Soooooooo my friend Amy was standing by my bedroom dresser wearing a tight T-shirt that exposed her midriff, which I remember specifically because the little pink jewel in her belly bar was reflecting the sunlight from the window and I thought I was super pretty. Anyway, we were just hanging on a random Saturday—literally nothing interesting—and she was reaching into my top drawer to get a hair tie when she stopped.
“Woah, what the heck is this? You’re joking, right?” she said. “This thing is like…eight inches or something!”
“So?” I said, feeling my face redden a little. She was my best friend, but that didn’t mean I went around showing her my sex toys. Not usually, anyway. “It’s not that big, right? Like, it’s normal.”
“Normal?” Amy laughed, reaching into the drawer and pulling it out, holding it up in the air and giving it a wiggle. Her eyes wide. “Damn, what guys have you been with?”
“It’s not that big,” I repeated, feeling my stomach tighten. But seeing her, standing in the middle of my bedroom floor, holding it aloft, I had to admit that it looked pretty huge. “Anyway, don’t shame me! I like it.”
“Yeah right!” she laughed. “There’s no way you can take all of this.”
“Of course I can!” I said, feeling suddenly defensive. “It’s nice!”
She laughed. “It doesn’t look nice! It looks painful!”
“Well, I guess it is a little bit, at first. But once your body gets used to it…once it’s like…all the way inside you and you’re grinding on it then—” I realized she was watching me with a little smirk. “Shut up!” I said, pulling my robe tighter around my body, my hair still damp from my shower.
“I didn’t say anything!” she laughed.
“You’re pulling a face!”
She shrugged, wrapping her hand around the shaft of it and contemplating, feeling the weight of it in her hand, squeezing slightly and raising an eyebrow. “I can’t see it.”
“Fine,” I said, kneeling up on the bed and snatching it off her, my robe falling open slightly. “Want me to prove it?”
Amy laughed. “You wouldn’t dare!”
“That’s what you think!”
I slipped it beneath my robe, lying it on the bed between my legs, running my hands down the sides of it, taking a deep breath, trying to psych myself up. I wasn’t wearing any panties, and I felt Amy’s eyes on me, the silk robe suddenly feeling thin and immaterial.
As best friends, we used to get changed in front of each other without ever thinking about it, and we’d even shared a bath together once when we’d book that hotel that was way too small. But that was years ago, and this was a very different situation…
…but it wasn’t my fault she didn’t believe me.
I found my clit and began to circle it.
“You’re really going to do this?” Amy said, our eyes locking for a moment as I continued to touch myself beneath the silk. It felt weird to be touching myself in front of her, but it’s not like she could see anything, and it somehow gave me a strong thrill of exhibitionism, which very much helped what I was trying to achieve…
I knew I’d have to prove it to her eventually, but for now I ignored her, closing my eyes, trying to lose myself in the sensation. I pictured a faceless, nameless man, imagined his hands on me, his body pressing against mine. I worked myself for a few minutes, my breathing getting deeper, feeling myself opening up, softening, getting ready.
“Sarah,” she said. “You don’t have to do this. I was just joking, you know?”
“Mmmhmmm,” I said, half-agreement, half-moan. “It’s okay. Don’t…mmm…don’t worry about it. I want to, now…”
I opened my eyes to see Amy nodding solemnly, sitting down on the edge of the bed and watching me. I moved the head of the dildo between my lips and then gasped slightly as I pushed the tip of it inside me, gripping the bed sheet as I did so.
Amy bit her lip.
“Can I…can I see?” she asked, crossing her legs.
I nodded slowly, gasping again as I slid it another inch deeper, feeling it begin to stretch me, just a little. “Okay…” With my other hand—the one not pressing the dildo into myself—I opened my robe. Amy’s eyes went wide.
“Holy shit, Sarah.”
I looked down at myself.
