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Allison

Category: Anal Sex
20.05.2021
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“Uncle Joe, please! I’m serious, OK? You have to stop sleeping with my friends!”

Lilly, my niece, was livid. I’m not exactly sure how she found out, but then I hadn’t exactly been going to great lengths to hide it either. Emily and Laura were both consenting adults. Sure, I was twice their age. But it was they who had come to me.

Laura had been the first and it was a magnificent fling. Maybe I had just been oblivious to subtle cues, or maybe she really had skipped zero to fifty-nine and started flirting at sixty. I’m not sure. But she had seemed to come on so overtly, and yet without giving in. Completely committed to being a fierce cock tease.

At first I had thought that she just wanted the attention. And my attention she most certainly had. But being forty and her nineteen, I never figured that she would actually put out and I attempted to seem reserved and casual. For a couple of weeks she seemed happy to position herself as the subject of any fantasies that I might have. Then one evening she had taken my hand and and run it up under her skirt to where I found her to be as physically aflame as I.

Emily was an interesting case. We had carried on on and off for about a year. Her fascination was with being a sexual submissive. But that eventually lost her interest and she moved on.

“How many of your friends do you think I’ve slept with?” I asked.

Someone must have made a big deal about it, and now she was making a big deal out of it.

“It doesn’t matter,” she practically yelled.

I tried to reason with her again, “Your friends are all adults. What’s the big deal? It’s not like I’m chasing them. They started it.”

“It’s gross,” She replied. “Men your age shouldn’t be sleeping with women my age.”

“But it was OK when you seduced your former professor who, by the way, is at least 10 years older than I am,” I shot back.

“That was different!” She was yelling now, but she knew I had her and she started to smile a bit. “That was me!”

“uh huh. So it’s OK for you to seduce a man in his fifties but it’s not OK for your friends to seduce me. I get it,” I sang sarcastically.

“It’s not just you,” she explained. “It’s your friends. They’re my friends too, but … my friends MY age are starting to hang out with them because of music and stuff.”

“I’ve seen a couple of your friends at some of the more interesting parties recently,” I acknowledged. “You’re worried that you’ll pick up a certain kind of reputation by association.”

“YES!” She threw her arms in the air, “I’m not into all that weird shit, but people are going to think I am! Don’t get me wrong. I love my older friends and family and don’t care what you do to have fun, but I’m tired of my younger friends assuming that I’m all into that stuff just because I know people that are.”

=====

Allison knocked on the door as she came through it.

“Hey,” she said and wandered down the hall to Lilly’s room. I didn’t think Lilly was home, but wasn’t sure and it wasn’t unusual for a few of her friends to drop in unexpectedly. Allison poked her head in Lilly’s door, closed it and came back down the hall to the living room.

“I thought Lilly might be here,” she said casually and dropped herself onto the couch at the other end.

“I’m not sure where she’s at,” I said trying not to stare.

She was a real redhead with pale, smooth skin and the kind of warm and friendly smile that would intrigue anyone. Her hair was medium length and bit of a tangled mess. Her first attempts at dreads hadn’t really worked out, but somehow it looked incredibly attractive on her. I had often found myself thinking how nice it would be to run my hands up into her tangled top and taste the blushing lips below.

“You meeting Lilly?” I asked.

I used the question as an excuse to look in her direction. She was wearing three or four layers of shirts and scarves in various colors against the chilly winter air.

“I thought she might be here, so I figured I’d just sorta drop in,” Allison replied.

As she spoke she shifted her legs up onto the couch to sit cross legged facing me. She wore heavy black leggings under a pair of tattered and loose fitting Daisy Duke cutoffs. The power of suggestion is a powerful force. Even though her entire lower body was sheathed in at least one layer of heavy, opaque fabric the fact that only a few inches of loose fitting and frayed denim covered her crotch somehow gave the impression of sexual availability.

“What are you reading?” she asked.

“Oh, just a Terry Pratchett novel. Great light reading,” I answered.

Does this visit seem suspicious? Maybe I’m just being paranoid. But after the conversation I just had earlier today with Lilly, I can’t help but wonder about Allison’s motives for stopping by. It’s too much to hope for, really. I shouldn’t even let my mind go there. It’ll just end in her thinking that I’m a creepy old man. Pretty much the total opposite of what I’d want.

“You been reading anything in particular lately?” I asked.

“A little. No books, really. Just like short stories and stuff. I’ve been trying to write a little,” Allison said with a bit of a lift in her voice.

“Yeah? What have you been writing?” I asked.

“I’ve been trying to write some short stories and post them to different places on-line for writers to post stuff. I want to get, you know, like, feedback,” she said.

