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She Wouldn't Do What I Wanted, But...

Posted by: Age: 24 Posted on: 1 comments
3 likes 58 views Category: Masturbation Male-Female Tags: Male-Female, Masturbation Male-Female, anal fingering, stroking, masturbation, massage, ass crack

Another story from a client.


I kept trying to date this beautiful 'gypsy' woman for weeks. I call her 'gypsy' because she had that light skin, with long, black, curly hair. Very much a Spanish look. She also had big boobs on her short, skinny body, which I particularly like. I kept wondering what her nipples looked like. Where they dark? Were they big in diameter? I really wanted to know.

Finally, she relented and we went to a drive-in movie together in my classic 1966 Chevy Nova station wagon. It's perfect for movies, and we're lucky to have one of the last drive-in theaters in the country here.

Nothing happened. We watched the movie, that's all.

But the next day, she offered to cook a spaghetti dinner. I was all for that.

At her place, a big apartment in a huge old Victorian house, we ate, then she put on some music, offered a glass of wine, which I declined while she drank hers, and we sat around talking. I was horny, and fortunately I didn't have to do all the heavy lifting.

She offered me a massage. How cool is that? I accepted, and found myself shirtless on her bed, getting my shoulders rubbed. I knew it had to progress, but how to make it happen?

I then rubberd her shoulders. After five minutes, I suggested she remove her T-shirt. She did, but kept her bra on - for a moment. She then removed that as natural as could be, as if I was always there to see her pretty boobs, and as if it was no big deal.

They were bigger, but floppier than I imagined. I had been hoping more like balloons. Nature was thinking more like mushrooms, or toadstools, or something. Still, I wasn't disappointed. Her nipples didn't meet my expectations, or my imagination. Instead of big and dark, they were pink and little, not unlike a boy's. Oh, well. Just the fact that she was there naked in front of me, was just fine.

She returned to my shoulders, but then worked her way rather quickly down my back. She pressed her fingertips under my belt a couple of times, then simply asked, "Why don't you get more comfortable?"

My dick was already hard and for some reason, I was concerned about her seeing me excited. Then, I decided, it was no secret I found her attractive, so let come what may. I took off my pants, and my cock stood right out at a 45-degree angle.

She had a twinkle in her eye, as if she had never seen a cock before. Perhaps she hadn't. She simply said, "May I...?"

I stood right in front of her, and she reached out and ever so gently touched her fingertips to the very tip of my penis. I'm sure you know that first-touch magical feeling.

She had me lay on the bed, while she removed the rest of her clothing. I wasn't ready to see such a hairy crotch. I had assumed she'd be hairless or at least trimmed like all the women you see in porn. But, this was a real, live woman. I really wasn't all that disappointed. I wanted to touch her rather large labia hanging down through all that black hair, but she gently pushed me down on the bed, and said "This is all about you, tonight."

And with that, she started ever so lightly and slowly touching my scrotum with her fingertips. I gladly accepted the attention. Each stroke of her fingers caused my prick to jump a half-inch in the air. I felt that orgasmic feeling building.

But, it only built so far. She kept ever so lighly touching me. Pretty soon, every part of me was internally screaming for her to just grab my cock and jerk me off. I wanted to cum! I even opened my mouth a couple of times and asked her to 'finish me off.' 

And she wouldn't. She didn't. She had a mind of her own. She kept up the light scrotum tickling, and that's all she would do.

This went on for a good ten minutes. I was in the strangest kind of agony. I was loving it, but wanted more. Perhaps you've had something in your life like this. Otherwise you wouldn't understand what I was going through.

Then it was her turn. I was still rock-hard and feeling a sort of ache in my balls. Come to think of it, my dick was starting to ache a little too. It had been hard for too long.

Still, I'm a polite and caring individual. She deserved to get her treatment, and I did exactly what she asked. She wanted more shoulder rubbing. Then, she wanted me to massage directly on her puffy breasts. I was in a new kind of heaven, and soon, my slightly aching dick and truly aching balls were mostly forgotten. I tickled her hard little pencil eraser nipples and she really liked that. 

Then she got up. I didn't know what she was planning, until she turned over on all fours with her skinny little ass up in the air and wide open. "Would you be so kind as to massage my ass crack?"

Weird, but, well, of course I did it. I started lightly rubbing my finger up and down her crack, between her lower back and just before the anus itself, as she went "Mmmmm" several times. Evidently, it was having the desired effect on her. As I was doing this, I kept staring at her most attractive pink, puckered asshole, with a bit of darkening about an inch in diameter, and radial lines, very slight natural wrinkles, all leading to the center. It was having an effect on me.

I felt the cum rising, and there was nothing I could do about it. She hadn't touched me at all for five minutes. All that was happening was I was staring at her anus while stroking the area just above it. Oh, and then I caught a wiff. Not what you'd think. It was a sweet, phrenome-laden odor, that sent me over the edge.

I tried with all my might to prevent it, but the pulsations started up, and I was shooting squirt after squirt of cum against her hip, her blankets, and some landed on her back.

She was delighed, but chastised me for not letting her see me cum. She later exclaimed that seeing guys shoot is a big turn-on for her.

Not knowing exactly what to do, but realizing my moment was over, I knew I had to reciprocate. I continued stroking the ass crack area, then decided to see what would happen if I stroked that portion between anus and vagina. She didn't complain. I then ever so lightly pressed my index finger against her anus itself, and was rewarded with another "Mmmmm!"

I slowly pushed my finger in a bit more. Finding we needed some lube, I pulled my finger out, and stuck it in my mouth to coat it with saliva. Realizing it had just been in her ass normally would have grossed me out, but on the contrary, that caused my penis to start hardening up again.

I stuck my wet finger slowly in her ass, only up to about the first knuckle. She asked me to pull her inner labia with my other hand. That's right, she wanted them pulled. It turns out that's a bit difficult with a hairy woman, and one who's exuding lots of girl juice (which I should have known I could have used as the anal lube). After a few incorrect gropes, I got a pretty good hold on her slippery inner labia, and pulled lightly. 

"No, harder," she practically screamed. I noticed her voice was a bit jittery. In fact, her whole body was shivering. 

So, I pulled harder, and felt something happing with my finger in her ass. It was kind of rhythmic. Oh, she was orgasming! She started off slowly, but within a few seconds it was a screaming, I mean really loud, crashing orgasm. I had to let go of her labia and wrap my arm around her so she wouldn't throw herself off the bed.

So that's how the evening went. Afterward, she offered to jerk me off for real, even give me a blow job, but I'm a sort of one-shot guy. Even though I could have probably gotten fully erect again, the good time was over for me.

No, I didn't date her again. I would have liked to, but she really likes her wine, and I don't drink alcohol at all. I used to drink way too much, so now, I have to be careful to stay away from all such influences.

The story doesn't end badly. Soon afterward, I met this very interesting African-American girl...



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