Traveling Young Man ( Tyler Wells & Jaclyn)

[Tyler Wells]

We head for the door to our room and Tyler stops to offer a morning kiss. Misses my mouth and I notice he’s not quite ready to go out.

“Wait a second Tyler.”

I set my bag on it’s wheels and go into the bathroom for a washcloth, come back out and wipe the corner of his mouth to get rid of the toothpaste.

“You need someone to dress you in the morning Tyler.” #Giggle

And off we go. The security line is so short that we breeze through and inside the terminal find our gate. Boarding is in 30 minutes so no reason to seek the airline lounge. All that’s open is a Cinnabon. We get in the short line.

“We’ll get a hot breakfast on the plane Tyler, after takeoff. So I just need a coffee. Oh and I’m going to stand because we’ll be sitting for around 5 hours and I need to stretch my legs as long as possible.”

At the front of the line, I order a large black coffee and step aside so he can order and pay. We pick up our stuff down the counter and head for the gate where we stand near the lane to board, realizing that first class is called first. Stand near him and touch his hand briefly with my free hand.

“I’m having a good time together, Tyler. Under difficult circumstances too I guess but that’s how traveling goes these days.”

Sip of my coffee.

Phoebe is so together. So with it. Just a fowad thinking, nice Woman. She pampers me. She Mothers me and She lets me stand on my own two feet. And she fucked me last night My first sexual experience. How lucky am I the young man thinks. To have it be with such a Dynamic, Beautiful Woman.

She is an answer to my lack of self-confidence prayers.

They sip coffee as they stand in line. Sleepy people looking at them. The lovely put-together Blonde Women and the college kid with the knapsack and wrinkled clothes.

As the Boarding Annoucemets start to roll in. The young man turns to Her. And asks.

" Phoebe. Would you ever consider giving me. Your contact information. I won't stalk You or anything. But. You know. I'd like to stay in touch "

The boy sips his coffee. Loving standing next to Her. She always smells so nice. His minds drifts back to an early morning image of Her going up and down on his cock with Her mouth as she sips Her coffee and looks at the Boarding Gate desk. Waiting to Board the Jet and sleep.

 

[Jaclyn]

The preboarding announcements start and he asks for my contact information.

“When we’re settled Tyler, sure.”

Not going to ditch my boarding pass on the airline app right now. First class is called and we shuffle through the line and then stroll down the bridge. Inside, I stow the handle to my luggage and boost the bac into the overhead.

“Take the window Tyler. I’ve seen this all before.”

Settle back in my seat and swipe away the airline app to select what I want to give him. Not Business, that has an address. Not Home, that too has an address. He gets Friend , phone and friend email, because both can be blocked. Hold my phone toward him.

“Give me a bump.”

Flight attendant is hovering. I decline so I can finish my Cinnabon coffee, better than what the plane has.

“So I don’t know if I said, I live in the Tampa area. Where in New York do you live Tyler?”

 

[Tyler Wells]

The preboarding announcements start and he asks for my contact information.

“When we’re settled Tyler, sure.”

Not going to ditch my boarding pass on the airline app right now. First class is called and we shuffle through the line and then stroll down the bridge. Inside, I stow the handle to my luggage and boost the bac into the overhead.

“Take the window Tyler. I’ve seen this all before.”

Settle back in my seat and swipe away the airline app to select what I want to give him. Not Business, that has an address. Not Home, that too has an address. He gets Friend , phone and friend email, because both can be blocked. Hold my phone toward him.

“Give me a bump.”

Flight attendant is hovering. I decline so I can finish my Cinnabon coffee, better than what the plane has.

“So I don’t know if I said, I live in the Tampa area. Where in New York do you live Tyler?”

"I live in Westchester area Pheobe. Not far from the City. "

The boy settles in, bumping his phone with Hers to get Her contact information.

" I've never flown in first class before Phoebe. Gosh, thank You. So much. "

When they offer him a small glass filled with Oranje Juice, the boy takes it. The Hostess says it's a mimosa. The boy looks at Phoebe.

" this has champagne. Right Phoebe? " when she nods Yes. The boy smiles

" well after last night. I'm celebrating. And so should You ".

With that, the boy turns around , saying to the airline hostess

" one more mimosa Maam. for My friend here "

Shy wink at Phoebe

 

[Jaclyn]

Okay, not what I needed but one won’t hurt. Plastic glasses because we’re still boarding and perhaps 20 minutes if not more from takeoff. Weather out the window looks fine. We touch plastic cups.