“Cool,” I stated in what I thought would sound like a positive sort of encouraging manner. “Where you been posting to? There are a lot of places on the web to publish stuff too.”

Her eyes darted about just a little, “Just … one or two sites for writers. No place in particular.”

I raised one eyebrow conspicuously.

“Hmm. Dodgy. What, are writing erotica or something?” I jested.

Allison giggled and said, “No! No. Well, maybe a little.”

Her eyes rolled to the right and down to look at the floor. She smirked nervously. I laughed quietly and rubbed my forehead with one hand. My life is starting to read like a cheesy script.

“Dear Penthouse Forum,” I thought to myself.

“That’s pretty funny. Let me guess – Literotica?”, I quizzed.

She looked startled.

“It seems like all of my female friends are into that site,” I teased. “Have you gotten good ratings?”

Allison smiled into her lap. “Some,” she said. “It’s OK. Some of the female writers are really hot. And some of the men, too. Though mostly the men don’t seem to understand what women want to read. And when they try to write from female perspective it’s just … “, her hands wrung the air, “… obvious that they aren’t women. Some of the gay sex stories are wicked hot.”

What is it with women and gay sex? I asked a female friend once and she replied, “I don’t know. Why do straight men love lesbians?”

I’m not going to ask for her nom de plume. Let her offer it up if she wants me to read her stories.

Resting my chin in my hand I smile and ask, “Any stories you like in particular?”

“Well, yeah,” she says blushing. “But I don’t have a computer. I’m always using someone else’s.”

“Ah. Hey, I was going to make some tea. Want some?” I say getting up.

“Some Lady Grey would be great if you have it,” she answers. “Can I use your computer?”

I pause for just a moment on the way to the kitchen.

“Sure. It’s over there on the desk,” I say.

I’m not sure where this is going. Somehow I seriously doubt she’s going to summon erotica from the Internet to share. Even in light of fairly recent events, it’s just too much to hope for. Laura and Emily were just flings. I can’t let myself think that all of Lilly’s friends want to have sex with me. That’s completely unreasonable. And maybe a bit creepy on my part.

Knowing that she’s busy at the computer, I hang out in the kitchen and do a few dishes while I wait for the tea water to boil. The warm water relaxes me. The tea kettle steams and I pour two cups of tea. Lady Grey for Allison and Earl Grey for myself.

“Do you take milk?” I ask loud enough for her to hear me.

“Yes, please. Just a little though,” Allison replies from the living room.

I bring two cups out and approach the desk.

“I saved a bunch of links in Live Journal. Private, so no one can see it but me,” she explains.

Turning her head and smiling up at me she says, “I mean, if you want to check it out.”

Allison’s voice drops to an indistinct mumble and she seems unsure of herself.

“Sure,” I say trying to sound encouraging but not too eager. “Let me grab another chair.”

Allison shifts her chair to the right so I can get another chair in next to her. She clicks open a story and quickly scrolls down a ways.

“We should read these out loud,” she says. I can hear a little panic in her voice. She’s scared for some reason. Maybe she’s wondering how safe I am, or if this was a bad idea.

Highlighting a paragraph she says, “Here. You read first. This part is pretty good.”

I’ve never been able to read erotica or porn with a straight face. The best I could manage was a bad Hercule Poirot imitation. Allison started giggling and then laughing. By the time I had gotten through a couple of paragraphs of vanilla erotica she seemed much more relaxed.

Allison read the next story fragment in a breathy voice that reminded me a little of Ginger from Gilligan’s Island. We went back and forth like that for a few stories. The effort of reading aloud comically distracting me from the content.

Then she clicked open a journal entry that had three small pictures of a woman giving head. Allison paused.

“This was, uh, for research,” she explained. “So I could describe what was happening.”

The next journal entry was a set of photographs of women in different positions of submission having their mouths fucked. Their faces were dripping with saliva. One woman had her arms behind her back. Another was obviously masturbating. I noticed that they all had red hair.

The next entry was a series of photos from the same scene. A beautiful redhead grimaced while one thick cock was being shoved up her well greased ass and another was forced into her mouth.

Allison and I looked at each other. Her face was flush and her lips moist. My eyes followed her left arm down to where her hand was held firmly between her thighs.

“What do you want, Red?” I asked quietly. “What are you after?”

“I want to know what it’s like to be used,” Allison answered. “Like a toy or a sex slave. Don’t even pretend you care about me getting off.”

I cocked my head to one side and said, “I’m not sure that you know what you’re asking.”

She was silent and still, but for her breathing. I reached around her shoulders and ran my right hand up into her tangled red hair. I took hold of her scalp like a basket ball and pulled her head back gently.

