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Introduction:

He was a 21 year old virgin who needed help.
“Watch out!”

Diane ducked as a basketball bounced next to her on the sidewalk and flew over her head. Two young men came running towards her.

“Jesus, guys! What are you trying to do? Give an old lady a heart attack?” she asked, laughing.

“Old, my ass, mom” said her son Chris, as he bent to give her a kiss on the top of her head. This tall, slender, gorgeous, late-in-life baby could not have looked any more different from his best friend, Henry.

Henry scooped up the ball, grinning at his ‘second mom’. “Sorry, Ms. V – it got away from me”, and he planted a kiss on her cheek.

Her boys – best friends literally from the day they were born. Diane and Carol, Henry’s mom, met in the maternity hospital, where they shared a room. Their sons were born on the same day, almost at the same time. Diane was alone; Chris’s dad was not able to cope with having a baby at age thirty-five. Carol and her husband, Paul, were first-time parents. They became like family, and the boys were inseparable. Paul filled the gap for Chris’ absentee father. Diane stepped in when Carol was killed in a car accident ten years ago.

Whereas Chris was the good-looking athlete and popular, Henry was not. He was not as tall and was always a big boy, but had the personality of a star, and was one of the smartest kids in their class. Henry supported Chris in all his sports. Chris defended Henry against every bully that went after him.

Diane thought back to their Senior Prom. Chris’s date was the most popular girl in school, and they could have gone to the prom with the other popular kids, but Chris insisted that they go with his best friend. Little did he know that Henry had his own plans. He invited five girls, who otherwise would not have gone, to go to the prom with him. Diane and Paul hosted a dinner at her home, so that the boys could afford a limo. Her favorite picture was of the boys in their tuxes, one on each side of her, kissing her cheeks as she wore a corsage they bought for her.

“Mom? Henry’s eating here tonight”, Chris called from the driveway.

“So why would tonight be any different?” she called back. Diane had a sad smile on her face as she walked toward the house.

Paul and Diane knew that on any given weekend, if either boy’s bed was empty he would be at his best friend’s house. Now, the boys were home from college for the last summer before their senior year. Diane knew it was probably the last time they would all be together, and she wanted the summer to be perfect. She and Paul had planned joint outings, special dinners, and got tickets to summer concerts and baseball games. There was also a huge 21st birthday party for them. It had been idyllic, but it was fast coming to an end.

After dinner, Henry helped clear the table as Diane loaded the dishwasher. Chris came into the kitchen after answering the telephone.

“Hey, Ashley just called and invited me to the lake this weekend. That’s okay, right, mom?”

“You don’t have to ask me, sweetie, but thank you for the consideration.” Diane glanced at Henry, and saw a look of pain flash across his face.

Chris slapped him on the back. “Sorry man. The woman always comes first, you know. Besides, you’ll have the whole room to yourself.” He chuckled and went upstairs to pack.

“Well, I guess I’ll go then,” Henry said, setting down the last of the dishes.

“You know you don’t have to. Your dad won’t be back until Sunday, so you’re more than welcome to stay here.” Diane reached up and ran her hand through his short buzzed hair.

Henry looked down, a little embarrassed and shuffled his feet. “Thanks, Ms. V. but… ”

“No buts. You’d be doing me a favor by keeping me company. Besides, I think you still owe me a chance to win back the money I lost to you in gin.”

“Thanks, Ms. V. I’ll go help Chris pack.” Henry turned and left the kitchen.

Her sweet boy; Diane knew how hard it was for Henry to watch Chris go off and have fun. Her heart ached, wondering what the next year would bring. Chris would be off to pursue a career in television broadcasting; Henry would take his degree in forensic chemistry and end up at Quantico. But she had a feeling these two would always be as close as brothers.

It was supposed to be another warm night. Diane walked into the kitchen to get some ice water, when she heard the bounce…bounce…bounce of a basketball. She went outside to find Henry standing in the middle of the driveway, just bouncing the ball.

“Henry? Why don’t you come inside, sweetness? It’s hot. I’ll get you something cold to drink and maybe we can play some cards.’

“No” said Henry as he turned away.

Diane walked over to him, placing her hand on his back. “What’s wrong, baby?” she asked softly.

“Nothing”, he said sharply.

“Henry, you’ve always been able to talk to me. Come on, what’s wrong?”

