My Evolving Transition – Ch. 03

Road trip from embarrassment

The most gullible person in my town and world was me. After that night when I willingly let two strangers fuck me, people I knew snickered or mocked me. I can say one thing I enjoyed it will it was happening not knowing that it was a trap.

There were signs I should have paid more attention to before blindly going to that party.

“I’m going to have you craving cocks and turn you into fag, before you know it,” was one of Tiffany’s taunts, while nailing my ass with her strap-on dildo. I paid little attention to those taunts back then, as she was turning me on with her strap-on buried deep in my ass. Those were the early warning signs that I should have paid attention to and ignoring them.

Back then, I had no idea what my true orientation was, or to have sex with anyone but Tiffany.

I was a sheep and Tiffany was my shepherd, before I knew it, I was craving her to use her strap-on, on me. I hadn’t twigged to what she had set in motion, and what was to come.

It was all leading towards the New Year’s Eve Party when her plan was hatched. That’s when my world turned upside down. It wasn’t just about having sex with men, it was how much I loved it and how my profile changed or looked in my town. and at the time loved it. I found out, that while a man had his cock buried inside my mouth, I couldn’t help but look up into his eyes. That look, as I milked his cum into my mouth drove me wild with lust. It was a minor distraction while his friend had his cock buried deep in my ass.

I was oblivious to the outside world while this went on, I was in lust for their cocks.

Then my entire world turned on its head. Within an hour, images started appearing on the internet and cell phones, of me covered in cum and engaging in acts of gay sex. Tiffany stopped taking my calls, and soon I knew why. It was all a nasty plan of hers, she had a reputation for breaking boy’s hearts. I later found out why.

I felt ashamed, and depressed, and locked myself in my loft. I isolated myself from everyone, even my mother. Here I was in deep regret, on the verge of a breakdown, and contemplating dark thoughts. I knew I needed to get out of town, ASAP.

I had money stored for college that I used to buy a bus ticket. So, I wrote a letter and left it on my bed for my mother to find.

Then, early the next morning I snuck out and caught the bus interstate and planned on doing a tour around the country.

*

The first bus trip out of town was a 4-hour journey to the state’s capital, where once there, we had a three-hour stopover until the tourist bus arrived.

So, I spent a few hours window shopping at the nearby mall before I had a snack and beer at a bar. What caught my eye the most, was all the girls dressed scantily in the mall. I admired how they easily could walk the streets dressed how they were. A part of me wished I could wear clothes or a dress like them or be one of them. The last thing on my mind was, wanting to hook up with them. Tiffany killed my love of girls or women, for the time being.

Then it was time to catch the bus interstate and to a national park region. I sat in the rear of the bus. That’s something I always did. Nerds sat at the front, and dudes sat at the back. It’s something I picked up while in High School.

During the first few days of our trip, my thoughts and dreams haunted me. I kept seeing images of cocks and me sucking them, and the New Year’s Party, orchestrated by the Puppet-master, Tiffany.

While on tour, we ventured through farmlands, mountains, and the odd town, before staying in a cheap motel for two nights in some big city, I didn’t know where.

My voyage was only supposed to be for around a month, so I packed light.

It was winter when we left but we were in a warm state, with no snow or rain here. I wasn’t planning on staying away for too long, or factor in that altitude brought a colder climate, and I didn’t pack for the cold.

In my pack were a few boxers, socks, T-shirts, a blanket, a towel, plus showering items, as well as the clothes I was wearing. At the time I had gym shoes, socks, Dolphin shorts, boxers, and a tank top T-shirt with a band’s logo on it. By the time we had our second stop-over in a big city, it was getting colder. So, I bought a lambskin hooded jacket, an Indian poncho from a thrift store, ripped denim short shorts, and patterned yoga pants.

I was still only planning for a month’s trip.

So, here I was at the time, wearing Dolphin shorts, gym shoes, and my hooded poncho, and using my blanket as a pillow, while on the bus. I was looking at people, farm animals, and the country scenery, while semi-unconsciously daydreaming about nothing. Only potholes broke my focus.

At times when we were high up in the mountains, it felt colder. So, I wore my hooded poncho and yoga pants and wrapped myself in my blanket to keep warm.

When we had stopovers or rest stops, we all disembarked to stretch our legs or went to find some food. We usually had a few hours to kill before we left the area. So, there was time to check out the local bars and food shops.

Up in the mountains, I felt ultra cold, wandering outside, so I only went outside briefly before returning to the comfort of a warm bus.

One month turned into two in no time. I bought another bag to hoard my new clothes and items.



After my second month of touring, we made it to warmer areas, and I started looking at women wearing fewer clothes once again. I was back thinking about sex again, fantasizing about women and wanting to fuck them or to be one of them.

After two months of journeying the country and into warmer weather, I had gotten used to wearing and walking the outdoors, dressed like what the girls were dressed casually like. Well, I was a stranger in a strange land, so why not dress up?

I even bought a pair of tanned cowboy boots with an inner zipper, that almost reached my knees, from one of our stops. My hair was slowly starting to grow longer, and it was now shoulder-length. By now I had even purchased a long-sleeved fishnet top. I was living the life.

Ask me why, I didn’t know myself, why or why I imagined I was a girl. Maybe I was on holiday and it was part of the adventure.

**

My current booked coach led me to another big city. After three months on the road, I was beginning to feel frisky and started to crave sex, once again. In my current frame of mind, I wouldn’t say no, to anything with a pulse.

We had a two-night stopover in the next big city, and the first thing I did after booking into a motel near the bus stop, was shave, shower, and then head to the nearest bar.

I wore my cowboy boots, tassel brown shorts, and a college basketball top, (no boxers, but I wore socks) and headed downstairs to the motel bar.

The motel bar was a dive, and so was the motel. So, I walked outside and saw a bar across the road. Without thinking I crossed the road and entered, from the outside I couldn’t see inside the venue, as the windows were painted over, with what looked like old hippie art.

When I went inside, there were people scattered in all areas. There was trendy 80’s pop music playing, as I looked around until I spotted the bar.

Once there, the bartender gave me a strange stare.

“What on Earth are you wearing?” he asked as I ordered a bourbon on the rocks and sat down, on a stool at the bar.

“I am a tourist, and just here for a couple of nights,” I replied.

Before I knew it, a young man/boy sat on the stool next to me.