Nervous to start having sex again, Any Advice?

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Let's just say I'm not exactly the most experienced person when it comes to sex, I've been with both men and women but men more, I'd class myself as a bottom as I enjoy it more than topping! Anyway, I've bottomed 4 times with different guys, my first time barely felt anything, some intense sharp pains but the guy was pretty respectful it being my first time, the second time I enjoyed pretty well, the guy was very well endowed but very obviously knew what he was doing, third time was pretty painful even tho the guy had a average dick size he plowed away and me being quite a shy guy I just took it and not long ago I met a guy who was pretty well endowed again and he kinda shoved it in brutally. I've recently joined Grindr again as I've been wanting to jump back into it as my situation is better now and I have my own place and it's so much easier to meet guys and have a place to meet but now I'm nervous too, what happens is I plan a meet but before we can confirm I get too nervous and wonder if I want to do it, I ultimately don't go through with the meet. I wouldn't say I'm scared too meet and I'm not sure why the hesitation but there's something stopping me and I'm not sure what it is, Has anyone got any advice on why this is happening? if you've been through the same thing or have any advice on what I should do?
 
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I would go with my instinct. There's a reason why you're not going through with it and rightly so.

Something is keeping you from going through with it. Could be that it's what's keeping you safe? Bringing a complete stranger into your home is never a good idea on so many levels. Not only do you not know anything about them, but now they know where you live.
There are some strange people in society, not all with good intentions. Better to err on the side of safety. I'd thick twice before I let a complete stranger in my home for 15 minutes of gratification.

Listen to why you are not going through with these meet ups. It may just save you from heartache in the future. Just my two cents worth.
 
Nothing wrong with a bit of caution. If you are going to entertain bringing a man into your home, please at least speak on the phone with him first. As @Gj816 pointed out, "not all with good intentions" is spot on. Meet and get a vibe perhaps at a coffee house or outside in a safe spot (i.e., not in the woods or in some alley).

Years ago I let a guy come to my home and he was totally wacked out on crack. He was paranoid and was looking under the bed, in the closets, and other places because he thought somebody was there. What a nutcase. I got him out of the house and never made that mistake again of letting a stranger just show up at my place.

As far as being on the bottom of things, you need to be upfront before you actually get down to it that you need to get used to his dick inside you before he can start plowing your ass. It takes a minute to get used to him if he has some girth. You already know that every top dude is not the same. Enjoy it though, but make sure you interact with the guy in person if you can before he comes to your home. (just my 2 cents worth)
 
I always meet a guy for a drink before I invite him to my hotel. Chatting on line is one thing but talking in person helps me determine if I want to take his cock or not. Even then they can change once the clothes come off
 
Get tested so you know your STI status.
Stock up on condoms, lube and other accessories like lube injectors & enema kits. Massage oil? Sure.

Always meet somewhere neutral first. Relax and enjoy his company. Meeting in person is half the battle except it's not a battle--you're both in it to hook up. :)
 
I'm certain if the guy you meet can't go a video chat first... That's a sign it won't work out. In this age of technology there's no excuse. Even if it's for a few minutes. It's amazing the vibe you can pick up from seeing them talk live online. Heck, maybe even an online jerk session if time or location allows... Also weeds out the "driving to a neutral location for nothing first" issue (though I'd still meet at a neutral location first even AFTER the Zoom, Skype, or Snap call regardless).

Also, I'm no expert on this (at all). But those profiles of "...don't wast my time...", "... no back and forth..." are red flags in my book. Let them know your reservations up front.
 
I had this exact same thing happen to me from a 9” guy who just shoved in, no lube and powered to finish. It hurt and actually caused damage to my hole.

Soon after I started having regular sex with an average sized guy and it still hurt, to the point I was never enjoying it and we stopped doing anal.

For two years after that, I felt unsure if I ever wanted to, or even dared to have sex again, with anyone. That I’d always feel the pain and never the joys of sex. My sexual confidence was gone. I had a few blowies and wank sessions, but would stop meeting guys whenever they wanted to top.

I tried using average sized dildos to see if it would ease the tightness, but because they are a lot more solid than a hard cock, I couldn’t tell if it was better, or felt like that because of the texture.


Eventually I met a guy I really liked, and he was above average (not quite 9”) and I was terrified. What if it always hurt? What if we could never have sex. And after I told him, he was so understanding and only ever did anything I was comfortable with. And when we did finally have sex for the first time, because he knew what I had gone through and how it felt, he was so patient, so gentle and made tue whole thing so pleasurable for us both. It was still so tight, but he was so great.

I learnt from it all, that yeah, take your time, and ease yourself back into it with someone who knows what’s happened before and will be gentle with you and help you with your sexual confidence.
 
