The Christmas holiday break was coming to an end. It was great to come home and see my family. I hadn’t been home since I left in August. Now it was time to get back to school. The trip from where I live in Naples to Tallahassee is a little more than a seven-hour drive.
My Father was disappointed in my grades for the fall semester. After having a long conversation, he thought it best if I concentrated on my studies. He insisted that I leave my car at home for the semester and gave me money to take the bus to Florida State.
I looked up the schedule for the bus. It was crazy. A seven-hour drive by car takes twenty-one hours by bus. The bus makes over seventeen stops as it zig-zags across the state. I looked into flying but it was expensive and nothing was available for several days.
It hit me, pocket the money my Father gave me and hitchhike back to school. It is a straight shot up Interstate 75. It shouldn’t take much longer than if I drove my car, and I will have an extra hundred dollars to party with when I get back to my dorm.
The next morning, my parents drove me to the Greyhound terminal. Carrying a backpack with a hidden cardboard sign with large letters that read FSU, I said my goodbyes. As usual, my Mother cried. She always gets emotional when I leave. My Father gave me the evil eye and told me that I better pick up my grades or he wouldn’t pay for school. Then, he hugged me.
As soon as they left the building, I went out a different exit. The terminal was a short walk to the entrance ramp to the Interstate. I pulled out my sign and prominently displayed it for drivers to see. It was only a five-minute wait before a truck stopped. I ran up to the passenger door and climbed in. The driver was a young man. He told me he was heading to Bradenton, about two hours north. It was a good start.
Exactly two hours later, the truck was rolling down the exit ramp for Bradenton. It came to a stop, I grabbed my backpack, thanked the driver, and hopped out. I crossed the street to the northbound entrance ramp, pulled out my FSU sign, and waited. Time was at a crawl as I waited. I wasn’t as lucky getting a ride and started to regret my decision to thumb a ride rather than beg for my car. It was a half-hour when someone finally stopped.
A beautiful BMW Z4 pulled over. It was a convertible but, because it was a brisk sixty-three degrees out, the top was up. Too bad, it would have been fun driving with the top down. Like the first ride, I ran to the passenger door, opened it, and lowered myself into this high-performance roadster. As I settled in I looked at the driver. I laughed out loud when I realized that the person driving this land rocket was an old lady.
She looked at me and with a slight annoyance in her voice asked, “What the hell is so funny?”
The look on my face must have given me away; she knew. I was hoping she wouldn’t throw me out of the car. I waited too long for this ride.
With a sheepish look on my face I said, “When I opened the door, I didn’t expect…”
She interrupted, “Expect what? A Grandma? An old lady? Your Nana?”
“Well, you have to admit, this isn’t the typical car a mature…”
She cut me off again. “Tread lightly here. After all, I am your chauffeur.”
This woman was pretty fearless. She took off up the entrance ramp merging onto the Interstate like she was exiting from a pit stop at the Daytona 500. I glanced down at the speedometer, we were already exceeding the speed limit and we weren’t even out of the merge lane yet.
I was hanging on to the door handle, just slightly frightened. The car was weaving right and left, passing cars like they were standing still. “I appreciate you stopping to pick me up. My name is Paul. I’m on my way back to school. I am a junior at FSU.”
“Nice to meet you, Paul. My name is Darlene. Today is your lucky day. I work in Tallahassee and that is where I am heading. I saw your sign, that is why I stopped. We just have to make a stop at my house in Crystal River.”
This is luck. It is almost as good as driving myself except her driving almost made me shit myself. It was still better than sitting on a Greyhound bus all day and night. “Wow! That is great. My Father wanted me to take the bus. Thank you so much.”
There was a long silence. The purr of the engine was hypnotic. As we climbed up the Skyway Bridge I glanced over at Darlene. She was wearing a dress that was hiked up high on her thighs. Her legs were bronze and muscular. Then I noticed that with every bump in the road, her tits had a little bounce, she wasn’t wearing a bra. I couldn’t believe this senior citizen was starting to give me a hard-on.
She busted me staring at her. “What are you looking at?”
I was at a loss for words. Like a guilty child, I defensively lied. “Nothing! Why?”
We were flying past Tropicana Field. I wanted to change the subject. The only thing I could come up with was to talk about baseball. “Are you a Tampa Bay Rays fan?”
