Justin

Hello, and welcome to my first story for Literotica. I plan to write stories based on my college experiences. But before I went to college, I lost my virginity to Justin. I welcome your ratings, comments, and suggestions. Please leave them here or send me a message. Thank you for reading, and I hope other stories can follow.

September 2023 Edit: Dear readers, Justin was the first story I wrote, and it contained typos and grammatical errors. This edit, with the help of kenjisato, corrects those errors. Other than that, I did not make any changes to the story.

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To know who I am today, I must go back to September 2012. That was when I went away to college. I had just turned eighteen the previous April, and this was my first time away from home. All week, I was trying to figure out what to take and what to leave behind. I ended up taking three suitcases full of clothes, one suitcase with all my shoes, and three boxes of stuff I could not part with.

I woke up early that day, knowing my life was about to change. I got out of bed, took off the t-shirt that I had slept in, and looked in my bedroom mirror. I saw someone who was scared but also very excited about a new adventure. In the mirror, the naked reflection was of a teenager who was five feet seven inches tall and 120 pounds, with long black hair and hazel eyes. I had European features that came from my Italian father and Portuguese mother. I took a closer look and saw my 32C chest. I placed my hands on my breasts and lightly stroked my swollen nipples. Turning around, I saw a medium-round butt that I was told was my best feature. I was lost in thought when I heard my mom yell, "Ashley, are you dressed yet? Breakfast is ready!"

I came down the stairs, and my dad was reading the morning paper. Yes, my dad was a Luddite. He was the only person in the neighborhood who still had a print subscription. My mom, as usual, was making sure the eggs were perfect and the toast did not burn. We were financially blessed, and my mom had been a stay-at-home mom since my older brother had been born.

Mom served breakfast at the kitchen table, and we sat eating quietly. I knew my mom and dad were remembering two years ago when they drove my older brother to college, and here they were, taking me. They were going to be empty nesters, and although my dad was ready to have his wife to himself, I'm sure my mom was going to have a hard time finding out what the next phase of her life was going to be. Breakfast was done, and while my mom cleaned up, my dad started packing the car. He looked at everything I was planning to take and said, "Good Lord, I hope all your things fit into our SUV."

I rolled my eyes and went back to my room for one last look.

Well, this is it. We got in the SUV, and as I was getting into the back seat, my dad took out a stack of Beatles CDs and picked up Sgt. Pepper. My mom closed her eyes, and I knew she would be asleep before we got on the freeway. I was accepted to a college that was a three-hour drive from our home, and I was glad I had this time to reflect. I closed my eyes and started thinking back on my life up to this point in time.

Both my parents were devout Catholics, so religion had always been part of my life. Although I had always gone to public schools, catechism and receiving the sacraments were mandatory. As I grew older, I started to question my religious teachings, and by the time I turned sixteen, I began to rebel and do things behind my parents' backs. Going out on dates was one of those things.

My Catholic guilt was still strong, so most dates ended with the boy being very frustrated and me having feelings I did not quite understand. By the time I turned eighteen in early April of my senior year, those feelings had become overwhelming. By then, I was having fantasies about what I would do once I turned eighteen. So, when my first real boyfriend, Justin, asked me to go to the senior prom, I gladly accepted, hoping that we would do more than just dance.

Justin and I started getting serious in the middle of our senior year of high school. He was six months older than me, and we had similar backgrounds. I'd known him since middle school and had always thought he was very cute. By his senior year, he was over six feet tall and had a very athletic body. He was the starting forward on our varsity basketball team. I knew he had previous girlfriends who were older than him, and early on, he told me one of them took his virginity right after he turned eighteen. The fact that he was more experienced than me made him even more attractive.

I love birthdays because my mom always makes them special. My eighteenth was no exception. Mom knew how much I liked Justin and said it was okay for me to go on a date with him for my birthday. It was the first time Justin and I went out with the full blessings of my parents.

Justin picked a very fancy Italian restaurant. It felt nice to get dressed up, so I wore a silk blouse and a short pleated skirt. The restaurant was perfect for the occasion. It had only ten tables, and the waiter spent time making sure our water glasses were filled. Justin told them ahead of time that it was my birthday, so the tiramisu birthday cake was complimentary, along with most of the staff singing Happy Birthday.

After our superb meal ended, instead of bringing me home and ending the date, Justin drove us to a quiet, secluded place to park. We started by just talking, but then he leaned in and gave me this wonderful kiss. At first, the kiss was soft, with our lips just touching. Our eyes were closed, and our hands were on each other's shoulders. Eventually, the kiss intensified as our lips parted and our tongues began probing. Making out in a car has always been awkward, but we didn't care. Justin broke the kiss and brought his lips to my neck. I leaned back, took hold of his head, and guided him back towards my mouth. Determined to go beyond just kissing, Justin moved his hand under my blouse and rubbed my tits over my bra. In the past, Justin would never get this far, but tonight I was feeling daring. I reached back and unclasped my bra, and Justin brought his hand under the bra. As we kissed, Justin caressed my breasts, and my nipples hardened by his touch. This was the farthest I had been with a boy, and those feelings of guilt started creeping in.

