Ultimate Sissy Fail

This is the story of the perfect sissy getaway.

This story contains subjects of crossdressing and interracial male sex acts if this offends you please don't read. Everything except one or two events happened, Now, there is some embellishment. I had to tell someone. I decided to tell everyone.

A little bit about myself. I am in my late 50s. My adventures in crossdressing didn't start until about five years ago. I was shoe shopping with my wife when I spied a pair of red five-inch, peep toe, platform, pumps, ankle strap, and with both bow and zipper in the back. At the time, couldn't have told you what they were other than being the sexist shoes ever. I don't know why imaging fucking wife while she was wearing the shoes gave me an instant hard on. I brought her over to look at them and she said no way in hell would she ever wear anything like that, I was instantly deflated. It seemed for the next week all I could think of were those shoes. I got online found a pair online in my size, I ordered them as well as a garter belt and full fashion stockings.

When I received notification of package arrival, I hurried to the post office. My cock was hard the entire trip to the post office again over just a pair of shoes. I couldn't wait to get back home and try my shoes and stockings. From that moment on I have been a closet cross-dresser and wanna-be sissy.

I cross-dress at home as often as I can, and I travel about once a year. I have never gone out in public dressed except to get the occasion bucket of ice in a hotel. After years of been inundated with numerous sissy, interracial, cuckold and hypnosis porn. I wanted to go the next step and suck and fuck an actual cock, go on the town to a tranny club and mingle with other likeminded cross-dressers to talk about my life style. Finally, I would like to evidently find an alpha male to dominate both my wife and me.

I planned a trip to accomplish first few steps to see one if I would enjoy or just fantasied about sucking cocks and having sex with a man. Planning for this trip began months ago when my plans to visit a large Midwestern town were cancelled. I told work I was going on vacation. I told my wife I was on a business trip. I planned my three-day trip to that midwestern town, I knew it had establishments with gloryholes, and LGBTQ friendly shows, clubs and bars. Also, I could stay at a hotel/casino for free and just have a short drive to town.

The excitement was building for weeks, I ordered new dresses, matching garters and multiple pairs of Italian stockings, an open bottom full girdle and new of course new shoes. I had a glamour outfit including a nice short black dress, and I found the best sissy outfit it was centered around pink and white pokkadot open bottom brief girdle and bra set, a nearly matching pink pokkadot rockabilly swing dress, a pink petticoat, and finally a pink pair of 4inch chunky heel Mary Jane pumps.

The week prior I read what seemed to be hundreds of stories on Literotica, anywhere I could find time. I watched numerous sissy videos, I would edge myself multiple times a day without relief. I was so brazened I would masturbate just feet away from my wife in the living room. I wanted myself to be at the peak of sexual frustration, so I would be a sex crazed sissy in a town full of strange cock.

I ordered a new cock cage online, it looked to be industrial strength steel, weighing nearly six ounces. I only tried it on once, it seemed to be very heavy. I didn't figure I would be wearing it long, just in the adult bookstore to help me from getting out of control.

The day before the trip I ran out to the drug store for some what I would hope to be blow-job proof lipstick (bubblegum pink and a very whorish red) and some condoms, I only wanted magnums sized condoms anything less would be settling for less. The only package of magnums was a package of 36. I didn't think I would need that many, I was planning to be a total slut but that was ridiculous. I would pick up some en route.

All the preparations were made, I was totally shaved.

I planned my first day. I would drive to a rest stop, there was one conveniently located within twenty minutes of the adult bookstore which was the first stop on my slutty journey. At the rest stop I would put on a garter belt and stockings under my track pants. From there it was to the bookstore where I would sit at the gloryhole and suck at least four cocks. Then to the hotel for a relaxing bath, a calming drink and prep for my first night out on the town. I would finish my night at the local club and hopefully return with a play partner for the remainder of the evening.

Arriving at the truck stop, I parked at a remote spot. I gathered my whore bag with all my clothes, I went to the men's restroom. Sliding off my track pants. I pulled the pink stockings up my smooth legs. I attached the stockings to my panty girdle. As I was inserting my butt plug, I thought I heard someone else in the bathroom. I froze, I looked through the gaps in the door, I couldn't see anyone. I continued my dressing. I pulled up my pants and headed back to my car. I opened my car door and a man approached He said

"Yo cocksucker, come here and suck my cock."

I replied "I don't know what you are talking about."

"Look anyone wears stockings and panties in a men's restroom is a cock sucker." He said.

He undid his zipper and pulled his cock it wasn't impressively long but it was...

I HAVE TO STOP RIGHT HERE... I SAID THIS WAS MOSTLY TRUE... THAT PREVIOUS PARAGRAPH WAS TOTALLY FICTITIOUS.

Unfortunately, it didn't really happen like that. This was how my first day really went.

The evening before my departure, my wife and I enjoyed a quiet evening. I had a nightcap and I went to bed at a decent hour, since the day ahead had a long drive. I fell asleep fast, but it didn't stay that way.

I tossed and turned all night, like a kid anticipating Christmas morning. Finally, about 4am I decided to move to the couch as not to wake my wife. It was shortly after 5am when I realized something was dreadfully wrong, I was laying in a huge pile of sticky wet and cold cum. So much for edging myself for a week. Now, I must explain to my wife the wet spot on the couch.

