Friday was only two days away when we made our plans for the evening. James would meet me about six o’clock, it would be more than dark enough to head out and we would catch up with some others. Halloween only comes once a year but this Halloween was different.
First it probably would be the last time I went trick or treating, at fourteen your opportunities are getting limited after that. Second this Halloween landed on a Friday, this was good, I would stay out later than if it was a school night. And last something would happen that I never thought could happen to me, at least not until I grew up a bit.
So, here is my account of what happened that cold dark night on the last day of October.
James showed up dressed like a hobo, his face stained with charcoal, an old black hat, clothes ripped and ragged. My mom was nice enough to make me a skeleton costume. It was great, all black she sewed on white bones, from a distance it really looked like a skeleton walking up the street. We were about to take off when the old man started in with the third degree.
After explaining we were going around the neighborhood first, then down High Street to Whitcomb Ave and Tower Road where we were assured of getting a better selection of candy from the “upper class” people. I thought we were in the clear. I was about to close the door when he came with the dreaded question “What time will you be home?”
“When we finish,” didn’t cut it with him. After a little negotiation we decided on ten o’clock. When I thought it was ok the old man hollers out the door “Forget the ten o’clock.” Before I could protest he mumbled, “Eleven will be ok if you’re inside at someone’s house.”
Our bags were chock-full of candy when we split from the rest of group heading down towards Whitcomb Ave. No one else wanted to go with the exception of Betty, which was good. Betty wasn’t the best-looking girl, a little overweight, long black stringing hair, and a mouth full of metal braces.
Everybody liked her, but she was just plain goofy. I liked Betty a little more than most and so did James; we both had a crush on her. She looked weird in her outfit, a long witches dress, a pointy hat and high heeled boots making it problematical for her to walk.
It was her idea when we came to the section of road with no houses or street lights on it. Even if it was a short section, maybe taking only three or four minutes to walk, it was still a creepy place. We followed her into the woods right off the sidewalk and waited behind a large oak. Then there were three of them, maybe only ten years old. Just as they walked by, we jumped out scaring the shit out of them. We laughed our asses off as they went running back from where they came from. When James went to look for more victims approaching for some mysterious reason I reached over taking Betty’s hand. At first, she resisted giving me a ghastly stare.
My hand was soggy with sweat from anxiety as I intertwined my fingers around hers. James was still looking for someone to come up the sidewalk when I leaned closer to Betty extending an arm around her pulling her towards me. Then in a flash my mouth plummeted onto hers locking into an embrace. Before either of us had a chance to contemplate what was happening Betty had fallen back off the oak tree she was leaning on tumbling my body on top of hers while we both held the kiss.
This was too easy, even if I had a crush on this plump, goofy, and gawky girl I never expected I would be on top of her. If looks could kill, then James just killed me when he came back to find us. Even in the dark I could tell he was pissed off. Then we heard some others coming into range and we sprang into action jumping out at them as they passed
At first, they froze, eyes wide they were frightened until they realized what was happening. Unfortunately, they were a couple of years older than us and they didn’t like being scared. With them in hot pursuit we took off into the woods running for our lives until we hit familiar territory leaving them in the dust as the three of us maneuvered up the narrow path towards our own neighborhood. Exhausted we collapsed under a thicket of pine trees.
Betty kept staring at me, and James kept staring at the both of us. The air was chilly along with the mood. While running we had developed a sweat and it was taking its toll as we started to shake from the cooling perspiration and laughter of the episode. The suggestion we head back to my house was gladly accepted.
As we walked backed Betty had both hands occupied as James and me each held one. The old man was glad to see us since it was only nine o’clock. After some reassurance that we were in until curfew he headed up to bed while we headed off to the playroom in the basement. That’s when the real scary stuff started too happened.
With my parents in bed two floors up, we cranked up the music and heat a bit. The old furnace in the next room was pushing out hot air warming us up from the nippy outside, so much that I was again sweating in my costume. Looking around I could see poor Betty must have been dying in that long dress.
She kept fidgeting with the dress pulling it up and letting it drop letting some air up under it. But in the process, she was doing more than that; she was getting me excited showing the flesh of her legs. I only wished that James wasn’t there, maybe I could get some more action if he was gone.
Looking at James I could see he was having thoughts about her too, every time she raised that skirt his eyes would follow every flap of it. The long black witches dress had now been pulled up to her knees while she had her legs spread. My imagination was running wild while watching her sit on that sofa.
Taking a seat beside her then joined by James the three of us sat in silence listening to the music. James took the first move resting his hand on her knee when she raised the dress up. With his fingers making circles on her bare skin Betty slightly turned to me, smiling then tilting her body towards me and resuming the kiss we started earlier back in the woods. I accepted the proposition but quickly became nervous about the situation, not sure how to proceed with James there, not sure if I even wanted to continue Betty held the kiss for several minutes until I broke free.
My eyes popped out when I looked over at James who was now rubbing not only her knee but had the dress further up her leg and was kneading the flab of her lower thigh. I decided then that she was a hot bitch who was looking for something, and I was the guy who had what she wanted.
Back to the kissy-face but this time my hands traveled onto her stomach hoping to get to her tits, and I wasn’t rejected; the roughness of her dress had no impact on the softness of her tits as my hand roamed over the small swells on her chest. My dick was hard and trapped inside this stupid costume, almost to the point it hurt. It wanted out.
