My best friend growing up with Stephanie. She was the funniest and most crazy person I knew when I was in high school. She was into everything, sports, band, drama, and very popular. Even though I was in most of the same things she was….I wasn’t as popular. It didn’t hurt that she was one of the prettiest girls at school. She even was on the homecoming court. Stephanie was this vibrant 5’7″, 115lbs, with strawberry blonde hair, it was wavy and big, green eyes, a wonderful smile, she rarely wore any makeup and was naturally beautiful. She looked amazing in a pair of jeans and her small chest looked perfect on her lean athletic frame.
I, on the other hand, was average looking at best standing 5’11” 155lbs, in athletic shape, with white blode hair, blue eyes, and freckles. We had been friends since kindergarten and she was the first girl I ever kissed. Our parents were good friends so we did loads of things together. We even had sleep overs.
Stephanie and I were always playing sports together. She didn’t want to play softball and was pretty good at baseball. We played baseball in the summer, football in fall, basketball in the winter, and track in the spring. Of course when she got older she played on girls teams and I on the boys teams. We always went to dances together and has load of fun being goofy and messing around. She had a very quit wit and we could jaw it up over anything. Her friends were the popular girls and always questioned her why she hung out with me. We never publically told anyone we were dating. Stephanie got hit on by all the elite jocks in school but she always passed.
You are probably wondering why???
Well, Stephanie and I did have one secret. She was gay. She told me when she was sixteen one night when we were alone in the basement of her house. Stephanie was shaking nervously and she was very emotional. Even though we had messed around a little and made out, she had always known she was different. I guess people might of seen her more of a tomboy because she seemed to hang out with the guys playing sports and didn’t like dressing up. That was one of the things that made her a cool to me. I was honored that Stephanie had told me and swore to her never to tell anyone. She hugged me and we kissed as friends. The relief on her face from telling me was evident. I was happy she felt comfortable telling me.
Over the next years, we went to prom together and dances. Stephanie hated getting dressed up but put on a false front to appease everyone. So it came as a shock to everyone when I started dating a girl from out of town my senior year. Stephanie was happy for me but I could tell it also upset her. She had used me as a shield to not date any other guys from our high school. Once everyone found out, guys were hitting on her constantly. After turning away most of the popular single guys in school….rumors began to swirl. Stephanie was scared that if anyone in our small conservative town found out she was gay that she would be ostracized. So she asked me a huge favor.
Stephanie’s plan was that we go to this party at one of her friend’s house together and we make out. Even though I had only been seeing this girl Tara (who I met through working at a pizza place) a couple of weeks, I was unsure if I should do it. I told Stephanie my concern. She begged me to help her squash the rumors. I could never say no to her and agreed. I thought about telling Tiara but opted not to because I was afraid of what might happen.
That Friday night I drove to pick up Stephanie. She was dressed much more feminine than the usual jeans and a T-shirt. She wore a tight fitting red and white top, her flat toned stomach and belly button were showing and she wore a very tiny white skirt with heels. She even had on makeup. She looked like and 80’s pop star. Her hair was done up big and high too. She looked stunning. I made a scene when I saw her because she looked so nervous. Her parents were thrilled to see me pick up their daughter. They immediately asked me about Tara. Stephanie gave me a concerned look and I knew what to do. I told them it didn’t work out. Stephanie’s parents were so happy. They along with my parents had always dreamed of Stephanie and I dating. Which made it awkward for the both of us. After talking and giving each other weird looks, we got into my car. Stephanie took my hand in hers as she thanked me for doing this. I told her it was no problem because that was what friends did for each other. We went to the party and Stephanie made quite a scene entering with me. She looked so hot and all the guys couldn’t stop staring. We split up and the girls cornered Stephanie immediately asking why she was with me. Some of the guys told me how lucky I was and some thought I was seeing two girls. The word player got passed around often.
Stephanie and I got back together. We held hands as we walked out behind the house. We stepped away from the crowd. We had a good laugh at how people were talking about us. It got awkward when I looked at her in a lustful way and told her how great she looked. I don’t think she liked the way I was acting and I quickly covered my tracks when I told her I was just putting on an act …or was I??? Stephanie asked me when we should make out in front of people. Usually at these parties with all the beer around, people started getting wild after a few hours and even more crazy later on. I suggested we wait for more people to get drunk and maybe after one person got sick. There were always one or two people that would get totally plastered either getting sick or doing a crazy stunt. We opted to wait. Our hands got sweaty from holding onto each other as we walked back in. It didn’t take long for the party to get wild. People were fucking in the bedrooms and on the couches in the basements. We were hanging out in the living room when Stephanie moved onto my lap and whispered in my ear it was time. There was a small audience and we kissed softly. We pecked and moved my hands around her lower waist. We had both had a few drinks but Stephanie was a bit more inebreated and began to slid her tongue in. Her hands went to my face. The kissing was amazing and she was really going for it. I got into it too. Our hands started rubbing all over. I even slid a hand up her top. Her top flipped up over her small perky breasts. Stephanie didn’t stop me from feeling her up as kissed her neck. She whispered to me it felt so good. She looked at me with her green eyes encouraging me to keep going. Her hands reached down between us and she rubbed my crotch area. It didn’t take much to get me hard. We kept going at it. She sat up on me and acted like we were fucking. I sucked on her tits making her tiny nipples hard. Something electric was happening and the onlookers grew in number. I noticed and pulled Stephanie’s top back over her expose breasts. We stopped and composed ourselves. Stephanie hiked her skirt down over the pink thong she wore as she moved off of me. We got up and went to get some fresh air to cool off our raging hormones. We stepped outside. The air felt really nice. I stretched out my arms and smiles at Stephanie. She had her hands rubbing her arms to keep warm. She gave me a sheepish grin and asked me if they audience had bought it. I joked well if they didn’t, you sare fooled me. I laughed loudly but she gave me a simple, “Yeah.”
