Anal Summer Ch. 06

Story Info
A cumming of age anal adventure.
10.2k words
4.75
77.5k
37

Part 6 of the 10 part series

Updated 06/07/2023
Created 10/27/2014
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

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.

*****

Once finished with our early Tuesday morning fuckfest, Madison and I took another shower, this time together. "Come, my dear," she beckoned. "We have to rinse off the milk and honey." Showering with a sex partner was not a first for me, but it was still a novelty, and I couldn't keep from kissing her as the hot water cleansed our bodies while we were locked in a deep embrace.

She gazed at me through the water and the steam. "Do you get it?" she asked. I thought that keeping my mouth shut was the best policy since I really didn't get it. I felt overmatched. "It's seminal fluid," she teased. "You're milk and I'm honey. Milk from your cock and honey from my pussy."

"Mmmm, sweet honey!" I replied, playing it by ear and flying by the seat of my pants as usual. We kissed again, long and deep. Almost everything seemed surreal, dreamlike, watching the suds collect and drip from her pointed aureoles when I soaped up her large, firm breasts. It was strange that I'd already had so many of my sexual fantasies realized with Madison and I'd only met her three and a half days ago. But I felt so close to her in some sort of strange sexual bond, a shared appetite for something between each other that was hard to find. To many, it was one that was frowned upon or considered disgusting or weird, unnatural or taboo. We were kindred in our love of anal sex, something rare for men and more scarce than unicorns when it came to women.

She loved receiving my cock anally just as much as I loved giving it to her there!

Still, I was inwardly intimidated by her; her wealth and her beauty and the fact that I felt (or, deep down, knew) that she flat out didn't need me. I was still afraid to show her just how taken by her I was, for what could I give her beside screaming orgasms? Really, there was nothing outside of my cooking and fucking that made me the least bit valuable to her. I tried to push these thoughts away and be grateful for the fun we'd already shared. I didn't want to scare her away, and I knew what my role probably was: Boy Toy. And expressing any feelings of reservations would end my tenure in that position.

Once all the cracks, crevices, nooks and crooks of our bodies had been washed to our satisfaction, we stepped out to dry off. Madison opened a cabinet door and retrieved a large towel as I stood there. She took it in her two elegant hands, unfolded it, walked to me and dropped to her knees. Softly she sopped up the droplets of water that clung to my skin, starting with my legs. I'll admit that at first I felt insulted that she seemed to think I was incapable of drying myself, but then I realized my youth and lack of confidence were causing me to be stupid. She was just being sweet and caring, worshiping my body and showing affection. Working her way up, she brushed the towel over my groin so as not to arouse me and then continued to pat me dry once past my waistline.

Once we were eye to eye again, we were both in the mood once more, but we had a full day ahead of us. "Wow! You just made me want to fuck you all over again!" I exclaimed, relishing in the open, expressive sex talk.

"Yes, but we can't," she replied wistfully. "But hold off and just think of how much better it'll be later tonight when we get together." The inner jump in my mood was hard to hide: She wanted to hang out with me again, and tonight! Madison smiled knowingly, having seen right through me again, peering into my soul and seeing my naked joy rolling around inside me. "I'll come by the restaurant when you're about to get out. We can go for a nice, romantic stroll down to the harbor walk, see the boats down at the marina; then, through the park, pick up a bottle of wine, rent a movie and relax quietly together."

"Well, as long as you don't make me watch an over-the-top action flick full of violence and explosions," I said through my sarcastic smirk. We both laughed at that and got dressed, kissed our goodbyes and went our separate ways down Market Street.

After hitting the gym and taking yet another shower, I stopped off to pick up two coffees and headed over to The Bistro to discuss business and my new position and schedule with Gemma. Because of Paolo's defection over to Big D at The Catch of The Day, coupled with our growing success and steady upturn in business, we had to hire two more chefs and figure out where I would best be utilized. Gemma greeted me with a wide, chipper grin. She was in a good mood and radiating energy despite being seated in the dining area with various papers and invoices. Paperwork, checks and balances, payment of bills, orders to be placed; this was the end of the business that I liked the least, yet I would inherit a good part of it as the downside of my promotion.

