Always Be Closing Ch. 03

Hi, my name is Tom Jacobson but you can call me Marcy. I am 23 years old man. I'm 5'9" with light brown hair and a slim build. This is my third story about what happened on my first business trip after my luggage was lost. It all started when my coworker Tina convinced me to wear one of her spare outfits so that we didn't lose the business. She did a great job making me look very convincing after getting me a set of silicone boobs and even a very realistic looking fake pussy that she managed to glue over my cock, completely concealing my last vestiges of manhood. My last story left off with a shopping spree before we met up with a prospective client for a second meeting.

After getting back to the hotel we both showered and started getting ready for the meeting. Tina took her time making herself up first and then helped me pick out an outfit. We finally settled on a silver corset, just like the pink one I wore earlier, for the top and a tight black mini skirt that hugged my hips as I walked.

The skirt was so tight that Tina told me that I would have to wear a thong. She handed me one that had a sheer front panel that left my fake pussy clearly exposed. I had never worn a thong before but found the feeling of the thin strip of material tucked between my ass cheeks to be very sexy. Every movement that I made reminded me of the skimpy panties that I wore under my tight skirt.

Tina helped me attach a pair of thin black thigh high stockings to the garter straps on the corset. The stockings had a black line that ran up the back of my legs and Tina was very careful to make sure that the line was straight before we left.

I slipped on a pair of black high heels before Tina started with my makeup. By now I was getting used to walking in heels and it was starting to feel natural to me. Since I had been practicing talking as a woman too I was also starting to feel more comfortable and realized that I was beginning to use my new feminine voice without even thinking about it.

It took Tina 45 minutes to apply my fake eyelashes and get my makeup just right, but what a difference. This time she plucked my eyebrows, which weren't very thick to begin with but now have a very feminine shape. With a little bit of color in my cheeks and some dark red lipstick I was now unmistakably a woman.

After finishing up with my makeup Tina knelt between my legs and spread my knees apart. After pushed aside my panties I felt her finger slip inside of my pussy and along the length of my flaccid penis.

"We need to make sure that you stay lubricated down there. Just in case." She looked up at me with a wink and helped me straighten my skirt.

I spent another ten minutes in front of the mirror tossing my shoulder length light brown hair around and practicing pouting and winking before Tina said it was time for us to go.

"Ready? I just got off the phone with Tom. He wants up to meet him at a Japanese restaurant across town for drinks and a little sushi. If we leave now we should just make it on time."

"I've never had sushi before, but I'll try anything once." I said with a wry smile.

"This is a very big opportunity for us so we need to make this meeting count." She emphasized the word need and her message was very clear to me.

"I understand Tina. I'll do whatever it takes to seal the deal."

"Good, now let's get a move on."

It was ten past nine when we arrived at the restaurant and were told that our host had already been seated. The hostess led us through the restaurant to a dark hallway in the back. The hallway was lined on either side with thin translucent paper walls. The light coming through the paper walls cast a yellow glow on us as the hostess showed us to our table.

She slid open a door revealing a small private room and pointed to our feet before letting us enter. I noticed a small pile of shoes on the floor and added my heels before stepping into the room.

The only light in the room came from four red paper lanterns hanging in each corner of the room. The table was low to the ground and our host and another man were both sitting cross legged on the floor which was covered in a straw mat.

As Tina and I entered the room our host, Tom, stood up and commented how nice we both looked before introducing us to the other man in the room.

"Ladies, this is Robert Peters. He is our head of technology. I figured that he should be here to help me make my decision."

Tom introduced the two of us to Robert and we took our seats.

I sat next to Tom with Tina and Robert sitting opposite us. Robert was across from me and Tina was across from Tom. They had already order a bottle of sake before we arrived and poured us some after we all sat.

Tom was an older gentleman; he looked like he was in his 50's, with salt and pepper hair parted on one side. He wore a white button-down shirt and a pair of tan dress pants. The top two buttons on his shirt were left open.

We spent about 20 minutes discussing business before moving on to lighter conversation. Tom had a warm personality and we fell into an easy rapport in no time. I noticed that he was being very attentive to my sake glass and never let it get empty. I was enjoying the atmosphere and the conversation and didn't bother keeping track of how much I was drinking.

After the first round of sushi I felt his warm hand on my knee. When I looked down I realized that by sitting with my legs crossed I was exposing both the tops of my stockings and part of my thigh above the stockings as well. I put my hand of top of his and gave him a little squeeze as I turned to him and flashed a little smile. He leaned into me and with his face brushing against the nape of my neck whispered into my ear to tell me how nice I smelled. His hand slowly circled my knee and began moving up my thigh.

