First Time Anal Fisting
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First Time Anal Fisting
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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.
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.
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.
I could still feel his ass grip on my hand an hour later. It was intense!
“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.
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.
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.
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.
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.
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.
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!
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
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).
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.
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Trimmed my riot of herbs, cherry tomatoes & peppers. My thumb is Incredible Hulk green this year! https://t.co/TmYxtWCW05
Big sis,
little sis,
both sis = exhibitionist!
(w @ProutySarina) https://t.co/mkPV25WFfb
A neighbor has a rooster just far away enough to be charming…
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Dainis Graveris May 6, 2022 October 10, 2020
Okay, let’s get one thing straight from the outset: anal fisting is definitely NOT for the faint of heart. However, if you find yourself occasionally dabbling in other forms of butt play, you might want to consider spicing up your game with a handful (pun intended!) of fisting techniques.
And no, you don’t have to go all-in at the first attempt. You can slowly build your way up and gradually introduce one finger at a time up your — or your partner’s — derriere.
Take our word for it: do it right, and there will be no going back for you. Anal fisting can be one of THE most orgasmic and intimate sexual acts out there.
Did we pique your curiosity? If so, here’s a brief summary on how to fist yourself (or anyone else):
First, discuss your hard limits and safe words. If you are a receiver, get an enema. If you are a giver, wash your hands, trim your nails, and use latex gloves.
Relax and lube up. Have the receiver lie on one side. Insert one finger and gently work your way up until you get all five in.
Anal fisting is any sexual act that involves the penetration of the anal canal using all five fingers.
However — and this is an important however — the fister’s hand does not have to be shaped like a fist. We’ll discuss that in more detail later.
Another widely held but incorrect belief about fisting is that it’s all about heavy thrusting.
The reality is that, yes, anal fisting may involve thrusting — but you can just as well use your hand to simply stroke or fill up the asshole.
Finally, many people (wrongly) associate anal fisting with pain and severe discomfort. While fisting certainly has its place in power play and BDSM, it does not have to be painful.
In fact, it’s best to keep it on the gentler side for health and safety reasons.
Don’t think you can handle anal fisting just yet? Perhaps squirting could fulfill those same hardcore fantasies. Watch this video from School of Squirt that shows you a really effective way to make girls squirt.
If you like to feel filled up and stretched to the limit with the best anal stretching toys , fisting can also certainly help with that.
However, you can take the intensity of the sensation up or down a notch by changing the position and movement of the hand and fingers.
What’s more, the human hand can offer a much wider range of sensations and types of stimulation than conventional sex toys.
Just think about it — it’s like having a dildo with five independently moving shafts!
Like other forms of anal play, fisting can help you reach the big “O” by stimulating the prostate or the G-spot by massaging the posterior vaginal wall.
However, fisting allows you to apply a lot more pressure on your sweet spots compared to more vanilla options such as fingering or sex toys.
You might be able to orgasm just through the stimulation of the anal canal alone!
In addition to the purely physical sensations — which can be wonderful — many people are into anal fisting because it allows them to play out their BDSM or humiliation fantasies.
There aren’t many better ways to fully submit to your Dominant and give them total control over your body.
Others fantasize about being gang-raped or double-penetrated, and fisting can definitely give you a stretch similar to that of having multiple dongs inside you.
And then there’s the fact that anal fisting still has the reputation of a taboo practice. And taboos make for the best fetishes.
That said, perhaps the main reason so many people are drawn to fisting has to do with something much more romantic: intimacy. You didn’t see this one coming, did you?
If you think about it, though, it’s not that surprising.
As we’ll see in a bit, anal fisting requires a high level of trust and constant communication between the two partners — before, during, and after the act.
That’s not something you necessarily get with “regular” sex.
Before we get on with our step-by-step fisting guide, we need to make sure you have the basics covered.
When it comes to anal fisting, thorough preparation is absolutely vital to avoid unpleasant and potentially dangerous incidents.
The importance of lube cannot be overstated. The anus is not self-lubricating, and you will be inserting an entire human HAND in there.
You’ll be needing copious amounts of lube to get the job done.
If you’ll be penetrating using your or your partner’s hand only, silicone lube is your best bet.
It has a thicker consistency and lasts quite long, which should minimize the need to reapply it too often.
However, if you plan on throwing toys into the mix as w
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