Testing A Theory
SmokinDriver
Testing a Theory
By Smokindriver
This is a work of fiction. No person is being represented here in any truthful way. This takes place in a world where there are no STDs, unwanted pregnancies or non-consensual sex. Enjoy the story.
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Advanced Reader Copy Edition: December 17, 2022
Copyright ©2022 Smokindriver
Send feedback to: smokindriver@yahoo.com
All rights reserved. No part of this publication may be reproduced, distributed, or transmitted in any form or by any means, including photocopying, recording, or other electronic or mechanical methods, without the prior written permission of the author, except in the case of brief quotations embodied in critical reviews and certain other noncommercial uses permitted by copyright law.
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All characters depicted in this work are fictitious. Any resemblance to real persons, living or dead, is purely coincidental. Names, characters, places, brands, media, and incidents are either the product of the author’s imagination or are used fictitiously. The author acknowledges the trademarked status and trademark owners of various products referenced in this work of fiction, which have been used without permission. The publication/use of these trademarks is not authorized, associated with, or sponsored by the trademark owners.
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Table of Contents
Chapter 1
Chapter 2
Chapter 3
Chapter 4
Chapter 5
Chapter 6
Chapter 7
Chapter 8
Chapter 9
Chapter 10
Chapter 11
Chapter 12
Chapter 13
Chapter 1
Has anyone ever done something or said something that made you stop and think about it? It made you do a double-take? Like the first time you saw someone breathe in a balloon full of helium and then spoke in their munchkin voice. I had one of those times when I was sitting in the library during my 8th grade year of middle school. It was 1979. I had the newspaper because I wanted to read about the game from the previous day.
Two girls that I knew stopped by to grab the classified section. I never read the classifieds. They started pointing, giggling, and then talking. There was a personals section and one said: Wealthy man traveling to Europe. Looking for a companion to go along. Send a picture and phone number to PO Box xxx NYC NY.
The girls started talking about if they’d go or not and one of them said seriously that she would. I looked up from the sports page and said, “It sounds like he just wants someone willing to put out for him while he’s on his trip.”
Julie said, “Duh. If he isn’t too old or too ugly, I’d go.
Kelly was nodding in agreement. They talked a bit more about it and then went on about some of the other ads in the paper. I was going to point out that they also had jobs in the classifieds and they could get a job and then pay their own way but I let it go and went back to reading the sports page.
That night I thought about the discussion some more and then over the years it would come back to me. I’d heard the joke about a lady who said that she was a lady and not a whore. The guy asked, “Would you have sex with me for a Billion dollars?” She said that she would. His reply was, “Now that we both agree that you’re a whore, we’re now just negotiating price.”
Which brings us to today, March 15,1987. My name is Brad Johnson. I’m on a plane heading to Bermuda for Spring Break. I’m in the last semester of my Junior year at Florida State, working on a degree in Hospitality Management.
My last name is Johnson but my mom’s last name was Kensington. As in the Kensington Collection. A hotel group started by my great grandfather Eliah Kensington, back in the 1920’s. When the depression hit the US, Eliah was well off and saw the bubble that was ready to pop in the stock market. He made a few million dollars as the country was about to take a dive and run onto hard times.
There were plenty of people that had money and had wealth but even some that were well off lost most or all they had with the crash in the stock market and the economy. He first bought the Gracie Mansion in New York City on 88th street overlooking the East River. He did the same type of thing in most of the major cities. Eliah started what today would be called “Boutique Hotels” for those that wanted quality and privacy over loyalty points and big chain hotels.
The Kensington Collection has 200 hotels with an average of 50 rooms per location. That is 10,000 rooms with an average 70% occupancy rate. Some hotels are larger and some are smaller. Some were private homes or vacation homes, some were once government buildings, train stations, churches, castles, or vineyard estates. In some cases the vineyards are still producing wine and are an attraction for the hotel.
I was on the plane on my way to spend Spring Break at the Loren. It only had 45 suites but the location and amenities suited me fine. I didn’t need beer bongs and 10 guys sharing a room on Daytona beach. My grandfather had set up a generation skipping trust for me when I was born. It helped him and his taxes at the time and when I turned 18, I was old enough to be the trustee as well as the beneficiary.
My mom has her own trust and Dad works for the company as COO. They’d inherited a place in New York City where the company is headquartered. I see them at Thanksgiving and Christmas. Other times of the year, I’m attending Florida State. Summers, I do what I want and sometimes go home for a week or the whole summer.
As I flew over to Bermuda, I thought back to that day in the library. I wondered if I took a trip over the summer what kind of women would apply to be my traveling partner. I thought it might be fun to test the theory of what the girls were saying at the table that eventful day.
The stay in Bermuda was relaxing. I didn’t study or have any classes to get to. I slept in late, ate well and enjoyed the pool, beach, and scenery of the resort. I hooked up with two women while I was there. I’ve found that only the very rich stay at our hotels. There are very rich divorced women, and families that travel with their children or send their children to nice safe hotels.
The first was a divorced woman from England. She was in the bar the second night that I was there and I sat and talked with her for a while and bought her a few drinks before suggesting that she come back to my room. When she saw that my suite was nicer than hers, she was impressed and in the end I don’t know if she seduced me or I seduced her but when she left in the morning she was regretting that it was the last day of her holiday.
The other woman was from Boston and was in college and on Spring Break with her friend. Her parents were paying for the trip and would rather her be away from the big party scene in Daytona and Fort Lauderdale. They paid for her and her friend to travel to Bermuda and hang out in the safer and more sedate resort.
We met at the pool, then on the beach and later in the bar. Friday night and all Saturday before I flew home was spent in my room naked and sucking, licking, and fucking our brains out. We had room service and her friend called a few times to make sure that she was alright. When I packed up to fly home, she was passed out, exhausted, on the bed and I was a happy boy.
Back in Tallahassee, I was ready to try out my experiment. I already had a PO Box from when I was a freshman living in the dorm. It was set up because I knew that I'd be in Tallahassee for four years and would move around some. It was a big box since I didn’t stop by very often and never knew what packages I might receive.
I wrote out a classified ad and then called it in to a few papers. The Orlando Sentinel, Miami Herald, Atlanta Journal and Constitution and Tallahassee Democrat each ran the ad for a week.
“Wealthy young man, looking to travel the world for two months this summer starting May 1st. Looking for an adventurous lady to accompany me on the trip. If interested, please send a letter telling me about yourself, a phone number to contact you and a current picture to PO Box, XXX Tallahassee FL.”
Then I just went back to class and waited a week before I started to check my box for responses. Over the next two weeks, I received 72 replies. A third of the pictures were nudes or topless, polaroid’s of women from 18 to 42 years old. White women, Latin women, Asian women, and black women all sent letters with descriptions of themselves and why they wanted to travel the world.
A few jumped out at me. One was very demanding telling me that she wouldn’t be having sex with me but that she should be the one that showed me the world. She had a list of places that I’d take her. Her picture was a girl in jeans and a nice top but nothing special. I just laughed and tossed that one on the stack of rejects.
One woman was from Miami and smoking hot. Her letter let me know that she didn’t have a passport but for the right amount of money she’d travel to me and show me a good time. If I wanted to take her somewhere in the US she’d be happy to escort me but there would still be fees on top of the travel costs. She was obviously a hooker but made me think about a couple of the others that I saw.
One girl was local and wasn’t 18 yet but would be by the time we left for the summer. She’d be graduating but not until a couple weeks after the scheduled departure. She asked if the date could be pushed back until she got out of school or if she could join me after the start date. Her name was Jody and was a sexy thin blonde girl with pretty blue eyes.
Another local that made the list was my age and went to FSU. She was a tall black woman that played on the women’s basketball team. She said that she wanted the adventure and it would fulfill a few fantasies that she had. She sent a picture but not a nude. She was light skinned and had her hair straightened and up. Her long neck and pretty face was very enticing.
A blonde with big tits in Atlanta and a brunette from Orlando rounded out my top round of candidates. Either could be a model and both were free for the summer to travel. The one in Orlando asked to be called after 3 pm but before 6 pm. It made me believe that she had others that she lived with that might not approve of her taking the trip. It made me interested in who that might be.
