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Judy’s Halloween

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I still don’t know exactly how I got myself into that situation. It may have been a bet, It may have been a dare, or it might be that I was tricked. The upshot of the entire affair is that I found myself with my neighbor’s 18 year old son manhandling me and eventually fucking me senseless.

Perhaps I need to start at the beginning with a description of myself and my marriage to Jim. We had been College sweethearts who married and have been together for 10 years this November.

Being a college athlete, I have maintained an active lifestyle and held my college weight up till the present day. At 5′ 5″ I weigh 120 lbs. Jim is forever trying to get me to dress sexy, and show off my trim athletic shape and particularly my firm C cup tits. Normally I resist his requests and although I have been in public in some very revealing outfits it was only while on vacation far, far away from home and family.

This past Halloween, our neighbors George and Helen, invited us to a dress up house party. Although I wasn’t really interested at first, Jim finally convinced me to go. The choice of costumes was to be decided by the performance of our Alma Matter football team at the homecoming game. If they won, Jim chose what we would wear. Since they were, in my opinion, outclassed by the away team, I jumped at the chance to win the bet and dress Jim in some foolish or uncomfortable costume for the party. Well as luck would have it, the home team won which meant that Jim got to choose our costumes. No amount of wheedling by me would get him to reveal the secret until the night in question.

I was somewhat shocked by the costumes that Jim chose for us. I was presented with hose, garter, thong, and push up bra, all covered by a short skirt and tight button front blouse. When I was dressed, Jim directed me into my highest pumps and whistled as I turned for his inspection. For his part, Jim was dressed in tight leather pants, with a leather vest on his otherwise naked upper body. I thought that he looked a bit sinister in that outfit, but it was Halloween after all. I asked Jim what our costumes meant as we walked next door, but he just smiled and led me on. When we reached the front door, Jim opened the bag I thought had contained a hostess gift. Spun me around, and before I could stop him, handcuffed my hands behind me. We had played some bondage games in our time together, but never anything so public. As I turned to protest, Jim pushed a gag into my mouth and quickly secured it behind my head. He then clipped a dog collar around my neck, attached a leash to it and rang the doorbell.

The door was opened by Leo, our neighbor’s son. I thought his eyes were going to pop right out of his head when he saw how we were dressed. He gave me a long hard look up and down before inviting us inside. There was nothing to be done. Jim, holding my leash led me into the house followed by Leo who, I had no doubt, had his eyes locked on my ass. The party was in full swing as we entered, but many of the men turned to take in my predicament as we entered the room. I also saw several of the women cast disapproving looks my way. Jim, followed by myself and Leo passed through the room and went straight to the bar. He ordered himself a drink and then ordered a double Jack and coke for me. I do not normally drink so I had no idea what he was doing until he pulled out my gag and poured the drink into my mouth. I had no choice but to swallow since the alternative was to ruin my blouse and probably the carpet too by allowing the drink to spill down my front. I certainly did not want to put on a wet shirt display for everyone. I was still feeling the burn of the drink in my throat when Jim placed the gag back into my mouth and led me away from the bar.

Suffice it to say that most of the men at the party enjoyed talking to Jim as they ogled me. Within an hour’s time, Jim had forced 3 double drinks down my throat and undone two of my blouse buttons so that the tops of my breasts were clearly on display to the men he talked to . Leo was rarely far away and I caught him several times as he stared openly at my exposed breasts which were thrust out on display by my pulled back arms. For my part, I was beginning to feel quite drunk as the drinks took their desired effect.

Apparently, Jim was beginning to feel his drinks too and said he had to make a pit stop. Unluckily for me, Leo was close at hand to take my leash as Jim made his way to the washroom.

“That’s some costume”, he whispered in my ear as soon as Jim was gone. “How would you like to be my pet for the night?”.

I could only grunt through my gag.

“Tell you what. Let’s pop out to the work room and see if we can improve your outfit” he said as he led me on unsteady legs, down the hall and through a door into the work room. Alone behind closed doors, Leo grabbed me by the waist, leaned in and kissed my neck, sending a chill down my spine. He then moved away and picked up a short length of braided cord from the bench. Quick as a cat, he moved behind me, pulled my elbows back and lashed them together. As he did this, I felt my shoulders pull back, my breasts jut out and the remaining buttons on my blouse strain.

