1. This site uses cookies. By continuing to use this site, you are agreeing to our use of cookies. Learn More.

Advice for First Time Ever With a Guy?

Discussion in 'Physical & Sexual Health' started by Mlh88, Jan 16, 2020.

  1. Mlh88

    Regular Member

    Joined:
    Jan 16, 2020
    Messages:
    8
    Likes Received:
    0
    Location:
    United Sttes
    Gender:
    Male
    Gender Pronoun:
    He
    Sexual Orientation:
    Gay
    Out Status:
    Out to everyone
    Hey everyone,


    First time ever posting on here.


    First, I just want to say thanks. I’ve been a reader of the site for a long time even before I was out, and while there were many days I thought I would never be brave enough to come out of the closet, these posts inspired me to finally build up the courage to do so.


    So I didn’t come out until I was 27 (I’m in my early thirties now). Long story, but I lived in a rural town and was scared and nervous about it. I live in a larger city now.


    Even though I’ve been out for several years now, I am still a virgin. I’ve never even kissed a guy (or girl) before. Crazy, I know, and trust me, I really want it, but I started a new career when I moved and sort of pushed my personal life to the backburner, but it bothers me that I put in all of the work building up the courage to come out, but have yet to still enjoy any of the physical and sexual perks of that.


    Jumping forward, I’ve dipped my toes into the online dating world, and I’ve been speaking to a guy I really like and that I think I would really like to be my first. He’s a bit older than me, and I like the fact that he is older and more experienced, and I feel like I’ll be more comfortable with him taking control and guiding me a bit.


    I definitely want to bottom for my first time, this is the way I’ve thought about it and planned out for so long now. I read the sticky thread about this but I have a few concerns/questions that I hope you guys can help with.


    First, I know it’s a crazy question, but any tips on kissing? I don’t want to be terrible at it the first time lol.


    Onto the sex part, any tips for oral sex? I want to make sure I do a good job for him, I have some idea of what to do but any tips I’d appreciate.


    Second, onto the actual anal sex, what is the best way to prepare myself? Should I not eat certain foods or things beforehand? I’ve never even used a finger for that so this will definitely be something new for me (I’m not sure how big he is).


    What I would really like position wise is to be on my back so I can be looking at him, but I also want to do what’s going to be the easiest and most comfortable and enjoyable. I really want to be able to take all of him on this first time and be able to really enjoy that and this experience that I’ve been waiting on.


    I’ve purchased lubed condoms and lube as well, do I need anything else?


    My main concern is just to make it special for not only me but also him, the more I know he’s turned on, the more I’ll be turned on.


    Any tips or advice is greatly appreciated. I know saying that I want it to be perfect is a high bar to set, but I do want to it be really great and for us to both be very happy at the end.


    Also, I’m hoping our relationship will continue, and I’d ideally like us to have sex on a daily basis (with him always topping and me always the bottom). Is there any tips on this as far as me needing to do anything differently to be prepared to do it so regularly?


    I know this is a long post but I sincerely appreciate any help you guys can provide. Thanks again.
     
  2. Horus

    Regular Member

    Joined:
    Jan 10, 2020
    Messages:
    28
    Likes Received:
    5
    Location:
    San Diego California
    Gender:
    Male
    Gender Pronoun:
    He
    Sexual Orientation:
    Gay
    Out Status:
    Out to everyone
     
  3. Horus

    Regular Member

    Joined:
    Jan 10, 2020
    Messages:
    28
    Likes Received:
    5
    Location:
    San Diego California
    Gender:
    Male
    Gender Pronoun:
    He
    Sexual Orientation:
    Gay
    Out Status:
    Out to everyone
     
  4. Mlh88

    Regular Member

    Joined:
    Jan 16, 2020
    Messages:
    8
    Likes Received:
    0
    Location:
    United Sttes
    Gender:
    Male
    Gender Pronoun:
    He
    Sexual Orientation:
    Gay
    Out Status:
    Out to everyone
    Hi all,

    I’m going to bump this thread up again and also ask an additional question I thought of as well (sorry for all of the questions).

    We’ll definitely have a discussion first to ensure he’s clean, but if so, is it generally safe to do oral without a condom? What about oral with swallowing?

    Again, thanks for all advice, I just really want to be able to do and enjoy the things I find a turn on, safely and enjoyably.
     
