Dan's Conditioning

Miss Kendra was standing over Dannie, looking down, proud of her creation. Dannie was an excellent example of what a sissy ought to be. She was down on her knees, legs spread wide, in white thigh-high nylons. Her little sissy cock was dripping precum down onto her white mini skirt, as its head protruded out of the waistband. Miss Kendra strutted around Dannie. She enjoyed the sight of her sissy's cute little ass cheeks peeking out from the bottom of her Minnie skirt, and Dannie's high heels aiming back toward her.

Dannie's arms were folded behind her back and secured firmly with hot pink bondage tape. Her back was arched, driving out her luscious breasts. This position flaunted her cleavage and massive fake tits in a hot pink leopard print bra. Dannie's chest may have been counterfeit, but no one would be able to tell. They were perfectly perky, plump, and flawlessly blended with makeup effects comparable to the work of Hollywood artists. Even Miss Kendra now enjoyed the view of them.

A long string of saliva trickled down from Dannie's gagged mouth, onto her breasts, puddling in her cleavage. Her lips were coated in hot pink lipstick. Miss Kendra trailed her fingers through the puddle between Dannie's tits. She rubbed it across Dannie's face, smearing her excessive make up.. Wet tracks of eyeshadow, mascara, and tears streamed down her face. Miss Kendra became turned on as she looked down at Dannie's running makeup and watering eyes. She leaned over, low enough to ruffle and tease Dannie's pink wig.

"Turn around, my little slut," Miss Kendra instructed as she stood directly in front of her sissy. Miss Kendra licked her lips and enjoyed watching Dannie struggle as she shuffled around on her knees. When Dannie spun herself one hundred and eighty degrees, she was forced to look at herself in the mirror with her mistress standing behind her. Miss Kendra petted the top of Dannie's head and teased her hair again.

"Look what you have become. Such a sexy little slut you are now. I love it! I'm so proud of you. Did you ever think this is how you would end up? One blow job that you just couldn't resist brought you here. I did try to warn you that day, remember? You were just so eager to get your dick sucked. You just have one more step before you're truly a sissy whore. I really think you're ready for it. I can't wait to watch it happen," Miss Kendra cooed.

THE BEGINNING

Dan had just turned eighteen and graduated from high school. He was always quite a shy guy, and as a result, he never had very much luck with the girls at his school, even though he was a tall, handsome guy. Quite a few girls showed interest, but he would always become awkward and lose confidence while talking to them.

None of that was on Dan's mind today, however, as it was finally summer. Dan was looking forward to a period of absolute freedom before he went off to college next year. He lived at home with his single father, but this summer, His father would be traveling for work. Dan was thrilled with the idea of having the whole house to himself for almost the entire summer.

Dan received a text message from his best friend, Jim, inviting him over to hang out. On the ride over, Dan had the radio blasting, and he was singing along, bobbing up and down in his seat, simply thrilled with how well his life seemed to be going. Dan thought that maybe he and Jim would go out tonight and try to pick up some chicks. He could bring them home to his newly vacant house, and perhaps even get lucky! That was if he could overcome his own awkwardness.

Dan arrived at Jim's house, and as he parked his car, he noticed that Jim's car wasn't there. He thought this was strange since Jim had texted him and invited him over. "Oh well," he thought, "Maybe it's in the shop." He strolled up to the front door and rang the doorbell. He waited there patiently and heard a great deal of scurrying around. After a few minutes, Jim's mom answered the door.

"Hey Dan, what's up?" She asked. She leaned on one side of the door frame, and seductively cocked her hips. Dan froze and stared awkwardly.

Jim's mom was younger than most of Dan's friend's mothers, though Dan wasn't precisely sure her age. He always thought she could pass for late twenties or early thirties, though she was probably closer to mid-forties, based on Jim's age. She was the kind of woman who would regularly be asked for ID when she went out to a bar. Not only because she appeared young physically, but she also dressed in very youthful attire. She had a very playful and vibrant personality as well. However, you could still detect an intense wickedness underneath those layers, if you paid close enough attention.