“Let’s take a look then. That’s much better” he announced as he grabbed my hips and spun me around for a better look.

In no time at all, he had me backed up against the bench and was again kissing and nibbling my neck as his strong hands ran over my ass. The attentions of this young man were beginning to arouse me but I moaned a protest into my gag. This did nothing to stop Leo from slowly sliding his hands up my sides, and around to massage my breasts. My breasts have always been a very effective erogenous zone for me. Since I let my first high school boyfriend feel me up, having a man squeeze and stroke my breasts has almost always resulted in me losing control and having sex with him. That’s what happened with Jim and that’s what was happening now with Leo. I started writhing and moaning as he kneeded my breasts and pinched my nipples through my bra. I was starting to get really horny, but I was also beginning to realize that I had to pee too. Worse than that, the need was becoming quite urgent. Somehow, amid my drunkenness and arousal, I was able to form the word bathroom so Leo understood my need.

“Gotta go?” he queried?

I nodded my head vigorously in response. With his hands on my hips to guide and steady me, Leo took me back into the house, but instead of heading directly for the ground floor half bath, he pushed me up the stairs, along the hall, and into what appeared to be his bedroom. I started to panic and began trying to talk through my gag, thinking that I was going to pee myself. I was relieved for a second, when he led me into his private bathroom, but then began to panic again when I realized I could not free my hands. I was going to have to let Leo help me with this. Seeing the confusion and concern on my face, Leo smiled.

“OK Judy. I don’t have a key for the cuffs and we don’t have time for me to go find Jim, so I’m going to help you with this” He said. “First, I’m going to remove the gag so you can tell me if I need to do anything. No yelling, or calling out, or I will leave you here to pee yourself. Got that?”

I nodded my head and Leo removed my gag, quickly replacing it with his lips. When he broke our kiss he shushed me and then led me to the toilet. This close to relief, the urge became stronger and I had to concentrate hard on holding it in. I had no time to react as Leo pulled up my skirt, grabbed my thong and pulled it down to my ankles. He never took his eyes off my neatly trimmed bush as he lifted one foot then the other to completely remove my underwear. He then helped me sit and I was finally able to relieve myself.

“OH GOD thank you ” I moaned as I voided my bladder.

“We can’t have you dripping on the floor, can we” Leo said when I was done.

He wadded up a bit of tissue, pushed my knees apart and reached in cupping and rubbing my pussy with his tissue filled hand.

“Leo. This isn’t right.” I said. “You shouldn’t be doing that.”

“You can’t do it yourself. What else can we do?” he replied still rubbing and squeezing my crotch.

“Leo. It’s dry” I said. Hoping he would stop, before my growing excitement at this situation became apparent to him. “You’ve had your fun, now let’s go back downstairs”

“Oh no Judy” He replied, “I did you a favor, now you owe me one in return”

He helped me stand, then pulled my skirt down. And led me back to the bedroom. Once there he spun around, grabbed me by the waist and started kissing me again. In my inebriated state, my reactions were down and before I knew it he had pressed his tongue between my lips and was once again massaging my breasts. I tried to back away, but when the backs of my legs hit the bed, I lost my balance and we both tumbled down onto it. I tried to tell him to stop, but with his lips still locked to mine it just came out as a moan. Instead of stopping he moved his hands to the front clasp of my bra and popped it open. As his hands grabbed my bare tits, and diddled my nipples, a wave of arousal coursed through me and I knew I was lost. He broke our kiss and dropped his head to my exposed chest. He pressed my tits together and alternated sucking hard on my nipples. It was more than I could stand and I shuddered with a small orgasm.

Before I knew what was happening, his hand was up my skirt and his finger was pressing into my wet pussy.

“I thought you said you were all dry” he laughed. “Something must have made you get wet again”

He returned to sucking on my nipples and stroked two, and then three fingers in and out of my sopping wet cunt. I was lost and I knew it. This teen boy had managed to turn me into his slut and he knew it. I was moaning and begging him to keep going, when he pulled back and looked me in the eye.

