Dear Ty

Dear Di,

I’m graduating in less than a month, and not once have I experienced orgasm. Part of the reason for this is because I find it incredibly hard to do anything sexual, even masturbate, if there’s any chance that someone might hear. How can I calm down to pleasure my lady parts?

—All Tensed Up and Nowhere to Go

 

Dear ATUNG,
No one should have to experience the milestone of graduation without having experienced another milestone: the joy of an orgasm. Let’s focus on how you can get yourself to hit that high. Your main problem, as you’ve identified, is your inability to calm down. You say that you’re worried someone might overhear the solo sex sounds you make. As it turns out, it’s not too difficult to control your moans, especially when you’re twiddling your twat alone. In addition, pussies don’t actually purr when you pet them, nor do they make awkward slurping sounds that can be heard through a closed door. In short, stop stressing that someone might hear you, because they very likely won’t. Furthermore, you can control when you touch yourself, so if you’re truly that worried about someone hearing you, simply masturbate when no one’s around. Besides, if someone does hear you, chances are they won’t actually care that much. Everybody does it.

My next piece of advice is to clean your sheets, put on a silky nightgown, pour yourself a glass of wine, and watch a movie (porn or otherwise) featuring a leading man or lady who gets your panties wet. Don’t expect that you’ll orgasm, but start experimenting with touching yourself. Pinch your nipples, rub your clit, slide a finger or two inside of you. Just play around with what feels good, and truly focus on the sensations as they come. With practice—and perhaps the help of something battery-operated—you’ll eventually be coming too.

Love,
Di

 

Dear Di,
I’m a happily employed sex worker. I recently started dating again after ending a one-year relationship. I’ve taken a few months just being single to heal and move on from what happened between me and my ex-boyfriend, and I can say with confidence that I’m once again ready to try my hand at romance.

Naturally I’m a bit nervous about it (who wouldn’t be?) but the only thing I’m having trouble calming myself down about is my job. I took my job while I was still with my last boyfriend, so we talked about it before, during, and after my transition into this unorthodox line of work. I know that there are other people out there who will be just as supportive and understanding of what I’ve chosen to do, but how do I make it easy for them?

I don’t know whether the right thing to do is to mention what I do early on, the way I would with any other job, or to wait a while until there’s a certain level of mutual trust. Should I ask how my dates feel about prostitution before mentioning it, and take a cue from there? I’d like to avoid the “You’re a WHAT?!” confrontation as much as possible, but I also don’t feel obligated to say, “Hi, I’m your date, and I’m also a hooker.”

What do you think, Di?

—Pro Amateur

 

Dear PA,
You sound like a really conscientious person who is clearly ready to start a healthy and mature relationship after what sounds like a bad breakup, so kudos to you.

I wish I could walk you through this process step-by-step, but unfortunately, I don’t have the perfect script for you to follow. I think the best way to tell the people you’re dating about your profession will differ according to the personality types of your dates and how interested you are in pursuing a relationship with them.

Although sex trade talk certainly isn’t on the agenda for the majority of first dates, you can expect that most people will want to know what you do for a living within the first 30 minutes of a rendez-vous. I can understand why you might want to hold off on talking about your profession until there’s a certain level of trust established between you and your date, but to do so, you’ll likely have to lie to him or her right off the bat. If you end up continuing a relationship with this person, you’re going to have to tell them eventually, and trust me, there’s no quicker way  to kill a good thing than by admitting to fibbing

If I were you, I think I’d be honest from the get-go. When your date inevitably asks you where you work, I would start by saying that your job is unconventional, but it’s something you really enjoy, and then tell the truth. Expect the other person to be a little suprised and curious at best, or downright repulsed at worst. If he or she can’t take it, politely end the date and move on to someone who can.

Assuming you’re going out with a person who is open-minded and willing to continue the date, I would then share with him or her what you enjoy about your job. Expect the other person to have a lot of questions, so you should be willing to provide honest answers (assuming, of course, that the questions are respectful in nature). I would also be prepared to talk about safetyanyone you might be getting intimate with in the future will likely want to be assured you’re doing your work in safe way.

As you move forward in a relationship, I would encourage you to remember that the two of you will likely face challenges that other couples won’t. Weather the storm by allowing each other to make mistakes and by being extremely open and honest about your and your partner’s boundaries and expectations. There will be some fumbling along the way, but as long as neither person expects the other to handle every difficult situation perfectly, I think you’ll find you can make it.

Love,
Di