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Judy's November

By: ArtyGee



If you haven't read Judy's Halloween, you probably should before going on to this one.



Everyone in the neighborhood knows that Jim goes hunting with the guys for a week in late November every year, and this year was no exception. It was 4:30 AM when I kissed him goodbye on the front step and headed back to bed. I was a bit too awake to fall right back to sleep and my mind began to wander to thoughts of what Leo had done to me on Halloween. As I thought of Leo and his cock, his young ever-hard cock, I became increasingly excited. I soon had one hand in my crotch and the other kneading my breast and pinching my nipple. My nightie was annoying me so I stripped it off and got back to pleasuring myself. As I did, thoughts of Leo pressing his thumb into my ass as he fucked me from behind kept passing through my mind. I had never been interested in anal, but the memory of the unique feeling of what he had done to me really cranked up my libido. I couldn't resist. I grabbed my vibrator, flipped over and assumed the doggie position. I lubed my thumb in my pussy then pressed it into my ass, as I stroked the vibrating phallus into my sopping pussy. A loud moan escaped my lips as I relived the thrill of what Leo had done to me.

Suddenly the sliding door flew open and before I could react, I was pushed forward, sprawling on the bed. My hands were quickly pulled behind me and fastened with handcuffs. Before I could regain my senses, I was flipped over and found myself looking up into Leo's face.

"God Judy. When I looked in through the patio door, I thought I might get a peek, but when I saw what you were doing I couldn't resist popping in to give you your cuffs back," He laughed. "That was one of the hottest things I have ever seen. You had your thumb in your butt didn't you? I thought you said you didn't do anal." 

By now he was sitting on my thighs which controlled my legs, and with my hands pinned behind my back he had unobstructed access to my tits, which he took full advantage of.

"Leo. GET OFF ME." I yelled as I struggled. "Get off me or I'll scream bloody murder." I grunted as I squirmed to throw him off me and stop the arousal which had begun to grow.

"OK. OK. Don't start screaming" he said as he started to climb off the bed. "Oh I forgot that I brought something else you forgot at our place"

With that he whipped out the gag and fastened it in place. Now all I could do was mumble and groan as he once again attacked my chest, kneading my breasts and pulling hard on my nipples. When his hands started to slide towards my crotch I once again began to struggle. Unfortunately he had all the leverage and apparently he had come prepared. In no time he out two pieces of cord and tied my ankles to the foot of the bed He then spread my knees wide and secured them to the sides of the bed. There was no way for me to close my legs, or free my hands. Leo was in complete control.

"You know, you are one amazingly sexy MILF, and there are a couple things I missed out on last time that I want to try this weekend." he said as he picked up the vibrator and inspected it closely. "Firstly, I want to try eating some pussy. Then when I have you hot enough, I'm going to take your cherry. I saw you playing with your ass, and I know you want it."

He stood beside the bed undressing as he spoke. When he dropped his boxers, I couldn't stop myself from staring at his cock as it was revealed. Ramrod straight and iron hard, he took it in his hand and stroked it as I watched. After a couple strokes, he lay down with me and started kissing and nibbling my neck, driving me wild with desire. After a few minutes of this torture, he started kissing and licking his way down my body. He must have spent 20 minutes on my nipples and breasts, sometimes sucking in an entire mouthful of tit flesh before letting it pop back out. When his journey ended at my pussy, it was flowing like a river, and I was ready to beg my young lover to fuck me. But he was in charge and that's not what he wanted yet so he slipped between my spread knees and started kissing my sex. I do not know how such a young guy could be so good at cunnilingus, but Leo was an artist. He licked, sucked, and kissed my labia, sometimes licking the entire length from back to front. He flicked my clit with the tip of his tongue, He sucked my clit in and out of his mouth in rapid strokes. Within just a few minutes, my rear was arched up off the mattress, I was straining at my bonds and balancing right on the edge of one of the biggest orgasms of my life, and then he stopped and sat up. I was frantic and started to squirm around and plead through my gag. 

"Am I doing OK?" he smiled. "Or do you want me to stop and go home? Just nod your head if you want me to keep going."

I knew that if I just shook my head no I would be alone again, but I was out of my mind with arousal, and felt my head vigorously nodding up and down before I had made the conscious decision to have him continue. And continue he did. For almost an hour he brought me repeatedly to the brink of orgasm but left me hanging on the edge. By that time I was a babbling idiot. I could focus on nothing but my need to come. Leo was in complete control. He stared into my eyes as he adjusted my bonds so my wrists were tied inside my ankles and my elbows were fastened to my knees. Secured in such a manner, He was free to position me for entry from a number of different positions. His choice was to lay me on my back, and again secure my knees to the sides of the bed. This left me immobile with both my holes completely at his disposal.

"Are you ready for some more fun?" he asked as he picked up the vibrator and turned it on. "Just nod yes if you want me to continue."

Once again, my head was nodding before my brain commanded it. Leo smiled and rubbed the vibrator up and down my pussy, and around my clit, before he lined it up and buried it in to the hilt. With all the stimulation I had that day I knew it would only be seconds before a monumental orgasm swept over me. Leo sensed the same thing and pumped it twice before removing it from my pussy and pressing it to my asshole. I started to panic as I realized that he meant to take my anal cherry and there was nothing I could do at this point to stop him. Both the vibrator and my ass were slick from my juices and when he started to press the buzzing toy to my rectum, I felt it begin to stretch my hole and slide in. Leo was agonizingly slow as he rotated and pumped, pumped and rotated, I had never felt so full and the vibrations traveled from my rear into my pussy, keeping me excited. I moaned and begged through my gag, but Leo just kept his eyes glued to mine as he worked that toy in a little further each time he pumped.

