Enviable Positions

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. 

When I was younger, I always knew I was different, and being different came with enormous baggage and difficulties. I just never realized the kinds of difficulties I would have if anyone else knew just how different I was. When that day comes it can be so overwhelming that you can feel like there is no place you can go to hide from the shame. That was my life, until three days ago.

On the outside, I was a very successful sales manager for a private company based in the UK. I loved my job, especially when I didn’t have to come to the office every day. Working from my home in New York, I could meet with customers without ever leaving my bed. I had the career I had always hoped for and the mate I dreamt about in high school. A stunning brunette, who had a mysterious side to her, that was only masked by her beauty. From a distance, I had it all. Great home, a spouse at my side, and the career I always hoped I would have… but there was more to me than people saw on the surface.

I grew up confused and trying to figure out which skin to wear. Being around my four older sisters didn’t help. I grew up knowing so much more about wardrobes, hairstyles, makeup, and dating boys than I ever needed to know…. and a lot of it wore off on me. When I wasn’t their punching bag, I was their mannequin. I became used to wearing women’s clothing a lot back then. So much so that it became a part of me and I eventually learned how to pass as a woman.

When I met my eventual wife in college, my sisters made fun of me, and while the joke was easily dismissed as sibling rivalry, none of them really knew how much truth there was to the story. I tried to keep it hidden and like most crossdressers, I purged often. I even tried to stop after Kelly and I got married, but I realized, disconnecting from it was like asking me to disconnect an arm or a leg… I just couldn’t do it.

So I tried keeping it hidden which became harder and harder. Knowing I had to make a decision, I tried leaving little hints around the apartment. Kelly either didn’t pick up on the hints or dismissed the panties and nylons as her own. Not long after celebrating our 4th wedding anniversary, the decision was ultimately made for me, when she caught me after coming home early and unannounced.

She was furious at first and over the next few weeks. The shock of seeing her husband dressed in her best black dress with black nylons and leather pumps was just too much to bare. I tried sitting down with her after she left to stay with her folks, but she was not willing to listen to any explanation I was willing to offer – even though it was the truth. The cloud of deception was too great and we decided to divorce.

The divorce started out very ugly. She was angry and our world was going to know about it. It started with her calling my office and asking to speak to her “faggot” husband a few times. My assistant tried to keep it quiet but rumors began to spread as Kelly began calling the main switchboard.

Things settled down after she realized that alimony wouldn’t be there I couldn’t keep a job, and after the judge ordered us to go to counseling, we began talking again and she started to understand more about my past. She could never accept it but she did understand. We finalized our divorce without having to pay much in alimony and she moved to a new apartment in Long Island. I found myself with newfound freedom and a half-empty apartment. While I began spending more time at the office, I was now free to dress how I wanted and enjoy the private solitude; but I was still very lonely and sad that Kelly was gone.

It was about six months since the divorce and my days were spent either at the office or at home. I found it harder and harder to concentrate on work when I was home – especially when my wardrobe was growing and the place was becoming less and less like a bachelor pad.

My assistant who was a very nice young lady spent a lot of time with me. I think she might have suspected something, but she never asked. The closest thing to approaching the subject was when she asked me if I was going to the Halloween party.

I wasn’t really ready to have any fun outside of my apartment, but she pushed harder and harder each day until I gave in. She suggested we go together, but I didn’t want to create any issues for either of us, so I simply agreed to see her there.

The question was… what to wear? I thought long and hard about stepping out which I had only done once in college before I met Kelly. I then thought I would look for a costume that I could rent, but I had waited too long and there was very little to choose from. Faced with very few options, I decided to take a chance. I figured, that I would go make a quick appearance and leave.

So I picked out the most elegant gown I had. Pulled out the princess crown I had in the jewelry box and decided to go as a beauty pageant winner. I order some cheap flowers from a florist nearby and then proceeded to get ready.

I made sure I was as authentic as possible. Starting with a black lace bra and panty set, adding a matching garter belt to hold up the sheer tan nylons. I then slipped on the gown, fixed my makeup and hair, and slipped on a pair of high heels. I took a few pictures before I headed out and took a cab to the party.

When I arrived I could tell there would be little chance of rumors later on – considering the costumes I saw as I walked around. Strangely enough, no one recognized me. That is until my assistant Jennifer walked up to greet me.

“You made it,” Jennifer said.

“Yeah.” I said.

Before I could get another word out of my mouth…

Jennifer said, “You look fantastic.”

