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Hi,

My Girlfriend is 35 years old & still a virgin. From what shes said & various things (what I've been told by her family etc) I believe her.
We have been dating some time & I've told her that I'm in no rush & we will take things at her own pace.
We have been masturbating regularly & shes cum's with me fingering her (though I have not penertrated)
We have tried full on sex once & it didn't go so well - all abit clumsy etc however she is now ready for another go.
Now what should I expect? I've told her it may hurt but at her age is it likely to me any more painful than if she was younger? What about bleeding?
At the end of the day I dont want to hurt her. I want to support her the best I can & know what to expect just in case she freaks (esp if she starts to bleed)
I will of course be using a condom & lube.

Thanks

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It might be best for her to speak with either her GYN doctor, and/or her marriage advisor in her church.

Although many women have a hymen and a little pain and bleeding with the first intercourse, a few have a tough hymen and need a little help resolving that. That can be dealt with in the doctors office. but it takes an exam to assure that she's ready.

As far as your prior experience, you are right to take it slow. Have some lube on hand, and high points for a condom. You might also just plan on a few times where you give each other mutual naked massages, with full body contact and lotion... with the agreement that there will be no intercourse. This could help build trust and also assure that you won't go farther than she's comfortable with.

If you two havent' already, you might read up on the latest self-help sex books:

"Sex is Fun" by Kidder Kaper
"The Guide to Getting it On" by Paul Joannides (Goofy Foot Press)
"Sex for One" by Betty Dodson

All are pretty good and liberal.
For a more conservative approach that is all text, try "Everything you Always Wanted to Know About Sex" by Dr. David Rubin.
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