The bright sun through the window of the restaurant encompassed Gemma in golden light. Her hair was done up in a loose bun, and the crisp, white apron tied tightly around her waist adorned her trim, shapely form. She wore no makeup, this early anyway, and looked beautiful in that natural state. Damn you, Madison, I thought to myself. Gemma was my boss and a person I'd worked with until Madison began kidding me to see if an attraction existed. I always knew Gemma was very pretty but was always able to brush those thoughts away. Well, until I secretly witnessed Gemma expertly devouring Big D's cock like a pro. That woke something in me that made me view her in a more sexual way. She wasn't just good old Gemma any more. She was a woman! And, sure, I enjoyed stealing glimpses of her firm ass from time to time, but I tried to confine my view of her as my co-worker, and now, my boss. And now Madison's inquiries had sexualized Gemma to me and had her popping into my head at times when she ought to be the furthest thing on my mind. What idiot would hit on his boss? It would be the end of my tenure as head chef, not because Gemma would fire me but because I would never feel comfortable around her again.

Not to mention that the thought that her rejection of any advances toward her would be scary and intimidating. Well, I was smitten with Madison anyway.

Gemma's blue eyes flew open with exaggerated excitement at the large coffee I brought her. "Thirteen miles this morning," she exclaimed in an over-the-top proclamation about the distance of her morning run as she opened the sipping tab on the plastic lid of the cup.

"Wow, impressive," I retorted.

"Yup! Feeling stronger and going faster every day," she beamed. "Thanks for the coffee," she added and then took a sip.

"Perhaps we should get down to business," I said, wanting to sound focused and ready.

"I have two guys dropping by for interviews in an hour," she said.

"What about Rocco?" I asked.

"I don't have full confidence in him yet, and I think he needs to learn a lot more before he's behind the line."

"Yeah, but he knows the menu. We're going to keep him around, right?"

"Yes. He's just not ready for the line. As far as you are concerned, I need you open-to-close Friday and Saturday--that goes without saying-and then on Sunday, open until the dinner rush is over. You'll have Monday and Tuesday off. Be back on Wednesday early to do the ordering and the prep work, then open 'til the dinner rush ends. The same on Thursday, okay?"

"Sure. Not certain what I'll do with all the extra time off, but I'll take it," I said sarcastically, though with a smile.

Gemma held my hand and looked at me, a wave of seriousness washing over her. "You are a very important part of the equation here, and I don't need another burned out executive chef walking away."

"I would nev..." I began to interject.

"I know," she cut me off. "Still, I want you fresh and rested, plus your new duties require you here in the morning to make up the specials and do the ordering," Gemma added. We continued to talk shop and iron out details. Gemma and I would interview the potential chefs together, however, I would have final say.

Then she asked me about Madison and if I had seen her.

"I barely know the woman," I asserted, not entirely truthfully. "We hung out on Saturday night, as you had put together."

"Yeah, I was nervous and out of line Sunday morning," Gemma confessed. "I wanted to apologize, but we got so busy, and..."

"It's alright, Gemma," I interrupted. "I know you have a business to run, and you don't want the staff complicating things by..."

"...fucking my customers!" she cut in before I could finish my sentence, and her serious face cracked into laughter. I must say I was relieved when I realized she was putting me on but couldn't hold a straight face for long. We both laughed, and it seemed to snap us out of our awkwardness. "I have no right to tell you what to do outside of here," she allowed in what was truly an apologetic admission. Gemma seemed truly sorry and embarrassed. "I just don't want you to get into a rut again," and of course she was referring to the depression I went through when Kerry tore my heart out of my chest.

Gemma had been the one who saw me fall into that hole of despair and sadness. She had been the one who worried when I didn't show up for work at The Catch Of The Day. It was Gemma who called my best buddies Johnny and Tommy and asked them to find me. It was Gemma, with the help of Davey, who found me passed out in a rat hole of a bar on the wrong side of town. Davey and Gemma carried me to her apartment to sleep off the two-day Glenlivet bender I was on. And she did all this while orchestrating her coup d'état at Catch Of The Day. Gemma worried about me and cared for me while concurrently working her master stroke on Big D, leaving him and his restaurant flat and taking trade secrets with her as well as half the staff. Poor Big D! The big jerk never saw it coming, even though he had it coming.

I'd awakened on Gemma's sofa the next day to Davey, Tommy and Johnny. "Where am I?" I asked, not fully awake or fully sober.

