Ashley's College Experience

by Alex Storm

 

Chapter 1: The Deal

I looked at my sister and couldn't believe what she'd just asked me to do. "What are you saying?"

"I want you to go with me and Colin to his frat's Halloween party! You'll have fun!" She said, totally skipping the strange part.

"No, what was the other thing you said?"

"I want you to go as Colin's friend Rob's date. No strings attached. Just a date."

"Jimmie, has being a sorority girl bruised your brain? Let me point out a few things; A: I'm not in College; B: I don't date College men because C: I'm A GUY!!"

"Look, I'm not asking you to 'show him a good time' or anything, just pretend to be a High School senior for me for one night, go out with him, then never see him again. Besides, it's not like you've never dressed up like a girl before. And don't tell me you didn't like it, 'cause I know it's true. You even looked good, cute even."

That was true; I had dressed like a girl on a few occasions. My sister used to give me "makeovers" when she herself started experiments with makeup and girls clothing. And there was one Halloween where I went out dressed as a girl, a Cheerleader to be exact. I looked so much like a freshman cheerleader (and I was an Eighth grader), that one of my sister's junior boyfriends tried to get my phone number. It was the thrill of fooling this guy that led to some of my more recent "cross dressing" experiments, the ones she doesn't know about. Like how I've mastered the art of passing for a female, using makeup padding and the right underwear. I've tested my skills a couple of times; one time the cable guy was met at the door by a sexy, flirty co-ed wearing really short shorts and snug little tank-top. I know the guy was completely fooled, because he invited me to meet him for drinks. Poor guy, I'm only 16! (Though I told him I was 22, and he believed it!)

My favorite memory of being dressed was at this years Youth dance at the youth center. I convinced my parents to let me go alone to the dance. They went to dinner; I went deep into my mother's closet. I found a sexy little cocktail dress, hose and shoes. I took a cab to the dance, with the cabbie checking me out all the way! At the dance, I was astonished! I figured they would think I was a High School girl, or maybe a College intern working at the center, but almost everyone thought that I was one of the 20ish year old community mentors for the local girls. People would tell me how great it was that beautiful, young woman would take time out of her life to provide a good role model to troubled girls in our community! When the women chaperones said it, they meant it; when the men said it, they were trying to check me out! My former soccer coach even slow danced with me! And I kissed him goodnight (O.K. so there was more than 'goodnight' kissing going on then.) Since then, I have been expanding my wardrobe and looking for another opportunity to "dress up". You see I wasn't bothered by the concept of going out dressed as a girl.

I was bothered by the idea of having my sister spoil my fun.

"Look sis, I know how much you love your boyfriend, and how you'll do anything to please him, including finding dates for his lame Frat Brothers, but couldn't you find him a date who's a little more girlish, like, I don't know, A REAL GIRL!" (I had to be convincing, if I gave in too quickly, she might suspect that I WANTED to do this for her. O.K., I wanted to do it for me too.)

"Ashton, don't you think I've tried all my friends. They're all busy, or have boyfriends, or don't like guys, or know that Rod is¼.", she trailed off at the end.

I was worried. "Rob is what? Gay? A sex pervert? An axe murderer? What exactly is Rod, Kimmie?"

"Rob¼Rob's a bit of a nerd. He's really nice, but he's just a little¼different. I think he's been on like 3 dates his whole life, and he's definitely still a virgin. So he's the perfect date for you; He'd be happy to be seen with a pretty girl, he wouldn't try anything with you, and he probably won't expect anything from you anyway. See, it's win-win. I make Colin happy, by finding his bro a date. You make Colin and me happy by going out with Rob. Rob makes us happy by getting us into the Kewlest party in town. And, after the party, Colin makes me happy!" She said with a small smile.

"What about me? How am I "Happy" in this grand scheme of yours?"

"First, dear sweet brother, you get to hang with cool College people all night. Second, you get to help out your loving sister. Third, I'll pay you $50." All right, I had my in, I'll just act like I'm doing it for the money. Now I had to seal the deal.

"Make it $100 and you've got yourself a deal! One question though; if Rob finds out, what do we do, dear, sweet sister?"

"Well, we tell him that it's a Halloween prank. That'd score Colin points with the Frat. See, win-win for everybody. So you'll do it? Honest?"

