Urban Cowgirl

Urban Cowgirl

Bill Shanahan

Sometimes, I like to cruise country music bars for sophisticated women. A sophisticated woman knows how to dance and is willing to do the horizontal mambo on the first date, if she meets a nice guy, such as myself. I'm not really trolling for lasting relationships, but....

One Friday night at the Showtime Ballroom, I saw her. I quickly got into the line dance as close as I could to her. I guess, to me, she was cute more than beautiful from her black Stetson to her black and white inlaid boots, she was... cute. I could tell in spite of her fancy Western shirt and denim vest, she had boobs. Below, her jean skirt showed nice legs although when she turned it didn't go quite high enough to see her panties. As soon as the music stopped, I asked if I could buy her a drink, she chose white wine. I guess she wanted to keep that nice waistline nice. Not sharing that concern I had a bock beer.

She invited me to sit with her at a table. There were several purses there so I presumed she was out with her girlfriends. We chatted a while. Then her friends returned and after getting her phone number, I excused myself for a restroom break. I danced some more with other girls; got another phone number, and it was approaching Friday night closing time, so I decided to get out of Dodge. I figured I would call her on Monday or Tuesday night.

As I headed for the exit, I heard, "Hey, Bill!" and turned around. There she was.

Carla complained, "You never came back for a dance, Bill!"

I wasn't sure what was going on, but she took my arm. I replied, "I'm sorry, Carla."

She said, "It's okay. You can make up for it by coming to my place for a nightcap."

I quickly realized that she was more sophisticated than I originally thought.

I ended up following her to her place. She sat me down on a couch in her living room. She got me a beer, took her hat, boots, and vest off and sat down close beside me.

I took a sip of my beer, then put it on the coffee table, and I never quite figured out who kissed who, but just like that we were making out on her sofa. With the vest off her upstairs became more impressive. After I unfastened her bra with a little fumbling, she suggested that 'we take this to my bedroom.

In her bedroom we smooched and unfastened each other's shirts. When the big reveal came I was astounded at what wonderful tits she had. She caught me looking at her breasts. She asked, "Like my boobs, do you?"

I was a little embarrassed, but managed to croak out, "You have a rack to end all racks. Absolutely amazing!",

She had a rack that any Victoria's Secret model would be proud to carry. We took the rest of our clothes off. She had a fantastic ass; her waist and butt matched her tits. It was like a nine-dish dinner and I couldn't decide which delectable item to enjoy first. I settled on grasping her buttocks and deep kissing her. She said, "Shall we?"

I told her, "Just a minute." I went to her dining table and retrieved her hat. I want to do it cowgirl style and I want you to wear your hat.

She said, "No one ever asked me to do that before!" but she was smiling when she said it.

I laid supine on the bed with my six and a half inches pointing to the sky, or actually toward the ceiling of her bedroom.

She confessed, "I've always wanted to do this, but I never had the nerve." The nice thing about the hat was that it was not an impediment to my viewing her magnificent mammaries although it did obscure her beautiful, bedroom, blue eyes. I could tell she often wore bikinis because she had tan lines, more on her bottom than her boobs. Her hair was coal black. There was no escaping the fact as she bounced up and down on my rod, shaking those boobs, that Carla had one gorgeous body. I rated the sex as very good, not great, but promising. She seemed like the type that would be willing to take suggestions without becoming defensive. As I got to knew her better, I came to appreciate her wit, her unfailing good humor, and her niceness. Although she was beauty contest pretty, I thought of her more as being cute and pleasant to be around. I would rate our first sexual performance as a 6 or a 7. After a few weeks we were consistently having 9's.

I learned that she had worked three years in the fast food industry while working on an associate's degree in accounting, and now she was an accounting supervisor in a small manufacturing and distribution company. She supervised bookkeepers doing payroll, receivables, and payables accounting. My degree was in finance but I had minored in accounting, so when she talked about payables, for example, I knew what she was talking about.

