Anal Summer Ch. 04

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After pulling up my pants, I took a spot on the loveseat in Madison’s living room. Madison was still strutting around naked except for her thigh-high stiletto boots and shiny black latex elbow gloves. The click-clack that the stilettos’ heels made when she walked was like an instigating hand rapping on the door of my libido. The boots and gloves themselves were a shiny black, and now Madison’s skin also had a hot buttered look, glossy and glazed. Her large breasts, shoulders, neck and perfect, plump ass all glowed with sex, the beautiful contours of her figure all shining, enhancing the sexy beauty of her form, her lovely face flush with her natural color.

Wordlessly, I stared at her, in awe of her. Waiting for some alarm clock to ring and rouse me from this dream that was too good to be true. She seemed to be looking for something, and I was not sure what, but I was enjoying watching her walk around so much I didn’t want to interrupt.

She’d asked me to come into the living room and have a seat. I didn’t know what her plans were for us but I didn’t care. Madison was full of surprises, and I had already learned to sit back and let her take the lead. Anticipating what she would do next had me in a state of constant excitement. I had pulled on my walking trunks but remained shirtless.

“I can’t seem to find that little book they leave behind everyone’s doors,” Madison said.

“What book?”

“It’s a new service. They give out a booklet, like a catalog, and it has several local restaurants’ full menus, and they will pick up and deliver for you.”

“Like a service? Independent of the restaurants themselves?”

“Yes, dear. Exactly.”

“Well, did you want to go out and have dinner? I mean real dinner… with food.” I grinned, our recent sex fiesta still on my mind.

“I’d rather order in,” she replied flatly.

“Really? It’s so nice out.”

“I’d rather stay in and fuck more,” she said, looking directly at me with those gorgeous, seductive eyes. She spoke short and to the point in such a straightforward, emotionless way that made it incredibly sexy.

This open, free sex talk was new to me, and I loved it. I was as sex-crazed as any other man my age but inhibited as well. I loved pornographic movies but had only seen about four or five spread out over the years because I was ashamed to rent them. I feared someone from our small neighborhood would see me and everyone would know.

Hell, I was too shy to buy magazines with centerfolds in them! So I masturbated to the memories of the sexual encounters I’d had or to the faded images of those few, wonderful porno movies I had seen. But just the other night, I found out you didn’t need to be married or date a girl forever to get a blow job.

Meanwhile, Madison had found her “Restaurants to You” book and reentered the living area.

She walked past me to an end table that held a fancy looking telephone, her pulchritudinous back displayed as she looked through the book without even consulting me.

After flipping through several pages she stopped, without turning to look at me, and asked, “Do you feel like a steak?”

“Sure! I love steak!”

“Rare, I’ll bet.”

“Yep! Same as I like your pussy.”

The book was open to the restaurant menu she’d decided upon, and she placed it on the end table. When Madison picked up the phone to place the call, she bent at the waist to get a better view of the menu. Her flawless round ass, slick and gleaming, framed the pink lips of her pussy which was peeking through the top of her thighs above her glossy, black boots. She dialed the number as, unknown to her, I crawled across the floor to her. I was drawn to her ass like a moth to a flame. I had already eaten my fill of her asshole and honey pot just thirty minutes or so before, but seeing her in this pose had me hungry for more already.

I heard her say, “Yes, hello. Restaurants to you? Yes, I’d like to place an order.” A small pause, and then she continued, “Yes, to Grill 53.”

By then I was upon her, so close I could smell the wonderful aroma of her sex. Without warning, I buried my face in her ass, sniffing and tonguing her in a savage sneak attack! The sudden quiver in Madison’s voice revealed her shock and ecstasy, but she quickly regained her composure and continued to order our dinner while I ravaged her anus and cunt with my mouth.

And amazingly, continued to have a conversation, almost as normal, with the person on the other end of the line Every now and then while she talked her voice would give some small sign that someone was going down on her.

Strange things were happening in my sex-engulfed mind! I didn’t know quite what they were, but engaging in a torrid oral sex act while an unsuspecting person was on the phone was intriguing. That edgy risk where that same unsuspecting person might figure it out. Maybe I secretly wanted him or her to know! A connection with a third person during sex had me running down every sexual corridor in my mind. That wonderful almanbahis feeling of shame once again! Much later, I would find it was voyeurism’s tricky friend, exhibitionism. I would love to fuck her or eat her out while she was on the phone with somebody like Cate. “Shame, I love you!” I thought to myself.

