tagTranssexuals & CrossdressersWorking My Way Through College Ch. 01

Working My Way Through College Ch. 01


It was the first week of the fall semester, and I still didn't have a place to stay. I had been sleeping in my car each night, and showering in the men's locker room each morning. I was standing in the Student Union Hall looking at the dwindled list of low rent housing units that were still available. "If only I had gotten here a few weeks earlier", I thought to myself. The only places listed were out of reach for what little money I had after tuition, books, etc. I was feeling desperate since I also still needed a job, my grant money was almost gone, and my student loan check hadn't arrived at my P.O. box yet.

As I looked down from the bulletin board, my hopes of finding a cheap place dashed, a voice came from beside me.

"Hi, I'm Dale", he said. I was kind of startled - I hadn't noticed him arrive. "Hello", was all I could muster in response.

I looked him up and down quickly. He was a white guy in his mid-to late 40s with dark hair and a trim build. Kind of average looking. In his hands were a binder, and a picture of a house with a paragraph under it, and some tear-off phone numbers. The kind you see on the board.

"Looking for a place?” he asked.

"Yeah. They're all too expensive for my budget, though", I replied. I felt like crying. He must have noticed.

"I was going to post this, but now I think I'll wait", he said.

I took another look at the picture. It was a small, one story house, with a small yard, and no other houses visible in the picture.

"Too expensive for me", I said.

He looked at me with what seemed like deep sympathy, and said, "Why don't I buy you a cup of coffee".

"Sure", I said. Why not? I didn't have anything better to do. Otherwise, I'd just have to go back to my car, drive to a rest area, and sleep. I was sure tired of that car by now.

We walked a short distance to a coffee shop, where he had me take a seat at a table while he ordered some coffee for us. Before I sat, he gave me his binder, with the house-for-rent ad. While I waited, I looked at the picture again. My mind wandered, and I began to picture myself living in a house, instead of my car. I pictured the refrigerator full of food, and compared that to the McDonalds meals I had been eating for the last 2 weeks. I pictured myself sleeping in a bed, instead of my backseat. A television and a couch, instead of my car radio. It was a dream, compared to living out of a car.

The paragraph under the picture read, "Furnished 2 br, 1 1/2 bath. 1800 sq ft. w/attached garage. Rent negotiable. Please inquire". Definitely more than I could afford, but it was nice to dream for a minute.

Dale sat down across from me, and handed me a cup of coffee. We made small talk for a few minutes, like "What's your major, how long have you been in town", stuff like that. Eventually, I had told him all about my dire financial situation, and the fact that I was living out of my car. He seemed genuinely sorry for me. Not that I wanted any pity from anybody, but I was in a pretty pitiful state just then.

"Why don't you move into my rental house", he asked.

"That HAS to be more than I can afford, Dale", I told him.

"Not so fast", he said. "I just inherited it from my sister who passed away", he told me. She had been sick for a long time, he explained. Now that she was gone, the house was sitting empty, and it was paid for. All he needed to do was pay the taxes each year, and keep it maintained, he explained. If I stayed there, I could help him out by keeping it clean. We could work out the rent details after I found a job.

"What if I can't find a job", I asked?

"I'll help you get some work", he said with a smile. Somehow I knew he meant that.

It was all too good to be true, but here he was making me an offer to live there! I could go from living in my car, to living in a house not far from school. Of course I jumped at the chance.

"Let's go over there now", he said. It was Friday afternoon, and I didn't have any classes until Monday morning, so I followed his BMW in my old Ford, until we came to the house. It was just as it looked in the picture. Small, but well kept.

Once inside, he gave me the quick tour. The kitchen was small, but had a dishwasher, refrigerator, even a microwave, and a toaster. The living room had a nice couch and loveseat, an entertainment center, with a nice TV, and a small stereo. A couple of lamps, and a large picture window with a view of the back yard. The drapes were cheap looking, but I didn't mind at all. The bathroom in the hallway was tiny, but had a shower stall in it. No more going to the locker room to shower, I thought to myself.

He led me into the small bedroom on the left. "This will be where you stay", he said. "I hope you don't mind".

I didn't mind. It had a single bed, which was much better than that back seat I had been sleeping in. A chest of drawers, and a nightstand with a lamp were all that were in the room. It was furnished very cheaply, like most guest rooms are, I supposed. Still the drawer space, and a small closet would be all I needed. I was grateful.

