Sex With Emily - Sexy Stories: Pegging & Partnered Orgasms

Episode Date: June 20, 2023

I’m introducing a new series today that you literally helped me create: 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 very 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. Finally, she orgasms for the first time during penetration, but you’ll never guess how she got there.If you have a Sexy Story you would like to share on the podcast, send it to [e-mail] with “Sexy Story” in the subject line! Please only include information (such as names) that you are comfortable being read aloud on the podcast.Show Notes:How to Talk Like a Good Little SubORDER MY NEW BOOK! Smart Sex: How to Boost Your Sex IQ and Own Your PleasureTAKE THE SEX IQ QUIZ! Email proof of purchase to [e-mail] and I’ll send you a link to take the quizVIIA Hemp Co’s High Love Libido Gummies (code EMILY for 15% sitewide + Free 2pc High Love THC Libido Gummy Sample Pack)More Sex With Emily: Instagram | Twitter | Facebook | TikTok Hosted on Acast. See acast.com/privacy for more information.

I kept breathing and riding and visioning him with her and watched him suck my breasts with his eyes closed until I came aloud, waking the steps on and the neighbors. Unpologetically, because finally, I've gotten mine. Oh my God, the story's amazing! Congratulations! She got her orgasm! Yeah, wake up the neighbors! I wake up the neighbors!

You're listening to Sex With Emily. I'm Dr. Ambley, and I'm here to help you prioritize your pleasure and liberate the conversation around sex. I'm introducing a new series today that you literally helped me create 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, they're very first threesome. It's hot. This show gets hot. 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 sexwithemily.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. Please rate and review sex with Emily wherever you listen to this show. My new article, How to Talk Like a Good Little Sub, is up on sexwithemily.com. Check out my YouTube channel, social media and TikTok, it's all at

sexwithemily for more sex tips and advice. If you want to ask me questions, leave me your questions or message me at sexwithemily.com. slash ask Emily or comma hotline. 559 talk sex or 559 825 5739. Always include your name, your age, where you live, and how you listen to the show. Totally cool to change your name

or choose to remain anonymous. Lastly, this episode is bought to you by via Hemp Company. Okay, I get it. You're not always in the mood for sex. And I'm going to be honest with you the past couple months, leading up to my book Smart Sex, the release I've been struggling to get in the mood myself. With so much going on lately, sex was like the last thing on my mind at the end of the day. I've talked about this before, and I just wanna say, I think that using cannabis gets a really bad rap

because first off, I don't know about you, I had bad experiences. People would give me edibles like in college or whatever, you'd eat a big cookie or a brownie or you'd take a big bong and you'd be so high and then you're like, I could never do that again. But this is what I wanna say about cannabis right now. ViaHep Company for example makes these amazing, high-love THC libido gummies, which

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Yes, they do also have Delta 8, Delta 9, and other THC-free products. Art of what? 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 6. 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've become very open with exploring my body and I've 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. So, Sasha, great time to explore. Side-down.

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 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. I 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 changed her mind or even thought about it. Okay, that is amazing. Why is she thinking about that? He's been asking her for something. Not sure that she's into it. She's gonna give you any indication. And then he's leaving work and a date and gets a photo of his wife wearing the strap on. Now that is hot.

She then proceeds to peg me that night and was communicating the whole time and making sure I was enjoying it. After she peg me and has completely changed our relationship for the better. We are able to communicate better than we have ever before when talking about sex. She even brings it up to me without asking sometimes. Oh, 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. It becomes fun. She brought it up without him asking. Oh, 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. 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 having dinner and on date night.

I love this. Okay, Graham, thank you so much for your story. I think we're going to love a lot from this. I do think that pegging is becoming a little bit more acceptable right now or a little bit more, I don't wanna 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 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. 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. I'm going to glory hole up sticking it up, but all the holes, 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.

I'm talking about straight man right now who don't usually experience this kind of penetration. Obviously men in the gay community are more likely to experience it. 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 will. And I found an interesting as well and just side note, a lot of men have talked 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 feminine or it's not masculine enough or maybe it doesn't feel good. Obviously, not every sex act 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 than try things. That maybe we'd normally not try for whatever reason, for whatever label we assigned to it.

But if you're just like, yeah, I got this prostate, 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, it's 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 relationship, and any kind of relationship, I think it would be so helpful to know what is going on 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 on this together. Let's all keep learning, okay? And it is pride month. So. Let's all keep learning, okay?

And it is pride month, so what a great time to go back in. Okay, this is from Calvin 39 in Alaska. Hello, Dr. Emily. My wife and I listened 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. Being together for so long at such a young age, we explored different parts of our sexuality together.

