This Thing Called Life Ch. 04

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Jack meets Jackie.
4.4k words
4.65
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4

Part 4 of the 10 part series

Updated 10/05/2022
Created 05/26/2013
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After pulling into the hotel parking lot, I left my suitcase in the car, not sure if I should be doing this. I had learned a lot about myself from Becky and Mark and had a great time but I still loved pussy like it was honeysuckle rose but then again why was I constantly thinking of Tree and his immense member that had opened both me eyes and my ass to the world.

I felt butterflies in my stomach, or maybe they were bats, my guts were churning something awful with the sense if I entered these doors my life would change permanently, and even more pressing was if I saw Tree I wasn't sure my knees could hold my weight any longer. Ah, first world problems.

As I stood there certainly looking like lost puppy, something unexpected happened. Two women and I use that term loosely given the secrets of this particular hotel, walked from my opposite direction towards the hotel. One was blonde and stunningly hot with porn star lips and looks, with an ass that was wrapped tightly in a sexy black skirt and a red silk blouse that parted just right at a set of amazing tits -- and then there was the pretty one.

She was tall, about five seven with olive skin and long raven hair that reached down most of her back. Her face was absolutely beautiful and seemed to have very little makeup as clearly it wasn't needed but she did wear just the right amount and color of lipstick. What was even more striking was her smile, a beautiful thing that added to her beauty. And her body was perfect proportion, shapely, sexy, all woman I swear, it must be, but probably wasn't.

She had her "friend" held to her side, elbows locked and they laughed and enjoyed life and I sat there wishing I was in on the conversation. As they approached the entrance she caught my eye and her face reddened slightly and she shot me a little bit of that smile. Her hazel eyes locked with mine until she disappeared into the hotel.

Though my life had changed so much in recent weeks and I experienced more lovers in that time than I had in my life prior I really didn't have feelings for any of them, simply enjoyed the best of what each had to offer, but right here in this moment on this date and time in front of this hotel full of trannies I think I may have felt something for a woman for the first time since me ex-girlfriend who was busying herself with a guy's pierced cock up her ass.

Any doubt I might have had went the way of the dinosaur after seeing that beauty enter, so I did the same. She was nowhere in sight when I entered so I took the elevator to Ashley's room and knocked. When she opened the door she was fully nude, a bit sweaty and at full impressive staff. She jumped up and down in joy and I appreciated how her tits seemed to be waving at me. She kissed me on the lips which caught me off guard and then squeezed me tight.

"Jack, you're back!" she said, and her tits on my chest were making me hard.

"Hey!" someone said from inside the room.

Danged if there weren't a naked man tied spread eagle to each bedpost, his cock was moderate sized but active as it was dribbling pre-cum and dancing about of its own accord.

"Jack, Austin. Austin, Jack!"

"I'm a fan of your city," I offered and reached to tip my cowboy hat I forgot I wasn't wearing.

"We're in the middle of something here!" Austin said, clearly not cordial but I did interrupt after all.

"Austin, you're such a pussy," she said and walked towards the bed and turned backwards, reverse cowgirl style and inserted his dick in her ass as she faced me. She talked to me as she rode his dick up and down.

"Tree won't let you stay for free; you'd have to do some work but its perfect timing because we have a job this evening."

"Oh, yeah baby, fuck yeah, your ass is so tight, oh fuck yeah," Austin said.

Ashley's tits bouncing were mesmerizing but I tried to stay focused on her words, the struggle was like trying to do long division in my head.

"We'll have to make some changes before you go with us though," she said and started riding him faster.

"What kind of changes?" I gulped, losing a little of my growing erection, just a little.

"Oh fuck, oh yeah, oh damn, I'm getting close, oh fuck, yeah," Austin gasped. Austin was becoming a buzz kill.

"Nothing permanent, don't worry, see Maria, she will hook you up with Tree's salon down the street and then meet me back here in two hours."

"Oh fuck, I'm gonna get it, I'm gonna, aaaaaaahhh," Austin bucked and lifted his body deeper into Ashley lifting her whole body in the air as his back arched, then back down onto the bed where he pumped again and again into her ass, lucky guy Austin was. "Yeeeesss, fuck, yeeeaaahhh!"

