tagTranssexuals & CrossdressersYoung Guy Goes To College Ch. 05

Young Guy Goes To College Ch. 05


Sorry that this took so long to post. I will try to get the next chapter out quicker if there is positive response.


The sound of my sister Robin and her incredibly hot roommate Kelly coming down the stairs to my hopefully new girlfriend, Julie's room had me scared to death. It's not that either one of them scared me but it was the predicament that I was in, and how I was dressed, that had me worried. My name is Jacque (Jack) and the girls other roommate Julie and I had played some kinky sex games that had me get dressed in Julie's clothes. This led to some great sexual adventures between the two of us but I was now starting to think that maybe I had allowed Julie to take the game too far.

I was handcuffed to Julie's bed, on my knees facing forward with my butt up in the air. I was wearing my sister's clothes of a denim miniskirt and a pink ISU t-shirt that had been ripped less than 30 minutes earlier. To make matters worse I was also wearing my sister's lacy pink thong from Victoria's Secret and a pink underwire slightly padded push up bra with a couple of pairs of panties stuffed in there for extra padding. I also had full makeup on. But the real embarrassing thing was that my miniskirt had been flipped up onto my back and my thong panties pulled to the side so Julie could fuck my pussy/ass with her eight inch long and very thick strap-on dildo. My ass was still gaping wide open from the fucking Julie gave me and I loved every minute of it.

When I noticed that Robin and Kelly were looking in on me from the hallway I tried to explain but I had Julie's worn (and very moist) bikini panties stuffed in my mouth. After Kelly nearly shouted, "What the FUCK!" my sister Robin finally asked, "Jack, what the hell is going on here?" Again I tried to explain but it is tough to explain the most incredible 24 hours of your life when you have size 7 (that's a medium for those who don't know) cotton bikini panties in your mouth; especially when they taste so good because Julie had been creaming the entire time that we were at the Laundromat and especially when Julie made Ann take off her top and give it to me to wear to 'fix' the damage Ann had done.

Fortunately I did not have to do much explaining because as soon as Robin had pulled the panties from my mouth (she didn't fix my skirt so my ass, pink thong, and gaping asshole were on display) Julie came home and ran down the steps trying to get to me before her two roommates did. Robin looked at me, rolled her eyes, then looked at Julie, "What did you do to my brother?"

Most people would probably be apologetic if they got busted in a compromising position, but not Julie. Her response was a quick, "Nothing that he didn't enjoy. Little Jackie here has had a great time. Hell, I even made him a man."

Kelly couldn't keep out of the conversation, "Looks more like you made him a woman." As she said that she started laughing and was headed out the door but Julie stopped her and started to explain everything that happened. And I mean everything. From me falling on the ice, to Julie and I switching clothes, to the rounds of sex we were having with bigger and bigger things going in my pussy/ass.

Robin was silent the entire time with her mouth slightly open. When Julie was almost done and had explained us going to the Laundromat, talking with Jim, the incident with Ann, the vibrating butt-plug, and the great strap-on sex Robin cut in, looked to me and asked, "Did you enjoy yourself Jackie boy, or should I say girl"?

This question made me think for a moment. I definitely loved the sex with Julie. I had never thought of my ass as an erogenous zone but every time that she played with my pussy/ass I swear I came harder than ever before. So I hesitantly said, "Yes, I enjoyed it."

Robin asked if I liked wearing Julie's clothes. Again I responded that I did enjoy wearing girl clothes. About the time that I was going to tell her that I was wearing Robin's things she realized that everything that I was wearing was hers, not my new girlfriend Julie's. Robin then asked Julie why I was in Robin's best mini-skirt, and was that her new lacy pink thong from Victoria's Secret? Robin then pulled up Ann's t-shirt that I was wearing and got a little pissed when she saw that I was also wearing my sister's new pink bra. "Julie, why couldn't he wear your things? You have plenty of slutty stuff. I was thinking about wearing those undies to the Sig Ep (Sigma Epsilon Fraternity) rainbow party tonight."

Julie kept a straight face and told Robin that she tried to use her things but that SHE, as she was pointing to me, is a size smaller. She thought that Robin and I were the same size. Instead of trying to really defend her actions, she just looked at Kelly and Robin, pointed to me and said, "I think she looks cute, don't you?"

