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. He began to get clingy and rub my upper back.
“My, my, I dig your rags, honey, I don’t ever remember seeing you here before,” he said, in a girly accent.
“I’m not from here, I’m from out of town,” I replied.
“Honey, you’ve stumbled upon the suburb’s only gay bar,” he said, trying to nibble on my ear.
It was then it occurred to me, that he was hitting on me.
“I didn’t know, I’m staying at the motel nearby, and it looks like a dive,” I said.
“Hmm, honey that happens all the time. They either leave in a hurry or leave here happy,” I pondered his words.
"What will you do, lover boy?” he said, with a hand under my basketball top, targeting my bulge.
What the hell have I got myself into? As I blocked his advance. Before taking a sip of my drink.
“Well honey, I can welcome you to the bar by giving your cock a good sucking,” he said, in a seductive way, with his hands back inside my shorts and rubbing my cock. I started getting aroused but then started to think about it. It’s been over two months or so since Tiffany fucked with my head and now this strange boy was too.
“Let me finish my drink and I’ll think about it, maybe later,” I said, taking another sip.
“All good, Honey, and I’ll have you cumming like a train before the night is over,” he said and planted a kiss on my lips. He then skipped away like a girl, and sat with a group of like-minded young guys, in a booth.
I just smirked and shook my head.
“Your first time in a gay bar, buddy,” the bartender asked.
“We never had anything like this bar or any gay clubs, where I’m from,” I said.
“I gathered that. Hey, buddy, if in the future you go to another gay bar, do not wear what you’re wearing. Look at them, they might be gay, but in here, most of them, are wolves, and you look like prey,” he said.
“Oh, okay. I’m on holiday and just wanted to express my inner self,” I answered.
“On a plus side, this is one of the better gay bars I’ve worked in. Most of the guys are clean and well-behaved. Jacko over there, I wouldn’t put too must trust in him, he’s been a bit of slut, since his teens,” he said.
I took a sip from my bourbon and ordered another.
“That there is Jeremy or Jessa, he’s clean, and looks after himself,” he said, as he handed me my drink.
Once, I’d finished my drink, I left the bar and went to the dancefloor. I started to dance around to the beat of some disco track, which was almost like a rave song. So, here I was basically, moving my feet on the spot and waving my arms in the air, and wiggling my ass around.
To the other regulars, I must have looked like bait to them, dressed the way I was. I was hit on by a few of them before Jessa surprised me from behind.
He reached over from behind and caressed my bare thigh, and soon reached around and rubbed at my bulge. Jessa looked toned and cute, and I got an instant hard-on. It made me comfortable, that it was him after the bartender had raved about him.
“Hey honeybuns, looking for action?” he said, snuggling up to me. He had his hands in my shorts in no time. I didn’t resist. In no time my cock and balls were out of my shorts and in his hands.
We started smooching while on the dancefloor. He caressed my cock, before stroking it. We faced Jacko and his friend’s table, Jessa was sending a message to them, I suppose. As he had me facing them panting, with my shorts near my knees and my cock in his hands. I couldn’t help but grind my ass back into him and his bulge.
“Oh, good, you want to play,” he whispered into my ear while stroking my cock.
“You can say, that,” I nervously said.
All my trepidations from three months ago were just a memory. I’m in a fag bar and a young fag was getting his way with me.
Here I was on a dancefloor with a younger man gently caressing my cock, facing me towards the booth where Jacko and other likewise fag boys were. He was biting my neck and making me forget my worries and where I was. I was beginning to drift off and go with the flow.
I was acting like some of the girls from my past, lost in love and lust, and starting to lose myself to him. What was I doing, do I have no morals? Soon, I let all my anxiety go, and he made me cum.
Maybe it was that he was good-looking, and for the first time in months, I was forgetting my hometown dramas.
He soon had my flimsy tassel shorts down to my ankles. I didn’t care that an audience was glancing at me or us. Jessa kissed and bit the back of my neck. I closed my eyes and began moaning. Luckily the music was louder than my moans, or my groans when he penetrated my asshole with a finger.
I stepped out of my shorts, so I could give Jessa a better access to my butt. My cock was sloppy with cum and pre-cum, and I was moaning more. I could tell my cock was bleeding cum as I felt the liquid running down my bare inner thighs.
It was then, I noticed that the other fag dudes who were dancing near us were now getting it on as well, with their partners.
The bartender had said Jessa was clean and a good kid, so I decided to take the risk. Even if he acted like a bit of a Femboy, he had me hooked.
“Are you staying at the joint across the road,” he whispered.
“Yes,” I stuttered.
