#3106: Many Ways To Have Fun
Original photo: @monica_figueras
Callie is invited to have some fun with her friends, Jerry and Leona. She’s more than happy to join them, especially when they ask her to bring a strap along for the night.
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Transcript
I’ve been friends with Jerry and Leona for a long time. I met Leona first. We had been friends since school and spent a lot of time at each other’s houses, doing each other’s makeup, sharing gossip, and experimenting. I’m proud to say I was her first kiss, but I never wanted more. I was always a free spirit, in love with trying new things and testing new experiences, so settling down was never something I was interested in, unlike Leona. She went through her share of relationships until she found the man of her dreams—Jerry.
By extension, I became his friend as well and spent a lot of time at their house, especially on weekends. We would cook, have fun, play board games—nothing unusual. Sometimes I would brag about my sex escapades, though I knew better than to go into too much detail. I assumed Jerry and Leona might be uncomfortable with it, so I kept my mouth shut. As it turned out, I was dead wrong.
At the end of one of our usual evenings, Leona sat beside me on the couch, her eyes avoiding mine. I knew her too well not to recognize the sign that something was on her mind, so I pushed her to open up. Soon enough, she said something I never expected to hear.
She wanted to invite me into their bed as a third.
At first, I was shocked. I had always assumed they were more than satisfied with their sex life and didn’t need me for extra excitement. Clearly, I was wrong. I felt torn—messy kissing was one thing, but having sex with my friends was something else entirely. Leona didn’t pressure me, but she made it clear that both of them were excited about the idea and wanted nothing more than to see me in their bedroom.
Curious, I asked what exactly they expected me to do and what role I would play. Leona’s cheeks flushed bright red before she finally admitted what they wanted. She wanted me to bring a strap and use it on both of them. I chuckled in surprise. I had only mentioned owning one once, and it had clearly left an impression. I took a deep breath, weighing my options. I knew accepting could complicate things between us, but I was also undeniably curious. After thinking it through, I told her I was in. Leona visibly relaxed, the tension leaving her shoulders. We agreed to meet the following weekend in a more intimate setting.
A week later, I arrived at their house fully prepared. I brought the strap and wore my best underwear. They were already waiting, eager and clearly willing to do whatever I asked as long as it led to them getting fucked. I loved seeing it.
Jerry’s voice shook when he asked what they should do. I instructed them to go to the bedroom, strip, and wait for me. Leona mentioned it would only take a few minutes, and I nodded. I had my own preparations to make.
I undressed, leaving my underwear on, and strapped on the harness—a set of thick leather straps with a ring at my crotch. I adjusted it carefully, slid the dildo into place, and tightened the harness until it sat securely. The dildo was bright pink, slightly rounded rather than realistic, just the way I preferred. I smiled as I gave it a small push and watched it bounce.
I didn’t bother knocking before entering the bedroom. They were clearly waiting. Both of them stared at me, mouths open, their eyes trailing over my body and stopping at the strap. It was flattering. Leona looked beautiful—her light brown skin glowing, her curves soft and inviting, her dark curls falling over her shoulders. Jerry was more toned than I’d expected, subtly muscular, his cock already hard.
They didn’t quite understand what I wanted at first. I stepped closer to the bed, the strap bouncing as I moved, until it hovered between their faces. Their excitement was obvious. I instructed them to show it some love, and Leona’s smile widened. They turned toward each other, pressing their lips to the toy, kissing the soft silicone. I couldn’t feel it, but I wished I could. Wet marks formed as they kissed it, and when Leona reached the tip, she eagerly licked it before taking it into her mouth. Jerry continued kissing the shaft as I watched.
Leona grew more enthusiastic, taking the toy deeper, and I decided it was time to give Jerry his turn. I pulled it from her mouth, glistening with saliva, and guided it toward Jerry. He hesitated briefly but complied, awkward at first. Soon enough, his confidence grew, and he began to enjoy it. Leona watched, teasing her nipples, clearly aroused by the sight. Jerry was nearly moaning around the toy by the time I pulled it away again.
I considered them both, deciding who would go first. Leona was nearly trembling with anticipation. I chose her. She eagerly lay back and spread her legs. Jerry looked on, just as eager as I was.
Leona was slick, her breath heavy as I pressed the tip of the toy to her slit, teasing her. She whimpered as I slowly pushed inside, her body tensing as I began to thrust. I took my time. There was no need to rush.
Jerry watched from the side, but he could be more useful. I motioned him closer and encouraged him to use his tongue. He didn’t hesitate. The sight was perfect—Leona stretched out, the strap sliding in and out, Jerry working her with his mouth. I increased my pace as her reactions grew stronger, gripping her knees and thrusting harder until she finally came apart beneath me. I continued until she lay still, smiling blissfully.
I pulled the strap free and turned my attention to Jerry. He was more than ready. Within moments, he was on all fours, his cock hard and waiting. I pressed the toy between his cheeks, rubbing lightly. He groaned as Leona stroked him. When I finally pushed inside him, I went slow, careful of his reactions, teasing him as I worked him open.
Jerry loved it. His reactions made that obvious. I picked up the pace, enjoying the power and watching him unravel. Leona stroked him faster until he came hard, spilling onto the sheets.
Finally, it was my turn.
I loosened the harness just enough to move the strap aside and climbed onto the bed, spreading my legs. I told them I wanted both of them, and they didn’t hesitate. Two tongues met me at once, competing for my attention. I leaned back, grabbing their hair, letting myself be worshipped.
Their mouths worked me perfectly, the sensations overwhelming. I gave in completely, riding the pleasure until orgasm washed over me, leaving me breathless and spent.
When I came back to myself, Leona and Jerry lay beside me, eyes already drifting back to the strap.
And I was more than happy to give them more.