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Long Lasting Pleasures

We met Jay and Gale a few months ago. They were a really nice couple who seemed very much in love. Although we talked about sex once in awhile and she shared some interesting personal things with me, they seemed to be totally monogamous in their thinking, so any liberal sexual ideas never came up.

When Ian and I heard they broke up, I wondered if it was because of some of the things she told me awhile back. As it turned out she shyly told me that Jay was “wearing her out.” And she went on to explain that he always treated her well, but when they had intercourse, it would be nice up to a point, but it usually went on past her own enjoyment. She’d come, but it took him what seemed like forever to come. She said it got to the point to where she wasn’t enjoying intercourse anymore. “Oh Wow,” I said, “most women would be thrilled if a guy did a lot more than a ‘slam, blam, thank you Ma’m.’” “Well,” she said, “that’s what I thought, but a marathon screw session is okay once in a while, but always, not so much—it gets kind of hard on the pussy—excuse the pun.” We laughed. “But actually that’s the other part of the problem. Jay’s pretty well-endowed and when he gets hard, he gets hard as a rock and stays that way. Which is nice for awhile, but not when it’s overtime.” “Wow, really? Of course, most women would like a guy to stay harder much longer than a lot of men really do.” “And that’s probably true,” she said, “but really, it gets tiring time after time. I wish he’d do more oral and other stuff instead. Perhaps we’re just not sexually compatible.” She seemed sad, even though she said he was a great guy.

(I think I sensed the seeds of their breakup in that conversation.)

Well, as it turned out, she was offered another job back East and she decided to take it. She wasn’t leaving for a couple of weeks, and was staying at her sister’s until then. “So,” I said, “it’s really over between you and Jay, huh?” Gale: Yeah, really, he’s a nice guy, but we just couldn’t get over the sex thing.”

Well, I got to talk to her again a couple of days later. During the conversation I said, “It’s really a shame that you and Jay didn’t find the sexual connection. Sex is really wonderful.” Gale: You and Ian seem to. Me: Yeah, we have, but we have our differences as well.” And I went on to explain. “Actually, Ian has a softer approach to sex. He likes a lot of oral and caressing, and he has to work at postponing orgasm. On the other hand I like it hard and love it when he lasts a long time. But he always pleases.” Gale: Oh My God, Jay would love you. Me: Hmm, he probably would and I’d probably like him. Gale: Wow, that’s really interesting. So in a sense, you and Ian sound a little like Jay and me. But you don’t seem to have any problems. Me: Well, we don’t. I guess we meet each other halfway. He makes a real effort to stay longer, and I make the effort to avoid getting too excited where I squeeze the hell out of him and cause him to have an orgasm sooner than we’d both like” Then I stopped for a second or two and said, “Tell me, Gale, have you ever been sexually adventurous? “ Gale: Oh, well, before I met Jay, a little. Me: Well, Ian and I do have a wonderful sexual relationship, but every now and then we allow each other a bit of sexual freedom. Gale: Really? Like what? Me: W-e-l-l, over the last few years we’ve met a couple of very nice couples, and some pretty nice single guys and gals. Gale: Wow, really? Me: Yep, and every now and then I meet a guy like Jay who really drives me wild. Gale: And Ian doesn’t get jealous? Me: Not at all. He’s totally in tune with his own sexuality—and mine—and actually loves if I’m truly enjoying myself with someone else. Gale: Wow, I would have never thought you and Ian. Then she said, “Holy cow—it just occurred to me that Jay would really love to have sex with you! And you’d probably love it with him—at least for a time. Me: Yeah, I think I would. And you know, I think Ian would be just the kind of guy who would totally please you. I know for sure that he’d love to share an experience with you. Gale: Oh my, really? Me: Yeah, and I like the idea very much—and I know Ian would also.

So after she talked with Jay, he kind of liked the idea, so we arranged to get together.

When the night came, we talked a bit to make sure everyone was agreeable, and then we decided to go into different bedrooms.

I thoroughly enjoyed being with Jay, but I could see why Gale would be disappointed—and I was absolutely sure she was having a wonderful time with Ian.

