Getting A Date With Kim

Posted in: Chance Meetings | First Time | OTK

Chapter Thirty Nine: Getting A Date With Kim

Sunday afternoon I was cruising down Main Street when I noticed Kim Douglas sitting on the bench outside Drug Mart. I hadn’t seen her since our brief encounter at the mall. Kim was one of the sexiest girls at Garfield High. She had a fabulous figure, long red hair and a beautiful face.

I figured Kim was on a break from her checkout job. Even though she had pissed me off the last time we met; I decided to try my luck with her. It wasn’t in my nature to carry a grudge, especially when there was the possibility of getting some pussy and getting it from a girl as sexy as Kim was a real incentive.

I slammed on the brakes and quickly wheeled my car into the Drug Mart parking lot. I shot down the aisle and pulled up in front of the bench. Kim was wearing her usual outfit; skin tight jeans and a short tight fitting top that left a portion of her stomach bare and emphasized the alluring swell of her large perfectly formed breasts.

I ran the passenger side window down as I cranked up the old Bradley charm. I put on a big smile and said, “Hi Kim. How’s it going? Working hard today?”

Kim looked up, took a drag off the cigarette she was smoking and said, “Oh no! Not you again! Would you believe it, I even went to church this morning. I guess I didn’t pray hard enough. And yes I’m working hard; not like some rich jerks, who have nothing better to do than drive around in a fancy car all day.”

Undaunted by this opening, I continued to smile saying, “I’ll just park the car and keep you company for a while. You look a little lonely sitting out here all by yourself.”

Kim replied, “Please don’t do me any favors Mr. Bill Bradley. I’m perfectly content.”

Ignoring this comment I said, “It’s no trouble at all. I’ll be right back.”

I figured that Kim would probably be gone by the time I got back to the bench. I decided that if she was; there would always be another time. But as I walked through the parking lot, I saw she was still sitting there and I took this as a very good sign.

When I sat down beside her, Kim took a final drag off her cigarette, blew the smoke in my general direction and crushed the butt out on the sidewalk. Then she said, “Well Bill, have you got any unsuspecting little girls into your secret dungeon room lately? I’m a little curious. Besides spanking them, what other kinky things do you do?”

“Why don’t you drop the attitude Kim? You might find that I’m a very nice guy if you would just take the time to get to know me. I’m an Aquarius and Aquarians are unusually sensitive and very artistic. I’m also left handed and lefties are proven to be typically more intelligent than the average population.”

Kim replied disgustedly, “It figures that the first thing you’d do is start bragging about yourself Bill. Why don’t you tell me how rich you are? Who knows? Maybe that will impress me. But I doubt it.”

“Look Kim, I don’t brag. I tell the truth.” This was a lie. I hardly ever told the truth. Lying was second nature to me. I couldn’t help myself.

Then I continued, trying to wrangle some sympathy from Kim, I said, “I don’t know what makes you think I’m rich. I work part time for my dad to get my money. I work late at night installing security systems and its very hard work. Sometimes when we have a rush job, I work all night and then go straight to school. Yes I drive a new car; but only because my dad can write it off as a business expense. The car belongs to Pro Tec; not me. Yes my old man has money. I’m sorry if that pisses you off. But just remember it’s his money, not mine. Whether you believe it or not, I don’t get anything that I don’t earn.”

As I concluded my little speech, I thought I detected a subtle change in Kim’s attitude; but I don’t think she was quite ready to let me know it. Of course most of what I had said was a lie. I never worked on school nights and my dad gave me the car. I did work for some of my money, but my parents had given me a credit card for any incidental expenses.

Still apparently unwilling to give me a break, Kim said in sarcastic baby talk, “Oh the poor little boy. Does him have to work real hard and all night too? That’s just terrible!”

I figured that now was the time to hold it or fold it. I called Kim’s bluff by getting up from the bench and starting to walk away across the parking lot. It took some self control; but I didn’t even glance back. The gamble paid off. Before I got very far I heard Kim call out, “Bill wait a minute. Come on back. I’m sorry.”

