Secret Life Pt. 01

My wife allowed my crossdressing as a part of our marriage. Her theory was it made me horny, and she would reap the benefits of it. There would be numerous times when we would travel, I would be wearing panties, a bra and pantyhose under my regular clothes.

My wife Jamie, was 41, successful, confident and loved that I was adventurous. She worked from home in insurance claims. She found my stash of clothes one day at my place while we were dating and never wavered. The next day when we woke up and got ready, she told me to "wear the panties in my bag." She knew I had a nylon fetish and would oblige to it at times. She began to buy more clothing to wear and our sex life was hot.

I travel for work about once a month, sometimes I would fly, sometimes I would drive depending on where our meetings are located. Jamie would request I wear panties and nylons when I travel and sometimes take a picture at a rest stop for her. Once in a while, I would make a video for her masturbating in my lingerie.

One particular trip, I was driving to a destination 6 hours away. Before I left, I slid on a pair of red panties, black thigh high stockings with no socks, and a shaper. I wore jeans, black loafers and black long sleeve button down shirt. Jamie approved and added more lingerie into my suitcase.

I drove down to the conference and got to the hotel. I snapped a picture and sent it to Jamie. She sent a heart emoji. Some of the Vendors were set up down below, I got to my room and put my suitcase away, freshened up and took a walk down to the Vendor section.

There were assorted Vendors lined up. The products ranged from software, to finance, to equipment. I stopped by a few Vendors and chatted with them. I stopped by one of the financing ones to chat with our current representative Patrick.

Patrick helped with the financing of our operation. He was in his early 50's, good looking and in good shape. He was knowledgeable and always worked for our company.

He was in good spirits and we chatted. His assistant Lori was there and he said "You can watch the booth, I am going to take Chris for a drink here."

We walked to the hotel bar and he ordered us drinks. We chatted about business, the industry etc. I had a little buzz going and forgot I was wearing black nylons with no socks with my jeans. Patrick went to the restroom and I noticed the cuff of my jeans were at my ankle. I pushed them back down and Patrick came back to the bar. He ordered another round and leaned over to me.

He softly and slowly said "How long have you worn pantyhose Chris? I've suspected you had pantyhose on before when I had seen you."

My face turned red. I scrambled for any words, I meekly replied "For a while, my wife knows."

Patrick nodded and softly replied "I have an attraction to men that embrace their feminine side. I was hoping to see you here today and check to see if my hunch was right."

I was speechless, Patrick continued. "Do you dress for men Chris? Or is it just for you and your wife?"

I replied "For myself and my wife. She likes it because it excites me."

Patrick looked at my eyes and said "Does it excite you that you got caught? That I know you have nylons on right now? Do you want to show me everything you have on?"

My cock was rock hard under my panties. I had never been confronted since my wife found my stash. I looked at Patrick and said "I am going to use the bathroom." I walked to the bathroom and tried to gain my composure. I was embarrassed but yet excited.

I came out and sat down. I looked at Patrick and said "So, what do you want? Are you going to blackmail me or something?"

Patrick calmly looked at me and said "Oh no, not at all. I wouldn't do that to you at all. It will be our secret. I would just love to see what else you have on that's all. But it will be awkward for you to see me now when I visit your office, won't it? Maybe granting my request will make it less awkward."

I finished my drink. I was kind of drunk and my nerves translated to excitement. A part of me wanted to be exposed in lingerie in front of another male. Every Crossdresser at one point thinks of getting caught and the steps that follow.

I looked at Patrick and said "Come up to room 453 in 10 minutes" I got up and went to the elevator.

I got to my room and took a breath. I slid off my shoes and jeans. I stood in my thigh highs, panties, shaper and shirt. I slid my shirt off and grabbed my purple silk robe. My nerves were gone, the way Patrick talked to me made me feel sexy. It was an odd feeling.

Soon there was a knock at the door. I opened it slowly and Patrick was there. Patrick had a bottle of whisky with him and a bucket of ice. He looked at me up and down and smiled. He nodded and said "Even better than I expected, you have great legs. I bet in heels they even accent your tone more."