What Dan was sure of, though, was that she was stunningly sexy. She was tremendously tall. She made level and direct eye contact with him whenever they were face to face. This consistently set off Dan's anxiety, causing his eyes to quickly dart toward the floor. She was skinny, but she still had the right amount of curves to her. She had an overall tight and fit form with an hourglass shape, small waist, and broad hips. Her hair was long, thick, and wavy. It was a magnificent, platinum blonde color. Which went really well with her eyes that were a beautiful pale blue-sapphire. She had this fascinating predatory type of stare, which was cast over Dan as she eyed him up and down, amused by his discomfort. She had a petite, cute nose, perched above her huge voluptuous lips. Today, they were accentuated by a pastel hot pink lip gloss with a perfect hint of sheen to it.

Dan couldn't help himself and let his eyes wander up from the ground to her magnificent breasts. They were made even more prominent by a skin-tight, low-cut tank top and a hot pink push-up bra, which he could make out from the straps, and the bright pink cups visible below the thin fabric of her top. The tank top was cut short, just above her belly button. Dan couldn't help but notice the soft, subtle outline of her abs.

His eyes continued to wander, and Dan took notice of her low-rise yoga pants. They were so low, in fact, that Dan couldn't help but notice the hot pink waistband of what he assumed were thong underwear emerging from the top of her pants. They hugged snuggly over her perfect hips. Dan really admired her long legs. His eyes continued downward, and as they reached her feet, he got a glimpse of her hot pink toenails. Dan mused to himself that she must really enjoy color coordination.

"You alright there, honey?" Jim's mom asked after an awkward moment of silence.

He gulped and answered back, "Yea, sorry, is Jim here?"

"No, I sent him to the store to get some stuff for dinner tonight. You can come in and wait for him. He should be back in just a little bit."

Dan responded, stuttering, "OK, sure."

He followed her into the house. He couldn't help himself from gawking at Jim's mom's tremendous ass. It was hefty, but not oversized. It fit her body perfectly with that perfect heart-like shape. He thought to himself, "she must do a thousand squats a day to have an ass like that." He walked behind her, mesmerized by the subtle bounce of each cheek with every step she took.

When they reached the kitchen, she told Dan to take a seat at the island, and he complied. She walked to the refrigerator and opened the door, and then bent over to rifle through one of the drawers. She was bent over just enough for Dan to get an excellent glimpse of her hot pink v-cut thong as it peeked out of the top of her yoga pants. She grabbed a box of strawberries and leaned over the island, right in Dan's sightline. Showing off her cleavage. She raised one eyebrow, then took a bite of a strawberry. Her lips puckered around the fruit, as she looked Dan straight in the eyes.

"Strawberry?" She asked, but Dan declined.

"So, I heard you just turned eighteen the other day," Jim's mom inquired.

"Yea, just this past Tuesday," he responded.

"Oh, that calls for celebration then. How about a birthday drink? Do you like bourbon?"

Dan froze up, unsure of how to answer. He opened his mouth, but nothing came out.

"Don't worry... I won't tell," Jim's mom interrupted, chuckling, "Hey, if you can go to war, you can have a drink at my house... So, what do you say? Bourbon, on the rocks?"

"You know what? sure, why not?" Dan's attempt at confidence was diminished by his shaking voice.

She gave him a subtle smirk and then made up two glasses of bourbon with ice. She handed Dan his glass and held up hers. "Cheers!" She exclaimed, and they both knocked drinks then took a sip. They placed their cups on the counter, and Dan noticed that her glass appeared only half-full, looking more like what he remembered from TV and movies as a typical pour. His heart began to pound; his glass was filled almost to the brim.

"So... eighteen, huh? Now you can get yourself into some real trouble..." she purred, biting her bottom lip. She looked up and made direct eye contact with Dan, but before he could respond, an alarm for the dryer rang out in the laundry room.

"Oh shit, be right back," Jim's mom said with a sigh.

She strutted into the laundry room and started to empty the dryer. Dan was left sitting alone with his bourbon. He took a big gulp of the drink and let out a breath he realized he had been holding. He was relieved to no longer be in the presence of someone so startlingly sexy. Before his heart could return to a natural rhythm, Dan heard Jim's mom call out from the laundry room.

"Dan, can you come give me a hand?"

"Sure thing," Dan yelled back. He stood, then grabbed his drink, and walked back to the laundry room.

"Can you help me carry one of these laundry baskets?" She asked.

"Sure, let me just put my drink down," he replied.

