This story is the first in a short series about a shy college geek turned confident stud. It is a spin off from the "Kimmy's Adventures" series I've previously published. The initial setting is the same day that Kimmy wins her first 3000-meter U.S. National Championship (Kimmy's Adventures-Timmy's Virginity), but the location is New York City. It then flashes back to Timmy's college days.
As most of you who follow me know, I like a little story with my sex so once again, there's a gradual build up to the sex scene.
This is a fictional story from the recesses of my perverted mind. Any resemblance to any real people or places is a coincidence. All characters depicted are 18-years of age or older.
Timmy's Adv.- Sorority Tutor Story
x
"Three...two...one...Clear!....And that's a wrap boys and girls! Good show today," said the production manager. "Oh and congratulations Tim Terwilliger, our new weekend weatherman." A clatter of chatter and applause went up from the morning news crew and on air staff as people began to move and talk.
And just like that my first broadcast as the weekend weather person for a major national network was complete. I had barely taken my microphone off the lapel of my jacket when the anchor woman, Stacey McPhearson, turned in her seat to congratulate me.
"Nice job Tim," the attractive ginger haired broadcaster said, displaying her beautiful white smile. "I like the way you snuck in that 'shout out' to your friend Kimmy the runner. It's a nice touch. Allows the viewers to see your personality a bit.
"But I have to ask," she continued, now with a mischievous grin, "why'd ya call her Freak? Sounds like there might be a good story behind that nick name of hers."
I hesitated at first wondering how I should answer Stacey's question. In the past I would have considered a woman like her way out of my league. But, she's the one who 'opened the door' with her provocative question, so I thought, 'what the hell do I have to lose?'
"Well thanks Stacey, I appreciate the compliment" I started. "As for your question, it's too long a tale to tell now. How about I explain it to you over dinner at this nice Italian seafood place in Little Italy that I heard about. I've been dying to try it out."
"Oh aren't you a smooth one?" she laughed, assuming I was hitting on her. Which I guess I was. "Listen Tim, I appreciate the invite, but I have a...boyfriend...of sorts...and..."
"Cool," I said interrupting her. "Bring him along. I'm new to the big city and really don't know anyone. The more people I meet the better." Inviting her boyfriend seemed to throw her off for a second and made my intentions appear more platonic.
"Yeah, well, he's actually away on...business...for another week," she said, with a bit of disconsolation in her voice. "Besides, we both have to work tomorrow morning. I was just gonna cuddle up with a good book and go to bed early."
Very often this was the reaction most women gave me when I first asked them out. Let's face it. I'm a bit of a nerd. I look more like the geeky kid brother next door than the heart throb, sweep them off their feet type. But through the confidence building and tutelage of Kimmy and the sisters of Chi Omega, I'd learned to use wit and humor to be resolute in my quest.
"It doesn't have to be a late dinner," I persisted. "Say like five-o'clock. You'll be home and in bed with your book before 10 p.m." I gave her my best puppy dog look. "Anyways I think my story will be better than your book."
"Steamier than the latest Danielle Steel novel?" Stacey quipped dubiously. Danielle Steel? I wondered if she was still relevant since my Mom use to read her books when I was young, but decided to keep my thought to myself.
"You'll have to join me for dinner and find out," I responded coyly.
A long pause ensued before Stacey responded, "Oh what the hell! It's just dinner, right?"
Not exactly the enthusiastic response I was hoping for, but at least she agreed to go.
xx
It was a little after five when Stacey's Uber pulled up to the restaurant I'd been waiting outside of for about 15-minutes. It had been a gorgeous spring day and the afternoon's last rays of sunshine bathed the city in its warm glow.
The door to the late model sedan opened and I saw two feet adorned in black ballet flats appear attached to two long gorgeous legs. Her gams were visible through the front split in a flowing white, ankle length sun dress. My eyes followed a path up her voluptuous body from the curve of her toned calf, to her partially exposed thigh, up the buttons on the front of her gown to a plunging neckline that exposed an abundance of creamy white cleavage.
Stacey was careful at work to always down play her sexiness. She wanted to be taken seriously as a professional journalist. As a result, rarely if ever did she wear anything that displayed her bountiful breasts. Luckily for me that night she wasn't following her work dress code.
I briskly moved across the sidewalk and offered Stacey my hand in assistance.
"Well thank you Tim," Stacey said, somewhat surprised at my chivalrous act.
"My pleasure Stacey," I responded. "You look very pretty this evening."
"Ever the charmer, eh?" Stacey asked a little suspiciously. "Well I have to say I like the outfit you're wearing tonight." She paused to admire my wardrobe that consisted of a my best blue jeans, a dressy white tee-shirt with a beige vintage linen blazer and beige sued loafers.
"Would I be spoiling your impression of me if I told you I just got most of this outfit today in a thrift store in the village?"
"Not at all," Stacey giggled cutely. "I'd call it prudent. Half my wardrobe is from vintage stores. Trust me, I know how difficult it is to survive in the city." I chuckled in response, then motioned her towards the restaurant entrance.
As we waited to be seated, I appreciated the fact that Stacey had worn flats rather than heels. As it was, she stood at least two inches taller than my 5'7'' frame. Over the years I'd come to terms with the fact that I'm not the most imposing of figures, but I still was self conscious from time to time. Especially, when I noticed jerks at the bar looking in our direction and blatantly laughing in surprise that Stacey was with me. Then I thought, "fuck them!" I'm the one dining with an intelligent, gorgeous woman, while they're jerking off with each other.
Stacey and I were somewhat surprised when the maitre d recognized us from the television and thanked us for dining at his restaurant. He instructed a hostess to take us to a booth in a more secluded corner of the dining room. I quickly thanked the gentleman and slipped him a $20-bill.
A few heads definitely turned in Stacey's direction as we proceeded to our table. She attracted a few autograph seekers as well, but for the most part we were left to ourselves.
By the time we'd finished our salad course, we'd shared with each other the obligatory family information and particulars about our career paths to that point. Upon taking another sip of her pinot grigio, Stacey changed the topic.
"Oh by the way, did you happen to see your friend Kimmy's race today? It was so exciting. I was cheering her on at the top of my lungs and I never met her before."
I nodded my head in acknowledgement. I'd watched it right before I headed to the restaurant to meet Stacey. I'd already sent Kimmy a congratulations post on Instagram. I couldn't have ben more proud of her.
