The Sensei

As I said this, Naomi's expression warmed. She reached over and grabbed my hand. "Of course, Jake. I've been silly. I'm asking a lot of you and I'm not 'putting out' as you yanks say. You don't have to explain yourself to me. I understand. I'm sorry for being childish about it."

On the way back to our apartments, she asked me if I wanted to spend the night. I agreed. A few hours later, we were lying on her bed, watching TV. Naomi was wearing a very thin tank top, with no bra, and tiny pajama shorts that showed off all of her slender legs. It was as if she was trying to get a rise out of me. And she succeeded. I had an erection from nearly the moment I walked into the apartment, and I was certain she noticed.

As we watched TV, though, she was unusually quiet. I had the distinct feeling that she was trying to build up the courage to say something. Sure enough, she eventually came out with it.

"Can I ask you something personal, Jake?"

"Um, okay."

"How many girls have you...um...been with?"

"You mean slept with?"

"Yes, shagged. Not snogged."

I knew the exact number immediately, of course, but I pretended I had to think about it. Eventually I said "more than 10, less than 20."

"And is it always...um...like that?" she motioned toward the wall separating our apartments, clearly referencing my encounter with Lynne a few nights before. "Is it always that...intense?"

I smiled. "Not always, no. Depends on the situation. And the person. Why?"

"It's just that, well, I've only ever been with two men, and when I heard you the other night, I...well...I just couldn't help thinking that maybe there's a lot I don't know. I know I'm being incredibly forward with you, Jake, but I wonder if you could describe it for me. What was she like? What did she do?"

Over the ten minutes or so, I described, in considerable detail, my night with Lynne. Naomi hung on my every word, occasionally interjecting with questions. She wanted to know every little thing Lynne did that I found sexy. I tried to describe the things I remembered, but it was often difficult to find the right words. But I did my best, and the effort to relive the encounter succeeded, if nothing else, in making me enormously aroused. My cock was practically bursting out of my shorts.

And that's when things got interesting.

You know, Jake, I've been thinking. It's not fair for me to ask you to play this role, to be this boyfriend surrogate, while not ever taking care of your needs... "

"Naomi, it's really okay..."

"No, hear me out, Jake. I want to propose a deal, a bargain if you will. I want to learn from you. I want to learn how to be a good lover to Liam. I want to know how men tick, what gets you worked up, what you really like and want. Don't take this the wrong way. I'm not going to have sex with you, Jake. I can't do that to Liam. But if you're willing to be completely open with, to tell me absolutely everything, to share all your desires and fantasies, I am willing to provide that...that...outlet for you."

I can only imagine what kind of expression I had on my face at this point in the conversation. I'm sure it was some mixture of shock and confusion. I understood what she was asking of me, but she was being pretty cryptic about what she was offering in exchange. After a few moments, I finally spoke, "what do you mean by 'outlet'?"

She smiled. "Well, Jake, I've been thinking about this all afternoon. If we're going to go down this road, we need some clear ground rules. In exchange for your...um...candor, I'll...um...let you see me. All of me."

"You mean see you naked?"

"Yes, and you can...um...touch yourself...wank...in front of me, whenever you want. In fact, that's part of what I want to learn. I want to see how you do that." She paused before continuing, "but that's it, Jake. The rest is for Liam. I'm not going to touch you and you're not going to touch me. And I'm not going to touch myself in front of you, either. Only Liam gets to see me come."

"Do you think he'd be okay with the rest of what you're proposing?" I asked skeptically.

"Doubtful," she conceded, "but he doesn't have to know, and I'd be doing it for him. If I can learn how to really please him, he'll benefit from it for the rest of his life."

There was a real earnesty in her voice. This didn't seem like some rationalization she'd come up with just to justify cheating on her fiance or alleviating her loneliness. She seemed to have genuinely convinced herself that this would ultimately benefit her relationship.

"Are you sure you won't regret this? I really don't want to be a homebreaker here."

"Homebreaker? Is that what you yanks call it?" She was smiling. "You're a sweetheart, Jake, but I've thought a lot about this, and it's okay. Do we have a deal?"

"Yeah, I guess we do," I said, reaching over to shake Naomi's hand. "So what next?"

