Teen Cruise

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For summer vacation, my dad decided to take the entire family on a cruise. Frankly, I wasn’t very excited about it. For one, the entire family included my 7 year old brother, whose primary language was his own, generally interpreted by others as screaming and incoherent jabber, but that’s what happens when you are constantly hyped on soda. Secondly, at the age of 15, I was in the very rare position where I was neither a child nor an adult. I was too old to really enjoy kid stuff without being seen as strange or disturbing, and I was too young to enjoy the adult stuff because society said I wasn’t allowed to yet. This was going to be a circle of Hell for me.

Or so I thought.

The cruise ship we got on was massive. I’ve never seen anything manmade so huge in real life. How could the thing even float on the water? We walked up the ramp over the water – the part that made me the most anxious and nauseous – and onto the main deck. To our left, there was another deck two floors above us, and the highest deck of the ship was another 4 floors above that one.

“Come on, our room’s this way.” My dad gestured over to a doorway leading into the heart of the ship. He guided us down one of the hallways of the ship through the horrid traffic of other cruisers and tourists as we tried to find our room number. As we crossed through an intersection, I accidentally collided with a girl, and sent both of us tumbling to the floor.

“Oh God, I’m so sorry.” I apologized, helping her up. As I made eye contact with her, my heart fluttered for what could possibly be the first time ever. She was a cute young thing around my age, slim and fit as can be, long dirty blonde hair and skin like cream. She wore very loose and revealing clothing; a loose pink shirt that was tied in a knot just underneath her tiny bustline and a pair of beige shorts. The first few buttons of the shirt were open, making the collar loose enough that it threatened to slide down her shoulders. Granted the whole ensemble made sense, considering the sun drenched cruise we were embarked on, but I couldn't imagine any parent allowing their daughter to dress so lightly around other people.

"Max, come on, before the REAL rush comes through." my dad called.

"Okay!" I called out, then turned back to the girl. "Excuse me." She gave me a smile as I left, and I couldn't help but feel most of the blood in my body rush to my face. She was quite cute, and I really wanted to stay and know her more, but I didn't want to get lost on this huge dreadnought of a cruise ship. Dodging past other vacationers with my bag in tow, I caught up with my family. The sugar rush that was my brother was bouncing around, despite my mom's best attempts to calm him down.

"Here we are." My dad announced, unlocking the door to our cabin room. It was a modest room with two queen-size beds. Great. I'd be sharing a bed with my little brother. At the age of seven, he just learned how to be seriously annoying and completely unpleasant to be around. To top that off, he was a kicker in his sleep, and doubtlessly we were going to be sharing the same bed. I looked over at the chair and table in the corner of the room, contemplating how I might sleep in it comfortably. Probably not. The floor looked like a better alternative.

I placed my bag at the foot of the bed on the opposite end of the room, and my brother made this huge Spiderman leap onto it, ruining the perfectly folded bedsheets in a single move.

"Anthony, dear, don't jump on the bed." My mom scolded him in a calm tone, but experience told both of us that wasn't going to work.

"I wanna go down to the pool now!" he wailed in a cacophonous tone.

"In a little bit, honey. Now stop jumping around on the bed. I want to have a walk around of the ship."

"Actually, Martha, we don't need to do that right now." my dad said. "After a two hour drive, I'd like to put my feet up for a while."

"Okay, then. Anthony, Max, go get dressed in your swimsuits. We can hang out at the pool for a little while."

My brother let out a cry of joy and started stripping off almost immediately. I turned my back to that, since I didn't want to see his willy flopping about, and I dug through my bag searching for my swimming trunks. The entire time, Anthony was jumping around on the bed in between stripping off clothes. I kept my head down and away from him as I went to the bathroom to change. When I came out, he was dressed in his swimsuit as well. My mom and dad slipped past me and closed the door behind them. They came out a few minutes later. My dad was wearing a pair of flat-colored swimming trunks. He was a tall thin man with clean grey streaks in his hair and a pair of glasses, all of which made him look like something straight out of Mister Rogers' Neighborhood or perhaps President Bush. He looked completely out of place in swimwear, but if he had any sense of self-awareness or indignity, it didn't show. Mom was beside him wearing an ocean blue one piece swimsuit. She looked like a slightly older Lea Thompson - that woman who played Marty's mom in Back to the Future. She was... admittedly hot, but I wasn't about to tell anyone that. People would think I'm a creep for thinking my own mom's hot.

