First Time is Never Like the Plan

Warning: This is not a happy story. I'm writing it partly because I've been asked a number of times about it and partly for cathartic reasons. For those reasons, I'm going to stay as true as my memory allows, without getting into erotic embellishments in the interest of entertainment.

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This is a story about the time that I lost my virginity. I wish it were a story of wine, roses, candy, satin sheets and Prince Charming but it's anything but that. An unromantic tale that involves an insecure girl (me) a jerk (Prince Charming) and even a wicked witch of sorts. There is no hero and no virtuous maiden the events just happen. I was in grade 12 and just turned 18.

Grade 12 started for me much like grade 11 ended: uneventful. That was in a word the way I was feeling with myself, I'm not sure if I was depressed I just wasn't feeling anything. Each morning going to school filled me with a heavy malaise, the type felt most in my eyelids. I wasn't popular, I wanted to be popular, but I had no idea where to even start on that front. I wish someone had told me that being good at ballet, being good at math, being nice to people and liking my teachers wouldn't add up to being the belle of the ball. Really I didn't even need to be the queen but I didn't like it when the other kids made fun of me.

Growing up lanky also didn't help as I became pretty self conscious in a bad way. I certainly wasn't ugly, adults would always tell me how pretty I looked, but that was the problem kids my age didn't. Being slight and thin, my breasts didn't grow to mammoth sizes; or much of any size really. Top that off with the glasses, frizzy hair usually pulled back and an awkward shy manner and you have some wide open Friday nights.

As for being picked on, it was very difficult for me, it always seemed so immature. The boys I could deal with, I smiled at them and they were mostly nice to me. The girls on the other hand, well some of them were just really mean. I couldn't understand why some of them hated me so much. When I wasn't leaving them alone I was trying to be nice to them, but the latter just made it worse.

This one girl, Amanda, picked on me every chance she got. It's as if she planned her day around picking on me. It upset me horribly because we were friends in middle school, but she went the popular skip class to smoke route and I went my way. It gave me little satisfaction that people thought she was ruining her future, we lived in the now and the now more or less sucked for me.

The things she would say were so silly but after a while they would just get to me, like "Michelle, Michelle has a face like a gazelle" or just the timeless, "here comes horseface" or the charming, "Mich the bitch". The other kids would laugh and snicker or often join in if I showed any emotion.

It probably wouldn't have bothered me as much as it did if it wasn't for the fact that she had the one thing that I wanted more than anything in the world: a boyfriend. I was so jealous of her or anyone who had a boyfriend. Hand holding couples always looked so happy together.

I would daydream picturing myself walking down a busy street with my one guy holding my hand knowing that I was his one girl. In a crowd of people we would stand out shining in happiness. Brought back to reality by my mom's snapping fingers, "Mich! Are you still on the planet earth? Wake up and get your head out of the clouds."

The only place I could dream in peace was my bed. I would pull the covers over my head feeling completely isolated from the world outside. There I created entire movies in my head, starring me in happier settings with a co-staring boyfriend. As of late these dreams were getting more and more heated. Sweating between the sheets, I pleasured myself most nights. Since I turned 18, I had been masturbating to the point of a bad habit. Strangely frustrated and unfulfilled, I would drift into deeper dreams. There, my only worry was waking to the sound of my alarm telling me it was to go back to school again.

This is how grade 12 was for me. Not only did I feel lonely at school, but I also felt lonely at home. My older brother had moved out a few years earlier to go to university. At least his antics broke the monotony from time to time. As for my parents, with nobody to yell at, they seemed docile in a strangely sad way. I never really caused them any trouble, at times I figured that maybe I should, if for nothing else then to put some life into them.

I still really enjoyed dance class and was getting really good at ballet by this time. My instructor even thought that I could have had a future in it if I wanted it. In hindsight, I think she was just trying to motivate me, but the positive vibes felt good nevertheless. I had performed at the local performing arts centre where I was able to lose myself. I just had a different confidence on stage; like I was somebody else, maybe a princess or a debutant.

