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.
