2 For 1: A Beginner’s Guide To Double Penetration

SeanCody.com

For the well-bottomed, nothing feels more like home than penetration. But what about double penetration?

In this article, we’ll show you the best positions and angle of entry for double penetration and why all that pressure feels soo good.

We’ll also show you how to hit your prostate every time.

But first, it goes without saying, double penetration requires lots of lube! Don’t skimp on the lube. Put it on his entire cock and inside your ass- sometimes we forget to put it inside the butt and on it.

Pro tip 1: Inside your ass and over your ass. And all over his cock from the base to the tip. Drench the cocks. There’s two remember?

If you need some, there’s some good lube here for 35% off when you use code grind.

Got your lube? Let’s go!

Creating The Perfect Storm.

One of the keys, DP experts agree, is creating an environment where the bottom is relaxed enough to take two penises at once.

If you want to take two dick but not sure how?

Pro tip 2: you can start by taking the pressure off your legs and ass.

Pro tip 3: before you do anything have them eat your ass for at least 15 minutes. It’s the least they can do! Insist on it.

Then get on your back and get ready for sex position #1: The Cocky Cowboy.

Winter Getaway 2

This GIF is from Winter Getaway Day 2 with Lane, Brody and Joey. Click here to join and watch the full video.

Sex Positions for double penetration

1. The Cocky Cowboy

1. Tell the top to lay down on his back on the edge of the bed.

2. Sit on his cock – face him.

3. Top #2 is standing behind you now

4. You’re gonna fold over and start making out with the first top.

5. When you’re ready, Top #2 can start eating your ass again with the cock inside. The more ass eating the better, right?

6. Now Top #2 is going to be eager, dripping with cum.

7. Make sure he starts with 1-2-3 fingers until there’s some room to work with. Grab his cock and insert the head first. Now wait.

8. They are both in!

9. Now you’re going to ride Top #1 while Top #2 thrusts from behind.

You were warned, cowboy.

2. The Sausage Sandwich

For this one you’re gonna be laying down.

1. Same. Tell the top to lay down on his back on the edge of the bed. His legs should hang over the bed- toes touching the ground.

2. Now sit on his meat at the edge of a bed and lay back flat. Your back flat on his chest – not facing him.

3. Legs up!

4. Top #2 can now see a dick inside your ass and your ankles are on his shoulders.

5. When you’re ready, he can insert 1-2-3 fingers until there’s a small gap. Grab his cock and insert the head first. Now wait.

6. They’re both in.

7. Now they can BOTH thrust. Top #1 is thrusting up and Top #2 is thrusting from the side.

And the best position for double penetration is…

3. The Double Topping

Our favorite.

This is so good we’re just going to show you. [Very NSFW GIFS.]

Winter Getaway 2

This GIF is from Winter Getaway Day 2 with Lane, Brody and Joey. Join here to watch the full video.

Not bad eh?

Still got your lube handy? For the next section we’re gonna talk about a big ol’ whopper you can use to practice.

Practice kits are 35% off here when you use code grind.

But how can I get fucked by two guys without pain?

Two dicks can most definitely stimulate the prostate, which we talk about below, but how to avoid the pain?

You know what they say… practice makes perfect.

You’ve got two options.

1. you can use two toys or

2. you can combine your partner’s dick with a dildo

Either way, these whopper dildos are perfectly curved and tapered to break yourself in. And got good reviews!

Both whoppers can reasonably simulate the effect on your anus.

To boot, American whopper dildos are 35% off with free shipping when you use code grind.

But the general consensus is this: Penises are better. Of course! But this is like flight simulator… you can mess up and nobody will know!

What about the prostate

Wonder why two dicks are better than one? More pressure! Part of the reason why all that pressure feels so good is you are pushing on your prostate with twice the meat!

Wanna try now?

You can get a “sneak preview” of what that will feel like by massaging your own prostate as you masturbate.

But where is it?

We’ll show you.

For this section, we’ll use a modified technique called The Sexhalation Method to massage your own prostate.

Step 1: Gently press your middle finger against your anus

Step 2: Inhale to a count of four and squeeze your sphincter shut.

Step 3: Exhale to a count of six and release the sphincter.

Step 4: Repeat until you draw in your entire finger.

Step 5: Gently probe the anal wall upwards towards your navel.

The prostate is located behind the anal wall in the direction of your belly button (two to four inches from the sphincter). Be careful! The prostate is very sensitive. Do not poke and prod. Caress and stroke. Press gently. Use feather-light touches.

You’re looking for a walnut-sized fleshy ball hiding behind the anal wall. Finding it is a little like playing hide-and-seek, only you’re using your finger rather than your eyes. The prostate is behind the anal wall in the direction of your belly button (two to four inches from the sphincter). Be careful! The prostate is sensitive.

