My best friend Doyle and I were half drunk at the bar we usually visit after work, when an attractive young woman walked by.
"Man, look at that tight little ass. I'd give my left nut to fuck that ass," he said.
"Shut up--you've got Francine," I said.
I sort of have a thing for Doyle's fiancee, Francine, and it always rubbed me the wrong way when Doyle got like this. Francine wasn't what you'd call beautiful, but for a slim little woman, she had the most incredible butt. From the first time I saw her in jeans, I was in love. I regularly awaken from sleep to remember a dream I'd just been having about her ass. It was that good.
"I don't get you, man. Francine has a way better ass than that woman."
"You think so?" He looked at me.
"For sure. Ten times better," I said, in a strange rush to defend her. As soon as the words left my mouth I felt as if I'd let my secret slip. He didn't seem to notice though.
"Maybe, but it's not like I get to do her back there," he said, still staring off in the direction of the woman who'd just walked by again.
It was a surprise to hear him discuss their sex life like that. For some reason I was happy to hear that she was denying him full access to her behind. Our conversation moved on and I tried not to daydream of his fiancee's ass.
Two days later I was sitting at home alone in the evening, watching television when my doorbell rang. It was Francine, alone. Wondering what she was doing at my door and trying to not stare all at the same time, I invited her in.
"I'm sorry to bother you, but I need to talk to someone. I'm having problems with Doyle," she said.
My heart thrilled to hear those words, and I worked at maintaining a comforting appearance. "Oh. I didn't know."
"He wants me to do something, something I don't want to do. Something sexual."
I raised my eyebrows and she continued.
"He ... he's fixated on having anal sex. He has been since we got together. It's not something I want to do. And it's gotten worse. Now he's threatening to call off the wedding if I won't let him."
What could I say? I didn't know where to start. I wanted to comfort her, but not as much as I wanted to steal her away from him. My mouth opened, and then closed again without making a sound. She started to cry.
"I love him, but he's such an asshole. You should hear the things he says. He said that when he leaves me, I'll have you if I want. He, well ... he claims you're in love with my butt."
However true that sentiment was, an urge to steer the conversation elsewhere seized me.
"If he's such an asshole, why do you stay with him?"
"I don't know. It's hard to explain. He's so forceful, so demanding, that it makes me crazy. But I like it too, you know? I'm drawn to it."
She had this faraway look then, and hearing her talk about him that way didn't make me happy.
"So why don't you do it, then? Let him have what he wants?"
She stifled a little sob.
"I did try. But it just didn't work. No matter how slow he tried to go, it just wouldn't fit. It hurt so much," she said, her tears getting stronger again.
"I don't know what to tell you."
She took a deep breath and her tears slowed. She took another deep breath, and lifted the bag she'd brought. When she looked me in the eye then, there was a determination there that hadn't been when she'd arrived.
"Is it true what Doyle said? About you liking my ... my ass?"
Too flabbergasted and confused by the moment to speak, I just nodded. Hope filled me like it never had before.
"Then I want you to help me. If Doyle needs me to have anal sex, then I will. With you," she said, and then she spilled out the contents of her bag onto my coffee table. There was a tube of lubricant and three strangely shaped black rubber cones, each larger than the last.
"What are those?"
"Butt plugs. Doyle would eat his heart out if he knew the things you're going to do to my ass," Francine said, and then she began to pull off her jeans!
Before I knew it she had all of her clothes off, and I was down to just my jeans. She brought her toys and pulled me into my bedroom. She leaned over the side of my bed and looked back at me. I just stared at her magnificent curves, overcome with wonder. Seeing her ass presented to me that way was like a religious experience for me. My mouth fell open and I just froze there.
"Don't just stare. You can touch it, I want you to. Go on, feel it."
I moved closer and dropped my hands to her round buttocks. I couldn't believe I was actually touching her, it was like one of my dreams come true.
"Maybe you could give it a kiss."