I replied "Thank you, does this satisfy your needs now?"

Patrick smiled, "yes it does, but don't you think it would be nice for you to have a drink with someone all dressed up in your sexy lingerie? You can relax after your long day of traveling."

I shook my head and grabbed 2 plastic cups from the bathroom. Patrick scooped some ice and poured a drink for us.

I sat on the bed with my drink, Patrick sat on the chair next to the desk. I looked at him and said "What got you into your affection for Crossdressers?"

Patrick took a sip and said "I was out in Vegas for a convention, I was partying and it was late. I ended up playing slots at 2 am at the New York, New York hotel. There were 2 near passable crossdressers walking back to their room. I approached them and asked them to have a drink with me. I ended up going to their room that night and having amazing sex. I think I came 4 times in like 3 hours. It was incredible.

Patrick took another sip and continued. "I still date women, but I love encounters with crossdressers and fembois now. The taboo of them wearing panties, nylons, etc just turns me on. "

I could see Patrick was getting aroused and was staring at my legs. My cock was semi hard under my panties. Hearing Patrick speak was arousing.

I took a slam of my whiskey and looked at Patrick. I whispered to him, "you can touch my legs if you want."

Patrick got up and walked over. He put his hand on my nylon covered knee and I felt a rush of electricity. He moved it up and down my legs down to my toes. He leaned over and brought his lips to mine and soon we were kissing. My cock was rock hard in my panties as I felt feminine and sexy dressed in my lingerie.

Patrick broke off the kiss and asked me "Do you want my cock?" I nodded and he slid off his dress pants and underwear. His cock was about 6 inches and thick and rock hard. I instinctively reached up and stroked it. Patrick said "Slid up on the bed."

I slid up on the bed and his hands roamed to my legs to my precum soaked panties. I stroked his cock and he told me to lay on the side.

I laid on my side and he rubbed my ass and thighs. He moved his cock to my lips and I opened them up. He thrust his hips forward and I had my first cock ever in my mouth.

I opened my lips and let Patrick slide his cock in and out of my mouth. I remembered to replicate what my wife did and suck as he thrust inward. His hands roamed my nylon covered legs and panties. My cock was rock hard in my panties as we continued.

Patrick tensed up and whispered "I'm cumming" as I tried to swallow my first load of cum. I kept up for the most part until the end when a last spurt coated my lips and nose. Patrick pulled away and slid up his pants. I looked at him and said "Can you grab my phone? I will send my wife her tribute video."

Patrick walked over and grabbed my phone. I licked more cum off my lips and slid down my panties, and began to record a video on my phone. My cock was rock hard. I stroked my cock and after only a few strokes one of the largest ropes of cum blasted out. I moaned and whispered "Oh Jamie" to the phone. I regained my composure as Patrick watched.

Patrick grabbed a towel out of the bathroom and brought it to me. He smiled and said "That was hot, do you want to split a Pizza? We could have it brought up here."

I nodded and Patrick ordered a Pizza. I went to the bathroom and brushed my teeth and cleaned up.

I sat back down on the bed and Patrick and I chatted. He asked about my dressing, how it started etc. I told him one night my wife told me I had to wear nylons if she did. It tripped something in me, where we had sex 6 times that night. He asked if I had ever thought of dressing fully with makeup etc. I told I had thought about it.

There was a knock at the door, the Pizza was here. Patrick looked at me and said "I should make you go get it, but I will be nice this time." Patrick went and got it and we ate and chatted some more. WE talked about our schedule over the next 2 days. I got up and cleaned up and straightened the room.

I walked back, still dressed in my robe, shaper, panties and nylons. If fett exhilarating and sexy to just walk around another guy dressed in lingerie. I think Patrick enjoyed it as well as he got up and stopped me. He put his hands on my shoulders and said "Kneel down and suck me, before I go to bed.

Without any hesitation I knelt down. Patrick unzipped his pants and slid down his underwear. His cock was 3/4 hard. I reached out and stroked it and slid my lips over it again. I slid my lips over his cock and began to suck it. I stroked his cock at the same time remembering the methods my wife used on me.

