Business Trip Sissy

Being a married crossdresser, business trips can offset the lack of dressing I do because of my marriage. Don't get me wrong, my wife knows I dress, supports it and encourages it when we travel. But the difference between living alone and being able to dress most of the time versus being married and having family, friends etc be a part of your life is huge.

My wife suspects I am bi-sexual. When she found my stash of clothes when we were dating, she asked if I was with a man before. Before I could answer, she moved onto a different question seeing I am sure her mind was going a million miles per minute when she saw my heels, pantyhose and lingerie in a suitcase.

I am bi-sexual and feel very passive and submissive when dressed. I had a regular in my younger days, and loved being on my nylon covered knees feeling his cock explode with cum into my mouth. Being married and my wife being a prominent woman in the community, I don't fool around much with other men in my area. But when I travel, I have no restrictions.

My company recently enrolled me in a 3 part class in a city about 5 hours away. The company said I could drive my own vehicle and get reimbursed for mileage. My wife sometimes goes on these trips with me. This time she declined, which gave me a week to prepare for the trip.

I work earlier than my wife, so I am home earlier each day. Each day for a week, I would put a dress, bodysuit, heels etc into the storage part of my truck. The day of the trip, my wife picked out a pair of pink panties and tan pantyhose for me to wear under my business attire. She always encourages me to wear lingerie when I drive and travel.

That morning, I stopped in the office and then took off for my destination. I was wearing khaki pants and a light blue golf shirt. I did pack a pair of shorter khaki shorts to wear in case it got warmer. About an hour out on my trip, I pulled into a rest stop and slid on my shorts over my pantyhose. I slipped on my loafers and continued my trip.

I had gone out on some hook up sites prior to my trip and had plans to meet a guy named Frank at my hotel when I got there. I needed some supplies for the room, so I swung into a Walmart about 45 minutes from my destination.

I debated on putting on sweatpants prior to walking in, but chose not to. I strided into Walmart with my pantyhose covered legs fully exposed. I felt sexy, exposed and very much like a crossdressing sissy. I walked over to the pharmacy section and picked out a 3 pack of enemas and lube. I walked over to the pantyhose section and picked out a pair of tan Leggs sheer energy pantyhose and a pair of off black ones. I walked to the alcohol section and picked up a 6 pack of beer and checked out.

Most people didn't notice my legs, the clerk did though. She smiled and said my legs would look good in black nylons too. (I do shave my legs and have better legs than my wife). I blushed and walked out.

I decided to change back into jeans to check into my hotel. I checked in, douched myself, and sat back down in my pantyhose and panties at my computer. I logged into my email and sure enough there was a message by the guy I had chatted to prior. He said he would be there in 45 minutes. I put the shorts back on and headed out to my truck.

I had brought an empty bag and walked out to my truck to get my clothes. I packed up my dresses,lingerie, heels etc and went back to my room. A couple glanced at me when I walked by in my shorts and pantyhose.

I got back to the room and chose my outfit. I chose my red wig, quickly put some makeup on and then chose a black skirt with a pink top. I put on my shaper underneath, slid on my black slingback heels and cracked a beer.

I looked in the mirror, I could have done better with the makeup, but I think this guy just wanted my ass anyways.

I finished my first beer and I heard a knock at the door. I looked at the peephole and it looked like Frank.

I opened the door and Frank followed me in. He was exactly how he described himself, 5'11, stocky build around 45 years old. He smelled good, and sat on the bed.

He wasted no time and said "Lets see that ass slut," I got up and turned around in front of him. He reached under my skirt and slid my skirt up to my hips. "It looks better in person, I will say that Krissy. (which is my crossdressing name). He quickly gave my ass a good smack and aggressively grabbed it.

He patted the mattress and said "Get up here on all fours and suck my cock." I got up there and he got off the bed and stood at the end of it. He took off his jeans and underwear revealing a nice 6 inch cock with some girth to it.

He put his head on the back of my head and I moved my mouth to his cock. I was back in my sissy element, on a bed dressed like a slut, my pantyhose and panties exposed, sucking a cock.

I sucked his cock, licked the underneath and licked his balls. He was rock hard. After 10 minutes Frank pulled away and said "Did you douche yourself sissy?"

I nodded and I pointed to the lube on the desk in the hotel room. Frank came up behind me and said "Pantyhose down, or ripped?" Before I could answer I felt his hand puncture a hole into the gusset. A tearing noise happened after and I felt my panties being pulled to the side.

Frank fingered my sissy pussy and spanked my ass for a minute. Pretty soon I felt the head of his cock rub my sissy pussy. He put his hands on my hips and said "It's time to get fucked Krissy."

