Will Work For Food

Copyright M.C. Questgend 2017 – all rights reserved

Reproduction and copying by any means is not allowed under copyright law. This is a work of fiction.  Any resemblance to characters, living or dead, business establishments or events are entirely coincidental.

WARNING: This book contains material of a very explicit sexual nature and is intended for adult audiences only.  The author does not condone unsafe sexual practices. 

For ten years, I seemed to have my life in order.  Still single, I had a great job, a nice car, and a fantastic apartment.  But like most things, they don’t last very long. I was called into my boss’s office and was informed I was being let go because of the company’s financial difficulties.  While I was hopeful that it was only temporary, I still needed to make sure I had income coming in.

After four weeks, my severance package was all but gone.  I had no choice but to cash in my retirement package to stay afloat but that didn’t last long either.  The scary part was I was not seeing any offers come in for a new job.  No one was hiring and time was running out.

I had to lower my options to just have a job.  I tried searching for anything from a waiter to a file clerk to a janitor… a huge change from the analyst job I had; but once again I was struggling to get the foot in the door – either because I was overqualified or because they were looking for a specific image.  Strangely enough, I always thought the discrimination was driven in the other direction where women were being passed over in favor of men… now I am being passed over in favor of women.

Actually, this gender challenge opened a new opportunity but also presented some challenges.  Being a closet crossdresser, I had already mastered my look, but no one ever saw Jenny. Since I was in crisis mode, I fought with the possibility of introducing Jenny to the world and ultimately came to the conclusion that I needed to try anything to stay on my feet.

So, I gave it a shot.  I applied with a number of businesses as Jenny instead of Jerry and while I did receive more interest, the issues remained.  Jenny did get an interview with a company not far from my apartment. This was a tough one.  When Jenny showed herself, she was usually dressed more like a whore than a professional businesswoman.  So, the choice of wardrobe was critical.

After going through my closet, I became frustrated that I couldn’t find anything decent to wear.  This meant I had to go shopping.  I returned from a second-hand dress shop where I bought most of my clothes and where the sales staff knew me.  They were a little shocked to see me looking for something more conservative but were very helpful and found exactly what I needed.

The day of my interview, I got cleaned up – shaving from head to toe.  I then stepped into character.  I put on my favorite lace bra and panty set.  I slipped into a pair of black tights and put on the new grey skirt I bought.  After putting on a white blouse, I moved to the vanity mirror and began the make-up process.

I had to remind myself that this was for a job interview and not for a night on the town.  So, I stayed conservative with smokey brown eyes and rose-colored lips.  I then moved to my hair adding some extensions to lengthen my hair to my shoulders. After a few accessories – earrings, bracelets, and a necklace, my transformation was complete.  I walked back into the kitchen and sat at the table going over my resume and trying to anticipate interview questions. 

I decided to walk to the interview since it wasn’t far and I needed to calm down. Since I had never been out dressed before I was scared, I wouldn’t pass or worse, I would be recognized.  I stopped at my favorite coffee shop on the way and picked up a small drink and sat at one of the tables reading the newspaper. I looked around a bit and I was pleased that no one had really noticed. 

I arrived at the office building and sat in the lobby with three other female candidates.  I watched them carefully as they sat with their legs crossed while playing with their hair or checking their make-up.  I on the other hand was sitting with my legs together and the folder on my lap.  It was clear I looked nervous, so I tried to blend in.

As I started to cross my legs as I reached for my purse, I heard my name called.

“Jenny?” the receptionist called.

I paused for a moment then answered, “Yes, that’s me.”

I got up and followed the receptionist to the conference room. After she walked away, I stood in the room waiting for the interviewer to come in.  Still nervous, I walked around the conference room table and stared out of the large windows overlooking the parking lot.  I was still going over everything in my head and getting more nervous by the minute.  Just then a voice startled me from behind and ended my nervous daydream.

“Good morning, Jenny,” a man said.

“Good morning,” I replied as I turned around.

