My first witten story of this kind. I had been a part of this site reading stories for years and now I finally have one of own to add. I would like to make this into a series but with my busy days, I won't promise anything. Constructive reviews would be appreciated. Hope you enjoy
I was never a popular guy. I left my old school with not many friends and started at a new one that was a quarter of the size as the last. It was a bit strange to go to such a smaller school, but it didn’t matter much to me at the time. I just wanted to get it over with. I was always a bit of a loner and shy as hell, so I was closed off quite a bit from everyone. There was one girl who was quite persistent in changing that. Jessica became friends with me fast for reasons unknown. Maybe it was a because I was the new guy, but she was different from anyone else I knew. She had a group of friends which she brought me into, but I never really seemed to fit in. Jessica wouldn’t give up though. She insisted that I come out with her friends bowling or going to see a movie. I always stuck close to her because she was the only one I felt comfortable with. We had great times and we would often talk on the phone.
Before I go on, I guess I should describe her a little bit. She had beautiful light blonde hair that went just passed her shoulders. She stood a little higher than five feet and had a small frame. I always thought she had a “cute” complex to her, but she was always very pretty in my mind. Maybe I was just biased because she was my friend. Her breasts were a good handful, I think about a B cup, but I could never tell exactly from looking. She had a great ass as well. I especially loved it when she would wear tight fitting jeans. She never acted slutty, but she had a confidence to her. She wasn’t one of those that would give it up to anyone. I had always wanted her, but felt I would never amount to anything worthy. I was content to stay her friend if that is what she wanted.
As for me, my name is Simon. I guess I was considered an “average Joe.” I stood just short of six feet with shaggy brown hair. I grew my mustache and beard out just a little bit that made me look attractive, though I had no idea why when I wasn’t trying to be appealing to the opposite sex. I wasn’t very muscular, but I was fairly skinny for my height. I always prided myself on my wit, being able to out think most people. I tended to be an analyzer, always looking at things before I went through with them to make sure I wouldn’t get screwed. My best feature, however, were my eyes. I had gotten quite a few compliments about them from girls then. I always took it as a kindness aspect. They were a shade of green, about the color of grass as its full potential. Even though I really never noticed it, a few girls would look just a little longer than normal at them. Unfortunately to them, I suffered from light sensitivity from my astigmatism, forcing me to wear sunglasses almost all the time while outside. Even some brightly lit rooms required me to wear them. I’m glad I didn’t have the problem at school though.
Anyway, this particular time came around late in the school year. Prom was coming up and I didn’t even bother to consider going. I couldn’t dance, so there was no point in making a fool of myself in front of people. No one else shared my idea of it though. All of the students were busy making preparations for the dance. It was two weeks to go and it seemed like most everyone had their dates for it. Jessica refused to tell me who she was going to go with, so I didn’t bother asking her anymore about it. Despite the fact that she was a grade below me, I had to share some classes with that grade because of transferring from another school. Jessica happened to be in one of those classes which happened to be Biology. Due to our assigned seats by last name, I was sat away from her. I usually watched her since she sat in front of me to my left. Today I could tell something was wrong with her, like she was nervous about something. I made a mental point to ask after class what was wrong
“Simon!” the teacher spoke from the front of the class.
“Yes ma’am,” I said quickly after snapping my attention to the teacher.
“Tell us what carbon dating is”
Quickly racking my brain from taking Biology the previous year at my old school, I answered, “It is when scientists determine the estimated length of time that a subject has been around on this planet by studying the decay rate of carbon inside. It’s typically used to date back about 60,000 years.” The teacher, obviously thinking that I wasn’t paying attention, raised her eyebrow in astonishment.
“Anything else you’d like to know about it?” I asked. This received a chuckle from some of the classmates.
“No, that will be all. Thank you,” she continued teaching the class. I noticed Jessica looking at me with a smile on her face. I gave a small smile and nodded my head in her direction and turned to the textbook following the lesson. Fifteen minutes later without any more incidents and the teacher assigning homework, the class ended. I gathered my things and walked to Jessica’s desk to walk with her to the locker before next class. Leaving the classroom, I could tell by her walking that she was nervous again.
“Jessica, what’s wrong?” I asked.
“Nothing Simon, I’m alright,” she replied.
