Anal Summer Ch. 07

Reaching down, I once again used the palm of my hand to grip her buttocks and pry open her crack. Then, by manipulating my saliva and pussy coated finger, I found my target.

By gently rubbing the saliva around the soft, expanding flesh of her butthole. Joanne's lack of a reaction gave me the guts to push further.

Perhaps she was just okay with an outer anal massage and not up for penetration. I decided that, given Joanne viewed giving me oral pleasure as a mutual experience, the worst thing that could happen was that she would ask me to leave her anus out of it and just go back to blowing me.

Pushing my finger tip into Joanne's rectum was pleasantly uneventful. My finger was in her anus, and she went right on sucking me off. She never protested or missed a suck stroke, even with a fingertip in her ass. The new sensation on my finger felt good.. I thought if I paid close attention to the feelings experienced on my finger, I could get a better picture of what anal sex felt like. The smoother, tighter rectal canal felt almost like a pussy but only hotter and tighter. I tried to imagine how that would feel to cock.

My index finger tip was just starting to slip into Joanne's anal pucker. Now in complete awe of her skill as a cock sucker, I marveled that she never stopped blowing me. As my finger penetrated her deeper and deeper, she let out a low moan of pleasant surprise, muffled by my meat in her mouth. She Took a finger in the ass as if it were expected and never took my manhood from her mouth to complain. She just continued to blow me.

After a few seconds, I felt my finger sink deeper as outer the rectal muscles slackened slightly. At that time I didn't know the inner workings of the sphincter yet, so I was working on instinct, feeling that shoving my finger in forcefully might hurt her and end the fun. That instinct served me well as my assumptions were right. Looking back at that now, I guess I was born to make love to female rear ends. Within a minute my index finger was in as far and deep as could be.

Joanne had changed the pace of her oral stroking to super slow motion, coming up to the crown of my penis, then almost off completely, then going downward to take the entire length down her throat all the way , I marveled at how she was not gagging or choking on my hog.

When I slid my middle finger in to the pink fruit that was her steaming sex she began to climax again. Having fingers in her asshole and her pussy at the same time sent her into ecstasy.

Joanne took my cock out of her mouth and kissed it as if to say thank you; then pursed her lips and ran them up the underside of my prick. This sensation was amazing. It's the most sensitive area on a cock, and Joanne knew it. Her soft, wet lips pursed and kissed and glided free. It felt so wonderful, and I didn't want it to end.

A sexy thought crossed my mind: I realized that I was triple penetrating her. That realization made me almost blow my load in her mouth right there. She knew it and again engulfed my entire beef pole down her throat as she sucked hard and fast.

"Do you want to taste my cum?" I barked, half out of courtesy, half out of the horny kinkiness I would exhibit when near climax.

"Mmmm!" was the only sound she made, and it sounded like approval. I was losing my mind and my inhibitions as I got close to coming.

"Oh, yeah, that's it. Suck me, ssssuck my cock!"

"Mmmm!" she vocalized, like a person would if they were told something delicious was being served for dinner.

"You want to taste my cum?"

"Mmmm!"

That wonderful, familiar feeling began to approach, lit on fire by the sensations of being sucked off by a pro while feeling the hot crush of her asshole on my finger. The surge of heart-stopping pleasure ran through my body my, full testicles tightened up and the sensation and my extremities seized. I was coming, and hard. I started pumping my finger in and out of her asshole like a piston while I fired multiple salvos of come rockets into Joanne's willing mouth. She swallowed in time to my pulsations, sucking down every trace of hot juice.

Receiving fellatio from a woman who was good at it was all the difference in the world, and it more than lived up to the hype. She sucked down hard and cleaned the pipe, then licked and sucked off any remaining come from my cock and balls. Joanne sucked 'tll it became too sensitive, and I had to squirm and wiggle my hips to get her to stop. She removed my now laccid penis from her mouth gently and rested her head in my lap. This put blow jobs in a whole new light for me. They are not overrated; they're wonderful, I thought.

After a moment, she raised her head turned to me and said, "You can take your finger out of my ass now, Larry," in a tone that was something less than happy, even a little angry. I was so stimulated and relaxed, I forgot myself and hadn't pulled my finger free from her rectum.

