She was recently divorced and had a one year-old son. Since her divorce she has been living in her parents basement which they had finished as an apartment and had been hoping to rent it out for some additional income. She was very experienced in the ways of pleasing a man. She was an exhibitionist who would do anything, anywhere, anytime. This is the story of our first date.
1 st Date My friend Greg and I were meeting my friend Portia and her friend Courtney, whom I hadn’t met, out for an evening of drinks, jokes and telling lies. Greg and I were both in our early 20’s and recent college graduates. Greg had just moved to town and I wanted to show him a night on the town and met the girls at tavern in our local bar district.
I noticed a very strong sexual connection with Courtney from the start. Something about how our eyes flirted with each others on first contact. I knew that she was into me and she knew that I was into her from the start. I found out through conversation that Courtney she was about a year younger than me had a son and was recently divorced. That didn’t seem to matter. I didn’t want to scare her away and get too intense too quickly with her so we just all continued to drink and catch up on what was going on with our lives.
Towards the end of the night, Greg decided to go to the bathroom and it was just Courtney, Portia and I at the table. I am typically a pretty calm and laid back guy who isn’t too forward but for some reason I felt the need to seal the deal and bluntly said to Courtney, “So, when are we going out?” right in front of my friend Portia.
What? Did that just come out of my mouth? Me? Portia, knowing me, knew that this was out of character for me and turned and watched Courtney intently for her response. I will have to admit that it was a pretty bold and cocky move but it was done with such precision and confidence while not breaking eye contact with her gorgeous ice blue eyes.
She said, “I don’t know, Ryan. How do I know that you’re a good guy and will know how to treat me right?
I said confidently, “You don’t. That’s the excitement of it. You can look at a roller coaster all you want but you won’t know how fun it is until you get on and ride it.”
That quickly sealed the deal and we set a date for the next week as we stood out in front of the bar before saying our goodbyes. We couldn’t seem to find a weekend that we were both available soon enough for our liking so we picked a Wednesday night to go out on our first date.
As we live at exact opposite ends of the city, she suggested that meet at a restaurant somewhere halfway and I suggested The Plaza which is a nice shopping district near downtown even though I offered to come pick her up. She said something about not wanting guys to come to her home on a first date. Understandable, there are all sorts of weird freaks out there in the world and she didn’t know me from Adam. Afterall, she did have a little boy to protect as well.
She was waiting at the restaurant bar with a drink when I arrived. She was wearing a pair of blue jeans, a v-neck sweater and looked casual but very sexy even though it didn’t appear that she had put much effort into it. Her mid-shoulder length dirty blonde hair contrasted nicely with her black sweater and her perfume would make its way to me as I hugged her.
I quickly got a drink and she said that the wait for a table was about 10-15 minutes. I said very confidently, “I’ll fix that.”
As I was walking towards the hostess stand towards the front of the restaurant not knowing how I was going to “fix” the table situation I was thinking to myself, “Wow! Had this been years of aggressiveness building up in me and finally needing to come out or am I just being a complete jackass?”
I was then interrupted by young lady walking towards me who looked like a waitress carrying a few menus who asked, “Frank – party of two?”
I said, “I most certainly am, let me get my date from the bar.” I walked back into the bar area like a triumphant war hero with a waitress unknowingly in tow saying, “Ma’am, this way to your table,” as she extended her arm to Courtney’s left.
Courtney looked very impressed and smiled up from her drink at me trying to figure me out with a coy smile. I walked proudly behind her not knowing how that all just happened but I wasn’t going to let Courtney know that I just lucked into getting us a table.
I played it off once we got to the table as I am naturally a very humble person and asked her to tell me about herself. After we ordered food and another round of drinks for us, we exchanged our life stories for more than an hour as we ate.
She was raised by a boarder-line cult farm family about 45 minutes outside of the city who she had to run away from at 17 in order to evade an arranged marriage by her parents and shortly thereafter joined the Army. She suffered a broken pelvis during “Hell Week” and was honorably discharged.
Even though we didn’t have hardly anything in common other than the fact that we both lived at home with our parents (me a recent college grad saving to buy a house and she had made amends with her parents once her son had been born) but there was a certain “spark” between us. Before there was a lull in the conversation I turned to her and said, “You ready to get the hell outta here?”
