Never been this far. How should I proceed?

[Batya33]

There's a simple short word when a person doesn't want to be sexual or would prefer to have a date in a public place. "No."

[Andrina]

Well, you're the one who signed up for this abnormal situation, and it remains abnormal. You've tried show and tell with zero improvement. You either wait 50 times longer than average for each baby step, hoping for the best and that she turns into an unselfish person, or quit now in frustration. Nobody else is living your life, so that's your decision to make.

[Wiseman2]

3 hours ago, iamwhatyoumademe1129 said:

 everytime I go to pick her up, she tells me to come inside her house. One thing leads to the other, and then we are naked for the rest of the day. 

If you feel this is teasing, stop doing it. You both seem inexperienced and she told you she doesn't want sex. Please understand "no" means "no", whether it's oral sex or intercourse. She's only willing to go so and so far. There's nothing abnormal about that for a conservative 20 year old virgin. 

This has nothing to do with making her orgasm. She's inexperienced. And she's a virgin. And she has already told you no to intercourse and oral.  Please stop hanging out nude and the heavy petting etc if you can't handle it. Please remember no one owes you sex. 

[lostandhurt]

I see a lot more frustration in your future.  It sounds like she is still learning what she likes and doesn't like and frankly she sounds a little uptight which makes it very hard to bring them to climax.

 It is good you want to bring her to orgasm but that shouldn't be your ultimate goal, your goal to give her pleasure and if she has an orgasm great but you aren't a failure if it doesn't happen. 

 As far as this 90% to 10% thing that is a very bad way of looking at the intimacy between you two.  First of all you both are very new to all this separately and together so relax and let it happen.  Just because you are good to go right now and know how to bring yourself to orgasm doesn't mean she does.  Does she touch herself? Has she ever had an orgasm?  Slow  way down and enjoy exploring intimacy as a couple.

  If you don't want to get naked and would rather go out for lunch of dinner or whatever make that clear.  "Come inside"  "Not right now, lets go have dinner and then we can have some fun inside"  You have a voice in all this too.

  There is no finish line you are racing too to take your time.

 Lost 

[iamwhatyoumademe1129]

On 1/2/2024 at 12:09 PM, lostandhurt said:

I see a lot more frustration in your future.  It sounds like she is still learning what she likes and doesn't like and frankly she sounds a little uptight which makes it very hard to bring them to climax.

 It is good you want to bring her to orgasm but that shouldn't be your ultimate goal, your goal to give her pleasure and if she has an orgasm great but you aren't a failure if it doesn't happen. 

 As far as this 90% to 10% thing that is a very bad way of looking at the intimacy between you two.  First of all you both are very new to all this separately and together so relax and let it happen.  Just because you are good to go right now and know how to bring yourself to orgasm doesn't mean she does.  Does she touch herself? Has she ever had an orgasm?  Slow  way down and enjoy exploring intimacy as a couple.

  If you don't want to get naked and would rather go out for lunch of dinner or whatever make that clear.  "Come inside"  "Not right now, lets go have dinner and then we can have some fun inside"  You have a voice in all this too.

  There is no finish line you are racing too to take your time.

 Lost 

Update. 

Relationship is good. Recently we started having sex. And that’s where the problem begins. We are each other’s first. Before we had PIV sex, we would kiss and do oral on each other. That was really good. Just by kissing me, she would get wet. First time we had sex, she was very horny as well. It was good, but neither of us finished. I thought it was the condom, so I changed brands. Over the last two weeks, we had sex three more times. But she said she was not as horny. I still can’t cum from sex. According to her, sex is good, but she is not as horny as she used to be a few weeks before. She was also on her period last week.

 

Also, we have sex in her house. And her family is there. So we always have to go slow and being careful with any noises. She gets kinda nervous when having sex with me in her house.

 

I can only cum when I masturbate. Normally I masturbate 3-4 times a day. Not being able to finish during sex is frustrating me a lot. Using a condom sucks. I can barely feel anything. And she does not want to use birth control. The thing is I have no problem ejaculating when I masturbate with a condom. I dont know why that happens.

