Riding Cheri

The frequency of visits to see Cheri wasn't as often as these stories might imply - we were friends for a very long time. 

When I called Cheri for what would be our third "date", I asked her to explain role play and why she had asked me about it.

"Haven't you ever had a fantasy, Will, a dream about something you've always wanted to do but have never done?"

"Well, as a matter fact, I have. I've always wanted to ride a bucking bronco in a rodeo with the crowd cheering for me and to win some sort of trophy, but I never rode a horse in my life."

"That's not exactly what I was looking for, but it doesn't matter," she replied. "Pick me up for brunch tomorrow and we'll go friom there."

The reason for our "dates' always being early in the day is that initially i asked Cheri that I be the first client of the day. Whether or not I would use my mouth on her, I didn't like the idea of fucking after some other guy, and she agreed, hence the brunch dates. 

i also offered to wear a condom but she dismissed it. "You haven't fucked anybody since your divorce, right?" she asked.

"Right," I answered truthfully.

"And how long were you married?"

"Twenty two years."

"And how many times did you cheat on your wife?"

"Never. I intended to once but never actually did."

"You see, Will? I believe you and I feel safe with you. I'd rather not have a condom in the way if we can do without it."

So the next day when we entered the restaurant lobby, she had a new idea. "You ask for a booth and I will ask for a table near you. We'll order the same thing (her favorite fruit salad) but eat separately. You can pay for our meals when we leave."

That seemed a little odd but I never questioned her instructions or her motives. When we were seated and had ordered our meals, I got a text on my phone.

Her text: "Every chance you get, look over and watch me. I'm not wearing panties. When you start eating, watch me while you eat."

My text: "Okay, but..?"

Her text: "Just watch."

I looked over and when nobody else was aware, Cheri slipped her skirt up over her knees, tenting it so that only I could see up her skirt. I could see the dark patch of her pubic hair and it turned me on. She smiled at me as she began rubbing her pussy with two fingers.

Her text: "Unzip your pants, pull your cock out and cover it with your napkin in your lap."

I actually was relieved to do as she said because there was already a bulge in my pants. I continued to watch and she continued to rub herself until the waiters brought our salads. Once we were basically alone again, she texted me again.

Her text: "Slide your napkin off your cock and don't cover it unless someone comes by."

There weren't very many people in the restaurant, especially in our area, so I complied. 

Her text: "These strawberries are good, but they need to be juicier."

Then I watched as she rubbed a strawberry through her slit and then slipped into her mouth. My cock rose to full attention and I wondered why she wanted to tease me. 

Her text; "Pick up a strawberry, and when I wipe mine in my pussy, put your strawberry in your mouth at the same time that I eat my strawberry, and imagine what mine tastes like."

Fucking hell! I didn't want to eat anything anymore, I just wanted to go over, throw her on her table on her back and fuck her senseless.

Eating the strawberry made my cock ache. I tried to ignore her and actually eat something but my stomach was feeling queasy; I wanted to get out of there. But I couldn't help myself, and I looked over at her again. She was pushing grapes inside her pussy, one by one.

Her text: "There are too many grapes in my salad. I'm saving some for later. Are you hungry?"

My text: "This is fucking killing me. Can I fuck you in the car?"

Her text: "No fucking until we get home; ready to leave? Your cock looks ready, lol."

I struggled to get my erection into my pants but managed to zip up safely. By the time I stood up she was already walking toward the lobby. I didn't wait for the checks but left cash on both her table and my booth. 

She giggled all the way to the car. "God, men are so easy. I bet I could have made you come, untouched, right there in the booth if I had enough time."

I didn't argue because we both knew she was right. My only goal was to get her home and bang her brains out. As soon as we started out of the restaurant parking lot, she pulled her skirt up, slid down in the seat a little and reached between her legs. To my painful dismay she produced a wet grape, seemingly glowing with her sweet honey. She put it under my nose.

"Just smell how delicious this grape is, Will. Take it in your mouth and hold it there."

It was like having her clit resting on my tongue. Her hands unbuckled my pants and unzipped the fly. She fished around until she pulled my cock out. 

"You can swallow the grape now, Will. And I have another for you, right.....here."

She plucked another grape from her pussy and pressed it to my lips. I sucked it in as she ran a finger around the tip of my cock. 

"Don't swallow it until I give you five strokes," she whispered into my ear. My cockhead swelled.

Her fist gently squeezed my shaft and stoked up and down so slowly that I involuntarily groaned. She counted slowly as she moved her fist. "One.....two.....three.....four.....five! Okay, Will, swallow the grape."

I didn't even chew the damn thing, I just gulped it down. We were just five minutes from her house and I wondered if I would make it.

She licked my ear as she slid the last grape between my lips and whispered softly to me. "I love teasing a man's cock, with my hands, with my mouth and with my pussy. Now I'm going to stroke your cock ten times but using my mouth. And if you can take it without coming, your visit today is free, Will. But I must warn you; I have a very hungry mouth."

At that point I didn't care what she charged me; I was going to choke her with my load and then fuck the hell out of her. She moved her mouth up and down the shaft even slower than she did with her fist. I pulled into her driveway as stroke number six pressed her lips down around the base of my cock. I grabbed the steering wheel, dug my heels into the floormat and waited for exstacy to happen.

After the ninth stroke she removed her mouth, opened the car door and got out of the car. I rushed into the house and she quickly got down on her hands and knees on the carpet, flipped her skirt up over her back and said, "Fuck me, Will, fill me up."

I unbuckled my pants and slid them down around my knees, pulled my cock out through my boxers and slid it into her with one thrust. It was like fucking melted butter, her warm wetness soaking my balls and my boxers. I didn't even try to hold back, I just let it go, grunting like a pig.

Cheri didn't move. "Don't stop, Will. Grab my hair and ride me like a bronco." She was panting, as aroused as I was. "Fuck me, Will, fuck me hard and fast!"

It was like a dream come true. I grabbed a fistful of her hair, pulled her head back just enough to see her smiling(?) and then pounded into her with all my might. Wet slapping noise filled the room and when I got close I released her hair, grabbed her hips and fucked her like I owned her. I came a second time, sweat dripping from my chin. I wondered if she had come as well and as I pulled away from her I saw her fingers rubbing her clit. 

I flopped down on my back, soaked and exhausted. When she got up I asked, "Did you come, too, Cheri?"

"Yeah, and lucky for you that I did, otherwise I'd be sitting on your face right now."

Later as I was getting ready to leave, I smiled at her. "That was the best fuck of my life and even better because it was free."

"If you will recall," she said with a knowing grin, "I never gave you the tenth stroke. I'm never free, Will."