Flashbacks Pt. 04

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"It's in the hole!"
3.2k words
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Part 5 of the 5 part series

Updated 06/07/2023
Created 12/05/2015
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Please read part one or part two and then forward by chapter before you read this. (Or say "fuck you" to me, and read them like a porn version of Twister, skipping up and down the line. OR, realize that you typed the wrong URL and you should actually be at Disney.com. You pervert.) Part one is just a plain sex story, an intro into what my life became, but starting from part two the plot starts. I'm not going to waste people's time recapping what came before.

"There is nothing wrong with being scared... as long as you don't let it affect you until the danger is over." - Robert Heinlein

"When in doubt, mash the accelerator." – Han Solo

*****

I put the glass of drugged liquid down in front of me, centered directly in the ring of water left on the table from when I had picked it up. An ounce or so still sloshed gently inside.

"What will the drink do to me?" I asked, frightened. It's not everyday that someone freely admits to being a criminal and THEN drugs you...

"Make you less thirsty, I guess," she smiled like a cat that finally cornered the mouse, "and maybe get a little caffeine and sugar in you for what's coming up next."

"But what will the drugs do to me?" I asked, angry and scared. Ok, ok, scared and a just a little angry.

"There weren't any drugs in there. Just a coke."

"But..." my voice trailed off.

"As I said, it was a test of your trust in me. I don't need to drug you for that; I just need you to prove you're on board, that you'll try and make yourself a better and happier person. I don't like drugs, personally. If someone wants them, fine for them, I suppose..." she mused, "but I like to feel everything in life, to drink it in with huge gulps while being totally awake. So no drugs for me," she concluded.

"On board for what?"

She smiled at me, genuine joy, painful to be near. "Your long journey from a homosexual top to a versatile lover of all genders. It's hidden deep inside you, you know, it'll just take time to pry it out of you. If you let me."

So later I was showed back into the plush suite by the motherly woman, real name "Tara", and had a better chance to look around.

The night was cooler, so the windows were closed. Gauzy drapes covered the windows, and behind them, just visible, were the classic hotel privacy sliding drapes.

Even the backs of them had a marble pattern, a pattern that swirled through the marble floor, black and red and blue's shading into the stark white marble. I noticed that some areas of the room that should have marble, in just a fancy place; had been replaced with deep, thick carpet in sweeping arches that changed the room from "high society" to a work of warm art.

I couldn't tell you why it worked, but it did. This room, with it's small yet detailed crystal chandelier, swept amber light over the room, just dark enough to be exotic and comforting, like a blanket that has just come out of the dryer. It was made for romance and sex.

Two women came into the room, and I thought, HELL no, I didn't sign up for this. I didn't want a wet slit, not to be rude; I wanted a hot body with a nice meat stick.

One woman was a little pixie blonde, who couldn't have been more than 5' tall. Her brown eyes were alive under her freckled forehead. She was shapely, but in an athletic way. Cute as a button (what makes a button cute?), small breasts, feminine but not deeply curved, and a skip in her step that made her curls jump up and down. She didn't walk so much as bounce into the room and stand in the corner, an I- know-something-you-don't-know grin plastered on her face.

The other woman was about average height, with dark brown hair that fell in gentle waves down over her shoulders, with a lot coming down over her chest. She had nice breasts, C's maybe, I really didn't have any experience in that... But she did show cleavage, enough to make most men look and many women glare. Her body was slightly overweight, not fat by any means, but at the top end of "normal". She had curves, and she was one of those women who could have abs or breasts, but not both at the same time. She didn't have abs.

It was her face that was arresting. Sharp, severe angles, deep set black eyes, and a face that fell into angry when not actually thinking about something. Someone had hurt this lady in the past, BAD. She stalked into the room, went to the opposite corner, and glared at me like I was about to do something.

Tara came back into the room, and said, "I just wanted to remind you that today is $2,000. Also to tell you that Sarah," and she pointed to the blonde, "and Tara – yes, I know, two of us? Two Tara's." She shook her head slightly. "She likes to be called T."

"So we call her that," I guessed.

"Oh yes, my dear, you most certainly do," Tara said emphatically.

"So you can do what you want with our little hooker friend, he'll be here in just a few minutes. But T and Sarah will watch, and maybe make comments. One of them might even join in. It's your first step, you know, dear, and..."

And she got interrupted by that beautifully muscled man gliding into the room. He was completely naked, and his hairless body was, once again, gleaming faintly from some oil. I heard Tara say something else, but I didn't notice it, and I certainly didn't realize she had left the room.

He walked up to me, looked straight into my eyes – we were both almost the exact same 6' tall – and took my head with both hands and started to kiss me. Soft, lovely kisses, kisses that lasted and trailed over my body, kisses that licked my ears and forehead, kisses that nipped at my lips. And I gave as good as I got, not as skilled but just as enthusiastically. My tongue rolled over his eyebrows, with the grain, from the face to the edge, and then started again with little licks.

