First Time Express Part 6: Cinco

When we entered this railroad car naked, I thought my night was ended, for the most part. This railroad car had a long, narrow hallway, and on the side of it were what looked like prison cells, complete with iron bars.

"Ms. Hoyle," I asked, "is this the lockup area?"

I didn't like that she answered me by sliding open one of the cells.

"Just step in, Mr. Hanover. This might take a few minutes, or this could be your place until we let you off tomorrow morning."

"Please, Ms. Hoyle, I don't believe that I've broken any of your rules."

She motioned me to get in, and so I stepped in and allowed her to close the door.

"You're going to meet an officer here. She is going to give you a test. If you pass, you can proceed."

She then went further down the hall, and so I stuck my head through the bars as much as I could to see where she was going.

I noticed that the other ladies, including Ace E, Two-Lina, Dr. Treyla, and Fouranny were still there.

"Don't worry," Ace E whispered, "this is all part of the fun."

"This doesn't feel like fun," I whispered back, but was still loud.

"Trust us," said Treyla, "remember how it didn't seem like fun to hold it in, but it turned out to be something great?"

"Yeah, and I kind of got in trouble there, and the car before that, and the car after you, doctor!"

"She's not keeping you in lockup," said Fouranny.

"I feel like I'm locked up here."

"Trust us," Two-Lina said, "if she was going to do that, she would have given you back your clothes!"

Then there was a voice from down the hallway. "Gals, you're needed down here!"

The four of them ran off toward the direction of Hoyle's voice. For a few minutes, I could hear them talking, and in some cases, it sounded like some were begging.

After a while, I heard a voice I didn't recognize, and she cried out: "Quiet, lassies, we'll settle this once and for all! I'm gonna get him."

I heard the sound of footsteps approaching the cell door. The door opened, and there was a woman whom I didn't recognize. She had very fiery red short hair, and she was wearing a blue police uniform with a short skirt. She also wore some stockings with garters, and high-heeled boots that went up to her knees.

"Mr. Hanover, I'm gonna need you to be comin' with me, if you please."

In spite of the girls trying to calm me earlier, I felt like I was in a lot of trouble.

As I stepped to the door, she held up her hand to signal me to stop.

"I've got to put these on yah, lad."

She had a pair of handcuffs on her belt, and she put them on my wrists. They were soft on the inside, but they were locked.

"Follow me, laddie."

I walked down the hall, and saw that her outfit looked good from the back. I wondered why someone representing law enforcement on this train would dress so proactively.

We walked past the cells until we were in a bigger section of the car, right before the exit door. There were six chairs set up, and all the gals from the other cars, including Hoyle, were sitting in them, still naked. I thought I would sit in the empty chair, but she led me toward the wall.

I noticed that there was something there like the massage table in the last room, but it didn't have any split legs at the bottom. It was just something for me to lie on, and she ordered me to lay on it so my head was facing away from the other ladies, and they had a view of my ass.

She then uncuffed one of my wrists, and then made certain that I was cuffed from behind. I realized that my ass was literally on the line, and I wondered if I could say if anything could get me out of this. At first I was afraid that I would be in lockdown for the trip; now I was beginning to wonder if this is how these women exacted justice.

I mean, I wasn't totally innocent. I did bend the rules.

"Sorry I can't make ye more comfortable, Mr. Thomas Hanover, but this is a hearing."

I couldn't really see her, but she was behind me now, addressing the other women. I tried to turn and see, but I couldn't really do that, so I had to look at the wall.

I was able to turn and face a window, and I saw the train going by a town. I could see some buildings, and even faint lights at some of the windows, and I actually envied them. I contemplated shouting to them for help, but I knew that wouldn't happen.

"All right, ladies, you know me, I'm Officer Cinco, and I'd like to ask ye all some questions."

Cinco? I knew that in Spanish, Cinco meant five. I began to wonder if she is the next woman in the series, like Ace E, Two-Lina, Treyla, Fouranny, and then some variant of five, following the theme of playing cards.