“Thanks, so do you,” I said commending her on her sexy cop costume.

We made our way to the back of the room where we sat down and chatted for a few minutes.

“I really can’t stay long,” I said.

“Hey, you made it here. That is a start,” she replied.

“I feel really uncomfortable,” I said.

“I know, that’s why I brought you back here.” she said, “I wasn’t sure if you would really dress for the party.”

I was now stunned. How did she find out?

“What? You didn’t think I knew?” she asked, “I see your credit card statements, remember.”

“Why didn’t you say anything?” I asked.

“It was none of my business.” she said, “Besides, I figured you had gone through enough already with the divorce.”

We chatted for a few more minutes and I couldn’t stay any longer, so Jennifer and I began to walk out together. As we stumbled through the crowd heading for the exit, we were stopped by a young woman neither of us recognized.

“You look absolutely smashing.” the woman said in a very pronounced British accent.

“Thank you, you look great too,” I said softly.

“I am loving the party. I thought that it would be very stuffy, but you Americans know how to go all out,” she said.

“Yeah. It is definitely not the typical day in the office.” Jennifer said.

“I must ask, I love your dress, where did you get it?” the British woman asked.

“I bought it online,” I said softly.

“I’m sorry.” the woman replied as she leaned over to try and hear me over the noise of the party guests.

“I bought it online,” I said

She then leaned in closer to me and said, “That was probably smart.”

The woman then took me by my arm and handed Jennifer her phone and asked her to take a picture of the two of us. Jennifer took the picture and she could tell I was really uncomfortable and whisked me away. She walked me down to the cab and I handed the remaining rose I kept as a gesture of thanks and friendship. She gave me a hug and helped me into the car.

When I arrived back at my building the doorman helped me out of the car, not realizing who I was.

“Good evening Miss.” he said, “May I say you are looking lovely this evening.”

“Thank you,” I said in my best girly voice.

I walked to the elevator and he asked, “May I ask who you are visiting?”

“Oh… my brother Nick Magnes,” I said.

“Let me call him and let him know you are on your way up.” He said.

“Please don’t. I want to surprise him. I haven’t seen him in a year.” I said.

He looked at me very closely and then said, “He will be thrilled to see his sister in such a great outfit.”

I went up the elevator and quickly walked into the apartment. Relieved, I stepped out of the gown, leaving on the nylons and lingerie. I slipped on my favorite robe and poured a glass of wine. I sat down in front of the window and stared out over the Manhattan skyline remembering the exhilaration of being out in public.

Monday morning, I went into the office, still a little scared of someone recognizing me from Friday night. Surprisingly, no one did. I sat down with Jennifer in my office and we talked for a few minutes about the day’s agenda. I was also surprised she didn’t bring up Friday night either, that is until one of my friends knocked on the door.

“Hey Nick, sorry to interrupt, but I wanted to talk with Jen for a minute,” Jeff said.

“Sure Jeff what’s up?” Jennifer asked.

“It’s nothing important, I was just wondering who the tall blond was,” Jeff replied.

“Tall blond?” Jennifer asked as she looked over at me subtly

“Yeah the one in the black dress, she was carrying a dozen roses.” Jeff described.

“Oh… Danni… she’s a good friend of mine.” Jennifer said.

“Do you know if she is seeing anyone?” Jeff asked.

“Well, she just got out of a relationship. That’s why I asked her to come.” Jennifer replied.

“Do you think I can get her number?” Jeff said.

“No Jeff, but I can introduce you to her if you want.” Jennifer replied, “I will call her and set something up.”

“Awesome, thanks.” Jeff replied, “Nick… you missed one hell of a party on Friday.”

“That’s what I heard,” I replied, looking at Jennifer with the same subtle grin.

Jeff closed the door to my office and Jennifer and I both started to laugh uncontrollably.

“Well, you pulled it off,” Jennifer said.

“What’s that?” I asked.

“You know how Jeff is about spotting hotties in the crowd…. And he found you.” She said.

I didn’t know what to say, but she was right. The two of us talked for about an hour. I realized she knew a lot about the issues Kelly and I were having and about my past. I had always trusted her, and after learning what she knew, I trusted her even more.

Later that afternoon, Jennifer came into my office and informed me that the VP of Sales Operations wanted to see me in his office. I walked down to his office and was greeted by the CEO of the company, Kristov Conellroy.

“You must be Nick Mangus.” Mr. Conellroy said.

“Pleasure to meet you,” I replied.

