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Walnut Street: The New You  

JimmyB7474 59M
0 posts
8/15/2017 10:50 am
Walnut Street: The New You

Back in the day I had a number of “one night stands” while living at the Big House on Walnut Street. But there was this one time I had a “one day stand”. I remember that event and it makes me hard to this day, years later.
It was a moderately warm summer day, not one of those where you're baking in the sun, but nice. It was just after 4:30 pm on a Monday and I decided to stop by my local K-Mart for a few needed things, before going home. Nothing major just a few snack and stuff.

For the record I'm not the best looking guy on the planet, but I do all right with the ladies, I'm just shy of 5 ft. 10 and tip the scales at just over 160 lbs, with dark hair and blue eyes. Being single I am always on the lookout for someone to warm my bed, even if it's just for the night. Granted I prefer a long-term relationship but they really hadn't worked out for me in the past.

Walking through the household goods on my way to the electronic section I just happen to spot her. She was standing looking at some clocks, she looked to be around 5' 5" tall and I'd say at around 130 pounds or so. An older woman than the college co-eds I normally hang with. She was dressed in business attire. A dark brown blazer over a lighter color cream camisole top; with a dark brown wrap around skirt that fell to just below her knee. Her shoes were low heels with dark nylons.

She was just the kind of woman I tend to look for, the overlooked diamond in the rough so to speak. I could see from her profile that she was cute. So I busied myself with looking at some picture frames while watching her out of the corner of my eye. Her hair was dark and fell just to her shoulders, and hung loose. She wore dark sunglasses so I couldn't see her eyes. I did notice that she wore a couple of rings, but neither was a wedding band. After a few moments she moved off towards the women section, I watched her shapely ass as she walked away. Since I didn't want to appear to be stalking her, I continued on my way to pick up a few things, all the while keeping an eye out for her. I grabbed a couple of boxes of cereal and a few other things, and headed through the woman's section towards the checkout counter.

Fate as it would seem had other plans for us. Turning an aisle at random, and not at all watching where I was going, I ran directly into the lady as she was coming out of the bra aisle. Granted the collision wasn't hard enough to knock either of us down, or even to hurt us. It did however allow several things to be knocked out of our hands and into the floor.

We both quickly apologized as we started to pick up our packages; I did notice that one of the things that had fallen to the floor was a black lace bra in the size 40 DD.

Since we had already gotten over the awkward meeting stage I said. 'I'm Jimmy."

With a quick smile she replied "I'm Judy."

"Again, I'm sorry for running into you." I said. "I should have been looking where I was going."

"It's okay, no damage done."

My father always said 'No risk taken, no fun had.' With that adage in mind I said, "Tell me Judy, I know it's early have you had dinner yet?"

She watched me from behind the dark lens for a few sections before. "Actually I haven't, and I skipped lunch."

"Well then would you do me the honor of having dinner with me?"

"That all depends on what you have in mind for dinner."

This reply was not one I was expecting. So I replied. "There's Subway across the parking lot from the store, unless you had someplace other in mind."

"Subway would be just fine."

The lunch crowd had come and gone, and the dinner grown hadn't started to come in, so the place was almost empty and we were able to get our sandwiches right away and sit down in a quiet out of the way corner booth.

We made the usual small talk as we ate. I found out she had just turned 30 and was working as an accountant in a local firm. She said she was single with no , living in a nearby house with a roommate. I also found out her eyes were a deep brown and she had a smattering of freckles across her nose. Her lips were full and just begging to be kissed.

She finished her sandwich and wadded the paper into a small ball. After a few seconds she then looked at me with a smile and said. "I hope you aren't expecting sex after dinner."

I laughed as I quickly thought up a decent response. "No I wasn't, it wasn't that expensive of a meal."

She laughed and seems to relax a bit, as if she had been on her guard through out the meal. "So tell me Jimmy, speaking of sex, what are you looking for in that department, other than a woman that is."

I'm not normally accustomed to a woman that was this blunt so the question caught me somewhat off guard. When I didn't reply she said. "Come on, you can tell me, that worse thing that can happen is that I slap your face and walk out."

"True." I agreed.

"Well?" She prompted.
With a grin I said. "Let’s see, I like a woman that is not afraid to show her body off."

"You mean like a strip tease?" She asked taking a drink of her diet coke.

"That too." I said with a smile.

"Then what do you mean?" She asked with a smile. I had a feeling she knew where I was going, but wanted me to spell it out.

"I'd like a woman who is an exhibitionist." I said, fully expecting her to get up and walk out.