My parents adored my performances gathering a real sense of pride. I didn't even mind wearing the revealing tutus; they actually made me feel pretty and graceful. I loved being told I was pretty even if the loudest voice was my dad's. All the adults agreed too, after the performance praise would rain down as I was told, " what a lovely young lady" I was.

At school, I always did my homework on time and with care. This earns you points with teachers but not with your peers. Math is what I liked best and while I didn't like the idea of being a math geek, I didn't see any reason to not do something I liked. This attitude found me in the math club, the president of the math club...yet another subject of ridicule. Far from the Prom Queen, I was Queen of the Nerds.

I wouldn't have minded if I could have gotten a date out of it. Contrary to what you might be thinking, the math club wasn't a great place to find a date. Some of the boys were nice, but they were at least twice as awkward as I was and even more shy. They never made eye contact with me and some openly shook when talking to me. My level of maturity wasn't at the stage of making concessions to my ideals. None of them measured up to my vision of the pair that stands out on the busy street, radiating happiness in their wake with each fresh step.

As a result, I mostly just hung out with other girls. I had my two best friends, Angie and Sara, who were probably my equal on the social ladder. Ladders aside, we loved each other with an unspoken understanding of each others plight, and still talk to this day. The times we were together I will always treasure, but boys were always scarce from our gatherings. Angie would have a shy boyfriend every now and then, but they would never go all the way.

We were virgins, but that doesn't mean we didn't hear about the students at school who were having sex. The whispers always went around and some of them just had to be true. I had no illusions about what sex was, I had seen a lot of videos and there was no doubt that I was jealous of those who were doing it. It felt like it was us and them and we were far removed from the world the popular girls.

My 18th birthday came, and it came with no boyfriend to buy me flowers. I still got my weekly ridicule from Amanda and I remember it hurting me extra that week. I went to the washroom and didn't want to come out, I wouldn't have been able to forgive myself if she saw me crying. I really hated her and I felt helpless around her. She had the things that I wanted: popularity, sex appeal and a hot boyfriend.

Her boyfriend was Brian K and he was on the swim team. He had short brown hair that sort of curled at the back, dark brown eyes, clear skin, quirky smile with dimples and he was tall but not too tall. He made me think of a darker Jason Priestley. He always wore his swimming team jacket and that just made him look even hotter. He was the type of guy that could have made me the centre of the room; made me stand out on a busy street. Ooohhhh, I was so jealous of her!

Brian was in one of my classes, chemistry, and he wasn't a bad student. I don't know what he ever saw in a bitch like Amanda. Well, it was probably her boobs, but that's just about the only good thing that anyone could say about her. Seriously, she wasn't even that pretty.

Often in chemistry class, Mr. Courtnar would place us into random groups of four or six, and for the first time in the year I was placed into a group with Brian. This was remarkable given that this was May and the year was almost over, I must have been in a group with everyone else at least twice. Not that being in a group with him gave me any sense of satisfaction, quite the opposite, it scared the daylights out of me.

As the students arranged themselves at the benches with their newly formed groups I didn't want to move. I had butterflies in my stomach and I felt like going home. It was probably 5 minutes before Mr. Courtnar asked if I was lost in his sarcastic way that makes you feel like an idiot. I swallowed hard as I knew that I would have to face him.

What bothered me the most was that he probably just didn't think about me at all. I was a nobody to him, well less than a nobody, I was the girl that his girlfriend picked on. He had seen her do it, although he had never said anything to me himself, he never raised his sword to my defense either. I was so scared that he would mention my insults or further them. All of this turned out to be for nothing, he actually seemed like a pretty nice guy.

I don't remember what the experiment was but I do remember having one of the best times of my then short life. Brian talked to me! He talked to me like I was a person. It felt natural, it felt like the class just wasn't long enough. I had fun, he had fun, I could just feel, well chemistry! I felt like I was ether peroxide and he was oxygen; we would explode if we came into contact! :) sorry for the geeky joke :)

The feeling couldn't have been lost on him I thought to myself as I almost skipped all the way home. Of course with every minute that passed the shadow of reality was chipping away at my fantasy until it hit me like a rock: He was my biggest enemy's boyfriend and I really was scared of my biggest enemy. I was in no position to fight her for his hand. Firstly, I didn't think I could win, and secondly, what if I lost? I would be humiliated beyond my worst nightmare. I decided to put it out of my head and to go on with my existence; I mean nothing had changed, it was all in my head anyway.

