Beginner's Luck

Devon's orgasm lasted a long time and I kept my hand wrapped around his cock while he came down. Aftercare, you know. Eventually coming back to his senses, Devon's first reaction was embarrassment. "I should clean myself up..."

I pressed on his chest and shook my head. "Relax, I've got it." Reaching behind me, I produced the damp washcloth I had brought along for exactly this reason. I gently wiped Devon's chest, but stopped before I got the last bit of cum. This I scooped up and put in my mouth. "Yum." That certainly got his attention and I enjoyed helping him remain comfortable as he recovered. I really wanted this whole experience to be wonderful. But I had to be careful of one thing.

Devon was now looking at me with puppy love in his eyes. That's normal and calls for tact. Luckily, I had a good card to play when he asked hopefully, "Can we do that again?"

I smiled and shook my head. "No sweetie, not with me." He didn't seem able to process this bit of news. "Oh, you young guys! I know you'll be ready again soon and you'll be taken care of, believe me." With a sly smile I gave Devon a kiss and then reached for my phone. Moments later Katie walked in and high-fived me.

"Tag, I'm it!" she cried.

Last I saw, Devon was wide-eyed as I left and Katie took my place.

Some time later I had a quick conference with the girls while Devon returned to his gofer duties. But he would be interrupted before long. The plan was for the girls to give him as many handjobs as he could take throughout the rest of the day, which for a young guy would be a lot. That way he would experience some variety and also learn a little self-control. A guy's got to have some stamina if he's going to please a girl someday.

I watched proudly when I saw Emily intercept Devon as he was completing a chore. She led him off to a private area for another "lesson". It felt rewarding to be giving this sweet boy such a lovely gift.

The next morning there was another pow-wow of the females. Apparently, Devon had acquitted himself well. He was unfailingly polite and grateful and had experienced no less than five handjobs with as many girls. The last of which, Ariana, said she thought he could even have gone again. But she put him to bed, where he no doubt slept like an angel.

Good thing, too, because we had another lesson planned for Devon the next day.

***

I sat down across from Devon during breakfast, unable to keep the Cheshire Cat grin off my face. "I thought you might still be in bed after the day you had yesterday."

He immediately beamed at me and sighed. "That was the most amazing... I don't know what to say."

"Say thank you".

He looked me in the eye soulfully. "Thank you."

"You're welcome," I said, helping myself to some bacon from his plate. "Tired?"

"No, I feel great!"

"Good, you're going to need your strength today. When you're done, go find Nancy. I believe she has something to say to you."

I flounced off smugly, delighted in the knowledge of what was to come. Devon must have wolfed down the rest of his breakfast because I noticed Nancy leading him away just moments later.

Nancy had been chosen to give Devon his first blowjob. She made an impassioned case, describing her love of the act, her commitment to superior technique and ongoing improvement and even provided references (which was an amusingly long list). The girls scheduled to take over afterward also had stellar credentials. Devon wasn't going to know what hit him.

I pieced together the story of what happened afterward. Apparently Nancy had Devon hooked and fascinated from the outset. She sat him down in the TV room (with the door guarded by a co-conspirator) and matter-of-factly informed him what was going to happen. She even asked for consent, which was enthusiastically given. But the dear guy wanted to talk a little first -- he wanted to make sure he wasn't taking advantage of her!

Ever straightforward, Nancy assured him she was there by choice and indeed, relished the task. She remarked that the TV room, with its movie style seating, reminded her fondly of the blowjobs she'd often given during midnight showings of Rocky Horror. It turned out Devon was one who enjoyed a story and Nancy began cuddling and touching him while she recounted her scandalous college years.

Growing up, oral sex was a subject of revulsion among her innocent friends. How could a girl do such a thing? Having resolved to never participate in something so disgusting, Nancy surprised herself by discovering, with her college boyfriend, that being on her knees was her very favorite thing. She loved providing such exquisite pleasure and enjoyed how she felt and looked doing it. Nancy also found being an avid "swallower" rather than a "spitter" put her in demand. She described a few incidents to an awed Devon: the time she gave blowjobs to two different guys on the same day; the first time she made a boy cum on her face; the night she found a friend on her knees at a party sucking cock and asked politely if she could help.