“I didn’t mean to startle you, please have a seat,” he said.

I sat down across from him at the table and began the interview.  After the normal Q&A, we moved to more personal questions.

“So, what do you do for fun?” he asked.

“Oh, I like to read and watch television,” I replied.

“Oh, a little more of a homebody, huh?” he asked jokingly.

“Yeah, something like that,” I replied.

“Do you spend any time outdoors?” he asked.

“Not really, I am a private person and really passed the social interactions when I am not at work,” I replied.

“I know what you mean.  I am surrounded by people all day and sometimes I just want to be a hermit – even for a little while,” he said.

“Exactly,” I replied.

He continued to look over the resume and application and as the interview was ending, he gave me the next steps that would be taking place.

“So, I will turn your information over to our security team so they can complete your background check and once that is done, we can schedule you for a follow-up interview with the department head who will make the final decision,” he said.

I was floored.  Background check?  I am screwed. I completely forgot about that. They will pull up the information on the app and figure out I am not a woman. Forget not getting the job, what will I do after that information is discovered? No matter what the legal rules are, the information is bound to get out, then what will I do?  I didn’t know how to respond so I sat quietly.

“Is that okay?” he asked.

“Oh, sorry, uh yeah sure,” I said, “Can you tell me how long before you make a decision?”

“We plan to fill this position by the end of the month,” he said.

We shook hands and I left the building and walked back home.  On the way, I had a number of things running around in my head.  What was going to happen if they found out about me?  Will I get the job anyway?  What am I supposed to do this month?  I am already struggling to make ends meet and I didn’t have anything left in the reserve tank to take care of my bills.

With everything I was thinking about I didn’t realize I passed my apartment and kept walking down to the edge of downtown.  It was getting late and when I realized how far I was I started to hunt for a cab to take me back home.  As I tried to stay in some highly lit areas, I was getting scared about being in a bad part of town all alone – especially in the vulnerable attire I was in.

I was passing a local bar hoping to find a ride and as I walked by the front door, a man walked out.  Obviously drunk, he stumbled out the door and bumped into me.  After struggling to keep my balance, I stared at him with an angry look. As he looked up at me and saw me walk away, he began to follow me and yelled out propositions.

“Hey, Cutie, how much?” he asked.

I simply ignored him and continued walking down the street.  He however did not let up.

“Come on, Honey, how much?” he said.

After a few more inquiries, I finally responded.

“More than you can afford,” I said.

“Oh, are you that good?” he asked.

“You’ll never know,” I replied.

“Are you sure about that?” he asked.

“Go back inside,” I said requesting he go back into the bar.

“Come on one hundred bucks,” he said.

He got no response.

“Five hundred?” he asked.

Again, no response, but it got me thinking about my current situation.  Was there a number that would make me stop and turn around?

“You are not worth five hundred anyway you whore,” he said.

I don’t know why I stopped and responded, but I did. 

“I guess you will never know,” I said.

“Oh, really, I have it right here, Honey,” he said as he pulled a wad of cash from his tight jeans.

“Looks like you are a little short,” I said as he continued to walk towards me.

“Oh Honey, don’t worry about that,” he said as he reached into another pocket and pulled out another wad of money.

After looking at about a thousand dollars, I started to think, what would I have to do to earn that kind of money? Before I knew it, he was standing right in front of me and I felt that since he tried this hard to get my attention and I was in need, I figured I would take him up on his offer.

“So, what do I get for a grand?” he asked.

“Well, what do you want?” I replied.

“The whole night,” he said.

There was no way I was going to give him the entire night, but I didn’t want to leave empty-handed, so I compromised.

“Well, for three hundred, I will give you head,” I said with some hesitation.

“I want more than that,” he said.

“How much more?” I asked.

“I want to fuck you in the ass,” he said.

While I had never done that before I often dreamed about it, but I wasn’t going to let him fuck me for free.

“That will cost you another five hundred,” I said.

“Eight hundred, are you kidding me?” he said.