The experiment was working and I was surprised at the quantity and quality of the responses. I first called the blonde from Atlanta, Amy. She was excited to hear from me. She was twenty-two and worked as a dental assistant. When I asked about her job, she said that she’d quit and look for another one when she got back. The call was interesting and I told her that she was a possibility and that I’d get back to her either way.
The last was another that intrigued me. Her name was Tiffany and she was a teacher. She was off for the summer and wanted to travel and see the world. She was married to a plumber and had been for the last five years. They had no children and her husband had been her high school sweetheart. She needed to get away and see the world before she settled down and became a mom or family woman for the rest of her life. She needed the adventure.
Tiffany was tall, with long straight dark hair, brown eyes, and a killer body. Her breasts were small but looked good on her body. She sent a picture of her topless in just a pair of panties. Her body was twisted so I could see her breasts and her well-shaped ass. I hadn’t planned on women that were married or willing to quit their jobs but it made for some interesting thoughts as I contemplated my next move.
There were some that were just a “No” even if there were no others to compete against. I thought that maybe I should write them back and let them know that they didn’t make the cut but then thought about parents, boyfriends or husbands that might see the letter. I could call but then I’d have to listen to them complain, cry, or beg and I wasn’t up for that. I decided to be a dick and just not reply.
I called the ones that I was interested in. Tiffany in Orlando and Amy from Atlanta. I also called the two that I liked that were local. Jody was the younger girl that was only 17. That meant that I was 4 years older than her but at 21 years old, she was currently off limits. I thanked her for her letter and we talked for a bit about her school and my school.
She finally said, “I saw that you were local and decided to send you a letter to see if you’d call. I don’t have a passport and couldn’t sneak away for two months without being disowned. I appreciate you calling me back. It made my day.”
“If you’re serious about going with me, I’d take you away for a weekend and not leave the U.S. If you wanted to see New York, Chicago, Boston, or some other city we could get away.”
There was a long pause as she thought about what I said. She said, “Really? You’d take me on a trip. We’d fly in a plane and stay in a hotel?”
“If I’m in town, I’d be happy to. You’d have to be 18 so I didn’t get in trouble. What would you tell your parents?”
“I’d leave a note that I was staying the weekend with a friend and would see them after school on Monday. I do it often enough. My birthday’s this week. This weekend my parents will want me around for cake and ice cream. How about the following weekend? I've never been to any of those cities.”
“We can call it a date. Do you want me to pick you up at school or somewhere else? I’ll check to see what’s going on in the different cities and can either let you know or surprise you. Unless there’s a particular place that you’d like to go to.”
“Any of those places would be great. There’s a Burger King a block from school. It would be better if you picked me up there. What should I bring?”
“Bring a small bag with any makeup and personal items. If you tell me your size, I can pick up any clothes so you don’t freak out your parents or wrinkle your dress.”
“I can put a few things in my backpack as if I was going to visit a friend for the weekend. It’s cool that you’d buy me clothes. I’m a size two. If you’re buying a bra, I’m a 30B.”
“I’ll pick up a few things and we can shop in any city we decide to explore.”
“Now I’m getting excited. This is so cool. Is there anything else?”
“My name is Brad, I'll pick you up at the Burger King near your school. Tell me what time you’ll be there so I can look at flights. I’ll be driving a black BMW convertible.”
“I get out of school at 3:00 and can be there by 3:15.”
“I’ll be there at 3:15, a week from Friday.” I gave her my phone number and hung up the phone.
I sat back in the chair. A girl that I’d never met was willing to lie to her parents, meet me at a restaurant away from her friends and get on a plane with me just because I was willing to buy her a ticket. She knew that sex was expected as she was one that sent me a topless photo. I’d buy her a bra and some sexy clothes. I felt funny but she was 18 and not much different than a freshman starting out in college in a couple months. It was she that was sneaking around, just like the married woman in Orlando. It seemed like their problem, not mine.
I then called the other local girl. She was a little older and more confident when she spoke. Angela was a light skinned black girl. She played on the school’s basketball team. She was interested to see if I’d call but had basketball camp over the summer and didn’t have a passport so it was more like she was daring herself. She didn’t send a nude or seminude photo but did send a picture.
She was 6’1” and played shooting forward. She was fun to talk to and we were both having fun. I finally asked, “So if you couldn’t go with me around the world, were you hoping that I’d take you somewhere for a week or a weekend in the states? Or did you just want to come over and have some fun?”
“You haven’t even bought me dinner yet? What kind of sugar daddy are you?”
“I have a food card for the cafeteria.”
“So do I. I’m on scholarship. Why don’t you take me somewhere nice?”
“I’ll pick you up and take you to one of the finer places in town. Should I wear a suit? Do you want to get dressed up?”
“My roommate is bitching at me about going out with someone I’ve never met. She says it isn’t safe.”
“She can come along and be your chaperone.”
I heard her put her hand over the receiver and talk to her roommate. They went back and forth. Angela came back on and said, “Tracie will go with us. Can you give us an hour to get ready?”
After she told me that she lived in the athletic dorm and told me what door they’d be at, I told them that I’d be there in an hour. They were both tall and athletic as expected. Tracie got in the back and I held the door for Angela.
We drove down to Andrew’s for dinner. We didn’t have reservations but they had a few empty tables. After we were seated the girls both ordered whiskey sours and I ordered a vodka martini before dinner. When the girls picked up their menus I told them to order what they wanted. I was happy to have dinner with two lovely looking ladies.
Angela said, “Thank you. Have you eaten here before?”
“A few times. The potato crusted grouper is good, the steaks are good. I haven’t had a bad meal here yet. Everything’s good. Just pick what looks good to you.”
“I was looking at the chicken stack,” was Angela’s reply.
Tracie said, “The New York Strip looks good to me.”
“That’s a good choice. If you want any appetizers or a salad, you should look at those as well.”
When the waiter came with our drinks, we skipped the appetizers but all wanted a salad. The girls ordered their meals and I ordered the chicken marsala. We all took a sip of our drink and the table was quiet.
Tracie broke the silence. “So you put an ad in the paper to see if you could get some slut to go away with you for the summer. How did that work out?”
“It was kind of an experiment.” I told the story about when I was in middle school and the time with the girls in the library. “I wanted to see if anyone would respond, how many would respond and what types of people would respond. I had two that just called me an asshole and couldn’t believe that I’d even suggest something like I did. I had 72 responses. About 25 sent nude photos or topless photos. All of them seemed to know that I planned to share a bed on the trip.”
“Do you still have them all?”
“I have them in piles but the trash pile isn’t in the trash yet.”
“How many did you call?” Angela asked.
“There were four that I was interested in. They all have problems.”
“What’s my problem?”
“You don’t have a passport. You have other commitments at the time we’re supposed to be going.”
“Oh. What about the others?”
“One also doesn’t have a passport and won’t be 18 until Wednesday. One will have to quit her job. One is married but was up front about it. She had her ring on in her picture.”
Tracie asked, “And you still picked her?”
“Husbands, jobs, parents, and roommates didn’t stop them from writing letters. There were some students that had passports and were off for the summer. They just didn’t do much for me in their letters or pictures or both. One was smoking hot but was just a hooker and said that she’d come with me for cash. I could pay by the day, week, or month, plus travel costs.”
“What do you expect from Angie for the meal tonight?”
“Well it’s actually two meals. Yours and hers but I’ll take what she offers me. We didn’t make any agreement or set expectations before we went out.”
Angela asked, “Do you have a roommate?”
“No. Are you looking to move in or just looking for someone to pawn Tracie off on?”
She smiled and giggled. “I just wanted to know if we went back to your place, would we be alone. I kind of liked the fantasy of someone that is a stranger and all that.”
“I won’t tell you anything more about me. I can blindfold you as we drive to my place if you want. I don’t have a blindfold but we can use Tracie’s shirt.”
“I don’t know your last name. Just Brad. It will feel naughty when I get back to my dorm.”
