Losing gay virginity

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Guys spill the beans on how they lost their virginity

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It’s true what they say – you never forget your first time.

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Against a fire door, on the 22nd floor

By RS

During my mid-teens I worked as a paperboy.

I’d arrive at the cornershop about 6:30am to sort out my round – double-checking addresses, inserting supplements into the broadsheets, that sort of thing.

The other delivery staff would be there as well – including, for a few brief and wonderful weeks in late 1998, a girl named Carla.

I’d try out my woefully inexpert flirting on her, she’d sometimes laugh, I’d often blush.

Then I’d tip the pile of papers into my sack and head out into the cold morning.

My round included a row of rather ropey tower blocks, so I’d spend a lot of time in smelly lifts going up and down flicking through the grubby tabloids in my bag.

One day, presumably distracted by a feature on the Spice Girls (very much my thing at the time), I accidentally posted a Daily Star into the wrong letterbox.

The cantankerous old hag wasted zero time calling the shop, outraged, so at the end of my round, the shopkeeper insisted I go back and deliver her paper as promised.

On my way back to the estate, I bumped into the lovely Carla, who’d just finished her much cushier round.

She offered to accompany me as I made the extra drop-off.

In the lift – which genuinely stank of piss, and took an age to get to the 22nd floor – Carla began kissing and groping me.

It was great – she tasted of strawberry Hubba Bubba.

Having stumbled out onto the correct floor (and delivered the paper like a pro), she dragged me into the fire escape stairway, dropped her Adidas poppers to the lino, unzipped my fly and pulled me into her.

It was brief, urgent, hurried.

I went up that tower block a boy, and came down it a man.

A man with spunk on his Reebok Classics.

A case of sibling extortion

By JS

Jessica was a posh girl with an infuriating family.

Wining and dining her cost me a fortune, considering I was only a warehouse gimp at the time.

After about three months she informed me she was ā€˜considering taking things to the next level’, but the onus was on me to sort it all out and make sure it was perfect.

My parent’s house was a no go – mum never left the place, when we were there, and besides, Jessica preferred to stay in Chigwell unless absolutely necessary.

Her massive pad was ideal, but her sister – about five years older, never kissed a boy – took it upon herself to cockblock at every opportunity.

After three successive weekends of sis refusing to leave us in peace, I basically bribed her to go to the cinema.

Knowing full well she was in a position to name her price, the wretched girl even strongarmed me into treating her pram-faced mates to a post-film Nando’s.

That was a week’s wages for me back then, but slave to my hormones that I was, I gladly handed over the dosh.

At least that gave me and Jessica a good four hours to go at it.

She bled, which was unfortunate, and everything smelled of latex, but I thought it was poetic, tender and even a bit magical.

losing gay virginity

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In today’s episode, my best friend, Allie, and I talk about our experiences when we lost our virginity (but not by each other).

We compare how it feels for a straight woman versus a gay man.

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Between villages

By RC

I grew up gay in a tiny Somerset village.

Well, somebody had to.

While all my friends were copping off in fields, I stayed home playing video games.

One girl at school said she was bi and tried it on with me a few times.

As much to shut her up as anything, I told her I only liked men.

Like an angel, she told me about another boy in a nearby village who was the same.

She gave me his number, we texted back and forth.

One summer night we met, on a crossroads by a field.

The only light was moonlight – our only soundtrack the washing-machine rumble of the nearby A361.

We held hands, shared a cigarette, and gently gave ourselves to each other.

It was his first time too, so we were both clumsy, uncertain but forgiving of each other.

Though we never saw each other again after that, I walked home feeling 10 feet taller.

Maybe a few years down the line I’d have experienced my first time at uni, or in a club or whatever.

I’m glad it was him, then.

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We also discuss how women experience ā€œblue balls.ā€

If you’re a free subscriber and you’ve been following me for a while, I hope you’ve enjoyed my content thus far. Yeah, I’d got off with girls, but I was a virgin until I went inside a girl at 15.’

How does a straight woman lose her virginity?

By having an erect penis enter her vagina; pretty much the inverse of the straight male experience.

Like their male counterparts, the straight-female group also viewed non-penetrative trysts as ā€˜heavy petting.’

Medically speaking they’re not wrong; a willy injection does define a female’s virgin-free status.

But this isn’t the only reasoning.