“Take it or leave it,” I said hoping he would leave it.

He looked me over for a quick second before responding.

“Do you have a place?” he asked.

“No, but there is a hotel around the corner,” I said.

“Deal, let’s go,” he said.

Shocked, I wasn’t sure what to do.  As we walked to the hotel, he had me wait until he checked in and when we got in the room, he started to unzip his fly. 

“Money first, honey,” I said.

He threw the cash at me and moved closer to me.

“Open up sweetheart,” he said as he pulled his cock out of his pants.

I still wasn’t sure I could go through with it, but he put his hand on my shoulder and pushed me to my knees and since I was down there anyway, I figured I would give him what he paid for.  So, I took hold of his firming cock and stroked him gently.  As he grew and got harder, I began to lick the tip of his cock, which he was appearing to enjoy immensely.  I continued to stroke and lick him while my other hand was wrapped around his legs and my hand firmly on his ass.

He began to move back and forth trying to get me to take more, but I was perfectly fine tickling his cock hoping he would come early, and we would be done.  I wasn’t that lucky.  He grabbed the back of my head and forced me to take every inch he had to offer. 

“Oh yeah, that’s it, take it all,” he said as he moaned.

I was in no position to respond as I almost choked on his hard cock.  I continued to pleasure him orally and noticed that his hand came off the back of my head and he began to bend down running his hands down my back.  His massage was starting to turn me on, but I had to be very careful as I didn’t want him to find out I was a man.

“Okay, okay… get up,” he said softly.

He moved to turn on one of the lights and I immediately stopped him.

“Lights stay off sweetie,” I said.

“Okay, bend over,” he said.

I unzipped my skirt and pulled my panties and tights down just far enough to expose my tight ass.  He moved behind me and I could feel his hand reaching for my hole.  I moved his hand over my ass and began wetting my ass. With my other hand, I reached for his cock and pulled him closer to me.  I positioned his cock right up against the opening of my virgin pussy and with his help pressed it further until the tip had penetrated me.

“OOOOHHHH, you are so big,” I said.

“You are so tight,” he said.

“I’m a virgin sweetie, give me more of your meat,” I said as I enjoyed the feeling of his cock inside me.

He continued to slowly penetrate me.  In and out and as he began to move faster, I had to slow him down.  We continued to enjoy the connection we were making.  I did my best to control his wandering hands and while he got through a couple of times and nudged my fake breasts, I was able to keep my true identity under cover.

“I want to cum in your mouth,” he said.

“No, come in my ass honey,” I said, “I want to feel your load shoot inside me.”

“UUGGHH… UUGGHH… UUGGHH,” he grunted as he continued to fuck my virgin hole.

“OOOO… AAAHHHHH… Come on baby cum inside me.” I said.

With a couple more insertions of his cock in my ass he was ready to explode. Before I could keep him inside me, he pulled out and jumped in front of me while I was still trying to gather myself. I looked up and caught his load all over my face.  He rubbed his cock all over my face and onto my red lips.  I couldn’t resist and opened my mouth and licked his cock and cleaned off all the cum he had left. When we were done, he zipped up and walked out, leaving me on the floor in the dark, covered in his juices. 

As he left, he simply said, “You were definitely worth the grand… thanks whore.”

I got up and struggled in the dark to get to the bathroom.  I cleaned up as best I could before turning on the light. When I looked in the mirror, I could see how destroyed I looked. I immediately ran to the door and locked it so no one would come in.  I then picked up all of the money and put it in my purse.  I went back to the bathroom and washed my face.  My ass still sore from the pounding, I delicately cleaned up back there and called a cab.

I got home and went and took a long shower.  Afterward, I started to sit at my computer, but I was still too sore to sit.

I checked my email and got a message from the company I interviewed with earlier in the day.  They wanted to have a second interview as soon as possible. Now I was wondering if they had even done the background check, but that didn’t matter, I was close to having a job. If I had to dress up every day to pay my bills I knew now that I could. The next morning, I called the number that was in the email and spoke to the gentleman who interviewed me.

