Gail's Adventure


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."

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