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Halloween Party

"Losing my virginity."

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Famous Story

After two weeks of begging my step-mom, she had finally allowed me to go to a Halloween party. She was very protective of me and was worried about me getting exposed to drugs and alcohol. An important fact she didn’t know was that it wasn’t a normal Halloween party. At sixteen years old, losing my virginity was all I was trying to do. Everyone would be wearing costumes with masks and it was sure to result in lots of sex.

The party would take place in a house with about a dozen rooms and the only catch was that the entrance was two hundred dollars. I had saved up for a long time to buy my costume and pay my access into the fun. I was all set; the only thing would be finding a girl that was down to fuck.

The couple of days before Halloween seemed to last forever but that gave me a chance to think about my approach. My costume was a button-down shirt, dress pants, and a mask that covered my face. My target was to find a girl who wanted to be dominated in bed. It was a simple plan but there was no guarantee it would work.

On Halloween night, I put on my costume and left for the party before my step-mom got home from work. I was nervous but I would be going all out with my persona for the night no matter what. If it didn’t work then it would just be two hundred dollars to see a bunch of girls dressed like sluts.

When I arrived, I was asked for and ID to make sure I was above sixteen years old. There was no alcohol or drugs but there were lube bottles and condoms placed on the coffee table in the living room.

“How many people are you expecting?” I asked the organizer, who was an older man.

“Enough for everyone to get laid,” he said.

The house filled up with high school students in a matter of minutes and it was clear that I would have to find my lane among all the competition. I couldn’t tell who was who but it did surprise me to actually see some of the girls wearing short skirts and the more daring ones showing off their bodies in their lingerie costumes. These were some of the girls from my school that walked the hallways in their uniform and it was great seeing them in much more revealing clothing.

Some guys were getting head in the living room and others had taken a couple of girls upstairs to have a threesome. I had to act and find a girl who was alone like me. All of them seemed to be either with their boyfriend or with another girl.

“Fuck, I look like a loser,” I thought, feeling my face redden under the mask.

I waited in the living room couch for a few minutes to see if a girl arrived by herself. I saw some older couples walk in but there seemed to be nobody for me. All the girls looked amazingly hot but there was one that stood out from the rest.

“When did she walk in? How the fuck did I miss her?” I thought, looking at her perfect ass as she bent over to look at the items on the coffee table.

She was wearing a sexy school girl costume that left little to the imagination and a black mask that covered her entire face. The white top barely contained her big tits and the skirt didn’t cover more than half her ass. Her black panties wedged between her round ass cheeks and the black stockings accentuated her legs to perfection.

“She has to be older with a body like that,” I thought as I marveled at how she moved her hips to the loud music.

I wanted to go up and talk to her, but I feared making a fool out of myself even if I was wearing the mask. It was like her hotness paralyzed my entire body except for my dick, which was begging to escape my boxers. Some guy walked her way and at that moment she turned to walk towards me.

“Hey, you shouldn’t be here alone,” she said.

“I know, not going like I expected” I said.

“Don’t worry, I come here every year to save one lucky boy,” she said.

“You do!?” I asked in surprise.

She reached with her right hand to feel my throbbing cock through my pants. I looked around the living room and noticed that most of the guys were looking my way. I had gone from loner to having the hottest babe with me.

She then grabbed my hand and led me across the room to the stairs. My eyes took in the beautiful sight of her ass and the lovely lace detail of her panties as we went up the stairs. We walked to the end of the hallway and found the only empty room left.

“You have a condom?” she asked, opening the door to the room.

“I’ll go get one,” I said, turning around to go downstairs.

“It’s ok,” she said, grabbing my arm and bringing me into the room.

She locked the door and then sat on the bed with her legs crossed, which brought attention to her thick thighs.

“So you are dominant?” she asked, looking at me.

“Huh?” It took me a second to understand.

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“Yeah, that’s the idea.”

“That’s really hot,” she said before adding, “Show me what you got.”

