Taylor Swifts Sex Education

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."

She wrapped her long delicate fingers around my shaft and squeezed it. My dick throbbed in her grip and her eyes went wide. While holding it in one fist, she used the index finger of her other hand to touch the soft head. She might have been curious but I was aroused.

"I've seen porn of men ejaculating on different parts of a girl's body and even on her face or in her mouth. I can't imagine what that tastes like."

Here was my opportunity!

"Would you like to find out, first hand?" I asked.

"Ugh, no, at least not in my mouth, but maybe just to see it and taste it."

"Start stroking it, and talk about it and I'll come anywhere you want."

"Will there be a lot? Should I get a towel or something?"

"Depending on how excited I get, maybe a mouthful."

"Wait! Let me get something to catch it in."

She jumped up and went to the cupboard. I watched her tight young ass in those tight blue panties and decided that she wouldn't have to work long to make me come. She returned with a large coffee cup, knelt in front of me and regripped my dick.

"Grip it gently in your fist and stroke it slowly. Look at me and talk dirty; tell me anything you can think of and I'll let you know when I'm ready to shoot."

"Okay," she said. She followed my directions, her hand working seriously on my shaft.

"I like your dick; it's bigger and harder than I imagined."

"That's good, keep going," I said, looking down at her thighs.

"I want to see it when you come, I want to see it splash or dribble into the coffee cup."

"Work your fist a little faster and keep talking," I said, "Cup my balls with your other hand."

When she did, I thought I would lose it. My balls were nestled in her warm palm, her grip was tighter and moving up and down my shaft and it felt wonderful.

"What turns you on?" she asked, seemingly at a bad time.

"Your legs, your pussy, your ass and your mouth," i answered almost moaning.

"My mouth?" she asked, her hand slowing down.

"Yeah, your red lipstick makes me want to fuck your mouth," I groaned.

Her eyes lit up and she gripped just the tip of my dick. This was a smart girl and she caught on fast.

"So, I guess if you fucked my mouth, you'd want to come all over my red lips?"

"Mmmm," I groaned, wishing she would resume stroking.

"What if I put your dick in my mouth and got my red lipstick all over it; would that turn you on?"

"UHHH" I groaned, feeling the rise from my balls.

She could sense that I was losing control. The coffee cup sat by her knee, and I needed to tell her to grab it quickly. But there was no time. Every guys knows that once you know you are coming, you have about four seconds before your dick erupts, there is no way to stop it. Unless you have someone who is experienced at edging you. But this was not the case.

I looked down as she moved her hand to the base and slipped her mouth down over my dick, taking as much as she could into her mouth. Seeing my dick slip in between those tight red lips was all I could stand and I shot my load without time to warn her.

She recoiled as the first rope spilled into her mouth. She took her mouth off, realized what was happening, and grabbed the coffee cup. I grabbed my dick and masturbated into the cup with several more spurts. She sat back on her butt on the carpet.

She grabbed the coffee cup from me and spit into it several times.

"Damn, that stuff is NASTY!" she muttered.

"Well, that takes care of a couple things you wondered about."

She got up and ran to the bathroom and I tucked and redressed by the time she came back. When she reached the chair, I noticed the crotch of her panties had a large wet spot. Time for opportunity number two.

"I can see by the wet spot in your panties that you liked something about that."

"I'm glad you were clean because I wanted to feel it in my mouth, but I didn't want THAT to happen!"

"I'm sorry, but you teased a little more than I expected and I couldn't hold back."

"I'll try to remember that next time when I'm with a guy."

"So, since you're wet and your body is excited, would you like an orgasm?" I asked.

"You mean so you can brag to your friends that you fucked a teen idol? No."

"I didn't say I was going to fuck you; I asked if you want an orgasm."

"I've had orgasms, that's nothing new."

"Have you had an orgasm from someone licking you?"

She stared at me in disbelief. "You mean, down there?" she asked.

"You must have seen it in porn, so yeah, down there."

"No fingers or your dick, though, right?"

"Nope just my tongue."

She slipped off her panties and sat in the chair so she could put her long legs over the arms of the chair. Her golden pubic hair was soaked. Her beautiful legs were right there, open and inviting. She still had her blouse on and the whole picture was erotic to me.

I sat on the floor in front of her and leaned in close to her pussy and I looked into her eyes. There was a look of uncertainty and the slightest hint of lust. I winked at her and pressed my face between her thighs.

