Anal Summer Ch. 08

I used the bathroom to change into shorts. I wanted to kiss her goodbye but didn't think I should, so I just said goodbye and thanked her as she headed down the stairs while I went up to the roof.

As I reached the top of the top flight of stairs, I could feel the heat of the summer cooking the roof stair housing. I pushed the door open to find that I was not alone. The sight that awaited me was that of Kate on a lounge chair. She was on her knees bending over, her beautiful ass facing me as if ready to be fucked from behind by some invisible cock . She wore a tiny red thong bikini. The thong string was not wide enough to cover the circumference of her sphincter, its perfect roundness overlapping on both sides of the thong. Straight wrinkle lines like a star emanating from the center of her butt hole were clearly visible as her butt cheeks yawned open because of her body position. The magic triangle of red bathing suit material covered her womanhood but revealed her loose pleasure trench, as her camel toe was apparent. Kate was reaching for her radio and using the tuning knob to fine tune a station she was listening to, completely unaware of my presence. I was enjoying the view to say the least but I didn't want to startle her. After a bit, I finally said, "Good morning, Kate."

Kate looked over her shoulder at me with an open-mouthed expression of unexpectedness.

"Oh, hi," she stammered as she realized the show she was giving me. I loved having her at the disadvantage. After her teasing me in the hall and her overall intimidating beauty and persona, it was nice to catch her like this with her nether region gaping at me. I also held a revenge card, as she knew that I must have heard Roger's embarrassing performance, or lack thereof.

Kate's posterior was not the only breathtaking scenery. The view of the old neighborhood on one side and the harbor and open ocean beyond it was another. The deck was large and covered most of the roof. It was well maintained and would be an awesome locale for a party. The sun shined down on the beautiful cloudless June morning.

Kate quickly turned around and into a less compromising position. "Uh, good morning. You surprised me there."

"Sorry." I walked over and then sat down on the lounge chair next to Kate's. She was clearly embarrassed not only by the view that she gave me but of her behavior and shortsightedness in taunting me yesterday. "Please accept my apologies and please, please, please don't gloat, though you have every right to. I'm sorry that I ribbed you yesterday. I was just trying to have some fun in a flirty kind of way and thought you would find it funny. I never wanted to make you feel embarrassed."

"Kate, it's okay...I'm a guy, and we don't mind teasing about our sexual activities. It was kind of fun...so don't feel bad, its nothing." She looked a tiny bit relieved but I could tell she was still squirming about what she knew I had heard. "As far as gloating is concerned, I don't have anything to gloat about."

"I appreciate your answers, and I can tell you are being the bigger person than I was just yesterday."

"Its nothing. Hey, this is one hell of a view up here," I said, trying now to move past the subject.

"Thank you for being nice."

"Kate, really, it not necessary. Chances are we will hear each other again, and we are in the same situation so there is no shame... in a weird way how there's no shame between sex partners . it's like we are all one big group of shameless sex partners. I said in an attempt to smooth things over and deal with the situation while making Kate feel better. She was on the hook long enough, and I don't like being there myself, so I was taking pity on her. But I wasn't realizing how creepy I must have sounded.

I spread out my towel on the lounge chair next to Kate's and removed my shirt. I thought Kate had said her piece and was content when to my surprise she continued: "You know, I wish it were that way."

I looked over at Kate and said, "Like what?" not understanding her meaning.

"Us all as a group of sex partners."

Not knowing how to respond to that, I just smiled and nodded my head.

It only took about a minute for her to say, "Would you mind?" I turned to see Kate in her thong bikini holding out a bottle of oil. I was bothered by this, as she was Madison's friend and neighbor, and now she wanted me to rub oil on her almost naked body after telling me that she wished we were all a group of sex partners. I knew where this could lead and was not at all comfortable with it.

"Oh, come on, Lawrence... it's no big deal. Just on my back."

"Well... okay."

