostate was making of all this. My hand was so hot.

Finally, he exploded on his belly and chest, and I scooped his cum up with my right hand and fed it to him.

He calmed down, and I verrry slowly withdrew my hand from his butt.

“WOW,” I sighed.

I could still feel his ass grip on my hand an hour later. It was intense!

Comments

Dubdub 2012-10-27 11:36:44

“He said that right as he had his first orgasm, his brother rammed his entire cock right up his ass … It hurt like a bitch, but to this day he still associates that very full feeling with pleasure…” Okay then. No big deal. Nothing to see or mention here, moving right along.

I like huge things in my ass because I associate it with the pleasure of being ass raped by my brother…. What a fond memory you helped him relive.

/s

Reply

    Kendra Holliday 2012-10-29 18:05:57

    I know, it’s pretty crazy, right? I’ve used sex to address past demons myself. It’s a safe and loving context to do it with a caring person, on your own terms.

    Reply

BigRedOne 2012-10-28 19:05:10

I have long been interested I how we all work out our life experiences through sexual play.

This post reminds me of two of my former lovers.

The first was a beautiful “older” woman (38 to my then 26) who taught me about bondage, anal sex, squirting and how to have a positive sexual relationship without any expectation of long-term commitment.

She eventually shared with me that a decade before she had been tied up and anally raped by her former boss, after hours, in his office. The most troubling part for her, the part she rarely shared, was that when she remembers it during sex she cums particularly hard. We talked about it a lot and she came to the conclusion that sex and orgasm under those conditions was a way for her to regain a sense of power and allow herself to continue to enjoy sex.

A number of years later I met a shy teacher who had a very adventurous side to her sexuality. Her experiences should be a book. The more she told me about all the men she had been with and the risky/exhibitionary sex she had engaged in the more turned on I would get. I have never understood why some people are negatively impacted by their partners’ history. There are few things sexier than a partner who brings quality experiences into the bedroom.

She shared with me that when she was 12 her father left the family, not to be seen again for many years. Less than a year later she became sexually active and ever since has had intense sexual fantasies about having sex with her father as part of a plan to lure him back to the family. I became the first person with whom she explored this idea by having several “father/daughter” role plays.

She also talked to me about the fact that her daughter was the product of being gang raped at a party where she passed out from too much alcohol. She said the ironic thing was that she would have happily fucked them all had she been asked, but they didn’t and didn’t use protection.

She also had fantasies about being tied up, and physically and verbally humiliated. She asked me to help her live this out since she knew I would while still treating her with respect and love. It was intense and wonderful.

I know that a significant number of women have rape fantasies but I am curious how many repurpose traumatic events, sexual or otherwise into sexual pleasure and power.

Reply

    Kendra Holliday 2012-10-29 18:09:39

    Wow those are fascinating examples. I roleplay past traumatic experiences and it is therapeutic for me. My partner is awesome to assist me in that way. It certainly is deep and personal, requiring trust and aftercare.

    Reply

      David 2013-10-05 06:37:46

      hello. I don’t know where to begin. I would love to be fisted. but I do not know how to go about doing it. I used huge toys but I just don’t feel satisfied. please help.

      Reply

MrE 2012-11-07 21:14:33

Loved the story you related…very hot. Interestingly, I received my interest in anal through a cousin who kind of “diddled” me when I was younger…probably around 11 years old. It was a “game”. Ever since, I’ve had an interest in all things anal for both parties.

I had been at myself for years with progressively larger toys but yearned to share it with a female and have anal sex with a female. I’ve fantasized about receiving a female’s fist for many years and finally had an opportunity with a pro for my first time fisting AND first time strap on. It was AWESOME and for 3 years have been wanting to do it again, but alas, my wife is not open minded to such things in the bedroom. Sucks to be me. L

Lucky your friend had someone like you to share this with.

Reply

Sineo 2013-11-26 04:03:56

Straight guy into receiving anal fisting here, and I must say I am jealous of this guy. Having an enthusiastic women come to me with a question like that is a dream for me. I have been fisted but it has always been because I asked for it. Turning that around seems mindblowing!

Reply

tony Gorrin 2019-02-05 13:05:21

I been reading the comments here and a lot of them are at least three or more years old. My first experience with the idea of anal fisting start with a magazine called Puritan… I later was in Ca;California( Santa Barbra) and met this female playing her guitar on the stoop we hit it off immediately and before long was having sex in her living-room she went down on me and started to give me a blow job. Back then I can receive head for hrs without cummimg. I told her this after she was sucking and deepthroating me for like 20 minutes she said we will see about that she redouble her effort and after bring me close to the edge she started playing with the rim of my asshole and, well i couldn’t believe it possible but my dick grew and extra inch and was twice as hard as steel .. finally to push me over the edge she swallowed my entire length balls deep while sticking two fingers three knuckles deep in my ass. I shot off like a rocket emptying my balls deep in her stomach… Well needless to say from that moment on I got more and more curious with ass play and anal fisting Still to this day looking for a female to indulge with my fantasy. Let me finish this with I am not gay not even remotely. Just looking for that right female to come along and play with me

Reply

Tubeflyer 2020-12-25 20:49:31

I was partially paralysed as young man. I retained the ability to walk but lost nearly all feeling in my genitals. That may be the reason I started extreme anal play. Anyway I could find to get some sensation. Or perhaps I would have got there regardless. My partner really got me off one night with up to three fingers in my butt and this married well with happening upon a porn magazine (long before the internet) that showed gay fisting. So I knew it could be done. We went from there and it took 3 months to get her whole hand in my ass. She’s 5’ 11” and while she doesn’t have “man hands”, they’re not petite. She’s never had a particular interest in the act, doesn’t get off on it at all (other than an almost clinical curiousity). But that makes me even more grateful as she’s never said no, never judged and was always willing to help. I think we did it monthly for at least 6 years and then it became a random part of our sex life (I had niggling concerns and although never hurt myself, it’s pretty invasive). After a long break however, it would reliably take at least three attempts before she could get back in. Overall, it was part of our life for 20 years. After a break of nearly 15 after the last, we’ve tried again. Several times. But at nearly 60, it seems the sands have shifted, it seems there’s no room anymore and I’m no longer that stretchy. After giving it maybe ten attempts, we gave up. My memories are still a great help to getting off and if I could relive any sexual experience, it would be to get roughly fisted. The best sex ever (and I don’t think I’d change my mind even if I got all that lost feeling back).

Reply

    Kendra Holliday 2020-12-26 11:41:05

    Thank you for sharing your experience – this is a good PSA for others, with different messages. Your partner sounds wonderful in that she is GGG – good, giving, and game. I highly recommend you and all my readers look into the teaching of http://www.joanprice.com – she is my mentor and is all about ageless sexuality.

    Reply

Leave a Comment

Please see the Community Policy for comment guidelines and rules.

YouTube RSS

Archives

Twitter

WordPress › Error

There has been a critical error on this website.

Learn more about troubleshooting WordPress.