Help with penetration via masturbation?

Contributor: catrazz catrazz
I've only had sex a grand total of two times, and both times were terrible and super painful. He and I aren't together anymore, so I'm alone and in need of some "affection". So I recently bought a dildo.

The problem is that well... I noticed that I'm still "tight" even after warm up and can't seem to penetrate with my dildo. I also used lube.

I guess I just want to know how I can ease myself into this? What do I need to do? I want that penetration, but it's still hard for me. I'd appreciate any advice. Thank you. <33
11/24/2015
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Contributor: GingerAnn GingerAnn
Engaging topic analysis of Penetration:

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Hi! So I am really new to anal penetration, I've only done it a handful of times then stopped for a month or two because we both lost gusto for it...

Double penetration harness for two dildos?
i've been looking for something like this, but i can't find anything, so i was wondering if anyone here could help - what i'm looking for is a harness
11/24/2015
Contributor: TheToyGuy TheToyGuy
Interesting.

What dildo do you have?
11/24/2015

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