A Crash Course in Losing Virginity

Sorry for the delay in stories, my life has gone to shit. Sorry if this seems a little bit odd, or a bit not-sexy, but like most of my stuff, it is true, this actually happened, and we all know real life doesn't always make for the most flowing, sexy, perfect story. Sorry if it's not great, I haven't written one of these for years....and sorry the intro was so long, the story wouldn't make sense in sequence without it...especially if I add another Crash Course story later. Hope you enjoy. And let me know what you think. Thanks!

*

So, it had been waaay too long since I had gotten any. My long-term relationship with Brandon had fallen apart, he had started dating (and moved in with) some new girl, and there I was, a law school student, sitting in my apartment on weekends never doing anything or going anywhere. It was official: my life was boring.

I had some friends; I was even still talking to Brandon. He'd even call me now and then, and we'd talk. That all stopped around the time he moved in with his girlfriend, and around the time Matt came back into my life.

Matt had always been a part of my life. I met him at summer camp back when I was in middle school. While there, I found out that he lived only a town away from where I did, although the summer camp was hours away from where we both lived. After camp let out, we hung out as friends, and even dated casually late in high school. After we'd been dating for awhile, his family moved into the house across the street from us. What luck. We found any and every excuse to hang out after that. We said we were helping each other with homework, tutoring, whatever we could think of.

I dated Matt for awhile, but our parents didn't particularly like that the two of us were dating, so eventually the relationship broke up and we went our separate ways. We both dated other people, although we would always hang out and end up fooling around with each other between relationships. There were even several occasions that I can recall where we'd be fooling around, and one or both of us would be cheating on our significant others at the time. That all lasted until I met Brandon.

While I won't go so far to say that Brandon was insecure, he wasn't crazy about the idea that I still hung out with Matt, especially considering the fact that I had cheated on several of my boyfriends with Matt. Long story short, I never ended up cheating on Brandon with Matt -- I never cheated on Brandon with anyone for that matter - but I largely ignored Matt, or at least, I didn't go out of my way to hang out with him while I was dating Brandon.

The years with Brandon were some of the best years of my life - I was young, in love, and everything was perfect. But nothing good lasts forever, and almost 5 years later, my time with Brandon was over, and those 5 years were reduced to 2 ½ egg boxes worth of memories, which now sit in my closet collecting dust.

The break-up between me and Brandon occurred about the time I entered law school. I knew that law school wasn't going to be easy, but I hardly anticipated that it would be quite as miserable as it really was. It was hell. And I -- still not having learned from some of my past mistakes -- I took all my frustrations and struggles out on Brandon. Ya, needless to say, he was gone from my life within a month or two of my starting law school.

For almost nine months, I sat around, boyfriend-less and miserable. I went to law school, talked with my friends, sometimes went out to dinner with them, but something was missing. My friends said it'd get better, but really, it didn't. I'd gotten to the point where I felt like no one cared. My life seemed to be falling apart in front of my eyes...my GPA went from a 3.97 in my undergrad college where I was a valedictorian to 2.44 in law school...barely in the bottom third of the class. It wasn't that I wasn't trying, I just felt like I no longer had anyone backing me, anyone believing I really could do it, the way I'd had all through undergrad. And I didn't have anyone like that in law school. Whether that's why my GPA dropped or that's just the excuse I came up with, I don't know. But let me tell you, it was much easier in undergrad when I had someone there for me, 24/7. Besides my GPA having gone to crap, I wasn't happy being in law school. I didn't like most of the subjects I was taking, and the only real friend I had was more of a leech that I just couldn't get rid of. But that was life.

Time passed, and although I cried less, I was still very upset about the fact that me and Brandon had broken up. Some people said I was obsessed, and maybe I was, but the break-up really tore my world apart. When I eventually heard the news that Brandon was going to move into a new apartment with his girlfriend, that was it for me. Depressed, unhappy, you name it -- if it was a negative emotion, I felt it.

