The Virgin and the Cougar Ch. 01

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Max was 20 when he started dating 18-year-old Ashley. He was a virgin as was Ashley and they had agreed that they would keep it that way, at least for a few months. They fell in love quickly and talked about how many children they would have. She let him caress her breasts and, occasionally, rub her pussy through her panties. She returned the favor by rubbing his cock through his pants but that’s as far as it went. Max was OK with that and contented himself by jacking off frequently.

Ashley’s mother, Candace, was divorced and didn’t have to work outside of the home due to the very nice settlement from her ex-husband as well as child support for their daughter that would last until she turned 21 or graduated from college.

Candace was a terrific cook and invited Max to share their table whenever he wanted. She knew that he was living alone and ate at fast food places most of the time. She and her daughter both enjoyed having him visit and he enjoyed spending time with them as well. Candace was almost a surrogate mother to him. Since he had never known his birth mother he grew close to her and her daughter over time. Very close to Candace eventually!

Max missed his father who was a construction worker until he was killed in an accident. He had never had “The Talk” with his father. That was when Max was sixteen and an aunt took him in until he graduated from a strict private high school run by a religious organization. Now he had a job and lived on his own. Other than the occasional exploration of a date with his fingers, he had no sexual experience and little knowledge of how sex between a man and a woman worked.

One evening he stopped by Ashley’s house hoping to be invited to stay for supper. He got a surprise when Candace opened the door wearing a very thin white robe through which he could clearly see that she was wearing only white bra and panties!

“Uh, ummm, ” he stammered, struggling to keep his eyes on hers, “is Ashley home?”

“Not tonight, ” Candace answered, “she has an evening class and is staying with a girlfriend tonight. Come on in, I’ve got dinner in the oven and there’s more than enough for the both of us.” Her smile put him at ease, at least a little bit and he accepted her invitation. He assumed that she would excuse herself and put on something less revealing but she headed for the kitchen leaving him to close the door. She didn’t seem at all uncomfortable with him seeing her so scantily clad.

Max followed Candace to the kitchen where she handed him a bottle of wine and a corkscrew. While he opened the bottle and poured two glasses she finished the meal preparation. They sat on a couple of stools at the breakfast bar and made small talk while they ate. Max carefully avoided looking directly at her breasts that could be seen bulging at the top of her bra or her long smooth legs that occasionally touched his when she twisted toward him. The closeness to a lovely and barely dressed woman was having an effect on him. He had to adjust his growing cock when he thought she wasn’t looking his way.

Eventually Candace asked, “Are you uncomfortable with the way I’m dressed? I wasn’t expecting company tonight.”

“I’m so sorry!” Max exclaimed, “I should have called.”

“You know better than that, we’re practically family. You can stop by whenever you want, you’re always welcome” Candace told him as she glanced pointedly at his crotch, “It’s just that I can see you’re aroused.”

“I’m sorry, this is really embarrassing. It’s just that you are so beautiful!” Max exclaimed. “Oh God, I’m practically engaged to your daughter. You must think I’m perverted!”

Candace smiled and put her hand on his thigh as she told him, “Actually I’m flattered that a young man is as obviously affected as you are by me. It’s OK, don’t be embarrassed, you’re having a natural reaction. Do you want me to call Ashley and have her meet you somewhere to take care of that?”

“Oh no!” he quickly answered, “We don’t, you know, do that…at least not yet. We’re both virgins.”

It was Candace’s turn to be embarrassed, “I’m sorry Max. I assumed that you two were having sex. I’m not really surprised that Ashley is a virgin but I assumed that you had experience.”

“I shouldn’t be talking to her mom about this I guess,” Max shyly told her, “but she wants to save herself for marriage or at least a formal engagement. I just assumed that she wanted me to do the same.”

“Believe me, that would be a mistake,” she told him in a serious voice, “the first time you two have sex is going to be awkward and messy. That sort of thing can make your wedding night far less romantic and erotic than it should be.” She stood up and motioned Max toward the living room, “lets talk about it over there. I’ll clean up later.”

Max admired the movement of her ass under the almost sheer dressing gown as he followed her into the next room. She sat on the couch and patted the space beside her, “sit down and let me give you some advice.”

