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My Sister's Proposal

By: fubar769



I was 23 years old with a degree in Computer Science. I started my first real job right after graduation and I was happy to land it given the tough economy at the time. The good news was that for the first time in my life, I was making enough money to contribute to my saving account each week. The bad news was that the people around me knew I had extra cash and were quite outgoing about asking to borrow money from me. 

My sister called me 10 minutes after I got home from work. What a surprise she was on her way over, no doubt to borrow money. She graduated high school a few months back and just turned 18 a few weeks ago. She drove a piece of shit car that she invested more money in repairs than the damn thing was worth. She didn't care because since she loved that car. The problem was that she worked a minimum wage job in retail and she was saving to start community college in two weeks. She borrowed $50 here, $100 there and by August she owed me over $500. Here it was Friday, my payday and conveniently she was stopping by again. 

Before she arrived, I changed in to a pair of shorts and a T-Shirt so I could start to unwind. I grabbed a cold beer from the refrigerator and took my place on the recliner to watch the baseball game on TV. Before the game started, there was a knock at the door and my sister walked in like she normally does, without me having to get up.

She's about 5'3" tall with short brown hair. She was wearing her typical attire consisting of short shorts with "Juicy" printed on them and a slinky tank top. She worked at a clothing store and spent most of her check buying new clothes that advertised "Juicy" each week. She was convinced that she was saving a lot of money buying the clothes thanks to her employee discount and never saw the logic that she'd be saving more money if she didn't spend it.

"Hey big brother," she said walking past me to have a seat on the sofa. She dropped her purse and cell phone next to her. She crossed her legs and peeked at the TV for a second.

"Hey. What's up?" I asked, waiting for her to ask for money. 

"I'm starting school in two weeks. You live 8 minutes away with traffic. I was thinking that if I moved in here with you, I could save a lot of time and gas money commuting to school." She suggested. 

She knew I was big on saving money so she threw in 'save money on gas' to win my approval. I knew she just wanted to move out of Mom and Dad's house and get a taste of freedom. I know what a pain in the ass it can be to live in their home under their rules and I'm glad I was able to get in to a good school on a scholarship so that I could get the hell away for a few years.

"How are you going to pay rent here? You owe me $500 already and you can barely make ends meet as it is," I stated truthfully.

The look on her face turned from confident to sadness when she heard me state the obvious. Her money situation was not going to improve living here with me. It was just more convenient for her. She glanced at the floor for a few seconds, and then an idea came to her.

"Yeah, my job sucks, but you have a good one," she indicated as if somehow that justified me helping her. "What if I work it off around here?" she offered.

"Work it off? How?" I asked.

"I could cook, clean, take out the trash and do the laundry around here," she begged looking around knowing her argument was pointless since I am a clean freak and my apartment was immaculate. 

"I need to move out of mom and dad's house. They are driving me crazy," she confessed almost in tears.

"How long has it been since you've gotten laid big brother?" She asked.

"Well, it has been seven months since Amy and I broke up," I confessed, wishing she had not reminded me I have not had pussy in seven months. I've been so focused on finishing school and work that I didn't realize that much time had passed.

"Seven months!" She exclaimed. "No wonder you're grumpy sometimes! Let me fix that for you right now."

I was shocked to hear my little sister offer to help me out in that department. I never looked at her in a sexual manner before. Sure, I knew she had a great body and was popular with the boys, but I never thought about fucking her before. The idea of screwing my sister was approved by my cock immediately since I felt it surge in my pants as she walked over.

She knelt between my legs on the floor and began to rub my cock through my shorts. I took another swig of my beer and looked down to watch her skinny fingers rubbing the outline of my penis stuck in my shorts.

"Wow. You really are my BIG brother," she said squeezing my cock for effect. 

She moved her mouth to the end of my cock and blew in to my shorts. I felt the warm air from her mouth on the head of my cock. She unfastened my belt, tugged on the zipper and pulled my shorts and boxers off. My semi-erect cock sprung out to greet her hand while she started rubbing it up and down. I felt it getting harder and harder with each gentle stroke and I closed my eyes to take in the sensation, not wanting to think of my sister pleasuring me.

I jumped a bit when her tongue first touched the head of my engorged mushroom head. Her hand guided my penis in to her mouth and she began sucking on the tip. I sat there with my eyes closed for a few minutes while she licked and sucked my cock while using the wetness from her mouth to lubricate the rest of my shaft with her hand. I knew from her technique that this was not the first time my little sister sucked a cock.