"Ah I see, like those women in all those girls gone wild videos"

"That's an extreme form of it, yes, but not what I had in mind."

"There is more than one way?" she asked.

"Yes there are several things that fall under that heading." I said slowly warming to one of my favorite subjects.

"Like what."

"Have you ever ran around in public without any panties on in a just a short skirt?" I asked

"No, I haven't. Besides, my figure isn't cut out for short skirts."

"I think you've got the perfect body for it." I replied.

"Thank you, but I don't see how that would be a turn on for you."

"Well the thrill for the voyeur comes from seeing the normally unseen." I replied. "It all stems from the current view that seeing the female body is somehow taboo."

"And you don't believe that?" She asked.

"No, I don't." I replied. "There's a lot of hang ups that could be solved by de-tabooing the human body."

"I hope you're not expecting me to strip down and take a stroll through the store."

"No, of course not. Not that I wouldn't enjoy that. But that isn't what I am talking about." "Then what kind of exhibitionism are you talking about? Me flashing people in a trench coat?"

"Again that is just a version of what I'd like to see you do."

"I'm listening."

"Here's the kind of outfit I would love to see you in; a simple button up blouse and a short skirt. Minus the bra and panties of course."

"Of course." Judy replied with a smile.

"Well, in that kind of outfit we could always go shopping and stuff where you'd bend over or squat down, showing me and the world what you've got."

"I see." She replied. "Isn't that illegal?"

"Only if you get caught." I said. "The beauty of this is most of the time you look perfectly normal, only under the right conditions does your nudity appear."

"And seeing that is what gives you the thrill."

"Oh, it'll get your motor running as well. Trust me."

After a few moments she said. "How short are we talking?"

"Mid thigh or a maybe little higher."

"Really? Do you think I'd look good in something like that?" She asked.

"Yes, I think you'd look great in a lot of things, including the nude." I replied with a smile, yet being perfectly serious.

"I am sure that I don't have anything like that." She said after a few seconds of thought.

"We can solve that." I replied.

"Is that an offer to buy me a new skirt." She said.

"Of course." I replied

"And all I have to do is take off my panties and let you see my pussy a few times in public?"

"Correct, and your bra as well."

"And no sex?" she asked.

"Let's take it one step at a time shall we." I replied.

"Well I can't take them off out here." She said. "I'll be right back." She then got up and went into the ladies restroom that was a short distance away.

After a couple of minutes she came back out and sat back down at the table.

"I can't believe that I am doing this." She said.

She sat across from me with her arms folded across her chest, looking nervous.

"Relax, the only ones that know are you and me. But if you walk around like that you'll attract more attention than other wise."

"I haven't gone without a bra in years." She said.

I reached across the table and took hold of her hands and pulled them towards me. The shirt was doing a fair job of hiding the fact that she was braless; the only tail-tale sign were her nipples that were poking hard against the thin material.

"See nothing is showing at all." I replied.

"Still it feels odd, like everyone can see them."

"So can I look?" I asked.

After a few seconds and a couple of quick look around she nodded in agreement.

I quickly ducked my head beneath the table. "Judy, your skirt is still blocking the view." I said from beneath the table

Judy paused a few second then hiked her skirt up enough to allow me a peek at her pussy. I could tell it was covered with dark hair but not to bushy.

"Are you done?" She asked in a low voice as I sat back up.

"Well, shall we go shopping?" I replied with a smile.

I watched as we walked back into the store, knowing there was nothing between her ass and the material of her skirt. It was a view I was really starting to like. As she started to push the cart towards the women's section again, I place my hand on the top of her ass. She looked at me and said. "You sure no one can see my tits?"

I just smiled. "Nobody that would realize that you don't have a bra on. Unless."

Stopping dead in her tracks she look at me and said. "Unless what?"

"You start running or jumping up and down."

"I'll try to keep from doing that." She replied as she started pushing the cart towards the women's section again.

The first stop we made was into the nylons department where I picked up a pair of fishnet hose for her.

"Fishnets?" she asked.

"It's all part of the look." I replied.

"As long as I don't end up looking like a cheap ."

"I promise you won't."

Shopping for the right skirt proved to be a fruitless endeavor when they had nothing in her size that was short enough for my liking.

"Now what?" She asked.

I came up behind her and kissed her on the neck, wrapping my arms around and giving her a hug. "You know what?" I asked into her ear.

"What?" She asked.

"That right now I could lift up you blouse and show those lovely tits of yours to the world."

Breaking from my embrace she turned quickly to face me. "You wouldn't dare!"