Mom grabbed a few beach towels out of one of the bags and we left the room. The foot traffic was terrible; parents dragging kids even more cacophonous than my brother into rooms, infants screaming, and a few couples bickering over one thing or another. I swear I heard a couple of F-bombs dropped amidst the din, but nobody else seemed to notice or mind.

We headed up a couple of flights of stairs, guided by maps conveniently plastered on the walls near doorways and stairways. I took note that there were two pools on the cruise ship. There was one on the bow of the ship, one a few floors above that one. According to the legend, however, it was strictly adults only. I could only imagine why...

We got to the pool and found it already jam packed with people. Anthony went racing across the pool grounds to jump into the water. I walked over with my parents to find a good seating area. After two circles of the pool, we made our own seating arrangements by moving a few of the empty beach chairs around to the same spot.

"There we go. Perfect." my dad said, then sat down and crossed his legs. He pulled out a book from seemingly nowhere - probably tucked away in the towels without my notice - and settled himself in for a good read. Mom spread the beach towel over her bench and put on her sunglasses before sitting down to relax. I decided to relax in a sun for a bit as well before jumping into the pool.

From my perch, I could see most of the pool and the many goings on. A quadrant of the pool had a volleyball game going on, and elsewhere people were simply swimming around and relaxing. Some twenty feet from us was the lifeguard, keeping a vigilant watch over everything from his tower of a seat. The noise all the people made was dissipated by virtue of being outside, but occasionally some kid would belt out some ear-stinging cry for one reason or another, violating the state of zen I felt myself falling into over time.

I don't know how long I laid there. I lost track of time after maybe five or ten minutes, and I didn't immediately register the shadow standing over me.

"Huh? Oh, it's you!" I said once I stared at the figure for a few seconds. It was the girl I collided into in the hallway.

"Hey there. Would you like to go for a walk?" she suggested, offering her hand to me. I felt my insides twisting around a bit out of confusion and excitement. This hot girl was actually paying attention to me!

"Uhh... sure. I'm gonna go for a walk, dad." I said to him as I took her hand and got to my feet.

"Alright, son. Don't go too far." he said dismissively; he was more interested in his book and at fifteen, I was able to look after myself. My mom had no input; her sunglasses obscured her eyes, but her relaxed position implied that she had fallen asleep. The girl led me away from them, across the pool back to the entrance of the ship.

"You're a pretty cute guy." she said, leaning up against the hull of the ship. "Where are you from?"

"I - uhh... California." I answered.

"Oh yeah? I'm from Utah, myself."

"Really?" I asked. "Are you a Mormon?" My dad told me some strange things about Mormons. For whatever reason, there were a lot of them in Utah.

"Yeah, but I don't know if I really believe it. Aren't all religions kind of the same anyways? Believe in God or burn in Hell forever?"

"Yeah... my parents make a big deal about attending church, but aahh, it's boring for me."

"Oh, I should probably introduce myself properly. My name is Penny."

"Max."

"Soooo, Max. You have a girlfriend?"

"I... no."

"Oh goodie for me. I don't have one either - a boyfriend, that is - and it's gonna be pretty lonely and boring otherwise on this cruise."

"Where are your parents?"

"They're up in one of the first class areas right now. Counting their money, if I had to guess. Rich parents, you know how it is."

"Yeah... I don't, but yeah." I looked down as Penny as she grabbed my hands and pulled them behind her so I was holding her in a loose embrace. She was being remarkably forward, not that I was complaining. I was just in utter disbelief that such a hot girl was flirting with me! She was still wearing those clothes from earlier. I swear that top was being held up purely by the laws of decency. As I continued to look at it, however, I realized that it was actually transparent a little bit!

"Hee hee, like what you see?" she asked, noticing my gaze. "You know we could sneak away for a little bit and we could do all sorts of naughty things!"

"I-I don't think my parents would like me going somewhere they don't know I am." I replied, though I loathed myself intensely for saying that. I never had a girlfriend and by extension I was a virgin, but ever since I hit puberty, I knew without a shadow of a doubt that I was fascinated with girls and that I'd give anything to spend time with one. Fortunately, my response didn't seem to deter her an inch.

