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Weird Conversation With Unexpected Results

Posted by: Age: 28 Posted on: 2 comments
4 likes 787 views Category: Masturbation Male-Female Tags: asshole, mutual masturbation, first time, finger

Another story from a client.


Cherelle and I work together in an office. The company supports photographers – a long story. Anyway, every now and then, the two of us are the only ones there. Over the course of literally months, our conversations have become more personal, more risqué. We had arrived at the point where we both admitted masturbating. I had a delicious time after that wanking many evenings away while imagining her masturbating too.
She's a perfect girl of Polish descent. You may not know what that means, so let me tell you: She's short, like maybe 4'11", so blond you could almost call her hair white, and she wears her straight hair long, half-way down her back. She is small-breasted, which I happen to like, has totally smooth complexion, and is very light. I doubt she gets out in the sun much. Oh, and she's four years younger than me at 24. Oh, and did I mention that we're both single? I'm not dating because, well, I guess I don't really know how. I'm usually too shy around girls. I would have been that way with Cherelle too, but working in the same office, and sometimes just the two of us, of course we got to talking. I do believe she's as shy as I am, and so she doesn't have any kind of relationship either.
So, we got to talking about wanking, and one day she asked me exactly how I do it. I may have turned a bit red in the face, but decided to answer honestly. I told her I like to put on porn and build up slowly. I told her I wrap a hand around my penis and don't even stroke at first. I just sit there looking at it and admiring the hardness. Finally, I start stroking. Then I admitted to what I thought was the embarrassing part: I like to lightly brush one of my nipples with my other hand. There, I said it!
She took it all in without saying much. Then I decided to not ask her how she masturbates, but what she wishes for when she masturbates. It turns out that it was a stroke of genius.
She was, fortunately, as frank as me with her answer. She told me exactly and it got me so horny I almost exploded right on the spot.
What she said was that she wished she had someone to lightly rub their finger around her asshole. That's what she wanted. You may think that's weird, but, well, maybe it is, but I'm sure people can be a lot weirder than that.
This was a humungous opportunity and I almost missed it. I could barely answer that at all, but what I said turned out to be something like, "Well, who would qualify? I mean, who would you want to rub your asshole like that?"
Guess what she said?
"Anyone. It doesn't really matter who does it, I would just like to experience that."
I just about fell through the floor. I'm pretty sure she was giving me the opportunity of my lifetime right here. On the other hand, I could blunder badly if I offered to do what I think she was asking for and got it wrong. She may think I'm a total geek or just hate me forever. Pondering it for a moment, I decided two things:
1. We've gotten to know each other enough that she wouldn't hate me. Maybe just chastise me and then forget about it for a week. Oh, it would be totally embarrassing. It would also hurt me to my core if I actually offered to do that for her and she turned me down.
2. This was too good of an opportunity to pass up.
So, in what I have to admit was a shaky, hesitant voice, I said, "Would you like me to do that for you?"
And she said, "Hell yes!"
Boy oh boy, I couldn't even wait for the day to be over. It was the longest afternoon of my life. Finally, we were done with work, and she followed me in her car to my place. I'm so lucky that I have no roommates.
I let her in and she drew in her breath. "So, you're a musician."
No, actually I repair musical instruments and sell them on eBay. I hope to do it for a living someday. She seemed actually impressed by all the guitars, amps, drums, brass instruments and things strewn throughout my apartment.
We went right to the bedroom. I gently kicked the cat off the bed, and pulled back the spread. Now, she was starting to look a bit hesitant. I was becoming concerned. I mean, one sees so many movies where right before the sex thing starts to happen, the people get interrupted, or someone will say one wrong thing or something, and the whole mood falls entirely apart.
Not this time, however. She was like, "Should I just take off my clothes?"
I mean, how direct is that? I was in heaven! "Yes, and I will too."
Oh, I suppose we could have been more ceremonial. Maybe had some wine. Maybe take each other's clothes off slowly. But we didn't. We just undressed and threw our stuff on a chair. Oh my! She was the most beautiful thing I've ever seen in my life. I mean, I've seen porn. What guy hasn't? But here was this beauty right here in my bedroom, so close I could touch her. I could even smell her. It was a very slight, and I must say, pleasant odor. Not perfume. Something more natural. It was her!
"So how do you want to get?" I asked. Not romantic, I know, but this evidently wasn't a romantic thing.
She jumped on my bed on her hands and knees showing me her totally smooth pussy and asshole. I think the word is gobsmacked. That's what I was. I love women who shave. To me, it signifies that they enjoy being sexual.  Her ass, too, was as smooth as a baby's bottom. Now I know why some guys call their girls "Baby."  My heart was beating surprisingly hard and fast. And speaking of hard, my penis was sticking out like a sword. She must have noticed, but didn't say anything.
And there she was, waiting for me to do something. But I had to take a moment to just admire her, and try to let my heart calm down a bit. I noticed more than my heart. I was shivering - or kind of shaking. I don't remember that ever happening to me before when I wasn't cold.
She simply said, "Go ahead."
So I did. I reached out, almost hesitantly, and then started doing exactly what she asked for. I started ever-so-lightly swirling my finger around her asshole.
It was obvious she was in absolute ecstasy right from the start. She was just saying "hmmmm" and kind of moaning.
I did it for her for a very long time, still shaking slightly. I noticed that her vagina was getting shiny right at the slit. By gosh, she was lubing up. She was totally enjoying this!
Now, I kept wondering whether I should do something more. Should I put a finger in her pussy? But she hadn't said she wanted that. I figured this was the first time and probably wouldn't be the last. I pride myself on being a patient man, so I just didn't do anything more. I just kept swirling around her asshole.
Well, maybe not so patient. I started experimenting with pressing my fingertip in a bit. Just as I was getting almost in to the first knuckle, she kind of bounced around in the bed so she was now laying on her back. I guess she was done.
"Would you mind if I touch it?" she asked. I figured she meant my dick, and so I just laid down next to her on my back, and said, "Cherelle, I'd absolutely love that."
She must have read somewhere that the frenulum is a sensitive place, because the first thing she did was place a fingertip on my frenulum; you know the little ridge of skin on the bottom side just below the head. My dick involuntarily jumped an inch at the amazing touch. That must have concerned her, because she immediately pulled back.
"No," I said, "That felt great."
So, she did it a bit more. Then she grabbed my whole cock in her hand. She didn't stroke me or anything. She just held it for perhaps 5 seconds.
And, guess what happened? Right. I came! All over her hand and my stomach.
By the twinkle in her eye, and the single word she uttered, "Gosh," I knew all was well. Much more than well.
Directly after that, she started putting her clothes back on. I took the cue and did the same.
We went to the door, and I saw her out, but not before thanking her profusely. Thanking her was a bit difficult, because she was trying to thank me at the same time.
So that was last Tuesday. Oddly, at the office we haven't had any alone time to talk it over. I also don't actually have her home number and she doesn't have mine. I'm dying to talk with her about it and set up another, well, I guess you'd call it a date. I'm pretty sure, or at least I think, I hope, she feels the same way.



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