Sex With Emily - Pegging, Threesomes & the Sex Breakthroughs That Changed Everything

Starting point is 00:00:00 One question I'm asked all the time is, Emily, what products do you actually recommend? And that's exactly why we created shop sex with Emily. Every product in the shop is something my team and I have personally researched and tested or recommended because we genuinely believe it can help you of better sex, stronger intimacy, and just more confidence in the bedroom. Whether you're shopping for yourself, your partner, or both of you, we've made it easy to find products that actually work. head to shop sex withemly.com and discover your next favorite bedroom essential. You know, when I talk about embodiments, sometimes people don't really, like, what do you mean? It means that he was in the moment.

Starting point is 00:00:43 He's telling you a play by play. He remembers what happened, but he also remembers how he was feeling. This is the first pillar of sexual intelligence, by the way, being embodied. Hey, everyone, welcome to Sex with Emily. I'm Dr. Emily Morris, and my mission is to help you prioritize your pleasure and liberate the conversation around sex. Whether you're looking to improve your relationships, have better communication, explore your desires, or simply have your best sex ever, you are in the right place.

Starting point is 00:01:08 Before we jump in, make sure you're following me everywhere. It's at Sex With Emily on Instagram, TikTok, YouTube, Facebook for even more sex and relationship advice and more resources. Go to Sex Withemly.com. Sign up for my free weekly newsletter. I hear I give a really good newsletter. Shop my curated sexual wellness products and picks at shop, sex with Emily.com and explore hundreds of articles, download free guides, and everything you need

Starting point is 00:01:35 to have the best sex ever. And one more thing, I'm taking sex with Emily on the road. My new live show, The Best Sex Ever Tour is coming to cities across the country. It's basically live coaching meets comedy, meets audience Q&A, and we're getting into it. There has been magic happening in these rooms. You just have to come experiencing it. There's real conversations about sex and dating and relationships and we become very close by the end of the night. Visit sex withemly.com slash events for dates and tickets. And thanks for listening or watching and for being here. And thanks for prioritizing your pleasure.

Starting point is 00:02:12 Today I'm going over some of our listeners' sexy stories. You share your juiciest, most personal success stories with me. And I read them aloud on the show because sometimes the best way to learn about sex comes from other people and their experiences. First, parents who sent their kids, away and tried pegging for the first time. Hear how it went from the husband's perspective. Next, a married couple of 20 years have an unexpected night on the dance floor involving a chance meeting with a hot stranger. And then their very first threesome. It's hot. This show gets hot.

Starting point is 00:02:45 I'm just going to tell you. Finally, she orgasms for the first time during penetration, but she'll never guess how she got there. If you have a sexy story you would like to share on the podcast, send it to Feedback at Sex Withemly.com with sexy story in the subject line. Please only include information such as names that you're comfortable being read aloud on the podcast. All right, everyone, enjoy this episode. Dear Dr. Emily, I've decided to write a little update on my pegging journey. I've been with my wife for 12 years and married for six.

Starting point is 00:03:30 I've always been very open with my partners. My wife, on the other hand, is very quiet and less open about sex and talking. about it. Recently, I become very open with exploring my body and I found out on my own that I like to have my butt played with. You guys, hold on. I love when you explore anal during masturbation. Solo Sesh. Great time to explore. Side no. After suggesting it to her for a few months, I'm happy to say that we've officially pegged. Yay. We're all cheering for you here. We've done it multiple times also. We even searched and bought a bigger strap on together and went to the sex store together. Because I thought this is like, this is so ideal. I love when you go shopping

Starting point is 00:04:13 with your partner together for toys. We shipped the kids away and made a date night out of it. One day, I was just about to finish work and she asked me to let her know when I was leaving. Didn't think much of it because I always let her know when I'm leaving. After leaving work, she sent me pictures while wearing the strap on. I instantly got excited because it was the only time she gave me any indication that she'd change your mind or even thought about it. Okay. That is amazing. You guys, think about that. He's been asking her for something.

Starting point is 00:04:40 Not sure that she's into it. She doesn't give any indication. And then he's leaving work, end of date, and gets a photo of his wife wearing the strap on. Now, that is hot. She then proceeded to peg me that night and was communicating the whole time and making sure I was enjoying it. After she pegged me, it has completely changed our relationship for the better. We are able to communicate better than we have ever before when talking about sex.

Starting point is 00:05:05 She even brings it up to me without. asking sometimes. That's a dream. That's what I'm talking about. Let Graham be a testament to this. When you start talking about sex with your partner, you're going to start to crave it. You're not going to be able to talk about anything else.

