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A Fantasy of Mine

Story Info
A thought I've had a number of times. It is always evolving.
2k words
4.14
19.8k
8

Part 1 of the 2 part series

Updated 06/09/2023
Created 09/10/2019
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I have saved up my money for an "All Out Vacation". My destination is a smaller-large city in a legal weed state. I have only packed a few toiletries, along with a couple of slutty outfits and wigs. I am 50 and I stand 5'8" 140 lbs. with semi well-defined legs. Even at my age, I can still fill the rod as solidly as I could 30 years ago. The trade-off is I can't get off a dozen times a day anymore.

So my flight/room are booked, I have chatted with some like-minded people online the past few months. I have taken the time to save a few glory hole locations (the first one on the list is in the airport men's room,) and gay bathhouse addresses to my contacts. I am about to play with more dicks in a week than I have in my life (I count 48 as of right now).

Getting off the plane I am buzzed with excitement. I have the next 5 days to suck cock where no one knows me. Plus, I am but fifty feet from the first glory hole of the trip. So I step into the long narrow bathroom and listen to my loud echoing footsteps on my way to the back. As soon as I open the stall door the generous hole becomes visible. By the time I get the door locked and my bag set down there are already 2 fingers circling the hole. I kneel down and lick his fingers. As I settle in on my knees a perfect 5" thin cut super rigid cock pops thru the hole.

My lips leap like a frog on its prey. I forget I am in public, I forget all my plans. There is just this cock right here in front of me. My lips clamp down on his tip as my tongue swirls. I drop till my lips touch are pushing against the wall of his belly. I buck hard, and puke fills my throat. I keep him buried like a plug until I can work it back down. Its been over a year, and I impale my throat as if it was last night. I soon pick up a rhythm with my forehead playing the bass drum on the stall wall. He begins to shoot as I am swirling my tongue on his tip with no warning. I instinctively rock my head side to side while lowering my lips down his shaft. I moan while I feel my own cock strain for freedom, as I drain this stranger.

Once I have milked him dry. He says thank you 4 or 5 times while zipping up and heads out. I sit on the toilet and savor the saltiness I have missed. Well, time to get this vacation started. I grab my bag and storm out without a thought of cleaning the cum off my face. I find my way to the front of the airport to grab a cab and give them the name of the motel recommended by the Dominant Mistress I talked to online.

Once at the front desk, they inform me I have been upgraded to a jacuzzi suite at no extra charge and that I have several messages. He hands me an envelope with my room key and wishes me a pleasant stay. The room is a white leather couch and old all gold Las Vegas-style decore. The Jacuzzi elevated in the corner with a mirrored wall and gold trim. I open a cooler on the table, full of my beer. I remember the notes. One says have a beer and get cleaned up, the other was I will be in the hotel bar. So I grabbed my toiletry bag, got cleaned up and headed to the bar.

When I turn the corner into the bar, I am amazed she is better than her pics. Tight ass jeans showing off that large round ass. Black leather thigh-high boots with 3" heels. A thin white blouse hiding a white push up bra working overtime. She smiles and we go thru the small talk introductions. She sounds relieved that I look like I said I did and actually showed up. After chit-chatting about our online conversations and me giving her face to face verbal consent, she invites me back to her room.

Once she lets me into her suite, I quickly realize it is mine as well. When I turn around to say something, she has unbuttoned her shirt fully. And I forgot what I was going to say, She orders me nude, so I undress and fold my clothes to make her happy. She nods, and says better than what I expected, but could always look better! Just then, there is a knock at the door. She lets in what looks like 2 40+ curvy blond women in leggings and tight t-shirts along with a retired plumber. The 4 of them talk in the corner for a minute then the plumber guy tells me I am with him and leads me to the bathroom.

He takes a wrench from his bag and removes the showerhead. Threading on a shut-off valve and hose with enema nozzle. Once the water is at temp he uses the shut-off. He orders me in facing the back. I push my ass back feeling for it but he is applying lube. He strokes my back and puts me at ease. Before I even know it I have a 4" wand in me, and I didn't even notice. The water comes slowly at first but that initial trickle is replaced with a gush. Once I feel like I am too full and say something. He just pets my back and says shhh.

As my knees turn in and push my ass out to try and accommodate the water, he shuts off the flow. He slowly removes the metal wand from my ass, and I leak a little bit before I expel my contents on the shower floor. The water comes faster the second time, and I fill quickly. After my third round, I am clear. He reaches for a bottle of wine, and an enema bottle from his bag. Soon the entire bottle is in my colon. He tells me to stay put, and not to expel until I am told to. He then turns grabs his bag and walks out.