“You’re a horrible liar, you know,” my traditional reply for when I knew she was lying.
“I’ve just got a lot of things on my mind with Prom and end of year exams coming up,“
“It’ll be alright. We’ve got another month and a half before exams and I am sure you’ll have fun with your date at Prom,” I replied back to her as we reached her locker. She got a little more nervous with the mention of Prom and I knew she wouldn’t tell me.
“We’ll see,” she said back to quietly.
“Alright, I gotta run to class. See ya after school.” I said as I left. I made it to my last class, Writing, just before the bell went off. Since I was a loner, I tend to have a lot of free time and I build alternate realities as a result of it. Writing class was a blessing for me in helping me put my ideas to paper and letting them grow. It was easier to keep track of them when you could actually look at the story.
Anyway, after a writing session and homework given for the weekend, class ended as well as the school day. Making it to my locker and dropping my books off that I didn’t need, I went to Jessica’s locker and found her there waiting on me. He walked together to the bus drop, where we would wait for her bus. I lived too far away for the bus and had to be picked up by my parents. She was nervous again as we sat down waiting.
“Jessica, are you going to tell me what is really wrong or do I have to annoy you until you break?” She looked down for a moment before looking into my eyes.
“Simon, will you go to Prom with me?” Now for the first time in a long time, I was shocked. I truly did not see this one coming.
“I thought you had a date,” I replied more in a question than a statement. She shook her head.
“No, I thought that you would ask me and so I kept myself open for you. I figure now is the last chance to get a date before it is too late.”
“But why me?”
“There isn’t anyone else I want to go with,” Still in shock, I looked away. Never before had I been so blindsided as I had now.
“Yes Jessica, I’d love to take you to Prom,” She smiled and hugged my chest tight.
“Thank you, Simon.” Her bus arrived and she gave me a kiss on the cheek before she grabbed her things and headed for the bus. Rubbing my cheek where I had just gotten my first kiss at, I walked slowly to where my parents would pick me up. I was terrified…I had no idea how to dance.
Those two weeks went by quickly as I dreaded the arrival of Prom. I managed to get a last order for a tux rental for the dance and Jessica had already gotten her dress. Prom was tonight. As I was putting on my tux, I couldn’t but be nervous about tonight. I had told Jessica she would have a great time with her date at Prom, but that was before I learned that I was her date. I thought that I was going to fail to live up to that expectation. My parents were going out of town for their anniversary and let me borrow the car for Prom. I live about thirty minutes away from Jessica and the town is in the middle between us. Pulling in her driveway, I nervously walked up the steps to her home. After knocking on the door, her father answered it. Now I had met her dad plenty of times, but this was the first time as his daughters date. We shook hands and announced to Jessica that I was here. A moment later, she emerged from downstairs where her bedroom was.
She was gorgeous. She had a knee length black strapless dress that sung tightly to her body. Her hair had been done with curls in it, making it appear much shorter than what it really was. Her makeup was done perfectly across her face. I have never been one who really liked make up on a girl, but she pulled hers off beautifully.
“You look absolutely beautiful Jessica,” My eyes were riveted to her as she blushed profusely. I pulled out a corsage and held my hand out for her wrist. She offered it to me as I slipped the corsage onto her. She smiled as I looked up at her.
“Have her home by midnight, Simon,” her father said to me.
“Yes sir,” I said. I was astonished that he let me have such a late curfew. I escorted Jessica to the car and opened the door for her, closing it behind her before walking to my side. I got in and drove to the school, making a little small talk and me commenting again on how beautiful she looked. We made it to the dance without a problem and went inside. The planning committee had gone all out with the decorations and the place looked nice. Music was already playing and several couples were dancing on the dance floor. We found a table to sit at and Jessica walked off to converse with some friends she had seen walking in. I sat nervously at the table alone. I was completely out of my comfort zone by being here. I stood up and walked over to a window to look out at the night.
“What am I doing here…” I said to myself quietly. Not paying attention to my surroundings like I usually do, I felt a tug on my arm. I turned my head to find Jessica pulling me to the dance floor. Stiff legged, I reluctantly followed as a slow paced song started playing. Unsure of what to do, all I could do was stand there. Jessica took my arms and put them into the proper place and begin to gently sway back and forth to the music. I smiled slightly at her as she looked at me.
