Boy And Man Sex Stories

Boy And Man Sex Stories




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My life in sex: the man who sleeps with straight men
‘I learned the hard way not to let things get out of hand.’ Illustration: Lo Cole/the Guardian
Original reporting and incisive analysis, direct from the Guardian every morning
© 2022 Guardian News & Media Limited or its affiliated companies. All rights reserved. (modern)
My ‘male-on-male playdates’ are guilt-free and fun
T here have always been men who have sex with other men, but don’t consider themselves gay or even bisexual. I should know; I’ve been sleeping with them since my schooldays. I prefer sex with straight men because they don’t want romance; with gay men there’s always the possibility that they could get the wrong end of the stick and want something more. I’m in an open marriage with another man, so I’m not interested in falling in love.
The advent of the internet has made these discreet, anonymous encounters with curious men incredibly easy. There is little, or nothing, in the way of guilt. As one man told me: “Sex with another man is not being unfaithful to my wife – it’s just fulfilling my needs and desires.” I’ve even encountered straight men who have “male-on-male playdates” with their wives’ blessing. I was initially sceptical, but this arrangement seems to work for everyone: the wife knows she has no competition from another woman; the husband knows he does not want a life with another man. It’s the definition of “no strings attached”.
Other straight men are keen to try a threesome with a gay couple, as my husband and I have discovered using hook-up apps. Personally, I prefer one-on-one encounters, but watching my husband spend a couple of hours with another man can be huge fun. There have been bad experiences. One very tall police officer got a bit carried away, swore undying love and wanted to leave his marriage. I learned the hard way not to let things get out of hand. Now I make it clear that I’m only interested in a couple of hours of fun, before sending them back to their wives and girlfriends.
Each week, a reader tells us about their sex life. Want to share yours? Email sex@theguardian.com .
Comments on this piece are premoderated to ensure the discussion remains on the topics raised by the article. Please be aware that there may be a short delay in comments appearing on the site.


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The intimate, the harrowing, the sweet, the surprising — the human.
Because sexual violence strikes just about wherever it wants.
I’m a rape victim. I didn’t know I was, but America has convinced me I am.
When I was 18, I volunteered at the Mother Teresa House in Kolkata. At night after work, I had my first drinks and joints on the hostel rooftop. I remember topping a glass with vodka and trying to chug it.
On the wall of my hostel was a poster for Ayurvedic Indian massage . Higher than the Himalayas, I pictured a young female masseuse and sauntered there. The masseuse turned out to be the opposite: a wrinkled, lanky man with a graying beard.
But I did not want to be rude, so I paid rupees, roughly about five dollars. He asked me to strip down to my underwear so I did. I lay prostrate on a musty bed. His fingers were long and cold, but his touch on my back was soothing.
I blamed myself for my naivete. The world is not all roses.
I woke up with his penis inside my anus. I didn’t know if he had penetrated multiple times, but I shoved him off. He rushed to pick up his pants and handed me back the rupees. Fear-stricken, he pleaded with me to not report him to the police. I yelled at him to get the hell out, and he did. That was a month before my first heterosexual intercourse. 
Feeling filthy and violated, I trudged my body home. I stood under the hot shower of the hostel and traced the contour of my anus. I don’t remember if I was crying, but I remember standing under the shower for a long time. I was raised in a Christian family that taught me my body is my altar, and in a Confucian society that taught me my body is my parents’ gift.
I shared what had transpired with fellow Americans at the hostel, and they sympathized by offering more weed. Curled in a ball and still high, I passed out.
For whatever reason, I haven’t been scathed. I did not turn in the old man. I blamed myself for my naivete. The world is not all roses, and the crooked timber of humanity will deflower you if opportunities arise. I returned to the Mother Teresa House the next day. I did not go through the gauntlet of sterilizing medical and legal procedures. 
I don’t presume to know what it feels like to dwell in a woman’s body and psyche. But I suspect that the intensity of psychological distress may be culturally amplified. I don’t think the ancient Greek philosophers and Japanese samurais who were anally penetrated as boys developed lasting psychological traumas.
In contrast to Dionysian Greeks, Christians espoused sacrosanctity of the body and paranoia over organs of pleasure, while also preaching confession and forgiveness. The global obsession with chastity seems driven not only by evolutionary biology of genital infections and paternal uncertainty, but by the patriarchal structures that sought to ensure male domination over female bodies.
