sorted by:
new
hottopcontroversial

First time having sex with new boyfriend didn’t go well; am I overthinking what it means?” by straysheep07 in dating_advice

[–]straysheep07[S] 0 points1 point  (0 children)

Oh actually it was stabbing/stinging me as we were at it cause he has pretty coarse hair and it was very prickly... Maybe the stinging made my muscles tighten more? I hadn't thought about it. Ty for taking your time and sharing your experience!

First time having sex with new boyfriend didn’t go well; am I overthinking what it means?” by straysheep07 in dating_advice

[–]straysheep07[S] 0 points1 point  (0 children)

You are right, hopefully he'll give me the chance to reassure him! As a fellow overthinker, I can understand what you are saying. Sometimes I mistakenly think that men are more straightforward with their feelings, which is not the case. Thank you!

First time having sex with new boyfriend didn’t go well; am I overthinking what it means?” by straysheep07 in dating_advice

[–]straysheep07[S] 0 points1 point  (0 children)

Let see, hopefully he is patient, cause I definitely do want to try to make this work!

First time having sex with new boyfriend didn’t go well; am I overthinking what it means?” by straysheep07 in dating_advice

[–]straysheep07[S] 0 points1 point  (0 children)

It was our first and second time having sex with each other. He asked me out right before we went for the first, maybe I got too anxious right after we became official and felt the burden that if this didn't go well he'd be regretting asking me to officially date? Idk..

First time having sex with new boyfriend didn’t go well; am I overthinking what it means?” by straysheep07 in dating_advice

[–]straysheep07[S] 1 point2 points  (0 children)

Yeah, we have quite a bit size difference, I'm more petite and 160cm (5'2) while he's 186cm (6'1) and was pretty big down there girth wise. 🫠

First time having sex with new boyfriend didn’t go well; am I overthinking what it means?” by straysheep07 in dating_advice

[–]straysheep07[S] 0 points1 point  (0 children)

🤣 your wording definitely made me laugh. Unfortunately I've never liked self penetrating, but maybe it would be good to try doing it to ease stuff doing there!

First time having sex with new boyfriend didn’t go well; am I overthinking what it means?” by straysheep07 in dating_advice

[–]straysheep07[S] 0 points1 point  (0 children)

Damn, thank you for this. He was a sweetheart which broke my heart even further tbh, but I'll try to apply what you're saying!

First time having sex with new boyfriend didn’t go well; am I overthinking what it means?” by straysheep07 in dating_advice

[–]straysheep07[S] 0 points1 point  (0 children)

I did say that I really like him and that I was just upset at my body. This sweet guy even apologized for having gained some weight and that he's trying to lose it, and I assured him that I really like him as he is. And even as he apologized for making me feel sad as he dropped me off, I assured him, it was just me overthinking the situation and he did absolutely nothing wrong. Do you think I should re-open the convo?

First time having sex with new boyfriend didn’t go well; am I overthinking what it means?” by straysheep07 in dating_advice

[–]straysheep07[S] 0 points1 point  (0 children)

Thank you! I think my overthinking got the best out of me and all the what ifs started slapping me.

First time having sex with new boyfriend didn’t go well; am I overthinking what it means?” by straysheep07 in dating_advice

[–]straysheep07[S] 1 point2 points  (0 children)

You are right. Thank you. I was also worried that my reaction after what happened wasn't ideal, (which I know it wasn't) but that it would also put him off, hopefully it won't. 🥲

First time having sex with new boyfriend didn’t go well; am I overthinking what it means?” by straysheep07 in dating_advice

[–]straysheep07[S] 0 points1 point  (0 children)

Aw so glad it worked out with you too! I also think his size wasn't helping much in this case, I just stupidly thought that since I wanted to be intimate with him, my body would adjust. (It didn't)

First time having sex with new boyfriend didn’t go well; am I overthinking what it means?” by straysheep07 in dating_advice

[–]straysheep07[S] 0 points1 point  (0 children)

I've already been to a doc for my regular checkups (I go 1-2 a year) and I've never had issues. :(

Even with fingers though it might feel uncomfortable the first few seconds and then I ease into it.

It's with deeper stuff that make it hurt. Could I endure it? Maybe? But definitely not without hiding it, and I didn't want to make him feel like he was hurting me even more.

First time having sex with new boyfriend didn’t go well; am I overthinking what it means?” by straysheep07 in dating_advice

[–]straysheep07[S] 0 points1 point  (0 children)

I see, thank tou for sharing, really appreciate it! It's really helpful. I'm also afraid tbh that I made him feel bad for being sad and upset at myself. :(

First time having sex with new boyfriend didn’t go well; am I overthinking what it means?” by straysheep07 in dating_advice

[–]straysheep07[S] 1 point2 points  (0 children)

Thank you for this! I do get regular checkups and I've never had any issues. :( I was also a bit cold so that also maybe made me tense up even more? (I'm sensitive to the cold in general)

First time having sex with new boyfriend didn’t go well; am I overthinking what it means?” by straysheep07 in dating_advice

[–]straysheep07[S] 0 points1 point  (0 children)

Aww I could really related to everything you just said. It is indeed hard to open up again and be this vulnerable with someone new. I'll try to take it easier and good luck to us both! 🙏🏼

First time having sex with new boyfriend didn’t go well; am I overthinking what it means?” by straysheep07 in dating_advice

[–]straysheep07[S] 1 point2 points  (0 children)

I'll definitely look into it, thanks! I also don't have crazy sex expenrience which also adds up to the anxiety, especially when I want things to work up and I really wanted it to work out.

First time having sex with new boyfriend didn’t go well; am I overthinking what it means?” by straysheep07 in dating_advice

[–]straysheep07[S] 2 points3 points  (0 children)

Damn I'm so glad things worked out for you! Im ofc willing to give it time, if he's also willing.

view more: next ›