Anal Summer Ch. 09

This story is a work of fiction even though parts of it were inspired by real-life incidents. Any similarity to real people, living or dead, is coincidental. All the characters are 18 years of age or older. Do not read this story if it is illegal to read about explicit sex where you live.

Edited by H.S.

*****

Friday, and the marathon was about to begin: Open-to-close at The Bistro.

I was excited; I had a good workout at the gym and had done well with my purchases at the fish market thanks to an associate of Davy's who hooked us up with a great deal. And Gemma and I were able to make up some quick specials for the weekend. All of this was accomplished very early in the morning.

We had another busy night and were officially the "it" place.

I didn't get a chance to see Madison, as she was flying out to visit her mother and wouldn't be back in town 'til Monday.

I already missed her. It hadn't even been a full week since I met her, but I was already smitten with her, to say the least. Madison's absence did clear the way for Gemma and I me to hang out at Davy's after work, and again on Saturday. I hadn't been there in what seemed like forever, so it was good.

Davy greeted me with a smile and said in a loud, jovial voice, "Hey, stranger! I thought you went missing again," he continued, referring to my disappearance when Kerry broke my heart. A number of old friends were there. It was just like old times, and I was feeling grateful, not only for the great friendships but for the familiarity of the old neighborhood and being fortunate to have grown up there.

Sunday was another very busy day, and it seemed the beautiful summer weather brought the tourists in full force. Sundays were always busy, but the season had increased our business, too. When Monday rolled around, I was glad for the day off. After the gym, I went to the beach and relaxed. I got home from the beach at about 5:00 p.m. and showered off the sand and salt.

I was about to go back out an go for a walk to enjoy another beautiful evening when my phone rang.

"Hello?"

"Why, hello, how are you?" said a very sexy and welcome voice on the other end. My heart jumped for joy just hearing it.

"I had the day off and don't have to work tomorrow, so I'm feeling great. How about you? How was your weekend?"

I was doing it again, acting like a thirteen year-old with a crush and limited social skills. My rapid-fire speech showed my nervous elation.

"Well, mother and I just took it easy and just sat around catching up."

"Oh, how nice, are you still there?"

"No, I arrived about 3:00. I called you, but there was no answer."

"Sorry. I was at the beach."

"It's fine, really. I was just wondering if you would like to go for a walk tonight."

"That would be great. When and where would you like to meet?"

"My place as soon as you want to be here."

"Okay. I'll see you at 6:30."

I showed up to find Madison waiting for me in front of her door. She wore a simple but classy teal colored spaghetti strap summer dress, sandals that wrapped themselves around her calves, and a plain necklace with a small mother of pearl charm that hung from her elegant neck. Her clothes, coupled with her beauty and air of sophistication, gave her the look of a Greek goddess. She held me in that sexy stare of hers 'til I was close enough; then she flashed that smile. Trying to play it cool, I returned her smile with one of my own.

"It is so good to see you," I said, not wanting to sound desperate or tip just how much I missed her.

Having known her for just a little more than a week, I realized that there was so much I didn't know about her, and yet it seemed like I had known her forever.

Madison suggested we take a stroll across town to get away from the old neighborhood for a while.

Lately I had wanted just that, to get away from the place that was not only my home but was partially ingrained in my DNA. There were so many good things about it, yet for every yin there's a yang .

Ignorance, intolerance and small-minded thinking were rampant. Free thinkers and anyone who dared be different were outcasts, so there was a need for a break from the place from time to time.

It was warm and dry with the perfect breeze as we set out on our stroll, a stroll with no particular destination in mind as far as I knew. We walked and talked; she told me about her trip, spending time with her mother; and her love for art. Madison mentioned that her new necklace was a gift from her mother and how she and her mom were both very different but also very alike.

As we walked and talked in the warm summer weather well over an hour, I had not realized how far and to where we had wandered and realized that we had drifted into a corner of town that was once designated as the "adult entertainment" section of the city. It was far removed from its glory days now and was mostly a rundown mishmash of check cashing offices and boarded up storefronts. The burlesque theaters, once so prevalent in the area, were down to just one old fashioned adult cinema and two ratty strip clubs whose neon and chaselight signs were mostly broken or in some cases didn't work at all. The burnt out bulbs and broken letters were symbolic of the busted up block where they resided .