I share my experience not to challenge the authenticity of rape traumas or condone the atrocity of perpetrators. I would like to merely question the perceptions of penetration upon male and female bodies, and also upon white and colored bodies. If perceptions diverge, then these distinctions should be acknowledged in educating young males about their gender privilege. If they don’t, then may stern justice prevail over mercy.
As for me, I remain straight to this day, though I occasionally spice up my sex life with homosexual encounters. Life is messy, but I had to pick myself up from the dirt and live. So I do.

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It was no secret that Bobby had a crush on me in the fourth grade… By Amy Friedenberger
It was no secret that Bobby had a crush on me in the fourth grade. I knew it, everyone knew it, and I can’t say I was opposed to the novel male attention.
The innocent crush didn’t last long. A group of girls, being typical females even in the fourth grade, confronted me during a bathroom break one day, and mid-hand-wash I was told, “You know, he only likes you because of your boobs.”
For many girls, starting to develop breasts is a sign of becoming a woman. But for those who mature early, it can be a source of trauma with long-term effects.
That first fourth-grade revelation was the beginning of many unwanted boob-related situations.
In my junior high art class, I simply leaned against a table, and was greeted with a surprised “Whoa!” from the guy across from me. Confused, I looked down and saw that I was giving him a generous look at my cleavage.
High school was no different. I played soccer throughout, and always considered myself to be like the other girls, never thinking that I had large breasts — until our team sat down to some game films. I was appalled by how large they looked on the screen, moving up and down as I ran.
The next day at practice, everyone was talking about how their breasts shrunk when they worked out. No matter how many bench press reps I did or how hard I exercised, my boobs never diminished in size.
“Your boobs are huge,” one of my teammates said to me. I started wearing three bras every time I played.
By my senior year of high school, I was up to a D cup. After going to my friend’s house for a cookout, I was later told that after I met the girl’s uncle, he’d jokingly commented, “Your friend is pretty big up there.”
Breasts, as a concept, are not only considered sexy, but are seen as a comedic element to a woman’s appearance, only adding to overall self-consciousness. In 1986, Playboy published a list of 300 synonyms for breasts. They ranged from the more common “bazookas,” “bosoms” and “knockers,” to the not-so-common “zingers” and “angel cakes.”
Now here I am — a double-D cup. I’m not going to be one of those women who shouts, “Woe is me! My large breasts are a burden. I wish I didn’t have them.” I wouldn’t trade them for a B cup just so I could sleep on my stomach or eliminate the back pain.
But they make me incredibly conscious about how they look to others and how I’m perceived because of my chest.
I notice when men start off looking me in the eye and then do quick eye drop to glance at my breasts.
I try not to wear low-cut tops, and even button-down shirts are a challenge because the buttons are tight at the middle. When I go to job interviews, I always yank my top up; I don’t want anyone to think I’m trying to use my chest as an advantage.
Having to constantly worry about how my breasts look is certainly a burden. Yet what it comes down to is whether I continue to allow my breasts to control me or just stop caring and learn to love them.
The educational diagrams of happily postpubescent girls were no preparation for what actually happened during a girl’s first period. Graphic details aside, starting my period in a third-world country at the age of 11 wasn’t exactly how I envisioned my entrance into lady land. Unfortunately, I did as any other girl would: I cried, I yelled at my mother, I took evening angst walks alone.
When the estrogen attack subsided, I realized a perk of the big P. The esoteric, wonderful emergence of boobs was going to surface from the inner depths of my immortal being.
Simply put: Lady boobs! I was going to be a real girl!
Of course, the land of lady parts didn’t turn out to be sunshine and happiness and B cups. Instead, I resembled a brown Marilyn Manson — long, dark hair and an entirely masculine chest.
Like Manson, I too longed to be a real girl. I spent unrecoverable moments between the ages of 11 and 17 searching my chest for any type of growth. After a severe bout of scrutiny, I almost convinced myself I had breast cancer. Then I realized that if puberty couldn’t locate my boobs, cancer would hardly have better luck.
Yet, as in every underdog story, things could continue this way for only so long. There I was, floundering in the lull of summer before college. I had no plans, no job, no money, just ever-comforting reruns of “The O.C.” and the company of Susan, the poodle.
It took one insignificant laundry day to change everything.
I was transferring clothes to the dryer and discussing with Susan why she shouldn’t have such a judgmental face when an unusual amount of change fell to the tiled floor. Flabbergasted, I counted out nearly $1.50 — the first substantial amount of money in my possession since I spent my net worth on a pair of Ray-Bans.
Since saving money is a concept to be learned in your early thirties, Susan and I headed to the only place $2 was worth anything: Taco Bell.
