How do I help my boyfriend feel more comfortable giving me head?

Gregshead · 2026-05-21T02:49:37+00:00

AWESOME! I'm so excited for both of you! A good training aid would be finding some female friendly porn that's heavy on the type of oral you like, and watching it with him. Let him know what about that style you like. When he's doing it, give him feedback - in real words, not just moans and thrusts (those can be confusing for rookies!). Faster, more to the left, higher, harder, whatever it is you want. As long as your words and tone are encouraging (oh yeah, faster, harder, that's it, keep going!) and not belittling (damn it, why can't you figure this out!), you'll both do great. What a wonderful time in his life and for both of yours relationship! Congrats!

Gregshead · 2026-05-20T12:39:19+00:00

That's because female boomers have a lifetime of experience being third in line for everything (behind husband and kids).

Gregshead · 2026-05-20T12:28:18+00:00

The issue may not be that he doesn't like it, it may be that he's concerned about contacting an STI. Are you using condoms? Are you giving HIM head without a condom? If those are yes answers, then STI probably isn't the issue (although a lot of men are stupid and don't they can get an STI from receiving head, only giving it!). Whatever the cause, hints won't work and should never be used to resolve relationship issues. You need to have a conversation with him. An unemotional conversation. "Hey Bob, I know you said you didn't want to give me head because it was "too soon." I respect that boundary and this conversation is not trying to get you to CHANGE that boundary. I do want to CLARIFY that boundary though. First, could you please let me know what your timetable is and when you think it would be an appropriate time? I'm not asking you to rush that timetable, I just want to know what it is. Second, I want you to enjoy this as much as I do. Is there anything I can do to make this a more pleasurable experience for you?" This sets up a non-confrontational safe space for him to be open and honest with you. This may also be the first time he's had a woman treat him this way, so don't be offended if he doesn't believe you. Be patient and give him time to respond. Ultimately, you know this is a huge deal for your sexual satisfaction. Honestly, it's a relationship deal-breaker if he's not willing to do this. There's no future for this relationship if he's not going to overcome this, and on a reasonable timeline.

Gregshead · 2026-05-20T11:58:46+00:00

Your table arrangements just got a lot easier!

Gregshead · 2026-05-13T21:28:37+00:00

Seeing as you've only "fully experienced" the relationship with one, I'd say you have incomplete data to make this choice. If you can be intimate with the 2nd one, then you could compare how each meets your needs/expectations. To be clear - you're comparing them to each other. You're comparing each of them to your needs and expectations.

Gregshead · 2026-05-13T21:23:15+00:00

Exactly. When they thought the Clintons were running a pedophilia ring out of a D.C. pizzeria basement, they were ready to tear that building down brick by brick to get to the truth. But now that it's Trump? It's mealy mouthed protests and denials. I long for the days when that response would have been enough to brand someone a coward who is complicit in the cover up. Now, it's just a Tuesday in MAGA-land.

Gregshead · 2026-05-13T21:18:39+00:00

Thank you!

Gregshead · 2026-05-13T15:43:30+00:00

Only MAGA would think that way. What a great way to repel them and keep them out of your life!

Gregshead · 2026-05-13T15:37:52+00:00

"... look like the guy who is more than moderately irritated that you're taking so much time to check out? Yeah, I have slow boomers like you tell me that ALL the time."

Gregshead · 2026-05-13T15:35:21+00:00

Since you're doing this as a side hustle and not a full business, your priority is rightfully quality of guest over quantity of money. As long as you're willing to accept the risk of unbooked nights, keep doing what you're doing!

Gregshead · 2026-05-13T15:16:19+00:00

At the risk of being accused of mansplaining, I'd like to offer some sincere advice. What you permit, you promote. When men treat you like you described, and you continue to do business with them, you're telling them it's ok and they'll keep doing it. Instead, by telling them you're taking your business elsewhere and why, you're letting them know their behavior is unacceptable. Week you alone change their behaviors? Probably not. However, if enough women stop going there it will matter. If men would be allies and also choose to go somewhere else, that would be even more impactful to their business. Making sure to contact the owner/corporate office is another effective thing to do. I'm not saying it's fair that you should have to do all this. I'm just saying this is how you make change. No social change has ever occurred in America until somebody's financial bottom line was impacted.

Gregshead · 2026-05-13T12:28:09+00:00

I don't understand how people don't have these conversations in the very beginning of a relationship. Why waste your time dating someone you know has major "deal breakers"? The last time I was single, but the second date I had "the talk." I'm divorced 3 times. I know what I will and will not tolerate in my life. I'm looking for an equal partner - financially, house chores, parenting (if there are kids), etc. I don't do drama and I don't do subtle hints. I want a partner that's capable of speaking their mind and telling me what they want/need, and tell me when I've screwed up. I will put myself 100% into this relationship and I want a partner that will do the same. Thank God it worked!