Robin was starting to get over her shock and I think she wasn't really that pissed that I wore her things. She started to smile a little and looked me in the eyes. She then asked me if I liked wearing makeup. I admit that wearing make-up was a little unusual for a guy but the way I was dressed it really made sense. Without thinking I said, "It makes me feel pretty."

Kelly who had been trying not to bust into laughter the entire time that this was going on finally couldn't hold it any longer. She started to laugh so hard that she was actually breathless. Her huge boobs started to jiggle under her t-shirt. After a good fifteen seconds of laughter, Kelly finally asked, "How long are we going to keep him a girl instead of a boy?"

Julie then got this real serious look on her face. "Well.......that's a problem. All of Jack's stuff was dirty from the broken glass, tequila, and beer so we went to go wash it. I asked Ann to keep an eye on our things so we could come back here and fuck. I left Ann there in just her sports bra and sweats and told her we would be back in 15 minutes at the most. Well, we fell asleep. And 15 minutes turned into an hour and a half. Ann got all scattered brained when a couple of guys came into the Laundromat and kind of freaked out. So instead of staying there and watching our clothes, or taking them out of the dryer and bringing them here, she took all of our stuff home with her to Nebraska (We were in central Iowa). So we don't have any boy clothes for Jack until Ann comes back next Sunday."

Robin who had been pretty quiet for everything that had gone on said almost with a thud in her voice. "What do we do now? We are so broke that between the three of us we have about $150 bucks between us and Friday (today was Saturday), rent is past due, and that money is for food and beer for the week for the four of us now. The way we drink, if we have to buy our own booze, we won't make it past Monday and that is if we eat Ramen Noodles."

Kelly answered her earlier question on how long they should keep me a girl. "I have an idea that is a little crazy, but I think it might work." After a while I figured out that this hottie might actually have a bigger bra size than IQ but at the time I had no idea so I listened. "If we keep him dressed up, we can go out every night, drink for free at the Station (the local college bar) or one of the frat houses. Sig Ep is throwing a party tonight, I still want to go. If we bring Jack, they won't let us in. If we bring Jackie, Robin's little, and to be honest, kind of cute in a geeky way, sister, we'll drink for free every night. Let's ask Jim for an extension on rent until Jackie is back home. We can't afford to buy Jack any new clothes, but between the three of us, I'm sorry two of us because Julie is a little too big in the butt, we should have no problem with outfits. Plus, I have a gift card to Victoria's Secret that I can get him some bra and panties that will fit her."

When Kelly mentioned Julie having a big butt I thought I heard Julie mention a combination of "skank, whore, bitch, and slut" but I didn't care, I asked to be uncuffed because I had to pee really bad. All of the girls kind of laughed that they had this long conversation with me still tied to the bed and my state of undress that was anything but ladylike. As they uncuffed me, I got up, fixed my thong, smoothed down my skirt and headed up stairs. As I was walking away I heard a lot of whispers, some laughter, and caught bits of conversation including "do you think he could pass as a girl.......we're not taking him to a rainbow party, are we.......what's the worst thing that could happen......mom would kill me if she knew........he is kind of cute dolled up....."

After I peed, I actually sat down and used two sheets of paper just like Julie had asked me to this morning; I looked in the mirror and was a little disappointed that my lipstick was a mess. Maybe I was more comfortable in this new role. As I was headed downstairs I was met by the three girls coming up the stairs. They told me that it was my lucky day that they were going to save me and help me pass as a girl so I could have fun drinking during spring break. If I didn't go along with everything they said I could go back home to Mom dressed the way I was right now. I quickly agreed and followed every direction they gave me.