That warm cozy drunk feeling came on about 10 minutes in. After 15 minutes I was just as drunk as I really wanted to be for this experience. The door opened at probably 20 minutes I would guess, and the wine just jumped out of me while I pissed. It was the 2 forty-somethings. They laughed at first but, told me to wrap up in a towel and come to the bedroom, so I follow them. They have pots of wax and moisturizer on both sides of the bed. Looks like I am going hairless. I lay on my stomach and they start on my shoulders and they work to the middle and down at the same time.

At about the time they are getting to the middle of my back. My Mistress comes in with the gift of a blunt. Her outfit replaced with a black crotchless nylon catsuit and red heels and panties. She walks over crawls up spread eagle 10 inches in front of my face. The 2 women just keep going. She rolls over into doggie and pushes back against my mouth. My tongue throws that red string to the side in short order. I try to bury my tongue in her ass but its too tight. But after a little coaxing she loosened up enough I managed to slide in fully. At that time she dismounted the bed, lit the blunt and handed to me. Leaving without another word.

By the time they are at my feet and wanting me to turn over, I am wanting to stop. My desire to finally fully submit to a woman was right in front of me, and she wanted this. So I hit my blunt and rolled over. They are making fast work of me though. In no time at all, they reach the fold in my leg then jump over my hard cock to my shoulders and work their way down. I have been rock hard the whole time. When they get to it the one girl holds it back with one firm grip while the other waxed. once they are finished, they ask me to slide to the edge of the bed and pull my knees back. I remember the warmth feeling soothing, then Bright Lights! They stand me up and fully moisturize my entire body. At one point I was getting a well-lotioned handjob from one woman. While the other lubricated my ass. So far that will be the best part.

Less than a minute after they leave, a woman in her mid to late 50s comes in with several boxes. She introduces herself, as she starts opening a box. She pulls out a FF breastplate (silicone tits made into a vest) and fastens it around my neck. I instantly have the largest most beautiful set of tits I have ever seen, and so realistic. Now a bra and panties are handed to me. She instructs me to set the panties off to the side until we do something with that bulge. The bra is a black vinyl maybe rubber push up with red and white lace trim. She grabs my sac and gently puts my balls back inside me and tapes the skin to my ass to hold them inside. She places a long strip of tape on my cock at the base and runs it the full length. She then turns me around, reaches between my legs and grabs the tape down and back to secure me tight to my asshole. Stopping the tape short of my tailbone and ensuring its in place.

Now she pulls out the most beautiful thing I have ever seen. Just like the chest piece, only a pair of shorts with the thickest ass you have ever seen for someone my size. Once I slip into the super snug fit, I give it a slap. Thick and juicy, 2 perfect half basketballs. I am about to be so hot! She then laces on the Black latex with red silk trim and chrome rings corset super tight, and I look like the perfect bimbo body on a straight-up dude face. She sits me down in the bathroom and starts my make-up. I finally get some conversation out of her, she works the make-up counter and the high-end retail shop in town. I figured as much, or maybe a bored trophy wife.

She steps back and gives me a look. She pulls out 2 pixie style wigs, a strawberry blond, and a platinum blond with blackish undertones. After trying both on quickly she chose the platinum. Then the little black backless keyhole turtleneck tube dress slipped over me, Just long enough to cover the lines of the latex butt implants when I bend over. She pulls the skirt up and under my glorious tits and fixes garter strings to rings on the corset. On slide black silk thigh highs with a bright red stitch up the back, that feels marvelous with plenty of tension from the corset. Now the crown, black 4" heels with red soles.

While I am admiring myself in the mirror she sends a text, then starts painting on the glossiest brightest whore red lipstick I have ever seen. She is just finishing up as my new Mistress walks in. She tries to come in business-like but the shock of how well a little money can make a man a hot woman read on her face. She recovered and started telling me what my limits were in question form. She did good, didn't miss one, and asked clarifying questions that were well thought out and things I hadn't considered. After we are both happy with the limit conversation, she escorts me to the bedroom. I am not going to lie, the heels were a trip, drunk and high for my first time in years. On the dresser is a mirror with 2 long lines of cocaine and a straw...So are you ready to party...to be continued

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ima_milkwoodima_milkwood2 minutes agoAuthor

I only write when I drink. I have some written but finding time to edit when sober...

AnonymousAnonymousabout 10 hours ago

None of your stories are finished. Are you still working on them?

Shelscott45Shelscott45almost 3 years ago

So Jealous!! Sounds Like FUN!!

BrendaNWBrendaNWover 4 years ago
lovely

Doing well till the drugs, don't need them she is already drunk .. please write more though as you do write well ,

DianeRedfernDianeRedfernover 4 years ago
Nice try but...

too much too fast, sweetie. You have some great ideas and funny moments here but it's like the main character is an erupting volcano trying to get all of it at once. Try a more measured approach but do keep at it dear.

xoxo, Di

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