"Yes, I'll do it. Who else will know about this little caper?" I asked, not wanting to show too much enthusiasm.

"Just you, me and Colin will know. I picked up a costume for you; I'll bring it up to you later. And Ashton, one more thing."

"What is it, Kimmie?" I asked, I had to start to prepare, and she was killing my mood.

"I would have given you $200, and my car for next weekend. See ya later."

D'oh!!

 

Chapter 2: Costume Changes

As I looked at my sister's choice for Halloween costumes, I was reminded about her one major flaw: her modesty. My sister is a beautiful girl, some would even go as far as to say hot, but she doesn't see herself that way. She has a great figure, but she never shows it. Her swimsuits have always been one-pieces, her underwear is always a sensible, modest style, and her dresses are never too flashy. Too sum up, her clothes are boring. Mom's stuff is actually sexier than Kimmie's. It's sad really, when you think about it.

Case in point: the costume she picked out for herself. If I looked like her, and with some work I can, I would go as a sexy French maid, or a Playboy bunny, or a naughty nurse. But she's going as the Little Mermaid. Now, this costume could be made sexy, with two shells for a bra and a sheer wrap around the legs to be the tail, with the rest the body showing. But she's wearing a body stocking with a green bikini top over it, and a tight green skirt for a tail. Not an inch of that sister of mine is showing. It's a damn shame.

My costume is in a similar vein: a witch. Not a sexy Elvira, slit up to your hip, neckline to you waist witch, just your typical black dress that goes down to you ankles, no neck showing at all, witch. Boring, to say the least. And now she's standing here, smile ling, asking me what I think of my costume, and I really wanted to go with something else. I had to think fast.

"Well Aston, what do you think? Do you like them? I didn't think you wanted anything too showy," she said, with a proud smile on her face.

"Sis, I love 'em, especially yours. You are gonna blow Colin away. But¼"

"But what?"

"I had a little something else in mind. You wouldn't mind if I came up with something on my own, would you? " I hoped to hell she would it was O.K.

"Oh, no problem, I'll just take this back to costume shop. What did you have in mind? You're not going to pick some god-awful costume and ruin this for me, are you? Remember, if Rob doesn't like you, no money for little Ashley!" she said, a little bit of fear showing in her voice.

"Don't worry Kimmie, when I'm done, Rob's not going to be the only boy who likes me." The ball was in my court now. I was going to take this as far as I could, and nobody was going to spoil my fun.

Since I had only a day to get ready, I had to move fast. I had to come up with a costume that would fool a bunch of drunken frat boys. I needed something that would totally convince everybody who saw me that I was a girl. I thought long and hard, then it occurred to me, the one costume that every guy with a pulse wanted to see a girl in: the classic sexy schoolgirl costume! That would be the best one ever! If I did it right every guy, not just Rob, would want me! Maybe even Colin! (Why did the thought of Colin thinking I was hot turn me on so much?) I had to get moving right away!

I wanted to put this costume together myself, so I wasn't going to buy it at a store, but I did need a few things. I volunteered to take the Witch costume back. At the shop, I picked up a blond wig with pigtails, since my brown hair was too short. At the house, I looked for a nice dress blouse. Luckily, my sister had quite a few of them. Underneath the blouse I would wear my body briefer and my breast forms. I had learned how to tape my chest to get cleavage, so I could unbutton my blouse a bit.

I started to have trouble when I started looking for a short, pleated skirt. I didn't have a chance to go out and buy one mom had nothing 'school girl appropriate', and forget about my sis having any thing like that. Then I remembered she was on the tennis team. The tennis team wears short, pleated skirts! I ran into her room and rummaged through her closet. I found it on a hanger. I held it up to my waist. Oh, my how short it was; it barely went past my upper thigh. This was going to be great!

I knew I could find knee socks in either my mom's or my sister's rooms, but I wanted something different. I always liked it when schoolgirls, or women pretending to be schoolgirls, wore those socks that went over the knee, but I knew neither of them would have those. Then I thought about thigh-high stockings. I've seen schoolgirl costumes with those, and they looked hot! I got into my mom's underwear drawer and looked. Success! She had a pair of black, lace top, thigh high stockings. Then I found the garter belt, and I knew I would have fun at the party. After all, men love women (or boys who look like women) who wear garters and stockings. I ended up buying the shoes I wanted at the local shoe outlet. They were a pair of platform Mary Jane's with a blocky 4-inch heel. Just what the sexy schoolgirl is wearing these days!

