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Pegging Online Course:
Discover the Fantastic World of Strap-on Butt Sex

With
Lola Jean
,
Sex Educator & Dominatrix
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About This Course

Explore a different kind of anal play with Lola Jean’s introductory course to “Pegging”. Learn about the techniques, toys, positions, and best practices in a fun and engaging manner. Be brave and overcome your fears and hesitations about the subject to enable a new path of pleasure!

What You Will Learn

What You'll Learn

  1. Understand tools and prep for pegging
  2. Explore hand play techniques
  3. Develop skills for pegging penetration
  4. Address fears and hesitations around pegging

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For everyone. Singles, couples, all genders and orientations.

Your Instructor

Lola Jean

Sex Educator & Dominatrix

This Sex Educator and Pro-Domme brings a refreshing understanding of sex, sexuality, and kink. Jean provides individuals with tools and information that are designed to push individuals past what they think they are capable of.

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Lessons and Classes

Total length:
30-60 min
  1. 1. What Is Pegging
  2. 2. Common Pegging Fears & Expectations
  3. 3. Tools & Preparation
  4. 4. Hand Play
  5. 5. Penetration
  6. 6. Aftercare
  7. 7. All Your Pegging Questions Answered
  8. 8. How Do I Get My Partner Interested In a Kink
  9. 9. What to Do With My Hands During Pegging
  10. 10. Is Anal Play Enjoyable for People With Vulvas

