Fun and Games

Chapter 3-1

Chapter 3

Di, for all her enthusiasm for s*x, didn’t want a relationship. We hooked up a few more times. s*x with her was always amazing. She had no intention of getting serious.

I went back to the apps. Di didn’t care if I was hooking up with other women. Jobeth might have cared, but all I got from her was complete silence. Nary a word. She blocked me from texting her, the social media we shared, even the dating app we both confessed to using in the past to find partners for s*x.

I didn’t want to date a woman like Jobeth again. I wanted an actual older woman.

Surprisingly, there were plenty of them looking for younger men.

Even so, it took some looking to find the right woman.

Attractive.

Blonde.

Blue eyes.

Looking for s*x, not a relationship.

But I found her.

Or rather, she found me.

Her first message to me went straight to the point.

Emma: You’re cute.

Emma: Are you into cougars?

Emma: I’m looking for something simple.

Emma: And by simple, I mean s*x.

The picture she used as her avatar was presumably her. She looked vaguely familiar, but then again, I was in the habit of pursuing older women that were blondes. The sweet spot for me was the 35-50 range, especially women who were well maintained and elegant.

Emma had a reddish tint to her hair that looked natural, but the small avatar picture didn’t give much in the way of detail.

Me: That’s exactly what I’m looking for

The next question caused me to clench up.

Emma: Do you have a big c**k?

I considered lying. That was only going to get me in trouble. I half dodged the question.

Me: I’m gonna be honest. I’m average

Emma: Good. Men with big c***s tend to think that’s all they need.

Emma: I’m looking for a man who can please me.

Emma: Can you do that?

Me: I can EASILY do that

I was trying to balance between being confident and humble without sounding like I had nothing going on.

Apparently I passed the test because she wanted to set up a meeting. I liked how she scheduled the time.

Emma: Make sure not to plan anything for afterwards.

Emma: Things might progress quickly.

We didn’t meet at a fancy restaurant or even a crappy restaurant. Not a bar. I suppose it was a good thing we didn’t meet at the library.

It was a pretentious art gallery with an overpriced coffee bar attached. Or maybe it was an overpriced coffee bar with a pretentious art gallery attached.

I suppose Emma chose the place because it gave her the chance to wear a dress that was form-fitting without being slutty. Revealing, but subtle at the same time. She said she was going to be wearing a pink dress with red flowers. The large red flowers over her breasts weren’t exactly understated.

I wasn’t sure exactly how much older than me she was, but even if she was twice my age, she was in incredible shape and her face told me she was, at most, forty when she said on her profile she was fifty.

A cougar looking for a cub.

I was that willing victim.

After our initial greeting—a handshake where I got to touch her warm, soft hand—we sat and ordered our overpriced coffees.

And then we talked.

Or rather, she quizzed me about everything possible in my background.

Education.

Past and current jobs.

Past and current girlfriends.

Parents and family.

Hobbies and interests.

I felt like I was at a job interview.

I didn’t have a chance to ask any questions of my own.

She took it all in and didn’t blink at my honest answer of how my most recent serious relationship had ended though I kept some of the details about Jobeth vague. Nor was she upset that I labeled my relationship with Di as a friends with benefits situation.

When I asked about her interest in my family, she said she wouldn’t sleep with anyone who didn’t have some sort of connection to his family.

“It just shows a person with human connections to the world.”

She wasn’t amused when I said my hobbies and interests were video gaming and s*x.

After I said that, she drummed her fingers on the table while sipping on her coffee.

“Did I pass the interview?” I asked her.

Emma laughed. “Is that what I made this seem like?”

“To be honest: yes.”

“Are you turned off?”

I shook my head. “No. I love being grilled by a beautiful woman.”

She scoffed at my compliment. “Try not to be so obvious in your flirting. But answer this question for me: are you submissive or dominant in bed?”

I looked around nervously. The coffee bar was half empty and no one seemed to notice her question. Or maybe I just imagined that myself.

“Uh…neither?”

“That’s a terrible answer.”

“I mean, it’s not like I have to be in charge all the time. And sometimes it"s fun for her to do the work. I wasn’t looking for some dom-sub thing, if that’s where this is going.”

“Oh, honey, you have no idea where this is going. But you sound like a switch. I can work with that.”

I found a bit of boldness and managed to ask her, “Are you dominant or submissive?”

She smiled. “Would you like to find out?”

She insisted we go to her place. I was fine with that.

Her house was f*****g amazing.

Maybe it wasn’t exactly a mansion, but it was f*****g close.