 

Chapter 3: Getting ready

The day of the party, I told my sister she could have the main bathroom, and that I would use Mom's bathroom. I told her that I would need a lot of time to get ready, and reminded her that I was doing her a favor, and if she were bothered by anything that I did, she would be letting Colin down. She gave me a quick, "Yeah, yeah, whatever," and went to get ready herself.

Since my parents were gone, I had mom's room to myself. I took a nice, long bath using mom's special soaps and bath oils, and I used her razor to shave off all my body hair. As I dried myself, I was amazed at how soft and smooth my skin felt. And I smelled pretty too! Now it was time to get dressed. I started by taping my chest. I wanted to have a nice amount of cleavage, but I couldn't give myself too much. Then I slipped into my briefer, after tucking myself in securely. Once I had it on, and I put the breast forms into the cups, I had a very feminine shape. I had a nice rack, too. Next came the garter belt. I thought it looked dumb over the briefer, but I really liked having garters and stockings. Then I rolled the stockings over my legs. God, this felt good! I fastened them to the garter straps and looked at myself in the mirror: from the neck down I looked like something from the Victoria's Secret teen line. Too bad I couldn't go to this party as a lingerie model!

Now came time for the shirt. I left the top two buttons undone, giving me just a hint of cleavage. Next came the skirt; wow was it short! Once I got it fastened, I took a look at myself in the mirror. As I moved, the short little skirt showed my stockings and my garters, heck, just standing showed stocking top and the edge of the garters. Once I put on the shoes, the effect was even worse! Oh, I was going to break some hearts tonight! Then I put on the wig, and secured it to my head. As I caught my reflection in the mirror, I was impressed; even without the makeup I now looked like a sexy schoolgirl. I quickly sat down at mom's makeup table and started putting on my makeup. I decided to go with an overdone, too much makeup look. It took awhile, but I eventually got the look I wanted, right down to the "Fuck me red" lipstick, and nail polish to match. Now I looked like every guy's favorite fantasy, the slutty, sexy schoolgirl built for sex.

Since I couldn't let an opportunity like this get away, I decided to take pictures of myself in costume. I listened to figure out where my sister was; she was still in the bathroom. I quickly ducked down the hall to my room and got my digital camera. I set it up to take pictures on a timer. I then took as many pics as I could. I started with me standing, then me leaning down to "pick up books". Then I sat at my desk, then me sitting with my legs crossed. Then, my favorite, me sitting on the edge of the desk, legs crossed seductively, looking right into the camera. I checked the pictures on the monitor and they looked great! Photo spread material if I ever saw it. I started to save them onto my computer when my sister asked if I was ready. I told her I was, and she wanted to see my costume. I opened the door and stepped out into the hall.

Kimmie stood there and stared like she didn't recognize me. "Who the hell are you? Ashton, this isn't funny; get out here right now and send your little slut home! We don't have time for this and we had a deal!!" Oh my god, she didn't even recognize me! She thought that I was some girl I snuck into my room. As I though about what to say to her, she looked passed me and into my room. "Kimmie," I started, in my best girl voice, "Ashton isn't here, and he's gone for the night. My name is Ashley, and I'll be going to the party as Rob's date. I can't wait to go out with a college man. They're dreamy!"

Kimmie's face flashed with anger, "Oh no you're not. Ashton and I had a deal, and if he thinks that he's going to see one cent of that money, he's as big an idiot as you are a slu¼wait a minuet, what did you say your name was?"

"The name you gave me, sis; Ashley."

"OH-MY-God," stammered my poor, confused sister, "Ashton what did you do to yourself? You look more like a girl than most of my friends. I can't believe it! Your voice, the make up, the costume, your body?! How did you do it?"

"Just a few things I found around the house." I said, still using my girl voice, "I looked up the makeup tips and the rest on the internet." I hated to lie to her, but how do you tell your older sister that you've been secretly planning to do this for months? "I knew how important this was to you, so I decided to do it right. You're not mad, are you?"

