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Sex & Love

Penile problems big and small, clean and clogged

I’m a 33-year-old straight guy with a small dick. I have a girlfriend of seven years. When we met, I was really insecure and she had to spend a lot of time reassuring me that it didn’t matter – she loved my dick, sex with me was great, it was big enough for her, etc. I broke up with her...

Should The Cougar sever ties with The Kid?

There’s this boy – he’s 29; I’m 46 and female. We met when we were 23 and 41. I was not and am not into little boys. The Kid chased me, and I turned him down for months – until I got drunk one night and caved. It was supposed to be a one-night stand, but it isn’t anymore. We’ve never been...

How does a queer woman navigate a world of mansplaining heteros?

I’m a queer woman. When I entered my 30s, I realized that I was more queer/bi than I had previously allowed myself to be, and I started exploring my attraction to cis heterosexual men. Five years later, and I’m in an incredible GGG relationship with a cis het male. He’s everything I have...

After years of free porn, is it time for a penance?

Over the years, I have consumed what I believe to be an average amount of porn for a 44-year-old hetero guy. I have never paid for it, and I am now facing a troubled conscience for that fact. I could obviously just subscribe to some site or other now, but that would benefit only one...

Three kids, a long-term marriage and a sex life that sucks

Straight male, 48, married 14 years, three kids under age 10. Needless to say, life is busy at our house. My wife and I have stopped having sex. It was my decision. I get the obligation vibe combined with a vanilla sex life, and it just turns me...

O, the woes and worries of the aging virgins

I’m a 31-year-old straight woman. I have a good job, great friends and average attractiveness. I’ve dated close to 30 men at this point, and I can’t wrap my head around this: I’ve never had a boyfriend or dated anyone for more than a couple months. It’s really starting to wear on my self-esteem. I don’t believe anything is...

What to do about the scourge of our nation, Fox News?

My father is a friendly, kind, all-around good guy. We get along well and always have. But I now have to avoid all political discussions with him. He was always a bit socially conservative, but now he gets a lot of batshit crazy and simply dumb ideas from the scourge of our nation today: Fox News. How can we stop the dumbing...

Is going out to fulfill vomit kink considered cheating?

I’ve been aware of my emetophilia since a very young age and have always kept it private. No need to tell me about the health risks, I’m aware, and I’ve only ever indulged this kink through videos online. The actual substance doesn’t turn me on – I have no desire to be puked on. For me, the fantasy involves being with someone...

Is it illegal to buy a hot guy’s used underwear, sweaty tanks?

I’m a 49-year-old gay man. I’ve become friends with a 21-year-old straight guy. He’s really hot. He’s had to drop out of college and return home. I know he needs money, as he hasn’t found a job yet and has resorted to selling off old music equipment. I would love to have some sweaty clothes of his, namely his underwear, but...

Expat needs to make kinky proposal to boyfriend ASAP

I am a 20-something, straight, cis-female expat. How long do I have to wait to ask my German lover, who is übersensitive about the Holocaust, to indulge me in my greatest – and, until now, unrealized – fantasy: Nazi role-play? He is very delicate around me because I am a secular Jew and the descendant of Holocaust survivors....

Sex questions from an uninhibited audience

I was honored to speak at JCCSF – Jewish Community Center of San Francisco – last week as a part of their “Uninhibited: About Sex” lecture series. The audience submitted questions on cards, which were ably put to me by Jourdan Abel, who was wearing a wonderful uterus-themed sweater. (Check out my Instagram account –...

Physical, sexual compatibility important in healthy marriage

I’m a 24-year-old male, married three years, monogamous. My wife and I are religious and were both virgins when we got married. I’m sexually frustrated with two things. (1) How can I get her to give me oral sex? (She has never given and I have never received oral sex. I regularly give her oral sex.) She is afraid to try it,...

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