I felt a twinge of fear, knowing the bad reputation of the area, but Madison seemed intrigued by it.

That was a surprise to me, because despite being highly sexual, Madison was a high class, high society person. Yet Madison was not disgusted by the area at all but amused by its unsavory and downright sleazy nature. It was a kind of joke to her: something so bad and tacky that it was good. She was surprised it still existed, a place she had read about, yet had never seen.

For me, it was a place I avoided. The pink glow from the adult cinemas and peepshow lights did their job in casting a spell. That pink red light called to you; attracted you like a bug zapper drew a mosquito. Something magical about that red glowing ambiance made you want to go and engage in some naughty behavior. Thus far, I'd been able to fight off the temptation.

In this end of the city people were regularly robbed, beaten, or worse. So personal safety kept me away, but not wanting anyone from the old neighborhood driving by and seeing me walking out of a peepshow or a triple-x movie theater strengthened my willpower. I feared being recognized almost more than I feared getting stabbed by a pimp or a drug dealer.

Twenty dollar blow jobs were available from streetwalkers who looked like they had bigger dicks than mine hidden somewhere up in their miniskirts. The few who were real women looked like they had seen everything but the wind. There were still a few "book stores," as they were called. The "Freedom Book Shop" had a billboard that boasted "25 cent private peepshow booths" and "the world's best selection of magazines, books, movies, toys, and novelties."

I looked at Madison and said, "I think we should turn around."

"Why?"

"This is a rough area."

"I know. That's why I have waited for a big, strong man to escort me here," she said in a playful tone.

"So is that why we walked this way?"

Madison's devilish smirk said it all. She'd had this all planned.

"Well, I can't go by myself now, can I? You know, all that dirty talk and the porno we watched got me thinking," she said, her hypnotic, sexy eyes locking me into their tractor beam.

"Thinking about what?" I said, scared of the answer.

"In the porno, those women were getting two or even three holes filled at once."

Fear of her next words clutched my heart and lungs. What crazy plan did she have?

"Yeah, and?" I answered perturbed. Now I was convinced that she wanted to hire a male prostitute. I hated the very idea. I felt jealous; freaked out. Dammit, lamenting to myself privately, why did I ask her if she wanted to try a D.P.? It's my fault. I put the wild idea in her head.

There were not many male streetwalkers around this area, unless of course it was one of those tranny hookers, and most of them were gay and had sex primarily with other men. She'll be out of luck... and I won't go along with it, no way, no how! I said to myself.

"I was thinking we could try using some toys."

So relieved was I that I couldn't immediately process the sexy magnitude of what she said. I felt stupid for thinking Madison wanted to hire a prostitute.

"Toys?" I recovered.

"Yes, Lawrence dear, toys." She looked at me as if she were losing a bit of patience.

The idea stirred the butterflies in my stomach, but pleasant surprise and joy as well.

"You were asking how I would feel about double penetration. Well, I want to be double penetrated, just like the lucky women in the porno we watched." Madison's voice took the sexy, flirtatious tone and packaged it with her naughty stare.

"You really want to go in there?" I said, motioning towards the "Freedom Book Shop."

"Yes. Well, not quite. You will go in there and get me what I need." Madison was above this, so her plan, although not well thought out, was for me to do the dirty work for her.

"Me?"

"Yes, you."

"I won't leave you alone here ...not here." I said gesturing with my hands (as we Italians often do) pointing out our surroundings.

She looked around and thought better of standing out by herself; then said, "Well, then I guess we will go in there together."

"Don't you think we should just head back? Maybe stop for a drink?"

"Lawrence, are you being shy again?" Madison said, showing mock annoyance.

"What if someone sees us going in or out."

"Who cares? ...I thought you had grown past this. Let's go shopping." Just like that she snatched up my hand and led me toward the "Freedom Book Shop." Madison had taken me off the spot and made the decision for me. I was okay with it. By taking charge again, she was liberating me from my guilt and inhibitions.