"You did all this, for me?" she asked. I nodded back. "You have to be the best bro¼I mean sister ever. But don't you think that costume is a bit much? And when did you grow boobs?"

"Kimmie, I picked this costume to distract people. They see this, they automatically think 'girl' and don't question it. I think it will increase OUR chances of pulling this off. And the breasts, a little tape does wonders." I said with a smile.

"I'm just worried that some guys might get the wrong idea about you. You look really sexy, and guys respond to that kind of thing," she said, with a look of quiet acceptance on her cute, mermaid face.

"Uh, sis, do you forget who you're talking to? I am a guy. And don't worry, I'll be fine."

Then, the doorbell rang.

"They're here!" Kimmie squealed, "Wait up here. Colin is going to freak out when he sees you, Ashley." She said as she went down the stairs "He's always had a school girl fetish, I might have to keep you two separated!"

Oh, this was going to be one fun night!

 

Chapter 4: Out with the boys

I heard Kimmie open the door, heard her tell the guys what great costumes they had, heard her kiss Colin. Then she said, "Ashley, come on down. Rob is here!" and then to Rob, "You are going to blow a gasket when you see her." This was my big moment. I took a deep breath and walked slowly down the stairs. Halfway down, I saw Rob; he wasn't bad looking or anything, but he wasn't a hunk either. His costume was a wizard. He looked at me, not with the "I'm going out with a stripper/schoolgirl" look I expected, but with a little disappointment. Kimmie spoke up first, "Rob, this is Ashley, my friend from school. Don't worry, she's older than she looks." Another lie, he was maybe 5 years older than me. "And Rob, this is my good friend, Ashley. Rob's the president of the Frat. And he invited us to the party."

"I believe that I had something to do with that too," said a familiar voice from the next room. It was Colin; he was dressed as a pirate, with a blousy shirt and tight pants, and eye patch and a bandana on his head. He looked like a guy from the cover of one of those romance novels. Actually, he looked hot. (Why did I keep thinking of him that way?) And I realized he was giving me the look! His eyes looked down to my sexy shoes, then back up to my cute hair, back down my legs again, then back to my chest. He was totally checking me out. "Ashley, I hardly recognized you," he said. Since he started dating my sister, we'd seen a lot of each other, but he'd never seen me like this. "Rob, you're a lucky guy. You want to switch dates for the evening? Kimmie won't mind," he said with a chuckle. My sister gave him a "behave yourself" look, and Rob said, "No, Kimmie's your girl, you keep her. Let's get going, before the beer's all gone."

As we went to the car, I noticed Colin kept looking at me, even when he was holding my sister's hand. Rob seemed to not want to look at me at all. Rob drove, and his car was a big Caddy, so he was going to drive. We hit a problem when my sister tried to get into the back seat with Colin; her "tail" made it impossible to crawl into the back. Kimmie told me to get into the back with Colin (yes!) while she rode with Rob up front. Rob watched me the whole time I was getting into my seat. The skirt rode up a little, showing the garters. I looked over at him as I adjusted myself and saw he was smiling at me. I felt a rush! I started to wonder just what Colin was getting out of this, but I was definitely getting turned on. We pulled out and headed to the party. Since we had a little bit of a ride ahead of us, I tried to make myself comfortable. I crossed my legs, and then I realized my stockings were showing. Getting into the mood, I turned and smiled at Colin with my sexiest look I could. He looked at me like I was his girlfriend, the whole time talking to Kimmie about his day at work. The whole time he was talking to her, he never broke eye contact with me. As we left town, the car got dark. I shifted a little in my seat, turning towards Colin, and I was aware of him turning towards me. I moved my foot back and forth, and soon found myself running my foot up and down his leg. Then I felt something touch my leg. It was his hand! I couldn't believe it; Colin was starting to feel me up! His hand started to go down my leg, and I stretched it out until it came to rest on his knee. Then his hand started to go back up my leg. God, his hand felt so good on my leg! He kept slowly moving his hand up until he found my garters. Then he ran his hand around my thigh, and then he touched the flesh of my hip! I realized I was breathing heavily; I wanted this to go on forever. But we reached the next town, so he quickly moved his hand away.

