Midlife Teen Ch. 02

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Midlife crisis gets serious.
6.3k words
4.68
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22

Part 2 of the 3 part series

Updated 06/08/2023
Created 05/29/2014
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"Chelsea," I stopped her again as she opened the restroom door.

She turned and smiled at me as she said, "I was afraid you didn't actually know that."

"I do, and I will definitely remember it," I said as I pulled out my wallet and took a card from within. "Friday night... 7:00pm... text or call and let me know where to pick you up." I stepped up beside her to hand her the card and then I whispered in her ear, "dress appropriately naughty girl. That gives you three days to imagine all the things I'm going to do to you."

"Can't wait," she said breathlessly and finally fled.

On Thursday I finally got a text that told me to pick her up at her former place of employment on Friday night. It came complete with a devil horned smirking emoji. When I questioned the pickup location, she replied with a statement that she couldn't leave the house 'dressed appropriately' while the parents were there. So, on Friday I dutifully pulled into the parking lot to find her waiting outside in jeans and a t-shirt and carrying a pink backpack.

"Can we go to your place so I can change," she said nervously when I walked up.

"Why not just change here," I asked knowing the answer.

"But... I mean... someone there might see me... someone that knows me."

I leaned in and whispered in her ear, "I dearly fucking hope so." She was blushing furiously when I pulled back. I noted that that while the place wasn't deserted inside, it was also far from busy. "Let's go," I said taking her hand and pulling her inside with me. "The bathrooms are close to the door; I doubt any of your former co-workers will spot you." I gave her ass a swat to get her moving in the direction of the ladies' room and turned to watch the dining area.

It didn't take long for her to change clothes and when I heard her and turned, I could feel my mouth drop open in response. She was wearing a fluffy pink halter top that tied in the middle of her chest and had elastic bands on the top and bottom which were the only things keeping it in place. Along with that was a matching loose fit black skirt that was tantalizing in its shortness and just as fluffy and also held up by elastic at the waist. It had pink stemless rose buds decorating the waist and bottom edges. To complete the outfit, she had on strappy black leather heels of moderate height which showed off her pink toenails.

I offered her my arm, which she quickly took and we made our way out the door. "Don't trip in those," I chided her, "they're probably all watching." To which Chelsea blushed and jabbed me in the ribs. I walked her to the passenger door of my car and opened it but turned her back toward me before she could enter. "One moment," I said. I reached out before she could react or protest and pulled her halter top away from her chest far enough for me to peek inside. I confirmed there was no bra and also noticed that her nipples were very hard.

"What," she said in alarm and quickly knocked my hand away and pushed the halter top back in place leaving her hand on top of it.

I spun her around away from me again and lifted the back of her skirt and confirmed she was not wearing panties.

"You horrible man," she hissed at me and used her other hand to press and hold down the back of her skirt as I turned her back around.

"Those nipples of yours were awfully hard. Are you enjoying this you naughty girl," I asked playfully. Chelsea blushed deeply again and looked down at her feet. "I'll take that as a 'yes' then," I said as I leaned in so I could whisper in her ear. "Good girl, I enjoy it so much when a girl does the naughty things I ask her to do."

When I pulled away, Chelsea was still blushing, but she looked up with a confused look on her face. "But... this is what... you told me not to wear them."

"No," I said firmly. "I *asked* you to Chelsea. I will never *tell* you to do something and that is a *very* important distinction."

She smiled at that and hugged me. "Well then, I guess I will have to forgive you for peeping at me then. So, can I get in the car now?"

"Of course," I said and closed the door after she sat and then went to the other side of the car and got in.

"So, where are we off to?"

"Dinner and then a movie."

"Oooo, how original," she said condescendingly.

"If I start out predictable, it gives me plenty of room to improve," I smirked in response. I drove to my restaurant of choice about twenty minutes away, which was a fairly standard middle of the road place. It served as a low price date night destination, a family outing destination, and even as a late night college student hangout. It was fairly busy for a Friday night, and Chelsea was on display as soon as she set foot in the door. She stayed in a perpetual state of blushing until we were seated.

"I think they're all looking at you," I said with a smile.

"Stop it," she said and blushed deeper.