Tracie started to say something but Angela just gave her the look and she got quiet. I wanted to poke at Tracie and said, “Are you planning to come watch or did you want to go home after dinner?”
“I’ll think about it. It isn’t safe for her to go off with you.”
“You could write down my license plate number.”
“You could have stolen that from another car.”
“Are you studying Criminology?”
“Business. Angie is studying accounting.”
“Both are good degrees. I’m studying hospitality management.”
“You want to work in a restaurant or hotel? That sounds like bad working hours. Nights and holidays.” Angie said.
“Unless you own a few and can just pay others to run them. It never hurts to know something about what you own.”
Tracie said, “That’s right. You’re the sugar daddy.”
Luckily our salads came and our entrees weren’t too far behind. I ordered some wine and we shared a bottle. The food was good and we all enjoyed our meal. After dinner, the waiter took the dishes and asked about dessert. Both girls looked at me and I said, “Get what you want. I’ll have some coffee or maybe some key lime pie if you want something.”
Angela ordered the brownie and Tracie the fried banana split sundae. I had the key lime pie and a cup of coffee. Angie said, “The tournament’s over. I can’t remember the last time I had dessert.”
The desserts were good and hit the spot. As we were finishing. The waiter dropped off the check and the girls excused themselves to use the ladies room. I paid the bill and signed the slip. The girls came back and I stood. “Are you ready to go?”
Angela nodded and we walked out to my car. I held the door for Tracie to get in the back and then for Angela to get in. As I got in the car, I started the engine but didn’t put it in gear. Angela said, “Do you have an apartment with a bedroom? Tracie still isn’t convinced that you aren’t an ax murderer and wants to sit in the living room.”
“What if you have a screaming orgasm? Will she pound on the door, or come in and join us?”
“She had better not do either. I’ll scream her name if I want her to come and help me.”
“If that’s what you need to feel safe, I’m fine with that.”
We drove to my place and I showed Tracie where things were in the kitchen and got the TV on and gave her the remote before leading Angela to my bedroom. As the door closed, I locked it. I turned to her and asked, “Will you tell me your fantasy, Little One?”
“Just being with a stranger. A one night stand for now. I’m on the pill. All the girls on the team have to be. I’m not a virgin but I don't sleep around. You’ll be my first that I haven't dated for a month first.”
Stepping to her, I pulled her into a hug and then started to kiss her as my hand found the zipper and started to take off her dress. She kissed back and moved her hands to my belt buckle and then my shirt after my suit coat was tossed on a chair. We were both in our underwear and nothing else when we broke our first kiss.
“You feel good Angela. I guess we’re both sluts tonight. Let me see you naked before you get on the bed.” I lowered my boxers as she took off her bra and panties.
“You look good Brad. I like that you’re taller than me and you’re in good shape. I’m glad also that you’re not some really old creepy guy but are just doing your own little social experiment. Are you ready to fuck the slut that sent you a letter?”
“I am, but first I want to see if she tastes as good as the brownie at the restaurant.”
“Oh, yeah. I want to feel your tongue on my pussy. Then I can suck your cock.”
“You can suck me after I fuck you to get me hard so that I can fuck you again.”
“You do want me to be a nasty girl. Sucking on your cock after it’s been pounding my pussy.” She laid back on the bed and pulled her heels up by her ass to give me good access to her slit.
She had light skin with darker pussy lips and a wet pink pussy that was fun to lick suck and finger fuck to her first, second and third orgasm. I then kissed up her body and put my lips on hers as she reached down and guided my cock into her pussy.
“I thought that the black guys were big and white guys were small. You aren’t small at all. You’re stretching your slut. It feels good Brad. You make me feel good,” and then we were kissing again before I responded to her.
She moved her body in time with mine and thrusted up as I drove into her. She came one more time before I came in her. She was tired and asked about spending the night.
“What about Tracie and class in the morning?”
“Tracie can sleep on the couch and we don’t have class until 11:30. We normally have early morning practices. What about you?”
“I have a class at 10 but can drop you off at your dorm before then if you want to do the walk of shame. Tracie might not like that.”
“I guess I can go ask her.”
“You’re welcome to stay. I have extra toothbrushes, pillows, and blankets. Don’t put any clothes on before you go out there. I want her to see my cum running down your leg.”
“You’re as nasty as I am. I’ll be back soon.”
She looked over her shoulder at me as I watched her ass leave the room. She had a pretty smile. She was back a few minutes later. “Tracie doesn’t want to spend the night and the walk of shame wouldn’t be good for either of us. Can you drive us home?”
“Sure. Let me get dressed.”
“What happened to me sucking you hard and you fucking me again?”
“Do you want me to stand or get on the bed?”
“Stand and I can kneel in front of you.”
I think her getting on her knees and looking up at me with her pretty eyes, did as much to get me hard again as her lips and tongue on my cock. I had her stand and bent her over my desk as I entered her pussy from behind. She moaned and pushed back at me as I held her hips and started to move.
She saw the stacks of letters from the women and her eyes kept darting that way. I’d grab her by the hair and pull when she wasn’t focusing on me and our mutual pleasure. She was motivated and got into things as she started her next orgasm. She had two as we fucked but I wasn’t quite ready and came a few minutes after she did. We were both sweating and she said, “I need to take a shower. Do you want to wash my back?”
There was a big walk in shower in the bedroom and we were soon lathering each other. We dried and dressed. Tracie was asleep on the couch and her hand was in her panties. I looked at Angela and she looked at me. “I guess we’re all sluts tonight.” She shook Tracie to wake her up and we all went out to the car. I dropped them off and walked them to the door. I got a thank you from Tracie for the dinner and a hug from Angela for the entire evening. She said, “I want to read some of the letters you got. Don’t throw them away. Call me some time.”
As I drove back to my apartment, I thought about Jody and our trip the following Friday. Just one evening with Angela had given me a glimpse into what these girls were thinking. Testing a theory was teaching me a lot about what certain women were looking for. It was adventure, excitement and overcoming fear. The fear of mailing the letter to connect in the first place. Meeting a stranger for a meal or a hotel room. Giving yourself or trading your body for a meal or something else. Angela seemed to be a happy girl and pleased with herself. She also wanted more. Maybe it was more adventure or maybe she just enjoyed the sex. Only time would tell.
There were two more and another 70 letters. Did I owe the others something in return for their efforts? My experiment was going in some directions that I wasn’t expecting. I had some weird dreams and tossed and turned more than usual. I went to my Thursday classes after my morning workout.
That afternoon, I called Tiffany. “Hi Tiffany, it’s Brad. Is now a good time to talk?”
“It’s a good time to talk. Have you made your decision?”
“I’m getting closer. I have it narrowed down to two people. I’ve read both of your letters and seen both of your pictures. I was wondering if you’d like to meet in person or talk some on the phone to make sure this is a good fit before we’re stuck together for 8 weeks.”
“I’ve kind of resigned myself to living with whatever for the 8 weeks. I have hopes that you are what you say that you are and not just hiding behind a phone.”
“I’m only four hours away by car. I can drive down to Orlando or you can drive up to Tallahassee. It would be easy for me to drive down there but may be safer for you to drive up here.”
There was a pause and she said, “I don’t want to sound crude but if you just wanted to meet and talk, it would be fine for you to come to Orlando. I have lunch with students every now and then and it wouldn’t be out of place. If you were hoping for a test drive, I don’t think that me following you into a hotel would be a good thing. What did you have in mind?”
“I don’t have any classes tomorrow. I can meet you for lunch or coffee.”
“Can we meet at the Briar Patch in Winter Park around 1 pm?”
I'll see you then.”
As I hung up the phone I thought that if I really wanted to know for sure, that I should probably meet with Amy in Atlanta as well. I gave her a call and made plans for the following night for a late dinner in Atlanta. That meant flying so I booked a three legged flight from Tallahassee to Orlando. Orlando to Atlanta and Atlanta to Tallahassee.
