Ask the Intimacy Advisor: Opening Up

by Kristin T.

June 8, 2022


Maybe you’re embarking on a brand new relationship with a lover who wants to try something you’ve never tried before. Or maybe you are looking for new ways to bring the sexual spark back into an ages old romance. Either way, the quest for sexual fulfilment can sometimes send us to the edge of our comfort zones…and when people are about to embark on something new and exciting, it can be downright confusing…even scary…so folks are bound to have questions.

This edition of Ask the Intimacy Advisor is themed around questions from readers like you about issues like this. Whether you’re curious about opening up your mind to new possibilities, or opening up your bedroom activities to new participants just because you’ve always wanted to, it’s nice to get some answers or reassurance before you start a new journey of sexual openness. And most of the time, when one reader has a question like this, lots of other people do, too, so hopefully the advice given here can help you with some of your own relationship quandaries and conundrums!

Question: G’day to ya! I’m a 60 YO man, in a 17 yr marriage, with a 57 YO wife, where romance and intimacy have unfortunately fallen off the map. There are several reasons on both our parts. It was gray and stale and felt like an act of necessity, rather than love and closeness, for several years, before coming to a near halt (3-5 times a year). I’m not ready to be done, however. I’ve taken to seeking fulfillment outside of marriage. As it turns out, I’ve been invited to participate with another MF married couple, in a threesome relationship. It’s in the opening stages and I’m curious what might be some critical and often forgotten questions to ask of the other couple, when entering a situation like this. Your advice is appreciated! ~ Trigger

Hi Trigger. I have some suggestions of questions you can ask the other couple, but my first question for you, since you didn’t specify, is if your wife is okay with you entering this arrangement. Seeking extramarital sex is definitely not uncommon, especially in cases like yours where the sexual spark has just gone away, but it still has to be consented to by ALL parties involved or it’s just cheating. Perhaps she wants to have sex with you more often and hasn’t felt able to ask for or initiate it, or perhaps she knows some deeper reasons you two have stopped being sexual but you may be able to solve the problem through a solution you haven’t tried yet. Heck, maybe she’d even be interested in a swinging or partner swap arrangement or bringing a third participant into your bedroom! You never know until you talk about it. It may not be too late to get the sex in your marriage back before you seek it elsewhere.

That being said, if it’s been discussed and is on the up and up with everyone and you still want to join this other couple, the first thing to discuss will likely be the expectations of the arrangement, because you need to be okay with all of them. Will you truly be dating or in a relationship with the other couple, or would you only be participating in their sexual activities? The time investment necessary for those two options is likely to be very different, and you AND your wife need to be willing to make that commitment. Secondly, you need to be clear on their expectations of you and exactly how they would like you to participate with them during sex. Will you be directly having sex only with the female or with both of them? Kissing? Oral sex? Anal sex? Using toys? Establish what is and is not ok for you to do with each of them and for each of them to do with you. Finally, any time you bring a new sex partner or partners into the mix, it’s important to have the STI conversation and use protection until you are certain everyone is trustworthy, safe, and can present clean test results.

This type of arrangement can work, though it may not be easy. Hopefully it will bring you the sexual fulfillment you are looking for, and maybe it will even help you get your overall libido back enough that you will become more interested in sex with your wife again, too! Generally speaking, the more sex you have, the more often you want to have sex, so hopefully everyone consents and can benefit from you getting your sexual spark back with this other couple first. Good luck!

Question: I’ve have had feminine tendencies and have been cross-dressing since I was 14. I recently lost my wife. I’ve now decided I would like to start transitioning to be a full time female transgender person. It is something I have wished and dreamed about for a long time. At 55 years old, do you think it’s too old for this change? ~ Jamie

Congratulations, Jamie, for accepting this truth about yourself and finally allowing yourself to live your best life as your truest self. I am sorry for the loss of your wife; I am sure that was difficult and caused many challenges and changes in your life. Life certainly looks different for you now, but if you can use this new life as a catalyst for change, and as a chance to fully embrace the identity you’ve never been able to live as before, this may be as good a jumping-off point as any.

If you know it has always been your dream, it doesn’t sound like a decision you’d be making lightly. It’s my belief that you’re never too old to live your dreams, though transitioning may come with more challenges for you now than it would have if you had made the transition at a younger age. It may be best to start with small, easy changes while you think about exactly what other kinds of changes you want to make towards becoming a female transgender person. Dressing in women’s clothes full time and changing your hair and makeup may be the easiest change to make, along with deciding on your preferred pronouns and helping people in your life remember to use them when speaking to or about you. Be patient if they slip up; if they’ve known you as a male and by a different name and pronouns your whole life, it will take some getting used to, but you deserve to be addressed how you identify and prefer, and hopefully everyone will respect this adjustment.

You also need to decide to what extent you want to transition physically. It is possible to simply change your gender presentation without changing your sex; think about what is most important to you to help you feel like the female you have always known you are, and what you need to do (and are willing to do) to achieve that level of transition. Do you want sex reassignment surgery? Top? Bottom? What about hormone therapy to help change your voice, hair, and features? Is cosmetic surgery to create more feminine features on the table and important to you? The most important conversation you need to have as you embark on this journey is with your doctor. Find one who is open-minded and willing to advocate for you during this process, and they will let you know what is and is not likely to be safe, feasible, and effective as you make these medical changes you need as you begin to become a female transgender person. It will not be an easy journey, but I am sure you will find it to be a worthwhile one as you can finally begin to live your authentic truth.