I noticed throughout dinner that Robert was trying to look at my cleavage every chance he got. Since my corset had a plunging neckline that gave a great view of my fake tits I did everything I could to act as if I didn't notice. In fact I was flattered to have another man looking at me with such lust in his eyes. I even found a few excuses to lean across the table to reach for a piece of sushi in order to give him a better view.

Tom's hand caressed my thigh and occasionally his fingers slipped around and traced lines along the inside of my thighs. When he finally reached the top of my stockings and brushed against my bare skin I could feel him pushing the hem of my skirt further up my leg. In an effort to help him I readjusted my position and in the process pushed my skirt up over my ass exposing more of my leg to his curious hand.

I was enjoying the attention that I was getting from both men when I noticed that Tina was trying to get my attention.

"If you'll excuse me, I need to powder my nose. Marcy, would you like to join me?"

"Sure, my makeup could use a touch up."

When I stood up to leave our private room I realized that my skirt was still hiked up and I gave Robert a perfect view of my barely covered pussy from across the table. I didn't want him to be embarrassed that I saw him looking so I pretended that I didn't notice and didn't fix my skirt until I was in the hallway.

In the bathroom Tina confided that her stomach wasn't feeling well and thought that it might have been something that she ate. She needed to go back to the hotel but since we were paying for the meal I would have to stay and entertain Tom and Robert alone.

"Don't worry Tina. They're both nice guys I don't think it will be a problem."

"I'm so sorry Marcy, but I just can't stay like this. Thank you so much for taking care of this tonight."

Before I reentered our private room I decided to hike my skirt back up like it was before and give Robert another eyeful. I slowly entered the room and took my time taking my seat so that he would have plenty of opportunity to stare at my panty covered pussy.

Tom wasted no time and his hand quickly made its way to the bare skin on my upper thigh again. I told them what happened to Tina and apologized for her early departure.

They both seemed disappointed but understood.

We picked up our conversation again and worked our way through two more bottles of sake before Robert excused himself to go to the bathroom.

As soon as he slid the door shut behind him I felt Tom's hand slide across my panties. I leaned back as he rubbed the tip of my cock through my fake pussy. His touch was strong but gentle and he leaned across my and pressed his lips to mine as his fingers found their way inside of my panties.

My mouth opened as we kissed and lost myself in his embrace. I gently bit his lip as our tongues touched. I moaned when he finally slipped his finger inside of me and rubbed against the soft tip of my penis.

The door slid open again and Robert stepped back into the room as we both sat back up and tried in vain to act as if nothing had happened.

We finished the last bottle of sake and Tom suggested that we go up to his apartment for a night cap since he lived across the street. I took care of the bill with Tina's corporate card and the three of us headed across the street.

The building that Tom lived in was a new ultra-modern condo complex with a minimalist design. The large lobby was empty except for a desk occupied by a security guard.

We walked across the lobby to the elevators and rode up to the 19th floor.

Tom gave us a quick tour of his one bedroom apartment and proceeded to make us drinks before leaving Robert and I alone as he needed to use the restroom.

When Tom left us I moved closer to Robert as he took my face in his hand. Our mouths connected and he kissed me passionately. I kicked off my heels and pushed him into Tom's bedroom as we kissed. I fumbled with his clothes as we entered the bedroom stripping his as quickly as I could. Once he was naked I pushed him back onto the bed and crawled on top of him.

My hands were busy as I touched another man's naked body for the first time. My own cock swelled as my mouth kissed the soft skin of his chest. I pushed him up further on the bed and let my mouth drift lower on his body until I felt his hard cock pushing against my chin.

I lifted my head up and took his throbbing penis in my hands. The tip of his cock was already covered in pre-cum and I eagerly reached out with my tongue and licked up his juices. I savored his salty flavor on my tongue while I stroked his cock with my hand.

I lowered my mouth onto his cock while my hand continues stroking the base of his shaft. It felt so good having another cock in my mouth again I quickly took his entire length into my mouth. My tongue wrapped around the soft warm skin of his manhood as my mouth moved up and down his cock.

While I was sucking on Robert I felt a pair of hands grab me at my waist but in my current position I couldn't turn around. I assumed that Tom was joining us on the bed and felt his hands pushing my skirt all the way around my hips exposing my thong and ass to him. His hands slipped into the waistband of my panties and the thin fabric slowly slipped out from between my ass cheeks as he pulled my panties down my legs. I managed to lift my knees one at a time to help Tom remove my panties while keeping my mouth on Robert's cock.

