The High School Principal

The Cruise©

The school year finally ended. The Seniors graduated, which meant there would be a new batch starting in the fall. Lexi and Miranda both graduated and were off to college out of state. That meant I wouldn't be getting any more pussy from them. At least Lexi's mother, Marcie, was still available. Although she had started dating again, thanks to, according to her, my awakening her forgotten, or suppressed, sex drive again, she told me she would still be available for me almost anytime I wanted to fuck her.

I called my personal assistant, Mary, and asked her to come into my office. When she came in, I asked her to have a seat, and asked her, "Mary, have you heard anything about a cruise being planned for some members of the staff?"

"Yes, sir. In fact, Julie, you know, the receptionist, invited me."

"Are you going to go?"

"Yes, sir. It sounds like fun. I was really surprised when she invited me, but I'm happy she did."

"What can you tell me about it?"

"Well, can I use your computer for a second? It will be easier to show you."

"Of course. Go ahead."

She opened her computer remotely using mine. Then she showed me the announcement with all the details. It seems that someone had put together an adult's only cruise leaving from Galveston and stopping for two days at an adult's only island. It sounded like an all-inclusive fuck fest.

"Mary, are you sure you want to go on this cruise?"

"Yes, sir. I was really happy that I was invited. Everyone thinks I'm this shy prude. And, I guess I was before I met you. I took a big chance when I showed you my stories. You knew they weren't real, but they were based on my fantasies. You helped me live out some of those fantasies, and I am truly grateful to you for that. But I want to continue to explore more of my sexuality. I told you I took a chance by talking to you, and that worked out really well, so I took another chance and talked to Julie. She has been really nice to me and has encouraged me to take more chances. She told me she was bisexual, and she introduced me to sex with another woman. I mean, not another woman, but with her. It was different, but I enjoyed it. Then she told me about this cruise. She said I would have the chance to have a lot of sex with a lot of different people, if that's what I wanted. Now that I think about it, why don't you go with us?"

I thought about what she had just told me. That was a lot to take in. It's true that I introduced her to several sex acts that she had never experienced before. I had encouraged her to embrace her submissive side. And she had turned out to be a wild fuck. I enjoyed spending time with her. I was a little concerned about her being among a group of people who were so much more experienced with sex. And, if someone discovered she liked being submissive, they could take it too far and really hurt her. I felt like I should be there for her and to protect her.

"Mary, can you get me a list of the people who are going on this cruise?"

"Yes, sir. I think so. I think Julie knows."

"Thanks. I would appreciate it."

About an hour later, she brought me a list of names of the people who were confirmed. I was surprised at some of the names. I never would have suspected that they would sign up for an adult's only cruise that was going to an adult's only island where it was certainly implied that there would be sex involved. When they described it as an adult's only cruise, they didn't simply mean there wouldn't be any activities for kids. It meant kids weren't welcome because there was going to be some serious fucking going on. The announcement had even said the pool area was clothing optional. While I was surprised at some of the names, I wasn't surprised at some of the other names. I noticed Becky, the cheerleader coach, was confirmed. This could be interesting.

I called Mary back in and asked, "Mary, do you think you could get me a spot on this cruise?"

She smiled and answered, "I don't think it will be a problem. I'll have Julie come talk to you and give you all the details."

A short while later, Julie, the office receptionist, came in. She handed me a brochure that described the cruise in detail with the dates and prices. There was a brochure for the cruise ship and a separate brochure for the island resort. Unlike the announcement she had put together, the brochures were explicit in their description. I asked her if it was too late to sign up and she said she thought she could "fit me in." She had a big smile on her face when she said that, and I don't think it was just an innuendo.

I'm not sure why I had never paid any attention to her. I passed her every morning as I came in the office. She always smiled and said good morning and I always answered her with a smile. I now took the time to look at her, almost for the first time. She was in her late twenties, 5'7", 125 pounds, with auburn hair and green eyes. She had a nice smile, but what I noticed more was she had a really nice pair of breasts. I guess I had been staring at them because when I looked at her, she had a big smile on her face as she asked, "Like them? I can promise you that if you go on this cruise with us, you can play with them as much as you like."

