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Sex Ed for Adults: Firsts and First Times in a While

Sex educator Cassandra Corrado answers questions on gender dysphoria, anal sex and more

Sex Ed for Adults: Firsts and First Times in a While Image
Written by vhigueras
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This month’s Q&A is here to help you cope with big feelings. And while we’re feeling all the feelings, we’ve got some advice for your first time trying out anal play, too (hey, it’s important to be well-rounded). 

These are a few questions I’ve received lately, and they’re a lot to cover, so let’s get started!  

It’s been a long time since someone touched me sexually, and I might have sex again soon. I’m worried about panicking. How can I ease back into things?

If it’s been a while since you’ve had sex, getting back into the metaphorical saddle can be literally anxiety-inducing. Some people find that as things start to heat up, they feel much more comfortable than they expected. Other people get to that same point and have a strong reaction, needing to take a break. Both reactions are totally okay. 


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If you want to ease back into sexual experiences, start with non-sexual touch. If it’s been a long time since another person has touched you in any capacity, your skin and mind may be less attuned to what positive touch feels like. You can reacclimate your skin to positive touch by creating a self-touch ritual that you practice every day at home. Try setting a timer for 10 minutes and moisturizing or massaging your skin, paying close attention to how it feels. You can do this in a partnered capacity, too — just have your partner do the massaging. 

Once your body is attuned to what positive, nonsexual touch feels like again, try masturbation. Use your hands or your favorite sex toy (or both!) and explore what it feels like to engage with yourself sexually. Do any emotional reactions start to come up? If so, what? 

Once you feel comfortable with masturbation and self-touch, talk to your partner about what you’re feeling. A simple, “It’s been a long time since I’ve been with someone sexually, so I’m worried I might get emotional. I’d like to take things slow, and if I start to feel some feelings, can we just cuddle?” A considerate partner will understand where you’re coming from and will want to be there for you.

If, after doing all of these things, you still have a big reaction, that’s okay! Give your brain and body space to process. It may take a little bit to get totally comfortable with sexual contact again, especially if you’re also working through physical or emotional trauma, so give yourself time and space to feel all the feelings.

I have bad gender dysphoria and it affects my sex life, both during and after sex. How can I have sex and feel okay about it?

For folks reading this who don’t know what gender dysphoria is, here’s a very basic explainer: 

Gender dysphoria shows up when someone experiences a conflict between their gender and parts of their body’s experiences (like menstruation, for example). It refers to the experience of having intense emotions (like sadness, anger, or betrayal) in relation to your gender, your body, and how others perceive you. 

First things first: Experiencing dysphoria during and after sex is really common. It’s also pretty manageable! Focusing on creating gender euphoric experiences can help to counteract dysphoria. Here are some ways to make that happen:

  • Have sex with people who make you feel desired.
    As simple as it may sound, this is something that many of us (whether we’re cis or trans) struggle with. When our partners don’t make us feel like desirable people (or they interact with our bodies in ways that make us feel uncomfortable) it lays the groundwork for negative experiences.

    If you correct your partner on terminology or ask them to not touch you in particular ways and they don’t listen, then they’re not respecting your sexual boundaries. Have a bigger conversation with them to point out how this affects you, and if they still don’t make changes or they make you feel weird for asking for those changes, then it’s time to re-evaluate if you want to be having sex with them.

    A considerate partner will listen and make adjustments when you ask them to call your body parts by certain names or not touch you in particular ways — that’s just basic sexual respect.
  • Invest in sexual tools that make you feel awesome.
    What makes you feel most confident in your day-to-day life? Pay attention to those things. Now, think about the sexual fantasies that you might have. What’s happening in them? How do you look? How can you recreate those experiences outside of your mind?

    The power of sexual tools to help create a thrilling, positive, and enriching sex life can’t be understated.

    Lingerie that helps your body look the way you want it to? Hell yeah.

    A silicone cock that you can wear all day so that you’re ready for sex without needing to excuse yourself? We’re here for it.

    Dirty talk and sexting to help set the mood? Say it louder for the folks in the back!

    These things don’t have to be expensive to work, but think carefully about what key changes might be most helpful to you and then plan for how you can implement them.
  • Use your setting and position strategically.
    If you’re having sex in a bed, the top sheet that you’ve spent a lifetime ignoring could be your new best friend. For example: if you want to be able to receive oral sex, but seeing how it’s performed on you triggers dysphoria, strategically placing the top sheet over your partner can help you create the scene that feels best for you. To help set the scene more thoroughly, ask your partner to use certain head motions as they go down on you — all of those elements can combine to create a gender euphoric scene. And remember, you don’t have to get fully undressed to have sex. You can leave clothing on that helps you feel good (you just may want to turn on a fan to help moderate your body heat).

