How do I make my first time better?

[Anonymous]

Forgive me, this may seem stupid but I’m worried about losing my virginity. Only because the guy I want to take it is someone I've known for 5 years and we were together for half of that time. And didn’t talk/ weren’t official for the other half. We never had sex. Without getting into too much, I guess I’m just worried when we do if it’ll be underwhelming for him? We’ve both wanted to since day one. But I’ve tried to wait for better circumstances. Now we’re both adults and have our own places and transportation so It might be time but I’m not sure. But we’ve waited for so long that now I’m kinda worried he won’t like it? Like I held out for so long for something that might be average or meh. I clearly have no idea what I’m doing when it comes to sex and I’m scared I’ll be loose or something stupid. I’m pretty open minded on how it might go for me. I’m prepared for that. I guess my question is how do I make it so it was worth the wait? He was patient with me for the most part though he had his moments. IF I decide to do this. What can I do to make it better? Or make sure I don’t screw it up or embarrass myself.

[ohshee]

Ok first of all you can't screw it up the odds are he will it doesn't matter really what you do because I'm sure he's going to get on get up and be done with it that's what most guys do I hope that's not true for you as for your first time he should be worried about it as he should be making it special for you by lasting a long time I think that's going to be the downfall is he won't be able to last you really have me curious now and how this is going to go I do know what I would do if I was him but that's if I was him I can't really tell you what to do or what not to do because nobody knows what he's going to do I say just enjoy it I will tell you this if he gets on you and just start pumping away tell him to slow down because all he's going to do is work himself up shoot his load and he'll be done I hope it makes it enjoyable for you I hope he makes it good enough that you want to do it again soon because it is one of the most beautiful buildings in the world to share with somebody can you sound like you would be a fun person to share it with well let us know or let me know how it turns out I'm very curious that way I can tell you how I would have done it LOL have a good day good luck and I hope you have fun and I hope he shows you how beautiful it really can be

[Asker]

Thank you very much. I hope you’re right. I hope it’s not a situation where he ups and leaves afterwards. That’s a big fear of mine. Especially after trying to save my self for something special. That would break my heart. He likes to talk about how he would make it special. Of course that remains to be seen. I hope you’re right about not being able to screw it up. It’s just that I’m the virgin and he’s not and maybe I won’t be as fun as his past experiences with girls of more experience. Do you understand? A lot of women regret their first times and I don’t want that to be me for any reason. Be it his fault or mine. Thank you again. Your honesty is appreciated. And IF it happens I will try to remember to let you know how it goes. Haha

[ohshee]

If I can I would like to explain something to you can u send me a private message so I can do so there are things you can do

[Asker]

I’m sorry. I tried to message you and it said I have to be Xper 2?

[ohshee]

Really that strange maybe add me that might work

[Meldrum]

This scared of sex thing is just some jitters. Get together with him and let the foreplay begin. Is he experienced at all? If so, he'll guide you. You could start things off with kissing and fondling, get him going with a handjob, and take your time. Move from that to a blowjob and don't just suck his cock, make love to it. Do it right and he'll blow before you even get his cock in your pussy. That just means it gives him move time to work on you. Pure heaven for me has always been to drive my lady wild with my tongue and fingers. Let him get you hot and orgasm at least twice. I guarantee if you enjoy it he will too and get hard in a hurry. Once he enters, hold him back slightly and remind him you are a virgin and it might hurt but it's okay, go slow. You will find it to be quite enjoyable.

[Asker]

Thank you. This was helpful. Please excuse my naïveté but how does on “make love to it”? I guess I’ll figure it out haha but I think I’ve heard that expression before in regards to blow jobs and I guess I don’t fully understand what that entails.

