Pleasures with guilt – 6



“I think it’s easier for me to talk to you as opposed to mom,” he’d started as I simply nodded my head. “Maybe because you and I…” he added without finishing the thought, to which I again smiled, still nodding. “Anyway…Cheryl, my girlfriend, mom thinks she’s a bit of a prick tease, and maybe she is…but there’s a lot more to it than that. It’s complicated,” he said pausing, releasing a heavy sigh of his own.

“Aren’t most relationships?” I challenged myself. “Even the really good ones take effort,” I counseled, to which Jared now nodded his head.

“Yeah, maybe they do…but part of my problem with Cheryl is, my lack of experience, and her having quite a bit of it.”

Now I really was confused here. I wasn’t expecting to hear that. “I take it…she isn’t a virgin then.”

“No, she’s not. And it’s not that, that bothers me, or is really the problem.”

“Why don’t you tell me just exactly what the problem is then?” I asked. “Maybe…I can help you sort it all out?”

Once again he sighed, but then thanked me for listening to him. “Part of the problem is because she has had sex…and I haven’t. She sort of likes the idea that we’re taking things slowly.”

“Nothing wrong with doing that,” I told him.

“No…there isn’t,” he agreed. “And I like that we have been. What I don’t like…is when she tells me that what I’m doing is wrong, or that she doesn’t like it, or that because I am so inexperienced, that I need to let her show me certain things. She makes me feel stupid, inadequate,” he finished looking down at his hands, which he’d locked together in his lap.

On the one hand, I had to admire the girl. It was obvious she did indeed know what she wanted, and was in a way attempting to teach Jared that. On the other, I wanted to shake her…she was obviously going about it the wrong way. And if she continued to do so, I didn’t hold out much hope for this relationship.

He looked up at me with puppy dog eyes. “I mean shit Jen, I know I don’t know much…I don’t have as much experience with women as a lot of other guys do, I’ll be the first to admit it. But if I do, do something wrong, or something she doesn’t like, she gets frustrated with me, and then we’re right back to square one again,

and when that happens, it’s like days before we even attempt to do anything again. In the meantime, I’m getting more and more frustrated with her, and starting to wonder if this whole relationship thing with her is even worth it. Had it not been for you,” he grinned. “I’d have probably gone off on her…and not in a good way either!”

That one I did have to laugh at, easing the tension a little, as he finally relaxed.

“She might indeed be a bit more experienced in that department,” I told him. “But she’s not acting or being very mature either. You on the other hand have just the opposite problem. And maybe that’s where I can help at least a little anyway.”

“Help how?” he asked curiously.

“Well for starters, what is it she thinks you’re doing wrong? And what is it you’ve been doing anyway? Obviously…you’re still a virgin, yes?”

Jared nodded his head.

“So it’s obviously nothing to do with that…yet,” I added, winking at him. “So…why don’t we start with the first so-called problem area, and take it from there.”

Jared had finally relaxed enough to begin laying it all out. As I’d guessed, the main issue between them at the moment was with regards to oral sex, mostly on his end according to what he said.

“I take it, you have done this with other girls in the past? Or is this a first for you here too?” I asked him.

“A couple of times yes, but admittedly Jen, it didn’t seem to go as well with them either, so obviously I am doing something wrong here. And if I am…then I do want to learn and figure out what I’m doing that is wrong, or why they don’t like it. But so far, all I’m getting is a lot of negative feedback, and nothing positive. How the hell am I ever going to learn that way?”

“You aren’t,” I agreed. “At least not like that. But…if you’re willing, I really do think I can help you, and that I can do in a little different way than Cheryl obviously has been. So…if you’re willing, I am. But it’s entirely up to you.”

I saw the look of relief in his eyes as he glanced up towards me. “Then teach me,” he said. “Show me what I’m doing wrong.”

“First things first,” I told him. “Let’s set the mood, and get comfortable. That’s the most important thing, next to hygiene that is,” I said smiling at him. “Which means…you need a shower. So let’s begin with that. But…I’ll join you, and we’ll take it from there and go on to the next step once we’re all squeaky clean here shall we?”

I could see that Jared was definitely up for that. Once again wearing only his pajama bottoms and nothing else, his erection was already poking well up through the material of them as he sat there. He even looked down at himself realizing that he was, and blushed a little. I stood up, pulling him along with me, taking his hand. Once he was, I then reached over, grasping his hard cock through the lightweight flannel material of his pajamas, and then pulled him along behind me while holding it into his parents’ bedroom and their much larger shower.

We soaped one another from head to toe, even going so far as to wash one another’s hair. I also noticed as we did that, he had some obvious stubble growing around his pubic region, he shaved which I admired his doing, now taking the razor and beginning to shave him myself. I was pleased at his trusting me to do so as I quickly smoothed him up, likewise gently lifting his balls, shaving those as well until he was as baby smooth as I was once again.

I then skinned back the foreskin on Jared’s penis, washing him thoroughly teasing him a little as I did so.

“Ok, now it’s your turn to wash me,” I told him as I lifted one leg up on the corner shelf there in the shower stall. Jared knelt beneath me, his face only inches away from my pussy as he gingerly soaped me up once again, only this time looking at me as he did so. “Go ahead…take your time, wash everything, look at it as you do, familiarize yourself with me,” I told him. “But more importantly, enjoy yourself while you do.”

I didn’t have really long labia, but I enjoyed it when he pulled on each one stretching them out as he washed them, running a slippery finger alongside each of them, in addition to dipping the tip of his finger inside me. His look of utter fascination as he took his time admiring, just looking at me was arousing in and of itself. I could feel the moisture already beginning to pool between my legs, which he quickly discovered, looking up towards me, licking his finger off tasting me before sticking it briefly inside me once again.

We took an inordinate amount of time there in the shower, just touching, mostly looking, becoming familiar and acquainted with one another’s bodies, without the worry or concern of doing so in an attempt to get one another off. That would come later…much, much later.

By the time we were both so aroused, we’d have popped without even touching one another further, it was time to get out, drying one another off as we did. I then led him out of the room as opposed to lying him down on his mother’s bed. I didn’t want him to feel uncomfortable about doing that, or having any worries or concerns about leaving a trace of our activities there.

Leading him once again by the cock, he followed me back down the stairs into the living room where we pulled off all the cushions on the couch making a little bed on the floor. I lay down amongst them, propping my head up on one of the pillows, spreading my legs bending them at the knee.

“Take your time Jared, just look at me, touch me, do whatever you want…but just take your time, we’re not in any hurry here. And it’s also not a time for instructions, or orgasms…or anything like that. It’s just about fun, adventure, and getting to know me, ok?”

I could see by the smile on his face he was more than relaxed. Even his cock had actually deflated a little, becoming slightly flaccid again, but I was actually happy to see that as he positioned himself there on the floor, between my legs, and for the longest time, just looked at me.

Eventually I felt his finger again as he ran it up and down between my legs, ever so lightly…so teasingly, and I moaned, groaning pleasurably at his touch.

He smiled at that, laughingly, doing it again, playfully, erotically. And oh so sensually.

“I think I’m ready now,” he told me. “I want to taste you, lick you…eat you. But more importantly, I want you to tell me what I’m doing right…or doing wrong.”

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