Anal Masturbation Stories

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All I want for my birthday is a big booty...orgasm.
There’s lots of talk about how to achieve an anal orgasm with a partner , but what if you’re looking to give yourself that mind-boggling, life-changing booty O? I mean, it’s 2019, people! We’re independent women who are in charge of everything and anything having to do with our sexuality—including our anal orgasms.
New to anal masturbation? Don’t sweat it. We asked three experts to help us put together a foolproof eight-step guide to anal masturbation if it’s your first time.
“Anal masturbation isn’t just about the pursuit of getting off,” explains pleasure coach Tyomi Morgan . “It’s also about connecting with one of your erogenous zones that has been culturally stigmatized as a ‘taboo area.’” So set the mood and make your anal exploration time a sacred and Zen place. And what better time to do that than in the shower?
Try adding a few drops of lavender essential oil into the stream of your hot shower, suggests Morgan. “Create a spa-like atmosphere in your bathroom. Clean your booty, bend over, and allow the water from the shower to stimulate your anus. Breathe deeply, allowing the essential oils to relax your body, and connect consciously with your anus,” Morgan suggests.
“It helps to knock out a clitoral orgasm (err, or five) beforehand so that you’re already really turned on, in the mood, and ready for more action,” suggests relationship and sex expert Emily Morse, host of the SiriusXM Radio show and podcast Sex With Emily .
Start with your normal masturbation routine, then you’ll be prepped and ready to take your fingers and toys backdoor for more fun.
When you’re ready to get into it, try a little foreplay. “Start by stroking, massaging, and lightly spanking your butt cheeks, moving closer and closer to the anal opening,” suggests Kait Scalisi, MPH sex educator and founder of Passion by Kait . “Don’t worry about penetration to start—most nerve endings in the booty are right at the butthole.”
Don’t be shocked if it takes you a few tries to find the perfect position. “It’s no surprise that it can be difficult to maneuver the backdoor if you’re not used to the area,” says Morse. I mean, after all, it’s not exactly the easiest or most comfortable place to reach—especially if you’re not a flexible person.
So instead of holding your arm in a weird bending contortion, experiment with different positions until you find something comfortable. For example, you can lie on your back with a pillow under your pelvis arching your butt up, so you have easier access. Or get on your knees and bend over so that the area spreads open more naturally, says Morse.
“Solo anal play makes practicing relaxation and deep breathing easy,” says Morgan. And anal masturbation requires conscious awareness to feel pleasure instead of pain. So know this: Resistance against stimulation will cause tension and create a less-than-pleasurable experience. Tell yourself to relax while breathing into your anus, and this will assist you with training your anal sphincters to relax into pressure instead of resisting, says Morgan.
The anus isn’t self-lubricating like the vagina is, which is why it’s even more important to invest in some good, body-safe lubricant that can create a comfortable, friction-reducing experience for you.
Morgan suggests using a water-based lubricant, since it’s easy to clean up and nourishes the membranes of the anus. “My favorite is Muse Essence water-based lube because it’s pH-balanced and vegan. Treat your anus by investing in good products to maintain balanced health,” she says.
“The easiest and least expensive way to begin your exploration into anal masturbation is to start by using your own fingers,” says Morgan. Lube up your index or middle finger, and rub your anal opening and inner rim. You can increase the pressure and depth of penetration as you become more aroused, says Morgan.
Using your fingers during anal masturbation does require short nails, so make sure you’re cleaning up carefully beforehand to fully enjoy bum play.
“If you’re just trying to get into anal masturbation, a butt plug is a great way to start,” says Morse. But make sure you use something with a flared end so you don’t have to make an embarrassing trip to the emergency room to have it removed. “I love B-Vibe because they have beginner anal training kits as well as a range of snug plugs that gradually grow in size and are all incredibly comfortable to use.”
Look for toys that are simple plugs or others that vibrate for even more sensation, Morgan adds. “Anal bullets and vibrators, graded anal beads, glass dildos, and silicone dongs are also good options.”

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This post is part of Mashable's Masturbation Week . May is National Masturbation Month, so we're celebrating by exploring the many facets of self-love.
Look, we've all been there. Sometimes, the need to pleasure yourself overrides all common sense and you're left with an incredibly embarrassing — though hopefully very entertaining -- story to share to millions of strangers on the internet.
Here are our ten favorite stories of masturbation gone wrong from the depths of Reddit. Hopefully you can't relate to any of the horrors below.
"This story isn't quite as funny as some of yours, but... One time, when I was about 12 or 13, I had the sweet idea of taking the seeds out of a cucumber, putting it in the microwave, and humping it. I was super excited about my new cucumber fleshlight. I start humping, but instead of pleasure, I felt burning. I put the cucumber in the microwave for too long. I had blisters on my shaft for several days. They were excruciating. Let me tell ya.. Gym class was a new level of hell for me."