She smiled and said, “What do you have in mind?”
Having a plan in place prior to the date, I said, “Well, you ready for an adventure?” It was kind of an inside joke that she wasn’t privy to. She replied, “Always!” She grabbed her coat and we headed for the door.
See, I had dated multiple women who were from upper middle class families who expected to be wined and dined at extravagantly nice and expensive places. I wasn’t looking for that with Courtney and wanted to try something different. I was greatly surprised when she reached for my hand and snuggled up to my shoulder and arm as we exited the restaurant on a cold November night.
“This chick has got balls,” I think to myself while walking to the car. She is getting ready to get in a car with a guy with whom she barely knows and is heading to an unknown destination. Not sure if it was balls or stupidity. I guess I made her feel comfortable enough to trust me.
I drove to an older part of town about 10 minutes away called North Kansas City that is mainly a busy industrial area in the daylight hours and somewhat abandoned at night. What must have been going through the poor girls mind?
I then pulled into a parking spot on a street in front of this run down bar with 2 or three cars parked in front of the bar that was aptly called “The Dive.” Its name was exactly what it was. It was a place that I’ve heard about but had the chance to go to with my buddies yet. It’s definitely not a place that you’d want to take a girl on a first date.
We walked in and Courtney and I were clearly the only people who had a full set of teeth. “See what I mean by adventure,” I whispered to her as we walked in. She laughed and agreed.
The bar and barstools were to the right side of the room with four or five tables with chairs on the left. Various neon beer signs/posters and cigarette smoke hung throughout. In the center of the room was a narrow hallway that contained the doors to the bathrooms and through the hallway was a vacant room where there was a pool table and jukebox with a few bar stools and small hightop tables.
There were only a handful of people in the bar and they were all sitting at the bar with a crusty and heavily worn, older woman working behind the bar who was dangling a cigarette from her lips while she talked to the patrons. They all knew each other fairly well by their conversation and were surprised to see two young people who looked so out of place walk through their door.
Being a random Wednesday night past 8:30 pm, I didn’t expect too many more people walking in through the front door. It was just the kind of place that I was looking for.
See, this was a test for Courtney to see if she was capable of helping me break my stream of prissy girls who drank $9 martini’s (that was very expensive for a drink in the early 2000’s) who expected to be waiting on hand and foot.
I also thought this might impress her as I suddenly went from a guy who could get a table on demand at a ritzy restaurant to a guy who can roll up his sleeves and shoot some stick on the pool table in a dirty dive bar. And truthfully, I was and still am naturally comfortable in either environment.
I asked her if she wanted to play pool or have a drink at one of the tables. I was thrilled when she said that she wanted to play pool.
So I got us some beers and a few dollars in quarters for the pool table from the bartender and we headed through the hallway to the back room. It was kind of a perfect set up as we were secluded from the rest of the patrons and we had our own little private area to where no one was going to listening in on our conversation and we didn’t have to worry about other people watching us flirt.
I gave her a few quarters for the jukebox and she sexily walked over and picked a few songs and grabbed a pool cue. I took it easy on her in pool but she was actually pretty good in her own right.
I would casually miss a shot to where I knew that she would have to come over by where I was standing to shoot or perhaps to where she had to really stretch out to reach the cue ball across the table. Each time she would bend over, my cock would slightly stiffen for a few seconds leaving me in a constant state of arousal. As she was tall and slender, her ass was perfectly round and small and it popped out in just the right places.
As we drank more she would get more and more seductive. She was giving me seductive looks from across the table just before I would bend down to address the ball and as the night went on, she would purposefully choose to shoot a shot that caused her to have to wedge herself between myself and the pool table.
Eventually, it was clearly obvious that she was doing this on purpose because she would forego a shot on a ball that was sitting in front of a pocket and instead choosing a much more difficult shot just so that she could put that beautiful ass mere inches from my groin which contained a cock that was at half mast by this time.
As time went on, I don’t think that either one of us were hiding our sexual feelings for the other. As she would wedge herself between me and the table, I wouldn’t get out of her way quite as much and she would be forced to rub that fantastic ass on my stiffening cock.
As the games and beers progressed, she would linger just a little bit longer each time in front of me and I would slowly rub the length of my now hard shaft against her stunning ass.
