Monika's Slutty Business Trip

There are some real experiences in this story.

I was excited, I finally got to travel for business and get a hotel room alone. It was in a pretty populated area of the state, so it would be easier to hook up than normal. The weather had cancelled a few of my trips, So I was excited to get out of town, not be known by anyone and be Monika the slut for a few nights.

I painted my toenails red the night before I left. That morning I chose tan pantyhose under my jeans for the ride, and rolled up my jeans 2 cuffs.. I put on an ankle bracelet and wore my light blue low chuck taylors. I got a few looks when I filled up my vehicle and walked into the bathroom. The clerk was very nice as a couple truckers stared at me.

I got back to my vehicle and pulled away from the gas pumps to the parking lot. I logged into a gay/bi hook up site and checked my messages. I waited for my mapping to update, to show my location. I had a few messages from where I originated. I answered them and soon a message popped up. "Are you at the truck stop?"

I replied "yes I am."

The message was from "Truck Daddy" he replied "are you in the white Chevy truck?"

I replied "yes I am"

He replied "You had the ankle bracelet on? You looking to get fucked or suck cock? Were those stockings you were wearing too?"

I replied "If you are clean I can suck you, and yes I am wearing pantyhose."

He replied "I just showered, Green Peterbilt. Just walk over."

I nervously got out of my car, hid headlights flashed and I walked over to his truck. I climbed up the passenger side and he opened the door. He was a tall white guy in his early 50's. He pointed to his bunk and said "Let's go here, take off your jeans"

He stripped down and was naked; his cock was long and thin.

I took off my shoes, and slid my jeans off carefully over my ankle bracelet.

He smiled when he saw my toes. "Very nice color on your toes, you are a true sissy aren't you? What brings you here?"

I replied, "I am traveling on business, my hotel is 2 hours away."

I nodded and he knelt down on his mattress, and pointed to his cock. "What do you call yourself?"

I replied "Monika".

He said "Monika, crawl on your stockinged cover knees and suck my cock."

I crawled over as he stroked his cock. He grabbed his cock and slapped my mouth with it.

He began to talk dirty to me "How long have you worn nylons Monika?"

I whispered back "Since I was 16."

He moved his cock to my mouth and began to slide it in and out of my mouth.

"I bet you were so excited to be exposed in your nylons, ankle bracelet and sissy shoes, weren't you Monika?"

I nodded as I worked on his cock, he would pull out and slap my lips with his cock.

He would throat fuck me and slap my cheek with his cock. I could sense he was getting close and he asked me "Where does Monika want my cum?"

I went to reply and he pulled his cock out and jerked it hard. Cum erupted onto my chin, lips, nose etc. I leaned in and licked his cock as he came more. He moaned and said "Damn, you are a hell of a cocksucker."

He got up to get a paper towel and he looked down at me. My cock was 3/4 hard in my pantyhose, "I want you to cum in your nylons, and wear them to your hotel, and take a picture to send me when you are in your room. Then you get a paper towel."

I laid down and began to jerk off under my pantyhose. He knelt next to me and began to rub my legs and feet. Soon my body tensed and cum blew through the sheer material of my pantyhose. He rubbed my balls through my pantyhose as I continued to flood my pantyhose.

I took a breath as his cum dried on my face. He handed me a paper towel and I wiped as much as I could. He handed me a wet wipe and I got my face clean. My crotch was soaked with cum.

I got up and he said "Pull up your pants, I want a picture of your cum stained nylons when you get to your hotel."

I put my chucks back on and got to my truck. The cum was slowly drying in my crotch. My cock stayed 1/2 hard despite the mess it was in.

I got to the hotel and checked in, the guy working the desk was very nice, almost flirty. I got my key, brought in my luggage and then went back and got my Monika clothes. I went to my room and took off my shoes and jeans.

I took a pic of my very stained pantyhose and sent it to the trucker from the truck stop. He messaged back "I have you as a Favorite, next time I get to fuck you"

I stripped off the pantyhose and hopped in the shower. I shaved my bottom smooth and took an enema and gave myself a douche.

