Anal Summer Ch. 01

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.)

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My name is Lawrence Giovanni, and this is the story of my youth and sexual awakening. I was nineteen years old and not a virgin by any means, but saying that I had a lot to learn about women and sex would not be an inaccurate statement. With no less than eight sexual conquests under my belt, I felt (wrongly) like I knew it all. Delusions of adulthood mixed with slight boyish naiveté best describe where I was at as a young man, and with a raging lust for women and sex, I set out to fuck the world. I was on the prowl at every opportunity, always chasing, always wanting more.

The impression one might get of me is one of a misogynist who looked at women only as objects of lust. However, to the contrary, I loved and respected women of all shapes and sizes. I loved the way they walk and talk, how their perfumed skin smells, the way they touch up their makeup and tousle their hair, how they can reach into a giant pocketbook and pull out the exact item they want without looking.

I loved them dark, light, white, black, yellow and brown. I loved them tall and thin. I loved them voluptuous and curvy, big or small. I loved their long, slender necks, their delicate hands, their round hips and, yes, of course their breasts - and most of all, their asses.

To say I am and always was an "ass man" would be an understatement. I was fascinated by women's bottoms even before I saw that first porno flick at a friend's house. His older brother had videotapes scattered around everywhere, and I remember having sweaty palms and a pounding heart the first time I watched a tape of people having sex. In the middle of it, the heroine commanded her lover: "Fuck me in the ass." I watched with breathless joy, all the while hoping that my friends would not notice the enormous erection almost bursting through my fly. I was flushed, horny and agitated by the revelation of a sex act that included my favorite female part, and I went home and masturbated at least four times with the images of hot debauchery still fresh in my mind.

That was when my quest to get a girl to let me fuck her drier first began. It was a naughty thought, a taboo act in a forbidden place, and I looked at it as the holy grail of fucking.

Now all I needed was the girl and the balls to ask.

I lost my virginity to a lovely young thing . We had sex a few times, but the closest I got to fulfilling my dream with her was getting to lick her asshole while I was down eating out her snatch. A few sex partners later, I finally got up the nerve to ask the woman I was with at the time and was allowed to lube up and finger her bum ( all the while being nagged by her not to waste too much Vaseline "because I need it to remove my make up"), but when go-to time came she had changed her mind. Similar failures with several girlfriends afterward had me believing that butt banging only happened in porn films and Penthouse Forum stories.

Getting back to my hormone-dripping nineteenth year of life, I was working as an apprentice chef in an Italian restaurant in Little Italy. There was a clear view of the kitchen from the tiny dining area in this ten table sit-down. The chefs prepared the dinners while facing the patrons across a small counter top. You could call it ambiance or charm, or just a lack of a good location; it didn't matter, because we were jamming busy!

Gemma was the name of the woman who owned the establishment, and she was always working the tables, wooing new customers and regulars alike with her warm smile and charming ways to insure they would return.

As I was prepping a stuffed mushroom appetizer and stealing a peek at Gemma's athletic posterior, my eyes were caught by the two women sitting at the table nearest to the kitchen. They were waiting for the mushrooms and for Gemma's obligatory table visit.

That was when I noticed one of the women at their table staring at me.

She was gorgeous , she had a nice, understated beauty to her and a pair of the most sexy eyes I had ever seen, the kind of eyes that would make your cock harden immediately if she stared at you - Sexy smoldering eyes that stared at me as if to say, "I caught you looking at your boss' ass, and you were wondering what it would be like to fuck a superior." Eyes that seemed to know what you looked like naked, and also communicated an awareness of the power they held. She was a presence in the room, with a sophisticated air about her and her smart clothing, no doubt from Neiman Marcus or Saks. I easily identified her as one of the wealthy "new people" who were buying up buildings in the old neighborhood like a drunken sailor buying drinks at a bar.

I caught myself staring back at her and felt that, somehow, something had transpired between the two of us. The spell was broken when the head chef shouted, "Hey, come on with the 'shrooms," and Gemma finally approaching the table where Sexy Eyes sat. It was back to work for me, but as I plated the 'shrooms and pulled the next ticket off the order carousel, I took a sidelong glance at her table. Gemma was hugging Sexy Eyes, and my thoughts were interrupted by a vision of the two of them lapping each others' cunts. This image did nothing to help me lose the erection I didn't realize I had developed during the battle of eye contact with Sexy Eyes.