Max antalya escort sat down and Candace lightly rested a hand on his thigh as she told him, “My first marriage almost ended when my new husband took my virginity. The blood and my cry when the hymen was broken upset him. He wasn’t able to get an erection until the next morning. Then he had an orgasm so quickly that it was all over in a minute. He wasn’t able to satisfy me until a week after that. I’m not saying that it would be that way with you and my daughter but I strongly feel that the man should have experience before the wedding night.”

Max was embarrassed but strangely excited by her intimate story. His erection had wilted when she called attention to it but was beginning to grow again. Her hand on his thigh, alternately gently squeezing and softly rubbing it contributed to his excitement as well.

“You should find a willing and understanding young woman and have your initial sexual experience before you get married.” She continued, “I know my daughter better than anyone and she will expect you to take charge and make her first experience in bed with you a night to remember for the rest of her life.”

“I don’t know…she might feel betrayed if I’m not a virgin, we’ve talked about it.”

“Have you told her that you are a virgin?” Candace asked.

“Not in so many words, she just assumed that I am, I think. We’re so close that we don’t always have to communicate with words, you know?”

“I do know, my daughter and I are that close of course,” said Candace, “I know her better than anyone, as a woman and as her mother.”

“But I don’t know any other girls well enough to just ask them for sex! I can’t go to a hooker, I just can’t! What can I do?” Max asked her.

For almost a minute there was silence, then Candace looked into his eyes and slowly moved her hand from his thigh to the bulge in his pants and gave his cock a squeeze. Max closed his eyes and sucked in a quick breath. When he opened his eyes again Candace was smiling.

“You need an experienced woman to show you the ropes and I know one who is willing to do that for you…and for her daughter,” she softly told him as she gently rubbed his cock through the fabric.

“No, that wouldn’t be right!” Max exclaimed, but without much conviction.

“Who better than me?” she asked, “according to my second husband I’m damn good in bed and willing to help out a young man in need. From what I see and feel, you are definitely in need.”

With that she unzipped his pants and reached through the opening to get a better grip Max’s now fully erect cock. Max gasped and closed his eyes again. She stroked his cock while she un-buckled his belt. When she released it she moved from the couch to the floor in front of Max. He watched as she leaned forward and placed a kiss on the head of his penis and then wrapped her lips around the head.

Max groaned, feeling an eruption building deep inside of his balls. Candace pumped up and down with her hand while using her other hand to tickle his balls as she expertly gave him his first blowjob. It wasn’t long before the inexperienced young man exploded in her mouth. She swallowed his load, and then licked his cock clean and smiled up at him.

“Was that your first blowjob?” she asked.

“Yes, and I’m sorry I did it in your mouth,” Max answered, “It must taste awful.”

“Not really, kind of salty but I like it. See what I mean? If you finished that quickly the first time with Ashley it would have been over for you but she would have just gotten started.”

“I guess you’re right, but I should really get going.” Max said. “She might come home and catch us. I’d die if that happened!”

“Don’t worry about that, when she spends the night with one of her girlfriends they stay up until the early morning and then sleep half of the day away. Besides, I’ve only started showing you the ropes. You still have a lot to learn and I owe it to my daughter to have you ready for her,” Candace told him with a big grin on her face.

She got up from the floor in front of Max and motioned for him to follow her as she slowly walked toward her bedroom with a smile on her face. Max obediently followed like a little puppy. She had him under her thumb. As they made their way down the hall Candace nonchalantly shrugged out of her dressing gown leaving her dressed in only bra and panties. Max enjoyed the view as he walked behind her, holding his pants up with one hand.

Once in the bedroom, Candace directed Max to sit on the bed. She faced him, reached behind herself and unhooked her bra. Slowly she let it fall as Max watched. He thought he would die when he caught sight of her wonderfully full and firm C-cup breasts. He nearly did slip off of the bed when she slipped her panties down and he saw her nicely trimmed bush with two swollen lips below!

Candice flashed a knowing smile, enjoying Max’s reaction to her nudity. “We need to get you out of fethiye escort those clothes,” she purred. Max wasted no time stripping down to his birthday suit. In his hurry he lost his balance and almost fell over while pulling his briefs off.