As the car filled with light again, I realized that he was still looking me in the eye. "Sweetheart," he said, giving me a wink, "I never told you how much I liked your costume." My sister said thank you, but I noticed he was pointing at me. I mouthed "thank you" to him.

"Yeah, you look great, I don't think you've ever looked better."

"Really," replied Kimmie; I just smiled shyly.

"You look sexy. I bet a lot of guys are going to try and pick you up tonight."

Kimmie was really startled by this." You think I look sexy? You don't really think other guys are going to hit on me, do you?" Sometimes she was such a twit. I looked at Colin and gave him a smile, enjoying our little game.

"Oh, I think they will," said Colin, "Of course, they're going to have to wait until I've had my turn with you!"

I mouthed the word "Really", and he smiled and nodded. I now realized that Colin was getting into this as much as I was. My sister just started to laugh at Colin's comment, not realizing it was meant for me as much as for her.

Rob spoke up as we pulled into the driveway. "We're here!"

This was going to be a night for me to remember that was for sure.

 

Chapter 5: Party Animals

The frat house was all decked out for Halloween; lights, streamers, drunken college boys everywhere. It was almost stereotypical, like it had been lifted right out of some party movie. Rob got out and just stood there, while Colin got out, ran around and got the door for Kimmie. "Hey, Rob! Don't worry, I'll get Ashley out of the car too!" he said sarcastically. Such a gentleman! Then the four of us went into the house. Colin and Rob belonged to the Lambda Sigma Tau Frat, which was the biggest bunch of party animals this side of Delta house. As we got to the door, two people in costume, a guy and a girl met us. The guy was dressed as Zorro, if Zorro had decided to put on and extra 35 pounds of pure beer gut. The girl, well I hope what she was wearing was a costume. I mean, I guess she could have been a hooker, or maybe white trash. She had on a leather halter-top; leather micro-mini, torn fishnets, and enough makeup to make the elephant man look cute. The moment we got to the door, Zorro's eyes were locked on me. "Colin you swarthy sea-dog!" he said in a pirate like tone, "What took you so long? The party's been rocking for hours."

I stepped forward, tipped my head down while looking up at him, and batted my eyes at him. "I'm awfully sorry Mr. Zorro," I started, in my best little school girl voice, "It's my fault they were late. I was in detention, and they had to wait until the principal let me out." I kept up the bashful, sexy pouting thing I had going.

"Why did you have detention?" Asked Zorro, with a lot of excitement in his voice. "Were you bad?"

"Oh, I was very bad. I should probably be punished some more, Mr. Zorro, sir." I said in a breathy, sexy tone. Then I looked up at him and smiled.

Colin cleared his throat. "Bruce, this cute little thing is Ashley. She's a friend of Kim's." He said, and then he paused for a moment, "And she's Rob's date!"

Zorro, or Bruce I should say looked like he had been hit with a brick. "Good god, how did you get her, Robbie? Kim, please set me up with one of your friends as soon as possib¼OWW!" The Hooker, who had slapped him alongside the head, interrupted his comment. "Remember me, your fiancé, dumbass!" she said as she stormed into the house. Bruce ran in, yelling apologies and promises. As we went into the house, Kimmie took me aside. "Was that completely necessary?" she asked.

"No Kim, It was fun!" I replied. I loved the effect I was having on men so far.

"Well, I think you should know that Rob is not enjoying the whole "Ashley experience", you should try harder to make him enjoy himself."

"Hey, I'm just having some fun. If you are so worried about Rob, why don't you make him happy."

At this point my sister reminded me of our deal, and of how I wouldn't see any of my money if I screwed this up. While I was actually doing this for myself, I decide to give it a chance. Maybe Rob wouldn't be so bad anyway. I decided to catch up to him and find out.

Then I entered the house. Instantly, every eye fell on me. Over the loud music, I could hear whistles, and people asking who I was, people telling their friends to look at me, and one guy yelled, at the top of his Lungs, "I think I'm in love!" I started to work my way towards Rob. Unfortunately, either because of my shoes, or some subconscious urge within me, my walk had become a bit of a strut. And as short as my skirt was, let's just say that if people hadn't noticed me before, they were noticing me now. I found Rob getting a drink from the bar. I walked up to him and said, " Forget me already?" He looked at me and said, "Honestly, no guy could forget you. Want a drink?" I quickly accepted, and suggested we talk. Of course, the whole time, guys were checking me out and slapping Rob on the back in congratulations. We worked our way to a little corner of the house that had been relatively untouched by the party.