It must have been about half way in when Leo pressed two fingers into my pussy and started pressing on the vibrator through my pussy wall. This carried the vibrations through his fingers and up to my clit. Within seconds, I had an earth shattering orgasm, and clamped down hard on Leo's fingers and on the vibrator. Leo kept up his assault and within seconds, I came again, my entire lower body spasming repeatedly. It wasn't until I started to drop down from that high, that I realized that during my orgasm, the vibrator had been worked into my ass right to its base.

"There you go Judy" he grinned. "I thought you said you didn't like anal. How do you like it now?"

Of course all I could do to answer his question was to grunt and gargle around the gag. The vibrator was still running, but it was losing power and the previously strong vibrations were now reduced to an annoying tickle in my rear passage. Leo pulled out another piece of cord, looping it around my hips and up my butt crack, securing the vibrator in position so I couldn't squeeze it out. I was confused when he then got up and got dressed. He hadn't satisfied himself yet and it appeared he was leaving. 

"Judy, I have to run a couple errands. I'll take your car and be back in a little while. You just lay here and enjoy yourself. OK?"

I squirmed and tried to protest, but all to no avail and in moments I was alone and terrified. What would happen if Jim came home? What if a friend or neighbor came around? What if someone broke in and found me like this? But even with all those concerns, the tickle of the vibrator in my rear kept me on the edge of excitement. I had no way to gauge how long he had been gone, but when Leo returned the vibrator was completely dead. He untied it and removed it from my rectum and took it to the bathroom to clean it up. My ass felt empty, and strangely wide open. I tried to squeeze it shut as I heard Leo working in the other room. Soon he was back, picking me up and flipping me over. Still bound arm to calf, I was now in a kneeling position with my ass high in the air. 

"Gotta clean you out before we play any more," he said.

He pulled a box from the bag and opened it. It looked like a douche! He smiled as he grabbed some lube from the bag and lubed the douche and my asshole. Within seconds he was pressing the tube deep into my rectum and I felt the cold fluid filling my bowel as he emptied the bottle into me. He held everything in place for a few minutes, then carried me to the toilet and sat me down. I could not keep from voiding my bowels and the liquid squirted out. As soon as I was empty, he placed me face down again. This time he had warmed the douche up in a sink of water. The liquid was really warm and felt surprisingly good as it poured into me. This time Leo let it soak longer before he allowed me to release it. 

When he took me back to the bed, Leo had no trouble changing my bonds to a new arrangement. With just a few moves, he had me tied face down, with my hands bound together to the headboard, my ankles spread to the bottom corners, and my knees spread with ropes. It was a relief not to be doubled over any more, but I was terrified at what I knew was about to come. I heard some packaging rip and then the vibrator sprang to life. 

"New batteries" said Leo as he pressed the newly energized toy to my open pussy.

I started to squirm as I became excited by the vibrations. I had limited wiggle room and no ability to resist. Leo pressed the vibrator first into my pussy, then into my ass, and left it there while he stepped into my field of view and let me watch as he lubed his rigid cock. I moaned and tried to talk through the gag, but nothing intelligible came out. The bed moved and the vibrator was removed from my ass. I felt Leo's legs inside my own and then the hard hot head of his cock pressed to my stretched hole. I tried to squeeze my muscles and keep him out, but he was so hard that he was able to press in against my resistance.

"So tight...So fucking tight." he whispered. "That's it Judy. Squeeze me."

Then I felt him press all the way into me. He was bigger than the vibrator and his manhood stretched my hole even further. This was a completely new set of sensations, and not nearly as unpleasant as I had feared. He pushed his hands under me so he could work my tits as he started to stroke in and out. I became increasingly excited by the intense feelings this boy was awakening within me. As he fucked me, Leo kept up a constant stream of praise and encouragement. Within a short time, he pushed deep into me and I felt him pump jet after jet of his young come into my formerly virgin hole. 

Unfortunately, He had come before I had reached my peak. This left me horny and frustrated. I wanted, no, needed to come and couldn't bear the thought that I would be left hanging. I started to wiggle beneath him. I pushed my ass back into him as much as my bonds would allow. I moaned and pleaded into my gag, but I needn't have worried. Even though he had just pumped a huge load of his sperm into me, the excitement of what he was doing to me kept him hard as steel. He undid my gag.

The instant the gag was off I could not believe the urgency and need with which I said words I thought I would never say. 

"OH GOD LEO," I panted. "Keep going. Fuck me. Fuck my ass."

"See I told you." he sneered. I'll do you again, but this time, I want to watch your face." 

That said, he quickly untied me and flipped me on my back. I was so far gone that I couldn't stop myself from spreading my legs and pulling my knees up to expose both my open holes to this boy. I felt a flash of guilt and embarrassment as he pulled me to the edge of the bed. I was no longer tied up. I could scream, fight, get away, but all I wanted to do was lie there and let this young boy ravage me. In an instant his hard cock entered my ass again, and he started a slow agonizing grind of his hips. I could feel his wiry hair bristling against my pussy lips and ass. He reached down and began tweaking and pulling my nipples, which drove me further into passion. Then he slowly pulled out and slammed back in to the hilt, repeating the grind. This was agony. The grind was not intense enough to push me into orgasm, and although the single strokes were more than intense enough, they were not of sufficient duration. I was in a sexual hell, and Leo knew it.

