My name is Jane and this is a story about a period of my college life that I have fond memories of and deep regrets. We all do things when we are young that serve as lessons for later on in life. Some people refer to them as mistakes, but I prefer to call them experiences.
I was never the prettiest girl in school. I was average in every way. I came from a family that struggled financially so I never had the most fashionable clothing. I wasn't part of the popular crowd and didn't fit in with the nerds. I kind of drifted through the hallways mostly unnoticed. I had a few friends that I hung out with but not many.
I have decent-sized C-cup breasts and my butt is bigger than I like. I have long brown hair and brown eyes but don't have physical features that would make me stand out in a crowd. My clothing consists mostly of jeans and sweatshirts.
I had a few dates while in high school but nothing special. I was so socially awkward that I hardly ever got invited to parties and if I did, I would most likely be standing in a corner of the room with a couple of other awkward people watching others having fun.
I lost my virginity a couple of months after I turned eighteen on the night of my senior prom to a guy I barely liked but he was the only one to ask me out. The only reason I fucked him was because I didn't want to go to college as a virgin. Besides, I heard all the girls talking about having sex and I was curious to find out for myself what it was like.
For some reason, I didn't want my date to think it was my first time so I studied up on how to give a blow job and what to do the first time having sex by reading stories and watching videos on the Internet. I practiced sucking a dick with a banana and found I was able to get a good amount of it into my mouth.
Danny was my date who was on the heavy side with glasses and one of the awkward kids like me. I think he was surprised when I agreed to go to the prom with him. One of the reasons I said yes to him was because no one else asked me to be their date. I could be wrong, but it may have been his first date ever.
My mom helped me pick out a dress at a second-hand store. It was the first time I had a fancy dress. It was a tight blue, low-cut above the knee-length dress. I had never shown that much cleavage before. It was backless so I couldn't wear a bra either. To say I wasn't comfortable wearing something like that is an understatement but my mom was so excited and she told me how pretty I looked, so we bought it.
A friend of my mom's who worked in a beauty salon helped me with my hair and makeup on the day of the prom. My mom was in tears when she saw me all dressed up. My dad looked anxious probably because I was showing too much skin. I have to admit that I felt prettier than I ever had.
When Danny saw me, he got the biggest grin on his face and looked like he was about to drool. His hands were shaking when he pinned my corsage onto my dress. I'm sure he was afraid he might accidentally touch my breast in front of my parents.
After the mandatory pictures, Danny held the door of his father's car open for me like a true gentleman. I didn't realize that my dress would ride up my legs when I sat down because my dress was so tight. I think I accidentally flashed my light blue bikini panties and frilly garter for Dan as I was getting in the car. I saw his eyes widen and felt a cool breeze up my dress. I had to hide the fact that I was so embarrassed. I tried my best not to flash him again when he held the door as I got out of the car but I don't think I was successful.
When we got to the prom, I think people were surprised at how I looked all dressed up. People kept telling me how pretty I looked which made me feel better about myself. Danny and I had a great time with our friends. While we were slow dancing, I could feel his hard dick pressing against my thigh. I have to admit that being all dressed up, feeling pretty, and then feeling Danny's erection pressing against me made my pussy wet.
When Danny asked if I wanted to go up to the lake before heading to an after-prom party, I readily agreed. The lake was a known lover's lane and we both knew what he was really asking me and what I had agreed to do with him.
After he parked the car, we began to make out. Danny didn't waste any time fondling my breasts and pulling down the top of my dress to expose them. His eyes lit up at the sight of my breasts and he immediately began to fondle and suck on them. Having my breasts sucked was extremely pleasurable, more than I ever thought possible. I was also stroking his dick through his pants. He was shocked when I unbuckled and unzipped his pants to expose his hard cock. It was scary looking down at the first cock I had ever held or seen.
My first thought was, "This is why you've been practicing so go for it."
I didn't want to overthink what was about to happen, so I just lowered my head and began to blow Danny. His dick felt funny in my mouth at first but after a few bobs of my head and swirls of my tongue, I decided I liked sucking his dick. I especially liked it when he began to moan because I knew he was enjoying it. Danny's dick wasn't that big so I was able to get the entire length into my mouth. What I didn't plan for was for him to cum so soon and what I would do when he did. My plan was to have sex with him when he came.
Danny began to breathe faster and I realized he was about to cum. A moment of fear flashed through me and my instinct was to lift my head. However, Danny put both hands on my head and began to thrust his hips upward, making it impossible for me to take my mouth off his dick.
The only thing I could do was to keep sucking. I felt his dick pulsate in my mouth before the first wad of cum shot out of his dick followed quickly by two more. I wasn't sure if I liked the taste or not but by the time he shot the fourth wad into my mouth, I decided it wasn't too bad and kept swallowing. I was surprised by the amount of cum he had stored up in his balls; it seemed like he would never stop filling my mouth with his seed. Eventually, Danny's balls were temporarily drained and he released his grip on my head.