My next call was to the reservations desk at the Kensington Collection. I booked a room at Lexington Place in Buckhead for Friday night and asked about the following weekend to see what was available in New York, Chicago, or Philadelphia. She let me know that there was a big convention in New York and the hotel was full. Chicago had rooms and Philadelphia had a couple left. I went ahead and booked a suite at the Sophy in Chicago.
One last call to book flights for the trip to Chicago and it felt like a plan was coming together. It was early on Friday when I boarded a plane in Tallahassee for my trip to Orlando. I flew in and rented a car. I found the restaurant in the phone book and got a map to figure out how to get there. When 1 pm rolled around, I was at the Briar Patch and had a table for two. I recognized Tiffany from her picture and waved to her as she scanned the restaurant.
As she walked over, I stood and we shook hands. “Nice to meet you in person, Tiffany.”
“I’m pleasantly surprised and happy to meet you too Brad.”
We sat down and a waitress took our drink orders. I’d asked for a table out of the way with a little privacy. Tiffany then turned to me and said, “I was expecting someone older and not as good looking. I’d think that you could just ask your girlfriend to go with you.”
“I broke up with my girlfriend when she graduated at the end of the last semester. I have three more semesters to go until I graduate. Now two more to go after I finish this semester. This trip and the classified ad is the result of something that happened years ago and I wanted to test the theory. It’s been an interesting experiment so far.”
“So can you really afford a trip or was this just some kind of scam?”
“I’m wealthy, or what you’d call a trust fund baby. I don’t normally show it and doubt my old girlfriend knew more than my parents were well off financially. I drive a three series BMW and have my own apartment but she lived in the same complex. We met out by the pool one day. I plan to see this through. I would’ve picked you on your looks and letter alone but that ring on your finger keeps pulling at my ethics.”
“I haven’t lied to you but I’ve lied to my husband. I told him that I applied for a study abroad grant from the state. If I win I’ll be going to Europe for the summer to see different museums and study art. I teach both Humanities and Art Appreciation at UCF. We were high school sweethearts and have been married since I finished my AA degree almost 5 years ago. We’re in a rut or were too young or aren’t meant to be married. He’s a plumber and works hard but he’s into his work, his beer, and his sports.
“I like sports, I like beer and I like my work but we don’t seem to talk, and sex is less and less each month. I want to see the world, explore my sexual side, and then see if what I have can be salvaged or we’ll be moving on. We both work and can get by on our own income. I should have tenure in a couple years and once my student loans are paid off, I can buy a house.”
“I didn’t want to be the reason but I guess that just like I’m using you for my experiment, you’d be using me for your own. I’ve narrowed it down to two people and you’re in running. I’ll meet with the other one tonight but have a stack of letters on my desk if I can’t move forward with either of you. I appreciate your honesty but still don’t want to be that guy that breaks up a marriage. I do enough dumb stuff on my own that I don’t need to do it on purpose. Let me think about it for a couple days. I plan to decide in the next two weeks.”
“That sounds fair.”
We had a nice lunch and talked about growing up and our lives in college. Tiffany was very pretty and smart. After lunch I was driving back to the airport and thought that she’d outgrown her husband. She’d continued after high school to add to her knowledge, to her points of view, her understanding of society and different topics. Her husband had learned about plumbing and watched sports.
If there were a trivia contest they’d be a great team. He could answer sports questions and she could answer questions on art, history, science, nature, books, movies, and current events. The great pair in trivia was also two people living in different worlds. It made it easier to possibly pick her but it was still something I had to come to grips with.
At the airport, I didn’t have to wait more than an hour in the Crown Room before my flight was called and I headed to the gate. I didn’t want to rent a car in Atlanta so I got a cab out front and was soon at The Lexington, in my suite. I always seemed to go into critic mode as I visited my hotels. I wanted to feel what my customers felt. It was just 5:00 and dinner wasn’t until 7:00. I changed clothes into something a bit nicer and went for a walk around the property, before ending up in the bar.
The barman was older and had an inviting smile and gray hair. It was like he’d been at the place since back in the day. He told me about the history of the hotel while I sipped on a beer. Others came in and he’d take breaks in the story to serve the guests as others joined in listening. A few commented on staying at a Kensington over a Marriott or Hilton where you were just a number and dollar sign to them.
The hotel had a shuttle van and a town car for the guests to use as long as the drive wasn’t too far. I had the town car drop me off at the Buckhead Club. The hotel had a membership for the guests that wanted to have business meetings there. I was a guest but also a corporate member. I had on a suit when I walked in fifteen minutes early. If there was a problem, I wanted it solved by the time Amy showed up.
They asked to see my ID but after that it was all, “Yes, Sir and No, Sir,” from the staff. I was told, “Just sign your bill and it will be charged to your account. If you were just a guest at the hotel, it would be added to your room charges.”
“I appreciate you doing that for our guests,” was my reply.
Amy showed up wearing a little black dress. All eyes were on her as we were led to our table on the 26th floor overlooking downtown Atlanta. She ordered Champagne like it was a normal thing and then looked over the menu. “I’ve only been here once. It was for a Christmas party for a guy I was dating.”
“You look nice tonight.”
“Thank you Brad. You’re both younger and better looking than I was expecting. Of course you’ve seen a picture of me. How did you get us in here, it’s a private club?”
“I’m staying at a hotel that has a membership that can extend to their guests for meetings or meals.”
When my old fashioned and her Champagne was delivered, she ordered the escargot, a Caesar salad, and the filet for dinner. I had a Caesar salad and the halibut. My first impression was that all the other girls were using me to see and do things they’d never be able to see and do without me or someone with money footing the bill. Amy was very comfortable in the surroundings, maybe more comfortable than I was. She may not have asked for cash but she made me feel like the hooker from Miami did. She was going to collect her fee and in turn would put out. She had the looks to find another job when she got back. But I did have a few questions for her.
“Amy, I’ve narrowed the field and have a couple more to meet with. I want you to ask any questions of me so you’ll feel comfortable. I have a few for you. If I chose you to come with me, what would happen at your work? What about where you live? You’re also very pretty. Do you have someone in your life?”
“I can get another job. I’m just a dental assistant and they’re in demand. I can probably even get a raise so I’m not worried about it. I have an apartment over my parent’s garage here in Buckhead so I can come and go as I please. I have a guy that I see off and on and it will just be off when I go with you.”
“Do you pay rent or are you building your nest egg?”
“I don’t pay rent but do drive a nice little Mercedes that I pay for and of course clothes cost money as well. If I have to shop for a trip abroad it will probably wipe me out. Does the trip come with a clothing allowance?”
“I haven’t thought about that but if you come with me, I’ll make sure that we figure that out before we go. Where have you been and where would you like to go?”
“I’ve been to most of western Europe. London and Paris a few times. Mom took me to Venice as a graduation gift. I haven’t been to Amsterdam or further east than Italy.”
“I’ll keep that in mind if you’re chosen.”
Dinner showed up and she told me about her dad owning a few dental offices and being a dentist. She needed to do something and followed in his footsteps but decided on the dental assistant route since she didn’t want all the schooling to be a dentist and didn’t want to scrape tartar off people’s teeth all day as a hygienist.
She asked about me and the classified ad. I explained the whole story to her and she said, “I could have been one of those girls at the table. I was always fantasizing about that kind of stuff. When are you going to decide?”
“Some time after the weekend, if I had to guess. Maybe this week if I talk to everyone and have a chance to weigh my options.”
After dinner I signed my tab and she asked if I wanted to go out dancing or if a trip back to my hotel might help me make up my mind in her favor. I replied. “This is an experiment for me. I haven’t slept with the others that might be going and it wouldn’t be fair to them if I slept with you. The meal and conversation were in line with what the others received. I’ll give you a call in the next week or two.”
“Can I drop you at your hotel?”
“Sure.”
Looking back, I think she just wanted me to pay the valet that brought the car around and have one more chance at being invited to my room. She flashed me plenty of thigh and gave me a sensual kiss before I got out of the car. I stopped by for one last drink at the hotel bar and saw a few single ladies that would be receptive to a drink and an invite but I ignored the thought and made it back to my room alone.