Dan looked for a place to set his drink down while he took a sip. Jim's mom took advantage of this moment. She placed her pointer finger on the bottom of Dan's glass, applying pressure, slowly tipping the glass back, and forcing Dan to drink deeper than just a sip. He reached up with his free hand to pull her hand away. She slapped it down, saying, "don't be a bitch!" in A playful tone. She pushed the glass back further, as Dan was forced to finish the last of the bourbon.

She then grabbed the glass out of his hand, saying, "Good boy, that's how a man drinks a whiskey." Dan let out a few coughs due to the whiskey burning the back of his throat.

"Now, pick up that laundry basket and bring it to the bedroom with me," She commanded, playfully. Dan obeyed and picked up the basket. He tried to regain his composure as he followed her through the house, down the hall, and into the bedroom. "On the bed," she told him. He placed the basket on the bed and turned to walk out.

"Where do you think you're going, Mister? Too good to fold, are you?"

"Well, no... I guess I can help fold," Dan replied.

"Well, good, sit here on the edge of the bed, and fold this basket."

Dan complied, but felt dreadfully awkward; The basket was filled with mostly bras and panties. Jim's mom noticed that he was fumbling around as he tried to figure out how to fold one of her thongs. She demonstrated how to fold it while telling him, "I guess you haven't folded many thong panties, huh? That's ok, you'll get plenty of practice today. That's mostly all I have."

After a silent moment, she continued, "My ex-boyfriend used to make me wear them all the time. He was really controlling. Having a strict piece of cloth crammed up your ass will really keep you reminded of who's in charge. You know what I mean? Well, I guess not, but who knows, maybe one day you will."

Dan just sat quietly, not very sure what to say.

"Speaking of tight clothes," she said, "Why do you always wear such tight pants? They're like girls' pants. Can you even fit stuff in those pockets?" She grabbed him by his pockets and pulled herself right up against him, forcing herself between his legs. She tried to thrust her hands into his pockets, but she could only manage to get a few fingers in. She gave his thighs a little tickle. Dan just sat there frozen.

She went on, "See? You can't tell me that these pockets aren't useless. It can't be too comfy for your package, right? Every time you come over, I can see your bulge is all tight. A few times, I could even make out the outline of your cock." Dan's face turned to beat red, and he began to pull away from her.

"Oh no, Hun, don't be embarrassed! I'm not trying to make fun of you! To be honest, I have even enjoyed the view a few times. It looks like a nice, thick cock, from what I have made out, but those pants are just so tight. Can you even get a hard-on in them? You might break something!" She started to wiggle a bit, rubbing her hips deeper between his thighs.

"Oh, that sounds like fun," she laughed, " let's see if you can get a hard-on in those tight ass pants."

Dan sat on the edge of the bed, stunned, wondering whether this was really happening, or if he was dreaming. Jim's mom had moved back and walked over to the dirty laundry hamper. She pulled out a pair of her worn panties.

"Let's see if these will get you hard," she told him. Then she grasped the back of Dan's head and pressed the panties up to his nose, commanding him, "sniff." Looking down at his crotch, she observed as his cock began to swell in his pants. She removed the panties from his nose and then wrapped them around her pointer and middle finger. Next, she pressed her fingers, wrapped with panties, against Dan's bottom lip. "Open up," she instructed. Dan obeyed, and she inserted her fingers, covered in her used panties, into his mouth.

"Now suck on them. I want you to taste me," Jim's mom whispered into his ear. Dan was turned on beyond belief, and he eagerly began sucking on them. He was striving to get as much of her essence as he could. He was rock hard, and it was even a bit painful in his extraordinarily tight pants. Jim's mom gazed down at his crotch and noted his raging hard-on stretching his pants to the max.

"Well, that seemed to work. I always kinda figured you for a little pantie perv. Guess I was right!" She pulled her fingers out of his mouth and used them to stuff the entire pair of panties into his mouth. She grabbed him firmly by the chin and pulled his face near hers. She Gazed straight into his eyes, and in a stern voice, she directed, "You're not to spit those out. Unless I tell you to. Nod if you understand." Dan, still in shock, from his current situation, slowly nodded. "good boy!" She reassured him.

Jim's mom knelt down in front of dan. She placed her hands atop his knees and forced his legs apart as far as they would go. She rested her head on his lap, positioning her chin right on the tip of his cock. This made dan squirm.

