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Breaking Him In

I stepped off the train at Union Train Station in Los Angeles wondering if I should feel guilty, or proud, or if I should tell her at all. After all, Naomi has always told me she wanted to watch me get fucked by a complete stranger. But...would it make her jealous that I fucked a cute girl about the same age as me in the bathroom of the train to Los Angeles?

"I'm so happy to see you baby!" I smiled pleasantly and picked up Naomi and planted a deep kiss, sucking on her tongue and biting her lip.

"I have a surprise for you" she said with a sly grin on her face; I was hoping that she had finally convinced her sexy, dance teacher roommate to join us in our sexual adventures. "Did you shave this morning?" she asked raising her eyebrow.

"No honey, I shaved right before I left" I replied smiling - knowing that she loved me to fuck her while my entire body was shaved clean like a baby.

As we walked into Naomi's appartment I was abit dissapointed. Her roommate was not there, her things were packed, she seemed to have gone out of town. "So, if I'm not getting that threesome, then what is the surprise?" I thought to myself as Naomi walked into the room smiling wickedly and carrying a metal rod with shackles on it, a pair of genuine handcuffs, seven steel rings of different sizes, a leather paddle, a leather bull whip, and an 9 inch long metal rod that was half an inch in diamter, a dog collar with a leash, an o-ring gag, two 5 lb weights, and a box of surgical steel needles along with a box of paraffin. "So it looks like we have moved past the tie me up to the bed and rub warm oil over my cock and balls, place a rubber cock ring on me and ride me til her legs give out kinky sex status" I thought to myself smiling.

"Off with your clothes slut! And make it quick!" I stumbled and froze in shock as she had never addressed me in such a manner before. I quickly removed my clothes as the bullwhip struck my chest cutting my dress shirt and leaving a welt across my sore pectorials. "On your knees bitch!" she ordered as she swung the bullwhip once more upon my chest leaving another welt despite the fact that I was already on my knees.

She wasted no time in fastening my ankles to the spreader bar, fastening my hands behind my back with the cuffs, placing and tightening the collar and leash around my neck, and slapping me harshly across the face busting my lip open. "You will do as I say and when I say it you whore!" another slap echoed accross my face. "If you dissappoint me you will receive five hard lashings with the bullwhip. Understand dog?"

"Yes ma'am!"

"You will address me as Mistress Naomi you dogslave!" she responded as another slap sent my head spinning.

She pulled off her cargo pants revealing her strong athletic legs, her small, soft and perfectly manicured feet, her tight, round, perky, and muscular ass, and her soft, brown, juicy temple covered and protected by a thick, black, clean and shiny bush of pubic hair.

Naomi took my leash into her hand and walked behind me with the leather paddle. "Crawl slut! On all fours like the dogslave that you are. Crawl!" I started crawling on all fours while she kept me tight on her leash and start brutalizing my ass cheeks with the leather and wood paddle. My ass got redder and redder and stung to a painfull pitch as she spanked me unrelentlessly.

"Mercy! Mercy! Please Baby! I'm Begging You! Mercy!" I cried out.

"You just bought yourself 5 lashes you disobedient bitch!" she replied.

"No...No..Please Mistress....It Hurts...I Can't Take It...Mistress...Please!" I whimpered.

Once the turret of paddling ceased, I collapsed onto my belly. I crawled to her and began licking her feet and nibbling on her toes. I sucked her toes into my mouth and suckled and kissed her soft and beautifull feet much to her delight as she was letting out soft moans and began fucking my mouth with her feet. I moved up to her calves and lubricated them with my saliva and left teeth marks on her muscular calves. I crawled even more forward and boldly began to kiss her strong, athletic thighs. I was encourage by her deep, grunting moans and the heat and musk escaping her delicious cunt.

