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An Unexpected Pleasure

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“Hey man, you got a light?” the old guy next to me asked with a hoarse voice. He looked to be about 5’5″ tall, overweight, had a head full of roughed up black and gray greasy hair, and a shaggy beard. I guessed his age to be around 50. His jeans and flannel shirt were a little dirty looking.

“Sorry, I don’t smoke,” I told him.

“What the hell does a guy have to do for a light around here?” the guy said and smacked the bar before getting off his stool and bothering another patron.

I sipped my drink and watched the TV that was mounted in the nearest corner. It was showing a baseball game.

“So man, what’s a youngster like you doing here all by yourself on a Friday night?” It was the old guy returning with a lit cigarette.

“I don’t know, nothing else going on I guess.”

“Well that’s too bad. You look like the type who’d be out banging his girlfriend,” he said, laughing gruffly and putting a heavy hand on my shoulder.

“Look I’d like to be left alone, alright?” I said and shrugged his hand off.

“Okay, okay, I didn’t mean any harm,” he nodded and sat down.

I watched the baseball game and continue to work on my drink. As I was getting to the last few gulps I noticed the guy looking over at me again.

“Well man, sorry for bothering you before. I guess I ought to get back home to the old lady,” he sighed.

“No problem.”

As he walked out the door I shook my head and finished off my drink. It was getting to be time for me to head home too. The bar was depressing me.

“Hey! Hey you, man, can you help me out?” I heard the guy once again as I was nearing my car. I stopped, closed my eyes, and sighed. As much as I wanted to keep walking and drive away, I was too nice not to at least see what his problem was.

“What’s up?” I asked him as I approached him from across the dimly light parking lot.

“This damn trunk won’t start. I must have left a light on or something, the damned thing.”

“Hold on, I can pull my car over to jump it,” I said while reaching into my pocket for my keys.

“Come here first. Let’s see if she’ll turn over while I take a look under the hood.”

“Alright,” I answered and stood next to the truck. He opened the door and I hopped into the driver’s seat. As he stood near me I noticed he reeked of smoke and alcohol. “Got the keys?” I asked.

“They’re right here,” he said and fumbled around in his coat pocket. A moment later he pulled a black pistol out.

“What the hell…” I said and stared at the gun.

“Move over,” he ordered and shoved me.

I slid to the other seat and watched him closely as he climbed in the truck while keeping the gun pointed at me.

“Now you listen here kid. You do as I tell you and I won’t hurt you, okay?”

“Okay,” I said nervously. “Look, if you want my money, you can have it.”

“God damn it. I ain’t going to rob you boy,” he muttered as he started the trunk and put it in gear. The radio played quietly and was tuned into an AM country station. “Like I was telling you before, I need to go home to the old lady.”

“What’s that got to do with me?” I asked.

“I had my eye on you since you walked in that bar. You’re just the right type I was looking for. Young, handsome, and lonely,” he said and laughed. He sounded like he’d been smoking for most of his life. “That’s what the old lady asked for.”

“I don’t understand.” I said and noticed the gun sitting on his lap. I wondered if I could reach for it fast enough.

“You might be a good looking kid, but you sure ain’t the brightest are ya?” he said and laughed again. “My wife, she’s one of those sex addicts, you know? What do they call ’em? Nampho? Something like that I’m thinkin’. Anyway, I’m not the man I used to be, and she rides my case something fierce for that. That’s where you’re coming in kid.”

I was getting the point and I immediately felt sick. If this guy’s wife was anything like him I’d probably be too grossed out to even get a hard on.

“Sometimes she talks about how she wants to fuck a young guy like you. Never thought I’d find her one. God damn she’s gonna love this,” he said and reached for his cigarettes.

I shot my hand out towards the gun, but a bump in the road dropped the guy’s arm and blocked my motion. He quickly picked up the weapon and pointed it at me.

“I told you not to try anything like that boy,” he said and sounded sincerely pissed.

“Alright, it won’t happen again,” I muttered.

“Oh come on man, you get to fuck a woman tonight, don’t go and sound like you’re down in the dumps. I’ll tell you what, my wife, she’s a good fuck. Big ole titties and a nice round ass,” he laughed hard and coughed hard.

I watched the trees pass as we drove in the darkness. A feeling of relief made me relax and I started to see that the guy didn’t seem bent on harming me.

“You got to be careful with her though. I’m telling you this as a friend,” he said as he recovered from the coughing fit. I shook my head at the mention of friendship. “Once she gets all hot and in the mood, she won’t want to quit. And she likes to do some weird shit man. Weird shit!” he exclaimed and coughed. “One time, must have been a few years back at least, we was both drunk as hell, and she got all horny. So she tears her fucking clothes off and starts giving me this great blow job. Damn that was something else. But then she stood up and pissed on my cock. Man that was some nasty shit, but she got off on that.”

He finally felt comfortable enough again to get a cigarette as we waited at a red light. As he pulled the searing hot lighter out of the dash I considered using it to put a nice round burn on his face and hope to escape before the light turned green. Unfortunately it didn’t work out as we were through the intersection before he put the lighter back.

“So is all this talk getting you turned on yet?” he asked and rolled down the window a little bit.

“Not really. It’s kind of hard to when you’re being kidnapped and have a gun pointed at you,” I told him.

“Yeah, I guess so man. Like I was telling you before, I ain’t going to hurt you. I tell ya what kid. I’m going to put my gun in my pocket, alright?”


