Sexual Relationships
+1 y

Lost a bet with a guy. Now have to try anal. Tips?

The new guy in my life and I made a hockey bet last night and I lost. The term of me losing is that I have to try anal. I’m open to trying new things sexually but my ass has always been off limits. However, I don’t back out of a bet. Win or lose. He respects me, so I know he’ll stop if I want to stop. That said, it’s gonna happen. So give me some tips please. Cuz I’m scared shitless.
Updates:
+1 y
We had it and I loved it. Have had it again a few times since. He ignited a fire in my soul. It’s amazing!
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Most Helpful Guys

  • To try properly, I tell you, you have to do it the right way for you, and the right speed for you.

    First, consider that I'm a man that do anal in both ways : I fuck asses, and my ass is being fucked.
    Then I don't speak "generally speaking".

    First, discover your anal excitment. Anus is a erogen location, then let's train to stimulate it. You'll have to find how to stimulate your anus (feelings, thinking, etc.) while being stimulated.

    Use lub to start! Always. Spitting is not enough. Real lub, water based.

    To do so, start with your own finger or dildo, alone, and lubrificated. Rub your pussy first, and when you're really horny, then tease your ass : rub it with your finger pulp, with gentle pressure, till you want/desire/need to insert it, but don't.
    Rely only on your desire, excitment, but not your head. Don't think, do. Release yourself to pleasure.
    Do it twice or three times, then the next training session, insert one finger (or dildo) lubrificated. Do it gently. Slowly. And masterbate your anus this way. You may take pleasure, but not orgasm, then rub your pussy at the same time, and release your thoughts, just feel pleasure.
    You'll have to accept the idea that it is a sexual way, and it contains many pleasures. (but you are not bounded to like this pleasure).

    You have to manage this first step to go on the second.
    Secondly: during a sexscene, he'll have to make you really horny. No penetration (of any kind), but masterbation, oral sex, or any thing that tease you really hot! You can suck him if you do it, or a 69, but not to much, he will have to last some minutes. Don't make him cum.
    Then let him lick your anus during sex if he wants to, and he must then start by rubbing it (like you did yourself). Then, let him finger your anus (with only one finger to begin). Two fingers in your ass is the minimum to prepare you, but a dildo can be used too. Both, lubrificated, obviously.
    The best way to let him finger your ass, I think, is to let him do it when he gives you head. Being ass-fingered while pussy-licked seems to be a great pleasure for many girls. (and men, try to be sucked while being ass fucked... so great!)
    You have to feel his desire to fuck your ass (through his licking, fingering, rubbing, etc.) in order to be aroused, and at the same time, you'll experience 'not beeing in control".

    • When you will get some anal pleasure, you'll realize that there is nothing wrong, nor dangerous, nor so painful that it is unbearable. then you'll want more. Maybe will you stop him fingering your ass, and ask for his cock. Then, lubrificated, let him get in, slowly, glans first, then body... He must not hurry when starting doing your ass. He must let you time to stretch and feel right. Then, you'll find it just great, or not, and a new way of pleasure comes to you! Please, don't bet those things... It's better to choose the moment for those tests ^^

    • Actually you say water base lube however oil based is much better. The anis has a natural liquid that breaks down water based liquids. I would suggest using vasaline, it can be messy and oily but it is easy to apply and stays longe. But if you don't like it feel free to use water base, just make sure to re apply a few times.

    • You're completely right. But as she is new at anal, I tried to give her a mean advice with water based (Mannix Classic is great). The reasons are these : - It will be her first... then it won't last too many minutes, I assume. Water based is enough then. ^^ - Silicone or vaseline are greater, but messy (as you say), and could be uncomfrtable for some... and I think that the lube isn't something to 'manage during this moment XD Managing those kind of lube (pjur are greaaaat!), is for later, when she'll become more fluent with anal sex. - In addition, only water based fit with ALL toys and dildos. And if they use a dildo to tease her, it's easier to do all with a water based. Except if the dildo is made with glass, but I think it will be plastic, silicon, or metal... Then water based stay the must to start ^^ But finally, you're right! For long anal penetration, silicone or vaseline are really better! I think this advice is really complete XD Thank you for the point ;-)

  • Why has it always been off limits?

    Anyway, eat light the day before and drink strong coffee that day or whatever to clean yourself out, and wash yourself well in the shower or whatever; get WATER-BASED lube, no other kind, and have him use his finger on you first with plenty of lube to get you lubed up and ready. Have him enter you slowly, and it'll hurt, but then have him back off and wait a minute or two to subside; keep doing that until it feels more normal. Eventually it'll start to probably feel good, though maybe not right away. Let him cum in your ass and beg him to do so-- it'll drive him wild. Good luck.

    • Thanks!

    • Per your update: MMM... damn. Good girl.

    • Thanks for MHO

Most Helpful Girls

  • Start by masturbating your ass on your own as anal feels very different. Do a poop, get some lube and a latex glove and slip some fingers inside. For actual sex get him to do that getting the lube in as deep as possible. Rub your clit during actual sex. Doggy is the best position to start in. Good luck.

