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So for anyone who wasn't following my original post, here it is:

So I actually do really like this guy. I think he's really nice and genuine from what I know of him so far. We also do have a few things in common, even though it may not seem like it from the outset.

We messaged each other every day and on our third in person date I came to his place for dinner. He cooked dinner for me and we had a few alcoholic drinks and watched a movie. I was actually feeling kinda drunk and got my confidence up and I really wanted to kiss him. I started cuddling up to him and holding his hand and stuff. He said he'd been trying to be respectful and not come on to me or anything and just spend time together.

I kissed him but he seemed very inexperienced and not very good at it. Anyway we ended up fooling around a bit but really all it was I took my top off for a bit and we just kissed and cuddled. I asked him if he'd had sex before and he actually said that he hadn't. Then he said we're both drunk so let's not do anything sexual while we're drunk.

Afterwards he messaged me every day again. Three days later I came over to his place again and we got Uber Eats and watched some anime. I want to point out also that both times he had a hard on literally all night and I think it was bothering him but I wasn't sure what to do about it. I mean he was right that we were drunk the first time and probably wasn't good to have that as his first time.

So it was last night we were watching anime and then I stayed the night. We cuddled in bed a lot and it was really nice. We discussed about having sex and he basically said he wanted to but I'd need to take charge. The thing is I've actually developed feelings for this guy and I think about him a lot. I feel a bit silly because every time I think of him I get butterflies and just feel like my heart is going to jump out of my chest. So feel more like an infatuated teenager even though I'm 36 lol

The thing was when he said he was up for having sex, I felt ridiculously nervous and kind of just froze. It's not because I'm not experienced at sex, in fact it's very much the opposite lol I lost my virginity when I was 17-18 and since then I've done a lot sexually since then. It's just that I've never actually been with anyone in their 30's who has no dating or sexual experience. He hasn't put any pressure on me actually but I think I'm putting pressure on myself to make his first time amazing, you know? I also understand he might think it's great and just be happy to have sex for the first time. And of course he'd have nothing to compare it to lol Oh yeah and we also discussed that we both want a relationship and we want to date each other.

What I'm thinking though is, should I make his first time really special or should I actually try not to make a really huge deal of it? Like, should we go out for a nice dinner or something and then I can set up scented candles in the bedroom and stuff like that? Or should I not go all out like that and just do it? Or do I just ask him what he wants? I don't know why I'm feeling so nervous but this is a very big deal for me lol The only time I slept with someone who was a virgin was when I was a virgin myself too and just one other time when I was nineteen and this guy was twenty four and a virgin. But he wasn't really my boyfriend or anything and this was a very long time ago. 

Men, if you were (or are) a virgin would you want to make a big thing of your first time or would that make you feel more nervous?

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1 hour ago, Tinydance said:

 

 I was actually feeling kinda drunk and got my confidence up and I really wanted to kiss him. I started cuddling up to him and holding his hand and stuff. He said he'd been trying to be respectful and not come on to me or anything and just spend time together.

I kissed him but he seemed very inexperienced and not very good at it. Anyway we ended up fooling around a bit but really all it was I took my top off for a bit and we just kissed and cuddled. I asked him if he'd had sex before and he actually said that he hadn't. Then he said we're both drunk so let's not do anything sexual while we're drunk.

I dunno, but when reading the above (to me) it sounds like you're coming on a bit too strong for this guy. Too pushy maybe? Too soon (for him)? I agree with him that being drunk for the first time is not a good idea.  Sounds like he had his head on straight.

Why not slow down and just enjoy his company like he indicated he wanted to do?  You seem a little too eager for sex to soon.  Get to know this guy more, when sober - give it time.  You don't want to come on too strong, too soon, and put him off and chase him away. Don't shoot yourself in the foot.

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2 minutes ago, Capricorn3 said:

I dunno, but when reading the above (to me) it sounds like you're coming on a bit too strong for this guy. Too pushy maybe? Too soon (for him)? I agree with him that being drunk for the first time is not a good idea.  Sounds like he had his head on straight.

Why not slow down and just enjoy his company like he indicated he wanted to do?  You seem a little too eager for sex to soon.  Get to know this guy more, when sober - give it time.  You don't want to come on too strong, too soon, and put him off and chase him away. Don't shoot yourself in the foot.

No you are right and actually I felt really bad and I apologised to him afterwards about my drunken behaviour. I didn't start actually doing sexual things but I took my top off because he asked me if I wanted to relax in his t-shirt just around the house and I changed into the t-shirt. But I took off my top and bra for that and I just cuddled with him. And we kissed and held hands and stuff. But all this was initiated by me you're right.

I don't have to have sex yet and I don't actually care if I do it now or not. I mean I'm not a virgin so I'm fine lol I guess what I was trying to say is I'm feeling stressed because he expressed he would be up for having sex but to me it seems like a very big deal. I did discuss it with him and suggested we wait a bit more.