Nothing could even be done to make me crack a smile, or at least, not for long. It seemed that if anything made me happy, it was over way too quick, or somehow it would remind me of Brandon. I'd go somewhere, and it would occur to me (while there) that me and Brandon were supposed to have gone there, but we never found time. This, of course, ruined my mood for the whole time I was at the place. Random phrases that people would say to me would trigger thoughts in my head which would remind me of something me and Brandon had done, or something we had said. As we had been together for quite some time, almost everything I did somehow had some significance or could make me think of something that related to what used to be "us."

At one point, I decided I should buy a dog, because I thought that maybe a dog would make me happy. I bought a sheltie and named her Kailey. Only after having Kailey about a week did I realize that I bought a dog that was practically a clone of the dog Brandon had owned in high school. I hadn't thought anything about Brandon at the time I was buying the dog, but later I realized that I had a clone of his "Alex"... and of course, that cemented all of my friends' minds that I had lost my mind and was obsessed with Brandon. For awhile, Kailey improved my mood somewhat, but not as much as I had hoped.

The first time I remember actually being "happy" (or at least, "less miserable") about something after the break-up was 9 months after the break-up occurred. One of my previous ex-boyfriends, Matt, had been messaging me on facebook saying I should call him sometime. Now, as I mentioned, I had been ignoring Matt for quite some time, because Brandon was not particularly fond of him. Of course, now that I was no longer dating Brandon, there was no one to care if I hung out with Matt. Or so I thought.

But we'll get to that later. It was a Friday night when I finally decided I wanted to call up Matt and see what he was up to. Turns out, I woke him up, and through our talking, I got to mentioning that he should come to Indianapolis and come hang out with me sometime. As he had that weekend free, he left that night.

Matt didn't arrive at my apartment until about midnight. He pretty much looked like I remembered him -- tall, kind of skinny, dark brown hair, teasing eyes. Since he got in so late, we went to a local sports bar downtown, Jillian's, where we had dinner. While Matt had a beer, I just had a diet coke. I had no intention of getting drunk and accidentally sleeping with Matt. Ya, wait till you hear how that worked out. While we were at Jillian's, Matt noticed crowds of people all walking in one direction, and went outside to ask them where they were going. Turned out, there was another bar, Howl at the Moon, just a little ways down the street. Once we finished eating, we headed to Howl, where Matt convinced me that I should have a few drinks and loosen up. We both had a few beers, and I don't know if it was the beer or what, but a little while into the night, I definitely wanted to kiss Matt (well, I'd probably do more, but I'd start with a kiss). I didn't do anything though, because I was still trying to keep myself from doing anything that would end me up in bed with Matt. We stayed at Jillian's until about 2 a.m., when Matt suggested that we go back to my apartment and watch movies.

As I only had a small apartment, with very little storage space, I had only moved a very small selection of movies there. Matt picked out Coyote Ugly for us to watch, and we settled into the couch to watch the movie. About halfway through the movie, Matt reached out to try to tickle my knee. I don't know why, but ever since I was little, I've had this one ticklish spot on my knees -- and I had forgotten that Matt knew about it. I tried to fight Matt off, but all that did was fuel the fire and make him want to tickle me more.

It was all in good fun. I tried grabbing his arms and holding them away from my knees, but as Matt is quite a bit taller than me, and definitely much stronger, this didn't do much for me. Matt pushed back against my arms, and ended up forcing me off the couch and onto the carpet. We wrestled around for a bit on the carpet, pushing the coffee table clear across the room. Eventually I was able to wriggle my way out from under Matt. When I finally yanked myself back up and sat down on the couch, Matt surprised me by giving me a quick kiss.

I would have kissed him back, but it was such a quick peck that it was over like that, and I never had a chance. Matt acted as if the kiss had never happened, and went back to watching the movie.

It wasn't until we were about ready to hit the hay that anything else happened. Matt had settled down on the larger couch, while I was sitting on the loveseat after the movie had finished. I'm not sure what led into it, but Matt stretched out on the couch and made a comment about how he might as well make himself comfortable.

