Beginner's Luck

Devon was just adorable, like a friendly puppy. My first reaction was to question whether he was allowed to be on the boat at all, but it turned out his eighteenth birthday had been a week earlier. He certainly didn't look it and seemed utterly out of his element. But even the Fonz might lose his famous cool in the presence of two dozen scantily clad models. I had better explain...

This was a job I'd had for the past two years. Working my way through college as a stripper was considerably easier than waiting tables. Modeling was easier still. I jumped at the chance and found that as long as a girl didn't mind getting naked, there was good money to be made. So while I could honestly say it wasn't porn, it wasn't the Sports Illustrated swimsuit issue either.

I worked for a company that specialized in "amateur" videos. Which is to say, they filmed professional models pretending to be amateurs. Every summer they would hire a bunch of us to ride on a party boat for a week and film whatever happened. We were expected to get naked and show off for the cameras, but there was no script. No drugs were allowed, but we were free to drink as long as we didn't get sloppy. A handful of guys were along (who were NOT allowed any alcohol) to make it look like we were being slutty, but that wasn't actually part of the deal. They were mostly there to run the boat and be camera operators. Sure, some girls hooked up with them, but that was extra-curricular. It was a fun job, it paid well and if I changed my hair color the rest of the year nobody recognized me.

Devon was the younger brother of one of the male crew and they had finagled a job for him as a production assistant. That meant he had no particular duties, but could be asked to do just about anything that came up. He had clearly never been around a group of models. But unlike some other guys we worked with, he didn't stare and openly lust after us. The boat was about to depart and I noticed him working very hard to untangle some camera cables that didn't seem to need it. I sidled up to him and watched until he noticed me. I was wearing cutoffs and a rather flattering bikini top which Devon definitely noticed, but his eyes quickly went back to his work.

"Are you Joe's brother?"

"Yes."

"Welcome to the party boat! I'm Jessica."

He looked up again and shook my hand, making a hell of an effort not to notice my nipples. They were hard to miss as they poked through my top and I grinned at his discomfort. "I guess you'll be recording me a lot over the next few days."

Looking down at his wires again Devon mumbled, "Maybe. I'll try to be... Um, well, I'll try to be professional. I know it's your job."

The poor boy was so shy! But it was sweet that he wasn't ogling the girls and didn't want to be a creep. It spoke well of a boy his age.

"I'm sure you'll do fine. If you're not sure, just point the camera at me. I won't mind."

Devon nodded and fled below deck. I got a drink and found some of my friends from the previous year. They too had noticed Devon and how hard he was working to keep it together. What young man ever finds himself in this situation, with wall-to-wall models? And we weren't even naked yet. How would he handle that?

It was the usual routine on the boat. We made a big deal of leaving the dock, with music blaring and the girls dancing and flashing their boobs. Devon was tasked with bringing us drinks and immediately found himself face to face with some very attractive, half-naked girls. They seemed amused by his discomfort, but again it was classy that he was trying to give us space and not stare.

The rest of the day was partying, clothes taken off and put back on (or sometimes left off) and lots of flirting. We would tease the camera guys, posing or dancing provocatively and even gave a few lap dances. At one point I was on my friend Gary's lap while he filmed some POV footage and Devon was called over to record from another angle. My top was nowhere to be found and I was grinding away on Gary while Devon filmed. In this case, he had to look and I could see he was fascinated.

"Devon, have you ever had a lap dance?"

Wide eyed, he shook his head. I immediately hopped off of Gary, much to his disappointment, pulled him out of the chair and brought Devon over by the wrist. "Put that down for now," I told him, handing his camera to Gary. I wanted Devon to focus on his first ever lap dance. Facing Devon, I settled my bikini clad butt down and immediately encountered a serious erection. I smiled and draped my arms around his neck, while he gasped at the contact. The poor boy seemed stunned.

Moving slowly, I took Devon's hands and put them on the small of my back. He simply held me stiffly, so after a moment I whispered in his ear, "You can touch me. Go ahead, all over."

