His friends at school constantly belittled Darren once they learned that he was still a virgin. Even though he was seventeen, almost eighteen, and the ratio of girls to boys at his high school was five to three, he had never managed to have a girlfriend. At least, one who would have sex with him. He was so shy that his opportunities slipped away.

He worked off his frustration by working out with weights at home in the basement and running every day, even after school. One Saturday morning, he came in from his daily run and was about to go shower when his mother approached him.

“Darren,” she said, “my friend, Emily Grayson, is in a jam; her babysitter and backup babysitter, both just cancelled on her today and she needs someone to watch her son, Bobby, while she attends a garden club meeting. She’s divorced and her ex is supposed to pick up Bobby for the weekend about four o’clock. Would you help her out and watch him until his Dad gets there?”

Darren had met Mrs. Grayson only once when she was visiting, having tea with his mother. She was about forty, and a fairly attractive women, considering she had a ten year old son. He knew a couple hours with Bobby would be no problem, so he told his mother that he would help, and went upstairs to take a shower.

Later, when he rode his bike over to Mrs. Grayson’s house, he found Bobby sitting on the front porch, waving goodbye to Mrs. Grayson, who was getting into her car. As Darren came into the yard toward the porch, he caught a glimpse of Mrs. Grayson’s legs as she flashed them getting into her car. She noticed him and yelled out the car window, “Hi, Darren! Thanks for helping me out today. I won’t be long, so wait for me and I’ll pay you when I get back.”

Darren just nodded and watched her drive away. He and Bobby went inside and decided to watch a movie. The movie was almost over when Bobby’s Dad drove into the driveway and beeped his car horn. Bobby jumped up and went out to the car and his Dad drove away. As the movie ended, Darren heard Mrs. Grayson’s car come into the driveway.

A couple of minutes later, when she came inside, Darren stood up and smiled at her. She looked at him, her eyes scanning up and down his tight young body and then she smiled back. “Darren, I’m a mess from the work we did at our meeting,” she said apologetically. “Would you mind waiting while I take a quick shower? It will only be a few minutes.”

“Sure, Mrs. Grayson,” he said politely, “I’m in no rush.”

“Wonderful!” she said. “Sit right there and I’ll be back in no time, and please, call me Emily.”

Darren turned off the television and just wandered around the downstairs of the house for a few minutes, and then he heard her coming down the stairs. Her short dark brown hair was wet, she was barefoot and clutching a fuzzy pink robe around her body. She went directly to the sofa in her living room and sat down and patted the cushion next to her.

“Come; sit down and let’s talk a while,” she said warmly. “I haven’t seen you in a long time and you’ve really grown up.”

She asked him how he liked school and his teachers, and wondered about his hobbies, and they talked several minutes. Darren was comfortable but suddenly surprised when she asked him, “Do you have a girlfriend, Darren?”

“No, ma’am,” he confessed easily. “I’m really shy and there’s nobody I’m interested in right now.”

“I’ll bet you’re still a virgin, aren’t you, Darren?” she asked boldly.

The question caught him totally off guard but he managed to answer softly, “Yes, ma’am.”

“Oh, don’t be embarrassed about it,” Emily said warmly, “I think it’s sweet. But you’ve fooled around with girls a little, haven’t you?”

“No, ma’am, not actually,” he said sheepishly.

She sat quietly staring at him for almost a minute and then shocked him by asking, “Darren, would you like to see my tits?”

He swallowed hard and a hand slid up his pant leg slowly. “I guess so,” he answered.

“You can see my tits and touch and feel them if you think you might want to,” she said, licking her bottom lip teasingly.

Darren felt his cock pants begin to tighten and he put his hand on his growing cock. He quickly assessed how safe and easy it would be so see and touch a naked woman and he said with a little more confidence, “Yes, ma’am, I think I might like that.”

She sat up straight and eased her arms out of the robe and let it fall off her shoulders, into her lap. Darren was treated to the sight of his first real tits, right in front of him. Emily arched her back and her breasts jutted proudly for his inspection.

“Don’t be shy, Darren,” she said encouragingly, “I know what boys like to do with tits; go ahead, I want you to do whatever excites you. If you want me to, here, I’ll close my eyes.”

Her hands were in her lap, holding the soft robe as she closed her eyes. Poor Darren was beside himself. He had heard his friends talk about feeling their girlfriends’ tits and sucking on them, and he wanted to be able to tell them that he had done it too. So he gently filled his hands with her breasts and their softness took his breath away.

He leaned forward and kissed the skin on one breast and then opened his mouth and tried to fill it with her breast. He accidentally licked across the nipple and she moaned softly. Darren flicked his tongue across the nipple and then suckled her with wet smacking noises. He began to enjoy the feel of her flesh and he moved to the other breast, repeating his sucking. She slipped a hand behind his head and pressed him against her breast and he nearly came in his pants.

He moaned and she realized that he was too excited, and she didn’t want him to come yet. She eased her breast out of his mouth and leaned back in the sofa. Darren was almost panting, one hand clutching his hard cock still restrained by his pants. She moved up to the edge of the cushion. “Stand up here, in front of me,” she instructed carefully.

Darren stood but showed her his bulge in his pants.

