I have been dating Brittany for about three weeks to this point in late 1990, and things have been great. We were still stuck in that new high school relationship bliss. Every time we saw each other in the hallway was always an excuse to make out, hug each other, and hold hands, declaring to the whole school that we are dating. I was ecstatic she was my first girlfriend, and I was so proud to get such a beautiful girl to date me. I was never the most athletic person in the school, nor the smartest. I always considered myself just average. My older sister, Emily, would always make fun of me for my lack of confidence with girls. She would say I should be over confident, that I was a decent looking guy. Yet I was still shy around girls.
I started masturbating just over a year earlier when I found one of my father’s playboys. Donna Edmondson was on the cover. I never thought about masturbating before that magazine, there was an article about women jerking off men, so with the beautiful images of Miss Donna I went downtown unlocking a whole new pass time for myself.
The first three weeks of dating, the only sexual thing Brittany and I did was me rubbing her vagina and her jerking me off. She told me she wanted to wait until a month of dating before we moved any further. She had sex with her ex-boyfriend within the first week and then he left her, so she wanted to be sure I wasn’t another sex craved teenage boy.
I was sex craved but I was scared to have sex with her, she would be my first. Or so I thought.
I woke up early that Saturday, the day I lost my virginity, to the sound of my mother and father arguing. I laid in bed trying to make the words of my screaming parents when I heard the front door slam shut. I got up and looked out the window and watched them still yelling getting into their 1981 Nissan Sentra. They drove off I imagine still screaming until they were blue in the face. I wasn’t worried about a divorce, at the time divorces weren’t so common as the are now.
I wandered from my room to the bathroom I shared with my older sister. Emily was 17 at the time, I was 16, I know she was my sister but I always thought she was beautiful. I never once thought of her sexually until I started getting into the Playboys and discovering my own sexuality. She had the same black hair I did, but with my mom’s blue eyes, she had nice firm B cup breasts and a slender body, not that big of an ass but it was shapely enough to turn on most men when she wore leggings.
The door was closed, and out of instinct I knocked. There was no answer so as I normally did I opened the door. The door opened revealing Emily topless listening to her walkman. It looked like she has just returned from her morning run. Being a 16 year old teenager my cock immediately went from limp to fully erect. I was wearing grey cotton sweatpants so my erect penis was as noticeable as her gorgeous naked breasts.
Emily yelped in shock, I started apologizing and then she noticed it, my dick standing upright. She yelled a profanity and threw her hairbrush at me calling me a pervert. I closed the door and went back to my room. I waited in silence until I heard Emily go into her room. I silently went and used the bathroom and returned to my room. I laid in bed thinking about what just happened, when my dick got hard again. With the image of my topless sister in my head I quickly jerked off.
I cleaned up and stayed in my room for another hour before I decided it was safe to come out. I grabbed my clothes and went back into the bathroom, I turned on the shower and stepped in. I finished my shower and turned off the water. I pulled back the curtain and Emily was standing there. She looked down at my penis,
“I thought it looked bigger.” she scoffed.
I was frozen in fear, I couldn’t say anything in response. She then took off her shirt revealing her breasts once again. I felt a twitch in my cock.
“Get out, I have to shower.” She said pushing me aside. She barely touched my shoulder and I could already feel my penis growing. I snatched my towel and scurried to my room. I heard the shower turn on, and I once again jerked off to the image of my naked sister.
I laid in my bed cursing myself for masturbating to my sister. I thought about leaving before I get into more trouble but Brittany was away with her grandparents, and my best friend Mike was at a track meet. I turned on my radio and decided to do some reading.
After about 20 minutes or so, I heard the shower turn off. Then an awful thought popped in my head. I had to see her naked again. I silently opened my door and snuck into her room. I quickly went into her closet and hid myself under some of her clothes. I left the door open enough where I could see a majority of her room, I was hoping all she could see was the normal pile of clothes.
The door to her room opened and Emily stepped in wearing only a towel. She closed the door and dropped her towel on her bed. I saw all of her this time, her breasts bouncing with each step, water still clinging on to her young bush. The beautiful vagina showing through the hair. Once again my dick was hard. I slowly moved to release my throbbing cock from its imprisonment, making sure I didn’t make any sudden movements.
Emily sat at the edge of her bed, facing me. She turned to the door and said something under her breath. She then bolted up and went out of her room. I heard walk down the hall to my door and knocked. I was petrified. She knocked on the door again calling for me. I didn’t answer. I was stuck under a pile of her clothes my cock in my hand, frozen from fear. She opened my door and then closed it. She came back into her room and closed her door, then I realized she was still naked. Why would she go to my room naked?
She walked to the closet and opened the door fully she looked through some of the clothes she had hanging. Her pussy was right in front of me. It was all I could do to not reach up and touch it. She fiddled through more of the hanging clothes before she bent down to go through the pile of clothes. My heart was beating so fast I was sure I was going to have a heart attack.
She picked up a pair of panties and then her eyes widened, she was staring right at me. She quickly threw clothes revealing me. I shifted quickly stowing my dick back into my shorts, before she saw it.
“What the fuck are you doing here?” She yelled.
“I’m sorry, I don’t know what I was thinking. I just wanted to see.” I stuttered out. She yelled for me to get out of her closet. I complied I slowly got out waiting for a hail of fists. I stood by her bed, staring at my naked furious sister.
“I went to your room.” She stated.
“I know, I heard you.”