Devon was about to experience his first oral sex from something of an expert, and part of Nancy's skill was that she understood how to bring someone new along. As she got Devon out of his pants and seated before her, she explained that she would go slow at first and that there was more to come if he could last a little.

Settled comfortably on her knees, Nancy began her joyful task. She could do all the usual things a good fellatrix can do, a few unusual things, plus a couple of things not many men ever get to experience. It's to Devon's credit that he lasted any time at all with her.

Satisfied that he was learning control, Nancy demonstrated some of her favorite techniques. She went fast, she went slow. She deep-throated. She rubbed his cock all over her face while making eye contact. Nancy also made sure he understood not all girls would be as uninhibited and he must get to know them before moving on to her next trick -- she coached Devon to put his hand on the back of her head and take charge.

"I don't mind having my head pushed down as long you remember I need to breathe once in a while." She let Devon experience that for a few minutes before continuing the lesson. "Some girls will like it if you're assertive and 'force' them to do what you want", she said, making air quotes. "I'm into that, so you can do whatever you like. You can even pull my hair. Go ahead."

Nancy had obligingly put her hair in pigtails for the occasion and Devon truly was treated to a blowjob fit for a king. And though he was too inexperienced to take any real advantage, Nancy made sure he gave her hair a few good tugs. Among other points of etiquette, she also told Devon he must always give a girl warning when he was about to cum so she could decide if she wanted to take it in her mouth. Of course, Nancy was a sure thing. But she made him verbalize it on the theory of performing as you practice.

In the end, Devon was left limp and drained of energy with Nancy smiling up at him at she gleefully swallowed. A real pleasure for her, she said afterward. She then sent him back to work, with fair warning that there would be more "instruction" throughout the day.

Truth be told, there was no shortage of volunteers. At first it was a novelty, but as word of Devon's kind and sweet nature spread, nearly all the girls were up for a "tutoring" session. Their resolve was further solidified after some negative interactions with the other guys.

Katie reported two of the cameramen sounding annoyed when they learned what the girls were doing for Devon. What about them?

"Not my problem," countered Katie.

I heard rumblings about this a few times before I was confronted directly by Todd. I had never liked Todd.

"Are you telling me," he asked incredulously, "that this little wuss is getting it from all the girls? The kind of sluts that are on this boat are giving it up for him, but not me? Not Barry? What the hell?!"

Nancy happened to be standing next to me and she quickly settled his hash. "Todd, there's a reason we like Devon," she said. "It's because he's a good guy. He's not entitled, he's not mean spirited and unlike you he wouldn't think of slut shaming anyone. Not every girl will just fall over on their back if you're six-foot-four, into MMA and have a lot of tattoos. The fact is, you're a vapid twit. Which means he gets it and you don't. So fuck off!"

That... was most definitely that. Better still, Todd was put off the boat shortly afterward for abusive behavior and I felt it couldn't have happened to a nicer guy. I waved merrily with my arm around Devon as Todd was escorted ashore.

The rest of Devon's day was as heavenly as Todd's was unpleasant, with girl after girl getting on their knees for him. The finale was Eva and Amanda together and they quite enjoyed giving him something most guys will never experience in their life.

In what was becoming our nightly de-brief, the girls mentioned Devon was gentlemanly to the end, which was great. But we also realized Nancy was right to teach him some assertiveness. More discussion was needed to bring along our young man properly. The next day was already planned out, but we also talked about showing Devon how to make a willing girl feel taken, womanly and even submissive if she were open to it.

Day three was rainy, which meant indoor action only. More photo shoots were planned, along with a lot of day drinking. That always led to good footage, plus the guys were on their best behavior after Todd got his comeuppance. Our curriculum for Devon that day was centered on him learning to pleasure a girl. Assuming it went well, we were planning for his "first time" that evening. The question was, which girl should do the deed?

The decision wasn't mine alone, though I felt largely responsible. It seemed dangerously like playing god -- who were we to dictate Devon's first time? Would we be stealing the opportunity from the future love of his life? Then again, without our intervention it could fall to some dullard of a girl in the back seat of a used Toyota.