I continued for a while, knowing that he just came and this one would be a lot more work. Patrick moaned and would thrust his cock into my mouth on occasion. He finally tensed up and I received my second load of cum into my mouth. I swallowed it down and Patrick pulled his cock out of my mouth. He pulled up his pants and I got up from being on my nylon covered knees.

He patted me on the ass and said "Let's try to make our schedules work tomorrow" I nodded.

I cleaned up, showered and changed into a fresh pair of panties and tan pantyhose before going to bed.

I slept off and on that night. A lot of thoughts entered my mind. I was a cocksucker, but I enjoyed how Patrick seduced me. He made me feel sexy. I loved my wife and the freedom she allows, but that was the best experience I have had.

I woke up early and worked out. I hopped on my computer and looked at Crossdressing videos on Youtube about makeup, etc.

I showered, slid on a pair of tan pantyhose and light blue panties with a white shaper. Over it I wore a pair of black dress pants, a purple button shirt and black loafers.

I walked down to the main floor and went to my first session and then my second session. I wasn't too concerned about anyone seeing my nylon covered ankles, a lot of men were now wearing loafers with no socks.

We were free on our lunch break and my next class was at 1:45. I stopped by Patrick's booth. He gave me knucks as I walked by.

I just smiled and he asked "How is your day going?"

I replied "good and yours?"

He replied "Busy as hell"

I stood next to him and slid my loafer off and on quickly. He looked down at my nylon covered foot and nodded. He had Customers flowing in, so I said "I am going to head out."

He quickly yelled at me "Pre Dinner cocktail at your room around 7?"

I nodded and went back to my room. I watched another video on youtube and the feeling of seducing Patrick took over. I had almost an hour and a half before my next session.

I made a list of things I wanted to buy. I was going to shock Patrick when he showed up at 7 pm. I googled some department stores and planned my outing. I went to an ATM and pulled out cash, so my wife wouldn't suspect.

My first stop was at a department store nearby. I browsed the women's shoes department and found a pair of black high heels with a slingback. I figured I was a size 11. I found a box and quickly took one out of it and slid off my loafer. I eased my nylon covered foot into the heel. It was electric, my cock twitched. I took the heel off and slid on my loafer.

A clerk walked over and said "Did you need any help or a different size?"

I shook my head and moved on to the women's department. I knew my sizes from trying on my wife's clothing. I found a checked schoolgirl skirt in a size 10, along with a pink turtleneck. I found a denim dress on sale as well.

I ran over to the hosiery department and grabbed 3 more pairs of pantyhose in black and tan.

I finally checked out.

Then I stopped at a Makeup store and looked at my list from my youtube video. I gathered foundation, lipstick, eyeshadow, eyeliner, lipstick and blush. I picked out some nail polish, remover and makeup remover pads.

The clerk was a male, he smiled as he saw my items. At this point, I didn't care. My obsession with seducing Patrick was overwhelming my thought process.

My final stop was a drug store. I stopped and bought lube, enemas and condoms, a cheap bottle of body spray and found a cheap wig on clearance from their Halloween items.

I got back to the hotel and unpacked my things. I hung my new female attire.

The afternoon sessions felt like they lasted a month each. Finally at 4:30 they ended. I ran to the hotel bar, ordered 2 tall whiskeys and Diet Cokes to go. I got back up to my room, stripped down and took a long hot shower. I shaved my legs and crotch smooth.

I got out of the shower, dried off and then attempted to paint my toenails. It took me a couple tries before they were done. While they dried, I pulled up my youtube video on how to put on makeup and began to follow the guide step by step. I looked in the mirror and was amazed how feminine I looked. My red lipstick accented my look. I was not passable, but looked feminine for my first attempt.

I finished my makeup, gave myself an enema and slid on a pair of tan pantyhose, red panties over them with my shaper as well. My toes looked amazing under the reinforced toe of my nylons. I sipped my drink and slowly began to feel a little drunk. My nerves were calming, but I was excited to see what Patrick would think of me transformed.