[Meldrum]

I could explain it in very simple terms, without getting banished from GAG I hope. Have you had a hot makeout session yet? Well, break that down to one single aspect. His penis. Nothing else exists but his cock. It's the only thing you will ever have forever. It's your one chance to make love and you want it to be memorable for him and you. You do everything slowly to start and then, with more passion as you progress, you bring him to the very edge, then let him cool his jets by playing with the balls, under the balls, between the balls and the anus. It's very sensitive down there. and once he's calmed a bit, you do the same thing. Hint: A man's penis has its own clitoris. It's right under the head, where the "helmet" has a small bit of skin where they come together. If you want him to cum buckets that will be the place to put your tongue. Work it girl. THAT is making love to his cock.

[Asker]

Wow haha. That was very helpful. I understand it a little better. There’s a method to the madness I see. I’ll probably be nervous but I guess I can try. Thank you very much for all your help. I enjoyed this conversation haha

[Boodica]

You should be speaking with him especially about birth control & sexually transmitted diseases. Have you any idea how experienced he is? You should be speaking with him about your fears & concerns. Not going with the flow & heat of the moment. Worry later about perfecting your technique. That comes with experience. If he doesn't know how you feel how can a relationship be genuine. If I had to do it all over again, I would make sure I was not making decisions when I was horney. I would make sure I got off on my own somehow. Hormones drive the urge to reproduce through sex hormones. If you feel reluctant or unsure or fearful, perhaps he is not the right guy. Pregnancy is life changing. Make sure you are prepared.

[Asker]

That’s very wise. I’m not ready for a child. And I do plan on starting birth control pretty soon. I think he’s the right one. I hope he is. I care a lot for him and for the past 5 years I’ve wanted to have sex with him. I’m just a little concerned I won’t be good enough… or good at all. You’re right though, I will talk to him about how I feel. That way we can better understand each other before we decide to do this. Thank you very much for your help. I appreciate it.

[loves2learn]

I think you may have built it up too much in your head hun. I mean the first time was good. I was ready. I’m glad we did it. It hurt a little bit not a lot, he lasted for 30 seconds and 15 minutes later we did it again.


I would say it took about a month for us to really get into a comfortable rhythm that we really liked.


First times are rarely spectacular. It’s the times after.


I’m still with the same man 20 years later. We have amazing sex and I can still surprise him.

[Asker]

That’s amazing. Well he’s not a virgin. He lost his virginity long before he met me but I’m 21. I guess that’s why it worries me so much. He’s experienced it before. I hope what happens for you happens for me. That’s such a blessing. Most women regret their first time and I never want that to be the case for me. Maybe you’re right. Maybe I’m overthinking it. Thank you for you answer. I appreciate your help and honesty.

[loves2learn]

Of course! You are so welcome. Just have him go slow. I wouldn’t worry about his number of partners. I’m sure he cares about you and you can learn each others bodies together.

[summiter]

Is he a virgin also? The big thing is to take it slow. Just get naked and take a long time exploring each others bodies. Talk about and plan for birth control ahead of time so you have one less thing to worry about. Consider some lube.. it works great. After he slowly goes inside you just have him stay still for a minute or so to let you get use to him inside you. Don't let him just start jackhammering away. Above all.. have fun and enjoy the moment. Your thoughts?

[Asker]

No, he isn’t a virgin. He’s been with a few other girls. He lost his virginity years ago. The birth control plan is a good idea. It’s all good advice actually. I’m still just wondering what I can do so he enjoys it. I guess there isn’t much I can do but I don’t want him to feel it was mediocre in comparison to the other more experienced girls he’s had sex with. Thank you for your help. I appreciate the advice.

[summiter]

Your first time should be about you and not him. If you want him to have fun maybe give him a good handjob first. He will have fun and a good orgasm no matter what. enjoy!

[Asker]

Is that true? That men enjoy it regardless? That it’s always great to a guy?

[summiter]

The guy will always have an orgasm... just enjoy the moment!

[Dargil]

Not trolling you. Where does your intimate relationship stand with him at present?

[Asker]

It doesn’t really exist much. We’ve been sexual with each other before. Flirty especially when we were together. We hadn’t talked in about a year and he reached out. And I’m so glad he did because I missed him. Anyway, we live in neighboring states so we don’t see each other like that and our relationship has always been long distance. We’ve been intimate before though. Just to a certain extent. Any help is appreciated.