"Well you should-"

"TAG! YOU'RE IT!" Anthony's voice came howling behind me, and before I could even think of responding, he shoved me hard with both his hands, causing me to stumble forward and collide into Penny. To my shock, our lips actually pressed into a kiss. It was an awkward one, as our lips didn't line up exactly and our teeth collided. It was a rather unpleasant experience, and I pulled away from her. My face must have been as red as a tomato. She didn't look phased at all by it. Just how unflappable was this girl?!

"I'm sorry about that." I said. "That's my brother, he's... well, I don't know why he acts like that. My parents said he has attention deficit or something like that. Basically he's hyperactive all the time and can't focus on any one thing. He's supposed to get medicine for it eventually."

"I see."

"Actually, do you think you could have lunch with me and my family later today?" I asked. "If we're gonna be together on this cruise, I think it's best if you meet my parents."

"It's a date! If that's the case, though, maybe I should go get dressed in something a little more appropriate for parent-meeting." Penny said. "I'm up in First Class, Room 4."

"I'm in room 216." I replied. "You want I should come pick you up?"

"Yeah, I'd like that. I'll go get dressed now, and until then... here's something to remember me by." Penny leaned in and gave me a kiss on the lips. A real one. She held me by my wrists so I couldn't pull away, not that I wanted to. It was a very warm and soft feeling, and it made my skin crawl in a very good way. Penny pulled away and gave me a smile before heading back into the ship. I stood there for a minute or two, recovering from the shock of my first kiss. There was something about it that made me even more attracted to her. If I believed in such things, I'd swear she cast a spell on me. She was very beautiful, and she was interested in me! Trying to keep my head cool and my loins calm, I returned to my parents, who had not moved from their positions.

"Hey dad, I invited a friend to join us for lunch." I said.

"Very good. What's their name?" Dad asked.

"Her name is Penny. I accidentally crashed into her when we were heading to our room earlier."

"Oh. Good to know there's no animosity between you two." Dad checked his watch. "Well, it is getting close to lunchtime. Go retrieve Anthony and we can go get dressed for lunch."

"Okay."

"By the way, does your friend know where we'll be eating?"

"No, actually. I planned to go pick her up at her room when we were ready."

"In that case, let's not keep the little lady waiting. Go retrieve your brother quickly."

I went over to the pool and scanned the water for my brother. He was on the other side, trying to join in on the volleyball game. I went over to the other side as he tried to serve the ball only to spike it into the water less than a foot in front of him. All the other players broke out in laughter at his performance.

"Anthony, it's time to go." I said.

"But I wanna play some more!"

"No, you're done. Dad's orders, let's go." As I said that, in my head I was thinking 'Don't throw a tantrum don't throw a tantrum don't throw a tantrum.' as my brother was known to do when he couldn't get his way. In front of all these people, I would be so mortified, and I didn't need him ruining my chance with Penny! Thankfully, he complied and climbed out of the pool. We went back to our parents, who were gathering up our effects. Mom helped Anthony dry off, and I folded and stacked up the towels that otherwise went unused.

"Here, son. Go on ahead so you can get dressed and retrieve your friend." Dad said, handing me the key to the cabin. "We'll be right behind you."

"Thanks." I left the pool area for our cabin, where I quickly stripped off my swimsuit and threw on my normal clothes. I didn't even bother heading into the bathroom to change. I was almost done by the time my family got back.

"You know where the dining room is, right, Max?" Dad asked. Mom went into the bathroom to change, and my brother jumped back and forth across the beds. "Anthony, get down!"

"Yeah. I'll just check the ship map if I get lost." I replied. "Don't worry, I'll find my way there."

I left the cabin and, with the help of the ship map I found my way to the first class deck. Unlike the rest of the ship, there was very little foot traffic here, most of it crew members. None of them paid me any mind as I knocked on Suite 4. I didn't have to wait long for Penny to answer the door. She was still dressed casually for summer, but at least now she was more presentable than her previous attire. Now she wore a tank top and short jeans that were... quite remarkably short, but at least a few inches longer than Daisy Duke shorts.

"I'm sorry, this is the best I could do." she said. "I didn't expect to be meeting parents, so I didn't bring appropriate parents-meeting clothes along."

"No, it's fine. I approve, at the very least." I said. The way her jeans accentuated her thighs made me very hot and bothered. Part of me really wanted to bury myself between them. Maybe if I played my cards right, I'd actually be able to?

