In this chapter, Daniel has sex with his first real job, Andrea. He also helps train Cynthia some more so she gets better at licking pussy. Daniel also recruits another female for Elite, for women only. This chapter contains regular intercourse, oral sex, lesbian sex, and group sex. This work is copyrighted, and not to be altered, duplicated, copied or published anywhere, including alternative media, without the written consent of the author. © Copyright 2025.
I'm Just a Gigolo, Ch 3
Andrea, My First Paying Job
On my walk to Andrea's place, I stopped for some flowers for her from a street vendor. Some daisies as opposed to roses, as I certainly didn't expect this would be a romantic relationship. I arrived five minutes before my appointment. I rang the doorbell and the door was opened by a butler or valet wearing the house livery. There was a maid setting up a silver service in the room the butler led me to, a type of sitting room. There were a half dozen powdery cookies laid out on a plate next to the silver tray. The butler asked if he could take my flowers, but I wanted Andrea to get them from me, so I declined.
"Coffee or tea, sir?"
"Coffee, cream, no sugar."
"Yes, sir." She poured me my coffee and she poured out a hot tea with some lemon for who I assumed would be Andrea. I took a seat and sipped my coffee while I waited. I made a mental note that Andrea liked hot tea with lemon. The maid left.
Andrea arrived about five minutes after seven, so ten minutes after I'd arrived. She swept into the room wearing a lovely dress which accentuated her cleavage. As Julie had warned, she was a little overweight, perhaps twenty to thirty pounds by my estimation. I stood up as she entered the room. She stopped on seeing me, and gave me the once over, smiling at what she saw.
"Daniel Bancroft, I presume," she said.
"Yes, Ma'am."
She handed me her hand saying, "Andrea Gormley."
Instead of shaking her hand, I bowed over it, kissing her knuckles. "Your servant, Andrea."
I reached down to the table and grabbed my small bouquet of daisies, handing them to her. "For you. May I say that your gown is almost as lovely as you are."
Andrea smiled again, accepting them. "Somebody raised you right."
"My parents."
She rang a bell and the maid returned. "Please put these in water and put them beside my bed."
"Yes, ma'am."
As soon as the maid was gone again, Andrea asked, "What did Julie tell you about our date tonight?"
"Only that it was a play, not which one."
"Have you seen Wicked?"
"Only the movie. I can't afford Broadway plays. I was disappointed they broke it into two parts."
"We'll remedy that tonight. Why don't you have a seat and tell me a little about yourself."
I spent around fifteen minutes telling her a little about myself, where I was born, where I was going to college and my degree program, my high school sports efforts and the like. The butler came in and informed us that her car was ready. I helped drape a stole over her shoulders and we went to the limo idling on the street, the driver holding the door. I helped her into the car and slid in beside her. I held her hand on the drive, gently rubbing the back of it with my thumb. Andrea took advantage of our closeness to put her hand on my cock, giving it a little squeeze before releasing it, checking me out.
"Mmm, nice," she said.
The driver dropped us off at the theater and Andrea handed the usher our tickets and he led us to our seats, good ones about a third of the way back from the orchestra pit, the middle section, on the aisle. I let her in and sat on the aisle. We had a chance to chat a bit more before the orchestra started warming up. I continued holding her hand during the first act, slowly and softly rubbing it. At the intermission, we got up and I used the restroom before rejoining my date and buying us a glass of champagne.
She'd apparently run into a couple that she knew. When I joined her they both gave me the once over, the woman developing a slight sneer as she figured out my age.
"My, my, Andrea, aren't you robbing the cradle," she said.
"Your friends?" I asked.
"Lincoln and Nancy Hawkins, meet Dan Bancroft."
I took Andrea's hand, kissing her knuckles again. "You need a better class of friend," I said.
"What?" Nancy said. Of course she'd be the most offended, the offensive one.
"Just because Ms. Gormley is no longer married, do you expect her to stay at home waiting to meet the next Mr. Right? She's still a vibrant, beautiful woman, who should be seen out in public, not withering away at home. I, for one, think she's very brave for choosing to find someone who can escort her to events like these, instead of staying cooped up. I hope I can have courage like hers when I get older. I admire her." I brushed her cheek with my lips. "Why don't we find our seats, I don't see any reason to spend more time here where you or I can be insulted."
Andrea's smile lit up the room. "I think we shall."
I took her arm and we went back to our seats, where she gave me a kiss on the lips.
"Thank you for that. Nancy's a harridan."
"Don't be afraid to stand up for yourself," I said. "You deserve to be treated like a lady."
I put my arm around her for all of the second act, and during the third, rested my hand on her leg, very close to her pussy, lightly rubbing her thigh. I could tell she was building some sexual heat. While her dress was too long to go under without being obvious to everyone, she spread her legs enough that my hand could drift closer to her holy of holies. At the conclusion of the play, I helped her up and led her out of the theater, her hand on my arm, with me patting that hand the entire way,
As soon as we were in her limo, which was waiting outside, she was wrapped in my arms kissing me. There wasn't enough time or distance to engage in major hanky-panky, but I could slide the strap off her shoulder and pull down the dress enough to reveal a half shelf corset, with her bare nipples pointing out like bullets. I gently tongued and sucked each one before pulling the top of her dress back up. She was practically humming with sexual tension. I checked my watch. It was midnight, the witching hour.
"Our date is over," I said.
"You aren't going to leave me like this are you?" Andrea asked.
"Of course not. It only means we can get to the good stuff."
She smiled again. She really had a good smile. I kissed her some more, doing a little tongue tango. All too soon, we reached her house and we straightened up before getting out of the limo.
Andrea led me straight to her bedroom, which had a huge bed, larger than any king size I'd ever slept in. I helped her with the zipper, and the dress dropped to the floor. I picked it up and laid it over a chair near the bed. Her nipples were still puckered and she had a wet spot on her tap pants.
"I'm sure I'm a little bigger than you're used to," Andrea said. "I hope you're not disappointed."
"Not at all. You have what would be called a Rubenesque figure. A hundred-fifty years ago, it would have been considered the female ideal, a lush, full bodied woman with a little padding. I suppose tastes have altered over time, but you still have curves in all the right places."
"Oh, God, you're good. Take off your clothes." She sat down on her bed.
"Do you want a show, or speed."
"A show."
I started humming the music 'You Can Leave Your Hat On' by Joe Cocker as I slowly teased my clothes off for her. When I finally pulled my underwear off showing her the goods, Andrea gasped.
"I knew you'd be good from my quick feel in the theater, but you've even better than I expected."
"I'm glad you like it," I said.
