Skipping Practice

This is a true story about my first sissy experience. Names and some details have been changed to protect privacy. All participants were over the age of 18 at the time.

Before I get into the story, let me give you a little background info. I had considered myself to be straight for most of life. It was until just before I graduated high school that I discovered I may not be as straight as I thought. I got curious while I was jerking off one day, and I ended up cumming to a video of a crossdresser getting ass fucked by a giant cock. That was the straw that broke the camels back. Before I knew it I was hooked. Twinks, shemales, crossdressers, pegging...pretty much every category but straight porn.

My absolute favorite category though was anything involving a sissy. Watching a sissy fully embrace her feminine side as she pleasing a nice thick cock became my go-to porn. Eventually, I started to fantasize about being the sissies in the videos. I wanted to dress up, make up and all, and then suck a real cock until I my mouth was flooded with warm cum. My girlfriend Abby had no idea about any of this. She was super kinky so maybe she'd be into it, but for now I kept my secret fetishes locked safely away in my closet. This is where our story begins...

It was a rainy day in March, and I was not looking forward to crew practice after school. It was the 4th straight day of rain which meant another torture session on the indoor rowing machine. I could barely walk from being sore so when my teammate Jay suggested we skip practice and hang out at his house.

Jay and I were seniors in high school. I've known him since he moved here in grade school. We hung out in the same group of friends, but I wouldn't say we were really that close. It wasn't until we joined the crew team that we started hanging out together more often.

After the final bell rang I headed to my locker to get my bag. As I closed my locker, I turned around and saw Jay gingerly walking towards me.

"Dude I can't handle another day of this. My legs are sore as fuck and my ass hurts so bad I can hardly sit down." He said.

"Tell me about it," I said, "Sitting on those stools in Mrs. Patterson's class was brutal." We started walking down the hall towards the parking lot. "I want to skip practice, but unfortunately Abby (my girlfriend at the time), Taylor (my sister), and my mom are working on some prom bullshit at my house. They'll harass me nonstop if I go home."

Jay started laughing as we pushed open the doors to the parking lot. "That sucks man. Well both of my parents work late so if you want, we can chill at my place. Oh and I was going to bum a ride to practice so you're driving." And without giving me a chance to respond he pulled his coat over his head, stepped out into the rain, and took off towards my car.

"Alright then." I said. After making sure my car was unlocked I zipped up my jacket and chased after him to my car.

It was a pretty uneventful car ride. By the time we got to his house though it was pouring rain. I found a parking spot on the street, but it was several houses down.

"Damn it's really raining. We're going to get soaked!" He said.

"Yep," I replied, "I have to change i to my workout clothes anyways." I grabbed my bag and we ran into his house.

Closing the front door behind us he said, "My mom is going to freak out if we drip all over the floor. Just strip down and leave your wet stuff here," he said as he peeled his shirt off. I squatted down, unzipped my bag, and rummaged around for some dry clothes.

"Well, I'll I have is spandex shorts and a t-shirt," I said without looking up.

"HA! Well you're going to look ridiculous!" Jay replied.

I zipped up my bag and looked up just as Jay was pulling down his boxers. His cock was hanging down literally 2 feet from my face, and I couldn't help just staring at it. It was impressive to say the least...just shy of 7 inches long and thick...very, very thick. His dad was half Pacific Islander which gave him the appearance of always having a slight tan. The dark brown head at the tip of his cock was one of the biggest I have ever seen! Jay was 5'9" and a fit 150 pounds, with a medium length black hair. He had relatively little body hair which made his shaven cock looked even bigger as it hung just below his balls.

Realizing I was staring, Jay didn't move saying "It's gotta be what...4...5...times the size of your baby dick," he said with a grin.

I snapped out of my trance and laughed nervously as I replied, "I'm just shocked your able to live with such a tiny dick." Thank God he interrupted me because for the briefest instant I imagined trying to fit it in my mouth which sent a surge of blood to my own cock. Dismissing the thought I turned around to undress.

"Don't be shy," Jay said in a mocking voice, "come on now...let's see the little guy..."

I hooked up thumbs in my waistband and pulled my pants down, bending over and intentionally mooning him with my bare ass. Fully nude I turned around, "You're not the only one with a big cock asshole." My own cock, slightly engorged from staring at his thick member, was in full display. "That's 8 inches of big dick you're staring at," I said posing with my hands on my hips.

