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Really nervous about trying a strap-on for the first time. Do I bring up the topic before or during sex?

Tagged as: Dating, Gay relationships, Sex, Trust issues<< Previous question   Next question >>
Question - (25 January 2017) 2 Answers - (Newest, 25 January 2017)
A female Denmark age 30-35, anonymous writes:

Hey dear community!

I've a girlfriend (she's 25) for a while now (about 1.5 years) and all in all its pretty awsome.

The sex is really amazing, far better than anything I ever had and she is feeling the same.

We really care for each other, even though she's kinda difficult sometimes but that is due to her past and I can live with it because I know she loves me and i can live with the "bad days".

We both have a really stressful study and she can't handle the stress very well. And thats where my "problem"/question begins.

I've never wanted much sex in my previous relationships.

It was ok but like a necessary thing to do. I could have fun doing it, but it was more like a time-consuming thingy and I had better things to so, you know what I mean?

This time everything is different.

I think about sex a lot and I'm kind of frustrated after a week without sex. Of course I try to not be a bitch about it because I know my girlfriend has problems with intimacy and just don't has the urge to get ^^^^^ed very often and when she does, it goes away really fast.

We are making compromises, because I don't want to push her into things she doesn't want to and she trys to make an effort once in a while.

But she is really shy with that topic, she would never say something in bed like "I'm not sure i want this" or stuff like that, that makes it sometimes hard for me to stop thinking because I tent to watch for sighns of discomfort so I don't hurt her or her feelings.

We make it work because we love each other and so on.

She's been with a man a few times to try it out. She hoped that she's not that gay but she is and she is pretty sure about it.

I myself never had the need to try it out I knew I was into women.

A few weeks ago I told her, that I would like to try out a strap-on because thinking about it turns me on (me on the receiving end).

We talked about it and she said, that she would be ok with trying it out so we went to a sex shop and look for harnesses and stuff.

A few days later we bought one and she was really supporttive the whole time. I was kinda nervous about it, I dont know why to be honest... i guess it was a mix of "not wanting her to feel pushed" and "I have no ^^^^ing clue what I need or want in a dildo".

Ever since the package arrived it's kind of awkward with the sex in the beginning. She's a bit anxious about me asking for the strap on.

She fears that I could really enjoy it and maybe want to try out a "real dick". I told her like a 100 times that just because I like her fingers during sex or a strap-on doesnt make me straight or bi.

The Questions:

1. Should I bring the strap-on topic before or during sex? I've no clue how to really ask her because I'm acually nervous about it too.

2. What the heck am I supposed to do?

We both have no clue (i'm thankful that we can laugh together about all kinds of stuff even in bed) and I'm not quite sure... it's like when you don't have a drivers licence.

You know how it looks when someone is driving a car, you can sit in the drivers seat and so some things but you acually have no clue how to drive.

3. What positions (i guess missionary) are good for beginners?

4. What length width of a dildo would you say is best for situation like this?

5. when do we stop? I dont expect to get off the first time and I just can't figure out a way in my head to tell her "hey hon, thanks for the thrust but its enough now"

I talked to a friend about this and she simply said "do what feels natural" but that is not really a help...

View related questions: dildo, her past, shy

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A female reader, singinbluebird United States +, writes (25 January 2017):

singinbluebird agony auntIm a straight female here but female is female, pleasure is pleasure.

DO NOT BUY a big dildo. Please start off comfortable, the new sensations should be enough. To each their own, but I think with dildo, bigger is NOT better. Invest in a decent size one that vibrates. I would say buy a regular size one ranging from 5-7 inches only, no bigger. Some women do not even use it for penetration but only for rubbing/vibration which can be pleasurable as well.

The best position is missionary. ALWAYS. Then you can gradually go into doggy but please make sure you comfortable entire time.

You stop when you want to stop.

If she is worried you will suddently want a real guy, just tell her its her you love and that youve always been into women. She should know that because youve chosen her again and again. she makes it sound like being gay is a choice and a mature human being would know thats not the case! Its offensive for her to assume this---I hope she can be more respectable next time.

Note: Just have fun and enjoy each other. Dont forget to laugh and kiss as you try new things/positions. Just make sure you enjoy each other's company. Good luck.

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A female reader, Andie's Thoughts United Kingdom +, writes (25 January 2017):

Andie's Thoughts agony auntIt really is about doing what's comfortable and being open. Tell her you're nervous and it'll put both of you at ease, a little.

Most women can't orgasm from penetration alone, so it should be a bonus, not the ending. Ask her if it's okay for you to guide her when you're done with the strap on, so you move her hand to you or something and she knows that's what you want instead, or you can take over pleasuring her.

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