The more time I spent with Carla the less I was interested in other women, no matter how sophisticated they were. After a few weeks, it wasn't a question of whether we were going to hang out or not, it was only whether it would be in my apartment or hers. Another few weeks and we moved into a three bedroom apartment, providing us with an office and a guest bedroom.

The only disturbance in our increasing intimacy and commitment was that she still liked to go out on Friday nights with her girlfriends. This was a little disturbing because it was on a non-Friday outing with her girlfriends that I had met her. We compromised to the extent that she only had a girls' night out, two or three times a month. As a personal favor, I had two friends tail her on two Friday nights, one on each Friday night. They both confirmed what she had told me, that as far as it went was making out in a car in the parking lot. I was unhappy about that but decided I should cut her some slack as long as it went no further than that and she was back at our apartment at a reasonable hour, whatever that was. It did seem that the nights she closed a bar or whatever at 2 in the morning were increasing in frequency.

I don't think I was totally in love, but I was enjoying my time with her more and more. I had two issues with her twice or thrice a month Friday night outings: I missed her while she was gone, and I didn't feel confident that even if she hadn't crossed a red line yet, she could anytime in the future. My red lines were pretty damn lenient. I was beginning to think that I needed to talk to her, with the idea that it would be better to talk to her now, rather than wait until I had no choice but to break it off. I wasn't ready to think about engagement, but I felt like being a live-in lover entitled me to some respect. I knew, and if she hadn't figured it out, she needed to know that my expectations for her would be higher once we started talking rings.

This was very difficult for me. When we were together, we just seemed to mesh. It seemed to me like we were compatible in just about every way. I just couldn't see her having to be with her girlfriends fifteen or twenty hours a month. I enjoyed going out with my friends, which I started doing on some of her girls' nights out. We'd meet somewhere at seven and by ten we were done. We didn't go to girlie shows or pickup joints; we'd usually go to nothing more exciting that a sports bar with a big screen television. We'd drink a few beers, maybe eat a few wings, and be done for two weeks or more.

I decided to talk to her about her girls' night outs. One Monday night after we had been living together for over six months, I started slow, not wanting to pressure her.

I said, "Carla, I have been thinking about the frequency of your girls' night outs."

She replied, "I'm glad you asked, my friends have been asking me about that. They want me to start going out with them every Friday night. We always have a lot of fun, but I told them I wanted to clear it with you before joining them. Is that what you were thinking?"

I answered, "Not exactly. I was thinking about having more Friday nights with you myself."

She explained, "That's so sweet, but Bill, don't I always make it up to you? Don't I come back to you horny as hell every Friday night after I go out with my besties?"

I admitted, "Yes, you do, although I think I might be more energetic if it was earlier."

She agreed, "That makes sense. For me things usually start slowing down around 11 or 12, although it seems like the girls like to go to closing. Why don't we do that? I'll start out with the girls having dinner with them at 6:30 like we usually do. You can come by and get me at whatever club we go to around eleven or twelvish. You usually quit earlier with your buds, right? I think that'll be a good compromise. I'll go out with my girls every Friday night, but I'll make it up to you by stopping earlier."

I wasn't completely on board with it, but it did seem like a compromise. I felt like I was giving more than I was getting but in human relationships you can't always have everything your way. Unfortunately, our first night under the new program was, at least from my point of view, a complete and unmitigated disaster.

I walked into the country music ballroom where I had met her a few minutes after twelve, thinking I'd give her plenty of space on the first night. She was wearing the same outfit that she had worn the first night I met her, seven or eight months ago. There were around twenty tables there but Carla was only two or three tables from the entrance. She was seated next to a good-looking guy sitting underneath an even bigger cowboy hat than the one she wore. She seemed very comfortable with him. They were holding hands. Her right leg was resting on top of his left leg. His right hand was far enough under her skirt that I intuited the position of his hand from the orientation of his right elbow. I walked over to her and asked, "Carla, are you ready to go?"

She looked at her new friend and in a very relaxed manner, said, "Jeff, let me have a few minutes with Bill."

Jeff pulled his hand out from under her skirt. At least he had the couth to not lick it while I was looking in his direction. She reluctantly, it seemed, removed her leg from his and then stood up.