We went back in. Stephanie said she was cold and I pulled her into me. She clung her arms around me and put her face down into my chest. I rubbed her back. We just held each other in the kitchen for several minutes rocking back and forth. Stephanie looked up at me. Her green eyes sparkled and she whispered to me, “Can we leave?” I said of course and we left shortly after. The drive back to her house was unusually quiet. Normally we always had something to say but this time felt very different. I honestly was just trying to drive safely as not to get pulled over as Stephanie was struggling with something on her mind. We got to her house. Her parents had left the lights on for her. We sat there silently listening to the radio. When the song finished, I got out and walked around my car to open her door. I helped her out because of her tiny skirt. She gave me another hug. I kissed her on top of her strawberry blonde hair. She then looked up at me and asked if I wouldn’t mind staying for a while. It was after 1am but I was happy to hang out with Stephanie.
I turned off my car. Stephanie waited and she took my hand guiding me to her front door. We went inside, turned oft the exterior lights and headed downstairs. We usually hung in the basement. There was a large piece of carpet on the concrete floor with an old couch in front of a small TV. We always hung out there talking or watching something. Stephanie’s room was just off there. She had a shaggy rug on her floor, a twin sized bed, a dresser and a pipe hanging from the ceiling to hang her clothes. She had sports posters on the walls. Stephanie held onto my hand squeezing it. I squeezed her back in a playful way. She then took me into her bedroom. I had been in there before but like I said something felt different. Stephanie had me sit on her bed and she closed the door behind her. She then moved up onto me and I fell back on the bed. She leaned over me and we kissed. Again, it got heated fast. Our tongues mashing together inside each others mouth. My hands pulled her top up and her hands went down to unzip my pants. My mind was electrified!!! I didn’t stop to question what we were doing and went with it. Stephanie, on the other hand, as she was sucking on my ear making me feel weak whispered, “I want you to be my first. ” I knew exactly what she meant and I was thrilled!!
Clothes were removed and we were on the bed naked. Stephanie looked so good naked. We had seen each other naked before and even showered together once when we were younger. She had developed and had become more feminine shaped. We rubbed our firm bodies together and kissed. Our hands gently touching each other. I started moving down on her. I wasn’t experienced but had heard girls like it. I sucked on each of her firm hand sized breasts. I sucked on each of their tiny nipple making them very erect. I kiss her abdomen that was flat and hard from all the sports she played. I moved down below her belly button. Stephanie was moving slowly and moaning. She stopped me and asked if I really wanted to continue downward on her. I felt the heat radiating from her trimmed pussy and said yes. I then warned her, and she already knew, I didn’t really know what I was doing. Stephanie asked me to move off of her and I did so, thinking she had second thoughts. I respected her and moved off to the side. Stephanie put her hands down between her legs. She opened them up and pulled herself apart. There was just a lamp on that shown just enough light on her. What she showed me was incredibly fascinating. She pointed out where she wanted me to lick and touch her. The upper part of her was for my mouth and face, the lowered and darker was for fingering. She began to masturbate for me. I had never seen a girl masturbate and honestly didn’t know they liked to. As a guy, I had masturbated for Stephanie once she knew how explosive my blasts were but and I did masturbate often back then. I was even bold enough to tell her how I had thought of her. She knew how I felt about her but I never pressured to being more than a friend which she appreciated.