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Transcripts

So you wanna know about pegging? Well, I'm here to tell you everything you need to know. I'm Lola Jean a sex educator and mental health professional. And this is butt stuff. You're gonna like it here. Pegging is an act where one person wears a strap-on and penetrates the other person anally. Now the person wearing the strap-on, they could be a vulva owner or a penis owner. As long as they're using that apparatus to penetrate the other person. The person getting pegged, could also have a vulva or a penis. As long as they have a butthole, they can be pegged. So someone might be into pegging for more of the mental aspect, a bit of power play, being submissive, the act of being fucked. They may also be into it for the physical reason. It's physically pleasurable to stimulate around the sphincter. And if they have a prostate, newsflash prostates like to be stimulated. For the person who's doing the pegging, the pegger, that person can feel that sensation on their genitals, that movement, that rubbing, kind of similar to sex and can find it physically pleasurable. There's also the power aspect. - I think that power switch is, for me, very exciting. At least I find. I think just because putting myself in a position, just like the switch of, I guess, being a penis owner and then switching out to be a little bit more vulnerable and let someone, I guess, have a bit more power or control over you, I think is a really... At least I find exciting. - There's an aspect of intimacy involved when you're penetrating someone and going in someone's butt. Now someone might be into pegging for more of the mental aspect, more of the fantasy. So the act of being fucked, the submissive aspect. Also, if you wanna be able to fuck butts, you need to have your butt fucked. You need to understand what it feels like. So why do I find pegging enjoyable? As the pegger, it's not a part of my body, I do find it physically enjoyable. I'm gyrating my hips. I'm grinding my mons against their body. - It's a power thing that women don't usually get to experience. So it's about this mutual connection and the pleasure is there, but it's almost secondary. - Now, mostly, it's mentally pleasurable. I really enjoy creating that safe space, allowing for someone to feel vulnerable enough to be able to access a new level of pleasure. I like introducing new things to my partners. - [Interviewee] Inserting yourself into someone's body is like, that's a big thing. - How are we learning about pegging right now? (foreign language) - Well, I just wanted to say thank you for letting me borrow your boyfriend's ass. - No problem, that's what friends are for. He's a huge slut anyway. - Porn is the most easily accessible outlet, but porn isn't teaching us how to peg. It's showing the most extremes. (moaning) (moaning) (moaning) Now porn can be a great tool for entertainment, or learning about something we might want to try but we shouldn't be using it for education. In porn, what you're seeing is acting. It's a show. You're seeing giant dildos ramming into butts. You're not seeing any of that prep work, you're not seeing anal massage, you're not seeing prostate stimulation. Pegging doesn't have to be this dominant and submissive act. It can be quite caring and loving and slow. Pegging is a process. (upbeat music) Putting something in your butt, isn't going to change your sexuality. You're not going to be a different person once you've had something in your butthole. You might have explored new pleasure, you might have found out something new about yourself. Like maybe you like being penetrated anally. Doing things with your butt is fun. You just discovered a new way to please yourself. The key to unlocking new levels of sexuality are in your butthole. I think everyone can benefit from having their butt fucked. I think the world would be a better place if everyone had their butt fucked, like once. (upbeat music) But like properly, maybe twice. (chuckle) (upbeat music) - Now, there are two main things that people are usually most nervous about or what might prevent them from getting into pegging in the first place, and those are pain and poop. (Lola blows air) (happy music) As a sex educator, I'm asked a lot how do I convince my girlfriend to do anal? The word convince is probably your first mistake. (buzzer noise) - I ran into kind of challenges with how to ask partners and then I, you know, I wasn't really aware technically of of the skills involved. So it was also, that was a hurdle for me too. So yeah, I, it's been a curiosity of mine for awhile but yeah, I've only really just started acting on it. - I was always curious and kind of interested to try it and it's whether, I guess the stigma from her perspective would be kind of I don't know a put in or whether she would take it as strange or whether she would see me differently. So I think that was probably the biggest hurdle for me. - [Lola] Don't put the pressure on them to be into or perform this act. Tell them why you're excited about it. Tell them that it turns you on, tell them why it turns you on. Give them information, what might be in their head about pegging. Isn't accurate. Maybe they've seen pegging in porn and assume it's going to be like that. - (moaning) - Oh yeah I feel that tight ass and you're pushing that vibrator against my tight little pussy you're getting me all nice and wet - Give them the time and space to think about it. Don't pressure them into doing anything. Let it be their choice, if they want to participate with you, explain how it might be pleasurable for them. - For women there's a bit of a taboo with the thing. Like, Hey, like I wanna, I wanna fuck your butt - [Woman] Why is that a taboo? - You know, I wish it wasn't. And I don't really experience it personally anymore, but but it's, it's kind of, you know there's this societal narrative that says women are supposed to be the receivers, the passive ones in sex. And I, it took actually like personally it took a while for me to really shake that off and emerge from that. - I don't know. I feel like the more I've done it, the more comfortable I become just kind of having that conversation and sort of bringing it up. But I mean, it's still kind of a challenge when I first meet someone, like how do you phrase it? How do you explain it? How do you make sure they're comfortable? And it's not something that's gonna make them feel kind of strange or out of place - Where are you from? Can I stick this in your butt? (laughter) - All right. So pain, that's a big fear. You don't want to