Then he took me into the master bedroom.

"This was my sister's room. I'll show it to you, but please keep out of here. I kind of want it to look like it did when she was alive", he said. I solemnly agreed.

It was very different than all the other rooms. Everything in there was very feminine. The bedspread on the large bed was pink with small roses printed on it. Four posts rose up from the corners of it, and they were painted flat white. The bed looked very soft and inviting.

A very expensive looking set of furniture consisted of matching dresser with a large mirror, a large chest of drawers, and matching night tables on either side of the bed, filled the room very tastefully. A pink vanity in the back corner had 3 mirrors, so you could see yourself from different views. Perfume bottles, makeup, and other feminine items were all over the place, as if a woman still lived there.

The master bath was very large, with a huge bathtub, and brass fixtures everywhere. In front of the large mirror were all kinds of makeup, lotions, etc.

Back out in the bedroom, he opened the top drawer of the dresser. Inside, it was filled to the top with bras and panties of all sorts. He left it open a few seconds, while I looked at it. The sight of all those panties and stuff made me kind of horney, but I felt him look at me, so I stopped staring. I looked back at him, and he opened the small drawer on the right. In there were stockings and garters, all very neat. Again he held the drawer open for what seemed like a long time, but really only a few seconds. I wondered why he was showing me her underwear drawers, but I didn't say anything.

"Definitely leave those drawers alone", he said.

"I will", I promised.

Then he opened the walk-in closet, and showed me all the nice dresses, and shoes in there. Some of them seemed pretty sexy for a woman I figured had to have been in her 40's, but I didn't say anything. After a few seconds, he closed the closet, and we went into the living room, and sat down.

We talked for a while, about my chores. Basically, I was to keep the place clean on the inside and let him know if there were any repairs needed, but he had a gardener that would take care of the outside.

"How am I going to pay for this", I asked.

"We'll just have to find you a job, wont we", was his reply.

After a while, he left, and I unpacked my car for the first time in weeks. I got everything setup just right, and went to take a shower.

When I got in the shower I found that the soap and shampoo were perfumed, and kind of feminine smelling. I didn't really care, since nobody else was around.

After the shower, I found that there were no combs on the sink, only a pink brush. As I brushed my hair, I thought how his sister must have loved pink. I found a robe on the back of the door. It was a faint pink in color, but again, nobody would see. I slipped it on, and went into the living room to watch TV for the first time in a few weeks.

There was nothing very interesting on, but I kept switching channels in hopes of finding something.

I began to notice the feel of the silk against my body, and how erotic it felt. I touched my nipple through the silk, and was delighted with how wonderful it felt. I let my hands roam all over me, and was getting very turned on. I wrapped the silk around my hardening cock, and almost made myself cum instantly.

Then I got a thought. I knew it was wrong, but I did it anyhow. I went into the master bedroom. By now it was almost 10:00PM, surely Dale would not be back. It would be safe to be in there, I thought. I turned on the overhead light, and the pink shade caused the room to glow in a very feminine light. My heart was pounding as I opened that center drawer where all those panties were. There were all kinds of them in there, in every color and fabric you could think of. I selected a pair of red nylon lace ones, and stepped into them. The feel was absolutely fantastic as I pulled them up and on. I wondered how women could walk around like this and not be horney all the time.

I decided to go back out to the living room in my pink robe and red lacey panties, and just enjoy the feel for a while. I was being naughty, and I liked it. I was touching myself and wondering what it must be like to be a woman for a while when suddenly, the doorbell rang!

I shot up off the couch, and ran to my bedroom. I dropped the robe on the floor, and grabbed a pair of shorts and a tee shirt. I put them on over the panties to save time.

When I opened the door, it was Dale. He didn't look as friendly as he had before, in fact he looked kind of mad.

"Come on in, Dale", I said.

He walked in, and when I shut the door, he took me by the hand, and pulled me into the master bedroom.

"I thought I told you not to come in here", he said loudly.

"I didn't", I lied.

"Yes you did", he remarked, and went to the dresser, opening the panty drawer.

"You've been in here, haven't you", he demanded.