I persisted in pulling her towards me away from James, slipping down between me and the sofas back while Betty raised her legs onto James’s lap. As she slid down so did I. It worked perfectly, James was being forced to the end of the sofa, but Betty and I both were lying on our sides. It was the precise position to be in, my dick was aligned with her crotch, and I started to hump her. James’s hand was still on her leg trying to get further up them.
After a little added maneuvering Betty was on her back while I crawled on top of her. James finally gave up the effort and rose to watch. I had the top two buttons undone working on the third; her chest would soon be exposed for my pleasure. Then Betty sort of woke up from her trance.
Betty started a very physical protest pushing my hands away just as the dress was open enough to reveal some flesh. Every time my lips went into the v of her cleavage she would pull my head back up while I pushed on trying for more. I was able to force one leg between her knees prying them apart until firmly planted in the middle of them.
There was sweat on our bodies from both the heat of the furnace and rising passions. Never once did she verbally object to my advances. The front of her dress was now fully open to her waist at the same time pulling the dress higher up onto her body. After pulling her bra aside her mouth opened stuttering out an objection. Confused and dazed I couldn’t understand what was up with her, why in hell did she let me go this far. Slumping against her warm body I felt the blood releasing from my dejected dick back into my body.
With my head nuzzled up to her ear, still breathing in small gasps, Betty mumbled about being afraid, afraid of going too far. James made some small talk with her about the unease, how she had excited us, after all we were just boys who were horny thinking she was also, we just wanted to fool around a bit. I lay on her chubby body while James continued his words of wisdom hoping to convince her. She confided that she was afraid of actually having sex, loosing her virginity and the nightmare of possible pregnancy. After a few minutes of those comforting words my breathing into her ear started to have an effect, I could feel the tension releasing its grip.
Again, in motion with her bra pulled aside, sucking in a puffy nipple while James continued his sermon while stroking her hand, Betty’s reservations diminished. She was content with the honesty of James’s conversation that everything would be on her terms. Uncertain, Betty incoherently mumbled that she didn’t want this to get out of hand but at the same time I felt her chest being forced up to my awaiting mouth.
As I sucked the nipple it grew in size as did my dick, James had worked his way around to the front while still holding her hand, glancing over I could see why, the belt on his pants was undone as well as the top snap and he was working at getting them open.
James reached over twisting the switch on the lamp leaving the room only dimly lit. My costume was straining to be off; the bottom was from a pair of way to small sweat pants. Reaching down I pulled them over my ass without her realizing it, then the hard part. I managed to get the front down over my dick that was poking straight out and upwards. Struggling I managed to strip them to my knees.
Betty’s black dress was bunched up at the waist; my dick was now nudging against her panties. With her legs widened I could feel her fat thighs riding alongside mine. James’s free hand was inside his pants beating his cock while still clenching Betty’s hand. When Betty felt the tip of my dick hit her panty protected cunt she awoke from her stupor once again. But James’s reassuring words calmed her to the point that I had both hands pulling her undies down.
I got Betty to roll over on her side again and her undies were down past her chunky ass checks when I felt another hand take the panties removing them completely off her legs. Old James to the rescue. It was at this point that I understood the fact that I might get laid tonight. But the boat started rocking when I forced my way between Betty’s legs.
Almost in tears she wanted to stop, her fears were truthful, and I knew it. Not wanting to hurt her, not wanting to be accused of rape I backed slightly off. Swollen and hard my dick needed release. I figured I didn’t have to fuck her to get my jollies, I would hump her until I came, by then James would probably have cum in his pants and we could all go home satisfied.
After promising and re-promising that I wouldn’t fuck her, that I wouldn’t even try to put it inside she consented. I lay sandwiched between her legs sliding my dick around everywhere except in her hole. The head of my dick oozing out slippery pre-cum would slide up onto her patch of black hair.
To my surprise James’s pants were tangled at his feet, his underwear bunched at his knees, a rigid dick pointed directly at us while he stroked it. I felt more wetness as my dick slithered around her crotch as Betty had rapidly became wet. On one upward push my dick caught the edge of her cunt before rising up onto her tummy. Then it happened again, when she didn’t make an objection to it I did it a few more times but would let it linger a little longer each time before removing it. Then I simply left it caught in her puffy cunt lips.
Betty began to whimper she was afraid of getting knocked up. James to the rescue again. He insisted she couldn’t get pregnant the first time you have sex, it was only after that first time you have to worry about it. That was what some people though back in those days. Yeah right.
But when James promised that I wouldn’t “do it” inside her making her double save I wished he would speak for himself. So here I have my dick resting in the outer crease of Betty’s cunt almost ready to blow my load, and she can’t make up her mind if she’s ready for it. Then the questions start about “doing it inside.” Great time for a sex education lesson.
I promised over and over again I would not under any circumstances let anything loose inside her, but she still was afraid to comply. By this time the head of dick is already out of sight. From all the lube we were generating it took no effort to ease into her a bit more, resting then a little more, resting again until I was engulfed entirely by her pussy. All five- and one-half inches were now buried deeply inside her. I dared not move from fear she will start screaming, but she didn’t.
I knew it couldn’t last forever; I looked over in the soft light at her dainty hand smearing clear pre-cum over the head of James’s dick. James’s eyes are tightly shut. My dick is the happiest it’s ever been. This was the finest night of my young life. I withdraw slightly then return it deeply. I did this over and over again for a few minutes before abruptly rolling off her to the floor breaking the control she has on James’s dick.