“Is this what you want?” I queried.

She attempted to nod her head and whispered, “Yes.”

“You’re offering yourself to me for my pleasure,” I restated. This could be dangerous territory. I had to make sure.

“Yes,” she answered.

“Yes, Sir,” I corrected.

Her eyes grew wide and she took a deep breath.

“Yes, Sir,” Allison repeated. “Use me like a dirty little red headed slut.”

I smiled and took a breath to contemplate. I stood, and walked over to the couch and sat back down. Allison’s eyes were on me.

“Come here. Stand in front of me,” I said casually. “I want to have a good look at what I’m being offered.”

Allison fumbled out of the chair and hurried across the room to stand in front of me.

“Put your hands behind your head and turn around slowly,” I commanded.

She looked awkward turning so slowly, but it gave me time to openly stare at her as I’ve wanted to do for months. I let her see me staring at her openly.

“Arms behind your back. Like in the photographs you were looking at,” I said standing. “And spread your legs. Wider. Good.”

I reached up and gently grabbed her back the back of the head again with one hand and ran the other down her side. I savored the curve of her waist and hip. My hand drank in the ripe firmness of her backside. I pulled her close and revelled in the fullness of her lips as they parted to welcome my own mouth.

“Remove your clothes,” I stated plainly. “Fold and pile them neatly on the couch. Do you understand, slut?”

She twitched at the word “slut”, but after a moment replied, “Yes, Sir.”

I stepped back and circled her slowly watching her strip. It was a modest display of functionality. There was no strip tease. Her clothing simply came off to be folded one piece at a time. She paused and turned her head to find me when she unfastened her bra. I locked eyes with her as she pulled it off. The pale flesh of her chest was exposed. Her breasts were modestly generous, but not large. Her nipples stood erect. I circled behind her most of the way and ran a hand up under an exposed breast, cupping it as if to weigh it.

“Very nice,” I whispered in her ear and stepped away again to let her continue.

Her Daisy Dukes hung on her hips loosely. She unsnapped them and they fell to the ground. The black leggings looked out of place. They were peeled down slowly. Self consciousness must have taken hold, because Allison was moving in such a way as to keep her thighs closed as much as possible. Finally she was completely and magnificently naked.

I stood in front of her, close. Her arms were folded over her tits and her thighs were slightly crossed. I closed one hand loosely just under her jaw. The span of my fingers was just enough to feel the veins pulse on either side of her neck.

“Is that how I told you to stand?” I demanded. “You tell me you want to be treated like a dirty little red headed slut and then you try to hide your body? The body you gave to me. Put your hands behind your back and spread your fucking legs.”

She looked afraid for a moment, but as soon as I let go she responded to correct her position.

I smiled and hummed approval as I ran my hands across her supple flesh. My palms slowly explored every inch of her torso. Her cheeks were flush and her breathing as heavy. She looked off in the distance as I openly took measure of her body. The passage between her thighs had been shaved smooth except for a small patch of red fur just above it. My left hand descended to grasp a buttock firmly while my right began massaging small circles just over that small patch of red fur. I could feel the warmth rising.

Every so lightly, I let my fingers trace a small zig zag down through the patch of fur. Even to my light touch, the flesh below immediately parted slick and wet. The scent of her arousal rose headily to my nose. She moaned slightly.

In a quiet but firm tone of voice I asked, “I assume that you know how to suck cock, but I wonder if you’ve ever had that pretty little slut mouth of yours fucked?”

“No, Sir,” she replied breathing heavily. “I’ve only had a cock in my mouth a few times. And I’ve never had my mouth fucked like in those pictures or videos.”

“Have you ever had a cock in your throat?” I continued my line of questioning while slowly and gently playing through the silken gap of her sex with my fingers.

Allison was breathing heavily and moaning.

“Not a cock, Sir,” She answered with some difficulty. “But …”

“Don’t you dare cum without my permission. I am nowhere near done with you,” I growled. “So, no cock in your throat. BUT … But what?”

She squirmed a little and closed her eyes.

“A dildo,” Allison answered uncomfortably.

“You’ve had a dildo in your throat? Teaching yourself to deep throat?” I asked, amused.

“Yes, Sir. In my purse, Sir. I love having it in my throat when I get myself off,” she blurted hotly, “Sir.”

The hand I had gripping her wonderfully plump buttock pulled to separate her cheeks. I shifted my grip and reached out a finger to rest on on her tight, brown back door.

“How about this?” I quizzed, “Ever had a cock up your tight little slut ass? Or maybe a dildo?”