Little did I know, Taco Bell would be my Mexican miracle worker. A month into our grotesque routine of treasure-hunting for burrito quarters, I noticed a change in my chest, an uncomfortable garroting by my bra, something that resembled cleavage.
I’ve never particularly liked turtlenecks.
What a sweater is to a hug, a turtleneck is to a strangle.
And as someone who’s well-endowed, I’ve tried really hard to avoid ever deciding that I needed to be dressed like a ’90s substitute teacher just so people don’t stare.
Because I made that decision, I thought that I deserved the cracks.
Look, pet names like “Honey” and “Love” are adorable. But no matter how sweetly you say it, “Jugs,” “you and the twins” and “Thunder Tits” will never, ever sound affectionate.
Yes, they may be funny, and if you’re a friend of mine and we have a good mocking rapport, I might not have the desire to hit you. But if I’ve just met you, keep your mouth shut.
So we’re all clear, there’s no graph that demonstrates that the amount something protrudes outward is proportional to how much you can openly and awkwardly talk about it. I’m talking to you handsy stranger at the bar, friend of a friend who suggests we play strip beer pong and starts with bras.
I’m not ashamed of my rack, but I don’t want a side of degradation with my small talk for it.
And because it would have never occurred to me to play tit for tat in public, I’ll share the story that helped me explain why I don’t think I need to have a sense of humor about it when you try to grope me in public.
One night in Sorrento’s a girl stood on a chair and started cheering. A strange guy walked up to her and said, “Show us your tits.”
She didn’t get offended, she didn’t tell him he was an asshole.
She just said, “You want to see my tits? You show me your dick first.”
The guy called her a b*tch and slinked away while everyone laughed at him.
And that’s when it hit me: I like myself, and I like my breasts, but don’t ask to see mine if you’re not going to ante up and show yours.
In fifth grade, I was the first girl in my class to wear a bra.
My measly 32AA training bra held up the “breasts” I’d developed earlier than the rest of my classmates. For an 11-year-old, I was well-endowed — a physical trait that did not follow me past my middle school years.
Wearing a bra was more of a nuisance than a blessing. The almost-adolescent male population of my class took particular notice of the fifth grade girls’ physical differences. They thought the horrendous process of puberty was utterly amusing until their voices started to crack.
As the only girl in my class with a bra, I became an easy target. Every boy wanted to know what it looked like, how it felt and what was underneath the thin material.
They wanted answers. So one braved the unknown frontier and elected himself to answer these questions: He was going to snap my bra strap.
I went to take a drink from the water fountain and, as my friends and I chatted, the fifth grade bully approached from behind me, inching closer to my back with every step.
As I bent down to sip some water from the fountain, I felt a strange hand on my back. He took my innocent water break as the opportune moment to find the answers to his questions. He grabbed my right bra strap and flicked it against my skin, causing a shot of pain to course through my shoulder.
Even as an 11-year-old I knew something was wrong about his actions. Because I had the only signs of development coming out of my chest, I became the target of his joke. There was only one solution to my problem.
I turned around and punched Justin in the face.
He walked away from my reaction unscathed, but no other boy in the class attempted to touch my 32AA bra.
During my final semester at Pitt, I’ve begun experiencing something absolutely wonderful: confidence. I look in the mirror and I see a young woman who’s proud of her majors, pleased with her accomplishments so far in life and even happy with her body.
Unfortunately, when I was younger, I did not like the way I looked. Even more unfortunately, I hit puberty earlier than a lot of my female classmates. So when my chest started growing, I apparently began hunching over in an attempt to hide my changing body from my peers. I say “apparently” because no one mentioned my bad habit to me, so I didn’t initially notice it.
Not long after entering high school, years of bad posture and trying to hide my chest caught up with me. My back went out. I was 14, and at the time, it was mortifying. I was the youngest person at the chiropractor’s office, and I went through months of rehabilitation to fix my back and posture.
Even though this is a fairly unusual story, it’s a story about a common problem: my failure to accept my body. Self-confidence issues related to our bodies are a big issue. They’re a universal anxiety.
While we primarily think of body-image issues being related to weight and obesity, for women, the size of our breasts is a big deal. Our breasts strongly tie into our self-image, and our self-perception is often overridden by the fear of how others will perceive us based on how we look. My lack of confidence regarding my girls started at a very young age, and it could easily still be a problem today.
Fortunately, now, at the end of my undergraduate career, I’ve come to a radical conclusion: my body — and my breasts — are perfect the way they are. Denying that from a young age only hurt my health — physically and, in many ways, emotionally.
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