“Hi Jenny, Thanks for calling me back.”  He said.

“No problem, sorry I didn’t call you sooner, but I got home late last night,” I said.

“Not a problem,” he replied, “I wanted to know if you wouldn’t mind meeting me for lunch today.” 

“Is there a problem?” I asked.

“No, I just had a few more questions and since I am going to be out anyway, I figured we could do that over lunch.”  He explained.

I hesitated and said, “Sure, what time did you want to meet?”

“How about eleven o’clock,” he replied.

We agreed on a restaurant that was easy for me to get to and finished the conversation.  I went back to the bedroom and realized I only bought one outfit for the interview and needed something else to wear.  Since it was a lunch meeting, I figured I could try and go a little more casual; so, I picked out a pair of tight leather pants and a loose white blouse. I fixed my hair and make-up again after the night of rough sex and went to the restaurant. When I arrived, John Gregory was already there and waiting for me.

“Hi Jenny,” he said.

“Hi, Mr. Gregory,” I replied.

“Sorry we had to meet here,” he said.

“No problem,” I replied.

We ordered lunch and he began to explain to me why he really wanted to meet away from the office.

“There were a few things that I wanted to clarify before I sent it over to HR,” he said as he pulled my application and resume out of his bag.

“Sure, if I can clear it up I will,” I replied.

“It is a little personal and I don’t want to just say it out loud, so I highlighted the portions that needed clarification,” he explained.

He handed me the paperwork and as I reviewed it I knew that the cat was out of the bag.  In my impatience to get the application completed, I forgot to fill it out as Jenny; so, my gender was incorrect.  What was also incorrect was my resume which had my real name on it.  Not easily explained away.

“I guess this means I am not going to get this job, am I?” I asked.

“Not necessarily, but it will have to be explained,” he replied.

“I would rather not have to explain this,” I replied.

“I understand,” he said.

“If I may ask, we didn’t need to meet to clear this up.” I said, “Why did you want to meet with me?”

John hesitated for a moment looking down at the paperwork.  Almost embarrassed to say another word.

“I saw you yesterday,” he said.

“Where?” I replied.

“At the bar on 10th street,” he replied.

Now I was embarrassed, but how much did he really see?

“I am not sure what to say,” I said.

“My concern is for you and your safety, not just for the company,” he replied.

“I appreciate that, but I am not sure what you mean,” I said.

“If I bring you into the company, what will we see?” he asked rhetorically, “and… how will your look reflect on the company?”

“I still don’t understand, I figured with this information, I would have no shot,” I replied.

“Your resume spoke volumes, but the concern is the look you portray.”  He explained, “It is clear you are very good at what you do, and you are certainly qualified for the position, but can you perform at that level every day… as Jenny?”

“To be honest, I am not sure.” I explained, “This was the first time I had ever gone out as Jenny.”

“So, you understand my concern?” he asked.

“I think so,” I replied.

We continued to talk, and I realized all he knew was that I was dressed as a woman and not about the night with the other “John”.  As we talked, I could see that he was becoming friendly and even complimented me on how well I passed as a woman.

“Can I ask you something?” he asked.

“Sure,” I replied.

“You said you don’t go out dressed.  Why did you choose to now?” he asked.

“I was in need of a job, and I was getting passed over.

I became desperate.  So desperate that I have done things I am not proud of.”

I explained.

“Sorry to hear that,” he replied, “I know times are very tough right now and I am not sure what I would do if I were in your situation.”

“Well lucky for you… you’re not.” I replied.

“I have to admit, you had me fooled,” he said.

“What do you mean?” I asked.

“I really thought you were a woman and I found myself instantly attracted to you,” he replied.

“You’re way too kind,” I said.

“It’s true,” he said. “I am very attracted to you.”

“I am not sure what to say,” I replied.

“Are you attracted to me?” he asked.

I was floored.  I knew he was attracted to an image, but never thought he would even go down that road.

