After the positive response to part 1, here’s another section of Justin Benedict’s admirably graphic story, reproduced by kind permission of Chastity Tales:
WHACK WHACK THWACK! “Ohhh!” I moaned after one of my early whippings. Gretch had tied me over the arm of the sofa with my pants and shorts huddling about my ankles, and she’d exercised a bamboo cane she’d picked up at a flea market.
“What’re you whining about, Miles?” Gretch had asked cheerily. “This is your dream!” WHACK WHACK SWAT! “You wouldn’t believe how your butt looks now, hon. You’ve got all these purple marks all over your right cheek.”
I’d turned with tear filled eyes to look at Gretchen in a snug striped turtleneck, slapping the cane in her hand. WHACK WHACK! I’d burst into tears. Gretchen had looked concerned and pulled me off the couch and began stroking my bottom, and then turned me around, pushing my scorched butt against the sofa, and she began to pull on my cock, which had lengthened.
“You want this, right, Miles?” Gretchen had breathed in my ear. “God forbid I do the wrong thing by you.”
I was biting my lip, trying not to sob further. “N-no Miss Gretchen..it’s what I need!”
Gretchen had laughed. “Miss Gretchen, huh?” She’d stuck a wet tongue in my ear and began toying with my cock all the more. My hands were tied, of course, to keep from jumping away when I’d gotten the caning, and now all I could do was writhe as she’d stroked my bulging cock.
Gretchen had pulled and stroked my cock until I began feeling the familiar pulsating at the base of my tortured penis, the pull of the cum, which was now rising. It had been several weeks since I’d had sex with Gretchen, and I at that time was not a masturbator, having given that up after college. Gretchen had at this point become quite used to my oral ministrations, and depended on these for her release, and had learned to make me go through all sorts of measures to “Get me in the mood” to actually be allowed to stick my dick in her.
Gretchen’s soft, beautiful fingers were now playing a lullabye on my long-denied cock, and her other hand was squeezing and pinching my bare bottom, welted as it was from the bamboo cane. I was rather worried that our housemate might come home and wonder why my fully dressed, sexy wife was standing, and stroking her hubby’s cock while his pants and undies were down on his Hush Puppies.
God, Gretchen’s fingers were incredibly skilled.
“Having fun, baby?” Gretch’s voice tinkled, and now she was kissing my ear, her tongue exploring my sweating neck as I gasped and my stolid erection began drooling excessive precum. I was getting closer to release. Oh, to cum in her hand. I wanted it so badly! My cock quivered as Gretch’s long, purple nails had tickled the vein crawling across the shaft.
“It’s such a thick, burgundy vein, honey” Gretchen whispered. “It almost matches the shade of my nails, but not quite….but I’ll make the vein purple in time.”
Oh, God, that voice. The way she could turn me into jelly! What kind of a monster was I creating? As Gretchen’s forefinger moved back and forth across the vein, her thumb tormented my frenum, and my balls felt leaden with backed up spooge of several weeks!
“Are you excited, hon?” Gretch had asked me. “Do you like this?” God, I was hotter than any sex experience previously… and I’d once been with a Playboy Bunny!
This was better than any blowjob, any time a girl had let me take her from behind… I’d just had my ass blistered, and now I didn’t know if I was going to be allowed to cum! Unbelievable!
Gretchen stopped for a moment. “I think you need to service me a little, baby. You’re having all the fun.” Gretchen had then pushed me to my knees and pulled up her white miniskirt. No panties! I’d gotten between her legs.
“Gretch, undo my cuffs.” I mumbled. “I need my hands to pleasure you.”
Gretchen laughed. “No you don’t, just lick away. If I don’t like it, no more playing with Mr. Willy” she’d said.
On my bare knees, scraping the hardwood floor, I’d licked away until Gretchen had experienced two shuddering orgasms… It had taken about forty-five minutes, but finally she’d dropped her skirt down and helped me up again, and resumed her operations on my sweating, painful organ.
