First Time With SisbyRoblover©
This is an adult read event that took place in my life. If you are not 18 years of age, please leave now.
Hello! Thanks for choosing my story. I hope you enjoy your reading. I have been reading members wonderful experiences and fictional stories here for quite some time now. I finally decided to write my first of many experiences here and share it with all of you. I have had sexual encounters with two members of my family, my sister and my mom. Neither of the two knew I was having sex with the other, even till this day and I think it is better this way.
This story is the beginning of a wonderful relationship that happened between my sister and me. It sparked a whole bunch of great events between us and still to the present day. All the events are true with slight modification.
I will start with the first time I had "fun" with my older sister. There has been other occasions since and continuing to the present day and will write about them in due time. Sex with my mom did not come till later after my sister got married, which was a little late in her life according to my parents. I will get to those stories out to you later on.
First Time With Sis.
When my sister and me were still living at home with our parents in our large 4 level, 5 bedroom house. I used to try and get a glimpse at Holly whenever I could. Our family was pretty liberal back then, we didn't always close our bedroom doors when changing or closing the bathroom door when showering, walking naked from bathroom to bedroom, stuff like that. Let me tell you, it was not easy for a horny guy like me growing up seeing two women walking about almost naked at times.
I have always had the hots for my sister Holly. We were really close growing up (still are). She is 10 years older than me. She was a really sexy and horny woman, still is now at 53. When I first took notice of her she had a body to die for, 5'9" tall with just the right curves and these wonderful 36C tits, a nice rounded ass, just the right shape and size, long shapely legs and the most well trimmed bush.
I used to wait for here to come home from work and go upstairs to change. I would hide in a spot where I could peek around the corner and watch her change. I would get as hard as a bar of steel. When she would finish changing and would go downstairs I would run up to my room for a quick jerk off session. This went on for quite a while, shower peeks, bedroom peeks and in the summer months seeing her in a bikini around the pool.
A few years went by. I was now 18 years old and my sister was 28. It was December 31rst, New Years Eve. My parents and some of there friends, along with me, my sister and her fiance were all going out to celebrate the New Year. My parents and their friends went ahead of us. My job at the local fast food joint had me scheduled to close up that night and I would not be out of there till about 9:00pm.
My parents asked Holly if she could stay behind and pick me up from work to get me home so I could get ready for the party. She agreed and said she would tell her fiancé to just meet us there.
With all things said and done, Holly picked me up and rushed us home so we could get ready. We were both crossing paths, bumping into one another running in and out of the bathroom from our bedrooms trying to get ready in a hurry. You'd think with such a large house we lived in we would have two bathrooms on our floor of 4 rooms. No, we had only one bathroom on our floor. God forbid if we touched yet went into our parents on suite bathroom. Holly had showered before picking me up. I went to my room, got undressed and was walking down the hall towards the bathroom when I glanced into my sister's room and saw her sitting on the corner of her bed. My jaw dropped as I stopped dead in my tracks, like hitting a brick wall. I could not take my eyes off of my sister. There she was, naked, her tits out in the open, putting on her pantyhose. You know, the type you don't wear panties with. One leg up on the bed and the other on the floor, causing her to expose her pussy, what a sexy sight! She stood up to pull the part up over her hips to her waist and looked up at me, stared for a second and said in a sly tone "like what you see kiddo?"
I was an idiot because all I said, as if in slow motion, was "Aaaaaaaa... Ya" and walked off with my hard on to the bathroom.
I hopped into the shower took in the feel of the water and started soaping up. I lathered up pretty well especially my dick as I started stroking it furiously with the thought of my sister's tits and pussy racing through my mind. I have never seen them that close. I came, shooting cum on the shower walls. I rinsed off, shut off the water and reached for my towel.
I had my towel over my head while I stepped out of the shower and started drying off my head not realizing Holly was there doing her hair and makeup. When I pulled the towel down to dry the rest of me I saw Holly looking at me with a shocked look on her face that quickly changed to a devilish look.
"Did you rinse off the shower?" she said. I looked at her with a grin.
