Harold and I have been doing some experimenting. There’s something kind of taboo about the asshole and anal sex – that animal thing of it being dirty. But we’re in the middle of toilet training a toddler and poop just doesn’t provoke the same amount of squick right now. Harold keeps saying that he wants to have every part of me so I know that he loves everything. Even the parts I think are gross.
I’m not actually grossed out by anal sex. I rather like it, assuming that it’s handled well. I haven’t had a lot of anal sex, and I do have some hang ups around it, but I have had some really great butt fucking. Notably, a time that it happened spontaneously on the kitchen floor with Joel. We used olive oil for lube. Amazing!
Usually, I fuck Harold up the ass with my amazing two-way. Poor boy has a secret desire to find a sweet young boy to fall in love with and be fucked by. Until then, we have our gender play. We did that last Saturday. I love sliding in the two-way and having Harold slather my big black cock with tons of lube. I like watching his hand slide back and forth. I push him onto his back and lick his cock, squeeze his balls. I cover my fingers in lube and slowly slide my index finger into his asshole. He feels so interesting inside. I can feel his prostate and it makes him moan. It tends to make me feel powerful.
At some point I totally lose patience and I just want to fuck him. He lifts up his hips and I rest his legs on my shoulders. I position my cock right at his rectum and very carefully push into him. Even so, he tends to spasm and I pause to give his body time to adjust. Once everything is fine and I’m buried in his ass I like to lean forward so I can kiss him. He wraps his legs around me. I feel like a boy and he feels like my girl. I love him so much – but I just have to fuck him. I can’t help it. I have to make those little humping motions. I can really feel him. I actually orgasm this way, but it feels different. Like I’m pushing my essence deeper and deeper into Harold.
He played with my ass over the weekend as well. We’re working up to anal sex. Saturday it was his finger in my ass and two fingers in my cunt while I held the vibrator on my clit. Wow! Just a slow in and out with all of his fingers felt amazing. I am now contemplating double penetration with both of my guys, but I’m not exactly sure how that works logistically.
Today we did another interesting anal related thing. I took Harold for colon hydrotherapy for his birthday! It sounds kind of scary and weird, but it was so cool. We went to a spa-like place called the Tummy Temple in Seattle. The whole procedure was very gentle and even spiritual in a way. I thought that Harold might enjoy it because he tends to eroticize enemas and this is a very deep cleansing. I think he had 35-50 gallons of water cycle through his large intestine today. I got to watch. I loved the machine that ran the water in and let the waste flow out again, with a lit tube for viewing colonic waste. Total steampunk! And Harold feels new and fresh in some indefinable way.
So, I’ll leave you with a few pointers for anal play: trim your nails, remove your rings, keep hold of anything you stick in there, and use LOTS of lube.