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How to introduce girls to anal (Data Sheet)
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polar Offline
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How to introduce girls to anal (Data Sheet)
“I have nothing to offer but blood, toil, tears, and sweat.” – Winston Churchill
“That's because you’re doing it wrong!” – me



This is a guide to getting to fifth base. Especially with girls that haven't done it before.

Why would you do such a thing? Because it’s a fun side dish to fish tacos, and given that not many chicks are saving themselves for marriage anymore, you’ll run into more anal virgins than the old-fashioned kind.

I’ve put it in the back door of about a third of my plates, with half of these, I got their anal v-card. Neither the size of my salami nor the size of her donut hole have been a major factor in my experience…so unless you’re Mandingo and trying to fuck a midget, there’s someone out there for ya.

So here's how to squeeze your Big Gulp into her chocolate starfish, especially if you’re looking to boldly go where man has never gone before (or that's what she told you, anyway).

Background Music:









Related reading:
https://www.rooshvforum.com/thread-60607.html – General Stalin’s data sheet, worthwhile read for an alternate take
https://www.rooshvforum.com/thread-14635...#pid242948 Samseau’s anal post in his pre-Puritanical days.
https://www.rooshvforum.com/thread-35046.html – Horus’ quick and dirty summary
https://www.rooshvforum.com/thread-57188.html – shitty OP, but decent discussion
https://www.rooshvforum.com/thread-5049.html - another discussion thread


“Back” ground
Cleanliness is generally a non-issue…you’re not likely to end up with chocolatey fingers, as the back door is generally clean until you go in deep, unless she’s had a bowel movement recently, or is holding one back. Take her word for it, or you could end up like Tucker Max ( http://tuckermax.com/stories/tucker-trie...not-ensue/ - don’t do this). It’s easiest to explore after you soap up together in the shower.

There are two sphincter rings around the hole, the outside one is “voluntary” (can be controlled AKA intentionally relaxed) and the inside one is “involuntary” meaning that it is not controlled. Both rings are very sensitive, and “forcing” them will hurt her. You need to get her to relax both before you put anything through them, and you need to stretch her out before you will fit inside. Porn does all of this off camera (spoiler: it’s not actually her first time), so don’t expect to go from zero to 60mph in 2.7 seconds.

You will need lube. I like using silicone lube, as it doesn’t dry or get sticky like water-based. Coconut oil is a good alternative, but may damage condoms. Some hardcore chicks will be OK with just spit, or spit and her juices.

Back door fun tends to be an acquired taste for her, and she’s not going to enjoy later steps until she gets comfortable with earlier ones. If she’s not comfortable or is hurting, stop; ditto if you see blood. Also, a reminder that anal carries higher risks of STD’s, especially for the receiving partner.

Don’t expect to hit fifth base in a single night, especially if she’s new to it. While I’ve gotten first night anal v-cards, on average it’s taken me two or three bangs to go through the below steps. With inexperienced chicks, you can round the bases a bit faster every time, but don’t rush or skip steps. A little alcohol can help lower inhibitions, but know the limits. Consent is key, consent is sexy, and none of this is medical or legal advice. IANAL.*

*I am not a lawyer. What did you think it meant?


0. Bang the hell out of her front hole
Before you ride the back roads of her Hershey highway, make sure to put down some quality lovin’ around the front. If you bang her out like she’s never been before, she’s much more likely to go with the flow. If she’s not having fun already, anal won’t turn the night around.

The more you rock their world in previous sessions and directly beforehand, the less anxious they’ll be about experimenting.


1. Help her relax around the back door
Lubrication needed: none
Risk of chocolate surprise: none
Difficulty: ★☆☆☆☆

A chick new to booty play (or one that has had bad experiences) will feel weird at first. The solution is to begin playing with her ass while you’re already delivering plenty of stimulation to her clit or pussy. It’s easiest to incorporate this into foreplay and continue from there.

Massage around her booty hole. Massage the area around the back door with your hands, while squeezing her cheeks with the rest of your fingers. Avoid the hole for now. Use both hands if you’re in 69, she’s in doggy on top, or on her stomach. If she’s on her back or you’re in missionary, you can support yourself with one hand while reaching the other hand under her.

Pro tip: If you’re into that whole thing, eat that booty like groceries (I’ll leave you with https://www.rooshvforum.com/thread-41987.html )…probably the best way to open her to the idea that back door activities can be fun. Use as a substitute or as an addendum to massaging her pudendum…just do take a shower and soap her up first.


