Mexican Adventure

It seemed I was going to be the focal point of our trio. They pulled out a red dress that hugged my figure and was tied around the neck. I stepped into the dress in my stockinged feet and moved my hips to allow them to pull up the dress, the shoulder straps were wide enough to hide the bra straps underneath. The dress was made from some organza material, had rows of short tassels hanging down. The square neckline was high enough to cover the bra but the massive size of the bust with the pointed nipples were very prominent. I was committed now and had to endure this. I had to get into a frame of mind where I could enjoy this. It would be a good laugh afterwards.

Vicky brought out a pair of heels. She had my male size and I guess converted it to female. Thank God the heel was lower, maybe 3 "and she fitted the shoes onto my feet. They were a little tight but I could manage. It took a little time to find my balance and I hung on to Vicky.

"Walk a little, one foot in front of the other. You'll get your balance quickly enough." Vicky let go of me and I walked a few unsteady steps. It got a little easier and in a few minutes I was feeling the balance. The shoes still hurt, but it would ease soon enough.

In the meantime, Dolly had painted her face. This was a hooker look straight from the streets. Everything was overdone and exaggerated. Her brows were darkened and heavy black liner surrounded her eyes. Massive black lashes were glued on. Rouge was applied to her cheekbones in a not so subtle manner. Ruby red lips, outlined in black pencil, completed the look. I wondered if I was going to look like that too.

"Sammi, sit here and let Dolly make you up. I've got to get dressed." Vicky still had the towel around her. And I was now Sammi. Was it a baptism by fire I wondered?

Dolly started on my face. I was watching in the large mirror over the dresser. First she applied some kind of moisturizer to my face and neck. I am not sure what she had in her hand, but she applied it to my eyebrows. They were now flat against my skin. She applied many layers. Then came a heavy layer of foundation. She plastered it on even covering my eyebrows. It looked funny to see my face without eyebrows. But I could see my face changing a great deal to what I was used to. Next came the eyebrows painted on. Quite thick in the center arching high and tapering down. I thought it might look like a clown against the foundation. But plenty of pink and grey eyeshadow later, right up to the higher brow line with thick lines around my eyes my hooker face was taking shape. The false eyelashes were as big as Dolly's. She applied many layers of mascara that the lids felt heavy. Lots of rouge of course. It wasn't discreet, applied in a wide band up my cheekbones. The black pencil outlined my mouth in an exaggerated bow and then fire engine red lipstick. I think she applied about 4 layers. Then another 4 layers of a thick gloss. My lips felt full and sticky.

For the final touches I had a set of large red hoop earrings clipped on. She attached some glue on nails of the same fire red color. I didn't think about getting those nails off in the morning. Some rings with large decorative stones. Sammi, the hooker, was ready. One final thing: hair. Dolly brought out a red haired wig which she pulled on my head. It was of medium length and she tugged and pinned it to my medium hair. She brushed it many times and probably applied a full can of spray to keep it in place. I was ready and stood up. I could see the outline of the big breasts through those massive lashes. What would people think?

"I think your clients would love you, Sammi," Vicky said looking at the finished product. She was also fully dressed and heavily made up. Dolly had the bright green dress, Vicky was in gold and I had the bright red. From lipstick color to heavy lashes, we looked like three cheap streetwalkers. That is the look they were going for. I was glad we were thousands of miles away from home. Although I admit my own mother would not have recognized her son under the powder and paint.

Dolly brought out a purse with a long strap. I saw her put some Dollars, the red lipstick, mascara, Kleenex tissues and condoms. "You never know you might need them," she said. I thought I would be lucky to find a girl who wanted to be fucked by a painted man in a dress. I wasn't thinking right. Dressed as I was it would be a man who would want to fuck me or have me suck him off. But you never knew. It was only later that I realized that I might need the condoms if some man were to pounce on me. Both girls appeared to have purses to match their dresses and I guess filled with the same stuff.

It was almost 7 pm. We took the elevator down, arm in arm, and went through the lobby. All heads, male and female, turned to look at us. I was glad that Dolly and Vicky were with me so I didn't stand out too much. We all stood out equally.

All three of us, arms linked swung our hips down the street. First stop was Dolly's tequilerias. There was a sidewalk table available. Dolly, took out her cigarette and lit up and kept the cigarette in her mouth and handed the pack to Vicky. She took one, lit up, blew a cloud of smoke and put it in my mouth. I have never smoked. I had taken a puff or two but never a whole cigarette.

