Ryan's Summer Pt. 02

She began to pull him over until he was on top of her again, forcing his penis to press to the bottom of her hole. Then her legs flew up and wrapped around his waist.

Ryan took a ragged breath and began to slowly pull out. With the head at the entrance, he paused for a second, hips suspended in air, weight on his hands. He looked down at the beautiful woman. He held the position, staring into her lust-contorted face. Seconds ticked by.

"Fuck me... fuck me," she screamed.

With a smile and an animal like growl he pushed back inside, slipping all the way into her until his balls slapped the cheeks of her ass.

"Oh God! Oh God! Oh Godddddd!" she moaned incoherently.

A moan escaped Ryan's lips as her warm hole pulsed around him. He paused for a second, catching his breath. Then he pulled out and lifted up on his arms and looked down at Mary's face again. She was staring back at him. Her blue eyes were deep pools of lust and he almost felt as though he could fall into them. He locked his eyes on hers and began to thrust into her, his hips moving up and down forcing his penis all the way into her before pulling almost all the way out. He began a steady rhythm. The room quickly filled with the sloppy sucking sound of mating sex organs.

Mary pulled Ryan down until his chest was pressed to her breasts. She held on with her thighs locked around his waist and her arms around his neck. A second later, she began to climax again. Now each thrust seemed to bring on another climax until she was lost in one long orgasm.

Within seconds Ryan felt his balls begin to tighten. The friction of Mary's tight hole was taking him rapidly over the top. He pushed as deeply as he could go and froze, sucking in his breath. Then a long moan escaped his lips as his sperm began to squirt into her. His mind went blank as the pleasure of his first ever climax inside a woman rushed through him. His sperm blasted against her walls and splattered back to coat the pulsing head as the thick cream filled her hole. After the first several squirts, Ryan began to move again, letting the clenching of her warm hole milk him like a velvet vacuum.

Finally when Ryan's balls were empty he pushed deeply inside and relaxed onto her body, her heaving chest matching his heavy breathing. Gently he kissed her lips, letting his penis rest inside her saturated hole. A minute or two later he raised up on his arms again.

Mary sighed as if she thought it was over and she waited for him to pull out.

However, Ryan had other ideas. With a smile he began to move his still hard penis in and out again.

The older woman's eyes opened in amazement when she realized that he was still hard. "Ryan," she gasped.

He didn't answer. Instead he began a slow and steady thrusting of his hips.

"You're going to kill me," she hissed. Yet her arms and legs squeezed him tight and she began to show signs of excitement again.

He began to move faster.

Within seconds, the cabana was filled again with their moans of pleasure and the sucking sound of their slapping groins. This time the coupling lasted a long, long time. Mary lost track of the number of climaxes as her body writhed on the lounge chair. Her hair was now matted to her head with sweat and her body was dripping. She welcomed Ryan's sweat as it merged with hers.

Eventually Ryan reached his peak for the second time and he thrust deeply into her and emptied his balls again, filling her hole to overflow. He collapsed onto the still trembling woman as his hard penis finally began to grow soft.

It was some time before either of them moved.

Ryan moved his hips back, his penis slipping from her with a sucking sound, followed by his thick white cum. He moved back and sat heavily on a lounge chair, allowing Mary's legs to slip down and her thighs to rest on his. His eyes stared down at the exhausted woman. Her eyes were still closed and her chest was still heaving. He could see the redness on her cheeks and neck where his whiskers had rubbed her. When his eyes drifted down to her groin, he almost gasped; her still swollen and ravaged sex lips were spread wide and his sperm was running out like a river.

Finally Mary opened her eyes. She stared up at Ryan with a look of admiration. However, it was tinged with regret. She had never planned on letting it go this far. She chastised herself for losing control as she slowly stood up and put her robe back on wordlessly. Then she sighed and a little smile showed at the corner of her mouth. She bent over and gently kissed him. "You're corrupting me," she said with a self-conscious smile. Then she quietly turned and before he could answer, pushed through the canvas curtains and was gone.

The rain had finally stopped and the sun was shinning as she walked carefully toward the house. Ryan's copious sperm was running from her now sore and saturated vagina. She chastised herself again for losing control. She knew that what she had just allowed to happen was crazy and dangerous. Yet, it had been years since she had been so thoroughly ravished. Her husband Lloyd was a good man but he had long since passed his prime. On the rare occasion when they had sex, she couldn't tell if he had even cum inside her. However, with Ryan, there was no doubt about it. The evidence was running down her thighs, all the way to her knees.

There was a wide smile on Ryan's face also as he finished his pool work and left for his next appointment. He felt like he was walking on clouds. He suddenly realized what it felt like to be a man: not cocky or arrogant but confident, with more than a little pride. An hour and a half with Mrs. Wellsworth had done more for him than all the psychoanalyzing in the world.

