Dear How to Do It,
I read the letter from “accidental size queen” with interest because I think she and I have something in common. I’m a woman and have been married to my husband for six years. He’s handsome, funny, and a great dad to our 2-year-old, and we are building a pretty great life together.
Why I’m writing is because his penis is quite small. He’s never brought it up and we’ve never talked about it, and so I hope that means he’s comfortable with his body. We have fun in bed beyond P-in-V sex. Clearly, all his equipment works (see: 2-year-old). We had sex before marriage, so it was not a surprise to me after vows were exchanged.
The thing is, the last couple of my boyfriends before my husband were pretty big. My last boyfriend was what I would call “porn star big.” And I Iiked it. They were both pretty good cocksmen, and there’s a special feeling having them be so deep inside. It’s a little hard to describe, but I’ll just say that it was pretty great most of the time.
And I have to say that I kinda miss it. No, I miss it a lot, actually. Not enough to cheat on my husband and hook up with my ex, but there’s a void in my sex life, so to speak. It was heartening to hear ASQ’s husband wanted to give this to her with a strap-on toy. So how do I get some of that lovin’? Is there a way to bring this up with my husband that doesn’t hurt or shame him, or make him second-guess what he brings to our sex life? Or am I just doomed to small-dick sex? I’ve thought about buying my own large dildo, but there’s no way I could keep that hidden here without him discovering it. There’s just not enough hiding spaces, and I’m not going to take out a safe deposit box.
—Size Queen in Retirement
You’ll want to choose your words carefully: “Doomed to small-dick sex” is a doozy. It implies that your husband is inadequate in size, that you’re deprived, and that this is a deal breaker for you. I imagine you were swept away by poetic license, but if that’s really how you feel, you have bigger problems than wanting to try to bring in a large dildo.
If I’m right and you are mostly satisfied during sex, think about what you want to say to your husband. There is rarely a way to approach a sensitive request in bed without risking upsetting our partner somehow. They might be squicked out or reject us. They might feel inadequate. They might feel like you’ve hidden something and be angry. Mitigating risk is absolutely an option—though not entirely guaranteed—and you, being married to the guy for several years, are best suited to figure out how to approach this.
Unfortunately, you’ve never talked about the size of his penis and how he feels about that, so we don’t have much insight. You might inquire about your husband’s general sexual satisfaction, and lead the conversation into mutual sharing of desires. You also might dive straight in and say “I read this column about long strap-on dongs and now I kind of want to try that.” It should all depend on how the two of you relate to each other and how the conversation is going in the moment. Presumably you can read your partner’s face and body language somewhat, and those inputs will help you monitor stress levels. One thing you’ll want to be careful of is pushing the conversation too far and overwhelming him with emotion. That’s one of the times when discussions tend to break down, which can cause bad feelings all around. If you feel like a break is in order, say that. Something like “Let’s take a breather.” Or “I’m getting overwhelmed; can we pause for a while?” Good luck.
The Question You Can Never Ask Men on Dating Apps
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Dear How to Do It,
My girlfriend “Kylie” (36) and I (43-year-old man) began dating 11 months ago. We met through Tinder and immediately hit it off. We are both divorced with three children each. Our custody schedules allow us a fair amount of adult time that we fully take advantage of.
While I have had a fun and varied sex life, Kylie married her high school sweetheart after graduation and had a dull, unfulfilling sex life with a selfish narcissist. They divorced 14 years later. During her marriage, Kylie never gave nor received oral sex, never was on top, and never orgasmed from sex. She began dating about a year after her separation and enjoyed catching up on some of the fun she missed out on by getting married so young. For example, she watches porn to masturbate and reads forums to learn how to give a proper blowjob. She tried anal sex, bought vibrators, and even had a one-night stand.
Our sex life is absolutely amazing. I am able to go for a really long time and Kylie is multiorgasmic and squirts vigorously when things really get going. So far she has been open to trying new things with me like light bondage, toys, anal (for both of us), and some other things that are new to me as well. For a single mother of three young kids who was with one person for 14 years and three others briefly before we met, she really gets into sex more than I had anticipated.
The “problem” with me is that I have this deep, long running kink/desire/fantasy to see my woman with another man. Not as a humiliation (cuckold) kink, but more of a “hot wife” where we would choose a man together and I watch and join in while they have sex. Thinking about seeing her riding someone else, having an orgasm, or giving a blow job to someone else while I’m inside her absolutely drives me crazy. Even as I can feel this tingle in my chest whenever the thought crosses my mind and my breathing increases. I don’t desire to play the cuckold role and watch it go down from the corner of the bedroom—I want to be fully involved with pleasing her. And pleasing her is always my priority No 1. Even though it’s my fantasy, the biggest turn-on for me would be seeing her absolutely overwhelmed with pleasure and doing something neither of us would ever forget.
Here’s the problem with this problem: One of the guys Kylie dated early on, “Ken,” had convinced her that the sex with her was so good he needed to share her with his best friend. So he gave the friend her number and let them sort it out. The intention was that the friend and Kylie would do this without Ken being present. The friend came to her apartment and nothing bad happened, but Kylie decided this wasn’t for her and asked the guy to leave. We only ever talked about this once, and the conversation got derailed by a phone call before I could get a better understanding of what changed her mind and what her thoughts are of a MMF situation. To me, it seemed like she might be into it. Kylie more than considered the thought—she proceeded to plan an encounter. That tells me that there is a way I could frame this and not have her feel like a piece of meat, which is my guess as to what happened the first time. Kylie hasn’t brought this up or even hinted that a second penis is on her wishlist. How can I begin a dialog that won’t make my girlfriend feel cheap, but rather loved and adored? I truly love this woman and will marry her in the immediate future. She knows I have a very kinky side and a really strong, above-average sex drive, so I don’t expect that she’ll be shocked when I bring it up, but my fear is getting a knee-jerk, “no way” response that I won’t be able to undo.