We walked to the entrance holding hands, the red lights from the "Freedom Book Shop" now enveloped us, its alluring magical force seemed to pull us in and catch us up in its debaucherous trap. I'd always had fantasies about coming here; I thought of the treasure trove of porn that lay within. Here was yet another new experience furnished by my new friend and sexual soulmate.

All the turn-on, all the anticipation, mixed with the fear of violence gave the feeling of a roller coaster ride just as it approached the big drop. Not only was I going to finally going to enter a new world of sex and porn, but of toys as well. What wonderful toys lay beyond the smoked glass doors of this carnal Valhalla? An image of of me jabbing a large rubber-studded phallus in a woman's gash sent my nerves scattering around my body. Pleasuring a woman with a vibrator or dildo was something I had been interested in trying. I had not had sex or masturbated in three full days (an eternity for me!) and the entire prospect of current situation was getting me horny. My heart pounded with excitement and tension. My hands were sweating, and squirrels were running around in circles in my stomach.

When we pulled the door open and stepped inside, the cool air conditioning hit us along with the smell of lemon-lime cleaning agent. The "Freedom Book Shop" was surprisingly neatly and modernly appointed and immaculately clean. Most importantly, it was an expansive emporium of perversions, a cornucopia of pleasure and earthly delights.

In the background, we could hear the overlapping sound of multiple people groaning and screaming with pleasure somewhere off in a corner of the store. It was the sound escaping the confines of several peepshow booths. There was an eclectic blend of people milling about the place. The regular trench coat crowd was there lurking around the shelves like sharks on a reef, and a guy with sunglasses and a Panama hat was buying every porno starring someone named "Nikki Sinn." Then there was another couple giggling and snorting at everything. For them, this was clearly something more novelty than erotic. All around us was an ocean of porno films of every imaginable kind, paperback books, magazines, and even inflatable vinyl women.

I wandered to the right side of the store and saw a row of twenty or so booths with separate doors. A man at a small counter top, who couldn't stop staring at Madison, was in charge of the change-making machine. I handed him three singles and he gave us back a dozen quarters.

"Lets check this out," I said to Madison. She was happy with my boldness and loss of inhibitions and was just drinking in the lewdness of the place and loving it. We ignored the sign that said "One Person Per Booth" and went inside.

I closed the door behind us, and a little red light came on overhead, illuminating the booth all red and setting the mood. A board-like bench dropped across the door, both providing a seat and insuring your privacy by barricading you in the booth.

Madison waited patiently as I dropped the coins into the slot. As soon as the money registered the sound and pictures came over the screen. The wrong ones! It was six or seven guys dressed in black spiked leather jerking off on another man wearing a Marlon Brando leather motorcycle hat bedazzled with silver studs. "Ewww! I screeched, as I hit the large button marked "Channel." The image changed to a woman pronging herself with a dildo. We watched for a few seconds, and to my surprise Madison reached forward and changed it, saying, "Okay, this is a little boring, now."

"Sorry."

"Don't be. It was okay at first, but it got old fast."

The channel changed, and we hit pay dirt. A beautiful blonde woman was sucking the dick of a black stud while another black stud fucked her up the ass.

The camera closed in and framed up the contrast of the creamy white skin of the starlet's flawless bottom and the pink circle of her rectal lips against the mahogany color of the beef staff that was fucking it.

"Mmmmmm, this is more like it," Madison hissed with unabashed contentment. We both watched and got very hot pawing and rubbing and fondling each other through our clothes, never taking our eyes off the screen.

After a while, the time ran out on our coins and the screen snapped off. We stood up and opened the door. The little red overhead light turned off . We walked past the man at the change-making machine. He was now deeply engrossed in the newspaper's sports page.

"Okay, let's do some shopping," said Madison.

A wall of rubber dicks, dildos in every color and size filled the wall, floor to ceiling. There were rows and rows of toys and novelties, things I didn't understand and had never seen before. An employee dressed in the store's standard purple-collared shirt uniform was carrying an armful of large black dildos named "The Mule." This "Mule" must have been a popular item, because the guy was restocking an entire shelf of them. The awe that I had was lost on him.

"Well, Lawrence, does anything catch your eye?" asked Madison, wrenching me from my thoughts.