“Do you want to take this to your room, because I so want to fuck you,” he said, while he licked and slobbered my neck and ear.
“Yes, yes,” I anxiously answered. I want him to fuck me as well.
“We’ll grab some booze and make a night of it” he bit my ear.
I picked up my fallen shorts between my ankles, and then wrapped them around my arm, like a sweatband or an arm guard. With my cock flopping freely underneath my basketball top, we then went to the bar and ordered some takeaway beverages.
Jack Daniels cans and a few mini-bar bottles, and I tipped the bartender for the night. All the time, Jessa was pumping his thumb into my ass, making me sigh slightly, and I was loving it.
I found it hard not to whimper while I spoke to the bartender. The bartender gave me a naughty wink, as he knew what was going on, and what was about to go on.
Outside the venue we acted like a normal couple, cuddling up to each other, I felt like the female in this partnership, whether I would admit it or not. By now he had his two hands spreading my ass cheeks apart and the two middle fingers of his right hand working my asshole, while we kissed by the traffic light.
Luckily my basketball top was big enough to walk in the darkness to not show the public I was nude underneath, as they walked by us from the front. We stopped briefly when the light changed, I leaned down to pick up the bag of alcohol. From behind people would know that my cock was free balling as I bent down. No one was nearby.
Once we were crossing the lights, we hugged onto each other's hips, once again. I carried the alcohol in my free hand, while he caressed my bare ass with his. As we were almost way across, he gives my ass a few small whacks, bringing a tiny grin to my cheeky face. The cars waiting for the lights to change were teased by him when he lifted my top. They had no idea in the night if I was a girl or a boy.
“I love cock in my ass, don’t you” Jessa announced, as he gave my ass another slap.
“So do I, yes, it’s to die for,” was my response. I didn't know what to say but agreed with him.
The world around us was oblivious to us, as we arrived at my motel entrance. We embraced like lovers, as he caressed my ass with both hands, while we kissed and groped. Then we entered the motel after I unlocked the night door with the key around my neck.
As we waited for the lift to arrive, the world around us would have known we were two fags if there were people around us in the lobby at 3:00 AM.
***
Once inside my motel, my top was gone in 5 seconds, he also stripped. My sandals and socks (which held my credit cards) were gone.
My cock grew once I saw what Jess unclothed looked like, he was tattooed on his chest and upper back, but I had none. He looked like he was a gym junkie, with a toned body, much like what I might have looked like after I left school if I didn’t quit gym class.
His cock was still flaccid and limp, but it looked as big as mine when I was rock hard.
“Wow, you’ve got a big package,” I said, admiring. He just winked.
“Wait until it wakes up,” he teasingly waved it by the bottom of his shaft.
He motioned me to the bed and to lay on my back. Once on my back, he crawled between my legs and placed my legs on his shoulders. Then his hand touched my cock and slowly caressed it.
“Ok, honey bud,” he said as he kissed the tip of my cock. We made eye contact before he then proceeded to swallow my whole cock down his eager mouth.
I closed my eyes and was moaning in no time. He was caressing my ass and even squeezing them apart and so on. It was a while since I last masturbated, other than edging on the bus, I had no sexual activity. So, it didn’t take long before I started the build-up in my balls.
“Oh God, oh yeah,” I moaned, I was close to passing out with pleasure. I hadn’t realized he was his middle finger inside my ass until I was about to cum.
As I started to cum, I opened my eyes. When I looked down towards Jess, I could see him lovingly licking my saliva-coated cock, from shaft to the tip, and went back to sucking again. Soon after, I let go and the first squirt hit his face. He then quickly swallowed down on my cock as I kept exploding. After he swallowed my cum, he didn’t stop there. He kept sucking for a good minute and bit after, then licked my cock, like an ice cream.
He then crawled onto the bed and lay next to me while catching his breath. I look down at his cock which was coated in pre-cum but still soft but at half-mast.
While he caught his breath and relaxed, I was fixated on his cock, and eager to play with it, before tasting his cock. So, I sat up and crawled over on top of him and started caressing his cock. It slowly grew, and when it reached over seven inches, I slivered down to the floor like a lizard and swallowed as much as I could.
He rose to a seated position, and I felt his hand scuffing my shoulder-length hair and encouraging me to go deeper. When I swallowed the whole thing, I popped my head up and gasped for air. I then began my bobbing motion of sucking down his shaft, then up, then back down.
Jessa let out a few moans, which encouraged me.
“Honeybud, you’re pretty good at sucking cock, if you want, you can take my love in your mouth,” that’s what I planned to do, anyway.