Gary was recording from the side as Devon slid his hands timidly up my back and down to my bottoms. His cock was rock hard under me, but he wouldn't go further. "It's OK," I told him. Reaching behind me, I guided his hands onto my ass. His breath sounded like he was running a fast mile. I gave him a moment before I decided to really blow his mind. Making sure Gary was still filming, I slid off Devon's lap, turned around and sat down again with my back to him. Then I slowly, gently reached down and adjusted his cock with my hand so it was aligned with my ass. Giving it a nice squeeze, I settled back, took Devon's hands and slid them up my belly to my breasts.

Devon reacted strongly, though he was gentle as he felt me up. It might have been the first time he touched a girl this way and I felt strangely honored. I could feel his erection twitching against my butt. After mere moments of this Devon froze and gasped. I was certain he was cumming in his pants, so I helped by moving rhythmically against him. He was struggling not to make a sound the camera would pick up, but couldn't contain a couple of soft moans that I could hear as I leaned back into him. He certainly moved against me as if he was having an orgasm and slowed down as it finished. I twisted to nuzzle his neck. "Was that good?"

He was speechless and could only nod. I stood up, making sure Devon had the chance to turn away from the camera -- I was concerned he might have a big wet spot. I faced Gary's lens and gave a big smile and a thumbs-up. It was just the sort of footage we wanted and Gary nodded happily before finally lowering the camera. Devon, meanwhile, bee-lined to the restroom.

The rest of the day was full of similar antics. Devon returned wearing a different pair of shorts, I noticed. The other girls teased him about our lap dance and he actually blushed a little. They all thought he was a very nice boy. Indeed, that night he was the main subject of conversation.

I was nursing yet another margarita on the couch below deck when Amanda sat down next to me. "That boy Devon -- what did you do to him?"

"Just a little lap dance. He was cute about it. Why?"

"Joe said it was the first time he saw his kid brother doing well with a girl. Apparently he was not popular in school."

I nodded ruefully, having seen it before. A kid gets a label and there's no changing it. Then the kid starts believing it. Such a shame. Has nobody seen The Breakfast Club in this day and age? For people like that, sometimes their best hope is to switch schools or wait for college to change things up.

Amanda continued, "Devon is so shy and seems so nice. Joe thinks you really made his year."

I again felt proud. More so, now that I knew a little about Devon's background. I decided to check on him. The guys were spread out around the lower deck and topside, some still performing their cameraman duties. Joe found me first and confirmed what Amanda had said. "Whatever you did to Devon earlier -- he's a new man!"

"Didn't he have a girlfriend when he was in school?"

Joe shook his head sadly. "Tons of girls who were friends, but nothing beyond that. He never could take the initiative."

"Well, I'm glad I could do something for him."

"And on day one, too! Thanks Jess. I hope it helps his confidence."

I nodded and continued searching for Devon. Turned out he was in a corner working with some of the video equipment. "Hey, you've put in your time today. Relax and talk to some of the girls."

Surprised to see me, he stood up fast. "Hi! Um, well... we've got all week. But I need to make sure this monitor works."

I took the gadget out of his hands and put it down. "Nope, enough work. Follow me."

Leading him by the hand, I introduced Devon around to the other girls. With a little coaching he was making eye contact, smiling and soon having a great time. I was sure he had never had this kind of attention, and never been around such beauties. Diana, a petite and mischievous looking blonde, touched his cheek and rubbed his arm. "Your brother Joe is a friend of mine. I'm so glad to meet you Devon. I'll give you some good stuff this week. To film, I mean."

I could see his face flush as Devon soaked in the attention. Word had gotten around and all the girls were super friendly with him, tickled that he had so little experience and suddenly thrust into this crazy situation.

The next day was more of the same. Devon had quickly become everyone's favorite and although he was obviously fascinated by the girls he never came off as anything but polite and kind. He even handed away the camera a couple of times rather than record the girls doing something raunchy. Amanda asked him about it and he replied, "They've been so nice to me. I didn't want them thinking I was creeping on them."

Amanda confessed to me that, unable to resist, she had kissed Devon. The boy melted in her arms, she said. Diana said much the same -- she had kissed him too! An idea occurred to me and I decided to round up the girls. Something had to be done.

We met on the bow. During the past day we had all gotten to know Devon a little and found him adorable, but also a bit sad. He had no real experience and was so polite that he couldn't possibly be direct with a girl. Eva had spent some time talking with him and confirmed what we all suspected: Definitely a virgin, had never even kissed a girl before this week. And he felt intimidated by the muscled, outgoing guys we had on the crew.