"Why? Are you gonna sleep there?" I asked.

"What? You gonna let me cuddle with you?" -- I could have dealt without the tone. The tone in his voice was almost one of mocking, which made me mad, and made me wish I hadn't said anything, but then I remembered that I have this bad habit of getting upset over nothing, so I decided to let that one go.

"Sure, you can."

When we were ready to get into bed, I came out of the bathroom to find Matt already tucked into my bed. I climbed in next to him, and turned my back to him, telling myself that nothing was going to happen. I know, I know, but I was still telling myself that. Not 5 minutes went by before Matt tried to tickle my knee again. I pushed back against him, and tried to keep his hands away from me. Of course, he was winning the tickling fight, being much stronger and all. Somehow, during all of this, we had gotten to the edge of the bed and not realized it...until I started to fall. I grabbed onto the shirt Matt was wearing, and he tried to grab onto me, but that didn't work. We ended up falling off the bed into a pile of arms and legs. It was actually kinda funny, even at the time.

I don't really remember exactly how it went from there, I just remember us both getting back up on the bed. Matt had started tickling me again, and the next thing I knew, he had both my arms pinned up above my head and had his body weight on me so I couldn't really move. Matt lowered his head and kissed me. It was a tentative, gentle kiss. He was sure of himself, but he wasn't going to force himself onto me. It was sweet.

I kissed Matt back, not quite as gently as he had me. Our breathing sped up as we both started to get excited. He let up my arms, so that he was no longer pinning me down. I wrapped my arms around him and we continued making out. We had to pause a few times to catch our breath. He soon moved from kissing my lips over to my neck, and he planted small kisses up and down my neck, causing me to squirm under him.

Matt eventually moved lower and started kissing his way down my chest, first over my shirt, then slowly lifting it up and out of the way. At first, he left it bunched up around my neck, but then seemed to decide that he wanted it completely off, so I arched my back to help him get it off. As I had not been thinking that anything was going to happen that night (and nothing probably would have had I not had the beers), I had a very un-sexy sports bra on, but that didn't seem to faze Matt one bit. Matt pushed the bra up and over my tits, and started to kiss them. He quickly moved to one of my nipples and took it into his mouth. He started by rolling his tongue over it gently, but quickly changed that to flicking it right on the bud. He was driving me wild and he knew it. He switched between my breasts several times. As one is considerably more sensitive than the other, he eventually solely focused on the more sensitive one. Once he had me twitching with every flick of his tongue, he moved on.

Matt then completely drew my bra over my head, threw it on the floor, and progressed kissing his way down my stomach. Upon reaching my jeans, he undid my belt and started to unbutton and unzip my jeans. When he started to pull my jeans and panties off, I lifted my hips so they'd come off in one smooth motion. With that barrier gone, it was all free game. Whereas I hadn't been sure I wanted to do anything with him, now that we'd gone this far, some of those thoughts seemed to vanish.

More thoughts of what I shouldn't be doing vanished as Matt stuck first one finger, then two, into my pussy. It had been so long since I'd been fucked or even messed around with someone, I practically could have cum right then. Matt pumped his fingers in and out of me, until I was dripping wet. Every now and then, he'd look up at me to see how I was enjoying it. And was I. One time that he looked up, our eyes met. He grinned this evil grin at me, and lowered his mouth to my pussy. I had shaved the night before, as I preferred a completely shaved look, but had not been keeping it up for the 9 months that I was boyfriend-less. He seemed to like that I was shaved.

He started flicking his tongue over my clit, eliciting little gasps with every flick. Between that and his fingers still pounding away at my pussy, I couldn't hold back anymore. My orgasm had been building for awhile, and finally reached its peak. I writhed on the bed in pleasure, groaning audibly, while Matt continued his ministrations.

