The Sex Party - My Sister

Each character in this story is over the age of 18.

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The Party

My name is Jake and I'm 29 years old. I'm single and have been for at least 5 years now, but this never bothered me. Before me and my last girlfriend broke up, we started experimenting with sex parties and once we broke up, I continued to go and so this has helped with me being single.

The parties had an anonymity to them, meaning that while they required guests to be fully nude, people where instructed to wear a mask to cover the face. I never really understood why this was. The only thing I could think of was that it made the event feel less pressure, knowing that you and another person wouldn't know who each other were so nothing awkward or unexpected would happen outside of the party in everyday life.

Anyway, people followed these rules and couples attending together would usually match masks in some way so they could tell each other apart. But me, my chosen mask was a full black and gold masquerade mask where the lower part came off so I could use my mouth when needed. I thought this would be mysterious but also elegant and attractive, and I wasn't wrong as helped pull quite a few at previous parties.

I was at sex party this weekend and I had the most exhilarating but shameful experience I've ever had. I had arrived around 9pm and the party had been in motion for a couple of hours now. The hosts house was massive and I could probably have fit my whole 2 bed apartment in the kitchen alone. I had a drink in hand and was chatting to some familiar voices I recognised from previous parties. When all of a sudden, my eyes caught sight of a girl walking post the kitchen into the lounge.

I typically wouldn't seek out someone to sleep with so early in these parties and would usually have the confidence once a few drinks have gone down, but this girl and her body had somehow caught my mind and wouldn't let go. I excused myself from the kitchen and headed to the lounge to find this girl.

I found her by the fireplace in the lounge, sipping on a drink by herself. She was beautiful, her blonde hair cascading down her bare shoulders, but even more captivating was the sight of her small perky tits, peeking out from her hair which laid on her chest and the smooth skin above her pussy. What also drew me to her was that she too was wearing a full masquerade mask in white and gold which matched mine. If I didn't know any better, I'd say that mask was made just for me.

I downed the last of my rosé, put down my glass and decided I would go over to her and see if I could work my magic this early into the night.

"You look as if you might need another drink," I said, my voice low and smooth on approach. "Or perhaps some company?"

The woman turned around to see me, and her brown eyes sparkled behind the mask. "Company sounds much more interesting than another drink. I'm Jess."

Her name caught me off guard and left me frozen in place for a moment.

My sister is called Jess. She is also blonde and has brown eyes. I thought to myself in the moment.

Surely this is just a coincidence? There is no way this is my sis-

"Hello? And you are?" Jess interrupted, bringing me back into the room.

"Sorry. Urm... Names are for people, tonight I am just a mystery," I said, trying to behave like I usually would at these parties. I never typically gave out my name to make sure someone wouldn't recognise me.

Jess laughed, "Mysterious stranger it is then."

I was slightly dazed at this point, with the sudden thought as to whether this was my sister or not. But I composed myself to continue the conversation at least.

"So, I've never seen this mask at any of these parties before. Is this your first time?" I asked.

Jess looked nervously around the room. "Yeah, this is. I've always wondered about doing something like this and thought to myself why not make tonight the night I try it."

"The first time is always the hardest I found. It took me a couple of parties before I felt like I was comfortable in this environment. But once you're in, it is very freeing." I explained. "So are you here with anyone?"

"No, I came alone. I couldn't imagine bringing someone along who I knew. Imagine if they knew this is what I was into." She said, slightly giggling.

I returned a giggle. "I know, if someone knew I was into this I'd probably go into hiding with embarrassment. So do you have anyone, like a partner you've left at home?"

"No I recently broke up, which is another reason I'm here to be honest. I was hoping this may help me move on and help with some of the holes that come with being single." She said winking at me.

We spoke for a while, and as the drinks started to go down, I would start flirting shamelessly with her more and more. Commenting on how perfect her body was and how nice her tits were as she slowly looked up at me. However, this whole time in the back of my mind, I was convinced that this was my sister. There were too many coincidences. For starters her name was the same as my sisters. She is blonde with brown eyes and my sister had also recently broke up with her boyfriend. My sister Jess is 22 and my height, which the girl in front of me looked, but I just wasn't fully convinced.

It is at this point I should explain a little secret about myself. For a while now, I've been into incest porn. Whether I watched it or read it online, it always turns me on and when my sister Jess turned 18, I started to notice her body more, how she had become a woman. I knew it was wrong but it was only in my head I assured myself. I never acted on this in real life and never tried to.

It is because of this that when thinking about whether the girl in front of me was my sister or not, I was sort of hoping it was. And the very thought that it could be started to turn me on. The longer I talked with Jess, the more erect my penis became and the more she noticed, as she commented on how she liked my toned muscles while touching my body. Which got even more of a reaction out of me.

It was eating me alive inside my head all this wondering, until I remembered my sister had a small heart shaped tattoo on the inside of her upper right arm close to her armpit. I couldn't see it now but I figured out a way to find out. Once Jess was holding her drink in her right hand, I raised my glass to toast her.

"Here's to your first party! Lets hope you enjoy it as much as I'd love to enjoy you." I flirted.

