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So, I’ve never been in a real relationship and I’m 31. I usually am busy taking care of my family’s drama and trying to get my life back on track, but I don’t know how to date properly or do relationships. I have trust issues and don’t know how to go about trusting a guy, much less letting him know what I am into. Any advise?

By Thomas Oldenough | December 4, 2019 | Comments Off on So, I’ve never been in a real relationship and I’m 31. I usually am busy taking care of my family’s drama and trying to get my life back on track, but I don’t know how to date properly or do relationships. I have trust issues and don’t know how to go about trusting a guy, much less letting him know what I am into. Any advise?

Thanks so much for asking.  I don’t know if you’ll appreciate my advice but it’s heartfelt.  You’ve never been in a relationship.  You’ve gotten wrapped up in family drama.  You’re trying to get back on track now that you’re in your 30s, but you have trust issues too?

I’m pretty sure the best relationship-finding advice I can offer is to talk to a counselor.  Not because you’re “crazy” – it’s another useless stereotype that counselors are only for “crazy” people, or that only “crazy” people go to counselors!

Instead I’m saying it because between trust issues and what you’ve said about dealing with family drama, a good counselor can help you separate yourself from your family drama enough to start having your own life.  And help you enough with trust issues to start having a life with someone else.  Besides your family, I mean.

The reason I’m recommending this is that with a little outside professional perspective, help, and support you may not feel like you have to choose between all of the above.  You can still support your family without being drawn in, establish yourself in your own social and career life, and maybe even find someone you can trust.  And maybe even find someone who’ll be into the same things you are!

I’m a kinky person and I’m guessing you may have some kinky feelings too.  And so it may surprise you when I say that kink doesn’t bypass the rights and responsibilities of vanilla relationships.  Kink extends those things, but a kink relationship is still a relationship.  There’s no “instead of.”  And as I’ve probably said in the past, when it comes to kinky relationships you’ve got to learn how to walk before you can crawl. 

We all have a real tendency to say “I can figure this out on my own.”  But as gently as possible I’m going to say that for most of us if that were true we’d have already done it!

The wonderful, awesome, best news in the world, though, is that you’ve taken the first big step: you’ve asked someone for help!  Good for you.  There are so many people who never do!  They just continue thinking “I can figure it out myself” until they’re 93 and not 31!

The second most important step, though, is to understand that this isn’t a question that can be answered in an anonymous ask.  Because all I or pretty much anyone can say is “talk to someone who’s trained to talk to people just like you.”  Not “crazy” people like you.  And me!  I’ve never been crazy as far as I know but I’ve gotten a ton of benefit from talking to various counselors over the years… once I got over the notion that I could “figure it out myself!”  You can too.

Best of luck, ok?  I’m not going to say “thank you” for asking this important question.  Instead I’m going to say “good for you!”  You’ve done the hardest part.

hi! long time fan, haha. what’s the best way to comfort an insecure Daddy without being patronizing? I’d love to tell mine how much I adore every curve and stretch mark and freckle, ect. but I don’t know how to do it without worrying that I’m breaking “character” or my “role” so to speak if that makes sense?

By Thomas Oldenough | December 4, 2019 | Comments Off on hi! long time fan, haha. what’s the best way to comfort an insecure Daddy without being patronizing? I’d love to tell mine how much I adore every curve and stretch mark and freckle, ect. but I don’t know how to do it without worrying that I’m breaking “character” or my “role” so to speak if that makes sense?

This is a wonderful question!  Thank you so much for asking.  It’s important to remember that Daddies and other men-identifying people can be just as self-conscious about our looks as anybody else.  And just as annoyingly difficult to convince otherwise!

As the old Red Green show tagline used to go, “If the women can’t find you handsome they should at least find you handy.”  Which was just ridiculously tragic, because, in fact, quite a few women are over the moon about “dad bodies” and “teddybears.”  (Also waifs, nerds, and other non-ruggedly-manly body types.)  This is something that wayyy too many men don’t realize.

So what’s the best way to comfort a Daddy who’s insecure about his curves, stretch marks, and freckles?  I honestly can’t say – I’ve had very little luck convincing anybody they’re attractive if they’re convinced they’re not.

It wasn’t till I started posting naked or nearly-naked selfies that I believed it.  It’s one of those weird “who are you going to believe, everyone else or my own lying eyes” things where I look at myself and I still can’t believe it.  I’m just outvoted.  (I don’t necessarily recommend he start posting nearly-naked selfies, and you might not want him to either, but he’d probably be surprised how outvoted he was.)