“So you got yourself a girlfriend or some chick that you’re banging?”

“Not these days,” I said. His tasteless vocabulary was starting to get on my nerves.

“Wait a second,” he said and started to laugh almost hysterically, “You’re not one of them fairy boys are you? Can’t bring the old lady a homo,” he went on laughing.

“Don’t worry, I like women.”

“Well that’s good. Ah hell, I bet she’d turn ya straight if you were gay. Damn she’s one hell of a fuck. Man, I’ll never forget the day we met. I saw her at a bar back where we were going to school. She had this little outfit on. Man! What a piece of ass!” he said.

“How much further is it?” I asked.

“Oh ’bout halfway there now,” he answered and flicked his cigarette but out the window before rolling it back up. “So tell me kid, how old are you anyway?”


“Damn fine. Man she’s gonna love you. I got to tell you I’m jealous kid. I ain’t been able to please her for a long time. These days she just kicks me out of the bedroom and plays with herself. Oh hell, I guess the old plumbing for us guys just don’t hold up that well.”

“Yeah, it happens sometimes.”

“Well at least she still has her toys. Seems like she’s getting them in the mail every couple months. The damn things fill up half of a dresser drawer.”

As we continued driving I imagined some overweight woman with saggy tits laying on a worn out bed stuffing a big dildo into her hairy pussy. It didn’t turn me on at all.

“Alright man, we’re almost there. I got to warn you, if she’s been drinking at all she’s gonna be a handful,” he said as we approached a small subdivision. I was somewhat relieved to see that the houses were actually halfway decent.

“I’m gonna tell you this again, don’t get any ideas about trying to get way. Alright?”

“Right,” I said.

“Good man,” he said and patted my shoulder. “Here we are, home sweet home.”

We pulled up to a small ranch style house on the edge of the subdivision. As the headlights of the truck panned over the yard I could see it wasn’t maintained at all and there was some junk lying around.

After the guy turned off the trunk I climbed out and stretched. I followed him to the front door and waited for him to unlock it. His drinking had affected his ability to work with such small devices like a key and lock, so it took him a minute to finally push the door open.

“In you go kid,” he said and pointed inside.

I walked in to find there wasn’t much in the way of lighting turned on. The place was pretty clean and seemed fairly nice. Much better than I had assumed since meeting the guy and riding with him. He led me down a hallway to the living room.

“Have a seat,” he said with a gesture. “I’m gonna take a leak.”

I sat down and looked around. I didn’t really notice much about the room because I was thinking about trying to run out instead. Then I realized that I had no idea where to go to get home or back to my car.

“Who the hell are you?” I heard a female voice say.

“Oh, um, I’m Drew,” I answered anxiously and looked at her. Her face was pleasantly attractive with high cheekbones and medium length narrow nose that came to a distinctive point, blue eyes, thin lips, and curly brown hair that went down to her neck.

“Did Henry bring you here?” she asked and walked into the room. I could finally see she was wearing a light blue bathrobe.

“Henry? Oh, yeah he did.”

“Henry, what the hell is going on here?” she demanded as the guy came back from the bathroom. She stood facing him with her hands on her hips.

“Well, uh, Alice, I found you a young man. Just like you always talk about,” he replied nervously. It was clear from his uncertain tone that she wore the pants in this relationship.

“Damnit Hank,” she said and picked up a half filled glass from a coffee table. The liquid looked like whiskey.

“What did he tell you to get you over here?” she said as she looked at me.

I glanced at Henry and then looked back at her. “He didn’t exactly tell me anything. I didn’t have a choice really.” I swallowed nervously after saying it.

“Oh he’s making that shit up. He didn’t know that this is just a toy gun,” he said and laughed before entering a fit of coughing.

“You poor thing,” she said with a compassionate tone and crouched in front of me before touching my cheek. I felt a sudden sense of relief at her show of mercy. “How could you fall for a toy gun?” she said with a laugh before standing up again.

I sat there humiliated and looked at the floor. It was going to be a long night.

“Come on then Drew,” she said and grabbed me by the arm and pulled me up.

I followed her down a hallway and into a bedroom. There was a big bed in the middle of the room and a couple dressers against one wall. Alice turned on a lamp that was on one of the dressers.

“Well, let’s see what you’ve got in there,” she said and sat down on the bed. She gave me one of those finger curling gestures, beckoning me her way.

I stood in front of her and waited. I was unsure of what exactly she wanted me to do. She leaned over and grabbed a rubber band from the head of the bed and tied her hair back with it.

“Come on, take your clothes off,” she said and watched.

I felt my face turning red while I stripped. I stopped when I was only wearing my briefs.

“What are you waiting for? Take those off too.”

I reluctantly pulled them down and put them with the rest of my clothes.

“Good,” she said and studied me slowly from head to toe. After she was done she rested her gaze on my cock. “Well you’re not the biggest tool in the shed, but I think I can make use of this,” she spoke as she held my cock in her cupped hand. She pointed it up and looked at my shaved balls. “Very nice. Nothing I hate more than getting those damned hairs in my mouth when I’m sucking cock.”

She stood up and walked over to one of the dressers and pulled open a drawer.

“Come here,” she said, so I went beside her. She made an O shape with her thumb and index finger and slid it to the base of my cock and then tightened it before sliding it off. Then she compared the size of the O to a few black looking rings in the drawer. Finally she found one she liked.

