tagTransgender & CrossdressersWorking My Way Through College Ch. 02

Working My Way Through College Ch. 02


Saturday morning, I awoke wearing the same panties and baby doll nightie I wore to bed. If I hadn't, I might not have believed what had happened Friday night. It felt pretty good to walk around like that, so I went to the kitchen, and made some coffee. As it percolated, and as I drank it, I couldn't help but think of the night before. Thinking how liberating it felt to be the submissive one, how nice it was to be taken with such wanton force, about how nice it felt to be the one in frilly clothing.

It was so different than my sexual relations with women, where I was always the one that was supposed to be the aggressor. I could still kind of taste Dale's cum in the back of my throat, and my ass was kind of sore, but that all made me feel even better about it somehow. I felt desirable, in a completely foreign way, and I liked it.

During my second cup of coffee, the phone rang. It was Dale.

"Morning, hon. Did you enjoy yourself last night", he asked me?

I hesitated, but answered, "Yes".

"Good, now get dressed in your boy clothes. You have a doctors appointment today." he said.

"I do", I asked?

"Yes, now get dressed, I'll be there in half an hour", was his reply.

I wasn't sure what he meant, but I went to my boy bedroom, and took off the baby doll, and pulled on a pair of jeans, and a tee shirt. I went to the master bath, and brushed my teeth, and combed my hair. I was kind of surprised that I looked the same as I usually did. Somehow, I thought you would still be able to tell what I had been up to. Some socks, and tennis shoes, and I was ready.

When Dale showed up, he knocked, and then let himself in.

"You ready to go", he asked.

I nodded.

"If you're wearing panties, you are going to be embarrassed", he told me with a stern look in his eye.

I blushed, and held up a finger for him to wait. Embarrassed, I went back to my boy bedroom, and changed out of the satin panties I had on underneath, and put on regular boy briefs. I thought what a shame it was, because the panties felt so good under my jeans.

Once dressed, we got into Dale's car, and drove off. He explained to me that I was going to a medical clinic to get a checkup. He said he needed to verify that I didn't have AIDS or any other diseases.

Within minutes we were at a clinic, and Dale told me to go to Suite 2A, and check in. He said he would wait at a nearby coffee shop, and I should walk over there afterward.

For the next hour, I was exposed to the worst kind of embarrassing poking and prodding I have ever felt. I am not even going to describe it to you, dear reader. When all was said and done, they told me to come back in a week for my results.

I walked to the coffee shop, where Dale bought me a bagel, and a cappuccino. We talked about school, and just regular things, as if nothing was going on between us.

When I was finished, it was about noon, and Dale drove me back to my new home. On the way he told me to get all my homework done by 6:00PM.

Walking into the house, I felt so good about having my own place. I could do as I pleased, without any distractions or pressures. As I cleaned up the morning’s dishes, I decided to change into a pair of panties and just my tee shirt. Those made me feel so liberated!

I got to work on my homework, and just kind of submerged myself in it. Before I knew it, it was 6:30PM, and the doorbell was ringing. I quickly grabbed my jeans, and pulled them up over my panties, and answered the door.

I opened the door to greet a rather attractive woman in her mid forties, I guessed. Her blond-grey hair was pinned up, which accentuated her square Nordic looking face. She had on a white nylon blouse, and I could see that she wasn't wearing a bra, because the nipples of her c-cup tits were plainly visible. A short blue skirt, and sandals made up the rest of her attire. I was impressed.

She had a small shopping bag in her hand as she sort of let herself in before even greeting me, and I noticed her blue eyes were angry looking. She shut the door behind her, dropped the bag, and suddenly slapped me!

"You fucked my husband last night, bitch", she said!

I wasn't ready for any of this. My mind was spinning a mile a minute. She slapped me again.

"I'm Ellen! Dale's wife. You fucked my husband, didn't you, you fucking whore", was what she said next.

I didn't answer, but looked at her shoes.

"Did you like sucking his dick", she shouted!

I didn't answer.

"Answer me, you cocksucking whore! Did you like sucking my husbands dick", she asked.

I didn't know how to answer. I was so totally confused. When she raised her hand to slap me again, I answered meekly, "Yes".

That seemed to calm her down, believe it or not.

"That's OK. I saw the pictures. You're just a whore. You'd suck any cock if they paid you", she said. "Besides, he has a nice cock. I like sucking it too"!