When I went up, he went down to my neck and with one sharp bite, gave me a deep, dark, delicious hickey right below my ear, and then he kept sucking and licking gently on it.

My cock was rising. Usually it's mushroom head rests on my stomach, but our groins were so close that it rose up to settle right between his balls, pushing them gently apart and pushing the top of my head between them, the mans equivalent of breast sex. Their soft, sensual skin closing their hairless warm, large balls around and over the top of my head. That lasted only a moment though, as his cock, straight as an arrow, rose as well and started to poke me in the stomach. Instinctively, we moved apart, and my cock leapt out of his embrace. I will never forget that feeling of hot, dry, radiant heat.

We shared a fleeting glance of a smile, and then he looked down. I was rock hard, or almost, and he put one hand down to hold my cock. I couldn't wait until he went to his knees and sucked me in like he had the last time, but he gently held me by my dick and bent over, doggie style, thrusting his ass at me.

What a glorious ass it was. Round, hairless, flawless, a freckle on the upper left hand cheek, with faint veins running through the muscles underneath. His beautiful puckered web of an asshole quivered, and I realized that he was doing those exercises that made the dick jump and the ass pop like that.

I went towards it like a hungry predator, but suddenly, T, the angry lady, was over his shoulder and handing me a bottle of lube. She turned to the pixie, who wasn't tall enough to have reached me, and said disdainfully, "He would've just shoved it in. No manners."

I was embarrassed that she was right, I was embarrassed that two women were watching me, I was embarrassed that they were going to make comments, and I was scared that one might even join in. And I did have manners... What I didn't have was ever, and I mean ever, having the chance to slam my cock into someone's ass.

My dick softened, going down to level, which for me was one step from limp, and the man took the lube from my hand and slathered it all over my cock. Up again it swept, and the man then took his lube soaked hands and rubbed them over his beautiful hole. He put one finger inside, just to make sure, and the pixie said out load, "He's ready!" Then she whispered in a stage whisper, "I love this part, when the head goes in."

The man leaned back over the couch doggie style, and looked up at the two women. I followed, and then decided I had to do this quickly before they distracted me again.

I took my slippery 6" cock, with its thick girth and its large cut head, and I pressed it against my target. The puckered hole resisted, and I pushed harder, and it resisted again, and for just a moment I wasn't sure he wanted it, and then he relaxed and my cock popped in and I sunk... so... deeply... into his asshole, and it was warm, and it was perfect, and my stomach bumped into his ass cheeks, and I wasn't totally in, because I couldn't get through his cheeks, and I tried to pull them apart, but I might as well have been pushing on a vault door.

Who cared? I pulled back, not all the way, and just started to ram myself in when Sara shouted, with an almost perfect imitation of Bill Murray, just way way higher, "It's in the hole!"

Again, a mood killer, but I was determined not to let her ruin it. I pounded away at him, going deeper, certainly staying rock hard now, and I started to sweat from the exertion. I looked down after wiping my face with a lubed hand, which didn't do me any good, lube and sweat mixing on my face, and I saw that his body, too, was reddening and starting to sweat. He wasn't doing anything, just taking it, but it was really getting to him. He was trembling, and every thrust made him lean forward a little. We fucked like this in smooth, hard steady rhythm, with every push leaving a forward xxxx on his part, and then I heard him for the first time.

He moaned. The perfect, perfectly silent god of a man had a voice, and he moaned, a low, exhalation of breath that sighed off into nothing. I slammed into him then, and started to pound away. He started moving the opposite way, pushing himself onto my dick, with a deep grunt of pleasure at every thrust. He reached back with his hands to spread his cheeks, and as I dove deeper, but still not in all the way, one part of my mind asked how he was still crouched over the couch doggie style with both hands spreading his cheeks so gloriously, so smoothly and strongly that his fingers left red marks where they slipped on the sweat, and I looked up.

His grunting and moaning was muffled now, as I saw Big T holding his shoulders, and Sara's skirt over his head, with her crotch by his face.

His sounds grew louder and louder, but were muffled, and I knew at that point that Sara, the little, young, blond mass of curls and smiles and adorableness had a dick and he was sucking it down just like he had mine, just a few days before. This was amazing, I had to see, and my begging eyes bore into her face with desperation, and she whispered to me, "It's in the hole", and she pulled her dress up, and yes, her beautiful cock, truly an average size, was slurped into his eager mouth. We went back and forth, and he tried to match our movements, but we didn't match, so he just ended getting pounded in back and forth in both directions.

His dick throbbed against my leg, and Sara's balls swung gently back and forth on his chin, and we slammed him harder and harder until T opened her fucking mouth and said "stop" and let his shoulders go. Sara stepped smoothly back, her glistening cock sliding out of his mouth. I was on the back swing, and so his falling forward popped my dark purple cockhead out of his ass and smack against my stomach.