"Wouldn't be funny, for you, if mom found your cum in there." She added
I looked back at the shower as she walked off to her room. All the while I was naked in front of her. I blow dried my hair shaved what hair I had on my face, brushed my teeth and the whole time thinking that my sister was there looking at me, at my cock not to mention the fresh image of her pussy in my mind. I finished up, went to my room and got dressed.
We left to go meet our parents. While driving we shared some small talk. She had her dress up enough so it would not touch the floor of her car. I couldn't help notice my sister's legs as she drove. She looked at me and said "Quit staring silly, your acting like a virgin"
I looked away and down, clenching my hands together and said in an embarrassed tone "I am sis... sorry". Holly looked at me in an angry yet concerned way and said "DON'T BE SORRY!" Then she toned down saying "You're a great brother, kiddo. I didn't mean to hurt your feelings. I just didn't think you haven't been with a girl yet."
I responded with "I'm not very popular with the girls"
Holly sighed; put her hand on my leg in a comforting way saying "It will come, give it time"
The rest of the ride was pretty quiet except for some more small talk. Finally, we got there. While looking for parking spot we saw her fiancé Dan parked sitting in his car waiting for us, we waved as we passed him and ended up parking at the complete other end of the parking lot. Before we got out of the car my sister asks out of the blue in a curious way "Is that why you're always peeking at me, is it curiosity?"
"No... Yes... No" I could only answer.
I never thought my sister knew I was stealing looks.
"Well which is it kiddo?" she asks nicely. Since she knew, I might as well confess. "Well it's like, not curiosity... not curiosity about sex... but... more like curiosity... about... you... I think you're really... Aaa... hot"
She sat back against her door in aw "You risk getting caught by mom and dad just to see me... like... to really SEE ME naked... WOW! I just thought you were looking like me as an object, like you do at the girls in your dirty magazine." I was a little shocked as to how she knew about the magazine I hid in my room.
"I... I'm...flattered... I don't know what to say." She said with a huge smile. Just then her fiancé Dan knocked on her window. As we got out of Holly's car he kissed her hello and asked "Is everything okay"
Holly quickly replied "Everything is fine. I just found out your future brother in law has a crush on some hot chick."
"I see, maybe you should let her know how you feel about her" Dan added while patting me on the back as we all walked to the reception hall.
Little did he know I already did. We got in, checked our coats, found our table. It was close to the front where my parents and their friends were sitting. It was getting close to 11:00pm. As we sat down our meals that the waiters were holding for us arrived. We ate as we watched people dancing and partying it up waiting for midnight. After eating I was wondering around the hall laughing at the drunken people and checking out the women and ogling over some of their attires, trying to get peeks at cleavage and legs. I ended up by the bar near the back of the hall and started talking to some guy when Holly saw me on her way to the washrooms.
"Hey stud, do you want to dance? " She asked.
"Sure" I said.
"But first I have to go to the little girl's room." My sister added.
"Do you know her" asked the guy.
"Nope, do you? I replied trying to look cool.
"I don't think she is coming back" the guy said
What took forever, I finally I saw her coming towards me with two drinks in her hand.
"There she is" I pointed out.
As we walked off to the dance floor she asked while holding one of the drinks up to me "Rum and Coke?"
"Cool, thanks sis" I happily replied.
"Do you mind if we stay back here, there's less people" Holly asked.
"Ok no problem sis" I replied.
Disco was what we danced to back then, it was really fun. I drank down my rum and coke of the evening and had a great time dancing. It was getting close to midnight now so we went back to the table. The bubbly came around and whet fast and so did midnight. We did the usual kisses and handshakes with everyone and by then the music was back and so were the people dancing.
I went to dance with my mom for a bit, Dan and Holly came to join us a few songs later. We were dancing the night away when the D.J. started to play a slow.