I couldn’t swallow his whole cock, but I kept sucking on his fully erect big cock. Once it had finished growing, it was the biggest thing I had sucked or I had played with, and I loved it. In time, I felt him swell in my mouth, and I knew he was going to spew cum inside my mouth.
As he spasmed, squirt after squirt, making me gurgle and choke on cum, before swallowing his love.
When he’d finished, I sucked and licked his saliva and cum coated cock, as he did to me. I then laid my head on his lap next to his cock and balls, and slowly licked them like a lizard, while he lovingly stroked my hair.
Soon after, he wriggled away from me, headed to my tiny bar fridge, and grabbed us a can of Jack Daniels and Coke each.
I was left bent over the bed with my knees kneeling with my arms crossed under my head until he returned.
When he returned, he gave my bare ass, a tiny kick. I climbed up on the bed and handed me a can.
Not long after we sat and drank our cans of Jack and Coke, he started stroking my cock.
“Round two,” I asked.
“No, it’s the Superbowl,” he answered. Leaving me confused.
He positioned me, face down on top of the bed, with his ass bent over it and my cock over the edge. He slapped my ass and spread my cheeks apart.
“I want to make love to you and breed you, Honeybud,” he calmly announced.
The first thing he did was finger my ass with two fingers, before applying KY or something similar into my ass. He fucked my ass like this for a short time, before using something like a plastic handle.
At first, I felt a little pain when he slid a foreign object inside and twirled it in circles in my hole. In no time that minor pain became warm and pleasant and soothing. The way he did it felt erotic, unlike the smash and bang of the New Year’s Party.
When he removed the foreign object to apply more KY, he smeared it around the entrance of my hole. My ass felt numb, but my cock couldn’t help but go hard.
“It’s showtime,” he announced.
Even though I desired to be fucked, a little bit of fear still crept in. I saw how big his cock can be.
He moved my legs slightly apart, as butterflies flew in my stomach, in anticipation.
Jessa rubbed KY over his big cock and began rubbing the head of his cock across my asshole. Then the head was gently pushed inside, inch by inch. I grimace a little as it spreads me open.
“Relax,” he softly said, as he lifted my ass slightly. Then he inched inside again, then I felt a lightning bolt hit me, as he forced himself deep inside. I let out a groan of pain.
He just let his cock rest inside, while I absorbed the pain. Then he started to inch in even deeper, he kept pulling back about an inch, then forced back in deeper.
I was groaning in pain and pleasure, as he started moving in and out, slowly. He also began to grunt as he was trying to split open my ass, so his cock could breed me without effort.
When he pulled his cock out, thinking I was too tight, and had given up. I began to pant and whimper.
“Please, I can take it,” I pleaded.
With that, Jess pushed back inside and started to thump his cock in and out, without mercy. At first, I thought he was going to injure me, but I held back any complaints.
Within two, maybe three minutes, he maliciously thumped into me and finally broke my resistance. I couldn’t see what had happened to my ass, I thought there’d be rips and blood, as my ass felt numb from all his effort.
My cock flopped around as he started to thump in and out of me, but this time he had full access to my busted asshole.
Oh god, this was better than last time. There wasn’t much pain, and it was like my last fuck at the New Year’s Eve party. By the men who fucked me there, I just felt fuller.
I was moaning non-stop, as my arm stretched full length and gripped my bed.
“Oh god, oh fuck, oh fuck me, oh fuck it feels good, oh god, fuck me, fuck me harder,” I moaned. As he started to give me a good old-fashioned pounding.
“I want your cock to open my ass so wide, any cock can be buried inside it, fuck me, fuck me good,” I pleaded and moaned, at the same time. My ass already felt split open.
“Your ass is so tight, it’s strangling my cock,” he said and let out a tiny laugh. I knew it was a struggle for him, as I felt the torture of him forcing his cock in hard and deep.
I had my legs crossed across his neck, while he grabbed my hips tight and fucked the resistance from within me.
Jessa smashed into me, deeper and deeper, hard and fast. I started to feel my balls tighten as my limp cock bobbled around between my legs. My breathing turned to constant moans, as I tried to hold on. In the end, I couldn’t hold on, as I suddenly began to twitch and then cum hard, as I clinched tight the quilt on the bed. He kept fucking me without mercy.
I was left panting and moaning, while he broke my ass.
“You just made me bust my nut,” I moaned to him.
“Ha, good, I’m coming too,” he groaned.
“Aww, fuck, I’m cumming,” he groaned, as I felt his cock grow inside my ass.