It was huge. It had a separate five car garage and a circular driveway. It sat on a chunk of land the size of which I couldn’t begin to guess. There was a pool in the backyard, but it was still early spring so there was no reason to explore that. The entryway was bigger than the house I currently lived in that was chopped up into three apartments. The living room was two stories and we could have played a basketball game in there if not for the grand piano, acres of furniture, and what seemed to be a small home theater. She could have charged ticket fees for people to come in and watch movies on the screen.

Other than a glimpse of the kitchen, we simply went through the living room, up the curved staircase to the second floor, where I was ushered into her bedroom.

At least I assumed it was her bedroom.

She walked in with the confidence of a naval captain taking command of a flagship. I went to the row of windows that looked onto the backyard of the house where I saw the huge pool and acres of grass.

“I guessed you were wealthy but I didn’t know you were super rich,” I blurted out stupidly.

Emma laughed at me. “I worked hard to get all this.” She set her purse on a table in the large room. The table’s only purpose seemed to be a place for her to keep her purse.

“High finance?” I guessed. “Stock broker? Real estate? Family money?”

She stepped out of her high heels and relaxed. I realized she was almost a foot shorter than me. “I don’t know. My husband probably worked in all of those at one point or another. He came from money as well.”

My c**k, which was starting to work on going full chub, suddenly deflated. “Husband? I didn’t realize that you’re married.” I probably had a shocked look on my face. I knew the rich operated differently than the rest of the world, but this was my first confrontation of that.

The last thing I needed was to be caught with another man’s wife.

“Was married,” she said as she approached me. My c**k started getting hard again.

I breathed a sigh of relief. “Oh. Ex-husband. Okay. You had me worried there for a minute.”

“I’m a widow,” she said and then turned her back to me.

“Oh.” I didn’t know how to react to that.

“Unzip me,” she ordered. Just the way she said it I knew it was an order. The weird thing was I wanted to obey because I wanted to please her, not just because I wanted to see her naked.

I unzipped her. The dress was rather modest and it clung to her curves. She didn’t let it drop to the floor. She was classier than that. She stepped out of it and handed it to me as she turned around.

I didn’t even get a decent look at her ass. She was wearing elegant white silk panties; no thong for her. Emma had class.

Her lingerie was that balance between ornamental and functional. She knew she looked good in it. Her skin fairly glowed. There was no body art on her other than her natural freckles. I checked out her t**s, still hidden by her bra; the silk dimpled with her erect n*****s. My eyes went further down her body. Her panties clung to her p***y but nothing was outlined.

I wanted to tear her lingerie off, but at the same time I wanted to just stare at her in her semi-nudity for the rest of my life.

“Did I break your brain?” she asked me.

“You’re beautiful,” I blurted out.

Emma laughed at me. “I’ve heard that compliment too many times in my life. I’d rather you just prove to me that you’re useful.”

“Useful?”

“I want you…” she held up a finger. “No. I need you to f**k me right now. Strip.”

The word of command was enough to get me moving. I kicked off my sneakers, didn’t bother with unbuttoning my shirt and just yanked it up over my head. I unzipped my jeans and shoved them down with my underwear in less than a second.

I stood naked before Emma with my small c**k at full mast.

Emma took a step back and drank in my body with her eyes. I might have a small d**k, but I kept myself in good shape because I had to impress women in some physical way.

“Very nice,” she said, reaching out to caress my balls.

I whimpered a tiny bit and shied away.

A laugh on her lips, Emma said, “I didn’t expect you to be shy.”

“I wasn’t expecting you to touch me. I mean, I haven’t even kissed you yet.”

“Would you like to kiss me?”

“Yes. Kiss you and everything else.”

Emma stepped up to me and lifted her chin. My c**k kept us apart, but I bent forward ever so slightly and allowed my c**k to be compressed by her body.

Her lips tasted like strawberries.

That was ridiculous because a woman like Emma wouldn’t wear strawberry lip gloss like a middle schooler.

Her hand went behind my neck and we moved toward the bed that was easily the size of a medium-sized Old West ranch. I wound up on top as we got on the mattress but she silently insisted we roll over so she was riding me. We kissed the entire time. I tried to get her bra off but my efforts were wasted.

With her knees on either side of my body and her p***y, still covered by the white silk, pressing on my c**k, Emma sat up and reached behind her back. With no effort at all she unhooked her bra and freed her t**s.

They were gorgeous. Maybe she had had plastic surgery. Maybe she was just naturally beautiful. They weren’t fake, however. Maybe they didn’t sit high on her chest like an eighteen year old’s would have, but they were still incredible. Her n*****s were on the small side, but wonderfully puffy and pink. A few natural freckles dotted across her breasts leading me to believe she had to tan topless. I decided she was the sort of woman who got regular treatments in a tanning booth during the winter.