I was so bewildered by this turn of events, I didn't even object.

She smiled, and took my arm in hers, and walked me into the living room. Her demeanor changed just like that. She sat on the couch, and told me to stand in the center of the room.

"Take off your clothes", she said sternly.

I was stunned. I knew I was going to do as she said, but my stomach was filled with butterflies at the realization that this woman I just met was going to see that I was wearing panties under my jeans. As I took off my shirt, trying to figure out what to do, she picked up the phone. As she dialed, I tried to take off the jeans and panties at the same time, to avoid the embarrassment.

"Stop! Just the jeans, bitch", she said.

I dropped the jeans, and blushed as she started talking on the phone.

"It's me, Ellen. HE'S WEARING PANTIES ", she said into the phone.

"You picked a good one this time, Dale. This bitch wears panties when she doesn't even have to", she laughed. She paused. "White nylon ones with a floral print". Another pause. "Turn around for me", she instructed.

I turned so my back was toward her. I felt like I was on display when she whistled, and said "Oooohhh... Nice ass, Dale. I don't blame you. I'd fuck that bitch myself if I was a guy".

I was embarrassed and flattered at the same time. The fact that she was referring to me as a female was a confusing thing for me.

She had a few more words with Dale before telling him to come by around 9:00, and hanging up.

"OK, off to the bathroom with you", she said, picking up her bag and taking me by the arm again.

Once in the bathroom, she pulled out a can of shaving cream, and a Lady Shick razor. She told me to shave every part of myself completely, and then meet her in the bedroom. As she left, I dropped my panties and entered the shower. After adjusting the water temperature and pressure, I decided I would start with my legs, and work upwards. I shaved first one, then the other leg, noticing how smooth and sexy they felt when I was done. I shaved what little hair I had on my chest, and underarms, and figured I was done, so I turned off the water, and stepped out. Toweling myself off, I felt so horney at the sensation of being hairless like this, and my cock started to get hard.

"You're not done yet, baby", Ellen called out to me from the bedroom. "Bring the towel, and come sit at the vanity for me".

I did as I was told, and she had me sit on the towel. She pulled a set of cordless clippers from her bag, and began removing all my pubic hair, even from my balls. As she did so, she was holding my now hard cock like a handle, using it to help her stretch my skin so she could crop my hair even closer. When that was done, she applied some shaving cream, and shaved me completely bald.

As she was shaving me, I got so aroused by the new sensations of being hairless, not to mention the fact that she was inadvertently stroking my cock, that I began to leak precum on her hand. When she was done, she held her hand up to my face, and told me to lick it clean. I did.

She went to the panty drawer, and pulled out a small black nylon thong, and threw it to me. Then the matching bra. "Put these on", she said, "Then take the towel, and shake it out the back door.

I put on the panties and bra, and as I did so, it seemed like it was a perfectly natural thing to do in front of Ellen. I carefully gathered up the towel, being careful not to let any of the hair fall to the floor, and walked to the back door in my panties and bra. Nighttime had fallen by now, and as I opened the door, I felt like I was being watched. I reasoned that the back yard was enclosed by natural brush and trees, but with the light on behind me, I felt totally exposed. If someone WERE out there in the darkness, they would definitely have gotten a real eyeful of me. I dismissed the idea as I finished shaking the towel, and went back inside.

"Now that you are smooth like a lady, let's dress you like one", she said as she stood up. "Let's pick out a sexy outfit for you".

She went over to the closet, and I followed. My dick was straining at my panties as she held up dress after dress, skirt after skirt, to my body. She finally decided on a black knee length nylon skirt with pink roses, and a sheer white nylon blouse. By the time she decided, she was very excited.

"I LOVE making guys over", she said with a squeal.

I believed her. Her excitement was contagious. My cock was drooling in my panties. When she saw the wet spot on the front of my panties, she said seductively, "We need to take care of that before you ruin your outfit".

She pushed me back onto the bed, and laid out her choice of clothing on the vanity chair. Then she came back to me, and lay on the bed next to me. Her hand sank into my panties, and retrieved my stiff cock, and began stroking it.

"You liked sucking Dale's cock, didn't you", she asked seductively.

I didn't answer.

"I saw the pictures. I could tell you liked it", she said as she continued to stroke me. "It's OK, I like watching sissy boys like you suck and fuck my husband".