“Do you suck?” he asked. “Will you suck me? It would be my first time.”

“Yes and yes” I replied totally out of control. “I’ll be your first, but that’s it. Then we have to stop and go back downstairs”

Leo jumped off the bed, pulled me around so I was on the edge. He dropped his pants and moved his cock toward my mouth. It was magnificent. Large and pink with a big head. And hard. I had forgotten how hard a teenage cock gets. I opened my mouth as he moved toward me and he pressed it in. I instantly started to suck and lick, flicking my tongue around the glans. Initially Leo stayed still, but soon he was stroking in and out of my mouth as I worked him over. It took only a few strokes before he groaned and squirted a huge load of cum into my mouth. I have never been a fan of the taste of cum or of swallowing it, but this young studs load seemed to slip effortlessly down my throat as I sucked him through his climax.

I thought that would be it, but I couldn’t have been more wrong. Leo never softened a bit as he pushed me onto my back and pulled my ass to the edge of the bed. Giving my teenage neighbor a blow job was bad enough, but even as horny as I was, I wasn’t prepared to let him fuck me. I couldn’t call out for help as anyone entering the room would see my state of undress and the semen spread across my lips and chin. I began to struggle but Leo easily pulled my legs straight up and hugged them tightly to his chest. In this position with my feet beside his head, I was both available and immobilized. Without saying a word, he pushed that still hard cock into my pussy all the way down to the root. Being penetrated in such a commanding way, took my breath away, but as he started to stroke, I started to groan and grunt with passion. Leo reached down and pulled my nipples as the intensity of his strokes increased. This caused me to groan even louder, and Leo pressed his hand over my mouth to silence me. The intensity of his fucking quickly pushed me to the edge. With my mouth covered, I couldn’t seem to get enough air through my nose and was starting to feel asphyxiated, then when I felt the strong jet of Leo’s cum, my orgasm hit me like a freight train. Stars exploded behind my eyes as I sailed into another world, spinning and flying into darkness.

When I came to, I was alone and my skirt was gone. Within a minute or so of my awakening, Leo returned to the room with a triumphant smile. He helped me into a seated position and pressed a glass to my lips. As I started to drink I realized that it was another Jack and Coke.

“That should have rinsed my cum out of your mouth” he announced as he began to kiss me and rub my breasts once again.

“Jim’s pretty drunk and I was able to get the key from him.” he announced. “Let’s get these cuffs off”

I assumed that he was done with me and was going to release me. I leaned forward to give him access to the cuffs as my head began to swim from the effects of that last drink. The instant my hands were released, Leo pulled my blouse and bra off. Before I could react, he was on me tying my hands to the head of his bed. Dazed from the last drink, I couldn’t even struggle much as he spread my legs and tied my ankles to the corners of the bed. When I started to protest, he simply popped the gag back into my mouth.

Leo got up and stood beside the bed to survey his handiwork. He smiled broadly as he stripped off his clothes and climbed into bed with me. We were lying skin on skin and Leo was alternating rubbing my pussy and squeezing my breasts, his young hard cock humping against my leg. He started kissing my neck and nibbling my ear lobes, which sent sexual chills down my entire body.

“Do you have any idea how long I have wanted to fuck a MILF like you?” he whispered “I can’t even count the number of times I have masturbated while watching you in your yard, or picturing you in my head.”

Leo moved away from me pulling a pillow from the head of the bed and stuffing it under my hips. This had the effect of arching my back and lifting my open crotch for easier access. He continued sliding down my body until he was lying between my legs with his face just inches from my pussy. He was so close I could feel his breath on me as he talked.

“Too bad we already fucked so much. I would love to eat your pussy” He moaned. “But I’m not a fan of cream pie. I watched a bunch of masturbation movies on the Internet though, and I want to try some stuff on you” He continued.

