Play it Again Sam Pt. 04

My thoughts were interrupted by a spill of light from the bathroom door opening. And then my mind went blank.

Gloria had taken off her dress.

She stood a moment to let me get a good look. I was more convinced than ever that she had been a dancer. Her body was long and lean. She wasn't bulky like an athlete, but every movement revealed lean muscle moving under smooth, perfect skin.

As I watched she removed her sheer bra, fully exposing perky, teardrop breasts. They were maybe a large B or small C, ideal in my book. They swayed infinitesimally as she walked over to me.

She put her hands on my shoulders as I was sitting on the bed. I was at optimal ta-ta gazing level. I didn't try to make eye-contact.

She arched backward a hair, to thrust her chest farther forward, and drew her knee softly across the swell of my cock through my pants.

"I can tell you like what you see. Why don't you unwrap the rest of your present?"

Before pulling down her panties, I drew her in closer and placed several gentle kisses along her waste-band. Her skin felt heavenly under my lips. I slowly peeled off her thong, revealing a divine pussy. Her lips were bare, with a small landing strip above.

I reached around to softly knead her full, firm ass. I breathed gently along her nether lips, then took my first taste.

She started to pull away, probably to get me naked as well, but I was going to do this my way. It was important to me that I take the lead tonight. I wanted an assessment of my sexual prowess, so I needed to direct the action.

I hooked one arm under her ass and stood up, lifting Gloria as I rose. She latched onto me to steady herself, but we weren't going far. I twisted around to lay her on the bed. Then I took a smooth thigh in each hand and lifted her legs up and out, giving me access to her pussy.

I got to work eating her out. After I had her wet and ready, I added fingers to my tongue. Gloria convulsed in her first orgasm in short order. Normally, with my wife, I usually went for at least two, but we had all night and I wanted to get through most of my repertoire.

I climbed up to lay beside Gloria, and we shared our first kiss. She did not seem at all put off by the taste of her juices on my face.

I moved both of us up the bed until we were propped up by pillows against the headboard. Gloria moved willingly however I positioned her, only taking the initiative to continue kissing me. She managed to remove my shirt along the way.

With one arm behind, cradling her, I used my other to rub delicately on her pussy. I dipped my middle finger into opening, followed soon by the index finger. This was something I had first seen watching pornography. It was a technique that seemed to get some of the most honest, orgasmic reactions from the actresses.

I slowly worked my fingers inside Gloria, until I was sure she comfortable and well lubricated. Then I curled them and started making a 'come here' gesture with both of them against the upper wall of her vagina, stroking her g-spot. I cupped my hand around her vulva and continued the motion, but now using my whole arm to pull up and push down. The motion looked almost violent, but I had learned with my wife that for the woman it was about equivalent with a vigorous fucking.

Gloria started making keening noises. Both her hands were gripping my forearm, but she made no effort to stop me. I kept pumping her pussy until she came forcefully, testing the soundproofing of my luxury suite.

Following her orgasm, Gloria flopped back, flushed and languid. I cradled her, using my free hand to softly run my fingertips over her heated skin, until she got her second wind.

"That was a new one for me. That doesn't happen often. But I feel like I have some catching up to do," she said with a smile.

I let her direct me to stand by the bed, where she quickly divested me of my pants.

My cock was rock hard, with a sizable wet spot on my boxer briefs showing my arousal.

Gloria rubbed me through the cloth, then leaned forward to take the head into her mouth. She nibbled lightly, before she yanked down my underwear and started sucking my cock in earnest.

I only had one woman to compare to, since my first few girlfriends never gave me a blowjob, but I couldn't imagine a better fellatrix than Gloria. I assume her technique was impeccable. I was too blissed out to really pay attention to specifics. What I did notice, what made the experience spectacular, was her enthusiasm.

She truly seemed to enjoy sucking my cock. She went at it with a joyfulness that made you think she was doing her favorite thing in the world. I had a very hard time not blowing my load in the first minute.

I've mentioned before that I used to border on the "premature" end of the spectrum. I solved that two ways. First, experience. There really is no substitute. Second, masturbation.