“Clink.” #Giggle

Take a sip.

“Okay, I don’t need more to drink until later this afternoon, after I make my sales presentation in San Fran. Okay please? Hopefully I’ll have something to celebrate too. So have you told your friends you’re arriving this morning? Landing 9:00 or so. I’ll need to change and go straight to my meeting. My rental had better be waiting!”

I pull up the rental car app and check status. Yes, they’ve caught the flight delay and are holding my medium size sedan for my arrival.

“Good, my rental is still on. Pays to be a Platinum member! And I plan to nap for part of the flight. Wake me if I snore.”

 

[Tyler Wells]

Okay, not what I needed but one won’t hurt. Plastic glasses because we’re still boarding and perhaps 20 minutes if not more from takeoff. Weather out the window looks fine. We touch plastic cups.

“Clink.” #Giggle

Take a sip.

“Okay, I don’t need more to drink until later this afternoon, after I make my sales presentation in San Fran. Okay please? Hopefully I’ll have something to celebrate too. So have you told your friends you’re arriving this morning? Landing 9:00 or so. I’ll need to change and go straight to my meeting. My rental had better be waiting!”

I pull up the rental car app and check status. Yes, they’ve caught the flight delay and are holding my medium size sedan for my arrival.

“Good, my rental is still on. Pays to be a Platinum member! And I plan to nap for part of the flight. Wake me if I snore.”

The boy smiles. As he gulps down his plastic cup of OJ and Champagne . ". Hey that tastes pretty good. I think I'll have another"

But when he asks for another the Airline Hostess smiles and says to him. " Young Man. I gave You one on the house. Without asking for ID. Let's leave it at one , okay. She looks at Phoebe and winks. "He's cute, is he Your little brother? ".

Phoebe does not find her sarcasm amusing. And retorts. " Is boarding finished. Will we be pulling away from the Gate soon? "

The boy settles back in his big reclining chair. Enjoying the amenities. He looks at Phoebe and smiles And Teases

" Hey Sis, Are You a member of the Mile High Club?" " Does that really exist ?"

Once again , Phoebe does not find references to being his Older Sister all that funny.

He chills a bit with her. Since She has been so nice and loving towards him.

"Yes, I texted my friends. They will try to get there for me. But they work. "

 

[Jaclyn]

I guess I’m still too sleepy to be at all in good humor this morning. Yes, I did have a lovely fuck last night but I’m still at least 3 hours short on rest and I’m very nervous about my presentation this morning. So I stay impassive through the exchanges and frown at Tyler’s silly attempt at morning humor. Mile high does not interest me. I try not to hate airplanes. He does tell about his friends and picking him up. Buckle up is called and we hand over our cups and other waste.

“We’ll figure it out Tyler. You’re riding with me if they don’t show, okay? But you may be waiting in the car or hospital waiting room while I make my sales pitch.”

We watch the safety briefing, pretty straight but it is 6 in the morning, and push back. I reach over and take his hand.

“Relax Tyler, everything’s fine. Please don’t push.”

 

[Tyler Wells]

I guess I’m still too sleepy to be at all in good humor this morning. Yes, I did have a lovely fuck last night but I’m still at least 3 hours short on rest and I’m very nervous about my presentation this morning. So I stay impassive through the exchanges and frown at Tyler’s silly attempt at morning humor. Mile high does not interest me. I try not to hate airplanes. He does tell about his friends and picking him up. Buckle up is called and we hand over our cups and other waste.

“We’ll figure it out Tyler. You’re riding with me if they don’t show, okay? But you may be waiting in the car or hospital waiting room while I make my sales pitch.”

We watch the safety briefing, pretty straight but it is 6 in the morning, and push back. I reach over and take his hand.

“Relax Tyler, everything’s fine. Please don’t push.”

Holding Her Hand.

Listening to Her. Knowing what we did last night . Together

" I'm not trying to push Phoebe. I just don't want to say goodbye. I really like You."

The boy squeezes Her hand and even though it is early. They roll to the Tarmac and they sit. And wait. And wait some more

He looks over at Phoebe. And though She is holding his hand. Her eyes are closed and Her breathing indicates She is in a drift slumber. As he looks at Her ,He remembers earlier this morning. And being on top of He, and in Her. The movements. The feel. Her eyes. Her lips. Her breath. The softness of her flesh . The hardness of Her nipples as he sucked them . Mostly he thinks about the way She looked at him as She sucked his cock. Her beautiful face and Her confident way of showing him She knew exactly what She was doing.