“Okay, let me get a few things straight,” she started and pushed me towards the bed. “First, if you’re worried about Henry bothering us, don’t. He’s probably already passed out in front of the TV. Second, I don’t want to hurt you, but if you don’t do as you’re told you might regret it. There’s lots of things in that drawer that I can use to make you dread every second you’re here. And third, you damn well better not blow your load before I get off.”

I nodded and swallowed. She must have noticed how nervous I was.

“Look, you’re going to leave this place in one piece. It’s up to you how much you enjoy it though, alright?”

“Okay,” I answered.

“Good, now lay down on the bed while I go get a drink.”

As she left the room I looked around for a few seconds. A quick glance in the drawer revealed that it was packed with all sorts of sex toys. Dildos and vibrators, a leather harness, the black rings, a few bottles of lube, and some other items I’d never seen before. I got on the bed before she returned and caught me snooping around.

She came back and took off her robe. All that she had left on was a pair of black panties and a black bra. She wasn’t overweight at all, but she did have the little tummy that many older women get at some point. Her hips were wide but proportional to her long, rather thick legs. She had a nice pair of heavy, slightly saggy tits. I felt a little better after seeing she wasn’t bad looking.

“Grab a pillow and lay your head on it at the foot of the bed,” she said as she set the drink down. “Nope, closer to the edge of the bed so your head is hanging off of it,” she told me. “That’s it, good,” she added while taking her panties off and then grabbing her drink again.

She turned so her back was to me and then stepped backwards so her legs were on each side of my head before sitting down on my chest. I stared at the thick outer lips of her pussy.

“Lucky for you I was in here pleasuring myself when Hank brought you in, so I’m pretty wet already. But I love orgasms, so it looks like you’re in for a long workout.”

She started to use the hand that wasn’t holding the drink to touch herself. I could hear her putting one or more fingers into her wet pussy.

“Open your mouth,” she said firmly and stood up.

I opened it halfway and watched her with wide eyes. Her hand came down and pushed it open wider, and then she spread her lips apart and lowered herself over my mouth.

“I hope you know how to eat pussy,” she said and took a swig out of the glass.

Unfortunately my experience with going down on women was pretty minimal, so I tried my best to wing it. I flicked my tongue on her lips, pushed it inside her and licked around, and fucked her with it. Luckily she smelled decent and didn’t taste half bad.

“You can do better than that,” Alice said and grabbed my hair and pulled my head firmly against her crotch. “Push that tongue of yours inside.”

I tried to please her and repeatedly pushed my tongue as far in as I could, but she wouldn’t accept that.

“God you’re terrible at this,” she said and stood up. “I’d get off faster if I used my fingers.”

She lowered herself again but only far enough so that her pussy was right above my face. Her hand went to work and didn’t take long to get her near orgasm.

“Open your mouth wide again,” she said with her commanding voice. “Good boy.”

She set her drink down and grabbed my hair again. Her fingers rapidly worked her clit.

“No closing that little mouth of yours. And don’t you dare try to turn your head,” she told me.

Seconds later her body tensed up and she squirted a load of clear sticky fluid that hit me on the upper lip and went into my nose and mouth. I coughed and tried to turn away, but she slapped the top of my head and deftly gripped my hair again. Her fingers went to work again and she squirted another small stream at my forehead.

“That’s more like it,” she said with a tone of satisfaction as she smothered my face with her sopping wet cunt.

Alice let go of my head and stepped away. She guzzled the rest of her drink and then sat next to me.

“Since you were so worthless with your mouth I think you need to redeem yourself,” she said. “Turn around and get on your stomach and put your hands on your back. That’s it. Now put your ass in the air,” she said, but I hesitated and she slapped my leg hard. “Good boy.”

I felt a leather belt wrap around me just above my hips. It quickly tightened and I heard a clicking sound. She grabbed one of my wrists and fastened it in something that was connected to my hip. Seconds later my other wrist was secured in the same fashion.

“Legs apart,” she said and helped me spread them.

“Ever had a cock ring on before?”

“No,” I answered meekly.

“Well there’s a first time for everything,” she said as I felt a ring roll over one of my balls and then the other. “Get used to it because at this rate you’re going to be wearing it for a while,” she added as she bent my cock and pushed it through the ring.

I heard her walk out of the room and then come back a minute later.

“I think the best way you can even the score for that pathetic display earlier is with your tight asshole. I hope you like having things inside there.”

I felt her squirt some lube on my crack and rub it in before squirting more and massaging that into my skin as well.

“What’s the biggest object you’ve had in this thing before?” she asked as she pushed a finger inside me.

“I don’t know.”

“I’m sure you do,” she replied as she fucked me with her finger. “Well this hole will be gaping when I’m done.”

She ran two fingers all the way inside me. I suddenly felt thankful that my masturbation sessions often included some fingering of my own, so what she was doing was not all that unpleasant. But her comment about my asshole gaping was bothering me.

“You seem to be taking this a little too well, so let’s skip to four fingers. Oh, much more resistance. That’s too bad,” she said as she slowly forced them into me, “because you’re going to have to take in a lot more than that.”

I let out a grunt of pain as she finally pushed four fingers all the way in. All that remained was her thumb. She turned her hand around back and forth a few times before rapidly pushing them in and out.

“Let’s see here, I bet I have a nice big toy to use. Yes, here we go,” she said and I felt the pressure of what felt like an enormous object against my entrance. “You need to stop being so tense. You’re making this way too fucking hard on yourself.”