Starting point is 00:05:19 It becomes fun. She brought it up without I'm asking. The connection that we are able to share from it is awesome. Now I crave the times when she tells me to bend over and the way it connects us. Thanks again, Dr. Emily. Thank you, Graham. Thank you for listening to the show and for talking to your wife and sticking with your sex life, investing in it, and really making incredible progress here.

Starting point is 00:05:42 Like, I'm so inspired that you not only were able to get your needs met, try to strap on, you graduated to a bigger strap on, you had healthy conversations, and now your wife is like initiating and down and wants to talk about it when you're, you know, having dinner and on date night. I love this. Okay, Graham, thank you so much for your story. I think we get a lot from this. I do think that pegging is becoming a little bit more acceptable, right?

Starting point is 00:06:07 right now or a little bit more, I don't want to say mainstream, but pegging, and if you don't know what pegging is, I feel like I often have to explain it if we've been listening, but pegging is when typically it is a vulva-owning partner that she buckles a strap around her waist, and essentially she's wearing a dildo, and there's different sizes, and that straps on, so essentially it's like she has a penis, and then she penetrates her male partner. And we all know the prostate can feel incredible when stimulated for so many penis owners. You can have different kinds of orgasms. It can be really intense.

Starting point is 00:06:39 And this is a really vulnerable act, too. Like, let me just say that. Men are so used to being the penetrator. They're the ones who are giving it. They're the ones who are like sticking it in things. And since boys are young, they're like, I'm sticking it in the apple pie. I'm sticking it in the wall.

Starting point is 00:06:55 I'm going to glory hole. I'm sticking it all. All her holes you're sticking it in. But men don't often get to be on the receiving end. to feel what it's like to receive, to be penetrated. And I'm telling you, giving up all of that control for your own pleasure and allowing yourself to receive is a whole new level of sexuality and, frankly, humanity that we don't often talk about.

Starting point is 00:07:20 I'm talking about straight men right now who don't usually experience this kind of penetration. Obviously, men in the gay community are more likely to experiences. They're not always switches. There's a lot of gay men who actually don't receive, who don't enjoy being bottoms, if you well. And I found an interesting thing as well. And just side note, a lot of men I've talked to about this, let me know that there is still taboo for many in the gay community about receiving and about feeling that it is maybe

Starting point is 00:07:47 feminine or it's not masculine enough or maybe it doesn't feel good. Obviously, not every sex apt is for everybody. But I'm just saying when you think about sex, you think about the psychology of sex and a lot of things that are keeping many of us from experiencing pleasure. I mean, the good thing about sex is that a lot of the challenges we have are in our mind. Like, it's not about our body. It's not about our penis. It's about our mind. And if we can work through shame or stress or traumas that we have around sexuality, then we can really learn to be present sexually and try things that maybe we'd normally not try for whatever reason, for whatever label we assigned to. We're

Starting point is 00:08:28 it. But if you're just like, yeah, I got this prostate, it might feel good when penetrated, let me try it, you know, why not? I'm down for that. All right. Thank you for that inspiration, Graham. And in my book, too, this is reminding me of stuff I talk about in the book, is like, we really can work through most of our sex challenges if we just understand what's holding us back, learn how to communicate about it, and find trusting partners. That's it. I would love to hear your experiences, no matter what your, no matter how you identify, no matter what kind of relationship you're in, I would love to hear from some more men, some more penis owners, about their prostate experience. And definitely if you're in a gay relationship, straight

Starting point is 00:09:09 relationship, any kind of relationship, I think it would be so helpful to know what is going out there, what you guys have learned about your own bodies, even if it worked for you or didn't work for you, right? So we're all in this together. Let's all keep learning, okay? Okay, this is from Calvin, 39 in Alaska. Hello, Dr. Emily. My wife and I listen to you religiously here in Alaska. I am 39 years old and she is a few months older. We have been married for over 20 years and have been together since we were 16.

Starting point is 00:09:39 Being together for so long at such a young age, we explore different parts of our sexuality together. So far, it's been an amazing ride and will only get better as we are starting on our journey of being empty nesters. You guys, empty nesters have their like a whole life ahead of them to just explore sexuality. On to the threesome. This was a couple years back and I was in the army. We had discussed threesomes in the past, but only as pillow talk.

