An anonymous pal asks, "Can you think of any encounters where you were particularly pleasantly surprised? (In other words, you didn't expect that much and it turned out to be surprisingly great.) How about unpleasantly surprised (expected great, turned out to be disappointing)?"
I tend to go into random encounters with low expectations, which is fine because I'm easy to get off, so anything above a baseline of "I came" is a pleasant surprise, but that's not particular. I could probably point back to things in the past of this blog, but that's no fun. So I'm going to try to recall a few times off the cuff when I was pleasantly/unpleasantly surprised.
I remember I went on a few dates, actual dates, with a guy who was very nice but seemed to have no desire to get into my pants at all, to the point where I was about to ask him why he wanted to keep dating if he wasn't going to at least try. Turns out he thought I was significantly more innocent than I am (significantly more, like he thought I might be a virgin) and was kind of confused by the fact that I was kind of putting out signals. But he was fairly innocent, and when he finally got up the nerve to ask if I wanted to come back to his place after a date, maybe for coffee or a movie or something, I was so horny that he could have gotten lucky in the car on the way to his place if he'd wanted to.
We got there, we sat on the sofa, I said something along the lines of, "You can kiss me if you'd like," because clearly he needed some encouragement and it was either that or just start taking off articles of clothing and see what he did. He kissed me rather chastely. I'm not a chaste kisser. I don't want it to seem like I was bulldozing over his objections, but I was putting out every womanly signal I had, short of trying to wave the pheromones from my pussy into his nose.
I don't recall exactly what broke the ice, but whatever it was, shortly thereafter I was half-naked on his couch, he was pulling down his briefs (briefs! so adorable), and I got the first pleasant shock of the evening when his cock emerged and he was definitely larger than average, which the tightness of the whiteys hadn't allowed to be evident before. I know, you'd think there would have been a giant bulge, but it looked normal sized until his shaft just kept coming out of his undies.
Still, I was figuring he wasn't going to be an enthusiastic lay, given his need to have The Joy of Sex thrown repeatedly at him. But first off, he ate pussy like a champ. Didn't want a blowjob, just wanted a snack in the box. I came repeatedly, and while I'm fairly easy to get off, repeatedly from oral signifies a better than average time.
Then I thought, okay, he's making sure I get mine and he doesn't want any in return because he's a hair trigger. That's okay. I had totally gotten mine. If he pressed in and came immediately, I would still have called it a good date. But he had stamina. When he got inside me, I had to concentrate on not getting split in two, and then he started slowly thrusting in and out, in and out, until he was bottoming out and then pulling back until just the head was inside me, and I came again, which I expected would maybe signal an end to his performance.
But no. First missionary, then from behind, then he pulled me on top even though I was pretty blissed out by that point and started jackhammering into me from below, and then finally he pulled out and asked politely if I could suck him the rest of the way off, which didn't take too long but was still a respectable finish. Thick, ropey cum, but didn't taste too strong, and then we snuggled for a bit until I felt him getting hard against me again.
I asked him if he needed more, and he seemed a little sheepish, like he was afraid I wouldn't be up for it. I very nearly wasn't, but this was in my younger, more elastic days, and I just helped him into me from behind and we spooned and fucked slowly for what felt like ages until he said he was ready to go off and I just let him go inside me because I was extremely tuckered out by that point.
You may ask why I'm not currently married to this guy. The answer is that we just weren't a good fit in other ways. I set him up with a friend of mine, who thanked me profusely after because she hadn't had to jump through the hoops I did, and we saw each other a few more times in various places, then drifted apart. But that's a nice memory. I wish I'd ridden the train a bit longer than twice, but I got off plenty during those two times.
Now, the less pleasant part of the question. I can think of a few, not as detailed because who wants to remember disappointment. There was a guy in high school who had supposedly bedded every single girl I knew, to hear them tell it he was amazing, and my standards were lower at the time. He was a total dick during our date (I am so glad I've grown out of needing to have a date with someone to fuck them), not to me as much as to the waiter, which is a deal-breaker for me, but I knew he wasn't dating material and I was basically sitting through the previews to get to the movie, as it were.
The movie was terrible. He took me back to his place, his "party pad" where his divorced dad had custody and was never home from work, and we rounded the bases pretty handily, and then I was blowing him and he came in my eye, which doesn't bother me the way it bothers some people but threw me off a little because he didn't warn me at all, just grabbed my head and spewed. And then it took forever to get him hard again, to the point where he had to watch porn to get it up, and then wanted to keep watching the porn while fucking me from behind like I was basically a sex toy. I got off, just, and he barely made it out of me before painting my lower back white. I would have let him cum inside me but Catholic school makes rhythm method practitioners of all its inmates.
That was disappointing to the point that I needed to go home and get fucked by Mike to wash the bad taste out of my mouth (figuratively speaking; I don't think the guy tasted bad or I might not have continued the evening at all).
The other underwhelming experience that comes immediately to mind was in college. There was the drop-dead gorgeous girl who had hinted to me that she was interested in pursuing some experimentation with the fairer sex in the bedroom, and I'm always open for "girl's first lesbianism" parties. She was porn star gorgeous. No, she was model gorgeous. And I wanted to undress her in the worst way. I had seen glimpses of her hidden delights but never the whole package.
Let me tell you, whatever other disappointments I might have had, seeing her naked was not one of them. I suppose I shouldn't have expected much from the rest of it, since it was her first time, but rather than be nervous or excited she was like a cold fish, and then she basically wanted me to eat her out while she lay there and provided no feedback until finally she gasped a few times, then pushed me away and said the evening was over. I wasn't particularly depressed to hear that, honestly, since she'd provided very little in the way of enjoyment for yours truly. I kept the image of her naked in my head for a while though. God, if she'd been at all a good lay, but she wasn't. I guess she decided she didn't really want to sample sapphic bliss after all. I heard from a guy who had fucked her that she wasn't a cold fish with him.
I could probably summon up more, but I'm going to leave it with those. Like I said, disappointments aren't as fun to remember as pleasant surprises, and now I'm wishing I knew where the guy from my first story wound up, and if he was up for a threesome.
I hope this answers your questions, anonymous pal, and thank you for asking them. If you'd like to ask any questions of me, even silly ones, my inbox and comments are always open, and I respect anonymity as you can see.
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