“You are very beautiful, Jessica.” I said with a little bit of confidence.
“Thank you Simon, I wanted to look really nice for you.”
“I don’t mean just right now,” I replied to her, “you are beautiful all the time. I’ve just never had the courage to say it out loud.” Jessica snuggled into me after hearing the compliment. I held her close as we continued to sway to the song. The song ended soon after and I claimed I needed to use the restroom and would return. Making my way there through the number of people, I stood in front of the sink filling my hands with water. I splashed it on my face then looked at my hands. They were shaking hard because I was so nervous. I cleaned the water off my face and took a couple deep breaths. Feeling better about myself, I exited and found Jessica sitting at the table. I pulled a chair next to hers and sat down.
“I’m sorry I am bad about this sort of thing,” I said to her.
“I know,” she said quietly. I took her hand and held it. She smiled at me as a another slow song came on. This time, I led her to the dance floor. Feeling a little confident about what I learned earlier, I took the lead while holding her close. I could smell the scent of her perfume as she rested her head on my shoulder. I ran my hand up her back, massaging it lightly as we danced.
“I’m glad you asked me to come to the dance with you,” I whispered in her ear. She snuggled closer into me and gave a content sigh. The song ended and I asked her to dance with some of her friends for the faster paced songs while I made a call to my mother to check in. Stepping outside and pulling out my cell, I dialed my mothers cell number.
“Hey Simon. Are you having a good time?” she asks as she picks up.
“Hey Mom. I am. How’s the anniversary?”
“It’s going good so far. How’s your dance?”
“It’s getting better.”
“Good, glad to hear. I have to go. Have fun. Love you.”
“Love you too Mom.” I clicked off the phone and put it in my pocket. So much for getting a distraction from the fast dances. I went back inside and stood against the wall watching Jessica dance with her friends. The way they danced was provocative and caused quite a result inside my pants. Embarrassed, I told myself that this was not the time or place for that. Still, I couldn’t help but watch. It was hard to not watch with a date that beautiful. I thoughts started to drift again as the girl began grinding against each other and I mentally slapped myself for the thoughts and forced myself to walk away. I sat down at our table and focused to try and get rid of my erection. It was only seconds later that I felt someone take my arm and dreaded hearing that the fast music was still on. Jessica pulled me back out to the dance floor and I froze as she turned around and started to rub up against me. This definitely didn’t help my erection and I knew Jessica could feel it. The moment she felt it, she looked back at me for a moment and I could tell she had a different look to her, especially her eyes before turning her head back. I was really embarrassed at that point and apologized as I started to walk away. Before I could take more than two steps, Jessica grabbed my arm and pulled me back towards her. She put her hand behind my head and pulled down as she leaned in and kissed me full on the mouth. To say I was shocked was an understatement. The kiss lasted several seconds before she pulled away. I blinked a couple times to make sure that that had just happened. The look on her face after I did nothing was disappointment and she turned to walk away. This time I grabbed her, spun her around, and kissed her. I put my arms around her and pulled her tight to me. I didn’t care that I had an erection pressing against her anymore. I was enjoying the kiss that I wanted for a long time. I broke the kiss and looked into her eyes. I could she that she was feeling lust at that point. I smiled at her before briefly kissing her again.
“It took you long enough, Simon,” she said.
“I am a slow learner. Was it good?” I asked. She pulled me towards her and kissed me passionately. “Does that answer your question?”
“It certainly does.” I looked around at the other couples. They were completely oblivious to us under the low light and loud music. Feeling a little bit bold, I pulled her head close and whispered in her ear, “How would you like to get out of here?”
“I thought you’d never ask,” she replied as she started to guide me off the dance floor. We collected our things off the table and she told her friends she was leaving for the night. I waited by the door and escorted her to the car. Starting it up, I noted that the time read 9:45. I asked where she wanted to go and she said my place since she knew my parents were out of town. The fifteen minute drive was short lived as I thought about what could happen. As I pulled into my driveway, my nervousness had returned as I got out of my side and walked over to open her door. Jessica stepped out and immediately kissed me, not helping my nervousness at all. I pulled away and escorted her to my door and unlocked it. I let her in first before I followed and closed the door. For this being the first time at my house she looks around at the items sitting on shelves that my family has collected for years.