Kate flipped onto her belly and was lying face down. Her body was as pretty and sexy as her face: a complete smoke show. All of her was right there; wonderful long legs, her neck, back and waist were so tempting; and my favorite part, her gorgeous ass, was worthy of an award. Looking at all of this I wondered to myself how in the world was it possible that Roger couldn't keep it up for this amazing, sexual creature. Still, I was annoyed by the prospect of rubbing oil on her. This could go so wrong. I cautiously put some oil in my hand and rubbed the middle of her back, being careful not to go too low. Kate began to moan and coo like someone was eating out her pussy. This made me uneasy and once again I found my affections and loyalties for Madison looming large. Then I quickly applied more oil to her lower leg and calf area. I rubbed quickly and spread the oil up to the back of the mid thigh. Then I stopped. Her beautiful bottom was right there, and I was certain she wanted me to rub both of her golden globes and her crack in hopes of seducing me. It was a test of my willpower. Normally I would have given anything to touch a woman like this. After all, this was at the time (and sometimes still) what I lived for, a beautiful ass. It took everything in me to keep from burying my face between her amazing cheeks, but I was sure I didn't want to risk it, so I stopped. Kate seemed disappointed, but I was inwardly proud of my own willpower. I went back to my lounge chair and lay back, half wanting to just get up and leave. Kate would not give up, and after about three minutes she said, "Okay, you turn."

"No, really, Kate, it's okay. You don't have to." But as I said it a handful of oil splashed onto my chest. Kate began to spread and massage the oil over my chest, then to my shoulder and down my arm. Her hands were talented and the oil had been warmed up by the sun. It felt great, and I thought that she couldn't overpower me and I could stop her if I felt uncomfortable at any time. So I let her continue. It turned out to be more of a massage than a simple application of suntan oil. Between being warmed by the sun and soothed by Kate's massaging hands, I was deeply relaxed by this experience.

I began to drift and doze off, somewhere treading the line between sleep and consciousness, and slowly teetering towards the latter. A split second before my doze graduated to a snooze. I was jolted upright and to a fully awake state to find my shorts pulled down and my cock exposed to the world! During my little nap, Kate had continued her massage all the way down into my shorts. My cock was as hard as a diamond. It was coated with a liberal amount of suntan oil, the sunshine on my oiled member created an almost blinding glare. Kate had one hand wrapped around the base of my tool, and her other hand cupped my scrotum. She stared at my hard-on in awe of its shining, erect glory.

"It's true... It is beautiful! And I can't believe she really fits this entire thing up her ass," said Kate, both truthfully and shamelessly, making blunt and open dirty talk, stating the obvious as crudely as she could. I knew what she was probably getting her jollies doing so.

What was it about these women? Was I a toy to them, a fuck machine devoid of choice and feelings? These women would touch me and fondle me and just assume that a man wouldn't care and wouldn't rebuke their selfish advances. They must have felt their friendship to Madison superficial and inconsequential to risk losing it. The anger began to rise in me. Last night it was Margot; this morning, Kate. Who were these fucked-up people, and did they know something I didn't? I was sure that Madison was just fucking me 'til something better came along, but I had developed feelings for her. I had held out hope that there was a chance, however slim, that this world-class woman would fall for a muscle head chef from the old neighborhood, with a high school diploma and a degree from the university of hard knocks. Was I nothing? Just a possession; an object that could be borrowed? Did Madison tell them it was okay? All of this had my blood boiling with a vexed fervor I hadn't felt in a long, long while.

"WHAT THE FUCK ARE YOU DOING?" I exploded. The look of surprise and fear washed over Kate's face as she cowered in a ball on the deck, jumping up out of my lounge chair red faced with eyes bulging.

"I'm sorry! I'm sorry! Please don't hurt me," Kate begged through a mask of tears and fear.

This angered me even more: "Please don't hurt me!" What the fuck did she think I was, some kind of wimpy loser who abuses women? Is this how these new people viewed us? I thought to myself.

"Please don't hurt me," I mocked back at her. "Don't flatter yourself." I continued.

"I'm sorry! I have just been so horny and Roger can't keep it up..." she said between sniffles.

"So you just violate the next guy nearest you without permission?" I barked back.

"...then I heard how good you fucked and how big and beautiful your penis was ... and I... and I..."

"...thought you would try me out, like borrowing a cup of sugar from your neighbor!" I said, growing angrier."

"Why are you so mad?" she fought to say through sniffles.

God, this entitled bitch was a clueless, heartless yuppie scumbag, I thought disgustedly. My involuntary erection was making a large tent in my shorts, and I thought of whipping it out and jamming it in her mouth and fucking her throat to punish her for her transgressions. Thinking better of it I dismissed the idea and instead took a deep breath.