He slowly pushed his cock in my well lubricated pussy, I could tell I haven't been fucked in a while because it hurt and I had to bite down on my sleeve not to scream. Frank could sense and said "Relax Krissy, It won't hurt for long."

Frank methodically picked up the pace, and my pain transformed into pleasure. He began to fuck me hard, and he would smack my ass about every 5 strokes. He pushed down where I was laying on my stomach and began to drive my sissy pussy hard. My cock was rubbing against my nylons and panties and was becoming harder and harder.

All of sudden he pulled out and had me lay on my side. He knelt next to my face and jerked his cock a few times until cum splattered all over my nose, eyes and open mouth. He brought his cock to my lips and I licked it clean. He got off the bed, and went to get me a towel.

I laid down on my back, I was so close to cumming. Frank brought me a towel and I wiped my cum splattered face. Frank quickly put on his underwear and jeans and left.

I got up and wiped my makeup off, I was still horny and debated about getting myself off. I decided against it. I changed out of my ripped pantyhose and panties, ate part of my dinner I picked up and chilled out.

I had pent up energy, so I decided I would work out. Then I thought, maybe I will work out with pantyhose under my shorts. I was horny and in full sissy mode after the day and slid on my tan Leggs Sheer energy pantyhose. I put my gym shorts on and my tennis shoes and headed to the fitness center.

There was one person in the fitness center, an older man walking on the treadmill. I walked over to the elliptical and stretched out. It felt invigorating to have my pantyhose on in public again. I got on the elliptical and began to pedal. I worked out for 30 minutes, burning up energy. The friction between my pantyhose and shorts caused my cock to stay half hard during my workout. The older man was at the water cooler when I walked over to get a drink. He took off his headphones and said "you were moving on there, I see you did get a run in your pantyhose though."

I looked down and yes a run in my pantyhose was visible by my achilles up the back of my calf. He continued "I'm sorry I was looking at your legs, I was wondering if you were wearing nylons or not. Then the run appeared. "

My stomach churned, and I replied "Obviously I am." I walked over to get a towel. He asked me "Do you wear them for circulation problems?" I should have replied yes, but stupidly said "no, I just like wearing pantyhose."

He gave me a look of lust, I was nervous but this is what I wanted. He looked at my legs and said "You have amazing legs, better than 90 percent of the women I know." I replied "Thank you, " and got another glass of water.

I took a sip and looked at him. His cock was causing his shorts to tent. I looked at him and said "It was nice meeting you, and I went to walk out of the fitness center. He quickly blurted out "Want to go in the steam room? My wife is in our room."

I turned around and said "We can go to my room."

I took the stairs and he followed me to my room." I swiped my card, opened the door and stripped off my shorts and shoes. I was just in my pantyhose and workout shirt. He stood by my bed, with no conversation I knelt down and he slid down his shorts.

His cock was about 7 inches and thin. I quickly engulfed it and began sucking it. I took my mouth off of it and talked dirty to him. "Did you like my pantyhose? Did you want to rub them when I was on the elliptical?" While I stroked his cock.

I could tell he was going to cum and I stood up rubbed his cock on my pantyhose covered ass. I stroked his cock and turned around. Cum blasted from his cock onto my pantyhose covered cock. I rubbed it in my pantyhose as he kept spurting cum.

He pulled away and pulled up his shorts. He looked stunned. He shook his head and said "That was incredible.." I looked at him and said "I'll be ready tomorrow at 7:00 AM if you want to cum over." He nodded and left my room.

I took off my pantyhose, rinsed them and hung them up in the bathroom. I was only down to my black pantyhose for wearing, and I figured I could wear these for working out and if I got a visit at 7:00 AM tomorrow.

It was past 9:00 PM, so I decided to shower and get ready for bed. I had a great sissy day. I needed to cum, but I figured I would save it for after my shower.

I finished my shower and put on my black Leggs sheer energy pantyhose. It was the only pair I had that had no runs or cum stains on them. I put on a pink bodysuit as well and laid in bed to pleasure myself before I went to sleep.

I grabbed my phone and decided to look at some porn, while I jerked myself. An ad for a gay hook up site popped up and I accidentally hit the pop up. I went to close it and decided to say I will make a profile. I went through the process of setting it up. They asked for a profile pic, I took a picture of me laying there in my black pantyhose and pink bodysuit and it got accepted. The site asked for a profile heading. I entered "Hotel sissy looking for Daddy".

I waited for the confirmation and soon I was on the site. My cock stiffened as I scrolled through the members. Soon I received some chat requests. A few of them I ignored, until I got one I had to respond to. It was from "HungDaddy4". I opened the message and a picture popped open with a black cock that was 8 inches long. My cock twitched in my pantyhose as I stared at it. Soon a word message followed "R U real?"