“Oh my god, you are the most beautiful woman I’ve ever seen!” he croaked.

Candice suggested that he scoot on up the bed and lay on his back. Once he was in position she climbed up beside him, breasts swaying, and ran her fingertips over his body lightly. Her touch on his cock triggered twitching and increasingly heavy breathing for the inexperienced young man. She straddled him, staying elevated on hands and knees, and teased him by running her nipples up and down his upper torso.

“Have you ever seen a real pussy up close?” Candace asked her horny young man.

He softly replied, “Only in pictures.”

With that, she reversed herself over him, placing her pussy just above his face. “Well, ” she asked, “what do you think of that? You can play with it if you want to.”

Once he was able to speak, Max replied, “It’s beautiful” as he brought a hand up to touch it. He gently squeezed the outer lips together then spread them apart. He ran a finger lightly between the lips and she responded appropriately with a quick breath followed by a moan as his finger passed over her clit. Feeling embolden by her reaction, he slipped a finger into her vagina.

Knowing that his first time would be a short exercise, Candace reached between her legs and helped place his finger on her clitoris. “That’s my happy button, you can always make a woman happy if you play with it a little.”

Max took the hint and slowly stroked from top to bottom between her lips, occasionally slipping a finger into her. He made sure that he gave her “hot button” as he’d heard it referred to, special attention. He marveled at how soft and smooth she was down there and noted that the more he stroked, the more wet her crevice became.

For her part, Candace was getting extremely turned on. Knowing that her smoothly shaved pussy was on full display to a young man for his first time got her hot. Having him administer an intimate massage to it got her wet. She couldn’t keep herself from stroking and licking his balls and cock while he pleasured her.

“This is a bad idea,” she thought after a few minutes, “he’s going to cum before I ever get him inside me.”

With that thought she pulled away from him just long enough to turn around facing him. She lifted her right leg over his body and positioned her pussy over his young cock. “I’m going to take charge this time,” she said to Max, “but next time (she knew there would be next times even if he didn’t) you take charge. Ashley will expect that.”

With Max’s eyes scanning her bare torso, Candace spread her pussy lips with one hand and grabbed his cock with the other. She slowly lowered herself until the head of his cock was between her labia. Max could feel the warmth.

She looked into his eyes as she gently lowered herself until his cock was fully engulfed within her hot box. Max was in heaven as his cock slipped slowly into her and he felt her wonderful warmth engulf it. It was a sensation like nothing he had ever experienced. He closed his eyes and reveled in the feeling of being so intimate with a woman.

“Hey!” he heard her say, “you aren’t going to sleep are you? Because if you are I’m going have to assume that you’re gay!”

He quickly answered, “Oh no, I couldn’t fall asleep now even if I swallowed a bottle of sleeping pills! I never imagined how good it would feel…I’m in heaven I think, is this all real?” He said this with a grin, somehow keeping his sense of humor under the most erotic circumstance he had ever had in his life.

“OK,” Candace told him, “I was just checking. The best is yet to come…or is that cum? Whatever…hold on boy, I’m going for a ride and you’re who I’m riding!”

With that she raised herself up until just the head of his cock was buried in her pussy, then dropped down until she hit bottom. She began a rhythm that set her breasts in motion, mesmerizing her lover. He alternated between watching her animated breasts, her face and the wonderful thing that was happening to his heretofore-virgin penis. He loved seeing it disappear into Candace only to reappear glistening with her juices. He loved the sounds of their lovemaking. He wanted this moment to never end. Unfortunately he felt his orgasm building and couldn’t stop it.

“Oh god! I’m going to cum already! I’m sorry, I’m sorry!

“Go ahead and shoot your load Max, it’s OK. Cum for me, shoot it into my soft wet pussy! Fill me up with that big stiff cock of yours!” she exclaimed.

Candace’s dirty talk pulled him off the edge into a huge orgasm, more powerful than any he’d ever had jacking off or even with the blowjob she had given him earlier. Max felt like it would never end.

“That’s it Max! I can feel you filling kaş escort me with your hot cum! Give it to me baby! Keep it coming, don’t hold back, I want it all you stud!”

Max kept thrusting his hips up to meet her downward motions until he couldn’t manage it any longer. He felt totally drained, weak all over.

