STRUGGLE SESSION: Coming In Third, Coming In Condoms, Coming In Strong… and More!

...To the woman nervous about having a threesome with two hot people, they’re obviously into you and think you’re hot too — the guy reached out to you, after all — and you would bring something that all their hotness can’t match: novelty. If they’re good at having threesomes, they’ll make you feel like the very special guest star you are. Late Bloomer (via email) weighed in on the same call via email… Longtime listener and reader from Vancouver, Canada. I’m a late-bloomer gay guy in my 50s and I really like your advice to the woman who was insecure about her looks before having a threesome with two hot people. I recently had a threesome with two hot guys in their 20s and I have to tell you… I got jealous when the two of them were at it without me. I grew up with low self-esteem and it came up during those moments. I was grappling with it afterwards. Your advice really helped with my insecurities. I’m a guy in my 50s who had a threesome with two guys in their 20s! There’s a lot to be grateful for here! Thanks, Dan! You’re welcome, Late Bloomer — and, hey, even if you weren’t included in the action (BUT YOU WERE), there are worse things than watching two hot guys in their 20s going at it right in front of you! And before we leave this topic: Jonathan shared his own perspective on being the least-hot person at a threesome — nice work if you can get it — along with steamy details about his most recent (but certainly not his last) threesome. So, a recent caller told a casual sex partner — a man she was rawdoggin’ College-of-Cardinals style — that she didn’t wanna know if he was fucking other women but she wanted him to start using condoms with her if he did start fucking other women. JJ72 made a good point… Saying, “I don’t want to know if you’re sleeping with other people, I simply ask that we start using protection then,” is a bit of an impossible request. If he told her they need to use protection now, he might as well have told her, “I slept with someone else.” I don’t want to defend this guy’s behavior, but she should be more realistic of what to expect of casual sex partners. If someone is having unprotected casual sex with you, it’s best to assume they’re having unprotected sex with other people as well. Jonathan seconded JJ72… Agreed. The dude awkwardly reaching for a condom packet halfway through a scene when he’s never done it before isn’t the best way to broach the topic. And a point I made a few weeks ago… condoms are good for birth control. They’re somewhat good at STI prevention. But if you’re doing oral, the condom does nothing. And then JJ72 jumped back in with a good critique/reminder… Dan acts like condoms give 100% protection against STIs. A few weeks ago there was a cheater who gave his wife an STI and Dan just assumed he didn’t use a condom. It is much more likely an STI remains symptomless if located in the mouth; in the genitals it usually gets painful which most people will get checked out. That alone means a lot of transmissions happen orally — and I don’t just mean blowjobs. You actually can get some STIs from kissing or licking. I’m not saying forget about condoms. I’m saying please get checked even if you are using them. “External and internal condoms, when used correctly and consistently, effectively break the chain of STIs transmission and are cost-effective.” — World Health Organization I’ve consistently pointed over the years — consistently to the point of constantly — that condoms… when used correctly (which many people fail to do)… offer good protection against syphilis, gonorrhea, chlamydia, and HIV and less effective protection against STIs that spread through skin-to-skin contact, e.g. HPV, herpes, molluscum. Syphilis, gonorrhea, and chlamydia can also be transmitted orally (HIV not so much), which is why it’s not a full STI check if you’re not getting a throat swabbed too. I feel like I’ve rattled these facts off a million times… and I do sometimes get self-conscious about repeating myself, and may have neglected to rattle this off the last few times the topic has come up. But it bears repeating, and I will err on the side of repeating it the next dozen or so times condoms come up! Said SavageListener… For the woman with the language barrier in the group sex setting, I wanted to recommend the Making Out In… series. They’re phrase books for dating/intimate language. I used it when dating in Korea and it made a huge difference in my comfort level just to know what was being said. Maybe you can find “Making Out In Belgian” or whatever language you need. The books are on Amazon! Good luck! There are seventeen books in the Making Out In series…. but only three cover European languages: English, Spanish, and Italian; so, anyone trying to get laid in, say, Germany ist im Arsch. And we don’t know what European country that caller was fucking her way across… but if she’s currently fucking her way through Brussels… she’s going to need Making Out In editions in German, French, Dutch/Flemish (West and East Flemish), Luxembourgish, and one or two other local dialects! (PSA: You can fuck Belgians in Belgium but you can’t talk dirty to Belgians in Belgian in Belgium — or anywhere else — because Belgian isn’t a language spoken by Belgians in Belgium…. or anywhere else.) Q9 in this month’s Quickies was from a cis woman who wondered if fantasizing about having a dick means she’s trans. Alex has some good advice and a sex toy recommendation… I think your message points you to being a woman who would like to penetrate — and although you can’t yet connect a strap-on to your nervous system, the new models of Straponme get as close as they can (they cost a lot of money, unfortunately). BTW: If you haven’t already, the moment you put yourself out there as a pegger, you’re going to have a queue of men hoping to be penetrated. So, spend less time wondering on your gender identity and more time getting a strap-on. Q5 was from someone wondering whether it was possible to ask a partner — in a sexy way — for something they wanted “in the moment,” i.e. once the sex was already happening. Said dimples_and_dumples… Asking for what you want is sexy. Just say it confidently and without shame and it will be sexy. Also if you’re afraid to say it out loud, saying something in a loud whisper is also always sexy. D&D is right… up to a point. Asking for what you want confidently and without shame is going to be sexy… and it will most likely get you what you want… so long as what you want falls within the not-nearly-as-narrow-as-it-used-to-be band of familiar sex acts/activities/kinks. “Spit in my mouth,” when said with confidence and without shame, will get your mouth spat in. “Shit in my mouth,” said with equal confidence and no shame, will get you, er, dumped. Says BiDanFan… Completely off topic, but if Dan is still doing Muppet Faced Men (ahem), I nominate Yungblud. OMG! That smile! So Muppety! Thanks, BDF! (While I haven’t named a Muppet-Faced Man of the Week for ages, I’m still doing (ahem) Muppet-Faced Men… whenever I get the chance.) Okay, here’s a question that came in for the column this week that I’m not going to run in the column… I’ve had a decent amount of non-monogamous fun… strictly friends-with-benefits arrangements, always casual. But a younger friend has asked for advice about her non-monogamous situation and I’m not sure what to tell her. She’s dating a non-monogamous man who is married. His wife is fine with it — in fact, her wife also has a boyfriend. She has fallen in love with this man (another woman’s husband) and they are “dating” seriously now. She says he might be her “forever person.” My concern: She is only 34 and has school debt and wants very badly to buy a house and get her life together financially. But from what I understand, the man she’s seeing already has this with his wife. It’s sad to see my friend with nowhere to go from here. A different boyfriend — a single boyfriend — would be able to move in with her someday, share the rent and other expenses, contribute to a deposit on a home, etc. As things stand, my friend is just getting by and essentially getting by alone. Do you think if things gets more serious between her and this married man that he should help her out financially? Friend In Need Have some advice for FIN? Drop it in the comments…