hurt someone else who has the butt. And if it's your butt, you're scared of that getting hurt. The key is to go slow, communicate and breathe. There's a ton of ways to get eased into the process without putting the dildo right into your butt. Pain can be avoided, if you have a lot of pain with anal sex, you're probably doing it wrong. Anal penetration can be eased into, there's a variety of ways that you can relax the sphincter without going straight into anal penetration. It's a gradual process working up to that dildo. Don't think that you have to take a giant cock right away. Maybe you only take fingers. Maybe you take a smaller one. - I mean, it's kind of it's not really something that you're taught. (laughter) They skip that in sex ed in high school so - Ms. Jensen, is it true that people can tell when you're menstruating - [Ms. Jensen] Pay more attention to your hair and your nails and plan to wear your prettiest dress. In other words, be your most attractive self - Ms. Jensen, what about dancing? Can you, when you menstruating? - [Ms. Jensen] it's not a very good idea to skate or ride horseback or play fast games like volleyball and basketball or do strenuous dancing like square dancing. - If we're talking about butts you can bet we're going to talk about poop. Poop happens, they're butts. It's to be expected. It doesn't always happen, but it can be messy. But there's different things that we can do in terms of preparation and cleanliness whether that's wearing gloves having cleaning supplies nearby or douching beforehand - [Man] I was worried about the cleanliness. You know, like is it going to be a mess? You know - I'm all right with mess just so you know, don't worry about that, okay, cool. - [Narrator] Soon, Molly will be a young woman like Genie, having dates, going to dances and lovely romantic dresses and making new and important friends. There are so many wonderful things to look forward to. (orchestral music) Growing up, it's an exciting time. (orchestral music continues) - Hi and welcome back. Today we are talking all about pegging. - And a lot of butt stuff. - I'm Lola Jean, I am a sex educator and mental health professional. And today I am joined by Dominus Eros. (calm music) - I've been doing tantric healing for quite a while now, as long as a sex educator and pro-domming. So a lot of it really encompasses a lot of my interests in life, my passions in life. And first and foremost, I want to bring pleasure and to bring education of pleasure and how to go about that. (calm music) (slurping) (sighs) (thuds) Your ass does have a technical function for you. It is to take the poop out of your body. No matter how much prep you do, there's gonna be some stuff that can happen to a certain extent. - Potentially. - Potential something, especially for, let's say you've prepped all you wanted to prep. What if you're having a long session, right? And then things can move through your system. You're having a lot of movement. Just physically, things are moving in your system. So stuff can happen. We will go over steps so that you can make yourself as comfortable as possible, whether it's pre-prepping with flushing out. If you're not someone who's into flushing out, then what else can you do? Having things on the side so we can have easy cleanup. - Some people, especially if it's their first time, they like doing enemas with the water enema to kind of flush it out of your system. Some people really like the ritual of it, that they're like cleaning their body for someone. After you've been doing this for a bit, you tend to develop a relationship with your bowels, so you kind of know where you're at. Some people like to say to eat like a super clean diet. I don't think that's super necessary. Like, don't eat a giant burrito like an hour before. (buzzer sounds) - So we're going into about how cleanliness can be so efficient and easy with condoms. Whether it's a toy, whether it's the full-on dildo apparatus regardless of what you're using. - We should be using condoms on twice. - It's just makes it easier to clean up. There are a lot of toys on the market that are not steel-based. Steel's super easy to clean, I mean. - But also you can pass STI's. - Correct, so having it across the board just makes it easier, it's efficient. You can grab a secondary glove to peel off in case poop had happened, right? And then it's easy to throw away as well. - Well, so one of my best tools, one, because I have claws. (cat meows) So that is good for protecting those and also making you feel better if I'm gonna go into your butt. - Don't wanna get cut, no. - But all it took was just one situation where I went in without gloves, some poo happened, easy solved, wear gloves, if it happens, take it off, throw it away. I'm not getting lube all over my hands. It's just a really easy cleanup mode and I really like the ritual of it of, like I'm putting on this glove, I'm gonna be taking this care with your butt, it's just really nice. What about lube? - Lube, lube, lube, lube, please. You do not wanna go in dry. Anal tears happen. - Fissures, yeah. - Yes, you don't want that. You wanna try and avoid that as much as possible 'cause again, it's gonna make the experience uncomfortable and you don't wanna be uncomfortable. Then is whether you like something creamy versus something that's more slippery. Do you want something H2O based, water-based or do you want something that's more oil-based. Use as much as you need, don't under use. That's the worst thing you can do is like under using lube. Use all the lube, you can buy more, it's okay. - [Lola] Don't use sparingly. - [Dominus] Use it, it's your personal pleasure, enjoy it. (gentle music) - Let's talk about toys. - I saw that we had one that we definitely wanna talk about. Let me go get that for you. There you go. - So this toy is really nice. It has a lot of weight to it. It's also really easy to clean because it's made out of steel. So, technically this end is supposed to be for the G-spot, this end for the prostate, but you can really use those interchangeably. What's also nice is instead of this kind of in out motion it's really just the rocking that needs to happen in order to feel that pressure. - I have Netflix going on and we're just doing this. Feels really good, that's a real Netflix and chill. And then again, it's very simple, it's very easy to use. - It's also conductive so you can warm this up. If you wanna make it really cold, you can do that too. - To be a dick with that too, you know what I mean. - But you can run it under warm water before you insert or add your lubricant. - So