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A close friend of mine and I had been having playful no-strings-attached sex for a few weeks, and I decided that I trusted him enough to share my newfound obsession. I usually liked to keep the focus all on him. I absolutely loved it, though for me, it was definitely more satisfying psychologically and emotionally than it was physically. I listened to interviews with a woman named Strap-On Jo, who claimed to be an ass play and pegging specialist. It was like I was in some alternate reality. I only let a couple inches go in at first, but as he relaxed, I was able to go farther. I had a decent amount of experience on the receiving end of anal, so I knew how painful it could be if done wrong. When my boyfriend came over that night, we spent a few moments just cuddling while I wore my strap-on. He nodded me on in encouragement, but also stopped me occasionally when he needed a break. I flipped the dildo upside down so that the curve would still be targeting his prostate, but I was totally caught off-guard by how insanely awesome it looked to see him in this new position. The dildo slipped, bent around, and missed his butthole a few times before I could get it into him. His was at least three inches in, so I had to root around with my finger all the way inside before I was able to find it. When I pegged him, I generally wasn't seeking my own orgasm, but that was my choice. I went with a dildo called the Mistress and a comfy cloth harness called the Joque. Now we both had penises.

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Watch First Time FEMDOM Sessions: Kendra's PEGGING Initiation on Fucking bf's arse If that really is her first time, she's a born natural.

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Bertha from Fairfield Age: 25. Is there a man who is interested in debauchery without obligations, in secret from the second half.
Description: I was sitting back on my heels with my thighs outside his hips, rocking my hips back and forth in little humping movements, which made my knees and hip flexors ache. When my boyfriend came over that night, we spent a few moments just cuddling while I wore my strap-on. Right before I took the plunge, we exchanged loving smiles and he said he was ready. His was at least three inches in, so I had to root around with my finger all the way inside before I was able to find it. It also made me really think about my gender identity. I had a decent amount of experience on the receiving end of anal, so I knew how painful it could be if done wrong. I hopped back in bed with him, and we cuddled and recounted the entire experience from start to finish. His butt was right there, ready for action, and his penis was dangling just below it. I could hardly contain my excitement. I ran to the bathroom, carefully took off the harness in order to avoid getting butt juice all over the place, and left it in my bathtub to clean later. I flipped the dildo upside down so that the curve would still be targeting his prostate, but I was totally caught off-guard by how insanely awesome it looked to see him in this new position.
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