“It is a pleasure to meet you.” he replied, “I am looking forward to seeing how you are going to bring Leslie on our side.”

“Leslie?” I asked.

Just then, Conellroy shook VP Williams’ hand and left the office.

“Want to fill me in?” I asked sarcastically.

“Sit down,” Williams said.

We sat at a small table in the office and he laid everything out for me.

“How well do you know Limitless Enterprises?” Williams asked.

“Can’t say that I know much,” I replied.

“Well, they’re our biggest account, and just found out last week they were going to pull out.” Williams explained, “We invited the CEO to visit with us and we didn’t make any headway, that is until this morning.”

“What changed?” I asked.

“She said at breakfast this morning that she would be willing to negotiate a new five-year contract under one condition,” Williams said.

“…and that condition is?” I asked.

“That we send this person to London to negotiate the deal,” Williams said as he handed me a file folder.

I opened the folder and there was the picture of me in drag and the British woman I met at the party on Friday.

“Now I want you to know there are no judgments here.” Williams said, “You do great work Nick and I wouldn’t ask if it weren’t this important… but it is.”

“I don’t know what you are asking me to do,” I said.

“I think you do.” Williams replied, “If we lose this account, the company goes under. Three hundred jobs… gone in an instant. If you can pull this off, we will make it worth your while.”

I paused for a brief second, then asked, “What happens if I can’t close this deal?”

“Then we go under,” Williams replied.

“Okay, what if I don’t want to do this?” I asked.

“We can’t afford for you not to do this,” Williams said implying that there were no other options and I was no longer being asked to participate, but ordered to.

“I am going to need some time to think about this,” I replied.

“I understand, but I need an answer by the end of the day tomorrow,” Williams replied.

When I returned to my office, Jennifer was waiting for me with two boxes labeled Limitless Enterprises.

“These just arrived, Nick,” Jennifer said.

“Thanks, I’ll take them,” I replied.

“Is everything okay?” Jennifer asked.

“Uh, yeah. I am going to take the rest of the day off.” I said as I walked into my office with the boxes.

“Nick, is everything okay?” Jennifer asked again.

“I’m not sure.” I replied, “I guess I just need to think about things.”

Jennifer was somewhat confused and started back to her desk.

“Jen… Do you have plans for this evening?” I asked.

“No,” she replied.

“Would you like to have dinner?” I asked, “I think I need to talk to someone I trust.”

“Of course, Nick.” she replied, “Do you want to meet somewhere?”

“If you are okay with it, I would prefer someplace a little more private.” I replied, “Would you like to have dinner at my place?”

“Sure, how about 8 o’clock?” she asked.

“Great… and thanks,” I said as I picked up the boxes and started home.

Rather than cook, I ordered Thai food from a restaurant close by that I knew she liked. I cleaned up the apartment, which wasn’t hard since it was still half empty.

Jennifer arrived right on time and the two of us sat down for dinner, and I laid out the details. I was surprised at how attentive she was and how she stayed in control even when she learned that her job was in jeopardy.

“So what are you going to do?” she asked.

“I don’t know.” I replied, “I think I am screwed either way.”

“I don’t think so,” she said.

“Well, if I go through with it, I risk being outed, if I refuse I can almost guarantee they’ll do it.”

“What if you turn it in your favor?” Jennifer suggested.

“What do you mean?” I asked.

“What if you no longer work for the company?” she asked.

“Then the company goes under.” I said, “I don’t know that I would want 300 jobs on my head.”

“No, what I mean is what if you negotiate your release.” she said, “Blackmail them instead.”

“Sounds interesting, what did you have in mind?” I asked.

Jennifer and I spent the rest of the night talking through the scenarios and had a solid plan going forward, but there was something left out. Something I didn’t anticipate… fortunately, Jennifer did.

“Now who is Leslie really expecting?” she asked.

“What do you mean?” I replied.

“Is she expecting a woman or a man dressed as a woman?” she asked.

“Does that matter?” I replied.

“It might.” Jennifer explained, “If she’s expecting a woman and she sees a man instead, the negotiations will end and now you’re exposed not just to the company but to Limitless as well… who knows how far that will travel. The reputation of the company and you will be even more damaged.”

“Any suggestions?” I asked.

“I have one, but I am not sure you are going to be comfortable with it,” she replied.

After she told me about her idea, my initial thought was… she was right, I wasn’t totally comfortable with it, but it did allow me some control over the situation.

