In the late 90’s I was fortunate enough to inherit a significant amount of money from my Dad’s brother. He had done well in life and was a relatively unknown philanthropist. Uncle Carl had been my idol when I was a kid, next to my Dad, of course. Uncle Carl taught me how to play golf, and recognized what he thought was great potential. He paid for golf lessons with several pros and subsequently he and I enjoyed many rounds of golf with my Dad.
Uncle Carl was unfortunately a heavy smoker and we were not too surprised when it got the best of him. After his funeral, my Dad informed me of the money we both had inherited. Dad paid off his remaining mortgage and invested the rest. I was unsure of what to do with my inheritance, so I consulted Merrill Lynch in Nashville, where I was living at the time.
They assigned a consultant named Scott Swift to me and we hit if off very quickly. He was originally from Pennsylvania and I was from New York. Our similar experience dealing with winter weather growing up and our mutual love of golf enabled us to enjoy time together outside the professional arena.
Eventually, Scott left Merrill Lynch to “handle family business matters.” I had never actually met anyone in his family and it was not my nature to pry, so I just wished him good luck when he left. We managed to keep in touch and to occasionally play golf.
In October, 2008, Scott called me and asked me to come to their home in Hendersonville. Both he and his wife sat with me over lunch and a very unusual and unexpected conversation took place.
“Will, have you heard about our daughter’s recent success?” Asked Andrea.
I honestly replied, “What does she do?”
Andrea looked at me with disbelief. “Our daughter is Taylor Swift; you don’t know of her?”
“I’m sorry; I’m embarrassed to admit, but no. What does she do?”
“She’s a musical teen idol. She has record deals, has been on tv and at the Grand Ole Opry,” explained Andrea.
“I haven’t paid attention to what is new in the music world since the 70’s, so I apologize. I meant no disrespect to your daughter.”
Scott smiled at his wife. “You, see, Andie, this is why I thought of Will after our discussion the other night. He’s a nice guy; we can trust him, and she’ll be safe with him.”
Completely in the dark, I interrupted as politely as I could.
“Excuse me, Scott, but I’m confused; what is going on?”
Scott looked at Andrea and she answered my question.
“Taylor will be 19 in December and going on tours soon and we’re concerned about something, something very private and personal.”
“Does she need a bodyguard or something; I wouldn’t be any good at that,” I admitted.
“Actually, we’re concerned about her sexual safety,” Scott said.
“That’s right. I had “the talk” with Taylor years ago and she’s a smart girl. But we’d like to know that she understands men and that she won’t be emotionally taken advantage of,” explained Andrea.
“So, what is it you want from me?” I asked, still in the dark.
“We’d like you to spend the afternoon with her, maybe even spend the night if she wants, and see how she feels about sex with a man,” Scott said.
“Good God! You want me to have sex with your 19 year old daughter? I’m 46! Why not get one of her young boyfriends to get with her?”
“She doesn’t have any serious boyfriends and the ones she knows all want to be with her for the publicity,” Scott said. “We want to be sure that she can try whatever she wants without the worry of her falling in love with the first boy who has sex with her.”
“Oh, my God, this is crazy; she doesn’t know me and why would she have anything to do with a guy my age?”
“I’ve mentioned you several times and told her you would be here today,” explained Scott. “She is under no obligation to have any sex with you and there is no pressure for you to try to seduce her.”
“And we just want her to know this is all confidential and private, that no one will know of anything that goes on between the two of you,” added Andrea.
I took a couple deep breaths to calm down and clear my head before accepting the obvious.
“What is she expecting of me?” I asked.
“We don’t know for sure,” Scott replied, “but we did tell her that we asked you here to clarify any personal or sexual questions about men.”
“So, you want me to see her today, now?” I asked.
“She’s waiting upstairs in her room; I’ll take you,” Scott said.
Scott stood up and I followed him up the wide stairway and down a long hallway. He rapped his knuckles on the door.
“Taylor, honey? It’s Dad. Can we come in?”
“Sure, Daddy,” came the soft voice from inside.
I had somehow never seen her and I was instantly star struck. A tall slender girl stood there by a window wearing a silk peach colored blouse, a short skirt with the hem just above her knees and low heels. When I stepped close to her, she was actually tall enough to look down at me.
