Teaching the Church Lady

"What do you..."

"Think, Sugar, what would make a man like me happy?" I pumped my still wet cock a couple of times with my free hand and waggled my eyebrows.

"Oh," she said. "I've never... been able to... I'm not good at that at all." "It didn't seem like it when you had that dildo in your mouth." I smirked at her. "Suck my cock clean and make me hard. I want another go at you."

"But... you're dirty."

I didn't want to hear it. I needed my cock deep in her mouth. I wanted her lips pressed against my belly as she took me down her gullet. I tapped her face with it, leaving a smear of come on her cheek. As menacing as I could, I said, "Now, Honey. Put that mouth of yours to some good use for once."

With a little grimace, she reluctantly opened her mouth. I slipped the head past those fuckable lips and began rocking it forward and back, still soft, but interested. She just sat there, letting me fuck her mouth, not participating in any real way. I needed more."Use that tongue and your hands for something or our deal is off."

She shot me a glare, but started working her tongue over my cock's base and she raised her hands to hold me still. I pulled back out, leaving only my head in her hot cavity, "Lick the head, run your tongue under the base and then fuck my slit with that tongue of yours."

I have to say, it was a trip to give her directions. It made me feel a little powerful when I'd say something and she'd do it, no matter how bad her attitude was. It made me hard just thinking of how much I could control her. I pushed back into her mouth, "You keep that up, Sugar, and I'm gonna be ready for round two in just a few minutes."

I knew she wasn't enjoying this part of our little agreement as much as I did, but I didn't care as long as she kept up with me. I moved my hips as I gripped her hair harder and pushed my cock all the way to the back of her throat. I could feel her start to gag so I pulled back just a little bit and then pushed in again. Her face was red and tears streamed out of her eyes as I fucked her mouth deeper and harder with each stroke. She slipped a hand between her legs and started rocking back and forth as I fucked her. As I pushed down her throat, she moaned, sending pleasure shooting up my cock and I almost wished my plan was to come down her throat. It would have made me happy to see such a proper lady drink my jizz, but time was getting short even if I had no place to be since I had given up my chance for a room for the night. I was sure that someone would notice that her shop wasn't closed down and quiet for the night and I didn't want to be interrupted during round two. I had some big, nasty plans for her plump ass.

I pulled her head back. "Okay, honey pot. You've been a good girl to get me so hard. Now I want you to lie down on your back in the floor and hold your knees up to your chest."

She quickly pulled her hand out of her pussy and rubbed the tears off her cheeks. "Will we be done after this?"

I moved over to the desk and got the lube and that fat dildo. Her question kind of irritated me. I was trying hard to make this as good for her as it was for me, but I guess she just didn't get it yet. I finally said, "Yeah."

"Oh." She almost sounded like she was sorry about that.

She was waiting just like I had told her to be. Her tits were still tight and high enough, even if her belly as a little soft, but really, all I had eyes for was that sweet gash of hers. I stared at her pouty cunt liking how nervous she looked. "What are you going to do with those?" I gave her my best smart-ass smile. "I wanna watch you use them like you were fucking yourself with your fingers just now."

I almost laughed as she her mouth gaped and worked. She looked like a damn fish as she flushed a pretty pink.

I knelt down between her legs and put the dildo on the bulge of her bell. Her cunt lips were still puffy from the fucking I had given her and a thick string of my cum leaked from between the gaping slash. I pulled some down with my finger and worked it towards her asshole. I smeared it around as she squeaked, "What are you going to do?"

I bent down without acknowledging her squeak of protest and ran the flat of my tongue over it. She jerked upwards as I worked it around, making sure I got every little dimple on it. "Oh my... Oh, that feels... It's so... filthty! Soooo... good too."

I fumbled for the dildo and put it in her hand that had gone slack as I tongued her in a place that I bet no man had ever been. When I glanced up, her hair had finally come down from that stupid ponytail. Her thrashing at the newest sensation I had given her made it splay out wildly around her head. Her cheeks were pink either from embarrassment or being so aroused. Between strokes of my tongue I said, "Get to work, Sugar. I wanna see you come again."

I moved away just enough for her to slide the toy inside her slit. She started out slow, working it in and out with little flicks of her wrist as she bit her lip and avoided my very interested stare, but soon she was pumping it almost as hard as I had fucked her. I took the bottle of lube and coated my cock and then squeezed some just above her tightly closed asshole. I should have probably prepared her better, but I didn't really want her to know just how thoroughly I was going to have her.

As she fucked herself in the pussy, I hefted her ass up and angled my cock so that it was easy to start my slide into her. She gave a little scream and tried to scramble out of my grasp as I started to push my thick, blunt head into her ass, but I had experience with a reluctant partner before. My old cell mate hadn't wanted me to fuck him in the ass the first time either. I put pressure on that tight ring of muscle with my thumb and worked it in. "I told you I wanted to fuck you in every hole. Now, just relax and bear down."

I wasn't going to be delicate about this. I got the feeling that she really needed to hear some dirty talk to get her going. I also wanted her to remember just what kind of man she had allowed to invade her cunt and her ass. "I want to come inside your ass. I want it to drip down your legs when you go to that car of yours, and I want you to remember just where you let me fuck you every time you move for a few days."