a nice training tool that we're going to use to get over the sensation of something that's in your butt is a good old butt plug. Now, this will vary from person to person what they like. It's got small neck, so it'll just be in there and what it's going to do is just train your butt to having something in it. This will not get to your prostate. So it is not a prostate toy, know the difference, anyone can wear this. So it's fun for all parties. You got my personal favorite one. This is my personal toy, actually. It's a little more bulbous. This is going to get more prostate action. It feels really good. As you can see here with the hooks, this part is gonna hit against your perineal, which feels really nice. It's gonna give that good pressure, root of the cock kind of pressure, this little finger do hickey here. Now, this is your trigger thing. So for instance, if I'm the person who's playing with me I can just be like, "Hey dear, how are you doing?" - Common mistakes people make when getting their dildo for pegging is that it's either gonna be comically large or about the size of a baby carrot. Now both of those aren't necessarily a good idea for your first time pegging. If you have one that's too small, maybe the idea is that it's not going to be as painful or take as much but the smaller ones are going to be very difficult for the person doing the pegging because it's just gonna fall out a lot and you don't have to take the entire dildo. Now, the ones that are comically large you want to be able to take the biggest dildo you can. And it makes you feel like more of a stronger person but that's not necessarily a good idea for your first time, either. Anal stretching is a lot different than anal penetration. You will learn if you like anal stretching. You will learn if you feel like you need something wider, something to fill you more. But I don't recommend using that for your first time. We tend to recommend more, less silicone based products and things that have a bit more give and more solid like plastic or steel, - 'Cause they're tough. - potentially glass. - Prostates, like firm. It doesn't like a lot of mushy stuff, it likes firm, it likes good pressure. So getting things that are gonna give you a good pressure, the ones you want to use. (calm music) Clean up, so there are a ton of things you can do. You can go super cheap and just get a rag. And if you're okay with washing a rag, rag is reusable, it's very green. I like being green. I use rag a lot of times and I made sure that the bag is clean, of course, and I like the wet drag. So I create my own kind of wet net kind of feel for it. And then you can always bathe afterwards for yourself. If you want to just wash up, if you are at a party, or a place where you don't have options of water being used and definitely wet ones are always going to be used. - Yeah, wet ones are just great. - Wet ones are great. I mean, they're disposable, wet wipe, you wipe your stuff back there and you just chuck it out. - I'm a huge fan of puppy pads in general because I make a bit of a mess, but they're really great for on the go. If you're gonna be somewhere, just pack in one, traveling with it and then you can throw it away when you're done. They're very absorbent. And if you're a super anal, you're super anal about it. There's also products like UV, UVee it's a UV light system. And that can kill that really small percentage of any bacteria that's left after your initial cleaning parts. - So if you've cleaned all your toys and all your products that you're using, you want to make sure you put it away for a cleaning. You miss a lot of money to these toys and you want to make sure that the investment last long time. So what you're going to do is depending on certain toys some of them actually come with a nice little protective velvet covering, whatever it is. And if it doesn't get some kind of like little baggy, that sort of show off that could protect versus steal can get jagged, you know what I mean, nick something the wrong way. If you put it in your bag with your keys it can get a little damaged. So it make sure you cover it, wrap it up, put it away. It's your toy, it's your money, don't just throw it. (upbeat music) (plastic butt jiggling) (Lola laughs) - Before we get to penetration, we want to explore the butt hole with our... We should always be starting our dildo penetration with hand penetration first, and for a number of reasons. One, is by using our hands we have more tactile ability than we do with a dildo, which is not part of our bodies. We can understand where it is that we're going for. If someone with a prostate, we can understand where the prostate is and what that feels like. The person who's receiving can also understand with that tactile motion. The person receiving can understand how that feels for them too. To recognize this when they then receive dildo penetration. And for the person doing pegging, to recognize that of where they're aiming with the dildo. The other reason, why it's really great to do this beforehand, is 'cause then we get some more prostate engorgement. So, a little bit less work for us to do when we do go in with a dildo penetration, the prostate's already going to ideally be engorged. There's less work we have to do with the dildo. All right, hi, we're again, back with Dominus Eros. And now we are moving on to the hands-on portion. I have Dominus, starting in a face up position. We really like this as a starting position. One, cause I can see his face. We can communicate, I can see your non-verbal reactions. - Which looks extremely relaxed right now. This is right where I want to be. This position was also great because we can be able to move his legs forward or back, that's going to tilt the position of his pelvis, which if his prostate was a bit further away, we can have more access to that. So, the first thing I'm going to do is, I'm not going to go straight for penetrating with a finger either. I'm applying a nice amount of lubricant to the glove and I'm going to start with a really nice anal massage. The goal, just being to relax the sphincter, relax the muscles around there. - I generally like a nice copious amount of lube. If it feels like a cannoli is back there, I'm ready to party. Yeah, there you go. - [Lola] That feel like a party? - Yeah, it feels like party time. For me right now, I'm feeling very relaxed. It's slightly pressure. Same time, it's very essential because there's a lot of nerve endings and blood back there to feel really magical for the sphincter. - Great. (women giggling) - And as you're applying you