  • Have a look at my opinion here. It might help:

    What to expect during anal sex? ↗

    • I am pleased it went OK!

    • Thank you for MHG!

  • Try and Make a new Bet, I Bet... You ain't Gonna like the Anal. xx

    • Welcome to Gag Town. xx

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What Girls & Guys Said

2 25

  • I know this probably won't change your mind but my advice to you is not to do it.. sure its new experience and its exciting and you may find yourself willing to do it eventually if your partner really wants it... its not pleasurable feeling at all and it gonna hurt you and it will keep hurting for a while after you do it ... there is really nothing good about it only the excitement of the action what makes people like it... you dont need to back out from the bet but you can change it... of course you made it clear that its gonna happen but I think you should reconsider... there is nothing good about anal you are not missing out on anything

  • Find a comfortable position yiu can easily get relaxed in. Use plenty of lube, and TAKE IT SLOW! Start with something small, then gradually build up to the size of his penis. I'm sure you'll do fine :)

  • Lots and lots of lube!! Haha! And I would start with a plug!! There is this set you can buy that will make your fisrt time amazing!! It is a three pack of progresive plugs and if you spend a week or so with each pug in for a certain amount of time every day or multiple times a day you can get super comfortable with having you ass wriped open like that.

    • Oh and washing it out!! Oh might want an enema or something to just flush it! Here is a good page that will help!!
      www.elitedaily.com/.../1541343

    • Lol! That is great! ;) so happy fir you both!!!

  • You had me at "scared shitless". 👍👍

  • Lube, relax, go slow, use something else for a bit first like fingers or a toy to get used to it

    • Congratulations girl

  • lots and lots of lube

  • Seems like a dumb situation to do something you don't want to do intimately. If you don't want to do it you shouldn't. You rub me as the type that people can take advantage of. You don't want to have anal sex (an intimate act) but agreed to do it over a bet.

    Are you two already a sexually active couple?

    • Yes we are.

  • It won't be that bad honestly, you just need to relax. Use lots of lube, slowly build up to his penis, don't just immediately shove it in. Work in a finger, slowly getting used to it, introduce a second, and then eventually his dick.

    And most importantly of all, patience. It's gonna take a while to get used to him inside of your ass, but eventually it'll start feeling tolerable, and possibly even good.

  • Ahahaha sounds like a bet i did with a girl except the loser gets it up the ass... luckily i won. have lube with you and if it hurts at any moment tell him to stop

  • Google it. If you've never shoved objects up your ass you're likely not going to like it, and it's gonna hurt. A LOT.

    And you better be shitless, or it will be all over. ;)

  • An enema is not required but not a bad idea, you need to use lots of lube and possibly start with a butt plug first. Have him push his dick in a bit and hold it there until your used to it, then a bit further and hold it until he's fully inserted then he can start to pump it in and out. Good luck and have fun!

  • Use a condom and PLENTY of lube, and just go slow. Keep topping up the lube every few minutes. Oh and unless you plan to stop entirely, don't let him pull out. My experience of anal is if she pulls away or I pull out, it's much harder to get back in and will usually hurt more than just pausing but not pulling out.

  • I need tips like... wherr do i find a girl that will honor a bet like this lol go slow and get a silicone/water based mix lube

  • Lots of lube

  • LMFAO, I'm not sure I can give you advice, but the question CRACKED me up. i would suggest a lot of KY gel. good luck

  • Anal sex can be tricky but it just takes a little thought and consideration to make it more fun than you can imagine for both of you. The critical success factor is your control of the initial penetration. I strongly recommend the spoon position. Use a good lube like Astroglide Gel. You don't need a lot of it, just enough to make everything good and slippery. Spoon up in front of him. He has to stay completely still until you tell him he can move. This is critical. Reach back and place him against your anus and press back with firm, constant pressure. Breathe and relax. Don't be in a hurry. You have all the time in the world. Push back internally like you're going to the bathroom. Before long, your sphincter will start to relax and he'll start to slip in. Just keep up the firm, constant pressure. If at any point the pain gets to be too much, just pause right where you are and wait for things to relax. If you need more lube, have him apply a little and you move him out and back to work it in. Once you're fully impaled, pause and focus on how it feels so you can replicate that feeling. Then slide him out and do it again. It'll be much easier the second time. Once you're fully impaled again and are ready, he can take very slow, short strokes to get you used to it. As you acclimate, he can increase the intensity. He'll likely not last long and so be prepared for the spasms of him cumming up your ass. As you get better at it, position won't matter and it'll be similar to vaginal sex except that he'll possibly need to slow down on the initial entry. Since he's into anal sex, he's more than likely a booty man so doggy will be a popular position over time.

    • Doggy is already the favourite lol

    • I agree

  • Get it, she's scared shitless!! Lol

  • ask him to go slow

  • lube, relax and guts.

  • tell you'll do something else

    3some or girl on girl sex

    • Nope. Threesomes and girl on girl are on both of our NOPE lists.

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