"No me dear, I wouldn't, but you could at any time."

She looked around at the shoppers nearby and said. "I don't think so."

I smiled and said, "Well there isn't anything here that will do. At least in the skirt department."

"So now what?" She asked as we started to walk to the front of the store. "Road trip!" I replied.

"To where?" She asked.

"What about J. C. Penny’s?" I asked. "They're a plus size shop."

"That's over at the Eastman Mall."

"So, I'll drive." I replied.

After a few seconds she replied. "Ok."

We quickly took our purchased to the checkout and headed towards my car. It was a Black '95 BMW Series 5, with leather interior, while it wasn't the newest thing on the block, it was well maintained.

"Nice car." Judy said as I helped her into the passenger side. This bit of gentlemanly behavior seemed to take her at a bit of a surprise.

I started to start the car when I looked over at her and said. "Hike up your skirt, let the kitty get some sun."

"What?" she asked shocked.

I quickly reached over and pulled the tie on her skirt.

"What are you doing?" She hissed.

"I want to see your pussy as I drive." I replied.

"Won't you be too distracted to drive?"

"I'll have to control myself." I replied. "You could always put on the fishnets as well." We had after all put all the purchases in the back seat.

"But someone will see me." She said.

"I doubt it, plus we'll be moving. Now why don't you change into the fishnets."

After a few seconds, and once we had moved into the light afternoon traffic she said. "Ok, I will."

She then reached behind the driver’s seat to pull out the package the hose were in. She quickly kicked off her shoes and slowly slid her hose down, teasing me as she did so. She repeated the process with the fishnets, which actually went well with her outfit. Her skirt had slowly loosened as she did so, affording me a better view of her dark pussy. "Now if you set the seat back, it'll help disguise the idea that your pussy is sunning herself." I said.

She set the seat back to a lower angle and I flipped her skirt all the way open. "Looks good enough to eat." I replied with a smile.

"Are you sure no one will see me?" She asked nervously.

"I'm sure, just lean back and relax." I replied as I lowered the power windows on the car.

After a few blocks, with the warm summer air blowing on her pussy, she says. "I am getting to like this. It's naughty and yet kind of exciting."

"See, I knew under that cool accountant exterior was a wild lady trying to get out."

"Oh, you did, did you?" she said looking at me.

"It was a calculated risk." I said as we pulled to a stoplight.

"Oh, Shit!' She said and quickly pulled her skirt over to cover herself as a car pulled up beside us.

"They can't see you." I said as I flipped her skirt back over.

"You sure?" She asked as the light turned green.

"It's not like we're going through a drive in." I replied. "Hell, you could take the skirt off and no one would know but me."

"Not yet." She said with a smile.

A few stoplights later we pulled into the mall, I parked at the opposite end from J.C. Penny’s "Well how was the drive?" I asked as I helped her out of the car. She retied the skirt so it wouldn't flap open as we walked.

"It was fun, once I got over being so nervous."

"I could tell by the look on your face, you were enjoying it." I said as I opened the door to the mall for her.

"Ooh." She said. "That air is a bit cool after the sun."

"Like that huh, Sexy?"

"Maybe."

"I'll take that as a yes."

The fashions at J. C. Penny’s was just what we were looking for and within a few minutes we had a few skirts for her to try on and headed towards the dressing room. I waited patiently outside the dressing room as she changed into the first skirt. It was a dark blue number, but wasn't quite short enough for me. A few of the others were either too long or didn't fit her right. She then came out in a very short white pleated tennis skirt that seemed custom made for her.

"Turn around."

Judy did a slow turn for me, the skirt seem to cling to her shapely ass in all the right places. Looking around to see that know one could see her I said. "Bend over."

"Like this?" She said bending over at the waist, her shapely ass pointed in my direction.

I could see her pussy lips just peaking out. "Looks like we have a winner."

"But my blouse doesn't really go with this style of skirt."

"Well I'll just have to buy you one." I replied

"What's the catch?" She asked.

"It must be a button up number."

"Ok, you're on." She replied.

She quickly slipped back into her skirt and we continued shopping and trying stuff on until we had her a complete white outfit. The dark fishnets and shoes making a sharp contrast and seemed to go well with her hair.

Judy asked the clerk if she could change into her new outfit as we paid for it. The clerk had no problems with it. A few minutes later she came out looking even better than when I first saw her. "Well?" I asked as we stepped out of the store.

"I think you look like a million bucks." I replied as we started down the mall.

She was self-conscious at first as we browsed the different shops.