That said, I felt his fingers gently stroke my pussy lips. He worked some moisture from the inner lips to the outer and made slow teasing strokes up and down my labia. He alternated these with a gentle rubbing across the hood of my clit, until I started to moan and writhe with the pleasure he was inducing. I didn’t want to respond to this teenager’s advances, but I couldn’t resist the strong arousal he was inducing in me. I felt my clit enlarge and stick out. When he saw this he started to concentrate his strokes there rubbing and pinching my clit, driving my arousal ever higher. I pulled my legs, tightened my thigh muscles and prepared for an orgasm. Then suddenly, he stopped touching me. I pulled at my arm and leg bonds, I whipped my hips around, but could not generate the stimulation required to carry me over my peak. When I started to calm down, he began the gentle stroking again.

By the third time he had taken me to the peak and stopped, I was delirious, and gasping for breath around the gag.

“If I take the gag out will you be quiet?” He asked.

I nodded my assent.

“You wouldn’t want my mom to come in and find us like this would you?”

I shook my head vigorously.

Leo removed my gag and once again lay beside me kissing and stroking my body and breasts.

“You see how it is for me? You making me so excited, and I never get a chance to come.”

“Fuck me” I whispered horsely. “Please fuck me now.”

Leo was on me in a flash, pressing his rigid dick fully into my pussy. In this position, his cock rubbed my clit on every stroke. In and out he stroked while he pressed his lips to mine in a wild passionate kiss. I came almost immediately, but Leo kept up his frantic thrusting driving me to new heights. I could do nothing more than wiggle around beneath him as he continued fucking me. When I heard him grunt, I knew he was coming again, and I followed him into bliss.

In the afterglow, Leo pulled the covers over us and cuddled me. I was so relaxed and content, that I must have dozed off for a while. I woke to the feeling of something leaking from my pussy. I was leaking our combined juices down onto the bed.

“Leo. Leo” I whispered. “I have to get up and go in the bathroom”

Leo awoke and rubbed his hand from my hip to by breast, squeezing my nipple. I could feel his cock beginning to press into my leg as he did.

“Don’t bother about that” He smiled. “We’re not done yet anyway.

“Not done yet.” I thought. “How many times can he possibly get hard in one evening?”

One at a time, so that he could keep control, he switched my arm and leg bonds so that when he was finished, I was face down with my buttocks raised by the now damp pillow at my hips. When he was done, he lay between my legs with is hips pressing into my buttocks and his cock lodged in my pussy. I was just starting to enjoy the quick shallow thrusts, when Leo pulled back and sat on his hips.

“This is no good. I can’t get in far enough.”

With that announcement, he once again untied my hands but this time pulled my wrists down and tied them to my ankles. I was now in a kneeling posture, with my face and shoulders pressed into the mattress and my ass raised high presenting unobstructed deep access to my pussy.

When he pressed his cock into me this time, he went all the way to the root and groaned in satisfaction. Now he took long slow strokes. He would pull out until just the tip of his penis was touching me, He would then rub up and down making sure to rub my clit, then he would press in to the root again. Periodically, he would push himself all the way in, then lean forward, grab my tits and make a series of short stabbing thrusts, then it was back to slow and agonizing. It took a while, but eventually his thrusts began to increase in speed and I could hear him panting.

“Does Jim ever fuck your ass?” He panted

“No Never” I replied. “Please don’t. I’ve never wanted that” I pleaded

Leo lubed the tip of his thumb in our combined juices and pressed it into my exposed rectum. I had never felt so full or so tight. I could feel, internally, the friction between his thumb and his cock, and the combination of that new sensation and the now rapid thrusts of his cock, pushed me into a massive orgasm. I heard Leo groan and felt him shoot another load of his spunk deep into my pussy.

This time he did not pull out. After removing his thumb, he simply rolled us on our sides and cuddled in the spoons position until, once again, I fell asleep.

When I woke, I needed to pee. Badly. I woke Leo, but instead of untying me he simply picked me up, carried me into the bathroom, and sat me, doubled over, on the toilet. When I was done, he wiped me off, then used a warm washcloth to clean away the dried up discharge that had leaked down my legs and buttocks. When I was clean and dry, he picked me back up and set me in the armchair in his room. He pulled my legs apart and draped them over the arms of the chair quickly tying them there. Even counting all that I had endured tonight, I had never felt so exposed in my life.

