Cowboy Up

by Just Plain Bob

Copyright© 2018 by Just Plain Bob

Fiction Sex Story: A look at one man's life.

Caution: This Fiction Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   Cheating   .

I met Christine at a seminar on Industrial Relations. It was mostly bullshit from people who had never held a tool in their hands and had no real world experience. They were full theories that they had learned from textbooks, but my company was paying the freight so there I was.

When we broke for lunch I headed for the hotel restaurant. I stopped at the bathroom to take a whiz and when I got to the restaurant I found that all the seats were taken and the greeter told me there was at least a twenty minute wait. She asked for my name so she could add it to her list, but I told her to forget it; I’d go someplace else for lunch. I heard a voice say:

“I wish I could do that.”

I turned and saw an extremely attractive brunette sitting on a chair in the waiting area.

“Why don’t you?” I asked. “There are a lot of restaurants in the area.”

“No car. I could walk to one, but I’d never get back in time for the afternoon session of the seminar.”

“Not a problem. You can ride with me if you think you can put up with a dirty old man for an hour.”

“You’re not old.”

“I’ve been a dirty old man where good looking women are concerned since I was thirteen.”

“I’ll chance it” she said and stood up, took the arm I offered and we headed out.

The Village Inn was the closest so that is where we went. On the drive over I asked her where she worked and was surprised to find out that she worked for the same company I did only out at one of suburban offices. She didn’t have a car and had taken the bus to get to the seminar.

We chatted over lunch and I found out she was single and shared a house with two of her friends. From me she found out that I was single and had a three bedroom house.

“Why does a bachelor have a three bedroom house?”

“Planning ahead. I won’t be single forever and I expect to have kids eventually so I’ll need the extra bedrooms and my father convinced me that it was better to build equity than collect rent receipts. I had enough in savings for a down payment so I went ahead and bought a house.”

She gave a small smile at hearing that and then we discussed the seminar and I found that she had the same opinion that I did of what was being spouted. The waitress had put everything on one check and when lunch was over Chris asked me what her share was and I told her it was my treat. When we got back to the hotel meeting room she thanked me for taking her to lunch and then she went to her seat and I went to mine.

When the seminar was over I spent ten minutes talking to a few others I knew who were in attendance and when I got to the lobby I saw that it was pouring down rain. I saw Chris standing at the door looking at the falling rain and I remembered her telling me she had to take a bus to get to the seminar and I knew just what she was thinking. She did not want to go out and stand at the bus stop in the rain and wait for the bus.

I walked up to her and asked if she would rather ride with me than wait on a bus and she smiled and said that she would indeed. By the time I got her to her house I had a date with her to go to dinner and dancing on Friday night.


On Friday night when I picked her up I met her two roommates. Brenda was a blond sexpot and her overall appearance screamed out “Fuck me! Please! Somebody fuck me!” Maria was a good looking redhead with a slim body that didn’t look strong enough to carry her breasts which I guessed were 38’s or 40’s.

On the way to the restaurant I noticed Chris looking at me with a bemused smile and I asked her what she was smiling about.

“I saw the way you were looking at my roommates. Nothing new there. All guys look at them the way you did.”

“Why does that make you smile?”

“Because I know what guys want to do to them when they see them.”

“Once again; why does that make you smile?”

“I smile because I know something that all the guys who look at them don’t.”

“And what might that be?”

“They are both dyed in the wool lesbians and are way into each other.”

“Hopefully the fact that you are with me on a date means that you don’t share their views where men are concerned.”

“That would be a safe assumption.”

We talked over dinner and we learned a lot about each other. She was one of six kids and the only girl and as a result of playing with her brothers and their friends she grew up as a tomboy. She had gone to college on a basketball scholarship and had been working where I work since she graduated.

“I know what the company pays so you should be able to afford a car. Why are you taking buses to get around?”

She had been smiling while we were talking, but when she heard that question the smile disappeared. She stared at me silently for maybe ten seconds and then she aid:

“I don’t need a car because I don’t have a driver’s license.”

“They are easy enough to get.”

“I don’t have one because they took mine away from me.”

I figured from her tone and response that it was a sore subject with her and I’d best back away from it so I said nothing, but then she went on.

