Chris' Journey Ch. 01

Chris' Journey Pt. 1

Im Chris and now 25, but this story starts when I'm 18. I'm from a small country town and my family is very conservative. I began having bisexual thoughts but still preferred girls. None of this was known by anyone. Being chubby and having a 4 inch dick( being very generous), I was always scared to talk to girls.

Porn was always my go to. That's when I discovered trans porn which led me then to gay porn. I was needing to lose my virginity and wanted a man to do it. I downloaded a gay hookup app and started anonymously talking to local men but was afraid of getting found out. So I continued to jack off while chatting with strangers about them fucking me. I also started a NSFW account on social media and was always role playing or talking about these guys fucking me one day.

It was a long summer of dreaming. I decided that summer to start working on my body but mainly my ass. I would sometimes go to the gym but did a lot in the privacy of my own room.

Towards the end of the summer I had managed to shape up my ass into a fairly good looking ass that could hopefully get some cock. Plus I had lost a little weight although still chubby.

August came and college was right around the corner and I had decided that I was losing my virginity once and for all. My family helped me move in and thankfully/sadly I had a roommate that I was friends with from high school. We got settled in and my family left.

The first few days were pretty uneventful but then orientation began and I knew no one so I could be free. They had us pair up and I was with a hot guy, Sam, and we started talking and got to know each other. I told him I was gay and he was super cool about it.

We broke for lunch and he was kind enough to ask if I wanted to eat with him and we hit it off but sadly I learned he had a girlfriend. That deflated me real quick and I tried not to let it show.

The rest of the orientation went as planned and as we were leaving he asked if I wanted to go get supper. So we went and ate nothing crazy but as we got in his truck he said "look I'm not gay but I've always heard guys give better head"

Shocked and a little lost for words, I finally spoke "I've heard that to but I've never done it, but if you want I could try."

He very quickly pulled his 5 inch cock out and shook it. "Hell yeah"

I leaned over in the seat and started stroking him and was so happy I was finally touching a cock that wasn't my own. As he drove in silence, I finally licked the tip and tasted cock. I then wrapped my lips around him and started sucking. Hearing his grunts and moans had me hard and happy. I worked my mouth up and down his hard cock savoring the taste of his warm cock and the precum that was oozing out.

He pulled in to the parking lot at his dorm and laid his seat back a little and closed his eyes as I sucked him. I sucked for probably ten more minutes when he tensed up and moaned as he began cumming in my mouth. I tried my best to gulp down his slightly salty cum but some escaped my mouth.

After he quit squirting globs into my mouth, I licked up what escaped and cleaned up his cock. No words were exchanged as he put it away and we got out, but as I was walking away I heard him, "thanks Chris, that was great."

I smiled, "anytime".

With that I headed to my dorm and thankfully my roommate was out so I laid down and stroked myself and came harder than I've ever came before falling asleep.

I woke up the next day with a smile on my face and cum on my breath. I showered and went job hunting. Luckily, there was a department store that was hiring and I got the job.

Knowing that I would have a steady income of spending money plus what I had from my summer job, I headed to the sex shop and bought a dildo, a douche, and some lube. I put them in a plastic sack and rushed back to my dorm and hid them.

Once my roommate left, I went to shower (thanking god we had a bathroom we shared with just the room next to us) and did the dirty work to clean out.

Once out of the shower, I lubed the dildo and my hole and slowly started pushing it in. After a few tries, I finally got it in all the way and stared fucking my ass. I then suctioned it to my chair and started riding it. I even filmed my hole taking the dildo for my social media, which got a good amount of likes. I ended up cumming hard as I fucked my tight hole and cleaned up.

I decided to update my hookup app with pictures and began searching for someone to fuck me. I talked to a number of guys but one stood out. He was a 58 year old man with a very hot cock that he said was 7 inches. We began planning and decided to meet at his house the next day at noon.

The next day I showered and cleaned and headed to his house, which wasn't to far from campus. When I pulled up, he was just getting out. I got out and we walked inside like we didn't know each other.

Once inside, he grabbed my waist and pulled me in for a kiss. It was electric, as his lips met mine and my arms went around his neck. My cock stirred and I could feel his bulge pressing into me.

