4. Manwhore Vs Cougar

I got to the hotel room stated on the keycard after a quick stop at the drugstore for condoms.

Damn this sugar thing might have its perks after all, no wonder all the babies are happy.

Shit! I really must be in and out of this thing. I really don't want to get too comfortable and get sucked into this lifestyle.

I decided to get comfortable and stripped to my undershirt and leave my pants on, should she wanted to undress me. I just didn't want to get my shirt and suit jacket wrinkled when I checkout of this room. I was tapping on my phone checking on my messages when she called me.

"Baby, I'm going to be a bit late, I got room service delivering you their finest cigar and whiskey. I read on your profile that you like them. So, wait up, I'll be there in an hour." She told me seductively.

"Virginia, you don't have to do that, I'll wait for you either way. But thank you for thinking about me. I'll see you in an hour." We talked a bit more then she ended the call.

Seconds later there was a knock at the door, I opened it and let the room service in, and leave her to set the whiskey and the cigar.

I tipped her and ask if I could light it here. She said yes and that this was Ms. Clark's specific instructions, as she flirted her answer to me. I just smiled and thanked her and ushered her out.

You can give it to her another time, now it's time to earn your money...damn!

How am I feeling so degraded but excited at the same time? Shit!

I decided to go to the balcony and light it out there and feel the afternoon breeze. My brain was still wrapping around the concept of how I was so anxious about being paid for sex. I usually do it the other way around. But this was actually turning me on I was still semi erect up to now, as I kept on touching my dick to calm myself down. I know, I would leave her sated hours from now.

I draw the cigar smoothly and taste the fine tobacco. This was the one bad habit I picked up, hanging out with the rich kids at the boarding school. We would sneak out and light their dad's expensive cigars and talk about girls and the hot tutors.

But being a boxer, I was surprised to find my cigar smoking habit fit perfectly amongst them. Even the committee like to reminiscent the old days, where there were still ringside cigar smoker. You would see old pictures of boxing match with clouds of cigar smoke. But I really need to slowdown, this had been two days in a row. It will definitely effect my endurance and my weight lifting performance.

It was an hour later when she found me in the balcony finishing off my whiskey, while I let the cigar died out. She was looking fine, as she take my hands and pulled me inside.

"Gary, you have no idea how long I've been asking for you to Adriana. You are very handsome and sexy baby." She took my hand and pushed me lightly, to sit on the bed.

"So, you're a boxer? I've seen your  pictures. I'm liking the tats..." She kept on slurring her words as she took off my undershirt and throw it on the floor. Then she caressed my bruises and said that she like the beat up bad boy look.

Oh fuck! Well then...I'm getting turned on. This fucking manwhore wants some....

She was stripping herself leaving nothing for the imagination as her sheer nude lingerie showed her nipples and her sexy strip down there. She was definitely a cougar, she knows what she was doing.

Damn I'm stiff, my dick is hard for her...

"Get up Gary and kiss hard me and throw me to the bed and fuck me senseless." She lowered her body down and whispered in my ear making me groaned.

Fuck this! I'm fucking doing this!

I got up and took off my pants, she smiled widely as she saw my dick springs out of my briefs excited to meet her. She giggled as I throw her to the bed and crawled on top of her and started kissing her.

She was moaning, as I was groaning to her little touches. My abs was still sore but my dick had far more urgent matter to attend to. I took off her bra and the thong making both of us naked and horny.

I was under her, sucking her, drawing out her moans. She was fisting the sheets, her back was arching upwards as she was feeling my tongue in her. I was gripping her thighs keeping her in place. She was moaning and then screaming my name, telling me that she was about to come.

Then I took her legs to my shoulder and gripped her waist tighter. She was liking my rough handling, as she moaned louder, and gripped my hair roughly, and pulled me closer to hers. I took her until she bucked, and climax in my mouth.

"Fuck Gary! You're so fucking good baby. Come here, I want to taste that big dick of yours." She told me as she instructed me to kneel, and wrapped her sexy lips on my dick.

She was a pro at sucking cock. I was high instantly, I was cursing and moaning her name again and again, telling her to go faster and deeper. Then I told her to stop, and put on my condom.

"Enough...on all fours Virginia, I'm going to fuck you hard. You're such a good cock sucker, you will earn your reward." Then I fucked her hard and fast.

She climax several times, before I finally let myself climax.

There! Building rapport done! You have done good my little guy.

I talked to my dick, as I discarded the condom. Virginia was fast asleep, when I left her in bed second ago. I took a quick shower then left her to go back to my place. I needed to do my daily boxing routine, since I still couldn't do my standard four hours extensive training because of the beatings couple of nights ago.

I called Fred to inform him, that I was not going to meet him at the boxing club.

"Fred, I'm doing weights at home, you can come if you wanted. But I'm good to train by myself tonight....um...yeah, ok then. See you tomorrow." I hung up on him. Secretly glad that he decided not to come to my place.

I spent two hours from warm up to conditioning, then finally for strength. I was gunning for three, when I just couldn't take it anymore. It was the cigar, I really need to quit.

I took a quick cold shower for five minutes, then switched to a hot one for ten. I was beat, as I finally slumped to my bed naked, I drifted off to sleep only to be greeted by my alarm the next day.