What if Cate accidentally walked in one night while I was sliding my cock in and out of Madison’s delectable rectum? The way I loved to watch people having sex made me also want to be watched or eavesdropped upon. Amazing how I was getting off at the thought of some third person’s involvement, even if only over the phone.

“Yes, I’ll take the baked haddock,” Madison was ordering while I continued to take long, lapping licks of her cunt. “Yes, and the New York sirloin. Yes, rare.” On that note, I jammed my tongue full up into her bunghole, causing her to flutter and trip on a few words. But somehow, she managed to finish placing the order. She hung up the phone and without missing a beat, she chided me. “Oh, you naughty boy! You just can’t keep your mouth off of my fun holes!” I was eating her out from behind for a while longer when she confessed that she wanted my cock and stepped forward, away from my pleasuring mouth.

I arose and followed her as she stepped seductively to the center of the room, waving her beautiful bottom, her stiletto heels clicking and clacking as she walked. She lifted one leg and rested her booted foot on the coffee table, her other leg standing ramrod straight, then she placed one of her gloved hands on her knee, the other hand beckoning me to her.

I unbuckled my pants while I approached her slowly. When I was within arm’s length of her, she put her arm around my waist and drew me close. Her other hand went down from her knee to her twat. I watched as Madison used her fingers to spread open her cunt lips and display her clit to me.

“I want you to fuck me like this, standing, and I want you to fuck me nice and slow, in my pussy.” By now, Madison knew well her role as a sexual muse and teacher. With slow, serpentine movements, her hand snaked its way to my hard prick from where it had been strumming her clitoris.

Madison took a firm grip on my manhood, and her feminine hand, adorned in shiny black latex, encircling my swollen cock looked almost artful in an erotic sort of way. The colors and shapes both rounded and angular made me think it would make a wonderful photographic print in some gallery somewhere. The skin tones and pinks and purples, the fleshy, bulbous cock in stark contrast against the sleek lines of her long, yet dainty, hand, and those elegant fingers all wrapped up in the darkest black you could ever imagine! I loved how big my cock looked in her hand.

With just a little effort, Madison aimed my dick toward her inviting pussy. I peered down and saw her pink lips stretch over the swollen purple knob of my tool.

“Now you will fuck me slow,” she ordered, “and you don’t get to come. When the delivery man gets here, you will stop fucking me and get dressed.” I eased my hog up into her in slow motion,inch by rock-hard inch. “You will open the door. I will robe up and pay him. We will sit down, have dinner, and then after that, you can come any way you want.”

“And what if I come before?” I asked, half teasingly and half pleadingly.

“Then you dress, you pay for dinner, we have dinner, and you lose your chance of fucking my ass,” Madison announced, and then encouraged, “Just relax. Feel the warmth of our bodies intertwined, my pussy impaled on your cock. Be one with your senses. Feel my hand stroking your lower back and your buttocks.”

“Stop!” I blurted, adding, “You’re going to make me come just talking that way!”

“No!” she answered. “You won’t come until I say you can. You’re going to hold it back, almost like holding back having to pee.”

“Really? That works?”

“Yes,” she assured me. “Now, I want you to imagine that you have a stick of chalk in your anus, and I want you to squeeze your rectum and buttocks as if you were holding on to it.”

“Ummm, okay,” I volunteered, as puzzled as the day was long.

Madison continued: “Now, slowly, I want you to move your ass and pretend to write our names in cursive with that imaginary stick of chalk.” I did as she said, and it seemed to be working. My compulsion to orgasm was receding. “Now, every time you feel like coming, breathe deeply and stop squeezing that chalk. Later on, when you do finally come, you will come even harder than before because of this practice,” she told me. “Remember, Lawrence, it’s a process, and it’s a process of pleasure.”

This slow motion humping felt awesome! Her fleshy, pink vaginal lips surrendered to my hard, tube steak, stretching her. To this day, I still marvel at the tightness of her twat and how it would open to accommodate my length and width. It felt like hot, wet velvet inside her. Slowly, I inched deeper and deeper until I was as far in as humanly possible. I gave her a long, slow almanbahis yeni giriş series of humps in an upward motion to facilitate the standing sex position Madison had chosen to teach me.