Early the next morning, Jen and I went to the office and I cleared out my desk, leaving all of the company-related assets in place. Jen did the same and the two of us returned to my apartment. We then made the call.

“I wasn’t sure you were going to call me today. I heard about your early morning visit.” Williams said.

“Yeah sorry about that, but I felt it best that we make this look good and keep the suspicions to a minimum,” I replied.

“So I take it you have made a decision?” Williams asked.

“I have,” I replied, “I looked at the information about Limitless and the amount of money the company is going to make on this five-year contract is a little more than seventy-five million dollars…. I want five million.”

“What?” Williams shockingly asked.

I explained to Williams, “I figured the 75 million is going to cover the company for the next 10 years, but either way I am not going to be there to see the fruits of my labor. So I will resign my position and we will put together a contract that will pay me 5 million dollars. 3 million up front and the other 2 on delivery of the check from Limitless.”

“And what if you can’t close the deal with Limitless,” Williams said.

“Then sue me for breach of contract.” I replied, “The bottom line is, it is to both our advantage to win this deal. You guys are in the black for the next 10 years and I can retire.” I explained, “If I can’t deliver, my reputation is already damaged and you are no worse for wear.”

“I’ll need Conellroy’s approval on this,” Williams said.

“That’s fine, I will send you the bank information to wire the funds to, and once I have confirmation, I will get started,” I replied.

At 6 o’clock that evening, I received a call from the bank in Switzerland, confirming the deposit. I immediately transferred the funds to a second account I set up to ensure the funds would not be removed later.

I then began packing for Europe. About an hour later, Jennifer arrived with luggage of her own.

“What are you doing?” I asked.

“I am going with you,” she said.

“I can’t ask you to do that,” I replied.

“Do you think you can spare some of that 3 million?” she asked.

“Yeah, I can,” I replied.

“Good, then I am going with you. We will work out the details later.” She said.

Before I met with Leslie at Limitless, There was some work to be done. I wasn’t meeting her for another four weeks, but there was little time to waste

We landed in Amsterdam and rented a one-bedroom flat for the month. After getting settled in we went out the next day to see the town and meet with a plastic surgeon.

Jen had made the arrangements for me to have breast implants. It was initially rejected by the doctor, but offering to pay cash to have it done changed his mind. The surgery was not too rough on my body. There was very little pain and outside of the soreness from the skin stretching around my breasts I was fine.

Jen also hired a hairstylist and makeup artist. I was becoming more and more ladylike with the hair extensions sewn in and learning more about how to apply makeup. It wasn’t too bad since I was already well-trained by my sisters, but I learned a little more about colors and which one’s best suited me.

The hardest part was the electrolysis and waxing. I was not very hairy, but what hair was left needed to go and that was not easy at all. The rest of the transformation involved spray tanning and the wardrobe.

For the next couple of weeks, Jennifer and I went shopping all over Amsterdam, buying everything from dresses and business suits to kinky lingerie in the Red Light District. Along with the physical transformation, I had to learn how to walk and talk like a woman. Jen taught me so much over the course of the month. I don’t know what I would have done without her.

During that time I learned more about women than I ever thought possible without actually being one. Jen took me through the confident walk, timid and shy looks, and even helped me write and use my hands without breaking a nail.

She then took me in a different direction.

We went to dinner every Friday night and she would pick out my outfit and observe me dress, fix my hair, and apply my makeup. She tried so hard to get me to be more comfortable and every time I stepped out I did just that. I enjoyed the thrill of having men and women look at me. Jen noticed this too and wanted to make sure my comfort level included other aspects of my transformation.
The week before I left, we went to dinner and walked through the Red Light District. While there, we stopped at one of the establishments and Jen was picking out men for me. I freaked out and rushed out into the street. Jen followed me out and could tell how scared I was, so we walked back to the flat.

I sat on the couch for a little while so I could calm down and Jen walked in and sat next to me.

“Are you okay?” she asked.

“I am not sure I can do this,” I said.

“I understand, I thought you might want to experiment a bit.” She said.

“Listen, it’s not like I have never thought about it, but to be honest, I am not sure I am ready to have sex with a man,” I replied.

“Okay, how about with me?” Jen asked.

“What do you mean?” I asked.

“What if we role-played and I played the man?” she suggested.

“I don’t understand,” I said.

“Give me ten minutes and come to the bedroom.” She said.

“Wait… what are you talking about?” I asked.

“You’ll see. We are going to try something, trust me,” she said.