But let’s talk about something else for a second.  You said you didn’t know how to do it without breaking out of D/Lg character with him.  First of all I’m gonna say there are a million ways to do it in character: just shower him with “handsome, gorgeous, sexy Daddy” or “big, strong teddybear Daddy” or maybe “can I kiss you everywhere you’re handsome, Daddy?” 

But I’m also going to say it’s ok to say “Daddy, I’m going to have to put on my big-girl pants for a minute and have a heart-to-heart talk.”  Because even in 24/7 relationships there are going to be times when you and he have to talk like adults in a relationship… which of course you both actually are!  Kink relationships are still relationships!  They don’t erase or invalidate vanilla-relationship responsibilities, they extend them.  And that can include things like conversations about mental health, biological health, financial issues, work or school schedules, and reassurances about self-esteem.

Best of luck to you and to your very lucky Daddy.  And thanks so much for asking about this!

🙈 Back with another cockwarming (ish) question. Can someone cockwarm with their mouth? Or is that something different? And thank you for answering my previous question.

By Thomas Oldenough | December 3, 2019 | Comments Off on 🙈 Back with another cockwarming (ish) question. Can someone cockwarm with their mouth? Or is that something different? And thank you for answering my previous question.

What a sweet question!  And you’re welcome about my last answer too.

Readers may remember that cock warming (as defined by Urban Dictionary, for instance, means…

cock warming
The act of a man slipping his erection into his partner’s vagina or ass in order to keep warm – a more intimate version of spooning.
eg. “Jake held Jenny close for a bit of cock warming before they fell asleep.”

You may also remember the nerdy tidbit that it seems to be popular with fans (and fanfic writers) of Korean K-pop.

If you ask me I’m going to say that while one can cock-warm someone with their mouth I prefer the term cock nursing.  As in…

“Meanwhile, under his desk Jenny softly cock nursed Jake while he did important Daddy spreadsheet things on his computer.”

Thanks for asking!  Let me know whether you think cock nursing is different from cockwarming.  (I think either way it’s a wonderful feeling.)

By Thomas Oldenough | December 3, 2019 | Comments Off on

Because an older, experienced Daddy is always going to be supportive, isn’t he, monkeybutt?

By Thomas Oldenough | December 3, 2019 | Comments Off on

generalgrievousdatingsim:

since when did THIS

become sexier than THIS?

generalgrievousdatingsim:

fucked up that we don’t make belts with loops for holding blades or pouches for storing coins and dried herbs anymore

Hmm.  Why would anybody think a plain old belt was sexier than one with built-in pouches and pockets and sheathes and holsters with auxiliary thigh straps, cuddlebug?  I mean, all a D/Lg Daddy can do with a regular belt is double it in his big strong hand…  😏

(Don’t get me wrong!  As a former professional journeyman leatherworker those other kinds of belts are so much fun to make, and they really are good for carrying swords or hammers or coins or dried herbs!  But take it from an expert: plain old Daddy belts are just soo much better for spanking naughty Little elves and minxes, aren’t they?)

By Thomas Oldenough | December 3, 2019 | Comments Off on

It’s been almost a year since the corporate incels who runTumblr’s corporate owners wet their pants.  Luckily they haven’t figured out that “female-presenting kisses” are even more erotic than “female-presenting nipples…”

🙄

By Thomas Oldenough | December 3, 2019 | Comments Off on

the-innocent-ginger:

Cute date idea: you win me a huge teddy then make me hump it while you watch once we get home

An older, experienced Daddy who understands that not everybody is ready for penetration finds other ways to help you  show  get off, doesn’t he, appleseed?

By Thomas Oldenough | December 3, 2019 | Comments Off on

Just a reminder that not wanting a dick pics isn’t the same as not wanting a dick.  

Paradox: Guys who don’t send dick pics get asked for dick.  Guys who do send them don’t get dick!

I’d say “it’s a great mystery” except… well… it’s not a mystery at all, is it?  🤷‍♂️

By Thomas Oldenough | December 3, 2019 | Comments Off on

50shades-of-impregnation:

Sooooo many ways to have you on, over, and in my lap, kittywhistle.  This might be my favorite one of all!

By Thomas Oldenough | December 3, 2019 | Comments Off on

stayathomedaddy4u:

50shades-of-impregnation:

Wake her up with your fingers deep inside her

When I wake up in the middle of the night, as I often do. As I just did…