Reddit user pizz901 shared the horrific tale:
I have epilepsy. One night I was going at it in my bed and lo and behold I have a seizure. So naturally my parents hear something and have to come in to me seizing on the bed dick out porn on the computer. Very embarrassing to have to find out from them (since I lose a bit of memory of the event and am unconscious during it). All I can say is it must have been one hell of an orgasm to make me seize (more than the usual jerky cumming movements anyway).
This story comes from Reddit user funny-chubby-awesome :
"My high school best friend, let's call her Hillary, approached me about masturbation. I was the expert on sex, as I had a bf and had gone down on him 1.5 times. I told her my technique (rub it 'til it feels good, don't stop) and she showed me that month's Cosmo. Find your best O ever - the G-spot. We read the article and she tells me she had tried with her fingers to no avail. We decide it needs to be stimulated with something more penis-like. We (mind you, we are VERY experimental 16 year old girls) decide to try it with hot-dogs that night at my house.
She comes over, I go to the fridge and find we only have SPICY KIELBASA! I show her and we decide to still try but cover them in condoms. We sit on my futon, slide our pants/undies down, throw a blanket over our laps... I remember thinking, "Am I sure I want to do this?", but I hear her, like, moaning so I....plunge ahead. IT HURTS! And it's like burning and I feel weird. At that moment my mother BURSTS in (drunk) and starts screaming at us! She insists we're doing drugs and questions the blanket over us. I finally convince her to leave and remove the sausage. Hillary hands me hers and I go to throw them in the wastebasket. That's the last thing I remember.
Hillary says I passed out and she got my mother. They called an ambulance and the EMT was grilling Hillary about what we were doing. I wasn't breathing. My mom started ranting about drugs and Hillary panicked and told them what was going on.... I wake up in the hospital to: my father (can't look at me), my mother (can't stop laughing), Hillary (in the corner, beet red), and a doctor explaining that I have a latex allergy and had broke my hyman, causing anaphylactic shock.
TL;DR: I masturbated with a condom-covered hot dog and nearly died. And my whole family found out."
Redditor Fapfapthrowaway5573 shared a horrifying tale featuring a grandma and a knife:
One time [my grandma] was staying at my house in the downstairs bedroom. My room is upstairs and the first one at the top of the stairs. I had no lights on or anything (this was before I discovered porn) and I was doing the deed. Well, my door creaks open, but for some reason I didn't think anything of it. I thought I saw a figure but I thought it was my imagination. Well, I keep doing the deed and someone shuffles in and slowly is walking around my room. I realize what is happening and I stop, only to look closer at the figure and she is HOLDING A FUCKING KNIFE. I just stay still and she leaves the same way she came but holy shit it was weird.
Tl;Dr: was masturbating in dark room when my sociopathic grandma walks in with a knife, makes a circle in my room then walks out.
A now-deleted Reddit account posted this nightmare of a masturbation story:
One time I had poison ivy but before I even realized it, I had masturbated. I woke up and my eyes were swollen shut and my vagina was covered in poison ivy. It itched so fucking bad I took a hairbrush and just went to town. You ever see those pornos where they pump the vagina up and make it all big and puffy? THAT'S WHAT HAPPENED TO MINE after scratching with a hairbrush for so long. It was disturbing and I never tell this story in real life.
Komodokid on Reddit learned the hard way to always check your surroundings:
13 yrs old in a beach town on the Mozambican coast, middle of nowhere. No tourists, not a soul, just miles of beach. I walk 30 mins down the shore for some alone time, climb up a sand dune and sit down to start my business facing the epic horizon.
5 mins in I hear someone snigger behind me.
About 30 people from the local village, mostly teens but also women and kids, are standing in a group just staring at me. All burst into peals of laughter when they see my face. I just bolt, trying to outrun the shame, but the village kids are running alongside up on the dunes, and they have no trouble keeping pace, just pissing themselves laughing and doing wank gestures.
An anonymous user on Tumblr shared this scarring story:
I was masturbating under my sheets once and my cat was in the room, I was watching porn not paying attention and next thing I feel is claws being dug into my cock, she thought I was playing a game because the sheet kept bouncing, couldn’t masturbate for a week.
Beatenpear shared a traumatizing memory on Reddit:
Back when I was like, 13 or 14, my bedroom used to be right across the hall from the bathroom, with my parent's room at the far end of the hall. I would often play a little five on one late at night and then quietly walk across the hall to the bathroom to clean up. So here's where it gets interesting, at some point at that age I was having a reoccurring problem where when I stood up I would get really light headed. (I think it was because of dehydration?) so one night at about one in the morning I started to rub one out and everything went exactly as planned until I went to clean up.