I waited and she called me into the bedroom, where she stood in front of the bed wearing a black corset and a strap-on dildo that was bigger than my real thing.

“Come here, Danni.” She said.

I walked over to her and she took me by the hair and pushed me to my knees.


“Wait…” I said before she pressed the dildo up against my lips.

“TAKE IT.” she said, “SUCK MY COCK.”

I knew what she was trying to do, but I wasn’t sure it was working. She then picked up my chin and slapped me across the face.

“I SAID, SUCK MY COCK, YOU WHORE.” She commanded.

I opened my mouth and she slid the dildo into my mouth. Slowly at first until I got it nice and wet. Then pushed it deep until I began to gag.

“That’s it. Take that nice cock.” She said.

As I continued to engulf this thick wet rubber toy in my mouth, I noticed I was really getting turned on. Jen noticed it too.

“Oh my, what do we have here?” Jen said as she noticed, I was poking up through the miniskirt I was wearing.

She stood me up and spanked my ass. She then slid down my panties and put a chastity harness around my package, then pushed me back to my knees where I continued to orally pleasure her.

“Get on your feet.” She said.

At this point, I was not going to disobey her. She bent me over onto the bed and began to wet my clit with her finger. Over and over again she massaged my opening and slowly slid her fingers inside me.

“Do you like that you sissy?” She asked.

I don’t know what compelled me to say it, but I responded, “Yes mistress.”

“Do you like my fingers in your ass?” She asked.

“Yes, mistress,” I repeated.

“Yes, what?” She replied.

“I like your fingers in my ass,” I said.

“Do you want more?” She asked.

“Uh Huh,” I said in approval.

“You want me to stick my dick in your ass?” She asked.

“Yes, mistress,” I said.

“Tell me what you want.” She commanded.

“I want you to fuck me,” I said.

“What?” She said as if she never heard me.

“I want you to fuck me, please,” I said.

She then stood up and slowly pushed the tip of the strap-on up against my wet hole. Pressing harder and harder until the tip found its way inside me.

“OOOOO…” I moaned.

She continued to push inside me and with every inch the pain turned into an exhilaration I had never felt before.

“OH YES… “ I said.

“You like that?” She asked.

“YES,” I replied.


“YES,” I replied.

She then began pulling back and forth sliding that long thick dong in and out of me.

“UH… UH… UH… OOO… YEAH…” I expressed wanting more.

“YOU… TAKE IT… DEEP… YOU… FUCKING… SLUT.” She said as she really began to punish me.

“AH… AH… NO… OOWWW….” I said as I moved my hand behind me to try and fend her off.


She continued to abuse my hole until I was numb. Then she pulled out causing me to fall to the bed. She hit my ass again flipped me over and hoisted my legs up in the air. She removed the clamp and slid the dildo back inside me. The feeling was just as intense. As she pushed in and out of me as I had one hand on her hip pulling her forward and the other wrapped around my own package.

“COME ON BABY, I WANT YOU TO CUM.” She said angrily.


Just then without warning, I shot my load all over myself. Jen slowed down and gave me a chance to relax then pulled out and rubbed the cock over my cum covered stomach. She then moved up to my face.

“OPEN YOUR MOUTH.” She commanded.

She rubbed the cock over my lips and repeated, “OPEN YOUR MOUTH AND TAKE YOUR MEDICINE.”

I slowly opened my mouth and she slid the cum covered dildo back in. With her other hand, she wiped up what was left on my cock and stomach and let it drip onto my lips from her fingers.

When she was done with me she gave me one more slap to the face then proceeded to the bathroom where she took a shower. When she returned she was dressed in a simple pink bathrobe and helped me up so I could get cleaned up as well.

“So did that help?” She asked.

“Uh… yeah, I think so,” I replied.

She got me into the shower where she washed me down and after drying me off she brought me a glass of wine and a new nightgown to wear. The two of us fell asleep in each other’s arms and remained there until morning.

The last night before I flew to London, Jennifer and I went to dinner one last time. She was going to head back to New York after dinner, while I went to earn the rest of my retirement the next morning.

“I almost forgot.” Jennifer said as she handed me an envelope, “I had you upgraded to first class.”

“You didn’t have to do that?” I said.

“Well, I figured a millionaire shouldn’t have to fly coach.” She replied.

“Listen, I really want to thank you for everything.” I said, “You have helped me in more ways than you can imagine.”

“I know, but you are doing the work.” She said, “I just wanted to make sure you were prepared for anything. That’s what a good assistant does.”