Were the girls right? Is this hearing part of the process? If so, it was getting way too theatrical.

"Now, I'm going to ask Mr. Thomas Hanover the same questions, and I want you to respond with raising your hand for a positive answer. Do not speak out, as I don't want him knowin' what your vote is."

Officer Cinco then walked back to me. "Mr. Thomas Hanover, I'm warnin' you, if you're lying to me, I will punish you with this."

Officer Cinco then took out a baton from her belt that I had noticed before. At first I thought she was implying she would hit me in the face from the way she showed it to me, but then she got into position at my ass, and she was holding it over her head.

She clearly meant to spank me hard if I was lying! I realized that I had better tell the truth.

"Okay, now, there is a report that Miss Two-lina said it was okay for you to enter her glass enclosure while she was in the tub to show her masturbatin' to your nude form. Did she ask you that, and did you do it?"

"Yes," I said, "yes to both. I never touched her while I was there, and didn't touch myself as requested..."

"That's enough, Mr. Hanover. Show of hands, how many say he be tellin' the truth?"

At that point, I strained to see who was voting for me, but I couldn't see anyone at that angle.

After what felt like a while, Officer Cinco said: "Okay, Mr. Hanover, you're in the clear, for now, no spankin' just yet."

I was relieved, but frightened as she slapped the baton on her other hand for emphasis.

"Now the second question: Dr. Treyla said ye could come on her tits. Did ye do that?"

"Yes," I said, "she said I could, and even though I thought it was too much, but she assured me it would be okay if I said it was an accident."

"So you we're aimin' for those big titties of hers, Mr. Hanover?"

"She asked me to. It was like a game. I wanted to play."

"I see. So, did you actually wipe them off? You know you weren't supposed to touch the ladies."

"Not anyone naked, and I got that. There was a cloth in between. I wouldn't want to touch my own semen."

"Okay, you heard him, ladies, let's vote. Did he go too far?"

There was that silence again, and I could feel the wind as she raised up her baton, ready to strike.

After a minute, she put the baton down, softly in her hand. "It would appear that no one believes you went too far, Mr. Hanover."

I sighed in relief. There was only one questionable area now.

"All right, Mr. Hanover, now Ms. Hoyle says that she saw you possibly inside Fouranny when you were asked not to go under her underwear or touch her at all with your penis. Did you violate those orders?"

"No. I didn't go under the thong, at that point. She pulled it down a little, and I did feel some area, like the crack above the asshole. I was using the front me to rub the back of her, and I kept my dick... my penis pointed down."

"Let's a lot of rules bent, Mr. Hanover. Let's see if they vote you goin' too far."

Again, I heard nothing and saw nothing.

The baton was raised, but it again came down softly in Officer Cinco's hand.

"They aren't voting against you, Mr. Hanover."

"That's great. Can I get out now?"

"Not quite yet. There is one more question."

"What?" I reared my head up and realized this looks bad. I tried to change my tone. "I mean, what... is it, the last question?"

"When you were in the first room with Ace E, you were asked to come in your pants."

"Should I not have? Was that some kind of test? Did I fail it?"

"What we're asking is if Ms. Hoyle's sitting upon you, with her naked vagina on a boner in those soft pants, led to your ejaculation."

At this point, I could lie. It was Hoyle who wanted me to play by her rules, but even in the engine, she allowed me to touch her tits, something I still hadn't done in these cars so far.

"Yes. She did that. I probably should have just kept rubbing it in those pants to come on my own, but she did sit on me to make it easier for me to... release. If she violated her own rules, I don't mind."

"Did she ever do that again?"

"Actually," she did that once before, "she gave me her first kiss in the engine. I didn't know if that is part of the program, and she let me feel her breast, like while it was still in her overalls, so there was cloth over it. To this point, none of you have let me feel your tits yet, and I just assume that's for another car..."

"I see. So is Ms. Hoyle deserving of punishment?"