“This is a very nice house, Simon. I like it. What does your room look like?” I was near frozen stiff when she said that. I hadn’t even contemplated that scenario. Still, trying to be brave, I motioned down the hall to my room. As I was opening the door, I was very glad that I had the foresight to have straighten my room the day prior.
My room was very bland to say the least. My wall were wooden slats with two windows. In the far corner was my bed facing my closet in the adjacent wall. To the left corner sat a corner table with shelves. They were covered in Lego designs that I built from imagination. Other than carpet, a long bench sat at the foot of my bed and a dresser stood in front of the window between my bed and table.
“Nice room,” she commented as she glanced around. I could tell by her stance she was just waiting for me. I knew that girls didn’t really like shy guys and I knew I would blow this if I act as such.
Stepping towards her, I embrace and kiss her passionately. She wraps her arms around me as she reciprocates the kiss, pouring her feelings into it. My hands travel slowly up her back, lightly massaging her spine. Her hands find the buttons of my shirt and slowly begins to undo them. She pushes my jacket and shirt off as I run my hands against her dress and up her back. Her hands move lightly up my chest and she begins kissing me more passionately as she runs her hands through my hair. My fingers travel down her upper back and I grab a hold of her zipper. I unzip her dress and let it fall effortlessly to the floor as I resume kissing her. I wrap my arms around her and lean into her, causing her to step back against the wall. I easily unclasp her bra and watch it fall to the floor to join the dress. I step back for a moment to admire the sight before me. She blushes and tries to cover herself, but the blush is hardly seen in the darkness of the room. I move back in and start kissing her more passionately this time. She becomes more confident with herself and lowers her arms and wraps them around me. With her pressed against the wall, she grasps my head and kisses me more fiercely. I reach up with my hand and begin massaging her breast. Our breathing get heavier as we get even more turned on. She leans forward and pulls me towards the bed while still kissing me. She pushes me on the bed and then straddles me.
“ I have waited a long time for this,” she says to me. She brings her head down and slides her tongue inside my mouth. I follow suit and slip my tongue into her mouth begin wrestling with tongue as my hand slides up her side. I cup one of her breasts and massage harder than before. She moans lightly as she feels the pleasure building inside her and begins to grind herself against my crotch in an attempt to have an orgasm. I bring my other hand to her ass and begin squeezing it every time she moves forward. I lower my head to her breast and lightly flick my tongue across her nipple. She moans louder and clutches my head with her hand against her breast. I eagerly suck her nipple and swirl my tongue around it as my other hand squeezes her ass harder.. Her breathing becomes heavier and she grinds against my crotch harder as she gets more turned on. My cock is so hard from seeing her turned on. I can feel her rubbing her pussy against me through my pants. She moves her hand down to my pants and begins to unbutton them. Feeling this, I move my hand from her ass to her front. I slip my hand inside her panties and feel the smooth saved area above her pussy. She looks at me with such lust in her eyes as she reaches inside my boxers and grabs my cock. She squeezes lightly and rubs up and down slowly. I find her clit with my thumb and run it over with the slightest touch. I feel her hand on my cock squeeze hard as she feels the pleasurable feeling. I roll over with her so that she is now on the bottom. I pull my hand out and admire for a moment how sexy she looks before I move my head down and begin kissing the inside of her thighs.
“Oh Simon, that feels so nice,” she says between deep breaths. She stops me for a second as she pulls off her panties, then lays back to let me continue. I make my way slowly toward her pussy, dropping a kiss every couple centimeters. I feel her squirm as I get closer to her pussy, wanting me there so bad. As I reach it, I pass over it to her other thigh, but not before I give a very small lick to her clit. She spasms so hard from the unexpected move and moans loudly. I kiss up to her mid thigh before I reverse direction back to her pussy. As I get there, I kiss around her pussy, constantly teasing it. As I get to the top, I lick her clit again. She breathes sharply before grabbing my head and holding it in place. I flick my tongue across her clit to hear her moan again. I start to do short light licks on her clit as I move my hands up to her breasts. She rakes her fingers through my hair as she feels her orgasm building. I tweak her nipple with my fingers as I lick her clit harder. Her body begins to shudder and I can tell that she is going to cum hard, very soon.
