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.