The dildo was half way inside me already, my hips were gyrating unconsciously on the shaft of it. My breasts, heavy and full, had fallen either side of my body, my nipples hard and pointed upwards. My pussy, smooth and glistening, was spread wide. I hadn’t expected to see myself looking so obscene, but I understood her exclamation now.
“See,” I managed with a grunt. “It’s going in.”
“Yeah…” Amy breathed. “It is…”
I slid it a little further. Another inch.
“Fuck!” I yelped.
Amy sat up straighter, shuffling toward me slightly. “Are you okay?” she said, her face concerned.
I nodded, tears in my eyes. “It just feels good, that’s all. Can you…”
Oh god, was I really going to ask this?
No. It was too weird. It was crossing a line.
“Never mind,” I said.
“What?” Amy asked, shuffling closer still. “What’s wrong?”
“Can you help me?”
Amy’s face flushed even redder than it already was. “Help…how?”
“Just…help,” I said, letting go of the dildo and opening my legs wide for her. “Please.”
I couldn’t bring myself to say the words, but it was clear what I wanted. Amy, still sitting on the end of the bed, leaned forward and gingerly placed two neatly manicured fingers on the base of the dildo and pushed it.
“FUCK,” I gasped.
Amy looked mortified, pulling her hand away from the dildo and placing it on my knee. “Oh my god, are you okay? I didn’t mean to—”
“Do it again.”
“Really?”
My back arched a little and I moaned. “Does it look like I’m joking?”
Amy smiled, looking a little flustered and embarrassed, blowing some of the blonde fringe out of her eyes. She leaned forward and—watching me closely—pushed it again. This time, when I made a noise, it seemed to encourage her rather than deter her, for she gripped the base of the dildo and pulled it out a little way before pushing it in even deeper.
“Oh my god, yes. Amy. That’s it. That’s…that’s really helpful, actually...”
Amy nodded, her eyes transfixed between my legs, on my body, on my face, at the way I was taking it. She pushed a little deeper, and I felt my body relax even further, feeling safe in the hands of my best friend.
I wondered what the hell was wrong with me and then decided I didn’t care.
“More,” I said. “Give me more.”
Amy nodded, and to my surprise, she used her other hand to grip my thigh, prying my legs further apart, making me gasp as she sank the dildo deeper inside me.
“You’re so wet…” she whispered, pushing it a little deeper. “I think you might actually be able to do it…”
“Oh, fuck,” I said, tears in my eyes, feeling the stretch now. “How much further?”
“Just a little more,” Amy whispered. “You can do it…”
Her gentle words of encouragement did something to my body, and I felt myself relax even further. We stayed like this for a moment; Amy holding the dildo steady as I moved my body cautiously, easing myself further down it. I felt the sweat beading on my forehead, and for some reason, I felt the urge to push my breasts together for her, squeezing them with my forearms, presenting them to her. They bulged, my nipples hard, and I took pleasure from the fact she was looking.
“Kiss me,” I said suddenly, surprising myself.
Amy froze, one hand still resting on my thigh, the other resting on the dildo three quarters of the way inside me. “Kiss you?” she repeated “What are you talking about?”
“I mean…” I laughed slightly in spite of myself, my breath catching as she adjusted the dildo slightly. “Sure. Why not, right? You’re already fucking me…”
“Ew, oh my god, I’m not!” she said, sounding disgusted. But I noticed that she did not pull her hand away, keeping a firm grip on the cock buried inside me.
“Just... please?” I said, hearing a little whimper in my voice. “It’ll help me relax. You want me to take this whole thing, don’t you?”
She looked from my eyes to my lips, down to my pussy, then back up to my eyes again. “This is weird,” she said, but she still didn’t pull away.
Maybe she just needed a little push. Maybe she just needed to see how much I needed her, how much I appreciated her, how much I valued her as a friend. We’d been through so much together, and I knew that if I just showed her how grateful I was, then she’d understand.
With the dildo still buried inside me, I grabbed my tits and started to grind…
Hot as always Wordsmith, love the “A bet turns into lovers” troupe