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.
