Paulina

Paulina on the Train

Continuing the adventures of Paulina, the cross-dressing teen.

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More stories featuring Paulina: "Making Money With Mr. Jack". She is a little younger in that one. "Paulina Gives Her Virginity". Her first oral and anal experiences with a man. "Getting the Dishwasher Fixed". Set a few weeks after giving her virginity. "Paulina is Heard Masturbating". Her stepdad and friends here her get off.

I awoke Saturday morning to a still dark sky. Dawn was still an hour or so away. I went to the kitchen for some Coke. It took me a few minutes to feel fully awake. I went back to my room and got dressed, picking out jeans that made my ass look extra cute, as well as a tight pink girl's sleeveless polo. The pink lipstick and nail polish I got with Beth matched it well. Navy blue Keds, my sunglasses and pink Saints ball cap rounded out my outfit. I went to the bathroom, then grabbed my purse and bag and headed for the door. Before leaving, I taped a note to my door that said "Please feed my turtle." I knew my stepdad would do it, as he fed the fish in the aquarium every day. He wouldn't let my little turtle go hungry while I was gone.

The walk down the street was quiet and peaceful. The sun wasn't fully up yet, and the birds were just starting to wake up and sing. If it wasn't so early in the morning, I'd love this time of day, but I never was a morning person.

The bus was right on time at 5:55 AM. Only a few people were on the bus that early on a Saturday morning. The bus driver looked half awake like everyone else but gave me a cheerful `good morning' when I got on. I gave him a sweet smile and reply.

The ride was quiet, with only a few more people getting on the bus before heading across the river. The trip over the Greater New Orleans Bridge (It was not called The Crescent City Connection yet) was always nice. I loved seeing the river with the ships traveling up and down its muddy waters. I enjoyed riding the ferry as well.

The closest stop to the Union Passenger Terminal was the first one off the elevated expressway that led off the bridge. It was a quick two block walk from the bus stop.

Entering the station, I saw several people in the waiting area with their luggage. I walked up to the big polished limestone counter to buy my ticket.

"May I help you?" The Amtrak ticket agent asked.

"Yes, sir. Round trip to Picayune please" I answered sweetly as I handed him cash.

"When are you returning, young lady?"

"Sunday evening, sir."

"Traveling by yourself, are you?"

"Yes, sir. I'm going see my aunt and uncle for the weekend."

"Well, you have a good time, miss. Train departs at seven o'clock promptly" he said with a smile as he handed me the tickets.

"I sure will!" I gave him a sweet smile and wink before I went to the pay phones. I knew he was watching me walk away, so I put a little swish in my hips for him to enjoy.

It was 6:35 and I needed to call Bunny before I got on the train to let them know I was coming.

"'Ellow?"

"Hi Bunny, it's me. I'm getting on the train in a few minutes. The ticket guy said `the train departs at seven o'clock promptly'. I imitated his voice as best I could.

"Haw! Yer funny, girl! Me an' Jimmy'll be waitin' fer ya when ya git off. You enjoy that ride darlin', and we'll see ya soon."

"Okay Bunny, I will. Can't wait to see y'all!"

"Us, too honey."

We both hung up anticipating the fun we were going to have.

The ride on the train was very pleasant. Crossing Lake Pontchartrain early in the morning was very pretty. I decided to get breakfast since the dining car was open. I didn't know that when dining on a train, you shared a table with others instead of having your own. The host gave me a wink as he seated me at a table with two businessmen. One was in his late 40s or early 50s, and the other in his late 30s. Both were in good shape and very handsome and looked wonderful in their stylish business suits. I couldn't resist turning on the charm.

"Good morning, gentlemen" I said with my prettiest smile and sweetest, sugary voice.

They both stood up before I sat. "Good morning, young lady. How are you today?" the older one asked.

"I'm great, thanks. How are y'all doing?"

"Better now" the younger one answered. I gave him a sweet smile.

"Might I ask where such a lovely young lady is traveling to by herself today?" The older one asked. He reminded me of Jack. I felt my resistance to his charm begin to melt away. Had to resist...

"I'm going to see my...aunt and uncle in Picayune. It's been so long since I've been able to see them. It's going to be so fun to see the country. They even said they were going to get me some nice boots. I don't have any yet." I held my leg out from the table for them to see.

"I'm sure they're gonna be lovely on you, miss" he replied nicely.

"Oh, I hope so. I want some pretty cowboy boots, with silver tips and high heels!" I giggled deliberately when I said this.