can just kind of put pressure on there, the perineum. And you can start giving a bit of an anal massage, so that you can use your fist and using your knuckles. Just kind of rolling that around. You can do it super slowly. Just applying nice pressure. How's that feeling over there? - [Man] Good. - Yeah. It might've been a little bit difficult to see a closeup of the butt hole in that shot. Luckily, I have a solution for that. (plastic butt smacking) I can start with a nice anal massage. So, in here I'm just taking my knuckles and I'm getting that between the cheeks and just kind of grinding my hand in this general direction. I can use actually quite a bit of pressure here. We sit on our butts all day, so this will feel really good, no matter whose butt it is. If it's a valva owner or a penis owner. - So, in the world of tantra, there are points. Now, where that area is is very close to my root chakra and they'll also call the sphincter area, sacred spot. - So, I'm going to take my thumb and again, I'm not penetrating here but I'm gonna run that down until I reach the butt hole. And then at the very bottom of it, there's a little lip, that thumb kind of sits in, and again, not penetrating, but once I find that, I'm gonna apply a little bit of pressure and I can use my body weight to apply that pressure downwards. - [Dominus] Yeah. And so, right now I'm feeling a bit of pressure. Could be a little fiery for some people. And then you could also use your kegels to kind of engage, along with this kind of pressure points. And it's a soft way of getting to someone's prostate in a way, without penetration, if someone's just trying to get a feel for it. - Now, to get to that tantric point, what we're going to do is take our thumb and I'm going to slide that, down the butt crack until I get to the anal cavity. And there's going to be a little bit of a lip that's a bit pronounced, it will sit in. And I'm going to push down just slightly. It doesn't need to be here for that long, a period of time. Now, once I do that, I'll exit and I may go back to that anal massage. You may have found it a little bit difficult to see the butt hole in that last shot. Luckily, I have a solution for that. (cheerful music) So, if I take my thumb and I'm sliding it down the butt crack I'm going to stop just at the bottom of the anal cavity. And there's going to be a little lip that my thumb's gonna sit in. And now if I push, that might happen too. (Lola laughing) I should have not done that as much, I knew it was gonna happen. But that should be how hard that you're going to press into the bottom of that anal cavity. Should I get new donut? - [Crew Member] Yeah. (Lola laughing) Careful of sex injuries. You want to be careful with the butt hole. But usually your partner won't be a donut, so, you'll probably be fine. I'm gonna take my thumb gonna again, going to the bottom of the anal cavity. And I'm gonna apply pressure just in that lip, in that opening. Maybe for 30 seconds or so. And you're gonna to let go and go back to that anal massage or back to that anal massage with your fingers. (cheerful music) Now, I want to penetrate the cream filled one. I have Dominus, starting in a face up position. We really like this as a starting position. One, 'cause I can see his face. We can communicate, I can see your non-verbal reactions. So, the prostate doesn't need a ton of stimulation or a ton of movement. Very small movements and pressure. There's a couple that the prostate seems to particularly like. One, is just moving my finger upward and applying pressure and holding it there. I can also just tap. (Dominus breathing and groaning) - [Dominus] Yeah. Again, if you're looking for the prostate and you can't find it, you can just move your finger from left to right and push downwards, till I feel something that's slightly harder than the rest of the area. And again, I can ask my partner for feedback. (Dominus groaning) Is that the spot? Is that it? Yeah. - That just might be. (giggling) - [Lola] So again, I can go side to side. I can press down. I can apply pressure. Or I can apply pressure as I go side to side. Or I can just keep my hand there and let him do the work. - [Dominus] Basically, I can move my tushy around. Get some nice motions. I can rock on it if I need to, if I want more direct pressure, I can move and tilt my pelvis one way or I can sort of press open and allow it to insert me in a different way. So, depending which way you want to move, keep experimenting with all that. See what works best for you. - And I can bring my wrist up, down, if I want. Up is for more pressure on the prostate, down is for less. Now, once we're ready for anal penetration, what you're going to do, since he is facing downwards we're gonna be going into a downward direction. The prostate is closer to the genitals. So, we're gonna our middle finger, just because if we don't know where his prostate is, it might be far, our middle finger is the longest, usually. (Lola giggling) And you're going to stick your middle finger just at the opening. And now when she does this you're gonna be the one to take her in using your muscles, using your "push pull", using your PC muscles, your kegels. Is he pulling you in? - Yeah, there we go. Let me know if you want more or less pressure. - What are you feeling- - Wow, he's really sucking me in. (women giggle) It's very cool. - You're going to push your finger downwards and you can kind of make a, metal detector, left and right. You're gonna feel something that's slightly harder than the rest. It's not a specific shape. It's not a walnut. (woman laughing) But it's a, it's slightly harder. (crew member laughing) It should be all gooey in there. And you're gonna feel something that has a bit of texture and that's going to be what you're targeting. It's not gonna feel like a particular shape. Yeah, that feels good. So again, just moving our finger side to side. And then be weary when you exit, there might be a little bit of cleanup involved. So, make sure that you have something nearby to clean up. (Lola sucking) Apple. So, I'm going to exit you now. Is that cool? - Totally fine. - All right. - So generally, (Dominus breathing) I breathe and push. So, the breath and push allows me to sort of open up and flower my sphincter, which allows it to relax. And then she can just pull out really nice and simple. There's no resistance, I'm not fighting it. You don't want to fight exit strategies. - You don't need a partner to explore your butt. You can always go fuck yourself. And who better to show us how, than tantric healer and professional