I thought he was just confused or curious.

I took a sip of my coffee and casually said, “You’re cute, but I am sure you have other options.”

“Not like you,” he said.

I could see now that his curiosity was turning into infatuation. 

“What are you saying?” I asked.

“Let’s get out of here,” he said as he stood up from the table.

I got up and grabbed my purse and we walked out of the restaurant together as he gently put his hand on the small of my back.  We walked down the street and continued to talk.  The conversation was more about him than me.  He was single and while he dated a lot, he never had a long-term relationship.  He was becoming increasingly depressed over this, and his impatience was getting the best of him.  As a result, he started to question his own sexuality.  It was clear now that the meeting was not company related.

“I think you need to figure out what is going to make you happy,” I said.

“I know I was always happy when I had someone in my life,” he replied.

“I am sure you have friends,” I said.

“It is not the same.  Most of my friends are people I met through work,” he replied, “My close friends are not around much anymore.”

“Why not?” I asked.

“I am not sure,” he replied.

“Maybe because you are trying too hard to keep them close to you,” I said.

“Maybe,” he replied, “I just don’t understand why I can’t meet someone like you who I can talk to.”

“You can. You just need to be patient, the right one will come around,” I said.

We continued walking down through a park.  I started to feel sorry for him and I took his hand, which I could tell boosted his mood a little.  We continued talking and he started asking questions about sex.

“Can I assume you are gay?” he asked.

“Never assume,” I said jokingly, “Honestly I don’t like labels, but if you must know, I am bisexual.”

“Oh, sorry, what’s that like?” he asked.

“What do you mean?” I asked.

“Being with a man and a woman,” he clarified.

“I am not with them at the same time.” I explained, “It has to be right for both of us.”

“I have always thought about that,” he said.

“Thought about what?” I asked.

“Being with a man… or someone like you,” he said, “Sorry that didn’t come out right.”

“It’s okay… I understand.” I said, “How many relationships have you had?”

“I guess… two,” he answered.

“What were those like?” I asked.

“Short,” he said.

It was clear that he was not very experienced and was lacking in confidence.  I was really feeling sorry for him.  We were getting close to the end of our visit together and he had asked me if he could call me sometime and of course I agreed. At this point, it was clear that I was not going to work for the company, so I told him to remove my name from the list of possible candidates. 

“Hang in there.” I said, “The right one will come around.”

“Maybe,” he replied.

I leaned over and kissed him on the cheek and said, “Don’t feel sorry for yourself… you will end up dating hookers and they don’t give a damn about your feelings.”

As I walked away, he asked, “Like you?”

I stopped immediately and slowly turned around. 

“I saw you last night,” he said.

“You did?” I replied.

“I know that you are not a pro, but apparently you’re good at whatever you did for him last night,” he said.

I stood there motionless.

“I’ll make a deal with you,” he explained, “You give me one night a week and I will get you a position working at night in the file room. You will be the only one working at that time, so you won’t have to try so hard to cover up.”

“One night a week?” I asked.

“I really enjoyed our time today.  I want it to continue,” he said.

“This is not the way to build a relationship,” I said.

“True, but if you want this job, this is what it will take,” he said.

I felt like more like a whore than I did just a few hours before.  I was now working as an escort. 

“Okay, deal, but only while I work for the company – agreed?” I suggested.

“Sure,” he replied.

“If I find a job somewhere else… that’s it,” I said.

“Of course,” he replied.

We parted ways and I waited for the call from HR, indicating I had the job. What I got instead was something completely different.  A few days after meeting with Mr. Gregory, he called me and informed me that I did not need to report to work, and I could work from my home.  A few hours later a courier came to my apartment and delivered a package that included a standard employment contract, my first two monthly salary checks – in advance, and a handwritten note.

The note read…

“Rather than have you report to the office every day, I would prefer you work on your appearance.  Since you would report to me, I can control the attendance and employee evaluation process for you, and you will never have to report to the office. Take your first check and use it to fix your financial situation and purchase what you need for our “one on one meetings.  I will be in touch.”