[Dargil]

You have had intercourse with him in the past?

[Asker]

No no ! We’ve just talked about sex. And we came close to having sex. Real close. But it never happened.

[Dargil]

The two issues you have to accommodate are physical and psychological. The physical one is straight forward. If you do self pleasure or he has fingered you and can pass two-three fingers or an object perhaps one inch or so across. You won't have a problem here. Just be sure to have personal lube or lotion available. Even if you get plenty wet, it is inside and you need to be wet at the... doorway. Don't relay on nature. If you can't do this, there is a routine that can help.

[Asker]

A routine?

[Dargil]

Yes. I have been with two virgins. The first went poorly. The second, we worked out a plan to make it go easier. It did.

[Asker]

Oh ok. What made the first one go poorly may I ask?

[Dargil]

Because I didn't know how to introduce a virgin to sex. I was ham fisted.

[Asker]

Huh? Lol

[es20490446e]

Slowly and with time.

[Asker]

Ok. I will try to remember that. Thank you very much.

[es20490446e]

Have a nice day 👌

[Jamie05rhs]

Well, let's back up a little bit and examine an important truth: first time sex is almost never perfect. The first time doing anything is almost never perfect. The reason you were waiting in the first place (correct me if I'm wrong) is because you wanted it to be SPECIAL -- not "perfect."

You say you've known this guy for 5 years and been with him for half of that time. What was your relationship like during the other half? And why? What were the issues that were keeping you apart (relationally, not sexually)?

[Asker]

You’re right I do want it to be special. Our relationship was always long distance. Towards the end of the relationship he just was pulling away a lot. And there was a lot miscommunication and misunderstanding. I guess it was just hard being far apart and the longer we were together the harder it got. For both of us. We were still kids. I was 16 he was 18 when we got together. After that we broke up we still talked on and off. We just weren’t effectively communicating. I’m not going to bore you with all the silly details but it was just rough. My feelings never dwindled though.

[Jamie05rhs]

I don't mind "silly details;" I won't be bored. But just share as much as you're comfortable with. :) Hmm. So you faded out... but here you are back together again. What was the catalyst that caused you two to re-enter each other's lives?

[Asker]

I appreciate your patience ☺️. We aren’t back together. We’re just talking again. There are talks of a reconciliation and if we do get back together; talks of doing that with each other. He reached out to me. I’m not aware of what made me cross his mind after so long.

[Jamie05rhs]

Interesting. Has he said anything to you about what his intentions are as far as a relationship?

[Asker]

He implied he wanted to do couple things we weren’t really able to do before. Like dates and dinner and seeing each other more often. And of course sex. I can’t tell how sincere he is being though. We’re both kind of busy right now. So it hasn’t happened yet.

[Jamie05rhs]

He could have been bullshitting about the dates and dinners. A lot of guys offer that as a trade-off to get sex. Though I'm not saying that's necessarily the case with him. I don't know the guy.

[Asker]

Yeah he could be. I hope not. Like I said it is different now then when we were kids. Being long distance we didn’t get to do dates and dinners and things like that. We hung out only a few times. but I told him I won’t be doing anything if we aren’t in a relationship. So hopefully he takes me seriously. Because I want to take that next step with him. And I have wanted to since we met 5 years ago.

[Jamie05rhs]

Well, don't rush it (the sex.). You've waited 5 years and you didn't die; you're just fine. So you can wait another year if you have to. Just to make sure!

[jeremy_09]

just do it and after about 10 times you'll know what you're doing, plus the 10 times will be pretty great anyway

[Asker]

Haha well I hope you’re right. I just hope I don’t bore him before we get to 10 or something. 😓 Anyway, thank you for your advice and honesty. It’s appreciated.