"Those do sound mighty fine! So, what's your name, miss?" the younger guy asked. "I'm John Smith, and this is Jackson White."

"But you can call me Jack" The older one smiled.

Omygod, another handsome Jack! What were the odds?

"Nice to meet you, gentlemen. I'm Paulina." I held my hand out in a ladylike manner. They both took it gently. "Traveling for work, I assume?"

"Yes, ma'am. Going to Hattiesburg. We have some business at the university there Monday, but they invited us to see their football game and enjoy the weekend there." John answered.

"Oh. I guess I'll be getting off the train before you two" I said with a little pout. "Would you mind if...if I sat with y'all until my stop at Picayune? I saw some younger guys staring at me. I don't like young guys like that. They...look at me kind of creepy sometimes and make me feel uncomfortable. I prefer spending time with older gentlemen like you. I mean, if that's okay. I don't want to intrude." I said with sweet, doe eyes.

"Sure you can! No one's going to look at you like that if you're with us" John said with a big smile.

"But of course, Paulina. We can get a table in the lounge car and you can sit between us. You'll be nice and safe."

"Oh, thank you, Mr. Jack! I really appreciate it!" I had to stop myself from getting up and giving him a big hug.

The waiter brought our food and we talked as we ate. I was on my best ladylike behavior and truly enjoyed giving my attention to these two men. They were clearly attracted to me and were definitely enjoying my flirtation with them. We were all thinking to ourselves how much fun it could be if we were alone.

When the check came, I felt a hand on mine as I moved to open my purse.

"I've got the check, Paulina. Don't you worry about it" John said with a smile.

"Are you sure? I have money. I don't want y'all to think I'm a mooch or anything" I said with a pout.

"Nonsense. You're a wonderful young lady and we're happy to get your breakfast." Jack added.

"Thank you, both of you. That's very nice. I appreciate it." I said sincerely.

Standing up, John offered his hand. "Shall we? The lounge car is at the end of the train."

"Lead the way." I took his hand as I gave Jack a sweet smile.

We passed through a couple of coaches before arriving at the lounge car. It was an observation lounge, with wraparound windows at the end. They offered me a seat in between them. The chairs were comfortable and swiveled. As they sat, they pulled theirs closer to mine. I smiled as they did so. A little cocktail table sat in front of us.

In the early 80s, people often had cocktails at breakfast while traveling, and they could be ordered from the dining car. A waiter appeared to take our order. He was an older black gentleman with a nice smile. Ironically, his name tag said "George".

"G'd Mornin' suh, miss. Can I get yuh anything?" he asked Jack.

"Three Mimosas. And make sure it's a good bubbly."

The waiter looked at him, then at me, then back at him.

"Three, suh?"

"Yes, George, three. She's with us." Jack handed him a twenty dollar bill.

"Yes suh, if you say so, suh." George shook his head slightly as he walked off with our order.

"Mr. Jack—"

"Please just call me Jack" he smiled.

"Okay, m- Jack. I've never had a Mimosa. What is it? Does it taste like the flower smells?"

"Have you had Champagne before, Paulina?"

"No, but I've had red wine. I like it."

The two men gave each other a pleased look.

"It's like bubbly white wine, with orange juice."

"Oh, I love orange! It sounds very good."

"It usually is. It's a morning drink, so that's why we're having one" John added.

"I can't wait to try it then."

George returned a few minutes later with a tray holding three champagne flutes. He deftly served our drinks despite the rhythm and wobble of the train as it moved. He had obviously done this for years.

"Heah you are, young lady" he said as he handed me a flute.

I gave him a sweet smile. "Thank you, Mr. George." He smiled back.

"Suh," he spoke to Jack, "Give a wave if yuh need a refill or anythin'. Ah'll be right ovuh."

"Thank you, George. That'll be all for now."

Taking his cue, George went back behind the bar and into the little attached storeroom to do whatever he was doing before.

"Cheers" Jack said as he and John lifted their glasses, waiting for me.

"Salute!" I said as I clinked each of their flutes with mine.

We each took a large sip before continuing our conversation.

"So, Paulina, how old are you?" John asked.

I gave them both a coy smile before answering sweetly. "Old enough."

Jack raised an eyebrow upon hearing this. John's smile got a little bigger.

"I assume you live in New Orleans?" Jack asked.

"Yes, born and raised there. I love it."

"Me, too. My family's lived in the Garden District for over a hundred years now."