She spasmed nervously and replied, “No, Sir.”

I stepped away casually toward the couch and moved Allison’s clothes to a nearby chair.

Pointing to the couch I instructed, “On the couch, on your knees. Now turn and put your hands on an armrest.”

I walked to the side of the couch, grabbed her by the hair and pulled her forward and down.

“I want to see those beautiful tits swaying over the edge of the couch,” I explained.

It was an uncomfortable position that required a some effort to hold. More than half of her torso was over the edge of the couch. Her breasts were just generous enough to have a tiny amount of sway to them. One of her hands snaked back between her thighs where I knew it would be rubbing her hot little hole.

I held her by her hair and gently commanded, “Dirty little red headed slut, tell me again what it is you wanted.”

She was struggling to maintain balance.

“Please, Sir. Use me however you want. Use me like a fuck toy,” she gasped out stream after stream of obscenity. “Use me like a cheap fuck hole. Like I’m is just something to jerk yourself off with.”

“Get your hand away from your cunt,” I snapped. “If your good, I might let you get yourself off later.”

We were both crazy with the moment. I let her head and torso drop and quickly removed my jeans and underwear. Allison raised her head and saw my throbbing cock bob in front of her face.

“Show me what a good cock sucker you are,” I growled.

She raised up and lunged forward. Her lips parted around the head of my cock and she continued to thrust herself forward until she had fully impaled her face on my cock. I reached down with both hands and gripped her head tightly against my body. Even though her lips were planted against my pelvis and she was starting to gag, I tried to thrust deeper.

I pulled back out her mouth for a moment and let her get her breath. Her eyes were already watering and she gagged up long strands of saliva. But she looked hungry and her mouth parted in anticipation.

I slid the head of my cock into her hungry mouth and commanded, “You wrap your slut lips around my cock and suck. And you keep your lips wrapped around my cock.”

She obeyed immediately and I began to slowly fuck her lips and mouth. I rocked gently, holding her head in my hands.

“I do enjoy a nice leisurely mouth fuck,” I say to the top of her head.

Her ass is sticking up in the distance. I bend forward, turn her head to the side a bit and lean forward. My cock is once again balls deep in her little whore mouth. I reach out and grab her ass with one hand. Her ass is so beautiful from this angle. I can feel her gagging and starting to panic below me. I grab a handful of her hair and use it to pull her forward even more for a moment.

I let go and withdraw from her mouth just enough to let her breathe. I take my time and vary my strokes. Slow, fast, deep, shallow. All that exists is my cock and the little red headed fuck toy impaled on it.

I pull her off my cock and push her back further onto the couch. She must be tired and sore by now from holding that position for so long. But her spit covered face betrays nothing but a bizarre primal lust.

I reach over to an end table and pull an unlubricated condom out. My cock is too wet. I use Allison’s hair to dry excess of drool from my hard cock. I roll the condom down my cock and grab her head again.

“Suck, you little whore,” I spit. I’m as lost to the moment as she is.

Allison leans forward and wraps her lips around my cock once more, this time covered in latex. I fuck her mouth and throat mercilessly with slow, deep strokes. She barely even gags any more. After a dozen strokes, I know my cock is lubricated enough. That virgin ass has been teasing me from a distance for too long. I must have it.

I pull out of her mouth and she watches me walk around behind her. I slap her ass lightly and Allison moans. I put one knee up on the couch. I leave the other foot on the floor for traction. Allison raises her ass up high.

“You’re hoping to get that greedy little cunt of yours stuffed, aren’t you?” I taunt.

Allison’s chin is still dripping with saliva and her lips and throat are probably swollen and sore.

“Yes,” she coughs raggedly.

“Right idea, wrong hole,” I snarl and place the head of my cock against her virginal back door. Like Allison’s face, my latex covered cock is slick and dripping with saliva.

“Relax,” I command, “and push yourself back onto my cock.”

I hear her whimper. I reach around and run my fingers across her cunt. Allison moans and rocks back a little. Her cunt is incredibly wet.

“Your ass is long past due to be fucked and you know it. You’ve been fantasizing about having your ass fucked, haven’t you?” I accuse while strumming her swollen cunt lips.

“Yessss,” she hisses back.

I spit at the spot where my cock has pressed against her back door and rub my cock in circles to spread it around.

“Focus on relaxing. Take deep breaths,” I tell her and angle myself to push forward.

I grab her hips and pull her slowly back as I press relentlessly forward. I feel her tight hole resist me, but I hold my cock on target with one hand while whispering “relax” over and over. Allison whimpers, but it only serves to further arouse my lust. After what seems like a small eternity of whimpers and resistance, Allison lets out a cry of surprise as I feel the head of my cock pop past her ring. Her head jerks up and her breathing is sharp. I reach around and find her cunt is still slick and swollen with desire.