In some cases, having penetration as the definitive ā€˜doing it,’ makes other acts feel less intimidating.

It also allows girls to explore their sexuality while assigning particular significance to their ā€˜official’ first time.

This was the case with Laura, 23, who says:Ā ā€œIt was important to me that I lost my virginity to someone I loved.

ā€˜Until I met my first serious boyfriend at 19, I was an ā€œeverything butā€ girl.’

As well as putting penetration on a pedestal, this group also considered some insertions more valid than others.

Apparently, some instances didn’t count as sex because ā€˜it slipped in by mistake’, or ā€˜we were just testing it out’.

Again, this seems to be a way of ensuring the first time fits with the girl’s criteria.

A little unusual perhaps, but, in a society where guys earn their man-card while women are deflowered, not altogether surprising.

What has a hymen got to do with female virginity?

Sod all.

When female virginity guaranteed paternity and freedom from STDs, an imperforate hymen was a handy ā€˜intact-o-meter.’

This was the premise for the ceremonial hanging of bloody sheets from the battlements for all to see.

Realistically, this thin membrane can be easily ruptured by exercise, tampons or even plain old growth spurts.

It has no bearing on sexual experience.

However, for those determined to bust-a-hyme on their wedding night, there is a growing market in hymenoplasties.

For straight couples, does having anal sex count as losing your virginity?

If you want it to.

There’s no accepted definition for how bum sex relates to virginity, so it’s pretty much up to the individual.

In some religious communities, unmarried women go ā€˜everything butt’ as a means of safeguarding their technical virginity for marriage.

There’s method to this madness.

If we view virginity primarily as an absence of sexual contact, it could be considered that we have several virginities, from kissing to boob squeezing.

So, as a woman you can be an anal aficionado but concurrently a vaginal virgin, or you can view the experience as absolute departure from Virgin Town.

The same goes for a man as the penetrative party in a botty bonanza.

How do lesbians lose their virginity?

By having sex with another woman.

In our heteronormative society, however, there’s a complete lack of discourse as to what constitutes sex between two women.

The one plus side is this gives the individual free rein to define their own sexual experience.

Shelley, 31, lost her virginity the first time she had mutual genital contact with another woman, whereas Helen, 22, broke the seal the first time she went down on a girl.

Some women lost their virginity the first time a partner brought them to orgasm, while others lost it the first time they were penetrated by fingers, toys or a tongue.

A myriad of Sapphic options.

Understandably, a recurring theme from our lesbian test group was intimacy being a defining factor.

As Leah, 26 explains: ā€˜I first ā€˜slept’ with a man, but personally feel I lost my virginity to a female.

ā€˜It was that emotional connection with someone.’

This is seconded by Anna-Maria, 26, who says: ā€˜I’d kissed/made out with a woman before, but the first time I had sex it was the intimacy that set it apart.’

How do gay men lose their virginity?

By having sex with another man.

Unlike lesbian nookie, there are points of reference regarding guy-on-guy sex, but these tend to revolve around anal penetration.

This is pretty reductive as only about 40 per cent of gay men areĀ anally inclined.

One such man is Anthony, 35 who says:Ā ā€˜There’s certainly too much emphasis upon anal as the definitive sex act between gay males.

Personally I feel my body is not built to enjoy it, either ā€˜actively’ or ā€˜passively.’

As for my first time, it was a huge leap and I can’t even remember whether we went as far as oral sex or just mutual masturbation.

But importantly, it was the whole act, including the kissing and cuddling, that contributed to losing my virginity.ā€

Due to the physical logistics and often categorical preferences (power-bottom, side, versatile etc), there are countless virginity-busting scenarios here.

Aaron, 29, broke his duck the first time he received oral sex, whereas for Gavin, 30, it was the first time he orgasmed with a partner.

Not to be dismissive of the old penetrative rumpy-pumpy.

Some of our test group did indeed lose their virginity this way,Ā butĀ considered part it of their first sexperience, rather than the qualifying factor.

As we said at the beginning, it’s highly subjective.

We can confirm that losing your virginity typically involves another person, genital contact and touching with the intent of causing and/or receiving sexual pleasure.

Otherwise, it really depends upon context, you and your partner’s boundaries, physical capabilities and, most importantly, how you feel.

Trust your instincts and, if they’re telling you that you’ve lost your virginity,Ā chances are you have.

We do hope you enjoyed yourself.

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