tagTranssexuals & CrossdressersYoung Guy Goes To College Ch. 01

Young Guy Goes To College Ch. 01


This might be a little long, but I wanted to set the stage. If there are good comments and votes I'll continue

As I sit in class today on my 22nd birthday I have this realization. When you ask most people, "What was the most significant thing that ever happened to you?" they might be able to give you a specific answer. If you ask the same person, "What one day in your life affected you the most?" Most people can't give you an exact date but can tell you what happened. In my case I know all of the details and I am perfectly clear on what day it happened. For me the day that changed my life forever happened exactly four years ago, my eighteenth birthday.

As I look back it seems like it was only yesterday.



A perfect time for a boy of 18 to travel to some warm exotic location and have anonymous sex with beautiful girls in bikinis.

I turned 18 four years ago today and instead of being a college freshman at the time I was unfortunately still a high school senior...in a school I hated.

And instead of traveling to some warm and exotic location, I was vacationing in a college town, in Iowa.

And instead of beautiful girls in bikinis, It was so cold (40 degrees at the warmest) that the best I could hope for was to get to see girls in sweatshirts instead of parkas.

Oh yeah, and instead of meeting drunk young college girls that would hopefully help me lose my cherry, I was visiting my sister and her two roommates who for one reason or another had decided to skip the trips to Arizona, Florida, and Cancun to stay in Iowa...don't ask me.

The reason I was up there for this spring break week is my Mom was insisting that I visit the college one more time with the hope that I could find a great job or maybe someone in the financial aid office would know of a scholarship that would help me come here to pursue my nuclear engineering degree. Dad passed away when I was 12 and Robin (my sister) was 14. Dad didn't have much life insurance and what he did have was eaten up by the hospital bills. Mom took the rest of the money and paid off the mortgage so we wouldn't have to worry about money as much.

That was pretty good thinking at the time, but unfortunately because of the crazy world of financial aid regulations Mom could only afford to put one kid through college at a time. Robin is the oldest and she had two or three years to go, so that means I either had to wait on going to school or find a job that would pay for everything. That's tough to do making seven bucks an hour. I was pretty much resigned to living at home to try to save some cash, but Mom insisted that I try one more time, so there I was.

I wasn't too upset. Being at the college for a week meant a week that I didn't have to be around home. Don't get me wrong, I got along great with my Mom, it's just everyone else. I got picked on a bunch back in my high school. I didn't really fit in with any of the social cliques. I was definitely not a jock. At 5'7" and 140 pounds I knew I was never going to be a great athlete. My family didn't have enough money to hang around with the country club crowd. I've never been interested in fixing up cars, so hanging with the gear heads wasn't for me either. The only group that I found any refuge with was the geeks. I'm pretty smart in math and science, but not a genius. My grades in English and history have always been C's, so I was definitely not on the honor roll.

But I'll be honest with you, the reason I got picked on the most is my name. Jacque Rene LaFleur. Yes, I'm a guy and for some God awful reason my parents named me Jacque Rene LaFleur. Usually when your first name sucks you can go by your middle name, or vice versa. But all three of my names suck ass if you're a guy. My Dad was French Canadian and emigrated to the U.S. when he was a kid. He wanted us to be proud of our French heritage, and definitely wanted me to be proud of my name. But LaFleur is French for "the flower", enough said. Rene is the masculine form of Renee in French, but the dumb asses in high school think of it as a girl's name. Jacque wasn't too bad in grade school because I always went by "Jack." But one day in middle school we had a substitute and when she called roll she asked if "Jackie" was here. I tried to correct her and say it was Jack, but to further my humiliation she mistook me for a girl. Long hair, short stature and being thin didn't help when you have a girl's name. I figured I had two months left of high school and then life would get better.

In college, or even just being in a college town, life would be better. It had to. Back then I was thinking "I'm going to enjoy the week with my sister Robin, her really hot roommate Kelly, and her kind of cute bisexual roommate Julie." I knew that Julie was bisexual because the previous winter break when Robin was home I overheard her arguing with her boyfriend Steve. I didn't know what the argument was about (it wasn't too serious because they are still together) but I heard Robin yelling at Steve over the phone, "Maybe I should just sleep with Julie, I'm sure she'll make me cum." I didn't bring it up to Robin at the time, and I thought "hell that happened a long time ago, three months had passed." I just wanted to enjoy the week and my birthday to the fullest.