“It wasn’t my finest hour. I caught my husband in bed with the bitch who was supposed to be my best friend. I went and got blind stinking drunk and was stupid enough to drive in that condition. I ran the car into a bridge abutment and totaled it. Luckily I had my seatbelt on and the airbag deployed. I was given a DUI and I saw no sense in buying another car until I can get my license back. Should get it back by the end of this month.”

“Still have the husband?”

“Hell no! I got rid of his worthless ass when I sobered up.” She smiled and said “He got his. He married the bitch and she cheated on him, caught the clap and gave it to him. I laughed for weeks when I heard that.”

“Didn’t sour you on marriage did it?”

“No, but I’m going to be a lot more selective in choosing the next one. I’m going to have to be sure of him before I say yes to a proposal. What’s your story? I would have expected a man your age to be married by now.”

“Similar to yours only times three or four. My fiancé Sarah had her bachelorette party and two days before the wedding I got a package in the mail. It was pictures of my fiancé having sex with three or four guys while her girlfriends stood around and urged her on. The package also had a note in it that said “Are you sure you want to marry someone like this?” I never found out who sent the package, but the answer to the question was no and not just no, but HELL NO!

“She tried to convince me it meant nothing. It was just a last hurrah before settling down to be a faithful wife and mother, but I wasn’t buying it. A year or so later she married some other guy and he caught her cheating on him and he shot her and her lover. A year after I broke up with her I met Marge, dated her for six months and then proposed. She said yes and moved in with me. Two months later I came home two days early from a business trip and caught her in bed with two guys. Her father and her brother.

“Next on the hit parade was Jackie. We went together for about four months before she moved in with me. Same deal as with Marge. Came home early and found her in bed with a guy. The guy quickly dressed and got the hell out and when he was gone I asked her why. She looked at me like I was brain dead and said:

“Did you see the size of his member when he pulled out of me? I just had to try on something that big if only to see if I could get inside me.”

“I’ve been a tad leery of relationships since then. It took me a year before I began to date again.”

Dinner was followed by drinks and dancing. We had a good time and I enjoyed being with her. When I took her home I did get a kiss on the cheek and a “Call me; I had fun and I’d like to do it again.”

The second date led to a dozen more. On the fourth date I got a knee buckling good night kiss. On the sixth we had a hot make out session in the car when I took her home. On the ninth she said she didn’t want to make out in the car:

“And since we can’t do it at my place without an audience I think we should go to your place.”

At my place we had steamy make out session. The next two dates ended up at my place and on the second one she asked

“Why are we wasting time? We both know what we want to do.”

“I’ve been taking it slow because I didn’t want to scare you off.”

“That’s nice to know; that you don’t want to scare me off. Lead me to your bedroom. I want to see if we have a future.”

“What do you mean?”

“A few of my friends have gotten married and then divorced because they found out that they were not sexually compatible with their men. In all the cases they didn’t have sex with their partners before marrying them. Both parties were virgins when they went to their marriage beds and both said that they wouldn’t have married the men they did if they would have known beforehand what they were getting into. I know what they are talking about because I also experienced it. I didn’t go into my marriage with Jeff as a virgin. I’d had a few boyfriends before he came along and I’d dumped a couple of them because they were lousy lays.”

“So if I don’t ring your chimes tonight I’m history? Thanks, but no thanks. Grab your coat. I need to get you home.”

“What? You can’t be serious. I’m ready to go and you are saying no?”

“That I am.”

“You aren’t making sense here. You are turning down freely offered sex? Why in the hell would you do that?”

“I have my reasons and that’s all I’m going to say. Come on; get your coat and let’s go.”

She got her coat and stomped over to the front door, turned and looked at me as she pulled her cell phone out of her purse and said:

“Fuck you Dave! I’ll call a cab. I don’t feel like being around you right now.”

She went out and closed the door behind her. I was moving toward the door to go out and catch her and tell her not to waste her money on a cab when I caught myself. The break wasn’t clean, but it was still a break. I caught her and talked her out of getting a cab it would just prolong things. As it stood right then it was over. Leave it that way was my thinking. I went into the kitchen, poured myself a generous amount of Jack in a glass over ice and sat down at the kitchen table and thought about what had just gone down. I had really liked Christine. Shit! Admit it Dave. It was more than just like. I honestly thought that the relationship was going to go somewhere. I finished the Jack and went to bed.


