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Anonymous (30)

It's been a long, long time coming...

My relationship is great, with one small problem - no matter what my girlfriend and I try, I'm not having an orgasm. Oversharing details inside... [more inside]
posted by Ed The Sock on Jan 12, 2014 - 30 answers

At least I won't be a *40* year old virgin

I'm a woman in my thirties. I'm in a newish relationship with a guy I really like. The problem: I'm a late bloomer who took it a little too far and before I got together with this guy I had absolutely zero sexual or relationship experience. What's the least horrifying, least embarrassing way to tell him this, and when should I tell him? [more inside]
posted by anonymous on Nov 13, 2013 - 25 answers

When do I disclose which embarrassing/awkward sexual history fact?

I'm an almost-30-year-old man who is very romantically and sexually inexperienced--basically virginal--thanks to insecurity (general) and insecurity (sexual identity-wise). Now I've found a great woman to date. But what do I tell her about my lack of experience (and the why of it). And when? [more inside]
posted by sauberbrezel on Sep 11, 2013 - 24 answers

Let's talk about ... virginity!

30 year old virgin. History of sexual assault as a teen. Terrified of sex for a number of related reasons. The fear is holding me back and stunting my growth. [more inside]
posted by anonymous on Jul 26, 2013 - 29 answers

Date or wait?

I'm a man in his mid-twenties. I've never been in a relationship. I've never even taken anyone out on a date. I want to rectify this, but I think my mental health and my living situation prevent me from doing so. Should I even try to date? If not, what should I do? Details inside. [more inside]
posted by anonymous on Jun 10, 2013 - 35 answers

How should I compensate for something?

How do I make the most of my smaller-than-average penis? Snowflakey details follow. [more inside]
posted by Rustic Etruscan on Sep 6, 2012 - 45 answers

How do I overcome my lack of relationship experience?

I'm a normal, well-adjusted, heterosexual, 30 year old male. And I'm a virgin. How do I get past this? [more inside]
posted by ann on a mouse on Jul 23, 2012 - 58 answers

I feel bad saying I'm a virgin, and I feel bad saying I'm not.

I feel bad saying I'm a virgin, and I feel bad saying I'm not. [more inside]
posted by anonymous on Mar 21, 2012 - 29 answers

How horrible is it to be a 30-year-old virgin?

How horrible is it to be a 30-year-old virgin? [more inside]
posted by anonymous on Jan 24, 2012 - 46 answers

This feels like a weird role reversal

A guy I've been on a few dates with told me he is a virgin. Questions ensue. [more inside]
posted by anonymous on Jan 20, 2012 - 18 answers

How to have sex when you suffer from eurotophobia

I want to have sex with my boyfriend for the first time, but I have an extreme phobic reaction to both genitalia and vaginal penetration. How can I possibly overcome this? [more inside]
posted by anonymous on Dec 3, 2011 - 44 answers

operation get laid by my birthday

I'm facing down 26 years years of virginity. Help me succeed at Operation: Get Laid By My Birthday. [more inside]
posted by anonymous on Oct 30, 2011 - 29 answers

What does a virgin need to know for the first time?

I'm probably going to lose my virginity in the next few weeks. What do I need to know? [more inside]
posted by anonymous on Aug 23, 2011 - 49 answers

I'll be your tour guide for this evening.

A twist on the "I'm a 30 year old virgin" question. The virgin in question is my girlfriend. [more inside]
posted by anonymous on Mar 10, 2011 - 18 answers

Would a ribbed condom hurt a hymen?

What type of condom is best for sex between a virgin male and a virgin female with and intact hymen? Would textures help or hurt? [more inside]
posted by anonymous on Nov 12, 2010 - 34 answers

Tips for losing my virginity via online hookup

Tips for losing my virginity via online hookup [more inside]
posted by anonymous on Nov 10, 2010 - 48 answers

Should this about-to-be-30 female virgin give up on exploring relationships with men? (NSFW)

So I'm a late-twenties bi woman, and I'm still a virgin who's never had a boyfriend or girlfriend (I prefer guys). I'm glad I waited this long, though - even when I was 18, my Asperger's had me feeling somewhat younger socially and emotionally, and I was nowhere near ready to date or do anything. But now I've reached the point where I'm ready to start meeting some nice prospects, looking for a relationship and, yes, having sex. (NSFW) [more inside]
posted by tamagogirl on Nov 1, 2010 - 15 answers

Virginal quandry

A question and moral quandary from yet another sad virgin.... [more inside]
posted by anonymous on Nov 26, 2009 - 17 answers

Is it OK for a woman to omit to tell a guy she's a virgin?