I couldn't pass this opportunity up, so I gave her my credit card and she went online to sign me up. She said she needed my passport number, so I grabbed my briefcase to retrieve my passport and gave it to her. She made a copy, added the number to the reservation, and said, "All done. Welcome aboard. I look forward to it."

The big day finally came. Julie had arranged an air-conditioned tour bus for us. We met in the parking lot and rode the bus to the Galveston piers. The boarding took a while, but when we had completed all the formalities, we took a tour of the ship. I had never been on a cruise ship and I was impressed. It was huge, like a floating hotel. It had all the amenities including several buffet areas with all the food you could eat, several bars with free drinks, a nicely equipped gym, and a couple of night clubs with nightly shows and dancing, not to mention several pools with hot tubs.

Once we got checked in and took our bags to our staterooms, there was a welcome aboard mixer where everyone could get acquainted with the other passengers. I saw Becky and waved at her. She smiled and walked over to me where she planted a big kiss on my lips. She said, "I'm so glad you decided to come with us. We're going to have fun. I'm looking forward to it."

I noticed there were two very attractive young ladies standing next to her. One of them looked familiar, but I couldn't place her. Both of them appeared nervous. Finally, Becky said, "Oh, Bob, you know Meghan and Sissie, don't you?"

"Uh, I guess that means I should know them. I recognize, uh, Sissie, is it? But I don't think I know Meghan. I'm sorry."

"Meghan and Sissie were on my cheer squad this past year, but they just graduated."

"Oh! O.K., that's where I know Sissie from. Yes, I saw you at the football games. I apologize, Meghan. I'm embarrassed that I don't recognize you. I'm not even sure how that's possible. You would think I would remember someone as beautiful as you."

Sissie had a big smile on her face because I said I recognized her, but Meghan had turned red. I guess she was blushing because I had called her beautiful. All of a sudden, I had a thought that hit me like a ton of bricks. I asked Becky, "Can I speak to you for a minute?"

We walked away from any eavesdroppers, and I asked, "Uh, Becky. You invited your students on a sex cruise?"

She just smiled and answered, "Well, they're not students anymore. I invited them and showed them the brochures, so they know what to expect, and they're adults, so what's the problem?"

While I was trying to come up with a cogent thought, she continued, "Do you remember when I came to you and said some of my girls were talking about your dick? Well, Meghan and Sissie were two of the girls. When I brought that to your attention, you whipped your dick out and not only let me see it, you let me suck it. And I loved it! Then later when you fucked me with that monster, I couldn't get enough. But something I didn't tell you is that I'm bisexual. Yes, I loved your dick, but I have always liked licking pussy. I have gotten very good at spotting girls who also like having their pussies licked. Every year I pick out two or three girls who are probably bi, or maybe full-blown lesbo, but I know they are willing to have sex with me. These two have been with me for three years. Yes, I brought them along because I thought they might enjoy themselves, not only with me, but maybe with other women and maybe even with some men. I know they are curious about you. They have heard that you are not only well-hung, but you know how to use it. I would love to have you fuck me again on this cruise, but if you play your cards right, I can arrange it to have you fuck some nice nineteen-year-old cunts, either individually, or together. Now, tell me that doesn't interest you!"

What could I say? Just the thought of fucking those two teens had me getting hard. I was also looking forward to fucking Becky again. I replied, "O.K., you're right. Who you fuck is none of my business. I will tell you I really hope we can get together again, but if you can arrange for me to fuck your two companions, I would forever be in your debt!"

She laughed and said, "I can guarantee you can fuck me again, and I'm positive those two girls would love to let you lick their little pussies and then fuck them. Hell, maybe we will have a party in my stateroom tonight. I'll let you know. I have a feeling you're going to need a two-week vacation after this cruise just to get your strength back. I'll talk to you later. By the way, if you want to see some cute little teenage titties, we'll be sitting by the pool this afternoon. Topless."

Well, now I was worked up. That conversation made me horny as hell. I walked around for a few minutes, nodding at some people I recognized. I think some of the people were concerned about me being there. They were looking at me as their boss, the principal, and not as just another horny guy looking for a good fuck. Speaking of a good fuck, I saw Julie standing near the bar, so I walked up to her and said, "Hey! Can I buy you a drink?"

