A young tom-boyish girls has her first sexual experiences with her best friend and step brother.
My First Sexual Experiences as a Teen
I always kind of wanted to be a boy because I grew up with all boys. When my dad passed when I was 11; I took over the whole role as boy. I rarely ever wore girl’s clothes and guys never really saw me as anything more than a boyish girl. I loved the feel of boy clothes and I liked only girls. My mom was free spirited and open minded; she believed I could like anyone I chose. I hated to be alone after school with my sister at college and my mom working and with Ron in evenings she allowed my friends to come over after school. My friends were a mix of girls and guys they would hang out and sometimes even stay the night. My best friend was Allison, but I called her Ally. She lived next door and her parents never minded her being over at my house. I was only 14; but Ally was 15 and played sports but liked girls too. She liked to wear basketball jerseys and liked wearing boy clothes too. Ally went to another school but after meeting my school friends we all hung out together. Whenever we were bored Ally and I liked to chat on the internet. We would sometimes show our boobs and even kiss each other sometimes on webcam. She and I were really close and she even slept in my bed with me when she stayed the night.
The summer of my freshman year was great. I went to high school parties with Ally we hung out all the time. During that summer we were sunbathing, swimming, or shopping at the mall. It wasn’t long before I really started to like Ally and she felt the same about me. It felt so perfect; we shared clothes and even kissed and at night sometimes pretended to be boyfriend/girlfriend by kissing and touching each other.
One Saturday morning my mom came home one day with Ron; Ally and I were in my room listening to music and being crazy in my room as usual. She told me she has some news she would like to share with us. She told me that “Ron and I are getting married in a few months; he will be selling his house and moving in with us next weekend.” We were surprised at first but I knew it was going to happen eventually. Ron was a really nice guy and made my mom very happy. We told her that we were happy for them and then she mentioned that Jason (Ron’s 17 year old son) would be moving in too. I felt a little anxious and awkward but I tried not to show it. It would be weird because Jason was the Quarterback for the football team at the same high school went too. We never much talked or hung out and I liked him a lot it. We had a class together and when his dad and my mom begin dating it we started talking. After a few months of our parents dating we talked all the time at school. He came over once with his dad and I was really shy. I mostly just hung out with Ally and we talked about how cute he was and we had really dirty minds. We kept fantasizing on how we could sneak into the bathroom and watch him shower or maybe spy on him late at night in his room. I could tell she liked him as much as I did. He was unbelievably good looking and he was the only guy either of us ever had a crush on. I felt a little jealous because Ally was older and better looking.
The weekend that Ron and Jason begin moving in; I watched from my bedroom window. My mom was helping arrange things as the guys unloaded the U-Haul truck. After watching for a few minutes, I got dressed and went downstairs to help. I offered the guys a cold drink of lemonade. Jason was all sweaty and took off his shirt. I felt like I was in heaven just to be that close to him half naked.
That night my mom and Ron went over to his house to clean up. I stayed in my room alone watching TV because Ally was at a Softball Tournament. I wanted to go spy on him so I went to go to the bathroom. I closed the door connecting his room to the bathroom. After I used the bathroom; I washed my hands, face, and fixed my hair I opened the door leading to his room and watched Jason as was putting up a poster on the wall. I walked over and held up the other side while he taped it. We started talking about how he liked everything so far. He went on to ask me a few questions like if I had a boyfriend, what I like to do for fun, etc. It was the first time he had tried to get to know me. After a few hours of helping Jason put away his things while we started to watch a movie together as laid sat on his bed. It was so relaxing laying there next to him. I felt so turned on but I didn’t know why. He put his arms around me and it felt so perfect. I closed my eyes and leaned into kiss him. He was shocked at first but kissed me back. We laid there cuddling watching the movie. After the movie it was getting late and I had school the next day. I said good night and went into the bathroom to shower. I thought about him the entire time and I knew I could never tell Ally about what had happened because she might be jealous. After the shower, I peaked in his room wearing only a towel. He was asleep on his bed in just his boxers. It turned me on so much I went back to my room and laid in bed masturbating.
The next morning, Ron took Jason and I both to school. He dropped us off and it was the first time people saw us together. People asked Jason why we were riding together. He told them that I was his “soon to be step-sister”. I wanted to be more than that though. I could never tell anyone that we kissed in his bed the night before but I couldn’t wait to do it again and maybe even do more.