Finally Austin settled down. Ashley rolled her eyes and flashed a fake yawn at me, clearly not a fan of Austin. Then she winked and flashed two fingers. In two hours I'd be back but I'd never be the same.

The last two hours will forever be referred to as the "two hours never to be mentioned again". As I stood in the full length mirror in Ashley's room I saw a naked body that was considerably thinner than I had been in a long time what with the multiple acrobatic sex sessions lately and not much time left for eating, but now I also was stripped of all hair everywhere on my body except for my head and even that hair was cut high and tight like I was in the marines. The lack of hair around my junk made it look even bigger as it was at full attention thanks to the poking and prodding of Ashley and Maria who were both dressed to kill, ready for a big evening.

The part that really threw me though was the makeup and full blown red lipstick that matched my crimson nails. I wasn't sure what to think but then Ashley dropped the blonde wig on me and damn if I didn't suddenly look a little hot if I say so myself. Ashley looked at the mirror from behind me as she adjusted the wig. She lifted the hair and kissed me square on the back of my neck and stroked my dick with a reach around.

A drip of precum formed heavy and drooped all the way to the floor. Maria rubbed some on her hand and licked it and I think she actually purred.

"Un pene tan hermoso," she said after the purr. I'm not sure what it meant but it sounded good coming from her.

Ashley got me to lift one leg at a time and she pulled on a pair of tiny black panties, more like a thong. My dick comically jutted about four inches out of the top of them. Maria leaned in and kissed the head, clearly that was helping nothing.

"No way can I fool anyone like this," I offered.

Ashley slid the back of the thong away and touched a finger to my ass which also wasn't helping.

"Where we're going we only need to have ass access so you're good, and hopefully this thing will soften sometime big boy," she said.

"And I used to think you knew me Ashley'" I offered and she replied by attaching two beautiful breasts to my front which attached with Velcro straps that wrapped very tight around my back, causing a momentary fight for breath. I reached up and squeezed them.

"Wow, they feel pretty good," I said, not taking my hands off them.

"Tree does everything right, just don't get crazy with them or you could have back boobs," she said.

"That's a thing?"

"In your case it could be so be careful," she said and removed my hands and covered my falsies with a matching black lace bra and dang if my cleavage didn't look like the real thing. They finished me off with a short skirt and a black knit top that was tight and prominently showed my boobs.

"That's so you have an excuse not to remove the top, if it was button down it would be too easy Jackie," Ashley said and smiled.

I looked in the mirror and indeed Jack had left the building. I would have gladly fucked the woman I saw in the mirror before me but since that was impossible, someone else would have to do it for me and that was going to happen soon enough. Maria and Ashley each kissed a cheek and Ashley lifted her IPhone to take a selfie, or maybe it was a groupie I guess, but either way the flash went off and the picture I saw was of three stunning women ready for a night on the town.

I asked about shoes and the women laughed and handed over ballet flats, saying I wouldn't survive the trip to the job site if I was to attempt heels, they were always thinking of me. They did hand me a pair of red high heels that they informed me I was to put on just before we went through the door and I was to stop walking as soon as possible.

And then it was a knock on the door that changed my life even more than my suddenly being dressed like a hot fuckable woman. Ashley opened the door and standing there was the woman who had entered the building earlier. She smiled and entered and touched my arm first then hugged me and the hug was electric, there was definitely something about her and she felt so soft, her immense tits were so soft but large and I never wanted to let go.

"Who is this sexy woman?" my hugger asked, and I realized the woman of my dreams didn't even know I was a man.

"Flavia, this is Jackie, it's her first job for Tree," Maria said in her cute accent.

"So nice to meet you" she whispered breathily in my ear.

In that moment and the whole ride to the job I just nodded through the girl talk, realizing I was so far out of my element and that I didn't even know what voice to use in my new getup, and worse, the Viagra we took before leaving combined with the lace panties was causing my erection to throb something awful, in fact there was a wet spot from my precum bleeding through my tight top at stomach level.

Thankfully we finally arrived at a college campus and Ashley drove the escalade up to a frat house littered with party debris on its front yard. A frat, I wasn't expecting this. In short order we were inside and I had changed my shoes. The heels lifted my ass and if someone were the right height they would be able to fuck me while I was standing.