“Mmmm, that’s it! Nice and slow. Just enjoy what my pussy feels like,” she whispered.

“It’s the second best feeling ever,” I admitted. “Almost as good as your asshole.”

I was able to slowly get used to the strange position we were in and gain enough balance to remove my hand from her waist and caress it down to her derriere. Then I worked my way to her crack and under, reaching all the way to her dripping honey pot that was occupied by my cock. I gathered some of her natural vaginal wetness on my fingers, her sweet honey flowing, making it easy to moisten my probing digits. With this warm, slippery cunt juice, I lubed her anal wrinkle in a soft massage, the promise of penetration in its spirit. With every tediously slow pelvic thrust and every circular sphincter caress, I applied increasing pressure. Not sure whether or not what I was doing would be successful, I would work my fingers into her pleasure ring unless she told me otherwise.

Madison never stopped me or questioned the intent of my ass play, so I continued. I could feel her sweet honey, now flowing; now running down her thigh.

I finally worked my finger into her brown eye and was presently surprised how much pleasure it gave me. My cock was still very deep in her vagina, and I could feel the finger in her ass tickling my cock through her fascia. Not only was the added stimulation good, it also added tightness to her pussy.

“Does this feel good?” I questioned.

“Mmmmm, ye-ye-es!” she struggled to speak over her ecstasy.

“I bet you’d like two cocks at once, wouldn’t you? One for your pussy and one for your ass!” I inquired, reveling in my dirty talk and turned on by the mental images the thought carried with it.

“Ohhhhh, yessss, t-two ccc-ocks, mmmmmmmm!” she managed.

“Two BIG, FAT cocks STUFFED in your FUCK holes!” I sneered, feeling momentarily dominant.

“I want t-two ff-ingers in my ass nn-ow,” she stuttered out in her almost catatonic state.

“Say ‘please,’ Madison!” I demanded.

“Oh hhhh, pp-lease!”

“‘Please’ what?!” I liked the control, turning the tables from earlier when my cock was in her hand and her tongue was lapping at my anus and I was under her power.

“Ppp-lease put two fingers up my ass!” she said, fast in one breathy utterance, as though she were only able to speak between gasps.

Madison’s cunt and ass were so dripping wet that my middle finger was already drenched by her juices and easily slid into her willing rectum next to its hand mate index finger. This only heightened the copulation for both of us, and it seemed certain we would both come within the next few sex-soaked seconds.

Then the door annunciator buzzed. Its annoying, interrupting sound reverberated through the condo.

“Well, I guess dinner is on me,” Madison sighed, willing herself back down into a state of serenity and teasing me with a coy smile. She slid me out of her passion pit, turned on her heels and walked toward her bedroom to dress. “Pull up your trousers and buzz them in, please,” she asked as she click-clacked down the hall. I got my pants back on, struggling to stuff my still-erect penis into them, pulled my shirt over my head and buzzed in the delivery man. I waited by the door for the delivery man to climb the two flights of stairs to the condo. Finally there was a tap, and I shouted the obligatory “Just a second.”

When I opened the door, I was surprised to see a delivery woman instead of a pimply-faced, teenaged boy in a ball cap. Not only was she an attractive redhead, but she was dressed in black leggings and a white tuxedo shirt with a black bowtie. The look was overall a good one, and it was apparent that “Restaurants to You” was trying to be more a professional and distinguished service than the ordinary pizza or Chinese food delivery.

She was pale and pretty with big, green eyes and wild, curly hair, and she was looking at my erection bulging in my pants.

“Here you go,” said Madison’s voice from behind me, stirring us from our wordless awkwardness. She had donned a full-length black silk robe, still in her stilettos and gloves, as she counted out the cash and tip for our dinner. The delivery lady’s eyes darted back and forth between Madison and me, and her pretty face had a look that said, “Ah, you two have been fucking!” She smiled at us knowingly, said her thanks and was gone.

The wonderful aroma of grilled steak reminded me how famished I was. “Dear, why don’t you go wash up, and I’ll set this on the dinner table,” Madison requested more than suggested. I went to the bathroom and washed my pussy-soaked hands and realized that I could still smell her cunt and ass. Then I remembered that her juices were all over my face, so I washed that, too, dried off and returned to the dining room.

Madison had almanbahis giriş transferred our dinners to plates and the fresh, hot dinner rolls to a small basket.

So, the table HAD been set for a reason!