After reading the note, I was tempted to return everything to John or turn him in, but I think we both knew that turning him in would not help me. It would do more damage by exposing me. If that happened, getting a new job would be next to impossible.

So, I did as I was instructed.  After getting caught up on all of my bills, I went shopping and purchased a new wardrobe. Not quite sure what John expected, I purchased everything from conservative business suits to sexy lingerie. I also took advantage of the situation and bought some extra protection… the type of protection that would get me out of this mess.

Over the next couple of days, I received additional information about my benefits package, retirement, and vacation time.  I also realized that John was responsible for getting it to me since I recognized the handwriting.  After the first week was over, I was relieved that I was not called in to work, but I realized my work hours would happen over the weekend.

“Hello?” I asked as I answered the phone.

“Hi Jenny,” John said.

“Hi.” I replied, “What can I do for you?”

“Well, I figured we could get together for dinner tomorrow night and spend the evening together,” he said, “Did you take care of the things I asked you to take care of?”

“Yes, I did,” I replied.

“Excellent, let’s get together tomorrow night and discuss how your first week was.”  He replied.

“Umm, okay,” I said.

We agreed to meet at the restaurant at which point I was expecting the evening to progress into something much more.  The next day, I got up and after a long shower, I began to pick out the outfit for the evening.  I had to consider not just dinner but what could happen afterward.

I wore a red dress with sheer nylons and black pumps.  Underneath, I wore a lace bra and matching panties.  I changed my hair color a little to accommodate the new hair extensions and made sure I had the protection I needed. The lipstick camera that was with the condoms I picked up just in case the evening went in that direction. Later that evening, I arrived at the restaurant for dinner, and like our first meeting, he was waiting for me.

“Wow you look great,” he said as he leaned in and kissed me.

“Thanks,” I replied.

“Are you okay?” he asked.

“I feel a little uncomfortable,” I said.

“Don’t worry, you look beautiful,” he replied.

We continued through dinner and discussed the working arrangements, the salary payment structure, and my working hours.

“I think if you and I can see each other once a week on Friday or Saturday night, that will work out nice for everyone.”  He explained, “You don’t have to worry about punching the time clock just be ready once a week and you will earn your paycheck.”

“Can you not cheapen it like that?” I asked.

“I’m sorry,” he said, “I figured that wouldn’t bother you since you were now a pro.”

“I am not a pro,” I said.

“Okay… okay,” he said, “Just remember our agreement.”

“Don’t worry, I know our agreement,” I said.

“Oh, yeah, I almost forgot, if you decide to leave before the end of your probationary period, I will send this to the news media,” he said as he handed me an envelope.

When I opened it, I was shocked to find a blurred picture of me as Jenny standing on the street with the “John” I had sex with.  The picture showed him holding the wads of cash and I appeared as a hooker would, negotiating my price.  The headline read “Transvestite solicits company management for employment.” It included my name, address, and phone number. I knew now I was in no position to walk away.  All I could do was try and make the best of it and hopefully gather evidence that would clear my name.

“You planned this from the start didn’t you?” I asked.

“Of course,” he said, “Do you think this is the first time I’ve done this?  I’m a pro like you.”

The rest of the dinner was very quiet.  He would occasionally make a comment or ask a question, but I simply remained quiet. 

“Let’s go,” he said.

I got up from the table and we walked out of the restaurant to his car. We drove to his home on the other side of town.  It was absolutely beautiful.  It was becoming clear that he was living well above his means – and he might be getting some help somewhere.

“How can you afford all of this?” I asked.

“Oh, the company has been very good to me,” he replied.

“No offense, but this place looks like it belongs to the owner of the company, not a department head,” I said.

“Well, like I said… the company has been very generous,” he replied as he handed me a glass of wine.