  5. Ram90

    Moderator Full Member

    Joined:
    Nov 18, 2015
    Messages:
    1,048
    Likes Received:
    359
    Location:
    Canada
    Gender:
    Male
    Gender Pronoun:
    He
    Sexual Orientation:
    Gay
    Out Status:
    Some people
    @Horus I find what you wrote so relatable, since I've been through most of what you wrote myself. I was in the closet for a long time, and came out after I turned 27, to a couple of really open-minded people who became my friends. And then I started dating. Until that time I never dated a guy or girl and never kissed either or was intimate. So my experience was pretty zero. Luckily enough, after a few horrendous dates, I had the chance to date and be intimate with two older guys (They were about a decade older than me) and they were kind enough to show me the ropes. Lucky huh!

    If you have a chance to date someone who is a bit older than you (in your case) then I'd say go for it. It helped me understand things better, in my case. I'm sure it will in your case too. :slight_smile:.

    I let both of the older guys steer me, as I had zero knowledge on kissing. We just came together, hugged for a while and they steered my head into the position they wanted before they kissed me. Of course, on later dates, I initiated stuff, but it helped in the initial ones if I let them do the steering. I wouldn't recommend french kissing, using tongue or biting the lips until you actually know the guy a bit better ha ha. I was brave enough to try tongue with one of them towards the end of our date/intimate moment. They just laughed and asked me if I wanted to try tongue action and I nodded. Ha ha. So I don't think it is wrong for you to talk about your inexperience and tell them what you would want to try. I instantly knew I would have a good time with those guys when they agreed. And it helped that I told them about my inexperience before we met. They knew what they were getting into with me.

    As for Oral Sex, it didn't help me that my first ever was a pretty big guy. He was very well-groomed down there and helped me understand how to fit it in my mouth and what to do. I think my tooth scratched him a few times and I almost bent the tool the wrong way ha ha, but he was sweet. Of course once you get into the heat of the moment it is difficult to control emotions. I almost gagged when he tried to force my head all the way down, but I stopped and reminded him I wasn't comfortable that way. So once again, I'd advise you talk before you start, that way they know what your expectations are. It helped that I took breaks and used my hand to service the guy in between, so that my mouth and tongue could get a break. That way the action isn't broken, you're just switching between your mouth and your hands. ALSO please, please talk it over with the guy about the action of cum in the mouth. I told both the guys I wasn't interested in tasting semen. I don't mind if it got on my hands, but a definite no-no for anywhere on my face or in my mouth. Set the expectations and be clear on what you're comfortable with. You can always try something new in the middle if you're brave or curious enough, ha ha.

    I haven't engaged in anal sex yet, but I have played around. When I wanted to engage in anal fingering and analingus/rimming, I made it clear to the guy ahead of time that I would be open to mutual analingus. So the both of us made sure to finish eating something hours before we met, take a dump, wash and clean down there with plenty of soap before we met. It also helped that we jumped in the shower for a quick rub-down with soap before we went at it. Regardless of whether that made a difference hygiene wise, mentally we both felt a lot clean, so it didn't feel icky/yucky to get into what we wanted to do. Just make sure condoms and lube are used. Like really used. Lots and lots of lube. Don't be stingy with it.

    Apologies for the essay. I hope it's somewhat useful. :slight_smile:. Good luck for your experience!

    --

    @Mlh88 Is oral sex without a condom pleasant? Perhaps. It is definitely easier without a condom? Perhaps. Is it safer without a condom? Probably not. A condom is advised to minimise the chances of contracting STDs and other infections. So it's definitely the safer way to go. If you don't use a condom for oral sex, I don't think oral sex with swallowing or without will make much of a difference hygiene wise. Other than that, you can do whatever you think will make the experience enjoyable to you. Just stay as safe as you can. :slight_smile:
     
  6. Mlh88

    Regular Member

    Joined:
    Jan 16, 2020
    Messages:
    8
    Likes Received:
    0
    Location:
    United Sttes
    Gender:
    Male
    Gender Pronoun:
    He
    Sexual Orientation:
    Gay
    Out Status:
    Out to everyone
    Hey Ram90, I appreciate your reply, not an essay at all, like I said, this is totally new for me so I’m grateful for any and all advice.

    Yes, him being older definitely appeals to me for that reason exactly, I feel like he can show me the ropes and guide me through the newness of it all.

    I actually asked about the oral sex with swallowing because I would like to have him cum in my mouth as long as we can do that safely, as that really appeals to me.

    Good tips on both the kissing and oral sex, I’ll let him sort of take the lead and guide me. I haven’t told him yet that I’m a virgin but he’s a really sweet guy and I expect that he’ll be more than accommodating of trying to make sure that I’m comfortable and enjoying the experience. Of course there’s those first time nervous jitters but I am extremely attracted to this guy and feel a good connection with him and I believe in my gut that he’s the right one for my first time and the nerves just give way to excitement for something I’ve been looking forward to for so long.
     