Chapter 7

Ryan was humming to himself as he rang the doorbell at the Billings house the following day. The weather had turned unseasonably cool but he hardly noticed. His every thought was consumed by what had happened yesterday. Images of Mrs. Wellsworth were constantly in his head. He could feel her soft skin against him and smell her sweet perfume. The only time he thought of anything else was when he thought of Mrs. Billings. She was different but nonetheless sexy and he was eagerly anticipating their meeting today. He felt that he was no longer quite the shy and inexperienced boy. In a few short minutes yesterday he had become a man. However, he was pretty sure that his innocence was what turned Mrs. Billings on. If that was the case, he was more than willing to continue to play that role.

The door opened and Ms. Baker stood silently for several seconds, staring at the daydreaming boy.

"Oh, I'm sorry," Ryan said when he saw her staring at him. It almost felt like she could tell what he had been thinking.

She was wearing a pair of tight white slacks with a low cut short-sleeved sweater. Both garments hugged her body like a second skin. Under the top, he could see that she wasn't wearing a bra.

"Come on in, Mrs. Billings has a patient with her but she should be done in a few minutes."

Ryan followed the sexy woman into the house, his eyes on her ample backside as it swayed in front of him. He had thought that she had a great ass but now he was sure. The slacks were so tight that the seam ran between her buttocks, separating and emphasizing each cheek. He felt his penis begin to twitch.

"I was just about to have lunch. Are you hungry?" she said without turning around

"No ma'am, I had a late breakfast. But I'll still join you if you don't mind?" His eyes still on her buttocks.

"Please do," she said, smiling over her shoulder at him.

Ryan could tell that she saw where he was looking. He stared back, flashing his handsome smile.

Ms. Baker had the makings of a salad laid out on the counter.

Ryan picked up a carrot and started to eat it as he leaned against the counter and watched her began to make her lunch. "So, Ms. Baker, is there a Mr. Baker... I mean, I don't see a ring? And... you're so pretty and all." Ryan felt himself blush again. He hated that.

Ms. Baker looked up thoughtfully, almost sadly. "There was a Mr. Baker years ago but we've been divorced for a long time. Actually, I'm engaged again. Well, not officially, but soon."

"Really?" Ryan was surprised.

"Are you surprised that I'm divorced or that I'm getting married again?"

"Neither, I was just curious." His eyes wandered down to her low cut top. He could see the soft white flesh almost overflowing the top. Her nipples were hard. He felt the familiar stirring in his groin.

"I've worked for Sandra for many years. I moved in about ten years ago, a while after her husband died. He was a lot older than she was when they got married but her husband's death still hit her hard. She needed somebody and I needed to get out. It's worked out well for both of us. Actually, Sandra is the one that introduced me to Vic... my fianc‚. He's a good friend of her husband's."

Ryan figured that Vic must be a lot older than Ms Baker if he was a friend of Sandra's husband, but he didn't say anything. Instead he reached over and grabbed another piece of carrot, and like the other day he "accidentally" rubbed his arm on her breast. As he brought the carrot back, the back of his hand touched one of her nipples.

The older woman paused and took a deep breath.

Ryan thought he was in big trouble. But after a moment when she began to work on her salad again, Ryan was relieved and suddenly very excited. Boldly he leaned his arm on the counter and slipped his hand under her arm. Then he reached out with his index finger and touched her nipple, using his finger to make a gentle circle around the tip.

Ms. Baker paused in the middle of cutting a tomato. She didn't look at him but instead dropped her head and closed her eyes.

When she did nothing to stop him, Ryan opened his palm and grasped her breast. He suppressed a moan when he felt her soft flesh in his hand.

Suddenly the kitchen was filled with sexual tension. Ryan's penis was pulsing in his shorts and Ms. Baker had begun to breathe heavily. He grew bolder and began to squeeze her breast. Then he pushed her shoulder back until she turned toward him. He saw that her eyes were open but glassy and he wasn't sure if it was from fear or excitement. He reached out and now with both hands began to squeeze her breasts.

"Ryan," she whispered, her eyes hooding over in obvious pleasure. "I'm... I'm almost a married woman," she pleaded weakly. But she didn't stop him as he boldly slipped both hands into her top to grasp her breasts.

He lifted them out of her top.

"Oh God," she moaned.

Then Ryan pulled her into his arms, her warm breasts pressing to his chest. Instead of pushing him away, she turned her face up to him expectantly.

Ryan pressed his now hard penis to her stomach and bent his head until his lips met hers. She moaned through her opened mouth as his mouth covered hers and his tongue slipped inside.

Suddenly there was a noise from upstairs... voices and a closing door. The two of them jumped apart and looked toward the steps. Fortunately, most of the kitchen could not be seen from the balcony.

