Personal Training Ch. 03

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An old friend has a proposition for Annie
2.5k words
4.46
16.9k
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Part 3 of the 15 part series

Updated 11/02/2022
Created 05/18/2014
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MissPrim
MissPrim
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It was another day of frustration. You would think that the life of a self-employed writer would be stress free, but it is not. No matter that I work in my pajamas with the television on in the background. People who tickle a keyboard for dollars enjoy a status somewhere between squat and jack. But the accident threw me out of my job. I was in bed for three months, not very mobile months after that, and there were bills to pay. Fortunately I had a skill to exploit and a laptop in my bed. But things are far from wine and roses in my little world. For one thing, there are the clients.

Some clients just did not get it. The last one, for the third time, requested pitches for pieces for the next month, and you know what? After the first two sets of pitches, I'd given her my best ideas. If she didn't see that I couldn't waste my time with her anymore. I needed money, not endless discussions how I might make that money.

But the truth was, most of my frustration was centered more in my loins than my work. That was the part that got me. Yeah, yeah. I had a bad year. Yeah, yeah, I didn't have enough fun. What if I didn't want to have fun? What if I didn't want to throw myself into the arms of the first guy that I found attractive since the accident? Maybe I had too much hurt to even think about it? Damn, damn and damn again. I couldn't stop my randy thoughts about that guy in the gym. 



I pulled up my latest assignment on my computer. Okay, it wasn't due for three weeks. However, if I don't do it now, and waited until it was due, three other jobs would come up wanting to be done "right freakin' now." The subject matter didn't help much. "Sex Secrets--How He Loves to Love You." 



This article didn't help my horny thoughts. My hand wandered to my clit. 



No! That wasn't enough last night and I couldn't take the hyper-excitement of being partially satisfied. 



My cell phone rang. 



"Hi, honey," said a silky voice. 



Oh geez, it was Jack, my old boss. 



"What's up, Jack?"



"I'm in town. Want to get together for dinner?"



"Will there be wine?"



"As much as you like."



"Yeah, sure, you old cheapskate." Jack's parsimony with his cash was the stuff of legend.



"You've hurt my feelings," he said. 



"Like you have any to hurt."



He chuckled. "Okay, I'll pick you up."



"Seriously, you'll spring for the gas?"



"Bitch. I'm already here."



I got up from my bed and peered out the window. 



"Really, another new car?"

I stared at the sleek black Mercedes with a bit of awe. 



"Will you hurry up, or what?"



"What, afraid you'll miss your reservation at Hooters?"



"One," he said. 



"Jack, I'm not ready."



"You have to ten, and you are wasting time. Two."



"Bastard." I hung up the phone, and shedding my robe, grabbed a pair of dress black pants, black lacey shirt and one of my sparkly jackets. I had no way of knowing where he'd take me. But this combination worked for most places. I'd wear a dress, but I still needed a knee brace to keep things together for me. I slipped on a pair of pointy black flats, grabbed my purse and cell phone and was out the door. 



"Ten," he announced as I climbed into the car. 



"Ass," I said. It was always "ten" when I got in his car. 



He laughed again. Jack had brown eyes, and was handsome, even for his early sixties. His black hair turned salt and pepper, but I thought it made him appeared more distinguished than he deserved. He was rich too. Oh, not from his own efforts. Daddy made the money. He promptly threw Jack out of the house when Jack refused to takeover the family business. But after Jack's mother died, father and son had a tearful reunion, and all was good again. Jack could have any woman he wanted, but the problem was he didn't want any woman for more than a few nights. And it wouldn't be me anyway. He liked a specific type, very tiny, very thin. Someone his near six-foot frame would tower over. 



His clothing, a gray camelhair jacket and black pants and shirt weren't clear clues as to our destination. But it was obvious he'd gone all out for this night. His hair had that close shaven appearance of someone who'd just had a haircut and he was wearing cologne. 



"Where are we going?" I said. I was feeling more than a bit suspicious. Something was up. 



