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What I Learned From Sex With A Younger Guy

Sex Stories

Breaking up is always hard to do.


The dissolution of my last relationship was no doubt one of the most difficult things I've had to do in a minute. But it had to be done.

Love cannot thrive in a space where respect doesn't live.

And no matter how many times the man I loved claimed to love me, the clear and resounding truth was that he had no idea how to truly value me.

I was meek, I was weak, and the harder I held onto him, the more I lost the woman I had worked so hard to become. At the end of the day, it was either him or me, and I finally learned how to be strong enough to make and maintain my decision to stay away from a man that's purpose in my life had been fulfilled.

Nevertheless, the clarity and the peace that I felt soon after allowed me to make no apologies for it. Not a single regret. My sense of self-worth was back in full effect, my self-love was well underway, but my confidence was at an all-time low following the cycle of toxicity and emotional abuse that was my on-again off-again relationship with my ex.

I honestly didn't know what I needed after something like that, aside from alone time, my breakup playlists on repeat, and plenty of journaling and self-reflection. I was putting in the work to return to me, but I still felt somehow out of reach. I had no idea that not having any expectations about what I needed would lead me into the arms of a much younger man.

What's more, I had no idea that he'd come equipped with the exact remedy I needed to reconnect with the self I had lost.

It all started back in July. Our shared birthday weekend was the beginning of a lot of things, namely the spark of our connection. I felt it the moment our eyes met the night before, on the eve of his birthday festivities that a friend, his sister had invited me to. The party before the party. My birthday fell on Sunday and his that Saturday. I had absolutely no birthday plans for my 26th birthday but he had them all for his 20th. How could I say no?

Maybe it was my quarter-life crisis revving up to run wild, but I remembered him as the kid brother of one of my friends that I first met on New Year's Eve two years prior. Back then, he was 18 and I was in the limbo of a relationship so whatever attraction I felt came to an abrupt and speedy halt. But now, a blink away from 20, instead of a red light saying “stop," I only saw “proceed with caution." While we were on the river (celebrating his birthday), I admired his caramel skin and taut body while he walked around shirtless with an air that commanded. And a smile that absolutely dazzled.

At the end of the night, we made our way to a lounge and stole glances at each other across the table. He continued to be very intentional about the way he took me in like I was the glass of water his thirst called for. It was the same one I held in mine. The desire I felt there was too hot to look away. But logic would override my lust that night as we parted ways and he wished me a happy birthday and thanked me for joining him at his. He was too damn young. Little did I know, it was a prelude to our relationship.

I was willing to allow the idea of him to remain a fantasy of what could never be until a couple of days later, I found myself on his couch with his lips at my neck, alternating between kisses and soft bites. I learned what it was that day. I wanted him, but it was more than that. He made me feel desired, like I was the sexiest thing he'd ever laid eyes on. It felt specific and genuine in a way that I didn't know my confidence or my ego needed, but it did.

He kissed me with hunger, and although I wanted to back away from him for the age difference alone, it was something I hadn't experienced in so long. I valued myself and felt valued by other men since my ex for my mind, for my creative, maybe even for my heart – but he added another layer to the wholeness that escaped me. I wanted him because he made me feel wanted.

High as f*ck, hot as f*ck, horny as f*ck – hours later, we made our way upstairs to his bedroom to surrender to the tease we had created for one another.

It was such a turn-on to experience the effect I had on him. I felt so powerful as I took him into my mouth, sucking him into oblivion. He gripped the sheets so hard, arching up into me. He returned the favor, slipping on protection and then entering me. We sighed into each other's mouths, a deep exhale, expletives on our tongues. Sex with him was like letting go. Each thrust was the culmination of gaining something new: relaxation, surrender, rebirth, renewal. It was an awakening and in the wake of being dormant for so long, I was reminded of what it was like to feel alive.

When he orgasmed, it was like music to my ears – the most intoxicating sound. We made out afterwards for what felt like hours before he had enough and decided he wanted more. I giggled to myself. It's quickly become one of my favorite things about him – aside from how womanly he makes me feel – even in moments where he comes too quick, it's made up to me by a second, third, and sometimes fourth round of lovemaking. He's as insatiable as I am.

