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Should I Masturbate With a Quarantined Guy Over Instagram DM?

And all your other most pressing questions for adult film legend Tasha Reign

Every day, porn star and University of Southern California journalism grad student Tasha Reign wakes up to a curious string of emails from her fans, a devoted group of men and women she lovingly refers to as “Reigndeer.” Said Reigndeer ask her questions — so many questions — about her perspectives on sex, love, relationships and life itself, and as someone who’s had more firsthand experience in these areas than four adult women combined, she’s become uniquely up to the task of answering them. Bi-weekly then, Tasha will select a few of these questions and provide her insight, advice and expert wisdom in the hopes that she can help you fuck and love better, too. 

My boyfriend recently revealed to me that before we started dating, he attended swinger and sex parties. I’m not comfortable with anything like that, and while he says he’s okay with that and not pressuring me, I’m afraid that he’s eventually going to resent me — or even attend one and not tell me. 

I’m to the point where I don’t know if I want the relationship to move forward because I’m so fearful of that happening. Do you find that people that have had that lifestyle previously can be happy with just one person? I’m not saying I’m not adventurous in bed; I’m just not comfortable bringing someone else (or multiple people) into the bedroom.
I can totally empathize with your concern over your man wanting “more.” In your mind, he’s already seen what “more” looks like, and why wouldn’t he want to go back to that? 

Well, I can assure you that, despite your fears, it’s absolutely possible to have experimented with abstract, sexual lifestyles and then continue on a more “normal,” happily monogamous path. I know this because I’ve been in his exact position. 

I’ve escorted. I’ve created porn with multiple partners at one time. I’ve had a threesome here and there. And for the most part, I’ve been sexually “promiscuous” by most people’s standards. Somehow, though, I lucked out, and my boyfriend Kyle doesn’t question whether or not I want to go back into that lifestyle. I’m thankful that he doesn’t, too, because if he was constantly asking me if he was “enough,” I don’t know how I’d handle it. 

Back then, l was young and free. Now, I’m older and less free, but I’m also happier and more at peace than I’ve ever been before. I may have had a fun time in my 20s and look back with fondness on those memories, but I cherish my life with Kyle and can’t wait to start a family. 

Sometimes in life, we have moments where we’re trying on “hats” of all different varieties just to see what it’s like and what we’re really about. Maybe that “swinger” hat was fun for him at the time, but it sounds to me like he’s ready to retire it. So if I were you — and if he hasn’t given you any other reason to distrust him — I wouldn’t give it another thought. Listen to what he says, watch what he does and let his actions be your compass.

I’ve been sexting a lot with an old, one-time hookup who recently got in touch with me after this whole quarantine thing happened. We stayed friends and have no bad blood, but I can’t tell if what’s happening between us is real or virus-related. Basically, how do I tell if it’s a thirst trap, or if she’s actually expressing feelings for me she never did?
I had a funny realization the other day — doesn’t this whole quarantine thing feel like the holidays, minus the decorations and seeing people in person? It does to me, at least in terms of my exes. During November and December, my phone gets blown up with odd texts from previous lovers or men that I no longer speak to, most of whom are home for Thanksgiving or Christmas and bored out of their minds with their families. People really want to reconnect during times of crisis or loneliness, and now that coronavirus has amplified both to an unimaginable degree, the crazies are really starting to come out of the woodwork. 

Is it possible that her attempt to reconnect is genuine and that she was the proverbial “one that got away”? Sure. Is it also possible that she’s just one of the many intensely lonely people putting feelers out in all directions so that they can have someone to talk to during an isolating time? Definitely. The only way to find out, then, is to ask. 

What’s stopping you from posing that question to her flat-out? You can always wrap it in a casual statement like, “Hey, I’m really glad we’re talking again and I’m totally down to keep doing it, but I just want to make sure this is genuine, not a virus-related thing.” 

That’s far more credit, though, than I’d give her if I were you. I’m a believer in the saying “an ex is an ex for a reason.” If you couldn’t work it out when there wasn’t a devastating global pandemic upending everyone’s lives, why would you suddenly be more compatible now that everything feels as though it’s crumbling? 

I totally get the feeling of wanting to connect with old partners and friends during an uncertain time, but honestly, there’s no time like the present to get involved with online dating, app dating or just flying solo — without the baggage of your weird exes weighing you down.

I have this one Instagram follower that I’ve never met who says he lives in Italy and is all alone during lockdown, terribly horny and depressed. He keeps asking me to masturbate with him over Instagram DMs, telling me he has no one and it would mean everything to him if I got off with him. I’m not opposed to it, but I probably wouldn’t if there wasn’t a pandemic going on. Should I? I mean, would that be like a kind, charitable thing to do at this point?
First of all, it’s comforting to know that other people view adult entertainment as a form of charity. I’ve always felt this way and wondered if other people outside of the industry do as well (though the Australian model who sold nudes for bushfire relief was a pretty stellar example). There are so many people who can’t engage in sex for myriad reasons, and the fact that they can now go online and be entertained by women and men is amazing. 

That said, I certainly hope you know that there’s no pressure or obligation to share yourself intimately in this capacity. It’s quite entitled that this person would think he can ask such a thing from you, and there are definitely repercussions of all sorts that come with sharing nude images and videos of yourself online (especially with a stranger). Plus, this person can get off to anyone on the internet. If he’s able to get on Instagram, he’s able to get online, where I promise you that he can find hundreds, thousands and even millions of other things to get himself off to in a time of need. 

In other words, it’s hardly your sole responsibility to entertain the troops.

I would think about this choice long and hard and maybe wait until there isn’t an international lockdown going on to make you feel one way or another. Depression and horniness are very real, but so is all the “free” — i.e., stolen — porn you can find online. This person will be totally okay with or without your nudity, but if you’re feeling kind, thoughtful and unconcerned about the potential risks, then hey, go for it! 

Feel free to send me your sex, love and relationship questions at [email protected]!

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