"Yeah... everything," I answered, unable to suppress my smile.

"Another big step for you."

"Yeah... what do you think of this?" I said, as I grabbed "The Mule" off the shelf and held it out for her to see.

"Mmmmmm, looks like a tall order... do you think you can handle it?" said Madison. Her playful teasing skills were top notch.

"I can handle using it on you."

"I bet you could, after I show you how." she beamed, loving her role as my "teacher." "But could you handle me using it on you?" Madison continued to playfully rib me, but also letting me know that there was a hint of truth in her jesting.

"No, I think we can skip that." I said.

"Is that fair, now? You get to use things on me, stick things in my vagina and my ass, but I can't return the favor?" If not for her smile and her poking me in the ribs with her extended finger, I would have taken her completely seriously. Somehow, I could tell that Madison would not have mentioned it had the thought not crossed her mind for real. She took a closer look at The Mule and smiled. "Well, we can keep this one in mind, but I would like to explore my options better," she said with a wave of her hand indicating the wall of dildos.

Madison began to examine them more closely, with the care that a 1950's housewife would inspect produce at the market.

She found another that she liked, pulled it off the shelf and handed it to me to hold while she looked some more. Finally, she settled on The Mule and another one called a "King Cock Double Penetrator," which was basically two rubber phalluses connected at the base and angled for simultaneous vaginal and anal penetration. The way Madison's eyes lit up when she found it was priceless

I looked around and saw that we were getting a few sidelong glances from other customers. Some with curiosity; some with pure envy of Madison's beauty. I was 19 years old, and she was 35. People found it intriguing and sexy, but most just liked Madison's sensual beauty. It turned me on a bit to know that people were seeing me with this beautiful woman who was clearly having a sexual affair with me, the younger man.

An attractive older woman who wore a "Freedom Book Shop" collared shirt with the neck unbuttoned to openly display her alluring cleavage approached us with cautious courtesy. Her large breasts had soft skin that was tan and freckled. She had a sexy biker chick look, and her black hair and dark complexion reminded me of those Mediterranean women I grew up knowing. When she spoke she had a sexy, smoky voice.

"Are we finding everything okay?" said the woman as she offered me a shopping basket. She must have been watching us and had every intention of speaking to us. Why else would she know I needed a basket to hold everything Madison was handing me? Her presence made me uneasy and slightly embarrassed at first, especially the fact that she was a woman about my mother's age, 40, or older.

Then that shameful feeling turned to an erotically pleasing feeling. I wanted this older, sexy woman to know, it was that new, weird thing I had discovered. Trying to understand why I was turned on by the woman interaction with us, it dawned on me it was like including her in our sex, like a strange three- way.

"We're in the market for some fun items. What do you recommend?" asked Madison, as serious as a judge.

"Well, I see you have picked out some really nice dildos; perhaps maybe add something that vibrates like a "Studded Climax Plus?" The woman showed us a pointed vibrator that was a white flesh color and had large studded protrusions all around it. At its base was a two inch curved piece of rubber running parallel to the shaft of the main part of the vibrator. The control on the bottom was a black and red textured dial that turned to control the speed of the vibration. The woman continued, "It's simple and basic, but it's wonderful! It has five speeds that you can control by turning the red knob."

The woman sounded like she was speaking from experience. That in itself was another log on the burning fire in my pants.

"What about this?" Madison asked the woman, referring to the two inch curved rubber piece on the "Studded Climax Plus."

"That's the plus," the woman smiled. "As it vibrates, the plus feature pops back and forth to stimulate your clit."

When she said that I almost busted my zipper.

Madison was sold on it. "It's a top seller, and I can tell you it's just amazing." said the woman.

Checking her out, she was sexy to begin with, but talking about using vibrators made her even hotter.

I saw the name tag on her shirt over her ample tits. Her name was Judy, and I was hoping she would slide out of her tight jeans and give us a demonstration.

And then Madison said to her, "We are both really into anal, what do you have that goes along with that?" It was again tough for me but somehow symbolic of how Madison described the sensation of anal sex, as I relaxed and accepted my private sexual fetishes being exposed to this strange, sexy woman, the more it turned into a pleasurable episode.