I’m a 33-year-old straight guy with a small dick. I have a girlfriend of seven years. When we met, I was really insecure and she had to spend a lot of time reassuring me that it didn’t matter—she loved my dick, sex with me was great, it was big enough for her, etc. I broke up with her once because I didn’t think she should settle for someone so small. After some hugely painful nights and another near breakup, we are in a good place now. We have lots of great vanilla sex, we love being together, and we recently got engaged. After everything I put her through—and I put her through hell—how do I tell her that being mocked (and worse) for having a small dick is the only thing I ever think about when I masturbate? I want a woman to punish me emotionally and physically for having such a small and inadequate dick. There’s porn about my kink, but I didn’t discover it until long after I was aware of my interest. (I grew up in a weird family that lived “off the grid,” and I didn’t get online until I got into college at age 23.) I’ve never been able to bring myself to tell anyone about my kink. How do I tell this woman? I basically bullied her into telling me that my dick was big enough—and now I want her to tell me it isn’t big enough. But do I really want her to? I’ve never actually experienced the kind of insulting comments and physical punishments that I fantasize about. What if the reality is shattering? —Tense In New York

“I was in a similar situation years ago with my then-girlfriend, now-wife,” said TP. “I was too chicken to tell her about my fetish and worried she wasn’t satisfied with my size, so I didn’t want to bring more attention to it. I eventually went to a pro Domme and felt guilty about doing it behind my girlfriend’s back.”

TP, which stands for Tiny Prick, is a prominent member of the SPH (small penis humiliation) fetish scene. TP is active on Twitter (@deliveryboy4m) and maintains a blog devoted to the subjects of SPH (his passion) and animal rights (a subject his Domme is passionate about) at fatandtiny.blogspot.com.

“I got really lucky because I found the Domme I’ve been serving for more than 10 years,” said TP. “It was my Domme who encouraged me to bring up my kinks with my wife. I only wish I had told my wife earlier. She hasn’t turned into a stereotypical dominatrix, but she was open to incorporating some SPH play into our sex life.”

According to TP, TINY, you’ve already laid the groundwork for the successful incorporation of SPH into your sex life: You’re having good, regular, and satisfying vanilla sex with your partner.

“TINY’s partner is happy with their sex life, so he knows he can satisfy a woman,” said TP. “That will help to separate the fantasy of the humiliation from the reality of their strong relationship. I know if I wasn’t having good vanilla sex, it would be much harder to enjoy the humiliation aspect of SPH.”

When you’re ready to broach the subject with the fiancée, TINY, I would recommend starting with both an apology (“I’m sorry again for what I put you through”) and a warning (“What I’m about to say is probably going to come as a bit of a shock”). Then tell her you have a major kink you haven’t disclosed, tell her she has a right to know about it before you marry, tell her that most people’s kinks are wrapped up with their biggest fears and anxieties… and she’ll probably be able to guess what you have to tell her before you can get the words out.

“He should explain to her that he doesn’t want to be emotionally hurt as much as he wants to feel exposed and vulnerable, and that can be a thrill,” said TP. “It can be hard for people to understand how humiliation can be fun. But humiliation play is one way to add a new dynamic to their sexual relationship.” —Dan Savage

I was traveling and forgot to pack lube, so I amused myself with some old conditioner I’d brought. It had some menthol in it or something and it tingled a bit, but it did the job. When I woke up, my dick had shriveled into a leathery red sheath of pain. I looked at the bottle again, and it wasn’t conditioner, it was actually a 10 percent benzoyl peroxide cleanser. After a few days, my leathery foreskin flaked off and the pain went away. Should I be concerned about my dick? —Onanism Until Cock Hurts

No, OUCH, your dick should be concerned about you. You’re the one who, despite having a foreskin to work/jerk with, grabbed the nearest bottle of whatever was handy instead of using the masturbation sleeve the good Lord gave ya. And you’re the one who didn’t read the label on the nearest bottle of whatever before pouring its contents all over your cock. Caveat masturbator! —Dan

I have a health question/problem. About a week and a half ago, the wife and I had sex. Being the genius that I am, I got the idea to put two condoms on because I thought it would help me last longer. (Spoiler alert: It didn’t.) The problem is, I guess the double condoms were too tight, and climaxing hurt quite a bit. For all intents and purposes, it’s like I duct-taped the tip of my penis shut and tried to blow a load. Even days after, the left side of my penis head was really sensitive and it hurt. It’s gotten better, but it’s too sensitive to touch from time to time. I have a doctor’s appointment to make sure I’m okay, but it’s two weeks away. I’m a little worried I may have hurt my prostate or urethra or something. From my basic googling, there doesn’t seem to be any medical advice about this. Help please? —Penile Problem Possessor

“The application of an external constriction to the penis did potentially cause the pressure in the urethra to rise, possibly traumatically, during ejaculation,” said Dr. Keith D. Newman, a urologist, a fellow of the American College of Surgeons, and a regular guest expert in Savage Love (his most prestigious professional accomplishment).

In other words, PPP, somehow those two condoms conspired to dam up your piss slit—aka your urethral meatus—and the force of your impeded ejaculation damn near blew off your cock.

“We sometimes see a similar phenomenon occur with people who wear constriction bands or cock rings that are too tight and try to either urinate or ejaculate with the ring on,” said Dr. Newman. “The result is a traumatic stretch of the urethra and microscopic tears in the lining of the urethra (mucosa). This disruption in the lining allows for electrolytes in the urine (particularly potassium) to stimulate the nerves in the layer beneath the lining (submucosa), thereby creating a chronic dull ache, such as PPP describes.”

Your urethra should heal just fine in time—within a couple of weeks—but there are meds and other interventions if you’re still in pain a few weeks from now. “The bottom line is never impede urination or ejaculation by obstructing the urethra,” said Dr. Newman. —Dan