I had this FWB, Jess, who was 33 at the time (I was 29). She had this energy about her - confident, playful, and completely unafraid to try anything in bed. We always had incredible fun together, the kind that left you catching your breath and wondering what could top it. Jess had a perfect body - curvy yet toned, and her ass was, well, something I couldn't get out of my mind.

One day, I decided to ask her. "Can I fuck your ass?" I asked, almost casually, though my heart was racing.

Jess raised an eyebrow and smirked, that mischievous glint in her eyes that always spelled trouble. "Sure" she said, "but only if I can fuck yours."

I blinked. "Wait, what?"

Her grin widened. "You heard me. If I get to fuck your ass with a strap-on, then you can have mine. Fair trade, don't you think?"

I"ll admit, it caught me off guard. I wasn't sure what to say, but the idea... intrigued me. Plus, I wasn't about to pass up the chance to experience her in a way I'd been fantasizing about for ages. So, I agreed, and we set a date. Both of us prepped - showers, clean slates, the whole routine.

When the time came, Jess took charge. She slipped into a black strap-on that looked both intimidating and fascinating. She teased me a bit, running her fingers along it as I watched, equal parts nervous and excited. "Lie on your back" she said with a playful smirk. "I want to see your face."

I obeyed, lying back with my legs raised, completely exposed. She lubed me up generously - her touch was gentle but firm, and her confidence put me at ease. Slowly, she pressed the tip of the strap-on against me, watching my reactions closely.

"Just relax" she whispered. "Trust me."

As she pushed in, inch by inch, I focused on the sensation - new, intense, but oddly satisfying. She took her time, letting me adjust before moving deeper. When she was finally all the way in, she paused, giving me a moment to breathe.

Then she began moving, slowly at first, watching my expressions with a mix of concentration and delight. As I got more comfortable, she picked up the pace, thrusting in a steady rhythm that had my whole body responding. Her free hand found its way to my cock and balls, stroking and teasing me as she fucked me.

The strap-on she wore wasn't just for me - it had a part for her too, and the more she moved, the more it stimulated her. Before long, her breathing grew ragged, her cheeks flushed, and she was moaning louder than I'd ever heard. When she came, her whole body trembled, and she collapsed onto the bed next to me, panting.

For a few moments, we just lay there, catching our breath. The strap-on was still on her as she smiled lazily at me. "Your turn" she said eventually, pulling it off and setting it aside.

"How do you want me?" she asked, looking over her shoulder.

"Doggy" I replied without hesitation. Her ass was a work of art in that position, and I wanted to savor every second.

She got on all fours, arching her back to give me the perfect view. I lubed her up generously, starting with my fingers to make sure she was ready. She moaned softly as I worked her open, her body relaxing into my touch.

Finally, I positioned myself behind her, and as I pushed inside, I felt the heat and tightness of her perfect ass around me. It was everything I'd imagined and more.