  7. Ram90

    Moderator Full Member

    Joined:
    Nov 18, 2015
    Messages:
    1,048
    Likes Received:
    359
    Location:
    Canada
    Gender:
    Male
    Gender Pronoun:
    He
    Sexual Orientation:
    Gay
    Out Status:
    Some people
    @Mlh88 Good Luck! I'm sure he will be accommodating. Just try to let him know ahead of meeting him. That way it won't be a surprise. Nervous jitters will happen ha ha. My first ever dates and intimate moments were with complete strangers. So I was very nervous, ha ha. But we did chat for a long time before we met, so it was still somewhat okay. Just stay safe and make sure you carry everything with you ha ha (Condoms, Lube, Pepper Spray) so that you have it with you just in case he forgets any of them. Most importantly have fun!!!
     
  8. Mlh88

    Regular Member

    Joined:
    Jan 16, 2020
    Messages:
    8
    Likes Received:
    0
    Location:
    United Sttes
    Gender:
    Male
    Gender Pronoun:
    He
    Sexual Orientation:
    Gay
    Out Status:
    Out to everyone
    Thanks Ram, I appreciate it. Obviously the part I’m most anxious (yet excited) about is the anal sex so hopefully someone can give some advice in that area. From what I’ve read, it seems like even for the first time, it shouldn’t be an issue for me taking all of him no matter how big he is as long as we use lots of lube and go slowly. We’ve been chatting and are building up to meeting for a date, I don’t expect anything more than a kiss to happen on the first date so I’m thinking maybe I’ll discuss it with him then. I already know he’s a top which helps a lot (as I have no desire to do anything other than bottom), and I’m hoping we can sort of plan things out on the date for our night which will hopefully be this week. I’m just so excited it’s finally going to happen and with someone as sweet as him that I’m so attracted to.
     
  9. Horus

    Regular Member

    Joined:
    Jan 10, 2020
    Messages:
    28
    Likes Received:
    5
    Location:
    San Diego California
    Gender:
    Male
    Gender Pronoun:
    He
    Sexual Orientation:
    Gay
    Out Status:
    Out to everyone
     
  10. LaurenSkye

    Full Member

    Joined:
    Feb 25, 2012
    Messages:
    1,133
    Likes Received:
    141
    Location:
    Cincinnati, OH
    Gender:
    Female (trans*)
    Gender Pronoun:
    She
    Sexual Orientation:
    Bisexual
    Out Status:
    All but family
    I'll keep these posts in mind for when I eventually have my first time. I doubt I could ever perform oral sex on a guy with a big penis because I gag easily.
     
  11. Ram90

    Moderator Full Member

    Joined:
    Nov 18, 2015
    Messages:
    1,048
    Likes Received:
    359
    Location:
    Canada
    Gender:
    Male
    Gender Pronoun:
    He
    Sexual Orientation:
    Gay
    Out Status:
    Some people
    You should definitely keep your comfort in mind at each and every point. :slight_smile:. If the guy you're with doesn't understand or care for your comfort and vice-versa, then I'd think he wasn't the right guy to be with. :slight_smile:.
     
  12. Horus

    Regular Member

    Joined:
    Jan 10, 2020
    Messages:
    28
    Likes Received:
    5
    Location:
    San Diego California
    Gender:
    Male
    Gender Pronoun:
    He
    Sexual Orientation:
    Gay
    Out Status:
    Out to everyone
    The whole is greater than the sum of
    The whole is greater than the sum of its parts. A penis, a toe a leg or just any one part of a person misses the whole picture. makes a person a fetish. A baby sees the world as things. A Man sees life, not things. Feel his whole body from his head to his toes.see him inside as well. Mind, Body, and Spirit makes him whole A Man is more than just a hole.
     
    LaurenSkye likes this.
  13. Aussie792

    Full Member

    Joined:
    Apr 5, 2013
    Messages:
    3,317
    Likes Received:
    62
    Location:
    Australia
    Gender:
    Male
    Gender Pronoun:
    He
    Sexual Orientation:
    Gay
    Out Status:
    Out to everyone
    I've no idea if you've actually gone ahead but, given the level of preparation you've gone into, I think the best thing to add is - relax! Thinking, planning and strategising everything down to how to kiss will make for an awkward, fumbling experience.
     
  14. Horus

    Regular Member

    Joined:
    Jan 10, 2020
    Messages:
    28
    Likes Received:
    5
    Location:
    San Diego California
    Gender:
    Male
    Gender Pronoun:
    He
    Sexual Orientation:
    Gay
    Out Status:
    Out to everyone