"Leo, just fuck me. Please stop teasing me. Just fuck me please." I cried

"Will you be my MILF butt slut?" he asked continuing the grind and pump action. "Will you let me do you? Do you in the butt any time I want?"

"Oh Leo. It's not right. I can't. You're so much younger." I babbled

He grabbed the vibrator and turned it on, stroking it over my breasts and nipples, then down past my clit and back up to my nipples again. I couldn't think, couldn't reason, couldn't take any more without going insane.

"Yes. Yes." I pleaded.

"Yes what?" He asked. 

He wanted me to say it for him, to beg him to use me as his personal sex slave, and I couldn't resist.

"YES." I screamed. "Make me your butt slut. Take me any time you want. Day, night, any time, any hole, just make me come now. Just fuck me hard Leo. Fuck me hard now!" 

And that is exactly what he did. He pumped me with a fury I had never experienced before and within seconds I was pushed over the edge into an orgasm of epic proportion. With the stimulation all centered in my anus, it was somehow different than the orgasms I had experienced from vaginal sex. Novel and exciting. These feelings took me back to my teenage years, when I had first lost my virginity. The intensity of my orgasms and the novelty of the sensations had turned me into a veritable sex addict. Some might even say, a slut. Jim knew nothing of me then, but Leo had re-awakened those feelings and I knew it would be extremely difficult to resist a new addiction. I knew deep inside, that I would indeed become Leo's butt slut, at least until the novelty wore off.

Judy's November Ch. 02



If you haven't read Judy's Halloween and Judy's November, this one will make more sense if you read them first.

Thanks to the readers who have commented on the first two stories, and thanks for the ideas for future adventures. I expand on some of those ideas in this chapter, but you'll have to read on to find out which ones. 




I must have fallen asleep after my session with Leo. It was mid-morning when I woke up and I could feel the ache in my muscles from pulling at my bonds. I checked my arms and legs and found no evidence of chafe, meaning that I had come through the session unmarked. As I lounged in bed, my mind drifted back to what Leo had done to me and what I had promised him. Would I really do it? Could I really do it? The small hollow in the pit of my stomach and the slight tickle in my pussy suggested that, yes, I certainly could. I could be this teenager's sexual plaything. 

The steaming hot shower helped ease my soreness and after I dried off, I pulled my hair back into a pony tail and slipped one of Jim's tee shirts over my head to cover my nakedness. Following my usual toast and grapefruit breakfast, I set about doing the dishes and the week's laundry. The house needed a good vacuuming so I put my wireless headphones on and went at it. As I moved the vacuum back and forth, I felt my breasts bobble and the tee chafing against my sensitive nipples. My mind drifted back to that morning and the working over that Leo had given me. Lost in thought with the music on, I was in a world of my own. Oblivious to my surroundings. That's why I screamed and nearly jumped out of my skin when I felt a hand grab my crotch and squeeze. 

"Hmm. Feels a little wet down there." Leo commented. "What have you been thinking about my naughty little MILF?"

"JESUS LEO! Don't sneak up on me like that. What the hell are you doing?"

"I thought that would be self evident," he chuckled. " I'm checking up on my butt slut. I thought I would just drop in for a quick feel and to give you a present"

I started getting wetter as this virile young man continued to feel me up, then pulled off my tee.

"Nice. Naked under the shirt. I like that. I think that should be the standard for the remainder of the week. Don't you pet? Oh and here's your present."

He produced the leather dog collar Jim had fitted on me at Halloween, and slipped it around my neck, buckling it snugly.

"I think every pet needs to have a collar in case they get loose. Maybe this afternoon we'll go downtown and get you a tag with your name on it."

An icicle ran down through my belly. What was Leo thinking? I couldn't let him do that to me. I'm a 35 year old housewife, and he's my teenage neighbor. This just wasn't right. But if it wasn't right. Why was I getting excited at the prospect of being his pet? Jim wasn't going to return for a week. What was going to happen to me before then? As all these thoughts ran through my head, Leo leaned in close put his lips next to my ear and whispered softly.

"The collar stays on all week, including the tag when we get one. No bra or panties allowed. Now get down pet. Get down on all fours."

This last command was punctuated by a sharp tug on my collar pulling me down towards the floor. I obediently sank to my hands and knees before my young neighbor. When I was down on all fours, he patted my head gently and stroked my hair from front to back.

"That's it pet," he soothed, "That's a good girl. Now come on over here and attend to me."

He walked across the room, dropped his pants and sat in the easy chair. His cock was sticking straight up between his thighs. He wiggled his finger at me and told me to come on over. When I reached the chair, he commanded me to suck him, and that's exactly what I did. I leaned forward and sucked his gorgeous pink cock into my mouth. I reached up to stroke him, but he slapped my hand away, and told me to use only my mouth, both hands on the ground. Leo grabbed the back of my head and pushed down until his cock pressed at the back of my throat. I gagged. He let me up a bit, then pressed back down. Hard. 

"Stop struggling pet. Stick out your tongue and swallow." 

And as I did, I felt his cock slide into my throat a bit. Further than any cock had ever been. He pushed and I felt it slip in further. I gagged hard and, eyes watering, ejected him from the entrance to my throat.