She suggested, "Let's step away, Bill."

We walked over to some chairs lined up against a wall, perhaps fifty or sixty feet away from where Bill and her purse were located.

I said, "What's going on, Carla?"

She seemed to consider a minute and then replied, "I guess I would say that Jeff and I have a strong attraction for each other."

I responded, "I already have a pretty good idea of that!"

She considered again for a few moments. "Bill, although we're living together, we don't have the commitment of a marriage or even an engagement."

I told her, "Sounds like you're trying to weasel around any concept of exclusivity."

She came back with, "I knew you'd understand. You're the best boyfriend ever. Jeff will give me a ride home." She kissed me on the cheek, stood up, and flounced back over to Jeff. She briefly spoke to him. He escorted her to the well-marked restrooms. I guess she wanted to pee before she fucked him. Disgusted with the whole thing, I headed for the door. On the way, I met a couple of her friends, I acknowledged them with a nod, and continued my march to my car.

Carla Wells

I met Bill at the Showtime Ballroom. It was one of the places that my besties and I liked to hang. There were always a lot of horny guys there, so it was a nice place to chill and just wait and see what happens, particularly on a Friday night. My besties and I hardly ever missed a Friday night. Some weeks we also went on a Wednesday, Thursday, or Saturday. If we went a second time, we preferred Saturday because there was no work the next day.

After a line dance, Bill bought me a drink. I invited him to sit down at my table. We chatted for a while, with a little flirting. I thought he was okay. He excused himself to go to the restroom and never came back. What kind of bullshit was that? I decided to take the bull by the horns and hooked up with him. The only kinky thing about him was that he wanted me to wear my prized Stetson while I did him cowgirl style. I really liked that after we were naked in my bedroom, he went down on me. No guy had ever got me off twice before he penetrated me. I didn't mind wearing my Stetson when I rode his rod cowgirl or reverse cowgirl style. After my first three orgasms, we agreed the hat was a little more. After the reverse cowgirl, we kept changing positions every time I came. After fifteen or twenty orgasms I thought this is enough. I couldn't believe he had a name for the fifteen or different positions that we did. Finally, he wore me down. Looking at my bedside clock it looked like we had been screwing for close to an hour.

I finally told him, "Hey, stud! I'm ready for a break!" In less than a minute he came and feeling him spurt copious amounts of baby juice inside me took me over the top for one last orgasm. A lot of guys either get up and leave or roll over and go to sleep after they cum. Bill got all lovey dovey, kissing me and caressing me. It just felt really good. I was thinking that I might be onto something here. He could fuck like a pro and took care of business before and after. I would make sure we had another evening scheduled before he went home. After we calmed down, I went to sleep with his arm around me in the spoon position. It felt good going to sleep and being held while I was still enjoying the afterglow of lust.

I woke up around six with him rubbing my tits and kissing the back of my neck. I thought I could stand some more of this. This time I only came four times, counting the time when he was inserting another load in me. I was a little sore, but it was a really good sore, and It didn't stop me from enjoying getting screwed again. Again, we went back to sleep. We woke up around eleven and I came four or five times counting when he ejaculated. This time, I forced myself to get up and take a shower, thinking what have you gotten yourself into. This was a really horny guy and I was loving every minute of it. We went to brunch and then went to his place. I took a bikini and we would hang by his pool until he got hard, and then we'd go to his apartment for another round of stress relief. Finally, about ten Sunday night, I kissed him goodbye, ending our weekend. I told him I would be available for booty calls during the week. He acted like I had finally satiated him, although I was very well satisfied also. I was a little surprised when he called me around seven Monday evening and asked me if I would like to come over. That resulted in my getting wet immediately. I jumped when I got to his apartment about twenty minutes later. We preferred his apartment because he didn't have a roommate. Sally was a really good roommate as well as being a good friend, but I didn't like flaunting that I had a stud and she didn't.