"Rob," I started, " is there some problem with me? You've seemed so unhappy since we first met, I hope it's not my fault."

"Ashley, you seem like a nice girl, and you look amazing, so I'll give it to you straight. I really didn't want to have a date for this party. I mean Kim and Colin were great to find a good looking woman like you to come here with me, but they didn't need to."

I was so turned on by the idea that I was passing as a woman so well, and amazed that Rob seemed so nice, that I almost forgot to ask why he didn't need a date. " I looked him in the eye and asked him why he didn't need a date.

"I'm involved with someone else."

"If you're seeing someone, why aren't they here, and why don't your friends know about it?" I asked, beginning to see a pattern.

"Let's just say, our relationship wouldn't be ¼understood by a lot of people."

I didn't know whether he meant he was gay, or what, but who was I to judge. I was a teenaged boy dressed like Brittney-friggin-Spears for god's sake. I took his hand and said to him "I hope you and this other person are happy. And if you're half as sweet to them as you were to me just now, I know you will be. Now then, Rob, what about us? What are we going to do?"

"Well, we're supposed to meet later, but if I have a date that's going to put a damper on the whole thing. I could take you home, but I get the feeling that you like it here." I nodded and smiled at him.

" I've got it! I'll cover for you! I'll stay here; you go to your "meeting". As crowded as this party is, nobody will notice if you're gone, and if anybody asks were you are, I'll tell them you were "just here a moment ago". Nobody will know you're gone."

"You'd do that for me, maybe I picked the wrong date for tonight. Are you sure about this?"

"Don't worry about me," I said, looking at all the guys in the next room, "I'll be fine."

"I have no doubt about that." He said with a grateful smile. "If things get sticky, my rooms upstairs, 202. If there's a sock on the door, knock first." I nodded. " Now give me a kiss." Rob said, starting to pucker up.

"Why, I thought you had another date?" I asked, but I was going to kiss him anyway.

"It's not every night I get to kiss the hottest girl at one of our parties. And be seen by the brothers!" he replied, nodding to the guys in the next room.

"Well, if it's all right with you, let's give them a show!" Rob smiled and said yes. I stood up, and then straddled him. I put my arms around his neck and brought my lips to his. I almost felt electricity as our lips touched. His lips felt rough on my lip-sticked lips. I slightly parted my mouth and his tongue quickly entered my mouth. For a guy with no experience, he sure kissed great. I ran my fingers through his hair, and his arms slid down my back. The right one caressed my thigh, while the left one squeezed my butt. We kissed like that for a long while, and then we separated. We were both aware of the guys cheering him on, but we tuned them out. Rob smiled at me and said, " they'll be talking about that for a while." I smiled back and said quietly, "They should!" We sat there a while, cuddled up together, then he looked at his watch and said he had to get going. I smiled at him and said, "So soon? We were just having fun," in a whiney voice. "Ashley, I'm sure you're going to have lots of fun here tonight," he replied, looking into the next room, and the drunken frat boys that were there. He gave me a quick peck on the lips and thanked me for everything, and then he disappeared into the party. Now I was alone! I quickly checked my make up. Once I was back in shape, I stood up and headed back into the party, this time I was really trying to sashay when I walked. I went up to the bar and stood for a moment.

A moment later, three guys were standing right next to me, trying to offer me a drink. This was like shooting fish in a barrel. I shyly smiled, giggled, and said, in my best little girl voice, "I'm not supposed to drink. I'm too young. Besides, there are SO many to choose!" The guys looked at each other, than at me, then the bar, then me again. Then one guy, who latter told me his name was Rick, reached behind the bar and got me a wine cooler. I was hoping for a shot, but when in Rome. I thanked the boys and headed back into the party.

