My story of ups & downs and the dark rabbit hole I'm recently falling into

It’s gonna be a lengthy one as I will note all the little details so maybe someone can draw a cause-and-effect relationship that I’m overseeing. It’s too much on my back so any kind of advice will greatly help.

22M/very good shape/very good diet/non-smoker

TL;DR:
Had a long-term relationship where sex was rare and felt like a chore. Struggled with condoms, overthinking, and performance anxiety, leading to little pleasure and never finishing. Recently started seeing someone new, but now I’m in my head even more. I get random boners all day but lose them the moment things get serious. The more I try to fix it, the worse it gets. Feeling lost and frustrated.


Full story:

My story starts in my teens. I could say I always had a way with girls, so I started dating fairly early (~14) and during that time I did everything with multiple girls but PiV. I was a little scared if I was too young to do all that, but it felt great and was a lot of fun. Never had any problems. At 16 I met the most beautiful and kind girl ever and we got together. However, she was very cautious/conservative person and I respected that it took her a lot of time to get ready for sex. A few months in we started with hands/mouth and everything was fine. About a year in she started feeling ready and wanted to have sex, but for some reason I was the one who was scared all of the sudden and I avoided it for months. When we finally made love, it was just kind of - unenjoyable.

I think there were multiple reasons for that:

  1. Condoms - oh boy how I hated those. I’m really big down there + uncircumcised so putting a regular condom on was a huuuuuge challenge. Also it was so tight it literally hurt me, but I thought that’s normal and just proceeded using such condoms (until recently, I will come back to this later). Just the thought of putting it on made me anxious, and there was a ~40% chance that it will just kill both my mood and boner and sex will fail. However, when I survived putting it on, I would mostly remain be able to have a good sex. At least for my gf, because the next point is:

  2. I just didn’t feel much of anything. I don’t know if it is psychological tho as I have noticed the same with blowjobs for me. Before it was by far my favorite thing, so hot and so enjoyable. However, I somehow made myself believe that I don’t feel anything, and when I start thinking about it I just get flaccid. There are days that I’m out of my mind when receiving a blowjob, and there are days where I don’t feel shit and just get soft. With real sex it was always very little feeling, but being aware of what I’m doing would make me horny enough to stay hard for a very long and have 45-min sex absolutely destroying her. However, it would end with me eventually getting soft and never once ejaculating from penetration with her in my life.

  3. I lied to her, a lot. And it made me feel terribly guilty. The thing is that she is obsessed about some things and fairly strict, and she was always telling that in her eyes masturbation is same as cheating. I masturbated since I was a kid, and I secretly always kept doing that. I wouldn’t call myself an excessive masturbator, but 3-5 times a week was probably my average. It was always enjoyable and stress relieving haha. I tried talking to her about it but I have seen that me telling her about it would be game over for us so my guilt just kept piling up.

This thing kept going on for years. Our relationship was pretty strong outside of that and she was very supportive so we just kept living our lives like that. I was seeing sex as a chore and a box that I have to tick here and there so I don’t feel bad about myself. I was avoiding it a lot. In total, we spent 6 years together and we maybe had sex for 30 times (I was living alone so we had a chance to do it every day).

I am a huge overthinker, so from the first time I was very concerned “is something wrong with me”. However, as a 17-18 year old you really don’t know anything, I was finding all the possible excuses for me and just continued being passive about it for years. I was more looking to confirm that “everything is fine with me” then I really wanted to enjoy sex. My gf and I broke up in one moment (it ended up being a few week “pause”) and during that time I had sex with another girl once and it was the only time in my life that I came during penetration and the sex was amazing. However, it was a relief for me that I was looking for and I got back with my gf because I really liked her on a human level. During the last few years of our relationship I was able to be hard and have sex as I was confident I’ll be able to do it, but it was just not that enjoyable.

The big part of it was also that I was starting to fall out of love, and few months ago I decided to break it off as I wanted to “heal myself” as I was frustrated because of years of not being able to enjoy sex I just felt so bad about it. Even while in relationship, I was always approached by so many girls and basically everyone around me thinks I’m an ultimate Casanova while in reality I’m a complete amateur who is totally unsatisfied sexually.

Honestly, I thought for years that my problem mostly lies in death grip + not being sexually attracted to my (now ex) gf. So first thing I did was I stopped watching porn and started using lube for masturbation. I never used it before because that would mean I would have to hide it from my ex gf. I also met one girl I was very attracted to, and we started seeing each other around a month ago. That’s where problems start.

First time we had sexy time everything was going flawless. I was rock hard, foreplay was amazing, her BJ skills were godlike. It was time for sex. I got up, took the condom from the drawer and went to put it on. It was a new package of brand I didn’t try before but size was “Plus”. Tightest shit ever, I tried putting it on and couldn’t, became soooooo frustrated and just gave up. Got soft and couldn’t get horny anymore. I thought it was a condom thing, and after so many years of dealing with that shit I ordered mysize condoms online. First of all as it may help someone, OH MY GOD IT IS SUCH A LIFECHANGER. Correctly sized condoms are supposed to be put on easily, and the difference is night and day. So I thought, problem solved.