dom, Dominus Eros. - So, it's time to set the lube, as they say. So, I'm gonna take a little dollop, if you will. And then I'm going to apply this dollop towards the end that I'm going to insert in me. Again, pick an end that makes sense for you right now. I'm just feeling nice and comfy. I'm gonna use the prostate end of this. So, as you do this, what you really want to do is just relax. Take a couple of breaths, like you were with someone was playing with you. But if you're just auto-playing you have no idea what that feels like, just take your time. You don't have to shove things in right away. Just go slow. (breathing) And generally with the proper amount of lube it will slide right in. And there we are, hello. And what I tend to do is, I let the weight hook itself. So from here, I'm just picking how much depth I want, right. And then once I figure, oh, there we are. And once I figured out the depth that I like then I'm just going to hang out and play here. And then once I feel comfortable and I feel like there's plenty of blood engorgement happening in my prostate, then I'm gonna get in some other play. So basically, if I was going to be stroking myself, I'm gonna be adding another type of stimulation. Some people like to add just a variety of tools or toys in conjunction with their play. You can totally do that at this point in time, right. So, once this is feeling good then I could try doing some hooked positions. So, this type of toy hooks into my prostate and I could sort of play with that and then move that along. And of course, with any positions we've shown you already I can switch my position for some good play and to make it more comfortable for myself. Now that I'm all warmed up, it's time for the main event. (Dominus groaning) (sexy upbeat music) - Now we are to the main event, I'm super excited. You're excited. I think we're all excited. Right, Lola? I'm excited. - Yes, so excited. All right. (Lola laughs) (sexy upbeat music intensifies) - And how we start this is always, we use protection. Next important level, lube. As we talked before, a lot of times what I like to do is start off with the tip and then I'm gonna spiral down. - [Lola] So I like situating the harness, more towards the top of my mungs. That gives really nice pressure on the cutters. Also, it brings a little bit higher towards my hips which gives me a shorter range of motion. So thrusting is going to be a bit easier and more natural. Cowboy or cowgirl is one of my favorite positions for pegging. It's especially great for those who don't necessarily want to give up control or want to still feel in the dominant position. It can also be great for allowing that person's first time pegging to be in control the penetration. - I prefer, this to begin with. Some people like to do just double leg, some like the Captain Morgan at soccer. I'm going to just be nice and relaxed here. I feel like I'm pretty well up from before. So this process can take a little bit for people. So for me, I like to just slowly get on top of it. It's like any other muscle you give enough time in a stretched position, it will relax. So if it feels like it's getting too deep, I can kind of just lean up a little bit. And I can just focus on smaller movements, which is again, getting towards that. What we showed you with the hands, tapping, tapping, tapping. Or I can move in and do a little windshield wiper action, just gain a little movement. I can move my huh-huh. I can move my hips in ways that are gonna feel pretty good. And I start to sort of turtle and crunchy and that's gonna hit, oh. - Are you having fun? - I'm having a lot of fun. - I'm inside you. - Right now is this is your first time? - No. (laughs) - Totally not a first time. - I'm gonna come so hard, it's gonna be in your brain. - Oh, you'll live my mind - Mm-hmm. - all week after that. - Yeah. I'm gonna make you smarter. Ah, yeah? - Mm-hmm. - Tip of my idea? - Yeah. - That's settled in? - You're going to grad school with my cum. - Oh God all that protein is gonna go right to my brain cells. (both laughs silently) - As the pegger, it's a really comfortable position. All you have to do is lay on your back and maybe elevate your hips. And it's really sexy to see someone on top of you, riding you. It's also great, cause I can be super lazy and just lay down. - So, you can stay here as long as you want. And again, you can listen to your butt. Please listen to your butt. But if you want to switch positions, again, practice safe exit strategy. (sighs) Uh. Oh, hello there, we're going to be doing doggy. It's a great position for a lot of people and for a variety of reasons. So for this one, I can have a lot of control in terms of depth. Because I can tell them, "All right, stay right there." And I can sort of move along with it or if I'm feeling pretty good, we'll have the person behind me take over and I'll just be here receiving. - [Lola] And once he's comfortable too. You can feel free instead of even moving your hips to just hold onto this and full limits to you too. (woman moaning) You don't have to have a ton of like separation (woman moaning) because again it's it's not your body part. So you might notice less if it slips out. - [Woman] Yeah. - [Lola] So keeping in there and more just rocking with. - [Woman] Yeah - [Lola] Mm-hmm Penetration can be a little bit difficult depending on height differentials. So, feel free if you're not really able to situate between your height of knee with and hip height, to move. So you're basically planking on top of them and that way you can caress. And also your body doesn't need to really work, you just have to thrust your hips a little bit. - That sounds perfect. (Lola laughs) Awesome. (chuckles) (both moaning) And I can just lean my entire body with him. (Dominus moaning) I can nozzle. And then when I'm ready for any kind of penetration, it's really just moving my hips. I can do them in circle, - Uh-huh, uh-huh. I can just thrust in. (moans) And this is gonna be very familiar for Volvo owners. - Now I can be a busy bottom, right? Like its moving around a lot too. (Lola chuckles) Or I can just stay here and be a nice little pillow Prince and just go, "You take the wheel." - But see, it's great, 'cause I don't really need a whole ton of movement or in order for him to feel a lot. - We showed you a couple positions and I'm going to show you some exit strategy and the cuddles. All the cuddles. - Mm-hmm. - You like the cuddles? - I love the cuddles. - I love the cuddles. - So I'm gonna be in charge of this, this time. - Go ahead. - I'm ascending slowly. Oh. - Oh-hoho-ho. (butt