My heart raced as I stood in the lobby waiting for him. It always raced when he was involved. It was the whole reason I was there, standing alone in the public lobby of the fancy hotel downtown wearing nothing but a negligee and high heels. I figured it passed as a dress. It extended all the way down to the floor and yes, it was backless and there was a slit all the way up both legs all the way to my hips, but you had to look at me to know I was wearing pajamas.
Most people didn't look, or if they did, hid their eyes or made do with passing glances.
Some did look though. There was one man in particular, older, heavyset, in a worn and wrinkled gray suit who did little to cover his interest. He was staring. At first, I had turned my back to him but I couldn't see the door that way. When there was no option but to just make the most of it I turned, arched my back, thrust my chest forward stressing the cleavage revealed by the deeply plunging front of the gown and allowing him to take in the way my nipples pressed out at the thin satin.
Tom was late. He had hinted to me that he might be. I was irritated for a minute until I realized it was part of the game. His plan all along was to leave me there on display.
A man walked up and tried to make conversation. He was young. I would guess in his late twenties. He was pretty. He was too pretty for me. I was pleasant enough but dismissive. I was waiting for someone, I told him. He said I was gorgeous. I thanked him. I moved away. My feet were beginning to hurt. I took a seat in an oversized chair.
"What? You didn't think Matt was cute?" read the text.
"Where are you?" I asked him. I didn't want to give up and leave. I was getting close though.
"Look over your shoulder," he sent. I did. I chose the wrong shoulder. He texted me to look over the other one. Craning and twisting my tit slipped out the side of the dress. I growled, stuffed it back in and looked again. He was in a black suit sitting at the bar. He had a lowball glass filled with dark liquid. He made a short toasting gesture.
"Asshole," I teased him. "Are you enjoying yourself?"
"Not as much as the fat guy across from you."
"Asshole," I teased him again. I put a little smiley face after it so that he knew I was playing. I was relieved, excited, and ready.
It was three months to the day since the lunch. We were casual friends at best. His wife was my friend and we had forced the husbands on each other. They turned out to get along well and had taken to playing golf and meeting up to watch football games. The day it all started, the four of us were supposed to meet for lunch but his wife was held up and my husband, never the brightest bulb in the string, had gone to the wrong restaurant. Sitting over burgers and beers we fought through the tension.
I wasn't unhappy. Really it was kind of the opposite. I was perfectly contented with my life and my husband. I think it was that perfect contentedness that caused it. It left me vulnerable to surprise. I told him I hoped no one we knew saw us together. There would be talk.
He said as long as we never had intercourse it didn't matter. The specificity of his comment intrigued me.
It felt like a dare. I told him how dangerous it was. I told him he didn't know me. He didn't know I had absolutely no limits. I told him I would do anything he asked me to. Double dare.
He asked me to go into the bathroom. He wanted my bra and panties. I laughed at him. He laughed back at me. He said I was all talk. He left lunch with my underwear in his pocket and I had a long tortured afternoon back in my office. The game was on.
For the next month, it was pretty tame. We would all meet for drinks and he would instruct me to blow my husband in the parking lot. He sent an outfit to my office, one of those tiny party dresses that teenagers wear to prom and met for drinks and flirted and pawed each other. He had me meet him in a park -- naked. We began to kiss. By the end of the second month, oral sex had been incorporated. At first, he just ordered me to spread my legs and sit still but finally, after a good deal of begging, he let me go down on him.
I couldn't help it. We were too far along now. I wanted the rest of it. I wanted his cock. I told him exactly what I wanted. I wanted to meet him in the afternoon. I wanted him to dress me. I wanted to be taken upstairs. I wanted to be fucked long and hard until I was sore for a week.
He told me it was against the rules.
I told him I didn't care.
He insisted all this only worked if we followed the rules but that he would think about it.
Waiting for him in the hotel, it was time. God, I wanted it. I watched him watch me. Everyone else in the hotel slipped away like in a portrait where the background is all out of focus.
"Are you going to fuck me now?" I texted him.
"No," he replied.
I looked at him with a raised eyebrow and then went back to my phone.
"Against the rules," he had sent.
"I was promised a good lay. You don't want to see me pissed off."
"No. I want to see you fuck," he said.
He snuck up on me while I read his last message and thumbed in a confused response.
"Maddie, I'd like you to meet Matt. Matt, Maddie. Shall we?"
I was silent in the elevator. The men stood on either side of me talking about nonsense. I think they talked about football. When we finally slipped into a small but luxuriously appointed hotel room, Matt dismissed himself to the bathroom and I had Tom alone.
"I see what you have planned but it's not what I wanted. I wanted you," I said in a pouty voice. I kissed him. I pressed my body against him. I felt him respond, twitching, half hard, against my leg.
"We made a deal. I can't sleep with you."
"Well, whats the deal with little Matty boy in there?" I gripped his cock. I still believed we would make love, any minute now.
"You said you would do anything."
"Mmmm. I will."
"Well, your challenge today... is Matty Boy."