"Oooo, really?" I replied excitedly. "I love the architecture there. Those old houses are beautiful. I've always wanted to go in one and look, but never knew anyone who lived over there."

"Well, maybe we could arrange something. John, don't you have an associate who lives in the district who travels a lot?"

"Yes, I do. I house sit for him and his family sometimes. Maybe you could...come see it some time? We can give you a tour."

"Yes, I'd love that!" Y'all are so nice!" I gave them my sweetest smile.

I hadn't noticed that I was almost finished my Mimosa and was starting to feel and sound a little giddy. The guys noticed and thought I could use another. Jack took my empty flute and swapped it with his half full one.

He raised his hand for a moment before George appeared from behind the bar and walked over.

"Another round, George."

"Three suh?" he looked at the half empty flute I was holding.

To everyone's surprise, I knocked the rest back in one gulp and set the empty flute on the little drink table in front of us with a big smile.

"Yes George, three."

"Uh, yes suh. Comin' up."

I giggled as George took the empty flutes away.

We talked some more and drank more. I got more flirty and giddier as we did. I also got more touchy-feely like I always did when I was around people I was attracted to. The Mimosas just amplified it.

Sitting in between the two men, my hands migrated from the chair arms to their knees, to their thighs. I unconsciously patted and rubbed them. Every now and then one of them would adjust himself, making the erection in their pants obvious.

Their hands roamed, too. The top of my hands, my arms, an occasional touch on my shoulders, or a stroke of my hair. I was in heaven from being touched so much. I had a naughty thought and wondered how good it would feel to take my clothes off right there and let them touch me all over. Of course it was just a tipsy fantasy, but it was fun to think about.

I was feeling good after the second Mimosa, and the flirty touching and feeling that was going on was getting me hot. I knew there wasn't much time until we reached Picayune. Excited and tipsy, I summoned my naughty courage and took a chance. I was going to have some fun before the ride was over.

"M- Jack? Can you show me where the bathroom is?" I asked sweetly.

"Sure Paulina. It's around that first corner."

I didn't think he took the hint, so I asked again.

"Could you, um, walk me over there? I think my balance is a little off" I said with a giggle. It actually was, after two Mimosas.

"Of course. Here, take my hand." He pulled me up gently as I took it.

I gave John a little wink as we walked to the "Water closet" as the sign above the door said.

As I was about to go in, I squeezed Jack's hand.

"Jack..." I said in a tipsy, sultry voice, "I think I need some help in here. Can you come in with me?" I gave him sweet eyes.

"Oh – of course" he said with a knowing smile. I think he figured out what I had planned.

As soon as the door was shut, I reached out and caressed the erection in is pants. It was hard and thick. The little room did not have much space, so he was directly in front of me when I sat on the toilet.

"Jack, I want to suck your big daddy dick. May I please?" I asked in my sugary sweet voice while giving him sweet eyes.

"I'd really like that. Open those pretty lips, Paulina" he said as he took his rock hard cock out. It was uncut, about the size of Bernard's, maybe a little smaller. Perfect to swallow.

Using a soft but firm grip, I stroked his cock a few times to get it as hard as possible. As I stroked him, I saw a drop of pre-cum ooze out of his urethra. I scooped it up with the tip of my pinky and stared into his eyes as I brought it to my tongue, which was out as far as I could extend it. I rubbed the drop onto the tip of my tongue, covering as much as possible. It was slightly saltier that Bernard's cum was, but that may have been because it was just pre-cum.

Turning my attention back to his waiting cock, I began by pulling back his foreskin and licking the underside of the head before moving down the shaft. I maneuvered one of my hands into his underwear so I could fondle his balls as I sucked. He let out an approving `mmmm'.

I took a deep breath and then swallowed his dick as I exhaled through my nose. After a few moments, his balls were against my chin and his pubic hair was tickling my nose. His cock was as far down my throat as I could take it.

"Mmm...Paulina...that's good" he said in a smooth voice as I deepthroated him. He ran his fingers through my hair and occasionally pulled it as I slowly sucked and swallowed his dick.

I increased the pace of my rhythm. It wasn't long before I felt him tense up and I knew he was about to cum.

"Ohh...I'm...I'm cumming...AHHHHH!!!" He pulled my hair tightly, pushing his cock down my throat. I then felt the surge of hot semen fill it up. I swallowed it down as fast as I could, not wanting to spill a drop.

After a few moments of heavy breathing, jack calmed down enough to speak.