"You need to work on that pet, but we have all week. OK finish me up. We have errands to run this afternoon."

Once again I sucked his rigid young cock deep into my mouth and worked my head up and down over his lap. It only took about a minute before he was flooding my mouth with huge jets of his semen, which I didn't need to be told to swallow right down.

"OK pet. Now that I'm looked after, it's time for a little grooming before we head out."

He clipped the leash to my collar and led me down the hall and into the bathroom telling me to get into the tub. What was happening to me? My hands weren't tied as they had been at Halloween or earlier today, and yet this boy was leading me around by my leash. I was obeying his commands and becoming intensely aroused by doing so. I was becoming his slut, his pet, and it almost made me come just to think it.

Leo then instructed me to start the water running and to sit down, which I did. The razor I use to shave my legs was lying on the shelf in the tub, and Leo smiled when he saw it. 

"Good. You probably have everything we need. Where are your fresh razor blades? I want to shave your pussy."

I couldn't have been more shocked if he had slapped my face. I trim my pubic hair and have sometimes shaved the sides to enable me to wear certain bathing suits, but I have never gone full Brazilian. I was in a daze as he lay me back in the tub spread my legs and directed the shower wand to my pussy. The flood of warm water felt amazing and I was quickly building toward climax. Without warning Leo cut the flow of water and I was left hanging. He gently soaped up my pubic hair and shaved me bald. It was intensely arousing to have this young man pulling on my labia to stretch the skin as he worked. I was on the verge of orgasm the whole time, but he had warned me not to come because my spasms might cause him to cut me. It was worse than being tied. He was very careful so it took quite a while for him to complete his task. He even made sure to shave between my butt cheeks and around my anus. 

When he was done he started the shower wand again and directed the spray of water at my denuded crotch. Without the buffer of those wiry hairs, the needles of water felt doubly intense. With his free hand Leo carefully rubbed all the soap away and then rinsed it down the drain. With a flick of the wand, he changed from spray to pulse and directed the flow at my clit. The intense pulsations added to all the stimulation of the shave, caused me to come almost instantly. My head fell back, my legs tensed and I let out a howl as, once again, my teenage neighbor brought me to a thundering orgasm.

After I had recovered and dried off, Leo led me to the bedroom and opened my closet. He picked through the hangers until he found a light summery shift. It had a scooped neckline, and came half way down my thighs. The thin material was intended to be worn over a full slip, but Leo had other plans.

"This looks good. Put it on. We need to go downtown."

I tried to protest, to negotiate, to plead, but in the end I stood before him, totally naked, under that semi-sheer dress. He clipped on my leash and led me out to the car.

"Let's go. You can drive"

I slipped behind the wheel feeling extremely vulnerable. As we drove along, Leo kept asking me how I felt. Was the wind blowing up my dress? How did I like the feel of it on my bare pussy? How did my nipples feel, all stiff and poking through the thin material? His stream of questions kept my mind focused on my state of undress, keeping me in a constant state of excitement. My lack of focus caused me to make several rolling violations. Luckily no cops were around as Leo said I would have to hike up my dress and "show some more skin" to avoid getting a ticket.

When we got to the store Leo had me park in back. We got out of the car and he told me to follow. The pet store was quiet with a young man about Leo's age behind the counter.

"Hey Barney. S'up?" Leo said as we approached the counter. "Meet my new squeeze. Barney, this is pet."

"Holy shit," blurted Barney, "You weren't shitting me were you? Is this really her?"

I had never felt so humiliated. Clearly Leo had told this boy about me and now he was getting to meet me in the flesh. As Barney stared at me, mouth agape, Leo told him that we needed an engraved name tag for my collar. Barney finally shook himself and asked us to follow to the engraving area. There were lots of different tags there. Barney suggested that the "large breed" tags would be most suitable, and Leo picked out a big shiny one, which Barney then engraved with "Leo's Pet".

When the tag was engraved on both sides, Barney suggested that the collar be removed so he could affix the tag, but Leo just told me to bend over the counter so Barney could reach. As I leaned forward, I saw Barney's eyes drop to my dress and watch, mesmerized, as it fell forward, giving him a great "downblouse" shot between my naked breasts. With that view in the background, Barney had a terrible time attaching the tag. His hands were shaking and he couldn't keep his eyes up on the collar. Suddenly he froze, looking past my shoulder for almost a minute before shaking his head and continuing his task.

When Barney was finally finished, I stood up and turned around to look at Leo. It was then that I noticed that a large mirror had been leaned against the display case opposite the counter. It was immediately obvious to me that Leo had placed the mirror so Barney had been able to look right up my dress. No wonder he had stopped dead. Instantly embarrassed, my entire face flushed crimson and a rush of arousal washed through me. 

"Well Pet," Leo said, "how about we compensate Barney for his work?" 

Leo knew I had left my purse in the car. I didn't know what he meant, but I wasn't sure I liked how he said "compensate". Barney said it was OK, that he had it covered. Leo insisted until Barney relented. That's when Leo turned to me and said:

"Pet, pull your dress up to your waist."

It was a simple command. I heard a roaring in my ears, I felt my heart pounding in my chest. I knew it was wrong, but Barney had already seen in the mirror. I reached down and pulled my dress up. Barney's jaw dropped and his eyes bugged out.

"Oh my God Leo. She's shaved. I can see everything. Her whole pussy. I never saw a real one before."

