!! OMG, Valentine’s advice: Your Friend Dorothy on love, sex and pleasure !!

Your Friend, Dorothy

Illustration by Eric Kostiuk Williams

It’s Valentine’s Day weekend, and our resident advice columnist Your Friend, Dorothy has answers to your love, sex and relationship questions in this special edition of her column: Horny-from-a-distance? Seeking connection with an old flame? Parenting an adolescent kid with a boob fixation? Dorothy can help.

Read Dorothy’s good advice after the jump, and scroll to the bottom to submit your own question!

Dear Dorothy,

My son has recently turned 14 and has an iPhone. We’ve learned that he’s started looking at porn.  He’s especially interested in LARGE boobs (especially cosmetically-altered ones).  The women he’s looking at are a lot older than him and doing things that I highly doubt most 14 year old girls are doing. I know all this because he’s been downloading pics and vids and didn’t realize they were saved to the family iCloud account (both my hubby and I are gay so I know it wasn’t either of us lol).We are both very sex-positive and have talked to him about different body types and sexual activities that are appropriate for his age. He just clams up and denies that any of it is his.  I’m sure it won’t surprise you when I say that he’s 100% not interested in talking with us about this stuff.

We worry that, as a kid, he’s going to have unrealistic expectations about sex and — more importantly — girls’ bodies.  The dilemma is that anything age-appropriate would be considered child pornography, and while we are not advocating for that, we have no idea how to help him develop realistic and age-appropriate expectations. I mean don’t get me wrong, when I was his age I had a thing for daddies, but I wasn’t expecting them to shoot pingpong balls out of their ass, or watching cum-drenched bukkake scenes with buckets of fake semen.

Seriously, how can we help him to develop a healthy sexual outlook towards sex and girls his own age?

A Concerned Dad  

Dear ACD,

Wow, I have to admit I’m really concerned about this email.  I mean, you must know that, as a parent, you have to do everything you can to prepare your kids for modern life and proper adulting.  So why on earth haven’t you taught this kid how to stream???  The amount of data he’s burning downloading that stuff is bound to be impactful to your wireless bill and think of the inconvenience of storing video after video of cumshots on boobs alongside reels of family birthday parties and holiday photos.

Just imagine what HIS kids will think when they delve into your family’s digital archives years from now.  Learning to manage our digital footprint is going to be essential for kids growing up these days.  You need to sit him down and have a conversation.

About all of the ginormous breasts he’s (denying) looking at, well you’ve got me there.  I cannot in good conscience send you to the “barely legal” section of a major, mainstream porn site.  Would the Sears Catalogue be too much of a step down?  How about a trip to the local art gallery to view the human body in its glory on canvas?

Or maybe watch some movies together… Portrait of a Lady on Fire features some great shots of boobs, as does that hilarious scene from Monty Python where Arthur Jarret chooses to be executed by being chased off a cliff by a swarm of gorgeous, naked women (remember: you’re trying to build character here).  It’s perfectly normal for kids to be interested in naked bodies and you’re right to be thinking of how you can introduce this in a healthy way.

I’ll also raise the importance of him interacting with actual girls and women IRL (which, if you’re already doing, bravo!). Given that the goal is for him to develop real relationships that are deep and meaningful (from which great sex will likley follow), perhaps it would be useful to make healthy interactions with girls and women a normal part of life.  This will also boost his confidence, too, when it comes time to flexing his game in person.  Granted, this is hard in these COVID times, I know.

Lastly, has he considered extra-curricular activities as a way to meet girls his age?  Say what you will about lugging a tuba around, but sweet jesus, do those kids in high school band get laid!

Dorothy signature

Dear Dorothy,

I’ve met someone online recently and I’m really keen to get intimate with them.  The only problem is he lives a few hours drive away and with Covid cases being so high in both of our areas it’s unlikely that we’ll be able to meet in person anytime soon.  Do you have any suggestions for ways we could have something resemebling a sex life togehter under these circumstances?

Signed, Seeking Other Situations

Dear SOS,

Excellent news, SOS!  Your problem is a common one and, thanks to human ingenuity and modern techonlogy, help is but a few taps away! If you’re stuck at home all high and horny, far from your lover’s embrace, why not invest in a COVID-safe Valentine’s Day gift?

Nothing says “looking forward to meeting you” like the Hush Teledildonic Butt Plug. It targets the perineum and prostate with a variable vibe that you or your lover can control from afar via a remote app while you chat on video.

Too intimate of a touch for a new flame? Maybe start with a socially-distanced walk while he wears the Diamo Bluetooth Vibrating Cockring. There’s something sexy about not being able to touch while watching him experience pleasure from a public-health-approved six-foot distance.

Toys can provide a much-needeed release (and something to laugh about) as you get to know each other. Enjoy the surprises that come out of limitations and, if things go well and you build the necessary trust, the two of you can make a plan to bubble up and get down.

Dorothy signature

Dear Dot,

Maybe it’s the COVID, but I have found myself spending too much time thinking about the past of late.  After taking my edibles a few nights ago, I got to thinking about a former lover — things ended fine for us, we just sort of drifted apart. He had this minor band that he was Very. Serious. About. I checked, found them on Spotify, and pressed play. 

The music is middling, sure, but I was having fun. Until a song called “He’s Insane” came on. Hand to God, Dorothy, the lyrics are about me!!!  Should I confront him? Should we hook up and I show him what crazy really is? 

Help me!

Dear Help me!

Thank you for this fascinating letter.  I hope it inspires many more readers to go sifting through the detritus of their former lovers’ creative work, particularly in these challenging times, when everyone is feeling super raw!

You didn’t mention how recently the relationship ended or how much time had passed between then, when these songs were written and this discovery.  I will certainly agree that it is totally weird for him to write a song (seemingly) about you.  So do you KNOW for SURE that the song is really about you, or is it just the edibles talking?  Sometimes I feel like Patti Smith is singing just for me.

Nevertheless, I suppose the only way for you to truly know for sure would be to talk to him. Many people are going around looking for things (and people) to do these days.

Mining past, amicably-ended intimacies is a great way to accomplish this. Who else do you trust? In fact, I’ve even heard it said that a good chat session with an ex can be worth ten years of therapy.

So, maybe pick up the phone?  You don’t have to open with the song.
Dorothy signature

Got a burning question, or just something burning down there? Get answers from Your Friend, Dorothy, the OMG.BLOG in-house advice columnist.

Receive thoughtful, compassionate advice from your friendly neighborhood den mother who’s been there, done that, fucked it, smoked it and lost her T-shirt on the dance floor. She’s po-mo, poly, pan and a social compass to help you land safely as you soar.

Email your questions to [email protected], message Dorothy on Mastodon at @[email protected], or DM @omgblog Instagram.

OMG.BLOG has an affiliate partnership with Lovense, the manufacturer of the toys recommended in this column.

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