I am so lame. I wanted to catch my words and shove them back in my mouth. I should have come up with a wisecrack or something clever to say. The more I checked her out, I realized that she was a very sexy woman. Very different from the girls at school. Darlene had a confidence about her that girls my age don’t possess.
She ignored my question, responding with questions of her own. “Do you have a little honey at school that you like to hang around with?”
“No one particular. I don’t want to be tied down. I do okay though.” That was a lie. There was no one in my life. I had a girlfriend in high school, but we never messed around. She was raised Catholic and wanted to wait until she was married. The fact was, I was a twenty-year-old virgin.
“Well good for you, Stud. You’re a hunk. I’m sure you do just fine with the women.”
As she was talking, she pulled her dress slightly higher showing more of her legs. I was trying not to be so obvious as I looked over at her. She started to brush her fingers over her left nipple. My dick was straining against my blue jeans.
Darlene reached across the console that separated us and ran her hand across my lap. “My-my, what have you gotten yourself into?”
Her touch almost made me come in my pants. I unzipped my pants and let her see my erection.
She screamed, “What are you doing?”
I was so embarrassed. “I’m sorry. I thought…”
“Well, you thought wrong. What was I supposed to do with that while I’m driving?”
That was not what I expected her to say. I had no response. We sat in silence for the next ninety minutes as we raced toward her house. She brought the car down to what seemed like a crawl as we passed through the town of Homosassa, a known speed trap. I scanned the dashboard and realized that we were still going well over the speed limit. Within minutes the red and blue flashing lights of a county sheriff's car was on our tail.
Darlene pulled the car over. She also pulled her dress down over her knees. She magically gave the appearance of an old lady. She rolled the window down and kept her hands in plain sight. I could tell this wasn’t the first time she was stopped for speeding.
“Paul, keep your mouth shut. I’ll do the talking.”
The Deputy walked over to the car. “Good afternoon, Ma’am. May I have your license, registration, and proof of insurance, please?”
“Certainly. Did I do something wrong?” She sounded so innocent.
“Ma’am, I clocked you at twenty miles over the posted speed limit. Is there a reason you were going so fast through town?”
I couldn’t believe it. This cop was looking to give her a break, a chance to explain. If it was me, he wouldn’t hesitate to write a summons for speeding.
“I am so sorry, deputy. I’m taking my Grandson Paul back to college in Tallahassee. I drove down to Bradenton to pick him up. I must have lost track of my speed. He will be a senior next year and we were discussing his future. He is my only grandchild and I want nothing but the best for him. When he graduates I want him to apply to law school like his Grandpa Al did when we were just kids. I wish he was still with us. He would have been so proud of Paul.”
Holy shit! She just made up a complete fabrication. Just a short while ago, she rubbed her hand across my dick. I was ready for her to take it in her hand and stroke it. Now I am her beloved grandson.
The deputy handed the papers back to Darlene. He leaned into the car and looked at me. “Son, you’re very lucky to have a Grandma that cares this much about you. Do the right thing and listen to her advice.”
He stood up and said, “Ma’am, I need you to slow down, drive safe and have a good day.” Then he turned back to his vehicle and left. No summons.
She giggled as we were on our way, about thirty minutes from her house. As soon as the deputy was out of sight, her dress was back up her legs again and she once again started to pinch her nipples to a hard point. My dick almost split my pants open.
I didn’t say a word for the rest of the trip. The fantasy I had, I was undressing this lady in my mind. She steered the car off the main road toward the Gulf of Mexico. I knew we were running out of land. I could smell the saltwater in the air. The road ended at a driveway but I couldn’t see the house. We came to a stop at one of the largest homes I’d ever seen.
I wasn’t sure what to do. “Should I wait here for you?”
“Don’t be silly. It’s Sunday. I don’t have to be in Tallahassee until tomorrow. We’ll spend the night here, get a good night’s sleep, rise early and I’ll have you at school in time for your first class. Then I’ll go to my office for my weekly grind.”
We walked into her house together. “My first class isn’t until Wednesday. I should call my Mother and let her know where I am.”
She looked at me with a wicked grin. “What are you going to tell her? That you missed the bus and you were hitchhiking and some strange woman picked you up. That you have no idea where you are. How do you think that will go over at home?”
I gave it some thought. “You’re right. I’ll just send her a text to let her know I am okay.”
