Chapter 2

Greg came up to me at school the following Monday.

“Hey Jerry, I’ll give you $20 if you set me up with Nadja again.” He said quietly in my ear.

“Make it $50” I responded without thinking.

“It’s a deal.” He agreed.

Well, they both wanted to do it. Greg was loaded and I was broke. I had some qualms about pimping out Nadja, it was just that my greed was more powerful than the qualms. Anyway, it went really well and they both reported satisfaction about the meeting.

Greg wanted to see her again and offered another 50, but Nadja wasn’t into it.

“That’s twice with Greg.” She told me on the phone, “He’s a sweetheart and all, it’s like I told you though, if you’re not looking for a relationship then it has to end after one or two times.”

“What if we send him to Helen for the weekend?” I suggested. There was a pause.

“I think that might work. Well, you know he’d have to work too, that Helen has mixed motives.”

I told Greg about Helen, and told him he’d have to pay me $100 for the setup. I told him honestly what it was about though, he’d have to clean and babysit for her.

“I tell you man, she’s a hot milf.” I added. “Just look her in the eyes while you do it to her. Yeah, and go down on her first, even though she’s hairy, you got to do that, right?”

“Sure man, I get it.” He agreed.

“If she comes, maybe you’ll get to see her again. Maybe.” I insisted.

I called Nadja to arrange it. “Come by my place tonight.” She said, “My friend Monica is staying for a few days, play your cards right and you could get lucky. She’s German.”

Monica was 50 or 60, tall, big breasts, plump ass, and surprisingly beautiful. She had a sort of peachy face, striking green eyes, and wonderful thick deep red hair to her shoulders. She was funny and flirtatious too.

There was something off about her though; I realized she was a bit fake; everything was artificial. Her face was smooth but her neck wrinkled, so she’d had a lift. Her hair looked great, but was obviously imposable for a woman her age. That wasn’t it though; it was her manner. She had a sort of over feminine way of moving and speaking, every gesture and expression was intentionally yet subtly sexual.

Naja was the opposite; as natural as could be.

“Monica, this is my boy Jerry.” She said as she let me into the small apartment.

The German woman stood and even though she was wearing flat shoes she was a little bit taller than I was. She smiled though perfect white teeth and proffered her hand, knuckles up. I accepted her challenge, I took it and kissed it.

That was oddly exciting; men just don’t kiss women’s hands anymore out in the real world, only here in Nadja’s place could such a thing still happen.

The women both laughed, because it was pretty funny.

“Who’s hungry?” Nadja asked, stepping into the kitchen.

“I’m always hungry, but darling you know I can’t keep this figure if I eat real food.” Monica said.

“So what do you eat?” Nadja asked.

Monica looked at me pointedly; “You know very well what my appetites are my dear!”

I helped serve, then we all ate. Despite her declaration, Monica ate too. I was mostly silent as the women talked, catching up after not meeting for a while. Monica told us of her adventures traveling in Europe and Asia as I stood to clear the table and clean up the dishes and kitchen.

That Monica was sexy as hell; she even had a sexy voice, everything about her seemed to scream sex. If I did it with her, would it better my chances with Nadja? I couldn’t figure it out.

They were still talking and talking, about people they knew but I didn’t. I decided on a daring move; I stood behind Monica’s chair and put my hands on her shoulders. Her monologue stopped for a few seconds, then she went back to telling Nadja about a rich old German she met in Spain, with a big penis and big seaside villa.

I began to rub her shoulders; not sexual, yet totally sexual. I pulled her cardigan up and out a little, and my hands were caressing her naked flesh. It was deliciously naughty; I didn’t even really care if it went farther, the audaciousness of my gambit was a goal of its own. To just put my hands on a woman like this, and get away with it.

I looked at Nadja; she’d said I should do it with someone, she’d insinuated her friend was into it. She nodded and smiled subtly, tactically agreeing to my move. I couldn’t see Monica’s face, she just sat there as if no one had their hands on her.

“You know, I think I might just go out for a while.” Nadja said, standing up.

“Really?” Monica asked, “We could share.”

I liked that idea; a threesome!

My fingers pulled her expensive hair to the side, caressed her neck and ears, and I noted slight grey roots at her scalp that didn’t lower my lust one little bit.

“No, I smell some chemistry in the room and I’ll leave you two alone.” Nadja said with a smile of generosity that seemed just slightly forced.

I ran my fingers though Monica’s hair, down her neck and arms. I stroked her face and forehead as Nadja pulled on a jacket and went out.

I wasn’t sure what to do; Monica seemed complacent, willing. She just sat there while I toyed with her hair for a few long seconds, and I realized it was up to me if I wanted to take it further. I stepped around in front of her, put my hand on her chin and tilted her face up as I bent forward so we were maybe 12 inches apart.

She grinned with excitement, her eyes sparkled, I had her unspoken consent to proceed. I lowered my face to hers and kissed her, letting go of her so that our only contact was at our lips. Gently, I slid my tongue into her mouth.

I took her hands and pulled her to her feet, wrapping my arms around her I pulled her statuesque old body tight, kissing her deeply. She let her arms hand slack, pretending that she didn’t want it as much as I did. She giggled a little though, as I kissed her neck and pulled the zipper of her tight dress down her back.

Her breasts were still pressing against my chest and our mouths were an inch apart. I felt her thigh press forward against the lump in my pants.

I slid the short wide sleeves of her dress down her arms, and to my surprise she was wearing a fitted corset; it held her waist tightly and at the same time supported her breasts. I stepped back to look at it and figure out how it comes off. There were crossed laces and it looked complicated. And very sexy.

