A Big Problem Pt. 01

Stacey sat in the dark watching television and drinking wine while she waited for her son, Andrew, to return from his date. Andrew opted to stay home for his first few years of college to save money. Stacey was glad he didn't leave home after high school. It had just been the two of them since he was two years old. Andrew's dad left when he was still little, so the burden of raising him fell solely on Stacey's shoulders. It required lots of sacrifices, but to Stacey it was worth it. They had a very close relationship that she wouldn't trade for the world. Andrew had essentially been the only man in her life for years. She dated casually, but not with much regularity. Stacey had grown accustomed to her life with Andrew and not having to deal with a boyfriend or husband. Not that she didn't have plenty of offers. At forty-two, she was still quite attractive and could pass for a woman ten years younger.

Taking a sip of her zinfandel, she heard a knock at the back door. It might have been cause for concern if Andrew hadn't mentioned that his friend Warren might be coming by to spend the night. Warren was practically a second son to Stacey. He and Andrew had been friends since sixth grade. Warren's parents were not very involved in their son's life. He had relied more on Stacey for emotional support and a sense of family growing up.

"Why are you knocking, Silly?" Stacey asked after opening the door to Warren.

"It looked dark," he answered. "I didn't want to startle you."

"Get in here." Stacey gave him a quick kiss on the cheek and a hug, as she always did. She felt bad that Warren's parents didn't seem to care much, so she always made it a point to show him some affection. "It's pretty early for you to be getting in. I thought you had a date."

"Yeah. She wasn't feeling too well, so I took her home." Warren put his backpack down. "Andrew's still out, yeah?"

"Yeah, he won't be back until late probably. You can watch tv with me if you want to," Stacey offered. It was only about nine o'clock.

"Okay. Is it okay if I have a glass of wine, too?" Warren wasn't quite of drinking age yet, but Stacey let him drink a little every now and then.

"Oh, alright. Just one, though. Okay?" Stacey didn't want to encourage it too much, even though she'd had at least three herself by that point.

The pair watched another episode of zombies. Stacey had another glass of wine and had a really good buzz going. Warren had openly snuck a second rather large glass himself. While they paused between episodes for Stacey to go to the restroom, Warren was working up the nerve to ask her advice about something that he'd been carrying around for a long time and was really struggling with.

"Mom, can I ask you something?" Warren and Stacey both hated it when he called her Mrs. Bell and calling her by her first name just seemed weird somehow.

"Sure, Sweetie. What's up?" Stacey was always ready to help her boys out. She loved watching them grow into young men and helping them through life's trials and tribulations.

"Okay," Warren steeled himself. "This is really awkward, but you're the only person on the planet I could think of to talk to about this."

"It's okay. You can tell me anything." Stacey meant it.

"Okay. So... I'm worried that ...God, this is embarrassing... I'm worried that I'm too big down there."

Stacey looked at him quizzically.

"I mean. Jesus this is weird. It's just..." Warren fumbled around trying to explain himself. "All of our friends are having sex, except me. Every time I get close, she gets scared and calls it off."

"Who's she?" Stacey asked.

"The girl. Different ones. It's happened more than once. Once they get a look at it, they call things off."

"So, Andrew and his girlfriend are having sex?" Stacey probed.

"Duh. That's not the point."

"Sorry. I mean, I knew, but I was just curious. I guess. I'm sorry, go on." Stacey felt a little bad for focusing on Andrew when Warren was pouring his heart out.

"I don't know what to do. How am I supposed to ever have sex if no girl will go near me? Or it?" Warren gestured downward with frustration.

Stacey's face scrunched up. "Just how big is it?"

"Pretty big. I've never measured it or anything." Warren was lying. He'd measured it. A few times. Even in the context of the current conversation, it was just a little too embarrassing to admit that to his surrogate mom.

"Is it like porn star big?" Stacey asked, trying to get some idea of just how large Warren's problem was.

"Pretty much, I think," Warren guessed. "It's hard to tell from a screen, you know?"