By the following Friday, I was beginning to think that we had something going on. It seemed like I was enjoying his fucking even more than the first time. From time to time, he would make subtle suggestions about things I could do to make the sex better. Most of them seemed to work. I felt a little weird because I was used to things cooling down with my lovers after a while. Instead, I was getting hotter and hotter. All I had to do was hear his voice over the phone, and I was wet. We seemed to both feel like twenty-four hours without fucking was too long. Eventually things seemed to level off and I was okay as long as he fucked me at least once a night. Weekends we were still like rabbits.

After about six weeks I moved in with him. Sally moved into a bedroom apartment with two other of my friends. I continued to bond with my besties on Friday nights, although I was just having a good time, while they were trolling for hookups. We often went to a Western-themed club named the Showtime Ballroom.

Bill was a great guy. He very subtly implied that my bedroom performance could be improved. Wow, did it ever get better! I questioned if he could make our sex better, but he did, in spades. He was the best lover I had ever had, but when I started trying out some of his suggestions and doing some of the positions he wanted to try even though they were new to me, I had about a huge increase in orgasms and pleasure. He seemed to like the improved me better, also.

I was starting to think he might be a keeper. As infatuated as I was with him, I felt like he was even more head over heels into me. The way things were going, I was starting to think he might be the one.

Women, I think it's true for all women, although all I know is my own feelings, and what my besties have told me about themselves, change during the month. At times in our monthly cycle, we might be totally disinterested in sex, although that doesn't seem to happen to me, to going almost full nympho, wanting sex all the time, morning, noon, and night, around our ovulation time.

I'm telling you all this because it happened to me on one of our Friday night girls' night outs. I knew I was unusually horny even before my girlfriends picked me up for our night out together. Bill was picking me up at midnight at the Showtime, so I didn't have to worry about drinking too much. Drinking some wine with our supper was making me even hornier. I think I was already damp before we left the restaurant to go to Showtime. It seemed like each dance and each drink at the ballroom just got me hornier. I was having a wonderful time with my besties even though it wasn't helping my horniness any.

Then I had a dance with a guy named Jeff. By this time, I was soaked down there. When I felt Jeff's manhood pressing against my thigh I just plain wanted him. I wanted his cock sliding in and out of my love canal. I was so hot that if he had tried to strip me in the club and screw me on the dance floor, I probably wouldn't have stopped him. I could tell his cock was large, possibly even larger than Bill's, and I wanted it stretching and filling my cunt.

I hadn't realized that it was almost midnight. Bill would be here any minute and I hadn't decided what to do. Jeff had his hand up my leg under my panties, and it felt so good. I was totally at ease with Jeff and what he was doing to my poor, defenseless pussy. I just plain wanted to satisfy my feelings of horniness, and I focused on Jeff being the guy to take care of me.

I didn't notice Bill until he spoke, asking me if I was ready to go. I was so ready, but I wanted Jeff's cock, not Bill's. I took Bill away from our table and started explaining to him that just for tonight, I wanted to be with Jeff. He seemed to understand, or at least he got the general idea. At least, he didn't blow up, so I returned to Jeff. I thought I at least had Bill's implicit consent, even though he didn't exactly say so.

I was ready to go. I told Jeff I thought we should go to his place, but I needed a potty break first. He escorted me to the restrooms, carrying my purse. When I got out of the restroom and walked with Jeff toward the exit, it appeared that Bill was already gone. I hoped he was okay with what Jeff and I were planning but at this point I was going after Jeff's cock, regardless.

When we got to Jeff's place, he introduced me to his roommate, Jerry. I expected Jerry would return to his room. He joined us for a drink Jeff and I sat on the sofa, and Jerry sat next to me. He was a fairly good-looking guy, a bit larger than Jeff both in height and width. Fine, we would have a drink together and then Jeff and I would go to his room and Jerry would return to his own room, right? Wrong! When Jerry started to follow me into Jeff's room, I stopped at the door.

I asked him, "What's going on, Jeff?"

He smiled and explained, "Jerry and I share everything. Have you ever been with two guys at the same time?"

I told him straight, "No, and tonight's not the night. I think it's best if I leave."

He said, "You wouldn't want to leave us both high and dry, would you?"