Jess' followed and raised her glass to mine. At this moment, my eyes darted to the inside of her arm, looking for the clear sign I was hoping for. And there it was. I could just about make out a small heart shaped tattoo as the other half wrapped under. We downed our drinks as my penis stood at full attention and jerked with excitement at the realisation that this was indeed my sister standing nude in front of me, who's body I was attracted to.

Jess then looked down. "Someone is very clearly excited to be with me", she said taking my penis in her hand and letting it rest in her palm. All 8 inches of my circumcised penis was hard as a rock and getting a little uncomfortable, I needed a release.

"Lets go somewhere quieter", she said winking at me as she grabbed my penis in her hand and led me through the crowd in the lounge and towards the stairs.

People at these sex parties would fuck anywhere and I had done this too, but considering it was Jess' first time, I could understand that maybe she would want to go somewhere more private. This would also remove any risk of people finding out we were brother and sister.

As I followed her heading up the stairs, my mind was racing.

I should stop, there is still time. THIS IS MY SISTER! I've imagined this so many times but can I really go through was this? Yes, this is what I've always wanted. No, it is so wrong.

I was fighting myself in my own head. Split on what I wanted and what was right. But the further up the stairs we got, the quieter objections in my head became and the more I was convincing myself that I was going to go through with wherever this took me.

She wouldn't know it was me. We could fuck and to her, it was just a random stranger. A I NEED this. I've wanted nothing else for so long.

We made it upstairs and moved from bedroom to bedroom until we found one free. We went inside and locked the door behind us. The room was dimly lit, curtains letting a sliver of moonlight into the room. I grabbed her by the hand, leading her to the bed where she sat down on the edge. I removed the bottom portion of my mask to free my mouth and she did the same. I noticed her soft lips, coated in a crimson red lipstick. The bottom of our masks clattered to the floor as I leaned in for a kiss, her tongue sneaking into my mouth, swirling around mine. Jess broke the kiss, she looked at my penis and then back at me with a devilish smile and slowly slipped off the bed onto her knees.

My penis was now at her eye line, inches from her face. I could feel her warm breath rush over it, sending chills through me. Then she reached out and grabbed it. She caressed it and slowly began stroking me a few times until she could see precum start to leak from the tip in the moonlight. Suddenly, her tongue was circling the head, licking up the precum as she then took my penis deeper down her throat.

I can't believe it. My sister is sucking my penis and she is really good at it.

I was in a state of pure ecstasy, the taboo of this was turning me on. I was convinced I was going to blow my load there and then, but I managed to compose myself. Jess really knew what she was doing She continued to stroke the base of my shaft as she bobbed her head over my penis. She paused bobbing for a moment and used her tongue to suck and play with the head, before continuing to take it further down.

During one of these pauses, I stopped her and walked over to the bedside cabinet to grab a condom. I opened it and passed it to her, instructing her to put it on me. To my surprise, she took the condom in her mouth and then took my penis in as well, putting the condom on me at the same time, while never breaking eye contact.

I can't believe how naughty my little sister is!

At this point, I was getting too worked up and needed a break. I didn't want to have my release just yet. I wanted that to wait until I was deep inside her. I pulled my penis away from Jess and caressed either side of her face, bringing her up to me for a kiss. I then gently pushed her so she sat down on the bed and then push her shoulders back so she was laying down with her legs hanging off the edge. I kissed her again and then broke away, continuing to kiss her tits and down her body. I could tell this was getting to her. As I reached her soft and freshly shaved pubic mound, I hooked each hand under her knees and lift them up towards her chest and slight apart.

Jess, my own sister, was now lying naked in front of me with her legs spread giving me a full view of her pussy. I could see her wetness in the moonlight. I got on my knees at the edge of the bed between her legs and breathed in her wonderful scent before slowly licking my way up her slit.

Her body tensed as I gently licked her clitoris in wide circles, then sucked on it, all the while gently probing inside her with two fingers, moving them in and out slowly. She moaned and writhed underneath me, grinding her pelvis into my face. I found her sensitive spot and flicked it with my tongue, causing her legs to tremble, and her pussy muscles to squeeze my fingers. She was close, I could tell, so I continued doing what I was doing until she came with a shuddering moan, her womb milking my fingers in a powerful spasm.

As she was coming down from her high, I slowly kissed back up her body, crawling on top of her, until I reached her mouth. I let her make out with her juices all over my mouth as we kissed passionately. As we kissed, I continued to crawl up the bed and she followed, crawling under me until we hit the headboard. This was it, I pulled away from Jess and stared into her eyes, my penis rubbing over her clit. She stared back longingly, before looking down and taking hold of my penis. She rubbed it up and down her slit before lining it up with her pussy.

This is it. There is no going back after this. I thought to myself. Nothing was stopping me now.

I began slowly pushing my penis into her pussy, her wetness lubricating me enough to slide in with ease as she stretched around me. I watched her face as I slowly pushed forward, inch by inch, until I was bottoming out deep inside her.

"God, you feel amazing," I whispered, kissing down her neck. I pulled out a little bit and pushed back in, watching her face as I worked my penis in and out of her tight pussy.