He began pulling my shirt off and I his, and as we began kissing again his hands squeezed my ass and one of mine rubbed his hairy chest as my other found the hard cock it was searching for.

Our breaths quickened and our hearts beat fast as we clumsily made our way to the couch. We fell onto the couch with me on top.

I broke the kiss, " I need to suck your cock."

"Go ahead" was all he said.

I kissed down his chest and then undid his belt and pants and pulled them off along with his briefs. His hard cock sprang free and my mouth began to water. I grabbed the base and like a hungry slut, started sucking on his hard mature cock.

"Ohhhh fuck, suck daddy's cock."

Hearing him call himself daddy drove me wild. I sucked harder as I looked up into his eyes. All I saw was lust from this older man.

"You are such a good cocksucker" he said as he rubbed my cheek.

I tried to deepthroat him, but ended up gagging myself and had to pull off and stroke him.

"Daddy your cock is so big and taste so good." I wanted this man to use me and I wanted it bad.

"You will get there, don't worry. You just need to keep trying." I took his advice and started sucking again. I tried a few more times to deepthroat him but failed but I did have a crazy amount of spit going.

"Are you ready for daddy to take your virginity?"

"Yes daddy." He had me stand up and pulled my shorts off and then my briefs. Then he laid me down on the couch and lifted my legs. I was a little scared as I had never been exposed like this in front of anyone, let alone a man 40 years older than me who was about to fuck my virgin hole.

"Relax and let daddy make you feel great."

He got down and started licking my tight virgin hole. The feel of his tongue on my hole and crack was driving me wild. I let our moans and whimpers as he ate me out. He then licked his way up to my hard but small cock and started sucking me while he slid a finger in my hole.

"Ohhh Daddy, fuck, this feels so good. Oh my god I love it"

He kept going like an expert and added a second finger to my hole. After some time, he pulled his fingers out and sat up on his knees.

"Do you want daddy to wear a condom or fuck you bare?"

Without thinking I said "fuck me raw and cum deep in me."

Looking back it probably wasn't my brightest move but I was young, dumb and horny.

He grabbed the lube that I had brought and put some on my ass and slid his fingers in me and then lubed up his cock and lined up.

"Are you ready?" All I could do was nod, then he began pushing in.

"Just relax and breathe." I took a deep breath and closed my eyes and relaxed until I felt his head pop in. My eyes flew open.

"Aaahhhhhh fuck fuck you're so big"

He leaned down and kissed me as he rubbed my ass. He would push in and stop, then push in more. The whole time he was kissing me. I then felt his hips on my ass and he pulled away from the kiss.

"See you took it all, let me know when you're ready." We were smiling at each other, but inside I was screaming. As he sat with his cock in me, the pain became less.

"Ok daddy, fuck me" he needed no other encouragement as he started pulling out and then pushing back in. The pleasure I started to feel gave me so much encouragement.

"Fuck yes daddy give me your big cock. Fuck my tight ass."

"Fuck baby you have a great ass. It feels so good."

He picked up his pace and started fucking me like a toy.

"Oohhh my god, fuckkk it feels so good daddy. You fuck me so good god I love it." I spoke but it wasn't real clear as I was experiencing pleasure I never imagined. He was grunting like an animal in heat as he dove his cock into my tight teen ass. I lay there rubbing and squeezing my chubby tits as he fucked me. I started to feel something inside me.

"Ohhh daddy I'm about to cum"

"Cum for daddy, shoot all over your sexy belly"

After a couple of pumps, cum shot out of me and all over my belly. Seeing this sent him over the edge and I could feel every vein in his cock pulse as he tensed up and buried his cock in my ass.

"I'm cumming." Before he could finish,

I felt a warmth deep inside me as he shot load after load of his hot cum in me. We kissed until his cock softened enough to slip out with a plop, as his cum oozed from my used hole.

We laid there for what seemed like forever but was only a few minutes. He got up and grabbed some tissues and we cleaned up. He kissed me before we left.

As I drove back, I could feel his cum leaking from my ass and I just smiled. I finally felt more like myself.

To be continued...