Barney was hyperventilating. I thought for sure he was going to pass out, and I was certain I was going to join him. Leo stepped behind me and reached around my arms. He grabbed the neckline of the dress and slowly pulled it down. I was so excited that I could barely breathe let alone object. When my tits were totally exposed, I heard Barney groan, as if he were in pain.

I was so embarrassed I couldn't look Barney in the face but with my eyes downcast, I noticed a bulge in the front of Barney's pants, and as I stood there, I saw a wet spot start to grow at the end of the bulge. He was so aroused he was coming in his pants. I hadn't touched him, He hadn't touched himself. Looking at my body and seeing my shaved pussy had gotten this boy so excited he had creamed his jeans. My brain reeled. That empty spot grew in my stomach as I stared at his crotch. 

The spell was broken when the little bell tinkled announcing another customer had entered the store. Leo pulled up my top and I smoothed down my hem so I was covered by the time the customer reached the counter. The woman glanced my way, then did a double take. It was clear that she was confused by what she was seeing.

"OK Barney. Thanks for your help. Might see you again later." Leo called as he led me from the counter. "Come on pet. Time to go."

The woman customer's look of confusion changed, and a look of distaste passed over her face. I followed Leo obediently out to the car where he told me there was one more stop to make, and gave me directions. 

"Leo. We can't do this all over town. Someone I know might see us. I can't do this. I want to go back home." I whimpered to no avail.

When we reached our destination, Leo led me inside. I was shocked to see that this was a sex shop. The walls and shelves were covered with an endless array of sexual paraphernalia. Leo seemed to know where he was going as he led me back through the displays to a counter near the rear of the store.

The man behind the counter was about my age, and looked me up and down appraisingly for a few seconds before he turned to Leo and asked if he needed any help. 

"This is pet," Leo nodded in my direction. " and she needs a tail." 

A tail? Oh my God, a tail! What the hell was Leo doing now? The clerk ran his eyes over me again and then asked Leo if he had anything particular in mind. I stood there in shock, as they discussed options. Pony? No too long and hairy. Cat? Nope too small. When the clerk suggested fox, Leo jumped on it.

"Fox. It's perfect. She's such a MILF fox and now she'll have a tail that fits her personality."

My mind was reeling how was Leo going to fit me with a tail? I decided then and there, that I was not going to let this boy glue a tail onto me when the clerk handed Leo a fox tail attached to a black rubber plug. I felt a chill at the prospect of that plug and where it might go. 

"I think this is perfect. Nice and red with a white tip. I'd like her to wear it home but she's a novice. Can you lube it for me?"

The clerk produced a bottle from under the counter and drizzled some on the plug. Leo told me to bend over and grab my ankles. I knew that my dress would ride up over my ass but I did as I was told. When I was bent over Leo stood on my leash ensuring I did not stand up again. 

"Would you like to do the honors?" Leo asked the clerk.

"No Leo no please. He's a stranger. Please don't let this man touch me." I pleaded.

I was pleading trying to maintain some small semblance of dignity, but deep inside I was hoping that Leo would not give in. I was not disappointed. The clerk stepped behind me and I jumped a bit as his hand slid over my buttock but Leo's foot on the leash kept me bent over. The clerk flipped the back of my dress up over my hips and ran his hand around my ass for a minute of so before he gave me a resounding slap. This was way beyond anything I could ever even have imagined. I was semi naked in a public place with a stranger feeling me up and I was so wet that I could feel a rivulet of my pussy juice run onto my thigh. 

"Looks like we didn't need the lube," sneered the clerk "this fox is running like a river." 

He slid his finger up my inner thigh picking up my juices which he transferred to my asshole. Then I felt the cold plug pressing at my anus. Oh my God. It was going into my butt. The clerk applied a steady pressure and slowly the plug stretched my bottom. I was still a little tender from this morning and I groaned as the widest part entered me. The clerk gave it a few in-out strokes of the widest part before slipping it all the way in. My ass closed around the narrow part of the plug and locked it in place. The clerk said he would check the fit. He gave my tail a tug, which caused me to clench my ass and the plug did not come out. Then he reached down and slipped two fingers into my gushing cunt and rubbed the plug through my pussy wall. I came so hard my knees buckled and I dropped to the floor. The clerk stayed with me, his fingers strumming my clit throughout my orgasm.

When the last spasms subsided, I opened my eyes and realized that I was now down on all fours, with a collar around my neck, a tail hanging behind me and a complete stranger's fingers deep in my cunt. I was truly Leo's pet.

The clerk wiped his fingers off on my thigh and moved away. Leo removed his foot from my leash and told me I could stand up. When I was finally back on my feet, I straightened my dress and stood next to Leo. He thanked the clerk for his help and started to lead me from the store. My tail was swishing back and forth as I walked. tickling the backs of my thighs. As we passed a full length mirror I caught a glimpse of myself. I took it all in. The collar, the leash, the short dress and hanging below the hem, the white tip of my tail. Although I wouldn't have believed it possible, my pussy started to melt again.

Thankfully, it seemed that our errands were done and I was directed to drive back home. It was a bit uncomfortable sitting on the tail and the butt plug jumped with every bump in the road. When we pulled into the garage, Leo said he had to go home and do some chores. He told me I could finish my housework but the collar and tail had to remain in place. I went to the master bathroom, threw the dress in the hamper and cleaned up the leakage from my pussy. I slipped Jimmy's tee back on went to the kitchen to pour myself a coffee. What the hell had just happened? What was I doing? What was Leo turning me into? All these questions and more tumbled around my brain. I was about to find out that this was just the beginning.



