Always Be Closing

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Lost luggage leads to unexpected changes.
3.9k words
4.62
122.3k
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Part 1 of the 5 part series

Updated 10/31/2022
Created 11/23/2010
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centrum1000
centrum1000
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Hi, my name is Tom Jacobson. I am 23 years old 5'9" with light brown hair and a slim build. I currently work as a software engineer for a rapidly growing outsourcing company. This is my first job out of college, but I've already been promoted twice. I am now the lead engineer on my team, which means that I will have to start meeting with clients. This is the story of how my first business trip changed my life forever.

I wasn't given much notice about this trip. Tina, one of the top salespeople at the company, called me up and said that the engineer she had lined up to join her for several high profile prospective clients had to cancel due to a family emergency. She didn't understand all of the technical issues and needed an engineer with her to close the business. Being young an ambitious, I saw this as a great opportunity for me move up in the firm. I told her that I would be happy to tag along. She told me to go home and pack because our flight was leaving in 5 hours. She said that she would arrange for the airline tickets and hotel accommodations, all I had to do was show up to the airport.

I flew out of the office and got home as fast as I could. I knew the trip was only supposed to take four days but I kept thinking that I was forgetting something and since I've never really traveled very much I ended up throwing everything I had into the largest suitcase I could find.

I made it to the airport with about an hour to spare. Tina was standing outside of the security line looking very anxious. I could tell that she was visibly relieved when she finally saw me.

"Thank god you made it. Let's go, we don't have much time."

Although the security line wasn't very long I did hit a snag. I was told that my suitcase was too big to fit in the overhead and that I would have to check it. Since we didn't have much time I couldn't argue about it and handed over my bag. After making it through security we raced through the terminal and made it to the gate just as they were making their final announcements.

I was shocked to find out that Tina had booked us first class tickets. The seats were so big and soft. I even had a glass of champagne waiting for me while we taxied the runway.

Once the plane started moving Tina turned to me and said "Don't worry Tom. I know this is your first sales meeting but you will do just fine. I'll handle everything. I only need you to cover any technical questions that they have. Usually these meeting go very smoothly. All of the prospects that I have lined up are ready to buy they just like to be wined and dined first."

"Ok, I'll try my best."

"Our first meeting is tonight at the client's office. We have plenty of time to go back to the hotel and freshen up first. Try to relax and get some sleep on the flight."

With that she turned around slipped on a face mask and tried to sleep.

I was way too nervous to sleep and ended up having a few drinks to calm my nerves. We hit a little turbulence on the way and the flight attendant stumbled as she was serving drinks. I got hit head on with a full glass of cranberry juice. My shirt was ruined, but thankfully I had plenty of spares packed away in my bag.

When we finally landed Tina looked calm and relaxed while I was feeling a little tipsy.

Tina didn't seem very happy that I had to check my bag and kept looking at her watch while I waited for it to come through the baggage claim. After the last bags were picked up it became obvious that mine was nowhere to be found. Tina said that we needed to go or we would be late for the meeting. I ran over to the lost luggage office and filled out the lost baggage paper work. I was assured that I would have my bag delivered to the hotel sometime that night.

We hopped into a cab and headed to the hotel.

"I can't believe you spilled your drink. And who checks their bags anyway?"

Tina was clearly upset with me.

"It's not my fault."

"If you had a carryon bag like everyone else we wouldn't have this problem no would we?"

"I'm sorry Tina. I can try to wash my shirt out at the hotel."

"Are you kidding me? That stain is never coming out."

The rest of the ride was silent as I racked my brain thinking of a way to save the meeting. We pulled up to the hotel and Tina finally said something to me.

"Listen, I have an idea. Just go up to your room and take a shower and I'll stop by in a little bit."

"What are you talking about?"

"Don't worry, it will be fine."

I got up to my room and cleaned up. Since I didn't have any clean clothes I put on a robe and waited for Tina. After about a half hour I heard a knock at my door. Tina pushed her way into my room carrying a large shopping bag.

"Ok Tina, what's your plan?"

"I brought one of my spare suits for you."