"Thanks. Yes, you can, but just so you know, the drinks are free."

"I know. It was just an expression. Just an ice-breaker to get you alone."

We sat at the bar and ordered a Margarita. As we were sipping the cool concoction, I asked, "Can I ask you something? I know Mary said you had invited her on this cruise, and that you two had been talking. Did she say anything about us?"

"Yes, but don't worry. Your secret is safe with me."

"Thanks. Can I ask, what exactly did she say?"

"Well, she said a lot after I got her to loosen up. She told me you had asked her out to dinner and when you took her home, she told you about her erotic stories. She said you had fucked her, and she had sucked your cock, and after you found out she fantasized about being submissive, you helped her act out those fantasies. She told me you guys had been fucking ever since and she loved it. Oh, and she said you had a huge cock."

"So, she really didn't tell you much, huh?"

We both laughed at that. I said, "Julie, I have never been on a cruise before, much less one like this. I'm not really sure what the protocol is. I mean, do I just walk up to someone I find attractive and ask, "You want to fuck?"

"Well, most guys try to be a little smoother than that, but, yeah, that's pretty much it."

I looked at her, smiled, and said, "Julie, you want to fuck?"

Again, we both laughed out loud, before she answered, "Yes. Yes I would."

We finished our drinks and I took her to my stateroom. As soon as we were inside, I took her in my arms, and we kissed passionately. When we broke the kiss, we got undressed and moved to the bed. As soon as she sat on the edge of the bed, I pushed her back and put my face in her hairy pussy. When I started licking, she gasped and said, "Fuck! Mary said you were good at eating pussy. She was right. No preliminaries, huh? You just dive face first into my cunt?"

"Well, I was going to say something like, why beat around the bush, but that wouldn't be right. I love to eat pussy. I know a lot of guys want to have their dick sucked, or some just want to fuck and get it over with, but I have always liked to lick the girl's pussy and make sure they get pleasure, and then I like to take my time making love to them. To me, it's not about fucking. It's about mutual satisfaction. I hope you will let me make love to you. It might be a while before we are finished."

"Please. You already know I'm bi, so you know I like to have my pussy licked. Take all the time you want. I don't have anywhere else to be. At some point before we're through, though, I am going to suck your dick."

I continued licking and sucking until I was sure she had at least two orgasms. Since it was the first time I had been with her, I decided I wanted to impress her, so I sought out and found her clit and started licking and sucking it, while finger fucking her with two fingers, until she had another two screaming orgasms. She was pulling my head as she said, "Please, no more. I can't take anymore. Fuck! My clit is so sensitive right now. No one has ever made me cum like that, not even my steady girlfriend. I'm going to have you teach her some new techniques! Now, please, come fuck me."

We fucked for about forty minutes while she climaxed a couple of more times. After I had cum in her pussy, she took my cock in her mouth and sucked me until I had cum again. We took a shower and got dressed. I kissed her before she left, and she said, "Before this cruise is over, we're gonna do that again."

* * * * *

I went down to the pool where I found Becky and her two young charges lying face down with their bikini tops undone. I said, "Hey, beautiful", and she looked up at me with a big smile. "Hey yourself. Want to join us?"

I sat down between Sissie and Meghan. I saw a bottle of suntan lotion next to Meghan, so I picked it up and asked, "Meghan, would you like me to put some lotion on your back? Wouldn't want to get burned your first day out."

She turned her head to look at me and answered, "Yes, please."

I put some lotion in my hand, then rubbed my hands together to warm it before applying it to her back and shoulders. I rubbed slowly, making sure to cover her entire back, and then started massaging her shoulders. She was moaning so I moved down to the center of her back and then to the top of her bikini bottoms. I then got some more lotion on my hands and started rubbing it on her thighs, first from the top and down the outside to her knees, and then back up the inside of her thighs until I was just below her pussy. She opened her legs as I did that, so I repeated it until I was just below her pussy again and I started massaging her upper thighs. I could tell she was getting excited. I stopped and asked, "Sissie, would you like me to put some lotion on you, as well?"