My hole finally conceded and I felt the toy pop in. I breathed deeply and tried my best to take it.

“That’s better. God that’s hot. I wonder if you can take all of it. Oh yes, look at that it’s half way. Three quarters,” she sounded genuinely excited. I felt the toy press against the inner wall of my bowel. “That’s almost all of it. I bet I can get the rest of it in there.”

“Ugh,” I grunted as she pushed hard against my insides causing a lot of discomfort.

“Take it! Yes! It’s all the way in. Good thing this ass of yours is bigger than your mouth,” she laughed. “Now you get to see how it feels getting fucked hard by this thing.”

She wasn’t nice enough to go slow. Instead she quickly pulled all but the tip out and then pushed it right back in until it hit the side of my bowel again.

“I can tell you like this because there’s some cum dripping from your cock already. Too bad you can’t see this dildo fucking you.”

Her pace quickened and I started to moan each time she pushed the object in. “Oh shit,” I gasped.

“Mmm you do like it. I thought so,” she giggled at me and slapped my ass. Her fucking didn’t slow at all though, and then suddenly she pulled the whole thing out.

“Time for something bigger,” she said and I sighed. I could feel my eyes starting to water. “Hmm, I’m not sure what to use. Oh I know.”

I felt her fingers again, including her thumb this time. She pushed the tips in and started to alternate between spreading them apart and easing more inside my ass.

“Don’t fight it,” she said. “You’re going to be the first guy I’ve fisted whether you like it or not. That’s it, my fingers are inside now, but the tough part is yet to come.”

“It hurts badly,” I said with a weak voice.

“You’ll get used to it. I just need to get past my knuckles. Oh, almost…yep, nearly in. One last push,” she said and then I felt her whole fist move inside.

I moan loudly and cried silently from the pain.

“Such a good young man. How does it feel to have my entire hand inside you?” she asked in a mocking tone. “It’s so hot in there. I think you need more than that inside though. I think I should go wrist deep now you little slut. I bet you’d love for me to fuck you like this all the way up to my forearm wouldn’t you?”

I shook my head but was too weak to say anything.

“I didn’t hear any objection, so here it goes,” she said and slowly pulled out until the wide part of her hand was stretching me open. “In and out, in and out.” She said with each motion. “You’ve got half my arm going in there. In and out,” she kept saying as she arm fucked me. After a couple minutes she said, “I think that’s enough for now.”

She was kind enough to pull her hand out slowly, but it still hurt like crazy.

“Look at that, your hole is wide open now. I think I might have to take advantage of that.”

I heard her doing something for a few seconds before coming back to the bed.

“How about some ice cubes? In goes one,” she said and I felt the thing slide right into me. “Another and another.” The cold feeling inside was a little strange.

“Gosh, I’d hate to have you freeze in there, so I’ll do you a favor,” she said with a laugh. I felt her stand on the edge of the bed. “Slide up the bed.”

She put her hands on my hips and pushed me nearer to the head of the bed.

“I can’t believe how nasty you are! I’m getting so turned on,” she said. I felt her hips grind against my ass. “Now let me help you out with that cold in there,” she said and sighed a few seconds later. That’s when I heard the sound of water gurgling and realized she was pissing into my ass. Part of me felt incredibly repulsed. But another part of me was intensely aroused.

She sat beside me after she finished relieving herself and softly stroked my cock for a few minutes while I held her sick idea of an enema inside me. The pain of my stretched ass was starting to increase as the muscle gradually returned to its normal size.

“Okay, you better use the toilet and empty that out, but not until I say you can,” she said and helped me off of the bed. “Easy now, don’t fall down.” She hooked her arm around mine and held me steady until I sat down on the toilet.

“Hold it in,” she ordered before sitting on my lap facing me. She spread her legs and sat up very straight before pulling my face into her big saggy tits “You like these? Here suck on this. That’s it. Oh that feels good.”

I sucked on her nipples as she held them to my mouth. This went on for a couple minutes before she wrapped her arms around my neck and smothered me with her chest.

“You can shit now,” she said. I immediately relaxed my ass and felt the dribble of warm water come out. Once the liquid was drained I could still feel the cold ice inside, so I pushed it out too.

“Now it’s my turn,” Alice said and she started pissing. The hot stream hit my cock and flowed down my balls. “Ahhh, so relieving.”

She stood up and helped me stand as well before wiping my cock and ass. Then she led me back to the bed where she put me in the same position as before.

“I bet you thought I was done with your ass. Well guess again. Now it’s time for a real fucking,” she giggled and slapped one of my cheeks.

I turned my head and managed to see her sliding the short end of a two headed dildo into her cunt. The end she pushed into herself curved upward so that once it was all the way inside, the opposite end stuck out like a real cock. After that she pulled a leather harness over the dildo and up to her pelvis and then tightened it.

“Mmm, you’re going to enjoy this,” she said.

I heard the lube bottle click open and felt it press against my hole followed by the slurping sound of it squirting into me, then more dripping around my hole on the outside.

“That should do,” she said and knelt behind me. “Here we go. Relax. Good, there it goes.”

The long shaft went in easily until she hit the back of my bowel with it and then pulled back.

“I never cared much for slow fucking,” she said with a laugh and started right in with a fast pace. “I always wanted to screw a guy in the ass. There’s nothing like payback for those times when they did it to me.”