"Again slave!" she demanded as she shoved her toes into my mouth. My head bobbed up and down and saliva dripped onto the floor as I ravenously sucked and slurped and bit onto her toes. She fucked my mouth with her luscious feet so hard that my jaw was sore. "You have 15 lashings in store. If you fuck this up I'll double them. Understand Bitch!" she stated.

"Yes Mistress Naomi" I replied subserviently.

"Now you are learning slut." she replied conceitedly. Naomi tugged on the leash and pulled me to my knees. My hands were numb from the cuffs and my shoulders were in pain. She placed her dripping wet slit above my face. I eagerly opened my mouth and stuck out my tongue. She lowered herself until the tip of my tongue was barely touching her clit. The musk from her cunt was intoxicating and made my cock ooze with precum. I opened my mouth even more and forced my tongue out more and pressed her clit softly. She let out a moan and then pulled apart her soft lips revealing her wet juicy pussy. My cock was aching, my balls were twitching.

"If you spill one drop - I double the lashings!" she stated as a thick, powerful river of warm, salty, and strongly scented urine poured out of her temple and into my wide open mouth. My first reaction was to gag. Then I wanted to spit it out. But her warning echoed in my ears so I drank it all down. I had drank a quart of her hott piss and licked my lips and corners of my mouth - hoping that I didn't spill a drop.

"Good Bitch! Good Bitch!" Naomi exclaimed laughing as she threw me with my back onto the floor. She securely fastened my leash to the foot of the bed. My hands were uncomfortably squished by my body as I lay with my back ontop of them.

Naomi left the room and came back with the long metal rod that was about 1/2 inches in diameter and pulled out the bottle of lube. After applying a thick coat of lube onto it she placed it upon the head of my throbbing cock. My heart stopped and my skin froze. My eyes opened wide with terror and my breathing halted. "Time to torture my dogslave. I want you to scream to your hearts content slut." she laughed as I began to shake and convulse trying to get out of my bonds. I began screaming and begging and she sat there laughing and teasing my cock head with the painfull torture to come. "What's my name bitch!" she demanded.

"Mistress Naomi Ma'am .... arrrgg ... ayyeeye ... owww!" I screamed as she forcefully rammed the metal rod down my cock. I could feel it stretching and tearing my cock in half. "Louder Bitch!" Naomi yelled as she fucked my cock with the 1/2 inch thick metal rod. Finally, she hit rock bottom and impaled my cock with the metal shaft. Naomi then placed a metal ring at the base of my cock head, another at the base of my cock and balls, the third just after my ballsack on the swollen and painfull shaft, and the last four between my shaft and my balls - stretching them and pulling them painfully downward. She then hung each of the 5 lb weights from each of my sore and tortured balls.

"Now it is time for your lashings." Naomi stated conclusively and satisfied with the result of her work thus far. As each of the 15 lashes hit my chest my entire body jumped in the air causing extreme pain to my crotch and genitals. After she was done I could feel blood dripping along the side of my ribs and down my shaft and dripping off my balls.

"Now the fun part begins" Naomi said with a nefarious grin spread accross her face. She pulled out one needle from the box and plunged it into my cock head sending me into shrill screams and pleas for mercy. As she inserted needle after needle in me my body and mind began to change. The pain was no longer unbearable. It was simply flowing through me. It hurt even more than before but it flowed into me where she inflicted it and flowed right out of my body once it had shot through every one of my veins - leaving my being free of pain, ready for the next shock; and the next needle did come so did the one after that and so on.

When she was done she let me rest. I must have slept for three or four hours. When I woke up, I found myself free of my bonds, and my body had been cleaned, and my dick was wrapped up in cotton sheaths. Not that I really needed it wrapped up. Sure it hurt like hell but it would have gotten better now that I was out of bonds.

"You don't think we are done do you?" Naomi said to me. "Stand up and bend over that table." She said gigling. "You wanted to fuck me in the ass and I told you no. Well now I'm gonna fuck your virgin ass and you will love it and beg me to fuck you harder and deeper. Understand?"

