A: Whether you are a male or female, the best thing you can do is to figure out what feels good to you. If you’re able to orgasm through masturbation, pay attention to what works for you both physically and mentally. It’s preferable that you feel comfortable with your sexual partner- comfortable enough that you can communicate this issue to him or her, not be worrying about it during sex, and be willing to try different things with time and without pressure to succeed right away.

[ Cross posted from Yahoo! Answers, where this SFSI Answer was chosen best answer to this question. ]

So here’s where I took a leap. I told FriendX about this sexual attraction she has for him. He was pretty shocked, but was cool with the situation. We talked about whether a relationship could just be sex, and how she and I are happy as a couple. We broached the subject of setting something up in the near future, something along the lines of a surprise for my wife. Next weekend is her birthday. I was thinking about greeting her at the door with him next Friday night. Maybe telling her that he knows everything, etc and we should live out her fantasy. What do you think about this? Should I do this? Any suggestions about how to do this? What should I do if they start screwing around–its not like husbands hang out while their wives are having sex with their friend? And lastly is this/me/her normal???

A: First off, we really wouldn’t recommend springing this on your wife as a surprise. That might work out well, but it might also be extremely awkward. The two of you have talked about her attraction to FriendX as a fantasy, but very often there are differences between what people enjoy fantasizing about and what they actually want to do in real life. Also, fantasies tend to leave out a lot of the dull but important details. What kind of activities are okay and what’s out of bounds? What kind of protection will everyone be using against STDs or pregnancy? Who will be playing with who? If either of you gets uncomfortable or just isn’t having fun, do you have the right to call a stop and ask him to leave, even if the other partner is still into it? Will it be a one-time thing or ongoing? If it’s going to be ongoing, will it always be all three of you together, or would it be okay for her to have sex with him without you? Is this just about FriendX, or are you interested in opening your marriage in other ways–like you having other partners as well?

It would be useful to have a serious, explicit conversation with your wife to answer questions like these with the clear understanding that you’re talking about actually doing it–not just talking dirty while the two of you have sex.

That would be the best way to get your question about how you’re going to participate answered as well. There’s no right or wrong answer. Some husbands do hang out, or hang out and masturbate, while their wives have sex with other men. Some couples have threesomes where everyone participates. Some couples have open relationships where one partner might have sex with a third party while the other partner just goes and does something else. What’s important is that the arrangement be agreeable to everyone involved.

And as for your last question, there is a substantial minority of married couples who include some kind of consensual extramarital sex in their relationship. The Janus Report, which was a survey of sexual behavior done in the early nineties, concluded that around 10% of people in their first marriages had had threesomes. And as I talked about above, a threesome is only one style of extramarital sex. So maybe that number is under-counting. The exact percentage probably isn’t important: the point is that you’d be far from the only couple to have included a third party in your sex life.

We’ve discussed restraints in the past, just kind of flirting with naughtiness, and I mentioned a few things like using a strap-on and tying him up and he seems very VERY interested. I am not an experienced Domme, and while I don’t always think along those lines, I am a pretty kinky gal, and it would give me a great deal of pleasure to do damned near anything to please this man.

I am concerned that restraining and flogging him or blindfolding him may remind him of horrors he has really faced. He tells me he wants these kinds of things and he’s strong as an ox, but I am concerned about his psyche. Are there articles I can read about topping a combat vet?

Life begins at 50! I just don’t want a new chapter to slam on my Sweetheart.

A: We’ve looked, but we can’t find any resources specifically about topping a combat vet. However we do have some ideas.

First, there is a significant chance that topping him will not trigger him. It’s still probably worth planning for, but you may never actually have to deal with it. Before doing anything that you’re afraid might be triggering, you and your partner may want to create a trigger plan. The best resource we’ve found about how to do this is geared towards adult woman survivors of childhood sexual abuse (The Survivor’s Guide to Sex, by Staci Haines) but we think some of it can be applied to your situation. The basic idea is to develop a plan with your partner of what both of you are going to do in the event of a trigger. How might he behave? How will you recognize it? What can you do to help him? How can you take care of yourself? What can he do in the moment to bring himself back to the present? This will likely be a longish conversation, and you may never need it, but if you do you’ll be glad to know what to do. Has he ever been triggered by anything before? How does he behave? If there’s any chance he’ll get violent, that’s definitely something you’ll need to address, whether by tying him up extra well or arranging another outlet for him or both. Also, since you can’t foresee everything, an important part of any trigger pan is how you’ll communicate in the moment. Will he be verbal? Will he be gagged? Will that be a problem for him? What will he need from you?