I walked with Penny to the dining hall. We didn't turn the first hallway before she grabbed my arm and pulled it around behind her so I was holding her like a trophy wife. I swear I could hear my heart pounding in my chest. This was no passing interest or flirting; whatever depraved thoughts were pulsing through my brain was a shared fantasy. She, too, wanted to go at it like a wild rabbit in heat, and the first chance she got, she was going to take it. For now, though, we had to play it cool.

We arrived at the dining hall and found my family seated at one of the tables. I pulled my arm away from Penny and tried to make myself look civil in front of my parents.

"Penny, I'd like to introduce you to my family." I said, ceremoniously gesturing to them.

"Hello. I'm Penny. Penny Rosenthal." she said.

"Hello, young lady. My name is Richard Hemerson." my dad greeted, shaking Penny's hand as she went to sit down. "This is my wife Martha, and over there is our youngest son Anthony."

"Say hello, Anthony." Mom said.

"HELLO!" he belted out loud enough that a few heads turned in our direction.

"In a civil volume, Anthony." my mom scolded gently. "Do not disturb the other patrons, and be on your best behavior for our guest."

'Yeah, don't fuck this up for me.' I thought to myself as I pulled up a chair next to Penny. Our hands clenched together under the table. For lunch, the waiter brought us some seafood pasta - some type of spaghetti combined with lobster, crab, shrimp and parmesan - and bread sticks. Before we began eating, our dad bowed his head to pray as was the Episcopal custom.

"Dear Lord in Heaven, we thank you for this blessed day in which we break from sewing the earth to come together as family and celebrate our good fortune. May this food that your creation and our labor provides nourish us and fill our hearts. In the name of the Father, we pray. Amen."

"Huh, I guess prayer is the same no matter what religion you're in." Penny observed as we began eating.

"What do you mean? What religion are you, if you don't mind my asking?" dad asked.

"Mormon, though I'm not so... adamant about it, I guess you could say."

"I see. Well, I personally believe that the path to God is not so straight and narrow. So long as you hold to the tenants to do right to your fellow man, I don't see any reason to split hairs about what version of God you see to worship."

I didn't know what to make of that. My dad was a very diplomatic individual, never polarizing, but I always felt a slight tone of judgement was underneath his veneer of neutrality. Maybe that was just my take on it since I was his son.

"Anyways, Penny, what do your parents do for a living?" he asked.

"They're real estate investors. They're also on this cruise, but they're... somewhere."

"What are your plans once you graduate high school?"

"I'm gonna go to college. My parents want me to get a degree in financing and work on Wall Street, but I don't know if that's what I really want to do."

"It's a very cutthroat business, working on Wall Street." my dad commented. "But it's a great way to make a lot of money. Max here I've been trying to convince to go to law school like I did, but he's more interested in pursuing computer science."

"It's a fast-growing industry, dad." I defended. "In ten years, almost everything's gonna be done by computers!"

"It's an incredibly niche market and highly specialized skillset to make a bunch of inexorably expensive calculators and word processors." he said in a calm but judging tone. "But lawyering, that's a business that never lets up. Hell, even medical school would make you set for life."

"I'm not just interested in making money dad. I want to do something that I'm actually interested in doing."

"I know, son. I'm just trying to help you decide what's best for yourself so you don't have to live day by day because of a worthless degree." there was a brief pause as he took another bite of his pasta. "But... that's a decision to be made another time. You have another three years to make your decision, and this is our vacation. Put aside your concerns about the future for now."

The rest of our meal was uneventful. My parents would occasionally ask Penny something inconsequential, like what Utah was like or her faith as a Mormon, but otherwise left us to our own devices. After lunch was over, dad ordered us all drinks. Penny, Anthony and I were served something called a Roy Rogers. It was this cocktail made with Coca-Cola and something called grenadine syrup. It was non-alcoholic, so we were allowed to have one. I found it to be quite an interesting flavor. It was bubbly like soda, but the flavor was different, both sweet and tart like a strawberry or some other kind of tart fruit. Either way, it was quite delicious.

I walked over to Penny, who sat down at a table near the window, staring out at the sea while she sipped her drink. I sat down opposite from her.

"Your family seems nice." she commented.

"At least my brother was better behaved this time." I said.