So naturally I was walking off and my mom said "Hey mister, you just don't leave a gal like that on the dance floor"
So I went back and had that slow dance with my mom. The song ended, my mom said she was going back to the table. When Dan told my sister to dance the next couple of slows with me I had a grin from ear to ear. I remember we were slow dancing to a Chris de Burgh song that was quite long. I was holding her with my left hand on her waist and the right one in her hand. We worked our way slowly into the crowd away from the table's view. My sister was different, couldn't put my finger on it. Then all of a sudden she puts my right hand on her waist and puts her arms around my neck. At that point, the guy from the bar I spoke to walked by giving me the thumbs up. My sister's tits pressed into me and our bellies touched. I was staring right into her cleavage and she caught me looking.
"It's ok... I like it" my sister said.
She then took her hand and slid my right hand down onto her ass. I couldn't help it. I delicately caressed and kneaded it while looking into my sister's eyes and saw her smile in approval. Wow it was like soft and firm at the same time. It gave me one serious fucking hard on. I know my sister felt it because she pushed into it.
"Someone better calm down, there's no shower here to jack of in. You'll have to take care of that nice cock of yours that I saw earlier, like you do every night" she said laughingly into my ear.
I couldn't say anything and looked away as if ashamed.
"I'm just teasing you. Don't worry about it. I do it all the time. I play with my pussy whenever I hear you whacking off in your room." Holly added.
"You could hear me?" I asked.
"D'uh our rooms are next to each other and the walls are not sound proof. Lucky mom and dad are downstairs or you'd get a beating every night... and not the type you'd like" she said laughing.
I was red and now horny knowing my sis masturbates to me beating off. Well the slows were over and we walked back to the table. It was around 1:00am and the sweet table came out. We all got up to get stuff before it all disappeared. After eating there was more dancing, mingling and drinking. 3:00am came fast.
"We should all get going before everyone leaves at the same time and it turns into a mad house. I'd like to get out of here before the sun comes up" dad said laughingly. "Are you riding with us or your sister?" my mom asked.
"With Holly, she plays better music than dad." I said jokingly
Dad and mom said they would see us at home and they left. Dan walked us out to my sister's car. Holly unlocked the doors. I got in the car and Holly had her car door open as she and Dan exchanged a few words between themselves which seemed to take forever. He kissed my sister turned towards me looking through her car door opening.
"Good night champ and good luck with that girl of yours, make me proud." Dan said loudly while winking at me.
Not knowing what to say, I smiled and said "yeah... thanks Dan"
"What an idiot." my sister said laughing after she got in the car and closed her door.
I looked at her with one eyebrow up thinking to myself, you're marrying this guy. She let the car warm up a bit and Holly drove us home. We were about 45 min behind mom and dad. Holly and I didn't say much on the way home. I stole a few more looks at my sister's legs, which were conveniently exposed. "No lights on, I think mom and dad are already in bed" I said while we pulled into the driveway.
"Probably, dad looked beat tonight. We'll have to be quiet" Holly commented.
I walked in first, followed by my sister. While taking our coats off, my mom called down quietly from the top of the stairs to make sure we were ok and tell us they were in bed and will see us morning or rather the afternoon in our cases. I watched my sister's ass shift up and down as we went up the stairs. As we passed my parent's room on our way to the other stairs that go up to our rooms we giggled as we could hear our dad snoring loudly. We reached the top of the stairs and Holly went towards our TV room. "Aren't you going to change?" I whispered out to her.
"Getting a blanket... Why? Do you want to watch?" She answered in a naughty way as she walked in to the room. I froze right there. She went in and got the blanket and came right back out and stood in her bedroom doorway.
"Well... I'll even let you help?" she whispered to me.
I was caught completely off guard, quickly gathered my thoughts and took a chance for once, swallowed and before I could say anything, Holly reached out and grabbed my hand pulling me in to her bedroom. I let out a "Yes!"
Holly giggled and shushed me saying quietly. "We have to be quiet."
I was already getting hard. Holly put out her extra blanket on the bed and turned her back towards me whispering "undo the snap then unzip me."
My hands were shaking, but not as bad as I thought. I undid the snap and lowered the dress zipper. It lowered down to the top of her ass. My heart was racing and my now rock hard cock was trying to bust out of my pants and I haven't seen her front yet. My sister turned around and lowered her straps over her shoulders and then slowly slid down her dress.
