Chicago Pt. 01

We had been in Chicago for a few weeks on a business trip that wasnt going well, and if I hadn't promised Lynn a nice night out I would've washed my hands of the deal altogether and left that night. Big payout be damned, it wasnt worth weeks of drama. She changed my mind in a way that I'll never forget, and as it turned out I ended up closing the deal a few days later.

It began as I walked into our hotel room after another frustrating day of endless arguments and document signing with out of state partners.

"Pearls, huh?" In an instant my bad day turned around. She only smiled in response. She's small for 22, but still quite nice to watch hop around the room in her evening dress. That night she took my breath away with beauty beyond words in a dress my credit card probably paid for just that day because she didnt own it before my meeting. I didnt really care; she has good taste and I always enjoy coming home to her. I placed my coat down on a chair as I walked out to the balcony overlooking the city.

With a deep breath of the cool city air I placed my hands on the railing, and tried to recenter myself before fulfilling my dinner obligation. The streets were aglow with brilliant hues of copper and ash. Specks of red and green cycled through the evening byways as the night owls began about their lives. Laughter and dogs could be heard in the plaza below, and a light breeze delivered to me the sweet perfume of my young companion as she slowly placed herself between me and the railing.

"How was the proposal, Daddy," she asked with a flat tone as she handed me a glass of my favorite wine. I felt her fumbling with my belt, but eventually felt her small, cold hands wrap around my growing cock.

"Not good," I replied as she lowered herself out of sight. I sipped my wine, looked out to the city, and continued, "we were finally making progress and talking closing today, but they want to renegotiate because one of their clients backed out at the last minute."

She popped my cock out of her warm, swirling mouth and I felt the cool breeze brush my balls as she uncovered them. "Hm, you think we'll have to stay longer," she playfully inquired before I felt my wet cock rest on her face as her warm mouth massaged my balls.

I looked down to respond to her, but when her big, blue eyes met mine her lips met my pelvis. She wrapped her arms around my waist to pull me closer, and every negative thought I had left me. She tightened her mouth around my hard cock, and swirled her head around so I could feel her throat gently milking me. Without pausing she unwrapped herself, and cupped my balls so she could reach them with the tip of her tongue as she massaged my length with the rest of her mouth. It took all the discipline I had and handful of her soft, blonde hair to keep from dropping my wine glass into the plaza. She stopped mouth fucking me so I'd loosen my grip, but kept me in her mouth so I'd know she wanted control of the evening plans. I put my free hand back on the railing and let her continue.

"Maybe another day is just what we need to reconsider how our interests here align with those at home,'" she remarked after pulling me out to take a breath. I knew she was talking about more than just business at this point.

I tried to respond, but she took me all the way in again before I could get a sound out. My eyes shot straight to the cityscape with disbelief, and I lost it. I had to place my glass down and hold the railing with both hands.

She gagged a little with my cock already bulging her throat and tightening the pearls. Before I was finished she pulled back enough to grab the base of my cock with one hand while keeping my balls cupped in the other. I watched the pearls loosen as she pulled me out just to cover them with what remained of my climax. A single strand of my warm cum connected her puffy red lips to her covered necklace. She took me all the way down again to make sure I was empty before standing and handing me my wine glass.

"Let's go eat, Daddy," she said with a smile before grabbing my coat and heading straight to the door.