Original subtitles

Penny and Devin.

Hi!

Come on in.

Have a seat.

Thank you.

Thanks for coming.

Thanks for being part of my workshop.

Oh, we're going to love this.

So I want to know from you guys.

Penny, we're going to start with you.

How much experience have you had with anal play?

Quite a bit, actually.

A surprising amount.

A couple of the companies that I work for do a lot of anal play, so I'm really good with a strap-on.

I have nails, so it kind of messes things up as far as finger play goes.

Right, we'll take care of that in a moment.

And when was the first time you started to experience anal play?

Well, it was several years ago.

I got into it and realized how pleasurable it was, and ever since then I've kind of been somewhat addicted to it.

That's Penny now.

And Penny, what would you say to women out there who might be freaked out by the idea?

I think it's an incredibly sexy thing for your partner to give you that kind of power over him.

Because stereotypically, that's their job.

That's what they have to do.

So to be given something so manly, it's very empowering.

And don't be afraid.

And what about guys who are nervous or freaked out about it?

Well, I think the biggest misconception or preconceived notion about anal sex is that there is pain involved.

And that's not true.

If you know what you're doing, if you prep yourself properly, and you have the right partner who knows what she's doing, it can be the most incredible experience ever.

I think that's true.

I think people assume that it's going to hurt the first few times, it has to hurt.

And I always tell people, if it hurts, you're doing it wrong.

Like you haven't used enough lube, you're not relaxed enough, there hasn't been enough warm up, and you have to listen to your body.

So, Penny, let's talk about those nails.

I know, I know.

Let me see them first.

I'm sorry, I'm a porn girl.

They require me to have long, luxurious nails like this, but it doesn't make for good anal sex.

Okay, well I think I have a trick that's going to work.

Can you fix me?

I will fix you.

Fix me!

Ordinary cotton balls found in anyone's bathroom.

Really?

I have cotton balls in my bathroom.

Okay, and some gloves.

So, what I think we should do is, these are big cotton balls, I would actually break them in half.

Okay.

Or maybe even in quarters.

And put them, you're basically going to put them in the fingers of the glove.

Should we try to blow off this glove to do that?

Do you mind my lipstick in your glove?

No, I like it.

Okay, great.

It's like you're kissing me.

So, I'm going to just shove these down here into the fingers.

And this is going to protect your butt, your nails, and the glove.

Because I think if you put this glove on straight, especially with your beautiful nails, coming straight from the manicure, it's going to rip the glove.

Definitely.

So, Devin, tell me a little bit about what you like during anal play.

Because I know some guys like anal play all by itself.

Some guys really need to have their dick played with while they're getting penetrated.

Do you have a preference?

I love my dick and balls played with while I'm having my anus stimulated.

Yeah, and does that intensify the sensation?

Absolutely.

For me, as soon as something goes in my ass, it's like instant hard on.

It's such a turn on for me.

Really?

And if you go deep enough, and if you find my prostate or my K-spot, it could lead to multiple orgasms.

Multiple orgasms?

Multiple orgasms when you can ejaculate, too?

Wow.

It's that pleasurable for me.

Wow.

Are we in for multiple orgasms?

I'm so excited.

Here's your other glove.

Thank you.

And is there anything you don't like?

If those are all the do's, what's the don't for you?

We have to really ease into it, because I am sensitive, but once I'm loosened up, I'm ready for anything.

But the don't is don't just jam anything in there, because that's a no-no.

Of course.

Because it will...

Ouch!

Yes, exactly.

And do you like to warm up with fingers, toys?

Do you have a preference?

I like it if a woman plays with me with her fingers.

That's the best way to start.

And then we just move on to the toys, but I like to start with the smaller toys and basically gradually increase to bigger and gradually, you know, kind of like climbing a mountain, you know?

That makes perfect sense.

Yes, if that's good enough.

Because it's all about the warm up.

It is all about the warm up.

And just working your way up slowly.

And then once I'm worked up, then I'm completely into it, and it's amazing.

Are you excited?

I'm so excited.

You got your gloves on?

How do they feel?

They feel kind of funny, because I can't, like, I can't feel my nail in there, but my nail is protected, and I'm like, here, will you squeeze it and tell me, this will be perfect, right?

Absolutely.

