Skipping Practice

Jay didn't say a word. He continued to stand with his hands against the wall and his legs spread. His perfect smooth brown asshole was completely exposed and ready for my cock.

I grabbed a bottle of baby oil fron the shower caddy and poured it over all 8 inches if my rock hard cock. Then I spuirted oil at the top of his ass, and used my hand to rub it all over. I made sure to slide a couple fingers in his asshole to lube it up before setting the bottle down.

My fantasy of fucking a man in the ass was about to come true. Using my hand, I guided the tip of my glistening cock right up against his asshole.

"Do it. Fuck my ass," Jay said in a passionate voice, "I want to feel that big cock inside me."

Slowly I pushed forward into his virgin asshole. His asshole was tight, but I could feel it opening up as I slid further and further inside. Finally I felt the head of my cock slip past the entrance, and his asshole engulfed my cock.

"Ohhh.." Jay moaned as the whole 8 inches disappeared inside of him.

"You're ass feels amazing baby," I said. I started picking up the pace, pulling my dick almost all the way out before shoving it in as far as I could go. Jay was pushing his ass back with each thrust, pushing my cock deeper and deeper inside of him.

"Yes! Harder! Fuck me!" Jay cried out.

By this point I was going to town and he was loving it. I would pull all the way put before plunging it back inside him. I was getting close to cumming.

"I'm gonna cum soon!" I said.

"Cum inside me!" he shot back in between moans.

I felt my cock pulsating so I pushed it all the way up his ass just as I started to cum. Jay clenched his ass as soon as I was balls deep inside him. "Ugghh," I moaned in totally ecstasy. Spurt after spurt, waves of pleasure pulsed through me as I emptied my balls. It just kept coming! I just closed my eyes and let out a sigh as my cock spasms began to slow. Finally it stopped and my cock popped out of his asshole, followed by gobs of my cum.

I took a step back to catch my breath and admire Jay's amazing ass. He was still standing there with his hands against the wall and his legs spread. I could see my cum leaking from his stretched asshole.

"Holy fuck. I wanted to get my ass fucked for so long," Jay said turning around, "I've used my mom's dildo a few times, but damn man...that doesn't come close to an actual cock hahaha."

"You used your mom's dildo?!" I exclaimed.

"Well...uhhh...I mean I washed it first...it's not like I just grabbed it from her when she got done using it!" Jay said nervously.

"Wow man," I replied trying to make him as uncomfortable as possible. "I have only borrowed my sister's dildo," I said with a smirk, "...well I tried my mom's but it wasn't big enough..."

A few months ago I found my mom's dildo in her nightstand. It was only about 6 inches long, but I loved to watch sissy's getting fucked while toying my ass and pretending it was. Curious, I went into my sister's room and found her dildo in a box under her bed. It was probably 8-9 inches and THICK! It took me a few times to get it all the way in, but it felt so good.

"Hahahaha you asshole!" Jay said pushing me, "Hand me the soap. I can feel your cum leaking down my leg."

I tossed him the soap and stepped out of the shower. While I was drying off I noticed a thong on top of a pile of dirty clothes. Despite cumming twice already I felt my cock tingle. I grabbed the thong and walked out of the bathroom saying, "Hurry up...I want my ass fucked before your parents get home..."

As Jay finished up in the shower, I walked down the hall completely naked to his bedroom to wait for him. I wasn't going to be naked for long though...as I left the bathroom I grabbed a lacy thong from a pile of dirty clothes. Jay didn't see me so I knew he was going to be completely surprised when he saw me wearing it.

When I got i to his room I held up the panties, imagining Jay's mom wearing them. "Dammmnnn," I said out loud, "I had no clue Mrs. S wore underwear like this." It was a red lacy thong with two little black bows on each side of the crotch. Even more shocking was the split in the back. "It seems that Mrs. S enjoys getting her ass fucked as much as her son," I said with a chuckle.

As I stepped into the panties I felt a chill up my spine. Of ALL the porn I'd had consumed in my teenage years, by far the best was anything involving a sissy. I just love seeing a sissy all dolled up and getting her asshole destroyed by a big cock. Over the years I had fantasized about becoming a sissy. Sometimes I would try on my girlfriend Abby's panties and fuck my ass with her vibrator, but she had no clue. In fact, nobody had a clue.

I pulled them all the way up, making sure to adjust the back so my asshole would be perfectly exposed. I had already cum in Jay's mouth, and his asshole, but I felt my cock stir as I struggled to tuck it inside the panties. I stood in front if the full length mirror in Jay's room to admire my ass. "Wow my ass looks great," I said before bending over to check that my asshole was easily acessible, "Yep. She definitely takes it in the ass."

I snapped back to reality when I heard Jay coming down the hall. I quickly jumped on the bed to surprise him. I laid on my stomach with my feet in the air and my ankles crossed. l propped myself up with my elbows, and turned my head to face the door just as Jay walked in fully naked dry his hair with a towel.

"Are you...are you wearing panties?!" He asked.

"Hrmmm...I don't think I'm wearing panties," I replied playing with him, "Although I can't really see my ass. Can you come over here and take a better look to be sure." I quickly glanced down at his thick cock before making eye contact, wiggling my butt just a little bit.

"Yeah youre right," Jay said with a smirk, "I need to take a closer look to make sure." Jay walked over to the end of the bed, his cock beginning to grow.

I got on my knees and spread my legs a little bit giving him full access to my ass saying, "This should help you see better." I was face down, ass up, and wearing red lacy panties...if my girlfriend Abby could only see me now.

Jay crawled on the bed and grabbed my ass with both hands. I could feel his breath on my ass as he said, "Yep. You are definitely wearing panties on that sexy sissy ass." He spread my cheeks a little bit exposing my asshole through the opening in panties. "Damn and they give me easy access to your tight sissy pussy!" I let out a soft moan as he rubbed his finger over my asshole.

