Cherry Bottom
by Shanna Germain

‘You okay, babe?’ Andrew’s voice above me was half sexual rasp, half concerned. His warm, oiled hands had moved from the outside curves of my ass to the inside of my thighs, and they were resting there, not pulling or teasing, just resting against my skin. I kept my eyes and mouth closed like I was supposed to and tried not to think about my naked ass in the air. I nodded against the pillow.

‘She’ll tell you if she’s not,’ Miss Suzanne’s voice came from the other side of me. ‘Won’t you, Cate?’ I nodded again, the rasp of the pillow filling my ear. Miss Suzanne pressed her cool, slim fingers next to Andrew’s, higher up on the inside of my thigh. The hot and cold of their hands made my ass break out in goose bumps. ‘See, Andrew? She’ll tell you. So stop stalling.’

Miss Suzanne’s fingers left my skin. Her heels click-clicked away, presumably to another one of the six couples whose husband was also stalling.

Andrew’s hands didn’t move. I waited, head on my hands, belly and thighs resting on the prop-up pillow, ass in the air. My bare body was still in goose bumps, although the room was warm enough. Some of it was anticipation. But most of it was fear – Miss Suzanne’s anal sex class was our last resort. If we couldn’t get Andrew over his fear of anal sex here, I was afraid it was never going to happen.

It had been difficult enough to ask for it – the way I was brought up, girls aren’t supposed to like any sex. And they definitely aren’t supposed to like it the way I liked it. And poor Andrew – he wanted so badly to please me, but couldn’t get over his fear of hurting me. No matter how many times I told him, no matter how much I begged for it. We’d tried videos and books. I’d even bought the smallest butt-plug at the store. Straw-sized, really, but still, he couldn’t bring himself to put anything inside me. Not even just a little bit. Bad experience, was all he’d say. But this class had been his gift to me, and I knew he wanted to please me that way, even if he was too afraid. So, now, here we were, being taught anal sex by Miss Suzanne Saunders, southern belle turned sex therapist. Our first two classes had been lecture and book-learning. Today was hands-on. Today was our last chance.

I concentrated on letting my muscles go loose, on breathing in through my nose. We’d just spent ten minutes playing, getting warmed up. A little strange, to share foreplay with a dozen other people in the room, but every time I looked up, they were all concentrating on their own space, their own bodies. It was like a yoga class in the nude. And despite his fears about anal, Andrew didn’t seem to have any fears about public sex. He just ran his tongue up and down between my thighs, reached up and ran his wet thumb over and over my nipple until I could only lean back and try to keep my moans quiet.

I wanted this so badly, I could already feel him inside me, the fullness of him, the weight. The way his balls would slap against me. Jesus, it had been so long, I could barely remember how it felt. I took a deep breath, tried to think of something else for a minute, to be calm so that Andrew would be calm.

Andrew’s fingers held steady at the inside of my thigh, one second, two. Then he ran them up through the crack between my cheeks. With one hand, he spread my ass cheeks open. With the other, he circled the skin around my asshole. Part of our class had been learning the anatomy of the asshole, getting used to its pink pucker, its hairless expanse of skin. Knowing that Andrew was looking at me like that, that he was studying me, made my pussy ache for his fingers. My asshole too. I wanted to reach my fingers underneath me, to ease the ache in my clit, but we weren’t supposed to move, so I squeezed my eyes tighter and tried to enjoy the ache. Maybe I could learn something too.

Andrew’s finger went around and around, tighter and tighter circles toward my asshole until finally, the tip of his finger pressed against it and I could barely breath. I wanted him, any part of him inside me so bad. He held his finger there, not moving it in or out…just resting his finger against it like it was a button he was deciding whether or not to press.

Miss Suzanne’s heels click-clicked toward the front of the room. ‘Okay, boys, I want you to get your fingers really well lubricated, the way we talked about earlier. We’re going in.’

The class broke into nervous giggles. I was glad to hear Andrew’s snort, the same one he gave at the comic strips at home. But his finger at my ass didn’t move. Against my legs, his thigh muscles tightened.

C’mon, baby. C’mon… mental telepathy, the only encouragement I could offer him. I hoped that on some kind of a subconscious level he could hear me begging, could hear how much I wanted him like this.

Miss Suzanne and her heels again, right at our table. ‘Can I help, Andrew?’ she asked. He must have said yes, because then her cool fingers were at my ass cheeks again, spreading them for him. My asshole puckered up against the cold. My tightening nipples crinkled the paper sheet beneath me.