I had missed my shot on the 8 ball and left a straight shot for her in the corner pocket. I purposefully stayed right where I was because it was exactly where she needed to be to shoot at the 8 ball. She again had to squeeze in between my body and the table and was slowly grinding her cute little ass against my completely raging hard-on as she gently slid the cue forward into the cue ball causing the cue ball to ever so gently hit the 8 ball.
As she was still bending over the table and as the 8 ball was creeping towards the pocket, she pushed back hard against my groin and slowly started grinding her gifted ass up and down against me as I put my hands on her hips to help guide her.
She started to rise and pushed her shoulders into my chest and then turned her head towards me and our lips met with such a raging passion as she slowly turned around without breaking our lip lock. We kissed passionately for several seconds, we both heard the 8 ball finally drop and we both smirked while in mid-kiss.
Before we got to a point of no return in the bar, I said that we need to get out of here. We can barely keep our hands off each other as we walk to the car. As we reach the car, I grab her by the small of her neck and kiss her passionately for what seemed like days. It would not have surprised me to see the sun rising by the time we broke the rousing kiss.
Finally we get in the car and take the 10 minute drive to my house. Those 10 minutes seemed like an eternity to the both of us and we are all over each other the second that the car is stopped in my driveway.
As my parents were in their retirement years, they had become gamblers and were down at one of the casino boats that we call “The Boats” here in town. This was the case tonight as I noticed that one of my parent’s cars was missing.
Courtney and I headed for my bedroom on the second floor shedding our coats on the way up the stairs. I turned on a lamp that was on my night stand which offered a very dim light once we got into the bedroom. As soon as I turned on the stereo, I turned to her and passionately forced her against the wall and our lips meet.
I ran my right hand behind her left ear and pulled her lips into mine. As our lips touched and our tongues brush against one another, I pull back slightly and to stare directly into her beautiful eyes and savored the moment. I then pressed my soft lips against her lips and as we fuck each other’s mouths with our tongues.
I moved my left hand to the right side of her stomach and rubbed her side just below her rib cage as I take her very full lower lip into my mouth and gently suck on it. Courtney reaches down with her right hand and rubs my cock through my jeans and just then sighs, “Oh fuuuuck” as her head tilts back and the her eyes roll into the back of her head.
I move down to her neck and kiss with wild abandon as she just keeps repeating, “Oh fuck, oh fuck me, oh fuck, oh God fuck me!” I kiss down her neck to her necklace and continue to peck her chest down to the top of her v-neck sweater as she is continuously rubbing and trying to grab my cock through my pants.
She reaches under my sweater and beings to pull it up my rib cage and easily slips it over my head as my left hand has made it to her right breast. I then start to pull her sweater and undershirt up over her head to reveal a small set of B cups in a black lace bra. Courtney pushes me backwards onto the bed as she reaches for the button on her jeans. She bends over and whispers gently in my ear, “Get your pants off because I am going to fuck your brains out.”
As she stands back up, and I fall onto my back, her jeans fall from her hips to the floor and I am transfixed by her beauty. After she steps out of her jeans she reveals a very tight and toned body and slowly turns around to show me that ass that has been teasing from the moment we first met while wearing sexy, black, cotton thong that frames her perfect ass wonderfully.
She says, “Is this what you’ve been looking at all night, dirty boy?”
As I nod yes, she turns back to me and realizes that I have yet to begin to take off my pants. She reaches for the button on my jeans and slowly unzips my pants.
As I lift my hips to allow her to slide my jeans off I notice her eyes grow wide and she is mesmerized by what is contained beneath the fabric of my underwear. She continues to remove my jeans and then removes her bra to show me two very cute tits. A little smaller than what I am accustomed to but I knew this prior as she obviously wasn’t built like Jenny McCarthy but sexy nonetheless.
She was very slender and toned with her perfect tight ass and I was very pleased by the beautiful young woman wearing nothing but a thong who was spellbound by my raging hard-on lurking in my boxer briefs.
She moves onto the bed straddling my groin with her thin but firm body. She gently lowers her black thong onto me coming into contact with my covered cock about mid shaft. Although we are both still in our under wear, it was as though we were one and didn’t have one stitch of clothing on.
She slides her pelvis forward while still on the shaft of my dick and as she reached the top of my cock and then slowly slides down until she is near the base of my cock.