"You're at Gemma's place," said Davey. "Look, kid, I know how bad you feel right now, but you gave everybody a scare." Johnny and Tommy didn't speak. They just gave silent, concerned looks. "I understand your heart is broken now, but this is not how you fix it," Davey continued in his most tender tone, lecturing me with caution and compassion. "Fuckin' women, they get us all, but you gotta man up, kid. Having your heart broken, it's a fuckin' badge of honor! You haven't lived until some fuckin' broad breaks your fuckin' heart. Even Frank Sinatra had his heart broken. Ava Gardner drove him fuckin' crazy!. There's no shame in it, but going on a drinking rampage all alone, now that's fuckin' stupid."

"I know," I mumbled. All I could do beside feel stupid was to listen, learn, and appreciate what good friends I had.

Davey's handsome smile crept along his tanned face, and he said, "I smoothed things out with your mama. She knows you're okay, and I told her you were at my place and you'd be home today. But I think there's still a chance she might fuckin' kill ya."

Johnny broke his silence and added, "I'm gonna kill him, too."

Now that the spell was broken, Tommy chimed in: "What did I tell you about those yuppie broads? Find 'em, fuck 'em, forget 'em!" It was then that I realized that these were the type of friends you kept around for life if you were lucky enough, but Gemma had been the catalyst who brought this search party together. So, when she informed me later that day of her plan to leave The Catch Of The Day, I felt indebted to her and had to follow.

So much had happened so fast, and it seemed like such a long time ago. Now I was Gemma's Bistro's

head chef, a title I had coveted for quite a while, at any restaurant. I was staring at Gemma now, trying to figure out what was up with her, because I had the feeling she was holding something back. Why else would she ask me about Madison? And furthermore, where had she, Madison, Kate and the uptight little land baroness gone to on Sunday night? I had flirted with the ideal of asking Madison, but I didn't want to seem possessive or nosy and scare Madison away. "So. Where did you and Madison and her friends go the other night?" I asked, as if I was just making idle conversation. After all, Gemma had inquired about Madison, and that led me to believe something was up between the two of them.

"Davey's," she replied.

"You brought her and her friends to Davey's?" I was perplexed by the notion. Davey's was that illegal, after-hours club, and it was almost sacrilege to take a "new person" there.

"Yup."

"And Davey was okay with that?"

"Yup. I asked him first."

"Uh, well, I guess."

"Don't worry. Davey has it covered," she assured me.

"What do you mean by that?" I wondered out loud

"Nothing. Just don't worry. We all wanted to talk, and now I guess it's time you and I talked about it as well," Gemma said. Here it comes, I thought, here's what Gemma has been holding back. "Madison and that Margot woman have deep ties to the marina and real-estate all through the city. Madison's brother George has pull with the city and state, and Davey has dirt on all of them and would rather make some mutually beneficial deals with them and with us and maybe, just maybe, save some of the old neighborhood in the process." Wow, I thought to myself This is some real heavy stuff.

"I want to know what kind of dirt we're talking here," I heard myself say.

"I'm not sure a hundred percent, but it has to do with zoning and bending the rules, stretching all the way to fraud with Margot and just personal gain as far as your new girlfriend Madison is concerned. She needs a few strings pulled in order to close some real-estate deals and have some construction permits approved. But her brother, George, now, that's another matter entirely. In addition to political favors and deals like Madison's, he has more issues."

"What?"

"Fast women, slow horses, and cocaine." Gemma allowed.

"Yeah, well, I guess that'll do it. How much is he into Davey for?"

"I don't know. Davey is vague when he has to be, and there are probably debts and favors that are owed elsewhere. But Davey would be able to help him, or..." her voice trailed off.

"Or what?"

"Or not. That's how he has George by the balls. Davey doesn't have to do anything about what George is into him for. He just doesn't have to help, similar to how he has the mayor and some of those city councilors, with a careful, gentle grip on their balls. It's more something with the women as well. I guess George likes them young."

That thought was repulsive to me. My face must have expressed my disgust, because Gemma added, "It's not that bad. Twenty-one year-olds impressed with his cash flow, and his wife is a city assessing department manager."

