Day 3: How to Pleasure Women, Whether Penis Size Matters & Orgasms [Part 1]

Day 3 of 365: Andy and Imogen cover matters of size (Part 1).

First topic: Does dick size matter?
  • John asked: “Could you spare a minute or two of the podcast talking about dick size? Yes, cringy, I know. But it is an insecurity for men, similar to height, hair, muscles, etc. Does one absolutely have to be hung (8 inches or more) to be considered good at sex and give women decent pleasure? Or can the average 6 incher do the job? Of course, different women have different preferences, but I still want your opinion.”
  • Well John, we can definitely spare a minute or two of the podcast – we’re going to spend the entire podcast talking about this stuff.
  • Make it clear it’s not cringy, it’s a legit question a tonne of guys ask.
  • My dick is 6.5 inches (roughly). So I’m not massive. Ask Immy if she’s satisfied, what her thoughts are on dick size?
  • John’s specific question – do you have to be hung to be good at sex and give women decent pleasure? So I don’t have a big dick, and I give women WAY above and beyond decent pleasure.
  • In her opinion, have all the girls we’ve slept with together cared about my dick size?
  • Guys stress about dick size – why? Because they don’t think they can please a woman.
  • Foreplay is more important.
  • How to have good foreplay. Read out a lot of the foreplay guide: https://killyourinnerloser.com/tinder-guide-4/#32-the-foreplay
  • Psychological play, teasing a girl, making her beg, etc.
  • I’ve had a tonne of times where I literally don’t use my dick. I mention this in my performance anxiety article.
  • Orgasms, or no orgasms – do girls care?
  • How many times do I make girls orgasm? Most of the time I don’t.
  • Do girls feel disappointed if they don’t orgasm?
  • Obviously imogen is just one girl, but remember we talk to and ask most girls we sleep with all these questions. And I’ve always talked to girls after sex about all these questions.
  • Screening: John mentioned “Different women want different things”. Yep. There will be a few women who WANT a huge dick. Maybe they’re super fussy and those girls literally won’t sleep with you if you’re
  • Guys with tiny dicks – eg 4 inches or less. What to do? Focus on foreplay, get into BDSM (I’ve got plenty of guides on my website), focus on sexual bucketlists.
  • Bathmate: You can use it to increase the girth (width) of your dick, and some guys also use it for length increases. I have a bathmate guide on my site. Bare in mind I get a commission if you buy through my site, so factor that in when you’re reading the guide.
  • However, let’s be clear: I don’t want you to go out and buy one thinking you need to make your dick massive in order to pleasure women. We’ll cover pleasuring women below. Get the bathmate because you think it’d be fun (it’s absolutely fun as hell) – not because you think you need it.
  • Talk about why it’s fun – makes your dick fat as hell. When you jerk off, it’s like it’s not your dick – feels really weird. Your brain keeps saying “Something is wrong, this isn’t my dick” – your hand is used to your dick being a certain size, so it feels weird when it’s bigger.
Second topic: Pleasing women vs just having fun WITH her.
  • Your job isn’t to please a woman or give her pleasure. I mean yes you do want her to feel good, obviously. But that’s not your mission.
  • Your mission is to have fun WITH her. It’s “you and me”, not “you vs me”. You’re on the same team. You’re exploring TOGETHER.
  • This isn’t a test – she’s not giving you a grade, or a score out of 10. She’s not judging you. Don’t feel like you have to jump through a bunch of hoops and do everything to please her – that’s a weird “transactional” view of sex. You’re not giving her something. You’re exploring TOGETHER. You’re giving each other pleasure – it’s not “man must make woman feel good”.
  • Try a bunch of different things with her. Experiment and just try stuff.
  • Sex is supposed to be fun for YOU too, so put yourself first. Obviously don’t neglect her, but you should be putting your own excitement and pleasure first. That way you’ll be really turned on and then you can share that with her.
  • Women get turned on by being WANTED. By being DESIRED. They get turned on by seeing that you are turned on by THEM. So get yourself really fired up (we’ll go into how to do that below). Make yourself WANT her, and focus on doing the things that really turn YOU on.
  • Become an animal who can’t control himself. Literally say stuff like “I can’t stop myself when I’m around you” or “You drive me crazy” or “You make me want you”.
  • Give out tonnes of compliments – “I love your tits”, “Holy shit you’re sexy”, “Jesus you turn me on so much”, “You have the hottest ass”. Girls get really, really, really turned on and feel really bloody good by you just saying whatever is on your mind.
  • Someone once asked me “How do I compliment women during sex? I literally don’t know how. Tell me what to say.” Really it’s about just saying whatever thought pops into your head. And thinking LESS, and just blurting it out. Eg if you think “Wow she has cute tits” literally just blurt out “You have cute tits”. If you think she looks pretty, just blurt out “You look pretty”. Stop overthinking it, it doesn’t have to be smooth or perfectly worded – just blurt out whatever is in your head.
  • 99% of my compliments are just random shit I’m thinking right in that moment. “God you’re hot” or “You make my cock so hard” etc. I’m not good at compliments – I’m just very GENEROUS with my compliments and I’m constantly telling girls how much they’re turning me on, I say it during the entire time we’re having sex nonstop.
  • Sexual bucketlists. How to write, how to explore, etc.
  • How to get her to write her own and share with you.
  • Sexual bucketlists also make it a fun thing between the two of you, and helps with retention. Talk about my concept of building things.
  • Every week you get to tell her “This week we’ll try this next thing from the list”. It’s an exciting adventure for both of you, and again reinforces that concept of “building things”.
  • Magic wand as a cheat to give mind-blowing orgasms. When you use it you’ll just automatically pleasure every chick – it’s a cheat code.

Shownotes:

Magic Wand vibrator for crazy orgasms (affiliate link):

Bathmate dick pump:

https://killyourinnerloser.com/bathmate/

Foreplay guide:

https://killyourinnerloser.com/tinder-guide-4/#32-the-foreplay

Sex guide/talking dirty guide:

https://killyourinnerloser.com/tinder-guide-4/#33-the-sex

Performance anxiety guide:

https://killyourinnerloser.com/performance-anxiety/#solution-1-give-yourself-permission-to-not-have-sex

It’s “You and Me”, not “You vs Me”:

https://killyourinnerloser.com/you-and-me

How to write Sexual Bucketlists:

http://killyourinnerloser.com/sexual-bucketlist

Building things with girls:

https://killyourinnerloser.com/tinder-guide-5/#12-build-something-together

BDSM guides:

https://killyourinnerloser.com/category/sex-dating/bdsm/

Immy’s Thoughts on Being Alpha:

https://killyourinnerloser.com/on-being-alpha/

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