[jeremy_09]

nope won't bore him i promise

[TheBigGuy9]

Are you doing this just cause or do you want him as your one and only? Why would you think you would be too loose? Get yourself a dildo to practice on, unless that’s the reason why you might think you’re too loose? Get one the same size of him or smaller. Get one with the suction on it and ride it forwards and backwards. When you’re bent over or laying on your back, the man is doing 99% of the work. My best advice would be to stay relaxed.

[Asker]

I’m not really sure why I think I’m loose. I know my bladder is weak sometimes and I know that has something to do with it right? I’m probably just being paranoid. I want to do it because I love him and I don’t think I’d want to lose my virginity to anyone else. It’s not just because but I want to make sure it’s right. I don’t want to mess it up somehow.

[TheBigGuy9]

You’ll be fine. If it’s something medical why you think you’re loose, then so be it. We all have our problems. You both have had to of fooled around before, right?

[Steve1071]

One thing is for certain if you’re constantly worrying while you’re in the middle of the act you aren’t going to enjoy yourself and you probably won’t even have an orgasm second you should read some materials on different types of sexual play between couples that way you have a little bit of an idea of what you are doing and you won’t go into it blindly second it’s only sex if you make a mistake no big deal it’s sex! Sex is a form of exploration and discovery enjoy it.

[Asker]

That’s a good attitude to have I suppose. I’m new at this so I’ll probably make a most somewhere but I shouldn’t think about it to much. Otherwise it won’t be enjoyable at all. I understand. Thank you very much.

[Valnac]

You’ve got the wrong attitude.
You are not a virgin for his pleasure.
You should concentrate on using him for your pleasure.
Make sure he uses protection and uses a lot of foreplay. You want to be sexually aroused and soaking wet.
Try to relax and enjoy it. It’s a moment you will remember for the rest of your life.

[Asker]

I know. I will try. Though, I think I will find pleasure if I know I made it a pleasurable experience for him to. Especially considering I’m not really sure what I like. Anyway, thank you for your wisdom. I’ll be sure to take your advice.

[Valnac]

👍 Good luck.

[GAGSucksBalls1]

NEVER lose it to "just a friend", NOT A GOOD IDEA

[Asker]

I agree. It won’t happen if we aren’t in a relationship. I think I’ve made that clear to him. I’m not big on the friends with benefits mentality. Especially when there’s actual love there. Thank you for your advice though. I appreciate it.

[Bklynbadboy12]

Don't do it lose it to some you love some special of you do it like this you'll regret it

[Asker]

Oh I do love him. A lot actually. He is a constant in my heart. So I want it so that when and if we do have sex he enjoys it. I know most girls feel discomfort or pain with their first times so I’ve come to terms that it might be the same for me. Ideally both of us would enjoy it but if I don’t the first time I want him to. Do you understand what I mean?

[Bklynbadboy12]

Trust me you both will enjoy it just don't over think it

[Asker]

Ok. Thank you.😊

[Bklynbadboy12]

Your welcome I hope you have an amazing first time keep me posted 😊

[Anonymous]

Have you done anything sexual together yet? Hand jobs? Oral sex? Been naked together? Masturbated together?

[Asker]

We’ve done some things. It just hasn’t gone all the way. The last time we did was probably around 2 years ago though. And I haven’t been with or interested in anyone else since. Not that I knew what I was doing before but I’m sure it’ll be hard after so long and already not being experienced in it.

[Opinion Owner]

Perhaps you should ease into it by doing some sexual things together without having PIV intercourse. Has he ever made you cum with his fingers? Have you given him a hand job? That would be a good place to begin? or perhaps you should simply take of your clothes and watch each other masturbate. That would be a learning experience for both of you.

[Asker]

We did do things to each other with our hands. I just…I know I’m pretty awkward and I don’t want to be during sex. I get nervous and I don’t know what to do. He has never made me cum though. I did oral with him once before and I don’t think I was good at it. I’m not completely sure but I don’t think so. Haha😅

[Opinion Owner]

Do you ever use a vibrator? Have him use a vibrator on you and it will feel wonderful. And ask him to give you feedback when you are giving him oral sex. That's how you learn.