I pretended like this was just more dirty talk to turn her on, but I really did want her to remember me. She struggled, the dildo now forgotten in her cunt, as I pressed my cock past that tight ring of muscles. Once the head was in, I thrust in a little, opening her virgin ass. I didn't want to hurt her, not too bad. She was panting, her tits jiggling as I sawed back in forth gently. When I was finally in almost to my balls, I took a minute to look at what I had done. "Oh, Sugar, I wish you could see how well I fit in you. It's like your asshole was made for my cock."

"Keep fucking yourself," I said as I took her hand and put it back on the dildo. I want you to be as full of cock as one man can make you."

She whimpered as I helped her stroke the now slick rubber into her weeping cunt. I moved in a little as she pulled it out. We did that a few more times until I saw a slight sheen of sweat start forming in the valley between her thick tits and the flush on her face deepen. Soon she was groaning, "Don't stop... O god... I never thought... I 'm so... fu-ull. And your cock is so... deep... Fuck me harder!"

Her ass was impossibly tight and slick with both her juice and the lube. It was an incredible feeling to have the slide of that rubber dong against my cock separated by just a thin bit of skin. I picked up my pace, matching her busy hand with the thrust of my cock into her hole. Fuck, I hadn't enjoyed Tiny's ass this much.

Soon, too soon, I felt the pressure in my balls increase. They drew up, tight and hard and I knew I was going blow my load into her ass. That thought pushed me closer, so I started putting it to her harder, I pressed down on her body trapping her hand and the dildo between us. I knew I'd only last a few more thrusts so I ground into her, working the nubby, ball end of the dildo against her clit. She screamed her release as her ass muscles clamped down on my cock almost painfully. I came with a hoarse shout.

For the first time during that whole experience, she touched me without me having to tell her to. She ran her fingers through my sweaty hair and kissed my forehead. I didn't have the energy to do much more than move my head but when I did she was looking at me, really looking at me. She had a soft smile on her now bruised-looking lips.

My eyes drifted shut as I felt her run her manicured nails over my back and down my side, a light gentle touch, one that I really didn't deserve. I was a bad man who had blackmailed her to do this with me. Normally I wouldn't have felt anything, but something about how she had just looked at me made me feel guilty for what I had made her do.

After what seemed like an hour she said, "It was my husband --my ex-husband-- who told me I wasn't good enough in bed for him. Thank you for proving him wrong, even if it wasn't the most conventional way to initiate our encounter. I enjoyed everything very much."

I'll be damned if I didn't want to cry even as my cock got a spark of life in it. There was just something about this sad, uptight woman that made me want to fuck her over and over. I opened my eyes again, "You like it enough not to call the cops on me?"

She gave me a smile with those still very fuckable lips her eyes crinkling at the corners, "I don't renege on my agreements, Mr... Robber."

When I was finally able to move, I eased off of her. She was a mess, so thoroughly fucked that anyone who saw her would know exactly what she'd been up to, blackmailed or not. They would also know, from her heavy-lidded eyes and slow, sensual movements, that she really had enjoyed it.

"I'm sorry I was going to rob you. I just needed a place to stay tonight." I thought about how this sounded and added, "I'm not sorry that we fucked though." I held out my hand to help her up. "Sorry about the clothes too. I guess I wasn't thinking of how you'd get out to your car."

She laughed, a low sexy sound that went straight to my balls. "It's winter. I have a coat."

I pulled on my jeans, stuffed my shorts into my coat pocket and then put on my shirt and shabby coat. I could hear her putting on her coat too. I couldn't stand the thought of seeing her all uptight and church ladyish again, so I kept my gaze on the floor. "Well, I guess it's goodbye then. And, uh, you were a real good lay. That ex of yours is either an asshole or he doesn't know his way around your body."

"The latter, I think," she said with an amused hitch in her voice. "My name is Anne and I'm here late on Monday evenings. The other businesses are closed then so we wouldn't be interrupted if you cared to... you know."

I looked up at her then. She held out her hand like she was at some fancy assed party and I was the guest of honor. I shook it, and felt a slip of paper slide into my palm. "You can call me Red."

She leaned in and kissed me. It was the kind of kiss that lovers give to each other, long and slow with the promise of more. When she drew away, I unfolded the paper. Inside it were two C-notes. "I thought you needed to pay some bills."

She shrugged her shoulder delicately, "I thought you needed a room."

She made her way to the back door. "I'll let you out this way. You can understand why it might not be wise for you to be seen. I wouldn't want to cause you any embarrassment."

I nodded, even though I knew that she meant she didn't want to have to explain what we had done. I pocketed the money. I could get a room for a week and have money to eat on. I stepped into the alley way. It had started sleeting.

As she closed the door, I heard her say, "Remember, Monday nights I'm here late if you happen to want an evening's entertainment. I also might have some friends who would like to meet you if you ever needed more money."

I walked into the night knowing that I'd come back as often as she'd let me. Maybe I'd take her up on the little side jobs too. A man can't have too much pussy, after all.