When I got to the girls' duplex I was in that hyper nervous, super excited mode. I was going to do nothing at least for that first weekend besides get drunk and hopefully finally get laid. Yes, I was still a virgin on my eighteenth birthday. Yes 18 year old virgins still exist. It was about seven o'clock as I pulled into the drive and I remember being greeted by the sound of a very loud stereo. Friday night in a college town, I thought to myself, "I think I could learn to love this." I grabbed my duffel bag out of the trunk and headed up the stairs to their side of the duplex. As I was climbing the steps I slipped on some ice and I went crashing to the ground. Now I wasn't too hurt, my ego was bruised much worse than my leg where I fell, but my bag fell out of my hands. As it crashed to the ground (literally crashed, I had a bottle of tequila stored in there) I thought, "Just great, that bottle cost like 20 bucks." I picked myself up, grabbed my bag and walked up the steps again. I was greeted at the door by Kelly who had a look of indifference on her face as she asked me if I was alright.

Let me describe Kelly. She is absolutely gorgeous. She is about 5'5" weighing 110 pounds with half of that in her d cup breasts. I can clearly remember what she was wearing that night even though it has been four years. A pink ISU t-shirt, no bra (her nipples were like diamonds), pink shorts that said "Angel" across the ass, a smile, and nothing else. I saw that her long blonde hair was pulled into a ponytail as she turned from me and yelled to my sister, "Robin, your brother is here." And she walked away without really inviting me into the house.

I walked into the living room and set my bag on the floor. Julie hollered at me from the couch to not get the floor wet. It is then that I realized how soaked my bag was. I took my bag to the kitchen and opened it up. The bottle of tequila was destroyed and the entire contents of my duffel bag were coated with some really nice booze. I picked through the shards of glass until I think I got rid of it all. Julie walked into the kitchen and said with a smirk, "Way to get rookie."

There are a thousand things that I could have said that would have been witty and appropriate but the only thing that escaped my lips was, "I slipped."

Julie came over to my side and told me not to worry, we could go to the Laundromat tomorrow. Just throw away the broken glass, take off your coat, grab a beer, and have some fun. After grabbing a bottle of Bud Light, I followed Julie into the living room and focused all of my attention on her nice heart shaped ass. This of course was noticed by Julie as she looked over her shoulder about ready to ask me a question. I didn't even notice her looking over her shoulder until she stopped suddenly which caught my attention. "Eyes up here soldier." Now I felt like a total spaz. Not only did I slip on the steps and get all of my stuff soaked, I was just caught checking out my sister's roommate.

It's not my fault, I'm a guy and as I said earlier, Julie is cute. Julie is a bigger girl than Robin, Kelly, or even me for that matter. She is about 5'10" and a little heavier at 165 pounds but the way she carries herself is really spectacular. She might not be the prettiest girl in the room, but she is the one always surrounded by guys trying to talk her up. She always dresses in a real classy way that borders almost on the smutty side, and tonight was no exception. Whenever I've seen her outside the house she is always wearing a dress or a skirt. She is all woman. Knowing that she is constantly horny (according to my sister) and the fact that she is bi got my 18 year old cock stirring.

Julie and I sat on the couch and chit-chatted with me trying to catch an occasional glimpse up her knee length skirt for about 30 minutes as my sister and Kelly kept walking from the bathroom to their rooms trying to keep up with the conversation. I was finished with my second beer and was on my way to grab a refill for Julie and myself when Kelly and Robin came into the living room dressed to kill. Robin had her keys in her hand as she talked to Julie, "Julie. Kelly and I are going out for a bit to The Station, we shouldn't be too late, do you mind keeping an eye on Jack?" Now, normally I would be pissed that I drove all this way to see me sister and as soon as I got there she decided to go out to a bar and leave me at home. I probably should have been pissed because of the way she told Julie to keep an eye on me, I don't need a babysitter! But before I said anything stupid, two things saved me. First my brain kicked in and realized that with Robin and Kelly gone, I might be able to make a move on Julie. The second (and probably more important thing) is that Robin and Kelly were already walking out the door.