I had this exact same thing happen to me from a 9” guy who just shoved in, no lube and powered to finish. It hurt and actually caused damage to my hole.

Soon after I started having regular sex with an average sized guy and it still hurt, to the point I was never enjoying it and we stopped doing anal.

For two years after that, I felt unsure if I ever wanted to, or even dared to have sex again, with anyone. That I’d always feel the pain and never the joys of sex. My sexual confidence was gone. I had a few blowies and wank sessions, but would stop meeting guys whenever they wanted to top.

I tried using average sized dildos to see if it would ease the tightness, but because they are a lot more solid than a hard cock, I couldn’t tell if it was better, or felt like that because of the texture.


Eventually I met a guy I really liked, and he was above average (not quite 9”) and I was terrified. What if it always hurt? What if we could never have sex. And after I told him, he was so understanding and only ever did anything I was comfortable with. And when we did finally have sex for the first time, because he knew what I had gone through and how it felt, he was so patient, so gentle and made tue whole thing so pleasurable for us both. It was still so tight, but he was so great.

I learnt from it all, that yeah, take your time, and ease yourself back into it with someone who knows what’s happened before and will be gentle with you and help you with your sexual confidence.
This sounds exactly like what happened to me, I think the experience has scared me and now I’m nervous to have sex again, but I feel like I’m wasting the guys time if I invite someone round for bjs cause I know a lot of guys can’t cum from a bj so that’s maybe why I keep backing out. The thing is I’m wanting to meet someone again, I’m always safe and I’m always upfront on what I’m ok to do but some guys like to be dominant and I’m like a shy guy but I’m always willing to let them know what I’m uncomfortable with.
 
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This sounds exactly like what happened to me, I think the experience has scared me and now I’m nervous to have sex again, but I feel like I’m wasting the guys time if I invite someone round for bjs cause I know a lot of guys can’t cum from a bj so that’s maybe why I keep backing out. The thing is I’m wanting to meet someone again, I’m always safe and I’m always upfront on what I’m ok to do but some guys like to be dominant and I’m like a shy guy but I’m always willing to let them know what I’m uncomfortable with.
Mate, I honestly understand this so well. At my lowest I thought that I would never be confident enough to have sex again.

I ended up deciding I had to turn it around and find a way to get over it, even if it took a while. So, when on Grindr (I know not the best way of meeting someone who might be able to help) it became the answer to the usual question “what you looking for?” I was totally honest about what had happened and how it was affecting me and the conversation afterwards tended to show who was sympathetic and understanding, and who was just after a quick fuck.
 
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You have to make sure that the guy about to fuck your asshole knows that if you say no you mean it.
I was fucked standing up by a guy with an average length but extra girth and he split my ass. The more I said no the harder he pushed, pressing me into the underside of the bridge where we did it. I ended up in hospital?
It took a long time before I offered my manhole to a guy again. I did, and enjoyed it, but the time I'd spent topping had made me more aware of what a good fuck is.
Likewise meeting new guys you've met on the net, make sure it's in a "safe" place and public for the first time, give yourself the chance to say NO.
 
I did have one guy who wouldn’t stop. He was a lot bigger than me and I was on my stomach. Definitely a painful experience. The worst part is he is my friends neighbor. It took me a while to trust someone after that.
I defiantly think this maybe the issue is the fact I think I realised in my moment is that this guy has no respect for me and the fact he just shoved it in when I told him it’d be awhile for me, I lost my ability to trust. This seems like my issue, cause don’t get me wrong I enjoy talking to lads but the moment the issue of us meeting comes up I’m making excuses and not wanting to meet.
 
Grindr wise, as long as you communicate everything and don't ghost anybody, the guy should understand any hesitations however everyone is on Grindr because they most likely want to hook up when they are on.

Sex wise, For me, positions are super important, I think more important then dick size sometimes. I personally can take a dick all day if I'm riding the guy when he's on his back. If I go on my feet from riding, then it becomes uncomfortable and much harder to take a dick. Same thing with getting fucked from behind (probably because it's similar positions, different angles). I would say start out slow, little bit of light fingering, start out riding, just sit on it, do some foreplay, keep yourself lubed up until you open up then ride it til your comfortable before letting him take over. See if you prefer spit over lubricant and what else helps.

After you're comfortable enough, flip over on your back and see how that works. I would not reccomend starting out on your back. To me the hardest positions are from behind and on my stomach. When I really want to get fucked I will do these and just get through the rough parts. When you're on your back, you can still be in control with your hips if it starts getting uncomfortable. Maybe you can take dick from all angles (and I will continue to be jealous) and you just have to be safe and try out everything.
 
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