Teen Brothers Sex Stories

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'I feel validated and there’s no pressure to commit'
I’ve only ever dated friends of friends or people I’ve been set up with. I don’t use apps because I hate small talk. Frankly, I was born in the wrong era and prefer a lust-filled limerick to a dirty DM. This aversion to strangers and digital dating does rather limit my pool of potential lovers, but it’s a rule I’ve stuck to since I was a teenager. A few bad experiences with men I had no connection to made me wary and mistrusting, so I stuck to being a serial friendship group snogger, safe in the knowledge that these men had already been vetted and approved by my trusted circle.
I’m now 32 and have been single for a few years. Nothing unusual there, however, the older I get the narrower my dating net has become, largely thanks to my self-imposed no strangers dating rule. As friends and friends of friends couple up, marry off or enter parenthood, I’ve found myself seeking coital comfort even closer to home. It began accidentally, but it’s developed into a sexual habit I’m finding hard to kick. Not only am I self-sabotaging my chance at forming real romantic connections, but the longer it goes on, the higher the chance of people finding out – something which can never happen.
When my last relationship broke down a few years ago, I was heartbroken. It had taken me completely by complete surprise and my self-esteem was crushed. After a few weeks of crying and drinking Oyster Bay through a straw, I rebuilt the barricades around my bruised heart and headed for the nearest sticky dance floor. On the lookout for nothing more than a few vodka tonics and a boogie to Beyoncé, I was happy to find my ego being stroked by a lovely looking lifeguard called Joe. Joe was sweet, complimentary and looked vaguely familiar. When he asked whether I recognised him, I was blank. He told me we’d gone to the same school. Still blank, I desperately tried to remember whether he was someone I’d ignored, been mean to or snogged. Laughing, he told me he was friends with Arthur. As in my brother Arthur. My brother Arthur who is 10 years younger than me. And just like that, Joe became the first, of several, of my brother’s friends who I’ve slept with.
I thought that Joe was a one off. That it was just a story I’d laugh about with my friends: ‘Remember when I was heartbroken and shagged my brother’s 20-year-old mate? Ha ha ha.’ But then Ben came along, then Jack.
Growing up, I hadn’t really paid much attention to my brother, or his friends. Other than buying them the odd bottle of Glenn’s Vodka or driving them to football, our paths hadn’t really crossed. Why would they? I was a decade older. They were doing the Nativity while I was sneaking into clubs. But after Joe, I couldn’t stop thinking about the way he’d looked at me when we were in bed. Like I was a treasure he’d been searching for his whole life. Other than the fact I am obviously a total catch, it made sense, it’s the oldest rule in the book. If you got with someone older, particularly at school, then you got kudos for it, they were automatically cool.
My brother would think it’s pathetic I can’t get a guy my own age
In my ‘real-life’ relationships, I’ve always fallen for men harder than they fell for me. They were always better looking and more intelligent. (Put the violins away, it’s just a fact.) Which meant I’d always had a gnawing feeling that I wasn’t enough and that they’d leave me. Which they did. But here, with Joe, the power play was reversed. He’d probably fantasised about me as a kid – not in an arrogant way, but in a fancying you mate’s older sister kind of way. Now, his childhood sexual fantasy had come true and I’d made that happen.
I met Ben at my brother’s 21st birthday party. Instead of the gormless, soft skinned cherubs I’d expected, the room was filled with boys who had suddenly sprouted stubble, inches (in height, in height) and personalities. Sure, they were overzealous with the Dior Homme, but I was hooked. Over the course of the evening, it became apparent that Ben had always had a school boy crush on me. Jokes were coming from all angles, including from Arthur. I imagine he’d have stop abruptly if he knew that Ben had slept in my bed that night, and many nights since. I know that Ben adores me in a meeting-your-celebrity type way, rather than a I-want-to-marry-you obsession and I’m fine with that. He’s eager to please and can’t believe his luck. I feel validated and there’s no pressure to commit – it’s a win, win. Well, it was to begin with.
Things took a turn when I slept with my brother’s very best friend on holiday last summer. I bumped into him in a bar and knew it was 'on' from the first Margarita. He told me he’d wanted to have sex with me since he’d seen me at football game a few years earlier. We ditched our friends for the nearest hotel. The sex was hot. This was the naughtiest I’d felt about sleeping with someone so close to home, but I couldn’t help but panic I’d gone too far. If this ever got out, it could ruin my relationship with my brother. We’re incredibly close and he’s sensitive and temperamental. He would be mortified. He’d think I was pathetic for not finding a guy my own age and would be utterly ashamed. I’m ashamed. I would be a desperate embarrassment. So, I keep it to myself – my dirty, sexy, secret.