She fucked me hard and fast like that for minutes. Almost every time she rammed the dildo in she hit would slam into the side of my cavity and cause me to flinch and moan at the same time. Despite that pain, it was starting to feel really good. She moaned with me from the sensations she felt as the end of the toy inside her shifted around.

“Lucky you, I think this thing is going to make me cum. Yes!” she exclaimed and picked up the pace in the midst of her excitement. “Oh God YES!” she yelled and her hips stopped moving steadily and started to buck in sudden wild thrusts which only added to my pleasure. Her hands pulled my hips back into her as leverage for her to push her end of the dildo into her pussy harder.

“I think I’m going to cum,” I managed to say, only to be disappointed when she pulled out.

“Hurry up and turn over while I grab some pillows,” she said and I was quickly on my back with the pillows under my hips. “I want to see you shoot your load.”

She returned where she left off with the fast pace and my excitement built back up right away, but it wasn’t quite enough.

“Please do it like when you were cumming,” I begged, desperate to finally orgasm.

Her hips paused immediately and then thrust forward over and over again before she paused and had me lift up my legs and bend them over her shoulders. When she started again I almost exploded. The dildo was now rubbing my prostate almost directly with each thrust. Moments later I felt the sensation of orgasm in my balls and I arched my back.

“Oh shit!” I cried out.

Alice responded with faster harder thrusts and I lost all control of my body. Every part of me shuddered and I writhed on the bed as she continued to fuck me. I felt the first stream of cum fire out into the air and land on my chest, followed by several more each time my prostate was hit. Once Alice saw that I was dry she slowed down and pulled out.

“That was incredible,” she said as she sat beside me. “I think that’ll do for your lousy pussy licking earlier.”

She leaned over and licked up the cum that was on me. Once she’d gotten all of it she milked the remaining amount from my cock and sucked it into her mouth as well. Then she straddled my hips and leaned over me so her face was in mine.

“Open wide,” she said.

I shook my head in refusal when I realized what she was about to do.

“Open your fucking mouth,” she yelled and slapped my cheek.

I whimpered and then opened my mouth. She plugged my nose with one hand and then held my chin with the other. Rather than kissing me, as I expected her to, she raised her head up and dripped my cum into my mouth slowly so I could watch it. Once it all was in my mouth she kissed me for a second and then held my mouth closed and forced me to swallow. I had to fight off the urge to gag.

“That’s better,” she said and glared at me as she landed a hard slap on my face. “I think you deserve more punishment for that. Get your ass in the air again.”

I slowly turned over and struggled to follow her instructions. My energy was nearly spent already, and I started to wonder how much longer I was going to have to endure this woman’s apparently insatiable desire to toy with me.

“I bet that hole of yours is pretty tender. But I think it’s going to suck my whole fist right up,” she said and pressed all of her fingers against my ass. “Come on, they’re going in whether you like it or not. I’m going to milk every bit of jizz out of you and then make you eat it. That’s it; my fist is almost in again. A bit more…there it goes.”

I grunted and bit my lip as my rear adjusted to her hand. I felt like I was about to pass out due to exhaustion.

“Oops, I forgot to get something to collect your cum in,” she said as she slipped her hand out and I shook under the pain. She grabbed her empty glass and set it under me.

“Can I have a drink of water?” I asked.

“Sure, hold on,” she said and left.

As I waited I felt my legs starting to quiver so I tried to spread my knees apart more, hoping that it would make it easier to remain in that position. Instead I ended up falling on my side. I didn’t bother trying to get up.

“What the hell are you doing?” she nearly yelled when she came back.

“I’m sorry; I was trying to spread my legs apart. I feel like I’m going to faint.”

“Oh alright, I won’t punish you for that then. Here, drink some of this,” she said and helped me sit up. “It’s some soda,” she added and held the glass to my mouth. I greedily drank from it. “Good boy. Drink all of it. That’s it.”

She put the empty glass on the dresser before grabbing my hips and pulling them in the air. Then she pushed my knees apart.

“Now where was I? Oh yes, milking you,” she said. Her fingers pushed into me, and she fucked me with them a few times before forcing her entire hand in again. The pain made me start to cry again.

“What the hell is wrong now?” she said.

“It hurts. My body is tired,” I said and pushed my face into the bed.

“Well get used to it, you little bitch. I’m not done yet,” she spat and pushed more of her arm into my ass. I groaned loudly into the bed. “Now stay still. Maybe when I’m done with this I’ll take those restraints off.”

She withdrew her arm until only her fist remained within me. Then she pushed softly against my prostate and held the empty glass under my cock which was already dripping.

I was too tired to care anymore. She massaged my insides for what seemed like fifteen minutes, perhaps longer. At first I felt only the pain from the stretching of my hole, but soon I felt so good. And a handful of times I thought I was going to orgasm but it ended up being more of like quick shudders of pleasure without any release.

“I see you still had a lot of cum stored up in there,” she said towards the end of the milking. “And I haven’t seen any leaking out for a while, so I guess it’s time to stop.” She pulled her fist out and I fell over. “You stay there. I’m going to wash up.”

At that point I didn’t have the energy to move. I was too tired to do anything, and in too much pain to fight her demands. I closed my eyes and waited.

“Now it’s time for you to empty this glass,” she said and rolled me on my back. I watched her through half-shut eyes as she tossed the glass back and drank the surprisingly large amount of fluid that looked like swirl of clear and milky white.

She demanded leaned over me and put a fingertip to my mouth. I knew what she wanted and opened my mouth. Again she let the viscous liquid slowly dribble from her mouth and into mine before plugging my nose and closing my mouth. I swallowed it and looked up at her. My eyes were still watering.

