crossdressing has always been my secret pleasure I even had a cache of out fits make up wigs and heels. it started when I was younger but evolved as I got older, now as I got older ive refined my skills and abilities and can pass as a girl when dressed. I had fooled around with guys before but I had never dressed for one only indulging in self pleasure with toys and my fingers. when I got off work on friday I was excited for the up coming three day weekend going home to get dressed up maybe go shopping and get some new outfits. I love going out in public dressed like a slutty girl im very pass... Continue»
After chatting for a few minutes on line, I was quite anxious to get over to his place. Bobby lived just south of the University and at 23, I was really looking forward to a solid afternoon with a young, hard stud. He opened the door and led me down the steps to the basement apartment in the house.
Bobby was 6 ft tall and weighed about 170 pounds. He was Aboriginal. He had jet-black, shoulder-length hair. As we started to strip off, he first revealed his hairless chest with its firm pecs and rock hard stomach. As he peeled off his shorts and underwear, he revealed a gorgeous cock that was quite big and had yet to realize its full potential. I finished peeling my gear off and joined him on the mattress on the floor. I went straight to his cock. Already about 7 inches in length and fairly thick, I gripped him with my hand and took him in my mouth. While swirling my tongue around his knob, I pulled his foreskin back to lick, tongue and taste his bulbous cockhead. He was extremely tasty and I proceeded to inch a bit more of him into my hungry mouth and throat.
As I worked the shaft of his amazing cock into me, I could feel it expanding as he filled my entire mouth and throat with his man flesh. He grew to his amazing 8 ½ by 6 inches in short order. I was now in my glory. I had a young, hot, big, thick, juicy and hard cock right where I needed it. I sucked Bobby and would have stayed right there forever, but he wanted a little taste of me. I swung around without letting go of him. He impaled his throat on my cock and we worked a 69 in tandem.
For me, I sucked his cock all the way to the tip where I would poke my tongue into his slit, swirl my tongue around his big knob and then take him all the way to the back of my throat, inch by inch. I would stay with my lips rubbing his pubic hair while I was swallowing on a piece of meat that would just stay right where it was as I swallowed over and over again, massaging his cock with my throat.
For Bobby, he was feasting on my cock like he hadn’t eaten in a week. Pulling my foreskin back, he sucked on my knob, lapping up the gobs of pre cum that had already oozed out of me before taking my entire 7 ½ inches all the way to my trimmed pubes. He rode up and down my shaft, occasionally releasing it to suck and lick the underside of my cock, all the way to my balls. He took my balls into his mouth one at a time and sucked each one rolling them around in his mouth. It was when he released the second one and stuck his tongue into my taint and started working towards my ass that I released his cock from the lip lock I had on it.
The two of us maneuvered around the mattress so that Bobby could have total unobstructed access to my ass. I lay on my back and pulled my knees up to my chest, grabbing my shins to provide Bobby with the access to my pucker that he craved so much and that I so wanted him to have.
Bobby wasted no time playing around. He pushed his face right into my ass and his tongue found my hole with ease. As I moaned from the pleasure, I strained to grab my glutes so I could pull my cheeks wider apart. I needed more tongue and Bobby needed more ass. He bore into me with his tongue. It felt incredible as Bobby fucked me with his tongue. I was pushing back on his face to get more of his tongue. He now had both of my legs held over us as he gripped the back of my thighs to get at more of me.
Bobby replaced his tongue with his thick index finger. He had all of it inside of me. He twirled it around, back and forth. Pulling it out, he squirted a bit of lube on my hole and inserted two fingers. While it felt wonderful, I still had an itch further up that his fingers just couldn’t reach. Bobby added a third finger. As he pushed all three of them into me, my sphincter clamped down from the invasion. He just slowly moved his wrist back and forth as his fingers bore into me, loosening me up for the prize.
Bobby removed his fingers. Grabbing me by the hips, he flipped me over and pulled me up to my knees. I bent forward so that the screams I knew were going to come from me would not wake the neighbours. As I buried my face in the pillow, Bobby buried his cock into me. The fire and searing pain were instant as his bone rubbed against my tight insides all the way up and into my bowel. I yelped into the pillow and pushed back hard on his cock hoping that he would give me just a minute to recover.
He leaned in to my ear.
“How’s that feel?” He whispered.
“Oh fuck,” I said. “You have no idea” was all the response I could offer.
The brief exchange allowed me a moment to get accustomed to his girth. Bobby was certainly filling, to say the least. His cock was all the way into my lower intestine and my canal was stretched to its fullest. I took a couple of deep breaths and as I pushed my face back into the pillow, Bobby began riding my ass. He started slowly at first. He would come out about a few inches and then slide it back in. It felt amazing. His slow, shallow pumps allowed me to adjust to his size and in no time, I was rocking back and forth on his cock as I continued to moan quite audibly into the pillow.
It didn’t take long before Bobby started to pull his entire length back out to my ring and then immediately thrust it back up into my soul. As he continued this steady welcomed assault of my ass, he took my pushing back on his cock as I sign that I wanted more. He quickened his pace. I kept rocking in an opposite motion to his thrusts. Bobby started pounding me with his pole and I was pushing back, screaming into the pillow which did a great job of muffling the screams I needed to release from the pleasure I was receiving.
Bobby worked away at me. His steady pounding showed no signs of ending. I too was enjoying the ride so much that I was hoping it would never end. Bobby reached around me and grabbed my cock while he pounded away. I was rock hard but had paid no attention to my own cock as I was so focused on his meat and the pleasure it was releasing throughout my entire body. As Bobby pounded away on my ass, his work on my cock had me to the point of no return. I raised up on my arms. Bobby grabbed a handful of hair with his free hand, like he was holding on to the reins. As he pumped my cock and pounded my ass, I was able to mutter.
“Bobby, … I’m … going … to … cum.”
I no sooner said it then a huge blast of my cream gushed out and onto the sheet below me. The spasm in my cock worked its magic throughout my entire body and as I shuddered from my first gush of cum, my ass contracted tightly around Bobby’s cock.
“Oh fuck, yeah!” He said.
His cock had hardened to steel and he thrust all of it up inside of me. I could feel his pulsating member deliver its first blast of cum off my inner wall about the time my second spasm came on and I shot a second blast into the sheets. With Bobby’s cock fully inside me, throbbing and delivering a new geyser of cum with each pulsating throb of his cock, the two of us delivered each other to a mind blowing simultaneous orgasm, the likes of which I had never experienced before. I shot about eight solid streams of cum into the bed sheets. Bobby’s orgasm continued for about four extra blasts after mine had started to subside. I don’t think either one of us knew when it was actually over. We both just stayed in our position. Motionless. Glowing.
As we slowly came back down to reality, Bobby withdrew his still semi hard cock from my tingling ass and collapsed beside me on the bed. I just dropped my head onto his shoulder and lay down in my own pool of cum. We were so content as we laid there basking in the afterglow of our love making.
“That was the best fucking I have ever had.” I said
I was thrilled when Bobby said that it was absolutely wonderful for him as well. But then he paid me the ultimate compliment.
“Would you like to get together again, maybe on a regular basis?”
And you just know we did. I was hoping he would stay and get his Masters Degree, but we did have almost two years of regular meets and he has called me both times he has returned to Edmonton on business.