"Did she break the rules? I'm assuming that she makes them. I don't feel violated by her, if that's what you mean. I don't want her impeached or anything."

"Really? You admit to bending her rules three times."

"True. I pushed the envelope. The ladies gave me permission. I assumed that I could do what they asked."

"What if they asked you to do something that you're not supposed to do?"

"I think they have, or they wish that I could do something to them that I shouldn't, like Fouranny wanted me to touch her breasts, but I figured I wasn't supposed to do that now. She didn't order me to do it.

Suddenly, Officer Cinco's face got close to mine. "Really? And if I were to ask you to suck my tits, would you do it?"

Cinco then unbuttoned her top, and pulled down a blue bra she was wearing underneath so her big tits spilled out. She shook them in my face. If I wanted to, I could easily move my head so I would be sucking those nipples until they were harder.

"Uh... Hoyle would have asked me to do that, but she hasn't done that yet. I don't think I should."

"Very well."

Cinco then buttoned her top and then raised up something above my head. At first, I thought it was an axe, and she was going to chop my head off.

Instead, it was a mirror, and she put it in front of me. I saw in the reflection that all the chairs were empty, all but one, and it was Hoyle, who was smiling at me.

"Mr. Hanover," Hoyle began, "you have passed Officer Cinco's test. You will proceed to the next car."

"Oh, good," I said, "can we remove the handcuffs?"

"Of course, lad."

I was pleased when Officer Cinco let me out, and as I was about to get up, Cinco put her hand on my back.

"Wait, Thomas," said Hoyle, "you haven't done the thing you're supposed to do in this car."

"Oh. What is that?"

"Well," said Hoyle, "what did you do in the last car?"

"I got to feel some Fouranny fanny."

"Now it's your turn."

I could see Hoyle leaving in the reflection, and this time, I was able to turn to see her go down the hall. I saw the four other girls waiting at the corner, to see how it all worked out, and they were smiling. They went down the hall, presumably to wait in the cell area, maybe.

"Were they ever voting?" I asked Officer Cinco.

"All but Hoyle left after I cuffed you in the back. She had already decided that you were okay. For now, she wants us to be private for a little bit. Why don't you lay down, and hold up that mirror at the level I had it before?"

I wasn't certain why, but I did it. She then got something out, and it was another mirror, and she positioned it so I could see my own ass.

"I thought maybe you'd like to see your own ass being touched by a woman's hand for the first time."

My cock got very hard once again, very quickly.

"May I?" She asked.

"Oh, please do."

She then used her fingers to lightly touch each ass cheek, and I couldn't believe how good it felt. As she kept going, the pleasure just kept rising.

"Feels good, doesn't it, Mr. Hanover? Hard to believe that it doesn't feel so good if ye do it yourself, but if someone does it to ye, it's absolute bliss."

"I most certainly am."

I really had to hold back from rubbing my cock the mattress under me.

"Just to let you know, I'd like to be touchin' in the crack, with your permission."

"You've got my permission, yes."

"I'm not going to touch your perineum; that's the area between ye cock and ye balls. That is for another part of this train."

When she touched me on the crack, it felt like she was touching my dick. It felt so good, I had to rub myself.

"Aye, ye like that, Mr. Hanover? Don't take this the wrong way, but I'd like to be kissing your arse now."

"Yes, please!"

She kissed me all over my ass, and I loved every press of the lips. She then stopped suddenly.

"It's okay if you want to rub ye cock on the mattress. Just turn over if ye need to come. It makes a mess if you're layin' down like that."

"I think I just might."

I turned over and saw my cock was pointing at the ceiling. I looked up and saw Cinco unbuttoning her top like she did before.

"Wait," I said, "can I take off your clothes? I never did that before."

Cinco stopped and buttoned up her top. "I think that will be fine and not violatin' the rules, Mr. Hanover. I'll let you start with my top. You know you're not permitted to be touchin' or suckin' certain things that will spill out, and by that, I mean me tits."