2. Relax the outside ring
Lubrication needed: some (spit or any lube)
Risk of chocolate surprise: minimal, if she practices basic hygiene
Difficulty: ★★☆☆☆

Here, you’re going to test the waters. Start by sliding a finger over her ass hole and see how she reacts. Best time to start playing with her is before she’s about to come.

Build up from incidental touching to rubbing it with your finger…preferably not the tip of your finger, but the wider part closer to the first knuckle. Use the same approach and pressure as if you were playing with her clit.

No effort at penetration; you’re massaging the outside ring, rather than poking her. You want her to stop puckering up and relax. Once she loosens up enough that your finger sinks in without much pressure, move further.

You can do this in any pose…reach under her if in missionary, use your thumb if in doggy or from behind.

Pro tips:
- Time your poking around to your strokes on her pussy.
- Add lube as needed in small amounts…if it’s dripping, you don’t need more.
- Also dedicate one or two fingers on one hand to butt stuff only, so you don’t end up putting that hand elsewhere (such as in her pussy or in your eye)


3. Relax the inside ring
Lubrication needed: a bit more (spit or any lube)
Risk of chocolate surprise: minimal, if she practices basic hygiene
Difficulty: ★★★★★

From this step forward, it’s easiest to put her on her stomach. Doggy is OK, and so is her on top. I do not recommend missionary.

Once she’s relaxed the outside ring, you can start massaging the inside one. Start with timing it to your strokes in her pussy. Get a sense for her contractions…if she tightens up with your stroke, ease off. If she’s looser, you can go a little deeper. Once she relaxes a bit, you can move back and forth more rapidly, but with very low amplitude. Remember that progress is measured in fractions of an inch. Add lube often, a little at a time.

This is where the wannabes are separated from the pros. It’s easy to hurt her by forcing things at this step by going too deep, too quickly. Don’t move further until you get your finger in to the second knuckle and she (at the very least) doesn’t mind you moving it back and forth, and hopefully openly enjoying it.

Pro tips:
- You want to cross the “barrier” of the inside ring the bare minimum number of times…once something is in, you don’t want to take it out and go back in. Don't do that "take it out, put it in, take it out again" shit you've seen in porn.
- Time your poking around to your strokes on her pussy. You can change up the timing once she gets more into it.
- If you don’t think it’ll break the mood and you’re extra squeamish, you can finger her through a condom (next best thing to the doctor’s latex gloves). It’s probably overkill, unless she's a disease-ridden whore (and if so, what the hell are you doing with her?)
- If your finger pops right in and you’re thinking “well, that was quick,” she could be in tune with her body thanks to dance, gymnastics, or yoga…or this might not be her first rodeo.


4. Stretch her out
Lubrication needed: liberal (add lube as needed)
Risk of chocolate surprise: low to moderate (generally not present near the exit between bowel movements…the deeper, the higher)
Difficulty: ★★★★☆

At this point, she should be loose enough that you can get one finger inside of her without much trouble. Until now, you should only put one finger inside her, and don’t use any toys.

From here, the goal is to stretch her (inner ring) out in order to make room for your dick head. The inner ring involuntarily contracts, and if it has something to contract around, it will relax a little with time, making insertion easier.

Build up to fingering her with two fingers (or your thumb) by going through the same steps. Keep them tight together as you insert, then expand. Apply lube liberally. On her stomach or doggy are best.

After two fingers, ideally, slowly put in a butt plug or other toy (“hey, let’s try something adventurous”). Warm it up in the palm of your hand so it’s not ice cold, and lube it up. Alternatively, use something like a graduated set of dildos or anal trainer kits. Toys should be smooth without rough edges or much texture, and ideally, have a butt plug style shape (narrow tip, bulb near the front, tapered shaft, flare at the bottom). Don’t stick anything without a flared end more than halfway deep, and keep an eye on it. Metal or glass are best as they are non-porous. If the toys aren’t glass or metal, put a non-textured condom on them.

If you don’t have toys, use two or more fingers. Her on top is the best position to finger her while you fuck…sit up against the bed and have her face you.

Focus back on fucking her for a bit as she gets used to the dimensions. Then you can add more movement to whatever’s in her back door. You don’t need to go deeper than an inch or so into her…more important is going wider.

Don’t move forward unless she was comfortable with two fingers.

Pro tips:
- Be careful and take it slow with toys, as you have less sensitivity to what’s going on as opposed to fingering.
- You want to cross the “barrier” of the inside ring the bare minimum number of times…once something is in, you don’t want to take it out and go back in unless you absolutely have to. Better to add a little more lube beforehand, and don’t pull things out all the way.
- Keep playing with her pussy! It’s better for her if it’s vaginal sex with a side of anal, rather than the other way around…or you digging in her ass without any other stimulation.
- Put her hand on (or tell her to) play with her clit for extra stimulation.