◊◊◊
Chapter 2
Saturday morning, I was back at the airport and flying back to Tallahassee. I spent the afternoon rereading letters and looking at pictures to see if there were any that slipped by. Amy wasn't my type. Tiffany was a great fit except for the husband. It sounded and felt like her marriage was on its last legs so I was going to stop worrying about it and let the chips fall where they may.
I studied over the weekend and made sure all my homework was done, projects were done and reading and studying was up to date and ahead of the teacher’s assignments. Sunday I played ultimate frisbee for a couple hours and then showered and watched some TV. I called Angela the basketball player.
“I wanted to call and say hi, and see how you’re doing.”
“Hey Brad. I’m doing fine but Tracie is still giving me a hard time. I think she’s just jealous that we turned out so well and she was on the couch alone with her fingers. Are you calling to take me out again or just looking for me to come over and have some noncommittal sex?”
“Either would work but I was just calling to make sure that you were okay with the night in general.”
“I had a great dinner and great sex. All that was missing was to let me read all your letters and see all the pictures. That and you asking me to be your girlfriend.”
“I don’t have a girlfriend and am not looking for one. I have one year left of college and then will be off to find some work. Probably in New York City.”
“I know, but a girl can dream about having that kind of sex every night. Sometimes I just say your name when I’m in bed to get Tracie pissed off.”
“You should go buy a big vibrator and name it Brad instead of Bob.”
“Who’s Bob?”
“Battery Operated Boyfriend.”
“Oh, I like that. Maybe I will. Can you loan me a few bucks?”
“Maybe if I take you to dinner this week we can pick something up for you?”
“What night?”
“If I told you then I wouldn’t be a demanding sex lord.”
“Sex Lord? Does that make me a sex slave?”
“Do you want to be?”
“Let me think about it and I’ll let you know when you call me to go out with you.”
“Good girl. Study hard and make good grades. You never know when you’ll be coming to me and asking for a job. I only hire the best.”
“I’m the best. The best you’ve had this week.”
“There was Amy up in Atlanta Friday night. She had this mole on her left tit.”
“Brad, you know that my tight pussy was the best you had. I’ll have to prove it to you again if you forgot already. Call me this week and I’ll be there.”
“Good girl. Have a good night.”
“You too.”
She was a fun one to talk to and play with. I loved her verbal sparring and self-confidence. I had a smile on my face when I fell asleep. Monday morning I went to class. In the afternoon, I called Tiffany and told her that she’d have to create her story but she was the one that I picked to take with me. She’d have a ticket waiting for her at the ticket counter in Orlando.
She was excited but also scared. She knew that when she sent in her letter that the chances were small and it was a small victory just to put a stamp on it. Now she’d been picked and the shit could hit the fan. She had to explain to her husband that she’d be gone for 8 weeks as we traveled.
“Brad, I may need to do some shopping before we go or soon after we arrive so I can have some nicer things to wear. I can’t buy them here.”
“I think we can fly you out in the morning and spend our first afternoon and evening in New York City. We can fly from New York to Europe and then enjoy our adventure.”
“That sounds perfect.”
On Wednesday, I finished my homework early and was ahead on all my reading and prep for the final exams. It was about 5:00 and I picked up the phone to call Angela. She answered with a little attitude. “Hello?”
“Put on your sexy undies and I’ll pick you up in fifteen minutes.”
“Fifteen minutes? I’m studying.”
“Pack your books and clothes for tomorrow and I’ll pick you up in fifteen minutes. Just say, ‘Yes, Sir.’ and get your ass moving.”
“Yes, Sir. I’m hungry.”
“Good girl,” was all I said before I hung up.
We drove out by the interstate and went into the Steak and Shake. When we were walking from the car to the restaurant she asked, “Did Mommy cut off your allowance?”
“No, I was just in the mood for a patty melt and they make good ones here along with milk shakes. If you just want to watch me eat, I can take you to Nino’s, later and you can eat while I watch you.”
“I like the burgers here as well.”
We had a nice dinner and then I drove over to a store out by the interstate called the Love Shack. “Where are we?”
“The Love Shack. I told you that I’d get you a toy for when I’m away this summer. I want to get a friend a gag gift as well.”
“Can I wait in the car?”
“No, you’re coming in with me. You’re a big girl now.”
There were a few other cars in the parking lot. There were a couple of 18 wheelers there as well. I guess they stopped for magazines, movies or maybe a blow up doll. As we walked in, I looked around and noticed a couple girls along with about seven guys. I recognized one of the girls from a class I’d taken as a sophomore. She recognized me as well but we were both in the same place shopping for the same things so there wasn’t much either of us could say. I picked up a basket so I wouldn’t have to walk around with a vibrator in my hand.
I didn’t think the girls would be shopping for handcuffs or girlie magazines so I walked their way thinking they’d be in the vibrator section. They were and when we walked over I said, “Hello, Cheyenne, how have you been?”
“Hi Brad. I’m doing well. Interesting meeting you here.”
“There’s a first time for everything. This is Angela, a friend of mine that I brought along to help me shop.” They said hello and I asked, “Are you an expert on these things? I’m buying a couple as gifts.”
“Stay away from hard plastic. Usually the price and quality go hand in hand. Be aware of the size, both length and girth. More than one speed can be nice but twenty is overkill.”
“I appreciate the advice. I’m sorry to interrupt your shopping.”
“I was a little embarrassed when you walked in but, fuck it. Not much I can do about it now.”
“And now I know where I can go to pick up horny girls.”
“That would be creepy. I think we have what we need. I’ll see you around.”
“Bye Cheyenne. See you later.”
They left and I looked to see Angela looking at the large selection of fake cocks. I looked at the prices and quality as well as reading the size in length and girth. The girth measurement was deceiving. I bought one for Angela and two more. I paid the man and we went back to my place.
It was an interesting night while we broke in the new toy while I was recovering from my last orgasm. She didn’t get much rest but enjoyed the evening. I woke up in the morning and she was studying at the table in the kitchen. I walked up behind her and kissed her neck, and gave her a hug.
“I’m sorry for taking you away from your studies last night. I’m proud of you for getting up early and coming out here to study instead of sitting at my desk and reading the letters.”
“My body feels used from all the orgasms last night. I had a lot of fun. I’m done with my homework. I’m just going back and reviewing the chapters in my business law class. It’s comprehensive and a lot to remember.”
“I’ll make you some breakfast. Bacon and eggs or pancakes?”
“Bacon and pancakes if you have some syrup.”
“Pure maple imported from Canada.”
“Whatever, rich boy.”
We had a nice breakfast and both walked to the campus together before going our separate ways to class. The next night was Thursday and after class, I went to the mall. I knew that Jody was a size 2. I bought her a suitcase and a few things like a pair of cotton panties from Victoria Secret and a sexy bra and panty set. I also bought her a little sexy nightie. A nice pair of jeans and a sweater went in the suitcase in case she needed something to travel in. Anything else we could pick up along the way.
Friday, I was in my car waiting when she walked up with a friend. I was glad that she was being safe. She came over and I got out of the car. I handed my driver's license to her friend. “You can write it down if it will make you feel better and she can call you if she wants to at any time.”
I turned to Jody and she was beautiful. Her long blonde hair went half way down her back. She had sapphire blue eyes and a smile that would light up a room. I asked to see her driver’s license. She was 18 and a few days old. I handed her license back and got mine back before we had to hit the road. We were pulling out of the parking lot when I asked, “Do you have any studying to do or can you leave your books in the car?”
“I have some clothes in my backpack.”
“We can put them in your suitcase.”
“Where are we going?”
“Out of town. Someplace we can find you a delicious meal and a room that makes you want to get naked.”
“It must be some room to make me want to do that.”
“We’ll search until we find it.”
We were at the airport by 4:00 and boarding with first class at 4:30. I was glad that Tallahassee had a small airport. We both had small suitcases for the weekend and I put them in the overhead space and let her take the window since this was her first plane ride. We connected in Atlanta and only had to walk three gates to get our next flight. We landed at 7 pm after gaining an hour in the air. I’d called ahead and the hotel sent a town car. We got off the escalator and there was a man in uniform with a sign that said, “Jody Walker.”