So I stood up to start my journey to the bathroom while using my phone screen as a flashlight. First step went fine, but by the second step I started to get light headed. My vision started to go black but I was halfway to the bathroom and covered in ejaculate so I made the decision to try and make it to the bathroom and then try and get my bearings back. As it turned out, that was the wrong decision. By the time I made it through the door of the bathroom my vision had gone completely black and I started to pass out and fall. I was only out for about a second, reason being I came back to conciseness when my head made contact with the toilet mid fall.
So there I was, lying on the floor of my bathroom in the middle of the night in the dark, covered in cum with my dick out, slowly coming back to conciseness when I heard my mom on the other side of the open doorway ask if I was alright. Apparently the sound of my head slamming against the toilet woke her up. All I could do was speak out a "uh... yeah..." and close the door with my foot so she didn't have to witness the disappointing sight that lied in front of her. A couple minutes passed and I was finally able to get up get back to normal.
So yeah, after that I started to drink a lot more water and be more cautious of my surroundings when I chose to "distribute some free literature".
Reddit user CultofMourning's birthday started horribly :
Woke up early on my 19th birthday and decided to pass the time with my favorite dildo. I’m under the covers, enjoying myself, when my mother busts through my bedroom door to sing me happy birthday. I moved my hands away from my genitals and just laid there while my mom sang. The lower half of my body was covered so she didn’t realize I still had the toy inside me. The whole time I’m thinking to myself, “please leave”.
Just...be careful out there, folks. Check your surroundings, use actual tools instead of cucumber, and learn from these people's mistakes!
Related Video: We revisited the trauma of watching sex scenes with our parents for your entertainment

Now Reading Let’s Talk About Masturbating In Quarantine
Anthropologists of yore could hardly have predicted that masturbating and bread-baking would serve as summer 2020’s premier pastimes. But in the midst of a global pandemic, while quarantine is simply a mandated way of life, most of us are nothing if not restless and horny.
“There are a lot of reasons masturbating can feel more important than ever right now,” says certified sex and relationship therapist Megan Fleming , PhD. “So many folks are feeling weighted down with all this anxiety and uncertainty, and masturbation can be a really healthy way to calm the nervous system.”
Orgasm — self-induced or otherwise — releases a whole flood of beneficial chemicals in the body. Dopamine levels spike, cortisol levels drop, and endorphins are released alongside oxytocin, a hormone most commonly known for providing feelings of warmth and well-being (folks sometimes call it the “ cuddle hormone ”). And, as Dr. Fleming sees it, solo sex can offer a welcome (necessary) sense of release as well as a form of escapism. “It’s a really excellent opportunity for you to spend some time exploring yourself sexually. You have time to try new things, delve into new fantasies, flirt with new turn-ons,” she says. “We call it solo play for a reason — we should really treat it like play .”
However, while we may find ourselves with ample time , plenty of us are quarantined in...less-than-sexy scenarios. Whether you’re back in your childhood bedroom, stuck home with your kids, or sardine-packed into an apartment the size of a parking spot with four roommates, “setting the mood” isn’t always easy. So, in the spirit of adventure, catharsis, release, and, well, pleasure, we reached out to women in varying socially distant setups across the country to talk about what solo play looks like for them. From masturbation coffee breaks and art-deco nudes to butt plugs and roommate snafus, here’s a voyeuristic peek at “getting off” in quarantine.
Laura P., 26, quarantined alone in New York City
“Working from home is driving me insane. I’m so restless. I’m dying to get out of the house. I work in film, so I’m used to spending most of my days out and about, on my feet, interacting with tons of different people. My girlfriend also works on film sets, so I’m used to seeing her every day at work and at home, but we’re quarantined separately.
“Obviously, I know this is something everyone’s been saying in quarantine, but I’m incredibly horny. At the same time, while I’m doing all this remote work (lots of random editing projects that are sort of slow and arduous), I’ve been having trouble staying focused. So I’ve found that masturbating can work as a quick, energizing coffee break for me. It helps get my brain back up to speed when I’ve been staring at a screen for too long. So when I hit a rut, I throw a hold on my calendar so no one will try to schedule a call, then I pull up some of my favorite OnlyFans accounts, and I touch myself. I’ve been using this amazing rounded tool I ordered online against my clit, and I have to say, it feels about as close to oral as anything I’ve ever tried other than...oral.
“Then, once I come, I wash my hands and get back to work, reinvigorated. I swear, it works.”
Ricky M., 31, quarantined with her partner in Chicago
“So I live with my long-term monogamous partner. We've always had a great sex life, and when we found out that we'd be on lockdown, our first response was: We're going to have so much sex! In reality, the opposite has been true. Our once concurrent schedules a
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