At 6'4" I towered over Jay. I was a lean 185 pounds with a swimmer's build, and shoulder length brown hair that made Abby jealous. I too shaved my cock and balls, but I went a step further and shaved my ass too.

Jay gave my cock a long look before saying, "I stand corrected...you don't have a baby dick after all! Congratulations!" After starring for a few more seconds he said, "I'm going to go get dressed. Just head downstairs and I'll be right there." With that he took off upstairs.

I caught myself staring at his ass as he walked up the steps. His ass was thick like a girl, and it reminded me of my girlfriend Abby's ass. Just thinking about it was enough to cause my cock to stiffen. After struggling to pull up my spandex shorts, I pushed my cock to the side and headed down to the basement. Not wanting him to see that I had a boner, I sat on the couch and used a pillow to conceal myself until it went down.

After a few minutes, he came downstairs wearing spandex shorts and t-shirt. "I didn't want you to feel weird so I put my crew shorts on as well." The outline of his cock was clearly visible as he walked over to the couch. On top of that, I could tell that it was semi-hard. "Damn my ass is sore," he said as he laid facing me on the opposite end of the couch.

As we chatted and watched tv, eventually the topic of sex came up. "I'll tell you what...you're a lucky man. Abby has massive tits." Jay said with a smirk.

"Dude you have no idea. They're huge." I replied making gestures of melons with my hands. "I love sucking on her nipples while I'm fucking her. I don't know why, but I absolutely love giant saucer nipples hahaha."

I am 6'4" with a swimmer's build, and at the time I was lean 185 pounds.

"Really? Me too man!" Jay shot back.

I had been dating Abby since my sophomore year. At 5'1", she was slightly chubby, with blonde hair that she always keep in curls, and beautiful light brown eyes. She had a great ass, but my absolute favorite part about her though was her watermelon-sized tits. She was a 36DDD with big brown areolas that were easily 5 inches in diameter. I was immediately hooked on saucer-sized nipples the moment I saw them for the first time.

"Not only does she have great tits, but she loves to get fucked in the ass," I said, "And she let's me cum in her ass too!" By this time my cock was rock hard.

"Holy fuck that's awesome. I love fucking a nice tight ass. The feeling of an asshole gripping your cock is amazing." He said. I glanced over and noticed his cock was stretching his spandex shorts like a caged animal trying to break free. He turned to look at me, and I quickly looked back at the tv. It was too late though...he for sure caught me staring at his cock.

As the conversation progressed, Jay asked me, "So, what porn have you been into lately?"

The question caught me off guard, "Uh you know...just chicks with big tits...the normal stuff." That was a lie. I jerked off last night, and it wasn't to chicks with big tits...it was a sissy riding her boyfriend's big cock. Well, it was really a bunch of videos...two twinks 69ing until they both came, a shemale with huge tits pounding her boyfriend's ass, a thick housewife pegging her sissy husband, and a skinny little femboy sucking a giant black cock while another black guy was cumming in his asshole. Even though I had a girlfriend, I had discovered that my porn of preference involved a guy sucking or getting ass fucked.

"Boring as fuck man," Jay said, "Personally, I've been watching a lot of anal. Chicks getting pounded in the ass...and even guys taking it up the ass. I just love anal what can I say!"

Holy fuck! He just said he likes gay porn! I could feel my cock stretching the spandex under the pillow on my lap. Should I tell him that I too have been watching gay porn?! Or should I truly confess that I have secretly wanted to suck cock since our "playful encounters" in the past?!

Before I had a chance to say anything, Jay threw a pillow at me saying, "I bet I could fuck Abby better than you!"

"HA! Doubtful," I said, "She loves my dick in her ass too much. Especially when I'm in this position!" I grabbed the pillow and slammed in down on my crotch in a humping motion.

"Hahahaha bullshit!" Jay replied. He sat up and grabbed a couch cushion and threw it on top of me. "Elbow drop!" He yelled as he jumped on top of the cushion, smashing it on top of me.

As we laughed and wrestled around with the couch cushion, suddenly I felt something on my hip. We paused. Jay was under the cushion. I hadn't even noticed that my shorts had been pulled down until I felt a warm wet sensation on the tip of my cock. Jay was sucking my cock under the cushion!

I pulled up the cushion and he stopped for a second to look up at me. "Keep going," I said. He looked back at my cock and then took the head back into his mouth.