“Not about this I can’t.”

“Of course you can. Henry, we’ve always been able to talk about anything.”

Henry threw the ball at the garage – hard. His face was red with anger as he turned to Diane and said, “You wanna know? Do ya? I’m fucking twenty-one years old and I’m still a fucking virgin!”

With that the young man dropped his head and turned away from her, walking towards the backyard.

Diane didn’t quite know what to do. She went after him, and found him sitting on the picnic bench. She put her arm around his shoulders.

“It’s going to happen, sweetness – and it’s going to be beautiful. Someday the right woman will come along and you will make her so very happy.”

“That’s bullshit and you know it. And wait for how long? Till I’m fifty and can afford a hooker?”

Diane pulled him closer; his head rested on her breast. She bent her head to rest it on the top of his. His arms went around her; his one hand coming to rest along side her breast.

“I just can’t do this any more. I can’t pretend to be happy for Chris. I can’t pretend to be everyone’s buddy. I can’t go back to college still being a loser.”

Diane put her hand under Henry’s chin. She tipped his head up so she could look in his eyes.

“Henry, you are a wonderful young man and…” Diane had nothing to add. She watched as his eyes got glassy. As she lowered her head to kiss his cheek, Henry turned and her lips met his.

She was so taken aback by this – she couldn’t move for a moment. The kiss was tender and sweet, but so, so wrong.

“Oh god Henry, I am so sorry” she said as she started to back away. Henry’s arms did not loosen.

“Why? Because I’m a loser? Because you’re ashamed of me?”

“No! No, Henry. It’s not that, baby. I love you, but …” His lips cut her off in mid-sentence.

He realized the person in his arms was a warm, living, breathing female. Henry pulled Diane onto his lap and firmly kissed her. His hand was no longer on the side of her breast, but was now cupping it – massaging it.

Despite the protestations running through her head, Diane found herself being drawn into this slow, sensuous kiss. Her nipples responded to his touch by becoming hard, and there was that familiar tingling sensation as her panties started to become moist.

‘Wrong, wrong, this is so wrong’ was all she could think as she half-heartedly tried to push away from him. Henry’s arm stayed tightly around her, the hand cupping her breast went to the back of her head – holding her lips against his. There was the unmistakable feeling of male hardness pushing into her ass. And his kiss – his wonderful kiss, seemed to go on forever.

When at last he pulled away, Henry looked at her intently. There was passion in his eyes when he finally spoke. “Ms. V? Diane? Please, please help me. I’ve never kissed a girl before. I’ve never touched a breast. Please?”

His eyes begged her. His bottom lip trembled a little as he started to move his hand back to her breast. Diane looked at her boy; her young man. She had so much love for him; she would give up her life for him. Right now, she was filled with the need to make his pain go away.

“But sweetness, do you understand I want your first time to be special? It should be with someone you love, not with an older woman.”

“But I love you. Don’t you see? This would be special; perfect to me.”

She was torn. Her mind told her to turn away now. Her heart told her that he needed this. Her body told her that she needed this. Diane bent her head and kissed his sweet lips once more. Henry held her close, one of his hands dropping down to her ass, squeezing it.

She ended the kiss, looking at him. Against her better judgment she said, “Then come on, sweetness. Let’s go up to bed. It’s time.”

Diane took Henry’s hand, leading him into the house. Henry watched her ass, as they climbed the stairs. When they reached the top, he pulled her to him for a passionate kiss.

“I need a shower” he said, burying his face in her hair.

“You use Chris’ bathroom. I’ll use mine. I’ll meet you in my room, whenever you’re ready.” She rose up on her toes and kissed him. “No pressures, Henry. Don’t worry about anything. We’ll just explore and see what feels good. Okay?”

His voice cracked as he said okay and he almost walked into the wall as he turned. ‘Oh god,’ he thought. ‘I’m really gonna fuck! Oh god.’

Diane spent a little extra time getting ready. She made sure her arms, legs and pussy were shaved. She perfumed behind her ears, between her 42C breasts, the small of her back and behind her knees. She slipped a short blue nightgown over her head and brushed her blonde hair until it shone.

As she came into her bedroom, she saw Henry sitting on the edge of the bed. He was still damp from his shower and he wore only a towel. His body was pale and round.

He stood as she approached him and exhaled, “Whoa….” as he looked at this curvaceous woman. Her nightgown hugged her body. Diane glanced down and noticed his towel was tented.