“That’s better. See, you just have to do as you’re told. Now, let’s see if you can properly eat pussy yet.” She positioned herself so her pussy was over my face and her head was near my cock. “Get to work!” she yelled.

I didn’t have the energy to do anything, and simply stuck my tongue out when she pressed her sex down on my face. I could hardly breathe with her big pelvis covering my nose and mouth, so I started to panic and turn my head. A few seconds later she got up on her knees.

“Fucking worthless mouth you’ve got,” she grumbled and got off of the bed. “Maybe you need more convincing that listening to me is the right idea.”

I cried to myself and tried to see what she was up to. All I could manage was a glimpse of her bent over by the dresser.

“I’ve wanted to try this thing for a while, and it looks like you’re the lucky victim,” she said as she stood on the side of the bed. In her hand was a black object that looked like a long wide spoon covered in leather.

She sat down and slapped my breast and nipple with the paddle to inflict a sharp pain. She hit me a few more times in the same spot and then started on my inner thighs. My head reeled and I felt like I was spinning. Then she inadvertently hit my balls with it, but it was hard enough to make me black out.

I didn’t know how long I was passed out, but when I came to my arms were no longer restrained to my waist. Instead I was on my back with my legs tied to the corners of the bed and my arms freed. Alice was lying on her back under me and had my head against her chest.

“Are you awake?” she asked softly as she ran her fingers through my hair. I nodded. “Good. I was a little worried. Do you feel okay?”

“I guess,” I said hoarsely.

“I won’t do that again. I didn’t mean to hit your balls before. Honestly, I didn’t,” she said and slid out from under me. “I’m not finished yet though. I need to get off a few times, and you’re going to help me. But don’t worry. You just have to lay there.”

I rubbed my head and then watched her pick up two long black objects and a bottle of lube from the dresser.

“Put your hands in the air,” she said and set down the black things. “Have you ever had your hand in a woman before?”


“I guess I’ll have to do all the work then,” she said and started to rub lube all over my hands and down my arms to my elbows. After that she put down the bottle and picked up one of the black things. It was a long latex glove. I squeezed my hand together and she pushed the glove over it and down my arm. She repeated the process with my other arm. Once it was on she coated both gloves with more lube.

“Sit up,” she said and squatted between my legs with her back to me. “Now you do exactly as I tell you and we’ll both enjoy this.”

She set her knees on the bed and spread her feet apart before raising her ass in the air. I saw that she had a toy stuck in her rear.

“Hold onto that butt plug. I’m going to push it out,” she said. I held the flat end that was sticking out and watched as she slowly expelled a plug that was at least two inches wide. As it popped out she sighed.

“Okay, now start working your hand into me. Don’t you dare try to shove it in fast because I won’t hesitate to turn around and slap you a dozen times.”

I formed my hand in as narrow an object as I could and pushed my fingers into her ass until the widest part remained outside. Alice reached under herself and grabbed my wrist.

“Let me do the work now,” she said. “I just need to slowly…push…in,” she continued while moving my hand into her ass. “Oh fuck that feels good. I haven’t been fisted in months. Okay now I need you to keep it in there while I turn over.” She pulled my wrist and took another inch of my forearm into her ass.

“Carefully now,” she said as she got on her knees. Being tethered to her this way fascinated me. “Okay, going to slowly turn over now. That’s it. Oh, no don’t let it come out. Good.” She cautiously dropped down on her back.

“Look at how wet I am already,” she remarked and stroked her pussy. “Okay, give me your other hand. Squeeze your fingers together. Good, now start pushing it in.”

I really didn’t do much. Alice held my wrist tight and eased my hand in. She was loose already and it didn’t take much work for my whole hand to be sucked in. I couldn’t believe she actually had both of my hands and part of each arm inside her.

“Pretty fucking hot isn’t it?” she asked when she saw my expression.

“Very,” I said.

“Well the best part is next. Hold those things in me again while I get on my knees. You’ll have to lie down as I get up, okay?”

I nodded and we slowly shifted positions as she said, but rather than kneeling she was in more of a half crouched stance. As she held herself there, with her hands planted on either side of my head, her breasts hung near my face.

“Good, now just hold your arms still while I do this.”

It was weird to see her that way with part of my arms disappearing into her. My cock had gotten rock hard during the whole process to the point where it was aching. The ring she’d put on me didn’t help with that.

She slowly lifted her hips up and my arms started to ease out. Once she felt certain that she could actually start fucking my fists she moved faster. Within a minute she stopped and let out a scream that made me blink. Her internal muscles clenched my wrists as she came.

“Holy shit,” she gasped. “I haven’t had an orgasm like that in years.”

Only seconds passed before she started to grind her hips again, this time faster than before. As her big tits swung around in front of me I couldn’t help but lift my head up and suck a nipple into my mouth.

“Oh fuck yes, suck my tit,” she said as she got a good pace going. “I’m going to cum again! Fuuuuck!”

She slammed her hips down in quick thrusts as she shuddered from the pleasure. All of her shaking pulled her nipple out of my mouth.

“I can’t stop cumming!” she yelled and her hips sunk down suddenly. I felt my hands hit the back of her body cavities which caused her to spasm and lose her balance. She fell forward on top of my face and the hand I had in her ass pulled out.