"You know, I'm not really fond about going to college for a business degree. Your family wants you to go so you can make a better life for yourself. My parents want me to go so I can continue adding to their fortune. They spent their entire life amassing their fortune and trying to avoid paying their fair share of taxes. I don't want to spend the next forty or fifty years of my life running away from the IRS. I want to do something I love AND make decent money from it; is that so much to ask?"

"I don't know. Better not let my dad hear you say that, though." I said. "He's the kind of person who believes that you can't have a job that pays well AND like it, not unless it's a job that's illegal or immoral or something."

"I'm sorry, but that's a really stupid thing to say!" she said fiercely. "That's... just... ugh, I don't even know how to put into words how stupid that is!"

"I know what you mean. Don't get me wrong, but I don't think anyone driving a garbage truck or shovelling roadkill is going to find much joy in their job, but I don't think you're supposed be miserable."

"No offense, but it's guys like him that stop me from saying what I really want to do."

"Could you tell me?"

"I don't know. I'm not sure I trust you yet." she finished off her Roy Rogers and leaned in to whisper suggestively in my ear. "But you are on the right track." She followed it up with another kiss on the lips, then stood up.

"Well, thank you for inviting me to lunch. I'm gonna go retire to my room for now, think about some things."

"Okay."

"I'll see you later, Max."

I watched Penny leave the dining hall, and I felt a sense of longing, like she just stole something from me and was walking out with it. Fact of the matter is she did steal something; my heart. I feel stupid for saying that, since I've only known her for less than a day, but she was attractive, and she was interested in me perhaps for the same reason. Maybe it was just teenage hormones, but I wanted to be around her, and do things with her. I did not like watching her leave, so I turned back to my drink. If only it WAS alcoholic, maybe it would help ease the discomfort in my stomach?

I didn't see Penny for the rest of the day after lunch. When the evening came, we went to a theatre room after dinner to watch Return of the Jedi. Seeing Leia in that slave girl outfit stuck in my head for the rest of the movie. I kind of just wanted to look at that for two hours. The movie itself was fine, but Carrie Fisher in a bikini loincloth was amazing.

After the movie ended, it was close to ten o' clock. My brother had his caffeine crash and had passed out halfway through the movie. I was getting rather tired myself, and I left with my parents back to our room. After brushing my teeth in the bathroom, I got dressed in my pajamas and climbed into bed. My parents would do the same half an hour later. As much as I tried to get to sleep, I simply couldn't, and for once it wasn't because Anthony was kicking my sides. I couldn't take my mind off of Penny and what she said to me. She was definitely interested in me, otherwise she would not have been flirting so hard.

At some point, there came a knock at our cabin door. My parents were asleep and didn't respond to it. I slid out of bed, careful so as to not wake neither them nor my brother up, and once I made sure the deadbolt was in place, I opened the cabin door.

Penny was standing there, dressed in the same outfit I first met her in.

"Hey there." she said. "Come on out."

"Huh? O-okay." I unfastened the dead bolt, grabbed the cabin key and put on my shoes. Hopefully this wouldn't take long; I don't think my parents would agree with me going out at night without their knowing, unsupervised, but I wanted to be with Penny, and I wasn't going to let this opportunity slip by.

"Come on." she said, leading me down the hallway. Despite the summer climate, it was pretty chilly out; perhaps it was because of the wind coming off the ocean? I tested my limits with Penny by wrapping my arm around her back as she made me do earlier today. She did not object; in fact, she leaned into me, resting her head on my shoulder.

"Sorry about running off so abruptly earlier." she said. "I needed to get away to think and... meditate on everything going on."

"Meditate?" I asked.

"Think of it like... praying, I guess. It's something they do in Asia and Buddhism. You basically clear your mind of all thoughts and reach a state of calmness. I find it helps me with the stress, but my parents don't like it when I do it."

"What did you meditate on?"

"I'll tell you once we get to my room?"

"Your room?"

We reached the suite wing, and she unlocked the door to her room and we stepped inside. It was a much nicer room than mine. It was slightly larger with furniture scaled up to match, and there was one queen-sized bed that dominated the back wall of the room. The light in the room was managed with a slider switch, and the lighting was currently set to dim.

"Wait, where are your parents?" I asked, seeing that the room was empty.

"They're in their own room. Suite Room One." she said, closing the door behind us. "This was my own request; they have money to burn, they could more than afford it."

"Why get a different room entirely?"