I replied "yes I am real." Another message followed "Can I fuck you?"

My cock was leaking precum, "Yes, if I can handle it."

He messaged back "hotel and room number, do you have heels as well?"

I sent my information and said "Yes, I will wear heels. You will have to message me when you get here, the doors lock at 10:00. I will let you in at the South door, nearest to my room."

He replied "I'll be there in 15 minutes"

I got out of bed, I took off my bodysuit, did a quick enema, lubed my sissy pussy and slid on a white thong over my pantyhose. I put on a black teddy, my pink robe, my wig and put some lipstick on along with some eye make up. I slid on my slingback heels and waited. Then I thought, shit I have to go let him in dressed like this.

At this point, my sissiness was out of control, I think I would have worn pantyhose and dress anywhere at this point.

Soon I received a message "here".

I grabbed my key and walked down the stairs to the entrance in my robe, pantyhose and heels. I got to the door and he was there, along with a girl having a cigarette. I opened the door and she laughed and said "Very sexy and slutty, I like it."

He looked me down and followed me up the stairs to my room. It was exhilarating walking throughout the hotel in heels and robe with a black man behind me that was going to fuck my brains out. The air breezed through my nylon covered legs.

I opened my door and walked in. He came in, closed the door and took control. He walked over to the bed and told me to lay down on my stomach. I did it with my head at the edge of the bed.

He quickly took off his pants and underwear, exposing his 8 inch cock. He brought the head of his cock to my lips and I eagerly opened them and began to suck his cock. He thrusted his hips to fuck my mouth, as I felt like a complete piece of ass for him.

He pulled out and climbed up on the bed. He had me roll over and soon I could feel his hands go right to the crotch of my pantyhose and sure enough, a hole was ripped in my black pantyhose. He fingered me for a while and then laid down. He told me to get lube, which I did. I lubed my sissy pussy and got back on the bed, I laid down a towel and he laid back down over it. I put some lube on my hand and stroked his rock hard cock.

He looked at me and said "Start riding my cock slut. You know you want to." I climbed up on the bed and straddled over his cock. I tried to slowly squat down on it, but my heels made me too wobbly. I slipped off my heels and threw them on the floor. It was much easier in my pantyhose covered feet and I slowly lowered onto his monstrous cock.

My sissy pussy was tightening up and I focused on relaxing it. As I lowered, he grabbed my hips and slowly thrusted his cock up as gasped with the pain of having this monster cock in my sissy pussy. I slowly started to slide up and down on his cock, it felt like his cock was hitting my stomach at times. All of a sudden the pain turned into pleasure as I rode his cock.

He was thrusting his hips up as I rode as well, he was getting into it and started calling me sissy white boy, and "said all you faggot white guys like to wear panties and nylons and get fucked by black cock. You are a dime a dozen."

He told me to get off and he maneuvered me on my back, he grabbed a pillow and had me sit on it. He bent my legs back and slid his cock into my well fucked sissy pussy. He grabbed my pantyhose covered ankles and feet and began to drill my ass. My cock was 3/4 hard under my pantyhose and panties. I was in a sexual haven. I looked in the mirror at the hotel and saw my muscular legs in black pantyhose being held up as I was getting pounded by this beautiful black cock.

He pounded me and began to hit a spot, where I got a sensation in my loins, after about 10 more thrusts, cum erupted from my cock through my panties and pantyhose. I yelled breathlessly "Oh my god, Oh my god" I had never had a sissygasm before. I turned my head and moaned as the pleasure continued. My panties and pantyhose were flooded with cum. He pulled out and laid down. "Now get on top reverse Cowgirl style, slut."

I maneuvered myself and he guided me onto his cock. Reverse cowgirl was easier as I squatted like a crabwalk as he fucked me. He grabbed my shoulders and thrusted into me as I came down. I was getting horny again in this position. We fucked for 5 minutes like that when he told me to get off and lay down.

I immediately obeyed and he straddled my face. He put his asshole by my tongue and I licked his asshole and balls. He finally put the head of his cock by my lips and gave it a couple jerks. Cum splashed all over my face, up to my wig, all over my lips. He gave me the best facial I have ever had. My face was coated with cum. He rolled off and I pulled down my pantyhose and panties. My cock was rock hard. I stroked it 4 times and for the second time in 10 minutes I came.

I grabbed the towel and wiped my face, ass and my crotch off. He quickly got dressed and left. My ass was stretched and sore. I never got up as I fell asleep in my ripped, cum soaked pantyhose and robe.

I finally woke up around 5:30 and my ass felt like it got a workout like no other. I showered and put on the pantyhose that guy from the gym came on.. I waited until 7:30. He was a no show. I packed, went to my class and drove back home, cherishing my sissy night and knowing I had another class here in a month.