"Shut up and ride," he said. "Take a nap. We'll be busy tonight."



Okay, my friend was an asshole. The basis of our friendship was that I accepted his abrupt manner and the domineering attitude. It was his essential nature. Oh, with other people he was the polite gentleman. Only with me did he let his guard down. When we worked together I was his office wife, best buddy and sometimes wingman. But that was all. For one thing I was married at the time. For another, and he'd tell you the same thing, he was a heartless dick. He couldn't love anyone and made no bones about it. And that was fine with me. 



"Hey, wake up."



I opened my eyes. We were at one of the Connecticut casinos. 



"I should have known. Do you have a coupon for the buffet?"



Jack chuckled. "As a matter of fact..."


I rolled my eyes. "They don't have wine at the buffet."



"Yeah, but you can get it at the racing book."



I saw my evening set ahead of me now. This was an old routine. We'd spend the evening watching races, while Jack made his bets and drank an endless supply of free strawberry daiquiris, his guilty pleasure.

"Did anyone ever tell you what an exciting man you are?"



"No."



"Thought so."



#



After a half dozen three-ounce daiquiris, Jack's mood changed. He let the last few races go by without getting up and placing his bets. Unlike him, he stopped laughing at my jokes and got very serious. I had a few glasses of wine myself, and had a little buzz on. 



"I don't think I can drive," he said. 



"Well, stop drinking and we'll leave in a couple hours."



"I thought we could stay here in the hotel."



"Jack, are you feeling okay? It sounds like you getting ready to spend money."



"Oh, what the hell. You can't take it with you."



I put my hand to his forehead. "You're not running a fever."

He grabbed my hand and kissed it. 



"Jack?"



"I've already booked the room. The key is in my pocket."



"One room."



"Yes. But there are two beds."



Oh geez. "I'll get a rental and go home."



He gave at me a calculating stare. 



"Okay, just help me to my room."



I should have known better. I was aware he was a predatory bastard. It just didn't occur to me he'd cross the lines we so carefully drew years ago. 



As soon as the door was open he pulled me in and shut the door. He pressed against me. 



"Have you ever wondered," he said, "what it would be like together?"



Of course I did.

Any woman who ever saw him thought the same thing. I swallowed hard. 



"Why don't you lay down on the bed?" I said trying to figure a way to get him off me. 



He stumbled over and sat hard on one of the king-sized beds. He looked at me as if waiting for me to join him. 



"Come here. I have something I want to tell you," he said. 



Reluctantly I went over and sat next to him. 



"You know, I missed you," he said his words slightly slurred. "Since you left, things haven't been the same...anyway, that husband of yours never deserved you."



"So you've told me," I said coldly. 



"And then he got you into that accident and he died and you nearly died too. I can't tell you how upset I was that he almost killed you. But you loved him, and I know how much you hate people trying to help you, so I stayed away. But it's been a year, so I thought..."



He fumbled around in his jacket pocket and handed me a box, a velvet blue ring box. I had to look and almost fainted. It was a one-carat emerald cut diamond, the type I joked I always wanted. 



"Jack?"



"It doesn't have to be for now. I just want you to know I'm serious about this."



Oh, fuck. 



Fuck. 



Fuck me. He gave me with such an earnest look that it broke my heart. 



"You are such an idiot," I said. 



"I know," he replied. And he leaned over and kissed me, tasting of strawberries and alcohol. 



"You don't love me, Jack."



"No, but I need you," he said. "God, you look so hot."



"Have you had your eyes checked lately?"



"Shut up," he growled. He leaned over again, the scent of the wool of his jacket and his cologne colluding to strip me of my senses. With his two hands he pushed off my jacket and nibbled on my neck. His hand strayed to my breasts, squeezing one then another. Finding my mouth he kissed me intently. First his tongue played with my lips and then dove in. God forgive me, I let him. Wine and frustrated sexual heat did their dirty work. I gave in to the need that tingled from between my legs and up through my attention starved body. My alcohol fueled decision made, I let loose. He didn't know what hit him. 