I was pushing Robert's cock deep into my throat when I first felt something pressing against me between my legs. Slowly it pushed harder against me until I felt something slip into my pussy. I moaned as Tom's hard cock pushed its way inside of me and rubbed against the length of my semi-erect penis. I almost came when I first felt the soft skin of his hard cock rubbing against my own cock.

After he finally entered me he paused long enough that I could feel his hard cock pulsing to the rhythm of his heartbeat as it pressed against the length of my penis. He slowly pulled his cock out sliding along my shaft with each thrust. I felt my own cock pushing in vain against the confines of my rubber pussy. My cock throbbed as I came with him buried inside of me. My cum exploded out of my penis and covered Tom's cock as he again pulled out of me.

I continued to suck on Robert's cock while I came but I realized that in his drunken state he might need more help to climax. I took my mouth off of his hard cock and reached my hand around grabbing Robert's penis while I pulled myself off of him. I took Robert's cock in my other hand as I repositioned myself so that his penis was directly between my legs. Guiding him into my now dripping pussy I lowered myself onto Robert. I heard him moaning as he entered me.

With my other hand I guided Tom's cock to my other opening hoping that my cum that was now covering his penis would provide enough lubrication for him to penetrate me from behind. I released my hand and moved it back around and grabbed onto Robert's chest with both hands to help balance myself. With Robert's cock fully inside of me I could feel the tip of Tom's penis pushing against my virgin asshole. Instinctively I pushed my knees as far apart as I could to ease his entry. The pressure grew until it finally gave way and I felt his hard cock filling me up from the inside. I gasped and felt a shockwave of pleasure explode across my body as he pushed deeper inside of me.

I ground my ass into his hips to meet his thrusts and slowly worked up a good rhythm with both cock fucking me at the same time. Robert was moving faster and faster as he pumped his dick into me. I felt something pulling against my skin and realized that my rubber pussy was separating from me and Robert was now left with me sliding my soft, but now growing, cock against his. He must have been too drunk or excited or some combination of the two to notice that he was now clearly not fucking a woman.

Unsure of what to do I decided that my best bet would be to keep my hips pressed against his so that he couldn't see anything and get him off as quickly as possible. Unfortunately, now that my own cock was now freed from its feminine prison it was rapidly getting harder as well. As Tom fucked my ass my now hard cock was furiously sliding along Robert's cock as I hoped he would cum soon.

In an effort to help Robert cum I reached around with one of my hands and started pulling on his balls. Moaning loudly as I grabbed him he pulled my face down to his and kissed me as his cock throbbed between my legs. Feeling his cock twitching against mine as he came pushed me over the edge and I came with him. I pressed his cock against his stomach with my own as we came shooting ribbons of cum all over his stomach. We kissed as his cock slowly softened under me and Tom continued his relentless pounding in my ass.

I collapsed on top of Robert submitting myself to Tom's fucking. He pushed deep into me and his cock grew as he filled me with his cum. He emptied himself inside of my ass in three long bursts before he slowed his pace and finally pulled his cock out of me. I could feel his cum dripping out of my ass down my thigh as I lay on top of Robert, who by now had fallen asleep.

Tom went over to his closet and retrieved a plush bathrobe. I recognized my opportunity and pushed my skirt back down my legs as I rolled off of Robert and sat up on the edge of the bed. I noticed the rubber vagina lying next to Robert and managed to sneak it into my purse while Tom's back was to me.

Tom walked over to me and gave me another kiss before saying "You made quite an impression on us tonight Marcy. I think we would be happy to do business with you. We will need you to come out and visit once a quarter of course. That won't be a problem will it?"

"I'd be happy to come back any time. We're here to satisfy whatever the client needs." I looked over and saw how late it was and realized that I needed to get back to the hotel.

Tom helped me get a cab and I headed back across town.

Tina was already asleep when I got back so I tried to be as quite as possible. I noticed that she had picked out an outfit for to wear to bed and quickly slipped out of my clothes. Tina picked out a one piece black satin teddy that had a boy shorts bottom. I stepped into the legs and pulled the shoulder straps up my body. The soft material felt so good sliding across my cock as I walked over to the bed. I slipped into bed next to Tina, whose back was to me, and wrapped my arm across her body as I snuggled up to her with my cock pressed against her bare ass. My hand caressed her body as I slowly drifted off to sleep.