I know this power trip can’t last forever
I told my close friends at the beginning, it was a joke that I had a thing for younger men. But the more it’s happened, the less I tell them. The majority of them are married, or living with partners and don’t understand no strings attached sex, let alone sex with what they describe ‘infants’. They think I should settle down. I think I should too. What started out as a bit of fun is now stopping me from forming actual relationships.
But I love the way these younger men make me feel adored, the way I hold the power. When I’m with them, I do and say things I’d never dare with a man my own age. I love the lack of responsibility they come with, there’s no agonising waiting for a follow up text or promise of drink dates. There is no threat. But this power trip can’t last forever. The boys are starting to form serious relationships with nice, girls their own age and where does that leave me? Alone and starting to think there’s no such thing as no strings attached. Maybe it’s time I relaxed my own dating rules. Even I know that being equals is more important than whether we’ve got mutual friends.
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Get Dear Prudence delivered to your inbox each week; click here to sign up. Please send your questions for publication to prudence@slate.com . (Questions may be edited.)
Got a burning question for Prudie? She’ll be online at Washingtonpost.com to chat with readers each Monday at 1 p.m. Submit your questions and comments here before or during the live discussion.
Dear Prudence,
My fraternal twin and I (both men) are in our late 30s. We were always extremely close and shared a bedroom growing up. When we were 12 we gradually started experimenting sexually with each other. After a couple of years, we realized we had fallen in love. Of course we felt guilty and ashamed, and we didn’t dare tell anyone what we were doing. We hoped it was “just a phase” that we’d grow out of, but we wound up sleeping together until we left for college. We knew this could ruin our lives, so we made a pact to end it. We attended schools far apart and limited our contact to family holidays. But we never fell out of love with each other, so after graduation we moved in together and have been living very discreetly as a monogamous couple ever since. I’m not writing to you to pass moral judgment on our relationship—we’re at peace and very happy. Our dilemma is how to deal with our increasingly nosy family and friends. They know we’re gay, and we live in a state where same-sex marriage is legal, so we’re getting pressure to settle down. I feel we should continue being discreet for the rest of our lives and blow off their questions. It’s nobody’s business, and I fear they would find our relationship shocking and disgusting. My brother, though, is exhausted with this charade. He thinks that if we get the family together with a therapist to talk through the issues, they’ll eventually accept it. I think he’s out of his mind, but I also want to make him happy. Is this one of those times when honesty is not the best policy? If so, how do we get everyone to stop worrying we will die alone? I’m also concerned about the legal implications of this—would the therapist be required to report us to the authorities? Could we go to prison?
Dear Greek,
I admit this is my first letter about homosexual, incestuous twins, but I’m going to take you at your word that you two are happy and that I should suppress the images that came to mind of two sets of brothers who lived together and came to unseemly ends: the pack-rat Collyer brothers and the twin gynecologist Marcus brothers . Let’s deal with your legal questions first. I spoke to Dan Markel , a professor at Florida State University College of Law. He said that while incest is generally illegal in most jurisdictions, the laws tend to be enforced in a way that would protect minors, prevent sexual abuse, and address imbalances of power. Those aren’t at issue in your consensual adult relationship, but Markel suggests you have a consultation with a criminal defense attorney (don’t worry, the discussion would be confidential) to find out if your relationship would come under the state incest statutes. Either way, it’s better to know, and if it is illegal, as long as you remain discreet the likelihood of prosecution is remote. Next, I suggest that you and your brother split the difference in your approach to family and friends. Blowing people off for the next couple of decades is only going to fan the flames of curiosity. But I also agree with you that having a family gathering in which you announce you two have found life partners—each other—will give everyone the vapors. Ultimately your choice is your business, but a limited version of the truth should back everyone off. When people ask when you’re each going to go out there and find a nice young man, tell them that while it may seem unorthodox, you both have realized that living together is what works for you. Say no brothers could be more devoted or compatible, and neither of you can imagine wanting to change what you have.
Dear Prudence,
I recently started a new job at a company that has been in the local news. Shortly before I was hired, the owner was sued, because while all the senior positions went to men, the rest of the staff was made up of extremely attractive women. I do not look like my female co-workers. I’m a brunette who’s over 25, and I’m not “curvy,” just one big curve. I’m slowly being introduced to our clients, and the first time I met one, he said, “Oh, you must be one of the new hires!” and everyone at the meeting laughed. Only after another client said it did I realize he was referring to my boss’s legal troubles. It’s astounding how many clients have now made the same joke. I overhead one client call me the “ nottie .” I’m now feeling pressure to try to look hot, when that’s not what I’m about. I don’t want to offend clients, but it’s insulting they feel they can say this to me. I would go to my boss, but I feel I should be able to handle this myself.