She had been watching me massage Meghan, so she said, "Yes, please. If you don't mind."

I repeated my massage on her back and shoulders, making sure to rub the sides of her breasts, and then the thighs until I was massaging the inside of her thighs, just below her pussy. Just like Meghan, she had opened her legs wide.

"Becky, I was thinking about getting some drinks. Can I get you anything?"

Oh, yes. I heard they make a really good Margarita. Would you mind?"

"Not at all. I had one earlier, and it was good. How about you girls?"

Meghan answered for both. "Yes, please. A Margarita sounds good."

I had learned that while Texas law required them to be 21 before they could drink alcohol, once we got past the twelve-mile-mark, we were in international waters and we were no longer under Texas jurisdiction. I went to the bar and got four Margaritas and went back to the pool. When I had given each of them their drinks, I asked, "Becky, how long did you plan on staying out here in this hot sun? I was thinking we could grab some snacks and go back to your room to relax for a while."

"Ummm. It is getting hot. How about it, girls? Do you want to go back to the room to relax?"

Meghan answered first, "Yeah. That sounds like a great idea. I am getting hot. Let's finish this drink and then we can go back to the room."

I followed them back to their room where Becky sat on one bed and the girls sat on the other bed. Becky took her top off and said, "I don't think we need these anymore" as she tossed it in the corner. The two girls followed her example and took their tops off, revealing two pairs of delicious, firm titties with hard little nipples standing straight out.

I decided to get the party going. I said, "Becky, I know these lovely young ladies are here because of you. We're all adults here, so I'm not worried about hurting anyone's feelings. I'm the only guy here and I'm looking at three very sexy partially nude women. I'm horny as hell, and I want to fuck someone. The question is, who wants to be first? Any suggestions?"

Becky said, "Well, for starters, you're overdressed, so how about we all get nude."

She stood up and dropped her bikini bottom, and the two girls did the same. It only took me about a half a second to shed my shorts and T-shirt. I heard Sissie gasp and say, "Holy shit! They weren't kidding. He's huge!"

Becky chuckled, and said, "I've already sucked that thing and he fucked the shit out of me. Let me tell you, he has enough to please us all. Anyone want to take the leap, or do you want me to take care of him first?"

Meghan was always the first to take the lead. Sissy was more reserved, almost shy. So, I was surprised when she asked, "Can I suck it?"

I looked at her, smiled, and said, "I would be very happy to have you suck me, Sissie. In fact, I have been looking forward to it." I moved to her side of the bed until I was standing with my cock right in front of her face. She reached out and wrapped her hand around it, gave it a couple of slow strokes back and forth, and then, very tentatively, stuck her tongue out so she could lick the head. Satisfied with the taste, she took several laps around the head before leaning forward and taking the head into her mouth. She wrapped her lips around my shaft and then slowly started bobbing her head back and forth. I could also feel her sucking me. It felt so good to have this little teenage mouth wrapped around my dick, it was all I could do to keep from blasting a load of cum down her throat. I looked at Meghan who was on her knees, leaning forward with her mouth open, and watching Sissie performing a very commendable blowjob. In a very soft voice, she asked, "Sissie, can I try that?" Sissie kept bobbing and sucking as she mumbled, "Unh Unh." I looked at Becky and saw she was smiling, obviously proud of her young protégé.

I put my hand on the back of Sissie's head, not forcefully, but just to silently let her know she was doing a good job. I said, "Sissie, that feels so good. You are really good at sucking cock. But if you keep this up, I'm not going to last much longer. Would you let me lick your pussy for a while? I promise to let you suck me again later, if you want to."

She reluctantly took my cock out of her mouth and allowed me to push her back on the bed. I kneeled between her legs and started licking her sweet little pussy. I thought I was in heaven. I licked her through several orgasms and when she couldn't take it anymore, I looked at Meghan and asked, "Meghan, can I lick your pussy now?"

"Oh, yes. Please eat me."

I repeated my performance on Meghan, and by this time, my dick was so hard it hurt. I looked at Becky and asked, "Can I fuck you now? I need to cum soon or I'm gonna bust!"