My question concerns the etiquette of losing your virginity. [more inside]
posted by anonymous on Jun 21, 2009 - 35 answers

Problems with sex

I'm worried about my new-ish sex life with my boyfriend. Please help me figure out if everything is alright, and if it isn't what I can do. [more inside]
posted by anonymous on Mar 19, 2009 - 24 answers

What else could I have said in this situation? (NSFW)

What else could I have said in this situation? (NSFW) [more inside]
posted by anonymous on Feb 3, 2009 - 67 answers

To Wait or Not To Wait

I always thought I'd wait for someone special to have sex for the first time. But I haven't met anyone special. Is pursuing a casual relationship a good idea, and how do I do it? [more inside]
posted by anonymous on Feb 2, 2009 - 24 answers

Where does the phrase "losing your virginity" come from?

Where does the phrase "losing your virginity" come from? [more inside]
posted by rzperllian on Sep 2, 2008 - 13 answers

Apart from that it's an awful idea.

What should I know about trying to have casual first-time sex at a fantasy convention? [more inside]
posted by anonymous on May 13, 2008 - 47 answers

Losing virginity

I've lost my religion and now I am going to lose my v-card, please help. [more inside]
posted by anonymous on Feb 11, 2008 - 42 answers

Why can't I get Gardasil at 27?

Why can't I get Gardasil after I turn 27? [more inside]
posted by anonymous on Jun 18, 2007 - 22 answers

libido odds

What is the likelihood my girlfriend will ever get any sort of horny? [more inside]
posted by anonymous on May 23, 2007 - 66 answers

Help with lack of romantic experience?

Help me get past my staggering lack of romantic experience. [more inside]
posted by anonymous on May 17, 2007 - 44 answers

Teaching the Non-Rational Part of Yourself that Risk Isn't Always Pain?

How do you convince a part of your brain that seems unaccessible by cognitive function, yet holds beliefs that are affecting your life poorly? The combination of two such "unalterable" opinions has me currently locked into a course that will exacerbate, not solve, some very long-lasting problems. [more inside]
posted by anonymous on Mar 20, 2007 - 29 answers

Am I too crazy to be in a relationship with a virgin?

I never thought that I would ask a relationship question, but I also never thought that I would be 28 and dating a virgin. Please help me with my virgin (and my craziness). [more inside]
posted by anonymous on Mar 19, 2007 - 32 answers

When does sex stop being painful (and start being possible)?

Did penetrative sex 'work' for you the first time? If not, how long was it before it did? [more inside]
posted by anonymous on Sep 17, 2006 - 24 answers

. . . ahh, anonymous posting

Condoms, penis size, and virginity. . . [more inside]
posted by anonymous on Sep 17, 2006 - 34 answers

Virginity is actually driving me insane ...

Here's the problem: I'm fat, I'm balding, I'm in my early thirties, I'm a virgin, and I am beginning to very much need sex. [more inside]
posted by anonymous on Jul 25, 2006 - 73 answers

Look out, world

How can I get over my confidence issues and find a girlfriend (or boyfriend) in Ft. Wayne, Indiana? [more inside]
posted by thirteenkiller on Feb 18, 2006 - 30 answers

Guys view on virginity

Would it scare off a guy to know that I'm 21, have never had a relationship (short or long term) and am still a virgin? [more inside]
posted by trampesque on Sep 8, 2005 - 45 answers

First time sex advice?

So my girlfriend and I have decided we're going to have sex. First time for both of us even though we're both adults. We're going to go away for a weekend to do it. Any advice for making it great? What do you wish had been different about your first time?
posted by anonymous on Jun 23, 2005 - 75 answers

Mid-Life Virgin?

I am a 30-year-old Chicago male, and I am still a virgin. [more inside]
posted by anonymous on Apr 30, 2005 - 60 answers

Should virgins kiss and tell?

DatingFilter: I'll kiss on the first date (hell, make out on the first date if it's going well). I'm pretty outgoing in general, and I don't think anybody would ever suspect I'm a Virgin and plan to be one until marriage. When do I tell? Is it weird that I feel bad kissing a guy on the first date and not telling him (point blank: Am I leading him on)? Help me out, please.
posted by anonymous on Jan 16, 2005 - 57 answers

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