"I wonder what they're all thinking? Do they all think you're my barely dressed daughter, that you're a troubled young girl with daddy issues, or that I'm a lecherous old cradle robber? What do you think?"

"I think you should be quiet," she said testily.

"Be careful how you sit, someone might notice your lack of undergarments."

"You're enjoying this, aren't you?"

"Maybe a little. The really important question though is, are you?"

Chelsea looked down at her hands and blushed again. I stopped pressing her and picked up the menu in front of me and started looking for something to eat. Chelsea followed my example and a waitress was soon standing over us taking our orders. She looked at Chelsea out of the corner of her eye more than once while we ordered.

"See anything you like," I asked her pointedly the third time I saw her do it.

"Sir," the waitress asked confused.

"That's the third time you've checked her out, or do you not approved of the outfit?"

Chelsea looked sharply at the waitress, but I kept the poor girl focused on me.

"That's not... I don't understand... I apologize if I've done something wrong sir."

"It's ok, I don't mind if you look. As long as you understand she's with me."

I saw Chelsea smile when I said this, and for once, she wasn't blushing.

"Very well sir, I'll just go um... put this order in."

We ate in relative silence, but I periodically made Chelsea uncomfortable by staring at her. After the fourth or fifth time I did it, she stuck her tongue out at me and I laughed.

"About time," I said, "I was worried I'd lost you."

We finished our meal and I drove us toward a nearby movie theater. When I ordered tickets for the 9:00pm showing of the latest Disney movie, Chelsea looked at me in confusion. The movie had been out for almost two months and would probably be out of theaters entirely after this weekend.

"Sorry, has my naughty little girl already seen this," I said as I snuck out a hand to tickle her side which made her squirm.

"No," she giggled, "but I'm a little old for Disney movies."

"Tsk, no one is ever too old for a Disney movie," I chided. "'That's the real trouble with the world. Too many people grow up.' Also, it's Friday night... how many people do you think will be out seeing a Disney movie?"

"Um, not too many I guess."

"Exactly," I said happily. "Or would you rather have a large audience while I molest you in the dark?"

"Pervert," she hissed at me with a laugh.

"For you, always."

We headed into the movie theater and took up seats at the very back of the theater and waited. By the time the movie started, there were only two other people in the theater; an elderly couple that sat several rows in front of us in what would normally be the best seats in the house.

"You better be quiet," I whispered in Chelsea's ear as I put the armrest between us up. "If they hear you and turn around, they'll see whatever we're doing."

"And what will we be doing?"

I ran a finger from her ear, down her neck, across her shoulder, and then slowly down the entire length of her arm until my hand came to rest over top of hers.

"Oh, nothing much," I said ominously.

I pushed her topmost leg with one finger until she relented and uncrossed her legs. I then ran my finger along the top of her leg from the top of her knee to the very high hem of her skirt. I repeated this on the outside of her leg and snuck a couple of inches past the hem of the skirt, but she did not move. The third time I repeated it, I did so along the inside of her leg which made her squirm, but she also parted her legs slightly allowing me to creep a few inches beneath the skirt again. When I stopped I took her hand in mine and started to entwine her fingers with mine, wriggling and stroking playfully. The movie started and I completely ignored it. We sat and held hands for a good ten minutes before I leaned over to whisper in her ear.

"How long have you been wet," I asked. Chelsea squirmed noticeably in her seat. "Since the restaurant where we ate?"

"No," she said nervously. "Since I changed clothes."

"Good girl," I whispered in her ear, "you could have lied." I ran my finger along the top of her halter top and back up her shoulder and to the back of her neck. "But I saw the little wet spot in the car when we were done eating." I couldn't see it, but I could feel her blush and I pulled her toward me. "I've been hard since I saw it," I said as I kissed her. She moaned softly as our kiss deepened and it was maddening to not only hear it, but to feel it on my lips, my tongue, and in my whole mouth.

As she melted into me, I moved my hand back to her halter top and pushed it firmly down to her waist. She made no move to stop me and my cock throbbed in my pants at the realization. We made out for several minutes and my hands danced around and across her nipples the entire time. When she finally broke away from me, I immediately moved my hand to her leg and began slowly running my fingers up and down its length. "Would you let me take you right here in front of them," I whispered.