He kept grinding into me until his sweaty palms made him lose his grip and he slid on top of my back. He lay there, kissing my neck. His cock soon went flaccid and slipped out from my ass, and his warm cum soon dribbled out with it. The cum trickled out and down my balls.
Jessa climbed over me on top of the bed, his dead weight was almost crushing me. He then rolled off my back and onto his side of the bed next to me, breathing heavily. I remained facedown and bent over the bed, with a satisfied smile.
Five minutes passed before I got up and cleaned myself up with a towel, that was sitting on a chair. Then, I went to the fridge and grabbed us one of those mini-bar bottles each, and a can of JD (Jack Daniels). We sat on the edge of the bed and drank them.
“Your turn,” He looked at me and handed me the KY. I felt obliged but didn’t want to.
We both drank a miniature bottle of spirits from the bar before, I spread KY over his ass and inside it, before trying to fuck him, as he did me. I attempted to give Tiffany the odd anal fuck, but she told me I wasn’t good at it, so we stopped.
His hole was tight, at first but it wasn’t such an effort as it was for him.
“Wow, that was an effort, didn’t think I was going get it in,” I said as if I had hit a trick shot in a game of pool.
“Being a little drunk can help, as long as you’re not too drunk,” he said.
“Meaning?” I said, puzzled with my cock buried inside his ass.
“It slows down the urge to cum,” he said. Funny, I had always thought too much alcohol made you cum too quick, I thought to myself.
“Now start fucking me slowly at first,” he ordered, and I did.
With every thrust, his ass sucked tight around my cock, and I could feel cum trickling out from my ass, with each thrust. Then I over exerted and I let off some gas from with my bowels, and out plopped more cum. That ran down the back of my leg.
I must have then fucked inside his ass about another 10-20 times before I started to cum. I felt glad as it was tiring and straining my lower back.
“Oh, fuck, oh fuck,” I groaned, as I dumped my love deep inside his ass.
With my cock still spasming inside. Someone bashed the wall from the next room, telling us to shut up. More like
“Shut the fuck up, faggots, or I’ll kick the door down and make you!”
Trying to be quiet and ignore the Wildman outside, I flopped on top of him, panting like a dog in summer.
Before I could do anything, Jessa had turned to his side and pushed me off him. He kissed me, before slivering towards my cock. he swallowed my cock, and sucked on it, to cleanse it.
*
Later, as we lay naked on my bed, and recovering, he rubbed my chest.
“Where are you from?” he asked.
“Out of town and interstate,” I said.
“Figured as much, can we fuck until you leave,” he said.
“Sounds good, but I think I might be back in a few months, once I tie up a few loose ends at home,” I said.
He stayed until lunchtime that day, and he fucked my ass several times and I tried again to fuck him. In the end, he stopped asking me to fuck him.
We fucked and sucked all morning, then we cleaned up. That afternoon we went clothes shopping. He picked out clothes that I would look good in, plus some make-up, only black eyeliner, and lipstick. The clothes were a bit girly, but I wasn’t complaining, he paid for them. Then we kissed and cuddled in public before he went home.
I wore eyeliner when I went to the bar that night. Jessa turned up after 08:00 PM, before we returned to my motel for one last time, with a 10-pack of JD. We fucked and sucked on thru the night. Then he fucked me one last time in the ass facing the balcony window for all to see.
It was agreed that I was his bitch, as I was a good cocksucker but a useless ass-fucker, so that’s how it was with us.
We exchanged email addresses and cell numbers. I planned to return during the mid-year break.
The next morning, I wore eyeliner, my skimpy denim shorts that had rips in them, my poncho, my fuck-me boots, and an Indian cowboy hat that Jessa gave me. I packed and had breakfast then headed to the Greyhound depot. The odd person looked at me, and the bite marks on my neck, as I sat waiting for the bus to arrive.
To me they were marks of a good time, not only was my neck covered in bite, but so were my shoulders, and breasts.
As I boarded the Greyhound bus a while later, I still felt tired and sore. I’d been fucked hard so many times in the past few days, that I was walked as if I had been horseback riding.
I sat at my seat looking at the gay bar, and the time I had here and there.
Then at 11:55 AM, the bus left the city. We had one more stopover, in a few days, before we headed home in ten days. I went to a laundromat and washed my clothes, all of them, while I did, I draped myself in my blanket. It was dark and no one was around.
*
I left home because my so-called friends had found out that I had gay desires. I’m returning with the same desires but unlike before, I didn’t care. I was slowly growing into a girly gay. Also, before I’d left, I was thin built or athletically slim, but I had noticed I had lost a little weight but had grown tiny man boobs over that time.
(To be continued...)
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