"Keep it in your mouth, like Dolly," Vicky said as she took out another and lit it. . I had a hard time keeping the cigarette in my mouth. Ash just fell, missing the jutting objects on my chest. I stubbed it out as soon as I got to the butt. The others had already finished theirs by taking drags.

Dolly ordered tequila with beer and some small appetizers. I was grateful for that. I didn't want to get drunk. I realized that I was sitting there drinking like a cheap hooker and recalled the conversation of last night with Dolly. I wondered if I could get those prices. As we sat there on the sidewalk, we attracted many looks. I felt very self-conscious. I kept pulling my dress down as it had ridden up when I sat. I could probably pass at a distance, but close up I was sure I would be read. No matter that the others were dressed and painted as I, they could pass muster. I would be a man in a dress.

"So do you think you could get those prices Dolly mentioned?" Vicky was smiling as she asked me the question.

"It's not funny, you know. I feeling funny sitting here dressed like this." I didn't like the joke.

"Cheer up. All these ladies make their money this way. It's a job. Besides, you're dressed for a party so lighten up and enjoy yourself. Enjoy your Sammi side." Vicky took another cigarette and lit up. She held the pack to me, I declined. She appeared happy to blow smoke in my face.

We ate our appetizers and drank more tequila. Two guys stopped and spoke in Spanish to Dolly. There were words exchanged and some laughter. I felt very self-conscious. The men left in bouts of laughter.

"What's up?" I asked thinking maybe they were talking about me.

"They were offering to take us and show us a good time," Dolly said. "They wanted us to show them a good time for a $100. For three beautiful hookers he needed to pay us $ 600, I said. They suggested that we could blow them for $50 for both and that we needed to go to that hotel if we wanted high priced customers. On the street, we wouldn't get that much. They only had $ 20 between them."

I could understand their logic. Sitting here in the fading light, streetwalkers would be in abundance.

Another guy spoke to them in Spanish. Even though we were talking in English, he interrupted in Spanish. Another discussion ensued much to the laughter of Dolly and Vicky. It seemed that Vicky was doing the talking now. Again, he left with a smile.

"And now what?" I asked

Vicky smiled at me, took a deep drag and stubbed out her cigarette. "He offered $ 20 to be blown by you. I said nothing under $ 50. I was correct, right? You wouldn't do it for less." She was laughing.

"Vicky, that's not a joke. It's bad enough I am sitting here dressed like a hooker like you guys, but I am not going to give anyone a blowjob. Got it?" I was getting a little angry as not to understand the conversation and their laughter.

"Loosen up, babe. So if you were offered a $1000 Dollar fee, would you blow a guy? May be ten minutes of work that means $ 100 per minute. Easy money. Would you do it?"

"No way," I insisted. "Not for any amount?"

Dolly who had been silent now spoke to Vicky. I could hear the laughter in her voice. I was sure they were talking about me. Why would I want to have a cock in my mouth?

"What's the joke?" I asked again. "Speak English please."

"We were saying how strange it is. When you are Sam, you would love to have us put your cock in our mouths. We did this and you enjoyed it. But now as Sammi you don't like the idea. We girls love to suck."

"Well, I am not a girl." I was quite adamant.

"Perhaps you should try it to see how we girls enjoy it," Vicky said. "You've never refused to put your cock in my mouths." She took another cigarette. She appeared to be smoking a lot.

"That's different. Sam enjoys Vicky's mouth on his cock. He is a man." I think I had made the point.

Vicky took a deep drag, blew out smoke. "So you don't care if I enjoy it or not. You don't always have to reciprocate either. Have you asked yourself what I get out it?"

I was stumped. Admittedly, I was only focused on my pleasure and not hers. She had a point. I didn't want this to continue as I couldn't win. Dressed as I was, I was vulnerable and would want to have them on my side.

"Sorry, Vicky. You know how I feel about that. I enjoy what you do to me. You know I would do anything for you, right?" She needed to know that I was really ready to please her.

"Really?" Vicky said. "I might hold you to that later. Let's go party." We all took a last shot of tequila, and stood up. Vicky and Dolly checked their lipstick and I felt compelled to do the same. I touched it up although it appeared that the gloss had protected the coloring.

