Judy's November

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.