She was as gentle as she could be, encouraging him to relax and let her take care of things. “I know, Darren, what your problem is right now,” she said. “I’m going to help you relax so you can enjoy things better.”

So he stood in front of her, his hands by his side, and watched excitedly as she unbuckled his belt, unzipped his pants and pushed his pants and boxers down to his knees. He stepped out of them without being told. Darren’s cock was fully erect, the tip crimson with the need to come.

Emily leaned forward, slipped one hand under his balls to hold them, and she slid her mouth quickly over the end of his cock. She set her eyes on his, which darted back and forth between her eyes and her mouth on his cock. She moved her mouth up and down on his shaft slowly and within thirty seconds he came, sending ropes of his cum into her experienced mouth. Still staring into his eyes, she swallowed his load.

His cock was still hard and he was panting like a race horse. His hands were fisted and he groaned, “Oh, fuck!” He didn’t know what to do next but she let his cock spring free of her wet mouth and she leaned back on the arm of the sofa. Darren flopped down on the sofa, staring at her erect nipples.

She gave him a couple minutes to calm down and then asked him in a seductive voice, “Have you ever seen a real pussy, Darren?”

Before he could answer, she swept the robe away from her body and spread her legs wide. Darren’s eyes opened wide as he stared at the dark hairy patch between Emily’s legs. “Wow,” he said with a whisper.

Emily shifted her weight, sliding down on her back and getting her legs close to him. Her head rested on the arm of the sofa and she encouraged him to proceed.

“Darren, I also know that boys like to eat a girl’s pussy before they fuck, so I’ll just lie here and close my eyes while you do whatever you want, and in a little while I’ll let you fuck me.”

She closed her eyes and squeezed her breasts with her hands, waiting to see what Darren would do. Poor Darren knew he was supposed to do something with his tongue, but he wasn’t sure just what. But he recognized this as a golden opportunity to experience pussy however he was supposed to.

He turned his body facing her and lay on the cushion between her legs. He moved his face in between her thighs and pressed his mouth into her slit. She moaned, primarily to encourage him. “Ah, yes, that’s it, just like that,” she whispered.

Her wet hairs tickled his nose as he pressed his mouth against her wet cunt, sticking his tongue in and out. She slipped both hands down behind his head and held his face tightly against her and he went crazy, fucking her with his tongue. He gasped for air, and suddenly realized that he liked the smell and taste and it was making his cock even harder.

He wanted to reach down to stroke his cock but his hands had slipped under her ass and he was holding her up against his mouth, voluntarily licking and sucking now for his own enjoyment and pleasure. Emily eased his mouth from her core up to her clit and gave him new instructions; “Lick me, right there Darren, and don’t stop.”

He soon realized what she wanted when he felt her swollen clit against his tongue. He flicked his tongue over it and sucked on it and her thighs cupped his face and her legs hooked over his shoulders. Darren was getting so excited he thought his cock might explode again, but he kept doing as he was told because Emily’s moans and jerking against his face excited him even more.

He didn’t even realize it when he had made her come, so she gently pushed his head to disengage his mouth from her sex. He sat on the sofa, his cock throbbing, his face glistening with her juices, and he waited for further instructions.

Emily sighed with contentment; her student had done well for his first time. She could have sent him home but she felt she owed him one more pleasure, which she would enjoy herself. “Lie back on the sofa,” she said, and he quickly complied. She got up and straddled his body on her knees and settled on his upper thighs.

She leaned forward, reached down between them and guided the tip of his cock into her slit. Darren’s eyes lit up and he whined like a baby, “Oh God, oh, God…” when he felt her pussy sliding down his shaft.

“Shhhh…” she said, leaning forward, putting her hands on his chest. “Try to relax and enjoy it for as long as you can.” He stared at her, mouth agape as his hands rested on her hips. Every time her body pressed down on the base of his cock he gasped and she knew he would not last long enough for her to come.

She leaned forward, her body almost lying on top of his until her face met his. Their lips were almost touching and she could smell her juices on his face. “I’m going to fuck you a little faster and I want you to come in my pussy,” she said with a husky voice. Then she said, louder, “Fill my cunt with your cum, Darren!”

She covered his mouth with her's and stabbed her tongue into his mouth, and he came instantly, instinctively bucking his hips up into her body, driving his cock deeper into her. The more he moaned, the tighter she formed the seal of her mouth over his, working her tongue in and out as he moaned.

She could feel the force of his warm cum splashing against the walls of her pussy. Although feeling this was one of her favorite pleasures, she wished that he would have lasted longer. She pressed her weight down on his body and let him pump his cock into her until she knew he was done. She lifted back up, sitting on his cock and watched his young face, no longer a virgin. He lay with his eyes closed, gasping for breath, and she could feel his cock still throbbing inside her. She knew she could fuck him again now and she would enjoy it, but she wanted to leave him wanting more.

When she finally released his cock, she went to the bathroom and brought back a wet cloth. She wiped his cock and balls clean as he lay there passively, staring at her beautiful mature face, waiting for and wanting more, ready to obey.

“When we get dressed, I’ll pay you for helping me today,” she said.

“Oh, you don’t have to pay me, it was no trouble,” he answered, “I’d come over and help you anytime you need me.”

She smiled knowingly.