"Because this whole cruise thing? It was my idea." Penny went over to the bed and plopped down. She patted the mattress with her hand, inviting me over. I sat down next to her. "My parents are going through a rough patch right now. Actually, no. More than that. their marriage is falling apart, and I'm sitting here from the sidelines watching it collapse."

"What's the problem?"

"Money, ironically. They spent their entire lives working to keep their wealth that they have barely spent any time together, much less spent time with me. A wet nurse has been more of a mother to me than my actual mom ever has been."

"I'm... sorry." I said. I moved to place my hand on her in comfort, but I didn't know where to do so without making it seem like sex was the context behind it. I stopped and put it back down.

"I wasn't lying when I said that was their entire life; makes me wonder if there was any personal reason they had me. Work work work, dodge taxes, make this deal, sell that to the highest bidder. And now they're arguing over expenditures because one thinks they're pulling more weight than the other. Money means more to them than me.

"I planned out this cruise so I could put them in a room together far away from their money and business deals so they could be together and hopefully come to a final decision on whether or not they REALLY love each other, and not just because our Mormon faith demands that we all have a family." She let out a cruelly amused and stressed laugh. "It's funny. This country is supposed to be the land of the free, yet the capitalist obsession with money and our drive to make and keep it shackles us more than any Soviet regime could ever hope to accomplish."

"And what about you?" I asked. "Why come along yourself?"

"I wanted to see the fruits of my efforts up close, and so I could decide what I want to do going forward. I already made my choice that I'm not going to go down their path. Whether or not I inherit their money, I don't care. I just want a man who loves me the way I am, who won't judge me for what I want to do, and we could all be together as one big happy family, and money will be a means to an end, not an end to itself."

"What DO you want to do?" I asked. I was terribly curious, since she mentioned people like my dad not approving of her choice.

"And this is one of the things I needed to meditate on; to know if I could trust you. I feel... you have earned the right to know, for being so nice and patient with me." Penny sat up and gave me a sharp, determined stare. "Simply put, I want to make love."

"Make... love?" I asked. For a moment I thought she meant between us, and my heart nearly leapt out of my body and out the porthole.

"Porn, to put it another way, but not just any old porn. Romantic porn. I want to do something for all the couples out there like my parents who prioritized things other than the family, to the point that their own family are strangers to them."

"And you plan to do this with... porn?" I asked. It sounded truly insane, but I was honestly intrigued.

"Not just porn. Also things to spice up the bedroom. There are all kinds of amazing things you can do together during sex. I want to make an industry that's all about keeping that fire alive. A relationship without sex is a very boring one!"

Once she was finished with her speech, Penny relaxed back on the bed and looked up at me.

"So what do you think?"

"It's a pretty insane idea." I said honestly. "But I think I could support such a thing."

"Thanks. My wet nurse Beth, though, is really the one who came up with the idea. I'm just running with it." Penny sat up off the bed and turned to me, holding my hands in hers. "You know, I really like you. That's why I brought you here tonight." she pulled at the knot holding her shirt together, and she shrugged it off her shoulders. I tried my best to remain calm as she removed her shorts as well, revealing that she was not wearing any underwear underneath. This was it. I was going to lose my virginity tonight. While I was ecstatic, I couldn't help but get overwhelmed by anxiety and... I guess what you could call stage fright. I worried about everything there was to possibly worry about. I worried about what my breath smelled like, if I'd be able to keep it up the whole time, if I might not like it. It must have shown in my expression or something, because Penny giggled and leaned in to give me a kiss.

"Relax, Max." she said. "This is gonna be the most amazing thing you've ever experienced!" She unbuttoned and pulled down my shorts as I removed my shirt. Once I was naked as well, Penny pulled me to my feet and into a tight embrace. This close, I could smell the sweet flowery musk that her body emanated. All my senses were on overdrive as I tried to take in every unique sensation that she provided. The warmth of her nude body against mine, her soft yet firm grip, and most of all, how my dick felt as it erected between her legs and pressed against her puffy slit. To my surprise, it was remarkably warm and moist, like someone was exhaling all over my dick, and that only served to make it harder.

"I can feel you getting more excited." she whispered in my ear.

"I didn't know that it... breathes like this."