Now that I am fully awake I realize that there is pain in my left cheek, oh no I must have bit my cheek during the night. If that wasn't enough, my lips feel cracked and painful. Looking in the mirror, my lips look like a dried-up watering hole in the desert. Great so much for any chance of oral sex. If that wasn't enough, I developed a case of hemorrhoids overnight. I have not had a problem there in over twenty years. What the hell is going on, I thought to myself. My body must be rebelling against the thought of my little sorted plan.

After careful consideration, I decided I would proceed on with the trip since the hotel was already paid for and I did not want to forfeit the deposit. Besides just be dressed I would still feel sexy.

I shaved and showered and decided to put the cage on, just to deny myself any excitement. So, as I was getting adjusted. I heard my wife coming down the hall and, in my haste, not to get caught. I pinched myself in the unit. Not fun.

Finally, out the door and on my way, now for a six-hour drive. About three hours into the drive on a long lonesome freeway, I saw flashing lights in my rearview mirror. I pulled over. As I see the officer approaching, I notice the large neon pink dildo sitting on the console next to me. I grabbed and threw it under the seat. How stupid. The Officer asked me why he pulled me over, I was going 82 in a 65mph zone. He asked what I put under the seat. I sheepishly responded a sex toy. He had me step into his cruiser while he checked it out. He came up smiling. He gave me a ticket for speeding and harsh warning for distracted driving. I don't know how he kept a straight face. So this trip gets better and better.

Continuing, on the road I decided I needed a break, so I pulled off for a drive thru lunch. I noticed that there was a big box store across the road. I needed a few items including makeup remover and I always like to stroll through the undies and lingerie sections. There was no parking close to the entrance and it was bitter cold out, sub-freezing. Grabbing my jacket, I proceeded across the parking lot. I was only wearing light weight nylon trackpants with nothing underneath. As I got closer to the door, I noticed a slipping of the cock cage. Oh no, I thought, I figured I would just run in to the restroom and readjust it. Imaged how mortified I was when I totally slipped out and it rolled to the store greeter (she was well in to her 70's). Bending down to retrieve it. She said

"I believe you dropped this"

I thought the couple behind me were going to pee their pants laughing. The must have realized what it was and what happened.

I grabbed the cage, thanked the women and hurriedly walked out the store with no dignity left. I heard the adage cold enough to freeze the balls off a brass monkey but that was totally ridiculous. Evidently, I totally shriveled up and it fell off.

I was about an hour out from the rest stop, where I planned to put on my garter belt and stockings. I saw the sign for a chain adult book store. Decided to swing by to check out the selection of toys. As I got out of my car, a truck and trailer rig pulled in the lot. A well-built black driver got out and headed in the store, I was right behind him. While I headed to the women's toy section, he headed to the gay video section then went to look at fleshlights. I so wanted to ask if he needed a hand, but since I was in my physical state and could not provide any service. I decided not to approach. I just longingly look as he took his new toy and climbed in the rig and then to the back. I so wished I was going in with him. Fantasy is one thing, but I've never wanted a man until that moment. I sighed heavy as I got back in the car. I purchased and inserted a small butt plug.

In no time, I was approaching the rest stop and I decided I would still put the nylons and garter belt and just go the other sleazy bookstore. I'll be damn, the rest stop was closed. So, I headed to see what the action was like at the bookstore. The parking was jammed full of at least thirteen cars. I walked inside and I was the only white man (except the staff) in the store. It would have been like shooting black cock in a barrel, if I was only able to play without contracting a STD. I was not worth the chance, I could always comeback if everything healed. Since I was here, I thought I could at least check out the booths and might get lucky and have someone play with my four inches of manhood.

I paid the three dollars and headed to the booths, there was only one open. I entered and locked the door. It was very dark except for the video lights. I put my quarters in the machine, selected a very bad video, and looked for a glory hole, there were none. Could this day get any worse?

Frustrated beyond belief I got back in the car and headed to the hotel. Upon arrival, I went strait to the bar and started to pound Gin and Tonics. After four, I headed up to the room. I remember the vial of lube and dildo was still in the car. I figure I would go out and get them and take them to my room. On my way to car I chatted with a nice woman. As we walked to the parking lot, then it happened my little butt plug squirted half way out. Now its hard to act nonchalant when you have butt plug falling out while you are walking. She turned away and I quickly put it back in place. I got to car grabbed the lube which was frozen. I headed back inside the hotel.

I decided to get dressed and go to the club. I started to put on my makeup. I finished up with the lipstick. I looked in the mirror and thought no one should apply makeup after too many Gin and Tonics. I looked like an understudy for the Joker. I sat on the bed and passed out. So much for going anywhere.

When I awoke in the morning with a headache, I also had a full-blown raging cold. That was it, I was done. Karma or other forces was telling me I was not destined to be a sissy. I hopped in the shower, packed quickly and headed home. As I was driving out of town, I saw a Goodwill donation box. I stopped put all my feminine attire and toys in the box and drove off.

As I walked the front door my wife looked at me and asked, "is that lipstick?"