How did he know, I wondered. The blinds were pulled, and the window was at the back of the house where only the yard and a wood line were visible. I couldn't have been seen.

I tried to deny it, so he went into the closet and pulled a laptop computer off the top shelf. I had no idea it was there. He clicked around a few times, and finally opened up a picture of me wearing the panties and robe, while admiring myself! I was so busted.

"Now what do you have to say", he asked?

I was so humiliated, I couldn't talk. I looked at the picture, and decided there must be a camera over by the vanity.

"You're wearing those panties right now, aren't you", he said.

I was mortified. Caught red handed - no, red pantied. Red faced, too, I might add.

"Take off those shorts and let me see, Panty Boy", he ordered.

Ashamed, I slowly undid the button on my shorts, and pulled down the zipper. Finally, I let the shorts fall to the floor, and stepped out of them, ashamed of the fact that I was now standing in front of Dale wearing red lacey panties.

"Take off the shirt, too", he demanded, "and put this on". He handed me the matching red lace bra.

I felt so humiliated standing there in a bra and panties like that.

He grabbed my arm, and roughly led me over near the vanity. "Look at yourself, bitch", he said.

I looked at my reflection for a few seconds, before Dale forced me to my knees in front of him.

As he was pulling his cock out of his pants, he was saying,” You look like a bitch, let's see if you suck like one, too. From now on you'll do as I say or those pictures will be all over campus. You want that?".

"No", was all I could say, as I was now confronted with a semi-erect cock for the first time in my life. He swung his cock and hit me in the face with it.

"Suck it, bitch", he said. He held my head with one hand and fed his dick to me with the other hand. I instinctively tried to resist, but under the circumstances, I didn't have the will. When his dick was completely in my mouth, he turned my head toward the vanity. He moved a perfume bottle, and suddenly I saw the camera pointed at me.

"Now I've got some nice pictures with you dressed in women’s underwear, and with a mouth full of cock. Are you going to do as I say, bitch", he said as he turned my head to look at him. He never took his dick out of my mouth, so I just mumbled "mmhmm".

He was fucking my face hard, and when I looked in the vanity mirror, I could see myself sucking him off. The sight made me very horney, as opposed to the scared feeling I had been having. I watched as his cock disappeared into my mouth, then reappeared, and I began to get into it. I started sucking, and squeezing it with my tongue, and kind of teasing myself in the mirror. I was surprised at how much I was enjoying this. Not just the fact that I was giving him a blowjob, but also the helpless feeling that I had. In some strange way, being forced to do this made it OK to be sucking his cock, and somehow that made me free to enjoy it.

"Yeah, suck it you little sissy whore", he moaned.

Somehow it made me feel even hornier when he said that, so I backed off, and said, "Cum in my mouth".

He grabbed my hair again and started ramming his hard cock in and out of my mouth, yelling, "Cock sucking sissy bitch. Blow me, you cunt".

Hearing those words made me feel even more horney, and by now my dick was stiff as a rock and sticking up out of the panties.

Finally, his whole body went rigid, and I could feel his cock twitch in my mouth. It spurted into the back of my mouth, and I swallowed it as quick as I could, while he was groaning, and calling me a Sissy Whore.

When he was done cumming in my mouth, he pulled out and put his dick back in his zipper, as I wiped the saliva and cum off my mouth.

"Go get your robe on, and meet me in the living room", he said coldly.

"Can't I just change", I started to ask.

"No, now hurry up", he said.

When I walked into the room, I felt very awkward, wearing this pink robe, with matching red lace panties and bra, while Dale was wearing his normal male clothes. Somehow it was different being on my knees dressed like that, while being forced to give him a blowjob. I must have looked pretty sheepish.

"Aww, come on in and sit down. You'll get used to dressing like that", he said in a matter-of-fact tone. I wondered what he meant by that. I didn't have to wonder long.

Dale pulled 2 twenties and a ten out of his wallet and dropped them on the coffee table.

"What's that for", I asked in horror, already knowing the answer.

"That's for being a good whore", he replied with a sly grin.

"I don't want that", I told him. I was shocked, and trying to maintain at least some of my dignity.

"You'll take it, you whore. If you don't, then you're just a slut. I'll let you know when I want you to be a slut, but for now, you're a whore", he said in a sharp tone. "Unless you want everyone at school to see the pictures of you sucking my cock, dressed like a bitch", he went on.