Sans nail.

Instant...

That is great, because I have had women put nails in there before, and sometimes it's okay, but other times, if they start doing certain things...

Like a little prostate massage or something?

Exactly.

And I'm always terrified, you know, to even use my hands.

I'm great with a strap on, but when it comes to my hands, since my nails are always done up...

You just avoid it.

Right, because I don't want to...

Oh, so we may teach Penny some new finger techniques.

I'm excited.

This is going to be awesome.

And this is a great idea, because when I walked into the set and saw her nails, I thought, uh-oh.

Exactly.

No, we will take care of you.

Don't worry.

This is going to be fun.

Okay.

So, you want to get started?

I would love to.

Get Devin a little naked?

And if I know Penny, even though she doesn't need to get naked, she will.

I hope so.

Yeah, take off all my clothes really quick.

So, as we talked about, it's all about the warm-up.

And I think a good beginning is just some external stimulation.

Just some lube on your finger, rubbing against the outside.

Even the anal opening is so rich in nerve endings, and it's so sensitive, that that feels really good.

And I think it also gets you to focus on the area, and gets you relaxed.

Because, again, you don't want to start penetration until your partner is totally relaxed.

Devin, do you like to have your cock and balls played with now, or will you just do one finger without that?

Um, I like my cock and balls played with any time.

Shocking.

Shocking.

I got the lube.

Okay.

So, feel free to do whatever you like.

Okay.

How do the gloves feel?

Good, actually.

Do you feel like you have sensitivity?

I can feel them with the pad of my fingertip.

Okay, that's good.

And then when I go here, I know that it's not going to hurt him.

So I'm not as hesitant to play.

Okay, good.

Good.

Another good trick is to use a vibrator, just on the outside.

That feels really good, and also helps some guys, yeah, really relax.

Really relax.

Okay, so let's start with one finger, and I want you to go in just, really just to that first knuckle, and stay there.

Let the ass get used to it.

You ready?

I'm ready.

Devin's ready.

Now, someone watched my first video, because Penny just did the pad of the finger trick.

Knock, knock.

I'm coming in.

Like ringing the doorbell.

So the pad of your finger, I saw you, you rubbed it right there.

The ass relaxed a little, and then you slid right in.

That was great.

How's that feel, Devin?

Oh, it feels great.

Okay, good.

You can't feel my nail, can you?

No, I can't.

Okay, good.

That's good.

This changes everything.

I'm so excited.

Okay, we know Devin is experienced, so I think you can go further in, but you're still going to go slow.

And remember, you always want to angle toward the front of the body.

So that, yeah, there you go.

Good.

Let him give you feedback.

Not a lot of, ton of movement.

Just, again, just to get the ass used to the feeling.

How does that feel, Devin?

It feels really good.

You can actually move it around a little more if you'd like.

Move around a little.

In and out, or what do you think?

Just kind of like wiggle it around inside.

See, I think some guys really like that come here.

It's kind of like when you stimulate the G-spot, which I know you've done a lot of.

So it's the fingers toward the front of the body, in this position, toward the front of the body.

And it's, instead of a lot of in and out, it's more of just a sort of almost a pulling motion, like a pressure thing.

Like that, but upside down.

And in my opinion, it's the best way to loosen yourself up.

Yeah, less movement and more... right, right.

Like less in and out.

I think going in and out, when you're not quite warmed up, it stresses out the sphincter muscles.

Yeah, I don't prefer the in and out for starting.

Yeah, it doesn't feel as good.

I think just staying in there and making that little bit of motion.

Also, I think people don't realize that at the tiniest amount of motion, it feels really good.

So people have to remember that it's going to register as much bigger than they think.

So remember, front of the body, that's where you're going to get the prostate.

And I think also people should realize that the more turned on the guy gets, the more his prostate is going to swell.

And it's going to be easier to find.

Yeah, actually she is getting there and I can actually feel it.

You can feel it.

And it feels really good.

But don't you think you can take more stimulation and more pressure once you're more turned on?

Absolutely.

Yeah, definitely.

So, it looks like you have this covered, Penn.

I think I'm going to leave you guys alone.

But if you need me, the lube is here.

Just call.

Thanks, Tristan.

Okay, bye.

Thank you, Tristan.

Go down more.

There we go.