THE FIRST EXCHANGE

Naomi smiled warmly. "Well you've already contributed quite a bit tonight, so I suppose I need to make a good faith showing of my own."

With that, she sat up and scooted over a bit on the bed, creating a little space between us. Then she moved her hands up to the spaghetti straps of the tank top she was wearing and slowly pushed them off of her shoulders. After a few more tantalizing seconds, she pulled the front of her tank top down, simultaneously exposing both of her breasts. To this day, that image is still burned into my retinas. Her breasts were flawless, large and natural, perfect for cupping in your hands, if only that was allowed.

"So you like?" she asked, with the confidence of someone who already knew the answer.

I just nodded, very much aware of the erection now bulging beneath my thin pajama pants. After what must have been at least 30 seconds of me just staring at her breasts, transfixed, I eventually spoke, "so...what now?"

She smiled again, "well, here's what I was thinking. I'll keep these out. Stare as long as you like. And while you're doing that, why don't you tell me another sexy story. You can choose. Just tell me about a memorable encounter."

My brain wasn't exactly firing on all cylinders, so it took me a bit to come up with a story to share, but I eventually thought of one. I began to tell her, haltingly at first, about the time my freshmen year of college when a sophomore girl I had just met led me into a closet in a dorm room and gave me an unexpected blowjob.

Before I had even got a few sentences into the story, Naomi interrupted me. "Jake, you should really feel free to...you know...touch yourself as you tell the story. I know you want to."

She was certainly right about that. My erection was so persistent that it was taking a significant percentage of my concentration just to resist grabbing it. So I stopped fighting the urge and let my right hand grasp my cock over my shorts.

I continued with the story, describing how the girl, a red-haired sorority girl who had come by our dorm to hang out with a friend, had chatted me up for a while and then, once we found ourselves briefly alone, had taken me by the hand and led me into a small walk-in closet in her friend's dorm room. I could tell that Naomi was hanging on my every word.

Once in the dark closet, the girl - her name was Carrie, I think - immediately went to her knees and began unzipping my fly. A few seconds later, my pants were down around my knees and my cock was in her mouth.

"Oh my," Naomi interrupted, "that's pretty forward. Are all American sorority girls so quick to suck cock?"

I shrugged, "not that I'm the expert, but...I doubt it. This was the only time something like this ever happened to me, and it was apparently part of some dare. But I'll get to that."

"So was she good it at...you know...sucking cock?"

"Um...yeah...really good actually."

"How so? What did she do?"

I explained that, in my opinion, the girls who give the best head actually let their hands do most of the work, that when it's done right, it should basically be a wet handjob, with the mouth providing the lubrication. I said that Carrie understood this and used her hands perfectly.

Naomi was astounded by this observation. "All this time I've been doing it wrong! Most of the time, to make it work, I end up having to move my head like a woodpecker. It's exhausting. And you're telling me I should just be using my hand to help?!"

"Um...yeah"

"Show me"

"Show you what? I'm not that flexible"

"Very funny. I don't mean with your mouth. I mean, show me how you use your hand. Take off your shorts and show me."

Why not, I thought to myself, and a moment later my shorts were down to my knees and my cock was standing at attention. Naomi's eyes went wide the moment my cock came into view. I started moving my hand slowly up and down the shaft of my penis, my eyes still glued to Naomi's perfect breasts.

"Is that how I should do it? Slowly like that?"

"Not really," I explained, "but you have to be slower and more gentle when there's no lubrication. Otherwise it can hurt."

"Hmm...I've got an idea." Naomi got up, her breasts jiggling wildly, and walked over to her dresser. On the top was a bottle of hand lotion. A moment later she was hovering over me, squirting the lotion onto my cock and right hand. As the lotion coated the length of my cock, I began moving my hand much faster, gripping it tightly. Naomi watched intently, like she was studying for an exam. She was now sitting next to me on the edge of the bed.

"Tell me the rest of the story, Jake. How did it end?"

"Well, at first it was so dark in the closet that I couldn't see anything. But eventually my eyes adjusted to the dark and I could see her. I could see that she was looking up at me. She'd take her mouth off my cock every few strokes and smile up at me, while her hand continued to stroke me. She was clearly enjoying getting me off."

"You liked the eye contact?"