She turned around and got in the doggy style position to show me her magnificent ass. I quickly got behind her and took off my pants and boxers to free my cock. I grabbed her ass and buried my face between her ass cheeks, which made my nose inhale the scent of her wet pussy.

“I can’t believe this shit worked tonight and I’m losing my virginity,” I thought, as I brought my cock closer to her hotness.

I moved her panties aside and ran my head over her wet pussy until I found her opening. I pushed in slowly to enjoy the feeling of my first pussy, but I was still aware that I had to play the dominant role I was supposed to play. I grabbed a fistful of her long hair and began thrusting into her like I had seen in so many porn videos.

“Fuck yes! Fuck me hard!” she encouraged.

I pounded into her and looked down to see her ass bouncing on my thighs. With my free hand, I squeezed her left ass cheek and spread it to get a better look at my dick penetrating her. The hot and wet feeling of her pussy was way better than any masturbation technique I had ever tried and it was quickly going to make me cum.

I slowed down my thrusting but pulled on her hair harder, which got a loud moan out of her. I didn’t want to cum fast, so I started distracting myself a little bit to get my mind off the pleasure I was feeling. The sight of her sexy body in her school girl costume made it nearly impossible to think about anything else, but I managed to delay my orgasm for at least a bit longer.

Her soft moans let me know she was enjoying the slow strokes, but I had other ideas that she would enjoy more. I let go of her hair and went back to pounding her. I slapped her ass cheeks hard while I decided on what exactly I wanted to do to her next. I had seen hundreds of porn videos and read plenty of articles online to prepare myself for this moment.

I placed her on her back, in the position I had fantasized about the most. I got between her legs and pushed my cock back into her hot pussy before reaching to open her top. I squeezed her bare breasts and thrusted deeply into her pussy.

“Ahhhh! Fuck! Fucckk!” she cried.

I moved on to pinching her nipples while I buried my cock entirely into her. The feeling of cumming came back and this time it would be tougher to delay the inevitable. I kept my cock inside of her for a moment to let the feeling pass and then moved my left hand away from her gorgeous breast to place it around her neck.

I fucked her deeply and choked her, making her scream, “Ohhhh! Yeesss! Fucckkk!”

She seemed to love what I was doing and there was no more stopping for me. I choked her with more force and squeezed her right breast until my balls were ready to erupt.

“Ahhhhnnnggg!” she orgasmed.

“Uunngg!” I groaned, feeling her pussy tighten on my cock and my hot cum filling her up.

I took a few seconds to recover before pulling my dick out of her and reaching down to the floor to pick up my pants.

“I’d love to see you again,” she said, “but I have to be discreet.”

“We could meet here,” I said.

“That could work,” she said, stopping to think about it. “Let’s meet here on Friday at this time.”

“You bet,” I said.

“Yeah, we could have more fun without the costumes,” she said.

She fixed her panties and left the room while I finished dressing. I was happy to have lost my virginity but it was time to get home before my step-mom got angry. I had gotten what I had come for and it would hopefully continue on Friday night.

I got home and only saw my mom’s car, which reminded me that my dad was out on business again. I walked in and saw my mom making herself dinner in the kitchen.

“I’m not that late,” I said, looking at the clock.

“It’s ok, no worries,” she said. “You want dinner?”

“No, I’m good,” I said.

I went into the bathroom to wash my face, but I stopped when I saw my step-mom’s panties on the floor. I picked them up to get a better look at them and then I completely froze.

“No fucking way! No! This can’t be! I fucked my step-mom!” I thought, feeling my body shaking in shock.

The lace detail was the same as the woman’s panties.

“Could it be that they have the same panties?” I thought, looking for a way to deny it.

I brought them up to my nose and the scent of sex from the soaked gusset confirmed my thoughts. I had fucked my step-mom without knowing it! She had told me at the party that she attended it every year to, “save one lucky boy,” and we hadn’t recognized each other’s voice because of the masks. It meant that she had cheated on my dad with who knows how many boys and I was now one of them. Not only was I one of them, but she had told me that she would love to see me again.

Published 
Written by Issabela
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