She had a sweet innocent smile, almost perfect teeth and steel blue eyes. The light from the window behind her illuminated her blond hair.
Scott introduced us
“Taylor, this is Will Norman, the fellow I have been talking to you about. He’s one of my previous clients and golf buddies. Will, this is our daughter, Taylor.”
Taylor shook my hand and invited me to sit down on her sofa. Her room was large, and furnished like an expensive hotel suite. There was music memorabilia all over the room.
Once Scott had left us alone, Taylor sat demurely in a chair across from me. She may have looked demure but she was confident and politely blunt.
“So, I guess my parents expect me to have sex with you, right?”
“Not exactly; they just want to be sure that you know everything about a man that you want to know.”
“Well, I’ve seen all the porn I need to know what men can and will do, so I’m not sure of what my parents expect today.”
“I think it’s all about satisfying your curiosity.”
She sat quietly for a minute, because neither of us were sure how to proceed.
“Dad told me that you’re divorced, and have no children. Why is that?”
“Why don’t I have kids? Because my ex-wife wanted a career instead of kids, the same reason we are divorced.”
I decided to let the elephant in the room out of the bag.
“Are you still a virgin?” I asked.
“Not in so many words,” she answered with a smile.
“Meaning?” I prodded.
“Well, I do masturbate, and my friend Karlie gave me a vibrator and a dildo for my birthday last year. She’s younger than me but she’s into modeling so she’s very sexually active.”
“Any sex with boyfriends, hand jobs, blow jobs, fingering?” I asked.
“No to all of that. I’ve seen it but it’s gross.”
“Anything with a girl, maybe with your friend Karlie?”
“No, I’m not gay, we’re just close friends.”
“Usually sex play with a girlfriend is easier than with a guy the first time,” I suggested.
“No, I’m just not interested in girls like that.”
“What are you interested in, really?”
She shifted in her seat, crossed her legs carefully, giving me a brief but distinct glimpse of her legs above her knees. I stared long enough to let her know that I enjoyed the glimpse.
“Well, I am a little curious about dicks,” she finally admitted, shyly.
“What about a penis makes you curious?” I asked.
“Karlie calls them dicks; I like that. So, why do they get hard so easily and how hard do they get?”
“If you will allow me to get a bit crude, let me say that primarily men like to fuck every chance they get. Many, many things about a woman can get into his mind and get him hard easily. His dick will get hard because it’s human nature.”
“What kind of things, you mean parts of her body or what she says or does, or…”
“For instance, you just crossed your legs and let me see up your dress. If you had opened your legs and let me see your panties, I would probably be hard already.
Her eyes lit up and her smile told me that she was entering into fun territory.
“Really?” she asked excitedly. “I never thought I could arouse a guy like that!”
“Trust me, it’s easier than you think. The promise or hope of getting into a girl’s panties for any activity will get us hard every time.”
“Can I see?” she asked, moving to the edge of her chair.
“See what?” I asked.
“Can I see you get hard?”
I decided if she wanted to play, it would be on my terms.
“Take your dress off and then you will see what an effect you can have on a man, or a boy.”
Kicking off her shoes, she unbuttoned her dress and shimmied out of it with no hesitation, exposing her long legs and light blue panties. I didn’t have to rub my dick; it moved automatically in my pants.
“Now, come over here and kneel down in front of me. Tell me that you want to see my dick, and by the time you get it out of my pants, it will be fully erect.”
“Oh, my God, I can’t believe I’m doing this,” she said.
But she did. She knelt on the carpet, looked up at me, smiling and said, “I want to see your hard dick.”
She unbuckled my belt, opened my pants and pulled down the zipper. She yanked my pants down to my knees while staring at the bulge in my boxers. When she yanked my boxers down to my knees, my dick sprung up in her face like a flagpole.
She sat back on the carpet, her hand over her mouth. I didn’t know if she was impressed or horrified, but I took the liberty of stepping out of my pants and boxers, proudly displaying some decent wood, just for her viewing pleasure.
“Oh, my God, it’s HUGE!” she said, but still smiling.
“And that’s just for showing me your legs and talking a little dirty.”
“Can I touch it?” she asked.
“That’s why I’m here; to satisfy your curiosity.”