"Oh definitely. There's something so intimate about that. I liked the smiling too. Some girls get so serious during sex. Playfulness is usually sexier."

Naomi seemed to consider that for a moment. Then she asked "So what then? Did she make you come?"

"Oh yeah. But not the way I expected. When I was getting close, I think she could sense it. She just stood up, abruptly, her hand still firmly stroking my cock, and she leaned in to kiss me. We hadn't kissed up until that point. It was a slow, intimate kiss. Then she moved her mouth up to my ear and whispered to me, 'come for me, freshmen.' Her voice was so sexy, so confident. Her grip was so firm. I came almost immediately after that."

"Wow, that's incredible. What happened to all the spunk?"

"Not sure. The floor of the closet, I guess. She pointed my cock away from her when I came."

"Well, I'm sure her friend appreciated that. Speaking of which, I can tell you're getting close now. Just shoot it onto your stomach and I'll get you a tissue."

Taking that as my cue to wrap things up, I took one last gaze at Naomi's breasts and allowed myself to come. Quite a bit of cum - more than from a typical wank - shot out onto my stomach, causing Naomi's eyes to again grow wide. As soon as I was done, she got me a tissue and immediately put her shirt back on. Soon we were back in bed, her nestled in against me, as if nothing had happened.

For the next severals weeks, this same general routine played itself out almost every other night. At Naomi's suggestion, we'd get naked (Naomi even took her shorts and panties off a few times), and I'd tell her about a prior sexual escapade while masturabating in front of her. As strange as it all was, it came to feel almost routine. We didn't do it every night, but at least every other. Before long, I was running out of material to share with her. I'd already told her about my most memorable encounters and even a few of the not so memorable.

HANDS ON LEARNING

Naomi seemed to get that I was only 22 and didn't have a limitless of supply of erotic stories to share with her, but I could tell that her thirst for sexual knowledge wasn't quenched. One night, as we were talking, I made the obvious point that there's only so much you can learn through verbal explanation or even demonstration. At some point you have to actually do something, you have to practice, to learn how to do it well.

Almost as soon as the words left my mouth, I worried that she might take them the wrong way. As much as I fantasized about her doing so, I really wasn't trying to convince her to break her ground rules. But I succeeded nonetheless.

"You know, you're right, Jake. If I actually want to learn how to do any of these things well, I'm going to need to practice them. I feel bad about it, but I still think Liam will be the ultimately beneficiary. So here are the new rules. I can touch you, as needed, but you can't touch back, at least not while I'm naked. Understood?"

I nodded. At that point, Naomi - who was wearing nothing but a pair of cotton pajama shorts - reached over and gently put her hand on my cock. I was so conditioned to the no contact rule that her touch felt at first like an electric shock. It was sensory overload. Slowly, gently, she began stroking my cock, doing a pretty good approximation of my own technique.

After a few minutes, she leaned over me and grabbed the bottle of lotion, which she now kept permanently on the nightstand. She squirted quite a bit onto her palm, rubbed her hands together, and then placed both of them around the shaft of my cock. Gradually she increased her speed, as well as the tightness of her grip. It felt phenomenal. The stimulation was so intense that I lasted less than a minute before erupting like a geyser. She was leaning over me so closely that some of my cum splashed up onto her left breast. She smiled when she saw it, as if admiring her handiwork.

After she'd gotten tissues for both of us and put her shirt back on, she asked me to give her feedback on her technique and implored me to be as honest as possible. I did my best.

Handjob practice continued for the next couple of weeks, including once in a movie theater and another time in the back of a train car. It was Naomi's idea on both occasions, but she was no doubt inspired by the story I'd told her about getting a handjob in the back of a school bus during a class trip in high school.

Eventually, I got around to asking Naomi something that had been bothering me since the beginning of our little training sessions: what did she do to satisfy herself? What was her own "outlet"? She seemed surprisingly reluctant to tell me, but she eventually admitted that she masturbated every few days, often after I'd left in the morning and she was on the phone with Liam. She thought it was important, particularly in light of what she was doing with me, to share as many of her orgasms as possible with Liam. Her orgasm was something deeply intimate that was reserved for him.

