My first time using a strap-on wasn’t even completely my idea! Though my boyfriend is a bit submissive, so I cannot say I was shocked at his latest request. We were talking about our sex life and if anything was lacking. He’s a wonderful pussy licker, and I love when he goes down on me. I know he likes me to be in charge generally. He likes when I ride him and take the initiative and ask him first. So he got this sheepish look on his face when I asked him if there was anything he’d like to try. I laughed and asked him what he was thinking. He said he’d always been curious to have a woman try a strap-on with him.
I wasn’t sure I’d be comfortable doing that, so I voiced my concerns. He said if I found it upsetting or offensive, we could drop it. I said I’d think about it. A week later, I said I’d thought about his request to try a strap-on, and I agreed to try it. He looked like a kid on Christmas morning. I knew he’d be excited, so I’d already stopped at the sex shop on the way home. I went to the closet and brought out the bag. He looked at it and asked what was inside. I dumped it upside down and a strap-on and a harness came tumbling out on the bed. He picked up the approximately seven-inch toy and examined it closely.
If we were going to do this, I wanted him to be as comfortable as possible. He stripped right down without even being asked and was on all fours, elbows down, ass up, in no time. First, I got undressed and stepped into this leather harness thing. I couldn’t help but laugh. I felt a bit ridiculous. Finally, I got the dildo part to snap in the front holder area and was ready to go. I drizzled some of the extra thick anal lube on the toy and coated it generously. I climbed on the bed behind him and asked if he was ready. He looked over my shoulder and nodded, grinning.
To start, I grabbed him by the hips and slowly started to ease the head of the strap-on towards his asshole. First, I pushed lightly, and he winced. I asked him if he was in pain, and he said no, continue. I pushed further and went slowly, checking in with him periodically. He said to just ease it all in, every inch. I did so, and it was soon all the way into him. Then, I moved back and forth slowly at first and then faster when he asked me to. I was going at a good rate, and he slipped his hand underneath himself and masturbated as I fucked him. He was in seventh heaven with pleasure.
I gave his ass a swat, and he giggled like a school girl, loving it. Then, I fucked him over and over. I could tell between his hand stroking his cock and me pounding him that he was gonna blow soon. I went even harder, and a noise came from him I’d never heard before. Sort of a cross between a squeal, a groan, and a yelp. He stiffened and blew it. He told me to keep going, so I did, then I gradually slowed down. Then, he told me to ease it out, and I did. He collapsed on his side, breathing hard from his post-orgasmic rush. After removing the harness, I climbed back into bed to spoon with him.
Finally, I lay next to him, and he whispered thanks in my ear for giving him such pleasure with the strap-on. I told him he was welcome, and it hadn’t been as weird as I thought. He thanked me by going down on my pussy and licking me to three incredible orgasms. I was a happy lady after that. He pleased me, and I pleased him. What more could a gal want?
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