    Positions can also help here, too. Adjusting your position can make you more comfortable physically and emotionally. Experiment with different positions that help you feel confident, comfortable, and physically present — it’s okay to practice these fully clothed, FYI. That can help give you a better idea of how you might enjoy things without the vulnerability of trying them for the first time while you’re having sex.
  • Watch porn or read erotica that’s trans-inclusive.
    If you look beyond RedTube and PornHub, you can find porn that includes trans actors and is ethically produced. Try Pink & White Productions, Crash Pad Series, and Foxhouse Films. Or, try finding erotica (even fan fiction) that speaks to you!
  • Develop an aftercare routine.
    You might think of “aftercare” as a concept strictly related to BDSM and kink, but the reality is that everyone can benefit from applying aftercare principles to their sex life. Aftercare is basically self-care and partnered care, intentionally applied to your post-sex world. Sometimes, aftercare looks like cuddling and watching a movie. Sometimes it’s a hot bath. Sometimes it’s going for a walk. Maybe it’s you getting dressed in an outfit that feels really you. Come up with a plan that works for you and your partners, and implement it when dysphoria starts to show itself. 

How can I prepare myself for my first time having anal sex?

Basically everybody has an asshole, so anal play is an option that anybody can do, regardless of their gender or sexual orientation. 

Anal play encompasses many different sexual behaviors, and they all count as “sex”! You might be using a toy, like a butt plug or anal beads, on your own or with a partner. Maybe you’re experimenting with analingus (oral sex performed on the anus) or anal fingering. Or, maybe you’re looking to try penetration with a dildo or cock. 

No matter what you’re interested in, there are steps you can take to be better prepared — whether you’re the receptive partner or the penetrating partner. But remember: No amount of preparation is going to make anal play pleasurable if you don’t want to be having it. So if your partner is pressuring you into it, it’s time to have a conversation about respecting sexual boundaries. 

  • Invest in lube
    The anus doesn’t self-lubricate, so using lube is absolutely essential here. Some people like silicone lubricants because they’re very thin and extra long-lasting, but they shouldn’t be used with silicone toys. Water-based lubricants are compatible with all types of toys (and barrier methods) and can offer some more cushion for the Booty Beginner. Water-based lubricants will need to be reapplied more frequently.
  • Consider your barrier methods
    The mucous membranes in your anus are incredibly thin. That means that they’re very sensitive and responsive to touch, but they’re also more likely to tear from friction or vigorous force than other parts of the body, making you more susceptible to infections (this is another reason why you should use lube, FYI!)

    Barrier methods can help protect you from STIs and make clean-up after anal play easier.

    If you’re considering using your hands to explore a butt, try unpowdered, non-latex gloves (Black Dragon makes black gloves that won’t show fecal matter). If you’re considering analingus, dental dams are your friend! If you can’t find dental dams, plastic wrap from your kitchen will do (just make sure there aren’t any tears in it) or you can modify a condom to use as a dam. For all other types of penetration, standard external condoms or an FC2 (with the plastic internal ring removed) will work!
  • Manage poop 
    If you’re planning on trying anal play, you need to accept something: You’re going to where poop lives, so don’t be surprised if you encounter a little fecal matter. Barrier methods can help manage the “OMG!” reaction if that happens, but there are other steps you can take to reduce the amount of fecal matter present.

    Go to the bathroom before anal play begins. Some people choose to use an enema before anal play, but it isn’t a requirement. If you decide that you want to use an enema, you can find the necessary bottles at your local pharmacy. They’ll likely come pre-filled with fluid, but go ahead and empty that out – remember, the anal tissues are super sensitive, so you want to be mindful of what you put in your anus. Refill the bottle with plain, warm water, and then follow the package instructions. (As a tip — do this well in advance, because it can get messy).
  • Practice patience
    As one of my mentors used to say, “nobody knows a liar better than your asshole.” What they meant is that your anal sphincters and pelvic floor are going to know if you aren’t feeling ready or excited about anal. No matter what anybody tells you, anal play should not hurt. With adequate preparation and lubrication (and a considerate partner) anal play can be comfortable and pleasurable — even your first time.

    So, don’t go from “I’m new to this!” to anal fisting all in one go. Pay attention to your body and slowly progress. Try external stimulation first, then gently try inserting a (well-lubricated) finger. Or, trying wearing a small buttplug. Once you feel comfortable with that, you can try to add more fingers. Remember, the average width of a penis or dildo is two fingers’ width.

    The partner doing the penetrating, especially if using a strap-on or their penis, may feel compelled to thrust forward. Don’t do that. Especially when you’re getting started with anal play, the receptive partner should move toward the penetrating partner — that gives them control of depth and lets them stop when they need to. It also ensures that an over-zealous penetrating partner can’t unintentionally do damage.

    If you’re the “I like to be prepared for anything” type, b-Vibe makes an anal training and education set.
  • Listen to your body
    I’ll say it again: Anal shouldn’t hurt. If it does, your body is trying to tell you something, so please, pay attention to it. Pause what you’re doing and figure out what could be causing pain. Do you need to add more lube? Reduce girth or length? Change positions? Stick to external play only? The only right way to have anal sex is however it feels good for you. So, if your body tells you “OMG no thank you!”, respect its request. Your anus has many nerve endings, so stimulating it should be pleasurable, not painful.    


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