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To me, it sounds like you're stilling having trouble with the first of these, in which case I suggest you work on that before trying to rope in another dude to screw you properly. The time-honored method of learning to anal stimulation is the use of a butt plug or a dildo. Get yourself a nice dildo and start using it.
There are a million models in all shapes, sizes, lengths, materials, and colors, but the silicone dildos from Tantusparticularly the "Silk" model, are probably the best I've run across for a beginner to use Also get some good water-based lube such as KY. Although silicone-based lubes have a lot of advantages, some of them interact badly with silicone toys, to the toys' detriment. Also, silicone is a little difficult to wash away, whereas a water-based lube is easy, easy, easy to clean up.
I'd avoid greasy lubes like Vaseline: they work fine with silicone toys but are a bitch to clean up and grease stain anything they get on. The path to success with a dildo is to take it easy, very very easy, and at all times concentrate on the pleasurable feelings that result. Put on a rubber glove, apply some lube to your asshole, then gently massage and finger yourself. Once you've gotten that far, you can haul out your dildo and use it to massage your hole, pressing very gently. As as you don't force it, your hole relax further, and eventually you be able to ease the dildo inside.
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