She uncorked the bottle of wine I brought and poured our glasses full. There was a short, uncomfortable silence, and Madison used her beautiful eyes to stare a smile out of me. Once we had a few bites of our entrees, we started to chat more easily. We didn’t realize ’til then how hungry we were. After a few sips of the wine, our conversation kicked into gear.

“If I may be so bold as to ask, who was the other woman you had dinner with last night?” I inquired, realizing that Madison and I had barely spoken about last night. We just saw each other, and then started to suck one another off!

“Cate? You met Cate.”

“No, the other one. The one who looked like a museum curator.”

“Oh, yes, how could I forget? Margot. Margot is her name. She’s a doll, and she runs the marina in addition to being a fine real estate baroness, ha ha,” giggled Madison at her own joke.

“So, do you work together, or are you just friends?”

“We’re friends, but sometimes our jobs cross,” she answered and then took another sip of her wine.

“And what exactly is it that you do?”

“I run my brother George’s company.”

“Which is?”

“Foss, Incorporated.”

“I’ve seen that name around town,” I offered, still clueless.

“Real estate, dear. We develop areas, build condos and shops, sell office space and even handle all the legal matters.”

“Like a brokerage, then.”

“Sometimes we’re the middle man in sales like your average realty office, but we own most of the properties we sell.”

“And I thought it was all those damned yuppies driving up rents!”

“Yes, the yuppies drew my attention to the area, and George was tickled when I introduced him to it. He told me I’d found him a gold mine.”

“Yes, you did, and at the expense of the natives,” I said with a slight anger growing in my belly. I hewed off a healthy slice of sirloin, lifted the fork to my mouth and used the chewing to slow and change the conversation.

“Poor Margot’s husband died four years ago. He was a lot older than her. Spoiled her rotten, and now that he’s gone, poor Margot doesn’t know what to do with herself.” Madison was happy to do the talking while I hid behind my sirloin and listened. She continued to say that she was working on Margot to get her brother George a slip for his yacht. She explained that, of course, he already had one, but there was another that he particularly coveted. The problem was, Thomas Thorn’s yacht was already there.

I finished my steak. Madison was not far behind me finishing up her entrée. “George and Thomas have a good, friendly little competitive rivalry,” she elaborated. “They’re about to race yachts this week. I’m trying to talk those two fools out of it. First, I’m going to tell Thomas to stop it.”

“Really? When?”

“When he takes me out to dinner tomorrow.”

“Oh,” I said, trying not to sound as crushed as I was. “So, you’re going out on a date with him.”

“Well, sort of. It isn’t going anywhere, and I’ll meet you when you get out of work.” She looked at me to regard where I might be in my mind about this. “You must know I see men all the time. To keep up impressions. It’s mostly for work and keeping in the public eye.”

“I’m only seeing one woman right now. And that’s you,” I retorted. I was a little hurt, and it showed.

“Oh, my dear,” she reassured, “You’re the only person I’m fucking, and I plan to keep it that way.”

“I’m not telling you what to do by any means,” I offered. Internally, however, I guess I had the beginnings of feelings for her but didn’t want to let them show. I thought that if I started to fall too quickly for her that I would scare her and her sumptuous ass and pussy away, so I tried to act as if I didn’t care.

“You’ll see,” she said cheerfully. “He gets to buy me dinner. But you get to fuck me!”

“Sounds good to me,” I replied and then explained, “I just want to fuck you and nobody else, and I don’t want you fucking everyone, either. But I don’t own you. Go out on your dates and let’s play it slow and have some good, hot sex sessions, and we can see where it leads goes from there.

This made Madison smile. She got to her feet and came over and kissed me. “You’re so sweet!” she said.

“You’re so sexy, and what did you tell Cate and Margot last night that was so funny?” I demanded, raising an eyebrow in mock scrutiny.

“I told them you were a terrific chef but a much better fuck,” she answered without hesitation, and I was so young and inexperienced that I wasn’t sure if what Madison was saying was true or not. “I told Cate your cock was about this long,” she continued, gesturing with her hands, palms flat and facing upward with a space between them signifying my approximate size. “And that you have a sense of adventure and weren’t afraid to fill all of my holes, yes, even my rectum.”

“Well, if that’s true, I’m both embarrassed and turned on by it.”

There was a slight pause in the conversation. Then Madison ventured, “You want to fuck my friends, too. Don’t you?”

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