Now, I masturbated, just like every young man ever (or close enough to make no difference). But, when I had the time, I started masturbating with a purpose- to go as long, with as much sustained pleasure, as I could. I learned to vary my rhythm and stop when necessary, then eventually I was able to translate those skills into the bedroom with my wife.

These days, I can go as long and hard as Julie. I've come to take pride in my stamina. The average sexual encounter lasts about fifteen minutes. I have no problem going longer unless I choose not to.

So I was a little disappointed in myself when Gloria had me shooting into her mouth in about eight minutes.

I put it aside. She was just too good.

I pulled Gloria up and kissed her. Normally, this might be time for some pillow talk before round two, but I was still feeling fresh, and ready to go.

I laid her back down on the bed and took position between her thighs to dine again. I didn't make her cum, only got her warmed up until I was sure there was lead in my pencil again.

Once my erection became uncomfortable pressed against the bed, I moved up Gloria's body, trailing kisses as I went. As our faces became level I bypassed her mouth and ducked around to nibble and suck her earlobe.

I slotted my cock in position by feel, then pushed in.

Gloria's intake of breathe was music to my ears. She was warm and snug. We soon settled into a rhythm, with Gloria working her hips to fuck back at me. After several minutes of missionary, I sat back on my heels and lifted her legs to drape her knees over my shoulders. Then I leaned forward on straight arms and used my legs to pump up and down.

"Yes, just like that! A little harder!"

I sped up and used a little more of my weight. Our pelvises were meeting with an audible slapping sound. Gloria had her eyes shut and mouth open, occasionally speaking disjointedly.

"Fuck...fuck...that's...shit...harder..."

I believe Gloria may have had several small orgasms. Sometimes it's hard to tell, at least for me. But there was no doubt about it when her pussy clamped down on me. She wailed and her legs shook like she was having a seizure. There is no better sight, sound, or feeling in the world than making a woman cum hard.

I gave her a moment to come down from her high. I hadn't cum yet, so I turned her onto her hands and knees. This was my favorite position, so I usually saved it for when I was ready for release.

Her ass was a work of art. It was full and round, but it barely rippled as I fucked her. Finally, the sight and feeling were too much, and I emptied my balls into her sucking pussy.

....

We went for round three later that night, but now that the test was complete, it was time for the professor to deliver her grade.

We did our debriefing in the shower. Well, technically we had de-briefed each other in the bedroom, but...never mind.

I had a hard time concentrating while watching Gloria scrub her nubile frame.

"I'll be honest, when you told me what you wanted, I didn't have high hopes. Frankly, I expected you to be terrible. But you weren't. In fact, that was one of the most enjoyable encounters I've ever had with a client. I won't say you were the best, but definitely in the upper echelon. Either your wife is a nymphomaniac with impossible standards...or she lied to hurt you. Speaking from experience, women can say some truly horrible things when we have our dander up."

I hadn't expected to be told I was bad, but it was still as if a massive weight had been lifted from my shoulders.

"I didn't give you the whole story before," I said. "My wife didn't tell me I was a bad lover, she wrote it in her diary. She used it as an excuse to cheat. She stopped saying it a couple years ago, but she never stopped fucking around on me. So, I thought I had become a decent lover... but I needed a third opinion."

And maybe a fifth, sixth, seventh... But I didn't say that. Wouldn't be polite to tell this gorgeous creature that I was already looking forward. As much as I had enjoyed fucking Gloria, I also wanted to test my "game," see if I could attract and satisfy someone who I wasn't paying. But that would come later.

"Well, in my professional opinion, you have nothing to worry about. Your cunnilingus was top notch, your touch was just right, and your aggressiveness was a big turn on. Different women like different things of course. If I had one criticism, it's that you were very quiet. Being so purposeful in your actions made up for it, but women like to hear you, just like you like to hear us."

"Hmm... Thank you, that's helpful. Honestly, I don't make many involuntary sounds during sex. I would have to make a conscious effort to moan or groan. That would make me feel silly, but maybe I should talk more, communicate, pay compliments."