I learned a long time ago that there is no rush when it comes to introducing a girl to receiving oral sex, and even less of a rush when she knows what it is like and wants it. I nibbled at her pussy lips, sucking her skin. I rubbed my face in her pubic hair and she gasped.

I placed my hands on her upper thighs and when I finally began lapping up and down her slit, I felt a slight tremor in her legs. I carefully slipped my tongue inside her, pressing my mouth firmly into her flesh. She moaned and her hips moved slightly against me.

I spent a long time alternating between licking her slit and her labia, flicking my tongue up and down across her clit and fucking her with my tongue as deeply as it would go. Her hands gripped the arms of the chair and her body moved against my mouth. I was rewarded with a constant flow of vaginal juices.

When I finally closed my lips over her clit and sucked gently on it, she slid her legs over my shoulders, closing her thighs tightly on my head. I was in heaven. She humped against my mouth, obviously ready to come. I did not back away but let her enjoy the feeling rushing over her young body.

She whimpered, "Oh, my God, oh, my God..." and I felt the muscles in her upper thighs tighten. I could feel the pressure building in her groin and suddenly she came, but she also squirted; something I had not counted on nor expected.

It went everywhere and I adjusted, struggling to swallow all that I could without disrupting her climax. She seemed oblivious of what had happened. Her eyes were closed, her head back as she continued to hump my face. i sucked and licked every inch of her pussy and thighs until she moved her legs off of my shoulders and sat back in the chair.

I sat in front of her, even more out of breath than she was, with the front of my shirt soaked. I didn't care. Looking at this pretty young girl in front of me, breathing hard having just come in my mouth was the most erotic moment in my life.

When she had come down from her excitement and looked at me sitting there, she looked apologetic.

"That's never happened before; I'm sorry," she said.

"Never apologize for coming in a guy's mouth; it's a privilege," I said.

"I mean that squirting stuff, i didn't mean to pee on you."

"Oh, it wasn't pee, trust me, it was just extra water in your body released with your orgasm."

She got up, stepped around me and went to the bathroom. I heard water running and she came back with a towel.

"You can wipe off with this. Take off your shirt and I'll rinse it off in the sink and go put it in the dryer."

I also gave her my tee shirt. She put on a robe after rinsing my shirts and she took them to their laundry room. When she returned I was sitting on the sofa bare chested but very relaxed and at ease.

She sat down next to me, smiling and very warmly said, "I'm sorry for my attitude earlier. I was afraid you were here just for your own pleasure."

"Well, I had no bad intentions but doing anything for or with you definitely is my pleasure, so I'm guilty I guess."

She laughed and leaned back into the sofa.

"I suppose I should continue to take advantage of your experience," she said.

"Anything you want to know, just ask."

"What I want to know is how a real dick feels inside of me and not a plastic one."

"I think I can help you with that because that episode in the chair really rang my bell."

She laughed out loud at my last comment. "You almost make sex fun," she said.

I was wondering how she would want to proceed, but she stood up, removed the robe and then took off her blouse and silky blue bra.

"What do you want me to do to get you hard again?" she asked.

"Just talk to me; tell me what you want me to do, tell me what feels good."

I kicked off my shoes and took off my pants and boxers. She was pleased that my dick was soft as I stood in front of her.

"Oh, good, I want to watch it growing," she said.

"Then buckle up, because you're in the driver's seat."

"Okay, let's see...I want to see your dick get really hard, and then I want to sit on it. I don't want you to squirt inside me, but I want to feel it inside me."

"That's a good start," I said, smiling.

She slipped her hand between my legs and cupped my balls in her hand. Just her soft touch aroused me. Then she wrapped her fingers around my dick and it began to harden in her grip.

"Maybe I should put more lipstick on; so you could think about fucking my mouth again."

"You don't have to do it, just talking about it is working."

Indeed my dick was fully erect and throbbing in her hand. I wanted to be hard for her. I wanted her to want it inside her.

"Your stuff tasted terrible but it excited me to have it squirting in my mouth."

"If you say much more, I'll be squirting in your hand!"

"Can you sit on the sofa and let me sit in your lap?"

"Sure, any way you want to do it is fine with me."

When I sat down, she got on her knees straddling my body. She leaned forward, offering her breasts to me. I kissed every inch of them, one at a time, licking and sucking the nipples. She let me do it for a long time and I was certain that I could feel her pussy dripping on me.