“Oh God. Don’t stop Simon. I’m going to cum. Ah god, I’m almost there. Ahhhhhhh.” I tweak her nipples a little harder while simultaneously giving her a long hard lick. She lets out a loud moan and her whole body spasms as she has her first orgasm. She breathes heavily as she comes down from her high. I crawl up to her face and begin kissing her, letting her taste herself. She sticks her tongue inside my mouth, showing me that she is still extremely horny. After a moment, she grabs my head and rolls us over, placing her on top. She leans up and grabs my cock. After stroking it a couple times, she lines it up with her pussy.
“This is going to feel so good. Are you ready to fuck me Simon?” Jessica says to me. I can only nod as she begins to lower herself down. My cock slides nicely inside her until she has all six inches of me. She gasps as she feels filled. She looks me in the eye and smiles. Slowly, she begins to rock back and forth, feeling my cock at different angles. My breathing gets heavier as she moves faster. After a minute of rocking, she begins to pick herself up just enough to leave the head inside before slamming down again. Her pace quickens and her moans only get louder, turning me on even more. I have always enjoyed hearing a woman moan, especially if I am the one pleasing her. I start to thrust into her and she slides down my cock, pleasuring both of us even more. She has her back arched and has her breasts pushed out in front. I reach up and begin lightly squeeze them as she continues to ride me. Her moans are loud now as she picks herself almost all the way off me before slamming back down. I continue to thrust into her as she comes down, making her squeeze my cock with her muscles. It feels so good and I can feel myself getting close. To make it last a little longer, I roll us over and put her below me. I then begin to fuck her hard as she wraps her legs around me, trying to pull me deeper inside her. I leaned my head down and moaned into her mouth as I kissed her passionately. She responded by wrapping her arms tightly around me, pulling my chest closer to hers as I continued sliding into her. She broke the kiss and looked me in the eyes with such lust that I almost wanted to orgasm right then.
“I have waited so long to do this Simon. God I can’t believe I’ve waited this long,” Jessica says to me through heavy breathing. I can feel her pussy squeezing me tighter as she gets close to her orgasm. I adjust slightly so that my cock rubs against her g-spot. Almost as soon as I do, she moans loudly and her pussy clamps down on me as she has a powerful orgasm. The feeling is almost too much for me and I pull out just in time to shoot off my first spurt of cum onto the top of her pubic mound. Despite still riding her high, Jessica grasps my cock and begins pumping on it to make my orgasm as hard as it can. I kiss her hard as four more heavy shots of cum land on her stomach. I lower myself easily onto her, careful to make sure that any post ejaculate doesn’t get inside her, and give her light kisses across her mouth. She smiles at me as she finally comes down from her orgasm. I roll over and lay next to her as I put my arms around her. Jessica snuggles her head against my shoulder and closes her eyes as she holds me tightly. I was enjoying the moment when my watch beeped off signaling that it was eleven o’clock. As much as I wanted to stay here as enjoy the feel of her body against me, I told her we needed to get going soon.
“Not yet,” she replied, “I don’t want to get up yet,” she said tiredly just before she kissed me. It was hard to say no to her.
“Alright, five more minutes. Then I have to get you home or your dad will have my head.” I said as I kissed her forehead. We laid there for a few more minutes before I insisted that had to get up. Jessica reluctantly listened and got up. Putting our clothes on took longer than expected since we couldn’t stopping kissing each other. Finally dressed, we made it out to my car with forty minutes left until midnight. Taking towards her house, we held hands in silence for the duration of the trip. As I put the car into park in her driveway thirty minutes later, I again walked around and opened her door. I walked her up the steps to her house before giving her a goodnight kiss. As she opened the door, I had to get this question off my chest. Wording it carefully in my head for fear that her father was in the living room waiting, I started.
“Jessica, I’d like to make this more than just a date to Prom. Will you go out with me again soon and be my girlfriend?” I waited for a moment while she looked inside before she turned back to me with a smile on her face.
“I’d love to be your girlfriend, Simon. I’ll see you tomorrow in school. Goodnight.” she said as she stepped inside. Happy with my answer, I walked to my car, ready to back home and anticipate my next date with Jessica.