"Yes Mistress Naomi" I replied with no desire to ever question her or to doubt her again. As I bent over the table she inserted a plastic tube into my ass. "Oooh, aahhhaaahhh." I gasped as a hot soapy liquid filled my ass.

"Hold it in. Good boy." She said to me and then sat down and waited for what seemed like forever. "Go to the toilet and relieve yourself." She ordered. When I came back she inserted yet another platic tube up my ass. "Rinsing time." She said as I felt icy cold distilled water fill my ass even more than the soapy liquid had before. Again, we waited, I waited. And then I relieved myself.

When I came back, my eyes fell upon Naomi, this beautiful, athletic young woman, with a thick thick 8 inch strap on. The harness was a black leather thong. And the dildo was a see thru purple dong that was 8 inches long and an enormous 3 inches thick. "You ready to loose your virginity slut?" she smiled wickedly.

"Mistress, may I...Mistress Naomi....may I please have another one...this one is scaring me." I asked politely.

"Another one? I can do that. Sure, You pick which one you want. Open that door." She said calmly.

Fear gripped me as I opened the cabinet door. Inside, was a green glass dildo the same size as her jelly strap-on, a black rubber dong about 10 inches long and 2.5 inches thick, another black rubber dong about 12 inches long and 2.25 inches thick, a pink jelly dong about 9 inches long and 3 inches thick, a 7 inch studded dildo about 2.5 inches thick, and a monster 7 inch long 4 inch thick multicolored glass dildo.

"Any day now slut. Pick your impaler." She said as she slapped my sore ass and pinched my thighs.

"Mistress, can I have the skinniest one?" I asked. "The one that is the longest *gulp* but the skinniest. May I have that one instead."

"Only if you beg like the nasty whore that you are." She said crossing her arms. I got to my knees and begged her to take my virgin ass with a 12 inch long, 2.25 inch thick dildo. When I was finished she laughed and said. "Silly boy, it doesn't matter which one you pick, i'm gonna fuck you with all of them anyways."

With that, she grabbed me, threw me over a table, fastened my ankles to the feet of the table and cuffed my wrists behind my back. She strapped on the 2.25 inch thick dildo, lubed it up, and began sliding it up my ass. It burned, and stung like hell up until it hit rock bottom. Or what felt like rock bottom. Then I felt like something was slowly tearing my guts out from the inside as she forced the dildo past my prostate. Once all 12 inches of the flexible dildo was up my virgin ass and my face was stained with tears, she grabbed me by the shoulders and pulled me towards her, causing the dong to move inside me and me to scream.

She fucked my ass with the 12 inch dildo for half an hour. All the way out, all the way in. She fucked me senseles, I found myself bucking against the monster and cumming all into her hand and licking it clean. She then pulled out the 12 incher and strapped on the 10 dildo and fucked me for about half hour with that. Then the 8 inch jelly dong was used to bring me to orgasm. "Now on to the big boys." She said while slapping my ass.

She strapped on the 9 inch long, 3 inch thick dildo and with one swift stroke impaled me on it sending silent screams out of my mouth along with guttural grunts of pain. "How does that feel slut?" she asked as she began spanking my ass and reaming me with the monster. "Tell me, how does your ass feel getting fucked out by this big fucking dildo?" she ordered me to answer.

To my shame and humiliation I was bucking against it and trying to somehow reach my cock to masturbate. "If feels good Mistress Naomi" I replied crying with shame. "It feels damn good, fuck my slutty ass, stuff me good and hard Mistress" I cried out relinquishing all inhibitions and impaling myself on the 9 inch shaft strapped on to this gorgeous Domme.

After she allowed me to cum all over my thighs and on the floor she pulled out of me and said. "Rest for abit. Then there is the last dildo you have to take care of." she informed me as she went and sat down to rest.