"That's fine. I would like to see them again."

"Go ahead. I will ask you to refrain from comin' on them."

"Oh yeah, I was probably pushing it at Dr. Treyla's."

"Actually, I donna like it. I think it's gross."

"Okay."

She came closer, and I got up and unbuttoned her top. Her tits strained to be released in the bra she was wearing under it. After the buttons were undone, she took the liberty of stripping it off and throwing it to the floor. When I went to see how to take off the bra, she lightly touched my forehead to stop me.

"I know you want to be fully stripin' me, but I would like to be keepin' this on for now. Trust me, it will be worth it, laddie."

She then cradled her big tits with both hands, and made them bounce up and down in her bra, making my cock even harder.

"Why don't you unbuckle my belt and unzip my skirt?"

Her belt was pretty tough to undo, and she had to help me out. I had to search for the zipper, and once I unzipped it, the skirt and belt fell to the floor.

She was wearing some matching blue underwear, and she turned around to show it off. It was a thong, and I got to see her wonderful ass cheeks.

She then turned back around and faced me. "You did touch an arse for the first time in the last car, so I think you should do mine as well."

Then she embraced me and put my hands on her ass, which felt very soft and hard all at once. She then put her hands on my ass, and she rubbed the front of her on my fully standing erect cock. The material of the thong was soft, and it was very wet and slippery.

We kissed each other for a long while, and I could tell that we were both getting very aroused.

"Are ye gettin' close to comin', laddie?"

"Yeah, but don't worry, I won't do it on you."

"Yah just plannin' to just stroke it off, then?"

"I'm open to suggestions."

"Well, Hoyle asked me to call her and the girls in to watch, if you don't mind."

"Not at all."

"In that case, I be wantin' to show you a little secret about this table."

Cinco backed away from me, and she walked around to a nearby desk and pulled out a mattress. I didn't think it was needed; the table was already padded.

"Can you be holdin' this, Mr. Hanover?"

I held the mattress, and I saw that there was a small kind of hole in it. Cinco took off the mattress and tossed it aside, then put on the new mattress, and she pointed to the hole.

"I saw ye be noticin' that hole there. If ye lie down on your stomach, you'll find that you can stick your cock through it. Go ahead and be doin' that, and I'll bring Hoyle and the rest of the girls out for a nice surprise."

"Okay," I said.

As Cinco walked away, I realized that there was something that I wanted to try.

"Wait," I cried.

"Yes, Mr. Hanover?"

"Before you do that, can we..."

I don't know why I was ashamed to say it, but I whispered it in her ear.

"That's not strange at all, Thomas Hanover. Why don't you finish strippin' me, and we'll be tryin' that?"

Cinco turned around and pointed to the clasp of her bra on the back. I unhooked it and it fell to the floor. She turned around quickly, and her naked tits swayed and bounced together. I wanted to touch them, and she could see that. She pointed to her thong.

I stooped down and then grabbed the sides of the thong and pulled it down. I could see her naked pussy, and it was very wet. It was also with red pubic hair. Again, I wanted to do something that I was not permitted to do in this car by licking it.

Cinco helped me to my feet, and then I turned around, and so did she. We then stood back to back, and butt to butt. I moved from side to side, and so did she. It was a nice feeling to have my ass rubbed by another ass. It wasn't something that really aroused me, but I had always wondered what it would feel like, and now I knew.

Once we had enough of that, I got on the mattress, sticking my cock through that hole. It felt cold at first, and it was also pretty tight. However, I moved my dick a little in it, and it was a lot looser and warmer, and I could easily bring myself to orgasm with it.

"Are you in? Feels like a pussy, right?"

"I wouldn't know. This is the First Time Train, and..."

"Aye, I see now. Don't be gettin' premature now. The girls want to see you comin'."

As she left, I had another idea. "Wait!"

She came back and said, "Again with the waitin', Mr. Hanover? I don't mean to sound impatient, but I think the girls are really waiting. Is there a problem?"