Andrew’s fingers left my body, coming back oiled and warm.

‘It’s like playing pool,’ Miss Suzanne said, her thin fingers still in place. ‘It’s all about speed and angles.’ Andrew’s finger back against me, pressing, pressing. I fought the desire to lean back onto the tip of his finger, to force him inside me once and for all. But part of our class promise had been to let our partner do all the work, go at his own pace, let him do only what he was ready for.

He increased the pressure, opening my asshole, careful to use the flat of his fingertip. ‘Go,’ Miss Suzanne whispered, and then Andrew pushed his way inside me. Just a little, just the tip so I could barely feel it, but oh Jesus, there he was.

‘More,’ Miss Suzanne said. Andrew pushed his finger farther into my asshole. Farther, until I was sure he had to be at the first joint. Having him in there like that made my pussy ache with that special emptiness that I loved. Andrew entered me to the knuckle. I imagined what he looked like behind me – starting to sweat beneath his glasses out of fear and excitement, his finger disappearing into my asshole.

‘All the way in,’ Miss Suzanne said. And then he pushed and his finger was inside me, tearing through me with that certain pain that is mostly pleasure. I bit down on the pillow, but most of the moan came out anyway.

‘See?’ Miss Suzanne said. ‘She likes it. You’re doing a great job.’

‘Jesus,’ Andrew whispered. ‘Oh fuck.’ Awe and arousal deepened his voice to a husky whisper. Hearing that voice – no fear in there – almost made me come.

Miss Suzanne raised her voice. ‘Okay, class, is everyone in? Foxes all in the holes?’ I’m sure the class laughed, but I couldn’t even concentrate to hear all the answers. All I could feel was Andrew’s finger in my ass, the way he held it there, so still, the way it filled me and at the same time made me ache for something more, something bigger.

‘Great,’ she said. ‘Now I just want you to wiggle your fingers in there a little bit. Not a lot, just enough to feel the room, to see what kind of reaction you get.’

This time, Andrew didn’t hesitate. As soon as she said wiggle, his finger started moving, up and down, up and down, inside me.

‘Okay?’ Andrew asked. But this time he wasn’t asking if I was okay. He was asking if it felt good, if he was doing the right thing in there.

My voice was all whisper and the pressure of not fucking his finger. ‘Yes,’ I said. ‘Yes, please don’t stop.’

Miss Suzanne click-clicked back to the front of the room, apparently trusting that Andrew had gotten the hang of things.

After a few minutes she said, ‘Ladies, now it’s your turn to help out. Gentlemen, your job is just to hold yourself still. Maybe for the first time ever, your ladies are going to fuck you.’

Andrew’s finger stopped moving in my ass. Light-headed, I pushed myself backwards onto Andrew’s finger, so far back his other curled knuckles rubbed against my skin. I let myself fuck him, showing him how much I wanted him like this, how much I wanted him inside me.

With each thrust, Andrew’s breathing quickened. His finger burnt and rubbed the inside of me in pain and pleasure. I was so full back there that the rest of me ached, empty and untouched. With one hand, I reached beneath me and fingered my slippery clit, letting everything build inside me. The fullness and the emptiness. The sweet burn of Andrew’s finger in my ass, the soft roll of pleasure through my clit. And the best part was Andrew behind me, bracing himself against the table, letting me fuck him, I hoped, without fear for the first time. Seeing there was no pain, that there was only pleasure.

I was close to coming, but I wasn’t sure if we were supposed to, if we’d been given the go-ahead, or if there was more I was supposed to do. And then Andrew moved his finger inside me, up and down, just enough to hit that spot and it didn’t matter if I was supposed to or not, it was happening. Everything sliding through me from Andrew’s finger out to my toes, up into my head. I cried out, and heard Andrew do the same.

I pulled forward, off Andrew’s finger, and let my head hang on the pillow. ‘Holy shit,’ I said. I had no idea where anyone else was in the room, or if there was even anyone else in the room any more. And then I heard Miss Suzanne’s heels click-click up. ‘Once you two have washed up, meet in the front room to debrief and get your assignments for next week.’ She put her hand, still cool as ever, against my shoulder. ‘Nice job, you two.’

When I sat up, Andrew’s face was pink and flushed. But he had the biggest grin on his face. Just seeing him like that, aroused and confident, made me wet all over again. He leaned down and kissed the lobe of my ear. ‘That,’ he whispered, ‘was awesome. I can’t wait to see what our new assignment is.’

I thought of his cock, the tip of it entering me, the way it would feel when he finally pushed inside me. ‘I can’t either.’