The next few weeks went by and for me it was pretty much go to work, go home, sleep, get up and go to work again. I did think about Christine a lot, but resisted all the urges to pick up the phone and call her. It was a Thursday, three weeks since the day Christine and I parted when I walked into my office and found Christine waiting there.

“About time you got here. I’ve been sitting here waiting on you for a half an hour now.”

“You’re lucky. It could have longer. I’m ten minutes early. What brings you here?”

“I need to know what happened. I thought we had something good going.”

“Not the time and place to talk about it?”

“Okay; give me a time and a place.”

I looked at her and thought “Do I really want to go there” and then decided to give her what she wanted.

“The Hideaway at five-thirty.”

“You aren’t just jiving me are you? You will be there?”

“I’ll be there.”

She left and as she walked away I wondered why I hadn’t just told her it was personal and I wasn’t going to talk about it, but even as I had the thought I knew why I didn’t. The fact that she was in my office waiting for me told me that she wouldn’t let it go until she knew why. I just decided to get it over with.

I didn’t get much done that day. It seemed like I was looking at my watch every ten minutes or so with five-thirty at the Hideaway on my mind. The day finally ended and I headed for my meeting with Christine. She was already there sitting in a booth in the back waiting for me when I got there. She had already ordered and there was a Jack over ice siting on the table waiting for me. I sat down, picked up the drink, took a sip and set it back down and looked across the table at her.

“Okay Dave; let me in on it.”

“Alice, Elise, Marge, Sarah and Jackie.”

“What does that mean?”

“You wanted to know what happened to us and I just told you.”

“You didn’t tell me shit; you just said five names.”

“Those names are why we cratered. You remember our last time together?”

She nodded a yes and I asked “Remember what you said?”

She shrugged and I said “Think back on it. What were the words that followed “Lead me to your bedroom?”

She shook her head in an “I don’t remember manner” and I said “Your exact words were “Lead me to your bedroom. I need to see if we have a future.”

“Remember it now?”

“Yes.”

“To me that meant you were saying if I didn’t do it for you I would be history. Think back to what I told you about my history with women. I never covered high school and college. From tenth grade to graduation I went steady with two girls and they both dumped me. It happened again in college. I met Alice at Freshman Indoctrination and by midterm we were going steady. She dumped me for a jock midway through our sophomore year. In my junior year I hooked up with Elise and she traded me in for another guy the third week of our senior year. Beginning to get the picture? You think maybe I was starting to wonder what was wrong with me that I couldn’t keep a girl? All of that shit behind me and then you basically tell me that if I don’t measure up in the bedroom I’m history? Can you imagine what it would have done to me if we had done it and then you started saying no to me when I asked for dates? Well fuck that shit!”

“I’m sorry you took it that way. I only meant it as a funny,”

“How was I supposed to know that? You had just finished telling me about your girlfriends and that you had dumped a couple of guys who were lousy lays. Right after that you hit me with if we have a future shit? No way I saw it as you making a joke.”

“Well that’s all it was. The reason I’m here is I wanted to know what was wrong and see if I could fix it. I was sure we had something good going before it left the rails and I wanted it to continue. I want to put us back on the tracks.”

She looked at me expectantly as I considered what she said. I’d also thought we had something good going and I had wanted it to continue. Like her I would like to put us back on track, but in the back of my mind there was a little kernel of ‘leery.’ It might not be manly of me to admit it, but I was afraid of being hurt again. If it happened again I wasn’t sure that I’d be able to eventually get over it. While she said she was joking when she said the future thing she had also said she had dumped a couple of guys because they didn’t measure up in the bedroom as far as she was concerned. I sat there looking at her as all those thoughts raced through my head. Suddenly from somewhere in my brain a voice said:

“Cowboy up Dave. You might never meet someone this nice again. Don’t let her go!”

I took a deep breath and asked “Would you like to have dinner with me tomorrow?”

Her smile when she heard that lit up the room. We made arrangements for me to pick her up at her place at six and she got up and headed home.


I arrived at her place at six and rang the doorbell. Brenda answered the bell and when she opened the door and saw it was me her face went hard and she said:

“Oh; it’s you.”