Another resource we can recommend is The Topping Book, by Dossie Easton and Janet Hardy. It’s geared towards the BDSM community, not specifically veterans, but it has a lot of great information about topping.

The other big piece of advice we have is don’t skip the aftercare. Aftercare is great to have as part of any BDSM experience, but it’s essential if you’re at all concerned about your bottom’s psyche. A good snuggly check in immediately afterwards and some explicit debriefing within a day or two will do several things. First, it will help make sure his experience is a positive one. It will also keep you informed as to how things are going for him, so you’ll have all the information you need to be the best top possible.

It’s not fair. It is so easy for him to cum and he gets to do it so often. It is hard not to feel some resentment towards him even though he really does try. He says he enjoys eating me out, and I believe him, but sometimes he is just not good at it. It doesn’t feel like he is in sync with me or my needs. We have talked about it quite a bit, and I even bought a book for him and underlined stuff that I agreed with or found helpful.

It is hard to talk about it thought. I try to communicate what i want, but in the heat of the moment it feels impossible to find words to describe what I need. When I do find the words, he seems to either just not get it, or he does exactly what I say to such extremes that it ends up not feeling good because you can’t just do the one thing to get me off. And then he gets frustrated because he is doing what I say and it still isn’t working.

A: It sounds like you have tried several of the things that we recommend when we hear this problem, but I will reiterate that communication is key to any successful sexual relationship. It might be helpful to talk him through the whole experience of oral sex. Or you could try to introduce a vibrator into your sex life. One thing to ask is whether you have ever enjoyed oral sex as much as you might want to with any other partner? If not, maybe oral sex is just not something that you are really into and you could try other types of stimulation to reach orgasm. Also, have you tried masturbating to see what you really enjoy and what you don’t? If you are comfortable with it, you could let your boyfriend watch you while you pleasure yourself so that he can see what your technique is and try to apply that the next time he gives you oral sex. Sometimes when you try to force an orgasm to happen, it can make it that much harder to actually cum, so try to relax and enjoy the ride, so to speak. If things get frustrating, it might be helpful to take a break and come back to it later.

Here are some websites that you and your boyfriend can refer to:
sexuality.org
sexhealthguru.com

There is are also video guides that you could try. We found one called:
“Nina Hartley’s Guide to Better Cunnilingus”

Also, here are some books that I can suggest if you would like more information:
“She Comes First” by Ian Kerner
“The Ultimate Guide to Cunnilingus” by Violet Blue
“Box Lunch: The Layperson’s Guide to Cunnilingus” by Diana Cage

Thanks!

(she is ridiculously hot though)

Also, if I do take her up on her offer, and we start hanging out more, how do I talk to her brother about it, without making him want to hit me?

PS. Thinking about this doesn’t make me an asshat of a friend and a pervert right?

A: You are definitely not a pervert because you are attracted to your friend’s sister. Most boys your age are attracted to one or some of the girls in their lives, and this is completely normal.

First of all, just because your friend’s sister asked you to “hang out”, it does not necessarily mean that things need to get physical between you two. You might want to talk to her to see exactly what she wants (dating, relationship, something physical, etc) before you decide to do anything.

Secondly, 3 or 4 years can be a pretty big difference, especially next year when you turn 18, when there could be legal concerns depending on how her parents feel about your relationship. We have read that in your state, the legal age of consent is currently 14 with parental consent and 16 without it. We are not lawyers, however, and these laws do change. Things could turn out ok, however. It depends a lot on both you and this girl, how mature you both are, and how both of your families feel about things.

You mentioned that you are afraid of your friend, this girl’s brother. You may want to try talking to him about how you feel and about what his sister has said, and see how he reacts to that. From there, you can gauge whether or not it is worth pursuing things with the sister.

A: There are several ways you can bring up the topic. For instance, it might be helpful to playfully bring up the subject during a neutral conversation moment so not to put pressure on him during your time being sexual. You could say something like, “Sweetie, let’s talk about sex and ways we can maybe spice things up.” Or, you could ask him if he has any sexual fantasies that he would be willing to share with you to get a sense of whether this might be something he is interested in and hasn’t known how to bring it up with you. Even if he doesn’t have that specific fantasy, it would be a good lead in for you to share about having a fantasy about spanking.

As another alternative, you could rent a movie containing the subject (“The Secretary” is a good Hollywood movie) and have a discussion about it afterwards, asking your partner what he thought, and if he might want to try something like that.

There are also plenty of rentable adult films that deal with spanking. You can look online at places like bluedoor.com (kind of like a Netflix for porn). And there are instructional type videos such as “Nina Hartley’s Guide to Spanking,” and other DVDs on Amazon.com (search for “spanking DVDs”).