So far, it's been an amazing ride and we'll only get better as we are starting on our journey of being empty nesters. You guys, empty nesters have their whole life ahead of them to explore sexuality. On to the threesome. This was a couple years back, and I was in the army. We had discussed threesome in the past, but only as pillow talk. It would really turn us on, and we would fantasize about another woman joining us. One Saturday, we were particularly horny.

The kids were visiting their grandparents in Georgia, and I 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 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 night clubs here in Anchorage. Something about that night was different.

It was carnal. Alkaha was flowing and bodies were sweaty as they moved on the 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 a racked as my wife and the stranger started to kiss well 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 backseat. 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 an 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 he ride a rottie? This is like a rottica, this is hot.

You guys with me here? Alright Calvin, I took this opportunity to fresh it out 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. Then it turned into a learning experience. My wife looked at her new friend and asked,

can you show me how you give blow jobs? 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 new found 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. As she went down in her friend, I slid my penis into her and it was amazing as always. While thrusting from the doggy position, the site 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 gonna keep reading because don't you guys wanna 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 condom 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 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 I see 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 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 like okay, that was hot, let's have some coffee and breakfast and play by play, this was hot, that was hot, but I could, 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 pantyhose and penetrative orgasms. Don't go away.

Hi Dr. Emily, I've been listening for about 5 years now. I appreciate the work you're doing and sometimes fantasize of working in the industry, uplifting individuals. Oh, Jasmine, I highly, highly recommend it. I love hearing it. There are 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 tickle 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 press 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 clitward and gorge. Love that you notice is at eight or nine years old. Because this is what happens, this is why I always tell y'all, get a mirror, look between your legs and your masturbating and see how everything blossoms and swells like a beautiful flower, like a Georgia-okief 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 just done to myself. For the longest, this was my primary method of masturbation until my late teenage years

when I discovered a discrete website for toys, where I purchased a couple of 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 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 boy front at 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-jectlating 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 for a play, oral, attentiveness, and gotten, and even sometimes put in short bursts that left me wanting more. I resented him for not putting me first sexually, and even more for cheating on me. I resented him for not putting me first sexually 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, Desmond. Thank you for sharing this. You know what 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, and sometimes traumatic things happen to us sexually, unfortunately we can't help but bring them into our 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 Thaisam 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 fully 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 maybe be feel like just a warm hole. So that day when he jumped up to the restroom, and what seemed like a rage after I declined sex, I assumed he jerked one 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 caught me charged as I felt a major difference in his style of touch. This 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 and clit against him. It felt incredible as I grinded my breathing began 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 tingles 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 watched him suck my breasts with his eyes closed until I came aloud, waking the steps on and the neighbors, un-ppologetically, because finally I've gotten mine. Oh my God, the story's amazing! Congratulations! She got it orgasm! Yeah, wake up the neighbors! I wake up the neighbors! Oh my God! Congratulations, Jasmine! Love the story. I think the most important vice 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. I've been practicing them with masturbation and I've lengthened and intensified my orgasm. I love it! That's edging! That's why 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. 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 volvas and press themselves into feeling orgasm at a young age. And then to also feel that when with a partner, it's not easy to get off them because your legs are closed. And so how do you make it during penetration? How do you make it work? And then this will experience with your partner and him being abusive and cheating.

And I'm like, oh my God, like what's gonna 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 your first time ever talking to him about sex,

doesn't sound like it was, but sometimes we have to remember it takes repetition, 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 vulva, which is how a lot of vulva owners are going to get there. We're not going

to get there by penetration. We need to be warmed up, we need to be turned on. So it would make sense that when you got on top, you were able to move in a way that stimulated your clitoris and your vulva because you would already been stimulated and turned on. So he did that four-play practice that we talk about of arousing you, your 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, might believe that it's all a literal networked nerve inside, outside. And so it's not so much about the penis going deep inside of her. It's about you being in 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 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. Gosh, I love all your breathing techniques too because 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. Maybe you left him. I don't know what happened. But I do love that you were able to

prioritize your pleasure and 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 it inspired so many others. Okay, that was so fun. I love hearing your success stories. Thank you for sharing them all with me. 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 just mean 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, and of course your questions, you can

send them to feedback at sexwithemily.com. That's it for today's episode. See you on Friday. Thanks for listening to Sex with Emily. Be sure to like, subscribe, and give us a review wherever you listen to the podcast and share this with a friend or partner. You can find me on YouTube, Instagram, Facebook, and Twitter at Sex with Emily. Oh, I've been told I give really good email.

So sign up at sexwithemily.com and while you're there, check out my free guides and articles for more ways to prioritize your pleasure. If you'd like to ask me about your sex life, dating, or relationships, call my hotline 559 Talk Sex. That's 559 825 5739. A go to sexwithemily.com slash Ask Emily. Special thanks to ACAST for powering the Sex with Emily podcast. Was it good for you? Email me feedback at sexwithemily.com. you