5. Get it in
Lubrication needed: plenty to start, usually none extra once you’re all the way in
Risk of chocolate surprise: low to moderate
Difficulty: ★★★☆☆

If she was OK with two or more fingers or a toy, you can try to put your hot dog in her bun. The biggest factor for being able to get your dick in her ass is how well you prep her for your size with multiple fingers or toys, so don’t go from one finger to your dick.

By far the easiest angle is her on her stomach, followed by her in doggy. Missionary takes a lot more work and a bit more flexibility on her part, and her on top is not for beginners. I’ll usually move her on her stomach and fuck her in the pussy while playing with her ass, then pull out from her holes, lube up my dick, and rub it on her ass hole as a sign of what’s next. If she’s fine with it, I’ll slowly make a move.

Take similar steps with your dick as with your fingers: rub against her, gently push the tip against her (without going into the inner ring), then begin working it in. I find the best angle to be a few inches forward on her pelvis as compared to her pussy, so I have to angle my dick head down into her ass…this seems to work better than going straight in. I push the tip of the head in with my thumb.

Add lube to your head and shaft as needed while you’re going in. But don’t pull out of the inner ring once you’re through it.

Pay attention to how tense she is. Tell her to focus on breathing deep, and get her to play with herself. When she tightens up, stop, or you might hurt her. When she is relaxed, make small back-and-forth movements (you can start slow, then build up to fast, but still small movements).

Getting the head in is the hardest part. It might not happen on the first time you try with a girl. That being said, if you can get the head in, you can get the rest in. It can take up to ten-fifteen minutes to get balls deep. Take your time. Don’t force your way forward!

Pro tips:
- Expect to need a lot of time to break her in. This isn’t quickie material.
- Take tiny strokes! You might need to stand still, or take ten strokes “staying in place” before moving in a little bit more.
- Get her to play with herself. Give her a vibrator if you have one handy.
- Avoid textured condoms (?) and anything with various warming, cooling, tingling sensations (?)…it will irritate her parts, and then good luck doing it a second time.
- Safe sex is important…that being said, raw is much smoother than condom…if she’s clean, and you both have been tested.


6. Balls deep
Lubrication needed: no extra should be needed
Risk of chocolate surprise: low to moderate
Difficulty: ★☆☆☆☆

Congratulations! You got the brown flag, and maybe a v-card to boot.

You can fuck any way you want, but you can’t go quite as rough as vaginal. Get her up from her stomach into doggy to get a bit more vigorous. Anal missionary is intermediate, and a good way to raise the passion levels. Girl on top is for experienced cow girls, or chicks that are into pain.

Get her to play with herself and get herself off before you come. Or reach around and play with her clit (I’m personally not a contortionist, so I leave that shit to her).

Pro tips:
- Reach under her and put your fingers or a toy inside her, to stimulate her G-spot at the same time. Bonus points for vibration. Warning: she might turn into a quivering mess, and you will end up with a clinger on your hands.


7. (un)wrapping it up
Pull out slowly, as it can be irritating to her parts. A verbal warning helps her prepare.

You might get some brown stuff on the tip of your dick. If you play in the mud, you might get dirty. Soap is your friend.

If you wore a rubber but didn’t come yet, pull out and turn it inside out. Then you can come wherever.
If you came inside her in a rubber, you may either want to hold your dick by the base until you can toss it out, or turn it inside out until you can clean up. Choose your adventure.

If you went raw, a rag to put under her might not be a bad idea (and maybe you should’ve thought about that before you fucked on top of your pillow).
Don’t forget to wash up with a good soap and take a piss to flush out any bacteria.

After you are both cleaned up, reestablish comfort with compliment and cuddle game. Tell her how good it felt and that next time will be even better for her. All that fun stuff.


8. And to finish with an inspiring quote…
[Image: Capture.png]
– the ladies

Data Sheet Maps | On Musical Chicks | Rep Point Changes | Au Pairs on a Boat
Captainstabbin: "girls get more attractive with your dick in their mouth. It's science."
Spaniard88: "The "believe anything" crew contributes: "She's probably a good girl, maybe she lost her virginity to someone with AIDS and only had sex once before you met her...give her a chance.""
(This post was last modified: 02-23-2019 06:00 PM by polar.)
02-23-2019 05:56 PM
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RE: How to introduce girls to anal (Data Sheet)
Isn't there another thread about this shit (pun intended)
02-23-2019 06:15 PM
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RE: How to introduce girls to anal (Data Sheet)
I'll stick with fucking their pussy instead as it's much a more purpose-driven device.