Around 6:40 I put on my skirt, turtleneck, and heels. I put on the wig as best as I could, but it was a cheap Halloween wig.

I sat on the bed and turned on the TV and waited for Patrick.

There was a knock at the door at 6:55. My stomach churned. 48 hours ago I was just a normal guy that liked to wear women's lingerie to travel or with my wife. Now, I was a Crossdresser fully made over, waiting for a guy that I sucked off twice yesterday.

I got off the bed and walked to the door. I could hear the clicking of my high heels. I opened the door a crack and peaked at Patrick. I said "Come in please" as I went behind the door as he opened.

Patrick closed the door and looked at me. He was shocked.

He finally spoke and said "Holy Shit, I didn't expect this."

I looked at him and said "I guess I wanted to try this and surprise you."

Patrick still looked shocked, "You look amazing, you are sexy as hell."

Patrick walked over to me and pushed me against the wall. He kissed my lips and lifted up my skirt. His hands roamed my ass and legs. He grabbed my hand and brought it to his cock. I stroked it through his dress pants and he pulled away and took off his pants and underwear.

I stood next to him and began to stroke his cock as he rubbed my legs and ass. He gently whispered "Suck it" I knelt down, on my pantyhose covered knees and began to suck/stroke his cock. I could taste precum as I continued to blow him.

He moaned and stopped me. He whispered "Stand up and take off your skirt"

I stood up, took off my heels and removed my skirt. I was standing before Patrick in my turtleneck, red panties and tan pantyhose. His cock was rock hard as he lustily looked at me.

He walked over and rubbed my ass and cock tucked under my pantyhose and panties. He moved his mouth to my ear and said "Have you ever been fucked before?"

I shook my head and he said "Let me be your first, do you have lube?"

I nodded and walked to the bathroom and got the lube. I looked at him and said "I also douched already"

Patrick said "Kneel down on the bed, your ass towards me."

I got up on the bed, Patrick, went behind and I felt his hands grab my panties and pull them down. He slid them off my toes and smacked my ass.

He then said "I am going to ruin your pantyhose" and soon there was a rip in the crotch of my pantyhose and I could feel my sissy hole exposed. He put lube on his fingers and slowly worked a finger into my ass, then a second. It hurt but I also felt sexy.

He pulled his fingers out and lubed his cock. Soon I felt it at the tip of my sissy pussy.

He slowly worked his cock into my sissy pussy, I bit down on a pillow to not scream. He pushed it all the way in and slid it out. He worked it back in and began to develop a rhythm as the pain lessened. He put his hands on my hips and began to fuck me with more intensity.

My pain went to pleasure as I could feel my cock harden under my pantyhose.

Patrick pounded me and began to taunt me "You are going to be my pantyhose wearing whore from now on, aren't you?"

I nodded yes and continued to enjoy the best sexual experience I have had.

Patrick soon tensed up and held my hips as I could feel his cock releasing cum into my ass. He moaned and held me in place. I reached down and stroked my throbbing cock and flooded my pantyhose with cum as I almost blacked out.

Patrick slowly pulled out and I instinctively got off the bed and knelt down in front of him and cleaned his cock.

He whispered "That was incredible" and pulled me up. He looked down at my nylon covered feet and said "I love the painted toes as well, it makes it even more sexy knowing that you wear nylons all the time and now have painted toes. What if you had to take off your shoes at some seminar?"

I smiled and said "I don't know..lol"

Patrick put his pants back on and said "I have clients to entertain, maybe later tonight or tomorrow before you leave we can meet?"

I nodded and Patrick left. I went and got a towel and began to sponge my ass, as cum was dripping down onto my ruined pantyhose.

Still in my makeup and ruined nylons I called my wife. She asked about my cash withdrawal and I told I was helping with prizes and entertained Patrick. If she only knew how I entertained him.

I finally undressed, took a shower and put on a fresh pair of pantyhose and panties. I put on my male attire and went to bar, had dinner and masturbated again thinking of my first fucking as a pantyhose wearing sissy.