The first thing they did was strip me naked. This was embarrassing because my sister hadn't seen me naked since I was 3 and Kelly had never seen me naked even though I did get a good peek at her in the shower this morning when she thought I was Julie (she didn't have her contacts in and is as blind as a bat). The girls then led me to the tub where I soaked, shaved, Naired, and let the girls work their magic on me. I think they washed my hair 3 times and used about a bottle of conditioner on my hair. After the bath I got out and started to dry off. I had never had a bunch of body hair, but being completely smooth felt very different, and very erotic. Julie rubbed moisturizer all over my body and I soon became very hard. She just sighed, got on her knees and deep throated my little cock. This time she pulled me close with a hand on each ass cheek. After about 10 seconds she used her middle finger from each hand to pull my asshole open. It felt like she could have shoved her whole fist in there if she wanted. When she fingered me I came instantly, and she snowballed me again so I could drink down all of my spunk.

After the blowjob I shrunk down to about an inch and a half and headed towards Robin's room so the girls could dress me as Jackie. Robin was not in the room and when Kelly saw my little cock she kind of laughed and mentioned that maybe I should have been born a girl and that they were doing me a favor because I would never get a hot girl with that little thing. The more I was around Kelly I figured out that she was really a bitch. She was super hot, but she could be just plain nasty when she wanted to.

On the bed were my clothes for the night. A slightly padded 34A violet "dream angels front hook demi bra" and matching small "starlet thong" which is full cut in the front to hide the fact that I was really a boy but a lace thong in back to show off my cute little ass. While I started to put those on, Julie started painting my fingers and toes with matching violet nail polish. After I got my new undies on, Kelly started working on my makeup and plucking my eyebrows. Fifteen painful minutes later my eyebrows were now in a feminine little arch and Kelly started working on my makeup including foundation, blush, eyeliner, violet eye shadow, violet lipstick and violet lipgloss.

After what seemed like an hour my sister who went to go get us some dinner (it was after 7 by now) returned. After she put the burgers in the kitchen she came into her room and when she saw me she started to freak out. I thought she was freaking out because I looked horrible. When she was still speechless I started to hope she was freaking out because I looked good. I looked at both Julie and Kelly for an explanation and they had these mischievous little smiles on their faces. I then looked back up to Robin and she wasn't really angry but almost pleading. "Why did you have to dress him up in violet? Why not red, orange, or yellow?" I was totally confused and had no idea what color my underwear, nail polish, lipstick, and eye shadow had to do with anything.

Kelly and Julie stated that all of the other colors were taken and they weren't going to switch their colors for the night. Julie was happy with orange and Kelly was happy with blue. Kelly then said that she had called the other three girls who were going to be there and they were set on their colors as well. Kaelie, a bleach blond with small tits was going as red and since she was a senior she was not giving it up. Trisha, a chunky red head loved the color green and said it was the only color that looked good on her for this party so she wasn't switching. And Sandra, a tall black girl, loved yellow, so she wasn't willing to change. Kelly then stated that only leaves indigo or violet and she's, pointing to me, already taken the tags off the new bra and panties so they are not returnable and we don't have money to buy new ones and we don't have time to redo the makeup, so deal with it and get dressed. Robin just looked at me and said sorry and started to get dressed herself.

I had no idea how big of a deal it is to have on the right color of underwear. I would soon find out.

When we got to the frat house I was really scared. Over my violet bra (which I was told not to add any extra padding) and panties (which had a maxi pad to hide any bulge) I wore a denim skirt, white camisole, violet tank top, and flip flops. My hair was done up really well after a few cuts to my bangs. My bangs were poofed up in front and my ponytail was set to the side. That look really emphasized how young I was. Even though I was 18 I could have passed for a 15 year old girl. I also had one of my sister's purses with me. Inside were only a maxi pad (just in case) and the tubes of violet lipstick and lipgloss.

The house was huge and usually held about 75 guys. Since it was spring break there were only 12 members there and a few friends and others around. As I said earlier there were 7 of us girls, really 6 girls plus me, but I was not going to let my secret out. I was afraid that if I was discovered I would get my ass beat. It was actually really nice pretending to be a girl. Anyone who was not a member of the frat had to pay a $50 cover charge. Girls got in free. I thought that was a lot for a party but the guys seemed to pay without batting an eye.

For the first two hours it was a lot of fun. Guys would bring me drinks. I felt that I was the center of attention, well at least one of the seven centers of attention. When I played foosball, they let me win and no one cared when I made a bad shot. Some of the guys creeped me out a little when they looked at me like a piece of meat, but it was flattering to get so much attention. One guy who did not creep me out was a freshman named Brian. He was tall and skinny and definitely a geek, but he was cute. I caught myself when I thought he was cute. I'm really a guy, even though I was wearing a lacy push up bra and lacy thong, I should not have been thinking that a guy is cute.