I glared at T and was going to tear her another hole to match her cunt when she said, "he's had enough – finish him," and he turned eagerly over. I pushed against his legs, and he lifted them up and held his ankles in the air. I went to shove my dick into him, and realized that in this position, I was going to slamming it home, plunge deep and hard and fast and deep again and I looked up and saw that Sara had moved to one side, and her cock was once again in his mouth. She was breathing heavily now, but still managed to look up at me and mouth the words "in the hole", before she blew her load.

I knew how much he wanted to swallow, but her dick had its own ideas, and she came over his face, covering his mouth and chin with delicate drops of pearl white. T swept forward, held Sara in a gentle hand, and started licking his face clean, leaving me pounding and pounding faster and faster, and he's groaning and grunting and heaving and sweating and I'm making noises over loader and faster and louder so low and almost growling as I pounded him, and it was so hot, so hard and heavy and musky and sensual and I was dripping sweat all over his chest and stomach as I thrust myself balls deep into his ass which was also covered in sweat and he was making noises faster and faster now, no words just growls, and then yelps, just ramping up to cum, and there's T cleaning his face from Sarah's white load dripping off his cheek and chin along with the sweat drops and it doesn't bother me because he's taking me in and I'm blowing his mind and giving him everything and Sara has now started leaning over T and scratching her back with long nails that left welts and none of this mattered because I was POUNDING away and then I stopped grunting and started just one long growl and punched my cock deep into his asshole and we both came at the exact same time.

He screamed, a shriek that shattered the glass for miles around, and I snarled and threw, I shot, I blew load after load after load into his ass, my dick just jumping as each spurt shot through into his ass and I was holding onto his hips so hard that I felt some of my knuckles crack and my fingertips were digging into his body and his cock was blasting cum straight down at the floor, at my feet, and he had quite a load too, not as large as mine, but good, and then we both stopped moving entirely and just hung together in that silent agony of bliss and desire to have been able to go JUST a little more and then I felt my foot get licked.

Sara was cleaning my left foot, gently but with swift licks, slurping up each drop, and I looked back up, and there was T right next to me, but the anger was gone, and it was replaced by a desire to please, and she asked me "can I help clean you too?" and I didn't know what had happened but she was a different person but she was still a woman and she wanted to lick my foot clear of his load, and it was just too far over the line for me (then), and my cock slid gently out of his ass, slipped down his crack, and slowly started going limp, and my balls started going away from my body, and T was just too much.

I stammered nonsense, and although I didn't say anything, she knew that I meant no, and she just smiled regret at me and said, "I understand, you're just not ready," and she took one hand and gently swept hair off of my face and left the room. She didn't stalk, she didn't stomp, she just left quietly.

The big man stayed there, and Sara finished my feet, knelt up, licked his ass clean, and as he stood up, she rose full height head to my shoulders, and gave me a big hug. He left silently, but my fuses were blown.

She helped me onto the couch, and then cuddled as the inside of the spoon, curled up like a cat. And just like a cat, she fell asleep in my arms. And after the warm glow had passed, I fell asleep as well.

We were woken by Tara, gently, rubbing our shoulders. I looked up at her sleepily, and then shot up, tossing Sara up and half off the couch.

"Did I do something wrong? Should I have let Big T, um, I mean, did I not do what Anne wanted? Am I over?

And Tara smiled, again gently, and said "of course not, dearie. Did you have fun?"

"Uh, SO yeah," I said, and I pulled Sara back onto the couch and held her in a warm embrace, part thank you and part sorry for the couch toss, and Tara glowed and said "You'll do things at your own pace. You did very well today, Anne will be pleased. And you should be too. Thomas (so that was his name – didn't matter, never saw him again) blew his load, you blew yours, and Sara blew hers, and T got to hold and watch and help and I know she's getting hers for a second time right now; so everyone is good. New experiences, lovey, that's all one can ask for. Remember, you're not being pushed. You're being invited into a world that you don't know you need."

Sara turned and gave me quick kiss on the cheek. "I don't think you're doing fine, I think you did awesomely," she said, and even though I had not touched her, I blushed with pride and happiness. Tara cleaned Thomas's clothing, Sara and I dressed, and we left the suite before our time was up.

I half stumbled up the stairs on the bus, and slumped into the crappy ass unforgiving seat. I rode back to my house on autopilot, walked into my house with a mumbled hello to my mom and dad, and went up to my room to crash. Sitting on the perfectly made bed (thanks, Mom) was ninety thousand dollars in nine neat, clean, fresh bundles of hundred dollar bills.

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READ MORE OF THIS SERIES

Flashbacks Pt. 03 Previous Part
Flashbacks Series Info

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