"It does. Now imagine how warm it must be inside me." Penny leaned into me and kissed me on the lips. She pushed more of her weight onto me until she was practically shoving me back onto the bed. We held the kiss and our hands explored each other's bodies. My hands clenched down on her small tight butt. It was amazingly firm and was an excellent place for me to hold her while we made out. Penny broke the kiss after several minutes, sitting up on my lap and wiggling her hips back and forth.

"Do you want to be on top or on bottom?" she asked.

"Uhhh... I don't know." I said. I didn't know how to fuck her, and I didn't want to botch my first performance because of stage fright.

"Alright, then, here's how it's gonna go." she said. "This is the Kentucky Derby, you're my valiant stallion, and I'm gonna ride you all the way into first place!"

My heart was beating so fast now I wasn't certain if I'd be able to contain myself. Penny lifted herself up slightly and held my penis straight up so when she sat down, the tip of my dick pressed against her tight warm hole. At first it just bounced harmlessly against her labia, squishing the puffy lips slightly, but then she rolled her hips side to side, inching the head into her folds. Once the tip was inside, the rest of my length went in just as easily.

It wasn't until I had several inches inside Penny that I realized her insides were tightening all around me! It was an amazing feeling, but at the same time I had this primal fear from something clenching such a sensitive part of my body. Penny leaned down over me and braced herself against the mattress. She bounced her hips against mine, pumping my dick in and out of her tight hole. The head flared up with such an incredible feeling that it paralyzed me. My limbs tensed up and my hands gripped at the bedsheets.

"Huh... huh, how does it feel?" Penny asked between heavy breaths.

"I feel... this is amazing!" I gasped.

"It's going to feel even better." she leaned down briefly to kiss me on the lips before she resumed her motions. I couldn't believe what was happening. I was actually losing my virginity! I was never told what to expect, but this was amazing! It wasn't just the feeling of having my dick tugged that I loved. It was also the warmth and softness of her body against mine. All the lesser feelings were much more intimate when we could feel them with our bare skin and when we were literally connected at the hips.

Penny continued to grind on my cock. Our hands and fingers interlocked, and she leaned down again to kiss me. This time, we held the kiss for several minutes. All the blood was rushing to my face; it was a wonder I even had any blood left to maintain my erection.

"Come on! Giddy up!" she teased, bouncing higher on my lap. My arousal helped me overcome my initial sense of stage fright, and I thrust up into her as she came down. As I got more into it, I started to take more of an active lead. I wormed my fingers out of her grip, and I wrapped my arms around her body. My thrusts got more and more frantic. I rolled the both of us over so I was on top before I resumed fucking her.

"Oh my!" she exclaimed. "I've never had my horsie ride me before! Keep going, horsie! Ride me all the way to the finish line!"

I let my primal instincts take over - or maybe they overpowered me - and tried angling my hips in various ways to achieve the best potential feeling in my dick. I could feel it starting to go numb, and I knew my first orgasm with a girl was just around the corner. When I came, I threw my head back and mouthed out something that I couldn't comprehend, even if my sense of self wasn't blurring from the climax. I braced myself against the bed, leaning down over Penny. She was staring up past me, her expression blank and her mouth slightly open. I looked down at our hips were we were so intimately connected. I could see our muscles quivering in the throes of our orgasms, though her stomach and legs were shaking a lot more violently than my own. I could feel her insides tightening around me even more. Was this what a girl's orgasm was like?

As I came down from that unbelievable high, I wrapped my arms around Penny. She returned the gesture. I allowed my legs to straighten out, pushing Penny up to the head of the bed with me so we were in a comfortable position for cuddling.

"Mmnn... you were an amazing horsie." she cooed, pulling me closer. I was still inside her, but I could feel my dick starting to limp and despite her muscles' best efforts, I slowly slipped out of her. My dick felt lonely and cold out in the open air. If I could, I would stuff it back into her and keep it there forever, but I knew that just wasn't possible, nor could I hold an erection for nearly that long.

"So... what does this mean between us?" I asked, my voice trembling a bit from the curiosity.

"I don't know. It could be just a fun fling between us, or it means everything." She answered. "Sex... is an important part of our lives as humans. It's the glue that binds us together, where we let all our walls down, and where we are as close as we can possibly be."

"I really enjoyed it."

"That's good! I enjoy it, too, and I wouldn't be able to be with a guy if he didn't love sex as much as I do!"

"There are really guys that don't like sex?" I asked. I found that hard to believe, considering all the masturbation talk that went on between the boys in my school.