Flash forward to closing time, and among the stragglers nursing their last sips of Chianti was Sexy Eyes and her girlfriend, who were in conversation with Gemma. Having finished cleaning and shutting down the kitchen, I washed up and headed out towards the dining area and the front door. I was greeted by Gemma, who motioned me to come over to the table. As I approached, she introduced me as the guy who made the "apps."

"Larry, have a seat and meet our new neighbor," Gemma said cheerfully through her sexy smile, and she reached back and pulled a chair right up next to her own and gestured for me to sit down. Once I was seated, Gemma said, "Isn't he so cute? And talented!"

I felt Gemma's hand on my shoulder; just a slight touch but enough to get my nineteen year old blood flowing as she continued talking: "Play your cards right, kid, and you can run this place for me," with her tongue planted firmly in her cheek, adding, "while I sit home and drink more wine!"

I noticed that they were now finishing up the third bottle and feeling no pain. The wine had loosened up Gemma's tongue more than was usual, which was quite a bit on a normal day anyway. Gemma introduced Sexy Eyes' girlfriend first, a hot ticket herself. She also looked like ready cash but piqued my interest because she looked and sounded like Janey Robbins, a porn star who was the object of many a hot jerk-off session for me. Her name was Katie, and she was also getting me hot.

Then Gemma introduced Sexy Eyes: "And this is Madison, my friend and new neighbor." Madison looked at me with those smoldering, piercing eyes and said in a low, breathy voice, "Yes. . . I think we kind of met."

Now I was having all kinds of sick and twisted fantasies involving all three women who were seated at the table. I didn't know how, but I knew I would not let this night pass without getting my dick into one of them, or all of them - who knows?

As the conversation continued, Madison kept up taking long, lustful glances at me. I found myself locked in a war of eye contact once again as I became more and more intoxicated by Madison's hypnotic gaze and the way she parted her mouth slightly and bit her bottom lip whenever I spoke.

Madison had silky brown, shoulder-length hair and would periodically curl the ends of it with her thumb and forefinger. She lifted her wine glass, and the way she held it in her hand and caressed the stem with her long fingers drove me wild. I was so captivated that the rest of the world seemed to fade away as if some cosmic force had slowed everything else to a crawl and turned down the volume.

I was roused to alertness by Gemma's hand pounding on the table to emphasize a point she was making: "Everything I could!" Gemma said, evidently in answer to one of Kate's questions. Alcohol was starting to take the edge from Gemma's charm as she became louder and clumsier. " I stole every secret! Every recipe! Every trick of the trade! I even stole his sous chef, or bus boy, whatever he was, when we were there!" as she now grabbed my shoulders and pulled me closer to indicate she was speaking about me.

I'd been so wrapped up in my little staring match with Madison that I missed the first part of the conversation, but it didn't take me long to catch up. There was only one thing this could be about: The legendary (and now very tired) story of how she worked as the head waitress just a few doors down the street at "The Catch of the Day." The place was an institution in town and was always one of the busiest restaurants in the city. It was run by the worst and most demanding of jerk owners, "Big D" DellaCroce. Gemma got fed up one day and just walked out, leaving behind a position that most up-and-coming chefs in the business would give their eye teeth for. She'd somehow squirreled away enough of her earnings to open her own place, a rival establishment, after learning the ins and outs of the business. It had quickly become one of the hottest eateries in Little Italy.

The truth was, first, we had both worked there and, second, Big D really was a big jerk. On the outside, Big D was a happily married man with four kids who ran the family restaurant that had been handed down generation after generation. On the inside, we who knew him best knew he was a cheap, angry bully who handed out table assignments in return for sexual favors. I'll never forget the time about a year previous I had forgotten my duffel bag in the basement of "Catch of the Day" after work. Luckily, I had a set of keys to the place (I opened for prep work in the mornings), so I unlocked the door and went downstairs to retrieve my bag.

Then I saw them.