Right there?

Yeah, that's good.

A little more pressure left.

A little more pressure.

Like that.

Yeah, baby.

You know what I like?

I do.

Move it around like that.

That is nice.

Get nice and push it up.

And then move on to something else.

Maybe a little better.

You want to do two fingers, baby?

Yeah, two.

Maybe a little more lube before

we...

Is that your spot down there?

Communication is crucial.

Remember to keep the dialogue going and give your partner feedback about how everything feels.

How about a little more pressure, baby?

Like that?

You

want to go a little deeper, too?

I can take it.

Now that you've got me nice and loosened up.

You're warming up real nice.

You're too good to me, baby.

You're too good to me.

Hello, little red butler.

Hello, condom.

I'm going to put a condom on it since we're using a silicone lube.

Okay, baby?

Oh, please do that.

Good.

I don't have too much, right?

Makes it all the better.

Just guide it in slowly.

Curved dildos and plugs are great for prostate stimulation.

Always aim the curve of the toy toward the front of his body.

How's that?

Oh, wow.

And it's good.

It's really good.

Oh, wow.

Oh, and that's true.

At the same time.

Oh, you double the pleasure.

Oh, wow.

What an afternoon.

Good Thursday.

Oh, so good.

I love your ass.

baby?

That's nice.

You like it.

You like my tap on?

I like that a lot.

A

little bigger.

Go a little deeper.

That's my boy.

I just love that.

Tidy.

Let's see.

Actually, right there.

That's a stretch.

Buzz, buzz.

What do you got there?

Five grades, baby.

Ah, I love that.

Put another condom on it.

Oh, look at that.

I surprised myself.

So, this is going to vibrate and bring you some pleasure as well?

Yeah, I think you're going to love it.

Oh, I'm going to love it.

I'm going to love everything I do to you.

I definitely want you to get something like this, too.

Oh, I will.

I got a whole line up of pleasing toys.

And I just like to please you, too.

I love pleasing toys.

Get it nice and looped up.

That looks so hot.

You know what?

Doggy style position works well if you're just starting to explore how to properly wield a new toy between your legs.

It gives you a chance to find your center of gravity, practice your hip action, and get used to the rhythm of thrusting.

Doggy style can also be an advanced position for hard and fast thrusting.

Do you need more of this?

I think I'm okay.

You can go deeper if you'd like to.

That looks so sexy.

Oh, that feels good.

Have him come back on the dildo while you remain still.

This way, he can control the angle, depth, and speed of penetration, and go at his own pace.

Don't move.

Can I turn it on?

Oh, wow.

Ooh, it's bright.

This dildo has a vibrator in the base, which means she can feel the vibration against her clip.

Plus, because it's a silicone toy, the vibration will be conducted all the way to the end, so he will feel it, too.

That was so awesome.

Geez, huh?

It's like a card show.

Oh, come on.

Start that thing up again.

Start it up for me.

There.

Can you feel that on your clip?

A little bit.

What am I getting back?

It's my thigh.

It's good.

You're balls on my thighs.

I love you.

That's nice.

In this sitting missionary position, he lies on his back and she comes between his legs.

Instead of her kneeling, like in missionary L position, she spreads her legs and sits back, using her arms for leverage.

She has easy access to play with his penis and balls while she penetrates him.

He can also touch himself, leaving her to concentrate on establishing a rhythm, since she's in charge of the thrusting action in this position.

Another alternative is flying missionary position, where she stands near the edge of the bed and he lays on his back with his knees bent and his feet resting on her chest.

He can have some more control over the penetration by gently pushing off her body for leverage.

She has access to his penis and balls, as well as his chest and nipples.

He can watch her as she penetrates him.

Just like that.

It's just the thought of it gives me heart.

It's just the thought of doing that.

Oh, it feels so good.

This is the part where all my toes curl up.

Oh, baby.

He's a good baby.

Using a vibrating dildo is just one way she can get off while she's penetrating him with a strap on.

Another way is to use a double-headed dildo, designed especially for use with a harness.

One end goes inside her and the other end slides through the o-ring on the harness to go inside him.

How does that feel, baby?

Oh, it's going to feel even better once I'm inside of you.

Like that?

A little bit lower.

Knock, knock.

Give us a hug.