Starting point is 00:10:04 It would really turn us on when we would fantasize about another woman joining us. One Saturday, we were particularly horny. The kids were visiting their grandparents in Georgia and I had just returned from Thailand for military training. We couldn't keep our hands off each other. We had sex about four times that day up to the first. this point. We decided to have a date night, which included dinner and dancing. My wife loves to dance. So after dinner, we headed to one of the best nightclubs here in Anchorage. Something about that night was different. It was carnal. Alcohol was flowing and bodies were sweaty as they moved on the

Starting point is 00:10:38 floor. My wife and I took our place in the middle of the dance floor. As the music was pounding and the crowd thickened, a young lady that was dancing in front of my wife turned around and started dancing with her. My penis became erect as my wife and this stranger started to kiss while dancing. After the kiss, my wife looked up to me to apologize for not asking for permission, but I just nodded my head to say that it's okay. After the green light, her and this female stranger started to dance again. Into the fourth song, the lady started to whisper and dragged me off the dance floor. My wife pulled me to the side and said, I like her. Is it okay if she comes home with us? Sure, I replied. On the way home, I drove while my wife and her new friend played in the back seat.

Starting point is 00:11:22 I would sneak glances of kissing and nipple play in the rearview mirror. When we got home, the ladies went to separate bathrooms to freshen up. I grabbed a few bottles of water and tile and all to put by the bedside as preparation for my wife having a killer hangover in the morning. The ladies came into the room and picked up where the car ride home had left off. Come on, Calvin. Does you write erotic? You guys, this is like erotica. This is hot.

Starting point is 00:11:45 You guys with me here? All right, Calvin. I took this opportunity to freshen up myself. When I returned to the bedroom in my boxers, the ladies were naked and gently exploring the inside of each other with their fingers. When my wife noticed me, she invited me over. As I lay next to her, both of the ladies pulled out my boxers and started to give me oral. It was awesome.

Starting point is 00:12:07 Then it turned into a learning experience. My wife looked at her new friend and asked, can you show me how you give blowjobs? At this point, I felt more like a live demonstration doll than a person. Hot, Calvin, what a good night. They played and licked my penis like a newfound toy while asking me, how does this feel? This went on for several minutes before the action picked back up. I needed to be inside my wife so badly that my back was aching.

Starting point is 00:12:35 As she went down on her friend, I slid my penis into her and it was amazing as always. While thrusting from the doggy position, the sight was amazing. My wife's face between her friend's legs and her friend with her eyes closed, moaning. Calvin, you're a great listener here, but this, I'm just going to keep reading because don't you guys want to know what happened? But Calvin. All right. I reached over and started manipulating my wife's clitoris until she came. She then pushed me back, grabbed and put a condo on me, and guided my penis into this other woman. I was excited, but terrified. I'd only had sex with my wife. I was afraid of not performing well and I was afraid of hurting my wife. I love that Calvin's vulnerable

Starting point is 00:13:18 in the moment of heat and eroticism. Calvin, you're so in touch with your primal sexuality and your vulnerability and your wife's into safe sex. I'm so down. You seem very embodied Calvin. And you know, when I talk about embodiments and these people don't really, you're like, what do you mean? It means that he was in the moment. He's telling you a play by play. He remembers what happened, but he also remembers how he was feeling. This is the first pillar of sexual intelligence, by the way, being embodied. My wife noticed my face and hesitated and she ever so gently bit me on my earlobe and whispered, it's okay. I want this. I then got out of my head and allowed myself to be immersed in the experience. Sex was amazing. It took about an hour for me to be completely drained. The ladies were still going at it. So I excused

Starting point is 00:14:07 myself to the downstairs bedroom to try to rest as they continued playing. My wife must have smelled the coffee and the breakfast I was making because she came down the stairs gingerly, almost skipping. She asked me if I enjoyed myself. I said, yes, my fantasy has come true and I'm all good. She replied, I had a great time as well, but I wasn't too fond of her personality. We need to try it again with someone we get to know first. Well, that was our first threesome. Kelvin, thank you so much for sharing your story and how sharing a fantasy come to life is just so erotic and how it completely worked out really well. I mean, all these moments, you've getting a blowjob at the same time, your wife being turned on. And I think it's funny that she's

Starting point is 00:14:47 like, okay, that was hot. Let's have some coffee and breakfast and play by play. This was hot. That was hot. Your personality, not so great. So now you guys can go out and find someone, you know, next level. I love it. Okay. Thank you so much for sharing that story. I love that you have been inspired by listening to the show in Alaska. You guys, I will never think about Alaska the same. way again. I'm just telling you. Thank you, Calvin. Stay right where you are because after the break, we're hearing sexy stories about pantyhos and penetrative orgasms. Don't go away. Hi, Dr. Emily. I've been listening for about five years now. I appreciate the work you're doing and sometimes fantasize of working in the industry, uplifting individuals. Oh, Jasmine,

Starting point is 00:15:40 I highly, highly recommended. I love hearing that there's so many people now who are interested in working in this space. We need more and more people. I love it. I recently had a breakthrough sexually, and I would love to share what has worked for me. But first, I'd like to share how I masturbate, out of curiosity, if there are any others who tickled their fancy this way. At the age of about eight or nine, I could remember laying in bed on my side facing the wall, almost in a fetal position. I pressed my knees together. I could feel my lips pressing against each other. The tighter I'd squeeze my legs, the more I would rock back and forth, the harder and larger my clit would engorge. Love that you notice this at eight or nine years old.