Candace pulled off of his wilting cock and lay down beside him on the bed. She kissed him sweetly. He regained his composure enough to return the kiss to which she added tongue action. Max ran a hand over her right breast stopping at the nipple for a pinch.

“Oh!” Candace exclaimed, “Where did you learn that?”

“I’m not totally inexperienced you know,” he smiled, “Ashley likes nipple play!”

“You naughty boy, you’ve been playing with my daughter’s boobs! You aren’t as innocent as I thought,” she said.

“Not any more at least…thanks to you!”

“So” she asked, “how was your first time?”

“Awesome!” Max answered quickly and enthusiastically, “I never dreamed that sex could be so good! Thank you!”

“You still have more to learn and it looks like your dick is about ready for the next lesson,” Candace said as she ran her fingertips lightly over his growing member. Max closed his eyes while his partner gently alternated between stroking his cock and running her fingertips over his nut sack. When she had him fully erect and twitching again she lay on her back and told him, “your turn to take charge Mr. Max.”

He wasted no time. Max helped her scoot to the middle of the king size bed where she spread her legs invitingly. He positioned himself on his knees between her thighs and admired the naked woman who was smiling up at him. She used her fingers to part her outer labia invitingly and he placed his cock between them at the opening of her vagina.

“Please fuck me,” she coyly said and he did! Max balanced on his knees and hands and quickly buried his young cock deeply in his girlfriend’s mother’s vagina.

Candace flinched and, as the teacher, told him, “You should take your time entering a woman, especially a virgin.”

“Sorry”, he replied, “I couldn’t help it. I hope it didn’t hurt.”

“No, didn’t hurt, but I’ve taken more man meat than she will have. Just remember to take your time with her. Now, give it to me like you mean it mister!”

Give it to her he did, slamming in and out like a mad man. Candace liked it hard and fast but didn’t want him to think that he could pound her virgin daughter like he was doing her. She encouraged him with moans and cries, grabbed his hips and pulled him into her pubis and bucked her hips up to meet his on the down-stroke.

Max lasted longer than he had the first time. He was enjoying the way he could pleasure a woman with his cock. He loved the way her breasts danced with their rhythm, the expression of ecstasy on her face and the way she wrapped her legs around him to pull him into her. It was a good ten minutes of furious fucking before he could hold back no longer and released another load of cum deep into her sweet vagina.

There was little warning before Candace sensed that Max was about to have his third orgasm of the evening. That’s the way she liked it, a man who could get it up and fill her up more than once a night. This young stud didn’t know it but he was giving her the best fucking that she’d had in years. She wanted to cum with him so she worked a hand to her crotch and fingered her clit furiously.

It worked. Max exploded in her less than a minute later. That triggered her orgasm as they came together. She flexed her muscles to grip his hard cock with her pussy, which resulted in her having a second orgasm as he shot his load of hot cum deep into her cunt.

“Oh god, I’m cumming, aaaaah!” Max shouted as Candace joined him with wail and furious bucking. Eventually they both ran out of steam and Max settled down on top of her, breathing heavily, totally spent.

Max eventually opened his eyes to see a contented look on at her face. A feeling of satisfaction swelled in his heart as he realized that he was responsible for her intense pleasure. “Thank you, thank you for teaching me how to make love to a woman,” he whispered, “I will always remember this lesson.”

“So will I sweet boy,” she replied softly. “Remember to take your time and make her pleasure your top priority. If you do it right she will thank you in many ways.”

“I’ll remember that and I’ll always remember my first sex with a woman,” he told her. About then they both felt his softening cock slip out of her dripping pussy. He rolled over on his back beside her and nearly fell asleep but she said, “You’d better clean up and go now. We wouldn’t want to fall asleep had have Ashley find us in bed together in the morning.”

Reluctantly Max climbed off of the bed and used the bathroom to pee and clean himself up. He returned to the bedroom and found Candace still naked, on her back, on the bed. As he dressed she said, “Your next lesson will be oral sex 101.”

“I can hardly wait,” he truthfully told her as he left her bedroom and she slipped into blissful sleep. That night, after he returned to his apartment, Max dreamed of having his head between his first lover’s legs with his face buried in her crotch.

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