We continued seeing each other almost daily, but all this was happening during our exam period which is incredibly stressful so we did not engage much in sexual activities. She would mostly come to my place to study, cuddle and talk. It was sweet, but I also felt like she was avoiding sex a bit since she was feeling bad about what happened before. I also did not force anything because I was too scared of failing again. Or better should I say, I would start teasing her and “asking for some” only when I was sure she will not give it to me. Also I was getting huge hard ons all the time randomly and they would last sooo long, but they didn’t result in anything. Until…

She visited me after my biggest exam (I just spent the whole night studying), was super stressed and just had a few pints of beer at the pub. I knew it is not a good time for any hanky panky but thought we will just chill as previous days. Got a random boner again, but this time she was into it. However, I just knew the things will go wrong and that’s how it ended up. She started going down on me, I felt like I don’t feel anything and boom it’s flaccid. I opened up to her and told her how I’m really stressed and anxious about all this and she was okay with it. We continued seeing each other but we didn’t engage sexually.
I also started to think and read a lot more about all this as I figured out I want to take the bull by the horns. However, I simply feel the more I think about it, the worse it gets. It sometimes seems to me the neglecting the problem was a way to go for me, but now I’m in too deep. I was too scared to even think of ED before, now I’m writing a long ass post about me here.

The reason is that the worst situation so far happened yesterday. It was the last day of the semester and since both of us are moving away after it, we knew we don’t know when we will see each other again. We decided to spend the whole day together, it was very nice and emotional but I knew we both want one thing to finally happen. I was looking forward to it for days, I constantly had random huge boners just from thinking about it. I was still scared but also I was hoping hard that yesterday was the day and “the curse will be lifted”. At one moment I got very horny and we got into it. The moment she puts my penis in her mouth, I start telling myself that I don’t feel anything and boom - hard on is gone. However, it became hard again the moment she stopped sucking it, and this time she wanted it inside. The moment I entered, I started thinking again that I don’t feel shit and boom - hard on is gone. I got so disappointed and frustrated that I’ve lost my complete focus and couldn’t rewire myself back in. She was trying for hours to play with it, asked to take a bath together etc. but the more she tried the more frustrated I was becoming as I have accepted a defeat and her trying something only made me feel worse because I knew I will eventually fail. Now I’m in such a bad place as I knew that was our last chance, I feel like I lost this girl and broke up with my ex because of the problem that only got worse without her. I have absolutely no idea how to fix this and become “normal” but it’s driving me insane.

Thanks for the read and any help is appreciated.

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Hey man. I read all of this. I’m a 35 year old guy who also dealt with this in my early twenties – it went away for a long time, but came back, so I researched it. I have been diagnosed with ADHD and anxiety. I wanted to reply because it reminded me of how I felt a long time ago.

Sex and arousal is actually about comfort. Look up the “thoughts - feeling - behavior” relationship from Cognitive Behavioral Therapy. Your thoughts are causing you to feel anxious and your body is no longer comfortable and aroused. Being touched is now something that is triggering those thoughts and your anxiety. This is tough, but it’s normal for a lot of people.

A woman pleasuring you with her hands, mouth, and vagina isn’t as immediately stimulating as your own hand – you’ve had years of practice! They’ll need some practice, too. What you can do to help them, and yourself, is this:

  1. Focus on the sensations and what feels good. Many sensations will be subtle, and the really powerful ones require you to be in an aroused state of mind and take time to build up to. The more you understand what feels good, the more you can communicate it to partners.
  2. There’s nothing wrong with you. Societal messages cause our anxiety about ourselves. Thinking like “why am I not rock hard while this beautiful woman is touching me” pulls you out of the moment, out of the sensations, and you’re no longer feeling comfortable.
  3. Be patient with yourself and your partners. It can take a long time to change how we feel in these situations based on new experiences.
  4. Be compassionate to yourself. Mis-sized condoms are frustrating! You were right to feel frustrated and lose the ability to feel aroused in those situations. Most people would have

The girl you hooked up with sounded patient and nice. I bet she had a good time cuddling and touching you. Its okay to be vulnerable with her about what you’re going through, too – maybe she’ll have some ideas, maybe not. She’s young too and trying to help a guy relax is probably a new experience for her as well. Don’t feel bad, she’ll encounter this with any partner she has in the future (unless you both get monogamously married forever – statistically unlikely but if so, congrats!)

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Also as a postscript, I also don’t feel much when a girl is gentle at the start of sex or foreplay. It’s not a mega powerful sensation, you know? Different story if it happens when I’m already aroused and stimulated for a while. I did used to lose my erections when I got anxious about that, now I just focus on the visual stimulation of how nice she looks or something else, instead of focusing on what my penis is doing at that moment

Wonderfully said!!!
I often wonder if I have a touch of ADHD or some other affliction that adds to my anxiety and is a boner killer….