Starting point is 00:16:22 Because this is what happens. This is why I always tell you all, get a mirror, look between your legs when you're masturbating, and see how everything blossoms and swells like a beautiful flower, like a Georgia O'Keefe painting. Check it out. I rocked back and forth as the pressure continued to build until eventually I came. It was such a great release. I just sat on the bed as my sweat cooled in awe of what I'd just done to myself. For the longest, this was my primary method of masturbation until my late teenage years

Starting point is 00:16:51 when I discovered a discreet website for toys where I purchased a couple vibrators and a plug. When I began engaging in sex, it was exciting, immensely erotic, and exhilarating. But that wore off fast when I realized I wasn't getting off. Self-pleasure always resulted in orgasm and it was pissing me off that I was becoming more immersed in sex and getting even less pleasure out of it. But the thought of voicing this to a guy who was inside of me crushed me. I was not only fearful of coming off as critical, but unsure how I wanted to be touched and handled. I just knew that it felt good to be caressed, held from behind, and have a dick inside me. After a somewhat medically induced six-month streak of celibacy, I came

Starting point is 00:17:33 close to climaxing with a man inside me, until I felt shame for the thoughts I was having and the waves began to fizzle. I'd gone through a boyfriend and a few flings before meeting my child's father, and long story short, things hadn't gotten better for my sex life. In fact, they'd gotten worse. I'd become involved with an emotionally abusive, bipolar, premature, decollating alcoholic. Wow. That's a lot, Jasmine. Four years into the relationship, I'd lost all hope of ever coming with this man. I'd ask for more foreplay, oral, attentiveness, and gotten it even, sometimes. but in short bursts that left me wanting more. I resented him for not putting me first sexually

Starting point is 00:18:15 and even more for cheating on me. These blockers and many more were wedged in my mind. Of course they were. This makes sense. I'm sorry. This sounds really, really challenging, Jasmine. Thank you for sharing this. You know, I just want to say that these things happen to us and we think we just move on sometimes or like we forget about it, but when really transformative, intense,

Starting point is 00:18:35 and sometimes traumatic things happen to us sexually, Unfortunately, we can't help but bring them into the bedroom the next time we're in the bedroom and for years to come. You know, of course, unless we work it through and we understand and go to therapy. The day I came, things were different. In fact, almost a year or so before I began voicing how I felt instead of putting my feelings aside to avoid arguments, I no longer allowed him to blame his minor woes and mishaps on me. I expressed that I saw him as selfish for not doing me how I felt I should have been done. I expressed that I needed foreplay and to feel wanted and him,

Starting point is 00:19:08 present during sex. I eventually stopped putting myself second to the man in my life and began rejecting him occasionally and expressed how having sex with him made me feel like just a warm hole. So that day when he jumped up to the restroom, in what seemed like a rage after I declined sex, I assumed he jerked off and was coming to lay down and go to sleep when he laid back down and reached his arm around me. He began caressing my vulva delicately as though it was his own. This got me charged as I felt a major difference in his style of touch. This was went on for about 20 minutes. I was juicy, and when he asked me to get on his dick, I couldn't wait. I soon dropped from squatting to a riding position, which allowed me to grind my pubic bone

Starting point is 00:19:49 and clit against him. It felt incredible as I grinded, my breathing became deeper, and the waves of pleasure came in heavier. I continued grinding up and down his dark, endowed shaft, as he buried his face in my breasts. This sent tangles through my lower regions. I looked down at him as he sucked my breasts with his eyes closed as though he was in his own heaven. I even had quick thoughts flash, oh, he loves breasts. I bet he looks at her breasts. I could feel the pleasure slipping away as I would think of the thought of him cheating. But then I let go and imagine what he would look like with his head buried between her breasts as he sucked mine. I kept breathing and riding and envisioning him with her and watch him suck my

Starting point is 00:20:30 breast with his eyes closed until I came aloud. Waking the stepson and the neighbors unapologetically because finally I've gotten mine. Oh my God, this story is amazing. Congratulations. She got her orgasm. Yeah, wake up the neighbors. I'd wake up the neighbors. Oh my God. Congratulations, Jasmine. Love the story. I think the most important advice that I've been given from you is to be honest. Had I continued to bite my tongue and allowed my partner to literally continue to use me as a calm dumpster, I'd still be coming alone. I would have sworn he didn't know how to touch a woman until one day he touched me just right. The breathing techniques got me there as well.