That night when he came from football practice Ally and I were in my room. We saw him walk down the hallway and we said “Hi Jason!” He looked in my room wearing his dirty football practice uniform and looked and smelled sweaty and Ally said “you’re all sweaty, you need a shower” and he said “I’m going to take one right now” and Ally said “can I watch?” as she laughed. He smiled and just went down the hallway towards his room. He went into the bathroom and closed the door to connecting my room to the bathroom. We heard the shower start and Ally tiptoed over to the door and opened the door quietly attempting to watch him shower. I was not surprised that she spied on him. She looked for a few minutes until I walked over and tried to look for myself. We couldn’t see much due to the steam on the shower door but we saw his naked body all lathered up with soap which turned us both on. She slipped quietly into the bathroom and grabbed his towel without him noticing. She ran back into my room and we both begin laughing hysterically. A few minutes passed and we heard the water turn off and the shower door open. He opened our door and hid behind it then asked “did someone take my towel?”
Ally and I both started laughing and she held the towel up and he said “can you bring it to me?” and she told him to “come get it.” He didn’t know what to say so he covered his penis and walked into my room naked and dripping wet to get the towel. We both laughed and she threw him the towel he had to take his hand off his penis to catch it. He wrapped himself and smiled then went back into the bathroom.
After he closed the door we were still laughing and she asked me “did you see it?” and I smiled (knowing I took a glimpse of his penis). We continued talking about sex although we were both virgins but we were both curious about the urges we had to have sex. We watched a movie and kissed for a little while in my bed because we were still really turned on from earlier.
Ally’s mom called and asked if she would come home. She got off the phone and said “I have to go, let me know if anything good happens.” As she grabbed her backpack and I replied “I will probably finish my homework, watch TV, and just go to bed.” She gave me a kiss goodbye and went downstairs to go home.
I finished my homework and then went in the bathroom to take a shower. I closed Jason’s door and made sure I kept my towel close by in case he did the same thing to me. After washing my body, I washed my hair. I turned the water off and the bathroom light went off. I got out of the shower dried off and wrapped the towel around me as I walked over to turn the bathroom light back on. I opened the door to Jason’s room and looked at him laying on his bed in just his boxers. I asked him “did you turn out the light on me?” He smiled “maybe, but it isn’t as bad as taking your towel.” I just smiled and said “that was Ally” and I went back in my room. I got dressed really quick putting on underwear and a sports bra then shorts. I came back in his room and sat down next to him on the bed. I said “do you play pranks on unsuspecting girls?” He said “I never knew you and your friend wanted to see me naked that bad.” I smiled and said “I could of resisted, but she couldn’t.” He smiled and laughed. He asked if she was always that flirtatious and why I was so shy. I said “I’m not that shy” as I cuddled up to him in his bed. We watched TV and he got up and turned out the light. I couldn’t believe I was cuddling next to him again. I was so turned on and we started kissing. He began caressing my body and I did the same to him. I felt his hardon pressed up against my leg. I knew I wanted him to do whatever he wanted to me. He started to touch me over my shorts and rub my clit. It felt so good I slid my shorts down and he rubbed me through my underwear. I was starting to get really wet and he slid his finger inside me as we kissed. I pulled my underwear down as he continued to rub my clit. He pulled off his boxers and put my hand on his hardon guiding me to stroke it slowly. I knew I wanted to feel him inside me; although I had never been this far with a boy and hoped it wouldn’t hurt too bad.
He started to finger and began licking my pussy as I laid there. I didn’t know what to do so I just allowed him to do whatever felt good. It felt amazing to have his tongue on my clit and his finger inside me. He went on to slide his hard cock in my tight virgin pussy slowly. I laid there really anxious but it felt really good once he got it inside. He slowly went back and forth with it as I laid there looking into his eyes. We continued to have sex quietly until he pulled out and came on his sheets a few minutes later. I felt like was that it? I knew there was more but I knew I needed another shower. I got up and went into the bathroom I couldn’t believe I just had sex for the first time. I cried a little in the shower and I wondered if I was good. I would hate to be bad my first time but all I did was lay there while he pleasured me.
I came out of the shower and wrapped a towel around myself. He came into the bathroom and gave me a kiss as I hugged him. I felt so close to him. He then got in the shower and I went into my room and laid naked in my bed. I couldn’t believe I just had sex. I called Ally but couldn’t tell her. I just told her I couldn’t sleep. After talking to her for a few it was ready for me to go to sleep. I covered up and fell asleep naked. It was the first time I ever slept completely naked and it felt so relaxing.
The next morning, my mom woke me up and I hurried to put clothes on to go to school. I thought about Jason the entire day and after school Ally came over. I had to confess to her it was too hard keeping it a secret. We sat down on my bed and I told her what happened. She seemed kind of jealous because she wanted to loose her virginity first. She asked me what seemed like a million questions about it. I told her that he would probably do the same to her if she spent the night tonight. She called her mom and told her that she was going to spend the night. We both knew what we were going to do and so we got ready for him to get home.
Around 5 o’clock that night; Jason came home from football practice. Ally and I watched he walked down the hallway to his room. He started the shower a few minutes later. We waited for him to get done with his shower as we both planned what we were going to do. We were both really nervous but we knew he wouldn’t turn down two girls who wanted to have sex with him.