I got out of the shower, and put on my wig cap. I began to put my foundation of makeup on. I lubed my sissy pussy and slid in my plug. I then slid on a pair of Hanes Silk Reflections off black pantyhose with Control top to keep my plug in place.

I finished my makeup, put on purple lipstick, 2 ankle bracelets, splashed body spray onto my nylon covered legs, slid on my platform open toed heels and checked the same gay/bi site I was on earlier. I decided on a white top and a short leather skater skirt. I chose a red wig and chilled out as Monika.

I got a few stupid messages, you know the ones like "host?" or "cock pic?. I ignore those, I have learned if you are more selective you find the right fit. In my younger days, I was in some situations that weren't comfortable because of not screening.

I opened a Michelob Ultra and sat on the bed. I was getting more messages and then I got one from "Dez" that showed 239 feet away. It said "What are you wearing now?"

I grabbed my phone and walked to the mirror and snapped a picture. I sent it and replied "Fairfield?"

I got a fire emoji and a reply "yes".

Now this wasn't the first time this happened. On another business trip (which I can write about) I hooked up with 2 different guys in my hotel.

He sent a picture of a 7 inch cock. "Up for a quick BJ? "

I was horny and replied "yes, I am discreet, are you?"

He replied "Yes I am, what room?

I replied "219".

He replied "Be on your knees when I walk in."

I messaged back "I am not leaving the door open, too many people are here."

He replied back, "I will use my master key to get in, don't worry."

My stomach sank, it had to be the guy at the front desk, before I could reply I heard footsteps coming down the hall.

I got on my knees, I heard him swipe his key.

I looked up and it was him. He was probably in his late 20's. He walked over to me and unbuttoned his pants. He slid down his underwear to his knees. His cock was almost perfect, 7 inches, clean and thick.

He looked down at me and said "good girl, now open up your mouth."

I opened my mouth and he slid his cock into my mouth. I began to suck on it and stroke it. He moaned and leaned back.

He whispered down and said "You smell great, get up on to the bed on your side."

I got up and he rubbed my legs up to my ass. He slid my leather skirt up revealing the control top of my pantyhose. He grabbed my cock and stroked it against the panty of my pantyhose.

I sucked and stroked him until he pulled out and jerked his cock a couple times. Cum splattered onto my top, my chin, lips and even my left eye. He let me lick his cock clean and then quickly zipped up and went down to the front desk.

I got up, cleaned myself up and unpacked and settled into my hotel room. I checked back onto my site and he messaged back "Are you available tomorrow?"

I messaged back "Yes after 2:00 PM"

He wrote back "I work 3 until 11 again tomorrow, at 2:30 I want you to be on your bed on all 4's ass ready to be used again. This time I want you in panties, thigh highs and just a nighty"

My cock throbbed thinking about it, the dominant personality of him was awesome.

I wrote back "yes". I will be ready.

I got a few more messages, but was happy with my first day. I took off my makeup and wig, took out my buttplug and decided I should eat something. There were a few restaurants in the area that were walkable.

I kept on my pantyhose, ankle bracelet and shaper. I put on jeans and a sweatshirt over it, with my light blue converse and walked down to a sports bar.

I ordered a salad and a few beers and headed back to my room. I made sure I walked by Dez and lifted my pant leg for him.

He shook his head and I headed back to the room. I was still horny, and debated what I should do. I decided to walk back towards the Workout room to see if anyone was there. It was all alone. I wanted to tease Dez a little more. I decided I would work out and tease him.

I went up to my room and slid off my black pantyhose. I put on a pair of sheer to waist suntan pantyhose, and put my black running shorts on. I put on some ankle socks, my running shoes and a t- shirt. I took the stairs down to the workout room. I got on the treadmill and ran 3 miles. I could feel the air moving through my pantyhose as I ran. I was feeling extra risky and decided to go to the store by the front desk for a Gatorade.

I walked to the little store and I noticed Dez couldn't stop staring at me. I bent down in front of the cooler as my running shorts rode up revealing my pantyhose covered ass. I walked to the counter and said "put it on my room tab" as I walked back to my room.