I also think it's OK to kiss and cuddle and fool around maybe a little because keeping in mind he hasn't really done anything sexual. So I think to go from zero to full on sex may be a lot. 

But just to return to my original question, if we decide to have sex should I make a big thing of it or not? Like should I do something special for it?

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Okay I am a guy so I will tell you straight.

Don't make it a big deal.  The bigger you make it the more nervous he will be about not knowing what to do.

Keep it simple, nice and slow and make sure you communicate.  Is oral on the table?  Never to early to learn right?  Maybe the next time you are over...

Guide him.  Guide his hands and his other part too 🙂

Be prepared for him not to last very long.  If he doesn't don't worry he will probably be ready to go again in less than a half hour. 

He is going to worry he will not satisfy you so let him know that learning what each other enjoys is all part of the fun.

 Lastly I don't think you were pushy.  He is a guy with a boner, you pretty much know what he is thinking right there.  He has waited a long time for what ever reason so just tell him when he is ready you are.

Oh and teach the guy how to kiss, you will be doing yourself a huge favor.

Have fun and relax.  I am happy you met someone that gives you butterflies

Lost

PS  You are the something special, he doesn't need anything else.

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2 hours ago, Tinydance said:

Like, should we go out for a nice dinner or something and then I can set up scented candles in the bedroom and stuff like that?

This is what women want. I doubt a guy cares about scented candles in the bedroom for his first time. 

I would nix all of that, as it puts too much pressure on the situation and is likely to make him more nervous. Relax and go with the flow, and don't schedule a specific day/date for his first time. That's not very natural. He'll do it when he's ready, and it would be better if you didn't try to make a big deal out of it. 

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I once was in his position, about 29 when I lost my virginity soo here's my two cents.

I felt really awkward about being a late bloomer, so we decided to take a day together to hang out. Prior to the big date (un planned conclusion) we chatted a lot, and she asked a few questions about things that turned me on. We started out and slowly escalated, we had other things to do through out the day. I was beginning to feel my oats and took a bit of charge, when I wasn't sure she guided me. It was an amazing night.

So I would say ask a few leading flirty questions from time to time. Ask if him about his turn ons, see if that's something you like too. When you two are ready be reassuring, take charge when he isn't sure. Down play if you have a bland experience, boost his confidence a bit. But most importantly work on the relationship, that for me was the best part. This will be his first time getting hit with those bonding hormones, so consider that in post fun times.

Sounds like you are onto someone good, best of luck!

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I may sound like a perv but I don't care: virgins (men) are the best. 

Okay first of all, it's not a big deal - it's a good thing. Don't act like it's a big deal, don't try to make it "momentous", just enjoy it. By all means, direct him in the act to show him what you like - but you should be doing that with every new guy in a relationship anyway. 

But here's why it's great: he's basically a blank slate. This is your time to show him what you like in kissing, foreplay, sex, etc. He doesn't have experience before that has tainted him or patterns that he's stuck in. 

Male virginity is awesome. Enjoy it. 

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24 minutes ago, Fudgie said:

Dude, it's true! If a guy is a virgin, that's a plus in my book. I'd rather a guy be a virgin than have a sordid sexual history with Lord knows what. 

I believe you, it was your wording that I found funny 🙂

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I mean I'd have sex just like you normally would but definitely sober and when you're both comfortable.  I've been in that situation - both when I was and when the guy was.  And each time it was once we were committed, in love, marriage potential.  That's why it was special.  But that's just me -and was just who we were - if you like having sex and he likes having sex in this kind of situation -meaning early on - then go for it.  You're both consenting adults.  Don't overthink it.

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15 hours ago, Tinydance said:

Or should I not go all out like that and just do it? Or do I just ask him what he wants?

I sort of have to smile, Tiny. L. 

I wouldn't know what to say to you in this case. Never met or been with a virgin man in my life lol.  Don't think I would want to either!  But, beside the point as I am married.

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11 minutes ago, boltnrun said:

I was 19 and my boyfriend was 20. He was a virgin. We just did it when we felt like it. He was delighted! 

Please do curb the drinking, however. It's a crutch. Plus, you want him to remember his first time, right?

It's true. I would curb the drinking before his first time, 2 drinks per person max. A little buzzed is fine but you don't want more than that. Keep in mind too that for many guys, whiskey d___k (ED brought on by alchohol intoxication) is a very real thing, especially in cases like these, where it's his first time.

The experience of deflowering awkward, nerdy virgin guys who are a bit on the "older" end and are all sorts of worried about it, needing a dominant woman to guide them a little is the best. I'm honestly jealous, haha 😃

Yes, I know how weird/creepy I sound, I don't even care! Haha

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6 hours ago, LaHermes said:

I sort of have to smile, Tiny. L. 

I wouldn't know what to say to you in this case. Never met or been with a virgin man in my life lol.  Don't think I would want to either!  