Watching Stephanie get off in front of me was awesome! She moved very slowly and sexy. Her whole body got into it and I inadvertently found myself touching my cock as I kissed her leg. She let me move in and she held herself open as I began to lick her where she pointed to. She told me I was doing good but needed to press my tongue in harder and move it around. I tried to do better but Stephanie was very particular. The good news was that I wasn’t deterred from getting better and kept trying. I moved her hands away and used one to rub just above her clit and the other I inserted a finger into her. She felt warm and wet. Her legs were spread open and she began to play with her tits. I really enjoyed watching her so much I had stopped doing oral. I was quickly reminded and went to work. Not having much experience. My tongue was getting a workout! I started making these low rumbling sounds and she loved it! I made louder rumbling sounds and the vibration seemed to excite Stephanie. Then I hit the jackpot! My knuckle had found this part of her pussy. It was hard and rubbing it in a firm circular manner really got her moaning. I continued to finger with licking and she became more sensual and erotic. Stephanie moaned my name and told me it felt so good. Begging me to keep going. She pinched and twisted her tiny nipples faster. The intensity in her bedroom grew until she let out thus much louder groan. Her whole body shook uncontrollably. I reached up groping her perky breasts as her hand gripped the side of the best hard. I licked her and expected for something to happen. What happened was her pussy got more suclant and moist. Stephanie’s whole body went from this intense fire to going very relaxed. I pushed up from between her legs. Her body broke into a sweat and she looked at me with her gorgeous green eyes. I joked if she wanted me to go again. She laughed and shook her head no. I was unsure when she paused before asking me…”You seriously would do that again?” I told her of course. My answer made her vulnerable and emotional in that moment. Her eyes watered and she told me, “I love you!” in a sweet honest tone. We had said it to each other and I naturally told Stephanie I loved her too. She asked me to come up on her and I did doing peck kissed up her warm wet body.
Stephanie and I kissed and was turned on by her willingness to taste her juices on my lips. We rolled over with her on top. She slid her body up and down on me. I recalled a certain conversation at how she thought oral sex on a guy was gross. I didn’t want to spoil the moment by thinking she had to do that. I was already hard and ready for the next step. She hovered over me holding my seven inch extra thick cock in her hand. She gently stroked me making me moan and looking down at it. I moved my hand up to he face and caressed it up to look at me. I told she didn’t have to do it. I was happy to satisfy her and how much she meant to me. Stephanie gave me one of her super sexy smiles and she hugged me. We kissed again and kept moving our bodies. Then the big moment came! Stephanie raised up over my cock that was in her hand. She lowered herself on me. My mushroom shaped tip entered her body for the first time. The sensation of being connected physically and our bodies becoming one was electrifying!!! My mind was going insane as it tried to record every thing I was feeling and seeing. My cock traveled deeper into Stephanie. She felt so amazing, it was warm and wet. She groaned crying out how big I felt. She began to sweat and exclaimed it much bigger than she had imagined. She winced as she went lower. Her pussy was so tight as it slid in and out of her. I played with her tits feeling her up as she moved very slowly up and down. Stephanie’s breathing was very heavy as she moved very very slowly down on me. She even swore under her breath that she might not be able to take much more. My whole body was alive!! The sensations burned into my brain. It felt so good I didn’t want it to end. In my overloaded senses, I couldn’t control myself and held her down on me. I held her narrow hips down as thrusted up into her. She yelped as I unleashed my seeds into her. My whole body jerked violently as I grunted every time another load passed out of me into her. Stephanie’s eyes got huge as she realized what had happened. In the intense moment neither of us could break away as just kept pumping into her more and more. When I had given her everything I had. She moved off of me and ran into the bathroom. I was now sweaty and a child came over me. I heard her pussy farts as she tried to empty herself. I moved under her bed sheets and waited.
Minutes went by until she flushed. My mind was playing games in my head how upset she might be at me. Instead she surprised me by slipping under the covers and hugged me. She put her face into my chest. I held onto her saying that I never wanted to let her go. I told her I loved her again and kissed the top of head. She looked up and we pecked sweetly. She told me she loved me so much and squeezed me hard. Her eyes were watery and I felt her tears on my flesh. I really was crazy about her and knew she struggled to understand the delima she had caused for the both of us. I knew I had to break up with Tara. I had been unfaithful to her and my loyalty was to Stephanie along with my heart. Even though I knew it probably wouldn’t work out for us.
We both were exhausted and sleep over took us. I woke up and the sunlight was poking through her window blinds. We hadn’t moved and were still naked when a gentle knock fell upon the door. It swung open as Stephanie was still asleep. Her mom saw me and her eyes got big. I have expected her to scream but instead she beamed a huge smile and mouthed the words ‘sorry’ closing the door. I always knew her parents liked me but didn’t realize how much in that moment. Stephanie stirred moments later. I kissed her head and she smiled with her eyes shut. She fell back sleep as I just looked at her sleep. I really didn’t want to let her go and she looked so happy. Stephanie woke up, she looked at me and we kissed after saying good morning. She told me she hadn’t slept that good in a while. She smiled and huddled against me. Her mom called down and said breakfast was ready. Stephanie called out loudly she’d be up in a minute. We got out of bed and I put on my clothes from the floor. Stephanie put on sweat pants and a T-shirt. I enjoyed knowing she wasn’t wearing any underwear. We kissed and hugged one more time as I slipped out the basement door. Stephanie smiled as she waved goodbye.
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