“FUCK!” she screamed after feeling the sudden exit. “Oh shit, oh shit, oh shit,” she said trembling and held still. “I don’t want to move. It feels so good, but I can’t take much more.”

I just laid still and let her do her thing. I was blown away by how much she was getting off and how rapid her orgasms were coming.

“Oh. My! GOD!” she shouted and pushed her pelvis down on my hand as yet another orgasm hit her. Her back arched suddenly and she fell on her side with my fist still stuck in her cunt.

“Pull it out. I can’t take anymore!” she exclaimed.

I started to pull out, and then I realized that I had the upper hand even though I was still bound by my legs. It was a split second decision, but I settled on getting a little revenge.

“Slowly. Pull it out slow,” she said as she lay on her side with one leg in the air.

I followed her instruction and eased my hand out until the wide part of my hand was just about to come out. But instead of finishing the exit, I pushed my hand back in quickly until half of my forearm was in her.

“What the…FUCK!” she screamed again and clamped her legs together as she endured another wave of pleasure

I kept fucking her rapidly. Each time I pushed in I tried to get more of my arm inside and eventually got about three quarters of the way to my elbow. Her body never stopped to spasm and twitch as I was doing it. I continued until she found the strength to grab my wrist and take control.

She lay there completely still afterwards. While I waited for her I pulled off the gloves and tossed them onto the floor. Then I untied my feet and pushed her into the middle of the bed so she wouldn’t fall off. I sat down and watched her breathing heavily and shaking.

“Alice?” I said.

She didn’t respond, so I rolled her on her back and patted her face softly. Her eyes opened.

“Are you okay?” I asked her.

She nodded and swallowed. “Yeah, just worn out and sore.”

“Okay,” I said and sat there, uncertain what to do.

“I guess I should think about driving you back,” she said and sat up.

I felt a sudden surge of energy upon hearing mention of being released.

“I’m sorry if I hurt you earlier,” she told me and reached for my face. It was the first time she had shown genuine care for me.

“It’s okay, I’m fine now.”

“Let me make it up to you, okay?”

“I don’t know,” I said. Her idea of making it up to me could mean just about anything.

“Nothing like what I’ve done to you, I promise. Actually I’ve wanted to suck your cock for a little while now.” She got rolled on her back and put her head on the edge of the bed. “Come here. Stand by my head.”

I did as she told me to. She carefully pushed my cock out of the ring and then released my balls from it as well. Then she took my cock in her hand and pulled me so she could put it in her mouth. For a few minutes she sucked and stroked it until I was hard again.

“I bet your girlfriends never gave a blowjob like this,” she said and slowly took a few deep breaths.

She wrapped her hand around the base and took the head in her mouth. Then she put her hands on my hips and pulled me towards her. She was right, this was unlike anything I’d felt before. As she pushed and pulled my hips, my cock fucked her mouth and throat. I felt her exhaling on my balls every few seconds as she worked me over. She managed to go like that for a couple minutes before she pushed me back and pulled my cock out of her mouth. Big gobs of saliva dripped from the tip and down her cheeks. After catching her breath she took the whole thing in again and resumed the deep throat fuck. She had to take another break before I started to feel the beginning of my orgasm.

“I’m going to cum soon,” I said as I looked down and watched her. Each time she pulled my hips I could see the swell of my cock in her mouth and throat.

She pulled me out again and took a breath. “Cum in my throat, don’t try to pull out,” she said with a gasp and then took me in her mouth again.

I leaned forward and put my hands on the bed as she continued. The sensations were so good. When my orgasm was close I started to move my hips and fuck her throat myself. She let go of my hips and let me do the work. I moved faster, slapping my balls against her forehead each time as I pushed in as far as I could.

“I’m gonna cum,” I whispered and Alice moaned out a response.

My hips moved even faster as the final seconds of buildup passed. Then I pushed in one last time and held still as her throat massaged me. As the orgasm hit my body stiffened but my hips shook. I felt my cock pulse repeatedly but couldn’t feel any cum shoot out. After a few moments of climax I relaxed and pulled out.

Alice sucked in a huge gasp of air and coughed immediately. I sat down and felt dizzy.

“Are you okay?” I asked her after she had been unable to stop coughing, but she couldn’t answer. I rolled her onto her stomach and patted her back firmly.

“Yeah, I’m okay,” she said finally and wiped her watery eyes.

She moved to the middle of the bed and put her head on a pillow. Even though she’d used me like a rag doll earlier, I felt like I wanted to be near her for some reason, so I sat next to her waist and watched her.

“Well Drew, you’re something else,” she said after a few minutes.

“It’s not like I had any choice,” I said.

“That’s true,” she replied and laughed, but not in a mocking way. “But you were a good sport anyway,” she said and closed her eyes.

Her chest was still heaving a bit as she recovered from the blowjob. I watched her big saggy breasts rise and fall with each breath. Then I looked down at her pussy and saw that it was oozing with her juices, so I reached out and gently pressed a finger inside. Alice’s body stiffened when I did it.

“I’m so sore down there,” she said and opened her eyes again.

She didn’t object to my touch so I kept playing with her. She spread her legs apart a bit for me and closed her eyes again.

“It’s probably about time you got out of here,” she said.

“I’d appreciate it.”

“Alright, just give me a few more minutes.”

I pushed three fingers into her loose pussy and slowly fucked her with them.

“This is why I wanted to get a young guy over here,” she said. “So eager and so much energy to burn. But you better stop. I need to clean myself up before I drive you back to your car.”

