He was My Boss

Story Info
A story of my first time gay.
1.4k words
4.44
45.5k
24

Part 1 of the 2 part series

Updated 06/08/2023
Created 02/06/2018
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Having finally finished high school, I was spending the summer working my butt off to get enough money to survive my collegiate freshman year in Austin. Mom and Dad are paying for my room plus one cafeteria meal a day and tuition but all other costs and expenses were on me. Being in a small Texas ranching community, jobs were few and far between. So far, I had halter broke 10 colts for a neighbor rancher, bailed and stacked hay (in the Texas summer), worked on a seismograph crew, strung about 2 miles of barbed wire and repaired 18 wheeler truck tires. But the most interesting job was unloading cedar fence posts, not because of the nature of the work but the education that came with it.

Bob had rolled into our sleepy little town with an 18 wheeled tractor trailer full of fence posts. He saw me at the truck stop, came over walking right up to me. This guy was the epitome of the Texas cowboy. Long legged, wide shoulders and tight jeans with a tee-shirt. He looked to be in his late 20' or early 30's with a George Strait look about him. Right away I wanted to look like him.

He looked me up and down and said, "You want a job?"

I asked, "Doing what?"

He said "Help me deliver these posts out and about to different ranches, you know the area, right?"

"Yeah, I do, how much you paying?"

We agreed on a price, and set a time to start the next day.

The next morning I arrived at the local cafe/coffee shop and saw him eating his breakfast. I had a cup of coffee while he finished and we took off to start the day.

I'm still not sure which is worse, bailing hay or tossing fence posts. Most of the posts were 8-10 foot long, about 6-8 inches in diameter and weighed about 50 - 60 lbs. each. It was a long, hot day and I was tired, but the sun was going down and the day was over. I climbed up in the cab's passenger seat hoping the A/C would start soon. We took off for the 35 mile ride back to town.

He started telling me about his life, his wife, and his small hill country property full of cedar trees. He then asked about me; where I was going to college, what was my major, my girlfriend. I answered as sparingly as possible. He then asked if I had fucked my girlfriend and I told him I had. Then silence.

Suddenly, his right hand landed on my left thigh, squeezed a little and told me how well I had done that day. I thanked him but his hand didn't leave my leg. He had to shift, but his hand returned to my leg again. I was getting a little nervous with the situation, but didn't say or do anything. I guess he interpreted my silence as some form of acceptance because he starting massaging my upper thigh, chatting away the whole time.

I was 18, I got hard working an algebra problem, now there was a hand just inches my balls. I felt myself getting thicker and stiffer. Bob noticed also and moved his hand up until it was resting against my balls. I tried to will my cock to deflate, but it now had a mind of it's own, I was getting really hard. Bob placed his hand right on top of my cock, feeling the shape and exploring, squeezing rhythmically as we drove along.

I was so shocked, I just sat there like a cow patty and watched his hand fondling my cock through my jeans. Damn, I was hard, heart racing, flushed and about to bust the buttons on my 501 Levi's. Then, suddenly we were in town. Bob placed his hands back on the steering wheel and acted as if nothing had happened. He pulled into the truck stop where my car was parked and said, "Same time tomorrow?"

I think I said "Sure", being a little alarmed, nervous and horny, I'm not sure what I said.

I drove home deep in thought about what had occurred, all the different emotions and anxieties running around my head. My cock was hard the whole way home. I went in, said hi to my parents and headed for the shower. The hot water felt good on my tired muscles. I started getting hard again thinking about the ride back into town. Shower, hot water, hard on and soapy suds, duh - I started stroking my cock and had a climax that actually buckled my knees.

The next morning, I considered whether to go back or not but only briefly. The allure of excitement and possibilities won the day, so I headed back into town. Day 2 started as did Day 1. I unloaded so many post that my arms and shoulders hurt. Our day had been completely normal, no talk of what happened, no indication or acknowledgement of any type. I thought to myself that maybe it was all my over active imagination.

The day was done once again as we headed back to town.

Not 5 minutes down the road, his hand dropped on my thigh again. I didn't move and I think I stopped breathing. Bob was a little bolder this time, making no pretexts of seduction, he just grabbed my cock and started rubbing me through my jeans and I was enjoying the sensation. I even spread my legs a bit to give him more room to maneuver. Once again, my 18 year old cock sprang to attention and I found myself squirming on the seat.

Bob looked at me and said, "You like this don't you?"

"Yes". I said, "Very much".

Perceived as a "go ahead", Bob told me to undo my belt and unbutton my fly, AND I did!! Like a deer in headlights, I sat there with my pants open. Bob reached in and took hold of my now rock hard cock and started slowly stroking me. I thought I had died and gone to heaven it felt so damn good. I was leaning back, slouched low in the seat with my eyes closed while he dove the damn truck and stroked me,

Suddenly, I felt the truck slowing down as he started pulling off the road. We stopped, I looked at Bob as he undid his jeans and pulled out his cock and started stroking us both. Bob then told me to stroke him. I had never touched a penis other than my own. It was soft and hard all at the same time. I liked it.

Bob said, "Let's get in the sleeper". At this point, there wasn't anything I wouldn't have done to continue this action. Once in the back, Bob pushed me on my back and lowered my jeans down to my boots, pulled my knees up and spread them as wide as my lowered jeans would allow. He raised my cock up and lightly kissed the tip, then started licking the shaft. My girlfriend had given me blow jobs before, but never did I have the level of euphoria that I was feeling at that moment. He then took me full into his mouth and started sucking me hard and fast. Bob quickly turned around and I was face to face with his rather large cock.

Bob told me to suck him too and to do to him what he was doing to me. His cock was a piece of art, perfect shape, very thick and about 6-7" long. I did to him what he did to me. I felt my climax building and told him was about to cum. He started sucking me harder and faster and I exploded into his mouth. My organism was so intense I let his cock fall out of my mouth, I think I was close to passing out. He jerked his cock a bit more and shot a load onto a handy towel.

We laid there in silence while we both recovered. We both got dressed, straightened up and re-started our trip back to town.

Arriving at the truck stop, Bob reached over and gave my cock a squeeze and asked, "Same time tomorrow?"

I went to my car and sat thinking for a while. I had to ask myself if I was now gay AND was I going to work tomorrow?

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15 Comments
AnonymousAnonymous4 months ago

LOVE IT. BRAVO! NO IFS OR BUTS. PERIOD.

I will read your other stories.

AnonymousAnonymous7 months ago

Loved it: 5- (4.6 = 92%, โ™กโ™กโ™กโ™กโ™ก-)!

AnonymousAnonymous7 months ago

Tgis is an EXCELLENT first-time-gay story.

There is a first time for everything.

AnonymousAnonymousalmost 2 years ago

I'm copy pasting an earlier comment:

Quote:

Anonymous - about 4 years ago

In the last sentence of the story he asks himself if he is now gay AND whether he will go to work tomorrow.

It is simple:

- He is now bi

- He will go to work

End quote.

AnonymousAnonymousabout 2 years ago

๐Ÿ’ฏ% = 5.0

๐Ÿ‘๐Ÿ‘!

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