“There’s a zipper at the back.” She told me, turning around to show me. “You can’t buy these in Europe anymore, I had it made in India.”

I pulled the heavy zipper down and peeled the thing from her. She was only a little bit wider without it. Monica was a woman who did everything possible to be as sexy as possible, all the time. That was both attractive and repulsive at once.

She turned to face me again, smiling her bright smile of seduction and putting her arms around my neck. She pressed her large tits against me and rotated her shoulders a little so they moved as she grinned at me silently, waiting for me to take the initiative. Her big breasts hung low on her chest, nipples forward. Smaller nipples than Helen or Nadja; Monica had never had a child.

My hands went under and I lifted them; they were soft, fluid, natural tits. She looked at me with a more serious expression for a moment.

“Things are moving pretty fast here.” She noted in her sexy European accent, “Are you sure this is what you want?”

“I’m sure.” I said with more confidence than I felt; she was right. What was I doing with her? She was a sure thing at this point, and I liked her, but she was 4 times my age. Freud would have written another book if he was here.

“Well then darling, I should tell you a few things.” She said, pulling up my tee shirt and throwing it to the side. “I’m a very experienced woman. Very. I started when I was 15, 45 years ago. I’ve probably had more than 1000 lovers; does that sound like a lot? It would be just one every two weeks, and really most men I only do it with once so that’s not really much at all.” She laughed.

Her skin was not too bad considering her age. Fairly smooth, complexion compromised but still attractive enough for a horny little bastard like me.

I pulled her over to the bedroom, turned her by her hips, and pushed her onto her back. Her long legs went up, her panties came off, and my young face went down.

She was smooth as a baby down there, and her vagina was extremely pretty. It was pink with symmetrical little butterfly like lips that waited patiently to know me. I realized that both Nadja and Helen had been damaged by childbirth.

To my pleasant surprise, the old woman tasted great. I did my thing with her; touched her body, rubbed mine against it, sucked her tits, bit her ears, licked her eyes, and generally adored her. She didn’t say anything, she just smiled the whole time, and tickled my stiff rod with her long sensitive fingers.

I got into position between her raised open knees, my hard cock was ready to go where 1000 men had come and gone before, when she stopped me.

“I have to warn you.” She said, “I’m sort of...”

“Yes?” I asked.

“Strong there. Well, actually I may have the strongest cunt in the world. I don’t do much for physical things, but I’ve been doing vaginal pressure exercises for 30 years. So if you go there, you might be ruined.”

“What do you mean?” I asked, my eager cock still in my hand between her open legs.

“Oh never mind, there’s no stopping now.” She sighed, so I went forward; I put my thing against her and pushed, and she welcomed me into her hydraulic cunt.

At first, it was just like the other two other women’s vaginas; wet and nice.

“Ready?” she asked, “Here it comes.” And she contracted like a fist; unlike a hand though, the pressure around my cock was perfect, all around and full length, in a tight wet excruciating ring. It’s difficult to describe the sensation, other to say that it was wonderful. The old woman just lay there below me, totally relaxed other than inside her amazing vagina, looking up at me with a knowing smile. “Do you like that?” she asked.

“I sure do.” I grunted, so shocked that I could barely speak.

“Go on now.” She insisted kindly, “You know what to do.”

Pulling out was the same as always, but it took a lot of effort to push back in while she was squeezing. I had to go slower than usual.

“Oh yes, that’s very good.” She sighed, “You’re a bit small, but so HARD!”

It was fantastic; her green eyes, her white teeth, her tight cunt, her long fingers brushing across my ass. I was really just holding on, I had to find a way of delaying my orgasm or it would be a fail.

I focused on the way her breasts hung to the sides, down near her ribs when she was on her back. The wrinkles and furrows of age on her neck. The grey roots on her scalp. It worked, and I was able to keep fucking for a while. Harder, harder! I had to make her come!

She rotated her hips a little, then began to lift them to meet my strokes. I saw her expression change, and I knew she was moving in the right direction, if I could just resist the mad pleasure of her iron cunt for a little bit longer.

I did; it took a little while, and every second of that was an eternity of pleasure. The pressure, the wild wet tightness was crazy. Why did she have to squeeze so tight, couldn’t she see it was too much for me? I stared into her eyes, her old eyes, beautiful eyes, eyes that had looked at many, many men. Eyes that had seen the world, and now were seeing me. A schoolboy, a teenager who’d just lost his cherry a couple of weeks ago, I was a novice and she was an expert. It was impossible! I couldn’t win.

Was this some sort of contest then? No, she wanted to come as much as I wanted her to.

Her fingernails cut into my ass and her face seemed just a little bit flushed. Could it happen? I was barely hanging on, her vagina was too tight, maybe, maybe...

Yes. She was there! the crazy sexy old slut stared into my eyes and she was coming. I didn’t want to, I had to; I came with her, squirting my American schoolboy spunk into her wonderful tight old vagina.

We lay together in silence for a while after we were done, her red head on my young chest as she played with my soft cock.

“Are you really 16?” she asked, “You’re a bit short.”

“I am really 16.” I confirmed, “My birthday was a month ago.”

“I do enjoy teenage cock.” She told me, “It’s a distraction, very exciting and naughty. Usually I spend time with older men, well, I’m getting on myself now so it seems like old men are not older than I am. Anyway, men who can keep me for a while, until we get bored with each other. I’m very lazy, but not rich enough to live the way I like. So, what about you? What are your ambitions?