Starting point is 00:21:08 I've been practicing them with masturbation, and I've lengthened and intensified my orgasm. I love it, you guys, that's edging. That's what I talk about it. I talk about breathing during sex, edging, learning your own body. Meditate, masturbate, manifest, everyone. Letting go is a major factor as well.

Starting point is 00:21:24 Whatever it may be, knowing that you deserve the pleasure you're getting can take you a long way. But most importantly, don't ever give up. And I know that although finding the ability to come from penetration may feel like it completes me, it does not. Thanks. Wow, Jasmine, what a journey we just went on. I'm so moved by your story. I think we can all learn so much from this journey. I mean, first, you talk about your early masturbation experience, which is really, really common for so many vulva owners to press their legs together or rub their volvos and press themselves and to feel an orgasm at a young age. And then to also feel that with a partner, it's not easy to get off them because your legs are closed.

Starting point is 00:22:05 And so how do you make it during penetration? How do you make it work? And then this whole experience with your partner and him, you know, being abusive and cheating. And I'm like, oh my God, like, what's going to happen? And then you were able to stand up for yourself in the same relationship. You were able to express your needs and you were able to be honest in a way that he could hear. Now, I'm not sure this was what your first time ever talking to him about sex. It doesn't sound like it was. But sometimes we have to remember it takes repetition.

Starting point is 00:22:31 It takes saying it in different ways, maybe different tones, different tones of voice, different times of day. You know, something that you said that time, he was able to hear you and realize, I love her, I care about her. I want to find a way to give her pleasure. And he started slowly caressing your Volvo, which is how a lot of Volvo owners are going to get there. We're not going to get there by penetration. We need to be warmed up.

Starting point is 00:22:55 We need to be turned on. So it would make sense that when you got on time, you were able to move in a way that stimulated your clitoris and your vulva because you had already been stimulated and turned on. So he did that foreplay practice that we talk about of arousing you, you're turned on, and then when you got on top, you were grinding your pubic bone against his. I want to remind you that the G spot is very close to the clitoris, and in fact, my belief that it's all clitoral network nerves, inside, outside. And so it's not so much about the penis going deep inside her. It's about you being on top and grinding, right, and knowing what felt good. That's one thing. And then You even talked about how your mind was wandering, which is probably one of the most common

Starting point is 00:23:32 questions I hear from people that like, why is my mind wandering during sex? How do I get turned on? What do I do? And how do I get back to the moment? I love how you so artfully explained how you were able to lovingly guide yourself back to the present moment and then incorporate this other woman that he was cheating on you with into your fantasy. And it all became hot. Like that is what I'm talking about, dissolving the ego, being present with what is, being embodied, and breathing.

Starting point is 00:24:04 Gosh, I love all your breathing techniques too. Because when we breathe, it allows us to be very present. It allows us to feel our body. Our breath is circulating down to our pelvic floor. I love all of this. And remember that cheating doesn't have to mean the game is over either. Couples can move through this. I don't know where your relationship is now, Jasmine, you did end saying like, you know, having this orgasm with my partner doesn't completely.

Starting point is 00:24:26 Maybe you left them. I don't know what happened. But I do love that you were able to prioritize your pleasure on your own time and you figured out what you needed physically, emotionally, spiritually, all of it. So I so appreciate you sharing that story. I know that inspired so many others. Anyways, that was so fun. I love hearing your success stories. Thank you for sharing them all with me.

Starting point is 00:24:49 This is just such a gift. And I'm so grateful for all of you for being so real, so vulnerable. so honest and sharing, you know, all of your, you're really your deepest, most erotic moments and your success stories about how the show has helped you. It just means so much to me and my entire Sex with Emily team. I love you all. I appreciate you. If you would love to share any stories, what you've learned.

Starting point is 00:25:11 And of course, your questions, you can send them to feedback at sex with Emily. That's it for today's episode. Thank you so much for listening to Sex with Emily. And if you love the show, please like, subscribe, and leave a review wherever you get your podcast. And hey, share this with a friend or a partner. It might just spark something. It usually does.

Starting point is 00:25:38 You can find me on Instagram, TikTok, YouTube, Facebook, and X. It's all at Sex with Emily. Oh, and I've been told I give really good email. So sign up at sex withemly.com for free guides and articles and more ways to prioritize your pleasure.

Sex With Emily - Pegging, Threesomes & the Sex Breakthroughs That Changed Everything

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