"Are you okay? Are you mad?" Thinking that I hurt or angered her I worriedly asked. I was also worried that even though she never gave me a sign the digital penetration of her anus was over the line,

she would be upset and I would be embarrassed . And to make matters worse, my secret fetish for anal was now known by someone other than me.

" Joanne, what's wrong?"

"What do you mean, what's wrong?

"You just seem angry and detached."

"I'm fine." Her answer was short and curt.

"You don't seem fine. Are you mad that..."

she cut me off: "That you stuck your finger up my ass," her words fast and perturbed.

"Well , um ... err ..yes, are you?"

"I said I was fine."

"Well, you don't sound fine."

"Well, it's all sinking in now."

It was then that I saw tears in Joanne's eyes. "Aww, Joanne, honey, what's wrong? What's sinking in?"

I asked in the most sympathetic voice I could muster.

"I just sucked my best friend's son's cock While his finger was up my ass. In a car. On a deserted street. What kind of desperate slut does that?"

I was dumbstruck. I really didn't know what to do or say.

"I had to leave my home and find another, and my fucking husband left me for the fucking nanny! Any more fucking questions?" She broke down further, not able to hold back the flood of tears she was so desperately fighting. I put my arm around her and tried to comfort her. After a few seconds of crying she lamented. "And now, this!! I'm drowning in sadness and now we can add guilt to the mix."

I began to realize that Joanne was trying to drown her sadness in lust to feel better, and it worked, that is, until the sex was over. I tried to hug her, but she shook off my embrace.

"Then you knew I was weak and venerable, you knew this would happen."

"Look, I thought..."

"You thought you'd get a blow job, and you were right, but then you treat me like some, something, like a whore and shove your finger up my asshole without asking if I was okay with that."

"Joanne, I'm sorry you never seemed to indicate that you..."

"That what I might need a little human contact and not just be used like an object."

"What?"

"I took a risk with you tonight. I risked your mother's friendship, and I needed some tenderness from you, Larry."

"Sorry," I offered I still wasn't sure what I had done.

"But instead of just staying basic and with what I was willing to do you degrade me and treat me like a cheap whore."

"We're only talking about a finger here."

"Yeah, only a finger." she mocked. "You are clearly just obsessed with ass," she yelled in a short accusatory tone.

"What?" I felt faint, embarrassed, ashamed, guilty and in fear that my fetish secret was so obvious.

"You stare at my ass all the time! You stare at everyone's ass, and we have talked about sex many times and I can tell by the things you say and hint at. you point out women and say, 'wow, she's got a terrific ass.' Just tonight when I told you that I had sex with two men at once, your question was 'How did you work that out?' (Joanne said this in a mocking husky male voice)

"You were dying to hear me say that I had one up my ass, weren't you? All that leads me to believe that you are way into ass."

"No I'm not. Don't' get angry, you're overreacting because you're worried about my mother finding out."

"Yeah, that too."

"Look, I'm just as in trouble as you are if she finds out, so your secret's safe with me." We just sat there in silence for a minute of two. Feeling the need to explain myself, I continued: "You had come through your pussy already, and I though that something different might be fun, so I tried playing with your ass."

At this, Joanne exhaled through her nose in a sarcastic snort of disbelief.

"You never stopped me or said anything. You just let it happen, Had you said no I would have stopped,. I thought you were enjoying it."

Joanne's expression softened and she seemed to be okay with my explanation. I continued: "I value you as a person and friend. I would never degrade you." At this, she made eye contact with me as if she was listening and being convinced. "I want to pleasure you and do whatever to make you happy, too. I would eat your pussy or fuck you, you say you didn't like my finger up your ass, well, I would have eaten out your ass if that's what you wanted. That or whatever, because I do care for you, Joanne. You're are not an object to me. You're my friend."

Joanne gave me a long deep kiss. We kissed like lovers, but it still had a hint of weirdness to it. We hugged a long embrace; an embrace of support and understanding.

After a short time of quiet Joanne said, "I'm sorry I overreacted. I was lashing out, and you just happened to be here. I took it out on you, and that was wrong."

"Really, Joanne, its okay."

"I have another confession to make."

"Okay, I'm here for you. We're friends, and you just need to unload and..."