We continued with dinner and afterward took one more walk around the city before heading to the airport.

“Oh yeah, there is one more thing I want to give you before you go,” I said as I handed her an envelope.

“What’s this?” She asked.

“Open it when you get on the plane,” I replied.

I then gave her a huge hug and quickly walked out of the airport to hail a cab. I hated rejection and having her reject a check for a million dollars would have been devastating.

I returned to the flat and got a good night’s sleep. The next morning I got up and dressed and headed to the airport. With my new passport in hand, I boarded my flight to London. When I arrived, I headed straight for my hotel, which was across the street from the headquarters for Limitless Enterprises.

I unpacked and prepared for my meeting with Leslie. I wanted to remain comfortable but cautious, so I spent some of that time in the restaurant of the hotel where I could be around people. After a fantastic lunch, I went back to the room to freshen up and headed across the street to meet with Leslie.

“Welcome to the United Kingdom,” Leslie said as she walked around her desk to greet me.

“Thank you, I appreciate you requesting me. It was a nice opportunity to see Europe.” I replied.

“It’s Danni isn’t it?” Leslie said.

“Yes,” I replied as she welcomed me to sit down.

“Unusual name.” she said, “but understandable.”

“I have to admit, I am glad we are able to meet under normal circumstances,” I said.

“Really, I thought our meeting was fine,” Leslie replied.

“Well, it was a little awkward, since there were so many people in costume,” I replied.

“And yet here you are still in costume.” She replied, “Although a very convincing costume at that.”

“Excuse me,” I said.

“It’s okay… Nicholas.” Leslie said, “I know all about you.”

I was floored. I had planned for her to believe I was a woman or find out I was a man, but not for her to find out my true identity.

“You see, your company was becoming somewhat lazy in their handling of my affairs. When I informed them I was going to take my business elsewhere, it was with the intention of motivating them.” Leslie explained, “I wanted to see how far they were willing to go to keep my business, and that proved out well for me… here you are.”

“I don’t know what to say,” I replied.

“Please don’t worry, your secret is safe with me… it is your colleagues, I would worry about,” she said, “, but I guess 5 million dollars is enough to satisfy both interests.”

I looked up at her with total amazement.

“Yes, I know about that too.” she explained, “I knew about that right after the wire transfer took place.”

“If you knew why continue? You obviously got what you wanted.” I replied.

“Well almost everything.” she said, “I have to admit I was shocked that you would go to such lengths to earn my business.”

“To be honest, I wasn’t doing it for you, but for the employees at the company,” I said.

“Ah yes, looking out for your fellow man. That’s admirable.” She replied, “Well I think we have delayed this long enough… shall we.”

She got up and showed me to the door and we walked through the office down to the first floor and back across the street to the hotel restaurant.

“Shall we have tea?” she said.

We sat down and had afternoon tea and discussed a number of things none of which involved the business negotiations.

“May I ask you a question?” Leslie asked.

“I think I should be the one asking questions since you know so much already,” I replied.

“Did you have a complete surgical procedure?” she asked.

“No,” I replied.

“Ah, so just the top half.” She replied, “Very good, they are stunning by the way.”

“Thank you, I guess.” I replied, “May I ask you something?”

“Of course,” she replied.

“Why am I really here?” I asked.

“Excellent question.” she said, “To be honest when I learned about the company’s agreement to send you to me, I was going to simply send them a check, but when I learned what you had done, I became intrigued by you and wanted to learn all I could.”

“Have you?” I asked.

“I have learned a lot.” She said, “…I admire you. You have been through quite a bit this past year and yet you still hold people close to your heart – even though you spend so much time alone.”

“Maybe I am searching for something,” I said.

“I think you have found it already.” she replied, “I think your real challenge is accepting it.”

“Accepting what?” I asked.

“Accepting who you are.” She replied.

She slid an envelope across the table. It was the 75 million dollar check for the company.

“Does this mean we are done?” I asked.

“It does, but I want to offer you something as well,” she said.

“What?” I asked.

“A chance to fulfill what you have always wanted,” Leslie replied.

“And what is that?” I asked.

“Meet me at this address tomorrow evening, and dress accordingly.” She said as she handed me a card and walked out.

I went back to the room and informed the company that the check was in hand. I waited for my second wire transfer to take place before releasing the check to the messenger. I then began to pack for home.