"Oh my god, Paulina, that was amazing! One of the best blowjobs I've ever had. You've got some real talent there!" he exclaimed after cumming in my mouth.

I gave the head a final little kiss before putting it back in his underwear and zipping him back up.

"I'm so glad you liked it. I just love doing that. Do, um, you think John would like one, too?" I said with a tipsy giggle.

"He sure as hell would. You stay put and I'll go grab him. Sit tight." He gave me a wink.

I undid my pants and peed while I waited. It wasn't long before there was a light knock on the door. I pulled up my pants and buttoned up.

"Paulina, it's me, John." He said quietly.

"Come in" I said as I unlocked the door. He stepped in quickly and locked it behind him.

Not wasting any time, I fondled his crotch with one hand and unzipped him with the other.

"Wow, Jack wasn't kidding. You are hot to suck some dick, aren't you?"

"Yes. I love doing it. I love the taste of cum and how it feels to swallow a big hot load. Will you give me one? Please?" I gave him doe eyes, which of course he didn't resist.

"Hell yeah! Swallow my dick, girl!"

His cock was a little bigger than Jack's, which wasn't small. As I sucked and licked it, I couldn't help but think that it would feel good stretching my little ass open. But there really wasn't time for that, nor did I have any idea what either of the two of them would think if they found out I was really a girly boy.

It only took a few minutes of my now expert efforts to make John cum. He gripped and pulled my hair as he shuttered and spewed in my mouth. I swallowed four or five times before his stream of cum finished. He was a little louder than Jack when he came, which made me nervous for a moment. I didn't George or anyone else to hear us.

"Holy fuck! That was incredible, girl! You sure know how to sick a dick good!"

I wiped my lips with a finger before answering with a giggle. "Thanks. I really like doing it. Your cum tastes good!"

"I know it does." With that, he leaned down and kissed me deeply. I was surprised, as I had heard that most guys wouldn't kiss a girl after she had their dick or their cum in her mouth. It was some weird straight guy hang-up. But John didn't seem to have a problem with it.

"So, um, we should get back. That old porter is already suspicious, I think. Jack might slip him some more cash to keep quiet."

That struck me as funny for some reason, like it should be a scene in a movie or something. I giggled as I brought my fingers to my lips.

"Shhh, it'll be our secret!" I took his hand and we walked back to the end of the car.

I carefully followed John back to our seats, as my balance was not quite perfect. A fresh Mimosa was waiting for both of us. As we passed the bar, George gave me an inquiring look, as if to ask `are you okay?' I smiled and gave him a little affirmative nod as I passed. He smiled in return.

Jack stood as we approached our seats.

"You feeling okay Paulina? Would you like another Mimosa?" he gave me a wink.

"I feel fantastic. And yes, another would taste great!" he handed me one of the full flutes.

"Salute!" We clinked glasses before taking a long sip.

"So Paulina, would you really like to see my friend's house in the Garden District? It won't be hard to set up" John said with a smile.

"Yes, that would be great! Could y'all both...show it to me? I'm really enjoying spending time with y'all" I said with a giggle.

"Of course we can. We might be able to make a `business lunch' out of it. What do you think, John?" Jack asked.

"You're the boss, Jack. It'll be whatever you say it is."

"Hmm..." I giggled some more. "Do you think...maybe there might be a nice present or something waiting there for me? I'd love a nice present. Older gentlemen like you two have great...taste!" I sucked the tip of my finger exaggeratedly. Both men laughed.

"Of course, young lady. Maybe, if I had your address, you might get a nice present sooner. Maybe you have a phone number we could call you at as well?" Jack asked with a knowing smile.

"I sure do. Can I have your cards? I know businessmen always have a lot of cards with them."

"Here you are. Keep these and write your info on the back of this one for us." John handed me their cards, along with his very nice fountain pen.

I had to take my time and concentrate on writing my prettiest, neatest script. When I was happy with the results, I handed it back to him. I drew a little diamond after my phone number. After all, I was royalty.

"Ahh, an Algiers girl" Jack said with a smile.

"Yes! How'd you know?" I giggled.

"That 392- number. Only on the Westbank, in Algiers."

"You're right!" I raised my flute up, which they both clinked.

We chatted some more until the conductor called for the Picayune stop.

I used my most ladylike voice. "Well, gentlemen, thank you so much for letting me keep you company. I really enjoyed spending time with you. I hope to hear from you soon." I couldn't help but giggle after speaking. I was still pretty tipsy from the third Mimosa.