By this time in my life I had gotten several blowjobs, but this was the first time I'd had a guy really sucking my cock and I loved it. He would lick the head before taking it as deep as he could. It was amazing.

Mid blowjob he suddenly stopped. Looking down to figure out why, I felt his hand grab mine and pull it down to his cock. I could feel his rock hard cock against his spandex shorts. Instinctively I started stroking it. After a couple seconds he stood up and pulled his shorts down, exposing his beautiful cock. Without saying a word he leaned forward and I opened my mouth to accept his cock.

YES! I was finally sucking a cock! I had fantasized about this so many times! I reached up with my right hand and started jerking him while I savored the taste of his cock. It was an awkward position, but I didn't care.

I sucked like my life depended on it. In, out, in, out, swirling my tongue around his velvety head. Suddenly he pulled his cock out of my mouth. "Hold up. My leg is starting to cramp in this position. Let's switch it up." He said. As he stood up, he pulled off his shirt and kick his shorts to the side.

Following his lead, I stripped down as well. What a sight. There we were, completely naked, both of us with raging hard cocks pointing straight out. As we stood facing each other, we were both entranced with each other's cock.

"You were right," I said, "We both have a solid 8 inches, but your's is definitely thicker."

"Not thick enough that you can't suck it I hope." With that he put his hands on my shoulders and pushed me down on me knees.

"Let's find out," I said just as he shoved his cock back into my waiting mouth. As I sucked I reached down and starting jerking my cock.

"Fuck that feels good," Jay said with a moan. I picked up the pace. I wanted to taste his load in my mouth. Just as I started tasting his precum he pulled his cock out of my mouth and said, "Hold up. I want to try something before I cum."

"Alright...what did you have in mind?" I replied.

"Hahaha you'll see. Let's go up to my room. it's a little more comfortable than the basement," Jay said as he started walking upstairs, "Don't worry...you're going to like what I have in mind..." He paused at the top of the stairs and bent over, pulling one ass cheek to the side with a smack, and then headed down the hallway.

The sight of his tight brown asshole caused my cock to starting dripping precum in anticipation. "He's going to let me fuck him in the ass," I said under my breath, and i hurried upstairs his room.

As I entered his room he was laying on side across his bed, with his enormous cock sticking straight out. I jumped on the bed facing him.

As we laid there I reached out and started stroking his cock. He gave me a smirk and grabbed my cock in return.

"I lied to you earlier," I said as I jerked him, "Lately, I've been watching a lot of...well...gay porn," I confessed, "Also some shemale stuff...sissies are my favorite...oh, and guys getting pegged by their wives. Basically anything that involves a guy sucking cock or getting butt fucked."

At that moment Jay gripped my cock extra hard, and started to jerk me faster. "I fucking knew it!" He blurted out, "What have you watched recently that you really want to try?"

"Well...last night I watched two twinks 69ing until they came in each other's mouth," I said, "And earlier you stopped me from tasting your cum." Then without warning I pushed him down on the bed and spun around so that my cock was right in his face. In one motion, I engulfed his cock with my mouth and slide my own past his lips, and onto his warm wet tongue.

I swallowed his cock as far down as I could, and then slowly pulled it out. Jay let out a moan each time I took his cock in my throat. Meanwhile, he took a different approach. Gripping my cock with his hands, he would stroke downward and suck at the same time. Each time he took me into his mouth I edged closer to cumming.

Suddenly Jay called out, "Fuck I'm going to cum!"

"Me too!" I cried out. No sooner than the words were out of my mouth Jay's cock started spasming. I clamped my mouth around the head of his cock and my mouth was flooded with his hot cum. Without even hesitating I started to swallow as much of it as I could, with the rest spilling out on my face. The sensation of swallow his cum put me over the edge, and like a dam breaking, I flooded his mouth with my cum. I could feel Jay trying to gulp down each spurt.

After what seemed like forever, we finally stopped cumming and I rolled off of him on to my back.

"That was the first time I've swallowed cum before," I said as I laid back and relaxed.

"Me too. I didn't know if I was going to do it, but once you started cumming I couldn't resist," he replied, "And by the way, you came so much that it's all over my face hahaha."

I sat up and looked at him and couldn't help but laugh. "It's all in your hair too. You shot some all over my neck and cheeks so you're not the only one covered in cum."