In the early hours of the morning, he tightens his embrace around me and brings me in closer to him to kiss my back, my neck. He slips his hands between my thighs in effort to initiate wetness where there's warmth. I writhe against him and he breathes against me in anticipation. It isn't as urgent and it doesn't demand. It's a slow dance that builds purposefully into a crescendo of completion. Sometimes we finish together, profuse sweating and heavy breathing. Other times, I finish alone and he taps out involuntarily. We touch ourselves while holding onto our gazes and I come again as I watch him make himself come for me.

The relationship between the two of us has quickly turned into a relationship of convenience with the only strings attached being a couple of guidelines we laid out: open communication and having respect for the other's health. I think he's drawn to me because of the enigma and I'm drawn to him for the thrill. We have a fun, easy-going vibe, have conversations about everything underneath the sun, and overall just have an understanding:

We know what it is, what it isn't, and what it will never be.

One thing's for certain, he has reminded me of who I am during a time where I needed an extra voice and I will always appreciate him for that and for helping me to undo some of the damage I incurred from the man before him. There is an absence of expectation – other than the ones that derive from our mutual pleasure.

We just are.

And whenever I feel a familiar ache between my thighs, I send him a quick text that reads: “Tonight?"

From there, he hits me back with says, “Come thru."

Happily, I oblige.

Have you ever been with a younger guy? What did it do for you? Let me know in the comments down below.

xoNecole is always looking for new voices and empowering stories to add to our platform. If you have an interesting story or personal essay that you'd love to share, we'd love to hear from you. Contact us at submissons@xonecole.com

Featured image by Getty Images

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You may not know her by Elisabeth Ovesen – writer and host of the love, sex and relationships advice podcast Asking for a Friend. But you definitely know her other alter ego, Karrine Steffans, the New York Times best-selling author who lit up the literary and entertainment world when she released what she called a “tell some” memoir, Confessions of a Video Vixen.

Her 2005 barn-burning book gave an inside look at the seemingly glamorous world of being a video vixen in the ‘90s and early 2000s, and exposed the industry’s culture of abuse, intimidation, and misogyny years before the Me Too Movement hit the mainstream. Her follow-up books, The Vixen Diaries (2007) and The Vixen Manual: How To Find, Seduce And Keep The Man You Want (2009) all topped the New York Times best-seller list. After a long social media break, she's back. xoNecole caught up with Ovesen about the impact of her groundbreaking book, what life is like for her now, and why she was never “before her time”– everyone else was just late to the revolution.

xoNecole: Tell me about your new podcast Asking for a Friend with Elisabeth Ovesen and how that came about.

Elisabeth Ovesen: I have a friend who is over [at Blavity] and he just asked me if I wanted to do something with him. And that's just kinda how it happened. It wasn't like some big master plan. Somebody over there was like, “Hey, we need content. We want to do this podcast. Can you do it?” And I was like, “Sure.” And that's that. That was around the holidays and so we started working on it.

xoNecole: Your life and work seem incredibly different from when you first broke out on the scene. Can you talk a bit about the change in your career and how your life is now?

EO: Not that different. I mean my life is very different, of course, but my work isn't really that different. My life is different, of course, because I'm 43. My career started when I was in my 20s, so we're looking at almost 20 years since the beginning of my career. So, naturally life has changed a lot since then.

I don’t think my career has changed a whole lot – not as far as my writing is concerned, and my stream of consciousness with my writing, and my concerns and the subject matter hasn’t changed much. I've always written about interpersonal relationships, sexual shame, male ego fragility, respectability politics – things like that. I always put myself in the center of that to make those points, which I think were greatly missed when I first started writing. I think that society has changed quite a bit. People are more aware. People tell me a lot that I have always been “before my time.” I was writing about things before other people were talking about that; I was concerned about things before my generation seemed to be concerned about things. I wasn't “before my time.” I think it just seems that way to people who are late to the revolution, you know what I mean?

I retired from publishing in 2015, which was always the plan to do 10 years and retire. I was retired from my pen name and just from the business in general in 2015, I could focus on my business, my education and other things, my family. I came back to writing in 2020 over at Medium. The same friend that got me into the podcast, actually as the vice president of content over at Medium and was like, “Hey, we need some content.” I guess I’m his go-to content creator.

xoNecole: Can you expound on why you went back to your birth name versus your stage name?

