Craigslist 1st Time Ever - Coached

At 18 I was fairly inexperienced, having only been with two women. Both times were a lot of fun but I had been craving the idea of being used by an older man.

I posted on the old craigslist that I was a 6' 190# athletic blonde 18 year old with a 7" cut dick looking for an older masculine verbal man to host and loosen me up.

I got a ton of replies but one stuck out. He was 50, 6'2, 7" thick, hairy with a silver goatee. His naked pics showed off his big muscular bear frame and immediately had me hard. He promised he would train me gently to be a good bottom. He told me to call him coach kev and I would be his jock boy.

We agreed to meet a motel between us. I pulled in, my heart rate through the roof nervous as hell. Soon I got his text, room 41. I was wearing sweats and a white T-shirt, and had to flip my already hard cock up into my waist-band.

I walked into the dimly lit room and saw him sitting on the bed wearing a suit.

"Damn boy, you are even hotter than your pictures. Are you ready?"

"Yes Coach Kev."

"OK. Strip down."

I removed my shirt, then shoes and socks, then my pants and boxers.

"Wow that is an excited jock boy! Look at that precum. I want you to use your fingers to taste it."

I complied, scooping the dripping precum into my mouth. The sweet/salty taste excited me.

"MM that's a good boy. Now I want you to shower up for me son."

I walked into the bathroom, heated up the shower and stepped in. Soon after I heard the door open and saw him there naked, his thick soft cock and big balls hanging. He stepped into the shower with me and without a word pinned me to the wall kissed me deeply. I loved it. His goatee against my face, tongue deep in my mouth, the feeling of being wanted and dominated. More exciting than anything else was the feeling of his thick cock against my ass. As we kissed he played with my ass cheeks and occasionally grabbed my cock and balls.

"Now turn around, coach is going to get you ready."

I faced the wall and felt his soapy hand run up and down my crack, cleaning me up. Soon he was done cleaning, but kept using his stout strong fingers to tease and prod my wanting hole.

"You like that boy?"

"Yes sir."

"Good, now take a deep breath."

I complied, and as I exhaled felt his thick forefinger enter my tight virgin ass up to his knuckle. He twisted it around and wiggled his finger. The feeling was unreal! I was so turned on and could feel me cock quivering. I was moaning in pleasure as he pushed his finger in the rest of the way while kissing my neck and rubbing my dick. Before I knew it he was out of me and I felt empty and wanting.

"OK. Shower is over boy. Now let's dry up and get in bed."

"Yes sir."

He dried us off as one while kissing my neck and ear and occasionally kissing me deeply. His cock was half hard now, much thicker than mine and the feeling of it against my body had me dripping precum. I walked over to the bed where he had laid a towel.

"On your back boy."

As soon as I was on my back on the towel he straddled me, aggressively dry humping me. Our cocks were slicked up with precum and he had my arms pinned to my side. It was the most turned on I had ever been and after a few seconds I came. I was so embarrassed.

"Holy shit boy! You really do like being used by your coach! But I'm going to have to teach you to not cum so quickly."

With that he slid down my body and took my cum into his mouth, swallowing it before sucking my softening cock, making it hard again immediately. Then he sucked on my balls, back up to my cock. He shoved my legs up in the air and without a word I grabbed my ankles like I had seen in the gay porn I had watched the night before. His tongue teased around my hole as I moaned and bucked my hips at him. His tongue pressed against my hole and it was the best feeling ever! I moaned and grabbed his hair and he flicked his tongue against my hole. As I loosened up his tongue entered my wanting ass. Before long his finger was back inside me, causing my cock to quiver. Far too quickly he stopped, crawled up the sheets and put his thick hard cock on my face. The smell was amazing and I kissed, then licked the tip, before taking half his cock into my mouth.

"Cover my cock with your spit boy, your ass is ready."

He then slid me up the bed and told me to grab my ankles again. Pressing his thick tip against my hole he asked if I was ready. I nodded yes and he kissed me deeply and pressed hard, but my ass was too tight.

"Looks like we need a little help." He got up and walked over to his suit, pulling out a bottle of lube.

"On your stomach, boy." As soon as I rolled over he spread my cheeks and drizzled the oil into my crack, then rubbed it around before fingering my hole. Again I felt empty as his finger left me and I looked back to see him smiling as he applied the lube to his dick. He then mounted me, rubbing his hard dick between my cheeks, sliding his big hairy body up and down on top of me.

"ON YOUR BACK, GRAB YOUR ANKLES."

I complied immediately and for good measure said, "fuck me coach, make my ass yours."

He lined up his thick cock again, told me to take a deep breath and bear down like I was shitting and then relax when I say.

"Relax." I relaxed and exhaled as his tongue entered my mouth again and his throbbing cock entered my ass. I gasped and clenched.

"Easy boy, easy. Relax or it will hurt. You ok?

"I think so coach. It hurts a little though."

"It will at first but I need you to be tough for me."

He kissed me again, with his tip in my hole. We made out for a minute as he slowly eased in deeper and deeper. Before I knew it I could tell he was balls deep in me, gyrating his hips. The feeling was amazing and I was moaning like a little whore.

"That's a good jock slut. Good boy. Ready to be fucked?"

All I could do was nod my head and he straitened up, slowly sliding his dick out of me before slowly easing it back in. The combination of pain and pleasure had me moaning and whimpering like a girl. He started picking up speed and my moans became whimpers of pain.

"That's right boy. That's my ass. Take this coach cock." He pulled out of me and I felt empty and shocked.

"Please put it back in coach I wanted more."

"Roll over boy."

As soon as I was on my belly I felt him pressing against my hole again. I took a deep breath and as I exhaled felt him penetrate me in one smooth motion. The pain was intense but I was so turned on I didn't care. He stayed deep in me, gyrating his hips, his big body pinning me down. AS soon as he started to fuck my ass again I yelped "i'm cumming" and shot my load into my belly and bed, my tightening ass milking his load out deep into me. The feeling of his cock getting even harder and he shot out rope after rope of cum into my ass was the best feeling of my life. He slowly humped me for a few more seconds after and slowly pulled out.

"That was a good job for your first time boy. Did you like it?"

"I loved it coach. Can we go again?"

He laughed, "at my age I can't fuck you again today but next Saturday you can come to my house and I can show you just how much fun two men can have together."