I was smitten by Jack’s powerful cock and was ready to do anything he asked. “What can I do?”
“You know that adult bookstore down on Main Street?” he asked.
I nodded affirmatively.
“I want you to go buy a series of butt plugs. You can start with any size you think you can handle, but make sure the last one is the biggest they have. And buy yourself a big bottle of lube.”
“Yes Sir,” I replied. I knew my ass training was soon to begin, and I wanted more than anything to be able to take Jack’s huge schlong up my ass like a pro.
“You can leave the toys here in the shed, but I want you to keep one of the plugs in your ass at all times. Also, buy a big dildo, one of those with the suction cup bottoms. We will meet back here tomorrow morning, and before you service me, I want to see you take that dildo up your ass.”
“Yes Sir,” I whimpered as I fantasized about getting bent over and fucked my Jack’s powerful tool. My penis was again erect, as I did a horrific job hiding my obvious excitement.
“I’m taking Martha out for dinner and a show tonight,” Jack said. “You can use the shed to practice tonight. Make sure you practice sucking on that big dildo too, cause I don’t want to have to retrain your throat again tomorrow. Now get dressed and get the fuck out of here.”
I was so excited to begin my anal training that I didn’t even bother to take a shower, leaving Jack’s cum to dry on my chest as I grabbed the car keys.
“I’m heading to the hardware store,” I said to Laura. Thankfully she had no idea what kind of hardware I was buying.
I bought three butt plugs, a large bottle of anal lube, and a fat 8″ black rubber cock. The clerk smiled curiously as I paid for the gear, but I was too far gone to care what she thought.
In the car, I lubed up the small plug and pulling my running shorts aside, forced the cone shaped toy into my virgin ass. With an audible pop, the plug firmly seated in my hole. The initial discomfort slowly subsided and by the time I pulled into the driveway at home, a huge wetspot had appeared on my shorts, my dick clearly enjoying the feel of the plug in my butt.
I snuck into Jack’s backyard and put my new toys into a drawer in Jack’s workbench. Already adjusted to the small plug, I lubed up the medium plug and worked it into my butt. I also unwrapped the big dildo and spent several minutes deepthroating the big toy, quickly overcoming my gag reflex and eagerly licking the big rubber nuts with the entire length of the rubber cock buried in my throat. Jack was going to be very pleased.
I spent the afternoon doing yard work, the medium plug firmly planted in my ass. When I saw Jack and Martha leave, I went into the shed and exchanged the medium plug for the biggest plug. It took several minutes to work that monster into my stretched hole, but when it finally popped in, I let out a relieved sigh. If I could handle this toy, I knew I could take the rubber cock.
My cock was again rock hard, so I jerked a load all over the rubber dick, before spending 20 minutes practicing my deepthroat skills. The natural lube of my jizz helped the dildo slide down my throat easily. Looking into the mirror over Jack’s bar, I watched myself take the slippery cock down my throat, knowing I had a huge butt plug impaled in my once virgin ass. In a little over 24 hours, I had been converted from a pussy-loving, 100% heterosexual into a cockcraving, cumloving, butt pirate. And I couldn’t wait until tomorrow morning to show off my improving skills to Jack.
I fell asleep that night next to Laura with the big butt plug firmly rammed up my now stretched hole. Little did she know that her husband was soon to be fucked by Jack, the “nice old man” that lived next door.
I was so excited the next morning, that I skipped my run altogether and knocked on the shed door right on time.
As I walked in, I noticed that my new dildo was stuck to the front window, swaying menacingly.
“Morning bitch,” Jack began. “I don’t want to have to remind you each morning to strip, so please undress each time you enter our little sanctuary.”
Jack was sitting in his recliner, watching porn on his big screen TV. A hot little starlet was getting tag-teamed by two big cocked studs and she was moaning and groaning like she was in the throes of a non-stop orgasm.
“Bend over boy. Show me how well you take instructions and let me see that butt plug.”
I bent over and grabbed my ankles, exposing my ass with the plug firmly planted in my rearend.
“Reach around and take it out,” Jack insisted.
I pulled the rubber toy from my ass, feeling the breeze from the overhead fan blow up my now gaping hole.
“Excellent,” Jack said. “Now get over there and show me your deepthroat skills on that black rubber cock. Interesting choice might I add; should have known you’d be a slut for black dick.”
I engulfed the rubber toy in one mighty slurp. As I began to bob up and down on the dildo stuck to the window, I did a comical double-take as I watched Martha come out onto the back patio to water the plants, only about 30 yards away.
I quickly ducked below the window sill, hoping she hadn’t seen me.
I felt a swift whack across my bare bottom as Jack hit me with a short piece of rope. “You dumb fucker. I told you the windows are tinted, she can’t see you. Get back up there and stuff that dildo back down your throat.”
Relieved, I went to work on the big cock, still somewhat uncomfortable that I was deepthroating a dildo as I watched Martha doing her housework.
“Do you think you can take that rubber dick in your boy-hole?” Jack asked as he stripped off his shorts and t-shirt, his semi-erect cock clearly pleased by my progress.
“Yes, Sir,” I replied, scared but eager to try.
Tossing me the bottle of lube, Jack continued, “Lube up your hole, spread those cheeks, and show me how bad you want a cock up your empty ass.”
I squirted the lubricant on my ass and positioned the big dildo at my opening, pushing firmly back as the toy popped through my ass-ring and easily, if somewhat painfully, drove into my gaping ass.
“Now fuck it,” Jack ordered.
As instructed, I began to rock back and forth on the rubber rod, the friction on my prostrate quickly replacing the discomfort with a feeling of immense pleasure. My cock was dripping with precum as I fucked the black rubber dick.
“Damn, you are one horny little slut,” Jack chuckled. “Never seen a recruit take to basic training like you.”
As I continued to fuck myself, Jack presented his cock at my lips. “Don’t just look at it, bitch. Suck it.”
I eagerly obliged and took Jack’s penis into my mouth, savoring the salty taste of his beautiful cock. As I rocked back and forth, I was getting fucked like a rag doll between Jack’s powerful face-fucker and the fat rubber toy.
After several minutes of this action, Jack pulled his now fully erect rod from my stretched jaw. “Didn’t think you’d be ready for this yet, but looks like you need a real ass-fucking now.”
“Yes, Sir,” I replied. “Please fuck my tight little ass with your big cock. Take my virginity, Sir. Take it now.”