I got up to my room. It was around 8:30. I showered again and came out and checked my phone. There was a message from Dez. "Can you wait until I am done? I need to fuck that tonight"

I didn't want to stay up late, but I couldn't resist this. "Yes, I will be waiting, just like you requested."

He replied "See you at 11:00 pm"

My cock throbbed as I was naked in my hotel room. I had 2 hours to go. I bet I could suck one more cock. I had a few messages I hadn't looked at. I browsed through them and I saw one from 400 feet away.

It was from Dknight. It said "great pics, I am hosting tonight."

I replied "Sorry for the delay, just getting dressed after shower."

He replied right away "Anything sexy?"

I replied "Of course". These are the conversations I like to have, not the one liner like "Can you suck and host."

He replied "You should get your sexy things on and get over here." After that he sent a picture. He was black, ripped and had a monster cock. I had to meet him, he was a beautiful human being.

I replied "any requests?"

He replied back "Room 440 at the BW, be fully dressed when you show up to my room, some fairies like to sneak into the laundry room and get ready there so you don't have to walk so far."

I replied ok "I will be there in a half hour".

I quickly lubed my sissy pussy and put in my plug. I slid a pair of tan Control top pantyhose with reinforced toe and my black shaper with the thong back. I went and did my makeup quickly, put on my purple tight bodycon dress and grabbed my laptop backpack. I emptied the contents and put my wig, strappy black heels, earrings and necklace in there. I put on my ankle bracelet.

I put my jeans on, a long sleeve shirt and my baseball hat. I pulled my brim down, so no one could see my makeup.

I went out a side door and walked to the Best Western. I walked in with my head down and looked towards the stairwell.

I walked up to the 4th floor stairwell and opened my backpack. I slid off my jeans, shirt and baseball hat. I stood in the stairwell in my dress and pantyhose. I put on my necklace, earrings, and wig. I slid on my heels and clasped the ankle strap and grabbed my backpack.

I opened the door and I realized I picked the wrong side of the 4th floor. The room was all the way on the other side. My heart was pounding, as I was in full femme and nowhere near passable. I was doing this for the opportunity to see that smoking body and cock. I quickly walked down the hall, my heels clicking with each stride. I got past the elevator and of course it opened. An older couple walked out as I walked by, both of them staring as I began to stride to room 440. They turned and followed me, finally opening their room 5 doors before room 440. I knocked on the door and he answered. He was in a T-shirt and basketball shorts and was on his phone.

He gave me the "Shhh"sign as he continued to talk on his phone. From the conversation, he was on the phone with his wife. I walked in and he nodded with approval. He took off his shorts and stood there. His cock was at least 8 inches and hard. He pointed down to the floor and I knelt down. He brought his cock to my mouth and I sucked his cock while his wife was on the phone with him.

He continued to talk for about another minute while I knelt on the floor of his hotel room sucking his cock. While this was degrading, it turned me on even more. Made to dress like a slut in the stairs of a hotel, now sucking a guy's cock while he was on the phone with his wife.

He hung up and pulled his cock away and motioned me to stand up. I stood up and came behind me and slid my dress up. He rubbed his rock hard cock on my pantyhose covered ass. He felt my plug and whispered "you came prepared." He pushed it in and out of me and then walked to the bathroom. He came back with Nail clippers and he punctured a hole in the back of my pantyhose.

He pulled out my plug and told me to "lean over the bed"

I leaned over and he tore my pantyhose more, soon I felt his cock at the base of my sissy pussy. He worked about a 1/4 of it in and pulled out, He slowly worked in more and more and soon his hands were around my waist as his monster cock was fully inside of me. My legs shook on my heels as he slowly gained a rhythm fucking me.

My body was numb, the pain I initially felt developed into a feeling of ecstasy as I got fucked. I was loving every minute of this. Between walking to his room dressed like a sissy, to pleasuring him as he talked to his wife, to being bent over like a hooker to be fucked, this was amazing.

He pulled out and laid on the bed "Let's see how well you can ride me, bitch. Or what do you call yourself when you are dressed like a fairy?'