Two days later, chemistry class came again and I wasn't looking forward to it. I was a nervous wreck, but I just kept telling myself not to let on that I was nervous and nobody would notice. 72 minutes passed and the class was over, no contact, no making a fool out of myself...I made it. I was halfway down the hall when I heard my name, "Michelle!" I turned around to the sound of, "Michelle wait up!"

It was Brian! He looked as hot as ever, maybe even hotter, his eyes seemed to sparkle. There was a sense of urgency in his face as if he was trying to catch a bus and if he missed it there wouldn't be another. He didn't have to go far to catch me but he seemed a little out of breath like he was nervous himself. I was caught so off guard that I didn't know what was happening. Abruptly, he came out with it, "Michelle...Michelle, you seem like a really nice person and if you're allowed that is, do you, maybe, want to come with me, like and my parents, to our cottage, maybe?"

You could have knocked me out with a feather. I stumbled and fumbled over my words until the best I could reply was, "What do you mean? I mean, what, you know, what about Amanda?"

"We broke up! That was, like, two weeks ago. Haven't you heard?" He said this as if the entire world should have known.

It was true that I hadn't really seen them together but I didn't keep tabs on them either. That didn't matter at all as all I wanted to do was jump out of my shoes and scream YES! Instead I managed to say, "Well I'm going to have to ask my parents."

I turned to leave in a hurry before he changed his mind. I heard a confused voice over my shoulder, "Aren't you forgetting something?"

Baffled at this, I said in my goofiest voice, "No, I have everything." Looking from my shoes to my shoulders.

"Well, then can I have your phone number? So you can, you know, tell me what your parents say."

I wanted to slap my forehead as my inner-monologue was chastising me for being an airhead. Phone numbers were exchanged and I was on my way to ask my parents; that was my next obstacle. I built this up in my head so much that I didn't realize just how much they trusted me. It didn't take too much deliberation for my mom to say I could go just as long as she talked to his mom and that everything was on the up and up. My mom sensed no problems, made sure about the sleeping arrangements and come Friday I was on my way. On my way to my first actual date. It was my first actual date with a boy and with the boy I so much wanted to have a date with.

The fairy-tale was rather short lived; it ended not too long into the trip. Brian was pretty rude and came off as pretty spoiled too. I think some of his charm was attributes I was projecting onto him due to his looks and our limited interactions. He teased his little brother, ordered his mom around and made me feel like I should be kissing his feet for letting me be around him.

The first night revolved mostly around Brian boasting of his swimming exploits, something his father couldn't seem to get enough of. I don't think he asked me one thing about myself. Another thing his father couldn't seem to get enough of was alcohol. Both of my parents drink so this didn't bother me that much but he would give Brian coolers too remarking that it would, "put hair on your chest son." Truly charming stuff. The more Brian drank, the more obnoxious he became.

I had my own bed to sleep in that night and nobody bothered me. I have to say that aside from the obnoxious behaviour I was still happy to be there. Him picking me, made me feel special, made me feel wanted. He was one of most, if not the most, popular guy in the school. He could have asked anyone, but he asked me.

In the morning, Brian was dead to the world, he didn't drink heavily, but probably enough to make him not want to get up. I spent most of the morning with his little brother down at the pond looking for frogs and other creatures of the deep. Around noon I helped preparing lunch with his mom. She was really nice. I almost felt sorry for her for being married to such a brute.

Brian eventually emerged from his sleep and was back to being obnoxious. Still his quirky dimpled smile made it hard to be too mad at him. He didn't really pay that much attention to me other than the odd request to watch him do something or other. Still this was more attention than any other boy had really given me, so I was happy to look on. I didn't really know how a boy was supposed to act and I really didn't know how I was supposed to act either.

