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Chapter 5
by wicker
what does tomorrow bring?
I Finally Get Some
The next morning, I showered and dressed. My Tuesday/Thursday classes did not start until 10. I walked around campus for a while thinking about what I could do with the ring. Dean Van Horne was my primary target, but before I did anything with her, I wanted to help myself a bit and become more accustomed to being with a woman. Unfortunately, campus offered few MILFS. There were a small number of MILF professors, but most were married.
I went to the two classes I had that day. I was off that night, so late in the afternoon, I decided to head into town and see if I could get laid. I rode my bike to a grocery store about a mile away from where I worked. It was outside an upper-middle class neighborhood. I had been there a few times to get snacks and such for my dorm fridge and new it to be MILF central. The problem I faced is that I assumed most single MILFS worked regular hours as they had to support themselves. But I banked a few having jobs with irregular hours or better yet, living off of an ex's alimony.
I parked the bike and chained it to the outside of a rail near a shopping cart holding bin and went inside the store. As I scanned the female customers who appeared to be between 30 and 50, it often became annoying trying to get a glimpse of their left ring fingers. Why couldn't hot married women wear tiaras in addition to wedding rings, so guys like me could more easily spot them!
After getting a few snacks for the dorm, I saw a likely target. It was a woman who could have been the poster child for what a stereotypical suburban soccer mom looks like. She looked to be about 40, had blonde hair in short pony tail, wore khaki capri pants, and dark green blouse. She had on sandals with fake gemstones on the straps. She looked to have a 34-34-38 body and was medium height.
I followed her discreetly until we both came to an aisle that was empty. My heart was pounding, and my chest grew tight. I walked up behind her. "Excuse me," I said.
The woman turned around and looked at me. She gave a polite, if not stiff smile. "Yes,"
"Aren't you Walter Smith's wife?" I asked.
"No," she said, "I'm not married."
Cha-Ching! Mental fist pump.
I got the ring into position. "I'm Davy," I said. I then hit the green button.
The woman's face went blank, and she stared right at me. I looked around and saw no one.
"Um, you really want to give Davy a blow job. You must give him the greatest blow job you can." I knew I had a full minute, but spoke quickly nonetheless. "You don't know why, but you just have to suck his cock as soon as you can, and um, you'll do anything for him if he agrees to let you suck his cock. Sucking Davy's cock will really, really get you turned on, and when he cums in your mouth, you will have the greatest orgasm you've had in years. You don't know why you must have his cock in your mouth, but you must and won't care why. After you finish, you will want to reward him and thank him any way he wishes no matter what."
I swallowed hard. I was trembling. Had I done it right? Did I talk too fast? Did I ramble? A minute is a very long time when you are afraid. Finally the women blinked a few times. She looked at me again but this time it was like she was seeing something she had long desired and had finally gotten close to it. She ran her tongue over her lips, and looked down at my crotch then up at me.
"Um, Davy, is it?" she asked.
"Yes, and you are?"
"Karen Winters," she said.
I extended my hand. "Nice to meet you."
She took my hand. She was growing very nervous, which made me feel better as I was more nervous than I had ever been in my life, so knowing I was not the only one made me feel slightly less so. She pulled me closer to her. "This may, well, um....this will seem strange, but...um...."
"What is it?"
She leaned in and whispered in my ear. "I just have to suck your cock!"
I decided to toy with her and see just what she would do to get my cock in her mouth. "Is this a joke? Am I on some hidden camera show?"
"No, I swear!" she said. "I can prove it to you!"
"How?"
"Um, I'm not sure," she said, "Do you have any suggestions?"
"Yes, first, go to the ladies room, remove you panties and bring them back to me, then pay for my groceries then take me to your car. If you do that, you can blow me in your back seat."
Karen blushed deeply. I could see the conflicting emotions of lust, embarrassment, and confusion at play in her. "Sure thing!" she said. "Wait right here." She grabbed her purse and hurried off to the restrooms.