She walked right over to him and took him in her arms. She pressed against him as they kissed, and his cock stabbed into her belly. He started moving his hands fast, all over her body. Diane stepped back, out of his reach.

“Hey, sweetness, slow down. We’ve got all night.” She turned and walked to the side of the bed, stopping to turn off the lamp on her bedside table. She folded back the bed covers and crawled into the middle. She patted the spot next to her. “Come here”, she told him.

As he walked to the side of the bed, his towel fell away, exposing his very hard six-inch cock.

“I’m not very big”, he said shyly.

“Oh, Henry, it’s perfect.”

Diane put her hand out to touch him and his cock jumped. She thought for sure he would cum at that moment. She crawled over and sat on the edge of the bed.

Resting her hands on his hips she quietly said, “It’s beautiful, Henry. Now I want you to relax while I take care of things. Trust me. It’s for both our benefit.”

With that, she gently took hold of Henry’s cock and lowered her head to wrap her lips around him.

“Fuck!” Henry almost screamed out when he felt her take him in her mouth. His knees felt weak and he thought he might pass out. ‘Holy shit’, he thought. His hand had never felt like that.

Diane went straight to work sucking him. She knew she had to get the first one out of the way, so that he could relax and enjoy himself.

Diane bobbed and sucked for just a few minutes before she felt him grab her head, forcing himself to the back of her throat. She almost gagged as he released a powerful stream of cum.

“Jesussss…” he moaned as he moved his hips, pumping his cock in and out of her face.

Diane waited for his spurts to end, and reached up to remove his hands from her head. Henry was visibly shaken and looked even paler than he had seemed. She took a moment to clean him, as he stood swaying and moaning.

When she was finished she looked up and smiled. She stood up and kissed his lips, so he could taste himself on her.

“That better, sweetness?”

“Uh Huh.”

“Now come to bed Henry. It’s time to play.”

With that she got back into bed and made room for him to join her. He got in and lay flat on his back, staring at the ceiling with a far-off look in his eye. He looked scared. Diane sat next to him and began to talk.

“Henry, let me tell you what happened. You were very nervous and if I hadn’t done that you would have exploded before you were ready. Next time, you’ll last longer. Okay?

“Uh Huh.”

“Now there’s just one thing you need to learn about a blowjob. Try not to hold the woman’s head to you. A lot of women will gag and get scared if they think they can’t get away. You can lay your hands on them, play with their hair, but don’t hold them there. Let them take care of you and it’ll be much more enjoyable. I promise.”

Henry turned on his side and looked at her mortified. “Did I hurt you?” he asked in a panicked voice.

She stroked his cheek gently. “No baby, no. I’m fine. You just need to learn how to hold a woman, Henry.”

With that, Diane scooted down in the bed and lay back on her pillows. Her nightgown slid up her creamy thighs to just below her pussy. She lay half on her back and half on her side.

Henry looked at the woman who was such a huge part of his life. He saw her big, beautiful breasts slip out the V of her nightgown.

Diane noticed his stare. “Do you want to touch them?” she asked.

“Uh Huh.”

“Just remember; always start gently, just like you did outside.”

Henry carefully laid his shaking hand on her breast and began to massage it. Diane smiled at the feel of his touch.

“Do you want to see them?” she asked. “Its okay, Henry.”

Henry just nodded. He carefully slid the blue strap off her shoulders. The gown fell away from her body exposing her soft white breasts. He ran his hand over her flesh and then took his finger and traced around her nipple, watching as it began to harden.

“They feel like velvet”, he whispered.

“Mmmm. That’s nice, Henry”

Henry continued his exploration, lifting them, feeling their weight, massaging them and gently squeezing them.

“Diane? Can I…”

“Sweetness, you can do whatever you like. Remember, start gentle. Your lady will let you know what she likes.”

Henry leaned over her, lifted her breast and covered her nipple with his lips, kissing it. He tentatively licked all around the aureole before flicking the nipple with his tongue. He watched in awe as her nipple became even harder.

“Ohhh. Go ahead, Henry – its okay.”

With that, Henry took her breast in his hand, placed his mouth over it, and began to suck. He was gentle and sweet. His hand started squeezing her in a milking motion, the longer he sucked. He switched to her other breast and devoted just as much care and attention to it.

