tagTranssexuals & CrossdressersYoung Guy Goes To College Ch. 04

Young Guy Goes To College Ch. 04


Sorry this chapter took so long to post...

As I stepped outside for the first time dressed completely in girl's clothes I started to think how I ended up in this situation. Everything I was wearing belonged to my sister Robin but I was dressed up by my new girlfriend Julie, one of Robin's roommates and occasional fuckbuddy. I was wearing my sister Robin's sexy little pink thong from Victoria's Secret and little lacy 34b pink push-up bra. I also had on her denim mid-thigh skirt, pink ISU t-shirt, black pantyhose, black flats, had my long hair pulled up in a ponytail threaded through a pink ISU baseball cap.

I think I better backtrack a little and tell you how the events of the last 24 hours changed my life forever. If you want you can read the first three chapters of the story, otherwise I'll try to make this quick. My name is Jacque (Jack), I turned 18 the day before and I just hooked up with my sister's crazy bisexual roommate Julie. Julie and I played a drinking game that had us switch clothes and ended up with us having sex a number of times, each time getting a little kinkier. When I arrived last night I was set for a fun week in a college town but the first thing I did was slip on a patch of ice that caused me to fall and drop my duffel bag that had a bottle of tequila in it. So all of my clothes were coated with broken glass and booze and I had nothing to wear.

So today, Julie was taking me to the Laundromat. I had asked her if she could just go because it was going to be embarrassing for me to go dressed as a girl to a public Laundromat. Julie got pissed at me because she told me that it wasn't her fault that I fell and if I wanted our little sex game to continue I better do as I was told. Julie was bi but she definitely preferred girls to boys and I better not push my luck. I definitely am not a manly man and only have a four inch cock and since I'm not hung like a stud, I better do as I'm told and be a good little girl and I thought that she would let me continue fucking her and then she would let me lick her sweet pussy until she came all over my face.

Julie had added a few items to my outfit to make me more believable as a girl. The first was to make up my face in a believable light way like regular college girls would do. She also put a little gold crucifix around my neck to have at least one accessory to look more natural. But the big thing that she did was to slide a butt plug up my tight ass to give me a little extra sway to my walk. Julie was happy with her work and said that I wouldn't be confused with a college cheerleader but I could probably pass as long as I didn't talk too much. I am short, thin, and with long brown hair. I hoped that she was right because I didn't want to be ridiculed and I didn't want our little sex games to end.

So I stepped outside the girl's duplex with a fully loaded laundry basket and headed to the Laundromat. Julie was right behind me and as she was locking the door she let out a low whistle. "Jackie (my girl name), if I didn't know any better I'd swear that you were a real girl with little titties and a cute little ass. I think this should go off with a hitch. One thing I want you to do is walk one foot in front of the other to give your hips some more sway as you walk" Just as I was starting to feel more comfortable and thought that this might be okay I heard the next door of the duplex shut and the girl's neighbor and landlord Jim say hi.

"Hi Julie" was what he said but I swear his eyes never left me. He looked me up and down. From my little black shoes to my nylon clad legs, a quick glance at my face and then he settled his gaze on my padded bra that he could probably tell was lacy through my thin pink t-shirt. "Who's this?"

"Oh, this is Jackie, Robin's ....sister. She is a high school senior and is up visiting to see if she wants to go to school here next year."

"I see", I swear he licked his lips as he looked me over. "You know rent is due pretty soon. Can she help pay the rent?"

Julie let out a little laugh and looked at me. She pushed something that looked like a car remote and the butt-plug in my ass started to vibrate. I was caught completely off guard and Julie asked me, "Well, Jackie, do you want to live here and help pay the rent?"

The vibrating in my ass made me speechless. I was able to get out a meek little yes and I almost came or peed my self because of the sensations in my ass-pussy. When Julie realized how much an effect the vibrating butt-plug had on me she started to laugh. She then told Jim that we had to get going to get our laundry done. She then picked up the pair of white bikini panties that I had worn last night and came in at least twice. She twirled them around her finger and then held them right in front of Jim. "Jackie has to get going and wash her little panties, Jim don't you think these are cute?" Jim was speechless. Julie broke the silence and said, "If you like these you should see the little pink thong she has on now. Seeya", and with that she threw the white soiled panties into the laundry basket. She patted me on the ass and guided me to her car. As I opened the back door and loaded the laundry basket into the back seat, Julie turned off the remote that controlled the vibrating butt-plug. When she got into the car she just laughed and said, "That was fun."

As I was about to say something she hit the remote again and let out a laugh. "Don't talk, play along, and remember for wearing the butt-plug I told you I would let you stick your little clitty in my ass and I keep my promises. Now be a good girl and let's get your laundry done. Oh, and I think Jim likes you, I bet he'd love to see you in that little pink thong and bra you're wearing."