I suppressed those feelings and continued to kiss Justin while allowing him to touch my breasts in a way they had never been touched before. It felt so nice to be touched. I peeked at Justin's pants, and I saw that they were also turning him on. Eventually, his other hand started wandering down over my blouse and back up under my skirt and towards my panties. I knew what Justin wanted, but I also knew this was not how I wanted to lose my virginity. I took Justin's hand and pressed it against my vulva, and I began to rub Justin's cock over his slacks. He looked at me, not understanding, and I said, "I'm not ready for more than this."

He allowed me to stroke him over his pants as a way of accepting how the night would turn out. He was very hard, and I knew it would not take long for him to come. His breathing quickened as I rubbed harder. He closed his eyes and said, "Oh shit."

He came, and I could feel the wetness under my touch. When he took his hand away from my panties, I was also wet. We both sat quietly. We were at a new place in our relationship, and both of us knew it would not stop there.

Justin dropped me off at our front door and drove away. I was hoping I did not look too flustered as I walked into the house. My mom was watching Dancing with the Stars, and she barely looked up. I rushed upstairs to my room, knowing what I needed to do. I took off my blouse and skirt, unhooked my bra, and got on the bed. I wanted this to last, so I kept my panties on and let my mind wander.

I thought about how Justin touched my breasts and how good his kiss felt. Just thinking about this sent tingles down my spine. I took off my panties, and I massaged my vaginal opening. I slowly inserted my finger into my pussy. At this point, I was so wet that I easily moved my fingers in a circular motion. My other hand went to my breast, and I softly touched my nipple. I increased the speed and pressure, and that feeling of nirvana began to build. I brought my hand from my breast down to my clitoris. I began by stroking my clit through the hood. I formed a V with my fingers and slid up and down the sides of the shaft. With one hand on my clit and the other deep in my vagina, I began to breathe hard, and then this intense tingling pleasure started in my clitoris. Immediately, it spread (somehow slowly and all at once) through my whole body, down to my toes and my fingertips. I brought my hand to cover my mouth, and I let out a muffled cry.

I woke up the following morning, knowing that senior prom was only three weeks away. However, those three weeks had just crawled by. I tried to concentrate on my classes, but all I could think about was how Justin and I could be together once prom ended. With the help of my closest girlfriend, I convinced my parents that I would be staying with her the night of prom.

The morning of the senior prom had finally arrived. I spent most of the day in anticipation. By late afternoon, it was time to get ready. I wanted to take a long shower so I could take care of something I had wanted to do for a long time. I wanted to be completely shaved for Justin. After I finished shaving in the shower, I applied moisturizer all over my skin and paid special attention to my bare pussy.

My dress for the evening was laid out on my bed. It was a light-blue, floor-length pleated gown. Opening my dresser's bottom drawer, I pulled out a Victoria's Secret floral lace thong panty and a smooth strapless bra. I took careful care to make sure my makeup was just right. Then I got dressed, and I was ready to face my parents. My dad did a double take as I walked down the stairs. It was a good thing he had no idea what I was wearing underneath my dress. In the end, it was the look on my mother's face that said it all. She looked at her daughter and knew whatever influence she had on me was a thing of the past.

Justin arranged for a limo for us and four friends to take us to a local restaurant and then to the prom. The limo pulled up, and Justin came to the door wearing a Calvin Klein tuxedo that he had rented. Of course, Mom and Dad embarrassed me by taking lots of pictures while Justin pinned the corsage on me and walked me to the limo.

The restaurant and most of that evening are fuzzy memories. I remember slow dancing with Justin to Kelly Clarkson's A Moment Like This. We started by dancing close together, but by the middle of the song, we were holding each other tightly, to the point that we were grinding on each other. Justin's hands traveled down my back, and he pressed me tight against him. I could feel him grow, and by the end of the song, he had a full erection. and my thong panties were soaked. After the song was over, we somehow made it back to our table and waited until it was time to leave the prom.

The limo once again arrived to take us home. Since my parents thought I was spending the night with one of my best friends, when the limo got to Justin's house, we both got out. He lived in a very fancy neighborhood where most homes had a pool. I had met Justin's parents before, and I knew they never stayed up late. Justin and I very quietly went through a side gate into the backyard. By the pool, there was a changing room just large enough to hold a couch.

Once inside, Justin took off his jacket, and we both kicked off our shoes. We sat on the couch and made small talk. But soon, both of us were lost in deep thoughts that were too raw to be said out loud. Suddenly, Justin leaned over and kissed me. As we kissed, Justin's hands started fumbling with the dress, but I was too impatient to wait for him to figure it out. I stood up from the couch and looked at Justin. I was nervous but determined. Standing before him, I slowly slipped out of my dress and tossed it on the couch next to where Justin was sitting. There I was, standing wearing a strapless bra and a thong that barely covered my pussy. I reached around my back, unclasped my bra, and tossed it next to my dress. Justin was paralyzed from just looking at me. First, his eyes met mine, and then they traveled to my breasts and down past my thong, down my legs, and finally to the toenails I had painted that night.