We walked around the huge home, which sat in the middle of a large piece of farmland.  Far enough off the road that no one would even suspect anything was going on.  He walked me around to each of the rooms and then into the master bedroom, which was almost as big as my apartment.  As I walked in and took in the enormity of the room, John stood behind me as he closed the door.  He turned on some soft music and walked up to me.

“Dance with me?” he asked.

I was in no position to say no at this point, so I put my purse down and began dancing with him.  As we danced, he started with his hand on my side and slowly moved it down my thigh and onto my ass.

“You really look stunning tonight,” he said.

“Thank you, you look great too,” I replied.

“I have waited all week for this night,” he said.

“What do you mean?” I replied.

He slid his hands up to my face and planted a deep kiss on my red lips.  I played along and we continued to kiss as we moved closer to the bed.  He then pushed me onto the bed and began to disrobe.

“Get undressed,” he instructed.

I didn’t know what to do.  I stood back up and started to take off my clothes.  By the time my dress hit the floor, he was completely undressed and ready for action.  He knelt down in front of me and pulled down my panties exposing my “secret.”  Still in the nylons and bra and struggling to stand in my high heels, he took hold of my penis and began stroking me.

“MMMmmm…. What are you doing?” I asked.

“Shut up and look beautiful,” he said.

I remained quiet as he continued to stroke me until I was nice and hard.  He then moved in and began to suck my cock. My knees buckled and I was having trouble standing, but he kept his hands firmly on my ass holding me up.

“Oh god, that feels so good,” I said.

“You like that don’t you,” he said.

“Oh yes… god yes…” I replied.

He continued to suck me until I was ready to explode.  He felt me shake and slid my cock in faster until I came in his mouth.  He continued sucking me until I was completely empty. He then stood up and kissed me gently on the lips and cheeks slowly laid me on the bed.  He continued to kiss my neck and chest caressing my fake breasts over the lace bra.  I was really getting turned on again as he caressed my entire body.  I turned him over to his back and returned the favor kissing him and slowly working my way down to his rock-hard penis.  I looked up at him as he moved his hands behind his head and stared back at me.  I took hold of his cock and stroked him gently then in one full motion swallowed him whole.  Pressing my tongue firmly against the underside of his cock while my lips surrounded his shaft.

“Oh god, that feels great,” he said in approval.

“You want me?” I asked.

“Oh yes, I want you bad…” he said, “suck my cock, Honey.”

“What do you want to do to me stud?”  I asked.

“I want to fuck you into next week,” he said.

“UMMM HMMM,” I said with my mouth full.

“I want to stick my cock inside you,” he said.

“UHHH HUHHH,” I replied.

“Then I want you to fuck me,” he said.

I stopped for just a second and looked back up at him.  His eyes shut, I wasn’t sure he knew what he was saying, so I just kept going.  I kept orally pleasuring him until he was ready to cum.  He pulled me off him and moved me into position.  Propping me up on my knees with my face buried in the pillow. He lubed up my ass and his cock and began to penetrate me.

“Uh… Uh… Uh…” I grunted as he filled me with his meat.

“Do you like that?” he asked.

“Oh yes, baby,” I said.

“You like my cock in your ass?” he asked again.

“Yes… I love it…” I replied.

“You want more?” He asked.

“Yes, baby, give me everything you got,” I said. 

I was so lubed up that he slid in and out of me easily.  It felt so great that I was getting hard all over again. He kept his hands on my ass as he pushed himself inside me over and over again.

“UUUUHHH… OOOOHHHH…. I’m gonna cum,” he said.

“Give it to me baby, cum inside my pussy,” I said.

“OHHH I’M CUMMING…,” he said as he shot his load inside me.

“Oooohhhh, I can feel your cum inside me,” I said as I turned to look up at him.

He jerked several times as he kept shooting cum inside my pussy.  When he was done, he pulled out and my ass tightened up causing me to fall to my side on the bed.  He noticed I was rock hard again and he pulled alongside me in my previous position.

“Your turn,” he said.

I wasn’t sure what to do.  Was he serious?  I guess he was.