I decided to push it just a little further and I continued walking. In a few seconds I heard footsteps coming up behind me and Kim grabbed my arm saying, “I meant what I said Bill. I am sorry.”

I stopped and turned around to face Kim. Then she said, “Look, I don’t have any more time now. My break’s over. I get off work at 9:00. Why don’t you stop by and pick me up then?”

I gave Kim another big smile and said, “Sure thing! It’s a deal!”

At 9:00 pm. I was pulling up in front of Drug Mart. Kim was there waiting for me. She got in the car and as we drove away she said, “I have a couple of hours before I have to be home. What do you want to do?”

I said, “I have something in mind, but I want it to be a surprise. You’ll find out soon enough.”

In about ten minutes, I pulled off the main drag. I was heading for my house and Kim asked, “Hey Bill, where in the hell are we going?”

I replied, “I said it was going to be a surprise. Just be patient for a few more minutes, we’re almost there.”

In a couple of minutes, I pulled onto my street and shortly thereafter, turned into the drive at my house. I said, “Here we are. This is my house.”

Kim said, “How sweet. You’re bringing me home to meet the folks and we haven’t even had a proper first date.”

I said, “Well actually Kim, my mom and dad aren’t home this evening.”

“Oh I get it now. You think you’re going to get me into that big house all alone. Sorry Billy Boy! Wrong! You can forget that plan. I’m not getting out of this car. Just take me on home if you don’t mind or even if you do mind. Otherwise I’m going to start screaming rape and we’ll see what your rich neighbors make of that.”

I said, “God damn it Kim! I just want to talk for a while. I want to get better acquainted, that’s all. But if you can’t handle it, I’ll take you home right now.” After saying this, I started the car and began to back out of the drive.

Kim said. “Oh hell, I don’t care. You’re so damned sensitive. I’ll go in for a while if it will make you happy. I don’t want to hurt your feelings again.”

I pulled the car forward again and shut off the engine. I got out, went around and opened Kim’s door. Then doing my best imitation of Boris Karloff I said, “This way to the dungeon if you please.”

I walked down the drive to the back of the house with Kim following close behind. When we got to the steps that led down to my basement apartment Kim said, “Wait a minute. Where do you think you’re going?”

I replied. “I’m taking you down to my secret dungeon. I thought you were curious to see it. You’re not going to chicken out on me are you?”

There was a note of uncertainty in Kim’s voice and I began to suspect that she wasn’t the street-wise tough cookie she pretended to be. She said, “I don’t know about this Bill. I think maybe you should just take me home. OK?”

I reached out, took Kim’s hand and began pulling her down the steps saying in a sinister tone, “I’m sorry, but it’s too late now. You’ve passed the point of no return.”

As we reached the bottom of the steps, I could tell by her voice that Kim was getting a little panicky, but trying to hide it, “She said, “OK Bill you’ve had your little joke. Please, I want to go now.”

I unlocked the door and pushed it open into the pitch dark basemen
t and as I pulled her inside, Kim started to scream. I kicked the door closed and flipped on the light switch illuminating my cheerily decorated kitch
en area. Then I began to laugh as Kim practically sank down onto the floor. I pulled her up and said, “My God! You really believed I had a dungeon down here.”

Kim didn’t reply for a few moments as she took in her surroundings. Then she said, “I don’t know what to think about you Bill. You’re very different and I’m not sure if that’s good or bad.”

I said, “I guess you’ll just have to find that out for yourself.” Then I pulled Kim close to me and kissed her. She responded willingly and very soon her lips were parting under mine. As we kissed I let my hands stray down to Kim’s sexy butt. As soon as she felt me touching her there, she immediately stiffened and pushed away from me saying a little nervously, “Hold on! Take it easy Bill; remember this is just a first date.”

