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A Middle-Aged Woman's Sex Dilemma

I'm not sure I'll ever have sex again.

I joke around about how much I want sex with young men (because I do), and I've shared some saucy details about my past sex life in my writing. But there are some details I've minimized or left out, and these details are the reasons I'm not sure I'll ever have sex again:

  • After my last serious relationship ended in 2012, I pretty much stopped being able to have an orgasm brought on by anyone but me.

  • I haven't had sex since the end of 2018.

  • The last few times I did have sex, intercourse was too painful for me to continue longer than a couple of minutes.

  • I usually cry before or after any sexual encounter.

  • I'm lonely when I'm not sexually active, but more emotionally unstable when I am, so it's hard to decide which is better.

Let's briefly examine each of these sex obstacles I'm hoping to overcome.

Inhibited Orgasms

I never thought I'd be having sex with strangers. All through my twenties and thirties, I only had sex with guys I was dating. Then I went through a difficult breakup, and I didn't have sex for five years. When I finally did start having sex again, I was dismayed to discover that it was a lot harder for me to cum. Now I had to rely on myself to make it happen, lying beside the guy in the post-coitus afterglow.

I hate it. If the guy cums during sex, I want to cum, too. But I'm not confident enough to tell him exactly what I need to get there. Usually, what I need is for him to keep doing certain things (oral and manual things, to be specific) for longer, but I'm too shy to ask. Why? Because he's a stranger. I don't feel as comfortable being honest with a stranger as I would be with a partner I knew and trusted.

I get a lot of pleasure out of having sex with young men, and there are advantages to having sex with someone you don't know well. It's definitely exciting, and I've learned a lot about myself from those experiences. I just wish those experiences included the guy giving me an orgasm before the night was over. I'm never completely satisfied as a result.

Chaste Since 2018

It's been four years since the last time I had sex. I guess it's not that big a deal. In the past, I've gone as long as five years. (Both times followed painful breakups.)

Having said that, it is a big deal. I want a sex life. Maybe not everyone needs physical intimacy, but I do. I'm a very affectionate, sensual person. I like being touched and held. I like sex. I'm just not having any.

Many factors have contributed to the fact that I haven't been having sex. There was a pandemic, and then I've been couch-surfing since December and have had very little privacy as a result. I've also been dealing with a decline in my mental health. When you're feeling suicidal, sex isn't a high priority. For months now, I've just been trying to get through the day.

Part of me worries that, after so long, I'll somehow have forgotten how to have sex, or I won't be able to enjoy it the same way. It's just hard to get back in the saddle after four long years. Especially because the last few times I had sex were far less than ideal.

Painful Intercourse

One time it hurt because the guy was crooked. Another time it hurt because the guy was thick. Both times it hurt because I also wasn't in the right mood.

Intercourse hurts if I'm not aroused enough and get tense. The last few times were like this. Intercourse was uncomfortable and I had to ask them to pull out after just a few minutes. It was frustrating and embarrassing.

Intercourse never used to hurt. Again, probably because it wasn't with strangers, so it was easier to trust the guy and relax. It was painful the last few times I tried to have sex, and I'm worried it'll be painful the next few. If there will be a next few.


Ah yes, the tears. I have complex PTSD, and I have to deal with a lot of triggers in life. If I get triggered before sex, the young man and I have to wait until I'm feeling okay again before we proceed. If I get triggered during sex, sometimes I can override the urge to cry and sometimes I can't. Tears after sex are often shed after the guy's already on his way home.

It was very rare for sexual encounters to make me cry in my twenties and thirties. I think there are many reasons why it's difficult for me to dodge tears now. Needless to say, crying on dates isn't fun, and takes away from the fun and pleasure of sexual experiences.

Sex and Instability

I often feel like my body wants what my mind can't handle. I wish I could just have casual sex and be done with it, but the truth is I'm vulnerable and need someone who understands me and can give me the support I need to feel comfortable and safe.

I think my mental health challenges may always make navigating relationships difficult for me, especially sexual relationships. I'm sensitive on every level, which can be a great asset physically (my whole body is essentially an erogenous zone) but can be a liability emotionally. I always feel things so deeply, and I think too much. It makes having sex feel like walking a tightrope: clinging to the pleasure while all of my worries and fears wait for me down below. There's a wonderful reprieve from my anxiety and sadness during sex, but they're always there to find me again later that night or in the morning.

Maybe not everyone needs physical intimacy, but I do. I'm a very affectionate, sensual person. I like being touched and held. I like sex. I'm just not having any.

If I Ever Have Sex Again...

I'm worried that any future sexual encounters I might have will play out like my last ones:

  • Sex with guys who don't give me orgasms.

  • Sex where I feel awkward.

  • Sex that's painful.

  • Sex that makes me want to cry.

  • Sex that leaves me anxious or sad.

I want to believe that the things I struggled with in my past sexual experiences don't have to limit my future ones. If I have sexual experiences in the future (which I fucking hope I do, which is to say I have hope for future fucking), I hope they'll look like this:

  • Sex with guys (or girls) who can bring me to orgasm.

  • Sex where I get some confidence back after a long hiatus.

  • Sex that feels good.

  • Sex that only makes me cry happy tears.

  • Sex that enhances my mood and my life.

Anything is possible, right? To paraphrase what a boss of mine used to tell me when I said something couldn't be done, "They got a man to the moon, Melissa - how hard can it be?"

Hopefully, I get a man in my orbit soon. I'll leave the "how hard can it be" joke to you.

- M.B.

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