Dear Nottie,
Your firm must have been a source of endless stimulation and even hilarity for the male clients for so long that they no longer notice that they’re flouting the normal rules of courtesy. I’m infuriated on your behalf, but please don’t let your response be to try to turn yourself into a hottie. Your job is to do good work for the clients, so I agree complaining to the boss will be awkward and won’t resolve the situation. When these jerks make their remarks, just ignore their implications. Upon hearing the “new hire” joke, reply: “Yes, I started in December. I really look forward to working with you.” In acting class they teach the importance of subtext. Good actors, through a facial expression, a pause, or a tilt of the head, subtly express their internal state. So you might say to yourself, “Yep, the Victoria’s Secret show has closed, and now real women are working at Letch & Co. But I will do you the favor of pretending I don’t know what you’re talking about.” That half-smile or raised eyebrow from you might just cause the jokers to reconsider their behavior.
Dear Prudence,
I have a beautiful teenage daughter, “Lilly.” My mother, who really loves dogs, recently got a new one. She asked me for name suggestions, and I gave her a list including “Maggie” and “Millie.” Shortly afterward she called me and said she had a strange request: She wanted to call her dog Lilly and wanted my OK. I was distracted with other stuff and didn’t object. When I told my daughter, she looked confused but didn’t say it upset her. Then my sister called me a few weeks later and said, “What’s up with Mom naming that dog Lilly?” Now every time I talk to my parents I have to hear their Lilly stories. I am bothered that the dog has my daughter’s name. I know this sounds petty, but maybe part of the problem is that my mother was not that into being a grandmother when my kids were little. Should I just let it go, or could I say, “Hey, do me a favor and call the dog Millie?”
Dear Name,
You are an ACDL , an adult child of a dog lover. It is disconcerting after one’s parents get a late-in-life dog to hear them natter on about their furry darling’s every yip and poop. I often get letters from people who are enraged that some family member with a new baby plans to appropriate a name they feel should belong only to their child. I admonish them that no one owns a name. However, I’m going to agree that it’s odd and even ridiculous for grandparents to give their new dog the same name as their granddaughter. So now that you’ve had your fill of four-legged Lilly stories, go ahead and tell your mother that you feel having two Lillys in the family is confusing and you’d really appreciate it if she renamed her pooch. Given the mentality of the older dog lover, I predict your mother will say that getting a new name would be too traumatic for her baby, and if you don’t like having two Lillys, you are free to rename your own daughter Millie. At that point just tell yourself that your mother adores her granddaughter Lilly so much that she gave Lilly’s name to the being she loves most in the world.
Dear Prudence,
I live with my boyfriend, who, in many ways, is a wonderful person—hardworking, smart, and funny. We are constantly butting heads over one thing, however. He is an extreme perfectionist. I’m not messy, but compared with him I’m a slob. He travels often for work, and lately I’ve found myself becoming anxious before he returns. He always notices if something has been put back in the wrong place, if I didn’t sweep under the couch, or if I bought the wrong brand of detergent. I make checklists the days before he returns, but there are things I miss. He thinks everything should look the same as how he left it. Should I just hire a maid, or is he being unreasonable?
Dear Cinderella,
Here’s a way for the place to look untouched when your boyfriend returns. After you see him off, get your suitcase, pack your things, and move out. If you aren’t ready to do that, before he comes home, forget the checklists and just live your life. When he returns, if he rages, threatens, or gives you the silent treatment, accept that his good qualities do not outweigh that he’s a bully who will make your life a misery. Imagine his reaction to the chaos a child might cause. People like him generally don’t get better; their partners just get more panicked. If he wants a perfect life, let him have one without you.
“ A View to a Thrill : Neighbor boys peep at my scantily clad daughters. Should I have them cover up?” Posted June 30, 2011.
“ Loving Thy Neighbor : I have sex with the couple next door. Should I tell my kids about it?” Posted June 23, 2011.
“ Fatherly Advice : Dear Prudence advises a dad whose wife fears he’ll abandon the family in favor of his long-lost daughter—and other Father’s Day advice seekers.” Posted June 16, 2011.
“ Businessman on the Road to Ruin : My wife doesn’t know I visit strip bars and porn theaters while away on business. But that’s not cheating, right?” Posted June 9, 2011.
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