Judging from her body language and her reaction to my touch, I began to conclude that Kim’s whole persona was nothing more than a bluff. In spite of her sexy body and great looks, I had the distinct impression that she had had very little experience. I was sure that her aloof sarcastic attitude was just a put on to shield her from advances by the opposite sex. Bottom line; Kim was afraid of sex and was doing a very good job of giving the exact opposite impression.

I put an arm around Kim’s shoulders and led her into my sitting room. I switched on a lamp, which bathed the large area with a soft glow. Indicating the large leather couch I said, “Take a seat Kim.” As Kim sat on the couch, I went over and switched on the stereo. I selected some smooth jazz and then I said, “I’ll be right back.”

I went out to the kitchen, opened a bottle of wine and filled a glass. I went back to the sitting area, handed Kim the wine and sat beside her on the couch. I said, “I guess you’re used to something stronger; but this is all I have.”

Reverting to her tough girl attitude, Kim took a drink and said, “I guess it will do.”

I thought to myself, it better do. I swiped that bottle from dad’s private stock and I expect it cost at least five hundred bucks.

Kim took another drink of the wine and said, “This is very nice Bill. You know, I didn’t think you really had a dungeon. But when I ran into you that day at the mall I could have sworn you were serious when you said you would like to spank me.”

“I was serious Kim. I would like to spank your bare butt. There’s noting wrong with that. I can’t believe you’re so straight-laced. You’ve never heard that a little romantic spanking can be a turn on? It makes me wonder how experienced you really are.”

I could tell this little jab struck the mark. I could see Kim’s attitude cranking up again. I thought how like Amber she was. I was beginning to discover that the sexiest looking girls were the most likely to be na├»ve and the least likely to admit it.

Kim took another drink of the wine and said, “Look Mr. Hot Shot, I have half the guys at Garfield High falling all over me every day. But I seriously doubt if there’s a line of girls waiting to go out with you. So you figure out who has the most experience. I only came over here because I felt sorry for you. It’s not like I have the hots for you. Please don’t flatter yourself by thinking that.”

Kim finished off the wine and then she said, “I know more about you than you might think Bill Bradley. I remember when you were trying to date Amanda Haywood. I don’t know what happened; but I do know it didn’t last very long. Little “Miss no tits” Amanda must not have been very impressed with you. I’m sure she’s moved on to better and probably bigger things by now; if you get my meaning?”

Kim had just managed to push the wrong button with me. She had me seeing bright red. I could feel myself loosing control and I knew that, no matter what the consequences, her ass was going to suffer. I think Kim could tell by the look on my face that she had gone a little too far. I saw her eyes widen as she slowly sat her glass on the table and began to scoot across the couch away from me.

Before Kim had time to fully react, I was on top of her tearing open the fastening of her jeans. In the next instant I was hauling her across my knees. I clamped an arm around her waist as she began to struggle. With my other hand, I began pulling down Kim’s jeans and panties. Now she began to kick her legs and scream out, “Let me go God damn you!!”

Kim was a small girl and although she was surprisingly strong for her size, she was no match for me. I got her jeans and panties down and began to set her beautifully rounded ass on fire with the palm of my hand. After a minute or so Kim began to cry out as I continued to spank her. She screamed, “Please stop! I’m sorry. I didn’t mean what I said! Let me go!”

I stopped and said, “Hold still then and listen to me.”

Kim ceased her struggles and lay still across my lap. Then I said, “I’ve taken all the crap from you that I intend to. I’m tired of hearing you say you’re sorry because it’s obvious you don’t mean it. You deserve a good spanking and I’m going to see that you get it.” After saying this, I went to work on Kim’s cute little butt again.

After another couple of minutes of some very hard spanking, Kim was crying as she said, “I am sorry Bill. I promise I am. I know I’ve been treating you kind of shitty. I won’t do it again. I swear.”

I now knew something else about Kim. She was like Cindy. She needed someone to lay down the law to her. I could tell that my recent actions had raised her estimation of me significantly and I intended to build on that. I said, “OK Kim, I’m going to let you up and you better behave yourself.”