"That would be good," she agreed. "Don't do any fake moaning, but tell us what you like, tell us if what we are doing feels good, how turned on you are."

I smiled. This is what I wanted. Constructive criticism. I briefly worried that she was blowing smoke up my ass. She was paid to make me feel good after all. But I thought she was being honest. Escorts in her price range were more like courtesans, smart and classy. She would have turned me down if she wasn't willing to give me an honest critique.

Plus, I may be dense, but I didn't believe she could have faked those orgasms.

We dried off and went to the sitting area of my suite. We talked some more. Gloria gave me some more tips and tricks to use in bed, but reiterated that I didn't have any reason to feel self-conscious about my abilities. I took it with a grain of salt.

Still, it was good to hear.

After a while we returned to bed for round three, which was softer and more reserved. She planned to leave in the morning. I'd be gone before that.

...

Friday July 15 ^th , 2016 Day 133

"What is love? Baby don't hurt me....don't hurt me....no more"

Sleeping with Gloria put a period on my marriage to Julie. While I couldn't divorce her as long as I was stuck in the time loop, when I slept with another woman, it truly felt over to me.

I got on with the business of living my life.

Being trapped living the same day over and over is somewhat like purgatory. In fact, I gave some serious thought to the theological ramifications of my predicament. I didn't actually believe I was in heaven or hell, but my life could resemble either one... if I let it.

So what does a guy do with eternity?

I binge watched TV shows. I ate in every restaurant that I had even had a passing interest in, as well as several hundred I hadn't. I saw every movie, play, and musical in the greater New York area. Went to every museum, landmark, and tourist attraction.

I used my newfound wealth to get into venues that I never could have afforded before. I spent like it was going out of style. I handed out thousands to street people. I tipped servers exorbitantly. I went to high end boutiques and had them pamper me. I went to a strip club, and made it rain with hundred dollar bills.

I was easily bored, so I did a lot of stupid shit. It was liberating to know that I could do pretty much anything, without consequence.

I perfected my technique with a garden hose. The Chinese have their water torture, I have mine. I got my ass kicked by Dr. Peters again the first time I tried it, though not nearly as bad as the first time. Which brought me to one of the goals I had set for myself.

What I needed to do, was learn how to fight.

...

I'm a big guy, 6'2, 210. Being about four inches taller than the average man, and broad in the shoulders with it, I was used to being among the biggest guys in the room. Especially among my white collar brethren.

So, I'd never had to fight. I was too big to be picked on, and too mild to do the picking. But I'd unconsciously thought that if the chips were down, I could fight. Like, I suspect a lot of men, I thought that I was an untapped powder keg of badass. I simply chose not to hand out ass whooping's.

But Dr. Dick had disabused me of that notion.

So now I wanted to address that imbalance. I wanted to beat him in a fair fight, and for that I needed training.

You can find anything in a city the size of New York. I had no shortage of martial arts training centers to choose from, and unlimited funds to make sure I got hands on instruction.

My first choice was krav maga. I had heard that it was maybe the most practical of the fighting styles, designed for real world situations. MMA training was easier to find, but I didn't want to do much grappling, especially with a naked Dr. Dick.

I worried that I wouldn't be able to learn. I was already in good shape, but I couldn't build "muscle memory." But I tried anyway. And either "muscle memory" is a crock of shit, or it has more to do with the brain than the muscles themselves. Because I had no problem picking up where I had left off every day.

For a while, fight training became my day job. I devoted several hours to it every day. I would train at one school for several months, then switch to another to sample their style. After I could hold my own against some of the advanced students, I would move on again. I didn't need to be an expert, just proficient.

I found something I hadn't counted on...I enjoyed it. I had been a regular at the gym for years, but I enjoyed the more...precise... workout from fight training. It was sweat with a purpose. And learning a form of violence was calming in a strange way. The forms to improve balance and coordination were almost meditative.

And yes, I'll admit that I enjoyed the fighting itself. Though perhaps my enjoyment was buoyed by the fact that I was never sore or bruised the next day.

Krav maga is an amalgam of more traditional fighting styles, with all the wasted motion and posturing removed. Since I enjoyed the... art of fighting so much, I decided I would check out the traditional schools as well.

