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Guys: what's your opinion on strap-ons?

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Question - (20 May 2013) 4 Answers - (Newest, 21 May 2013)
A female United States age 30-35, anonymous writes:

During an alcohol-fueled conversation with a (straight) male friend about a month ago, he let it slip that his ex-girlfriend had sex with him using a strap-on...and he loved it. My boyfriend has requested that I come up with some new things to do in bed, and I've been considering buying a strap-on and introducing that into our sex life.

He already gets INCREDIBLY turned on by anal stimulation; after the last time we had sex, I was stimulating his prostate with my finger (sorry if that's TMI...lol), and he said, "Too bad you can't do that and f*** me at the same time." For this reason, I feel like a strap-on would be a really good idea...seeing as how that is, essentially, what I would be doing.

I realize that this is something that I should probably mention to him beforehand, but I think it would be a lot more fun to just surprise him. But before I decide whether or not it's something I'm going to do, I want to hear from guys who have already had it done to them and girls who have already done it to a guy. Here's what I need to know:

1. What is the best way to "stretch" him beforehand so that it doesn't hurt excessively? And how much lube (and what kind) should I use?

2. What is the best position for us to be in?

3. Where is the best place (online) to purchase a strap-on? And what is the best type to use?

4. If you're a guy answering for yourself, what did you think of the experience? If you're a girl answering for her guy, how did he react to it? Was it pleasurable for you in any way as well?

Any help is greatly appreciated! ")

View related questions: ex girlfriend, his ex, sex life

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A female reader, So_Very_Confused United States +, writes (21 May 2013):

So_Very_Confused agony auntI've had several men love being done with a strap on.

usually we used doggy style (with me in back)

LOTS of good lube (anal-eze is specifically for anal intercourse)

Personally if I could find a strap on that would stimulate my clit at the same time I was thrusting it would be perfect.

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A male reader, Hennessy1989 United Kingdom +, writes (21 May 2013):

Hennessy1989 agony auntPersonally the thought would scare the hell out of me lol, but if your man seems to like that kind of stuff then maybe a strap on is a good idea

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A female reader, anonymous, writes (21 May 2013):

I have not done it, but I work with a bunch of guys who are not shy about discussing their sexual encounters with basically anyone willing to listen. My advice to you would be to make SURE he's into the idea before trying to stick anything up his derrière. There's a very big difference between one female finger and a fake d**k. Just saying. Good luck :)

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A female reader, anonymous, writes (21 May 2013):

I can't offer much advice, except; don't go overboard. I have a male friend who's GF sprung this on him and he was all for it, until it wouldn't fit, then got uncomfortable, then got painful. It was apparently a pretty big one, so, I'd start small - maybe some interchangeable options. But, I think it's a great idea.

I might start off first by being a bit dominating with him during prostate stimulation, talking dirty, asking him if he'd like to be fucked. Getting a bit dominatrix-y might give you an idea if he'd be into that. Start small, then work your way up :D Good Luck!

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