"Jessi," I groaned, pumping inside her. "I've wanted this for so long Jessi."

Her body stiffened as she pushed on my chest. She had a confused look in her eye, followed by a sudden look of realisation. "... What did you just say?"

Shit. I just called her Jessi. That's what I call her. Fuck, I think she's realised.

"Jake? Oh my god, IS THAT YOU?!?" her voice rising as she ripped my mask off.

I didn't stop, still pumping in and out of her, feeling her walls grip my shaft tightly with every stroke as she pushed continued to push against my chest. She took off her mask.

"I'm sorry Jess. I've wanted you for years, every time I've seen you, every time you walked past me in those little shorts I never acted on my desire for incest. But I saw how good you looked tonight and when I realised it was you, I just had to have you." I revealed to her, letting it all out in the moment.

"That's wrong, this is wrong" she whispered, her pussy clamping down on my penis, trying to push me out. "Please stop, we can't keep doing this."

"I know, but it feels so good, doesn't it? I love feeling your pussy around my penis and I can tell you love it too." - I whispered in her ear

She looked into my eyes and slid her hands up my cheek, she tried to offer a response, but all she could do is moan as her body succumbed to her sexual feelings. We kissed again, passionately, as I continued fuck her pussy in rhythm with her hips. "Doesn't it feel good having your brother's cock inside you?"

"Yes, yes, my brother's cock feels so good inside me," she moaned. "Jake, you shouldn't be fucking your little sister but please don't stop," Jess pleaded.

"Oh, so now you don't want me to stop. You want your brother to keep fucking that tight wet pussy of yours." I teased in her ear.

"Yes, please don't stop. Keep pounding my pussy. Fuck me harder, PLEASE!" She cried.

I stopped and pulled out of her. She cried begging me to put it back in, but I had other plans. I flipped her over, onto her hands and knees, and drove back inside her. "Say it again."

"Fuck your sister harder," she gasped. "Oh fuck. Jake is fucking his sister, his own sister-" - she screamed.

I pushed her head into the pillow. "Yes, I am."

"Oh my God, It feels so good when my brother fucks me." she moaned as she reached between her legs to play with her clit. I kept pounding her. My balls slapping against her clit with every thrust. Jess came hard from it all, moaning out my name as she collapsed into the bed. I slowed down as she shook beneath me, playfully slapping her ass as she tried to recover.

I didn't give her the chance. I pulled out of her and laid down to her side. She pulled her head from the pillow and turned towards me. She looked at me than at my penis standing up right, seeing that I was patting my groin, inviting her to climb on top. She regained her strength and climbed over me, stopping with her pussy hovering over my penis. She grabbed me penis and then stared at me, as she lowered herself slowly down until she bottomed out against me, her head whipping back as the feeling of me stretching her out sent a jolt through her.

Jess then began grinding, rubbing her clit against me, the walls of her pussy clenching around my penis. She leaned into me, her tits pressed against my chest as she kissed me deeply.

As she pulled away, she whispered into my ear, "I'm so glad you decided to fuck me Jake. I've always been curious about how your penis would feel inside me ever since I caught you jerking off when we were younger."

My eye widened in shock, my own sister was admitting to wanting me inside her, fucking her. I dove in for another kiss, grabbing her ass at the same time and she continued to grind into me.

I pushed Jess up, "Now that you know he it feels inside you, why don't you take it for a ride?"

Jess smiled at me and then began to bounce up and down, moving up until the tip was close to coming out, before then slamming back down. I laid there, mesmerised as I watched my sisters perky little tits bounce in rhythm. I reached up, grabbing each tit in each hand and massaging them, squeezing on her hard nipples which caused her to moan. She was riding me faster and faster. I knew she must be close to another climax and by now, so was I.

I moved my hands down, grabbing her hips as I thrusted upwards, meeting every bounce.

"I'm gonna cum," I said. "I'm gonna cum inside you," I groaned.

"I'm gonna cum inside my sister--" I knew I was wearing a condom, but the dirty talk and thought of cumming inside Jess was sending me over the edge.

"Do it," she said, moaning. "Cum inside me, fill my sister's pussy."

That was it, Jess' last words triggered that deep feeling in my balls. I thrusted one last time and bottomed out inside her. I shot my load while inside her, groaning out her name. The moment she felt my penis spasm, this triggered her biggest climax yet. She shook on top of me, her legs clamping together as she milked my balls with her tight convulsing pussy until I was empty. She then collapsed on top of me, both of us breathing heavily.

We laid there for a while, panting as my penis went soft inside her. She lifted her head off my chest and kissed me, then pulled away smiling.

"I can't wait to see you around," she said before climbing off the bed.

She picked up her mask of the floor and put it back on. As she reached the door, she turned to me, winked and blow a kiss before walking out of the room. I was dazed. I couldn't believe what I had just done. I picked myself up and walked back downstairs, looking to see where Jess had gone. I couldn't find her and so I assume she must've gone straight home and to be honest, I didn't want to stay either. I needed some air and space to figure out what just happened and what this means moving forward.