Clearly, this required action so I put forth an idea. The girls were a little shocked at first, but quickly saw it would be fun. Even better, it would put some of the boorish "bros" in their place. We decided Devon would be our project for the remainder of the cruise. I was elected to explain it to him the next day.

We were scheduled for a photo shoot. The boat would let us off near a lovely house with a private stretch of beach and all the girls would prance around mostly naked when we weren't busy taking photos. Camera guys would be recording nonstop. The photo area had all the equipment, plus a large tent. That was the makeup and sun block station. The girls were supposed to lotion up just prior to their photo shoot, after which we were free to frolic on the beach.

Once everything was in place I took Devon aside. "We've been talking about you."

"About me?"

"Yes, you've made a really good impression on the girls. Lots of guys act terribly around us in this job, but you've been a gentleman. And we know it's hard for a 'nice guy' sometimes."

"That's what Joe says. That I'm too nice."

"Well, for once, the nice guy is going to win. The girls have decided, if you're okay with it, to give you a great week. We want to give you some experience and teach you a little. But mostly, we want you to have the time of your life. You up for it?"

I might as well as told him he was winning the lottery. "You mean..."

Now I got close to him, putting my lips to his ear and boldly sliding my hand up his thigh. "That's what I mean. We are going to teach you how to use this," I said, giving his cock a squeeze. "And we're going to teach you how to please a girl. But you have to be patient and let us take you along our way. Deal?"

Again, the poor guy just looked stunned. I felt his cock jump within the fabric of his shorts. "I'll take that for a yes!"

I brought Devon to the tent to find several barely dressed models waiting and grinning. "We want the girls to look sleek and shiny in the photos, so they need sun block covering them completely. That'll be your job."

Good thing he was a healthy eighteen year-old, because this might have caused cardiac issues in a less hardy specimen. Devon gaped in disbelief. I don't think he understood it was real until Eva stripped off her bikini and stood up straight with her wrists crossed above her head. "Oh, Mr. Lotion Man," she lilted. "I'm ready!"

We smiled and nodded at Devon to get to it. I whispered to him, "Have fun, but go slow. See how she reacts when you touch her."

Eva grinned at me when Devon moved behind her, excited to be the first girl he would touch at the start of our "program". Devon squirted lotion into his hands and started at Eva's shoulders. He spread it around and moved on to her ribs and deliciously smooth belly. Then down her thighs and calves. She was enjoying it and I wondered how daring Devon would be. On the way up he headed for her back before I interrupted, pointing at her ass. "Missed a spot." His hands slowly, shyly spread lotion over her shapely butt, as Eva squirmed with pleasure.

Eva took over now. "Make sure you take your time up here," she said, nodding to her breasts. Eva was about a B cup with cute nipples. Perfect for his first time, I thought. Standing behind her, Devon slid his hands around her body slowly. Eva sighed as he felt her gently, but quite thoroughly. Then she turned and whispered to him. Devon began gently squeezing her nipples, bringing soft sounds of enjoyment from Eva.

"All around once more," I told him. "Make sure she's covered." Devon complied, moving his hands languorously around the cute blonde. Polite as ever, he backed off when he thought he was done. But Eva gently admonished him.

"Still one more spot." It was obviously her pussy, shaved bare and smooth. Devon hesitated and she again spoke close in his ear. With her directing him, Devon got his first feel between a girl's legs. Eva cooed softly and gave him a few more pointers. She then pronounced the job done, looking a little flushed herself. She gave Devon a sweet kiss, but then her expression turned devilish. "Next!" she cried.

Katie eagerly dropped what little was covering her and assumed the position so Devon could lotion her up. She was athletic with long dark hair, which she charmingly gathered up and out of the way. As Devon covered her with sun block the sheen glistened alluringly and the boy looked closer and closer to fainting. After finishing Katie's back she turned around and watched him do her breasts. Devon massaged the lotion onto her chest with a trance-like expression, allowing Katie to surprise him by leaning in for a soft kiss. She spoke into his ear briefly and then resumed kissing Devon while he moved his hands on her.