At eleven o'clock, the music was turned off and the frat president, Will, began to speak. "Ladies, We at Sig Ep would like to thank you for joining us in our party tonight. We hope that you have a wonderful time." At this time the other girls and I were taken to the bar that had 7 stools. Behind every stool was a small dry erase board and a marker. When Will showed me my seat, it was on the end right next to my sister. When he saw the resemblance he asked Robin if we were sisters. When she told him yes, he just smiled and said that this was going to be fun.

After we were all seated, 3 video cameras were brought out and turned on. Two were set on tripods and Brian was carrying the third one. Will then quieted down the crowd and began to speak. "Ladies, just to make this legal, I need you to look into the camera, state that you are over the age of 18, that you are here of your own free will, and that you can leave when ever you want." Brian pointed the camera at me. Even though I thought it was kind of weird I stated that I had just turned 18, was having a great time, and knew that I could leave at anytime. After the other six girls said the same thing, the president announced that the fun was ready to begin. He reminded the guys to treat the girls nicely and take turns. This concerned me and as I turned to Robin she took my hand and told me that she was sorry for getting me into this.

Will then asked all of the girls to state what color their underwear was. Starting with Kaelie on the other end of the bar who said she was all red, except for a hint of pink which got howls from the boys, down the line to me we all told these strangers what color our bras and panties were. The president then said that he didn't believe any of us and that we had to show him. Every guy in the place had their eyes on us. I was about ready to start laughing because no way would my prim and proper sister show anyone her undies. When I looked over though, she had already taken off her polo and was unbuttoning her jeans revealing her see through indigo boy shorts and bra. Looking down the line every girl was down to bra and panties in under a minute. I hadn't moved. Will walked over to Robin and asked if there was a problem. Robin explained that I was just nervous. Robin then quickly added that it was my period and didn't feel like taking off my skirt.

He leaned in close to my ear and whispered that it was okay to be nervous, have fun and you'll have a story to tell all the girls back in high school. He also said that I didn't have to take off my skirt as long as he could get a good view of my ass in my panties. I still sat there dumbfounded but Robin helped me by lifting my tank top and cami off in one motion. I then realized why the girls told me not to pad my bra. When my top came off I could hear some of the guys in the crowd mumble "....she's flat...she's probably a virgin...she better be good or I want my money back..." Those comments didn't bother me much because Will was leading me behind the bar out of view from every one else. Without asking, he spun me around so I was facing the crowd and had my back to him. Will then lifted up my skirt, looked at my panties, and spanked my ass HARD. I think I had a handprint on my butt for two days. When he was satisfied he led me back to my seat.

Robin leaned in and apologized again. She explained what was going on as fast as she could. This was called a "rainbow" party. The girls get to drink for free year round if they participate in three of these a year. Robin then told me the guys were not allowed to fuck us, and they had to keep their groping to a minimum. But every guy in here was going to go through the line and each girl was going to suck on his dick for two minutes. Each girl sucks at a different depth so if a guy can last through all 7 girls his cock will have all 7 colors of the rainbow on it. If he makes it without cumming, he gets his picture with his cock out surrounded by us. If he cums he is out. The guy who can last the longest without cumming gets the money. The house puts up 250 bucks plus the fifty dollar entry fee from each non-member.

She then told me it gets worse. There are 18 guys here and the girl who gets the fewest guys to cum in her mouth gets a punishment. The punishment is random, drawn from a hat, but they are bad. Nothing really illegal but close. Julie had to masturbate in her psych class to full orgasm once. Kelly had to walk home completely naked after one. Kaelie had to go ask one of her professors to get a higher grade on a paper and when he said no, Kaelie had to strip down and beg him to fuck her for an A. Robin then told me that her punishment once was a lesbian porn photo shoot where you could clearly see her face. The photos hadn't made it out yet because she paid the photographer a lot of money for them.

Report Story

bypantysubsissy© 41 comments/ 101791 views/ 28 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: