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Gail’s Adventure

Category: Mature
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My friend Gail came home from work one day, entering the backyard through the gate as she usually did when she heard people in the pool. She expected to see her daughter. Dena, and some friends lounging or swimming. That is basically what she saw, but there was also something she never expected. Paul was standing between two lounge chairs where Dena and her friend Lana sat laughing and staring. Gail immediately saw what they were staring at.

Paul’s bathing trunks bulged out obscenely, showing a prominent and quite large erection straining his trunks.

Gail stopped in her tracks, totally stunned and unable to move. When the gate slammed closed behind her, the sound sent Paul spinning around, trying to hide his erection even before he looked to see what caused the sound. Dena and Lana spun around to look. Joey was sitting in another chair already facing the gate. All four kids turned pale, but no worse than Gail did.

“”Hi, kids,” Gail managed, along with a feeble wave. Somehow her mind was still trying to comprehend what her eyes had just seen. She didn’t have any idea what to say, and instead walked quickly to the back door and slipped inside. She wondered what the hell had been going on? And what the hell would have happened if she had come home later?

Gail’s mind was racing. She and Dena had always had a very open relationship, including – especially – when it came to sex. Dena had made it to 18 and all through high school without losing her virginity. Certainly she had experimented a bit. She told her mom the first time she had seen a penis. She even got some pointers on giving blow jobs. How many Moms did that for their daughters? But this kind of thing was different.

“How was it different?” Gail thought to herself. She finally decided that it was different because it was in a group situation. That, and the fact that she had actually seen it for herself. She told herself to calm down. Nothing really bad had happened. They were laughing at Paul’s erection, that’s all. Not making fun of it, that’s for sure. She had seen the large bulge, and was very impressed. Probably the girls had been teasing the guys and saw Paul’s erection, and that’s all there was to it. Heavens, Gail knew her daughter had done much more. She had just overreacted. She calmed herself down, and by the time the kids came into the house she made them feel relaxed and normal.

“Time to eat,” she said. Nothing made things calmer and more normal than food, especially to teenagers.

Gail put a plate of sloppy joes in the center of the table and passed a bag of chips around. The kids seemed fine, all the nervous tension gone. They talked loudly and brashly, including some off color language and comments. Gail put up with that, so it was perfectly normal. In fact she liked it. Often she joined in. Secretly, it made her feel like a teenager again. She sometimes worried if she was being too liberal with Dena, but she thought she had turned out very, very well.

“Mrs. Ray, you look very sexy in that outfit,” said Joey. It was a normal comment – one any of them could have made, and often had. All the kids agreed, and Gail felt good. She was only 36, ate carefully, and went to the gym regularly. She was proud of her body, and glad to have these young people give her some feedback.

The other kids mumbled their agreement, with Paul being the loudest. That brought a couple more comments about him being attracted to her, as well as most any female, it seemed. Everyone got very quite after someone made the comment, “Be careful Paul will get a big erection again.”

Normally that comment would cause nothing but a little giggle, but suddenly everyone in the room thought back at the display Gail had walked in on. They had all ignored it as if it hadn’t happened, but now they were all thinking about it again, wondering what would happen.

Gail finally broke the tension. “It’s okay, Paul. I saw it, and it’s okay.”

Everyone breathed a little easier, feeling the tension released. Then Gail leaned over, gave Paul a little kiss on the head, and said, “In fact, it looked mighty impressive to me!”

It took just a couple of seconds for everyone to be sure they understood what was said, then they all erupted in laughter. Gail smiled and turned back to the kitchen while the kids enjoyed the moment. Unfortunately, it would lead to many other comments and more in the future.

*** Gail’s husband was a plastic surgeon. That is, her ex-husband. She had married at 18, he was a little older, and she became pregnant right away. He made a lot of money. He was evidently very good at his job. Also at seducing women, as at least two of his patients became his mistresses. After his third affair she divorced him, keeping this gorgeous house and the large in-ground pool. That had been great, because it caused her daughter and various friends to hang out there a lot. It was good to get to know her friends, and to keep an eye on what they were doing. Not that Gail was very strict with what they did. That was another reason they hung out there a lot. But she did keep up with what went on, so she had to ask.

“Just what was going on when I walked in?” Gail asked Dena after everyone else had gone.

Dena laughed. “Nothing really, Mom. We were just, you know, making a few dirty comments about breasts, and – well – do you know what tit-fucking is?”

Now it was Gail’s turn to laugh. “Yes, dear, I know what it is. Do you? I mean have you ever?”

“NO!” Dena answered, a little shocked. “No,” she said again, more calmly. “I think I would have mentioned that to you! Do guys really like that?”

“Well, yes,” Gail said. “Some of them, anyway. Of course, some guys will like anything you can think of – and a lot that you can’t think of. Just remember, whatever people do should be enjoyable for them both.”

“I know, Mom. And I think Paul must like tit-fucking, or at least thinks he does, because – well you saw how he reacted when we mentioned it.”

Gail smiled, and Dena continued. “Then when we saw his, ah, reaction, we made him stand there and give us a good look. That’s when you came in.”

“What if I hadn’t come home just then?”

“What do you mean? Nothing else was going to happen. We were just enjoying the sight. He seemed pretty big, didn’t he?”

She really was asking. Gail said, “From what I saw he is very large. One of the largest I have seen, though I couldn’t tell exactly how big.”

She saw that Dena was thinking deeply about something. “How many penises have you seen?” she asked her daughter.

“Just the two boys you know about – Danny and Trevor. Oh, and Bobby, when he stripped and ran through Beth’s party.”

Gail knew Danny was Dena’s blowjob, and Trevor was just some petting and stroking. “And how did they compare to Paul’s?”

Dena’s eyes got large as she said. “Wow,Paul seemed sooo much bigger. I think… I’d really like to see it for real.”

Gail didn’t like hearing that from her daughter, but she understood. She already had pictured what his dick might look like several times in her own mind. Of course Dena would be curious as well.

“Oh, you would, would you? Just stare at it?”

“MOM!” Dena was a little embarrassed. “Well, yes, sort of. But I think he likes me. We’ve been good friends, but I think he’s going to ask me out.”

“And how do you feel about him?”

“Oh, he’s really nice. And funny. I like him. I really want him to ask me out.”

“Not just because of his penis?” Gail teased.



It wasn’t long before Paul did ask Dena out. They had been out a couple times when one evening they came home from a date and were sitting in her living room. Dena knew her mom was in her room, and she knew that Gail wouldn’t interrupt her. She had often brought dates to her home, and her mom always gave her privacy. It was nice that she had a safe place to go, safe from strangers as well as a date who might get too carried away, instead of some parked car or something. And her dates never knew that they had another person just a few feet away.

Gail was relaxing in her room, listening to her ipod as she usually did in case her daughter brought a date home for a while. She didn’t know they were there until she heard a noise, then got up to check. Opening her bedroom door slightly gave a perfect view into the living room. She saw her daughter and Paul on the couch, but just as she went to turn around she saw Dena slide off the couch onto the floor.

Dena had been blocking Gail’s view. Now she could plainly see Paul’s dick, sticking straight up out of his lap, his pants around his ankles. Dena had slid onto the floor and kneeled right in front of him. Her blouse was unbuttoned, and her bra was unfastened and pulled free of her breasts. She reached into Paul’s lap and wrapped her hand around his erection.

His dick looked as big as Gail had thought it might be. Perhaps bigger. She knew she shouldn’t keep looking, but Paul’s dick had her attention. Not only was it possibly the largest one she had seen, it was definitely the best looking. She would actually describe it as pretty, and Gail did not think dicks looked very nice in general. She liked them. She loved them. But she didn’t think they looked especially nice. Paul’s, however, was pretty.

She loved looking at it sticking up, pulsing when the hand squeezed it, pulsing again when the hand stroked slowly up the smooth, hard shaft. The head was beginning to turn darker, especially when the hand squeezed tightly near the tip.

Gail was startled when she realized she was having these thoughts about her daughter’s hand squeezing Paul’s dick. She had been so enthralled with his dick that she forgot it was her daughter and her daughter’s boyfriend that she was spying on. But she couldn’t stop herself. She was turned on by this scene, so much that she couldn’t tear herself away. It was like she was observing a play or a movie, and the kids were actors, not someone she knew. Especially her own daughter.

Gail watched as Dena leaned closer toward Paul’s dick. She then started licking the head. Light, tender licks, followed by longer, harder ones just around the fleshy tip. Then she began licking the shaft, up and down, and back to the head again. Gail’s mind reflected on how well Dena was following the instructions Gail had given her a few months before, then was disgusted with herself as she realized again that she was spying on her daughter giving head. But still she was unable to pull away from the scene.

Gail continued to watch as Dena parted her lips and took the tip of Paul’s dick into her mouth. She could even tell that Dena was swirling her tongue around the head, and working just a little more inside her mouth. “How can she fit that big dick much further in?” Gail thought to herself. Her mind had pretty much given up the thought of who she was watching by know. Her hand had reached in between her legs and was now stroking her pussy.

Dena was working hard to keep Paul’s dick in her mouth. She tried to work more of the shaft inside, but it was a slow process. His dick seemed even bigger inside her mouth than it looked. Her hands gripped his shaft, pumping the six or so inches that was not in her mouth. Paul had his head back on the couch, loving what was being done to him. When he looked down at Dena, they smiled. Mostly Dena’s eyes smiled, because her mouth was stretched about as far as it could go. Still, she kept working at licking the head and whatever shaft was inside her mouth, and pumping the shaft as well.

As she was pumping, Paul’s dick seemed to grow even more, and get harder. He was getting close to exploding. Gail’s hand was reaching inside her panties, finding the wetness there and spreading it onto her clit as she rubbed it. She hadn’t seen many porn films, but this was better than they had been.

Paul reached around Dena’s head, holding onto the back of it with both hands. He looked as if he was in pain, but good pain. Getting ready to cum, he was nearly out of his mind it felt so good. He bent forward a little, and pulled his hands and arms tighter, forcing Dena’s head further onto his cock. Dena’s eyes bulged out as she felt his cock pushing further into her mouth. There wasn’t room for much more. She tried to fight back, pulling her head away, but Paul’s strong hands wouldn’t allow it. Dena was now just trying to breath as his cock filled her mouth completely, forcing its way in. Paul pulled her head harder and harder into his lap as he felt his orgasm coming closer. Dena’s hands now were off his cock, pushing on his legs in an attempt to keep herself away from him, to keep herself from being impaled on his cock.

They were both moaning, Paul wishing his orgasm would finally explode, Dena because his cock was forcing its way to the back of her throat. Finally with a loud groan, Paul exploded. His cum roared out of his cock and into his girlfriend’s throat. Dena’s eyes bugged out even further as she felt her throat fill with his cum. Now she couldn’t breath at all. Nor could she swallow. She felt like she was going to run out of breath and die while impaled on this hard cock in her mouth, but the moment passed as Paul’s grip lightened on her head after the first couple spurts, and she was able to pull her head back. Another spurt and she was able to pull her mouth entirely off his cock.

Dena was gasping for air. Deep breaths brought blessed air into her lungs. She also swallowed Paul’s cum as she tried to clear her throat and gasp for more air. One of Paul’s remaining spurts shot cum onto her face, but she didn’t seem to notice. As she was able to breath again, she again was drawn to the cock in front of her. It was still oozing cum and looking angry, though it was much softer now than it had been moments before when it nearly suffocated her.

Dena reached up with one hand to enircle the dick. Paul moaned as her hand stroked it, helping to coax more cum out of the tip. After a few strokes he opened his eyes to look down at her again. They smiled. She reached her head towards his dick, and flicked her tongue out to lick the cum hanging off the head. He groaned again at that, but was too weak for anything else. She felt his dick spasm a few times as she licked the shaft a little more and finished him off. He was drained.

Dena then wiped her hand across her face, just noticing the cum on her. She had one big glob on her cheek, dripping down, and some leaking out of her mouth that she hadn’t been able to swallow. That was the last Gail saw as she backed away from the door before she could be discovered.

Fleetingly, the thought of it being her own daughter crossed her mind again – kneeling on the floor with that big cock in her mouth, seeing her with cum dripping from her face – but she drove the pictures away as she sunk into her chair. Pulling her panties aside, she attacked her clit with one hand while her other hand went to her pussy. She put a finger deep inside her vagina, then two fingers, until she felt hot tingles all over, especially in her pussy, and could hardly keep still as her orgasm erupted. Slumping in the chair and biting her lip, she came in waves, one of the longer ones she could remember.

She had not quite recovered when she pushed herself out of the chair and onto the bed, reaching into the drawer of her nightstand and pulling out a dildo. Not even getting it wet first, she plunged it into her sopping pussy with a groan that surprised her. Reminding herself to be quiet, she worked the dildo in and out of her channel, quickly pushing herself to the edge again. It wasn’t her favorite dildo, but it was the one she grabbed first, and it was doing a great job. Very quickly she hit another orgasm, rocking back and forth on the bed, biting her lip to remain quiet, as her body was wracked with spasm after spasm.

She finally calmed down. She found herself sprawled out on the bed, not really remembering just how she ended up like that. The dildo was still deep inside her, so she slowly pulled it out, creating a couple more shudders from inside her pussy. It hit her that she had just had two incredible orgasms caused by watching her daughter, and of course watching that large, beautiful cock that her boyfriend had.

No, there she went again, thinking of his dick, and her daughter working it, as if it wasn’t wrong. The more she calmed down the more ashamed she was, as she thought of how wrong it was to even watch, let alone get so sexually excited by it. How would she ever face Dena? Well, Dena didn’t know that she had been watched, did she? Gail would just pretend she hadn’t heard – or seen – a thing.


The next morning was a Sunday, a slow moving day. Gail hadn’t slept well. She was bothered by spying on her daughter, but in spite of herself she couldn’t stop feeling a little tingle in her pussy when she thought about Paul’s dick. She was sitting on the deck with her second Bloody Mary when Dena came out to join her.

“Good morning,” Dena said, brightly.

“Hi, Honey. How are you?” Gail had to struggle to act normally.

“Good,” Dena replied.

“How was your date?” She couldn’t help herself.

“It was good.” Dena acted as if everything was normal.

After a short silence, Gail just had to continue. “Have you and Paul… done anything yet?”

“You mean have sex?” It seemed so much easier for Dena to talk about sex. Especially this morning, Gail thought, feeling very guilty.

“No,” Dena continued. “I don’t know if we will. Paul is really nice. He’s a sweetheart. But I don’t think I like him in that way.”

“Even with a dick as big as his?” Gail hadn’t meant to say that. It just came blurting out.

“Mom! Is that all you think about when you think of him?”

Oh, if she only knew. More guilty feelings started, then she noticed Dena was starting to smile.

Gail answered carefully, “Of course not, dear. But by that smile it looks like you’ve thought of it a lot.”

“Oh, Mom!” Dena moved closer, as if ready to share a secret. And she was. “Last night I saw it. I had felt it through his pants before, but last night I saw it, naked and up close.”

Gail felt a twinge between her legs, and tried not to act turned on or guilty, two emotions that were struggling inside her at the moment.

“Oh,” Dena continued, sensing something strange in her mother’s reaction. “Am I sharing too much?” She giggled.

Straining to sound normal, Gail assured her it was fine.

Dena kept talking, rapidly. “Well, I wouldn’t give a lot of details, but I do have some questions about it.”

“Shoot.” Gail winced as she said this because it made her picture Paul’s dick erupting. Not something she should share with her daughter.

“Well, we came back to the house last night…”

“Oh?” Gail said, trying to act surprised.

“Yes, we weren’t sure where to go, and I was thinking of getting a little intimate. So we came here and… well, we did get intimate.”

“Go on,” Gail encouraged.

“He was groping me, of course.” They smiled at each other. They both knew that a sexy girl like Dena had gotten felt up on most of her dates. As much as Dena allowed, and she allowed at least some most of the time.

“Anyway, he had me undone on top, and I was feeling him, and we both sort of got his pants off. My God, it seemed big!” Her eyes bugged out like they had last night, though not as much.

Gail thought she was getting moist between her legs. “So it is the biggest you’ve seem?”

“Oh, my, yes. By far. I don’t know how big they get, but I can’t imagine much bigger than his. I could barely…” She paused, then continued on a little less excited. “well, I could barely get my hand around it, and… well, I gave him a blowjob.”

Gail tried maintaining no expression on her face.

“That’s what I wanted to ask about.”

Gail said, “Okay. But we already talked about doing that.”

“I know. But… this was different. I mean, I licked it and stroked it.”

Gail interrupted. “You don’t have to go into detail,” she reminded her. She didn’t think she could hear about it without getting too turned on again.

“Sorry,” Dena smiled. She knew her mom got a little uneasy with this subject sometimes, but it felt so good having someone to confide in. Sometimes her friends were too judgmental.

“Anyway, the thing is, it was so big, I could hardly get it into my mouth!”

Gail blushed. She was very uncomfortable, but not for the reason Dena thought.

“I just got, you know, the head in, and I didn’t think I could do more.” She looked at her mom. “Are you okay with this?” Her mom looked a little troubled.

Gail was sure she was wet now. She felt like she just had to stroke her clit right now, but of course couldn’t. She just nodded her head.

“Well, it was so big I just held the head in my mouth and stroked it with my hands. It worked, because he was certainly enjoying himself. But then… well, when he was getting close, he took my head and, sort of, held it tight and, you know, forced his penis deep in my mouth.”

She looked a little hurt, or confused.

“He pushed in. I don’t know how far, but it felt like a lot. I couldn’t breath, but he kept pushing. I was actually scared until he, ah, started.”

“Cumming?” Gail asked. This wasn’t the time to get shy.

Dena nodded.

“And then he let go?” she asked, as if she hadn’t watched the whole thing.

“Yes. As soon as I could I pulled away. I had to breathe.”

“Was he done?”

“No! He kept cumming! He shot a lot. He got it all over, and I tried to help him. You said I always had to finish the guy up.”

“And you did a good job.” Gail added, before thinking. Dena looked at her strangely.

“Shit,” Gail thought to herself. “Watch what you’re saying.”

Gail continued, “It sounds like – you did a good job. But what was your question?” She hoped she had saved herself.

“Why did he do that? Why did he force himself in so far? I didn’t like that at all, and you said both people should enjoy whatever they do.”

“Well, Honey, he couldn’t help it. When a guy starts to cum he isn’t really in control of himself. Think of how you feel when you cum. He just naturally wants to push in deep, and he wasn’t even thinking about how it might be too big for you.”

“He should think about me!”

“Of course, but right at that moment he can’t think of you. Or anything. Can you?”

Dena thought for a moment. “I guess not.”

“Try thinking that the next time you do it,” she smiled.

Dena thought for a moment. “But I couldn’t breath! I thought he was going to keep holding me there until I suffocated!”

“Yes, but he didn’t, did he? He let you go as soon as he could?”

“I guess mostly I was afraid he wouldn’t. Maybe I panicked a little.”

Gail smiled and nodded.

Dena asked, “But Danny didn’t hold me like that. Just my luck that the guy with the biggest penis would try to shove it all the way in!”

It wasn’t long before Gail excused herself to go to the bathroom. Along the way she stopped to pick up her dildo again, and spent several minutes pushing it deep inside her pussy, making it spasm and giving her much needed relief. She couldn’t wait until Dena was out of the house and Gail could use her vibrator.


Paul continued coming over to the house, even though he and Dena did indeed stop dating. But they remained the best of friends. Dena seemed to be even more at ease teasing him, sexually, after their intimacies. She enjoyed commenting any time he got a bit of an erection or even when he didn’t, and the others joined in.

One day Gail was in the kitchen preparing food for the kids, as she often did. Wearing only a two-piece bathing suit, she caught the attention of Dena walking in and seeing Paul looking at her.

“Mom,” Dena said with a grin, “be careful, I think you’re giving Paul an erection.”

“Dena, leave the poor boy alone!” Gail said. Paul tried to cover the evidence.

“Oh, he can take it,” Dena said, as she reached over and patted the bulge in his trunks.

“Dena!” Gail said in surprise. Then, “I’m sorry, Paul.”

“That’s okay,” he said, embarrassed. “I can’t always control it.”

“Plus he thinks you’re really HOT!” Dena added.

Before Gail could respond, Paul tried defending himself. “Well, sure, all the guys do.”

Dena smiled broadly as she walked back outside. Paul just looked at his feet. Gail was speechless.

Finally Paul started to say something, and finally got out a sentence. “Mrs. Ray, can I ask you something?”

“Sure, Paul, what is it?” She was glad to change the subject, but that wasn’t what Paul was doing.

“You seem really open about… sex and stuff. And you ARE hot, so I’m sure you’ve had lots of experience.”

“Paul.” She started to cut him off. That wasn’t what she should be hearing. But he did call her hot again. He must really mean it, and that made her hesitate.

Paul went on. “Can I ask you a question?”

“Of course.”

“It’s really personal.”

“Paul, you can ask me anything. You know that.”

“Yeah. It’s just… well… it’s really personal, but you already know my problem.”

Gail didn’t know where he was going, and it showed on her face.

“It’s my thing. My, you know… my penis.”

Gail was speechless.

“You know it’s, well, bigger than other guys’.”

Gail nodded agreement, not wanting to comment.

“I’m just afraid it’s… too big.”

Gail had to say something. “Why do you think it’s too big?”

“You know, girls act like they’re interested to see it, and even touch it. But if I try to fu… ah, have sex with them, they don’t want to.”

Gail was uncomfortable, but knew he was really serious, and hurting. “Have you ever had intercourse?”

“No, and I think I’m the only one. And I’m already 19. Everybody says women like big cocks, but… Oh, I’m sorry.”

Gail smiled. “I’ve heard you say ‘cock’ before, Paul.”

“Really? I’m sorry. It doesn’t seem right to say it now.”

“We can say penis, or dick if you’d like. And women do like big penises. Or small ones. It has more to do with the man.”

“Really? It sure seems like the big ones are better for them.”

Gail knew what he meant. “Of course they talk about it. Especially young girls. But do you pick a girl because she has the biggest boobs?”

Paul smiled. “Well, it sure helps.” But when he saw Gail’s expression, he said, “No, not just that. There are other things.”

“Exactly,” she said. “It’s mostly talk. And breasts are much more important to guys than penises are to girls.”

“But is it bad? Why can’t I get laid?” His face flashed with embarrassment again at his language, but Gail didn’t let him apologize.

“Have you actually tried to have intercourse? I mean, actually tried to put it in?”

“Yes, I have. With two girls. We got that far, but they said it hurt too much so we had to stop.”

“Oh, I’m sorry, Paul. That must have been hard. I mean difficult.” Damn, trying to correct herself just made it worse.

“It was. Everybody thinks it’s so nice to have such a big dick. I think I’m too big to ever have sex.”

“Nonsense,” Gail said. “You will have lots of sex, with a lot of girls… if you want to.”

“But when?” He was almost pleading.

“Soon. You probably need… you may need a girl who has some experience, so she is used to having done it. And you’ll have to be careful, go slow.”

He seemed to be thinking deeply. “Are you sure? I mean, it is awfully big.”

“I’m sure it is,” she said, inadvertently glancing at his crotch.

Paul reached a hand into his trunks.

“What are you doing?” Gail asked.

“Would you look at it and see what you think?

“No,” Gail said quickly. “That wouldn’t be right.”

But before she was done talking he had pulled his dick out of his trunks, holding it in his hand. “Please,” he said.

“Paul, please put that away!” Gail ordered. What the hell…?

“But I’m desperate. You can tell me the truth, but only if you’ve seen it.”

He held his dick, his hands covering most of it. It wasn’t really obscene, except that his dick was out of his pants, of course! But she could see the fear in his eyes, in his voice. She couldn’t say no anymore.

“Okay,” she said. “Yes, it’s big, but it’s not abnormal.”

“But it gets bigger when it’s hard,” he said. She saw his hand squeezing it, encouraging his erection.

“I know,” she said, shielding her eyes from the sight but not able to look away. “I know, Paul, and I can see that it is big, bigger maybe than I’ve seen before.” She was thinking to herself – The damn thing kept growing in his hand. Surely it was done – it must be 8 inches long. And so thick!

How did she get into this situation. “Paul, it doesn’t matter. Girls stretch down there. They can get bigger to fit whatever you have.”

He looked at her, hopefully. “Really?”

“Really,” she answered. “You just have to be patient, get her warmed up slowly. You know, foreplay.”

“Are you sure? Even with this?” Paul looked down, most of his erection now exposed.

“Yes,” she answered. “Even with that.” She looked down at it again, a longer look, and she knew her pussy was wet.

“What the fuck?” It was Dena’s voice. She had just stepped back into the house. Paul had not gotten his hard penis back in his trunks, and her mother was standing right in front of him, staring at it. Before they could say a word, Dena was back out the door.


Gail knew she had to explain things to Dena as soon as the kids left.

“Honey, what you saw with me and Paul…”

Dena interrupted. “I know, Mom. Paul already told me. He was worried he was too big?”

“That’s right. Honey, it really is a problem for him.”

“I know, Mom. I guess we have to get him laid.”

Gail looked at her, saw the playfulness in her eyes, and they both laughed.

Dena said, “Maybe I can talk to Loretta about him.”

Gail looked at her. “You mean the slut?”

Dena nodded.

“No, Honey, Paul’s a nice guy. Don’t let him get mixed up with someone like her. He’ll find someone.”

The next day was too much for Gail to believe. Again alone with Paul, they talked about his problem again.

“I’m sorry to mention this,” Paul said. “But I think I know who I need to solve my problem.”

Gail was interested in what he had come up with.

“Someone older, experienced. Someone used to having sex wouldn’t be afraid of me, isn’t that what you said?”

“Well, yes,” Gail answered, not sure what he was leading up to.

“I know a couple of older women that are, you know, attractive,” he said.

Gail didn’t like his idea too well. “What makes you think they would be interested?”

“Well, I don’t know. I hadn’t gotten that far.”

Dena was standing nearby listening. She said, “Mom, you are the most attractive ‘older woman’ around.”

“Thank you, dear,” said Gail, not knowing why she changed the subject.

Dena said, “No, I mean – Paul’s problem.”

It took a few seconds to comprehend her meaning. Then Gail and Paul both backed away from each other, surprised and shocked at Dena’s suggestion.

“Dena, I am really…” Gail began.

Dena interrupted. “He doesn’t want a love affair, Mom. He wants a friend, a teacher. He wants some help. A woman who will be able to handle him. Who is better than you?”

Paul stood there, silently in shock, mouth hanging open. Gail had no idea how to answer Dena, so she said she had better leave.

A few minutes later Dena came into her room. “I’m sorry, Mom. I didn’t mean to put you on the spot.”

“Yeah, well… that’s okay, Hon. I think there is too much emphasis put on Paul’s virginity. He will be okay. Besides, I think he is the one you put on the spot.”

“He doesn’t think so. He thinks you would be a good choice.”

“What?” Gail was shocked again. “You talked about this?”

“Just now,” Dena said. “He was a little mad that I said that, but when he cooled off he admitted that you are sexy. Almost as sexy as me.”

“Thanks. But you trying to fix me up with a kid…”

“Mom”, she interrupted, “He doesn’t want an affair. He just needs to find out if his dick works. He needs someone who is understanding and patient, who is willing to be – unconventional.”

“Ha! Unconventional! That’s a good word for this,” Gail said.

“It’s a good word for you,” Dena continued. “Do you know how many of my friends can even mention sex to their parents? Hardly any! And here we are, able to talk details about my sex life – and sometimes yours. You are definitely unconventional.”

“Thanks, Darling. You are sweet. But that doesn’t mean I want to have sex with your friend.”

“Well,” Dena said, “He’d like to have sex with you,” and she left the room.

Gail sat in her room in a daze. It was so ridiculous an idea. Sure, Paul needed help, but not this. The one thing she couldn’t get out of her mind was the sight of his naked dick. My, that was a specimen.

She was thinking about her own sex life. It had been years since her divorce, and years since she had sex. There had been a couple of men, not too long after the divorce. She had wanted sex so badly then. She had one man on the first date, the other on the second date. That’s when she decided that since she couldn’t control herself, she just should not date at all. Especially with a young daughter. But recently, since Dena was now 18, she had started to think about dating again. It might be fun. And having a man between her legs would be great.

As she was sitting there, Paul appeared at the door.

“Sorry, Mrs. Ray. I didn’t mean to cause you problems,” he said.

“That’s fine, Paul, you didn’t. Besides, it was Dena’s idea.”

“Yeah,” he agreed. “I guess it was a silly one.”

“I am pretty old for you.”

“Oh, not that. You’re not old. I think you’re great. I just need to find someone willing.”

“You’ll find her, Paul. You are a great looking guy, and most women would love to experience someone your size.”

“But not you,” he said.

Flustered, she admitted, “Yes, Paul, me too.” She meant under different circumstances, but she didn’t say that.

“Really? You will? Damn, thanks.”

What had she done? What had she said? She sat quietly for a moment, thinking the unthinkable. Well, hell, if her daughter wanted her to, maybe she should. He was legal. He did need help. And if he was intent on finding someone, why should she miss out?

“Close the door,” she told him.

Paul’s eyes got big as he realized it was going to happen. And it was going to happen now. He closed the door and walked over to Gail, ready for whatever instructions she had. She reached up from her seated position and placed her hands on the waist band of his trunks. She didn’t pull them down, she just held them there.

“Are you sure you want to do this?” she asked.

She saw his dick twitch before he answered. She stood up and place his hands on her breasts.

“Normally you’d be kissing the girl, of course, but we won’t do that,” she instructed him. “And after you kiss a little you probably want to fondle these/”

Paul nodded, smiling.

“Now you want to get rid of this.” Gail was reaching behind herself to unfasten her top.

As Paul let it drop, revealing her bare breasts, he couldn’t take his eyes off them. They were very firm, and she had large areoles. Her nipples were getting hard and enlarged as he felt them.

“Go ahead and pinch them a little,” she encouraged. He was happy to oblige, and she felt tingles run through her body.

“When you get far enough that you think she might be willing to have sex, you have to be sure and give her lots of foreplay. You more than most guys.” She smiled at him as he looked up because of that last remark.

“Some guys can get away without too much foreplay, but you need to be very aware of it. Kiss her, kiss and play with her neck and her ears.”

“Hmm?” Paul expressed surprise at this.

Gail asked, “What? You don’t know that?”

“Not so much. The neck?”

“Yes, the neck is very sensitive for most women.” She took a hand from squeezing her breast and placed two fingers along the base of her neck. She pulled them along her neck and throat, saying, “Just lightly stroke along here. Very nice. And right here – the earlobe and right behind the ear.” She moved his fingers there, shivering a bit as his fingers had the desired effect.

“Kissing along the same places, light pecks and even licking a little with your tongue all feel great, but you can practice that on someone else.” Gail was getting very excited, but had to keep her composure.

She continued, “And when you play with her breasts, don’t just keep squeezing.” Paul immediately quit the squeezing he had been doing. Gail took his hands in hers, demonstrating as she spoke. “Stroke her breasts with your fingers as you did on my neck. Circle around the nipples. Squeeze the nipples. Feel the whole breast. Take turns doing all of those, and you can kiss them as well.”

Paul looked up at her, questioningly.

Gail knew what he was wondering. “Yes, you can kiss mine.” She moaned a little as he did. “Kiss lightly. Move around. Kiss one while you’re touching and feeling the other one.” He followed her instructions well, which made it difficult for Gail to concentrate on what she was trying to say. Some moans escaped from her, no matter how hard she tried not to.

“You’ve had an erection almost since we’ve started.”

“Oh, sorry,” Paul said, as he stopped what he was doing in confusion.

“No, no,” Gail said. “That’s fine. That’s normal. Keep doing what you were doing.” Oh, please keep doing it she thought to herself. “I just mean that guys are ready for sex much sooner than women. You must remember that. I’m just starting to get wet down there, which is what you need. You need the woman to have a very wet vagina.”

“Okay,” he said as he resumed his work on her breasts.

“You can lightly touch my neck and ears once in a while, too.” she reminded. Now lick my nipple. And suck on it. Pull it into your mouth. Ohhh, yesss! Ah, yes, that was nice.” If only all men wanted to follow directions this well.

It was a lie about her just starting to get wet. She had been soaked for a while now, but she wanted Paul to know to go slow. Not everyone would get as wet as her so quickly. Though it seemed she was wet a lot since spying on him getting a blow job from her daughter.

“Now with one hand, run your fingers slowly down over my stomach. Yes. Lightly. Down further.” Paul still seemed a little shy, not going too far down her stomach without being told. Now he went all the way down to her suit bottoms.

“Yes, the lower stomach is real nice.” She was having a difficult time keeping him going slow. She was ready to have him jump her, but she was supposed to be teaching him.

“Are you enjoying this?” she asked him.

Paul gasped. “My God, yes!”

“That’s good,” she said. “Do things that you like, and keep in mind what she likes. Keep changing what you are doing, taking turns among those things I showed you. Oh, that’s it,” as he sucked a nipple into her mouth. “And lick it while it’s in your mouth. Unngg! Yes. You can tell by her reaction what she likes the best. Every woman is a little different. Pay attention to what turns her on the most.

“Now slide your hand down lower – on my stomach – lower – over my suit. Keep going. Between my legs. YES! Damn, yes, that’s good. Squeeze. Ohh.

“Now move your hand down onto my leg. Stroke the inner thigh.” She hated to say this, but knew she should. “Softly, slowly. Yes. Tease me a little. Then back up to my crotch. Ohhhh.”

She really had to be careful. She was close to an orgasm, but had to hold off. It wasn’t easy.

“Move your hand under the suit. Feel the skin. Stroke it. Move your fingers down into the slit. Up and down. Back and forth. Oh, shit!”

“What’s wrong?” Paul asked, concerned.

“Nothing!” Gail practically shouted. “That’s good. It feels so damn good. Fuck!

“Do you feel how wet I am?”

Paul mumbled yes.

“That’s really wet. Girls probably won’t feel that wet yet. Feel my lips? My vaginal lips? Can you tell they are swollen? Feel them. That’s what she has to feel like.”

This was getting so difficult for her.

“Take off my bottoms!” she ordered, and Paul hurried to comply.

She spread her legs. “Look at my cunt. My vagina,” she corrected herself. “See how the lips are swollen? How they puff out? And wet? That’s how the girl needs to be. Now let’s get your trunks off.”

She was getting desperate. She pulled at his trunks, and he helped. His huge erection came popping out at her face. “Oh, God,” she thought to herself. “What a tool. It must be over 8 inches!

She reached out and grabbed his dick, wrapped her hand around it. felt it. squeezed it, stroked up the shaft, feeling the smooth, hot skin. She pulled his hand back over to her crotch. “Keep me wet,” she told him.

She stroked all the way up the shaft, running her hand over his glans. When she felt his dick twitch, she thought they had better start fucking before he blew his load.

“Okay, come up here,” she told him as she scooted herself to the center of the bed. He followed, and she put his hand back into her crotch.

“Find my hole. Put a finger in.” He did.

“Put two in,” she told him. He did, and she moaned.

“Are you okay?” he asked.

“God, yes,” she said, starting to hump against his fingers. “That is great. But be careful with girls. They probably won’t go in as easily.”

“Okay,” she said, not being able to say much more. She took hold of his cock and pulled it toward her vagina.

“Take out your fingers.” She rubbed the head of his dick along her slit. “Get this nice and wet before you stick it in. There’s the hole,” she said, pushing his head into her hole and wiggling it around. Oh, dear, it was so thick!

“Push your hips forward,” she told him and he did. His dick pushed against her hole, into her hole, spreading it open. Just the head went in, maybe an inch more before she groaned loudly.

“Are you okay/” Paul asked, as he stopped pushing.

“Hell, yes,” she said. “It’s so good. Pull back just a little and then push in some more.” She remembered to still teach him. She pulled his hand to her lips and said, “Try to pull them apart as your dick goes in. Less friction. Easier.” She was even having trouble speaking now.

He did as she said, and pushed it in another inch. She moaned loudly enough that he stopped once more.

“Again,” she said. His dick was stretching her, more than she had ever been strtched. It was pushing into her far enough to reach that sensitive area, her so-called ‘G-spot.” When he hit that she started erupting. No longer able to hold herself back, her orgasm overtook her. When her vagina contracted around the first few inches of his dick, he lost it as well. Holding it inside her, his cock spurted cum into her as they both lost total control.

After the first two spurts, he pulled back and pushed in again with another spurt. Rubbing her G-spot made Gail tremble again, shock waves pulsing throughout her body. She wrapped her legs around him and pushed her hips upward, hoping to get his cock deeper as her orgasm kept rumbling through her. His dick was getting softer and smaller so she was able to get it a little deeper into her before her orgasm finally ended.

Even before he was done cumming, he started apologizing. “I’m sorry, I didn’t mean to cum so soon.”

“It’s okay, Paul. I’m surprised you lasted that long for your first time,” she said as soon as she could speak.

“Thanks, Mrs. Ray. That felt great. Wow. We did it. I was almost in.”

“Oh, you were in. Believe me, you were in. You were fucking me very well.” She didn’t care about her language any more.

Paul seemed a little disappointed. “But it was only halfway in. I can’t get the whole thing in you, let alone a girl who is close to being a virgin.”

She felt he pussy twitch when he said he was only halfway in. What would the other half feel like, she wondered. “Oh, Paul, don’t be silly. The only reason you didn’t get all the way in is because you came. You work fine.”

He didn’t quite look convinced. Gail looked at his penis. It still looked a little firm. She confirmed that when she took it in her hand. She stroked his shaft a little and felt it respond. “The first time guys cum quickly. You held out really well. But the nice thing about young guys is they are ready for more very fast. We’ll just have to do it again, if that’s okay with you.”

He said, “Sure, sure,” and looked at her in amazement. She smiled at him, stroking his shaft and feeling it respond. Oh, yes, they were going to have a second round. What was it about this boy? She was thinking to herself. It couldn’t just be his big dick, could it? Maybe it was because he was such a hunk. He was actually very well built – great arms and chest, nice flat stomach. Or maybe he turned her on so much because he was ‘off limits’. – much younger than she was, not to mention being a friend of her daughter. Or maybe he was just the first chance at real sex in so very long. Or perhaps it was so exciting because she knew her daughter must be listening, picturing what they were doing. She imagined Dena was right on the other side of the door. But all these thoughts flashed through her brain quickly. She had no time to consider them at this moment.

Gail bent over, leaning towards his crotch. She smiled, sticking her tongue out, looking Paul right in the eye, as she moved closer to his dick. She was teasing him, and he loved it. Her tongue found the glans and licked across the tip as he moaned. She circled his head with her tongue, driving him crazy. Her hand was stroking his shaft. She reached her other hand down to his balls, pulling them firmly down and away from his body. She rolled them back and forth, squeezing them until he moaned in pain.

Gail parted her lips and placed them around his head. It felt hot and wet. She pushed his whole head into her mouth, then down onto the shaft. She couldn’t get very far because her jaw wouldn’t open far enough to let more in. She thought of watching her daughter do this same thing a few weeks before. No wonder she had had such a difficult time. This dick was huge! So thick that her jaw was already hurting with the strain. Fortunately, his dick had regained its hardness. He was ready to fuck again.

She continued playing with his balls and stroking his shaft. “Just lay there. I’ll get on top this time.” Placing her legs on either side of his body, she held his long, thick shaft straight up and rubbed it against her pussy.

“Get it wet,” Paul said, repeating her earlier instructions.

“That’s right,” she told him. “You remember that.” She was still wet, from herself and from his cum, and she was still hot. Her vaginal lips were still swollen, her vagina ready for him.

Gail lowered herself slowly onto his shaft. They both moaned with the feeling of his thick shaft entering her again. She got in 3 or 4 inches without a problem, but it was a very snug fit. She could feel the ridge around his head as it pushed its way through her hole, stretching her walls. Pleasure coursed through her as his ridge made its progress up inside her.

She raised herself up, then back down, feeling his ridge and his shaft slide along her channel, She was in heaven with the exciting feelings it caused all through her. When she lowered herself back down each time, she went a little lower and his dick went a little further into her. Each of those strokes caused new excitement as his dick forced her body to open further. She started bouncing harder onto his cock, feeling pain and excitement with each thrust.

“This is amazing.” Gail thought to herself. Never had anything so big been so deeply inside her, other than when she gave birth. She felt almost like a virgin as he was deeper inside her than anyone had ever been. Bouncing on him, she was penetrated his full length.

“Uh, uh, uh, uh,” escaped her as she impaled herself over and over on his cock. Feeling like she had a steel pole up her vagina, she was turned on like never before. She could feel her entire body tingle as her orgasm was about to take over her body.

“SHIIIIIT!” she screamed as her whole body spasmed, from deep within her pussy to her toes and fingertips. She ground her crotch into his, feeling his cock reach its fullest into her. She held there, pushing down, through several spasms, then lifted halfway up in order to drive down again, shoving his dick through her channel several times and causing more spasms.

“Are you okay?” Paul asked. He had laid there during her convulsions, unsure of what to do or even if she was hurt.

She had collapsed on top of him. He had not cum, his erection as strong as ever shoved up inside her.

“I am GREAT! ” she moaned. “And so are you. But we need to make you cum. I told you you would last longer the second time.”

“But you already came,” Paul said.

“So? You surely know women can have more than one.”

“Yeah, but…”

“But what? And I can have more than most women.” She smiled broadly, still excited, especially with the throbbing dick inside her. “Roll over.”

Gail held her crotch tightly to him as she rolled to one side, bringing him with her. Now on the bottom with Paul firmly between her legs, she wrapped her thighs around him and crossed her ankles, pulling tightly.

“Fuck me,” she ordered.

“But,” Paul started.

“Fuck me,” Gail repeated, gripping him tightly with her legs. “Hard.” She couldn’t believe how horny she still was. She had just had a fantastic orgasm, and she wanted more.

Paul started moving his hips slowly.

“More,” she said. She was pushing her hips into him as well as pulling him in with her legs. “Pull almost out, then shove it in.”

He did. “Uh. Uh.” He began moaning with each thrust as he tried driving his entire length at once. He was working hard.

“Lift my ass up,” she said. He put his hands under her and elevated her ass, her hips, causing his cock to reach even further into her. Her pussy was on fire.

“Harder!” Gail ordered. “FASTER!”

She was being impaled with his cock, even deeper than before, He was pounding her into the mattress. Her head was thrashing back and forth with the sensations that were unlike anything she had felt. Paul was finally fucking her like an animal, ramming as hard and as fast as he could. His dick was reaching unknown areas, it was stretching her even wider, nearly ripping her open, yet she couldn’t get enough. She felt his cock throb, getting even thicker as it seemed to fill the entire inside of her body.

“OH MY GOD!” Gail screamed. “”FUCK. ME. HARD. OH. DAMN. SHIT.” She said one swear word with each of Paul’s thrusts as she went crazy. Her insides exploded, her orgasm roared through her. The intensity was overwhelming, every nerve ending of her being was on fire.

Gail’s pussy contracted tightly around Paul’s cock. So tight that he began having trouble moving it in and out. Her contractions, however, were too much for him and he erupted with his own orgasm. She could feel him spurting his cum deep into her center. He held himself deep inside her, nailing her to the mattress with his dick as he shot his semen out several times. By then he pulled out and pushed in as he emptied himself into her. When he was done, his dick softened enough to slide of her easily, and he flopped onto the bed next to her.

They were both spent. They lay side by side panting, unable to breathe normally. Sweat coated their bodies, and Gail’s crotch, especially, was coated with cum. She didn’t care. They had both worn themselves out and were in a state of bliss.

“Wow!” said Paul. “Is it always like that?”

“No, it’s not,” answered Gail. “That was definitely unusual. But I guarantee if you fuck like that you will satisfy any girl. Any woman.” she corrected.

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