kissing) (butt tapping simultaneously) (group laughs) - That was really good. - Yeah? - I enjoyed that one. - Oh good. Oh great. (group laughs) - So, what? - Yeah. - What came up, is there anything that surprised you or anything that you learned, that's new? - Uhmm, yeah. I mean, I guess every time's a little different and you, you know, depending on your partner and how you communicate. One thing I was really grateful for, was how well you communicated and how like, how much feedback I got from you. That was great in terms of, not just in terms of spoken language, but in terms of body language and how much you were getting into it and your breath. It was really great. I'll, go official with that. (laughs) - [Man] Yeah. - Yeah. - I have to ask now, do you feel any more gay than you previously were? - Not really. No. - Yeah. (woman laughs) Still, still like women. - Okay. - So how you feelin'? - It was good for me, was it good for you? - It was really good for me. (Lola laughs) - Just because we're done with the pegging. Doesn't mean your job is over. Whether it's a high five, a fist bump, a booty bump or just a simple chat, after-care is important. And that's the thing that we never see in porn. That person, probably feels really scared that they're wondering if they're gonna feel different. If you're gonna look at them differently, treat them with respect after you fuck them. There's one thing you take from this, say, "Thank you. "Thank you for sharing your butt with me." (sexy upbeat music) - So we did it. - We did it. - You pegged. - I pegged! Yey! Can I have a high-five, yes. (group laughs) (sexy upbeat music intensifies) (both laughs silently) - If five chapters of pegging wasn't enough, there are always more questions and there's always gonna be things that I miss a little bit too. So I wanted to answer more of your questions and provide more clarity. First thing for all the prostate owners out there is you might be asking, "How can I tell if my prostate's engorged? "Will I know or will my partner have to alert me when they're inside my butthole?" And really it could be either-or. You could be able to tell if your prostate's engorged and feeling that either by using your pelvic floor muscles or by potentially physically feeling. But also your partner might be able to tell that, "Oh this is pushing on me a bit more than it did before." Or if they're experienced, they could just be able to tell through practice and repetition. So it might be more super obvious to some people than others. Just like everyone's prostate is a little bit different size and distance. So there isn't one answer to that directly, I would say in general, just default to the person who has the prostate. It's really about their pleasure and their body experience and reacting to that, but both people can communicate to each other and you can figure it out that way. If exiting is a part that is an odd sensation that you want to know enjoy, try adding something to that. So for entry or exit, a really great tool is vibration. It relaxes that part of the body, like no other. Don't believe me? Then just try putting it on your butthole now and seeing how that feels. It feels like a massage, it's really good. So you can add that, add that to your exit, add that to your entry, add that to your whole play. More butthole relaxation is breathing, and it's not just the breathing in and out for your sphincter muscles, but if something foreign is in there, the sensation in your butt, then just taking time to breathe and accept it. Think of it like a piercing that's foreign to the skin and it takes your body a little while to be like "Oh no, this is okay, we intended to do this." So just breathing and the more you do that the more normal that this will feel. For some people when there is a pulling out sensation, the only thing their body has experienced doing that with is poop. So like, "Oh my God, it felt like I pooped when someone exits". And also, you might, who knows? It could happen. That's in our poop and pain chapter, but again, more experience with that, experience pleasure. If being able to be like, "Oh, it felt like I pooped but I didn't poop". As you do this more, and if you enjoy it, you'll begin to associate this more with pleasure. That doesn't mean necessarily you're going gonna have pleasure when you take a poop, but with more practice, your body can associate the difference of the sensations. Of things that are going in or out of the butt, it will be able to associate those a bit more. But at first, yeah, it can feel a little odd. And your body's trying to recognize this. But try again, if it's something you enjoy, but not that part of it and maybe you can then change that association, and maybe your body gets used to it, and maybe your body really likes it. Let's talk about exiting techniques, exit strategy. We talked about breathing, so breathing in, taking a deep breath out. That's helpful because naturally our sphincter is going to mimic that with us, if we focus on it, so breathing in is going to potentially tighten and breathing out will release that. And that's when you're breathing out is when more movements should happen, than the breathing in. Now, other things you can do, and you can look at this in a mirror if you have a vagina, or if you have a butthole, which is everyone, is this flowering out. So it really looks like it is flowering. But when you push, so you're pushing with your vaginal walls, with your sphincter muscles, and you can see a bit of this flowering out. So that's what you're experiencing that you can also do to assist the exiting, but you don't have to do that as well. You could have a really intense breathing out while you flower out. You could just breathe out. You could just do this together as well. Exiting can be a very nerve wracking thing which is why I like to overcommunicate, which is why the nice breathing exercises, especially when you do it together, can be really nice. But it's also why we want to have something nearby to be able to clean that up, wrap it up, toss it out, wash your hands, whatever that you need to do. Make that as easy and uncomplicated as possible. But also know that mess happens. Sometimes exiting is super smooth, sometimes it's not. The main thing is that we want to avoid pain. We want to avoid fissures. So that's where the breathing, the sphincter muscles, working with them is the most important thing because if they fight you, that's where pain can happen. That's where problems or mistakes or something like that can happen as well. (gentle music) - How do I convince my