Ask Jay: Returning to sex, erotic massages, and seeking orgasms

Hello and welcome to another session of Ask Jay! I'm Jay, a sex-positive fellow from Nova Scotia who likes to talk about all things erotic, kinky, and romantic. Today we're going to talk about erotic massages, making sex more comfortable, and how to provide orgasms. Let's get started, shall we?

Returning to sex asks: I've been a widow for a few years and have just started seeing someone. After many years without sex, it's now quite painful. Can you recommend things to make it more comfortable?

Jay answers: My condolences on your loss. And my congratulations on your return to dating. I hope it's going well.

Getting back to sex can be unnerving after a long time away, especially with someone new. It's easy to feel out of practise.

Your body may not be accustomed to the sensations involved in sex and some of your muscles which would normally only get a workout during sex may be out of practise. This may cause some discomfort at first. If you're also nervous this may cause you to tense up and cause discomfort too.

There are a few things you can do to help with the pain. One is to try to relax and take things slowly. If you hadn't been jogging in a few years you wouldn't start off by sprinting the next time you put on your running shoes. Encourage your new lover to take things slowly and engage in lots of foreplay.

Don't be in a hurry.


You didn't say exactly what aspect of sex was painful, but I suspect (either because it's been a while or because you might be nervous) you might not be producing as much natural lubricant as you did before. This would make sex quite painful. Keeping some lube next to the bed and applying it to the exterior of your partner's condom just before penetration can make things much more comfortable.

Comfort in a bottle.


This might also be a good opportunity to try some sexy play on your own. Try out a traditional vibrator while you're alone. Experimenting with it, seeing what feels right (and what hurts) can help you get used to the physical sensations again. It will also help you direct your lover in ways that will hopefully avoid pain in your future encounters.

Finally, if you've played with toys and you've tried lube, and your partner is engaging in lots of foreplay, and you're still feeling pain then visit your doctor. Usually some sexual pain after a while without sex is normal and will fade with practise. But if the pain continues then there may be another issue and your doctor can help identify a solution.

* * * * *

Hands on learning asks: I want to surprise my girlfriend with an erotic massage, but I have no idea what I'm doing. Can you recommend some tips and moves?

Jay answers: This sounds like a great idea! Your girlfriend is likely to love this plan!

While massage is not my area of expertise, I can make a few suggestions. These are in no particular order:
  • Get some massage lotion or body oil. It'll make the massage smoother and feel better for her. If it smells nice, so much the better.
  • Take your time. Start off with a focus on the "massage" part of the erotic massage. Gradually move closer to the more erotic parts, then move away again. Return to regular massaging, then return to some light erotic touching during the massage, and back off again. Ideally you'll be mostly making her relaxed while occasionally adding some light touching between her thighs, around her breasts, up the back of her neck. A good erotic massage, in my opinion, is more about teasing than full on sexual.

  • Consider getting a Harmony Ball. These feel amazing on the skin, especially if they've been placed in the fridge first. They're also easy to hold so it'll give your hands and wrists a break.

    A massage giver's best friend.

  • In my experience a good massage is mostly about starting light and trying to gradually add pressure over a wide area without "digging in". In other words, try to use the palms of your hands (or fingers held together) rather than pressing with your fingertips. Move your hands in circles over large muscles. Start light and slowly add more weight, asking for feedback until you find a level of pressure she likes. If she tenses up, holds her breath, or says "ow" then ease off. You're there to relax her, not fix her muscles.


    Keep your fingers together and use your palm to massage.

  • Consider getting a massage yourself, from a professional. Ask for a relaxation massage and pay attention to what the massage therapist does. Where they start, how they move, their pacing. Try to replicate that.

  • Practice. As much as your girlfriend will enjoy an erotic massage, she'll probably enjoy two or three even more! Practise makes perfect, so keep doing it, maybe in different positions (face up vs face down) and with different lotions, different pacing. Ask her what she likes best so you can improve your craft.

Best of luck, I'm sure the two of you will have a lot of fun!

* * * * *

Seeking orgasms asks: My girlfriend says she can't cum during sex, but every other woman I've been with always had a happy ending. What can I do to give her a Big O?

Jay answers: A large percentage of women have trouble climaxing, or are unable to climax, from penetrative sex alone. Many (maybe even most) require some direct clitoral stimulation to reach the Big O.

My advice will vary a little depending on whether your girlfriend is able to reach orgasm during other activities. If she reaches climax with you during oral sex, for example, then you could focus on doing more of that (before and/or after) penetrative sex. That way she gets to experience an orgasm even if it's not while your penis is inside her.

You might also look at getting a small vibrator to use during sex. Toys like the Womanizer and bullet vibes are small and can be placed on her clit while you two are having sex. This is likely to feel very good for her and will likely lead to an orgasm.
It works while you play!


On the other hand, if you girlfriend doesn't reach orgasm during any form of sex (oral as well as penetrative) but does reach orgasm on her own, then perhaps see if she'd be willing to show you what she does to get off. It'll be a hot form of Show-and-Tell where you can learn what excites her. Does she need to be on top and grinding, does she use a specific type of vibrator, does she listen to music, play with her nipples? Having her describe and/or show you what drives her to the peak of Pleasure Heights will go a long way toward helping you get her there.

Finally, may I suggest that you take care not to make your girlfriend feel like she's under pressure to orgasm? Nothing kills the mood like feeling like you're expected to cum. It's great that you want her to orgasm, but if you accidentally pressure her to orgasm it may make it harder for her to get off. Keep the mood light, let her know you want to please her. The orgasm should be a happy side-effect of you pleasing her rather than your primary goal.