She would’ve walked right by him but I said, “You have to pay attention.” She looked up and saw her name. “It’s our ride to your special room.”
Her eyes got big and she said to the driver. “I’m Jody walker.”
I was nodding to him and he took our bags and we followed him out to the car. Traffic was mostly going out of the city so we made it in without too much difficulty. He pulled up to the Sophy and a woman met us and handed me two keys. “I’m Liz. You’re already checked in and your luggage will be up shortly. Please follow me to your room.”
Taking Jody’s hand, you could feel the excitement as we rode up the elevator with Liz to the 10th floor. She opened the door and said, “The Opus Suite is our finest suite. It’s 1400 square feet with a living room, dining room, full kitchen and king sized master. There are two bathrooms and the master bath has a sunk-in tub as well as an extra-large walk in shower with six shower heads. We have you booked for two nights checking out on Sunday. Per your request, we have a car waiting to take you to dinner when you’re ready.”
As we finished the tour and walked back into the living room. Our luggage showed up and after tips were handed out, the porter and hostess left us alone. I looked at Jody and she said, “I wish I had a passport so I could go with you all summer. I want to get naked in this room.”
“Go change into Jeans and a sweater. I’m taking you to dinner.”
She looked like she wanted to argue about staying and fucking but just nodded and scurried off to the bedroom with her bag. I checked out the view and we had a little balcony that had a couple chairs and a table in case we wanted to have coffee or a drink out there. I made a quick call down to the front desk and spoke to the manager and thanked her for the reception. I confirmed that we’d be down in ten minutes for the car and had her send up a bottle of Champagne and a few bottles of club soda while we were out to dinner.
Jody came out wearing jeans that hugged her ass and a sweater that fit her snuggly. “I’ve been so nervous about this weekend that I haven’t eaten much all week. I’m glad I lost a few pounds or I’d still be trying to button these jeans.”
“You look fabulous. It’s late here and an hour later back home. I’m hungry but didn’t want to eat airport food when we were going to be in Chicago with some great restaurants.”
She came over and gave me a kiss that let me know how happy she was and how special she felt. I let my mind wander and hoped that Tiffany had the same reaction when she first saw where we’d be staying. Jody and I rode in the town car to Gino’s East and I told the driver we’d find our way back or maybe walk. It wasn’t that far.
We walked in and she looked at me. I said, “Chicago is famous for many things and one is their deep dish pizza. Now you can say that you’ve tried it.”
“Is it better than regular pizza?”
“You can tell me after you’ve tried it. They call it pizza but could have called it something else. It’s like asking if cheesecake is better than, chocolate cake or a pancake. They all end in cake but are all different foods. This is like comparing spaghetti to lasagna. Both are noodles, red sauce and meat. They’re just different. So don’t try to compare. Just see if you like it.”
“I’ll have an open mind all weekend. I’m sure I’ll be trying many new things. Like that room. It’s bigger than my house. I’m in your hands all weekend.”
After ordering a pizza and a few sodas, we talked about her week. Who she told what and who she was going to tell what after she got home. She had her one friend Claire and she was the only person that knew everything. She was pleased that I understood and let her write down my information before we drove off.
It took a while to cook and when it came, she was tentative as she took her first bite using a knife and fork. She loved the sausage and the buttery crust. As she chewed, she smiled and nodded her head in approval. We decided to walk back to the hotel and it wasn’t too far. Maybe three-quarters of a mile. She carried the small box with her leftover pizza. I took it from her and walked towards the kitchen.
I heard her squeal and looked to see a bottle of Champagne on ice and two flutes on the table. There were also some chocolate truffles and chocolate covered strawberries. After dropping off the pizza, I asked, “Do you want to change into something more comfortable and have a drink in the bedroom or do you want to sit out on the balcony?”
“Both sound good to me.”
“The first glass on the balcony and the rest of the bottle I’ll lick off your pretty breasts.”
“Oh my nipples just got hard just thinking about that.”
I opened the bottle with a pop but not any shooting out. I filled the flutes and she carried the tray of goodies out to the patio. I pulled my chair next to hers and put my arm around her and made a toast to new experiences and lost inhibitions. She clinked glasses and took a sip before setting her glass down and turning to kiss me. She straddled my lap and put her arms around my neck. We made out for a while as I rubbed her ass through her jeans and she purred as we tongue wrestled.
When she pulled back and looked into my eyes she said, “I thought we might be at a nice place and do some fun things but never could I ever even imagine first class, this room or a guy waiting for me at the airport to drive us here to this room. It has all been amazing and we didn’t even board the plane until after 4 pm.”
“You must be something special for someone to do all this just for you.”
“I must be but you’re something special too, Brad. Let me finish this drink. The room is calling me to get naked or at least out of these jeans.”
We fed each other chocolates and sipped our own drinks until the lights of the city had lost their luster and we went inside. I started to close some blinds and she slipped off to the bedroom. After making sure the locks were locked on the hallway and patio doors I refilled the glasses and moved to the bedroom with both flutes in one hand and the chocolates in the other. They all were set on the nightstand and I turned when I heard Jody enter the room in her little nightie.
“You look amazing.”
“Thank you and thank you for the clothes. I’m not a virgin but feel like a little girl in a woman’s world. I’ve never had the things you’ve given me. Most of my clothes come from thrift stores or second hand from friends. It’s a good thing that I’m small.”
She came over to me and started to unbutton my shirt and when I reached for my belt she said, “Stop that. It was my birthday and I’m the one that gets to unwrap my present.” So I stood while she took me down to my boxers. It took a while but every time she looked at me, I got to see that smile and it was all worth it.
She asked me to sit and I wondered if this was spontaneous or she had planned it out. She again straddled me and we kissed but this time I could feel her pussy sliding up and down my shaft with her panties and mine in between us. She was grinding her clit and moaning into my mouth.
My hands were again on her tight little ass as she moved on me. Her breathing got faster and louder as her orgasm approached. I rolled her over and soon she was on the bed with her legs around me as I continued to grind her clit with the bottom side of my cock. When she came, she pulled away from the kiss and let out a long moan as her feet pressed into the bed and her pussy pressed up against me.
As she settled, I pulled back and took her panties off and tossed them on the couch in the bedroom. I lowered my boxers and she saw me for the first time. She sucked in her breath and said, “It felt big but now seeing it, I hope it will fit in my little pussy. I want to feel you inside me.”
After moving her on the bed with her head on the pillows, I kissed her knee and then went in to lick her pussy and begin my oral assault on her little pussy. She came twice more before I sat back and handed her some Champagne. I drank some and so did she before I moved between her legs and let her wet pussy suck me in. I pushed my pelvic bone into her clit with a little circular motion. She giggled and nodded in approval. “It looks like you’re all the way in. I’m full and can feel your cock pressing against my heart. You’re so deep.”
Her legs went around me and she pulled me into her whenever I pulled out. My cockhead never left her but she was getting long hard strokes and was encouraging me to go harder and faster. She came one last time as I started to cum. She was blissful as she purred her satisfaction. She was soon asleep and I got up to clean myself and came back with a washcloth to clean her. After brushing my teeth I turned off the lights and cuddled up behind her.
At 6:00 I was awake. I slipped out of bed and made a pot of coffee. I called down for some real cream and a newspaper along with some pastries and orange juice. From there I was transferred to the spa and booked some time for both Jody and me. I was on my second cup when she came walking out at 7:15. She walked over wearing the white cotton panties and my dress shirt from the previous night. I held her for a little bit.
In almost a whisper I said, “We have a busy day today. Your spa treatment starts in 45 minutes. They will pamper and massage you for a couple hours. Then we’ll come back here and I’ll fuck your amazing body. We have another appointment at noon. After our meeting you can shop and then we’re going to a nice steakhouse for dinner. After that we’ll have to wing it because I have no other reservations and the stores will be closed.”
“It sounds like a lot of new experiences for me.”
“Do you want some coffee or juice? I also ordered muffins and pastries.”
“I like it when you hold me. It feels so right to be in your arms. Let me get some juice and a muffin. I’ll be right back.”
