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Ask Ang November 19: Breaking Condoms, Difficulty Orgasming, and Anal Enjoyment

Welcome to Ask Ang, your anonymous campus sexual health resource, brought to you by H*yas for Choice. We are made up of a team of undergraduate students who work to answer your sex questions! We post questions and answers weekly on Sundays. Anyone can submit a question, and the anonymous form can be found here:

  1. I recently had anal sex (I am a cis woman) for the first time and found it somewhat enjoyable. What are some ways (aside from lube and preparation with manual stimulation) to make anal more pleasurable and stimulating?

We’ve gotten a few questions previously about how to make anal sex more enjoyable, and you can check out Question 5 of the October 9 edition and Question 3 in the November 12 edition for some of that information. You mentioned lube and preparation with manual simulation in your question (both incredibly important!), so outside of those tips, here are three key things we’d highlight for you:

1. Go slow! Let the receptive partner determine speed of the penetration, and don’t be afraid to start slowly.

2. Find your own rhythm! Play around with different grinding and rocking motions that might feel good for you. Don’t feel pressured to replicate the rhythms of vaginal sex during anal, and prioritize your comfort.

3. Figure out what works for you! Just as with any other sex act, there are countless different ways to do anal and different things will good for your body specifically. Trying different speeds, rhythms, positions, hygienic preparations, insertive methods (butt plug, dildo, finger, penis), and lubes to figure out what is best for you will make anal sex more enjoyable.

For more online tips, feel free to browse one of the following resources:

2. Why is it so difficult for people with vaginas to orgasm?

Media representation plays a huge role in this difficulty. According to Cosmopolitan, TV makes it seem like having an orgasm if you have a vagina is super easy (note: mainstream media representations of people with vaginas are overwhelmingly women, but linking vaginas and orgasms doesn’t just affect women, it affects all people with vaginas). Spontaneous orgams on talk shows and hamburger-induced orgasms in Carl’s Jr. ads (note: Carl’s Jr. is terrible in a ton of ways beyond orgasm-inducing hamburgers) constantly reinforce the link between vaginas and easy orgasms. Penetration-induced orgasms in pornography further contribute to the idea that mind-blowing orgasms are a piece of cake. This culture of easy orgasms makes it “difficult to turn off the thought that you should be having orgasms or to stop wondering when it's going to happen.”

Various medications can impact your ability to orgasm. According to the executive director of the Southern California Center for Sexual Health, Michael Krychman, MD, “medications like SSRIs (used to treat depression, anxiety, and other conditions) can diminish sex hormones in the body, and often lead to having crappy orgasms or no orgasms at all.” Other medications, especially the pill, can diminish your ability to have an orgasm, and it should be a conversation to have with a trusted medical professional to identify any potential medications that might be in the way of an orgasm.

While having an orgasm might not be a piece of cake, Alison Moon, author of Girl Sex 101, has some helpful tips that can help you have an easier time orgasming in the future. Moon lays out a three-step path to orgasm: Masturbate, Facilitate, and Communicate.

  • Regarding masturbation, Moon writes, “Experiment with penetration, glans stimulation, vibrators, hands, dildos, pillow humping… anywhere you can get your hands on yourself. Bottom line: try stuff… try different things, and learn to like different kinds of touch.” By expanding what you know feels good for you, more orgasms become much easier.

  • For facilitation, Moon explains that “your orgasm is up to you. A partner can help, but you’re the captain of the ship… Love candles? Light ‘em. Want a towel? Get it. Need a certain kind of vibrator? Bring it…. Help you help yourself.” Finding the right combination of factors isn’t easy, but you’ll never know if you don’t try.

  • Moon explains that good communication means that “when it comes to getting off, be a bossy bottom.” Once you’re familiar with yourself, you are able to communicate that familiarity to your partner(s). But communication with yourself is key, too. Unlearning the negative factors that society pushes onto people about vaginal orgasms requires establishing a connection between your body and your mind.

Finally, if you’ve never had an orgasm and you have no idea where to start, Moon has a super helpful guide that you can check out here.

3. I recently experienced a condom breaking during sex (I was wearing the condom and my partner was receiving). What can I do to prevent this from happening again?

  • First of all, both you and your partner should get tested for STIs as soon as possible, and if your partner is a cis woman she might consider using emergency contraceptives (such as Plan B) if she isn’t already using a second form of contraception. Even if ejaculation didn’t occur, genital skin-to-skin contact and pre-ejaculate fluid can transmit STIs and cause pregnancy.

  • As far as how to prevent a condom from breaking again in the future, the first step is to make sure that you are wearing the condom correctly. The condom should have about half an inch of space between the tip of the penis and the top of the condom. This space creates a reservoir for the semen after ejaculation. Make sure to place the rolled up condom over the tip of your penis when it is hard. Then, while pinching the condom at the tip, roll the rest of it down your penis with the other hand. Once the condom is on, make sure to smooth out any air bubbles, which can also sometimes cause condoms to break.

  • Additionally, try using some water or silicone-based lube if you haven’t already to reduce friction that can sometimes cause condom breakage. Make sure that you aren’t using oil-based lube, though, because oil breaks down latex and therefore can cause a condom to break.

  • Try out different brands and sizes of condoms to see what feels most comfortable to you. The condom should not be too tight, but also not so loose that there are gaps between the condom and the penis. Make sure, also, that the condoms you use aren’t expired--the expiration date is listed on the package--and that they’re not left in heat or direct sunlight.


Note: Questions may be edited for clarity and/or length.

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