It had been almost a month since I gave Bo his first experience with anal sex. Needless to say, he couldn’t get enough. As much as I had loved fucking my boyfriend for the first time, I had to be the strong one and force him to wait at least two or three days between each session. “You know it’s not safe or healthy to have anal sex as often as you want it, Bo,” I had to tell him the Friday before Halloween on the way to m...

Bo and I both had to work all day the first Saturday of October and it was an unusual day for us both. The night before, Bo had used my dildo that closely resembled his cock on me and we jacked each other off to intense orgasms. The feeling of Bo’s “cock” inside me fueled one of the most explosive orgasms I’d ever had. Earlier that night, I had sucked Bo’s real cock to a throat-filling explosion while using his largest bu...

“Can we please try the next butt plug today?” Bo begged as I drove home from school the Tuesday after Labor Day. We’d spent the previous three days trying our new butt plug trainer sets. Of course, we started with the smallest of three progressively larger plugs. But we both found that smallest one too easy. We liked the feeling of having something inside. But it seemed too easy. We didn’t feel like we were being stretche...

When I woke up that Labor Day Sunday, Bo had his left arm and leg draped over my naked body. His stiff five-inch dick was pressing against my bare ass. I reached down and found my own cock was moderately hard. He must have felt me move and slowly rolled over to face the wall. He was still asleep. But I rolled with him and snaked my hand over his hip to find his morning meat. I stroked him slowly, softly. My fingertips gra...

I got off work Saturday at four and drove straight to Bo’s house. I knew he had to work until six. But his brother Bobby and his friend Michael had invited me to tag along on their trip to an adult store on the outskirts of town. At 16, I was really too young to shop there. But Michael had offered to buy me a leather cock ring to wear around the house for Bo. He’d convinced me that Bo would love the way it made me look. A...

A couple Fridays after school started, Bo and I headed to his house, ready for the long Labor Day weekend with his house to ourselves. His parents had gone to the beach again, and we were set to spend most of the three-day weekend naked and alone, not counting the few hours we both had to work Saturday and Sunday. When I pulled into the driveway, however, his brother Bobby’s car was there. Bo sighed loudly and rolled his...

Just ten days after our camping trip, I picked up Bo for our first day back to school. He immediately began complaining about how much he was going to miss seeing me so much – and so much of me – since we wouldn’t be able to spend our days lying around naked. “We still have lunch and gym together,” I told him. “You’ll get to see me naked for a few minutes in the locker room.” My best friend and I had spent as much of our...

A couple weeks after our beach trip, Bo started bitching and moaning about going out of town again. He loved the feeling of being anonymous. He could be more himself, more effeminate, more the way he is when we’re alone without worrying about the wrong people seeing him. At the beach, we were on our own in a foreign landscape, and that made all the difference. I had started working on my dad about letting us go camping al...

I was standing under a hot shower when my best friend stepped in behind me and slid his arms around my waist to pull me into a tight hug with his limp dick pressed against my ass. It was exactly how Bo wanted to start every day, especially after sleeping naked together in his bed with no parents or brothers to disturb us. This particular Friday we were on our way to the beach. His parents had invited me to join them for a...

When my best friend’s parents invited me to go to the beach with them for the long Independence Day weekend that year, Bo decided he wanted us to spend some time alone first. So, he told them I had to work Wednesday and Thursday night when he knew I didn’t. Bo’s brother Bobby also was heading out with his girlfriend that Wednesday. So, we would have his house to ourselves a full two days and nights. I made a trip to our f...

Bo and I missed seeing each other a couple days because of our work schedules. Besides weekends, we’d been together every day for the last three weeks. And we’d spent almost every one of them lounging around his pool naked. It was cloudy and rainy, which meant Bobby, Bo’s brother, would be home all morning. We couldn’t be naked or take a shower together until he left. Bo and I weren’t exactly lovers. But we were getting c...

Monday was a gloomy, rainy day. But Bo greeted me at his front door like the happiest guy in the world. “Oh! My God!” he practically screamed. “Friday was amazing!” He wrapped his arms around me and hugged tightly, pinning my arms together. We hadn’t talked all weekend. So, he had a lot to unpack about our eventful Friday. “Where the hell did that come from?!” His eyes were wide, unblinking. I had let him dry hump my nake...

As usual, I headed over to Bo’s house at about 10 am. It was late in the second week of our summer vacation and I’d spent almost every day of it completely naked in his pool or bedroom. Just then I was wearing shorts, a t-shirt, and Van’s, my standard summer outfit. I had with me a small backpack with a couple towels and a bathing suit. This was all just insurance. I almost always had to wake Bo up with a quick text from...

I headed over to Bo’s house about 10 am on the first day of our summer vacation. He lived just a few blocks away. We’d spent every day of the last four summers in his pool. We both had just turned sixteen, Bo in April and me in February. So, this year I was driving my hand-me-down fifteen-year-old Jeep to his house instead of my bicycle. Bo and I met on the first day of sixth grade and found we had several classes togethe...