I got Kim up from across my knees and laid her back on the couch. Spanking her bare butt and now seeing the muff of red hair between her sexy legs had my tool at full alert and straining within the confines of my jeans.

As I finished pulling Kim’s jeans and panties off, she asked, “What are you going to do now?”

I kicked my shoes off and began taking down my jeans as I said, “You should know the answer to that Kim. With half the guys at Garfield High falling all over you every day, I’m sure you must have had some experience before now.”

Kim didn’t say anything at first, but when I turned toward her and she caught sight of my stiffened shaft she said in a soft trembling voice, “I’m not as experienced as you think Bill. It’s not that I don’t want to do anything, but…” At this point Kim’s voice trailed off.

“What’s the problem?” I asked.

Kim blushed a little and said, “It’s just that you’re kind of big and I’ve never really…you know…never done it before.”

I leaned over and kissed Kim on the forehead, the tip of her nose and then on the lips. Then I said softly as I began to unbutton her top, “There’s a first time for everything.”

Kim sat up a little and let me slip her top off. Then I unfastened her bra and slid it off to reveal her beautifully rounded breasts. The light pink nipples were already erect and as I began to gently suck on them, Kim let out a little moan of pleasure. I slid a hand down between her legs and found that her love nest was already very moist. It seemed as if the butt warming that I had just given her was paying dividends. With the tip of one finger, I began to gently massage Kim’s clitoris and I felt it coming up to attention. I moved lower placing kisses all down Kim’s stomach. When I reached her pussy, I slipped my tongue in to continue working on her clit. I knelt on the floor and continued to give her hot little pussy my full attention. In no time Kim’s bottom was bouncing up and down on the couch as the pushed her pussy up to my mouth. I slipped a finger into Kim’s love tunnel and found it to be hot and wet; but also very tight. As I began to work a second finger in, Kim cried out a little. In spite of her high state of arousal, I believe she was feeling a little pain. Kim had the tightest pussy I’d ever encountered.

I got up onto the couch
and into position between Kim’s legs. She looked up at me as I began guiding my tool into her pussy and said, “N
o we can’t do it Bill. That thing’s too big.”

I replied, “Just relax Kim. You were made for this. It’s going to be OK.”

As I slowly pushed forward into Kim’s tight pussy the resistance was considerable and Kim cried out, “No stop! It’s really hurting!”

Just at that moment, the head of tool slipped inside and I knew the battle was partially won. I said, “It’s in now. See I told you it would be OK.”

I pushed in a little further and then pulled back just a bit. I slowly repeated this maneuver; pushing in a little further each time. I could tell that Kim was beginning to relax as I slowly stretched her love tunnel and it began to accommodate my stiffened rod. However I knew the hardest part was yet to come and I decided to make it quick. The next time I pulled back I paused and then quickly applied full force as I thrust into Kim. She let out a scream as my stiffened rod broke through and sank fully into her.

Kim cried out, “No take it out; you’re killing me!”

I bent lower over Kim and said, “It’s alright baby. The worst is over. It’s going to be good now. Just give things a chance.” Then I began to suck on Kim’s nipples as I pulled my tool back a little and pushed inward again. I rose up and brought a finger down to massage Kim’s clit as I slowly began to move my tool in and out of her tight hot pussy. In a while I felt the resistance easing as I increased the length and speed of my strokes. Finally I could tell that Kim was beginning to enjoy the sensation of my rock hard shaft moving within her and she began to move with me. Now Kim began to thrust into my strokes as I drove my tool home on each inward stroke. Before very long I shot my load into Kim’s hot little pussy and a few moments later she reached her climax as well. We continued to lie together for a while; both of us breathing heavily with our hearts pounding.

Finally I withdrew from Kim and got up from the couch. As I looked down at Kim, I saw her eyes were closed and there was a smile of contentment on her lips. I asked, “How did you like your first visit to my dungeon?”

Kim sighed and said, “It was wonderful!”

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