The difficult part has passed. I press slowly in another inch and then pause while she adapts. I drool spit down the crack of her ass and watch it run down to where her once virginal hole is stretched tightly around my cock.

I rock subtly back and forth. Not enough to slide in or out, but enough to flex and stretch the muscles gripping me. Allison’s whimpers are taking on new characteristics. Every now and again a moan of pleasure escapes her lips. I push in slowly. My cock is about half way into her tight ass.

Allison moans, “Fuuuck, yesss.”

I alternate between gentle, stretching rocking motions and slow, minute slides until finally my cock is buried to the hilt in her ass. I rock gently there for a moment listening to Allison’s breathing and then begin to slowly withdraw the same way. Allison begins to whimper and moan more loudly. Her head is turned to the side, resting on the armrest. I see tears and grow concerned.

“Are you alright?” I ask.

Allison whimpers and a tear falls from the eye that I can see. I stop everything. Now I’m worried.

“Never felt like this,” she sobs quietly. “Hurts a little. But feels so good.”

Relieved, I begin slowly rocking my cock back out of her ass. As I get toward the end, Allison pushes back suddenly and deeply. She whimpers and I feel her ring tighten for a moment when she forgets to relax. My cock is buried fully in her ass again.

“Does my ass please you?” Allison stutters. “Does my tight slut ass feel good?”

“Your tight little ass feels amazing,” I confess.

“Please use it. It hurts, but I like it. I’m just a dirty little whore that needs her ass broken in. Break my ass in. Fuck my ass like you fucked my mouth,” Allison pleads.

I pull back in one long slow motion and hold her hips firmly away as I pull out.

“NO!” she cries.

“Roll over on your back, slut. I want to watch your face while I fuck your ass,” I snarl, hiding my concern.

Allison slides back onto the couch and rolls over. I pull her knees up onto my shoulders, slide my cock between her cheeks and press the head against her freshly broken hole. This time, gravity works with me and I easily slide up and in. She throws her head back and her face is a mixture of pleasure and pain. I let her legs drop to the side.

“You’re tight little whore ass feels so good. Tell me how much you like having my cock up your ass, slut,” I growl.

Allison moans and winces obscenities as I begin slow thrusts in and out.

“I love your cock in my ass, Sir. Fuck! Wanted it for so long. Oh! Never dared. Fuck! Yes!”

Even through a condom, after several minutes her tight greedy ass proves to be too much for my self control. I pull out and stand up.

“Get down on your knees in front of the couch, slut,” I command.

Allison obeys and gets into position as I peel the condom off of my cock. I grab her by the head and fuck her mouth mercilessly. She gags out of control and spit foams out of her mouth to run sloppily down her chin onto her chest and lap. She can tell I’m about to cum, because I feel her starting to swallow.

Over the top I go, still pounding my cock into her mouth like a mortar and pestle. She hums, moans and swallows as I pump stream after stream into her mouth. I hold myself deep until my cock begins to soften a little. Like a good slut, her hands are still behind her back.

I pull out of her mouth. Her chin and lips are covered in a frothy mixture of spit a semen. My cock is a bit of a mess, too. Once again, I use her tangled red mop to clean and dry my cock off as much as I can. Her hair is sticky and matted with spit and cum.

“Has this little slut pleased you, sir?” she asks.

“I am quite pleased,” I reply.

“Please, then, Sir. Can I get off. I’m so fucking close. Just a few touches,” Allison begs.

I get up and grab her by the hair and begin to walk down the hall with her in tow. At the end of the hall is a full length mirror. I push her down in front of it.

“Kneel and spread your knees. Wider, slut. I want to be able to watch in the mirror. I want you to look at yourself in this mirror while you get yourself off,” I tell her.

Allison takes that as permission, and her hands fly down to her cunt. Her face, chest and hair are a mess of drool and semen. She kneels wide legged at my feet with my hand gripping her by her red tangled top.

“Thank you, Sir,” she moans.

It’s not even a minute before her back arches and she howls and sobs herself through an intense and prolonged orgasm. As her orgasm begins to subside, I let go of her hair and sit down behind her.

After a minute, she opens he eyes and looks at herself again.

“Can I use the shower?” she asks.

“Absolutely. Towels are in the closet,” I say with a gentle smile.

She reaches down and explores around her slightly loosened ass with her fingers.

“Can we do that again? Maybe in a few days?” Allison asks with a tired smile.

Lilly is going to be pissed.

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