Now, as soon as you can move me as hard as you want.

Oh, baby.

Oh, wow.

Oh, it feels good?

Yeah, it feels really good.

I'm sweating.

It's my cheese pull.

Got your cheese pull?

Oh, man, that turns me on.

As she thrusts one end of the dildo inside him, the other end pushes inside her.

If he likes to have his cock stimulated during penetration, but you can't reach to do it, he can stroke himself.

You don't like that, do you, girl?

You need to cough, baby.

Oh, I'm so hot, baby.

I'm so in the milk.

I want you to enjoy this as much as possible.

I enjoy it every minute of it.

You can come whenever you want.

I just want to please you today.

It's what's important.

Oh, my knees.

Does it feel good for you, too?

Does it feel good?

I feel so good.

Oh, God, that's good.

I'm so enjoying this.

If she feels nervous about taking full control of the penetration, or if she has limited mobility, positions where he is on top, like cowboy and reverse cowboy, put him in the driver's seat.

In reverse cowboy position, she lays on her back and he sits on top of her, facing away from her.

She gets a great view of the penetration.

He can ease himself down on the dildo, then be in charge of the angle, depth, and pace.

He can find the perfect combination for prostate stimulation.

If he likes genital stimulation in addition, he can stroke his own penis as he rides the dildo.

For some men, this position can make them feel especially vulnerable, or self-conscious, or too much like they're on display.

So make sure it works for both of you.

For couples where the man is much taller or larger than the woman, she may not be able to sustain his weight on top of her.

In that case, try froggy or reverse froggy, so that he's crouching over her, but doesn't actually rest his body on top of hers.

There's a lot more in there, too, aren't you?

There we go.

Good.

Good.

I

think there's two in there.

You like them?

Oh, how does that feel?

Good.

You like them?

There's two.

There's three.

You want to try four?

You want me to try four?

You want four?

Okay.

I'll give you four.

As you add more fingers, always add more lube.

There's one.

Two.

Three.

You want the fourth?

Yes, please.

Now that I got you a little loosened up, I want to stick something else in there.

How many of these would you like to put in your butt?

Two.

What fans of anal beads love about them is the ability to experience one particular sensation several times over.

When the sphincter muscles relax, the anus opens up, a bead slides in, and the muscles close around it.

Do you think I need to put some more?

Because there's only three left.

I think so.

You think?

You think I can put one more in there?

I think you probably can.

Do you think I could?

Really?

Anal bead toys should always have a handle or base on the end for safety.

Well, there's only one left.

Do you want me to try and push it in there?

Do you think you can take it?

I think so.

Go

ahead and ask.

You like that?

Does that feel good?

Slowly pull the beads out, and it will create a different sensation from when they went in.

It's staying in your ass.

Do you like that?

Yeah, it feels real different, but good.

Different but good?

Can I stick something else in your ass?

What else do you have?

Did you already fit this whole thing in your ass?

It's crazy.

The whole thing, from foot to up to here?

That's awesome.

Butt plugs are great for men who like a feeling of fullness and pressure without in-and-out penetration.

To get his ass relaxed and ready for more, slide the butt plug in, then leave it in while you move on to other activities.

Oh, yeah, that's it.

Oh, that's it.

Get on your knees.

If you love to look at, squeeze, or spank your partner's butt, doggy-style position gives you the best view and the most access.

You can hold on to him for leverage or lean back on your hands.

Get it to you a little better?

A little bit faster?

I like watching you.

You're awfully quiet.

Do you like my dick in your ass or what?

I love it.

Oh, feel your thighs.

you like that better?

Just like that?

I like the way your ass jiggles on my dick.

In spoon position, both partners lie on their sides and she enters him from behind.

Spooning works well for people of many different body sizes and heights.

Because penetration is not as deep in this position, make sure the dildo is long enough since you will lose several inches.

This position leaves plenty of room for him to touch himself or for her to reach around to stimulate his penis during penetration.

There is also plenty of skin-to-skin contact.

This harness has a pocket inside for a small bullet vibrator so she can have her clitoris stimulated as she penetrates him.

For couples who've tried and enjoy doggy style and want to take it to the next level, give stallion position a go.

He stands and leans over the edge of the bed and she stands behind him.