But first things first. To the surprise of nobody, it was easy to get volunteers for Devon to practice pleasuring. We had commandeered a small stateroom to use as our "classroom" and drawn straws to see who went first. Courtney won and I decided to supervise. We gave Devon a fairly serious talk about how pleasuring a woman is an art and takes experience and patience. I was prepared to talk him out of any bad attitudes he might have picked up from one of those podcasts hosted by idiotic "influencers" who always seem to hate women. But fortunately, Devon had a better nature than that. He had been looking forward to his first taste of pussy for a long time.

Suitably prepared, Devon made out with Courtney for a few minutes before she got naked and comfortable. We then continued the lecture with a guided tour between Courtney's legs. She's a showoff and I could tell she enjoyed being a visual aid as I discussed her anatomy. I thought Devon's eyes might pop out when I asked her to spread herself open, more for fun than for education, admittedly. I pointed out that she was visibly wet and her clit was begging for attention. At my direction, Devon laid down alongside the lovely girl so he could touch her. He stroked her whole body before centering his attention on her pussy. Courtney told him how she liked to be touched, cautioning him that every girl is different.

I then prompted him to kiss between Courtney's thighs and work his way up. I gave him a little kiss too and watched with pride as he went down on a girl for the first time. And indeed, he was a natural. Devon paced himself and started slowly, which was good for both of them. But he clearly enjoyed himself from the get-go. Soon he was pushing his tongue into her wetness as far as he could. Without any prompting from us, Devon slipped two fingers inside Courtney while lapping at her clit. To her surprise, Courtney found herself cumming in mere minutes. She lurched and cried out and Devon hung in there until she was done.

Any good teacher hopes for the day a student truly achieves on their own, and I couldn't have been more proud. Courtney was momentarily indignant: "You must have done that before -- no virgin could make me cum like that!" Devon just grinned and shrugged, while Courtney fell back exhausted and giggling.

I pointed out, "Either way, he's not going to be a virgin much longer." Devon looked at me in surprise and I added with a grin, "A few more to go first. Have to make sure that first time wasn't a fluke."

Courtney got herself together and gave Devon a big kiss, adding that she was available for more practice any time. She sent in Sue, a very petite and incredibly beautiful girl of Korean heritage. It turned out 'Sue' was the American-ized version of her true name, Soo Yun, which in turn means 'lotus flower'. She quickly stripped and presented her lovely lotus flower for Devon. He was definitely getting a taste for pussy, though I encouraged him to again start slow. He then had the idea of giving her a massage, which was fine with Sue. The girl's ass was so perfect I was tempted to participate. When Devon had her flip over onto her back Sue remarked, "Usually, it's the Asian girl giving the guy a happy ending. Progress!"

Sue gave Devon an important lesson which hadn't occurred to me. She asked Devon to be a little rough with her nipples. I like mine treated gently, but Sue wanted Devon to squeeze enough for it to hurt a little. That was new for our young man and it took some convincing from Sue for him to not hold back. She had those brown gumdrop nipples which are easy to grip and Devon soon had her gasping and moaning. With some coaching, Devon alternated between squeezing Sue's nipples hard and then kissing them to provide relief. It was against his nature to inflict pain, but Sue pointed out there's a difference between harming someone and stimulating them in a way they enjoy and request.

Soon, Sue guided Devon down between her legs and kept her hand on the back of his head while he pleasured her. She enjoyed the trick he had employed with Courtney, fingering her and licking the clit at the same time. But to cum, she wanted him to focus on her clit. This was another good lesson, that different girls need different types of stimulation. I made a mental note to warn him that not all girls will readily verbalize this and might need to be drawn out.

Devon looked positively smug after drawing shrieks of pleasure from Sue, which were no doubt heard outside the little stateroom. Watching had gotten to me, so I decided it was my turn and Sue and I switched places. The kid was a fast learner, that was for sure. After just a few moments I felt certain we had given Devon a good start and he would do well pleasuring just about any girl who wanted it. I also felt good about giving him his first time later that day, but still didn't know which girl should be the one.