"The pleasure was all ours, Paulina. You're a wonderful and...talented young lady. We look forward to seeing you again. I think showing you that nice, old, uptown house will be a lot of fun." Jack replied with a sweet smile.

"Yes, I think we will really enjoy showing it to you" John added.

"Can you please walk me back to my seat so I can get my bag?"

"Yes, of course."

I held out my hand, which John took and gently pulled me up to my feet. Jack offered me his elbow. As we passed the bar, George was looking our way. I gave him a little wave.

"Thank you, Mr. George. The Mimosas were delicious. You have a wonderful day!" I blew him a little kiss.

"Thank ya, young lady. You do as well" he replied sweetly.

"Yes, thank you George. I appreciate your help this morning." Jack gave him a nod. He gave Jack a knowing look in return.

As we got to my seat, John reached up and got my bag down from the overhead storage for me. They walked me to the vestibule as the train slowed to a stop.

"This is your stop, Paulina. We'll be in touch real soon. It'll be nice to see you again" Jack said sweetly.

"Oh, I really hope so. Thank you again for being so nice to me. I really appreciate it."

"No, no, the pleasure was all ours. You turned it into a wonderful morning." John said with a wink.

The porter lowered the steps and set out the stool. Before stepping down, I gave Jack a big hug, along with a long kiss on his lips.

"Thank, I really enjoyed it. I hope we can do it again some time" I whispered.

"You're very welcome. So do I."

I turned to John and pulled him into a big hug as well. We kissed again, but without any tongue this time.

"We're gonna call you. I know I am! Maybe I'll get to see this tight little ass, or more..." he gave my ass a little squeeze."

"Hmm, maybe so. A nice present might help." I said with a wink.

"I give good presents!" he said with a chuckle.

"I bet you do" I replied with a giggle.

"Miss, may I?" the porter asked as he held out his hand.

"Yes, please." I handed him my bag. He set it on the ground and offered his hand again. I took it in mine and held it tight as he guided me down the steps. I turned one more time and gave Jack and John another wave. "Goodbye, gentlemen. Thanks again!" I blew them a kiss before turning back and concentrating on walking down the steps.

"Thank you, sir." I smiled at the porter and went to open my purse so I could tip him.

"No need, miss. The gentleman in the gray suit already took care of me. But thank you."

Bag in hand, I walked into the station waiting area with a swish of my hips for all the men watching to enjoy.

Back on the train, Jack and John were back in the lounge car discussing the recent fun they had with me.

"Man, I need a stiff one after that. I mean another stiff one!" John said with a big laugh. Jack laughed as well.

"Yeah you right, Jonny boy. George!" he waved his hand.

George walked over. "Suh?"

"Two Old Fashions, George. Make them doubles, with some good Bourbon" Jack ordered.

"Yes suh." He went back to the bar to make the drinks.

He returned with the two drinks and set them down. Before walking away, Jack asked him a question.

"George, what did you think of our young lady guest?"

"Nice girl, suh. Reminded me of the girls ah saw in Italy durin' thuh war."

"Yes, she sure is a little Italian beauty!" John added.

"Sumthin' diff'rent `bout that one, suh. Cain't put mah finger on it, though. Special young lady though, ah can tell that. You gents let me know if y'all need refills." With that he returned to the bar.

"Thank you, George."

Jack looked thoughtful for a minute.

"You know what, John? I think he's right. Somethin' was different about her. But with that sweet mouth of hers, it don't matter! I mean, she gives better head than my wife!"

"Better than any chick I've been with, either. Well, maybe not that creole girl Monique with those lips, but close!"

He and John gave each other a big "Cheers".

"So, Boss, what're we gonna get her?" John asked.

"I'd love to see that one in some lingerie, but she might be a little young for that. Maybe something for that pretty hair of hers?"

"Good idea. Maybe some gold clips or barrettes or something? She looks like she likes some gold, with that crown and bracelet."

"Excellent. I'll have Joyce at the office order her something when we get back."

"Say, Boss, how old do think she really was? I'm sure she's still in high school. I know she's eighteen yet."

"I think you're right, there Jonny. To be honest, she looks the same age as my little Julie, and she's sixteen."

"God, I hope so." He looked worried. "Good thing sixteen is legal, huh?"

"Sure is." he replied with his own relieved expression.

"Anyway, here's to seein' her again!"

Both men raised their glasses again and enjoyed the rest of the trip to Hattiesburg.