As I did, I began to wonder what kind of a home was I returning to. Things were different. Granted, I could go anywhere and do anything I wanted now, but I could never go back to my old life. I then picked up the card Leslie left for me. I figured it was the start of my new life so why not take one more chance?

So the next evening, I picked out my sexy red dress, curled my hair, and dolled myself up. When I went downstairs, a car was already waiting for me.

“Did I call you?” I asked.

“No Miss, I was instructed to wait for you.” The driver replied.

He helped me into the car and we set out for Leslie’s mansion. The drive through town was fantastic as I was able to get a glimpse of a number of historical landmarks. We drove through the countryside a bit until reaching her lavish home. I wasn’t sure what to expect, but based on Leslie’s signals, the evening wouldn’t be boring.

Leslie met me as we drove up, dressed in a very sexy dress herself.

“I am so glad you are here.” she said as she gave me a hug and a peck on the cheek, “Please come in.”

We walked into her home and immediately headed toward the backyard area. There I found two men along with a third who I could only assume was a butler or cook.

“Danni, this is Kurt and Michael. Boys this is my good friend Danni.” She said, “Danni, can I get you something to drink?”

“Yeah, a glass of wine would be great,” I said.

As the butler poured the glass of wine, Kurt and Michael were instantly clinging to my hips.

“Easy boys. We have all night.” Leslie said.

“Forgive me, but I am not sure what’s happening,” I said.

“Well, I thought that you shouldn’t have to rush back to America so soon, and perhaps we could get together and enjoy an evening together,” Leslie said.

“I am still confused,” I said.

Kurt leaned over and said, “Don’t be. There is no agenda, no expectations. We are just spending the evening together.”

I decided to see where the evening was going to go and turns out it was a very good evening. Kurt and I hit it off right away and talked most of the night, while Michael and Leslie continued to play in the pool.

“Would you like a tour of the grounds?” Kurt asked.

“Sure.” I replied.

The two of us walked around the backyard garden area and continued to talk. I learned he was from Liverpool, but spent most of his time in Chicago where he went to school. He now works for a large bank as an international trader and has known Leslie for a number of years.

I didn’t say much about myself other than I was from New York and had just met Leslie, but I didn’t have to say much as Kurt asked the one question I was hoping wouldn’t be asked.

“How did your family react to the change?” Kurt asked.

“What do you mean?” I asked.

“I would hope they were supportive, but I understand most families are not and reject people who are different,” Kurt replied.

“What else did Leslie tell you?” I asked.

“Nothing really, I just assumed and there are some physical characteristics that can’t always be hidden,” he said as he gently ran his fingers down my neck and across my ears.

“I feel so embarrassed,” I said.

“Don’t be. You are very beautiful.” Kurt said.

“It’s not that. I think I made a serious mistake.” I replied.

“Why would you say that?” he asked.

“I forgot to think of me and where I would be after all of this was over,” I said as I started to cry.

“I don’t understand.” He said, “You sound like someone with a good heart. Your choice is yours and yours alone.”

“Not when you make the choice because others may suffer in the process,” I replied.

“Let me ask you something… Would you have laid your life on the line for those same people?” he asked.

“Yes, considering the number of people sure,” I said.

“Then you have nothing to be ashamed or embarrassed about,” Kurt said as he put his hands on my hips.

As I felt his hands firmly on me, I started to get a warm sensation throughout my body and it was then I decided to take a chance and leaned up and kiss him.

“That was nice,” he said.

“Really,” I replied.

“Yeah, I’d like to do that again,” Kurt said as he leaned over and began kissing me sliding his tongue across my lips and into my mouth.

The thrill was uncontrollable and I found my hands sliding down his face to his lower back. Then I quickly pushed him back.

“What’s wrong?” he said.

“I don’t know if I can do this,” I said.

“It’s okay, maybe we moved too fast.” He said, “Let me take you back to the hotel.

“What about Leslie?” I asked.

“By the time she figures it out, you will be on your way home,” he said.

The entire ride back to the hotel was silent. When we arrived and I got out of the car and headed for the door. I turned back around and couldn’t just let him go without an explanation.

“Can we talk for a minute?” I asked.

“Sure” he replied and stepped out handing his keys to the valet.

We went up to my room and I asked him to sit down as I explained to him why I was struggling and confused.

“You have to understand that my reason for doing this was more to save jobs and the company I work for instead of just me.” I said, “If not for a friend of mine I wouldn’t have even considered kissing you, but she taught me quite a bit and when you and I kissed, all I wanted to do was jump in bed with you.”