"Maybe," she said breathlessly, "but we'd probably get arrested."

"Let's trying something else then," I said as I let my hand slip completely under her skirt. Her legs opened immediately and when I felt nothing but smooth skin I groaned and my head lolled against her shoulder. "Oh baby, did you shave for me," I gasped.

"Waxed actually, but I thought you might like that."

I kissed her again, more urgently than ever and my hand went to work beneath her skirt. She was sopping wet and I knew it probably wouldn't take long to bring her to orgasm. I concentrated solely on her clit only rarely teasing her opening without penetrating her. After only a few minutes of this she stopped kissing me and pushed me back a little. Her far hand gripped the armrest on the other side and she held on for dear life. She looked at me pleadingly and I wasn't sure what to make of it.

"Is that look because you want me to stop or to keep going," I said with a smirk.

"I'm not sure," she said through gritted teeth.

In response I increased my pace and her body began to shudder in the chair. She clamped her jaw shut to try and suppress any sounds. Finally, I slipped one finger into her just up to the first knuckle as I bore down hard on her clit with my thumb. She convulsed in the chair and her other hand grabbed the edge of my chair as she fought to ride her pleasure quietly. She succeeded, but barely, and quickly pushed my hand away as her orgasm started to ebb. While she watched me I licked each of my fingers in turn enjoying the taste of her.

"Just think," I said when I finished, "in a few minutes they'll be able to smell you down there, maybe sooner if the air conditioning currents are right."

"Please, let's get out of here. I can't sit through another hour of this in a wet chair," she said with a grin.

Numerous sets of eyes followed us through the lobby as we made our exit from the theater. Once in the car I took off toward home. I realized I wasn't going to wait the thirty minutes it would take to get there, so I made a detour after a few minutes and ducked into a parking garage. I pulled out my master key card and opened the gate to the deserted structure and let myself in. Chelsea looked at me sideways but made no comment. I went up to the fourth of the five floors and parked near an inside corner and got out.

"What are we doing here," Chelsea asked as I came around to her side of the car.

"It's thirty minutes to my place and I've decided I can't wait that long." I grabbed her around that deliciously bare waist and pulled her hard against me and kissed her roughly. When I finally broke away from her she gasped.

"And here I thought I was the only one that was all hot and bothered," she said with a smile. "This is awfully open, are you sure this is a good place to be fooling around?"

"Probably not," I said evilly, "but I don't give a damn. I want you. Now." I knelt down in front of her as she leaned back on the front fender of the car, but when I looked up I could still see a troubled look on her face. "I own the office building next door and this garage. It's used by the city government and *no one* works there on the weekend." When I saw her brow unfurrow I promptly burrowed my head under her short, loose skirt and buried my face in her crotch. She leaned back farther and spread her legs to grant me better access. I proceeded to make out with her very smooth and very tasty pussy. I soon had her wetness all over the bottom half of my face and I was driving myself crazy on her. I raised a hand and inserted two fingers into her and she immediately moaned long and deep. I focused my oral attentions on her clit and after only a few seconds she quickly tumbled over into an orgasm that almost had her tumbling head first over top of me. I quickly stood and caught her before that could happen.

"Wow," she said as her head lolled against my shoulder.

"Let me guess, boyfriend never did that for you before?"

"No, even though I did the equivalent for him regularly. Played with me a little of course, but never enough to do that."

"So I guess it's my turn," she said with a smile.

"No," I said as I stopped her. "Another time for that, I need to fuck you now my little slut."

Chelsea blushed and I was careful to look for any sign of anger at my dirty talk, but there was none. I quickly undid the laces in the front of her halter and practically tore it off her when they finally came lose. My head dove and I lavished some oral attention on both of her small breasts. Her breathing became heavier again and I stood to kiss her, tugging at her hair and pulling her tightly against me. When my hands grew frustrated at groping her skirt clad ass, I quickly pulled away, squatted down and yanked the garment to Chelsea's feet. She stepped out of it and I tossed it aside next to her halter top.