I can get my back up just like anyone else and her attitude ticked me off.

“Fucking A doddle it’s me. You want to take your pissy attitude and go and let my date know I’m here?”

She turned and walked away leaving the door open. I didn’t know if I was supposed to follow, but I decided not to. A minute later Chris came to the door.

“Why are you standing there?”

“Seemed to be safer to stay here than go inside where Brenda and I could get into it.”

She gave me a long look and then said “I’ll get my purse.”

She came back with her purse and we went out and got in the car and as I pulled away from the curb she asked:

“Care to tell me what happened back there?”

I told her and she said “I’m sorry. It was my fault.”

“Your fault? How is it your fault?”

“The night I stomped out of your place I came home in a pissy mood and Brenda and Lois asked me what was wrong. I told them you had thrown me out. I know that you didn’t really, but at the time that is how I felt. The way it went down to me meant you were throwing our relationship away. They both wanted to get in the car, drive over to your place and cut your balls off. It didn’t help any that I have been in a bitchy mood since that night. When I told them I was going out with you tonight they tried to talk me out of it. They said you would just hurt me again and that you were an asshole and didn’t deserve a second chance. They are unhappy with me because I told them to butt out. They are my best friends and have been since high school and they worry about me. Don’t let Brenda’s attitude get to you.”

After dinner we went to the Boom Boom Room for drinks and dancing and from the way Chris pushed her body against mine as we danced I knew how she hoped the evening would end. I wanted it too, but the fear of rejection following it was still alive and well in my mind. Once again from somewhere in my head the voice was yelling at me “Cowboy up Dave.”

At eleven-thirty we were in the car and I asked “Where to?”

She looked at me and said “Your place?”

She said it as a question. The voice in my head was screaming now “Cowboy up Dave; cowboy up and do it!”

I smiled and said “My place it is.”

When we got to my place she headed straight for the bedroom. There was no talking. It was walking through the front door and go straight to the bedroom. I followed along behind her. As soon as she was in the room her clothes were hitting the floor. It was all happening faster than I expected and as a result I was a little behind her in the shedding of clothes. By the time my clothes joined hers on the floor she had the bedcovers down and was lying on the bed spread out and waiting.

It was almost magical. I went down on her and my mouth gave her her first orgasm. She had two more when I made love to her in the missionary. She went down on me and got me up for a second round and I gave her two more orgasms. Then it was sixty-nine followed by a session of doggy and I got her off one more time.

I was all set to cuddle and snuggle when Chris sat up and said “Oh shit! Look at the time. I have to work today. You need to get me home so I can shower and change clothes.”

“On a Saturday?”

“We have an audit scheduled for Monday and I’m going in to see that we are ready for it.”

I hid my disappointment and got up and dressed. On the way to her place she apologized.

“I didn’t expect the night to end the way it did. Knowing I had to work today I should have waited for our next date.”

When I asked if we could get together that evening she told me she couldn’t because she would be absolutely beat and when I asked about Sunday she said she couldn’t because she had a baby shower to go to. I didn’t press it. When we got to her place she gave me a hot passionate kiss and then hurried inside.


The house kept me busy over the weekend. That was one of the tradeoffs when you went the build equity rather than collect rent receipts route. You couldn’t call the landlord to fix things. Monday I called Christine’s office and Mavis answered the phone. Mavis used to work in my office, but had transferred to the Hanover office to be closer to home and to her kid’s school. I asked for Christine and Mavis told me she was in a meeting. Because she was an old friend I asked I asked how she was doing, asked about her hubby and kids and then listened to her answers. Then, purely to make conversation I asked how the audit was going.

“Audit? What audit?”

“The one you had to work on Saturday for.”

“I don’t know anything about an audit and nobody has worked on a Saturday in this office in the two years I’ve been here.”

“I guess I’m thinking of something else. Say hi to Burt for me okay?”

As I hung up the phone I was shaking my head and telling myself I should have known better that to take back up with Christine again. If I could have gotten my hands on the voice in my head that kept telling me to “Cowboy up” I would have strangled it to death. I “Cow boyed up” and look what it got me. I was once again left with the impression I couldn’t get it done in the bedroom. Alice, Elise, Sarah, Marge, Jackie and now Christine. Fuck it! I’d start using call girls where the only one I’d have to worry about satisfying was me.