"I'm sorry. I just feel so unattractive, and you looked so good... I just ...I just..." she whined.

"You just what? Thought you would have me without asking first?" I said, still yelling but calming down a tad.

"I just wanted to see if I could still make a young man hard..." sniffle "I haven't been able to make Roger hard for so long, and I feel so ugly and unattractive." she said breaking down into a full-on crying fit.

I have never been able to withstand a woman crying, so I softened immediately.

"Look, look, Kate, I'm sorry I lost my temper, but you shouldn't have done that."

"I know... I know."

"Do you value your neighbor and friend?"

"Yes"

My imagination started to get the better of me. Did Madison arrange this? I wondered. She was already working with Gemma behind my back...well sort of.

"Did Madison say this was okay?" I barked forgetting to be nice.

"Oh, goodness no! Please don't tell her!" Kate begged.

Thinking that authentic, I dismissed the idea.

"Look, Kate, you are a beautiful woman. I find you very attractive and sexy. If Roger can't get it up for you that is his shortcoming, not yours."

"Really?"

"Yes Kate, really, and I won't tell Madison if you don't... okay?"

"Okay."

"If things were different and I met you first, I would be all over you. It's not anything you are doing, it's just bad luck...I'm sorry. ... but this is too fucked up for me to stay here now. I gotta go." I packed up and left Kate, her red thong bikini and her "blue bean" to themselves.

When I arrived at The Bistro and saw Gemma, it was weird for me. I'd had that dream that seemed so real, and it would be a while before I could work past it.

As usual, we were busy and the night flew by. Pangs of jealousy would hit me every thirty minutes or so; thinking of Madison out on her date with some rich high society jack-off was a stone in my shoe. I was in a bit of trouble I thought; my heart will be broken soon; I shouldn't have gotten close; I am a boy toy and that is all; I should just enjoy the ride to nowhere. I tried to stay as busy as possible. I couldn't and didn't want to have too much conversation with Gemma.

The entire situation and last night's dream were all too strange for me.

Gemma even noticed. She made a few attempts but sort of backed off, instinctively knowing I needed a little space. She was a good boss and a good friend. As long as I was doing my job well, Gemma didn't care. At closing, finishing up was easier as I had done not only my side work but everyone else's as well in addition to some prep for tomorrow. I was surprised nobody accused me of being on cocaine. I showered up and headed for the exit. Gemma was at a table of stragglers being Gemma and putting on the charm.

She saw me and waved. I thought for a second she was going to make me go over and talk to those people. It was like a rehearsed act. Gemma would say something to her audience like, "and here is the man behind it all-my executive chef," and I would have to talk to them and smile. Tonight I didn't feel like it, and Gemma knew it and just smiled and nodded. I waved back and left The Bistro.

It was another beautiful night and I wasn't sure what to do with myself yet. Madison had said that she wanted to see me, but no plan to meet ever materialized. So I walked down to her building. I could see that her lights were on, and therefore she was home. I started to wonder if Madison was having her "dessert" with Robert Thorne after all.

I rang the buzzer.

The door buzzed open without a word, so I opened it and went inside.

I knocked at the condo door, and Madison answered. She greeted me with a smile. That she was genuinely happy to see me made me feel good. She was in her sheer black robe, black bustier, her garter belt and thigh-high stockings. Her movements appeared to slowed by alcohol. It added a sort of clumsy cuteness so her.

She pulled me into the apartment and pushed the door closed, locking it. There was some soft music playing in a foreign language and candles lit all over the condo. Madison was still lighting them as I entered. She lit the last few and then turned to me with a smile, took a step forward to me and kissed me passionately. I hugged her, internally relieved and happy to find her alone and waiting for me.

We fumbled our way into an armless dining room chair. Then she guided me into a sitting position and the sank to her knees. Madison unbuttoned my pants and pulled them down and without a word took my hardening cock in her mouth.

All the events that had happened with Kate, and Margot, and the sex dream about Gemma had all helped me build up more come waiting to spring free from my now full testicles. After a few deep swallows, my hog was at its fullest and hardest.