I began getting close to orgasm yet again— “Your legs are shaking, honey…I think you’re ready to have a wet one, eh?” Gretchen laughed as she tongued my neck some more. “I bet you believe you deserve it, because you’ve made me feel so good, eh?”
I moaned, and my legs shook more and more.
“Well, I hope you liked your –oh-orgasms, Miss Gretchen.” I had said tactfully, and Gretchen had laughed deep in her throat…and all of a sudden I felt very close. It was coming fast. Damn! Gretchen now was slowing her masturbation a bit, and the semen receded back to my balls.
I relaxed, biting my lip and my cock drooped a bit, and Gretch began stroking faster again, pulling the frenulum. Watching Gretchen’s lovely nails as they played across my cock, I had begun getting more and more excited.
Slam! The door to the kitchen opened and shut. My worst fears were realized. It was Tom, our handsome housemate. “Tell him you’re busy in here, honey.” I whispered to Gretchen as she toyed with my organ. “It’s just… weird… keep him out of the room.”
“Hey Tom!” Gretchen had shouted out, “What’re you up to?” Tom had strutted right into the living room.
“Not much Gretchen, what about you?” His eyebrows had risen as he viewed me with my pants and undies down, my ravaged ass jiggling. Gretchen let go of my cock and stepped away.
“What the hell’s goin’ on?” Tom had asked.
Gretchen had smiled and picked up the bamboo cane, waving it about. “I’m just having a little kinky session with Milesy here.”
Tom laughed as Gretchen lashed my bare butt once or twice. He watched me twist and bounce, my hands still cuffed. “This is so weird, Miles.” Tom laughed. “Gee, do any of the fellows know about this?” Gretchen laughed, too, and whacked me a couple more times.
“Jesus-please Gretchen.” I begged, tears rolling down my cheeks.
“I’ll stop if you let me tongue-kiss Tommy here.” Gretchen laughed.
I stood up indignantly. “Absolutely not.”
WHACK WHACK WHACK! Gretchen lay the cane about me a few times, and I began crying heavily despite myself. Tom was grinning from ear to ear.
“Whatever you want, honey… but we’re married!” I had pleaded with her… and Gretchen had laughed and gone over and given Tom a big, tonguey kiss… and he’d ground his body against her as I stood, humiliated.
“I gotta go out, but we should do this again sometime!” Tom laughed, kissed Gretch again. “Don’t be a bad boy there, Milesy.”
Gretchen grabbed my ear “Say yes sir, uncle Tom.” She whispered in my ear…
I gritted my teeth. WHACK WHACK My ass was roaring. “Y-yes sir, Uncle Tom!” I sobbed, and his laugh was the last sound I heard.
Gretchen looked abashed. “Poor thing, you’re not mad at Gretchie are you-ums?” She kissed me deeply, and her soft fingers dropped to my sweltering cock again, and she began pulling it gently.
“N-no, I just didn’t want anyone to know— discretion and all that.”
Gretchen rubbed faster. “Oh, honey, discretion’s not that important… you’re just a sissy-boy… Tommy knows that. Why do you think he has to do all the repairs around here… you’re not mechanically inclined, you say, but really, you’re just a sissy-boy!”
Gretchen’s long nails moved faster and faster and my cock got longer and harder.
My legs wobbled again, and Gretchen’s fingers slowed down. “Please go faster, honey.” I begged. Gretchen looked annoyed. “I’m not your honey… I’m Tommy’s honey, maybe… but you’re just a wimpie boy, you know.” I looked at the floor, sad and abashed.
“Poor baby can’t cum?” Gretchen asked unsuspiciously. I shook my head and tears rolled down my cheeks. Gretchen giggled softly and rubbed a bit faster. I felt the impact of the backed up seed beginning once more to roll forth in my cock,.
Closer and closer I was to release. “Close your eyes, Miles.” Gretch whispered in my ear. “I’m going to give you a helluva surprise, baby, like you’ve never had.” I closed my eyes, bit my tongue and waited.
To be continued…