When I lifted my head, Danny said to me, "Holy shit, Jane, that was fantastic."
I was proud that my first and probably Danny's first blow job was so successful. I was worried I wouldn't be good at giving blow jobs but I could now put that fear behind me.
Danny was a true gentleman and told me, "Uh, if you want to get in the backseat, I'll take care of you, too."
I was a little confused which Danny picked up on and he said, "You know, I'll lick your pussy."
We hurriedly got into the backseat where Danny started playing with my tits again and began to rub my pussy through my panties. My panties were soaking wet by then and I didn't object when he pushed them aside and began to finger fuck me. I was more than ready to have my pussy eaten by the time he pulled my panties off me.
I felt a little shy when Danny was staring down at my unshaven pussy. No male had ever seen my pussy before. It was cramped in the backseat of the car but he maneuvered his big body so he could get his head between my legs.
Excitement shot through my body as I felt Danny's tongue begin to lick my pussy. He fumbled around which revealed his inexperience but I didn't care. I was young, horny, and was getting my pussy licked for the first time. I let him fumble around for a little while before I guided his tongue up to my clit.
"Oh yeah, right there. Oh yes, your tongue feels so good right there."
Danny concentrated his efforts on my clit until I reached orgasm. Getting my pussy eaten was so much better than masturbating. After I came, I looked up as Danny was releasing his dick from his pants and struggling to put on a condom. I had one in my purse but was glad I didn't have to pull it out. I didn't want him to know that I planned on fucking him that night too.
My legs were still spread wide as Danny climbed between them. I was more than ready to lose my virginity that night. I had to help guide Danny's dick into my pussy. I had masturbated with a dildo before so my hymen was already broken which made it easier for my date to penetrate me.
As I felt Danny's hard cock sliding into my pussy, I thought to myself, "I'm finally no longer a virgin."
I'm pretty sure Danny was a virgin too. It felt wonderful as he began to hump on me in the backseat of his father's car, fucking my virgin pussy. It wasn't the most romantic scenario to lose my virginity but I wasn't the first or the last girl to lose it in the backseat of a car.
After he came, Danny wiped off his dick, tossed the condom into a wooded area and we left to go to the party. I felt closer to Danny after that. We shared an intimate moment in our lives that night. You never forget the day or the person who took your virginity. It's a bond that Danny and I will share for the rest of our lives.
When you first start having sex, it seems you can't get enough. Danny and I had fun for the rest of the summer. It wasn't love, at least not for me, but more of a convenience to have a readily available sexual partner. My summer fling with Danny allowed me to gain more sexual expertise, especially with giving blow jobs. I began to enjoy sucking him off and swallowing his load and I'm sure he enjoyed it too. It was still difficult when we both went off to our respective colleges. We were going to miss one another.
I was able to get a few scholarships and some grants based on the family's low income. I had a work-study program too where I worked in the library on campus. Part of my job was working with athletes to help them remain academically eligible to stay on the team. I was never into sports so I had no idea who the good players were and didn't care which sport they played.
The nice part about working with athletes was most of them had great bodies. There were some great-looking young men who had muscles everywhere. They liked to wear tight shirts and shorts to show off too. It was difficult not to fantasize about them ravishing my body. However, I knew they had their choice of other girls to sleep with and probably didn't even know I existed. I mean, if they had a choice between a peppy cheerleader or me, they were going to choose the cheerleader.
I had the biggest crush on a guy named Tom who was the quarterback on the football team. I wasn't working with him but I noticed him every time he came in for his mandatory study time. Oh my god, he was so cute.
Tom has short blonde hair and blue eyes. He's over six feet tall with strong arms, broad shoulders, and a muscular chest. When he smiled, the dimples on his cheeks would melt my heart. There were many nights I would rub my pussy thinking of what it would be like to be Tom's girlfriend.
I would see Tom around campus but it was like I was invisible. He was always surrounded by other guys on the football team or the cutest girls on campus hoping to become his girlfriend. He had seen me in the library countless times but never acknowledged my existence. It didn't bother me; I was used to it. I just came to accept my fate as a plain old Jane.
For a couple of months, I was a nobody to him until one day while walking across campus, I passed by Tom and he said, "Hi Jane."
"Uh, hi Tom."
That's all he said but it made my day that not only did he acknowledge my existence but he even knew my name. My heart was fluttering even though I knew it probably meant nothing to him. I saw him several times since then and he would always greet me with that boyish dimpled smile but then I'd see him go off with a girl much prettier than me. Unrequited love was the story of my life.
