Chapter 5: Stretching Exercises

Like a kid on Christmas morning, Mark told Tara how she should stretch her pussy. He had clearly given it a lot of thought. “Every day when I’m at work, I want you to get your laptop and watch whatever porn turns you on. Then stretch your pussy a bit more each day with anything you want, using your vibrator on your clit. You need to have at least three orgasms before I get home at night. We will call this routine your ‘Stretching Exercises’ to keep it secret from Clara. How does that sound?”

Tara smiled, and nodded her agreement, “Three orgasms per day, you say? I will either do it or die trying!”

The next morning, Mark took Tara into his warm and loving embrace. The scent of his cologne mingled with her own lingering aroma of tobacco, creating a heady mixture that filled her senses. With a wink, Mark said loudly, in front of Clara, “Tara, I need to go to work now. Don’t forget your Stretching Exercises today - I hope you have a great workout.” Tara blushed at his cheerful mood and coded message. She waived him away, eager to begin her Stretching Exercises!

When Clara left for school, Tara found herself alone in the house, her heart pounding with anticipation. She quickly closed the front door behind Clara, locking it securely. The sudden stillness of the house enveloped her, amplifying the sense of freedom and liberation that coursed through her veins. Without wasting any time, she took her laptop to her bedroom and sat on the bed, her fingers hovering over the keyboard as she contemplated which video to watch first. As she navigated through the adult websites to find inspiration, her mind raced with excitement and possibilities.

Tara clicked on a videoclip that caught her eye, her heart thudding in her chest as she waited for the clip to load. The scene unfolding before her was both tantalizing and shocking, stirring a whirlwind of emotions within her. She leaned forward, her elbows resting on her knees as she gripped the laptop tightly, her knuckles whitening with tension.

Her breath quickened as she watched the woman on-screen, her eyes widening when she inserted a large black dildo into her pussy. Tara’s own body reacted instinctively, her clit throbbing in response to the explicit content. She reached down, rubbing it gently, enjoying the sensation as it sent waves of pleasure coursing through her. As Tara continued watching, she became lost in the world displayed on the computer screen, eager to embark on this new journey of self-discovery.

Tara reached for a Virginia Slim cigarette, then stopped herself. No, dedicated pussy gaping called for a naughtier, darker, taboo, cigarette. She extracted a long More 120 from its shiny red package, lighting it with shaking hands. The first drag filled her lungs with rich smoke, and her mind with carnal thoughts of endless desire. As she smoked and watched the video of the woman pleasuring herself with a large dildo, her pussy moistened, and she felt a desperate need to start her Stretching Exercises.

Tara got up from her bed and collected the things she wanted to use; a bottle of brandy, a pack of More 120s, and her ashtray. Then, from the first box she had shown Mark, she took out the nipple clamps and attached them tightly. The pain was insistent yet bearable. She gave them a sharp pull, sending a pulsing flash of electricity into her throbbing pussy.

From the second box, Tara got the vibrator, some lube, and her three different-sized dildos. She laid back on the bed with a pillow under her hips so that her pussy faced the ceiling, the perfect position for deep penetration. She wondered how long she would need to do her Stretching Exercises before she turned her tight pussy into the kind of cunt that she, and Mark, both wanted her to have.

Tara took a large swig of brandy, feeling it’s burn light a fire in her belly, then spread throughout her entire body. She lit a More 120 cigarette and let it dangle between her lips.

Tara began the stretching process, gently introducing the smallest, purple, dildo into her eager pussy. The sensation was foreign and initially painful, causing her to gasp involuntarily. As she adjusted to the intrusion, the discomfort transitioned into pleasurable waves that urged her to push further. With determination etched on her face, Tara pressed the dildo deeper into her core, welcoming the transformative journey ahead. She increased the intensity and depth of the dildo’s thrust, marvelling at how nice it felt to be fucked again.

Slowly, inch by inch, Tara filled her pussy with the toy. With her spare hand she took another swig of brandy, pulled on her nipple clamps, and smoked her cigarette. “I could get used to this Stretching Exercise,” she thought to herself.

Before long, Tara was pumping the small dildo into her pussy with wild abandon. She then put the vibrator on her swollen clit and, within seconds, had an incredible orgasm - her best since she married Mark 17 years ago.

Spent, Tara fell back and smoked her cigarette. She watched the smoke swirl and drift to the ceiling. She had just had her first orgasm in over a year but knew that Mark told her that she needed to have three orgasms each today, before he got home. She smiled at the second dildo, which was a solid eight inches long, flesh-toned, and much thicker than anything she had ever had in her. She was surprised at how real it felt in her hands. She knew where her second daily orgasm would come from.