EO: No, it was nothing to expound upon. I mean, writers have pen names. That’s like asking Diddy, why did he go by Sean? I didn't go back. I've always used that. Nobody was paying attention. I've never not been myself. Karrine Steffans wrote a certain kind of book for a certain kind of audience. She was invented for the urban audience, particularly. She was never meant to live more than 10 years. I have other pen names as well. I write under several names. So, the other ones are just nobody's business right now. Different pen names write different things. And Elisabeth isn’t my real name either. So you'll never know who I really am and you’ll never know what my real name is, because part of being a writer is, for me at least, keeping some sort of anonymity. Anything I do in entertainment is going to amass quite a bit because who I am as a person in my private life isn't the same a lot of times as who I am publicly.

xoNecole: I want to go back to when you published Confessions of a Video Vixen. We are now in this time where people are reevaluating how the media mistreated women in the spotlight in the 2000s, namely women like Britney Spears. So I’d be interested to hear how you feel about that period of your life and how you were treated by the media?

EO: What I said earlier. I think that much of society has evolved quite a bit. When you look back at that time, it was actually shocking how old-fashioned the thinking still was. How women were still treated and how they're still treated now. I mean, it hasn't changed completely. I think that especially for the audience, I think it was shocking for them to see a woman – a woman of color – not be sexually ashamed.

I hate being like other people. I don't want to do what anyone else is doing. I can't conform. I will not conform. I think in 2005 when Confessions was published, that attitude, especially about sex, was very upsetting. Number one, it was upsetting to the men, especially within urban and hip-hop culture, which is built on misogyny and thrives off of it to this day. And the women who protect these men, I think, you know, addressing a demographic that is rooted in trauma that is rooted in sexual shame, trauma, slavery of all kinds, including slavery of the mind – I think it triggered a lot of people to see a Black woman be free in this way.

I think it said a lot about the people who were upset by it. And then there were some in “crossover media,” a lot of white folks were upset too, not gonna lie. But to see it from Black women – Tyra Banks was really upset [when she interviewed me about Confessions in 2005]. Oprah wasn't mad [when she interviewed me]. As long as Oprah wasn’t mad, I was good. I didn't care what anybody else had to say. Oprah was amazing. So, watching Black women defend men, and Black women who had a platform, defend the sexual blackmailing of men: “If you don't do this with me, you won't get this job”; “If you don't do this in my trailer, you're going to have to leave the set”– these are things that I dealt with.

I just happened to be the kind of woman who, because I was a single mother raising my child all by myself and never got any help at all – which I still don't. Like, I'm 24 in college – not a cheap college either – one of the best colleges in the country, and I'm still taking care of him all by myself as a 21-year-old, 20-year-old, young, single mother with no family and no support – I wasn’t about to say no to something that could help me feed my son for a month or two or three.

xoNecole: We are in this post-Me Too climate where women in Hollywood have come forward to talk about the powerful men who have abused them. In the music industry in particular, it seems nearly impossible for any substantive change or movement to take place within music. It's only now after three decades of allegations that R. Kelly has finally been convicted and other men like Russell Simmons continue to roam free despite the multiple allegations against him. Why do you think it's hard for the music industry to face its reckoning?

EO: That's not the music industry, that's urban music. That’s just Black folks who make music and nobody cares about that. That's the thing; nobody cares...Nobody cares. It's not the music industry. It's just an "urban" thing. And when I say "urban," I say that in quotations. Literally, it’s a Black thing, where nobody gives a shit what Black people do to Black people. And Russell didn't go on unchecked, he just had enough money to keep it quiet. But you know, anytime you're dealing with Black women being disrespected, especially by Black men, nobody gives a shit.

And Black people don't police themselves so it doesn't matter. Why should anybody care? And Black women don't care. They'll buy an R. Kelly album right now. They’ll stream that shit right now. They don’t care. So, nobody cares. Nobody cares. And if you're not going to police yourself, then nobody's ever going to care.

xoNecole: Do you have any regrets about anything you wrote or perhaps something you may have omitted?

EO: Absolutely not. No. There's nothing that I wish I would've gone back and said to myself, no. I don’t think at 20-something years old, I'm supposed to understand every little thing. I don't think the 20-something-year-old woman is supposed to understand the world and know exactly what she's doing. I think that one of my biggest regrets, which isn't my regret, but a regret, is that I didn't have better parents. Because a 20-something only knows what she knows based on what she’s seen and what she’s been taught and what she’s told. I had shitty parents and a horrible family. Just terrible. These people had no business having children. None of them. And a lot of our families are like that. And we may pass down those familial curses.

*This interview has been edited and condensed

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Feature image courtesy of Elisabeth Ovesen

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