Sitting there watching Madison 's beautiful head of thick, shiny hair slowly bob up and down was truly wonderful. She now took me out of her mouth and kissed and licked my ball sac, she was about to do one of her best tricks, the one she loved to do. I sat back waiting for it with eager glee. She loved feeling the balls undulating and churning a new batch of semen through the scrotum in her mouth. She licked and enjoyed feeling and seeing me being taken over by sensation before her eyes. Madison flipped her tongue and started her favorite fellatio move, slowly drawing her tongue up past the ball sac to the base of the cock on the underside. She cradled the cock on her tongue and, not too fast but not too slow, dragged her tongue upward toward the head of the prick up to the tip, teasing the pee hole and tasting the clear precome. She would lick and flick her tongue, then open wide and forcefully swallow the entire plump piece of man meat. She loved the feeling of a full throat and loved the shocked, awed response from me. This time was no different except she was letting it all hang out, giving the best and sloppiest head she had given me thus far.

Her warm saliva ran down my cock and soaked my balls much like fucking her very wet pussy.

I looked across the candlelit room and out the window to the harbor. The boats and yachts bobbed in the tide like Madison's head bobbed on my tool. She took me out of her mouth and said, "Let's slow dance; slow dance in the chair."

Madison stood, then lifted her beautiful lace-stocking covered leg over me. Straddling me, she gently nudged my chin upward and held me there face to face. The eye contact was like sex itself; those sexy, smoldering eyes had the power to stiffen any man's dick, and she knew it. She slowly squatted down and funneled my rock-hard manhood into her open, dripping sex. As the swollen head was pushed past her moist labia minor, Madison gently bit down on her lip, a telltale sign she was hot, feeling pleasure and relishing the moment.

she lowered herself slowly. I felt her hot, wet pussy yield to my shaft. With her cunt slowly conforming to my size, she slid herself all the way down. She was so open and wet but still taking her time. When I was in her as far as I could possibly get, she just stayed there motionless.

She was on top, and were were face to face again.

I couldn't help it. I kissed her deeply. We didn't move. I was still and so was she. We just stayed there, loving the closeness. Madison stared at me and I stared back.

"Hi," she said, and it was then that I realized that we had not spoken since I arrived. So hot was our lust that I was naked and deep inside her sex without words.

"Hi," I said back.

"Mmmm, your cock feels so good, ... you are SO inside me!"

"Yes, so deep. I love how you slid down my cock so ice and slow."

"I have to... it's so big, and I don't want to hurt my pussy."

I kissed her again.

"Lawrence, dear, I want you to be still and let me fuck you. Just sit there and stay nice and hard for me...okay?"

"Um.. okay."

Madison put her feet on the floor and rode my hog up almost all the way off except for the cock head." She then began her slow descent, impaling herself on my rigid pole, then slowly up again. This time, she used her cunt muscles to squeeze my shaft on the way up. It felt so good. I wanted to return the favor so I swiveled my hips into an upward hump, trying to make a sexual collision of cock and cunt; the type of collision that sends both parties in to another level of pleasure.

"No, Lawrence, this time I want you to stay still and let me do the work. Nice and easy. If you go too fast then you'll come. Just relax, it's a process of pleasure."

She was right. It was wonderful, and she really knew how to work her pussy.

After a while I noticed how long we'd been fucking and marveled at my own control and stamina. Just a week ago, before I met Madison and started my sexual education classes with her, I could never have gone this long without coming. She fucked me for almost half an hour and was becoming more and more vocal.

Madison started to moan and breathe heavily. "Are you going to come?" I asked.

"No... I don't want to, nnn-not yet!" She slid all the way down and held herself there again for a long moment. I reached around and cupped her perfect buttocks with each hand. Madison cooed her approval. She stayed there motionless, perched on my manhood and then put her head down on my shoulder and held me, resting, to prolong our fucking.

"I don't want to come. This is so good, I love this, fucking like this ... this this position...being on top, riding your penis, almost as much as I love it up my ass."

Hearing those words almost made me come.

"Go ahead and come, come through your pussy so I can take this cock and slide it right up your fucking asshole."

Madison looked at me as if in awe; she was turned on by my dirty talk. But it was more than just that. She loved the idea, and she knew I was a freak for anal as much as she was.