How tight should I be?!

Sir, should I prepare myself by plugging/dildo-ing myself to stretch it wide or should I wait until I found a worthy Master to take my virginity from my tight hole? Is the first impression matter? - a single sub

Hello Anon,

So your question essentially is “what do doms want from a first timer’s hole?” Right?

There is no one answer to this question. Everyone’s different. A fisting top might want to fist you and need it wide open. Other doms might expect you to be very tight your first time and enjoy the pain involved in opening you up.

I wouldn’t worry about people’s expectations. Just recognize literally no matter what you do… someone is going to decide they’re not interested for any of a dozen reasons and there’s nothing you can do about it. Your best bet, is to decide what you want to do and then advertise it as the perk associated with your virginity.

Here’s two examples of what I mean:

“Sir, my virgin hole has had nothing more than a single finger in it and would be honored if you’d be the first dick inside me.”

Or

“Sir, my hole has never had a real dick in it but I’ve been so eager to take a real man I’ve practiced with dildos. I’m still tight, but I’ll adjust to the pain much faster so you can enjoy my hole.”

I’m betting though if you’re asking me you’re not sure what you should do. Personally? I’d recommend that you go ahead and practice with the dildo. The first time is pretty painful, but if you’re getting fucked once a week it’ll adjust pretty quickly to penetration. So if you dildo yourself twice a week you should relax sufficiently that you’ll be able to eat that dick up no problem.

“What about the tightness!?” I’m sure you’re asking. Do a quick google search on “kegel exercises”. Doing these exercises is pretty easy and no one can tell you’re doing them so you can do them anywhere. The exercises will help keep you pretty tight and at the same time increase the flexibility of your hole. There are other benefits too but those are the ones related to your first time most closely.

So get a dildo, practice fucking yourself so you can be ready and enjoy most of your first time, and do some kegels here too so you’ll stay tight and be flexible.

Another bit of advice with your first time and practice. Try several different positions. Fuck for a bit, change, then fuck again, change, etc. Different dicks are shaped differently and so are your insides. They’re slightly different from everyone else. You want to try different positions because you’ll probably quickly find one that’s WAY better than others.

I think the last thing I’d recommend is both learn how to finger and teach tops how to finger. To finger yourself properly stick a finger in your hole and then curl the finger up towards your dick and rub back and forth. If you do it right you’ll feel a firm broad surface and it will feel amazing. Once you know where to touch vary the stimulation a bit and again see if you can find a favorite method. The purpose in fingering yourself like this is to get a personal sense of where your prostate is. When you know where it is, you can direct tops to fuck in such a way that they hit it pretty much dead on and if they do it perfectly you’ll see stars.

Good luck. Let us know how it goes!

Got a question about sex? BDSM? Ask me!

Comments

Post a Comment

Popular posts from this blog

My thoughts on raceplay

Anonymous   asked: What are your thoughts on raceplay? Obviously, raceplay is consensual and racism isn't, so how would someone go about navigating the thin boundary between the two? It seems as easy as just open communication and setting those boundaries but it is a touchy topic to bring up in the first place so it'd be great to know more about it. This isn’t the first time I’ve answered on this question, but I think that an update is overdue. This is also going to be long so strap in and each section is going to talk about different angles, thoughts, and experiences with raceplay. Trigger warnings:  This post will contain discussions or racially motivated sexualized play. It may reference racial violence as part of historical context or for illustrative purposes. If you are not in a place to read this material, don’t. It’ll be here if you really want to read it later. About the Author:  I’m a white gay man in my 30s. I have engaged with raceplay with submissives (and a ...
Read more

Is that REALLY the core of who I am as a person?

I read constantly on D/s Tumblr blogs that accepting that you're a slave or faggot is the first step to truly being happy. That all else in your life will just fall into place, all because you've accepted a side of yourself that in reality, few people will ever see. But is that really the key to my happiness?? Career, family, friends, money, none will offer the happiness that being a faggot or slave will?? Is that REALLY the core of who I am as a person?? Or is it more a Tumblr fantasy?? Thanks for the question Anon! Statement: I read constantly on D/s Tumblr blogs that accepting that you’re a slave or faggot is the first step to truly being happy. Commentary: Ehhhhhhh. It’s a path TO happiness. It’s true that some submissives really spend a lot of time making themselves miserable trying to avoid being themselves, but that’s the same thing as being gay and denying it. Sure, there are subs out there for whom embracing their submissive side IS absolutely transformative but that’s...
Read more

Impostor Syndrome and BDSM

  Impostor Syndrome and BDSM Part 1 of 2 Dissecting Impostor Syndrome   I am extremely grateful to the many people who have worked to give this concept a name and language we can all use in discussing it. Impostor syndrome can affect subs or doms, but for the purposes of this article I overcame it as a dominant and wanted to discuss it in detail from that perspective because I know other dominants struggle with this silently. Even amongst each other we don’t often discuss it. It is always important to start by defining the topic of discussion. Impostor syndrome is a feeling that we’re in a position in life, in love, in our career, or in BDSM that we have not in fact earned and that if others found out we’d be exposed and humiliated for pretending to be someone we aren’t.  I’d say 2017 was the last time I was feeling impostor syndrome pretty severely. I know not everyone reading this will know who I am, so I’d like to discuss my background and bonafides not as ...
Read more