After he was done Ally said I will go surprise him. She opened my door and walked through the bathroom into his room. He was putting his boxers on and she said “Hey.. oh sorry, I didn’t realize you were naked.” He smiled as he continued getting dressed and he asked “did you need something?” She got a little nervous and said “oh, I was just seeing what you were up to..” He smiled and saw me standing in the doorway. We both sit down on his bed and he sits down between us. He looks at her and then looks at me and says “ok, what is it? You both he something going on.” As he smiled.
Ally leans over and kisses his lips and shocks him at first. Then I do the same. He was totally puzzled but then Ally helps him take off his t-shirt and undoes her shirt. He looks at me and then looks back at her standing there in just her white bra and jeans. She undoes her jeans and pulls the down. His erection is poking out of his boxers and I lean him back on the bed. Ally spreads his legs and gets on her knees in front of him sliding his erection into her mouth. I start to kiss him softly as I begin to take off my clothes.
Ally stood up and slid off her thong and was naked and laid next to me on the bed. I was laying there in just my bra and underwear as Jason spreads Ally’s legs apart. He was really hard and he slid it inside her fast as she clinched the bed he begin thrusting into her much harder as he did to me. She and I began kissing as I held her hand as Jason took her virginity. She started to bleed and I could see it but Jason didn’t stop. She was laying there almost in tears as we held hands. A few minutes later he pulled his bloody erection out of her and she got up and ran to the shower as the blood ran down the inside of her leg. I didn’t know what to say or do. I followed her into the bathroom as Jason cleaned himself off. She was sobbing in the shower. I took off my bra and underwear and got into the shower with her. We hugged as she cried on me. I told the same thing happened to me. We turned the water off and dried off she was so embarrassed that she went into my bedroom. I went back into Jason’s to get the clothes and see if he was freaked out. He said it wasn’t gross, he didn’t mind. He changed his sheets already and was going to take a shower. I went back in my bedroom and put the clothes down Ally was laying naked in my bed crying just as I did the night before.
I got into bed and we cuddled naked as she continued crying. I told her that he wasn’t grossed out and the same thing had happened to me. She just really wanted to die of embarrassment. We fell asleep that night and in the morning Ally got her things and left without saying much.
I tried calling her after school and she didn’t call back. I guessed that she was still upset. I look out the window and see her and Jason’s friend Will walking home together. I was glad to see she was alright but I was curious why she would be hanging around Jason’s friend Will. She called me back and we started to talk about Jason’s friend Will. She said that Will started to talk to her today at school and they really clicked. Will asked her to a party this weekend.
I was somewhat jealous because I wanted to go the party too. After hanging up Jason got home and I asked him about Will’s Party. He’s said “it’s not the kind of party I would take you too..” and I asked “why?” he said “it’s basement party”. I said “what?” and he explained “Guys take girls down the basement and when they turn on a black light. The girls give the guys blow jobs and they have sex.”
I was intrigued. I asked him “why would Will want to take Ally?” and he said “she’s not a virgin, so he’s got a better chance.” If your girl doesn’t have sex then you look lame. I told him I would do it if I could go. He smiled and said “I’m just warning you, that you don’t know what you’re in for…” I said “I can handle it..” then told me “You can could go as long as nobody knows your my step-sister”. I said “well not officially yet… Is it just people from Will and Ally’s school going?” he replied “I think so.” I thought perfect they wouldn’t know me anyway. I went back to my room and called Ally and told her that Jason said I could go the party. I didn’t tell her anything about the party but I knew she would be down for it.
Friday after school and Ally came over. I showered and got dressed. We were wearing matching tank tops and jeans. We anxiously awaited will to come pick us up. When Will pulled up Jason rode in the front seat and Ally and I sat in the back. I really didn’t know what to expect. Will had a few unopened bottles of liquor in the backseat of his truck. I felt nervous and hoped it would be fun.
When we go to the house; there were 6 other people there. The guys all seemed like they knew each other and the girls just stayed close to their guys. We all gathered in the living room and the one guy made us drinks as we walked up to the bar. We sat and drank for a few minutes looking around and listening to the music then the guy shouted over the music “ok, we’re all going downstairs to let the fun begin.”
Everyone walked down the stairs to the basement there were love seats and couches spread around the room and music playing down there. There were bottles of liquor being passed around and some were smoking joints. I knew I couldn’t back out now and just as we all walked down the stairs the door at the top of the stairs closed. I took a sip of my drink as Jason and I sat next to each other on one of the couches as Ally and Will sat across from us. We started talking to another couple named Nick and Britney that Jason knew. Jason introduced me just as ‘Katie’. The lights started to go out and a strobe light and black light came on. The guy announced “ok girls.. get into position.”