They didn't see or hear me, so I was able to avoid embarrassment for everyone by ducking around the corner. I could not believe what I saw and heard, right there where the employee lockers were: Our boss, Big D, with his polyester dress slacks around his ankles and Gemma kneeling in front of him with his massive cock in her mouth.

It was now plain to see why they called him "Big D."

I mean, I knew "D" stood for Dante, but the "big" must have been attributed to his hog. I stood there with the same heart stopping awe I had when I saw that first porno video I told you about. Part of me felt excitement. Part of me felt fear. I was a frozen statue of tension.

Watching Gemma swallow the monstrous cock was a shock in two ways. For one, I never suspected Gemma would blow Big D (she always told me she thought he was gross). For another, I could not believe how she was able to handle such an enormous member with such ease.

The dark coolness of the room seemed to lend itself to such a torrid, scandalous act. The slurping sounds Gemma made as her head bobbed rapaciously spoke directly to my own hardening prick. Her technique was very good in alternating the rhythm up and down the cock shaft. Every now and then she took it out of her mouth and stuck out her tongue and lapped the full length of the underside of his rock-hard tool. Then, once again at the swollen head of the penis she would tease the cock head with the tip of her tongue, only to open her mouth wide and make the giant dick disappear deep down her throat.

I was also getting an involuntary hard-on, and I even considered spanking it to the shocking scene before me but thought better of it.

Big D started to groan before long and commanded, " That's it, bitch, suck my fucking cock!" and now Gemma's head stated to bob more intensely but still in long smooth strokes. Big D reached down and grabbed Gemma's hair. "I love having my dick in your mouth, bitch, now suck me harder," he growled. Then he pulled back on her hair and stated to hump her face with careless force. I heard Gemma almost choking now and could see her legs tense up while she strummed her cunt more rapidly.

I could see the dampness of her twat through the black spandex leggings she wore. She was enjoying this, too. "Slurp, smack, slurp, mmmmmmhmmhhm, mhhmhm,hmmmm," were the sounds that struggled to escape from Gemma's meat-stuffed mouth as sweat beads stated to form around Big D's forehead. I saw his jaw drop open and his eyes squint up. He pulled his rock-hard cock out of Gemma's flushed red face and, using one hand to pull Gemma's head back by her hair, he jerked his dick with the other hand, taking aim at Gemma's face.

The amount of joy juice shooting out of his cock was impressive. It hit Gemma's face with a splashing sound. "D" continued to fire more and more of his hot spew on Gemma's face.

"You like my hot cum, you bitch?" he snarled. "Let me rub it in your fucking face!" he taunted, and he spread it all over using his now half-flaccid cock like it was a paintbrush. Then he pulled up his pants, zipped himself up and walked over to the corner where the linens were kept. He reached into the large, wheeled container, snatched out a dishrag and threw it at Gemma, who was still kneeling. It hit her in the face and fell to the floor.

"Clean yourself up!" Big D hollered. "You ever try and steal from the till again, and it will cost you more than a blow job to keep your position here!" And without another word, he turned around and walked up the stairs and out of the basement.

Gemma just stayed there wiping the cum off her face with the dishrag. I stayed motionless for what felt like an eternity until I saw her rise. I didn't know if she was just slow to get up due to feeling degraded or she was just trying to catch her breath. Eventually, she picked up her bag and put her long, black hair up in a ponytail and exited up the stairs. I was certain neither of them knew I was there, but I was still too petrified to move.

My thoughts were interrupted by a tapping on the front window. My mind snapped back to the present time with the repeated thudding. I was out of my memories and back to the game of chase here in the present. I looked around and saw Madison's cat-like eyes piercing into me.

She asked, "Where were you?" with a smile.

I said," Gemma just got me thinking about when we worked together down the street at 'The Catch of the Day,' and I guess I just drifted, sorry."

"Oh, don't be," she said, and added, "You must be tired."

"Not really, " I said, "I have boundless energy!"

"I bet you do," she retorted and then gave me those eyes again.

Thud thud thud, the window was being tapped. Annoyed by the interruption, I shouted, "We're closed whoever you are," without turning my head to see who it was.

Kate said, "Oh, it must be Roger." She rose from her seat and waved for him to come inside.