Around 5 o'clock he told me to come into town with him and then we could go down to the lake when we got back. I asked him why we didn't just walk to the lake but he told me that he needed something in town. We took his parents SUV and started driving but he didn't go into town instead we just went to the lake, which was about a five minute walk. He told me in an unconvincing voice that he didn't need to go to town anymore. He parked on the grass and we walked to the lake.

It wasn't a beach, it was just a dock by the water and there was nobody really around. We walked to the dock and stood on it for a little while but it's not like we had our bathing suits and we weren't going to go swimming. That was the first time he made contact with me, he hugged me from behind and told me, "I think you're so beautiful, like the most beautiful girl I've ever seen."

My heart almost melted in my chest. I had never been flooded with such pure happiness all in one moment. I had no words, I turned around and we kissed for the first time. I kept thinking that things couldn't have been going any better. The kiss was soft, on the lips and felt sincere. We finished with holding hands. I thought I saw the sun in his mischievous eyes.

He told me that we should go into town after all. I was swooning so hard I couldn't pay attention to all his erratic behaviour regarding where we were going. At that point I wasn't asking questions and I followed him to the SUV hand in hand. When he opened the door he told me to, "Get in the back", and sort of pushed me that way and followed behind me.

He didn't waste any time as I felt like he was attacking me, kissing me all over my face and I felt his hand on me too. I was dressed simply and comfortably in kaki shorts, a white t-shirt and running shoes. His hand was between my legs rubbing my pussy through my shorts. It didn't really feel good, more invasive. We had gone from a nice first kiss minutes earlier to him groping me in the back of his parents' truck. It was happening really fast, but I also wanted to impress him so badly. So I kissed back and let him feel me up I didn't think it would go any further.

He started to try to take my clothes off and I struggled but tried to keep it playful. I asked him, "Brian, what are you doing?"

His reply was blunt in his honestly, "I'm going to fuck you?" He grunted.

I asked him, "Please stop, let's just talk about it first, ok?" Without disguising his frustration he backed off a little bit.

"Brian, I've never done this before and I'm not sure I want to do all that, is that ok?"

He started to pressure me, saying, "Come Michelle, this is going to be my only chance this weekend, we're leaving tomorrow you know?"

"Yeah, but I'm just scared that's all, and maybe we can just take it a bit slower, that's all."

"Shit, take it slow and waste the weekend? I knew I shouldn't have asked you." He said with annoyance.

A wasted weekend? This broke my heart, considering the perfection I felt in the kiss on the dock. He kept asking me and pleading with me. It made me feel like I was letting him down and just not cool enough to do what everyone else just did.

I felt a bit of resolve in me and looked at him shyly, "Well, do you have a condom?"

A big smile came to his lips and took one out of his pocket. Obviously he had the entire thing planned. We were locked in kisses and caresses again. This time more gentle than our initial engagement. He seemed to have taken my temperature and was trying a different approach. Now he was being sweet and talking softly to me. Telling me how pretty I am and how much I was going to like it.

"It's your first time Michelle?" I nodded while looking deeply into his eyes. "Don't worry, you're going to be ok, it's only going to hurt a bit, ok?" I nodded again, putting my trust in him.

It wasn't long before my shorts came off and my shirt soon followed. I felt embarrassed and unprotected in just my underwear. "Do you like it?" I asked looking up at him for approval while laying on my back. He nodded with narrow focused eyes which left no doubt to his desire. With his eyes looking me up and down he worked his way out of his shorts. His dick pointed right out at me and it was as hard as hard could be. It looked really big, I had seen them in magazines and videos but having one right over me, pointed at me, made it look much more imposing. I started getting worried.

He consoled me, telling me, "Don't worry Michelle, just relax, it's going to be ok, you're going to love this."

Then he said something completely unsettling in his attempts to pacify me. "I do this all the time to my girlfriend and she loves it." I didn't even realize the freudian slip, I just wasn't happy about him bringing her up at that sort of moment for me. Before I had the time to scold him, he pressed his face up to mind and kissed me with an open mouth.