The Lifeguard and the Trucker

Jay looked down at my growing cock and a smile formed on his face. “You like it?” he said more as a statement then a question. I hadn’t really stopped to think if I liked it or not, it just sort of happened. “I guess you do” Jay said reaching for my dick before I could answer.

As he squeezed my cock a blob of cum dripped out. Jay scooped it up with his fingers and brought them to my lips. “Suck it” he said, and I allowed him to enter my mouth with the cum coated fingers. It was cold and slightly salty. I wasn’t sure what I liked more the taste of the cum, or the feeling of his large rough fingers in my mouth.

As I sucked Jay’s fingers, I could feel his large dick start to swell under me. This gave me a feeling of power knowing that I was making him hard. I started to slide back and forth on his cock which was still slick with his cum puddle.

“Get up” Jay ordered turning his body and forcing me to roll off. Kneel on the bed” Jay said standing up, his big dick bouncing as he moved. Jay removed his pants showing his hairy pubes and hairy, thick, muscled legs. He moved around behind me and took my hips in his rough hand. “Bend down” he said, and a trickle of fear ran through my body, but I did as he said.

Jay parted my ass cheeks in his big hands then bent forward bringing his bearded face to my ass. I felt his thick warm tongue run the length from my balls to the top of my ass and over my hole; once, twice, three times. Each pass was warm and wet. Then he backed up and blew air over the wet spot and my body tingled and goosebumps formed. A shudder ran through my core.

I heard Jay chuckle as I squirmed from the attention. Then Jay moved in again and started to lick my hole, darting the tip of his tongue at the hole. At first the sensation was “nice” and “interesting” however as his tongue moved deeper the feeling became “intense” and “amazing”

Jay kept pressing his tongue deeper and deeper into my hole and I grasped the bed to steady myself. My dick rock hard and oozing precum all over the comforter. Jay removed a hand from my hip and placed it on my back. “Bend over” he said, and I lowered my upper body laying my head on the pillow with my ass in the air.

Jay immediately moved back to my ass, driving his tongue deeper and deeper. His furry beard rubbing my inner thighs. I could not believe how incredible this felt having his tongue in my ass. My breath was ragged as he worked my ass. Soon I felt something else, it wasn’t Jay’s soft, warm, wet tongue. It was something a bit thicker and harder. Jay had started to place his finger at the opening of my hole and he was swirling it around the edge, then he started to slide forward.

At first it didn’t quite hurt, but it didn’t feel good either. It felt like I was full, if that makes sense. Jay did not stop he slowly moved forward sliding into my wet hole. The full feeling grew and intensified, and I brought my torso up off the pillow. “Relax stud” Jay said softly and kept moving in deeper.

Soon Jay’s finger was deep inside of me, and he held it still. “Breath” Jay said, and I tried to suck in air. “It hurts” I said through gritted teeth. Jay slid his finger out and my ass felt better instantly. Jay turned and sat on the edge of the bed. “Come here” he said, and I got up off the bed. Jay took my hand and pulled me in front of him.

I looked down to see this older, hot, hairy man in just the white t-shirt and leather jacket, his hair tousled making him look even sexier. Jay pulled me down to him. “Sit on my lap” Jay said, and I did. At first it felt awkward. I hadn’t sat on anyone’s lap since I was a kid.

Jay wrapped his arm around me the cool leather on my back and arm. He ran his free hand gently down my body exploring as his fingers traced each muscle and contour. “You are so hot man” He said, a distant look as he focused on my body. I placed my hand on his cheek and pulled him to me. Our lips touched and I slipped my tongue into his mouth.

Jay moaned and pulled me closer to him, his hand moved lower and brushed my hard cock causing me to moan. Jay then ran his hand over my balls and between my legs. I spread them slightly to give him better access. Jay’s finger slid over my hole still slick with his saliva.

Jay pushed just the tip of his finger into my hole, and I gasped into his mouth. Jay held me tighter and continued to push into me. Pain flooded my body, but Jay did not stop. He moved slowly still holding me, his kiss growing even more intense as his finger invaded my virgin hole.

After some time, Jay’s finger came to a complete stop and he just held it in place. He loosened his grip on me and pulled his mouth from mine. “Do you like that?” he asked, and I grimaced. “It sort of hurts” I said. “Do you want me to stop?” he asked looking intently into my eyes. I nodded my head yes, but to my surprise Jay did not stop. “Trust me you will enjoy this boy” he said in a gruff voice. A bit of panic came over.

“Please don’t” I said sounding weak. I did not like the feeling. “Trust me baby, I am going to make a man out of you” he said and covered my mouth with his. I tried to break away, but he held me in place. Jay started to run his finger in and out of my ass, very slowly as he held me tight in place. Pleasure started to mix with pain as he went, soon the pain was a memory as it was replaced by an amazing feeling.

My body relaxed and I wrapped my arm around his neck to kiss him as he finger fucked me. “I knew you would like this” Jay said pulling his mouth from mine. I buried my head between the leather jacket and his cheek and started to kiss and nuzzle his neck.

“Oh yeah baby, I knew you would like it” he said moving his finger deeper, faster and harder into my hole. I found myself spreading my legs even wider to give him better access. My mind was being overloaded; the smell of the leather, the feeling of his body, his finger in my ass. All the senses hit me at one time and my body started to jerk and sputter.

Jay kept probing and I did not realize anything could feel so good. Something that felt terrible now was incredible beyond description. I wanted it to stop and continue all at the exact same time. My breathing became labored and my dick started to throb. Jay continued moving his finger in and out of me with the precision of a piston.

“Oh. Oh fuck. Oh yeah” I moaned, and the voice did not sound like mine. “I am going to cum” I said not understanding how this could be possible considering I wasn’t even touching my cock. My body jerked involuntarily and then my dick started to shoot. Just as it did, Jay hit something in my ass and my orgasm was so intense that I held my breath. Once again, my cum splashed Jay’s chest and his leather jacket. Jay continued moving his finger as if controlling my orgasm.

When it finally was over my body just collapsed. If Jay had not been holding me, I would be on the floor. “That was beautiful” Jay said bending forward gently placing soft kisses on my forehead, cheeks and lips.