I was amazed at how well I was blending in here. No one questioned my gender; actually, I think a blazing neon sign could appear over me that said "Boy" and a lot of these guys could care less. I loved the effect I had when I moved into a room. Instantly, every guy seemed to be looking at me, watching me. It didn't matter if they were with a girl or not. I was an object of desire, and it was turning me on! I also noticed the costumes the women at the party were wearing. Some of them were like my sisters, not showing too much of anything, others were revealing in some way; a witch costume with a high slit, a barmaid that showed lots of cleavage. Only a couple of them were "sexy" like mine; a French maid, a Playboy bunny, and a nurse wearing kneepads who said she was the "head nurse"! So part of my allure was the fact that most of the women's costumes here did nothing for the male libido.

As I walked through the room, I smiled and flirted with guys as they came up to me. I was incorrigible. I would flirt, get the poor guy all excited, and then leave him hanging as I moved to the next guy. Thankfully, no one ever asked me any questions about my life, since I'm a poor liar. Rod's name did come up once, but my plan worked, and the "Cop" I was talking to didn't really seem to be bothered by hitting on his friends date anyway. So this is how I spent most of the party; acting like a teenage dick-tease and loving every minute of it.

On another trip to the bar, to get my 4^th wine cooler, I saw a familiar face, my favorite pirate Colin. He was standing by the bar alone. I walked right up in front of him and asked, "New in town, sailor?" He laughed, and asked if I was having fun. I told him I was probably having too much fun, and he smiled. I asked him where my sister was, and he said she was with one of her sisters, helping to console the poor girl because her boyfriend had just up and dumped her. I told him that Rob was taking care of some Frat business; Colin didn't seem to care what this business was he just seemed glad we were alone. I know I was. "So," he asked me, "you want to go somewhere a little more private?" I looked up at him and said, "My dear captain, I thought you'd never ask!"

 

Chapter 6: Private School

Colin took my hand and led me up the back stairs to the bedrooms up there. We stopped at room 203. I looked at room 202's doorknob; there was a sock on it. Way to go Rob! As we went into the room, Colin hung a tie on the door. "Shouldn't that be a sock?" I asked. "That would mean I had a girl in here and we were 'doing it'. Kim sees that and I'm dead. The tie means Frat business, people will still knock, but no one will question us being in here."

"Very smart," I said to Colin, " but why are you worried about people knowing I'm in here?"

A look of confusion spread on his face. "Well, for one you're Rob's date and Kim's 'friend'. It won't due for you to be seen in here with me."

I laughed, "Easy Colin, I was just messing with you. Why don't you sit down?" He sat down on a chair.

"So, do you like my costume?" I asked, standing in front of him, turning a little side-to-side.

"Yes," he replied, with an urgent tone to his voice.

"What do you like about it?"

"I like your sexy shoes, and your sexy stockings," he answered. As he said this, I tuned to the side and lifted my short, little skirt to give him a better view of my legs. "Damn, Ashley, you've got great legs."

"Did you like touching them in the car?"

"Yes. I didn't want to stop. I've been wanting this since we got here."

I walked over to him and sat down on his lap, my legs lying across his. His hand immediately went to rest on my knees, and I felt him through his pants. He was huge, and obviously turned on. I put my arm around him and looked him in the eyes. "Colin, do you find me attractive because I look the way I do, or because you know who is under the costume?" He took a breath. "I know you're Ashton, Kim's little brother. But I've never felt anything like this for a man ever. I hope it doesn't bother you, but I think my attraction for you right now is mostly because you look like the hottest girl I've ever seen."

"Actually, that was the right answer." I said, getting ready for the kiss I knew was coming.

"But don't get me wrong, knowing what's under the hood is kind of exciting too. I mean, I have fantasized about this once or twice, but the "girl" in it was never you."

"Well, it's time to make some new fantasies." I said, as I brought my mouth up and kissed him.

If Rob was a great kisser, then Colin was an expert! Our tongues danced back and forth, and our lips never parted. I ran my left and up his back, up to his hair, while I worked my right hand down his chest. Colin's right hand caressed my back while his left hand went to my chest first. He squeezed my breasts, and I moaned into his mouth. Then his left hand went back to my knee and started going up. I moaned again as he reached my bare thighs, but when he reached my crotch, I think I might have squealed. In response, I worked my hand down past his waistband, into his shorts. I was right; he was huge! Now I held his member in my hand, and rubbed it softly. He made a pleased sound into my mouth, and responded by rubbing me through my underwear! We were both getting so hot! I couldn't believe I was doing this with my sister's boyfriend. I couldn't believe that I could get him so worked up that he would do this with me. I knew exactly what I wanted to do next. I broke off our kiss, and looked Colin in the eyes. "Colin," I gasped, "I want you to make love to me. Now!" And then I kissed him again.