Inside were ten Frat members and four nervous pledges but they lost their nervousness when they saw us. The leader of the frat was a jock type, blonde hair and in muscular good shape who somehow had earned the nickname Tug.

"So pledges, you see what goes on when you join our Fraternity?" Tug yelled, a lot Tug did, I think he only had the one volume.

The pledges hooted and hollered and whistled as we spun ourselves, displaying the goods.

"So strip pledges, butt naked," Tug demanded.

They hemmed and hawed but when Tug informed them that this was the only way they'd get to fuck the women they couldn't strip fast enough. One of the pledges I'll call Eager was mentioning as he stripped that his father was in this frat and how important it was for him to join. The young men were in fine shape and all had similar cocks, about seven inches but with different thicknesses. Most were growing despite their nervousness.

"So this is how our frat rolls, we have women lots of women so we need to know our pledges can hang. But any pussy can get pussy so we want to know if you can fuck a woman's ass!"

The frat brothers hooted and hollered and two of the pledges high fived each other. One of the Frat brothers handed each of the pledges a tube of lube and then we were instructed to bend over. I raised my ass and slid the string of my panties aside. I was pleased to see it was Eager who chose me.

I heard them stroking their cocks wetly to get them full hard and then tug instructed them to start. Eager lubed my ass and stuck a finger in murmuring how hot my ass was and dressed as a woman I felt so slutty and hot. Flavia looked over at me and winked and my cock twinged. Eager slipped in and groaned.

"Oh fuck, your ass is so tight, it's so hot," he said and slid all the way in.

It felt very good, and he grabbed my hips and started working faster and faster pounding me good, he was indeed eager.

"Oh your ass is so good, it's so nice, I love my cock in your ass, you like me fucking you?" Eager asked.

I just nodded but heard the other girls squealing and moaning in delight.

"You're such a hot woman, I can't believe I'm fucking such a hot slut," Eager said and I was worried I would cum myself. He was building a rhythm and I felt his orgasm building but the problem was so was mine. It wasn't just his cock, it was seeing Flavia being taken from behind and Maria's Spanish serenade and the thought that here I was as a woman being fucked, fucked so good by a young hot stud, but then Tug opened his mouth again.

"Are you close pledges, are your little dicks going to cum in these hot ladies asses?" he yelled as usual.

The pledges groaned in unison and fucked even faster if that was possible. Tug leaned in, inspecting the merchandise. He leaned in to Eager and asked if he really wanted to be in the frat and Eager groaned and nodded said he loved this Frat.

"Well here's the deal, whoever comes is out of the Frat," he said.

The pledges all gasped. I felt Eager making the horrible decision, he stopped deep inside me but that apparently was even worse as my as was squeezing him, he pulled out quickly and grabbed the head of his dick tight.

"Oh shit, fuck, oh shit," he said and screamed not in orgasm but in frustration. Two of the other brothers pulled out and fought their impending cum also by grabbing their dicks but the pledge that was fucking Flavia suddenly groaned.

"Oh, oh, no, oh, oh, oh yeeeeeeeesssss...." His cum shot through his hand an immense load that covered his hand, his legs shaking.

The brothers hooted and hollered as the pledge was near tears at not being able to hold back but then all were drawn to Maria who was fucking back on her pledge with a vengeance.

"You like my hard cock in your ass you little bitch," he asked. That was so like him always fucking and swearing like that.

"Si Poppi, si, fuck me stud," she said and was loving every minute. Maria was grimacing and I figured it was due to her holding back touching herself.

"Yeah, that's it bitch, that's it, I'm gonna, oh fuck, I'm coooominggg......."

Maria jumped off him and turned her face to his dick. He yelled and shot spurt after spurt, painting her face. He was yelling and shaking all at the same time, unaware anyone else was even in the room I'm sure.

But those in the room were yelling and hollering and I saw a couple of the frat brothers rubbing their own cocks discreetly. Maria wiped the cum around her face and ate some as the guys hollered even more.

The pledge dropped to his knees unable to stand, his cock beautiful and slick danced on its own as he sat there trying to recover. Eager suddenly let go of his own erection for fear of any stimuli forcing him to cum. His dick smacked against his stomach, he had one that stood straight up when hard. I liked that about him. The other pledge also let go of his own as tug stepped forward.