Judy's November Ch. 03



If you haven't read Judy's Halloween and the previous chapters of Judy's November I strongly encourage you to do so before you continue with this chapter, and do remember that although I try to make it as realistic as possible, this is a work of fiction and as such may have taken some poetic license. 

A special note to those who comment. I really appreciate your supportive comments and constructive criticism, but to those who feel the need to leave nasty and or downright abusive anonymous comments: It's OK if you don't like this story go read someone else's. Please remember that if it wasn't for those of us writing these stories, you would have NOTHING to read. 




I was in a complete daze as I worked around the house. Leo had insisted that I keep the collar and tail in place, and with every move I made, one or the other surfaced in my consciousness. My collar would rub on my neck. The tail would gently brush the back of my thighs. I'd bump into something and the tail would cause the butt plug to jump in my ass. And always there was the persistant tinkle of my metal tag reminding me that I was Leo's pet. 

This was insane. Why was I acting like this. He's just an eighteen year old boy and I'm a grown married woman almost twice his age. When he had me tied up, I'd had no choice, but why not just reach up and take off the collar. Why not just pull out this silly tail? Yet every time I decided to do just that, my mind flashed to the incredible rush of his hard young cock sliding deep into my ass. Pumping and pumping. I would recall the intense feeling of humiliation as he exposed me to his friend at the pet shop, and my lower abdomen would turn to butter again. It was like I had returned to my youth. I was obsessed with having sex with this boy and I would be his pet if that is what it took to have him continue to fuck me like he had.

But he hadn't had he? He had let the sex store owner finger me to orgasm, but he had unceremoniously dropped me off like some discarded toy. He hadn't fucked me but that was all I could think about. Hoping, wishing, dreaming, that he would come through the door, pin me down and fuck me senseless. Wondering if he would do me with the tail and plug still in place, or pull out the tail and take me back there. The entire afternoon was spent with these thoughts spinning through my brain, cranking up my libido and causing my pussy to lubricate furiously. Several times I had to go to the bathroom and wipe a cloth around my crotch to clean up the constant flow of juice before it ran down my legs. As bad as that was, it was ten times worse when the housework was done. Then I had nothing else to distract me and my entire mind focused on Leo. How could I get him to come over? I couldn't phone him, I could only await his pleasure. It was maddening, frustrating, and intensely arousing all at once.

I don't drink much, and almost never when I am alone, but I needed something to calm my nerves, so I poured a strong Jack and Coke. That was a mistake. Every sip reminded me of that first night . Halloween. When Leo had taken his pleasure with me. I just couldn't stop thinking about him and what he, we, had done. By eleven that night I was a complete mess. I was buzzed on the drinks and I was so horny I was shaking like a leaf. I looked over towards Leo's house and saw that it was completely dark. THAT BASTARD. He had left me hanging here and gone to bed. I headed to the bedroom and pulled out my vibrator. I needed some kind of relief and if Leo had abandoned me it would have to do.

I peeled off the tee and lay on the bed, reached into the nightstand and pulled out the vibrator, as I was turning it on, I heard a tapping on the patio door. When I looked up, there was Leo's face pressed against the glass, looking straight into my soul shaking his head no. I jumped up, dropping the vibrator, and slid open the door. 

"Where have you been?" I scolded, "I've been going nuts all afternoon. Get in here and fuck me." I demanded, pulling him in through the door and sliding it closed behind him. 

"Quiet." he rasped "The neighbors are sitting out next door and they will hear you." This with a wry smile.

"What were you going to do with the vibrator pet?" he asked. "I hope you weren't thinking of making yourself come. I'm the only one who decides when you get to come, and how. I have a good mind to handcuff you and leave you here alone tonight so you can't masturbate while you think about that"

"Oh gawd Leo. No please don't make me wait any more. Please. Please. Tell me what you want, I need to come. I need you to make me come. Please." I pleaded hoping to escape the fate he had described.

"OK then. Not all night," he whispered, " only 'till my folks turn in and I can come back for you. Hold out your wrists."

My mind was in such a turmoil I didn't even think, I just reacted to his command. Before I knew it the cuffs were locked on my wrists and attached to the headboard. When I was secured, Leo leaned down to me.

"I went back to the sex store today and picked up another present for you."

Another present? What now? I watched as he opened a small paper bag and removed a big rubber thimble with a suction cup at the end. I had never seen anything like it before.

"I told the owner that your tits are particularly sensitive and he suggested that a pair of these would drive you wild."

My breasts are very sensitive and once a man starts to feel me up, I am putty in his hands. Leo knew this from our previous encounters and he was taking full advantage. He pressed and kneaded my tits pulling vigorously on my hard nipples. Leo moved his mouth to my left nipple, licked around it and then sucked it hard into his mouth until he had it totally wet with his saliva. He squeezed the thimble flat, placed the suction cup over my nipple and released it. OH MY GAWD. The suction produced by the expanding thimble pulled my nipple into a recess in the cup, causing it to almost double in size. I could feel my nipple continuing to expand as it started to throb in time with my racing heartbeat. Without missing a beat Leo latched onto the other nipple and when he had it wet and erect, attached a second bulb to it. I had never experienced anything like this. I looked down to see that my nipples had swollen with blood to the point that they more than half filled the cups. The center of my abdomen felt like it was melting and fireworks were going off in my brain.