Question: Do you guys happen to sell strap-on dildos that a man can wear to use on his girlfriend for something different once in awhile? I’ve been having a bout of E.D, and to be honest I want to try having sex with her with something a little bigger than me too. ~ Steve

E.D. can be frustrating, Steve; hopefully you’ve also talked to your doctor about addressing it long-term, but good on you for looking for alternative options so you and your girlfriend can still enjoy penetrative sex when you want it! Lover’s Lane stores and definitely carry options for strap-ons that can be worn by a man or a woman, including hollow ones like the Lux Fetish Vibrating Hollow Strap-on.

You may also be able want to try a toy like The Enhancer to help stiffen your erections and add girth and vibration, or a penis sheath or extender can also give you the pleasure of giving her something a little bigger, but it’s still you. This means you can still feel all the sensations of penetration because you’re doing it with your own penis instead of a strap-on. Many of these sheaths and sleeves have built-in cock or ball support rings which can also help you maintain an erection, and the extra layer of material between you and her vagina means you can last longer, so you can make the most of the erections you can get!

Question: My girlfriend wants to start experimenting with anal. Not just on her, but on me too! In my 47 years I have never even considered it, but I want to make her happy. I have limited $ being a disabled Veteran. What are some inexpensive toys that I can use when she is not around to acclimate myself to her request? Please help I am at my wits end here, and to be honest I can’t even believe I am considering this. ~ Wolf

Good for you for being willing to open up to this possibility, Wolf, and if it provides any reassurance, you are definitely not alone in your apprehension about anal play. Unfortunately it has earned a bad rap over the years, being considered dirty or often assumed to be only enjoyed by gay guys. None of those myths are true, though, and the truth is, almost everyone who has a butt can enjoy butt stuff!

The easiest way to begin this process is not necessarily with toys, but just with your fingers. Start circling around your anus on the outside with a finger, then apply some lube and insert just a fingertip inside your anus a little ways and circle it around. You can also easily enjoy this exploration in the shower, and you’ll likely find it very pleasurable. You can start to tease and please your girlfriend in the same way; have sex with her in the doggie style position, and gently run your finger around her anus, and begin to insert it a little when she expresses she is ready for that.

Toys are also great for anal training, with a good general rule being to start small and work your way up. Some plugs are sold in training kits with three sizes so you can do just that, like the B-Vibe Anal Training Set or the Her Little Gems Trainer Set. You have the bonus over your girlfriend here because you have a prostate, so you may find you enjoy anal pleasure way more than you thought you would once prostate stimulation gets involved! This Intro to Prostate Kit comes with all the beginner-friendly toys you need to start experimenting with all the pleasure this little gland can bring you, and once you have practiced yourself, you can let your girlfriend start stimulating your prostate manually or with toys! Just remember any time you’re playing anally that lube is your best friend, and have fun with it!

Question: I have a beautiful girlfriend of 8 months, and 6 months ago we started a sexual relationship. My question is sometimes when we have intercourse, she says it hurts because the head of my penis bumps up against her cervix. Is this normal, and is it possible my penis is too large for her vagina ? ~ Lightning

This is a good question, Lightning, and definitely a normal and common problem many couples experience. Just like every penis is different, women’s bodies are all different, too, and the exact size and placement of those internal parts of the vagina can vary greatly from woman to woman. Your penis isn’t necessarily too large; some women simply have a “shallow cervix”, making it very common to jab it with your penis during penetrative sex regardless of size…and as any woman who has had this happen will attest, yes, it definitely hurts!

The good news is there are several simple solutions to this problem. Try some different positions that will put some more distance between your groins, such as both of you lying on your sides while you enter her vagina from behind. Positions that put her on top may be a good option as well, as she can better control the angle and depth of penetration.

The sex toy industry has also stepped up with a solution to this problem. Traditional thick cock rings can act as a “spacer” so you are unable to penetrate as deep, but the Ohnut Penetration Depth Rings were created for this express reason. This set of four comfy, stretchy rings allows you to wear as many or as few at once as you need to keep your penis from entering her quite as deeply, preventing those painful cervix crashes. Experiment with different numbers of rings in different positions to figure out exactly what works best for each option; each one has a lip to hold it tightly to the next one so they can stack together without slipping or pinching. Then you can both play the night away pain free!

Question: My lover and I have talked about exploring some more sexual atmospheres. Is there a local site that has planned parties or gatherings for people with such open ideas? ~ Pick

Great question, Pick. It can be fun to expand your horizons and try out new settings and new groups of open-minded people for sexual exploration, kink play, group sex…whatever you’re looking for, really. And at least around most major cities, there tends to be a fairly large community of people who are also into these types of parties and scenes, though they may not be super openly advertised.

The best way to get invited to play parties, polyamory or kink meetups or “munches” (always a good place to start – basically just hanging out in a bar or restaurant chatting and getting to know like-minded people), and other types of sex or kink parties is to know someone who goes and have them bring you along. Being invited by a known member of the community is often seen as an alternative to the somewhat strict vetting process some groups may have, which is a vital part of keeping clubs or parties safe for everyone.

If you don’t know anyone who can welcome you into their circle, create a profile on FetLife if you haven’t already, and you can start to make friends and learn about events in your area on there., Adult Friend Finder, and even Craigslist all offer plenty of options for alternative dating and the BDSM community, so sites like that may be a good place to start as well. You may also be able to find out about events in your area through those free arts & culture magazines like Metro Times, Time Out, The L, etc. Good luck and have fun!

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