When it was time to leave I handed her the thong and bra that I’d bought her and she slipped on her jeans and sweater again. I walked her down to the desk and when they heard her name, the woman looked at me and then turned back to Jody. “We have your appointment and specific instructions. Please come with us.” Jody looked at me and then just smiled.
I said, “Have a good time. Enjoy your new experiences. I’ll see you in the room when you’re done.”
After leaving her in the hands of the staff, I went up to the concierge. A nice looking woman was behind the desk and asked how she could help me. “I’m taking my girlfriend to the cubs game today. I want her to look right but also comfortable. It’s a little cooler here than it was in Florida when we left yesterday. She’s at the spa for the next couple hours and I’m afraid she won’t have time to shop. We’re also eating at Morton’s tonight. Last minute. Do you have someone that can make sure that she has what she needs?”
“Do you know her sizes? Is there a budget?”
I gave her all the sizes, dress, shoes, bra, and her height. She took my room number and I told her, “The panties should be thongs.”
I went back down and had an hour massage of my own and enjoyed the rub down. I was back in the room, showered and wearing jeans and a t-shirt when Jody came back at 10am. She looked good. Her hair and makeup were done but not overdone.
“You look good. How was the spa?”
“Great, not so great and great.”
“What does that mean?”
“It means that they took me in the back and not one but two people had me get naked and then rubbed my muscles. They told me that it was the only way to fit an hour massage into thirty minutes. I felt great and it was wonderful. After that they said that it was time for grooming and gave me a short robe and had me sit in a chair. I felt like I was going to the gynecologist. They said something about thong bikini wax and trim. I look much different down there now.”
“The easier to eat you, my dear.” I said while imitating the big bad wolf.
She continued and told me about showering, then getting a haircut and makeup done. She came over and gave me a hug and kiss and there was a knock at the door. I went and opened it. The concierge came in with shopping bags. They both looked at me and I pointed to the bedroom. “Why don’t you show her what you bought and what goes with what?”
Off they went while I had some orange juice and a Danish. The woman left with a nice tip in her hand and Jody came out of the bedroom. “I was looking forward to shopping but the outfits she bought me are amazing. I couldn’t have done better.”
She had on another pair of nice jeans and a long sleeved shirt under a Cubs jersey and she was wearing a cubs hat. She had on white sneakers that had stitching that looked like a baseball. She looked perfect.
Looking her up and down I said, “Do you remember the plan from this morning? The Cubs game is the noon appointment. What was on the schedule for right now?”
“You were going to fuck me. I want you to fuck me. You fucked me so well last night.”
I pushed her back onto the couch and took off her shoes, her jeans and her thong. Her nicely trimmed pubic hair looked good and I could clearly see her slit where they had waxed away her fur. She still had on the jersey and ball cap and looked cute so I left it on. I got down in front of her and gave her a couple licks. “No hair on my tongue. What a pleasant surprise. You’re a good girl. Good enough to eat.”
After eating her to just one orgasm, I stood and removed my pants and pushed my already hard cock into her pussy. She was whispering, “Yes, yes.” The volume got louder as she got closer to and then experienced her second and third orgasm with me kneeling in front of her and then me on the couch kneeling behind her. I came in her from behind with my hand holding her blonde ponytail as it came out the back of her Cubs hat.
She went to the bathroom to clean up and then I went and also got cleaned up. I didn’t have any Cubs gear but as we walked up to the stadium just before noon. She could have been a model for the Cubs gift shop. Many men and women were looking at her.
We ate ballpark food for lunch and she loved shelling peanuts and tossing the shells on the ground while we watched the game. She put her shoes on the Cubs dugout right in front of our seats and got more than a few comments from the ladies in our section. The Cubs beat the Phillies 4-3 and we enjoyed historic Wrigley field. It was a fun day.
We went back to the hotel for a little while and I told Jody to call her friend and tell her she was alive. I had to go in and show her how to get an outside line from the hotel. I made sure that she connected and then left her alone to talk. She came out 15 minutes later. She straddled my lap and kissed me. “We got on the plane 24 hours ago. When I was telling her that I was alive and what we’d done so far. It felt like I was telling her about a week's worth of stuff.”
“Is she still worried about you?”
“She wants you to do the same to her next weekend.”
“I’m busy next weekend. But she has my address. I may have to move or something.”
“What time is dinner? What do you want to do now?”
“Dinner’s at 6:30. I promised you shopping. We can go out for a while.”
“I don’t know what I’d buy but would be happy to go look.”
We enjoyed a few hours of shopping, walking, holding hands and talking. We did get her a Hermes scarf and a couple of small framed paintings of different Chicago landmarks. One was Wrigley field. She was a happy girl when we got back with her purchases.
We showered together with some rubbing but not going into full blown sex. I got ready and put on my dress pants, shirt, and sport coat. I was out watching TV when she came out. She had on a nice dress, shoes that matched, and a lightweight coat to keep her warm. She looked amazing and I told her so.
Morton’s of Chicago was a great meal. I had club soda with lime since she couldn’t drink. We had a great meal and she loved her petite filet. I had the ribeye and it was fantastic along with the spinach and potatoes we had with our steaks. We started with small Caesar salads.
When we got back to the room. She sat on the sofa. I said, “We fly out at 1 pm tomorrow and we should leave here by 11. They have a nice brunch downstairs if you’re hungry.” I pulled a wrapped present from the shelf in the closet and handed it to her. “Happy Birthday.”
She looked up at me. “I wasn’t expecting anything.”
“It’s as much for me as it is for you.”
She just unwrapped it and pulled out the vibrator that I’d bought for her. “I wasn’t expecting this. I can see that it’s something to remember you by. How is it for you as much as it’s for me?”
“You’re going to put on a sexy show for me. Something else that’s new and exciting for you.”
“You want me to masturbate for you, with this toy here and now?”
I just smiled and nodded. “I’ve watched you all weekend. You like to be watched and looked at. It’s not much different than you doing a striptease or a lap dance. I’m sure when you’re done, we’ll be fucking. This is just foreplay.”
She hesitated for a minute but then stood and set her coat to the side. She turned away from me and pushed down her thong as her dress rode up her ass and she was straight legged with her heels on as she stepped out of them. She wiggled her ass and then turned back to face me and sat back on the couch with her feet on the coffee table. She let her knees fall outward as she started with her hand but soon had the toy teasing her lips, her clit and then plunging deep into her pussy.
The whole show lasted about 15 minutes but it was one of the sexiest 15 minutes of my life. Just when I thought that she had zoned me out and was doing it just for her, she’d look over at me with that sexy smile and beautiful eyes.
After she came she had to raise her voice to make sure I didn’t damage her dress as I helped her remove it and took her to bed. We fucked for a few round with her toy on her clit when I was fucking her and in her pussy when I was recovering beside her or in her mouth. It was close to 2am when we were both sated and lying together. Her head was on my chest and her leg was on mine.
“Brad, I wanted to get mad and leave when you suggested I masturbate for you. But then I thought about this whole weekend. We aren’t boyfriend and girlfriend. We’re doing a deal. We negotiated and you have more than lived up to your side of the deal. I decided to just bite the bullet, swallow my pride and be a little slut for you. A whore might be more accurate but then I got into it. I saw how you reacted and how your lust made me feel. I got into it and enjoyed it so much. Your cock and the way you fuck me is so different than the boys I’ve been with and how clumsy and unenjoyable they are. If I knew that every time would be like this, I’d be a whore for the rest of my life. Today has been amazing.”
“I’m no expert but I’d say that very few whores have days or weekends like ours. Don’t quit your day job and study hard in school so you can decide what you get out of life.”
“I’m about to fall asleep but thanks again for my best day ever.” I kissed the top of her head and she was soon asleep on my chest.
In the morning, she woke me by kissing my chest and rubbing her hands across my abs. We never spoke but made gentle love. She started on top but finished underneath me. It was a sweet time. I led her to the shower when we were done and we washed each other and I enjoyed washing her long blonde hair. She was out and I’d dried and brushed her hair. The first words we spoke was when she said, “Thank you.”