The boy grows a bit erect as he remembers. And he closes his eyes

The next thing he knows they are racing down a runway. Bumping fast. And taking off. He looks out the Window and sees a highway with cars and then miles of green fields scatterred with homes and farms. He came into Illinois yesterday a Virgin boy.

He was leaving Illinois with his Virgin label gone and his confidence with Women at an all time high .

 

[Jaclyn]

I come awake as we start takeoff and keep my eyes closed until we smooth out. Squeeze his hand.

“And I really like you too Tyler. We’re together this trip until you go off to visit your friends. After that, friends at a distance, okay please? I don’t do relationships. Just not how I roll these days.”

Announcement that the WiFi is available. I take out my phone and go through the rigmarole to connect and get internet and text message access. Send a quick note to my contact at the hospital. They’re still not at work so just keeping them informed. And next the flight attendant is offering drinks. I order coffee.

 

[Tyler Wells]

I come awake as we start takeoff and keep my eyes closed until we smooth out. Squeeze his hand.

“And I really like you too Tyler. We’re together this trip until you go off to visit your friends. After that, friends at a distance, okay please? I don’t do relationships. Just not how I roll these days.”

Announcement that the WiFi is available. I take out my phone and go through the rigmarole to connect and get internet and text message access. Send a quick note to my contact at the hospital. They’re still not at work so just keeping them informed. And next the flight attendant is offering drinks. I order coffee.

Phoebe orders coffee. Not a lot of words are spoken between them. He gets it. No relationship. Just txt /emails and IM buddies. The young man just stares out the window. Looking at clouds. The plane is too high up to see really any land mass or ground. When he does catch the occasional glimpse. It's a green patch of land. Almost in a perfect square or rectangle. The fight Tracker says they are somewhere around Omaha.

They pamper You so much in first class. A pre-meal snack. Fruit. Then a main meal with more fruit. The egg and sausage on a Croissant he had was quite good. But he as hungry. All that sex. He smiles to himself. Thinking

" You did it Buddy". . You got laid. And She is sitting no more than 3 feet from Him.

The boy looks at the flight attendant. With his new found confidence. She is older than Phoebe. Quite pretty. He wonders if She fucks. She must.

He smiles. And orders a Coke. Just to bring Her over. To look at Her. Smell Her perfume. Maybe Piss Phoebe off with another crack about being an older Sister.

Finally he says. Rather whispers after 10 more minutes of silence between him & Pheobe

" Phoebe. How old were You when You lost Your viginity. And to whom did You lose it to ? "

 

[Jaclyn]

His question is earnest and honest. Does he get the long or medium or short or no answer. Let’s see how he takes the short, harsh answer. I reach over and take his hand and lean close.

“I was thirteen when I had my first abortion. My uncle provided the sperm over the summer. I don’t know which time he did it got me pregnant. It was an ectopic pregnancy, meaning it wasn’t viable and would have killed me. I nearly died because my family wanted to force me to carry the baby to term and raise it because they were all about their church. I fainted in school and they rushed me to the hospital with blood running down my legs. My uncle did it again the next summer and this time I told the school counselor and she made some magic happen and I ended up with my second abortion and living in foster care until I was old enough to live on my own. I no longer have ovaries because of my uncle. I learned sex could be fun from a married college psychology professor. Not love, just gentle sex and fun for me and he taught me how to make it fun for him too. May he rest in peace.”

Okay, harsh medium version. What will this kid who loved me very nice for a first timer think of all this? Used goods?

 

[Tyler Wells]

His question is earnest and honest. Does he get the long or medium or short or no answer. Let’s see how he takes the short, harsh answer. I reach over and take his hand and lean close.

“I was thirteen when I had my first abortion. My uncle provided the sperm over the summer. I don’t know which time he did it got me pregnant. It was an ectopic pregnancy, meaning it wasn’t viable and would have killed me. I nearly died because my family wanted to force me to carry the baby to term and raise it because they were all about their church. I fainted in school and they rushed me to the hospital with blood running down my legs. My uncle did it again the next summer and this time I told the school counselor and she made some magic happen and I ended up with my second abortion and living in foster care until I was old enough to live on my own. I no longer have ovaries because of my uncle. I learned sex could be fun from a married college psychology professor. Not love, just gentle sex and fun for me and he taught me how to make it fun for him too. May he rest in peace.”