Dolly hailed a cab and we got in. Dolly sat in the front animatedly talking-to the driver in Spanish. Vicky crept nearer to me and her hands wandered up my dress. As I got in, the dress had ridden up exposing my stocking tops and garters. Vicky patted my crotch, but little dickie was still asleep in his tight cocoon. She tugged at my dress and I moved to let her pull it down an inch or two. She leant over and kissed me lightly on the lips. I saw the taxi driver's eyes pop out as he saw two girls in the back seat exchange a kiss. Dolly turned around, saw us and said something to the driver. They both laughed.

"Guys, we are going to Pancho's house. He always throws big parties. But I have a few minutes of business with him. He owns my building and wants to increase the rent. I will offer him some incentive to keep the rate low." Dolly was smiling. We knew what she meant with incentive.

"Pancho is a business man. He is into drugs, property and also has legitimate businesses. I think he also has some girls who take care of him regularly. I need him to renew the lease at the same rent as today. I don't think he speaks any English."

"Remember your promise tonight, and watch how I get out of the car," Vicky said into my ear as we reached our destination. This was an old house, with mature garden and wrought iron gates.

Vicky swung her legs out and exited the vehicle. I did the same and pulled down my dress. The pebbled walkway was not easy but it was just a short distance. We heard music and laughter as Dolly knocked on the door.

The door swung open and a huge guy with curling moustache opened the door. "Ola Dolly," he said kissing her on the mouth. He had on a white shirt that was made to fit his frame. Several buttons were undone.

"Ola Pancho," Dolly said and introduced us.

Pancho lent over hugged Vicky and gave her a light kiss on the lips. I was next and not spared the hug nor the kiss on the lips. I was happy it was just a touch on my closed mouth. His curling moustache tickled me a little.

There were some people there. All of them well dressed. Didn't see many in costume though. I wondered at that and whispered to Dolly, "I thought this was a costume party."

"Just wait, Sammi, the crowds aren't here yet. Pancho is our host and I wanted to be here before it gets too crowded. I have that business to settle with Pancho."

Pancho led us in and offered us champagne. I saw that this was expensive stuff and served in crystal glasses. We clinked and took a sip. It was chilled just right and I enjoyed it.

I saw Dolly whisper to Pancho and he beckoned for us to follow him. All three of us followed Pancho up a short stairway to a study with sturdy doors. Leather chairs, lots of books a huge TV Screen and a heavy desk took up the room.

Pancho sat on the sofa, Dolly sat next to him. Vicky and I sat on individual leather chairs opposite the sofa. Pancho took a cigar from the coffee table humidor and lit it slowly. He was puffing the cigar but looking at Vicky and me. His gaze settled on me and his eyes bore into me. Had he read me? Oh God!

I saw Dolly reach for the cigars too and light up. She blew a cloud of smoke and looked closely at the glowing tip. For a moment my mind flipped as I saw a big fat cigar between Dolly's lips. It could have been a cock. She was deep in thought. She broke off and was speaking to Pancho in rapid Spanish. Of course I didn't understand a word.

I leant forward and asked Vicky what was going on. She took a sip of her champagne and said," It seems Pancho is the landlord for Dolly's bar. The new contract is coming up for renewal and Pancho wants to increase the rent - it seems by a lot."

I could understand that. Dolly's bar was in a prime location on an important street with new hotels and restaurants. Although the premise had seen better days, I was sure that the location would be very lucrative. Tourists seemed to be everywhere.

There was another exchange and I thought that Dolly was trying to play up to him. She moved closer, legs touching and stroked his arm. He had that sparkling white shirt and I saw Dolly's red tipped fingers stroke it gently. Their tone was different. Dolly lent forward and I thought she was going to kiss Pancho. He backed off gently and puffed his cigar. His eyes were still on me.

A moment of silence and Vicky spoke to Pancho. I just followed their discussion and saw a big smile on Pancho's face. Dolly took a deep puff on the cigar and coughed a little.

Vicky and Pancho had another discussion and it seemed that the mood had changed. Dolly was smiling. I was the only one sitting there passively as I didn't understand a word.

Vicky turned to me with a smile. "Sammi, we have a little problem here. It seems Dolly can renew her contract with Pancho. Dolly wants to stay in her bar. It is making her a lot of money. Dolly offered Pancho a personal favor if he would close the deal right now."