Those concerns fell away as Sue decided to help. Devon, being a good learner, went with it and soon I had both of them lapping at my pussy. Ever had your clit sandwiched between two tongues, ladies? If not, you're letting the best things in life pass you by. Those two had me moaning and talking dirty before cumming my head off. Sue made a point of kissing Devon's lips clean and we all took a moment to relax.

Devon was again smiling from ear to ear. I scolded him with mock seriousness, "Don't look so damned pleased with yourself. Still two more to go before you get yours."

"Nice work if you can get it," he replied good naturedly.

Sue and I got ourselves together and sent in Amanda, followed by Katie. We gave them privacy, but got glowing reports afterward. It was unanimous that Devon was good at pleasing a girl, both in technique and in temperament. I think we all felt it was rewarding to bring along a young man this way. Once again, there would be no shortage of volunteers for Devon's big moment.

Devon was definitely ready for his own pleasure after taking care of five girls. It must have felt like an eternity to wait while we held a meeting to decide who would take his cherry. There were a lot of variables. Should it be the most enthusiastic girl? The most conventionally attractive? This whole thing had been my idea -- should it be me?

We all re-entered the cabin to find Devon sitting anxiously on the bed. Some of the girls were having fun keeping him in suspense, but I felt it would be cruel to delay any further. "Devon, you've been nothing but sweet and we've all enjoyed teaching you something this week. So it was hard for us to decide who would be your first. Just know that we all threw our hats into the ring. Enjoy!"

With that, we all began to file out of the room. Some of the girls gave Devon a quick kiss or words of encouragement as they departed. He was visibly shocked when I turned to go, having thought it would certainly be me. I stopped, looked him in the eye with a knowing smile and nodded, very much like Kate Hudson in "Almost Famous". It was okay, I was happy for him and he should have a good time. I closed the door behind me, leaving Devon alone with Emily.

***

As I said earlier, aftercare is really important. Equally important is setting realistic expectations. Emily was chosen to be Devon's first for a number of reasons, not least of which was that she was savvy enough not to allow Devon to fall in love with her. Indeed, she let him know gently but firmly that after their shared pleasures (as many times as he liked), she would not be spending the night or being his girlfriend later. This was, after all, an educational program, which she managed to say with a mostly straight face. Or so Emily told us the next morning. She was actually a little shy about it, having thoroughly enjoyed the experience herself. But we got it out of her that she and Devon had done it no less than four times! As for Devon, he was floating around with a visible glow. It was mid-morning when we, all the girls, held a meeting for the first time with Devon included.

We had put considerable thought into what would come next. Originally, the plan had been to give Devon his choice of the girl he wanted next as a kind of reward at the end of his "training". But we realized it would put him in an awkward position. He had such a kindly nature, Devon would not want to choose one person because he might feel he was slighting the others. After some discussion we arrived at another plan that didn't Devon selecting anyone and had the added feature of involving more people if they so desired. This was explained to Devon and I don't think the point was lost on him -- who ever has a committee of dedicated people putting their full attention and planning into your pleasure? Indeed, one of the reasons we started this was because Devon wasn't likely to overlook how lucky he truly was.

So we explained that for the rest of the day and into the next, if he wanted, he could be with a variety of girls. We would curate the order, again with an eye toward providing him a varied and comprehensive education. And also, incidentally, a few of the girls really wanted to get laid! They were sincere in wanting to give Devon a wonderful finale. But a few were also still invested in making the point that the other, more superficial and stereotypical "bros" weren't going to get any.

We sent Devon back to work, with the expectation that he would be having some lovely breaks throughout the day. Part of the fun was that he wouldn't know when it was going to happen. The order was chosen to maximize variety. Jenn was next to provide a different body type, as she was quite curvy. She ambushed Devon as he was cleaning the kitchen and they had a lovely time in the stateroom. The report was that Devon lasted a respectable duration and got to experience taking a girl from behind for the first time. Jenn said it was lots of fun, but that Devon was still being very nice. Perhaps a bit too nice, even.