partner to do the pegging? Do either be the pegger or to be pegged? (buoyant music) Um, let's just take convinced, out of our lexicon. Convincing isn't a good word, right? In an enthusiastic consent, informed society. But, we can make sure that people are educated and informed. That's a very important part of consent, if we think of the FRIES, a summation of that. So it needs to be informed, but it also can be freely given reversible. People don't have to do this, they don't have to. But, some people don't want to do pegging for reasons that have to do with shame, that have to do with stigma, that had to do with fear or past experiences. So it's important instead of, "How do I convince my partner to do pegging? "How do I understand what their experiences "and what they already know or think about pegging." And, "How can I help them form a new experience with that "and association and gauge if it's something "that would be right for them to try." They still don't have to, they still don't want to. They still might not like it, even if they do try it, and that's okay. But we wanna make sure that people are making informed decisions. So instead of, "How can I convince my partner to try pegging? "How should I approach my partner? "How should I approach my partner "and then after they respond, how should I respond to that?" And for that, my friends, we have a lot of worksheets. We have a lot of info charts. We have a lot of things you can watch and entertaining things. But it is more, how, and the way you say things. It's your prosody, it's your word choice, it's how you approach it. Are you approaching it with shame or you approaching it with confidence and enthusiasm? It's scary to bring things up to people, absolutely. But we really don't want to bring that, "Oh, you're probably going to hate this. "This is really embarrassing." But you're already assigning a value to something that you've probably been thinking about for awhile and something that you probably really want to try. Don't put that much pressure on yourselves. It doesn't need something that you need to immediately ask and have them say yes or no. It can be a process together, especially if they don't really know much about it. And a lot of people don't or they associate it with something that's just not what you're talking about necessarily. (buoyant music) "What if my person isn't into pegging me "and I want to be pegged or vice versa?" (buoyant music) So if, you're in a situation where it's not something that your person like, they actively don't like it for whatever the reason may be. They don't have to do that thing. Doesn't matter how much someone loves us or likes us. They don't have to do our desire no matter how much that we want to. And what you can do is ask yourself, "What is it that I want to feel that I desire "by being pegged or by pegging someone?" Identify what that is and then, "Is there any other way "that I can achieve that without asking someone "to do something they don't want to do? "I want the prostate internal simulation. "Maybe I can wear a butt plug while we have sex "that person's not engaging with my butt. "The butt plug is, I kind of am." Maybe that's a way of engaging with it without asking that person to peg you. Maybe you want more of that dynamic, you want the act of being fucked. You could just have your person, without a dildo, could grab your hips and kind of ram into your butt. And in the planking position, and in an all fours position, feels really fun and good. You get that feeling without being actually penetrated or just put your suction cup dildo on the shower wall and go to town on yourself. You get to have that physical sensation. You get to have that feeling of being railed. And if you're like, "Oh, but I wish it was a person." Hire a sex worker. You'll get the whole experience that you want, they're so professional. I don't know how many times that I can say this, but there's so many alternatives. If you're like, "That specific person doesn't want "to do the very specific thing that I want to do." You have different solution. And if that's a very integral part to any of your romantic or sexual relationships, then you need to make that very clear from the start. We need to understand that if someone doesn't want to do that then maybe that's not the person that's right for that sexual (buoyant music) or romantic relationship for you. But if it's not integral to your relationship, then plenty, plenty of alternatives that you can find to satisfy yourself. And them. - Where do I put my hands? What do I do with my hands? (bright music) - It's fun. When you're pegging, what do you do with your hands? Do you wrap them around their waist? Do you hold their neck, their hair? Where do you put them? This is one where it's up to you but I prefer not to take clues from porn. You can be able to hold the waist that can make someone feel secure. That can also feel a little bit dommy. But I like to really add moments of intimacy 'cause what you're doing is a very intimate act. But it's important, especially if this is a person you really like to establish that intimacy. If they haven't already communicated, they want more of a power play or a dom sub-dynamic. That's why the planking position is wonderful 'cause you have your full chest on their full back or your full back is on their full chest and you have complete skin to skin or if you are facing each other hands on their chest on their heart, hips can be nice too. But communicating with that person in where also they would like your hands maybe they're very sensitive about their hips or like love handle area. So they do not want you touching that. I personally like to put my hands on the chest just cause it's an area I like but it's also one where it's near the heart. I can feel the breathing and the breath, you know you could explain this and it could have some tantric relations. Sometimes we put our hands on like the chest and then the stomach area or like right above the genitals and we breath together. But also it is just a nice way of connecting skin to skin is great. And the thing with pegging is it can be very separated. So finding ways that we can make it less separated and add more of that skin on skin. Now, if you're doing a huge DS thing and that person is like shove my face in a pillow smack my butt and grab me by my hips. Then, you know, maybe you're not putting your hands on their chest, but trying to add things that add that skin on skin can really add a lot of intimacy to your pegging. (bright music)

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