"I drink only the finest breast milks."
"That's 100% Cambodian."
(This post was last modified: 02-23-2019 08:44 PM by Batman_.)
02-23-2019 08:43 PM
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Post: #4
RE: How to introduce girls to anal (Data Sheet)
Interesting guide!

Is it just me or is it generally quite easy to introduce girls to anal? Often you don't need much convincing and they are open to trying it. I even introduced a girl to anal today.

Usually I don't pursue it though.
02-23-2019 10:44 PM
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RE: How to introduce girls to anal (Data Sheet)
(02-23-2019 05:56 PM)polar Wrote:  Pull out slowly, as it can be irritating to her parts. A verbal warning helps her prepare.

You might get some brown stuff on the tip of your dick.

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02-23-2019 11:11 PM
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Repo Offline
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RE: How to introduce girls to anal (Data Sheet)
"Risk of chocolate suprise"

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02-23-2019 11:30 PM
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Rainbow RE: How to introduce girls to anal (Data Sheet)
Best way to introduce girls to anal is a dick in the butt

Bruising cervix since 96
#TeamBeard
(This post was last modified: 02-23-2019 11:32 PM by Cr33pin.)
02-23-2019 11:32 PM
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RE: How to introduce girls to anal (Data Sheet)
I just came here to use the term "Shit Stabber".

Cheers, that is all.

For entertainment and educational use only, your m8 Jackin'
02-24-2019 03:47 AM
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RE: How to introduce girls to anal (Data Sheet)
I rarely do anal. I know porn makes it look like its more common than 'normal' sex but I don't know I'm just not too keen.


Do you think anal makes girls more submissive? Do you think it should be considered in LTRs to make your girl more into you?
02-24-2019 03:58 AM
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Geomann180 Offline
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RE: How to introduce girls to anal (Data Sheet)
Funnily enough, two virgins I dated, a German and a Salvadorean, both lost their anal virginity to me first, then the normal one.

I recommend using warming lubricant. Feels grrrrrrrrrrrrrrrrrreat.

G
02-24-2019 04:40 AM
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lavidaloca Offline
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RE: How to introduce girls to anal (Data Sheet)
Your dick will get some shit on it most of the time in my experience. Its not the end of the world. Run to the shower afterwards and clean it up. You won't have some huge turd or dick covered in brown. You will have some flakes of shit on it. (Usually on the head)

I like to put my index finger in a girls ass while fucking them to get them open and warmed up to the idea of anal. This is way more steps than I do but definitely probably more effective.

This topic always makes me laugh because its so divided. Some guys love it others are repulsed by it. I think a lot of people are missing a good thing by avoiding it.
(This post was last modified: 02-24-2019 05:29 AM by lavidaloca.)
02-24-2019 05:27 AM
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Post: #12
RE: How to introduce girls to anal (Data Sheet)
Pro tip to relax the booty hole. Anal beads for a few hours before you do it. And you can fuck them in the pussy with it in but you will probably feel the beads.
02-24-2019 07:12 AM
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Dr Mantis Toboggan Offline
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RE: How to introduce girls to anal (Data Sheet)
With girls who have never done it before, I like to use a spooning type position to start out. Position yourself so that your hips are a little lower than hers (almost like she's sitting in your lap, but with both of you laying on your side) and her upper body at about a 45 degree angle from yours. YMMV but in my experience this is the best position for keeping her relaxed and allowing comfortable entry. The downside is that it's kinda hard to thrust, but once she gets comfortable with your dick in her ass you can switch to another position like doggy or reverse cowgirl.

Another one I like is a modified reverse cowgirl with her laying flat against you. This lets you grab her tits, rub her clit, kiss/bite her neck, finger her pussy, etc. If you can make a girl cum while fucking her in the ass, she will become addicted to you.

I got my Magnum condoms, I got my wad of hundreds, I'm ready to plow!
02-24-2019 02:59 PM
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RE: How to introduce girls to anal (Data Sheet)
Must be a younger thing, with porn, depravity and conditioning.

As an older dude, I find not many Mature Milfs will entertain ass play - usually balking at step 2-3 in above guide.

I'm ok with that.
(This post was last modified: 02-24-2019 03:42 PM by RatInTheWoods.)
02-24-2019 03:41 PM
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RE: How to introduce girls to anal (Data Sheet)



two scoops
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02-25-2019 03:44 AM
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RE: How to introduce girls to anal (Data Sheet)
Probably the best data-shit I have seen around here.

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02-25-2019 10:19 AM
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