Tara blew creamy smoke onto the dildo and slid it into her mouth. She imagined giving a smoky blowjob to a hung stranger in a dark alley. She imagined the stranger shoving his big cock up her pussy, or ass, from behind. With those dirty thoughts in her mind, she slowly pushed the second dong into her hungry hole.

After some determined pressure, the bulbous head of the dildo split Tara’s lower lips and sat lodged in her pussy. Tara gasped at the intrusion. She saw that her lips had become a tight white ring around the dildo. She could not imagine ever being more stretched but knew that she needed to continue her Stretching Exercises to change her pussy into a proper cunt. How could any woman take such a large penis? Well, if they could, so would she.

Tara began to move the large rubber cock deeper and deeper into her body. She stopped for a moment to catch her breath and add more lube. Then she resumed her Stretching Exercises, building towards her second daily orgasm, driven by her own desires, and the challenge set forth by Mark.

Bit by bit, Tara’s pussy gave way to receive the fake dick. Soon, she was able to stroke its full length in and out of her pussy. Her orgasm was almost upon her when she got a text from Mark, saying, “Hello sunshine! Hope you are having a great day.” The text contained four emojis that made Tara smile: a wink, a cigarette, an eggplant, and a three squirt symbols. With renewed energy and commitment to her stretching, Tara pounded her pussy and had her second orgasm of the day.

With the dildo still firmly inserted, Tara took a picture of her stuffed pussy and texted it to Mark along with the cheeky message, “Yes Mark, so far so good. Two cums down and one to go. Can’t wait to show you my progress tonight!” Tara added some emojis of her own to the text: a cigarette, two eggplants, and two squirts.

Mark heard the “ping” that he was hoping for and snuck a discreet look at Tara’s racy message, while trying to stay focussed on the business meeting. His dick started to harden at the thought of Tara doing something so bold and naughty. He was thrilled that she was willing to indulge his pussy-stretching fetish, and that she seemed to be enjoying it herself.

Tara relaxed and smoked another More 120 while she thought about how to get her third daily orgasm. She looked at the final dildo and couldn’t believe she had ordered it. She lifted it in her hands and felt its enormous weight and heft. It was amazing, and daunting - 13 inches long, as thick as a beer can, and dark brown. The packaging said it was sculpted from the real cock of “Bam,” a famous black porn star. Could Bam be the answer for her third cum of the day?

Tara placed the huge head of the Bam dildo against her open pussy and gave it a push. She felt her lips indent under its thrusting power, but it was not even close to fitting inside her. Tara was disappointed in herself, and with the thought that she might never achieve the dimensions she and Mark craved, she tried again to push the dildo inside, still to no avail.

With a final desperate effort Tara tried to take the huge black dong by sheer force. She used its suction cup to attach it to the floor and then mounted it. She closed her eyes, took a deep breath of smoke from her dangling More, and then sat down – hard. White hot pain shot through her pussy lips and she knew that this task was impossible for her. But then, she thought, this was just her first day. Mark was right, she needed to work at this gradually. She dreamed of the day when this massive rod would split her open, preparing her for the real thing.

Tara still needed to have her third daily orgasm and wondered how to do it. Tara’s horny gaze fell on the brandy bottle. Tara took a large swig of brandy and then slowly inched the neck of the bottle into her pussy, spreading it wider and wider. Tara pushed the bottle deeper into her pussy until she was stretched as far as she could go. She left the bottle inside her while she had another cigarette and thought how wonderful it was going to be to have three orgasms every day! With a cigarette dangling from her lips, Tara rode the bottle to her final daily climax.

Completely spent, Tara sent another text to Mark. It was a picture of herself smoking a cigarette with the brandy bottle sticking out from her pussy. Along with the picture were the words, “Mission accomplished, Sir,” and some emojis: a cigarette, 3 eggplants, and 3 squirts.

Mark got Tara’s message and, after a quick glance, excused himself from his business meeting. He went to a bathroom stall and, looking at Tara’s sexy message and picture, beat off and shot his cum into the toilet.

Later that night, after Clara went to her room for the night, Mark and Tara cuddled in bed. Mark cupped her large, pendulous, breasts and asked how her first Stretching Exercises went.

A Mark fondled Tara’s tits, she responded to his touch. Her nipples hardened and her pussy moistened. She felt the unfamiliar combination of lightness, hope, and fluttering-heart excitement. Tara turned to whisper into his ear, “It was ... Fuck ... ing ... Amazing!”

Tara then told Mark about her stretching progress. He insisted on hearing every detail, however minute, and she was happy to comply. She was pleased to report that she had three orgasms on three different objects, and that she had really tried to fit Bam inside her pussy, but without success. She said that she would work hard to get bigger every day. Her voice held a hint of excitement as she awaited Mark’s response.