Once I had settled down, Matt moved again so that he was hovering over me. I reached down and stroked his hard cock. I didn't remember him being quite so thick, but then, it had been seven years since the last time I had felt him. His dick was rock hard and hot...and he was dripping gobs of pre-cum. I knew we were going to need it too -- while he might not have been bigger than Brandon, he was definitely a ton thicker.

Matt moved his hips so that his cock came to rest at the entrance of my pussy. He slightly pushed forward, causing his cock to part my pussy lips and slightly enter my pussy.

He turned to me, "You sure you want to do this without a condom?"

"You ever had sex without a condom?"

"Yes" -- he might as well have said "well obviously" -- the tone told me that that was a VERY stupid question, and really, I don't even know why I asked, knowing the number of girlfriends he had had.

"Well you think you have anything?"

"No."

"Ok, then go ahead...."

So, Matt started to slowly push his cock into me. Really, he couldn't have done it quickly, it just didn't want to fit. When he realized it wasn't going to slide in with one smooth thrust, he lowered his body on mine, his cock still positioned at my entrance, and we started making out again. Meanwhile, he would thrust in, pull a little bit out, and thrust in again, over and over, working inch by inch of his hot thick cock into my pussy. When he finally had his entire cock sunk into me, and we were able to thrust freely, it was pure bliss. I'd never been filled like that before.

Matt started out slow -- he could tell I wasn't used to someone quite so thick -- if only because of the time it took for him to work himself inside of me. He thrust in and out of me until I was wet enough for him to speed up somewhat. His thick cock hit every pleasure spot on the inside of my pussy, seemingly all at once. As I was still getting over the fact that I really was fucking him -- something I had specifically told myself I was NOT going to do at the start of the night -- Matt lifted his body off of mine and continued thrusting. I looked between our bodies and watched his cock pumping in and out of me, while he looked down at me, watching the expression on my face. I've always liked watching that, so I'm sure he had quite a sight.

"Hey, how bout you get on top?"

So we flipped positions and I rode Matt. Being able to control the fucking made it even better, and I was ready to cum again in no time. After not getting any for almost 9 months, I was so out of shape, I wasn't able to keep going for very long. I didn't want to stop though, it felt so good. Matt grabbed onto my hips and held onto me as he pounded his cock into me from beneath. It wasn't long before I was moaning and groaning another orgasm into the pillows next to his head.

Despite my cumming, he was still going strong. I lifted myself off of his cock and moved myself into the position for doggy style. Matt got the message pretty quick, and moved behind me. As he grabbed onto my hips and thrust his still rock-hard cock into me, I grabbed onto the sheets and thrust myself back at him. The pleasure was overwhelming. I had never been filled so full for so long. It felt like nothing I had ever experienced. I was quickly ready to cum again, as doggy always does it for me very very well, much less when I had this hard and thick of a cock stuffed into me. I could tell Matt was getting close too. He was panting behind me, and his thrusts were getting a little more erratic. With a few final hard, deep thrusts, Matt shot his load deep inside of my pussy, groaning and moaning all the while. He kept thrusting, and a few seconds later, I joined him in my own orgasm. We both collapsed onto the bed and fell asleep soon afterwards.

Time passed, and we eventually did come to have sex again. And again. And again. But unfortunately, this experience has shown me that no matter how hard I try, I can only push away those depressing thoughts for so long...and that when Matt leaves (heck, half the times when he's here), they're back in full swing again. Ah well, for now, this works to push them off for a bit. Too bad it doesn't work better though.

Also unfortunately, when it slipped out to Brandon that I slept with Matt, Brandon pretty much stopped talking to me. Now, if I email him about something that would interest him, I sometimes get a text message back, but that's it. Now, that leech friend of mine has found a law-related job and doesn't bug me so much anymore. Now, the puppy's getting older and has found new ways to be more annoying everyday. And now, the summer's over again and I'm back in law school. With even less support than I had last year.

It's been about a year since the break-up, but it might as well have been yesterday. Nothing significant has changed in my life since then, if anything, things have gotten worse.

Hey, things can only look up from here, right?