"Are you sure?" he asked. "Yes!" I replied. He then asked me where. I quickly thought about it. Although being taken on the bed, like a real girl was tempting, I had my own fantasies. "Standing in front of the dresser, so I can see us in the mirror. You and your beautiful schoolgirl!" I replied. We quickly moved to the dresser, and Colin got behind me. I looked at us as he kissed my face and neck. We looked like a regular couple, a hunky guy and a dead-sexy girl. We were beautiful together.

Colin reached inside the dresser and got out some lotion. He put a little in his hand, and told me to put some one of mine. Then I felt on hand move my underwear to the side as the other started to rub the lotion along my bottom. I reached back and dropped his pants and shorts, then I found his penis and began to rub lotion into it. He started to sound very excited by this. Then I felt a finger enter me. It hurt a little at first, but I soon found I enjoyed it. Colin started to whisper into my ear, " Have you ever done this before?" "No, I'm a virgin." I whispered back, hoping he would get my meaning. I felt another finger enter me. I made a little moan.

"I can't believe a sexy girl like you could still be a virgin."

Still feeling the pleasure from his finger I responded," I've just never found the right guy before."

"Don't worry Ashley, I'll treat you right."

"I know you will Colin. I want you inside me."

He withdrew his fingers. I felt him moving his unit towards my hole, and then I felt the tip touch the opening. The anticipation was killing me. "Are you sure you are ready?" he asked. "Fuck me!" I begged. He slowly started to push into me. The pain was strong, but I loved how it felt. He kept working it slowly into me until I was opened up wide enough to take him. Then he started to work it in and out. This felt so good.

"You're a little tease, Ashley, aren't you? You've been teasing all the guys at this party all night, haven't you?"

"Yes," I panted out.

"You even tried to seduce me on the drive here, didn't you?"

"Yess." As we talked, he was slowly building up speed. I was totally enjoying being taken like a woman, like some naughty schoolgirl.

"You wore that sexy costume to try and get a guy to have sex with you, didn't you?" His words were coming in gasps now, his breath felt sexy on my neck.

"No." I responded, " I only wanted to have sex with you!" I moaned.

"Do you mean that? Am I the only guy for you?" He was almost pounding me into the dresser he was pumping so hard. I felt my orgasm building. I hoped he wouldn't stop until we were both done. I was only able to reply with an "Mmhm!"

"Ashley¼I have¼a¼question," he was panting between his words. I knew he was going to cum soon. "Will you be¼ my¼ girlfriend?"

I almost lost it right there, the thought of stealing my sister's boyfriend was the most erotic, sexy thing I could think of. I felt him start to twitch in side of me, and I knew my climax was right behind it. "Yes! I want to be your girlfriend!" Then I felt him spray into me, which triggered my release. We stood there awhile, panting, nuzzling, and looking at ourselves in the mirror. After we got cleaned up, we decided to keep this to ourselves, for now. We went back downstairs. The party was breaking up, and we looked for our dates. Kim was talking to a couple of 'nuns' and as we talked to her, Rob showed up, and he gave me a little wink. Did he know what happened in Colin's room, or was it our deal he was acknowledging? The four of us talked for a while, then the subject of getting home came up. I guess as Kimmie was coming up with her plan, she hadn't thought this far ahead. She wanted to stay here, but every minute I was here kept her away from Colin. And put her in danger of her scheme being discovered. But she was also afraid to have someone take me home. I could see the panic going on behind her eyes. Then Colin, ever the hero, came up with a plan.

"Since Kim's roommate is gone this weekend, why don't we take Ashley there. She could find something to wear, too. Kim, you could change at your apartment and either stay there or come back here with me. And tomorrow, someone will take Ashley home. Agreed?" Colin went through the plan like he'd made it up a long time ago. Maybe he did. I liked the idea of being on campus for another day, and I looked forward to more time with Colin. Kimmie agreed to the plan, and I said it was okay with me, so off we went to Kim's apartment.

To be continued?

 

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