In the meantime, Juan, the cleaner, had put up all the chairs except for the ones we were sitting on and had already locked the door. Gemma said, "It's okay, Juan. Let him in." Juan obliged and after momentarily fumbling with the lock, he opened the door for this Roger character. Roger, it seemed, was there to meet Kate and appeared to be happier about it than she was. He looked to be a real dork, anyway.

Gemma, always the hostess, said, "Come, Roger, have a seat," but the chairs were all up on the tables, so she stood up and gave her seat to him and proceeded to sit on my lap. I was a little afraid that in my very (and usual) horny state the feeling of Gemma's firm buttocks on me (and the knowledge of just how well she sucked a dick) would harden my hog and embarrass me in front of everyone, so I gently brushed her off and said, "It's okay. I'll stand." Then I realized I was already at half mast and now everyone at the table only had to look to see it. With a little quick thinking, I pulled my duffel bag around and covered my groin area.

Gemma looked up with a smile and said, " Larry, you're such a gentleman!" Madison also stood and said, "That's it for me. I think I'm going to head home. Gemma, can I borrow your chef here? Perhaps he will continue to be a gentleman and escort me." Between the compliment and the smell of her perfume, I was ready to "escort " her anywhere she wanted to go! She put her arm under mine and said, "Shall we?" and I said, "We shall!"

I was so beside myself with happiness and excitement at the possibility of getting some pussy. I had forgotten the tentative plans I had made with Gemma. In the restaurant business, almost every place closes at the same time, so there's almost nowhere to go. Fortunately, there were some enterprising people who were smart enough to capitalize on this lack of entertainment. The old fashioned speakeasy was alive and well and operating in the old neighborhood. With a small donation to the police department, these "after hours clubs," as they were called, were allowed to operate.

Gemma and I had been regularly going to one of these clubs after closing up the restaurant. Davey's was run by (you guessed it) a halfway connected guy named Davey. He was a handsome pork chop of a man in a silk shirt and gold chains, and he had the hots for Gemma. They had stuff in common; both ran successful businesses, both loved to drink wine, and both hated and scared the shit out of Big D, making Gemma feel safe and kindred to another person that openly hated the most popular guy in the old neighborhood.

On evenings when we were there, I'd enjoy watching Gemma and Davey flirt. It was kind of cute. I used to tease Gemma about Davey and his schoolboy crush on her. Gemma would giggle and mime me the one handed brush-off, as if swatting at some invisible fly.

Madison had now woven her arm around mine, interlocking our elbows. She gently nudged me and said, "Well, let's make our way." I couldn't tell if the look on Gemma's face was one of disappointment or of intoxication. Gemma did seem taken aback by the thought of me leaving with her new friend, to go God-knows-where. Seeming to catch herself, Gemma snapped to alertness and said, "Are you going to go to Davey's later on?" I answered, "Ahh, yeah, maybe ... probably, um, yeah," not knowing how to truly answer the question Gemma had posed to me.

I didn't want to be presumptuous and say "no" for fear that Madison would be turned off by me, assuming I'd be unavailable because I was banging her all night. I also didn't want to disappoint my boss and friend Gemma with a "no," either.

I said, "I'm going to walk Madison home, and I may drop by Davey's later on."

Gemma said, "Well, if you do, I'll see you there." Then, in her boss voice, she blurted out, "And drinks are on you for being late!" With a warm smile, as if to grant me permission, she waved a hand in farewell. Madison and I both waved goodbye and headed for the door.

Once outside, I felt the warm June night on my face. It was a beautiful night, warm but comfy, and the sky was clear and full of stars. Madison still had her arm in mine and made small talk about the neighborhood and me being a "native." As we made our way down toward Market Street I felt better and better about my chances with this sexy woman. Madison seemed out of my league on several levels, making me all the more aroused at the thought that this sexy sophisticated creature wanted me for one thing and one thing only. She wanted to fuck me and use me as a sex toy, and that thought alone was enchanting to a young man. As she held my arm, she said, "You have such nice firm muscles. How many days a week do you go to the gym?" Then she gently bit down on her lower lip and seductively flashed those eyes again. "About four or five times a week," I said, like a man roused from sleep.