"Let me guess," I summed up, "She doesn't know and is dirty, too, and Davey owns her." Gemma's half smile and silence were enough to confirm that I was correct. I found it funny how openly speaking about certain things was forbidden in the old neighborhood, as if interested parties could hear our conversation.

"So where do we come in?" I asked.

"Well, we have to cater the regatta ball at the marina. In return, Madison is having Ernest Plorde write a favorable review of The Bistro in the paper and talk us up on his weekend TV show." Gemma was grinning like the cat that ate the canary.

"That guy can be brutal. Madison never mentioned."

"I asked her not to as a favor to me."

I was flabbergasted and a bit hurt. How could they both keep this from me? Was I just a tool for both of them? A bargaining chip? A football? I began to protest. "I feel like I was kept in the dark here, and I'm not..."

"Relax!" Gemma interrupted. "This happened organically. I met Madison here on your night off. I saw her another time when I was out running. She was running in the opposite direction. She recognized me and stopped, and we talked. After that, Madison became more of a regular customer, and when you finally met her, none of this was on the table. That was Saturday. Sunday was the night we went to Davey's without you."

"Yeah, and?" I still needed some convincing.

"That's when Madison, Davey, Margot and I all started talking, you see. You and Madison hooked up before."

"What's it going to cost to cater the regatta?"

"All we have to supply is the sweat. The provisions will be paid for by the yacht club, city, state and private sponsors."

That was all very good news. I should have been above the moon, but I couldn't shake the feeling of being deceived and used. A sensible guy would have walked away from Madison, and perhaps even The Bistro. But the fact was, I was hooked on Madison guiding me through the sexual world. I was like a drug addict, and Madison's body was the cocaine. I was powerless to resist my desire to have it.

The Bistro was another addiction. We were the hottest new restaurant in town; I had earned one of the most coveted positions there, and there was no way I was going to go cold turkey from that drug, either. So I put my thoughts and emotions aside and focused on my work.

We had an impressive dinner rush for a Tuesday, but it slowed at about 8:15. Gemma approached a half hour later and told me to take the rest of the night off. I was somewhat shocked. "Larry," she explained, "you are the Executive Chef. Your line cooks can handle the last hour and clean up." She had a point. "You need to be in at 9:00 am to take inventory in the walk-in and do the ordering. And also figure out the specials for Thursday and Friday." Gemma convinced me to trust our line and said I had to think outside of just the kitchen now. I went into the basement to wash up and change, emerging a short time later. I could see through the plate glass window the welcome sight of Madison waiting for me. I looked for Gemma to say goodnight. She was at a table with three men in business suits, sipping wine and putting on the charm with a spade shovel. I recognized one man as the neighborhood city councilman but didn't know the other two. Gemma raised her head and smiled at me, giving a friendly wave of emancipation and returned to schmoozing her audience. I waved back and headed for the door, counting down each second 'til I would be with Madison.

Stepping out of the air conditioning into the warm, muggy June evening paralleled the gears of life, shifting from me being all business on the line to barely being able to contain my excitement at being with Madison, who looked amazing in a sexy, strapless summer dress. She immediately took my offered hand in hers and asked me how my night was going.

"Better now!" I replied with a smile.

We spoke of many things on our romantic stroll, but I lacked the nerve to ask about any of the details and dealings going on with Gemma, Margot, her and George, and Davey. Madison didn't offer, and I pretended not to know. I didn't want to risk spoiling the night. We both enjoyed the salty tang riding on the breeze, informing us that we were approaching the ocean, and therefore, the marina. The boats bobbed rhythmically to the beat of the waves and the tide, and we made a quick stop at a liquor store and then another stop down the street to rent a movie. Back in those days before when the Internet was barely new, people still rented their movies in cassette form at stores devoted expressly to that purpose.

We were looking through the available titles when I noticed a doorway near the back of the store. One look at the beaded curtain told me it could only mean one thing: x-rated films! I casually sauntered over to the back of the store for the purpose of sneaking into the adult section and renting a porno movie to watch with my new fuck-buddy. But what if she were offended? On the other hand, maybe she would love it! And then I was right by the doorway to the forbidden treasure chest of hot sex on film. My pulse was pounding! I looked all around the store to make sure it was empty of anyone I might know. The coast was clear. I looked for Madison, still not sure if I should ask her or surprise here instead, but she was preoccupied reading the synopsis on the back of some movie case in foreign film section.