As soon as they were gone I finished grabbing a couple of beers for Julie and myself and sat back down on my side of the sofa. We continued to chit chat about life, school, anything and everything. One thing that I had read about getting a girl to go to bed with you is to let her talk and keep the conversation about her and I was hoping it was working. I finally asked Julie how Robin and Kelly were going to get into the bar? They were only 20 and I didn't think that either of them had a fake ID. Julie laughed so hard beer almost came out of her nose. She composed herself and said, "Boy, you really don't have any idea how life works do you?" I shrugged my shoulders and had no idea what she was talking about. She then told me that most college girls had no problems getting into 'The Station' even if they weren't 21 yet. I still had no comprehension on what she was talking about and Julie could see it on my face.

Julie told me she was going to show me. She stood up and left the room for just a moment and came back seconds later. In that brief time she had adjusted her clothes and the results made me speechless. Her skirt that had been just above the knee was now mid-thigh and I was sure that any move Julie would make would cause her ass to be on display. Julie had also removed her button down shirt leaving her in a white tank top that clearly showed the lacy pattern of her bra underneath. That was all of the demonstration to know that Robin and Kelly would have no problem getting in to the bar.

I wanted to jump Julie so bad at this time my balls actually hurt as my cock started to grow in my tight jeans. To have any chance with this experienced girl I knew I was going to have to play it cool though. I asked Julie why she didn't go to the bar with my sister and other roommate. I almost came when she said she would rather celebrate my birthday with me but she also added that going out to a bar tonight would just remind her how much fun she was missing compared to last year in Cancun. Feeling pretty confident about what she had just said I decided to press the issue and asked her what was great in Cancun that she didn't have right here.

I thought for sure that she would say that she missed all of the guys (or girls) on display, or the warm weather, or hanging out on the beach; but Julie said she missed most the crazy drinking games that went on. I showed my ignorance to the ways of the world again when I asked what type of games? Julie's eyes lit up as she grabbed my hand and led me to the basement so she could show me two of her favorites. As we passed the fridge in the kitchen she stopped and grabbed a 12 pack saying we were going to need it.

When we got to the basement I was surprised how nice it was. Julie's bedroom was down here as well as a nice big carpeted room that Julie said they used for partying and "other stuff." Julie ripped open the twelve pack and pulled out two beers, one for her and one for me. The first game we were going to play was speed chugging. The rules are simple, pop open your beer and drink as fast as you can. When you are done you hold your can above your head upside down. If you don't win, you have to turn your can upside down as soon as the winner does, and you get soaked in beer.

"On your mark, set, GO!" Even though Julie shouted out the 'GO!' part, she beat me by about 1 second. When she turned her can upside down maybe one drop hit her lovely long brown hair. When I turned my can upside down I must have had three ounces still in the can so my hair and shirt got wet and I started to smell like a brewery.

Julie grabbed two more cans as soon as we set our empties down. I had barely just opened my beer when she screamed "GO!!!!" I got just over a swallow down when Julie had finished her second beer in just over a minute. As she tipped her can upside down, I followed suit and my head, shirt, and jeans all got soaked in beer. If I had to try to slam another beer right then I swear I would have puked. I thought now was as good as time as any and leaned over to give Julie a kiss as she was laughing at my predicament. To my surprise she welcomed the kiss and actually kissed me back. When I put my arms around her to hold her close (and hopefully grab that sweet ass of hers) she grabbed me by the hand and said it was time for another game.

She reached into the closet and pulled out two bats and said we were going to have a bat race. This game I knew. It was really pretty simple. All you do is lean over and place your forehead on the bat. You spin around as fast as you can 10 times and then run to the other end of the room. Nothing real difficult, pretty stupid even, but I just kissed Julie and she wanted to do this so I'm doing this. Again Julie was all energy and hollered out, "On your mark, Get set, Go!!!!!" I spun myself as fast as I could and after ten times around, I dropped the bat and tried to run to the other end. I spun out of control and fell flat on my face on the basement's carpeted floor. Julie was laughing hysterically behind me. She was laughing so hard that I thought she would piss herself.

I looked up from the floor and asked her what she thought was so funny. Then I realized why she was laughing. When she yelled go, she didn't bother to play the game. She was just watching my drunk ass fall down. I guess I couldn't blame her, I must have looked pretty foolish lying on the floor and covered in beer.