Step 6: Find and trace the contours of the prostate.

Once you locate it, trace your finger around the gland. Take a tour. Notice where it is. Make a mental note of how far in (and up) you had to go so that you can use this memory as a GPS for the next hide-and-seek adventure.

Step 7: Massage the prostate

You need to exert firm pressure without pushing too hard. Firm but comfortable is your goal. Start at the top of the prostate and slowly push down toward the center. Then go back up. Then start at the bottom and slowly push upwards toward the center.

Step 8: Massage the prostate while you masturbate.

You may or may not have had an erection while exploring the prostate. It’s now time to purposefully get one. Massage the prostate as you masturbate to climax. It is quite eye opening to feel your prostate enlarge as you’re about to orgasm and then feel the entire rectum—sphincters and all—rhythmically contracting as you ejaculate.

If you want to massage your prostate during masturbation but don’t want to go through the “hand yoga” contortions (let’s face it, you have to go through a bit of twisting and bending to reach the prostate with your hands) try using a commercial prostate massager like the Rude Boy.

Sex toys and lube are up to 35% off for The Gaily Grind readers here.

Can’t find your prostate or not sure if you have?

If you still can’t find your prostate it could be that your fingers aren’t long enough. You should try a prostate massager that’s shaped to match the form of the anus.

Here’s a closer look:

Pictured: Rude Boy inside the anus.

Notice how the Rude Boy prostate massager is shaped to hit your prostate gland two to four inches into your rectum (towards your belly button). To boot, it also stimulates your perineum- which is the space between your balls and your hole. The Rude Boy is 30% off with free shipping when you use coupon code GRIND.

If your prostate is positioned higher than average and/or your fingers are shorter than average it can get a little tricky. That’s where the Rude Boy can help. It’s also a bestseller and it’s rated five stars.

Aneros is 20% off and Rude Boy is 30% off + free shipping at AdamMale.com with coupon code GRIND.

You can also try different positions

For example, some guys have better luck laying on their left side and putting their right hand behind their back while bending their right knee.

One more thing about the prostate

You can also try a more indirect route to stimulating your prostate. Find the pressure point on the perineum directly below the prostate.

Do this: Put your index and middle fingers together and press the fingertips on the area between your anus and the scrotum.

Southerners call this area, “The Tain’t” because it “tain’t your ass and it tain’t your balls.”

Start at the boundary of your sphincter and gently press up. Move an 1/8 of an inch toward your scrotum and press up. Keep going and you will find the sweet spot—generally, it’s the most sensitive spot in a most sensitive area. Try different pressures and find the touch that you like best.

Bonus: Bottoms love it when you press on this while you are inside them.

It’s time for sex…with yourself

There is no substitute for a hard penis but there is a surrogate. Dildos!

But not just any dildo. A dildo with detailed specifications.

You need to buy one that…

Has a flanged base and is tapered. It’s the collar at the base that prevents the dildo from getting stuck up your ass without a way of getting it out. Trust me, there’s nothing fabulous about a trip to the ER. The lighting is bad, the outfits are ugly, and they have no concept of a VIP line.

Get 35% off sex toys and lube here

If you’re starting out, I recommend a tapered body with a smaller head and fatter base. Like the whopper!

You can also slowly build up your insertion tolerance with this 3 level trainer kit. All are solid black and made from soft but sturdy rubber.

Colt Anal Trainer Kit is 35% off with code GRIND

One more thing…

You can wring the last bit of semen out of your ejaculation by doing the following. Right after you ejaculate press between your ass and your balls and glide toward your balls. As you reach the scrotum, grab the base of your cock and squeeze all the way up.

You are squeezing the last bit of toothpaste out of the tube.

You’ll see extra semen come out that you didn’t know you had in you.

If you’re a “dripper” after you ejaculate this will completely end it.

What is good for you?

Some guys find prostate stimulation pleasurable while other guys find it annoying. Some men only like it after a certain point of sexual arousal.

While others like it at any time.

Still others don’t care for it at all. Individuals vary. What causes ecstasy for some causes boredom in others. It doesn’t matter whether you like prostate stimulation or not. What matters is that you experience the process. It is quite astounding to feel your prostate thicken and grow inside the anal wall as you get closer to orgasm.

For those who are getting started
The locator if you are new to anal sex

For those who are kinky
The rude boy for more hardcore action
[30% off with free shipping when you use code GRIND]

For those who want direct prostate action
The 3 speed sex machine
[35% off with free shipping when you use code GRIND]

For those who want it all
The luxury edition to make all your dreams come true.
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Watch porn star Colby Keller helps us navigate the prostate, below

Disclosure: This post is brought to you by Gaily Grind Best Picks Team. We mention products and services you might find interesting, and if you purchase them, we may get a small share from the sale. Affiliate links used. Have something you think we should know about? Contact us here.