I knew a couple of girls who worked for an escort service and I knew that they both provided ‘extra services’ on dates. Of course making that decision didn’t put an end to all the thoughts running through my head. What did I lack? I gave Christine my all and she seemed to have an orgasm or two. Was it just an act? It must have been. What was wrong with me? Maybe if I paid Lois or Tanya (the two girls I knew who were escorts) a little extra they could critique my performance and give me pointers.

Tuesday morning at work I debated calling the Hanover office and asking for Christine, but decided not to. We were done so leave it at that was my thought. Wednesday I spent most of my mornings in budget meetings and when I finally got back to my office Myra (my secretary) handed me a couple of message slips. One of them was from Christine and when I sat down at my desk I picked up the phone to call her. I got the first five numbers punched in before I caught myself and said “Fuck no!” I hung up the phone and threw the message slips in the waste basket. I managed to push Christine to the back of my mind and I had a pretty productive day.

It had been a long established habit with me to turn off my cell phone when I went in to work and only turn it back on once I left work and was in my car. I wasn’t surprised to see missed messages and voice mails from Christine. I deleted them without listening to them or reading them. Once home I fixed myself a bite to eat. Jack Thomas was retiring from his position as regional manager and I had been promoted to fill his position. His retirement party was Saturday and I had originally planned on Chris being my date for the affair. Fortunately I hadn’t yet asked her.

After eating I called Faraday Escort Services to arrange a date for Jack’s party and requested either Lois, or Tanya if possible. Luckily Lois was available and I made the necessary arrangements. A little back story is in order here. Where I am employed there are always social functions to attend. Some you can skip, but the others are more or less mandatory. You could skip them if you wanted to, but it wouldn’t be all that great of a career move if you get my drift. There was one of these functions coming up and I wasn’t seeing any one at the time. If you attended one of these events alone you stuck out like a sore thumb.

I was talking with Jack Thomas in the breakroom one day and I mentioned that I hated going to those functions alone. He told me about Faraday and explained how it worked and what the fees were. He explained that the place was not a call girl setup and the majority of the girls were strictly arm candy and didn’t even give you a kiss on the cheek at the end of the date. Then he said that there were a couple who would provide ‘special services’ but it was strictly an arrangement between you and the girl and that Faraday was not involved. Then he told me that I was interested in ‘special services’ (wink wink) I should request Lois, Martha or Tanya.

I called Faraday, requested Lois and took her to the function. When the function was over I mentioned that I’d heard she offered special services. We discussed things and I had a very enjoyable three hours at the cost of only three hundred dollars. I’d used Lois several times and she always handled my needs with a smile. She would only work through the agency, but she did give me her card so I could call her and make sure she was available before I called the agency. One day I called and she told me that she wouldn’t be available for the night in question, but to call the agency and request Tanya and she would let Tanya know about me. For almost a year I used the two of them when I needed (or wanted) a date. Then I used them between Marge and Sarah and then again when I was between Sarah and Jackie. Now here I was taking Lois to Jack’s retirement party. The irony of the situation was not lost on me. Here I was taking a girl recommended by Jack years ago to his retirement party.


Over the week I received several calls from Christine, but I didn’t take any of them. Thursday and Friday I hid out in my favorite sports bar after work. It was a place I’d never taken Christine to so I didn’t have to worry about her finding me. If she was even looking. That didn’t work out to well for me. Friday I’d been there about an hour and I was sitting at the bar watching the Arizona Diamondbacks playing the Colorado Rockies when something cold and wet was poured on my head and ran down my back. I spun around with fists clenched ready to punch some asshole out and came face to face with Christine’s roommates Brenda and Maria. The bartender had seen what happened and he tossed me a bar towel. I unclenched my fists and caught it and then screamed at the two cunts:

“What the fuck is your problem! Why in hell did you do that?”

“Because you’re an asshole and you deserve it” Brenda snarled.

“Fucking dirt bag!’ Maria chimed in.

“What the hell did I ever do to you to earn this?”

Brenda, still snarling, said “You fucked over our bud Chris and when you fuck with her you are fucking with us!”

“And just how did I do that?”

“Had your way with her and then kicked her to the curb.”

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