The other girls and I watched with amusement and satisfaction. This feeling was not shared by the camera guys, who were visibly jealous. One even asked when it was his turn to be on sun block duty, and Diana shut him down immediately. We were all enjoying seeing Devon get his first taste of honey.

After Anna and Faith had their turn it became clear that poor Devon needed some relief. I had been elected to take him through this milestone and he allowed me to steer him away toward another, more private tent. The remaining girls made a point of applying their own sun block, much to the disappointment of the guys who could only point their cameras and fume.

I closed the tent flap and had Devon lay down next to me. "Having fun?"

"Oh my god, yes. I can't believe this!"

"It gets better." I put a hand on his thigh and slowly slid it up to the hard lump in his shorts. "Would you like me to take care of this for you?"

The overwhelmed boy could only nod desperately.

I knew it would take barely a moment with how worked up he was, but we had time. Plus I was determined to be a good teacher, and that means... repetition. Propped up on my elbow I narrated what I was doing. I really wanted Devon's first true touch to be special and began with my hand on his chest.

"In a moment, but not yet, I'm going to touch you for real -- under everything. Has a girl ever done that for you before?" He shook his head. "I'll go slow." I started languidly stroking Devon's hair, his face, his chest. Then I slid my fingertips down his belly and felt his hard cock through the shorts again. I was thorough, touching and gently squeezing his full length. Then I just barely poked a finger beneath the waistband and made contact with the head of Devon's cock. He gasped as if in disbelief that a girl was finally touching him. It was time -- I slowly but firmly slid his shorts down and off.

Laying my head on his shoulder so I could watch, I reached down and slowly closed my hand around Devon's bare cock. He was iron-hard and I made sure to do nothing more than leave my hand on it. I didn't want to over-stimulate. "Feel good?" Already beyond verbalizing, Devon just nodded excitedly.

Slowly. Very, very slowly, I began to move my hand up and down his shaft. I suspected I could make him cum instantly with any sort of abrupt motion. It was almost a game to me. How long could I make this lovely boy's first handjob last? After a few strokes I stopped and gauged his control. He seemed momentarily settled, so I moved my attention to his balls. I just teased and tickled a little, but it caused Devon to lurch and pant. I backed off again and gently touched his chest. "Do you like how I touch you?"

More excited nodding. "Yes!"

"What do you like best?"

"When you stroke me."

"I thought so. Want me to do that again?"

"Yes, please!" He seemed increasingly desperate and I wanted my teasing to be fun, not cruel.

"All right. I'm going to stroke you again and this time I won't stop. Ready?"

A few gasped breaths and Devon steeled himself. "Yes." I carefully licked my palm and fingers, making everything very wet. Taking his cock in my hand again I stopped being gentle and careful. Now it was on and believe me, I know how to give a good handjob. I gave it a slight squeeze just below the head and began stroking. I've always believed a handjob should feel as close as possible to being in a pussy -- wet and tight. I moved my hand fast and firm, but not in a frenzy. My technique is very deliberate and I make sure to squeeze and twist a little as I stroke. I want to wring the orgasm out, making it last as long as possible.

Of course, I didn't expect Devon to last long at all. I was impressed he hadn't shot off the moment I touched him. His cock was very attractive -- average sized and nicely shaped. It was mine right now, but this was only the beginning. His cock would get a lot more attention this week.

I smiled idly as I stroked, with Devon's heart hammering against my ear. This was enjoyable for me too and I was curious how much he would cum. Young guys can usually do a lot. With my head on Devon's chest, I briefly considered stroking him onto my face. As fun as it is to surprise a guy with something nasty like that, I didn't want to complicate things. His first time should be simple and memorable.

Devon's cock began to stiffen even more in my hand. His whole body clenched and I urged him on. "That's it baby, let it go. Cum for me."

I kept my hand moving, letting him know the stimulation would continue. It's amazing to see a guy lose control and get a glimpse of heaven when they cum. Stroke, stroke, stroke. A strangled gasp escaped his mouth and his back arched as Devon went over the edge. It was indeed a lot -- four strong ropes of cum streaking his chest, with more escaping as I continued stroking. That's another thing, stroking through the orgasm and not stopping too soon. Lots of girls don't know to do that, I'm told. I continued wringing everything I could from Devon and hoped I was blowing his mind.