"You know, Sweetie, you probably just need to find the right girl. Some girls, especially ones without much experience, are intimidated by a big one. You need to find a girl that will work through it with you." Stacey's inebriation allowed her to elaborate. "I mean, I've seen a few big ones. I didn't run away or anything, but my first time with one was a little scary at first. But it ended up being amazing. Jesus, I still think about that dick!" Stacey was a little embarrassed about that last part slipping out.

"How big was it?" Warren wanted a frame of reference.

"It's hard to describe, like you said. I mean it was big. Pretty big." Stacey realized that wasn't very helpful. And Warren didn't look very encouraged. The alcohol started talking again. "You know what? Let me see it. Whip it out."

"Seriously?" Warren was shocked.

"Yeah. It's no big deal." They both paused and then laughed at her accidental pun. Stacey grabbed his arm when she laughed. He always loved how affectionate she was. "I mean, I'm like your mother. I'll set you straight," Stacey assured him.

"Are you sure it's okay?", Warren worried.

"Yeah. Go ahead. Just get it over with." Stacey urged.

Warren started unbuttoning his pants and unzipping his fly. Stacey covered her eyes and quietly giggled awkwardly, "Oh my God. I can't believe we're doing this!" Warren removed his semi-hard cock from his pants while Stacey's eyes were still covered. He had always secretly found her extremely attractive and the thought of showing her his dick really turned him on, but he was also pretty nervous.

"Okay, you can look," Warren announced, holding his cock in his hand.

Stacey took her hands away from her face and looked down. "Oh, that's not so bad. I mean it's big. It's pretty thick, but it's not like scary big."

"It gets bigger," Warren clarified.

"Oh." Stacey tried to hide her surprise. "Okay. You mean you're not hard yet?" Her curiosity was piqued. She wanted to see just how big this thing was.

"Not all the way," Warren explained.

"Well, I can't really tell unless it's, you know," Stacey clenched her fists and jokingly pantomimed a bodybuilder flex. They both giggled. "Do you think you can, you know, raise the flag?"

"I can try," Warren said nervously. He started stroking himself.

Stacey watched for just a moment and then went to get another glass of wine. When she came back, she sat back down next to Warren. She couldn't help but watch him masturbate as his cock grew larger.

Warren could only look down at himself. He was too self-conscious to make eye contact with Stacey. He had never masturbated in front of anyone before, much less a beautiful woman, and certainly not a beautiful woman he called "Mom." Warren started breathing heavier as he reached a full erection. The pleasure of his hand stroking his cock and the excitement of Stacey watching him was overtaking any nervousness he felt at this point.

Stacey realized she had been staring at Warren's growing erection in a trance. She shook herself from her gaze, "You doin' okay, Sweetie?" She instinctively rubbed his leg to encourage him. Warren moaned when she touched him. "Oops. Sorry!"

They both chuckled at her faux pas. The mood lightened a little and Warren felt comfortable enough to look at Stacey for the first time. He continued stroking himself as their eyes locked. Warren was breathing deeply with pleasure. He licked his hand to help lubricate his shaft. The sound of his wet strokes and heavy breathing dominated the room.

"It's really hard now," Warren moaned.

Stacey broke eye contact and looked down at Warrens fully erect penis. "So that's as big as it gets?"

"Yes." Warren stopped stroking and held it up by its base so Stacey could see.

"I'm not gonna to lie. That's a really big dick, Baby." It was easily the biggest she had ever seen, but she didn't want to let Warren know that. It might discourage him. "It's beautiful, Sweetie."

"Thank you." Warren appreciated the compliment. "But is it too big?"

"Well, honestly some girls would probably have a problem with that." Stacey confessed.

"Is it bigger than the one you had before?" Warren wanted a frame of reference.

"It's maybe not quite as long, but it's thicker for sure." Stacey licked her lips unconsciously. Warren had instinctively started jerking off again. Stacey tried not to think about how she was starting to get really turned on.