Before I stood I shifted my position and quickly removed my shoes and socks. When I was looking at her again, I saw that she was looking at me impatiently, so of course I slowed way down as I started to remove my button up shirt.

"All that urgency and now you're Mr. Slowly McSlowerson," she asked in irritation.

My only reply was to continue staring at her as she stood there naked in front of me. I undid my belt and made a show of dropping it on top of my shirt. As I slowly unzipped my pants I saw Chelsea bite her lower lip, which made my dick twitch in my pants. I removed my pants and dropped them to the side and began to wiggle out of my boxers. I saw delightedly that Chelsea's eyes had drifted south and were glued to my crotch. I turned her around and stepped up close behind her with my cock settling naturally between the two halves of her fantastic ass.

"I'm going to fuck you now slut," I whispered in her ear. I felt her body tremble against mine and she sighed heavily. I bent her over the fender of the car and became immediately thankful for the height of heel she had chosen... they were damn near perfect. I pushed just the head of my cock past her pussy lips and into her entrance, and then I stopped. She wiggled her hips slightly trying to get more of me inside her and when I stopped her from pushing back against me she growled in frustration. "I want to hear you say it Chelsea. What does my naughty little girl want?"

Her head lolled on the hood of the car and all she could do was whine in frustration.

"It seems my naughty girl has lost her voice," I said as I pulled back and slapped the right side of her ass hard. She yelped in response. "Well, it still works apparently. Be a good girl now, and tell me what you want."

Her head was still down on the hood of the car and I saw her shake it no as she tried to push back against me and find my cock again.

"Bad girl," I shouted and slapped the left side of her ass with my other hand. Her yelp this time was more lustful groan than yell and she sagged further against the hood of the car. "Tell me what you want slut, or I will have to keep punishing you." I slipped out of her and stepped close enough to lean over her and run my hands up under her and lift her off the car slightly. When I found her nipples I squeezed both hard between my fingers and she croaked and groaned at the same time. I put the head of my cock back inside her and waited.

"Fuck," she whispered. "I want you to fuck me," she said louder, "fuck your little teenage girlfr..."

Her last syllable was cut short as I slammed my entire length inside her and pushed her firmly against the fender again.

"Yes, good and hard," Chelsea moaned. I pulled out and repeated the forceful entrance several times and I noticed there was a nice trail of liquid running down the fender of the car from her.

"Faster," she said quietly when I paused.

"Is my little girl enjoying this," I asked without moving.

"No," she started, which I had anticipated and was met with an immediate slap on her ass. "Yes," she said loudly, "yes, I am enjoying it very much!" I slammed into her one more time.

"And what kind of girl enjoys this," I asked her firmly.

"Um me... that is... a naughty girl does."

I slapped her ass again and her whole body quivered in response. "Going out with an older man is naughty," I said as I slammed into her again. "Going out without any underwear is *very* naughty," accompanied another slamming entry. "But what kind teases and older man until he starts slamming his very hard cock into her," I said and thrust into her again.

"Oh god," she gasped. "The very slutty kind," she finally said softly. "Faster... please... faster," she moaned.

"Good girl," I said as I started to ease in and out of her at a regular but sedate pace. I had only taken three strokes when we both heard it. A metallic clatter from around the corner.

Chelsea froze and I heard her whisper "oh no... someone coming... going to see," she said panting. I took her long hair in my hand and pulled her up off the car and against me. Before either of us could do anything else, a homeless man pushing a grocery cart came into view on the other side of the car across the driving lane of the garage next to the outer wall of the structure. Chelsea started to raise an arm to cover herself and I quickly swatted it away and she blushed deeply as she saw the man's head turn toward us in response to the sound. I immediately resumed fucking Chelsea and she failed to suppress a moan from escaping out of her when I did.

"Hey dere missy," the man said drunkenly, "r you ok?"

"Answer him," I whispered in her ear.

"Yes sir," she panted, "I'm very, very ok."

"Ya sure... if he's getting his rape on dere's a police station right down da corner I can run to."

I sped up a bit in my thrusting and when Chelsea yelped I realized that when I pulled her up I had changed the angle of attack on her cunt. I suspected I was now banging squarely into her g spot on every thrust, which served only to spur my assault onward. "Tell him," I whispered.

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