"This is never going to work Tina."

"Well we don't have much choice now do we? The stores are all closed and we can't miss this meeting. Do you want to go back to the office and explain how you blew a $5 million dollar deal?"

I felt awful. The least I could do was try to save the meeting.

Tina dropped her bag and walked over to me. She deftly pulled the belt of my robe out and pushed it off of my shoulders. She looked me up and down as I stood there naked in front of her.

"This might just work. Back in the shower we need to shave your body, and I mean everything."

"What? I'm not shaving my legs!"

"Not just your legs, and you don't have a choice. We need you to look like a woman for this one meeting and then you will have your luggage back."

She had a point, it was just one meeting.

"Ok, I'll be right back."

"Hurry up."

As soon as I turned the shower off she opened the bathroom door and handled me a towel. I dried myself off while she was fishing around in her bag.

"Come over here and stand still."

She took out two rubber balls one at a time and put what looked like glue on the back of each one. Before I could even resist she moved over to me and pushed each one onto my chest.

"What the hell are you doing?"

"Don't worry, this glue is only supposed to last for a few hours and then it will wash right off."

When she was done I looked down and saw that I had two perky breasts. The color of the rubber was almost an identical match to my skin tone. I couldn't believe how realistic they looked. I reached up and took them in my hands. They even felt like real skin. The edges were glued to my skin so that you couldn't even see the seams. I even noticed that the nipples hardened as I pinched them.

"I slipped out to an adult novelty shop while you were in the shower. They said that these were the most realistic ones they had and that the nipples would respond to touch and temperature."

"Amazing."

"We can't have a bulge sticking out so I had to get you something special."

Tina pulled out another piece of rubber and the glue. She grabbed my cock in one hand and slid it into the rubber with the other. After a few moments she looked up and said "Perfect."

I look at myself in the mirror and my cock was gone! I couldn't believe that I now had a very realistic pussy staring back from between my legs.

I reached down and touched myself. Just like my new breasts it felt just like real skin and it looked very natural.

"You see, your cock is pushed down and held against your crotch so that it won't be visible or be able to get hard. The tip of your cock is positioned right here."

She pulled out another tube and rubbed something on her finger and then reached out and pushed her finger inside of my new pussy rubbing against the head of my cock.

"This way you can still go to the bathroom, or do anything else that a woman would normally do. That lube will make sure that everything is soft and moist down there."

Next, she pulled out a wig and pushed it onto my head. After a few minutes and many hair pins she was satisfied and said that it wouldn't come loose no matter what.

I turned to look at myself in the mirror and saw that I now had shoulder length light brown hair. I turned my head back and forth and my new hair swished around tickling my neck and shoulders.

"Almost done."

She opened up a makeup bag and started rubbing foundation all over my face. She glued on fake eyelashes and fingernails and finished me off with bright red lipstick. She squirted some scented lotion into her hands and rubbed it all over my body starting with my legs. I could feel my cock straining against my new pussy as her fingers glided across my freshly shaven skin. She worked her hands up my thighs and hips across my chest and finished with my neck.

Looking very proud, she looked up at me and asked me what I thought.

"I can't believe it, I look just like a woman."

"A hot one at that!"

My face felt flush at the compliment.

"Let's get you dressed we don't have much time."

I followed her out of the bathroom and saw an outfit waiting for me on the bed. She laid out a dark pleated skirt, silver silk blouse, matching see-through black lace panties and bra, black lace garter belt, silk stockings, and a pair of high heels.

I slid the panties on first. This lace felt amazing sliding up my bare skin. Every touch of the fabric sent a wave of electricity through my body.

Tina helped my with the bra and garter belt. She showed me how to pull the thigh high stockings up my legs and clip them into place making sure that they were on straight. She helped me button the blouse but left enough unbuttoned to show off a little cleavage. I slid the skirt up my legs and noticed that since I was a little taller than her it didn't cover very much of me. I would have to be very careful tonight.

Tina gave me a pair of small gold clip on earrings and then finally handed me her high heels. She helped my practice walking around the room for a few minutes and thankfully I have pretty good balance. I was able to get used to them very quickly.