"So gentlemen, some of you have more control then others but you liked the ladies?"

Nods all around but then Tug said, "Well we have a surprise. Ladies..."

I suddenly felt bad about the ruse but it was a job after all and I had to prove myself to Tree but it was on tugs cue that we all stripped though I left my top on. The brothers were all clearly in on it, there was no surprise just hoots and hollers but the pledges faces all went white without exception. Eager was clearly shocked as he went soft immediately.

"You assholes!" Eager yelled and went after Tug.

Eager got in one good shot but the brothers corralled him and got him in a full nelson, he stopped struggling physically but it seemed he was now struggling mentally. The other pledges were in shock but were watching us. The one who had fucked Maria was staring right at her hard cock.

I hadn't even noticed at first but all of us "ladies" were worked up and standing hard, likely from the fucking but also from the nude men and the Viagra. Flavia had a heavy eight inches, nice and thick and uncut which I had never seen before but I liked it on her, she truly looked like a woman despite her long appendage.

Then the mood in the room shifted when Maria went down on Ashley. Ashley moaned and squeezed her nipples as Maria groaned around Ashley's hard cock. Various "whoas" and "holy shits" filled the room as the women went at it.

Tug looked around trying to read the room then announced, "We're paying for it we might as well get a show, right?" Tug declared. Hoots and hollers actually drowned tug out for once.

Flavia stepped up to me and pressed herself against me, our cocks touching. We reached down and slowly stroked each other and then she kissed me. The world disappeared it did when my lips found hers. The only way I can explain is she was a woman and I was being knocked on my ass at the moment. I forgot about the room, the pledges and for a moment even my name. I hadn't felt anything like this since the woman I almost married. But the boobs brought me back.

Hers were pressed against mine I could feel how amazing they were by the way the pressed and spread against my fakes but it was that contact that made me realize she didn't even know who I was, or did she? Did she know I was the guy earlier and did she feel the same spark and if so was she okay with the whole cross dressing thing? Relationships are hard.

She breathed into my ear, "I don't want our firs time to be in front of others."

So she did feel something? There would be a first time? Move over cloud number nine I'm shooting for cloud ten here. As she pulled away breathily and gazed longingly in my eyes she finally winked our moment away the hoots and hollers returned.

Maria was now on all fours being fucked by Ashley and it was quite the show, I 'm so proud of Ashley, she knows how to work a room.

"You know boys, it's not gay to jerk off, and as you saw earlier Maria is a cum slut she will take all your loads," she moaned as she found a nice tempo.

Again Tug read the room and it appeared he was willing to live up to his name. He started to strip.

"We are paying these whores, let's give the little slut what she wants," he said and his brothers couldn't strip fast enough. Eager was shoved aside, the fight going out of him.

Before the brothers could strip the two pledges besides Eager who hadn't cum stepped up and stroked furiously in front of Maria's face as she begged for their loads in Spanish. One of the pledges touched his head against the other's cock by mistake but the other pledge pressed against it a little harder, their heads touching as they both shot simultaneously and yelled through double impressive orgasms.

Two other frat brothers stepped up, one shot immediately and another joined the one who hadn't yet. Tug watched from nearby enjoying the action as he stroked an impressive member. Suddenly one of the frat brothers got too close and Maria took him in her mouth.

"Holy fuck," he said and started to pull away but then his eyes glazed over and he leaned into it.

"Dude that's a dude sucking your dick," Tug said but appeared to get harder.

The brother nodded and looked back. "Dude, she's fucking good, oh fuck, oh yeah, fuck yeah, oh fuuuuuuucccckkkk....." he squirted and Maria took it in her mouth but there was so much it poured out some.

Maria took her mouth off for air and he grabbed her face and put it back on his cock.

"Keep sucking," he demanded and was moaning as she kept on. The brothers were really hollering now and two more shot on Maria around the frat brother.

Flavia stepped up and said and took one of the frat brothers in her mouth and he didn't resist, he closed eyes and moaned animal style. The others looked at each other wondering how good it could be and stepped right up to find out. Everyone was surrounding them and stroking hard dicks. Everyone who had already cum was hard again and in for round two. The one frat brother announced he was coming again and finally withdrew from Maria's mouth.

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