Leo leaned in and once again started massaging my breasts and twiddling my nipples while he kissed my neck. He knew from his experience that this was the way to get me wound up.

“Leo. You’re 18, I’m 35. I’m exhausted. I can’t do this again. You’ve worn me out.” I whispered to no effect.

Leo kept up his ministrations and soon, my body began to respond. When he slipped his finger into my wet pussy, he smiled.

“Maybe you can’t, but both your pussy and I can.” he said. “I’m cleaned up. Take me in your mouth and get me ready for your pussy”

When he stood his hard young cock was pulsing with his heartbeat as he pressed it to my lips. I couldn’t imagine him being any more ready, but could do nothing but open my mouth and suck him in. This time he took it slow and easy, directing me to suck and lick, occasionally pushing into the back of my throat until I gagged. All the while looking at my face and smiling at me as he watched. When he finally had enough, he pulled out and moved between my spread legs. He rubbed his wet cock up and down my crotch, pushing momentarily at my asshole, but moving away when I said I would scream if he did. Finally he aligned himself with my pussy. I was not as wet this time and it took Leo several part thrusts until he was able to push all the way in.

“This will probably be our last time tonight” he said. “I’m going to savor it.”

He leaned in and started tongue kissing me as he continued to pull on my nipples and make his long slow thrusts. As worn out as I felt, I couldn’t stop my body from responding once again to this young man’s attentions.

“Oh Judy. There you go” he whispered as he felt my pussy expand and get slippery on his thrusting cock. “I told you you could go again”

He leaned back to give himself access to my body and while he continued to work my breasts and nipples with one hand, used the other to rub my exposed clit. This was almost too much stimulation and I began to pull at my bonds, writhing and groaning softly as he worked me.

“I want you to be hot. I want you to be hotter than you have ever been. But don’t come. Don’t come” he chanted.

Just as I was about to reach my peak, he stopped. Dead still. No touching, no rubbing, no thrusting. I was teetering on the edge and he knew it. He had both hands on my hips keeping me from humping myself to finish.

“Squeeze me” he commanded. “Squeeze me with your pussy muscles”

After all the action tonight, my muscles felt a bit sore as I bore down, squeezing as hard as I could. A rush of pleasure passed through me, then I had to relax.

“That’s it. Again”

Again and again I contracted my muscles, again and again I felt a surge of arousal, but no orgasm. Finally Leo could take no more. He grabbed my tits and pounded his cock into me moaning loudly as he emptied his 5th load of cum into my body. That was all it took for me to join him in orgasmic bliss and I came as hard as I ever had.

When he pulled out of me, I felt a strange cool sensation in my pussy. When I looked down, I could see that it was gaping open and our combined juices were running out of me. I was too stretched out and weak to even care. Leo put a towel under me so I wouldn’t ruin his chair, then went to get another washcloth to clean me up. The warm cloth felt soothing as he wiped and dabbed around my entire crotch to clean me up. He sat on the floor between my spread legs and continued his ministrations until my pussy closed up and most of the leakage had stopped. It was at this point that I saw that the bedside clock read 3:00. I couldn’t believe that all this had only taken 4 hours. I needed to find Jim and I needed to get out of here.

Leo untied me and brought me my clothes, minus the panties, which he said would be his souvenir of our little adventure. Even after all this, I felt a little strange dressing in front of my teen neighbor as he watched my every move. When I was finished, Leo walked over to me and pulled me into him for another deep French kiss, but when he started to feel me up again, I pushed away and told him I had to go home before Jim started to wonder what was happening.

When I went downstairs, I found Jim passed out on a front room couch. I shook him, but he was too far gone to wake up, so I simply headed for home, where I showered and climbed into bed. Between my sore muscles and my sexy dreams, I had a fitful night’s sleep and was still in bed at noon when Jim showed up. Knowing how drunk Jim had been, I told him that he had gotten me too drunk last night, that I had returned home early. He didn’t remember much of what happened after 11 so I was off the hook.

I thought that was the end of the adventure, until the following month, but that’s another story.

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