It was wonderful and sweet, but Diane needed more.

“Harder, Henry – suck harder.”

He was timid, a little afraid of hurting her, but Diane’s hand went to his head and held it firmly.

“Suck harder, Henry. Come on, baby, I need it.”

Inhibitions pushed aside, Henry latched onto her breast as if he were expecting to be fed. A rush ran though Diane’s body and she moaned. Her hips began moving and her gown slipped higher.

She took Henry’s hand and slid it down her body – over her ribs, past her belly, down, down to her bare, smooth pussy. She moved his hand up and down, showing him how to touch her.

Henry stopped his suckling to watch her guide his hand. He followed her lead – moving it, caressing her skin. He ran his hand up and down her inner thighs. Diane opened her legs for him.

Her breathing got faster each time his fingers passed over her slit, but did not enter her. If he was trying to drive her nuts, he was succeeding.

“Oh, for god’s sake, Henry – put it in me!”

His hand stopped and he looked at her.

“Oh, my god. I’m so sorry.” Diane came to the realization. “Baby, haven’t you watched porn? Come here sweetness, I’ll show you.”

Henry just nodded. As if demonstrating a human biology lesson, Diane half sat up and spread her legs wide, bent her knees and began to show herself to him. She patiently explained the human female body, opening her lips to show him her womanhood. Henry watched but stayed mute, as she showed him and explained her hard pearl-like clit. She ran her finger in circles around it, rubbing it, so he could see the changes that took place in her body and on her face.

He was in awe of her tender hole and of its growing moisture. She sensed his hardening cock, as she drove two fingers inside herself to show him how to find her G-spot. He could hear the squelching sounds of her fingers moving in and out, and began to breathe more quickly.

The more Diane played with herself, the more her scent filled the air. Henry bent closer, then closer. She knew what he wanted, because she wanted it too.

She removed her fingers and held them under his nose. He reached for her fingers and sucked them into his mouth, tasting her for the first time.

“Lick me Henry. You need to really taste a woman.”

There was no hesitation. Henry lay down on his stomach, opened her hole with his thumbs and extended his tongue for the first time. From her sensitive perineum to her clit, he made one pass, licking her slowly, savoring her taste.

“Oh yessss….”

He looked up. Diane was lying back on the pillows with her eyes half closed.

Henry was always a good student, and this time was no exception. Up and down he ran his tongue, enjoying the exploration of her most intimate place. He circled her clit slowly, every so often pressing it with his tongue, and giving it a little flick. Diane was moaning.

“Now Henry, put your finger in me now” she panted.

Concentrating his tongue on her sensitive clit, Henry pushed his middle finger inside her wetness. Diane felt the heat rising within her. She rocked her hips, fucking his finger, moaning. Her hands went to his head – urging him on. He turned his hand and slipped a second finger in. He searched for her ridged, spongy area that Diane had explained was her G-spot. He felt the change in texture inside her, and began to rub.

Sucking, rubbing, touching, Henry was relentless. Diane’s body started to tense as if hit by shock waves. Her back arched, she clawed the bed covers and screamed.

“Oh God, Henry! C…C…Cumming!”

He was treated to the warm juices that began to flow from her quivering pussy. He continued his rubbing.

“No…, no…, no… - Goddddd…” she panted.

He pulled his fingers from her and buried his tongue deep inside her now very wet hole, licking and sucking her. He would not stop, and her body writhed under him. He held her hips firmly, and continued to drink from her, until her struggles slowed and stopped.

Diane was trembling, finding it hard to come down from her high. He rose from between her legs to lie next to her. Diane looked at the young man staring at her.

“Henry? Are you sure you’ve never been with a woman? Because, baby, that was amazing. You knew exactly what to do.”

Henry blushed. “You said the lady would let me know what to do, and you did.”

Diane smiled at him. “I don’t know if I have any strength left, sweetness.”

Diane absolutely glowed. Henry couldn’t believe how beautiful she looked. She rolled over on her side facing him, and stroked his cheek.

“My beautiful boy” was all she said, before she leaned over to kiss him.

She did not kiss him like a mother kisses a son, but rather as a woman kisses a man. She pressed her body against his and slid her hand down in search of him. She was greeted by his hardness. She ran her hand lightly up his shaft and he moaned in her mouth as they continued kissing.