I noticed I was an aisle over from the wine aisle, so I went and got four bottles of wine averaging about $20 a pop. Being only 18, I could never have bought this, but Karen could legally do so. I went back and waited by her cart.
A few minutes later, Karen came back. There were a couple more people in the aisle, but they were walking away from us. She looked around then took a pair of bright yellow cotton panties out of her purse and shoved them into my hand. I looked down at them. "A sexy woman like you should be wearing much sexier panties," I said.
She smiled and looked down. "Are you ready to check out?" she asked.
"Just a few more things," I said. Despite the fact I could not wait to get my cock in Karen's mouth, I did not want to pass up the opportunity for free groceries. I got some chips, dip, fruit, nuts, tooth paste, deodorant and shampoo. I also got some cloth reusable bags to carry the wine home in. Karen did not say a word as I finished. She paid for everything and sorted my things into separate bags. I followed her to her vehicle.
Karen drove a late model Nissan SUV. On the passenger door was a large sign Great Western Real Estate: Karen Winters Agent 555-3400 We put the groceries in the back. I noticed a soccer ball and lacrosse stick in her car. I smiled and rolled my eyes when I saw the soccer ball. She really was a stereotype! She had a Proud Parent of an Honor Student at Western High car magnet on the back. "Let's drive some place a bit more private," she suggested.
I agreed, and we drove to the end of the shopping center where the grocery store was located. The end used to house a restaurant but it had closed, and it remained empty. Karen parked in an empty part of the parking lot. Without getting out of the car, we took turns climbing into the back seat.
Karen fumbled at my jeans. She was obviously nervous and embarrassed but overcome with lust for my cock. She got my pants undone, and I lifted myself up and we got my jeans and boxers down. Karen eagerly went down my my cock.
I held her pony tail in one hand and stroked the soft blonde hair on the top of her head with the other. I closed my eyes and tried to think of a brick wall. I did not want to cum too soon.
Karen moaned onto my cock as she went up and down, stopping her sucking every few seconds to use her tongue or teeth to play with it. She knew what she was doing.
"Oh, god, Karen, you are fucking fantastic!"
I did not last much longer after that and came in her mouth. Karen bucked so hard, she bit my cock, but not enough to do any real damage. She eagerly sucked after her orgasm and kept it up until I was spent and started to grow flaccid. When I was limp, she pulled off, a thread of drool extending from the tip of my cock to her mouth. She used her hand to wipe her mouth. She was panting. She looked at me then quickly looked away. She looked down at her crotch. There was a wet spot there. Her mouth opened a bit wider and she clamped a hand over her crotch.
"Wow," I said.
She slumped back into the seat and stared at the back of the driver's seat. "Wow, indeed!"
I guessed she was embarrassed at the wet spot in her crotch and remembered I had given her the commands to get turned on by sucking me and having a tremendous orgasm, so she must have leaked quite a bit. She swallowed hard and stared ahead. After few more moments of not saying anything, Karen turned to me. "How can I ever thank you?" She asked.
"Stop wearing boring panties," I said jokingly. "You're too sexy for cotton undies."
Karen gave a nervous laugh. "Thanks," she said, "It's nice to be called sexy again. Anything else, though?"
"Sure, let me keep your boring panties as a souvenir, but more importantly, let's be fuck buddies, or better yet, suck buddies," I said. "I'll give you my number, and we can set more meetings for you to blow me when we are both free."
Karen nodded. "I can do that," she said with a nod and blush. "Anything else?"
"Well, you can send me some photos of yourself in your sexiest underwear from time to time, and you can drive me back to campus."
"Sure thing, Davy," she said. She wiped her mouth again. She reached into the front center console and took out some chewing gum. She handed me a piece and took one herself. After a few moments, she leaned over and kissed me. We climbed back into the front, and Karen drove me to my bike. I put it in the back, and she drove me back to campus.
What's next?
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MILF Master
A teen's dream
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