He took that as his cue and he started kissing my right ass cheek, moving closer to my asshole with every kiss. Just before his lips got to my asshole, he teased me by switching over to the other cheek and starting over. My cock was rock hard at this point, and stretching the panties so much I thought they were going to rip. Suddenly the kisses stopped and I felt his warm wet tongue against my asshole.

"Ugghhh...that's it baby...eat my sissy ass," I cried out in a sultry voice.

Jay grabbed both cheeks and spread my ass wide before he buried his tongue in my asshole. My girlfriend Abby loved to get her ass eaten, but I had never been on the receiving end before. Now I understand why she loved it so much. Jay was switching between licking the rim and pushing his tongue just past the opening of my asshole. Each time he pushed his tongue inside he would go just a little bit deeper. Finally my ass opened up, and he stuck his tongue in as far as it would go.

"Yes!" I cried out, "Eat my sissy ass!" I pushed my ass back against his face. My cock was leaking precum all over the panties. "Finger my ass daddy," I said.

Jay pulled his face back and placed his middle finger against my asshole. "If you insist sweetheart," Jay replied before pushing it inside of me. He started stroking his cock with his other hand as he began to finger my ass. I could feel myself opening up even more...almost ready for his cock.

"Mmmm...that feels good...stick another one in," I said. He pulled his finger out and replaced it with two, working them up my ass. My asshole greedily accepted them. "That's much better," I said looking back over my shoulder, "This feels great, but I think I'm ready for you fuck my ass with that big cock daddy."

Jay flashed a smirk. "Gladly sweetheart." He stood up and walked to his nightstand to get something. Rummaging through the drawer he said, "I think I have some lube in here." His cock was sticking straight out in front of him with a drop of precum on the tip. As he searched I leaned over and took him into my mouth, tasting his salty cum.

After about 15 seconds I stopped sucking his cock and asked, "What is taking so long?"

"Hahahaha nothing. It's right here. I was just enjoying the blowjob." Jay replied.

"Come on daddy...your sissy slut needs her ass fucked. You don't want to keep a girl waiting do you?" I said with a pout.

Jay laughed as he squirted some lube into his hand and rubbed it all over his cock. Walking back to the foot of the bed, he squirted more in his hand and tossed the bottle on the floor. I felt a shiver when he worked the cold lube into my asshole with his fingers. Then he climbed up on the bed and his slippery fingers were replaced with the tip of his cock.

My heart was pounding. I had fantasized about getting ass fucked for so long and it was about to finally come true! I reached down and started rubbing my cock through the panties in anticipation. Without saying a word he slowly started pushing the tip of his cock into my asshole. As he entered me, I could feel my asshole trying to resist the foreign invader, getting tighter and tighter the deeper he went. Then without warning the head of his cock slipped inside me and my ass opened to accept him.

"Mmmmm yes daddy..." I moaned as his cock slid all the way into my ass. "Fuck that feels so good!"

"Your ass is so fucking tight." Jay said. He kept his cock buried deep for a moment to give me time to adjust to having my asshole stretched by his 7" cock. Even though I had an inch on him, his cock was thicker than mine. Slowly he pulled out before sliding back inside of me.

"Oh my God...daddy your cock feels fucking amazing! I'm ready for you start fucking me!" I cried out.

Jay picked up pace until he was fucking me like the sissy slut I deserved to be. To this day, this was the best ass fucking I've ever received. I pulled my panties to the side and started jerking my cock as he fucked my ass. Each thrust rubbed against my prostate and got me closer to cumming.

As he continued pounding my ass, I decided to abandon jerking off and get on all fours. "FUCK ME! FUCK MY SISSY ASS!" I yelled. Jay starting going faster. I pushed back against his cock, matching his rhythm, my own cock bouncing with each thrust.

Jay was going to town on my ass with his thighs slapping my cheeks as he fucked me. Smack. Smack. Smack. I wasn't even touching my cock, but I felt the unmistakable feeling of an orgasm building.

"Ugghhhh.." I moaned, "I'm going to cum soon! Fuck me daddy! Make me your sissy bitch!" I couldn't believe it but I was just about to cum from getting my ass fucked!

"I'm going to cum!" Jay said as he furiously fucked my ass. Then it happened. It actually happened. His balls tightened and he shoved his cock deep inside my ass. "Oooooohhh," he grunted and his cock flooded my asshole with his hot cum. The feeling was too much for me to handle, and started cumming as well. I could feel each spurt of cum in my ass and I loved it.

After he finished breeding my ass for the first time, he pulled his cock out with a plop and flopped down next to me entirely spent. I looked down at the pool of my cum on the top of his comforter, "Uhhh so I'm really sorry but I came all over your bed. I wasn't even jerking off it just happened," I said as I stood up.

"Hahahaha honestly man, that was the best anal sex I've ever had so don't even worry about it," Jay replied, "Besides...a sissy is supposed to come when daddy fuck her ass."

I flashed a smile and peeled his mom's cum soaked thong off and threw it at him. "Thank you daddy." I said in my best girly voice. I grabbed my stuff and starting walking to the bathroom. His cum was leaking from my freshly fucked asshole. Stopping at the door I turned and said, "Oh by the way...I'm pretty sure your mom likes anal too. That was her thong."

"The fuck dude!" Jay yelled throwing the thong back at me. I laughed as I walked out of his room to go clean up. The whole time I thought about what my girlfriend Abby would think if she walked in on me getting butt fucked wearing panties. She's pretty kinky in the bedroom, but watching your boyfriend taking dick while moaning "fuck my sissy ass" probably wouldn't go over well. "Oh well," I said to myself, "luckily she has no idea..."