"See you a little later," he whispered in my ear, causing a rush of goosebumps down my back and arms, "I'll be back to play in a little while."

I begged and pleaded with him to give me some release, but he simply flicked off the light and exited back onto the patio leaving me with no recourse but to lay frustrated and suffering in the dark. For the first few minutes, I tried to shake the suction cups off, but they were on too tight. Eventually I just lay there, nipples throbbing, awaiting his return.

It was an eternity until I heard the door quietly sliding open and Leo returned. He grabbed my ankles and slowly, torturously, his hands moved up my legs. Gently pushing them further open as he did. Having suffered for so long, I was in no mood for foreplay. I wanted him to jump me. I wanted him to climb between my legs and push his beautiful cock into my dripping pussy. I wanted him to pull out the plug and drill his hard young dick into my ass. I couldn't help myself. I started to plead with him to do those things. Do anything to bring me off, but he just kept up his slow progression up my body.

"Please Leo. Please do something. Please make me come." I begged him.

Leo's response was to settle back to take in the view of his handiwork. Then he slid his hand over my hairless crotch and started to rub my lower abdomen. He was teasing me. Not touching my pussy lips or clit, but the rubbing was taking me to even higher levels of arousal. 

"Would you like me to fuck you in your wet pussy Judy?" he whispered. "I would like to try that to see what it feels like with your tail in." 

With everything else going on I had forgotten about the tail. Now that he reminded me of my submission, I could feel it beneath me tickling my thighs, turning me on even more. When he brought a finger down to tickle my clit, I spasmed and jerked but it was not enough to make me come. I was right on the edge but couldn't drop over. Quick as a cat, Leo stripped and crawled up between my legs pushing my knees up toward my shoulders. I felt the fat head of his rigid cock at the entrance and begged him to push it in. Push it in he did. I was so wet that there was no resistance as he slid in until his balls slapped my pussy lips. No resistance but an unfamiliar tightness as the butt plug squeezed his cock through the thin wall which separated them.

I came. I came hard. And as Leo pumped his cock in and out of my stretched pussy I continued to come continuously. My brain stopped functioning and I started babbling incoherently in grunts and syllables. I pulled at the handcuffs and whipped my head from side to side as the endless orgasms continued to wash over me. It was too much. I couldn't breath. I felt a strong jet of hot semen hit the top of my pussy and my entire being was wracked with an orgasm so intense that I lost consciousness.

When I awoke, Leo was removing the handcuffs and rubbing my wrists. 

"That was fun." he soothed "How are you feeling?"

I felt like a rag doll and told him so. After releasing the suction cups, he then rolled me over and removed the butt plug saying that although the tail was originally a turn-on, all it had done was get in the way of our fucking. 

"Get some sleep Judy" he whispered, "I'll be back in the morning." 

The sun was streaming in through the patio door when I came back from my morning shower and saw Leo standing there. The hot shower had helped, but my stiff muscles still complained as I rushed over to let him in. Leo swept me up in a big hug and kiss, pulled off my towel, and started running his hands over my naked body, kissing me and pushing his tongue into my mouth. My pussy started to respond immediately. Then he stepped back.

"Turn around and bend over." he ordered "

As I stood bent over, Leo moved close behind me and pressed his cock deep into my stretched asshole. The intensity of his penetration knocked the breath out of me with a grunt. It only took a few pumps into my ass before I felt a strong jet of semen squirt into my bowels. Disappointment flooded through me. I was just getting warmed up and Leo was already done. I needn't have worried.

Leo then stood me up and attacked my nipples. They were still tingling from the night before and they stood at attention immediately. When he had them nice and wet, Leo attached the suction cups again causing my nipples to expand and throb. I was now in a state of desperate need and told Leo that I needed release. In seconds I was lying on my back across the bed and Leo had his mouth on my pussy. As his tongue caused waves of pleasure, Leo reached up and started pulling at the suction cups sending spikes of arousal to my already overstimulated brain. As he continued to run his tongue up and down my slit, he pulled quite hard on the suction cups causing them to pop off. 

I looked down and saw that my engorged nipples looked almost twice their normal size. When Leo reattached the suction cups, they grew even bigger and throbbed on the verge of pain. Just as the throbbing started to subside, Leo grabbed the cups and started a slight twisting motion. At the same time, his mouth moved to my clit and sucked it in. Hard. My orgasm was instantaneous and huge. Once again my teen lover had taken me over the top.

When I had returned to earth, Leo suggest that we should have some breakfast, because what he'd just eaten hadn't filled him up. I laughed out loud, and the contractions caused my stretched asshole to leak some of Leo's juice down my leg. I quickly ran to the bathroom and cleaned up. As I exited the room, I caught a glimpse of myself in the mirror. My hair was a tangled mess, and my face had that "fresh fucked" look about it, but it was the suction cups on my nipples that drew my eyes. I stared at them in the mirror and couldn't believe how they looked. I was reaching up to take them off when Leo told me to stop.

"The guy at the store said I could leave them on you for a couple hours at a time, so that's what I'm gonna do." he stated firmly. "Pull on a tee and let's get on with breakfast. 

My pussy twitched. I really wasn't sure about leaving the cups on, but there wasn't any significant discomfort so I thought I'd go along with it for now. When I pulled on the tee, Leo commented that I now had some serious "pokies" which was an understatement. 

My goodness, Leo's appetite for sex was only exceeded by his appetite for food. He ate a huge breakfast, then sat back and watched me clean up.

