Dildo play

Dildo update! i had that itch deep inside my pussy again today and i so desperately needed it scratched.i put on some of my favorite lingerie and got my box of toys out for an early morning play session to start the day off right. i began with my trusty vibrator, which is pink,6in long,thin and is variable speed.(truthfully i only use one speed, love it on full power!) Only problem was my batteries were dead and i couldn't find any new ones. :-( **blushing** i guess i need some sort of rechargeable batteries or buy an economy jumbo pack for my vibrator. So i decided it was time to try my new dildo again. i bought this dildo thinking i could handle it, but my first two sessions with it were unsuccessful. It's a big life like dildo with balls & a suction cup on the bottom. This monster is black,8in long, very thick (with veins) and a large helmet head. i wasn't patient enough and over confident in my abilities first two attempts. But I was determined that this time things would be different. i put a condom on it and applied a generous amount of lube to both the dildo and my tight ass/pussy. i started slow, laying on my back i began working that enormous head in & out of my hole and totally enjoying it. My tiny clitty went limp and i was now totally focused on my hungry pussy. i then got up on my knees and started gently bouncing up and down, easing more & more inside my pussy until the head reach my sphincter. i back off, applied a giant blob of lube on the head and resumed until that big head pop through and i slid down until i could feel the balls on my ass. It hurt like hell, but i did it! This is where i need to be patient i thought to myself. i was now sweating so i lay on my back for a few minutes to catch my breath and savor my accomplishment. i was becoming accustom to the feeling of being completely full stretched and it just felt right. I started working my beautiful black dildo in & out and soon found myself up on my knees again bouncing up & down. Before i knew it, the pain had been replaced by lust. I was sweating and panting like a dog. i worked myself into a frenzy. I was moaning and begging fuck me with that big black cock ...yeah deeper, deeper... fuck my ass! i wanted to try different positions so I was frantically looked around for things to attach the suction cup dildo too. I fucked myself for almost an hour and my little clitty was still limp, but leaking a lot of precum, which i hungrily licked up. i was hoping to have an orgasm from penetration like a girl, but that didn't happen.So i eased my dildo out and started stroking my little clitty with two fingers and coaxed a hard-on.i frantically jerked off and shot my load and then the embarrassment & shame of what i had just done took over. It usually last for about 30 minutes and then i start thinking about what i'll do the next time. Three questions: 1.Have you ever cum from only penetration? Have any helpful hints on how i can accomplish this? 2.Do you feel embarrassment & shame after and orgasm? 3.Have you ever been in chastity? And do you think it will help with the anal penetration orgasms?