"I bet this cock wants out of these tight pants. right?" She asked, in a seductive tone, and bit her bottom lip. Dan nodded his head, yes. She then rubbed her fingers over Dan's constricted balls. "I bet these are tender," she said. Then she gave them a nice hard flick making dan quiver and let out a mumbled groan of pain. "I guess so," She said with a grin, "I guess you want these pants off then?" Dan nodded enthusiastically, yes.

"Good... cause I really want to get a good look, at that cock of yours." She unbuttoned and unzipped his pants, and then she dragged them entirely off along with his underwear, leaving his cock exposed. She grasped it with her pointer finger and thumb at the base and gave it a firm squeeze, which forced most of the blood into the head of his cock. This made the head throb and become excessively sensitive, which made dan tense up. As she observed and inspected his hard dick, her lips curled to a smile.

"Now that's a pretty cock. I'm not gonna lie, and I appreciate you keeping it clean-shaven for me." She pressed her lips up to the tip of his cock. Teasing it for a minute, before slowly pushing her tong out and licking the head like an ice cream cone. Dan couldn't help but lean back and let out a moan. After a few minutes, she stopped teasing and began to really suck his cock. She Gave an occasional deep throat causing her to gag, as loads of saliva oozed from her mouth and down Dan's cock. This was one seriously sloppy and wet blow job. The excess saliva was gushing down onto Dan's balls, and Jim's mom began using it to massage them.

Dan was thinking to himself, "I must be the luckiest guy alive." When suddenly, she pulled her mouth away and clutched dan's shirt pulling him to sit upright. She Looked up at dan, lipstick smudged, her lips wet with precum, and a string of saliva running from her bottom lip onto Dan's cock. She grabbed his cock again and began stroking it, ending each upward stroke with a twisting motion over the head of his cock. While giving him a sloppy wet handjob, she still stared up at him, looking deep into his eyes. She spoke, "I want to be honest with you now; I'm going to tell you a secret. I want you to nod if you're ok with what I tell you. Do you understand?"

Dan nodded. She continued, "If we're gonna keep messing around, you are gonna have to surrender to me. Really let yourself go. Do you know what I mean?" Dan's eyes were wide, and he made no motion as he tried to grasp her meaning. She smiled and went on, "I've been told that I can get very intense. I want to introduce you to a new world, my world, the things that I love, things you've never dreamed of. Once I start, there will be no turning back... but something tells me, you're not going to want to stop. Sound good?

Dan nodded his head yes, still in shock from the amazing hand job he was receiving, in combination with the words he was hearing. "Smart boy," she replied, then put her head back down between his legs, this time lower, laying her lips on his balls and beginning to tongue them. Dan was in ecstasy, overwhelmed with pleasure. All of the sucking on his balls produced loads of saliva. It began to trickle down his taint and between his ass cheeks. Jim's mom slid her hand under Dan's ass. She used her pointer and ring finger to spread his ass cheeks. Then she used her middle finger to start rubbing some of the extra spit around on Dan's asshole.

Dan started squirming and tried to get away, crawling up the bed. She countered by removing her mouth from his balls and taking a firm grip of his cock. Restricting him from going any further. She kept her finger pressed firm against his asshole, as she informed him, "Now Dan, this is what I was talking about. You must surrender yourself to me, or we have to stop right now. What do you think? Do you want to keep going?"

Despite his uncertainty and confusion, Dan nodded slowly. Without hesitation, she slid her finger into his ass, gradually, but also entirely. Dan moaned, taking pleasure in the feeling of the finger inside of him. Jim's mom gave Dan a wicked smile and purred, "see? Not so bad, is it? Don't worry, I'll make you a little butt slut yet," she said, as she began to slowly finger his ass.

"Now, you spit those panties out and tell me if your gonna cum. If I get cum in my mouth, you will regret it. Do you understand?" Jim's mom asked. Dan nodded again. She then began sucking his cock once again. Dan was in a state of euphoria. He had never felt so much pleasure. Before too long, Dan felt a second finger slide into his ass. Dan had never taken anything in his ass before, and her fingers plunging in and out of him brought a mixture of pain and pleasure, causing him to gasp and moan. This Sent him right to the edge of Cumming.

He spit out the now, soaking wet panties and urgently yelled, "I'm gonna cum!" Jim's mom immediately halted everything. She abruptly withdrew her fingers from his ass, stood up, and walked out of the room without uttering a word. She slammed the door behind her.