Jay and I started out with a bit of kissing and exploring, and then undressing each other—and we were soon on the bed naked. He did have a nice physique—and willy did look awesome. On the bed, we explored each other a bit as we lay side by side facing each other—and it is always nice to hear another man tell me how much he appreciates what he’s seeing and touching. And he did make my breasts feel pretty damn good all the way down to my pussy. I have to say, he looked and felt pretty damn good too—and when I wrapped one hand around his cock, Wow! It was very, very nice and definitely rock solid. But it was soon gone as he got between my legs and kissed his way up to my pussy. He didn’t spend nearly as much time as Ian does, but I was soon nice and wet and ready for action. He leaned over to get a condom, put it on and then he rubbed his cock a little between my pussy lips and my clitoris, and I felt the weight of it as he let it rest there.(I have to say, it did have a presence.) Then I reached over and handed him the small tube of lube. He put some on his cock and again rubbed it gently on my pussy—and then between my pussy lips.

And I soon felt him slowly slip between them and enter me in this nice Missionary position. Ah, soooo nice! And I just relaxed and savored the pleasures of a pretty awesome cock totally filling me up and going deeper and deeper inside me. Oh what a lovely feeling! When it was all the way in and he was tightly up against me, I gasped and said, “Hmmm, now that’s very, very nice.” He smiled and said, ”Yes it is, from my perspective as well.” Then he reached up to caress my breasts and said, “Very, very nice indeed.” And little by little he began pumping in and out, first with short strokes and then with varied strokes.

I thought to myself, “Now why would Gale not like this! Damn, that cock is awesome!.” I could feel it’s hardness, I could feel its strength—and I could feel it moving in and out of me making me feel absolutely wonderful. So what’s the problem?

He clearly did enjoy pumping and I have to say that I was clearly enjoying it as well. Yes, it was good—very good. But after about twenty minutes, I began to experience what Gale was saying, because at some point it started to become a bit overwhelming. Luckily, we changed positions and he entered me as I kneeled and leaned forward, and got into the Doggy position. And I have to say, yes, yes, and yes, it felt totally and awesomely satisfying as he pumped into me, faster and faster. But after awhile I also experienced a little discomfort as I remembered the fact that in this position, a cock goes very deep—and can get uncomfortable. But I guess it was more pleasurable than not, and I managed to move my body away a little when he went too deep. But I did get tired and just let myself slowly lower until I was almost lying down. In that position, he couldn’t go too deep (I have learned a thing or two!)—and it did feel good. From here we went into one lying down position to another—and in those lying down positions his cock felt extra special. But at some point, I realized I was becoming tired of the constant pumping, so I began to squeeze him a little whenever we changed to a new position.

After a few minutes he said, “Oh God, that feel soooo good”—and at that point we got back into the Missionary position. But this time, I decided to be in control—and as he pumped, I varied how hard I squeezed his cock—and I could tell by his expressions and his comments that it was having the desired effect—he slowed down. But it wasn’t too long before he was pumping faster and saying, “Oh yessssss.” I, in turn, was already working towards my orgasm and it didn’t take much to get there—as we both exploded with a pretty damn good orgasm.

There was no doubt that our experiences were wonderful. Gale’s experience with Ian was “absolutely perfect” she said. Ian took it nice and slow and built her up slowly with caresses and oral, and since his Willy wasn’t quite as hard as Jay’s she found it more pleasing, even with pumping. And since Ian would not have even wanted to continue pumping for too long, they both found the perfect spot to have an orgasm. And my experience with Jay was awesome. I kept him more excited by squeezing more than he’s used to, and when I had had my fill of pumping, I applied more squeeze—which he couldn’t resist, and we had a wonderful orgasm together.

Afterwards, we sat around, ate some snacks and talked about our experience. And then we talked extensively about their supposed “incompatibility.”

And we discussed how what I did with Jay might work for Gale, that is, things like getting into positions that would help her be more in control, and learning to squeeze more so he’d slow down and she could reach an orgasm when she’s ready. And that he could take more breaks of “other than intercourse” to give her some breaks from his thrusting.

When Gale and I were alone, I asked her, “Now that you know that Ian and I had a similar problem in reverse, do you think that you two could ever work it out so that you were happy sexually together?”

“Hmmm,” she said, “perhaps, perhaps.”

Well, as it turned out, they decided to have sex one more time before she left for New York. (And she said it had been really marvelous.) So, rather than break up, they decided to keep in touch. And she added, “Who knows?”

But in the long run, the one distance thing became too much, and they eventually hooked up with other partners. As for me, Jay and Ian, we did meet a couple of times with Jay, but after awhile he met a girl and it became more of a “seriously committed” relationship, so that put an end to our fun together. But, it was nice while it lasted—very nice.