Okay, harsh medium version. What will this kid who loved me very nice for a first timer think of all this? Used goods?

The boy sat there at 35,000 feet and listened to Phoebe.

In a way. He had wished he had never asked his question. Or. He wished She had just lied in her answer and said something like She lost her virginity at 16 in the back seat of a car to an older boy one summer who was going to college. That would have sufficed.

As Her answer ended the young man sat in silence thinking of what to say next. Finally he found the words

" I'm sorry things happened to You Pheobe. The way they did the first time. It shouldn't be like that. It should be like what You did for me this morning. Nice and loving. That's what it should be like "

". You know. I may live to be 100. And after today I may never see You again. Aside from the occasional IM or text. We may never even speak again. But as long as I live, I'll never forget You. Or Your name, and what we did this morning. That's how first times should be."

"Maybe someday I'll be lucky enough to meet a girl and fall in love and get married. And guess what? On my wedding night, I'll think of You for just a moment. I guarantee it ".

" And I will always be grateful to You."

The boy looked into Her Angelic face and beautiful eyes "

"Always"

He sat in silence fir the longest time. Looking out the Window. He looked at the Rocky Mountains for the first time.

There were a lot of first's in his life today

 

[Jaclyn]

I hold his hand as he talks out his feelings. Vague thought how nice it would be were he 10 years older. I wonder if he likes to cruise? I have plenty of money, finances aren’t the issue. But what do we have beyond sex? We shall see.

“I’m grateful to you Tyler. You caught me at a difficult moment last night and were kind about everything we did. Look, I try not to have a future, it’s more fun that way. Oh, I have business plans because I work for a living. I like this job because I meet new people all the time and occasionally like last night I find a new friend. Not often. Most people are only about using other people. You’re different. Where we go together though I don’t know. Let’s not push, okay please? And now I need to nap so I don’t fuck up my presentation.”

I recline my seat and seat yet still hold his hand. Another hour plus of flight and a snooze is essential.

 

[Tyler Wells]

I hold his hand as he talks out his feelings. Vague thought how nice it would be were he 10 years older. I wonder if he likes to cruise? I have plenty of money, finances aren’t the issue. But what do we have beyond sex? We shall see.

“I’m grateful to you Tyler. You caught me at a difficult moment last night and were kind about everything we did. Look, I try not to have a future, it’s more fun that way. Oh, I have business plans because I work for a living. I like this job because I meet new people all the time and occasionally like last night I find a new friend. Not often. Most people are only about using other people. You’re different. Where we go together though I don’t know. Let’s not push, okay please? And now I need to nap so I don’t fuck up my presentation.”

I recline my seat and seat yet still hold his hand. Another hour plus of flight and a snooze is essential.

Letting Phoebe sleep. Or nap. The miles pass away. Blue skies emerging. A new day on the West Coast.

Out of nowhere the first class cabin comes to life. Airline hostess collect the glasses and Newspapers and every other item.

Pheobe awakes with the bustle. Looking somewhat annoyed. She mumbles about needing more nap time. She offers me a weak smile as She checks Her phone. She heads to the Restroom and disappears for a stretch. With a make-up bag. The plane is on a slow descend path.

Phoebe re-appears and She looks brand new. Refreshed with a focused Game face on.

The next thing We know we feel the " Bump, Bump Bump" of the touchdown. The brakes and swoosh of air indicating another safe landing . " Welcome to San Fransisco the Hostess announces. " The local time is " 8: 15 am"

Phoebe mentions something about first class having de-planeing and luggage carousel privleges. " I hope my luggage is there" I say.

She whispers to me. " You did a good job earlier this morning keeping up with me. Make sure You keep up with me now "

And with that I'm following her lovely Blue-Jean clad ass and carry-on roller. Her blonde Hair blowing slightly on the jet bridge exit. The panting boy puppy-dog behind Her. Remembering looking at that beautiful naked ass when she headed to the bathroom this morning. I was half asleep but I looked.

But Phoebe was on a mission. Today was all business. I was a tag along. Knowing my friends had texted and suggested I get a cab to their condo development.

But I wanted to be a tag along. I wanted to spend as much time as I could with Her.

 

[Jaclyn]

We lead the rush down the terminal and I find the little convenience hotel where I intend to change.

“Okay, I’m going in here to change for my meeting. You go to baggage claim and find your back. I’m going to change and we’ll meet at the stairs down to baggage claim level. You’ve got my contact, text me if something changes.”