I went to several, but ended up giving up on them quickly. All the instructors wanted to "fix" me. They set a lot of value on tradition, and while I enjoyed the almost yoga-like stances and movements, when it came time to spar I reverted back to the more straightforward moves of krav maga.

I even tried yoga for a couple days. But after you get through with all that stretching, they don't let you beat on each other...lame.

But it did inspire me ask Ben if he knew a girl who liked a light spanking. I met Cassie at the Westin with several pairs of yoga pants...awesome.

I was about to give up on other fighting styles, when I walked into a small hapkido dojo above a Korean restaurant in the Bronx.

When I first met Sung, the owner, I felt an immediate kinship. It was strange, if he had been a woman, I might have likened it to meeting a soulmate. But... no way man, I am totally straight.

It was very strange. Sung was a taciturn man. I was never able to develop what I would call a true friendship with him. He was just too reserved to form any attachments in a day. As I got to know him better, I was able to shorten the 'getting to know you phase' and learn some of his background. But even with the almost...compulsion I felt towards him, I had to resign myself to the fact that we could never have a real two-way friendship until the time loop ended.

As for that weird...attraction for lack of better term. I wrote it off to our being kindred spirits when it came to the subject of martial arts. Kenji had some kind of military experience. He taught the traditional forms and katas, but he adapted them to be practical, and he mixed in other styles where they were more effective.

In a sad manifestation of the time loop's effects, I came to view Kenji as my best friend, but to him I was just a stranger that he met for the first time every day. His dojo became my home away from home, the fallback option for me to go when I couldn't muster the enthusiasm to come up with something new.

I continued training in martial arts. After a while it stopped being a means to an end and became its own reward.

But I was still going to kick Dr. Dick's ass.

...

Friday July 15 ^th , 2016 Day 297

"What is love? Baby don't hurt me....don't hurt me....no more"

I went back for my rematch after about six months of preparation. I knew he had some kind of training. Now that I had some myself, I could look back and say that he had a solid, but unremarkable skill set. More than enough to beat Sam 1.0, but the new and improved Sam was going to take his lunch money and chase him home to mommy.

I had gotten some fleeting revenge in the interim, most notably with the garden hose. Most of my other attempts were similar prank-level efforts. Since meaningful retribution was beyond me, I mostly harassed Julie and her lover in ways that I found amusing.

I once arranged for Dr. Dick's wife to meet me and catch them in the act together. It was quite the show, but in the end it was too real for me. I didn't really want a serious confrontation. It just threw me back into my depression. So long as I was in the time loop, I couldn't move on from my wife. On with my life.

For my own sanity, I couldn't let myself wallow in the aftermath of my failed marriage day after day. So when I did interrupt my wife's afternoon delight, it was usually with juvenile shenanigans designed to make me laugh at their expense.

But not today. Today I was serious.

I briefly tried to plan some distraction for Julie. The neighbors two doors down had a new baby. They used cloth diapers and paid a service to take away the soiled ones and clean them every couple days. A face-full of dirty diapers might keep her from interfering.

I was starting to think that I had an obsession with throwing shit in my wife's face. Must have unresolved issues.

In the end I didn't do anything. I figured if it looked like I was holding my own against Peters, she wouldn't interfere. If she grabbed him again, I wouldn't sucker punch him. I wanted a fair fight. If she grabbed me... well if the first fight had any silver lining, it showed I can take a punch.

I walked in the house after giving the lovers some time to get going. I'd walked this path many times by now.

There was Dr. Dick, pumping my wife.

I cleared my throat loudly. "HARUMPH-HRMM"

They froze for a second, then Julie started scrambling to get out from underneath Peters. She scooted up the bed and tried to pull the covers over her nudity. She was staring at me like I was a ghost, making little whining sounds. Tears already streaming down her cheeks.

I knew from experience that we could stand here staring at each other for several minutes if I didn't say anything. Julie never used the old platitudes of "it's not what it looks like" or "it doesn't mean anything." Her frantic ramblings were all some variation of "I'm sorry" over and over.