After I hopped up I walked over to Julie and kissed her again, this might be the best birthday ever. I told her since she wasn't going to do the bat races that I didn't want to do them either. I also told her the speed chug game was out because I was afraid I might throw up. Julie laughed at me and said I didn't want to play because she beat me so bad. I wasn't going to argue with the girl that I was hoping to get in the sack later that night so I just smiled. I asked her if there were any other games they played down there that we could play.

Julie smiled at me and said there was one other, but that I was probably not up for it. Not wanting to have this night end I said I was up for anything. That was the one moment in my life that changed my future forever.

Julie asked, "Anything?" I nodded yes. She then told me of this one wild game that was for couples and asked me again if I wanted to play. I of course said yes, did she just refer to us as a "couple"? Julie then said it was a speed race. No problem I thought, I might not be very big or athletic, but I'm pretty quick. I was shocked by what she said next.

"It's real simple, we see how fast we can undress and then dress in each others clothes."

It took half a second for my brain to figure out what she was saying. I almost objected but before I said anything stupid, I thought for a second. This means I get to see her naked!!!! This is going to be awesome! Before I thought out the consequences I hollered, "Go!"

As I pulled my blue tee-shirt off over my head, Julie took off her white tank top. Before I could undo my jeans, Julie already had unhooked her black skirt and let it fall to the floor. She was standing there in this great lacy pair of white bikini panties and a matching white lace bra that I barely saw through her tank top earlier. I was in heaven. As I dropped my jeans, Julie reached behind her and unsnapped her bra letting her 36C boobs free. I was speechless as I stood before her in my white jockeys. Julie quickly tugged her white panties down and her shaved pussy came into view. I couldn't move.

Julie noticed this and pulled my underwear down for me. My four inch cock was as hard as ever. (Yes I know, four inches when you're hard is embarrassing, but on my small frame I think that it's not too small. At least that's what I tell myself.) I stepped out of my underwear and Julie quickly put them on. She had my blue tee-shirt on in a second, and was buttoning up my jeans before I realized that she had even put any clothes on. She laughed at me and told me I was horrible at this and that she was going to have to help me.

With saying that she slid her warm white bikini panties up my skinny legs. They were actually a little loose in the ass but the warmth of the gusset where her pussy had just been almost made me cum. She slid her bra over my arms and stepped behind me so she could hook it up. Before I knew it, her tank top was over the bra and I was wearing her black knee length skirt.

She pinned me against the wall and planted a very rough kiss on me. Her hands were all over me, moving from pinching my nipples through the lacey bra and tank top I was wearing to groping my ass through the matching white lace panties. She moved her hand to the front of my panties and grabbed my dick so hard I thought I would scream out if her mouth hadn't been covering mine as she kissed me. She stroked me hard and fast and in less than two minutes of her expert hand job I was cumming into the little white panties. Julie broke her strong kiss and smiled at me, "You liked that didn't you?" All I could do was give a sheepish little grin. It was the most incredible feeling I have ever had. Hell it was the first time that anyone but myself had touched my cock, let alone made me cum. But I was a little embarrassed that I came so fast. I've overheard guys talk in the locker room that they lasted thirty or forty minutes when the fucked their girlfriends. I lasted less than two minutes and it was only a hand job.

Julie led me to her bedroom which was just off the main room in the basement. She threw me on to the bed and looked me up and down. She told me that since I already got to cum once it was my turn to make her cum. She pulled off my t-shirt that she was wearing and quickly dropped the jeans and white jockeys. As I started to take off her tank top that I was wearing she stopped me by saying, "Did I tell you to take that off. You'll do what I say and only when I say it. I prefer to have sex with cute college girls rather than little boys, so leave ALL of it on." She smiled and walked naked over to her dresser and grabbed her lipstick. She grabbed my mouth roughly and told me to sit still as I began to squirm uncomfortably. After a few seconds I now had ruby red lips. Five minutes later and many trips back and forth to her dresser, Julie had me completely made up with foundation, blush, eye shadow, mascara, lipstick, and lip-gloss.

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bypantysubsissy© 7 comments/ 158891 views/ 43 favorites

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