My legs were shaking as I replied "Monika" and I eagerly hopped on the bed. I began to straddle him with my face towards him. He shook his head and I turned around with my back towards him, reverse cowboy.

I steadied myself on my heels and slid my sissy pussy down his cock. I began to bounce up and down but would lose my steadiness because of my heels. I slid my toes back enough to where they came out of the shoe and only the strap was holding the shoe on my ankle. Now on my stockinged feet I felt stable and began to ride his beautiful cock.

He began to thrust hips as I was in my own world bouncing up and down on his cock. I got up and tore a bigger hold to expose my sissy cock which was rock hard. The movement and the situation put me into a state of euphoria and soon I shot a rope of cum from my sissy cock across his hotel bed. Cum continued to flow as I gave a subtle cry of pleasure as he pushed his cock into me. I finally put my hands on the bed, and caught my breath.

He pushed me off of his and said "I love when sissies cum riding me. Now finish me off with your mouth."

I flipped around and knelt between his legs. I began to suck his cock and he reached down and began to jack his cock. I put my mouth over the top of his cock and moved my hands to his balls. He jerked himself and let out a big moan. Cum shot up and blasted into my mouth, my nose, my eyes and even onto my wig. I finally put my mouth over the top of his cock and finished swallowing his cum. I got up and unbuckled my shoes and walked to his bathroom stockinged foot.

I wiped myself down, changed into my male attire and headed back to my hotel. I got back and it was 10:30 pm. I quickly stripped down from my male clothes and took off my destroyed pantyhose. I slid on a pink thong, tan thigh stockings, a pink corset and my pink robe. I put on my black heels and freshened up for Dez to come by.

Around 10:55 I turned down the lights in my room except for one. I got on the bed on all fours with my ass facing out. At 11:02 the door opened. My Stomach churned as Dez made his way in.

He whispered "Perfect." as his hands moved from my ankles to the tops of my stockings. It moved to my thong and he slid his finger into my ass. He slid it in a few times and then pulled it out.

He whispered "Did you just get fucked?"

I nodded up and down.

He whispered back "I can tell, your pussy is all puffy. Tell me the details."

I replied back "I met a guy online, he was staying at the hotel right by here, I dressed for him and he fucked me"

He whispered back "Was he big Monika? Where did he cum?"

I replied, "On my face."

He whispered louder "So he treated you like the cheap slut you are. He fucked you and came on you."

All of a sudden he smacked my ass three times hard and said "get on your back slut."

I laid on my back, he pulled my legs towards him, to where my ass was on the end of the bed. He spread my legs and slid his cock into my well fucked sissy pussy. He angrily thrusted in and out of my ass, holding onto my stockinged ankles as he fucked me. His whispers got louder as he said "You like getting fucked again slut? Working out in your sissy pantyhose so you can get fucked again, you are a whore."

I think the dirty talk turned him on more than me, he pulled out and pulled me off the bed onto my knees. He stuck his cock into my mouth and facefucked me for a second before cum blew from his cock into my mouth. I brought my hand out and jerked him into my mouth. He pulled his cock out and said "Open up Monika."

I opened my mouth and showed him his cum before I swallowed it down. He got dressed and left without saying a word. I got up, slid off my heels, brushed my teeth and slept in my lingerie.

The next day I was to leave back home. I slept some and woke up around 6 am. aroused in my lingerie thinking about the last 2 days. My goal was one more hookup before I left the hotel. I had a zoom meeting at 9:00 and I figured I would leave then.

I got up, had some coffee and showered. With me traveling, I wouldn't be able to make myself as Monika, so if I hooked up, I would be just a male sissy in pantyhose and panties.

I logged on and put in my profile "No wig and makeup today, but will wear whatever you want"

I got a few messages "Why can't you wear a wig" or "Just do a quick makeup job. I ignored those. I finally gave up and packed to leave. I did wear one of my remaining pairs of tan pantyhose under my dress pants with my loafers and no socks. Maybe I would stop at the truck stop where it all began.