“I want you to fuck me,” he said, “Stick your cock inside me and cum all over my ass.”

I slowly got up while he positioned himself.  I looked down at his ass, and noticed he was already lubed up; after slipping on another condom, I penetrated him.

“Come on whore, harder,” he said.

It was clear he wanted it rough, and I was willing to accommodate him considering what he put me through already.

“You want it,” I said.

“Yes whore, give me all of it,” he said.

I forced my cock into him as deep as I could and then instead of moving slowly to allow him to adjust, I rammed into him over and over.

“OOOOWWWWW, don’t stop,” he said, “Give me more… FASTER, FASTER.”

“You like it you sissy fag,” I said.


“You’re going to make me cum.” I said with each insertion of my penis.

“Please cum on my back, mistress,” he said.

I continued to force fuck him until I was ready to cum once again and pulled out and came all over his back.  I rubbed my cock over his ass and watched as it ran up his back.  He pulled himself up and fell to his side, while I stood there in front of him.  I eventually went to the bathroom and took a shower and returned to find him asleep in bed.  I was not sleepy and wasn’t sure if I should just leave or not, so I got dressed, picked up my purse which had my hidden camera, and went to the living room. 

I eventually dozed off on the couch but woke up before he did the next morning.  I found my way to the kitchen and made some coffee and sat down at the table.  John eventually joined me and thought I had left. We talked for a brief moment, and he “allowed” me to leave, so I called a cab and headed home.  When I arrived, I immediately connected the camera to my computer and downloaded the video that captured our conversation at the restaurant and our action at his house.  I needed a little more to get myself out of this but was willing to take my time… after all, I was having some great sex and enjoying my time as Jenny.

We continued the weekly sessions for about a month when I found that he was embezzling from the company and what he was doing to me he had done to a number of other employees. The tough part was exposing him without exposing me in the process. While I was passable as Jenny, I couldn’t let anyone find out who I really was.  So, while I tried to figure that out, I continued to meet with John, but things were about to change.

“Hello, John,” I said as I answered the phone.

“Sorry to call you on Tuesday, but we need to talk,” he said.

“What about?” I asked.

“I have to let you know that I have been let go by the company,” he said.

“Really,” I said, “What happened?”

“That’s not important,” he said, “I wanted to let you know they want to meet with all of the employees that reported to me.”

“Why?” I asked.

“I believe they are investigating me,” he explained.

“For what, embezzlement?” I asked.

“Maybe,” he said.

“So, why are you telling me all of this?” I asked, “Do you not want me to tell them about our arrangement and what I have seen at your house?”

“Well, that would be nice, but the real reason is that I wanted to protect your identity,” he said, “I thought it might be a good idea if you just didn’t exist.”

“What do you mean?” I asked.

“If they call you may not want to answer as Jenny,” he explained.

“I understand,” I said as I hung up.

I wasn’t about to be roped into his illegal activities – any more than I had already been.  So, I started putting my resume out again – making sure everything was correct and it was me… not Jenny. The next day, I got a couple of calls from the company.  When they asked for Jenny, I simply responded that they were calling the wrong number.  I was ready to put John and the company behind me, so I went ahead and changed my phone number, so I didn’t receive any other calls.  I had enough money saved up to cover my bills for a few months, so John and the company did take care of the current situation, but now I had to figure out my future, but now I had options… I could still look for a real job or continue the fun job privately.

While I waited, I started going out more and spending time at a dance club where I met a number of great people.  Some men… some women, but all fun.  On my way home one night, I walked by a newsstand and saw the newspaper where the headline read, “Businessman poses as a woman – embezzle millions.”

I read the article as I walked home, and it seems John created fake employees to embezzle money from the company.  The police had video evidence showing Gregory, posing as a woman, cashing payroll checks.  If convicted, he faces up to fifty years in jail.  I stopped as I read this and while I felt sorry for him, I just thought to myself… KARMA.

Don’t forget to tell me what you thought of this short story. Leave your comments today.

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