"You look spectacular! Let's go get this business!"

I looked at myself in the mirror and couldn't believe it. I didn't even recognize myself anymore.

"I'll do most of the talking but you need to practice using a female voice ok."

I cleared my throat and said "Ok, I'll try."

"Don't worry, you'll get it."

We headed out of the room and hopped into a cab. We made it to the client's office right on time. Tina introduced me as Marcy, one of their best new engineers. The meeting went well and I didn't have to do much talking at all. I noticed the client, Bob, stealing a few glances at me throughout the meeting. Each time I would get a little more nervous that he suspected something.

At the end of the meeting it sounded like he was going to go ahead and make the order and since we had taken a cab earlier he offered us a ride back to our hotel. Tina agreed but said that we needed to freshen up first. She took my hand and led me to the ladies room.

"You did great in there Marcy."

"I can't believe it. I could have sworn that he knew something was up he kept staring at me the whole time."

"He doesn't suspect a thing. He was checking you out because you look hot."

I couldn't believe it. Is it possible?

Tina turned to me and undid another button on my blouse, exposing a little bit of my black lace bra. We both reapplied out lipstick and headed back out to the lobby. Bob had already pulled the car around and was waiting for up in front of the building. Tina hopped into the back seat and I sat in the front with Bob.

Now that I knew what he was thinking I paid more attention to him. I was flattered that he thought I was sexy and I was still a little tipsy from the drinks earlier. I noticed him looking down at my legs at a stop light and let my body slide down in the seat a little bit so that my skirt would ride up and show a little more skin. He kept looking down at my legs as we drove the rest of the way and I happily continued with my show by letting my knees spread apart. By the time we reached our hotel I was feeling a little flush.

Tina invited Bob to join us at the hotel bar for a drink or two and when I looked down as I got out of the car I noticed that my panties were now clearly visible. I guess I gave him a little more of a show that I expected.

Tina led us to a table in the far corner of the bar that had two low leather couches facing each other. Tina and I sat on one side and Bob sat facing us. When the waitress came to take our order Bob took the initiative and ordered three martinis, extra dirty. He gave me a sly wink as he said that last part.

As we chatted over the first round I noticed him looking at my legs again. Since I had already given him one show I didn't see any harm in another one. I let my legs fall apart acting casual as if I didn't notice. I am pretty sure that he had a perfect view of my panties while we sat there.

We finished our drinks and ordered another round when Bob excused himself to go to the bathroom. Tina got up and took his seat across from me.

"Listen, these guys love the attention and we need to do whatever it takes to make sure we close the deal ok?"

"Ok, whatever it takes."

Tina was still sitting across from me when Bob returned. He took her seat and slid next to me on the couch. Our legs were touching as we continued chatting over the second round of drinks. After my second martini I was starting to feel a little drunk but knew that I had to keep up the act. Bob ordered us another round and let his hand fall onto my knee as we waited.

I don't think that Tina could see his hand on my leg from across the table. After a few minutes he was getting a little bolder and his hand started to move up my stocking covered thigh while gently squeezing me. I could feel my penis twitching at his touch. My head was swimming at this point.

Tina got up and excused herself right as his fingers found the edge the stockings. I was all alone when his fingers trailed across my bare tight. My breathing was getting heavier and I'm sure he could tell that I was getting excited. I was trying to continue that conversation as if nothing was happening but he moved in and pushed his lips against mine.

My body shuddered at the shock of him kissing me. He tasted like vodka. My lips parted and our tongues touched. His fingers were moving up my thigh and were touching the edge of my panties. His hand covered my panties and he gently rubbed my cock through my rubber pussy. Thankfully this contraption kept my cock from getting hard because I was so fucking horny at this point.

Bob's other hand reached out and slid around my neck pulling me into his kiss. He let his hand slide down my neck and land on my left breast. He was fondling my chest when his finger slipped into my panties and pushed into my fake pussy. I could feel his finger rubbing against the tip of my cock as he slowly fingered me. I was going to explode.