Jay stood up, his big cock bouncing against his stomach, "Well my parents won't be home for 2 hours, and I don't want dry cum in my hair. I'm going to go get in the shower. Care to join me? If you're lucky I might let you wash my back..."

As Jay got up I just laid there and thought to myself, "Wow. I can't believe that not only did I just suck my first cock, I just 69'd with a guy and it was one of the best blowjobs of my life. Don't get me wrong, my girlfriend Abby gives great head, but I don't think I've ever cum that much in my life. I wonder what Abby would think if she found out that I just swallowed a guy's cum..."

Jay really did have a great ass. I loved the way his thick ass looked as he walked out of his room. Plus I caught a glimpse of his asshole earlier, and I wanted a better look, so I got up and followed him to the bathroom.

It was a walk-in shower so we had plenty of room. After the water got warm, we grabbed some towels and stepped in together. My cock was getting hard again, and I made it a point to poke Jay ass with it as we got into the shower.

Jay squirted some shampoo in his hand before turning around to toss it to me. I noticed his cock was sticking straight out. "Perfect," I thought, "He's ready for round two."

The shower was big, but in order for both of us to be under the shower head at once we had to huddle together. As we rinsed the shampoo I could feel our cocks poking against each other.

"Hand me that conditioner." I said.

"You not only suck cock like a girl, but you have long hair like one too," he teased as he gave me the conditioner, "Here you go princess!"

"Fuck you," I said as I grabbed the bottle, "At least I'm not short like a girl."

Unlike Jay, my hair is light brown, thick, wavy, and it was down to my shoulders. "You'd condition too if you had beautiful hair like mine," I said as I rinsed the conditioner out of my hair.

Jay handed me a soapy loofa saying, "My arms are too sore to get my back, can you get it for me?" Then stepped out from under the shower head and turned around. I felt my cock jump with excitement as I stared directly at his glistening, wet ass.

"Sure," I replied as I started to rub the soapy loofa on his shoulders. Next was his mid back, then his lower back, and then finally that delicious looking ass of his. I rubbed the loofa in circles on his ass cheeks before using my other hand to slightly spread them to get access to his asshole. After I got his asshole nice and soapy, I reached under and started working on his balls. He adjusted his legs to give me better access.

"We need more soap," I said as I squirted the shower gel into my hands, "This loofa isn't doing the trick." I reached my right hand around his side and started soaping his rock solid cock. As I did, Jay arched his back so that his ass stuck out just a littttllee biiittt further giving me better access to his ass. I slid my other soapy hand up and down the crack of his ass, rubbing my fingers against his asshole with each pass.

Turning his head to the side Jay said, "Good thinking."

I reached down and massaged his balls for a few seconds before returning my soapy fingers to his asshole. Still jerking his big cock slowly, I rubbed my fingers in a circle on his asshole, and then pushed the tip of my middle finger inside. He responded with a soft moan so I slipped my finger deeper in his ass.

"...Uggghh that feels good...keep going," he said.

I worked my finger in and out of his ass while stroking him. As I felt him start to loosen up a bit, I used a second finger. He moaned in delight so I picked up the pace. In...out...in...out...each time I could feel his asshole relax and then grip my fingers. But I didn't want him to cum yet so I pulled my fingers out of his ass, and pulled him back under the water to rinse the soap off.

"Damn man why'd you stop!" Jay said in protest.

After the soap was rinsed off his ass I pushed him forward against the wall saying, "Because of this." I dropped down to my knees, spread his ass cheeks, and then buried my tongue inside his asshole.

Jay was caught off guard. As soon as my tongue slipped inside his asshole though he slid his hands up the wall to bre himself, and thust his ass back into face.

"Ohhh yeah...eat my ass...that feels so good," Jay said with his face against the wall.

I seitched uo my assault on his asshole by licking circles around the edge slowly before tongue fucking him as deep as I coukd get. This was not the first time I've given a rimjob. I love to eat ass. In fact, Abby regularly sticks her ass in my face, particuarly when she wants anal.

As I continued eating his ass, I started jerking my throbbing cock. Even though I had just exploded a massive load down Jay's throat, I felt like I had another gallon ready to go. Based on my previous experiences with Abby I could tell that his asshole was also ready to go. I gave him one last deep tongue fucking before I stood up, slapping his ass in the process.