“Why didn’t you say anything?”
“I was afraid of getting caught.” I said softly looking at my feet.
“That didn’t work too well for you, did it? Why were you in my closet?”
“I don’t know, I just had to see you again.”
“You wanted to see this?” She said twirling in a circle showing off her beautiful body.
“Yes.” I said quietly, I started turning away from her, to hide my growing cock.
“Did you want to touch these.” She said as she took my hand and placed it on her right breast. I stood still not believing what was happening. She stepped closer to me.
“Do you know why I went to your room?” She asked before she grabbed my cock.
“No.” I choked out.
“I wanted to have sex with you. I still do. Mom said you wouldn’t be open to this, but I knew she was wrong.” She said slowly rubbing my dick. I stayed quiet in the pleasure of another person touching me. Then I realized what she said.
“Wait, mom?” Was all I was able to get out. Emily stepped even closer and put her lips to mine. She stuck her tongue through the opening of my mouth. We stood there making out, her hand still rubbing my cock, my hand still moving on her breast. Emily broke out kiss and looked me in the eyes.
“Mom, Dad, and I have been having sex for 2 years now. I wanted to have sex with you but you were always so closed off nobody knew if you were being sexual until you got a girlfriend,” She moved her hand from my cock and stuck it inside my shorts. Her warm hand clamped around my cock. “Mom said that with your girlfriend you would never be open to having sex with your sister, I told her you would. Looks like I was right.” Before I could say anything about the revelation she kissed me again. She removed her hand from inside my shorts and removed my shirt.
“Wait, you and mom? And dad?” I asked out trying to comprehend what I heard. Emily sat me on her bed and stood in front of me. She put her breasts right in front of my face.
“Suck them.” She demanded. Before I answered she shoved my face onto her left breast. I took her nipple in my mouth and started sucking like I was a baby. She let out a soft moan.
“Mom used to have sex with granddad, grandma, and Aunt Maxine. She always wanted to have children she could have a close relationship with. The same way she had with her parents. Mom caught me touching myself and she showed me how to do it correctly and since then we have been having sex. She brought dad into the mix a month later.” Emily moved away and kneeled down between my legs. She grabbed the seam of my shorts and pulled them down revealing my naked erect cock. At 16 it was just over 6 inches, its grown since then.
“Not that bad.” She said slowly jerking me off.
“Have you ever had a blowjob?” I shook my head no. She bent down and licked the tip of my penis. She then engulfed the whole of my cock into her mouth. I was in an immediate state of Nirvana. She kept sucking and licking bobbing up and down. She looked up at me staring me in my eyes as I watched her suck me off. Within 30 seconds I was ready to cum. I tapped her on the head.
“I’m going to cum.” I was barely able to get the words out. She went down further taking the tip of my dick in the back of her throat. She gobbled on it for another few seconds before the strongest orgasm I’ve ever had to this point erupted through my penis. She coughed when the semen filled her mouth, yet she kept sucking, squeezing out every last drop with her mouth. Semen was dripping out of the corner of her mouth. When my dick started to go soft she let go.
“How was that for your first blowjob?” She asked with a wry smile.
“It was the greatest thing I’ve ever felt.” I said. She sat next to me and kissed me. I could still taste my semen in her mouth I was a little disgusted but I wasn’t going to say anything to stop what was going to happen next. Emily grabbed my shoulders and laid me down with her. We stayed kissing for a few moments before she broke away.
“It’s my turn.” She said softly. I didn’t know what she meant at first until she pointed down to her pussy. She was already rubbing her clit.
“Lick it.” She commanded. I moved down her body to in between her legs. She moved her hand and placed it in the back of my head and pushed me closer to her sweet pussy. I thought back to the playboy pictures I saw, and dove in. I put my entire mouth over her vagina and licked away. With every lick I tried to stick my tongue as far as it could go inside her pussy. She quivered.
“Put a finger in while you do it.” She said through moans. I stuck my index finger in, and slowly started to finger her. I kept licking tasting the sweet juices pouring from her pussy. It was the first time I’ve ever gone down on a girl, and I still think I did a good job going off of pictures from an old playboy.
After a few more moments she cupped my face and brought it to her. She kissed me and then took my finger that was just in her and sucked on it, tasting her pussy.
“I want you to fuck me.” She said softly. I stayed still.
“What’s wrong?” She asked
“I’m still a virgin.” I answered shamefully.
“I know, I wanted to be your first. Just put your dick in me.” She said. I moved my once again erect penis in front of her opening. She grabbed it and placed it in her. The wet warmth felt better than her mouth. She put both her hands on my hips and slowly pushed me deeper inside. She let out a soft moan. She kept guiding my hips for about a minute before I had to cum again. I moved out of her. She seemed to know what was happening. She went down and took my cock back in her mouth and sucked me until I came again.
“Don’t worry with more practice you’ll start lasting longer.” She said with a mouth full of my cum. She swallowed all of it and kissed me again slowly rubbing my dick waiting for it to get hard again.
“We are going again?” I asked in between breaths.
“Yes that’s how you’re going to get better.”
We had sex six times that day, and then every day for a month. I waited until I had enough practice with Emily before I had sex with Brittany. I didn’t tell Brittany what was going on until after we had sex the first time. I was worried that she was going to be mad but she was okay with it. She said she has been having sex with her younger sister since she was 14.
I hope you guys enjoyed the story there will be more to come I promise.