This is a fictional story in which everyone is over the age of 18.
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It had been many years since I had seen Michelle. We'd text on our birthdays, and I'd see pictures of her on Facebook, but seeing someone in person vs social media is different.
We had been high school sweethearts. I was a year older than her, and I moved away to attend college. I returned over the summer, but while I was gone, we drifted apart. We were still friends, but we didn't hang out as much or make out like we used to. We used to do everything together. We were in the same activities both in school and out of school. We worked at the same place, and were often over at each other's houses for dinner. Everyone thought that we would eventually get married. After she graduated from high school, she went to college out of state, and we lost touch completely.
We'd send text messages back and forth for a while, but eventually the frequency dwindled down to birthday and Christmas texts. I eventually married, but I would think about her from time to time. Thinking about what might have been.
After a few years, my wife and I divorced, and I moved to a different state to take a tech director job in a public school. With the advent of social media, we eventually reconnected. I noticed a post from Michelle that she had recently taken a job at a major tech firm in the same state, but on the opposite side. I reached out to her again, asking her about her job, her life, the usual. She said that she was working in the training department and her life was pretty boring. She didn't marry or have any love interests, but she loved to travel.
We eventually exchanged pictures. I was a bit worried at first. I'm not the greatest-looking guy. I had always wondered if my ex-wife had felt sorry for me, and then finally cut her losses for someone better looking. When I looked at the picture of Michelle, I was floored. She looked just like she did in high school. Her Hispanic heritage was highlighted by her brown eyes and long black hair. She stood (at least back then) at around 5'4" and looked to be a decent D cup. She looked like she was a little heavier than she was back then, but then again, who isn't? I commented that she looked great, but I didn't get a response back from her.
A few weeks later, I had the opportunity to attend a conference in the same city where Michelle lived. This whole time, I had been thinking about her more and more. Not only reminiscing about when we were together 20 years ago, but thinking about what might have been, if we had stayed together. I didn't get to travel to that side of the state very often, so I thought I would take a chance.
I texted Michelle that I was going to be in town for a few days, and wondered if she would like to have dinner one night. I held my breath, not knowing how she would respond based on our last interaction. A minute later, she texted back, "I'd love to. Let me know when you'll be here." I let out a huge sigh of relief and texted her the dates of the conference.
The weeks leading up to the conference were a blur; thoughts of Michelle consumed more and more of my attention. I even fantasized about what could happen after dinner; I fantasized about going back to her place or my hotel, having a few drinks while we caught up, and eventually having wild sex. The night before my flight to the conference (some bean counters figured it was cheaper to fly across the state and rent a car than to make the eight-hour drive), Michelle texted, asking about my travel arrangements. I sent her my flight information and that I was going to rent a car. She said that she had the next few days off, and that she would be happy to pick me up at the airport. Thinking this was a way to help my fantasy come true, I readily agreed.
That night, I could hardly sleep, anticipating meeting up with the woman that, 20 years ago, I thought I was going to spend the rest of my life with. I scrolled through her social media, looking at her pictures, pausing on some of the more revealing ones. There was nothing risqué, just some with her in a one-piece swimsuit on a beach. One thing I started to notice was that in a lot of the vacation posts, she would always mention that she was with someone else, a woman named Brittany. I couldn't see much information about Brittany, which wasn't too surprising. Seeing more and more posts with her, my mind started racing about who this other woman was.
Was she just a friend, someone she knew who liked to travel, or maybe something more intimate? I tried to dismiss the fact that Michelle and Brittany could be romantically involved. She didn't show any interest in girls 20 years ago, but maybe her tastes have changed over the last two decades. The thought of Michelle not being attracted to me caused my heart to sink. After a moment of thinking the worst, I decided that I didn't have enough information to draw a conclusion and to wait until tomorrow to make any judgments.
My flight was uneventful, and I grew more excited as the plane landed and taxied. My heart began to beat faster as I walked down the jetway, and I saw her. She looked exactly like her pictures. She was wearing a long-sleeved white blouse, unbuttoned far enough to tease, but not too far, she had on a brown plaid short skirt, and wore a pair of matching heels. She had a huge smile on her face as she closed the gap between us. She held out her arms and embraced me in a hug. With her heels, I didn't really have to bend over to embrace her.
"Oh my god!! It's so good to see you," she squealed.
"You too," I replied. We broke the embrace, and she stepped back to look at me. I took the opportunity to give her a good look.
"You look amazing," I complimented. She looked as if she had lost some weight compared to some of her online pictures.
"You too. I can't believe it's been 20 years." She stepped forward to hug me again. This time, I noted the faint scent of vanilla on her. I inhaled deeply, searing the scent into my memory. Luckily, I didn't have any checked baggage, so we were able to leave right away. We got to her car, and she drove me to my hotel. We filled the drive with small talk, mostly her talking about her life, living in the city, and some of the adventures she's had while travelling. While checking in, the front desk clerk looked at us and asked if we needed one or two keys. I looked at Michelle, and she winked at me. I turned to the clerk and asked for two keys. We took my bag to the room and decided to have dinner in the hotel restaurant.