I was with a virgin once but he was 19, not 30+.  I wasn't that far out of virginity myself at that point, maybe a year or so.  I feel like something is off when a man of that age is a virgin and seems in no hurry to change that.  Is he maybe one of those "wait til marriage" (nothing wrong with that) people and just isn't telling you? 

I knew a woman who didn't lose her virginity til her mid-40s.  She was gorgeous, but she had so many sex hang-ups that most men ended up running away screaming.  Anyone who is into adulthood and who is a virgin, I'd want more information before I go there.

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It seems to me that any man wants not to screw up in bed. And he wants to give the girl maximum pleasure. This guy's intentions are commendable and understandable. The only thing you can do on your part is to talk to him, discuss your future sex - what he expects from it and what you expect. During sex, you could teach him, say how you like, and so on. I think he will appreciate it and will gain experience over time. Good luck to both of you!

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12 hours ago, waffle said:

I was with a virgin once but he was 19, not 30+.  I wasn't that far out of virginity myself at that point, maybe a year or so.  I feel like something is off when a man of that age is a virgin and seems in no hurry to change that.  Is he maybe one of those "wait til marriage" (nothing wrong with that) people and just isn't telling you? 

I knew a woman who didn't lose her virginity til her mid-40s.  She was gorgeous, but she had so many sex hang-ups that most men ended up running away screaming.  Anyone who is into adulthood and who is a virgin, I'd want more information before I go there.

So if he is willing to do sexual things with her and talking about sex it's not a wait till marriage -I mean she seems awesome but I doubt he'd do such an about face. I was a wait till marriage and I changed my mind -but I was 24, had dated/had relationships/been engaged and was in love and did think I might marry the guy - but I changed my mind because I just knew I didn't want to wait in general and I was in a serious relationship. Also he's never dated - so that's also not consistent with a religious wait till marriage- often they at least date within the confines of the arranged dating situation.

(My bf at the time was not virgin - he was also same age and had been with very few - and as it turned out -not sure if this is related -he's been happily partnered for over 20 years with a man -now his husband). 

 

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On 6/23/2021 at 2:03 PM, lostandhurt said:

Okay I am a guy so I will tell you straight.

Don't make it a big deal.  The bigger you make it the more nervous he will be about not knowing what to do.

Keep it simple, nice and slow and make sure you communicate.  Is oral on the table?  Never to early to learn right?  Maybe the next time you are over...

Guide him.  Guide his hands and his other part too 🙂

Be prepared for him not to last very long.  If he doesn't don't worry he will probably be ready to go again in less than a half hour. 

He is going to worry he will not satisfy you so let him know that learning what each other enjoys is all part of the fun.

 Lastly I don't think you were pushy.  He is a guy with a boner, you pretty much know what he is thinking right there.  He has waited a long time for what ever reason so just tell him when he is ready you are.

Oh and teach the guy how to kiss, you will be doing yourself a huge favor.

Have fun and relax.  I am happy you met someone that gives you butterflies

Lost

PS  You are the something special, he doesn't need anything else.

Awww thanks Lost! What wonderful advice! Well this Saturday I suggested we play some indoor mini golf. It's winter in Australia so very cold outside in my city lol Afterwards we said I'll stay over at his place and we'll cook dinner and watch this anime show we're watching. I heeded your advice about not doing anything over the top special but I thought doing something fun and going out first might help us both relax. He told me before he likes mini golf and this is a themed mini golf so should be good. I'm not going to make a big deal about anything and probably just see what happens when we're cuddling and watching anime and stuff.

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On 6/23/2021 at 2:32 PM, MissCanuck said:

This is what women want. I doubt a guy cares about scented candles in the bedroom for his first time. 

I would nix all of that, as it puts too much pressure on the situation and is likely to make him more nervous. Relax and go with the flow, and don't schedule a specific day/date for his first time. That's not very natural. He'll do it when he's ready, and it would be better if you didn't try to make a big deal out of it. 

Yes very good point! I mean, I kinda want scented candles for myself but I also don't want to be cheesy lol I won't sprinkle the bed with rose petals don't worry lol

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On 6/23/2021 at 10:30 PM, Lambert said:

Tiny... just lending morale support! I think you got great advice here.

I'd probably just aadd-Just like we don't want him getting in his head about it  don’t you get in your own head about it either!

Yes thank you Lambert. I am nervous myself which is not usually like me (but can be occasionally). I'm putting a lot of pressure on myself to make sure his first time is good. But I mean, it'll be better than nothing even to begin with lol

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2 minutes ago, Tinydance said:

Yes thank you Lambert. I am nervous myself which is not usually like me (but can be occasionally). I'm putting a lot of pressure on myself to make sure his first time is good. But I mean, it'll be better than nothing even to begin with lol

Right... sex, a lot like pizza... even when it's not the best, it's still good.  🤣🤣🤣

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