My friends and I would frequent this particular bar not because of the waitresses, but they had TVs all over the place and great pub food. This happened to be the most central location for all of us, so this worked perfectly. Looking around, plenty of dudes would hit on the waitresses. Some liked it, some didn’t. I had always been advised not to pick up any waitress while they were working. From the various reasons they provided, I felt that advice was solid. So I would be friendly, very polite and humble.
One day an old friend Tom walked into the bar and I went over to say hello. All of a sudden Maggie came over and gave my friend a big hug. Tom introduced me to Maggie.
“Hey Maggie this is Dean. The best baseball player I ever played with.”
“Hey! Yes I know Dean. He’s the guy I call Cowboy.” She wrapped her arm around my shoulders.
“Why Cowboy?”
“I’d like to know that too,” I said.
“He’s a complete gentleman. I find that to be a huge turn-on.”
So did I…
“Hey Dean, she’s single. Go after her.”
“Maggie you’ve melted my heart. If I had a rope, this Cowboy would never let you go.”
She giggled and then squeezed my arm, then went back to work. Tom gave me the nod to say, ‘go hit that’.
A few days later on a Saturday I was meeting some friends to watch a Fox baseball broadcast. I placed an order with another waitress and proceeded to head toward the washroom located on a lower level. I walked downstairs and walked right by Maggie, who was starting her shift.
“Hey Cowboy! How’s it going?”
“Hey Maggie. Or should I call you Cowgirl? If only you wore the hat at work.”
“Haha. Well I do have a hat but I only bring it out on special occasions.”
“Yeah? What do you consider a special occasion?”
“A country concert. A hot picnic date. I dunno, any excuse to wear it I guess.”
“I definitely want to see that hat.”
She laughed and started walking up the stairs. I decided to pull a line I already used out of desperation.
“Maggie, if I had my Cowboy rope right now I’d pull you back down here.”
She stopped, looked at me, and to my amazement she started walking back down the stairs toward me!
“And what would you do with me, Cowboy?”
I pulled her closer to me by her tiny waist and went in for the kiss. She obliged, and she was a great kisser. She had naturally thicker lips that felt so hot whenever mine locked with hers while our tongue’s touched.
“I’ve wanted to do that for a while now.”
“So have I. I finish at 11:00 p.m. tonight. Do you want to meet up?”
“Sure. I’ll pick you up.”
We wound up having coffee that night and got to know more about each other. We had a makeout session and I had her nipples in my mouth. We didn’t do the deed.
The following night she called me and asked what I was doing on the Monday morning. She said to come pick her up around 8:30 and we’d do something. I drove to where she lived and knocked on the door.
“Hey Cowboy, come on in.”
She pulled me by the shirt and kissed my lips. She had cutoff jeans that showed off her amazing ass with a Texas state-looking belt buckle that was badass. She then took me to her basement. There was a pullout bed, a Cowboy hat and a couple condoms on the table beside it. I was pretty much about to blow my load right then and there.
“Are you gonna be my Cowboy?”
“Fuck yes!”
We started kissing passionately, and I needed my cock to spring out of my pants badly. I pulled her hands down to my pants where she loosened my belt and zipper, and started stroking my cock inside my boxers. I pulled her shirt off and started playing with her breasts. Finally she grabbed me and pushed me onto the bed where she then put the Cowboy hat on and straddled me, leaning down to kiss my lips and neck. Then she stood on the bed with that amazing, goddess-like body and started unbuckling her belt. The way she slid her jean shorts down, doing a little dance to slip them off was incredible. She wasn’t wearing any underwear.
She grabbed a condom off the table and slipped it on. The normal sized rubbers were always a bit tight for my dick.
“You have a nice cock. I want you inside me now.”
She lifted herself onto my rock hard cock and slowly pushed herself on it. She was trying to get used to my size, which was seven inches. The thickness of my Johnson made her tentative to work fast.
She began to get more comfortable riding my like the Cowgirl she was. The only thing she was wearing was her hat. I sprung into action by squeezing her amazing breasts. They had to be close to a size D.
“Oh fuck that feels good. Don’t stop that.”
She picked up the pace and really started to ride me. She was getting a bit louder, and suddenly her hat fell off. She stopped.
“Oh fuck, my hat. I don’t want to get off, you feel so fucking good.”
“I love your hair anyway. Keep going Cowgirl.”
She continued on and picked up the pace even more. I sensed she was getting close. I took my right hand and rubbed her clit.
“Oh fuck yes! YES! OH MY GOD!!!!”
I took my left hand and squeezed her right ass cheek just before she was about to cum. When she did she collapsed on-top of me, holding me to brace herself. Her body jerked pretty hard during climax.
“Oh my God that felt so good.”
I rolled her onto the bottom and I started to have my way with her wet pussy. I really started fucking her hard. The bed springs were making a pretty cool noise which gave me something to concentrate on so I didn’t cum. She was extremely sexy, and while I was pounding her vagina I really couldn’t believe it was actually happening. She was probably a fantasy to the many men that she served at the pub. All that popped in my head while I fucked her into another orgasm.
“Jesus Christ! Oh fuck yes! Keep going keep going keep going…”
She wrapped her arms around me to brace her body for the climax once again, screaming in my left ear while I nibbled on hers and sucked on her neck. I really wanted to hit it from the back. Her ass was a sight to see, and I was wanting to see it up-close and personal.
I got her on all fours and slipped my cock inside her, slowly pumping in an out. I started spanking her ass cheeks pretty hard. She turned to look at me with her beautiful eyes and made sure I knew she wanted more.
“I like that Cowboy. Keep doing it.”
Her slightly tanned ass started turning red while I fucked her hard and fast. She tried to duck her head down toward the bed and I wasn’t having that. I grabbed her long, beautiful dark brown hair and pulled it back.
“Yeah Cowgirl. You fucking love this or what?”
“Oh fuck yeah. You’re fucking amazing. Don’t stop.”
I pulled her hair back so I could suck on her neck while I fucked her. The slapping of her ass on my body was really loud. Her pussy was really wet and made fucking her that hard much easier.
“I wanna ride you again.”
As I went onto my back she picked up the Cowboy hat and put it on her head. She got on-top in reverse cowgirl position and really started riding me. She went up and down and in-circles trying to climax one more time.
“Oh fuck I’m cumming again. Yes, yes… YES!!!”
She grabbed my shins to stay balanced. I told her I was close to cumming. That’s when she did something I never saw before; she got up to grab her bottle of water. Then she pulled off my condom, poured water on her hand and stroked my cock for a few pumps. She told me afterward she did that to take the condom taste off my cock. Made sense because she started to give me a sloppy blowjob. Less than a minute later I was blowing my load all over her mouth. She, like the others, couldn’t swallow the load. I came all over her neck and chest with a ferocious load of semen shooting out of my balls. It was incredible.
“Holy shit you shoot a lot of cum. Do you always do this?”
“No girl has ever been able to swallow my entire load yet, Maggie.”
“Call me Cowgirl in the bedroom, Cowboy.”
And I did just that for the entire summer. We weren’t boyfriend and girlfriend but she was a girl and she was definitely my friend that summer. She even tried blowing me on-occasion just so she could swallow my load. To no avail. I was blessed! She wore that Cowboy hat many times that summer, and I even tied her up a few times. Once we were close to returning to school we went out separate ways. Senior year of college upcoming. How could I top off what I did the year before?