I still said nothing. I just laid there, thinking about how I did like sucking his cock. How good it felt to be taken like that. These thoughts, combined with the new sensation of being hairless was making my head spin.

"Did you like feeling his cock in your ass-pussy", she asked.

I just moaned. I felt like I was going to cum at the thought of being filled with his cock.

Slowly, Ellen kissed her way down my body, and pulled my panties down enough to expose my hairless cock and balls. She slid my dick into her mouth, and began giving me a wonderful slow blowjob. She stopped periodically, just long enough to tell me how much she liked having a dick in her mouth, and asking me if I liked it too.

Finally, when I was breathing hard, and desperate to cum, she stopped, and said, "Tell me you like it"!

"YES, YES, I like it", I pleaded!

"You like WHAT", she said and started sucking.

"I like sucking cock, and getting fucked in the ass-pussy", I exclaimed, as I shot stream after stream of cum into her mouth.

She didn't swallow at all, but she didn't spill a drop. She climbed up on top of me, and kissed me, letting my own cum drop into my mouth. It was a steamy kiss. I could tell that she was enjoying the fact that she was filling my mouth with cum.

"Do you like cum as much as I do", she asked?

Still shaking from my climax, I replied that I did.

"Good, because when your tests come back negative, you're going to get plenty of it", she said coldly, as she stood up.

"What do you mean", I asked, half knowing the answer.

"Dale has a whole list of customers lined up for you", she started. "Mostly local businessmen, whose wives don't satisfy them. After they pass the same kind of tests you did today, they pay us a handsome monthly fee for the pleasure of using you. That pays the mortgage on this place, plus a whole lot more. In addition, they'll pay you on a per-visit basis. The going rate is $100 for a blowjob, and $250 for a fuck. Anything else they want, you can set your own price - we don't care. We just want the monthly fee".

My head was swimming. Dale really meant it when he said I was going to be a whore. Up until now, I kind of thought I was caught up in a kinky sex thing. No, I was tied up in prostitution, and I was the prostitute.

"Hey, you get to live here for free, and take down a nice tax free income", she started, "Unless you want to be laughed out of school by those pictures".

The pictures! How could I ever let those pictures get out?

"When does it end", I asked.

"At the end of the school year, we will let you have all the pictures, and format the hard drive of the laptop", she explained. "But at that point, if you want, you can keep on being our whore. You'll make about three to four thousand dollars a week, so you might want to stay on".

Three to four thousand dollars a week. That thought kept running through my head, as I sat there motionless.

"Hey, you told me you like sucking and fucking. Why not get paid for it", she said.

I did the math in my head. For $4,000 I would have to blow 40 guys a week to make that much, or fuck 16, or some combination.

"That's a lot of sucking and fucking", I said.

"Well Saturday night there are usually parties. You'll make lots more than on a regular night", she informed me. "Besides, you told me you like sucking and fucking. Why not get paid for it"?

I thought about how much I did like Dale fucking me, and how sexy I felt while sucking his dick. Slowly I warmed up to the thought of being used by a bunch of men. All that money coming in would be a great thing, too. I reasoned.

"Come on, let's get you dressed. Dale will be here soon, and I want to make a good impression on him", she said with a sparkle in her eyes. "I just love turning guys into sexy little sluts! Take off those wet panties".

She was obviously excited, as she fished a red and black garter belt out of the dresser, and handed it to me. As I was putting it on, she found a new black thong, and a pair of black nylons. I slipped on the panties, and sat down. Ellen rolled the stockings up my legs for me, and had me stand up so she could fasten the garter to them while on her knees.

She hugged me around the legs, and rubbed her face into my panties, and said, "You're going to be so sexy when we're done".

That made me feel good. That and the way my smooth legs felt, now encased in the sheer stockings.

Next came the skirt and the blouse. When I put the blouse on, you could see the black bra I had on underneath. "Just a little bit slutty", Ellen grinned. She was really enjoying herself, and so was I. I really felt sexy.

She took me over to the vanity, and began applying makeup. Foundation, then blush, then eyeliner, lip gloss, the works. She was creating a masterpiece, and I was it. My face definitely looked feminine. She turned me around, so she could apply fake nails, and red polish that matched my lipstick. As it dried, she went to the closet, and brought out a red wig, and red strappy heels that matched my lips and nails, and also a matching red belt.

