Most of my other stories tend to get to the best parts fairly quickly so I tried to change things up a bit and get there a bit slower.
*****
I was excited when my company told me that myself and one other coworker would be traveling to the Miami office for the week to visit with some of our clients. I was mostly excited to trade the snow and cold of Chicago for the sun and warmth of Florida. I didn't know my coworker well but his name was Ben and he was probably about 45 and married. We worked in the same building but there were a lot of people so I didn't yet know everyone. I am Jeff and I am 24 years old working at my first real company after college. Ben and I were going to meet at O'Hare and I got there early so after I passed through security, I found a seat at my gate and alternated between reading my football magazine and scoping out the other people who would be on my flight, as I am sure all of us do!
Being a young, always horny and also single man, I of course was hoping to see some nice scenery on my flight but so far, no luck. Ben wasn't there yet and I was pretty bored when I saw a woman approaching with her child. The woman looked to be pretty attractive, wearing pink Juicy pants with a tight white tank top. She had dark hair and a slightly tan complexion for a white woman. She looked to be about 35 and the kid was probably 5 or 6. As she got closer, I scanned for the husband or boyfriend but didn't see one so I kept watching with my eyes peering above my magazine. Sure enough, she sat across from me, giving me a nice view of a more than ample set of tits albeit a slightly more than ample everything else too! She was occupied with her kid which allowed me to get as many glimpses of her chest as I wanted without getting caught. I always did have a thing for older women and I found myself wondering if she was married and where the husband would be while she traveled with the child.
As my mind wandered, I felt a sudden touch on my shoulder and turned to see Ben plop down on the seat next to mine and shake my hand. We chatted and exchanged pleasantries but in my mind I was a bit annoyed that this was taking away from my checking out women! Out of the corner of my eye I saw this woman reach for her ringing phone and tell the caller that she and the child were already sitting at the gate waiting. Here we go, I thought, the hubby is on his way. About 5 minutes later, an older woman approached the pair across from me, and I could immediately tell by her appearance that she was this other woman's mother. She looked to be in her late 50's or early 60's and was wearing a pair of white pants and an oversized black sweater. She wasn't as attractive as her daughter as her skin was showing signs of wrinkles and she was out of shape with a big ass. However, I did notice that despite the oversized sweater hiding her chest, there did appear to be a set of tits equal to or even bigger than her daughter's.
I surmised by their slightly olive complexion that maybe they were of Greek origin which I was a big fan of because of the dark hair and features. As Ben spoke to me about his hectic ride to the airport, I kept gazing across at both women now, just trying to hear what they were discussing and find out more about their lives. Again, neither woman would make most men do double takes but I found them to be attractive enough to imagine what they looked like without the clothing on.
Now Ben and I had single seats in different rows because our company booked them at different times but the plan was to take a cab together once we arrived in Miami. I had no problem sitting alone but I was pissed that my seat was in the last row. I didn't like the idea of waiting for everyone else on the plane to get off before me, not to mention the people that would be lined up to use the bathroom right near me. At least I had a window seat I guess.
We eventually boarded the plane and as it filled up, no one was taking the seat next to me and I started to get excited at the thought of some extra space. Just as I thought this, I saw the stewardess talking with someone and pointing to the back where I was. Great, what was going on? I saw another man standing there and figured out that this other person was in his seat so the attendant told them there was a seat in the back next to me. The person stood up and I saw that it was the mother I had been eyeing earlier. Her black hair showed some gray and was clearly a dye job but I appreciated the fact that she wanted to try and look good. From the side angle as she grabbed her bag from the overhead, I noticed I was right, it definitely looked like there was plenty going on under that big sweater. She made her way to the back and sat next to me, barely glancing at me or acknowledging me, but clearly indicating that she was upset about being separated from her daughter and grandson. I took in her faint scent from her perfume and felt my cock awaken in my slacks. I usually like to wear sweat pants on planes because they're way more comfortable but Ben and I had to go right to the Miami office when we landed so I was stuck in these tight uncomfortable pants. I thought I saw the woman glance down toward my crotch and then look at my face but when I turned my head, she was facing straight ahead. We were about to take off and the woman's daughter came to our row to give her mother something to read during the flight, giving me one more view of her tank top covered tits and then her big ass as she walked away.
I don't usually like to strike up conversations with strangers but I couldn't help but ask why she wasn't sitting with her family. She told me she wasn't originally going to come but then decided to so she couldn't get seats together. I decided to be nice and ask if she wanted me to switch with her daughter but she explained that her grandson was old enough that he needed his own seat so there was no way for me to switch with them but she thanked me for offering and reached out her hand to me.
"I'm Dina."
"Jeff. Nice to meet you."
"You too, Jeff. And are you traveling alone tonight?"
"No, well sort of. I'm on business and I have a co-worker in a different row that I don't know very well so I'm basically alone."
"I see. Well Jeff you're going to love Miami. Lot of good looking young ladies!"
As she said that, she had a strange smile, almost as if she wanted to pry into my romantic situation and see if I'd bite.
I replied making it very clear. "That's what I hear, Dina. I am excited for the downtime I'll have when I'm not working so I can go out and try to have some fun. I don't have a girlfriend right now so I am a free man haha!"
Dina laughed and told me that was surprising. I blushed and went to turn back to my magazine as our quick banter faded when Dina kept the conversation going by asking where I'm staying. I pulled the address out of my pocket and showed her and as she pulled her glasses down from atop her head, she told me that her hotel was only a few miles away.
"Oh nice, so you guys will be pretty close."
"No Jeff, just me. My daughter Ellen and my grandson are visiting her boyfriend and I didn't want to intrude and I also like my space so I took a hotel room nearby."
"I see, makes sense."
The people around us seemed to be starting to close their eyes at this point. This was an evening flight and so the lights were dimmed and it was nice and quiet. I was never much of a plane sleeper which is why I brought my portable DVD player and a few movies. As I dug out the equipment, Dina turned back to her own seat but I felt her glances as I did my thing. I decided to get as comfy as my outfit would allow so I kicked off my shoes and summoned the attendant for a blanket. When she handed me one, Dina said good idea and asked the attendant for another blanket. She was told that unfortunately there were none left, since the plane was chilly and several people had already asked for them. I quickly offered Dina my blanket and she just as quickly told me thanks but no, although I could tell she didn't mean it. I insisted she take it, telling her I could deal with the cold.
"How about you let me share it with you so we can both keep warm?"
I shrugged as if to tell her she seriously doesn't have to let me share but ok, I'll humor her and agreed to share it. She pulled her half over her and I did the same as I started one of my movies. Dina asked what I was watching and I offered her one of my earbuds so she could watch too. This is the situation many guys would dream of being in on a plane, but not necessarily with a much older woman who was not exactly a former playmate. I must admit Dina's face was pleasant to look at it and I could almost feel the heat from her body as we shared my blanket. I imagined what she would look like under her sweater with what certainly seemed to be a set of heavy tits. I desperately wanted to see her cleavage, much like her daughter was showing off for all to see.
About 15 minutes into the movie, I shifted in my seat and brushed Dina's hand, not entirely sure why it was where it was.