As she relaxed my mind was filled with a thousand thoughts. The 4 inch thick glass dildo will surely tear my ass. But the 3 inch felt incredibly amazing. However, 4 inches is a big leap, and if she is as rough with it as with the 3 inch, i'm gonna die. All these thoughts and fears came into my head. And I was wishing I had never come up to see her this particular weekend.

"It is time." she spoked soberly. She strapped on the 7 inch long, 4 inch thick dildo and lubricated it copiously. Mistress Naomi placed the head of the dildo at the entrance of my raveged ass and pushed it in about an inch of the way. "Relax baby." She spoke softly, gently caressing my hair. "How does that feel?" She asked while pushing the dildo ever so slowly into me.

"It feels. I am sore. But it feels good Mistress Naomi." I replied as my dick hardned. Naomi was pushing the dildo ever so slightly, half an inch, then half an inch more, than half an inch out, and so on so forth. "It is stretching me out alot, it is beginning to hurt Mistress Naomi." I said as it got to about 5 inches inside me.

She reached under and began stroking my hard cock and caressing my balls. "You know I love your big 8.5 long dick. It is nice and thick, 2.5 inches in diameter, and it stretches me out just right. I really like your cock. How do you like mine?" she asked giggling as my precum leaked onto her fingers. "You like my dick love? Are you happy with my fat cock you stud?" She asked me slapping my ass and shoving her fingers into my mouth. I licked them clean of my juices and she rammed the last two inches into me without mercy.

Despite the shrill pain I screamed "Yes Mistress Naomi. I love your wonderful cock. Fuck me Mistress!" I said to her and began begging her as she spanked me while fucking me with the monster cock. She was considerably gentle with me, only halfway out and back in. But it still hurt. None-the-less, I came like the nasty fuck toy that I am and she kept on fucking me.

"I'm gonna fuck you with my big cock until you pass out. You like that fat fucking prick don't you bitch?" She asked me rhetorically while pushing the strap-on deeper into me.

After I came about 3 times, she pulled out of me, exhausted, and lay down on the couch. "Eat me out, make me cum all over your naughty face." She ordered. I followed my Mistresses orders and ate her juicy cunt to my hearts content. I love eating her pussy. I love it when she grinds into my face and I love the taste of her love juices. I sucked her slit with passion and fervor until she came and came all over my face.

"Mmmm, good dog, now slurp my pussy clean, mmm, yeah, good fuck puppy." She said between gasps of pleasure. "I'm too tired from fucking you. Its hard being a guy. Damn, I can't feel my legs. You guys have it tough huh?" she said smiling.

"We get used to it after the first few times Mistress." I replied kissing her stomach and caressing her thighs.

"Put that big sore dick of yours to use slave." She ordered as she grabbed my shaft and pulled me into her eager pussy.

"Yes-yes-oooh-yeaah Mistress N-naomi" I replied gasping as my oversensitive cock was being squeezed and pulled into her dripping wet heaven. "Oh god Mistress, you feel so good, thank you for letting me inside you, thank you Mistress." I said inbetween my eager breaths as I pumped my proud manhood into my Mistress starving cunt.

"Yeah fuck me. Fuck me hard you dirty boy. Ram your fat cock deep in me. Yeah just like that, fuck me harder bad boy!" Naomi screamed as she came and convulsed all over my pumping cock.

"M-mistress Naomi, may I cum? Please I need to cum." I asked her beggingly. Her reply was to reach behind her pillow and pull out a leather cock ring which she fastened behind my balls.

"No you lazy mut! You had enough time to get used to it. Keep on fucking me and don't you dare stop! Understood bitch?" she asked with a teasing grin on her face while pinching my ass.

"Oh no, never Mistress, I would not stop for the world, I just wanted to cum that's all." I replied as I kept on stuffing her heavenly temple. She pulled me to her and planted a deep kiss, sucking on my tongue.

"Good boy." she said and started caressing my hair as she rolled her eyes back and another orgasm overtook her.
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