In one fluid motion, Diane lifted her leg and put it over Henry’s hip, so that his cock was touching her warmth. As they kissed, she rocked her hips against him, pulling another moan from his mouth. His kisses became more demanding, and his hand reached to cup her ass and draw her closer to him. His movements were instinctive as he prodded her with his cock.

He looked confused as Diane pulled away from him and lay on her back. She spread her legs and gestured to him to come to her.

With a look of passion in his eyes, Henry got up on his knees between her legs. He had his cock in his hand, poised above her mound. Diane reached up and guided him to her wet entrance.

No words were needed. The feel of her heat and wetness against the tip of his cock drew him in. Slowly, he eased forward. Inch by inch; he relished the feeling of his cock being buried deep inside her.

He became aware of not being able to push in any further. Henry looked down at Diane and bent to kiss her. As their lips met, her legs wrapped around his waist, and pure animal instinct took over.

Henry began to rock his hips, and his cock started to glide in and out, just a little. The longer he moved, the more he withdrew and thrust back inside her. This was unlike anything he had ever felt. The divine feeling of her hot, wet glove on his cock began to overtake him completely.

He braced his arms at her shoulders and began driving in and out, harder and faster. Diane met him thrust for thrust, with the same urgency. Her nails dug into him and she tried to pull him in deeper. Sweat formed on his brow and dripped down on her. Henry’s face contorted as he sought the pleasure he had dreamed of for so long.

In the silence of the night, you could only hear Henry’s grunts, skin slapping against skin, and an occasional squealing sigh from Diane.

Going down on Henry prior to this act proved to be a wise move on Diane’s part. He was all machine – movement and endurance. In and out, harder, faster, pushing himself until…until…

Henry’s arms stiffened and his hips pushed forward so hard, Diane was moved against her headboard. He threw his head back and let forth a yell.

“FUCKKKKKK…”

Diane felt his cock explode and his cum shoot all the way up into her wet hole, setting off another orgasm of her own. He kept pushing and pushing into her while he continued to spurt. Her hands gripped him harder as she tensed and moaned in pleasure.

“Ugh…ugh…ugh…” he cried, as he felt her muscles contract and milk him dry.

When at last there was no more, Henry collapsed exhausted on top of her, his head buried in her pillow as his breathing began to slow to normal.

His body involuntarily shivered. Diane lay underneath him, running her hands up and down his back. When he finally raised his head, his hips moved and his cock slipped out.

Henry carefully got off Diane and lay down next to her. She was still panting as he drew her into his arms. At the same time, they sought each other’s lips.

Gone was the boy, gone was the virgin. In her arms lay a man. They held each other, kissing, whispering, for a long while – basking in the afterglow of love-making.

“Diane?”

“Yes, sweetness?”

“Thank you. My god, thank you. I never thought…I never knew it would feel this good.”

Diane kissed him tenderly and said, “It was my pleasure, Henry. Truly, it was.”

“Um, I know that this won’t happen again,” Henry sighed.

Diane cupped his face in her hands and looked him straight in the eye.

“Shhhh, sweetness, don’t think about it. We still have the rest of the night.”
17 comments

TrollReport

2010-06-10 12:34:18
Me too, I want to learn how to write this pitiful smut too. Geez, wake up and go and get a book and find out what it's like to read something that makes sense, except for "o,o o, I'm cumming, oh, my that feels so wonderful." Sound familiar, yep it should, all her dumb assed stories sound the same. She logs in by other names to make them sound like they are praised, wow, an elaborate scenario, but she's now a legend AND she don't even let them comment anymore, too much trouble and they'll catch on soon if she did

Exakta66Report

2010-04-05 22:15:14
Very nicely done, ejls...I feel like I just got back from school...if you ever decide to teach night classes and are looking for students, let me know...maybe I can take a refresher course...lol.. I liked the way you alternated the action with Diane's own reservations about what she was doing...again, very well done...

mrdoitagenReport

2010-04-03 13:32:53
Very good, I like hot sex, please keep writing

Anonymous readerReport

2010-03-26 19:11:44
Maybe Obama could such my dick while ejls drinks from his fountain

lonesumboyReport

2009-08-04 17:45:30
Wow I love your story, I wish my aunt was opend minded like his mother to teach me the art of love and how too satisfide a girl or woman, I thank you for this story to open my eyes,in how to satisfide a girl now and pleasure her

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