"Shouldn't you be getting home?" I inquired "Won't your folks wonder where you are?"

"Nope." was his quick response " They left super early this morning and won't be back until Tomorrow night. That gives us lots of time to play."

Oh my God, did we ever play. There was hardly a minute when Leo didn't have his hands on me somewhere, or his cock in one of my holes. After a couple hours, he allowed me to remove the suction cups and OW did my nipples ever throb again for a minute or two. The feeling went away as Leo gently "kissed them all better" but they remained larger than normal for the rest of the afternoon. 

That night Leo stayed over and we made love like honeymooners throughout the night. I couldn't believe the stamina and intensity of this young man's lovemaking. Yes. I said it. Lovemaking. Somehow, what had started out as fucking had morphed into lovemaking. I knew he might restrain me again, but I also knew he wouldn't have to. I would allow him access to me any time, in any hole. 

In the morning I made him breakfast and he headed home to dress, then off to school. I dressed and went through my normal routine, but always with thoughts of Leo running through my mind. Several times I found myself just staring off into space and then realized that I had been thinking of our lovemaking and my pussy was wet. The rest of the week was a school week, but Leo would slip in both before and after school so we could have sex. He also came by after dinner and evening sessions usually involved some double penetration with his cock in one of my holes and the other stuffed with either the butt plug (tail removed) or the vibrator. I found these sessions to be extremely stimulating and came hardest when both holes were filled. 

Every time he visited he attached the suction cups and told me to leave them on for several hours, and every time, I did. By the end of the week, my nipples were swollen and very sensitive. Every move I made sent a jolt of stimulation through my nipples to my clit. I almost longed to put the suction cups on just for the protection they afforded me from the constant stimulation. My nipples were now pretty much permanently erect and had grown to almost twice their size 

I could hardly believe the week was coming to an end and Jimmy would be returning. How was I ever going to go back to my normal life after the week I had just had? Compared to what I had gone through with Leo, my life with Jimmy seemed lackluster and boring. I was stuck between a rock and a hard place. I could never leave Jimmy and live with my eighteen year old lover. I could not imagine returning to the banal existence I had without Leo. What was I going to do? I cried myself to sleep that last night before Jimmy returned. 

I was dressed in shorts and a tee when Jimmy walked in through the door. He grabbed me and pulled me in for a hard kiss on the lips. In no time he had slipped his tongue into my mouth and we were Frenching like crazy. 

"Whoa whoa there cowboy" I said pushing back, "What's gotten into you?" 

"I had a lonely week, and just wanted to show you how much I had missed you" he whispered in my ear. "Lets leave all that shit in the car and head back to the bedroom"

He took my hand and led me down the hall to the master suite, spun me around and kissed me hard on the mouth as he groped my tits through my clothing. It had been years since he had attacked me with such passion and I couldn't understand why he was so attentive now. 

"Let's have a look at those tits" he said as he grabbed the hem of my tee and pulled it off over my head. 

I panicked. I had expected that if we did have sex it would be that evening with the lights out and Jimmy would not notice my enlarged nipples. He had my bra off before I could react and his eyes went wide as my nips expanded to their new maximum in the cold air.

"Well, well, well. What have we here?" he clucked as he pinched and twisted my nipples " Looks like someone has grown a bit while I was gone."

I felt my pussy melt as Jimmy worked my swollen sensitive nipples. In no time I was begging him to fuck me. He responded by pushing me back on the bed and pulling off my shorts and soaked panties. His mouth was on my pussy in an instant and he pushed my knees up and back to provide him with better access. As he did I felt my stretched ass hole gape open. This was not lost on Jimmy. 

"Wow," he enthused, "doesn't that look inviting?"

With that he opened his pants and pulled out his rigid cock. I assumed he was going for my pussy and was a bit shocked when he slowly sank himself balls deep in my stretched anus and then started to pump furiously. It took almost no time at all before I was climaxing continuously while Jimmy plunged away at my back passage. I felt his flood of jism as he pumped an enormous load into my rear. When we both had calmed down a bit, Jimmy slid out of me and collapsed beside me on the bed. 

I couldn't help looking at him in total disbelief. He obviously had seen the changes in my body, but instead of asking me what happened, he had simply gone ahead and fucked me as if these changes were no surprise. I began to wonder what in Hell was going on. But I figured I'd better start trying to explain.

"SHHH." Jimmy soothed placing a finger on my lips, "I know all about it. I set it up."

I was totally gobsmacked. He had set it up? Set what up? What had just happened?

Jimmy explained how he had seen Leo take possession of me at the Halloween party and had watched as he led me upstairs and fucked me. He had then returned to the party, expecting us to be back down soon. When that didn't happen, he had crept back upstairs and seen us at it again, after which he had gone back downstairs and gotten drunk. The thought of his wife as a teenager's slut had been so exciting to him that he had approached Leo just before the hunting trip and laid out a plan of what he wanted him to do to me, giving Leo some money to buy props. The anal sex, the shaving, the tail, and the nipple stretchers. I thought it funny at the time that he didn't mention the dog tag, but I kept my mouth shut about that. The deal was, he said, that Leo would continue to have access to me as his reward for transforming me in ways my husband never could. 

It made so much sense now. Leo's short transformation from shy virgin to dominant master had been orchestrated by my husband. I could hardly believe it. But little did I know that I was soon to find out that Leo was only beginning his journey.