I tugged off his jacket. He worked the buttons of my shirt. I got his undone faster and his shirt was off before mine. He reached around and undid my bra, and my 38DDD's sprang out, released from their lace prison. Jack's eyes got very wide. 



"Shit," he said. "I knew they were big, but..."



"Shut up," I said. My tongue attacked his nipples and then worked its way down his chest, his abs and his bellybutton, my breasts rubbing each area before my mouth did. I swirled my tongue there, darting in and out of that little hole. He moaned a little, and I pulled at the end of his belt, and in one swift motion, released the buckle and jerked the belt up and out. Unbuttoning his fly and unzipping his pants, I pulled his pants down. His cock rose up under his shorts, and I tugged them down too, not bothering to take either his shorts or slacks fully off his legs. 



"I wish I had some lube," I said. 



"Jacket pocket," he said. 



"Seriously?"



"I come prepared."



"You've got condoms too?"



"Come on. You know I get tested every few months."



"Safe sex is happy sex," I said. 



"Yes," he sighed. "I have condoms too." 



"Good, but we're not there yet."

I reached over to his jacket, fished out the lube, and smeared a good dollop between my breasts. Cradling my flesh between my hands I lowered my breasts on his dick rubbing up and down the shaft. After all this time, it felt good to have a man's hard cock between my breasts. Little electric shocks traveled down my spine at the thought of what I was doing to him. I dipped my head down and licked the tip of his penis. His cock hardened more and a few drops of pre-cum pearled at the tip. 

 "Fuck," he said. 



"Oh, not yet."

I grabbed one of the condoms from his pocket and ripping the packet open, took it and rolled it on. 



"Bitch," he said. 



"Asshole," I replied. With that I plunged his dick in my mouth, and worked my tongue up, down and around it and then again. Gripping the base I added the strokes of my closed hand, my saliva dripping down his shaft. As he strained in my hand, my head lowered to his balls, while I moved my index finger to the sensitive spot under the head of his cock. While tip of my finger and my fingernail played with that, I teased his balls with my tongue. When I took one in mouth his back arched up. 



"Ah," he groaned. "Stop."



"Stop?"



"I'm not as young as I once was. I only get one shot at this."



"I just think you're out of practice." My head dipped back to his waiting cock. 



He put his hands on my shoulders, and sitting up, pushed me away. 



"I must be, to let you call the shots."

With that he pulled me up and across him, placing me on the flat of my back, while he turned, kicking off his slacks. He pulled at the waistband of my pants, and pulled them down, taking my underpants with them. Jack looked at my knee brace then.

"Just leave it there," I said. 



Moving between my legs, he pushed apart my thighs with his hands, and lowered his head to my clit. He lapped it lightly, his hot breath sinking into the middle of my mound. 



"Oh," I moaned. 



He picked up the pace, and the pressure, taking his tongue lower and licking the entrance of my pussy. Then he speared it. His cooling saliva on my clit, and the pressure of his tongue pushing inside me made me gasp. His hand moved to my clit then, and rubbed the soft folds of skin around it. 



"Oh, oh." 



He picked up the pace, his fingers becoming more insistent. My breathing quickened and I took his hair in my hands holding him tight against me. I came with pent up energy, my pussy bucking against his face. He pulled my hands away from my head and rising up pushed his cock inside me even as my cunt pulsed. I cried out again as he plunged deep inside me, prolonging my orgasm with his strokes. My tits danced with the force of his pounding.

Jack grabbed my hips hard with his hands and drove his cock in and out of me as he rode my orgasm to its end. It felt so good. It felt so very good to have a man slide in and out of me. 



His last thrust had brought him over the edge.

"Fuck, oh fuck!" he cried out.

With that he collapsed on my chest, breathing hard. There was a long silence while Jack lay on me while his breaths slowed. 



"Jack, are you okay?"



He pushed himself up and grinned. "If I knew you were this good, I'd have given you better performance ratings."



"Asshole."



"Bitch."

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