"Come with me." Stacey got up from the couch and led Warren to the upstairs bathroom. "Let's see just how big that thing is." Stacey had some training in statistics and was thinking about things like means and standard deviations that she could use to look up and give her some idea where Warren fell in the pantheon of big penises.

Stacey removed a wardrobe tape measure from the drawer and knelt down in front of Warren. She could see it much better in the light. "Keep it hard, Sweetie, so we get a good measure. Let me know when you're ready." Stacey was having a difficult time reconciling how much she was enjoying watching Warren masturbate.

Warren looked down and rubbed himself as Stacey peered up at him. She looked so pretty, kneeling there with his cock in the foreground. He was as hard as he was going to get. Warren nodded that he was ready.

Stacey pressed the tape to the base of Warren's shaft and ran it to the tip. "I can't believe I'm touching you," she marveled out loud. Angling her head to get a read, Warren's cock was just above her face. Warren exhaled at the sight and sensation of Stacey touching him.

"Seven and three quarters," she announced. "Now let's check the girth." Again, Stacey pushed the tape to Warrens penis at the base. She had to hold the base of his cock to keep the end of the tape in place while she wrapped it around. Warren moaned. "Whoa. Six and a half." She paused, her hand still gripping Warren's base. "Let's see about in the middle." She was much less careful about measuring this time. She was mainly just marveling at having access to such a big dick. She was now unabashedly gripping Warren's shaft as she held the tape measure around the middle of his dick. Stacey's mouth was just a few inches from Warren's glistening hard-on. She didn't realize it when she licked her lips and swallowed again.

Warren moaned as he felt her grip on him. "Umph. You're the only one to ever touch me like that."

"Aw, you poor thing." Stacey sympathized. How could this magnificent tool be wasted? And how sad for Warren, at his age, that he hadn't been pleasured by a woman yet? Stacey absolutely could not believe it, but she began stroking Warren's cock. "It really is beautiful, Baby." Stacey felt like she was almost having an out of body experience, like she was watching someone else jerk off her son's best friend.

Warren was equally dumbfounded that Stacey was stroking his cock. She stared at it while she worked it. Feeling it in her hands. Seeing the veins bulging from the meat. Feeling its weight. Stacey couldn't get her hand around its entire circumference, so she dropped the tape measure and used both hands to grip and stroke Warren's impressive girth.

As Stacey stroked Warren's dick in the upstairs bathroom, Andrew quietly entered the house through the back door. Like Warren, he didn't want to disturb as it seemed like the lights were all out. When he reached the base of the stairs, he could hear moaning and see the bathroom light come into view above the top step. He cleared the first few steps just in time to see Stacey take Warren's huge cock in her mouth. Andrew froze.

Stacey could only fit about half of Warren in her mouth. She worked the base of his shaft with both hands as she kissed, licked, and sucked the tip and first three or four inches of the shaft.

"Hold my hair, Sweetie," Stacey instructed before she returned to work.

Warren gathered her hair in his hands while she pleasured him. After a minute or so, Stacey looked up at him and licked his shaft from the base to the head. "You have an amazing cock, Baby," she cooed before returning to the task at hand.

After just a few more moments, Warren grunted loudly, "Fuck, I'm gonna come!"

Stacey took Warren as deeply into her mouth as she could manage and doubled her efforts until he filled her mouth. She did her best to swallow his load, but some trickled out of her mouth and down her chin. When Warren was done spasming, Stacey cleaned her chin and then returned to lick Warren's cock tenderly and kiss its hypersensitive head. Warren's body jerked with pleasure.

"Oh my God," Warren sighed.

"Feel better?" Stacey grinned.

"That was amazing," he sighed with gratitude. He'd had his first blowjob and prayed it wouldn't be his last. "Thanks, Mom."

Andrew snuck back through the living room and out the back door. He was afraid to crank his car and draw attention to the fact that he was home, so he quietly opened the driver's side door and sat inside. For the next forty-five minutes, Andrew masturbated while replaying the scene in his head over and over of the woman who raised him sucking his best friend's giant cock.