I didn't need any more invitation to worship her beautiful flesh than that. I knelt behind her and pressed my lips to the grand curve of her right cheek. Her skin felt impossibly soft and warm to the touch, almost creamy smooth. I softly kissed and licked my way around her rear, and I loved it. It was the ass of my dreams, literally, and I was in heaven. I began to slip a finger between her cheeks when she clenched them, stopping me.
"Wet it first."
I withdrew my finger and sucked it into my mouth. Looking back over her shoulder she laughed at me.
"Not you, me. I'd really like it if you wet it ... with your tongue," she said. She looked embarrassed at what she was suggesting.
I wasn't offended by her request, though. When I moved my mouth into that divine crevice between her buttocks, the faint smell of her sweat mixed with the fragrance of her arousal and it made me so hard that there wasn't enough blood left in my head for rational thought.
I dragged my tongue through her crack and found the tight little rosebud of her rear opening. She gasped as I dragged my tongue across it. My cock strained in my pants as I buried my face between her cheeks, licking her there in earnest. She moaned softly as I worshiped her, and after only a few moments in that pose I felt a spasm seizing my balls. I grunted into her butt as I came, my mouth pausing momentarily as I froze there in climax.
"Ted?" she said, as she turned to look at me. Her eyes opened wide as she took in my quaking hips and the dark stain spreading at my crotch.
"Wow, you really do love my ass," she said, giggling at the sight of me.
It was really embarrassing, so much so that I felt my face flushing. Her expression changed as she seemed to realize how embarrassed I was feeling.
"Don't worry, I understand. Your tongue felt great. Why don't you get the lube, and try starting with a finger?"
I greased up my index finger and slipped it between her cheek. I pressed it against her hold and I could feel her growing tense.
"Just relax, it will go easier if you relax," I urged her.
I pushed harder still and was amazed at how tight she was. Only after quite a bit of pressure and wiggling was I able to push my finger into her. She moaned at the intrusion, and it didn't sound like she was moaning because it felt good.
"Oh, go slow. Go slow."
I managed to get my finger in up to the second knuckle, and then I looked over at the smallest of the butt plugs. If she was ever going to get that thing inside her I was going to have to get more than a finger in her first. I slid my finger back out of the tight heat of her, and then greased up my middle finger as well. I tried to work them both inside her as gently as I could, but the moment I started to feel them press inside her she cried out in pain.
"Stop stop stop stop!"
I pulled away and she collapsed forward onto the bed. She buried her face in the blankets for a moment and I thought she might be crying.
"This is impossible. It's never going to work," she sobbed, turning to face me.
"Don't get down on yourself, it's probably just going to take some time," I told her as she lifted the greased up rubber toy and looked at it. She looked from the toy back up to me and gave me a little grin.
"I guess so. Maybe it would work better if I visualized it happening. I have an idea. Turn around."
I stared at her. Did she really mean what I thought she meant?
"I don't think so."
"Come on, don't be a prude now. You've already enjoyed this a lot more than I have," she said, gesturing to my stained pants. "Turn around."
She gave me a playful push and then I found myself turning around. I felt her nipples dragging on my back as she leaned against me, reaching around to undo my pants.
"Shhh." She had my pants down, and my underwear too. She pushed me down with a soft touch, and then I was bent over the side of the bed. I felt her touching my rear, and then something cool and wet against my crack.
"Just relax, it will go easier if you relax," she repeated my words with a teasing tone. She began to push against me, and I felt the tip of the thing pressing into me. She pushed harder, and I grunted as the entire nob of the thing invaded my ass.
"So that's how it looks. How does it feel?"
It felt enormous, and I wondered for a second if she'd switched to one of the bigger ones without my noticing. The sensation of her standing over me, holding my hips combined with the weird feeling of being filled did something to me. I felt myself getting turned on again. I willed it not to, but my traitorous cock began to stiffen.
"Huge," I answered, hoping she wouldn't see how much it was turning me on.
"Ooh, somebody likes it," she said with a laugh, and then I felt her hand close around my penis.
.... There is more of this story ...