She said, “Good idea, Stud. Make yourself at home. The fridge is stocked with beer, soda, and snacks. Help yourself to whatever you want.”
I went down a long hallway toward the kitchen. I passed a living room that was the size of my entire house. It had a wall of glass sliding doors that led out to a pool. Beyond that was the Gulf of Mexico. Water as far as the eye could see, the view was amazing. I grew up in a comfortable home and I wanted for nothing. This was a world that I was not familiar with. I became aware that Darlene was a wealthy woman.
As the winter clouds swirled above and the sun started to set over the water, the brilliant blue, gray, and orange combination in the sky was stunning. The view was mesmerizing. I felt a presence as I stood gazing outside. It was Darlene. She quietly snuck up behind me. I turned to comment on the sunset, she was standing there in a thick white robe.
“I am going for a swim. The pool is heated. I keep it at eighty-eight degrees. A comfortable temperature year round. Why don’t you join me.”
“I don’t have a bathing suit.” It was the only thing I could think to say. What an idiot I am.
She burst out laughing. “Okay then. You were ready to take out your cock in my car while I was driving. Now you're shy? What the fuck is that all about?”
She opened the door and stepped out onto the pool deck. She untied her robe and placed it on a lounge chair poolside exposing her nude body for me to see. There were no noticeable bikini lines. It became obvious to me that she rarely wore a swimsuit. I went outside to join her, shedding my clothes and releasing the erection that had been strangled in my pants for hours.
Darlene’s body was incredible. I wondered if she was a model when she was younger. Her tits were naturally firm, a muscular body with solid legs and a tight ass. Maybe she wasn’t as old as I originally thought.
Her eyes were focused on my dick. “Well, you have quite a weapon there.”
That made me laugh. No one ever referred to my penis as a weapon. It was exceptionally solid at the sight of Darlene. It was straight out like a diving board. She turned and dove in the pool. I followed her lead. The water was warm just as she said. Now I understand how she was so fit. She was swimming laps like an Olympian. I’m in great shape and I couldn’t keep up with her.
“Now I know how you stay in shape. You are a strong swimmer.”
“I was on the swim team in college. I never lost my love for the water. Even when I travel, I try to stay in a hotel with a year-round pool.” Then she reached out and pulled me by the shaft toward her. “How about you Stud? How do you stay in shape?”
It was now or never. The only thing she didn’t do was lie down, spread her legs, and beg me to fuck her. I knew what I needed to do, to follow what came naturally. I reached out and held her hand, leading her to the stairs out of the pool. It was cool out and it caused both our bodies to develop goosebumps. I also started to shrink. Oh God no! Not now!
Darlene took the lead, walking me to her bedroom. Even her sleeping quarters were as large as a small house. This woman lives like a queen. Her bed is on a platform surrounded on three sides by glass from the floor to the ceiling. The unobstructed view of water encircles her room. There were no curtains on the windows. Anyone outside could see in.
“You sit here and don’t move.” She placed me in a small chair with no arms across from her bed and then walked into a side room.
The anticipation of my first time, making love to this woman was building. I sat for what seemed like an hour waiting for her to return. In reality, it was more like five minutes. When she came back into the room, she had handcuffs and a silk scarf in her hands. I became very excited thinking she was going to let me cuff her to the bed.
That was not the case. She pulled my hands behind my back and handcuffed me as if I were being arrested. Then she used the scarf as a blindfold, slipping it over my head making it impossible for me to see. Her hand started to stroke my erection.
I could feel her straddling me. “Have you ever fucked an older woman? Don’t you disappoint me. That is a beautiful cock you have. I want it all night long.”
She guided me inside her. It was just like I imagined. The feeling was wet and tight. Her body was sliding up and down, I could feel her nipples touching my face. I think she was doing this on purpose, teasing me. I tried to bite one as it passed over my mouth. She pulled away. Now I wanted it and became aggressive, leaning into her, trying to nibble and suck it. Her hands were behind her back on my knees and I could tell she was leaning back, denying me access to her tits.
The way she was moving created a sensation like I’ve never experienced. I was building up. It was the same feeling as when I jerk off to a porno. I didn’t want to explode yet, but she wouldn’t stop. Up and down, two, maybe three more times. Then it happened. I couldn’t stop the eruption.