I opened my eyes to see her right cheek bulging from my cock pressing against it inside her mouth. She expertly slid the head of my dick over her inner cheek before sliding back further in to her mouth. She repositioned herself in front of me on the floor so that she could attack my cock from a different angle. This time, I felt my cock going much deeper in to her mouth and down her throat. Her tiny fingers were wrapped around the base of my prick as she took my bulging shaft deeper down her throat. Finally, I felt her release the grip she had on my member as her lips made it as far down as she possibly could before she started to gag. I knew she was trying to see how much of my cock she could fit in her mouth, but she was still about two inches short on her best effort.

My cock popped from her mouth and the suction broke the silence.

"I can't get it down," she said, "but I know it will fit nicely inside my pussy."

Although she didn't succeed, I had no complaints and applauded her efforts. She stood up and removed her juicy shorts and tank top. She had a really tight ass with a completely shaven pussy. She turned around with her back facing me and put her arm between her legs to grab my cock again. This time she was guiding it in to place at the opening of her moist pussy. I spread her ass cheeks from behind so that I could see my cock enter my sister for the first time. The inside lips of her pussy were a very light pink color and I saw the wetness on the inside of her spread lips as my cock head slipped in to place at the entrance of her hole.

She removed her hand from my cock and began to lower herself on to my throbbing shaft. My dick easily slid inside of my sister's wet pussy. She let out a moan as my cock continued to slide deeper in to her pussy. I confirmed that the word "juicy" printed on her shorts was a great advertising slogan for my sister's pussy since it was juicy.

I grabbed her hips and began to push and pull her up and down my cock, watching the slickness grow on the length of my shaft with each stroke deeper inside her. I had a great view watching the length of my cock slide in and out of her. I finally slammed her ass all the way down on my lap so that I could feel my cock bottom out inside her juicy pussy and reached around to grab each of her tits while she sat still with my full length inside her. She moaned and began to gyrate her hips in circles on my rock hard shaft, bringing herself to orgasm with me deep inside her.

I pushed her off and got to my feet. I bent her over the arm of the sofa and shoved my slippery cock back inside her. This time, I began so savagely pump her from behind like a jackhammer. She was moaning and groaning as my cock rammed in and out of her.

"So fucking good," she groaned, "Your cock feels so fucking good. I'm cuming again."

When her moaning subsided, I rolled her over on her back on to the sofa cushion and repositioned myself on top of her. I saw the lust in my sister's eyes for the first time when we made eye contact with me now on top of her. She bit her bottom lip as my cock slid back inside her. I put her knees on my shoulders so that I could pump her deep on the sofa. My cock bottomed out inside her and my balls slammed on to her ass with each hard thrust. I rammed my cock as far in as it would go and held it there as my balls began to surge. She had an orgasm while I remained motionless deep inside her. I felt the sperm begin to exit my balls and pulled out of her just in time to shoot a two foot rope of cum on her. The first shot emerged with such velocity that it landed on her cheek. The rope of thick white semen stretched from her cheek to her tits and my balls continued to pump cum all over her. When I was done, my sister was covered in my cum, but she enjoyed it. 

"How was that, big brother?" She asked feeling my cum on her cheek with her hand.

"You're a great fuck!" I said.

"You're pretty good yourself. Are you ready for a roommate now?" she asked in a sexy voice while shaking my sticky cock with her hand.

"Then we could do this whenever we wanted," she said with a vixen smile on her face.

She moved in the next day. We fucked at least 10 times per week for several months after that. I started dating a girl I worked with in December. Since I was already fucking my sister, I was able to take more time to get to know my new girlfriend before sex was brought in to our relationship. 

Although, I must confess that there were many nights where I fucked my girlfriend at her house and went home and fucked my sister right after anyway. My sister seemed to get turned on more when my dick tasted like another woman's pussy. It was not for many months that I learned she was bi-sexual, but that is another story.

My Sister's Proposal Ch. 02



My sister, Cindy, was my roommate for the past eight months at the time. We started having sex the day before she moved in and enjoyed each other's company many times since then. Our encounters tapered off a bit when I started dating Donna, who I worked with, but not enough for me to complain. Between my girlfriend and my sister, I was still getting laid more than the average Joe.

Things with Donna are a bit complicated since she lives in the city and I live in the suburbs. I work with Donna in the city, so I am the one stuck with the long commute most of the time. Most of our dates start right after work and if things go extremely well, I spend the night, if I have a change of clothes with me; otherwise, I have to make the long trip home afterwards. 

"I'll see you tomorrow afternoon, Cindy," I stated while heading out the door Friday morning with my briefcase and overnight bag.

"Cool. Have fun big bro," Cindy said, "Enjoy your hot date tonight."

"What are you doing tonight?" I asked.

"Susan is going to come over around seven and we're going to watch some movies," she said in an excited manner.

"Cool. Tell her I said hi. I have not seen her in a couple of years," I remarked.

"I'll be sure to tell her," Cindy said.

Susan is the daughter of our mom's brother, making her our first cousin. We don't see that side of the family much since they are the black sheep. My aunt is an alcoholic, my cousin Tom has been in and out of the juvenile detention center since he was 12 and now he's 23 serving time for grand theft auto. To me, Susan seems to be the only normal one from that part of the family, but I have not associated with any of them much for fear of any trouble that might soon follow. Besides, I've heard that Susan has some skeletons in her closet as well, but no one has elaborated on exactly what that meant. As long as she was in the apartment with my sister, whom I trusted, I was sure everything would be ok.

The commute to work was stop and go, as usual. Upon my arrival, I jumped in to my daily routine so that I could clear my plate of things to do as fast as possible. I wanted to be able to enjoy my evening. It was not until 11am that I noticed Donna had not peeked in my office yet to say hello. I decided to take a break and go see her. 

Her office was dark and still locked when I arrived. There was a note on the door. "Out sick" with today's date and a number to call in case there was an emergency. 

"FUCK!" I said to myself. I knew she seemed sick yesterday, but I was hoping she was going to climb out of it for today. I went back to my office and called her to see how she was doing. She answered the phone on the fourth ring, just before the machine picked it up. She sounded horrible. It seems she had a full blown case of the flu and tonight was off. I was disappointed, but certainly, I understood.

Around 3pm, some people started to organize a happy hour celebration just for the hell of it and word spread throughout the office. I have not been to happy hour in a while, so I decided I'd go and hang out with the office gang for a while after work to let traffic die down before I head back home this evening.

About twelve people showed up. I ended up staying at the bar until 9:00pm before heading home. I only had a few beers, so I was ok to drive, but I was tired since I have been up since 6am and was just now heading home in the dark. The weather was not that great either, which made the roads a bit slower than the usual off-peak traffic period.

It was about 10pm when I parked my car a few doors down from my apartment door. I gathered my things and unlocked the front door. Upon entering the living room, there were no lights on, but the glow of the television was more than enough to illuminate the room. It appeared the DVD playing had finished and returned to the main menu. It was a chick flick, of course. I heard faint music playing in the distance and some other sounds I could not make out from where I was standing.

I silently dropped my things in the entry way and made my way through the living room to the hall leading to the bedrooms. I noticed the light in my room was on and the door was open. There was some music playing in the background in an attempt to drown out the sounds from the foreground. I heard talking and moaning coming from my bedroom at the end of the hall. With the stealth of a ninja, I made my way to the entrance of my room hoping I was going to find something good.

To my delight, my sister and my cousin, Susan, were each lying on their back with their pussies facing each other. There was a purple double-ended dildo between them that disappeared in to each of their holes. It was at least two feet in length as far as I could tell. They took turns grabbing the middle of it and wiggling it in circles as well as back and forth to have it move in and out of them. 

Susan thinned out since the last time I saw her. She's 19 years old with long straight red hair. Her breasts filled out nicely in to what appeared to be a 34C. She was on the thin side for her height and seemed to be in great shape. From my view point, I could see the dildo moving in and out of my cousin, Susan, but my sister's leg blocked my view of her familiar snatch.

The women moaned and writhed on the bed with Susan taking command of the dildo. She worked it faster and faster in, out and around. Each woman fed off of the other woman's excitement. When they came in unison, Susan slid the dildo out of them. She jumped to all fours and took a position between my sister's legs. She was rubbing my sister's clit with her right hand and licking her juices at the same time. That is when she noticed my figure in the doorway and stopped cold.

Both women tried their best to cover themselves while looking at the entrance to the room. I entered the doorway so they could get a full look at me, putting to rest any fears they might have that I was an intruder.

"What are you doing home?" Cindy asked.

"Donna has the flu," I stated. "What are you two doing?" I asked sarcastically.

"Just playing," my sister said.

Susan was embarrassed and speechless. She was doing her best to keep the covers on her and remain still. 

"Why are you in my room and not yours?" I asked as if I cared that two beautiful, naked women were in my bed.

"You have a king size bed and mine is only a twin," Cindy pouted.

I didn't give a shit that I was blood relatives with both women. At this point, I wanted in on the action. My cock already made its decision since it was rock hard in my pants and was just waiting for the rest of my body to catch up and get this plan in to motion.

"Can I play too?" I begged.

I walked in to the room towards the closest side of the bed, where my sister was sitting.

"It's fine with me if you want to join us," Cindy said, reaching out to grab my cock through my pants as she has done many times before.

"You guys planned this!" Susan accused.

"Planned what?" Cindy asked.

"Planned this convenient intervention to persuade me back to being straight," Cindy said coldly.

"He doesn't know. Besides, I would never betray your trust." Cindy lashed back at Susan.

What I didn't know at the time was that Cindy was molested by her brother, Tom, who is incarcerated now. Tom forced himself on his much younger sister many years back, but the family covered it up so that Tom would not get in trouble. As a result, Susan was forced to bury her pain and live with the shame of being raped by her older brother on several occasions, mostly when he was drunk. Later on, Susan developed an overall distrust of men in general and could only feel comfortable enough with other women to be intimate. She has not been with any man since that horrible period of her life years earlier.

"Why don't you chill out over there and watch us for a while," Cindy motioned to Susan. Susan took a seat in the bedside chair facing the bed.

Cindy unfastened my belt and undressed me so that my cock was no longer confined by my clothes. I felt the pre-cum lubricating the tip of my dick when her fingers gently rubbed my purple mushroom head. She began to suck my cock as she did so many times before, taking it in to her cheek before sliding it down her mouth. At the same time, she worked the saliva from her mouth further down the shaft with her hand so that she could stroke me with her hand while expertly sucking the head. The head of my cock would pop out of her mouth each time with a loud pop as the suction she applied was broken.

My cousin Susan was watching my sister orally pleasure me from the chair with inquiring eyes. I could not tell what she was thinking, but the fact that she was not running away was a good sign. Cindy jumped on my face to assume a 69 position. I immediately responded by burying my face deep in to her pussy. Her hole was gaping open a bit from where the dildo penetrated her earlier. That made it easier for me to work two of my fingers inside her so that I could focus on licking and sucking her clit. My fingers slowly slid in and out of her where the cold dildo had been minutes before. I could still feel the coolness around her hole, which was obviously the result of something artificial being there. Cindy sat up on my face as she came. I removed my fingers from her and placed my mouth on her entrance. She sat down harder on my face to complete the air-tight seal so that her juices could flow directly from her honey hole in to my mouth without escaping.

Cindy jumped off me and mounted my cock cowgirl style. She positioned my cock at her opening and slowly worked herself up and down on my shaft. When I was all the way inside her, her hips gyrated around my pole like an impaled belly dancer. I felt her pussy opening more and more inside as her arousal reached a level I had not seen before. My cock slid in circles inside her rubbing every inch of her inner lining as it rotated inside her. She was mimicking the movement of the dildo Susan controlled inside of her earlier. She came with a vigorous shake before thrusting her hands forward on to my chest. She jumped up from my cock and rolled to the side. The wetness of her pussy leaked down my ass as the cold air hit my cock.

Cindy motioned for Susan to come over.

"You showed me some things with the double dong tonight and trust me, it is much better with the real thing darling. Let me show you," my sister motioned to Susan.

Susan slowly rose from the chair and made her way to the bed. My sister directed her to lie on her back. Susan complied.

Cindy directed me to take my place with my cock between Susan's legs, but insisted that she drive for now.

I complied. Susan spread her legs a little bit while I positioned myself with my cock between her legs. Cindy grabbed my cock and began rubbing it up and down Susan's pussy. The juices still on my dick from my sister's pussy combined with the juices coming from my cousin's pussy to form a slick family lubricant. My sister continued to rub my cock up and down Susan's slit, pausing from time to time to massage her clit with the underside of my shaft.

"Mmmmm," Susan moaned. "It feels so warm."

"It's much warmer than that cold-ass dildo and it is thicker too," Cindy confirmed.

Cindy jumped on her in a 69 position to allow Susan to eat her pussy while Cindy continued to control the rubbing of my cock on Susan's opening. Cindy tugged on me to move in closer so that she could pop the head of my cock inside of my cousin before pulling it out as fast as it went in. She repeated this for a minute or two. Each time my cock popped in and out of Susan, she rewarded my sister with some intense licking. Soon both women were in a world of their own. My cousin Susan was munching my sister Cindy, who in turn had my cock in her hand working it on my cousin's slippery entrance.

I'm sure that each woman came at least one time before Susan began to speak.

"Fuck me!" Susan said.

"Fuck me!" Susan said louder since the first time was somewhat muffled from her position between Cindy's legs, even though everyone heard her.

Cindy jumped off of Susan's face, but continued her hold on my dick.

"You want to feel my brother's cock inside you?" Cindy asked.

"Yes!" Susan confirmed.

Cindy rubbed my cock head around the outside of her hole to maintain her control of the situation.

"You want my brother deep inside you?" Cindy asked to confirm once again.

"Yes. Please fuck me. I want to feel his cock inside me. Please let him fuck me!" Cindy begged.

Cindy directed me to lie on my back so that Susan could straddle me. I was now face to face with my beautiful red-headed cousin as she positioned herself on top of me. The freckles on her face and her stunning green eyes reminded me of our youth. She leaned forward with her hands on my chest while my sister positioned my cock between her legs. 

I felt Cindy swirling my cock around Susan's slick opening while Susan slowly leaned back and sat down to take my dick inside her. When my cock head popped inside my cousin, my sister's hand slid to the very base of my shaft. Susan continued to lower herself on to my throbbing rod until she bottomed out on Cindy's hand.

When Susan's pubic mound touched my sister's hand, she moved my cock in a circle, just like they were moving the purple dildo earlier when they thought they were alone. Susan's eyes remained closed while she processed the sensations moving inside her.

Finally, Cindy released my cock from her grasp so that my cousin could take the rest of my cock inside her. Susan wasted no time taking more of me inside her. Susan gasped as my cock slid deeper and deeper into her slick pussy.

When her pubic bone met mine, she knew I was as deep inside her as I could possibly be. She let out a deep breath indicating that she had reached her first goal, which was to get as much in her as she could. Susan began to mimic Cindy's rhythmic grinding on my cock from just 10 minutes earlier. Susan worked my cock exactly like she worked the purple dildo earlier, except this time; she was not using her hands. She was using her hips to gyrate around me. The sensation was new and different to her, but she took it all in.

Susan's eyes remained closed as she pulled her hands from my chest to sit back even further. My cock impaled her even further as she spread her legs even more and leaned back to ensure she had every last centimeter of me inside her. While her motions were similar to Cindy's, there were some differences. I felt the arousal from my cousin deep inside her as the head of my cock randomly rubbed and probed different areas of her insides. My red-headed cousin seemed to be in a trance. It was as if the world around her no longer existed and the only thing left was my thick throbbing cock deep inside her pussy. She derived as much pleasure from it as she could stand before her body quivered and collapsed on top of me as my sister had done before.

"Fuck her hard," my sister demanded.

Without hesitation, I placed my arm around my cousin's back so that I could pin her down on me. I now had room to pump her pussy from underneath her. My cock slid in and out of her. I used my hands on her hips to show her the rhythm of our thrusts. I began to jack hammer her pussy without any mercy. Each stroke was vigorous and ended with my cock slamming all the way inside her. 

Her gasps increased and her body tensed. Susan let out a primal moan as if she were a cave woman grunting pure pleasure. My assault continued on her pussy as she came violently on top of me at least twice.

I felt like I was going to cum soon, so I pulled her off of me and rolled her over on her back so that I could pound her pussy in to the mattress. I took my position between her legs, and then pulled her legs back so that I could pound her. As my thrusts increased in intensity, Susan's face froze and her head arched back. She was moaning, but there were no words in her moans, just primal sounds. I pressed her legs back to gain some more room and leverage. Susan took my hint and pulled her knees back towards her ears, showing off her flexibility. That allowed me unobstructed access to continue pounding her pussy hard and deep.

"So fucking good!" she moaned.

"Fuck me harder! Harder! Harder!", she demanded.

I was already pounding her pretty hard, but found the strength to comply with her wish. I picked up the intensity. Her body shook each time my pubic bone slammed in to her, indicating my cock was in all the way.

"Don't stop. I'm going to cum!" She begged.

Her moans grew louder as the orgasm built inside her. Finally, with a roar, her body shook and the orgasm went straight through her body. At the epicenter of her orgasm, my cock was still drilling her, which sent multiple after-shocks through her. Between her moaning and the contractions on my cock, my balls could not hold back anymore. 

"I'm cumming," I stated.

I withdrew my cock from her slippery hole near the end of her orgasm and lay back on the bed.

Within a second of my cock leaving her, I was treated to the sight of both my sister and my cousin working my cock to milk every last drop of cum that erupted from me. When my balls could offer no more fluids for them to drink, they kissed each other passionately, which was a great finale for me on the evening. 

"That was soooo fucking good," Susan said.

"So does that mean you like dick now?" Cindy asked.

"Well, I like this one, "Susan said while shaking my cock in her hand. "Let's say that I went from lesbian to bi-curious," she laughed

Apparently, Cindy and Susan have been having intimate encounters since my sister turned 17. I had no idea Susan was a lesbian before and I had no idea my sister was bi. The three of us slept in my bed that night. I woke to both women sucking on my morning wood. What a way to start a Saturday!