My boyfriend and I have been together for 3 years and have been doing the long distance relationship thing for the past year. Luckily, we have the whole summer to spend together! We’ve made a ton of fun plans, including a 12 hour road trip up the coast of California… Which brings me to my question.
My boyfriend has always had a thing for fooling around in the car, and especially loves the idea of “road head”. While I’m definitely not trying to die that way, I’d love to meet him halfway and surprise him with some spontaneous car sex. I know he’ll love it no matter what, but I’m worried it’s going to be kind of awkward. How can I pull this off and make it a pleasurable time for everyone?
Thanks for everything you do,
I recently got out of a long-term relationship and jumped into dating—literally! Now I’m seeing three different people, something I’ve never done before, and need some advice on how to handle it.
Is there supposed to be a waiting period in between partners? Can I have sex with two different people in a week (with protection, of course)? If we use my sex toys, can I use them with multiple guys? Also, what’s the etiquette for telling a person I’m not monogamous in a way that won’t hurt them? I just want to be single and date around for a while, but it’s all so complicated!
Any advice would be appreciated,
Thanks for the sexual empowerment you offer to everyone. I have a question about introducing bondage and rough play with a new partner. How do you do it? I actually scared a guy recently when I asked him to choke me in bed. That is obviously not my future goal, so I’m hoping you can help me figure out a way to ease partners into it. Also, what’s the best way to tie someone up?
Thanks again for the great advice! I love your podcast.
Kelsey Continue Reading
Q: DEAR EMILY
My boyfriend of almost two years is skittish about sex toys. I’ve had them and used them with partners in the past (although those are long gone now) and I’ve been thinking of updating my collection. The problem is, I can’t seem to get my guy on board. He thinks that I want to use toys because I’m bored in the bedroom, or that it means he isn’t doing a good job. The thing is, he IS doing a good job. He brings me to orgasm more than any partner I’ve ever had!
I have been looking online and I really want the Womanizer or the We-Vibe Touch for Valentine’s Day. What do you suggest to help warm him up to the idea?
Thanks so much,
Mary Continue Reading
Q: Dear Emily
I’ve been with my boyfriend for around eight months and have still never had a REAL orgasm during sex. And as if this isn’t bad enough, I’ve been faking it! I know—it’s terrible! My partner has no idea, I just get so in my head about it and I want to make him feel good about his performance, but now I’m sick of performing. I want the real deal and I know I need to be honest with him, I just don’t know how to confess without hurting his feelings. How do I approach this?
Thanks, A Continue Reading
Q: Dear Emily
I met a man while traveling, we have been talking for a while since, and now he’s coming to visit. We haven’t been intimate yet, but I have a feeling that it will happen while he’s here. Which leads me to my question…
When I have sex, I produce a lot of female ejaculate, and if previous measures are not taken, the bed really isn’t suitable to sleep in after. I want to give this guy a heads-up, but I don’t really know how to approach this. Also I don’t want him to be disappointed if, for some reason, I do not “squirt” the first time with him (which has happened before).
Should I tell him beforehand? If so, how? Or should I just let it be a surprise?
With love, Sage
Q: Dear Emily
In the past year, I have been on a mission to have regular orgasms and since I’m currently single, this has been mostly a solo mission. I’ve been taking all of your advice: I’ve got the sex toys and the lube, I know where all my hot spots are and I know how to touch them, but I’m still only orgasming a third of the time. It’s so frustrating! Sometimes I will be right on the cusp of climaxing, but for some reason I just can’t get all the way there. What am I missing here? Help!
I have an issue I have yet to hear on your show. My wife of 19 years comes too quickly! (Yes, she actually orgasms and isn’t faking). It takes very little for her to reach climax and once she does, she is done. Me, on the other hand… I take a very long time. Obviously, this proves to be a problem as she comes first and is immediately done.
Because she comes so quickly, she is always in a rush to get me to finish. Once she is done she starts questioning me if I am done. Major turn off. She isn’t into too much foreplay and she doesn’t like giving oral sex (especially not to completion) so everything I have been taught falls apart completely. Is there anything you can suggest to make her last longer and be more into it? Thanks
Daniel, 52, Colorado
I’ve got a question about sex toy hygiene—I know you have a lot of sex toys and you use them pretty frequently. I am looking to step up my sex toy collection, but I’m worried about them remaining clean and sanitary for use. I’m 27 and haven’t had sex in a couple of years, but I want to start experimenting with myself. The only thing that’s holding me back is my fear of getting a yeast infection from dirty toys. What’s the best way to store and clean them? Also, is there a type of sex toy material that is bacteria resistant? Please help!
Xo, CJ Continue Reading