"I hope we don't run into anyone I know." She said.

"Why?" I asked. "So I bought you a new sexy outfit, so what." "This morning I didn't have anyone in my life to buy me a sexy new outfit."

"And now you do." I replied as we entered into a small shop full of novelty items.

After looking for a few seconds I asked her to check the price of an item on a lower shelf. She calmly crouched down and read me the number.

"What?" She asked as she stood up, seeing the look on my face.

"Bend over and tell me what that number is." I told her.

"Right, I'm still having to get used to not being a lady." She replied but did as she was told.

If anyone had come around the corner they would have been able to see her lovely ass with her pussy peaking between her thighs. It was a wonderful sight to behold, and I reached over and slipped a finger along her pussy's outer lips.

"Hey!" she said in shock. She turned and looked at me blushing a deep red.

"Sorry, I couldn't help myself, just had to pet the kitty."

"I'm sure you couldn't." She said with a smile that told me she enjoyed the touch.

We continued to shop and I told her I wanted her to crouch down but spread her legs so that I could see her sex.

A few minutes later she stopped a squatted down in front a low shelf. "What do you think of this?"

I smiled as I saw that her pussy was clearly visible to anyone that would happen by.

"Looks damn fine to me."

Judy stood up and walked over to me and gave me a quick kiss, my hand brushing her nipples as they pushed through the material of her top. As we walked out the store I noticed that the evening crowd was starting to come in. I was expecting Judy to want to leave but instead she headed into the next store.

The store was well lit, but with lots of shelves. We continued to browse through the items.

"Hey, Sexy, how much is that?" I asked pointing to an item on the bottom shelf.

Once again she crouched down showing me her dark beaver, and told me what the price was.

"A little to much for me." I replied as I helped her up.

Turning to walk farther down the aisle she noticed there was a couple of people just behind where she had been crouched down.

"Shit!' She said under her breath, "Do you think they saw me?"

"No, but isn't in exciting."

"Yeah, it is." She admitted as I undid a couple of buttons on her blouse. "What are you doing?"

"I've seen the kitty, time to let the girls out."

"Your awful, you know that."

"Yes, but you love it."

"Maybe." She replied.

"You wet yet?" I asked

"Very." She replied.

She turned around and then quickly stepped back, grinding her ass into my hard cock. "Feels like you're having a good time as well."

"You bet, Sexy, you bet." I said as I nuzzled her neck. "I could take you right here, right now."

"Not just yet." She said with a smile. "I want to shop some more."

As we walked she slowly started to untuck her blouse from her skirt. She then stepped in front of me really quick flashing me her lovely breasts.

"Wow." was all I could say as she quickly covered herself up again.

"I can't believe I just did that." She said with a smile.

"I loved it, Sexy." I replied as I slipped my arm around her as we walked one hand trying to loosen the zipper holding her new skirt on.

"Don't even think about it." She said when she caught me. "Can't fault a guy for trying." I said. "How about some shoes for you new outfit?" I asked seeing a shoe store nearby.

"Sure." She said

The store was mostly empty when we entered. The woman behind the counter looked kind of bored as she asked if we needed any help, we told her we didn't and headed for the woman foot wear department.

I started looking at some shoes on the bottom shelf, while Judy stood with one foot on a stool looking at the upper shelves. Giving me the best view of her pussy lips I'd had all day.

"You see anything you like?" She asked

"Oh yeah, something that looks great."

"But does these go with my outfit?" She asked as she opened her blouse again.

"Yeah, they sort of complete the package."
Walking over to where I was, she bent over at the waist, practically sticking her ass right in my face.

"Damn, Sexy, that's the best thing I have seen all day." I replied giving her ass a quick kiss.

"Oh really." She said setting down on the stool. "What about this?"

After a quick look over she shoulder to see that no one was coming she quickly hiked her skirt and spread her outer pussy lips to show me her clit. She then proceeded to slip two fingers in her wet hole. Quickly getting up she walked over and touch my lips with her juice soaked fingers.

"Hmm, tasty." I said. "Loved the show."

Picking out a pair of low-heeled white pumps she said. "Let's get out of here."

We paid for the shoes and headed towards the car, about half way to the car she let go of her shirt tails letting it fall partially open, giving me tantalizing glimpses of her Double D's. Just as we got to the car a gust of wind blew open her shirt, and much to my surprise she didn't try to cover herself.

I unlocked her side of the car and helped her in and then proceeded to walk around the car and get in myself. When I did, I found Judy setting there naked from the waist down, her new skirt in a pile in the floor. "Let's find someplace quiet." She said placing her hand on my crotch.