"So what's the problem?" I asked. "Let's leave and give her the room to close the deal."

"Well, it's not so simple," Vicky said. "It seems Pancho has his eyes on you. He can have Dolly anytime he wants. It seems he is interested in a hooker like you. He doesn't know you but the way you are dressed shouts 'hooker'." She paused allowing this to sink in.

"What?" I hissed, "He wants me to do something for him? Are you nuts? No way am I going to do anything."

Vicky turned to Pancho. His face was deadpan. Another exchange rapidly. I saw a troubled look on Vicky's face. She was quiet. Pancho was looking at me a big grin on his face.

Dolly spoke to us in English. "Don't worry guys. I can't let you do this for me. I am happy to have new friends but he wants too much."

"What exactly does he want?" I asked.

"Well, he wants to fuck you. I don't care. I have been used before. But I can't let you guys get involved. Let's go," Dolly stood up, stubbing out her cigar. She had a resigned look on her face and was almost in tears.

"Dolly, wait. You said that he wants me, right? Does he know about me?" Maybe it was tequila and champagne talking but I couldn't see Dolly so down. Not after she had given me such a welcome with her mouth earlier.

"No, no reason to tell him," she replied. She fumbled in her bag and took out cigarettes. She lit one and Vicky took one too and lit up. I saw their hands tremble.

I got this crazy idea. Before I could think hard about it, the words were out of my mouth. "OK. I will suck him off if he signs the contract now but he needs to give you two years of a rent freeze. Just a BJ, nothing more." I was looking at Pancho but talking to Dolly. I saw her eyes grow wide and mouth open in disbelief. Vicky was staring at me in disbelief too.

"Are you sure, hon?" Vicky asked. "Dolly does not expect this from you nor me and I don't know if you understand what you are suggesting."

"Look, this guy has been staring at me for the last 45 minutes or so. He is probably not going to let us go without a freebie. I am not sure what I am doing but let's finish this and get on to the party. I can't see Dolly cry. But you both better take care of me later." So there I said it. It didn't sound like a fair deal, but I sensed Pancho's fascination with me. "Besides, you guys made me look like a hooker, perhaps I should act like one."

Vicky and Dolly moved to a corner of the room and spoke in a low voice. I couldn't understand what they were saying. Pancho was still staring at me with that stupid grin on his face.

Vicky and Dolly finished their discussion and came back. A rapid burst of Spanish ensued. I am not sure how it was possible, but his grin grew larger. He was salivating. I hoped Dolly would make my conditions clear as I thought he might turn nasty if he found my boy bits. I was also worried he would try to touch my breasts and notice the foam. It could turn into a disaster. All of that would not be a problem if I knelt in front of him to use my mouth. My other body would be out of reach. Dolly and Vicky had to keep his hands off me.

"He agrees," Dolly said. "The pig! I offered to do whatever he wanted but he's got you in his sight. I even offered him my back door. The slimy bastard."

"Dolly, can you get him to sign something so I don't do this and he changes his mind?" I was trying to clear my head. Perhaps he wouldn't sign and I could get out of it.

Dolly and Pancho spoke again. He was upset and I could hear him raise his voice. But he finally got up and went to his desk. He wrote out a few lines on the paper and signed it. Whilst Dolly was reading it he was taking off his pants. Dolly was OK with the letter and tucked it into her purse.

I got up and smoothed out my dress. I was in for it now. Any error on my part and he would discover my true gender. Then I could imagine being torn apart by him. Dolly and Vicky too. I looked at Vicky; I was scared at what I had promised. Only now did I realize what I had said.

Vicky stared back at me. "So you want to suck his cock? You'll get your chance to be a hooker. But I am surprised you picked a big guy like Pancho." It sounded funny but her voice showed concern. She knew this could go wrong.

"Don't be stupid. I don't want to even if I am dressed like this. I just thought it would help Dolly. That's all. You two had better keep his hands away from my body." I had opened my mouth and put my foot in it.

Dolly and she exchanged a quick sentence in Spanish. Pancho had a lecherous grin on his face and was concentrating on me. Dolly nodded. She came over and looked in my purse. She took out the lipstick and applied more layers to my mouth. She then tore open a condom packet and went over to Pancho who stood there with his boxers down to his ankles in that white shirt only. Dolly took my hand and moved me closer to him. Vicky was stroking his cock to get it rising.