She drove to the Laundromat and would turn the remote on and off to keep me on my toes. She asked if I was close to cumming and I told her either I was going to cum or pee my pants. She corrected me and said, you're not wearing pants. You are wearing panties, hose and a skirt.

When we got to the Laundromat I assumed that we could just throw the clothes in and leave. I was planning to just stay in the car and not be seen by anyone else, being seen by Jim was bad enough. But Julie told me that you can get by as a guy just throwing your clothes in the washer and then doing something else. But girls have to watch their laundry otherwise pervs can steal your stuff, especially your panties. So I got out of the car and I realized that when I got out of the car that anyone would have been able to see up my skirt. I know I had on a maxipad to hide my cock but I didn't want to get found out or bring any extra attention to myself. I grabbed the laundry basket and threw all of the clothes into a washer. Julie laughed and stopped me and made me separate the clothes into two loads; her stuff and my stuff. She said normally she would separate things by color but since there was broken glass in my stuff she wanted to keep my things separate.

Julie put some detergent in, put in a few quarters, pushed the buttons and started the machine. I was expecting to go home so I was wondering what I should do. Julie handed me an issue of Cosmo and told me to keep my head down, read some, and that I'd get through this. She smiled and mouthed the words, "I want to fuck you" and then made her point by hitting the remote with three quick bursts and then one long buzz of the vibrator in my ass.

After calming down a little from the butt-plug I settled down and started to read my magazine. It didn't look like there was anyone else in the place but I saw a couple of dryers going. I was sitting across the room and I couldn't tell what type of clothes was in the dryer and I thought I might have been able to see a pair of red panties in one of the dryers. My answer on whose laundry it was was answered when this heavier, butch looking short haired blonde girl came out of the restroom. She was wearing a pair of sweat shorts, a sweat shirt, and a pair of flip flops. I thought it a little strange that she was wearing flip flops because it wasn't much warmer than freezing yesterday but today it was a little warmer and anything goes when it comes to college fashion.

While I was looking at the girl and what she was wearing I did not notice the expression on her face. Had I been a little more observant, I would have been more prepared on what followed next. I did notice that she was coming towards me and that she had big boobs under her sweatshirt. I heard Julie say, "Ann, don't" but I didn't see her hand before she slapped me hard across the face. Before I could get my hands up to protect myself and before Julie could get up and separate the two of us Ann threw a punch with her left hand and ripped my pink t-shirt at the top with her right hand. She ripped it so far that one of my arms was visible and my padded pink push-up bra was on display. Luckily the punch missed and Julie was able to push Ann back before she could take another swing at me.

Ann started to scream at Julie, "Who the fuck is this? Is this why I couldn't come over last night? I thought we had something good going on and right before I go home for spring break I find out that you're cheating on me with this little slut!"

Julie put her arms around Ann and I think I heard Ann start to cry a little. She was obviously upset and pissed and to be honest her slap didn't hurt that bad considering it came from such a big woman. I was actually concerned that Ann was okay and didn't think about covering up my bra. I have almost no chest hair and what I did have was under the cups of the bra. Julie kept calming Ann and started to run her hand through Ann's short hair. "Ann, settle down, let me explain. I told you the truth last night; I couldn't see you last night. The reason was because of Jackie here, this is Robin's sister. Robin and Kelly had plans so I decided to babysit Jackie here. It was Jackie's 18th birthday yesterday and Robin had a date and she didn't want Jackie to get in any trouble. So I had a few beers with her. Now let me tell you the truth, she and I did make out last night, but that doesn't change anything between you and me. I told you the first time we hooked up that we wouldn't be exclusive. I will still go out with guys and girls. When you come back after spring break, you and I will go out on a date and I'll make it really special for you....okay?"

Ann who I had first thought of as this big bull dyke started breaking down in full tears. She was a blubbering mess. In between sobs, she was saying that she was sorry. I think she apologized to me about five times and to Julie about twenty times. When Ann started to calm down a little, Julie gently caressed Ann's cheeks and looked her in the eyes. "We okay now?" Julie finished her question with a soft kiss on Ann's lips. Ann nodded yes. Julie then told Ann, "Show me that you two are okay, I want you two to kiss and makeup." Julie kissed me on the lips and then pushed me towards Ann. Ann was reluctant and gave me a quick peck. Julie smiled and said, "That's better."

Julie then looked down and noticed my torn t-shirt and saw my padded (and lightly stuffed) bra was half on display for the world to see. "Oh my God Ann, look what you did. We need to get home and fix her up. Ann, can you watch our clothes and switch them to the dryer when the washer finishes?" Ann nodded that she could.

While they were talking I tried to keep my shirt up so no one could see my pretty pink bra. Julie moved my hands away and tried to cover me but it wasn't working. Julie asked Ann what Ann was wearing under her sweatshirt hoping to find something to cover me up. Ann replied that all she had on was a sports bra and the sweatshirt. Julie condescendingly looked at her and said, "You should have thought of that before you tore her shirt. Take off your sweatshirt and give it to Jackie."