 

Also, I have tried everything to make her cum, but without success. She said she has never finished. And she does not like to masturbate.

 

Lately that’s all we have been doing. Me going to her house, and us having sex. She has mentioned its been a while since we have gone on dates. When we first started dating, I would take her out a lot. But now not really.

[boltnrun]

Too much masturbation renders many people unable to orgasm via penetrative sex. That's because you've trained your body to climax by using your hand. A woman's vagina doesn't feel like your hand, so your body doesn't recognize it as a means to orgasm. 

Three to four times a day is excessive. You're going to have to cut way back if you want to orgasm via intercourse.

Why won't you take her out on dates anymore? Don't you like her? Do you find her embarrassing?

[iamwhatyoumademe1129]

8 minutes ago, boltnrun said:

Too much masturbation renders many people unable to orgasm via penetrative sex. That's because you've trained your body to climax by using your hand. A woman's vagina doesn't feel like your hand, so your body doesn't recognize it as a means to orgasm. 

Three to four times a day is excessive. You're going to have to cut way back if you want to orgasm via intercourse.

Why won't you take her out on dates anymore? Don't you like her? Do you find her embarrassing?

I see. Would two weeks of no masturbation make me ejaculate during sex? I am on my first day of no masturbation, and it's hard ngl. But I will do my best. I will also not bring up sex during those two weeks. I don't want her to think I only want to see her for sex. I need to control my self better. I get hard just by hugging her. 

I love her. I haven't taken her on dates because I have no idea where to take her. And it is very cold outside.  Next time we see each other I wanna take her to the museum. But other than that I got no idea. And I don't have a ton of money.

[Wiseman2]

46 minutes ago, iamwhatyoumademe1129 said:

 we have sex in her house. And her family is there. So we always have to go slow and being careful with any noises. She gets kinda nervous when having sex with me in her house. Using a condom sucks. I can barely feel anything. Lately that’s all we have been doing. Me going to her house, and us having sex. She has mentioned its been a while since we have gone on dates. 

Sorry this is happening. It sounds awful to just go to her house with her parents home have sex and never have dates. If you don't like condoms, that's unfortunate. 

[iamwhatyoumademe1129]

5 minutes ago, Wiseman2 said:

Sorry this is happening. It sounds awful to just go to her house with her parents home have sex and never have dates. If you don't like condoms, that's unfortunate. 

Appreciate the help.

[boltnrun]

1 hour ago, iamwhatyoumademe1129 said:

I see. Would two weeks of no masturbation make me ejaculate during sex? I am on my first day of no masturbation, and it's hard ngl. But I will do my best. I will also not bring up sex during those two weeks. I don't want her to think I only want to see her for sex. I need to control my self better. I get hard just by hugging her. 

I love her. I haven't taken her on dates because I have no idea where to take her. And it is very cold outside.  Next time we see each other I wanna take her to the museum. But other than that I got no idea. And I don't have a ton of money.

I have no idea of the time frame that will get you unused to your hand as a means to ejaculate. That might be something a medical professional might be able to answer. They could also help you with your excessive desire to masturbate multiple times per day. I mean, how to you have the time and opportunity? You don't work or go to school?

You don't need a "ton of money" to go out and do things like a walk in a park or at an indoor shopping center followed by a cup of tea or an ice cream. That would cost you about $10. The walk would be free. 

[lostandhurt]

Okay first off jerking off 4 times a day is excessive even for a teenager.  If you are masturbating to porn or even fantasizing it becomes your normal so the real thing will not do it for you.  This is pretty common and the cure is to totally stop.  No jerking off and no porn.  The only way is cold turkey but it won't be easy because you have turned it into a habit, breaking that habit will be tough but you can do it by staying busy and when you get the urge distract yourself with something else.  How long will it take?  As long as it takes till you are able to fully enjoy real life sex and reach orgasm.

 As for her I can see how being in her home and having to be careful and silent would keep her from reaching orgasm.  Many women cannot orgasm from sex alone so don't put pressure on her or yourself as it will only make things worse.  Definitely work something out so you can be really alone together and have fun.

 Leave yourself alone and you will be just fine

Lost