Stretching Her Limits Ch 02

Gloria tried hard not to think too much about her consultation with Leo as the days passed. Whatever will be, will be, she told herself. She was thinking about his huge cock, however, and how she might approach their next meeting.

Her mind raced with questions. Were there male sex toys that catered for such huge penises? What if there were women out there who could take his full length and girth, as implausible as that sounds? Would he be prepared to pay for that? Would they have to pay him? Could you take that much dick in your ass? Could you have surgery to reduce the size of your penis?

She neatly jotted down some notes in a bulleted list.

Toys

Anal

Sex workers

Surgery

Porn

She wasn't sure about that last one, but she knew for sure that a man with a giant penis could get work in porn. Even if Leo didn't want to fuck on camera, he could easily make some extra money by setting up an OnlyFans account and posting videos of him massaging and sucking his huge member.

I wonder how he's getting on with that self-pleasuring, she thought, her visual image of him stroking and licking his dick interrupted by a phone call and her secretary informing her that her next clients were here.

"Thank you, send them in," she said, quickly shuffling her notes on Leo into a drawer and reaching for her computer keyboard to draw up the information she needed for her next consultation.

+++

Leo was bang on time for his next meeting a couple of days later. Gloria had continued her research and didn't feel she had much more to offer him.

"So," she began, "it turns out that your cock is too big for normal fleshlights or similar male sex toys. So, unless you can buy two and fuse them together in some way, you're limited there too."

Leo nodded, his face betraying sadness at the realisation that his sex life was going nowhere fast.

Gloria spoke slowly, putting on her most reassuring and gentle voice. "You could have surgery to reduce the size of your penis."

Leo perked up at the thought of having a smaller dick, until he heard Gloria's caveat.

"But you're looking at around £15,000."

Leo puffed out his cheeks and sighed. There was no way he could find that sort of money - that was half of his yearly salary and most of that went on rent, bills and essentials like food and petrol.

"God, I'm screwed!" he exclaimed.

"I feel for you Leo, I really do," Gloria said as she placed a hand on his arm, trying to ease his sense of exasperation. "I wonder if you would consider porn? It might help you raise the money for surgery."

Leo vigorously shook his head. "No," he said firmly. "I don't want to. It's bad enough going to the toilet or getting changed at the gym. No, I don't need to expose myself any more."

Gloria smiled sweetly. "That's fine. I'm just trying to give you options. As I've said before, this is a new problem for me so I'm just throwing things out there."

"I understand," Leo replied.

"How has the self-pleasuring been going," Gloria said, a glint in her eye appearing as she moved the conversation to slightly less confrontational ground.

"That's still fun. Was more fun when you helped me though," Leo laughed nervously.

"Well, thank you," Gloria said. She moved on quickly to another topic. "Leo, have you ever tried anal sex?"

His face screwed up into a scowl, clearly appalled by the idea. Gloria didn't need to wait for a verabel response. "Okay, fine," she told him. "Let's move on." She had no idea where she was going to move as she was completely out of ideas.

There were perhaps a handful of men in the entire world with cocks more than 10" when erect and probably fewer women who could take that much length. The chances of matching Leo with one of those women was infinitesimally small, and she did her best to explain that to him while not sounding too downhearted.

"I'm beginning to think that surgery might be my only option," Leo said, his words trailing off as he spoke.

"I think you're right," Gloria said. "If porn and seeking out sex workers is out of the question - and that's fine, of course - then that does seem to be the only option available to you. I'm sorry I haven't been able to come up with much more than that. Look, as a gesture of goodwill, I'm not going to charge you for this session."

"Thank you," Leo said, his face breaking into a smile for perhaps the first time since he'd walked through the door. "Could you take me, Gloria?"

Gloria's eyes widened at the thought. She didn't even possess a dildo as long as Leo's dick so she had no idea. She suspected not, and even if she could, wouldn't his enormous girth be the bigger problem?

"I don't...know," she stammered. She'd tried all sorts of things in the bedroom in her time but she'd never attempted anything like this.

"Can we try?" Leo asked.

She didn't want to have sex in her office. That would be an even bigger transgression than helping him suck himself off last week.

"Okay," she said, maintaining her calm and professional demeanour. "But not here, and not now. I have your number, I'll let you know a good time."

Gloria needed some time to prepare herself. She would have to buy herself the biggest vibrator she could find and start easing herself in before letting Leo have a go. How much could she take? She was about to find out.

A quick browse of her favourite online sex toy store was enough for Gloria to find the items she needed. One super long dildo and one very thick one. Three or four clicks later, and they were on their way, due to arrive the next day.

Gloria got home from work the next day and unpacked her new toys. She gave them a good wash and rinse before retiring to her bedroom to give her pussy the sort of workout it had never had before.

She started with the long vibrator, gently easing it further and further inside her until it pressed against something solid. She realised she had found her limit. Nothing - man-made or man-driven - was going any further than that. She pulled it out and lined up a tape measure alongside the dildo and was pleasantly surprised by how far she'd managed to take.

"10.5 inches," she muttered to herself. She smirked. Enough to just about take Leo's length. But what about his girth?

She pulled out her next toy. Nowhere near as long as the shiny vibrator that now glistened with her pussy juice, it was, she estimated, roughly the same circumference as Leo's penis. Now for the moment of truth, she thought.

With one hand rubbing her clit and thumbing the top of her cunt to provide some lubrication, she used her other to guide the tip of this giant dildo towards her pussy opening. She gasped as it pushed her apart, wider than she'd ever felt before.

"More lube," she said to herself, realising that if this was going to work, it needed to be as smooth as possible. Smothering the monstrosity in slippery lube, she gradually guided as much of it as she could inside herself.

It was slow going, but millimetre by millimetre she was able to push the dildo inside here, then take it out, until perhaps she could take an inch. More minutes passed and she reckoned she was two inches, then by the time she'd got to three, she had to stop. It was beginning to get uncomfortable so she called it a night.

That morning she restarted her pussy stretching regime and making sure she was as wet as she could get herself, she was pleased to feel the giant dildo going inside her a whole lot easier than the night before. By the end of her latest efforts, she was probably able to take about five inches.

"Getting there," she said to herself as she got out of bed and began to get ready for work. That night, she had another session, and again the next morning and after a couple of weeks, she was beginning to think the unimaginable: maybe she could take Leo and give him the pleasure he'd been craving.

There was only one way to find out.