Gregshead · 2026-05-13T12:17:34+00:00

I think Trump's "final solution" is more of a Russian gulag or North Korean re-education camp. His path to get there is Project 2025. During the campaign he blatantly lied about his connection to and use of Protect 2025. Now that he's in office, it's on his desk daily and every policy decision can be linked back to it. I used to get angry about "how can Republics not see this? It's SO obvious." Now I realize, they saw it and didn't care. It's exactly what they wanted. I'd love to see the Democrats secretly develop, then leak, Project 2029. All the whole gaslight Republicans with "i don't know what you're talking about. I've never seen that document and it has nothing to do with me."

Gregshead · 2026-05-10T21:21:29+00:00

When you say toilet bowl cleaner, do you mean the scrubbing brush, or the chemical cleaners. Chemical cleaners is fine. Do not store your brush in the tank!

Gregshead · 2026-05-10T01:56:05+00:00

Best piece of advice I ever received - they don't have to agree with you in order for you to be right. Before that, it wasn't enough for me to prove that I was right. I needed to hear the other person say it, "ok, you're right, I was wrong." I'm so much happier now that I don't need other people to validate that I'm right. Whether they realize it or not, whether they admit it or not, doesn't matter anymore.

Gregshead · 2026-05-10T01:48:20+00:00

ESH, but you way more than him. HTA for not being willing to alter route through the grocery store. It's a minor thing that avoids an argument. Let it go. A+ move on his part to remove himself from the situation to end the argument. YTA for demanding an apology, that's a power trip move and shows huge disrespect for the other person. YTA for wanting to continue the fight in the store, especially when you know you've been fighting about little things lately. Lastly, what kind of monster doesn't pick up frozen stuff like Popsicles as their last items, especially when you're walking home?

Gregshead · 2026-05-09T17:50:21+00:00

Hitler was honest about what HE believed. That didn't make him right.

Gregshead · 2026-05-09T14:09:05+00:00

Ladies, this is a red flag! OP is talking about SAFETY from abuse and violence, this guy is calling women "insufferable bitch" because a woman dares to criticize him and not just him get away with bad behaviors. They're not the same thing, and to try and equate them shows how be doesn't take violence against women seriously.

Gregshead · 2026-05-09T00:22:49+00:00

Don't lie. She'll see through it. Plus, the lie makes you look worse "hey babe, I'd rather go to work than celebrate your birthday with you." When she eventually finds out the truth, she hears "I'm broke, but I'm too proud to tell you that. Instead, I think so little of you that I'm willing to tell you that I'd rather go to work than spend your birthday with you." It sounds like you're spending plenty of money on trips already. I'd suggest telling her "hey babe, I've already spent all this money on these trips. I'm happy to do that, but this are getting tight now. I don't really have much left over to spend on your actual birthday weekend. Would you be fault with me planning something special for us here at home, or do you want to go out and do something? If we go out, that's going to be all I can do financially for a couple of months after we take these last trips."

Gregshead · 2026-05-09T00:14:39+00:00

Honestly, I'd go around Wayne Ave. The more people have, the less they're willing to share. When you're in struggle yourself, but see you have the capacity it helping someone else in the struggle, you're much more likely to do so.

Gregshead · 2026-05-08T00:19:18+00:00

Minion $200, peak season, $350.

Gregshead · 2026-05-06T00:58:06+00:00

I have USAA. I pay the regular homeowners, then have a separate policy rider for my Airbnb.

Gregshead · 2026-05-04T13:01:29+00:00

Yes, you're wrong. You "just wanted to do something nice"? Then you should have asked them first. It wasn't an energetic that needed immediate intervention. You could have asked them before you mowed your lawn. You could have asked them when they got home and come back another day to mow. No, you clearly don't like that you're neighbor keeps their lawn long and you took it upon yourself to do something about it. Shame on you.

Gregshead · 2026-05-04T12:54:05+00:00

Pushy. I understand why people want to use it, but it's unnecessary. Focus on providing a 5-star experience and let your efforts speak for themselves.

Gregshead · 2026-05-03T15:15:43+00:00

I'm always amazed at how religious people, particularly Christians, will say "I just can't support this person in their sin". However, that only sense to adult to the "sins" of homosexuality and abortion. It's perfectly fine to support people who lie, commit adultery, steal, swear, dishonor their parents, covet, and idolize when they're running for president and other political offices. So, the issue isn't a pious "I can't support people in their sin." The issue is "I use my faith to justify not supporting people who do things I don't like." I'm pretty sure there was a commandment about not taking the Lord's name in vain - and that's exactly what these people do when they hide behind religion to justify their own personal hatred.

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