"Shut up, Larry." Joanne cut me off again. "You have to learn when a girl just wants you to listen. I really didn't mind you playing with my asshole . It felt really good, good and dirty. I was aroused by how dirty and slutty I was being. But then after you made me climax the second time, I felt that 'down' feeling you get after you finish, and then I felt guilty and regretted it. You're my friend's son. How terrible is that? And, and, when you're worked up and horny you throw caution to the wind. But after you come and that tension is relieved, you feel silly and stupid or ashamed for being so nasty and dirty. Then I was frustrated and mad at myself and I looked for someone to blame... sorry it was you."

"Well, do you feel better now?"

"Yes. Just embarrassed for my behavior before, during and after."

"Stop feeling bad. Stop beating on yourself. And fuck Ronnie! He's a real jackoff, and he doesn't deserve you anyway."

That last part about her ex husband Ronnie especially made Joanne smile. After that night, we hooked up again when Joanne's girls went to Ronnie's parent's house for the weekend. We got very oral and had lots of sex, but I didn't dare go near her bunghole, because I wanted to dispel her belief that I was anally obsessed. (Even if it was true.) Eventually, Joanne called a halt to our limited stint as fuck buddies for fear of my mother finding out. So I didn't get the chance to fulfill my dream of anal sex with her.

Nevertheless, she would flirt with me, tease me and even get horny and desperate enough to call me when she knew the coast was clear. All of this was the reason for all the awkwardness of my present dilemma. This whole story made my public gym erection that much more difficult to lose right here right now in the present. Joanne-my old fuck buddy who's still my mother's friend- was blatantly looking at my groin area, drawing out my tension and embarrassment.

"Your muscle gets very big, err, umm, muscles have gotten very big, I mean," Joanne said with an exaggerated self-correction and a roll of the eyes. Then she stared at me again with that playful smile.

Now I was convinced she had seen the bulge in my pants and was in full enjoyment of just how much delight she was getting out of it.

I felt like a worm on a hook.

She continued her tedious pause with a smile and facial expression that conveyed a message without a word, as if, by E.S.P., she told me, "Yes, I've had that cock, and I can see that it's hard. I bet you would love to fuck me with it again."

I thought my best play was to just change the subject and ignore the giant, erect elephant in the room.

"Oh, hi, Joanne, You look terrific! How are the kids?" I spat out the words as fast as an AK47 fires bullets, wishing I was somewhere else.

"Why, thank you, Larry. The kids are great, and they're with their dad this week."

I wondered if that was an invitation to go over her place, or if she just enjoyed the flirt-and-tease.

Relishing the thought of giving me back the erection I'd fought so hard to get rid of, and thinking it best to cut this short and get on with my day, I said, "I'd love to talk, but I gotta be at The Bistro soon."

"Yes, your mother told me you are the executive chef there now... congratulations!"

"Thank you, Joanne, I'm really thrilled about it."

"Well, if you ever want to work out that muscle, um, I mean muscles, you know where to find me."

BOING!! My prick popped back to its rigid form. I caught her not-so-subtle remark and the words coupled with the memory of the hot, secret nights in Joanne's bed. My manhood responded without my permission.

Once in a great while, Joanne would call me when that extra glass of wine hit her and she was lonely.

There was times when the planets would align and she would be off work and her kids would be at her ex-husband's for the week. This was rare, but on those occasions I knew she wanted another hot, sweaty romp with me, but she didn't act on it, guilt taking over her lust. She would call me over only to back out and leave me blue-balled.

"Well, Joanne, if I don't shower and head over there, I won't be the executive for very long. It was great to see you."

.

I showered, changed and headed for The Bistro. I was relieved to be off of Joanne's hook.

I arrived to find Gemma at a table with two guys in suits whom I didn't recognize and a third man I knew to be a city councilman, and Margot at her uptight, mousy best. One of the unknowns was barrel chested man of about sixty with thick, white hair, square-framed glasses and a bushy handlebar mustache.

I later learned his name was Hal Maddox. Maddox was a fast talker with a booming voice. He was all business and seemed to command the room, a powerful man in real-estate law and a senior member on the board of the yacht club.