“I think I am missing the part where I object,” he said sarcastically.

“I don’t want to mislead you.” I said, “What you see is not the real me.”

I then unzipped my dress and watched it fall to the floor where I stood there in my red lace bra, heels, and nylons with a bulge pushing on the red lace panties.

As tears ran down my face, I looked at Kurt and said, “This is who I am.”

He got up and walked over to me.

“You are so much more than that,” he said as he put both hands on my face and kissed me passionately.

Before I knew it I had him on the bed with me on top of him kissing every part of his body. I ran my hands down his chest and began to unbuckle his pants. After getting him undressed, we slipped into bed and laid together savoring the time we had together.

I could feel his hard cock pushing on my thigh and I became excited as he slowly caressed my tits through the lace bra. I then took another chance and remembered what I was taught and slid down his body and began stroking his cock which was fully erect at this point.

“MMM… That’s nice,” he said.

I then licked my hand and stroked him more and I could tell he was getting more excited. Then I threw caution to the wind and began giving my first blowjob ever.

“OH…. OH YEAH… That’s it… OH YEAH.” he said gasping for air.

I remained silent as I continued going down on him. I found myself enjoying it more and more as his thick hard cock began to throb in my mouth. I couldn’t take my mouth off of him, even when he pulled me off.

“I want you baby,” he said.

“I want you too,” I replied, “I want you inside me right now.”

I jumped up on top of him and made sure I was nice and wet before he pushed inside me.

“OOOOOO…. YEAH…. THAT’S IT BABY… I WANT IT ALL.” I said as I slid over his cock and felt every inch inside me.


“MY VIRGIN ASS IS ALL YOURS BABY… COME ON… FUCK ME…, “ I said as I started to bounce on top of him, “UH… UH… UH… OH YEAH… FUCK… ME… FUCK ME…”

I could see him really getting into it as well, but he was far from done. He grabbed me and sat up while I was still enjoying his penetration. He turned me over and grabbed my nylon-covered legs and continued to bang me causing the headboard to hit the wall repeatedly.

“OH YES… OH YES… YES… YES…” I screamed with every thrust inside me.

All he could manage was continuous grunting as he plowed into me. As he began to tire, we moved to his favorite position which turned out to be mine as well. He stood me up, bent me over, and slid his rod in my ass.

“OH GOD YES… YES… FUCK ME BABY… FUCK ME…” I said as he slapped my ass.

“OH YEAH… I’m gonna cum baby,” he slowly whispered.


“OH YEAH… YEAH… YEAH… UH… UH… OOOOOHHHH.” he shuttered as he exploded inside me.

I felt each injection of his juices warming my insides as he continued to throb and stretch my pussy. He then fell forward onto my back. I reached back and gently helped him pull out and laid him on the bed where I laid next to him as we fell asleep together.

The next morning, I got up and noticed he was still asleep… at least most of him was. He was laying in bed exposed with an erection that just could not go to waste.

So I quietly slipped back into bed and took care of business. I quickly took hold of him and began licking his nob until I got his full attention and then took every inch in my mouth. Pressing my tongue against the underside of his massive cock. I could feel his heart beat faster and faster, but all he could do was whisper as I continued to polish him off one more time.

His head began to rise as he was ready to give me another gift of cum, but this time I was going to receive it orally as he spewed his cum into my mouth and onto my face. I loved every minute of it. Wiping his cum off my cheeks with his cock and licking him clean. He fell back onto the pillow and I slid up his side and gave him a peck on the cheek before heading to the bathroom to get cleaned up.

A few hours later, I was packed and ready to go to the airport, Kurt stepped out of the bedroom and wrapped his arms around me as I looked out the window of my hotel room.

“Where are you headed?” He asked.

“You know I am not sure, but wherever I go, it won’t be far from you,” I said as I turned around and kissed him one last time.

I headed to the airport and while I waited for my flight, I made a phone call, but there was no answer, but the phone was ringing… it was just closer to me.

“Can I join you?” Jennifer asked.

“I had a feeling you were not going to leave me alone,” I replied.

“Did you get the answers you were looking for?” she asked.

“More than I ever hoped,” I said.

“Good… would you like to talk about this?” she asked as she held the unopened envelope I gave her a few days earlier.

“Sure, but I did say to wait until you were on the plane,” I said.

“Then let’s get on the plane and talk about it,” she said as she got up and took me by the hand and we walked together to board our flight home.

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

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