In looking around on the web, here’s an interesting blog about spanking. Perhaps you can share some of this with him, or make it a topic of discussion.

There is another article about men spanking women written by Dr. Victoria Zdrok that you might show him if you are interested in him spanking you. If you are interested in spanking him, you might want to both check out Spank Your Man.

If he is interested in the spanking, you might want to take it slowly with the spanker spanking the spankee’s bottom and the spankee saying a number between 1 and 10 to communicate intensity. That way, the spanker can get a sense of connecting how s/he swats with the spankee’s experience.

Good luck!

A: It’s quite likely that the girls you’re having sex with do not know that your penis is unpleasantly sensitive right after you ejaculate. It’s possible that no one’s ever told them, and that they’ve had other partners who enjoyed being stroked post-orgasm–as some males do. My best advice for you is to tell them yourself. It might even be a good way to start a conversation about ways they do or don’t like to be touched that you might not know about.

A: Difficulty achieving penetration is not unusual when you’re trying sex for the first time. It is possible that your vagina is too tight for him to get inside, but that’s not very likely. It’s far more likely that the two of you just haven’t yet found a position that works for you. Other possibilities are that you have an intact hymen that is getting in the way, or that his penis isn’t getting hard enough to penetrate you.

Have you tried exploring your vagina yourself? The better that you understand your own body, the better that you can guide your boyfriend. The first thing to do would be to penetrate yourself with your fingers and get an understanding of your vagina’s position and angle. Pick a time when you’re comfortable and relaxed, and have some lube handy. We recommend using a water-based lube. Then when you and your boyfriend are ready to try having sex again, use your hands to guide his penis into the right spot and angle.

As for being too small: if you can fit two fingers into your vagina, you are not too small. If two fingers won’t fit, start with one. As you get used to the feeling, you’ll likely be able to work your way up. Your vagina is a muscle, and a strong one. If it’s clamped down tightly it can be very difficult to penetrate, but as you increase your awareness of it you can learn to let that muscle relax.

Also, you mention that your boyfriend had a hard time having an orgasm. Does he get erect and stay erect? Penetration is hard to achieve when the penis is not fully erect. If that’s the case, feel free to write us again and we can give some suggestions for maintaining an erection. As you gain confidence with your experiences you can try things such as masturbating him to orgasm, or doing oral sex.

Finally, if when you explore your vagina you find a flap of skin that’s partially or completely obstructing the entrance, that’s your hymen. Women’s hymens are all different, with some being very thin or barely there at all and a few being thick and nearly covering the vagina. If you do find your hymen intact and in the way, then it is going to have to tear before you can have sex. Hymens sometimes hurt a little when they tear, but sometimes not. Probably the easiest way to tear your hymen would be to use your own fingers. Put one or two fingers into your vagina and gradually increase pressure on the hymen until it gives way.

Lastly, if none of this works for you we suggest you see a gynecologist. They will be able to diagnose any problems and suggest a treatment.

A: Everybody is different, and it is hard to tell what this particular boy will think, if he even noticed it all. However, this should definitely not discourage you from talking to him or being his friend. Many boys are super impressed with girls who know what they like and are comfortable with seeking it out. It can make things a lot easier for both you and the guy you are with if you already have an idea of what you like. You are definitely entitled to your own sexual preferences, idea, and thoughts, and it is always a good thing to be open and assertive about them. If you find pressure from somebody about what you like, it does not at all mean that you are doing the wrong thing.

Even though this might feel quite embarrassing now, it should not have to impact how you interact with him.

He always was easy to turn on, and so never dealt with pleasing a woman when he wasn’t. Now he’s with me and I’m still, in my late 60s, substantially sexual. He’s thinking about whether he can get into pleasing me when he’s not aroused. I’m wondering what your advice is on this and I look forward to hearing from you. I am concerned that he will leave me hanging when I’ve got miles left to go my thinking is that each of us, whatever our capacity, should be filled up by the time we quit, but I don’t want to have to pull him to get what I need.

A: First we recommend you talk to him about your needs and your desire for him to participate in fulfilling your needs. People participate in partner sex for many reasons. Some people just want to get their own needs met and may not have previous partners request more. You may want to suggest he works on getting you off before you do anything to get him off. You may tell him all the things you will do to him right after you get off. Many men get excited by hearing dirty talk, but still need direct stimulation for orgasm. If you engaged in vaginal/penis sex you may experiment with different positions. Rear entry while on the side on a spooning position frees one of his hands to provide direct stimulation to your clit. You may also want to consider bringing a vibrator into your play together. Many women find that they can get off faster with a vibrator thus matching his need for shorter play. You may ask him to use the vibrator on you. If he is still reluctant, you two may want to considered couples counseling.