"You'd be surprised."

"I should get back to my cabin before my parents realize I'm missing. I don't think they'd appreciate me sneaking out in the middle of the night."

Penny simply giggled and gave me another kiss on the lips.

"Let's just stay like this for now." she said. "I'll get you back before morning."

  • * *

That night was the greatest night of my life. I would still look fondly back on it years later. We had sex several more times that night, and while my dick recovered in between, we explored each others' bodies. I gained a much greater appreciation for the female body from it. Penny's breasts were amazingly soft. I was careful not to squeeze them too hard out of fear of hurting her, but she assured me that it felt good either way. I also found out about this very tiny bulb just above her vagina that, when I touched it, made her squirm and gasp and left her breathless.

We eventually slept until about 4:30, at which point she woke me up and we got dressed to sneak back to my room. When I got there I slept for another two hours; despite the much less sleep I got, I never slept better, though I felt cold without Penny there to keep me warm. I could still smell her unique scent on me, which reminded me of a garden of flowers. My parents were none the wiser about my little escapade.

The next two weeks on the cruise was largely spent with Penny. By day we hung out at the swimming pool or played games in the game room, and at night I'd sneak out again to meet at her cabin to fuck repeatedly. She showed me all kinds of new positions I never imagined, and techniques to bring her to climax over and over again. Seeing how easily it was to shove her over the edge kind of made me wish I was a girl. She didn't have to cool down between orgasms, and she could even have them back to back. She also mentioned something about multiple orgasms, though that seemed a bit overkill when one was intense enough.

The last day of the cruise felt like I was preparing to leave paradise. The two weeks we spent together felt like an eternity, but at the same time it passed all too quickly. This evening we'd part ways and I didn't know if we'd ever see each other again. She seemed to know this, too, as her constant smile and grin was replaced with a somber look that made you know she was happy, but all too aware that the happiness was about to fade.

"Penny, I... I know we've only been together for a few weeks, but I think I like you. A lot." I said as we laid on the bed together in my cabin.

"Would you say you love me?" she replied.

"I... I think so, yes." My heart was racing at the idea. I basically just confessed to her, something I've never done to anyone before, and I knew doing so would set me on a single path inextricably. Despite my apprehension, I knew she was someone, THE one, I would do anything to spend the rest of my life with.

"I'm glad. I love you, too, Max." She gave me a tight warm hug and then slipped off the bed. She rummaged through the drawer of the nightstand between the two beds and found a pen and notepad. She wrote down a phone number and address and tore the page out of the notepad and handed it to me.

"I know it'll feel like an eternity in limbo, but once we're adults, and once you're able to go out on your own, come find me in Utah." she said.

"Thank you, Penny."

The dreaded evening finally came when we would have to say our goodbyes. I tried to pretend my relationship with Penny was a platonic one, but as we prepared to get off the ship, I made no attempt to hide it from my family. I held her in a tight hug for several minutes, even giving her one final kiss. I could see her parents watching on - I knew this when Penny headed to their side after all was said and done. At best, they seemed indifferent to our relationship, and at worst they were quietly judgemental.

"I'm going to miss you, Penny." I whispered to her.

"I'll miss you, too."

It was difficult watching her leave. Even though we had only been together on a fling for two weeks, I felt very close to her. I watched her for as long as I could until she was out of sight. Once we were in the car, I could feel myself starting to tear up. I turned my face down and to the window, pretending to read a book in my lap.

"Did you enjoy yourself, Max?" My dad asked, looking at me through the rear-view mirror.

"Y-yeah. Yeah, I did." I answered. He didn't ask Anthony the same thing, which made me wonder if he knew that I didn't actually sleep in our cabin the entire cruise. I wouldn't doubt that he woke up at least once and came to that conclusion. He was a lawyer, after all.

I quickly dried my eyes off on my sleeve and looked outside. I saw Penny one last time in the parking lot. She was in the backseat of a Bentley. I noticed that she was also crying. As strange as it may sound, seeing that actually made me feel better. It let me know her affection for me was also genuine, and that she was broken up to see me go.

I knew that once we were adults, and this would eventually come to pass for real, that I would reunite with her in Utah. We would attend the same university, get engaged, move into a large house and have three children; two daughters and a son. Other people may scoff at the circumstances of how we met, but our love for each other has always been sincere.