I felt so hopeless. He had me where he wanted me. I considered running away, and quitting school, but I couldn't. I had too much at stake to just quit. I'd never be accepted at another school if I did. I resigned myself to the fact that I would have to play his game. Actually, that thought kind of aroused me, since I had to admit to myself that I actually liked what I did a few minutes earlier.

He told me that on days that I didn't have classes, I would live, and _dress_, in his sisters room. I would spend all day dressed in drag, and at night, I would wear lingerie to bed. No stuffy pajamas for me. Also, I was not to go outside on those days. Since I had classes on Monday, Wednesday and Friday, I could dress any way I liked. I was to get my homework done the same day it was issued whenever possible, so it didn't interfere with my "Other Activities". Additionally, I had all day Saturday until 5:00PM to do as I wished.

"Now let's get you ready for bed", he said.

"But it's Friday", I complained.

"This time doesn't count. Now let's go. Into the bedroom", he told me.

He picked out a pair of pink satin panties, and a short maroon satin slip, and handed them to me. As I stripped off what I was wearing he went into the closet. I shuddered visibly when I felt the satin sliding up my legs. When I pulled them up all the way, I couldn't help but run my hands over my ass and my balls. My dick got hard immediately. The feel was so erotic. When the slip fell down over my body, it was like I was drenched in a smooth sensual liquid. It was so erotic feeling.

Dale came back with a brunette wig that was styled very nicely. I knew what he wanted me to do, and a day earlier I would have run out of the house, but today, I was liking it. I reached for the wig, and put it on, walking over to the vanity, so I could get it just right. When that was done, I noticed some red lipstick on the vanity, so I picked it up and applied it to my lips. When I was done, I admired myself in the mirror. The slip was short enough that you could seem my panties even when I was standing up. It was amazing. I could almost pass as a woman! And I liked it!

Dale was watching with amusement, and said, "Come over here".

"Why", I asked coyly.

"You know why", he said.

I looked at his crotch, and saw a growing bulge, so I decided to just go for it. I slowly walked over, in as feminine a way as possible, and sank to my knees. I undid his zipper, and pulled out his stiffening cock. I couldn't believe the change that had come over me. Here I was dressed in women’s intimate clothing, and about to give a blowjob, only this time I wasn't being forced. I actually wanted to do it.

I rubbed his hardening cock through his trousers as I looked up at him.

"Are you going to fuck my mouth with this?” I asked him. I was trying to be as feminine as possible, and I was enjoying it. He was getting very horney again, and I was enjoying teasing him.

He kicked off his shoes, and said, "Pull it out, and suck it, bitch".

I lowered his zipper, and reached in to find his cock. When I pulled it out, I began licking it, as I looked up at him, teasingly. I sucked it into my mouth, and it was still semi-hard. It felt so good to feel it getting harder in my mouth. Soon, he was fully erect, and pumping it in and out of my mouth.

"Take my pants off me, whore", he ordered me.

I undid his belt, and button, and slid the pants down his legs while not letting his cock out of my mouth. He stepped out of them, and then grabbed me by the shoulder and stood me up. His cock came out of my mouth with an audible "pop". I was amused. He spun me around, and slapped my panty-covered ass hard.

He said, "Get on the bed, bitch. On your knees", and with that he shoved me at the bed.

I knew what was next, and I was afraid. I was about to get fucked in the ass. Nobody ever did that before, but somehow it seemed natural under the circumstances. I saw myself in the mirror, and the sight of it made me horney. I looked pretty sexy, and I decided I needed to get fucked, if only to se what it felt like.

Dale had gotten some lube out of the nightstand, and greased up his cock. He took more lube, pulled my panties aside, and squirted it on my ass. Then he stuck 2 fingers up there. I was surprised it didn't really hurt.

After pumping his fingers in and out, he asked, "You ready to fuck me, bitch"?

"Yes", I said.

"Say it, bitch", he ordered.

"I'm ready to fuck you", I said. By now, I was rocking back and forth, fucking his fingers, and it felt good on my prostrate.

"Tell me what you want, you little sissy bitch", he said, as he slapped my ass.

"I want your whole dick up my ass", I replied.

"It's an ass-pussy, bitch. Call it an ass-pussy", he shouted.

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