I kiss him on the mouth quickly and turn into the convenience hotel. Quick transaction for a changing room. Bathroom with no bed and room to handle suitcases. Hang my dress and check for wrinkles. Good, no need to press or steam it. Pays to buy quality. Heels and I’m ready. Head back out and hand off the room key and head down the stairs to look for Tyler. Don’t see him but my rental car is right here. Send him a text.

### At the rental car booth right across from the stair!

The line is short and I have the car key in hand when I turn to look for him.

 

[Tyler Wells]

We lead the rush down the terminal and I find the little convenience hotel where I intend to change.

“Okay, I’m going in here to change for my meeting. You go to baggage claim and find your back. I’m going to change and we’ll meet at the stairs down to baggage claim level. You’ve got my contact, text me if something changes.”

View attachment 20807
I kiss him on the mouth quickly and turn into the convenience hotel. Quick transaction for a changing room. Bathroom with no bed and room to handle suitcases. Hang my dress and check for wrinkles. Good, no need to press or steam it. Pays to buy quality. Heels and I’m ready. Head back out and hand off the room key and head down the stairs to look for Tyler. Don’t see him but my rental car is right here. Send him a text.



The line is short and I have the car key in hand when I turn to look for him.

Like Phoebe had said. My luggage came right out. The boy was amazed at his good fortune. It pays to fly First Class

A quick trip down the escalator. And there She was. Wow. She looked stunning !

With a duffle bag on rollers and his back pack over his shoulder. He walked up to the Woman who showed him a whole Other World. The key in Her hand

Hey Phoebe. You look fantastic. You look like You are ready to take in the world.

She did have Her game face on.

She smiled at the boy and gave the same command as before when they got off the plane

"Let's Go, Keep Up"

He had to smile to himself as he followed Her like a pack-mule out to the Rental Car Garage .

He was always panting around Her. For some odd reason.

 

[Jaclyn]

The late model A4 was waiting in space 3. The trunk pops as I punch the key. My roller goes in and my carryon with my laptop go in the back seat. In the driver’s seat, I connect my phone to CarPlay and check the time to my destination.

“Sorry Tyler, I can drop you somewhere along my route because that’s all I have time for or you can wait in the hospital waiting room while I have my meeting. Could be 3 or 4 hours and I may have to go to lunch with my customers and I’m sorry but that means without you.”

He can see the route with the major cross streets. I put the car in gear and quickly get us onto the 101 headed for I-280 and California Pacific Medical Center.

”If you want to get off along the way, less than 20 minutes to decide.”

 

[Tyler Wells]

View attachment 20956The late model A4 was waiting in space 3. The trunk pops as I punch the key. My roller goes in and my carryon with my laptop go in the back seat. In the driver’s seat, I connect my phone to CarPlay and check the time to my destination.

“Sorry Tyler, I can drop you somewhere along my route because that’s all I have time for or you can wait in the hospital waiting room while I have my meeting. Could be 3 or 4 hours and I may have to go to lunch with my customers and I’m sorry but that means without you.”

He can see the route with the major cross streets. I put the car in gear and quickly get us onto the 101 headed for I-280 and California Pacific Medical Center.

”If you want to get off along the way, less than 20 minutes to decide.”

The young man looked at Her and he realized for the first time in that almost 17 hour period that there time had come to an end.

You can drop me off Phoebe at Your appointment stop. I'll get an Uber from there to my friends condo/apartment.

"It's been fun "

The boy reaches over and touches her long lovely thigh. Covered by Her Business Skirt.

"You were my first. And I'll never forget You."

" Thank You"

 

[Jaclyn]

“Thank you Tyler! I had a wonderful time!”

I pull into the parking garage at the hospital and we get out. I carry my purse and carryon bag with my laptop and he brings his luggage as we descend in the elevator. I take his arm as we enter the main lobby where I stop and set down my carryon. Turn and put one arm around his neck.

“One kiss for the road, Tyler. Text me if you want to get together out here. Or when you get home and I’ll text you then too just to make sure we both made it home safe. You’re sweet!”

We share our lips and a little bit of tongue and I let him go.

“Can’t ruin my makeup, as much as I want to. Travel safe, Tyler.”

I head for the reception desk and am directed to the staff elevator. My contact greets me as I step off and I use the ladies room and we go to the conference room. And I make the huge sale. And we go to lunch. I check my phone, hoping a little bit that Tyler texts me and hoping he doesn’t because he’s cute and I was getting attached.