—Would-Be Hot Husband
As with our writer above, there’s no way to guarantee your girlfriend won’t give you a “no way” response, and if she does, that’s her prerogative. Her feeling very well could be “absolutely not,” and if you encounter that and keep asking, you’re headed into coercion territory. Attempting to undo a firm “no” is not healthy.
In my read of your letter, Kylie has given you no indication that she might want to incorporate another man into your sex lives. You’ve got this whole story where she changed her mind and you can change it back when the reality is that it’s quite possible she was never interested in another man and only willing to meet with the guy because of Ken’s desire.
The next time the two of you have privacy and a couple of hours, ask her directly. Find out what happened, how she felt, and what she wants. From there, you’ll have a much better idea of where her boundaries are, and I do hope you’ll respect them.
Dear How to Do It,
I am in a relationship with a fantastic man with whom I was recently reunited after being separated by stay-at-home orders for a few months. We have been enjoying getting back on the bicycle, so to speak, but for one minor hangup. My boyfriend is self-conscious about having gained the “quarantine 15”—or closer to 25, as he would tell it. I honestly cannot tell the difference (20 to 25 pounds on a 6’2 large-framed person looks like nothing). I find him incredibly sexy as always, but I can tell he is self-conscious about being undressed around me.
Both inside and outside of the bedroom he is always very positive about my body—telling me how sexy he finds my body, kissing me all over, etc.—and generally does a great job making me feel like a sex goddess even on days when I’m not necessarily feeling myself. Now I feel like it is my turn to return the favor and I am coming up short. He seems to be uncomfortable and deflective when I try to compliment his body at all, which he wasn’t prior to his weight gain, and tenses up when I try to kiss around his “love handles” (his words).
In my previous relationships with women (I am a bisexual woman), these gestures were more well-received, so now I am not sure if my issues are specific to my partner or if it is a sign of some kind of general misunderstanding I have of body-positivity for men.
It makes me sad to see him so down on his appearance and I am cautious about discussing it further for fear of exacerbating his confidence issues. I also understand this is deeply personal to him and not something I can try to “fix.” Still, I feel like I can at least take steps to support him and I am not yet sure what those steps are.
It’s quite possible that your boyfriend doesn’t want to be reminded of something he’s sensitive about, and that your compliments cause him to focus more on the parts of his body that he’s unhappy with right now. Try targeting your compliments elsewhere. Thank him for all the positive feedback he gives you. Tell him he’s an amazing lover. Give him praise for his intelligence, his empathy, his organizational skills, or whatever else he’s good at. Essentially, remind him of everything he can be proud of and give him a break from thinking about his body.
Sometimes it’s difficult to understand what we need and articulate it, but you can also try asking your partner directly what you can do to help—or avoid to help. Good luck.
Dear How to Do It,
What advice do you have for a guy who will turn 40 this December and hasn’t been physically intimate with a woman yet? (Yes … I’m asking for myself.) I have diagnosed ADD and bipolar disorder. I’m not as nervous about the act as I am broaching these topics, because they’re both highly stigmatized. As far as the bipolar goes, I have it under control with meds and therapy, but I do feel she should know first.
I’m also aware of what movie this relates to. And it was hilarious.
—Old Man and the V
Disclosing is your choice, and I’m of the opinion that it’s only necessary when something is relevant to the other party. So, ADD—being likely to come to bear during the act of sex— is pretty important to disclose. A bipolar diagnosis, controlled with medication and therapy, may not be relevant to a casual hook-up. I disclose my ADHD diagnosis to most people, whether I’m having sex with them or not, because it affects most interactions. I don’t feel a need to disclose my OCD diagnosis until they see me checking the front door three times.
GoAskAlex, a sex worker and advocate, did a video for the 18+ magazine I co-founded on how to disclose disability. The gist of her advice is to state the fact plainly, with attention paid to how this relates to the person being disclosed to. We’ll use my ADHD again: At an event where someone is rustling through their bag during my talk, I’ll tell the audience, “I have ADHD, and I am currently unable to focus due to noise.” Dates usually encounter the concept when they try to take me to a restaurant, and I explain that we have to sit outdoors, or I’ll be struggling to turn speech into intelligible words against the background noise of other diners. Yes, COVID-era outdoor dining was a huge boon for me. The running theme is that I use this format: diagnosis, then how this affects our interaction.
That last part is crucial, especially with stigmatized labels. Stigma tends to come with assumptions that are inaccurate or not quite accurate, so it’s important to communicate what your reality is. Try to keep your explanation clear and concise. You may even ask your therapist to help you come up with a short paragraph that describes how your particular mental makeup is likely to affect potential partners.
Beyond that, I suggest that you read a couple of books—Emily Nagoski’s Come As You Are is a great primer on sexual response, and Ian Kerner’s So Tell Me About the Last Time You Had Sex is one of Rich’s favorites. Remember that porn is not a how-to guide. And build a baseline of back-and-forth communication with your partner to make direct discussion of sex easier. No matter how much experience and expertise you accrue, you’ll start from square one with every new partner. So practice having clear conversations about sexual desire and response. I think you’ve got this.
More How to Do It
Last night, I went on a date someone who I had met somewhat spontaneously a week or so ago. We were having a really great time—natural conversation, very similar interests, just a good vibe. I don’t normally click with people this easily, and I was so glad our connection didn’t start on an app, so I followed the mood a little more than I might have otherwise and went back to his place. We slept together, and it lived up to the rest of the night. But in the afterglow, he casually admitted a little fact that made me feel instantly betrayed.