I returned to the couch, kneeling on Justin's lap with my legs on either side. I leaned into him, and we kissed again. While we kissed, he used his hands to tease up one nipple before moving on to the other. Then he broke away from my lips, bent down to my breasts, and took my breast into his mouth. With his tongue, he flicked the nipple, making it even harder. I brought one hand over his head and arched my head back, enjoying the pleasure of his touch. I moved my other hand from behind his back to the top of his thigh and slid it up until I felt the hard shape of his rigid cock under his pants. Continuing the movement, I surrounded the shape of the shaft with my fingers, watching it grow thicker and longer.

Justin moaned into my breast, indicating the powerful rush of pleasure I had unleashed with that single stroke. His hands moved away from my breasts, down my stomach, and over my thong, stroking me gently. Then it was my turn to moan.

I knew we were at a point of no return. For a long time, I had waited for this moment, but I still felt uncertain. The one thing that I was certain about was that Justin needed a condom. I looked into his eyes and said, "You brought condoms, right?"

He looked back, eyes wide, and said, "In the jacket pocket."

He reached over for his coat and took it out.

With that out of the way, I slid off his lap and started unbuckling his belt. I guess it was his turn to be impatient because he got up, took off his shirt and socks, and dropped his pants. He just had on his boxer shorts that were tented, and I had only my thong. We looked at each other, and I said, "At the same time, okay?"

He slipped off his boxers, and I tossed my thong. We were both naked together for the first time.

Justin just stared at my pussy. Maybe he was surprised to find me lacking pubic hair. Or maybe he was fascinated with the smooth flesh of the mound. It did not take him long to recover because soon he was gliding his hand several times across my bare pussy before rolling his finger up to my clit and massaging it gently. All I could do was stand there with my eyes closed, breathing in and out.

I opened my eyes and stared at Justin's erection. Maybe doing that wasn't such a good idea because, as I got my first clear look at his length and width, I momentarily panicked. Rubbing it under his pants was one thing. Seeing it for the first time was altogether different. Surely, it wasn't meant to be this big. Surely, it was too long and too thick to fit inside me. Justin must have noticed because he smiled at me and said, "I'll go slowly, I promise."

Justin took my hand and led me back to the couch, so I was lying on my back, staring up at him. He opened the condom package and slipped it on his hard cock. That task completed, Justin got on top of me and kissed back up my stomach, across each breast, and settled down again by holding me in a passionate embrace and penetrating my mouth deeply with his tongue as his fingers started rubbing my pussy. He moved his hands over my vulva, testing my readiness for him. He didn't have to worry. The nervousness and uncertainty gave way to this tingling feeling between my legs. I was more than ready for Justin to enter.

He moved my hips forward so his cock was directly over my pussy. He lowered himself just enough so that he was located firmly at my opening but still not inside. He looked into my eyes and said, "Is this okay?"

All I could do was nod. Then he brought a little weight down on me, penetrating my pussy lips and sliding into me. I felt some initial resistance and pain. Yes, I was lubricated enough. Yes, I was aroused. But my body was taking some time to adjust. Justin, sensing that, took it easy. He slid up and down, going a little deeper, until the resistance and pain returned. Then he slowed down. He continued doing this, each time letting my body become more accepting of this new and unfamiliar sensation.

Despite feeling a little discomfort, I enjoyed his hard cock between my legs. A wonderful feeling began deep inside and spread all over my body. It turned into a pulsing sensation that came from the thrusts of his hard erection. I was so close to coming, but then I heard Justin cry, "Oh, Ashley, Oh God, Ashley!"

I felt his climax, spraying his seed into his condom. His body involuntarily drove into me, suddenly penetrating me deeper than ever before. That penetration caused my juices to flow, and I felt pleasure rippling through me. To Justin's credit, he did not pull out. He continued to move at a faster pace. He kept watching my face, knowing I was near. Justin reached down with his fingers and played with my clit. At the same time, he pumped up and down. Although he was not as hard, he still felt amazing inside me. That was when it happened. I let out a loud moan, and the strongest and most beautiful orgasm I had ever experienced overtook me.

Justin then stopped, and we held each other tightly as our breathing slowed down. As we both started to relax, he slipped out of my pussy, and he lay next to me on the couch. Holding each other, we both fell into a deep, deep sleep.

I didn't know how much time had passed, but I heard, "Ashley, Ashley, wake up."

I opened my eyes, completely disoriented. I looked up and saw my mom. She was staring at me. I panicked, forgetting where I was. But then I heard Magical Mystery Tour on the CD player and remembered I was in the back seat of my parent's car, going off to college. I looked at my mom and asked, "Are we there yet?"