Dinner was uneventful, and the food was delicious. We continued to talk long after we finished our meal. The conversation eventually turned flirtatious, filled with innuendo and double entendre. We'd gaze into each other's eyes, and occasionally, one of our feet would brush up against the other's leg. The last time it happened, I felt her foot running up and down the side of my leg. I shifted in my seat to lean forward, my hands folded on the table towards her. She imitated my pose, our hands just inches from each other. We gazed into each other's eyes again, and then she reached out to put a hand on top of mine.
"Do you ever think about what might have been? If we had stayed together," she asked quietly.
"Sometimes," I responded. "How about you?"
"When I left for college, I thought about you a lot, but then life happened, and I thought of you less and less. Lately, though, I've been thinking of you more and more."
"Same with me," I said. "I eventually got married, but it didn't work out, and we divorced after a few years. How about you, anyone significant in your life?"
"No. I was too busy with school then and work now. Although I do have a travel buddy that I'm close to."
"Is that Brittany?" I was hoping for an opening to ask about her.
"Yeah. She works at her husband's company, even though she doesn't need the job. She does it for something to do, rather than for the money. Whenever I go on a trip, she'll ditch her husband for a time, and we go and have a good time together."
"I wondered what the deal was with you, too. I thought maybe you were together."
Michelle let out a loud laugh. "Nothing like that. Although there was one time in Cabo. We had had too much to drink and we made out."
"Really!! I wish I could have seen that," I said with a sly smile.
"Ha-ha," she said mockingly. She then reached to take my hands into hers. "You missed your chance. But...." her voice trailed off, and her foot began stroking my leg again. Her gaze morphed to say "Take me upstairs and fuck me". The actions she was starting to take, along with the thought of her making out with another woman, caused my cock to stir a little. She raised her eyebrows and motioned to the door with her eyes. I smiled and said, "Do you want to get out of here?" She gave me a big smile and replied, "I thought you'd never ask."
We stood up and left the restaurant hand in hand and made our way to the elevator. I reached out to press the button, and then moved my hand around her waist. The wait for the elevator seemed to take an eternity. I slowly moved my hand down her waist to the top of her ass. She didn't do anything to stop me, so I grabbed her right cheek and gave it a squeeze. I noticed how tight and firm it was. The door dinged and opened. We waited for the people on the elevator to file out, and then stepped forward. We were the only ones in the car. I pressed the button for my floor and waited patiently for the doors to close.
As soon as they closed, I turned to her and pushed her against the wall, my hands on her tits, and bent down to kiss her, hard at first, then with more passion. I massaged her tits through her blouse and bra, and at the same time, she reached down and unzipped my pants, reaching for my cock, which was almost fully stiffened now. After what seemed like an instant, the elevator stopped and dinged. Michelle let out a sigh of disappointment that we had to stop. By the time the doors began to open, we had regained our composure. Seeing no one waiting, she grabbed my hand and practically ran out the door.
We made our way to the room, and at the door, I struggled to get the key out of my pocket. Michelle was all over me, reaching to unbuckle my belt. I was able to get the door opened just as she finished undoing the buckle. We stumbled through the door, my pants falling to my ankles. I stepped out of them and lifted her blouse over her head. She let go of my cock long enough to raise her hands to help remove her blouse. She then reached around and unhooked her bra. Tossing it aside, she started unbuttoning my shirt.
Frustrated that she was taking too long with the buttons, I reached up and tore it open, sending buttons flying. She pulled it off my shoulders and off my arms, throwing it next to her bra. She grabbed my hand and led me to the bed, stopping at its foot. She unzipped her skirt and did a shimmy, causing it to fall to her feet. Stepping out of it, she stood in just a black thong. She pulled me closer, embracing me and reaching up to kiss me.
I leaned down, our mouths meeting, tongues dueling, hands exploring each other's bodies. I would rub my hands all over her back, reaching down to grab her ass. She would do the same. We kissed passionately for several minutes. She broke off the kiss and rested her chin on my shoulder.
I wanted this when we were in high school, but I was too afraid to pursue it," she said. "But over the last few weeks, I've been thinking about you more and more. I've thought about what you were like, what activities you do, if you were in a relationship, what your cock would feel like inside of me."
I almost melted when I heard her say that. "I've been thinking about you as well. I wanted to fuck you so badly back in high school, but I was also afraid to pursue it. I saw that you're well-traveled, and I was curious about your job or if you were involved with anyone. I've recently fantasized what your tits would look like if you were bouncing on my cock and how you would taste when I ate your pussy."
"You'll find out tonight," she whispered. "Lie down on the bed."