The man next to him was a ferret-faced investment banker named Tim Yardley. Yardley was Maddox's lapdog and bobble-head doll. The city councilman was named Ken Maggio and was from the old neighborhood . He had shady dealings with all these "new people," but he swore they were compromises to keep the old neighborhood alive. I didn't know Ken well at all, but I knew of him. He was a classmate of my uncle's but had no idea who I was, and I was okay with that.

Margot never took her eyes off me and actually emitted a smile of recognition. Gemma greeted me with a smile and introduced me to all as "the star of the show." I met all formally, and we discussed the feasibility of some menu items, along with costs and logistics. Gemma also set up a impromptu tasting for all to attend later on that evening. All of them accepted and were happy that it meant that "Madison could attend."

"Yes, her input is of the utmost importance," piped up the uptight little mouse Margot.

"Agreed," barked Hal Maddox in his stern way, looking and sounding like a walrus that had somehow gotten an Ivy League education.

I fought back an internal wave of anger. Again, I was the last to find out, and all this planning was going on without me. Madison never mentioned it to me, yet this all seemed so prearranged.

I shot a look at Gemma. She returned it with a look that said, "I'm sorry, be patient, I'll explain."

I swallowed back my resentments as Gemma and the board of stuffed shirts agreed to have a sample tasting tonight at 7:30.

Before I knew it, we were in full swing. Diving into my work always made everything feel better.

My mind occupied, I forgot just how mad I was at everyone for keeping me in the dark. Even if it was an oversight, I was still a bit miffed.

By the time Gemma told me to put together the tasting menu I had forgotten every thing and concentrated on wowing the clients with my chef skills. The hours flew by, the way they always seem to do in our business, and before you knew it, it was almost 7:00 p.m. I saw Madison walk in and look directly at me. I hid behind my work because I was still too angry with the secretiveness. I was too busy behind the line to see everyone sit down, but Gemma wanted me to leave the kitchen and serve the tasting samples personally and field whatever questions the clients might have. Madison, for her part, was warm and friendly but stopped just short of tipping off our relationship, or whatever it was, to the others.

I had done a good job, and we closed a deal between The Bistro and yacht club. I guess we owed it to Madison for making the connection, but my cooking and Gemma's charm ultimately won us the job.

We were going to be granted access to the yacht club's kitchen, and they would buy all provisions. We would beat any price offered by anyone else provided that The Bistro got plenty of free advertising and would be listed as one of the event's sponsors.

The men left, leaving behind Madison and Margot, who were now in to their second bottle of wine.

Gemma was also sitting with them, laughing and throwing back wine like a sailor. I went back to the kitchen. Two of the new chefs, Bobby and Alfie, were there and were doing a fine job. As I checked the clock, it was already 10:00, and we were shutting down dinner service. I gave Bobby and Alfie final instructions about closing down and clean up and then retreated to the basement to shower.

When I arrived back upstairs Madison and Margot were the only non staff there. With Gemma, of course, leading the band and pouring the wine, laughing and giggling like school girls as I approached the table. They sensed that I was there and fell silent. Then Gemma broke the ice with, "Well, here he is!!" Gemma smiled at me with genuine appreciation. She was a little buzzed but also overjoyed that we had landed the catering job. She stood up, motioned me closer, and surprised me with a hug. So surprised was I that I never got my arms up to hug her back.

The hug was rough and tight. I felt Gemma's ample tits squash up against my chest, my unsuspecting hand brushing her firm, athletic hip. She was so close I could smell the wine on her breath. Gemma released me and gave me another long look. "You did it, kid!" she announced not just to me, but to Madison and Margot as well. The two women just looked on. Margot had a smile of inebriation while Madison gave me the sexy stare. I could tell that this success made Madison a little more attracted to me. I was pleased with the happy mood everyone seemed to be in, almost forgetting how mad I was.

"Bravo, Bravo!" said Margot. I realized this was the first time I had heard a word from the uptight, mousy, mystery woman.

"You have impressed me. That Hal Maddox can be such a hard man to please," Madison said.

"And to think I did it on such short notice," I said, my motives apparent to all, or so I thought.

"Well, sit and let's have a toast to you, our man of the hour!" Margot announced and motioned for me to sit. This was more warmth than I had ever expected to come from this mousy prude of a woman.

"Of course! How could I not have thought of that?" Gemma apologized, popping up to fetch me a wine glass from the rack that hung above the wait station a few tables away.