Paid Plaything (fiction)

Megan and I had known each other for years.  We’d always flirted but nothing ever developed.  Whenever one of us was single, the other was trying to make a relationship work.  Eventually, we ended up in different cities but stayed in touch over email and instant messenger.

Chatting online, the topic turned towards prostitution and why people who could get laid on their own relatively easily would pay for it.  I told her that I thought it was about power and control.  With negotiated terms and payment, you knew what you were going to get.  They worked to please you and you didn’t need to feel guilty about accepting it or obligated to make sure they got off.  It was really just a form of masturbation with another person as your masturbation sleeve or dildo.

She agreed and then asked the question that changed everything between us.

“Would you ever sell your dick for money?”

Kinda turned on by the question, I let her know that it all depended.  What the woman looked like, what she wanted to do, and whether I trusted her.  Obviously, I would never try and make a living off it, but it would be pretty hot to spend a weekend as a woman’s boytoy.

“What about for me?  I’ve wondered what it would be like.”

Now, definitely turned on, I told her that I’d fuck her for free, but it was a moot point because I was in New York and she lived in Chicago.  

Turns out, she wasn’t interested in getting laid, but in having a paid plaything for the power dynamic.  She wanted a sex slave for the weekend.  I sketched out a few ground rules, nothing dangerous, nothing permanent, nothing public.  

She offered a thousand dollars and a free plane ticket to Chicago.  We booked the flight for two weekends from now.  I put it on my card with the understanding that I had to make it to Chicago and would collect at the end of the weekend if I kept my end of the bargain.  Cajoling for specifics didn’t work.  She promised to stay firmly within the ground rules, but left it at that.

The two weeks zipped by and I was deplaning in Chicago before I knew it.  She met me at baggage claim and looked me straight in the eye.

“So, Woody, you know what you’re getting into?”

I told her she looked great and followed her to her car.  Settled into the passenger’s seat, I complied immediately when she told me to unzip my pants and pull my cock out.  With one hand on the wheel and another slowly pumping my dick, we made it back to her place.  I grabbed my bag and followed her inside.  

She had a seat on the couch and spread her legs, offering an excellent view.  She hiked the black dress up around her thighs, letting me know that she wasn’t wearing any panties.

“Strip naked.”

I stood in front of her naked with a hand on my cock.  She sent me to the kitchen with instructions to bring a vodka martini for her and the vodka bottle and a shot glass for me.  She took her martini and had me place the bottle and shot glass on the table by the couch.

She pointed at her knee and told me to start licking it as she sipped the martini.  I began there and started working my way down her thigh.  Her free hand sank into my hair and guided my head.  Before long, my tongue found her hips and slid up and down in long slow strokes.  Her fingers tightened and I circled closer and closer to her clit.  When she came, legs tightened around my head and I could feel her whole body convulse.

She pushed me back and poured me a shot of vodka.  I took it and started again, this time, licking, sucking, and slurping my way down from her calf.  After five orgasms for her and five shots of vodka for me, she was ready for a change of pace.

She stood, pulling her dress down, and had me bend over the couch.  I heard her heels click as she walked around behind me, but I yelped in surprise when her hand slapped down against my ass.  

“Not another sound or I’ll gag you and really whip your ass.”

She got in a few licks with her hand before producing a crop and whipping me mercilessly.  I tried to keep quiet, but as the blows rained down, a gasp of pain and pleasure escaped.

“That’s it, into the bedroom, I’m just going to have to tie you down and gag you.” 

When I saw the array of toys laid out on her bed, I knew I was going to really earn the money…