I reached my hand and grabbed his crotch. His cock was rock hard at this point. I looked around and saw that nobody else could see us so I unzipped his pants and pulled his cock out. His skin felt silky and hot in my hand. I couldn't believe that I was holding on to another man's cock. I started to stroke him under the table when he broke off our kiss. He took his hand out of my panties and gently pushed my head down to his crotch.

I slid off of the couch and onto my knees. I worked myself between his legs under the table and stared at his rock hard cock inches from my face. I slowly moved my mouth over and nervously licked the tip of his penis. He tasted sweaty and a little salty. I moved forward and took the entire tip of him into my mouth while swirling my tongue around.

Suddenly I heard a voice and froze. The waitress had returned with our drinks and Bob was chatting with her as if he didn't have his dick in my mouth. I waited until it sounded like the coast was clear and then I pushed my head down and slowly swallowed his entire shaft. It was hard for me to breath at first but I started to get the hang of it as my head bobbed up and down the length of his cock.

I reached my hand up and started to massage his balls while I suck his cock. My pace was getting faster when I felt his cock expanding in my mouth. I didn't know what to expect when the first stream of cum shot into my throat. I sucked hard so that I could swallow it all and then another shot of cum came out. I was working hard to swallow everything when his third shot of cum filled my mouth. It was too much for me and I could feel it dripping out of the corner of my mouth.

I kept licking his cock clean as it slowly grew soft in my mouth. After I finished cleaning him off I pushed his penis back into his pants and zipped him up.

I had forgotten all about Tina until I saw her sitting across from me as I reemerged from under the table with a big devilish smile on her face. I stammered nervously and said that I dropped an earring.

Shortly after his happy ending, Bob said that he was very happy with our meeting and would sign the documents in the morning before excusing himself for the night.

After he left Tina turned to me and said "I think you have a little something on your face Marcy."

I reached up and realized that some of Bob's cum was still on my face. Embarrassed I wiped it off with my finger as if it was just another crumb.

"I knew you would be a natural saleswoman Marcy. Good job tonight!"

"It's getting late and we have to prepare for tomorrow. We should head up to the rooms.

I followed her to the elevator and was about to press the button for my floor when she said.

"Why don't you stay in my room tonight? You don't have anything to change into in your room anyway."

I was still very excited and a little drunk so I said.

"Sounds like fun."

After the elevator door closed she turned to me.

"Don't feel bad Marcy, I've had to do all sorts of things to close a deal. It's just part of the job sometimes."

She then moved in and kissed me. Her tongue entered my mouth as she pushed me up against the wall of the elevator. Her hands were already under my skirt. She started rubbing my cock through the panties when the door opened on her floor.

She broke our embrace and pulled me out of the elevator. I followed her into her room and immediately started to tear off her clothes. She threw me down to the bed and adjusted my cock so that it was sticking out of the opening of my rubber vagina. I immediately sprang to attention as she buried her mouth on my cock. I looked down at her and watched the top of her head bouncing over the mounds of my breasts as she furiously sucked my cock.

After a few minutes she pulled her mouth off of my penis and climbed on top of me, straddling me with her legs. I reached up and took her breasts in my hands as she slid her dripping pussy down onto my hard cock.

"Oh god!"

She screamed as my cock filled her tight pussy.

I kept massaging her breasts and pinching her nipples while she fucked me. She gyrated her hips as she rode me. I've never been fucked like this before. She pushed her body up and thrust herself hard back down pushing me further into her with each thrust.

I knew I wouldn't last long at this pace and my cock exploded inside of her. She screamed again as my cumming pushed her over the edge. Her pussy was squeezing tight around my penis sucking every last drop of cum out of me.

After a little while she collapsed on top of my chest with my cock still buried inside of her.

We stayed like that for almost a half hour catching our breath until she rolled off of me and got up. She reached her hand out to help me up and started to undress me.

After I was naked, she tucked my penis back into fake pussy and again felt around the inside with her finger.

"I can't believe how real this feels. You could fool anyone with this thing."

Tina walked over to her luggage and pulled out a short red silk negligee and a pair of matching silk panties.

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