“Okay,” I said and pulled my hand away from her. Out of the corner of my eye I saw my clothes, so I got up and put them on.

“I’ll be right back,” Alice said and left the room.

I wandered over to the dresser and looked inside the toy drawer. Most of the toys were small, but one caught my eye. It was a butt plug much like the one Alice had been wearing earlier. I glanced at the door and made sure she wasn’t coming. Then I picked up the plug and put it in my coat pocket.

“Ready?” she said as she came back. She was wearing a pair of jeans and a white t-shirt with no bra underneath.

“Can I ask you something?” I said.


“This might sound weird after what you’ve done to me. But you’re a good looking woman. Why in the world are you with a guy like Henry?”

“Oh boy, well, we’ve been together for a long time. The years haven’t been kind to him though. He has his good moments, but he has a lot more bad ones. We pretty much mind our own business these days and that works for us. And thanks for the compliment. I don’t get many looks from guys your age anymore.”

“Sure,” I answered.

“Well let’s go,” she said and led the way to the door. As she opened it I realized I had to piss.

“Can I use your bathroom first?”

“Of course,” she said and followed me, but then she grabbed my arm. “Wait.”


She gave me a smirk and led me to the living room. “I bet you’re pretty upset with him.”

“Yeah, kind of,” I said.

“He’s not gonna be up for a while. Why don’t you piss on him?” she suggested.

“No way, it’s gross,” I said and gave her an odd look.

“Come on, I’ll do it first,” she said and undid her jeans as she stood right in front of Henry on the couch. She stuck her hips forward and held her pussy lips between two fingers. Then she pissed on his chest.

“That’s so messed up. Won’t he get mad at you?”

“He’ll never know what happened. Probably just assume he spilled a drink or something. Come on, your turn,” she said as she finished and zipped up.

I hesitated, so Alice took a gentle hold on my arm and pulled me in front of Henry. Then she unzipped my pants and pulled my cock out.

“Let’s see,” she said as she pointed it at him. “I say shoot for his crotch.” She lined me up so that she thought I was aimed right. “Do it.”

At first I couldn’t pee, but then it came out in a strong stream. As I watched it splatter over Henry’s pants I suddenly felt dirty, embarrassed, and ashamed.

“You really had to go didn’t you?” Alice said as she held my cock and smiled.

“Yes, I’ve been holding it for a while,” I told her. “I can’t believe I’m doing this.”

“Don’t sweat it, he deserved it anyway.”

I sighed as I finished and watched Alice tuck my cock back in and zip me up. When she was done she patted my crotch.

“Let’s go,” she said and led the way outside.

We got into her car and started driving.

“I hope you’re not feeling any ill feelings towards me,” she said softly.

I looked out the window and watched the trees pass. “Well I’d be lying if I said I don’t. But at the same time I have to admit that I had an amazing time, even if it did hurt a lot.”

“That’s good,” she replied.

“Have you done this before?”

“No, well, not exactly. About four years ago we had a family living next door and they had a son who was in college. One summer I caught him looking at me a lot when I’d wear swimsuits outside. So I decided to see if he would take the bait and I could seduce him. It ended up working and we had some interesting times together. Nothing at all like what you and I just did, but we did some pretty kinky stuff. That’s it though. Henry isn’t able to get it up anymore. He hasn’t been able to for like ten years. So mostly I am left to play with myself. Once in a while I invite a couple girlfriends over and we masturbate with each other and try out new toys”

The drive passed slowly and we didn’t say much for a while. I kept shifting in my seat, trying to find a position that didn’t hurt my ass so much.

“I probably shouldn’t even mention this, but…oh never mind,” Alice said.


She sighed and waited a few seconds. “Well I’ve those two girlfriends who are into some of the same stuff as me. I bet they’d love to spend some time with you. None of that pain and restraint stuff though, just a lot of kinky consensual fun.”

“I don’t know,” I said. “I’m not the type to do something like this once, let alone more than that.”

“Well you think about it. I’m serious. They’d be all over the chance to actually try some of the things that the three of us talk about when we’re together.”

We were silent until we arrived at the bar where the whole night had started. Alice pulled up in the middle of the parking lot and put the car in park.

“Here, take one of my cards. If you decide you want to take up my offer, or even if you want to get together with me again, call me. You can reach me on my cell any time,” she told me and reached into her purse. “There, it’s the number on the bottom.”

I looked at the business card. It was for a catering business. “What do you do exactly?” I asked as I tucked the card into my pocket.

“I’m a chef,” she replied.

For some reason I laughed.

“What?” she asked.

“Oh, I’m not trying to be mean. It’s just weird to think of you as a chef after this whole thing.”

“I bet,” she said and smiled.

“Thanks for bringing me back here,” I told her.

“Of course,” she said and watched me get out. “I hope you decide to call me. You’re a lot of fun.”

“We’ll see,” I said and shut the door.

Alice slowly pulled away and stopped by at the street. I watched as she drove off before I got into my car. The drive home went fast. I kept thinking back over what Alice had done to me and felt myself getting hard. Even the gross stuff was turning me on which made me laugh and feel embarrassed at the same time.

When I got home I found the butt plug I’d taken from Alice’s toy collection and put it in one of my drawers. As I covered it up with my clothes I grinned at the thought of cornering Henry in that dark parking lot and somehow forcing him to take the thing in his ass. I put Alice’s card on my desk and laid down for bed where I fell asleep thinking about her offer.

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