Breakup has left me [26M] feeling incredibly insecure sexually /u/AltmanFromAltworld Sex

This’ll be a little long and detailed, I’ll TLDR the end but I appreciate anyone taking the time to read this.

I’m a 26 year old male who has had phimosis all my life, I’d only had penetrative sex a handful of times. I was with my partner Lucy [24F] for 5 years. My condition was never an issue for her and we got by on hands and oral sex.

My relationship with Lucy deteriorated due to both of us losing attraction, we didn’t have sexual interaction for around a year and a half before I called the relationship off as it became platonic.

I met Sarah [22F] after a few months, we had seen each other around for years and she admitted to having a massive crush, the relationship was very intense from her end but I quickly got feelings. Initially I wanted to take things slow sexually. But on our 4th time meeting, after a lot of tension and foreplay, I gave her head, it ended with her having a convulsing orgasm after a few minutes.

I hadn’t had anyone orgasm and shake that intensely before, she wasn’t overly loud but it was like she zoned out, eyes roll back type deal. It felt great. After she messaged me saying she had never experienced anything like it, I was skeptical because, come on surely someone has gone down on her before haha, but even if she just said it to make me feel good, she clearly enjoyed herself.

She wanted to pleasure me as well so upon the next meeting I told her about my condition. I felt safe doing so because she was an understanding and kind person, she took it well, asking how she could do things for me without hurting me. Over the next few weeks we continued giving each other oral.

She meant a lot to me and I didn’t want to deprive her of proper sex, I knew about a method which would possibly allow me to have penetrative sex.

The relationship deteriorated a little in other places, she became distant when we weren’t together and my anxious attachment flared, she also started getting bad anxiety and I could feel a bit of a wedge coming between us.

When we were in person it was fine and she was excited at the idea of having sex with me. I initiated the usual way, gave her some oral orgasms because I was a little worried I wouldn’t be up to scratch at normal sex, and I was right unfortunately. I lasted about 45 seconds in missionary, she told me it felt good but I could tell it wasn’t as pleasurable as my other methods, she took a moment of watching me and proceeded to call me perfect and compliment me, something she did a lot of, which made me feel better.

I apologized and said I’d improve as it was the first time in a long time. She assured me it was okay and we spent the rest of the night together, discussing the new possibilities of me being able to have sex.

The next day her anxiety kicked in badly, I misjudged how she felt and assumed there was an issue between us, from there on out it became hard to meet and she became distant, calling things off 5 days later. She gave me the it’s definitely a me problem and not you, but wouldn’t give me further clarity.

Not knowing the reason has caused me to theorise many things and made me incredibly insecure about my sexual ability. I know it’s likely to do with other things but the fact it happened so soon after sex has left me feeling a bit disillusioned, like if I had been better maybe things would have been different.

I’m at the point of not wanting to pursue a new relationship out of the fear that my inexperience at 26 will cause issues. I’m not the type of person to have one night stands, I have to form a connection to be with someone. I’m scared that I wasted too much time not fixing my condition and that I’ve fallen so far behind that I can’t fulfill a partner, oral and hands can only get me so far.

TLDR: I have phimosis and haven’t had penetrative sex for years, after positive oral sexual interactions with my GF, I gave it a go and wasn’t good. The relationship ended the next week for likely unrelated reasons, but it has caused me to be insecure about my sexual ability.

This’ll be a little long and detailed, I’ll TLDR the end but I appreciate anyone taking the time to read this.

I’m a 26 year old male who has had phimosis all my life, I’d only had penetrative sex a handful of times. I was with my partner Lucy [24F] for 5 years. My condition was never an issue for her and we got by on hands and oral sex.

My relationship with Lucy deteriorated due to both of us losing attraction, we didn’t have sexual interaction for around a year and a half before I called the relationship off as it became platonic.

I met Sarah [22F] after a few months, we had seen each other around for years and she admitted to having a massive crush, the relationship was very intense from her end but I quickly got feelings. Initially I wanted to take things slow sexually. But on our 4th time meeting, after a lot of tension and foreplay, I gave her head, it ended with her having a convulsing orgasm after a few minutes.

I hadn’t had anyone orgasm and shake that intensely before, she wasn’t overly loud but it was like she zoned out, eyes roll back type deal. It felt great. After she messaged me saying she had never experienced anything like it, I was skeptical because, come on surely someone has gone down on her before haha, but even if she just said it to make me feel good, she clearly enjoyed herself.

She wanted to pleasure me as well so upon the next meeting I told her about my condition. I felt safe doing so because she was an understanding and kind person, she took it well, asking how she could do things for me without hurting me. Over the next few weeks we continued giving each other oral.

She meant a lot to me and I didn’t want to deprive her of proper sex, I knew about a method which would possibly allow me to have penetrative sex.

The relationship deteriorated a little in other places, she became distant when we weren’t together and my anxious attachment flared, she also started getting bad anxiety and I could feel a bit of a wedge coming between us.

When we were in person it was fine and she was excited at the idea of having sex with me. I initiated the usual way, gave her some oral orgasms because I was a little worried I wouldn’t be up to scratch at normal sex, and I was right unfortunately. I lasted about 45 seconds in missionary, she told me it felt good but I could tell it wasn’t as pleasurable as my other methods, she took a moment of watching me and proceeded to call me perfect and compliment me, something she did a lot of, which made me feel better.

I apologized and said I’d improve as it was the first time in a long time. She assured me it was okay and we spent the rest of the night together, discussing the new possibilities of me being able to have sex.

The next day her anxiety kicked in badly, I misjudged how she felt and assumed there was an issue between us, from there on out it became hard to meet and she became distant, calling things off 5 days later. She gave me the it’s definitely a me problem and not you, but wouldn’t give me further clarity.

Not knowing the reason has caused me to theorise many things and made me incredibly insecure about my sexual ability. I know it’s likely to do with other things but the fact it happened so soon after sex has left me feeling a bit disillusioned, like if I had been better maybe things would have been different.

I’m at the point of not wanting to pursue a new relationship out of the fear that my inexperience at 26 will cause issues. I’m not the type of person to have one night stands, I have to form a connection to be with someone. I’m scared that I wasted too much time not fixing my condition and that I’ve fallen so far behind that I can’t fulfill a partner, oral and hands can only get me so far.

TLDR: I have phimosis and haven’t had penetrative sex for years, after positive oral sexual interactions with my GF, I gave it a go and wasn’t good. The relationship ended the next week for likely unrelated reasons, but it has caused me to be insecure about my sexual ability.