I respected her reasoning, as strange as it was. It made sense to me that keeping something like that private, sharing it only with Liam, helped ease some of the guilt she must feel for everything she was doing with me. And it was at least consistent with her justification for fooling around with me in the first place, that she was only doing it to benefit Liam down the road.

ORAL EXAMS

To my pleasure, but not my surprise, after Naomi felt that she'd mastered the handjob, she wanted to add a new skill to her repertoire. It happened one night while we were lying on her bed, watching TV. When the show we were watching ended, she lifted off her top, which had become her way of indicating that she wanted to "practice."

As usual, she reached down and fondled my cock through my pajama pants until it was hard. Then she pulled my pants down as I lifted my hips to help make it easier. As soon as my pants were off, though, she moved down to the foot of the bed, between my feet, and slowly crawled toward me, her nipples scraping against my legs. As she crawled toward me, her eyes were locked on mine and she had a devilish grin on her face. I was pretty sure what she was going to do before she did, but the sensation as her mouth enveloped my cock for the first time was still amazing. She proceeded to give a more than satisfactory blowjob, using her hands to assist in the task, as I'd instructed her. She also maintained eye contact throughout, which was incredibly sexy.

After a couple of minutes, I was on the verge of coming, and I felt I needed to warn her, in case she didn't want to take the load in her mouth. I groaned, "I'm gonna come." She didn't slow down and, a moment later, I grunted and came in her mouth. She maintained eye contact throughout my orgasm, gradually slowing down. Then she sat up, smiled, and made a showing of a swallowing it all down.

As expected, after we got dressed and were back in bed, she wanted feedback. I told her, truthfully, that she did a fantastic job, that she did everything I liked from a technique standpoint.

"How about the end?" she asked. "I swallowed it like I'm supposed to right?"

I looked at her kind of funny. "Like you're supposed to?"

"Yeah, you know, I always heard that you blokes hate it when we spit out the spunk."

I laughed. "Yeah, I suppose. I've had a couple of girls spit it out before. Wasn't that big a deal, but was kind of awkward. But it's not like spit or swallow are the only two options. It doesn't have to go in your mouth in the first place."

Naomi looked confused for a second and then seemed to get it. "Do you mean I could let him shoot it on my face? Like a porno?" From the way she asked the question, I could tell she wasn't too enthusiastic about this third option.

"That's one option," I replied, "and I'd be lying if I didn't say that most guys, myself included, would probably find that option very sexy. It's probably not fair, but we're all to some extent conditioned by the porn we grew up watching. But relax, most guys don't expect you to do that, and there are plenty of other good options. You can aim the cum onto some other part of your body, like your breasts or your stomach, or you can just let it shoot out onto the guy's own stomach. I don't know that I can speak for all guys, but I would rather watch the cum shoot somewhere, really anywhere, than have it disappear into your mouth."

"Wow, I had no idea, Jake. You're just a fountain of sex knowledge. And honestly, I'm a little relieved. I never really fancied swallowing it."

The next night Naomi was again eager to practice. She ended up giving me another stellar blow job, this time while I was standing, and she finished me off by aiming my cock toward her breasts. The sight of my cum shooting onto those spectacular breasts was exhilarating. Afterwards, during our debrief, I told her that the key to a memorable blowjob was less about technique and more about context and setting. The most memorable blowjobs I'd ever had, like the one in the dorm room closet, stood out in my mind because they occurred when I wasn't expecting them or in a place that was a little risque.

In the following weeks, Naomi gave me at least eight more blowjobs, including one in a changing room at the local department store and one in a karaoke booth, much to the shock of the poor waitress who walked in on us mid-blow to see if we wanted more drinks. In the karaoke booth, she surprised me by intentionally aiming my cum onto her cheek and nose, the first time she'd let me come on her face. She seemed proud of herself afterwards, jokingly taking a selfie before she wiped away the cum.

ANOTHER KIND OF JOB

As much as I love blowjobs and handjobs, I was curious what else I might be able to "teach" Naomi, so one night, while she going down on me, I decided to tell her about Charlotte, a girl I dated briefly during my junior year of college. Charlotte, like Naomi, was well endowed, and on a few occasions, she used her breasts to get me off, clamping my cock tightly between them. As I began telling Naomi about one of those occasions, she pulled her mouth off of my cock and looked up at me.