Ideally, she will come at him from slightly above, the perfect angle for direct prostate stimulation.

This position works best if partners are about the same height or she's taller than him.

If couples want to explore dominant-submissive roleplay with their anal sex, doggy style can work well to help a woman channel her inner mistress and a man surrender to her will.

If he puts his head down while his butt is in the air, his body is angled well for her to stimulate the prostate.

Stallion position works best for men who don't want their dicks stimulated during penetration, since there isn't easy access.

Mmm, yeah, you love that dick, don't you?

You love that dick, don't you?

Fuck yeah, baby.

Yeah, you know it.

It's my turn.

It's a good fuck.

Yeah, you ready to give me a fuck?

That's good.

You like that?

That's good.

That's good.

Okay.

Oh, kiss my finger.

Try combining a hand job or a blow job with one finger in his ass to get him turned on and warmed up.

Of course I am.

I'm just, like, watching you.

Use the loop.

Get the loop.

You want the loop?

Of course.

Okay.

You want me to spit mix together?

Come on.

Mm, where do you want me to go then, huh?

I can do that for you.

What are you all about to get a hearty spread?

You're about to get a hearty spread.

Just

do it.

Just stroke it.

Just stroke it.

Stroke it?

Like that?

Like that?

Mm, like the head.

Yes, you know I like that.

Right in the front, right in the back.

Yeah, give me that toy.

Toy?

Well, I'm going to taste, but I have to step up there first.

Why don't you?

Is this where my fingers are?

Right in there.

I'm going to try to help him.

Oral stimulation is a great way to warm up his ass.

Use your mouth and tongue to explore the folds of his puckered opening.

Swipe your tongue around his anus or lick back and forth.

Experiment using the wide, flat part of your tongue.

Then try the pointy tip.

If you feel comfortable, you can slip your tongue just barely inside or move it in and out.

Big boy?

Thank you for trusting me.

You're opening up to me today.

Let me do that for you.

I'm really trusting you.

Does that feel good?

You can tell me if you want me to do something.

Do you want to get a toy?

Just for you.

It's warm.

It's good?

Do you want to warm it up for me a little bit?

You know what you want.

Be careful.

Now, is it easy for you guys?

Nothing compared to four fingers.

We're rolling on all day.

That's fine, that's fine.

When he keeps a butt plug in while you have vaginal intercourse, it intensifies all the sensations he feels.

Ah, ah, it's good.

It's really good.

How's the last two?

It's got to be the sexiest snowball ever.

I don't get the purpose of that.

Well, you are just impressing me today.

Which one do you want?

I think the anticipation is satisfying.

You're all open for me.

What are you worried about?

You can button your hip like that.

Glass toys are firm, smooth, and seamless.

Plus, lube clings to them nicely.

This is good.

This is good.

Does that feel good for you?

Ah, it's good.

Positions like this one, where she's on top, facing away from him, give her easy access to stimulate his ass.

You want more?

That's gross.

Do you see it?

Ah, I'm falling.

Sweetheart, I'm falling.

Okay.

Sure.

Well, anybody ever said there wasn't multiple orgasms for men?

They need to meet you.

Look at that.

Look at the black one.

You look at the black one?

You like this one, huh?

I do.

I would like this one, too.

Hot damn.

Put it in.

Put it in here.

Yeah, baby.

It's all you.

So, this one's silicone, huh?

This one?

Trust me, you're fine.

Put some water lube on it.

Oh, I can't even hold it to lube it up.

Just for a second.

I'm jealous.

I want one of these toys.

This toy is designed especially for prostate stimulation.

As you slide it in, aim the curved part toward the front of his body.

Once it's in, the outer textured part hugs the sensitive perineum.

He can feel the vibrator both internally on his prostate and externally on his perineum.

That's good.

Does

the vibration make a difference?

I suppose it really does.

There you go.

Why are you taking it out?

To play with you.

Take it easy.

I'll put it back in there, baby.

Don't worry.

Put it in, you meanie.

Let's play with you.

You

got it?

Come

Stop.

Stop.

Come on, baby.

Come on, baby.

You stick your finger up my butt again.

You want to make me cum?

You want to make me cum?

Stick your finger up my butt.

Here.

Thank you.

That's it, right?

That was fun.

That was fun?

You had a good time?

Good.