"No, I just thought of something. You threatened to spank me before, and I was wondering..."

"Ye want to try a spankin' now? Ye want me to use the baton or just me bare hand?"

"That hand, but not too hard."

She then slapped, and I felt it, but it didn't hurt.

"Can you do it harder?"

She did so, and this time, it did hurt, but not much."

"One more time but hard..."

She then did it before I finished, and I think she left a pink hand-shaped mark on my ass, temporarily.

"Care for another, Mr. Hanover?"

"I think I'm good, for now."

"Did that turn ye on?"

"I've been turned on for several minutes. But yeah, it did turn me on a little bit more."

"Well, glad to be hearin' it. Now, will there be anything else, or can I get the ladies now?"

"Feel free."

It's funny how I feared a spanking so much as a kid, but hers just turned me on so much. I thought I would come if I just moved a little bit.

When the ladies all entered the room, they started cheering. Since my head was down, I could really see them. Then Hoyle stood right in front of me, with her pussy inches from my face.

"I hope you realize now that we trust you, Thomas, and yes, we kind of set up this scenario with Officer Cinco. You never really were in trouble, as you did play by the rules. Some of our clients like that game, but others do not. That's why I had the girls warn you what was going on. We won't do that again unless you break a rule, but we can see that you don't intend to do that."

"You and Officer Cinco certainly made this trip a bit of an adventure."

"We wanted to do something that we should have done in the last car."

"Okay. What is that?"

"We'd like you to feel our asses."

"And we'd like to feel your ass," Ace E added.

At that point, I was surprised I didn't just come at the thought of this.

Hoyle turned around and said, "Go ahead."

I felt her ass, which was big and muscular, and it felt so very good.

I then could feel my ass being felt, and I saw Two-Lina feeling it up.

"About time that I got to do this," said Two-Lina.

The other girls were in line behind her.

This was going to be so pleasurable, so I tried not to move at all. I wanted to see if just the arousal of their touches alone would make me come.

Surprisingly, it didn't. Not even when I felt Ace E's fine ass, Two-Lina's tiny ass, then Treyla's very big ass, then Fouranny's familiar ass. Not even as they felt my ass.

After I had another feel on Cinco's ass, Hoyle then stepped up again.

"Have you truly not come yet?"

"No, I like to keep it in sometimes."

"In that case, I think it's time for a sneak preview. These next three railroad cars we call the Triple T, or Three Terrific Titty cars. As you might have expected, you will have three wonderful first-time experiences with boobs."

Hoyle shook her big ones in front of me, and I wanted to come. I started to really hump that hole my cock was in, not caring when I came.

Hoyle then stepped aside and was replaced by Cinco.

"Wait," said Cinco, "not just yet, laddie. Hoyle hasn't got to the preview yet."

"Really? There's more?" I was willing to delay my pleasure a little more.

"About twelve more," said Hoyle, whom I couldn't see, "ladies, I want you to take your hands and cover your nipples, like this."

I saw Cinco cover her nipples with her hands, and assumed they were all doing that.

"Now, find a spot on Mr. Hanover and rub him with your underboobs. Don't use your nipples. That's for later."

I then felt ten warm mounds on me in various places, and it was like being smothered in warm goodness. It was a feeling I had never had before.

I looked up and saw Cinco, who said: "Ms. Hoyle, can Mr. Hanover kiss my cleavage?"

"I permit it," she said.

Cinco then bent over me, and I buried my nose in her tits. I kissed any warm mound that I could.

The women were moaning as they rubbed me, and some were crying out: "Come for us, Thomas."

It was like they were cheering me on, and in less than a minute, I didn't let them down. I filled that hole in the mattress with semen, and moaned in great pleasure.

Then Officer Cinco dropped to the floor and started frantically fingering herself. From the way she was moaning, she brought herself quickly into orgasm.

The only thing left to do was wipe myself off with a towel they gave me, and it was on to the next railroad car.