It kind of broke the spell and we both went into the mode of getting dressed. We had brunch at the hotel and then packed for our trip home. Jody had more than what she came with and had to pack carefully. When we landed in Tallahassee, she came to my house so her parents wouldn’t freak out. I dropped her at school the next day and she said that her friend would drive her over to pick up the suitcase after school.
When they showed up, we all talked about the trip and how her friend felt before meeting me, after meeting me, after Jody had called her and now that Jody was back and had a permanent smile on her face. Her friend Claire felt better after I freely gave her my information and was greatly relieved when Jody had called.
I wondered if Tiffany would feel better if Jody called her. I asked Jody and explained that Tiffany would be going with me for the summer but didn’t mention the husband thing. It wasn’t my story to tell. Jody said that she’d be happy to talk to her and ease any fears, so I called Tiffany. I explained about Jody not having a passport and me taking her to Chicago. I mentioned the fear issues and asked if she’d feel better talking to Jody. The phone call was on my tab so both girls were safe from the phone bill inspection. Tiffany said that she’d like to talk to her.
I told the girls to lock up when they left and went to play basketball or frisbee on campus. There was always a pick-up game if you knew where to look. I worked up a good sweat and when I got back to my apartment, the girls were gone but a note was on the table.
Dear Brad,
I had a good talk with Tiffany and ended up telling her everything. Some things excited her and some things scared her but overall, she feels better about the trip. I wish I was going and Claire and I both plan to get a passport this year in case you’re looking for company next summer. I plan to go to the local community college so I should be around if you need a date when you get back from your adventure.
Love,
Jody
I didn’t feel the need to call either of them for more information. I thought about what I did and how I did it with Jody and if I wanted the same approach with Tiffany. Jody was younger and I treated her as such. Tiffany was older and I may not be as kind or generous. It was also 48 hours versus 60 days. I didn’t have anything set in stone but did have some ideas.
I finished my exams on the 21st of April and flew to New York City. There were 9 days before Tiffany would arrive. I walked in and found Mom home. Dad was at work and leaving the following day for 10 days of meetings in Switzerland and Germany.
I put my bag in my room but didn’t have too much since I still had my place in Tallahassee and didn’t sublet it although Angela talked me out of a key the last time she was over for a night of fucking and said that she may stop by and use my big comfy bed from time to time when she needed to get away.
Mom was in the kitchen and I grabbed a beer from the fridge. She asked, “So how is my long lost son that never calls home?”
“Poor Mom, the dial on your phone doesn’t work? I’m doing well. All A’s except for a B in Calculus for business. What a worthless class. How have you been?” I asked, as I gave her a hug.
“I’m doing well. I go to the board meetings, manage the investments in your and my trust. You don’t spend very much and the investments are doing well. Probably too well.”
“I’m taking a trip for a few months and will be visiting different hotels. I may be spending some money for a change.”
We had an arrangement where I put everything on my Visa card and paid the bill with a check. Mom and the accountants just saw what I paid to Visa and not what I spent money on. It gave them some idea on how responsible I was but not what I was doing day to day.
“Are you going alone or taking a friend?”
“Taking a female with me.” I could have left it there and my mom wouldn’t have pried. She let me fail or succeed on my own. She never asked if I was doing my school work but would ask about the grades at the end of the semester. I’d decided to tell her the whole story. I started back in middle school and then how it had nagged me off and on for years thinking about it. I was now in a position to test my theory and run my experiment.
“So you’re now you’re Professor Henry Higgins. Have you found your fair lady?”
“Nice analogy. I was surprised to have over eighty replies when the last of them trickled in. A few called me a creepy sick bastard. Most just wanted a chance to get away. A quarter of them had nude or topless photos with their replies. I ended up calling four of them and decided on a teacher in Orlando that is off for the summer.”
“What does she teach?”
“Humanities and Art History. She wants to see and experience more of the things she teaches.”
“So she’s older.”
“A few years, six or seven. The bigger thing is that she’s been married for five or six years. I went back and forth questioning her and myself before I finally let her be the judge of what’s right for her. It isn’t like I plan to marry her. She’s just the test subject in my experiment.”
“If you’d like to talk more about it before or after, I’d love to hear about it. How long are you home for?”
“I’ll leave on the 1st. A week or so.”
“Can you sit down with me and go over your trust and talk about some of the Hotels? If you can stop by on your travels and check them out, that would be great.”
“Yes and yes. We can do it now or any time next week.”
Mom was never the best cook and never tried to be. She had people that could cook for her. She lived in a city with more restaurants than any other. She ended up ordering a pizza and we played cribbage while we talked and enjoyed the evening together.
When we sat down, I found out some more about my trust. I was now a trustee and could do whatever I wanted but I left Mom on as a co-trustee to be able to do things when I wasn’t around. She had my vote during the board meetings. I owned 50% of the stock. She owned 50% of the stock. The trusts said that we couldn’t sell it unless we went public. This kept the higher executives in the company from asking for stock. We had to pay them well but we couldn’t sell or give it away if we wanted to.
Most board meetings had a motion to go public but Mom would vote against the motion and it was done. I’ve heard her and Dad argue over that one thing more than any other. Even if she said, “Yes,” I’d vote against it and that was one thing that needed to be unanimous and couldn’t be voted by proxy.
Beyond the shares in the company, my trust took in dividends from the company and also owned stocks, bonds, real estate and some art work. There were a few lock boxes with gold in them but those were more for rainy days and apocalypses. The nice thing about having hotels around the world is that it was easy and legal to have bank accounts around the world. I had ten bank accounts besides the four brokerage accounts.
When the totals came in I didn’t think I could spend it all if I wanted to and I didn’t want to. There was always an Island or something crazy but I could buy any car, house or boat that I wanted as long as it wasn’t an aircraft carrier. I was grateful for Mom and all the work she took off of my shoulders. She was one that I trusted and could depend on to do what was in my best interest.
◊◊◊
Chapter 3
It felt like the first day of school when I was saying goodbye to my mom. She gave me a hug, stood back and looked at me. She warned me to be safe, have fun and call from time to time. I took a cab over to the Gracie mansion and checked into the Master Suite. I rode with the town car to the airport and went inside with the sign while the driver stayed with the car.
Tiffany was wearing a sundress as she came down the escalator. I got a hug from her and we got her bags. On the drive into the city, we talked about her flight up and packing for such a long trip. I assured her that she could have brought two sets of clothes and they’d always be clean. We could have laundry done every night if we wanted.
When we got into the room, I told her to unpack her things and then we’d talk. She admired the suite as she went to the bedroom. There was a bar but not a full kitchen like the suite in Chicago. We looked out at the river and the park beside the property. When her clothes were put away, she came out and asked, “Why did I just do that when we’re leaving to go overseas?”
She sat down and I said, “Tiffany, can you tell me what Jody told you and what your expectations are while we’re together?”
“She said that it was like a dream come true. She was a princess and you were her prince until the clock struck midnight and it was all over.”
“What were your ideas before she called?”
“That I’d get to see the Louvre and some other sights by day and be your sex slave at night.”
“I wanted to set your expectations before we left. Jody had just turned 18 and sexually was very inexperienced. You’re older, more mature, and more sexually experienced. My expectations for you are higher. You’ll be my sex slave twenty-four hours a day, seven days a week. You’ill also be treated like a princess, stay in nice hotels, eat great meals and get guided private tours of wherever you want to go. Think of the best and worst and multiply it by ten.”
She sat quietly and tried to absorb what I’d just said. She looked up, “Can you give me an example of the worst?”
“You’re a beautiful woman but you have what, an A cup or small B cup breasts?”
“Right about there.”
“I plan to leave many of your clothes here. You can trash them or we can pack them away for you to pick up on your way home. I don’t think I’ll let you wear a bra most of the trip. We’ll be gone for two months. That means two periods for you. That means that I’ll only have your hands, mouth and ass during those times unless I’m in the mood to get messy and just fuck you and clean up later. I’ll use all three holes before we leave New York. Did Jody tell you about her toy?”