When all was done, she took me over to the full-length mirror so I could gaze at her creation. I was amazed at the difference. You could not tell that I wasn't a girl. A very sexy girl at that. The only thing missing were the boobs. Ellen took care of that. She brought out a pair of b-cup falsies, and had me unbutton my blouse, so she could insert them into my bra. DONE! I was now a fine looking slut, as Ellen told me.

"I'm going to name you Tiffany", she said. "You look so SWEET".

I was beaming with pride by now. We spent a few minutes practicing walking in the heels, and I caught on pretty quickly. Then quick turns to make the skirt move for me. I was having fun being a girl, and Ellen was having fun being one with me.

The doorbell rang. "Must be Dale, I'll get it, wait here", said Ellen.

I heard her open the door and say, "Come on in honey. Wait till you see. Sit down".

"Tiffany? Come here, baby", she called to me.

I gathered up my nerve, and walked into the living room, and stood in front of Dale, my weight shifted to one side. Dales eyes were all over me with lust. I felt so sexy right then. I could tell he wanted me. He held out his hand, and I placed mine in his. As he kissed the back of my hand, Ellen ran to the chair, and said, "I don't want to miss this"! Before she sat down, she hiked up her skirt, and dropped her panties on the floor.

As Dale took me in his arms and kissed me like I was a girl, Ellen spread her legs, and started to moan and masturbate. His hand found the curve of my ass, and started to squeeze it. It felt so good through the material of my skirt. Dale took my right hand and guided it to his already stiffening cock. I rubbed it while I kissed him back like a wanton slut.

Suddenly, Dale forced me to my knees in front of him. His sudden aggression caught me by surprise, and I felt so helpless there, staring at his crotch. As I reached up and felt his bulging cock through his pants, Ellen let out an "MMMMM, Yeah"! I looked at her, and saw that she was lost in her own little world, enjoying the show.

"I want you to blow me, bitch", said Dale, in a heated growl.

Ellen chimed in, "Yeah, pull out his cock and suck it, whore". Her fingers were really going to town on her clit by now.

My new red nails looked so feminine in contrast to his dark dress slacks as I pulled down his zipper, and fished out his cock. Dale slapped me in the lips with it for a few seconds, before shoving it into my open mouth. Ellen sounded like she was having an orgasm just then, but I didn't look. I just started sucking his sweet cock like I was starving for it.

Soon, Dale was holding my head and shoving it in and out of my mouth, almost making me gag. I felt so slutty, and so horney like that, my own cock was getting hard. I figured Dale was going to cum in my mouth, but Ellen called out, "Fuck me Dale! Stick that cock in my cunt and cum for me".

Dale dropped me, and went over and slammed his meat into Ellen. She screamed out each time he thrust into her. Soon she was cumming, and so was Dale. He was grunting each time he stuffed it in, and I could see cum leaking out of her wet pussy now.

When they regained their composure, Ellen called me over. "Clean up my husband's dick for me, bitch".

I crawled over, and Dale rolled over onto the floor, and I swooped down on his slick, cum covered dick. I sucked and licked it until it was clean. I truly enjoyed the taste and smell of their sex as I did so.

Ellen was watching intently, and when I was done; she spread her pussy, lewdly, and squeezed some of Dales cum out of her pussy. It ran straight down to her puckered little hole. "Lick my asshole, bitch", she told me. I crawled over, and lifted her ass off the chair a little so I could get to her ass better. I stuck my tongue out, and licked the cum off her tight little ass, and swallowed it. She took me by the ears, and smeared my face all over her sloppy pussy. "Suck my cunt, you slut. Suck me like you sucked my husband".

I was happy to oblige. Just because I had a new found love for cock, didn't mean I didn't like pussy any more. I licked and sucked all that sloppy pussy that I could. Just as she was cumming on my face, I felt a hand slide up my skirt. I looked back for a second, and found that Dale had come back to life. His prick was standing straight out again.

I went back to sucking Ellen’s pussy, as she fucked my face, even as Dale was sliding two greased fingers inside me. I kept going, as he lifted my skirt, and pulled my panties to the side. When He pressed his dick into my ass, Ellen Came again all over my face, shouting, "Yes, Dale! Fuck this little whore. Fuck her"!

He was inside me in a flash, and fucking away. I felt so helpless like that. I couldn't concentrate on Ellen anymore, so she pushed my head away, and went back to finger fucking herself and diddling her clit.

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