"What happened to the No Sex?"

"That was before I knew how turned on I would get." Judy replied as she started to undo the fly of my pants. "Can you drive while I suck you off?"

"I can try." I said as I started the car.

As I started to back out I felt Judy free my manhood from my pants and slowly start to stroke it. Then I felt her lick along the shaft of it, and nibble lightly on the head. I let out a groan of pleasure as I spotted an empty alley and pulled in to it. As I shut the car off she took my cock fully into her warm, wet mouth, sucking and licking like a champ. After a few more seconds of sucking she stopped and kissed me.

My hands reached beneath her blouse to tease her rock hard nipples, as she let out a sigh of pleasure. "Don't Move." She said as she quickly got out of her shirt and then out of the car. I started to get out of the car as she came around the front of the vehicle. Dressed in just shoes and fishnets. She then pushed me back down into the drivers seat and proceeded to continue to suck on my cock as I played with her lovely tits. Just as I was about to blow my load she stopped. She kissed me and then quickly turned around and mounted my cock. It easily slipping into her sopping wet pussy.

"My pussy's so hot baby." She said as she did so. 'So fucking hot baby, fuck me!" I responded by just grabbing her hips and thrusting deeper into her.



"Save you spunk for me Baby! I love spunk. I love it! Can't get enough of it baby. Save it for me please. I want to taste it and feel it on my tits!"

One of my hands reached around her and found her clit and started to play with it. This just sent her into new heights of pleasure as she leaned back towards me.

"Yes Babe, that's it. Make me cum babe, Make me cum!"

A few moments later she leans forward and really starts to bounce up and down on my cock. Her words becoming groans and moans of pleasure.

"I'm cuming baby! I'm cuming!" she said suddenly then lets out a small scream "Oh god! Oh God!" she then slowed down, still fucking me. "That was great Baby." She said leaning back against me again..

We kissed, as she rode be a bit more, then before I could say anything she quickly got off and was once again sucking on my cock and playing with my balls. It wasn't long before I shot my load all over her face and tits. As I sat there catching my breath she walked around and got back in the car, licking my cum off of her fingers. "Hmmm, good stuff Baby."

As I zip up my fly, I asked. "What now, Sexy?"

She looks at the clock built into the dash of the car. "I'd take you up for round two but I need to get the car back so Anita can go to work."

"Ok, maybe we can do round two at your place."

"Why don't we save that for next time." She said

"What about tomorrow night?" I asked

"I don’t think so, Baby." She said pulling her white panties out of her purse she accidently dropped them.

Picking them up I said, "These are mine."

"Go ahead and keep them, I don't think I'll be wearing them much anymore." She said.

I started the car and head back towards K-Mart, it wasn't very long before she realized that she was almost naked and started putting her clothes back on. She directed me to where her car was parked. I helped her put the few packages she had in the back of her car. She leaned over the open trunk and I came up and grinded my crotch into her ass.

"Sure you don’t want too?" I asked playfully.

"I'd love to take you up on that, but I really need to get home to my husband."

"Uh… Husband? OK - so you.. uh.. lied to me earlier?" I said as slipped one hand under her blouse to play with her tit.

"Yeah, how else could I get to know you better?” She smiled as I pinched the nipple, “You aren’t the only one looking for a little “strange” on the side.. right?" She replied as she closed the trunk and got into the car.

I leaned over and gave her a kiss as she started the car.

"Thanks for the clothes Jimmy. I’m sure you got your money’s worth Baby." She said flashing her tits at me one last time before giving me a wink and driving off.

“Damn!” I thought, “Now hubby gets the benefits of the new you.”

My blog JimmyB7474 is called Into The Woods (erotica) entertaining stories about a guy named Jimmy. Enjoy.


JimmyB7474 59M

8/16/2017 4:36 am

    Quoting sexyldy1000:
    Would love to go shopping with you!

Love the pic.. horny little devil with a sexy tail... very suggestive Luv. Jimmy B.

My blog JimmyB7474 is called Into The Woods (erotica) entertaining stories about a guy named Jimmy. Enjoy.


sexyldy1000 68F  
9607 posts
8/15/2017 7:16 pm

Would love to go shopping with you!


JimmyB7474 59M

8/15/2017 10:52 am

Leave a comment if this sounds familiar.... Jimmy B.

My blog JimmyB7474 is called Into The Woods (erotica) entertaining stories about a guy named Jimmy. Enjoy.


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