Jason spread his legs as got on my knees. I looked around and watched all the other girls get on their knees too. I undid his jeans and pulled them down along with his boxers. I stroked his erection and put it in my mouth. I wasn’t sure what to do so Jason guided my head up and down on it. A few minutes had passed and the guy announced “ok girls… it’s your turn.” Not knowing what to do I stopped as Jason stood me up and started to undress me. I watched as the other girls took off their clothes and when I was naked Jason had me lay on the couch. I looked over at Ally as Will was on top of her and they were kissing. Jason got on top of me and slid it inside me as we begin to kiss. He did me hard like he did Ally. It felt so good but it felt so intense with the loud music and black light. I couldn’t believe how my first real orgasm felt. It made me feel as if I didn’t want to stop it and then I felt as if I was floating. To my surprise Jason pulled out of me and got up as Will spread my legs and slid inside me. He held onto me really tight and thrust hard inside of me until he pulled out. The next guy was Nick, Jason’s friend he was not as rough as they were with me. He slid it in slowly and put his arm behind my head as he kissed my neck. It felt amazing and as I had another orgasm he pulled out. The party seemed kind of crazy because I could only hear moans over the music of the other girls. I felt drunk from the drink and I knew was naked on the couch. Jason came back over to me and was standing over me naked. He put my mouth over his erection and I started to give him and his friends blowjobs. I let them do whatever to me they wanted to me as I felt so out of it all I could do was lay there.
I must have fallen asleep because Jason woke me up a few hours later and helped me to get dressed. Ally was already dressed and standing over me asking me “are you alright?” I really had no idea where I was or what had happened since I fell asleep. Will took us home and Jason helped me into the house. Jason told my mom I was really tired and went to bed. He helped me into bed. I fell asleep and the next day I called Ally. She told me I was really drunk and gave all the guys blow jobs. I felt really slutty but I knew Jason took care of me last night.
Jason came in my room later and asked me “do you remember anything from last night?” I replied “I remember you carrying to my bed and putting me in it.” He smiled and I said “that was really sweet of you.” He sat outside by the pool and he asked if I was ok. He seemed really sincere about asking if I was ok. He told me it was a crazy night and he was happy that I was ok.
As our parents got married we continued having a ‘secret relationship’ and Jason sneaked in my room almost every night to have sex. I loved having a secret bf. My mom and step dad caught Jason coming out of my room. But they didn’t suspect anything. The week after my mom was picking up laundry in my bedroom and noticed Jason’s underwear on my floor. She began to see more signs that Jason and I were sleeping together. I was 15 and my mom and I were at the doctor’s office. My mom was in the exam room with me and she asked the doctor put me on birth control. I knew she knew I had been having sex. A few days later she came in my room and told me that it’s alright to have sex as long as I took the pill and the guy should use protection.
After I turned 16; my mom finally asked me about Jason and I sleeping together. I would bet she didn’t want me to hide it anymore. She would find my underwear and open condom wrappers in his room as well as his underwear in my room. She knew what was going on. She asked “Are you and Jason sleeping together?” I was really nervous and I knew I had to admit to it. “Yes” admitting to it. She looked at me and said “I don’t have a problem with it as long as you know what you’re doing” and I looked at her and replied “I lay there and let him do whatever he wants.”She looked at me and said “there is more to pleasuring a man than just laying there.” I replied “there is?” and she “well I had to teach your sister too so don’t feel ashamed.” She led me upstairs to her bedroom where Ron was laying in bed naked. He attempted to cover up by my mom said “I’m going to teach Katie a few things about pleasuring a man”. He sat there quietly as my mom led me over to him. She begin stroking him and then she started to suck him as I watched nervously. She caressed his balls as she sucked looking up at him. She said “now you try it” and so I got on the bed and began to suck him while I caressed his balls. She sat down in the chair next to the bed and watched Ron begin to lick me and pleasure me. She joined me on the bed licking and sucking my nipples as Ron thrust deep inside of me for the first time. He felt amazing to me. He did it slowly at first but he thrust harder as he felt me about to orgasm. I loved how he made me feel.
By the time I was 17, Jason had left for to the Marine Corps. I continued having occasional threesomes with my mom and Ron until I was 18. Ron bought me a new car for my 18th Birthday present which was also my high school graduation present. I left for college a few months later. When Jason graduated from boot camp we flew to South Carolina. We stayed in a hotel and Jason and Ron both had their way with me while my mom watched. Afterwards my mom had Jason while Ron and I played together. She enjoyed being with Jason because he was young and fit. He could last all night and loved thrusting hard. Ron loved my pussy and I did whatever he wanted.
When I started to date Justin (my present fiancé ) I was more sexually experienced and I took on the dominant role with him but he does make me into his submissive slut sometimes.
The Real Katie and Justin are at kinkybicouple.tumblr.com