Ann looked at me with pleading eyes asking me to stop Julie but I definitely did not have any control over Julie. Ann pulled her sweatshirt up and over her head revealing a nice set of boobs contained in a tight white sports bra. Ann had a little bit of fat on her but her boobs had to be at least 38D's if not DD's. Ann quickly covered up after she gave me her sweatshirt. I quickly put it on and Julie told me she would be right back. She led Ann to the restroom and told her that she was going to get her cleaned up before we ran home so I could change.

When they came out of the restroom a few minutes later, Ann's nipples were clearly visible through her sports bra. I could also tell that Julie had kissed her because there was a little bit of lipstick on Ann's neck. Julie kissed Ann on the lips and then took me by the hand to lead me back to the car. As we were leaving she reminded Ann to change our laundry and we would be back in 15 minutes with her sweatshirt. As I was walking out the door Julie used the remote for the butt-plug deep inside of me and turned it on full blast. The sensations almost made me cum right there. Julie opened the car and we both got in. She turned it off and said that she didn't want me to cum yet. While she was driving home she put her hand under my skirt and started rubbing my cock. Even though I had on pantyhose, thong panties, and a maxi-pad to hide my cock, Julie was giving me an expert handjob over all of the material. She told me she was so horny and that she wanted to fuck me so bad. We couldn't get home fast enough.

When we got home, I was glad that no one was around, my sister and the other roommate Kelly were still at their campus jobs so Julie and I could run downstairs and jump back into bed. Before we got into bed, Julie got on her knees in front of me and literally ripped the pantyhose off of me. She tugged my cock out of the side of my pink panties and told me to leave the rest of my clothes on. She then deep throated my little cock and hopped on the bed. She raised her skirt, slid her bikini panties off and said, "I promised if you would wear the butt-plug I'd let you fuck my ass....now's your chance." I didn't need another invitation. I grabbed the bottle of lube off the counter. As I was fingering her ass and getting her ready for a good fuck, she turned the vibrator on full blast again. I slid into her ass and within ten strokes; I came in her nice heart shaped ass.

Julie, who was getting used to me coming quickly, just asked me, "Was that fun?" I nodded that it was. Julie then surprised me by reminding me that anything I did to her, she got to do to me. She pushed me off of her and my little clitty-cock slipped out of her lubed ass. She reached into her bottom dresser drawer that I realized was really her toy drawer. She handcuffed me again to the headboard, but this time I was on my knees, butt up, and facing the wall. Julie then unhooked her skirt and showed me her nicely shaved pussy. She reached back into the bottom drawer and pulled out a strap-on dildo that had an eight inch thick dildo that was nice and thick and a smaller four inch dildo with clit stimulator bumps for Julie's pleasure.

Julie got on the bed and asked me if I was going to be good and quiet. I nodded that I would but I wasn't fast enough. She grabbed her warm, and very moist, bikini panties and stuffed them in my mouth. She then got behind me and pulled the butt-plug out of me. I swear that thing made a popping sound as it stretched my anal ring. I felt three things at the same time. First, I was glad that it was finally out of me. I'm surprised that with all of the pressure on my prostate that I didn't pee myself. Second, I felt wide open. Julie told me later that my asshole stayed open at least half an inch after she took out the butt-plug. I swear I could feel the cool air of Julie's basement bedroom filling my ass. Last, I felt empty. As glad as I wanted the plug out of me, I wanted Julie to fill me up again.

I didn't have to wait long. After applying some lube to her strap-on, Julie grabbed me by the hips and started fucking me. The strap-on was a lot bigger than the plug but feeling Julie's weight with every thrust felt so good. It only took Julie a few minutes and she really started to fuck me like she was on a mission. There were a couple of times when I think she might have torn my sphincter, but I didn't care. Another time when she really pushed I felt that the dildo might actually come right out my mouth. I know that wouldn't actually happen, but it sure felt that way. Julie only took about ten minutes before she came hard on the little cock in her and the stimulating beads that rubbed on her clit with every thrust. When she came, I came again, filling my little pink panties with cum.

Right after I came I drifted off to sleep. I wasn't asleep very long when I thought I heard Julie coming down the stairs. I still had her panties stuffed in my mouth so I couldn't say hi to her. I was still handcuffed to the bed and was unable to cover myself up. I had my thong panties pulled to the side so they were covering my cock but my ass was on display as the denim skirt was flipped up around my waist. Just as I thought Julie was coming into the room, I noticed that there was a note from her saying that she would be back soon from the Laundromat and that she would un-cuff me then. Just then I heard my sister's voice say, "Julie? You down here?"

Then I heard Kelly gasp and say, "What the Fuck!!!!"

To be continued...

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