I was in heaven she was wearing a red lace bra. I could see her perfect tits through it. The dress hit the floor and there were those nylons I saw my sister putting on. As I mentioned earlier, she wasn't wearing panties on. They had a white built in panty, which was practically see through. My sister turned her back to me once again.
"Unhook my bra... please." saying.
I was so speechless. I fumbled with the bra clasp, but managed to unhook it successfully and slid the straps over her shoulders. She let it fall on the bed while slightly leaning forward pushing down her panty hose from her waist, bending down even further to push them down to her ankles. Wow what a view of her ass and pussy. She must have been really wet because it looked like her whole crack was shiny.
Holly stood back up and turned around to face me. My sister was so beautiful and sexy (still is) standing naked in front of me, in her own room. "You like" she whispered softly.
I swallowed and just nodded yes. I had to suck my tongue back into my mouth because I think it hit the floor. I didn't know what to do but just stand there. Holly let me take in the sight of her naked body a few more seconds.
"Your turn kiddo." She whispered slowly.
My turn... I was thinking. My sister reached forward and started unbuttoning my shirt (I had already taken off my tie) and took each of my wrists to undo my cufflinks. She pushed my shirt off my shoulders and I pulled it off the rest of the way. She reached for my belt, unbuckled it, then the pants.
Once the zipper was open and lowered below my protruding dick, the pants fell straight to the floor. My dick was sticking out the top of my bikini briefs. My sister put her hands on my shoulders, looked straight into my eyes and winked her right eye at me.
She then squatted down slowly, sliding her hands down my sides to the waist band of my briefs and pulled them down to my feet. She looked up at me, looked at my dick, looked back up at me and whispered "Take a deep breath"
I breathed in and she swallowed my cock in one shot. She turned and pushed me slightly on the edge of her bed so I was now sitting. My sister kept sucking my cock with still her both hands at my waist. I really couldn't believe this was happening. I wasn't going to last much longer.
"Holly... Stop... I'm going to cum, I'm going to cum" I said quickly but quietly.
She stopped, looked up at me and said "Slide up a little"
As I did she climbed up onto me, she looked at me and eased her pussy onto my cock ever so slowly. Once I was in all the way, Holly moved ever so slowly in an up and down, forward and back rotary motion on my dick. "Your cock feels great in my cunt" she whispered. About five minutes of my sister fucking me, I started to move with her.
She leaned forward whispering "Don't move too much or the bed will creek... we'll go wild another time"
That was it, I murmured "Oh Holly, I'm..."
I was just about to tell her I'm going to cum.
She cut me off whispering hard saying "I'm cumming Robbie... cum for me... cum inside me... cum in your sisssssssster... Ooooo fuck I'm Cummmmming"
I pushed up into her and I shot my load, spurts after spurts of cum into my sister's cunt. She kept moving about slowly and our mixed juices were oozing out and down to my balls and toward my ass. She finally stopped, were both breathing hard staring at each other from the most intense fuck ever, my only fuck ever.
My sister climbed off me, slid down to my cock, looked up at me and licked me from my ass crack, over my balls to the tip of my cock, licking up our sex fluids. When she was done, I collected myself and got up off her bed, bent to pick up my clothes, she then stops me before I turn away, leans in and gives me a deep kiss on the lips. The taste of our juices was so sweet and horny tasting that I kissed her back passionately. Then suddenly Holly broke our kiss.
"My New Year's resolution came true." whispering to me.
"Mine too!" I whispered back.
We giggled at our stupid remarks. My sister then wrapped her hand around my semi hard and sticky dick giving it a couple of light squeezes leaning towards me. "You know I'm going to want more of this. I think WE need to go skiing this weekend?" Holly whispered in my ear.
"Yes... but let's not forget our skis" I quickly replied.
"Happy New Year bro" she whispered.
"Happy New Year sis" I whispered back. I snuck out of her room quietly and entered my room, closing my bedroom door behind me ever so quietly. Just as I dumped my clothes on the floor and crawled into bed I heard my parent's bedroom door open.
I will be posting more of our experiences. Thanks for reading.