Plain Jane Ch. 01

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.

One day I was working in the library and Tom was there with some of his teammates who were supposed to be studying but they were goofing around more than anything. I saw them whispering and looking my way. I didn't think anything of it at first but they kept looking my way so I couldn't help but think they were talking about me. When their study period was over, Tom came up to me and struck up a conversation. I was beyond thrilled.

We talked about our majors and the fact that I was a freshman and he was a junior. He was the starting quarterback on the football team but knew his playing days were over once he graduated so he was trying to keep up his grades. I was so entranced by Tom's charm that I didn't even remember the entire conversation.

Tom threw me for a loop when he ended the conversation by saying, "You're a nice girl, Jane. We should hang out sometime."

I managed to stutter my reply, "Uh, yeah, uh, s-s-sure," and gave him my phone number.

Then he left.

I wondered, "Did he really just say he wanted to hang out with me?"

Then I said to myself, "There's no way he wants to hang out. But why did he take my number?"

I didn't want to get my hopes up only to be disappointed. There is no way Tom would want to spend time with me when he had his choice of girls much cuter than me. Those thoughts were just my defense mechanism to protect myself from getting hurt. I desperately wanted to hang out with Tom in the worst way.

The next day, I received a text from Tom that read, "Hey, do you want to meet up tonight?"

I was shocked and excited beyond belief. My crush wanted to spend some time with me. I waited almost an hour before I responded because I didn't want to seem anxious.

"Sure. What do you have in mind?"

"I don't know. Maybe you could come to my apartment and we could watch a movie or something."

"That sounds nice. What time?"

"How's 7:30?"

"Great. I'll see you then."

He gave me the address to his off-campus apartment that he shared with a couple of his teammates. He said they'd be out for the night. I was so excited I could hardly think about anything else all day. It wasn't a real date but I'd be alone with Tom in his apartment. I figured he might want to have sex with me but I wasn't sure I should do that the first time we were together. However, I didn't know if I had the willpower to resist either. Besides, with my luck, he'd probably ask me for help studying for a test or something. I was afraid to get my hopes up out of fear of being disappointed.

I had no idea how to dress to "hang out" so I put on a little makeup and decided on a simple white tank top and jean skirt. I made sure to wear a matching bra and bikini panty set just in case things went as I dreamed. I was nervous and anxious on my walk to Tom's place. I didn't know what to expect when I got there.

When I got to Tom's place, it looked like a typical bachelor's apartment. There was secondhand mismatched furniture throughout the place but it was cleaner than I anticipated. His two roommates who were also on the football team, Steve and Mike, were out for the evening which I took as a good sign. Tom had me sit on the sofa while he grabbed us a couple of beers. I'm not much of a drinker but I took one anyway. Chills went through my body when he sat close to me on the sofa. Tom never put on a movie but we sat there and talked. We talked about our plans after graduation and places we wanted to travel to, just ideal chit-chat.

I was already feeling a little buzz from the first beer but accepted his offer to get us another. Things started to heat up when Tom came back. He must have sensed my nervousness because it seemed like he used the first beer and conversation to make me feel more comfortable.

"You're a beautiful girl, Jane, I wonder why we haven't talked more before."

"I don't know. You always seem to have other girls around who are much prettier than me so I didn't think you'd, you know, want to hang out with me."

"Don't be silly, those girls are such phonies, not like you."

Oh my god, Tom was really turning on the charm. I fell for it, too. One of the cutest hunks on campus was telling me how beautiful I was.

"I've wanted to talk to you before but I didn't think you'd want to hang out with a jock."

"I think you're a great guy, Tom."

He gave me one of his patented dimpled smiles and my heart just melted. Tom then leaned in to kiss me. I thought I had died and went to Heaven as our lips touched. I dreamed of that moment and it was even better than I had imagined. His kiss was so soft and tender. I immediately felt my nipples harden and my pussy get damp as we continued to kiss on the sofa.

When Tom reached to cup my breast, I let out an audible gasp followed by a soft moan. He must have known I was melting to his touch. I was afraid this was all a dream and that I was going to wake up at any moment.

I then felt Tom's hand on my knee and his hand gradually creeping up my thigh and I thought to myself, "If you don't want to have sex, you better stop him now."

I then thought, "Get real, you know you want to fuck him. You may never get this opportunity again if you stop him."

When Tom's hand reached my upper thigh, I slowly spread my legs to encourage him to go further. I moaned again as I felt his fingers slide along my panty-covered pussy and begin to rub me. My legs instinctively spread further as he began to finger me through the satin material of my panties. I began to rub his dick through his shorts. There was no doubt where this was leading.

Tom eventually pushed my panties aside so he could finger me without them getting in the way. I had fucked Danny plenty of times but I was never so turned on as I was that night with Tom. The only time he withdrew his finger from me was to take off my top and bra. I raised my arms so he could pull it over my head and he quickly unsnapped my bra to expose my breasts, tossing my clothes to the side.

"Damn Jane, you've got some nice tits. You have to quit hiding them under those sweatshirts you like to wear."

Tom immediately began to alternately suck on my nipples and then stripped off my panties to expose my hairy bush to him. He laid me back on the sofa and began to finger me with one hand and play with my tits with the other while sucking on them too.

He then asked, "Do you want to go into the bedroom where we have more room?"

I nodded my head and replied, "Yes Tom, I'd like that."

He took me by the hand and led me to his room where I took off my skirt which was my only piece of clothing left and watched him undress. He was wearing a tight T-shirt as usual and when he pulled that off, I was filled with pure lust. Tom revealed his chiseled upper body with broad shoulders, muscular arms and chest, and six-pack abs. His chest had a light coating of soft blonde hair.

When he pulled off his shorts and underwear in one motion, I marveled at his strong legs and erect cock which I guessed to be about six inches with a little upward curve to it. He turned around to put his clothes on a chair and as soon as I saw his tight ass, I couldn't wait to sink my hands into it. I was practically drooling at the sight of this adonis standing before me who was about to fuck me. At that point, I didn't know if he'd ever want to see me again but I didn't care. I wanted to fuck him. I needed to fuck him. My pussy needed to feel him inside of me.

We embraced and kissed again as I ran my hands all over his fine body, squeezing his muscles in the process. I grabbed hold of his firm buttocks and pulled him closer to me, his erect cock pressing against my stomach. He worked me over to the bed where I sat down on the edge, his dick in my face.

"Go ahead, baby, suck it for me."

Tom placed one hand on the back of my head, gently pulling me closer to his cock, not that I needed any encouragement. He was a little bigger than Danny and a little thicker. I felt his dick press against my lips so I opened my mouth and stuck out my tongue. His dick glided along my tongue into my mouth as I wrapped my lips around his hard member. My head began to bob as he moved his hips in rhythm to my movements. He was pleasantly surprised that I could take it all into my throat.