Ryan rushed over and sat down at the table to hide his erection and Ms. Baker quickly covered her exposed breasts. A second later, a middle aged man came down the stairs.

"Goodbye Ms. Baker," he said and waived as he headed for the door.

"Goodbye Mr. Lindsay," Ms. Baker answered and waived back. Then she turned to Ryan.

Ryan couldn't tell from her expression if she was angry or not.

"I think Doctor Billings is ready for you now Ryan," she said breathlessly.

When he stood up, his half-hard penis was still noticeable in his shorts. He saw Ms. Baker's eyes drift down. His face turned red.

"Sandra is going to think you're glad to see her," she suddenly quipped. Then she shocked him by reaching down and grasping his penis; moving her hand up and down several times and making it grow stiff again. "Have fun," she whispered before turning back to the counter.

By the time Ryan was at Doctor Billing's door, his penis had shrunk until it was only half-hard. He took a deep breath and opened the door.

Dr. Billings was sitting at her desk as usual. She looked up over her glasses as he entered and said, "Have a seat, I will be with you as soon as I finish filling out Mr. Lindsay's chart."

Ryan saw her eyes linger on his shorts and was pretty sure she could tell that he was excited. He sauntered over to the sofa, sat down and crossed his legs.

A few minutes later Doctor Billings got up and came over to the sofa. She was wearing a pleated blue skirt and matching blazer. Underneath she had on a white blouse with ruffles down the front. She sat down with Ryan's chart on her lap. "Okay, where did we leave off last week?"

With my cum in your mouth, Ryan thought but didn't say.

She looked at her chart and said, "Yes, we were talking about oral sex."

Ryan thought, I don't think we were just talking.

"Before we go on, do you have any questions for me."

"Uh... no, I don't think so."

"Come on Ryan, if I am going to help you, you must feel free to speak honestly."

"Well... uh..." Ryan stuttered, trying to think of something to ask, avoiding her eyes. He took a deep breath and said, "Uh... you... uh when you sucked me... uh you swall... swallowed. My friends say most girls won't do that." He paused and looked at her face. He thought he saw a slight blush.

"Well, that is somewhat true. My experience is that there are some girl or women that don't like the taste. However, semen is nothing more than protein and is not harmful... assuming that the man is healthy. Then, there are just as many women that would never spit it out. They feel that it is a way to show closeness to their lover. Personally, I love the taste as much as the feeling of closeness." The doctor paused and added, "Does that answer your question?"

Ryan felt his penis coming to life again. "Uh... yes it does, thanks."

"Okay Ryan, I know that you have had limited experience with girls and you stated that your problem was the size of your penis head. Do you think that that is your only problem with your shyness around women?"

"Well, I think so but I don't really know."

"Let's explore that if we can." The doctor looked down at her chart and made a note before she continued. "There are some boy, even men sometimes, that are generally embarrassed to be naked in front of a woman. Obviously there are many women like that as well. But the truth is, the naked body is the most natural thing in the world. We learned to wear clothes thousands of years ago to protect us from the elements and not from the view of other humans. Over the centuries, society dictated that we must wear cloth. However, in many cultures around the world, nakedness is a more natural state than wearing clothes." Doctor Billings paused again and tapped the eraser end of her pencil against her chin. "Are you embarrassed to be naked in front of women Ryan?"

"Uh... well uh... sure... I guess so." He thought of the first visit and how he had been naked in front of both women. That had certainly embarrassed him. But then yesterday with Mrs. Wellsworth... there wasn't any embarrassment then.

"Let's try a little experiment Ryan. Stand up please."

Ryan hesitated.

"Come on, stand up."

Ryan stood up with an uncomfortable feeling in the pit of his stomach.

"Take your clothes off."

"What?" Ryan said, thinking he had not heard her correctly.

"I want to see if you are embarrassed by being naked in front of a woman."

Suddenly all the confidence he had come in with vanished. His legs felt weak as he stood silently in front of the sexy woman and saw her lips were curled up in what could have been a smile. He could feel his face burning.

Doctor Billings was silent as she waited patiently.

The room was uncomfortably quiet. Ryan could suddenly hear the clock ticking on the wall; it sounded very loud. He had never noticed it before. His heart was pounding in his chest and his legs had turned to jelly. With trembling hands, he pulled his tee shirt up and over his head, baring his strong chest. Then he hesitated again, looking at Doctor Billings for any sign of a reprieve. When he saw none, he hooked his thumbs into his swim trunks and began to pull them down very slowly. Unintentionally he was teasing the doctor, almost like a male stripper. First his upper abdomen below his belly button was revealed. The muscles of his stomach formed a V that disappeared under his shorts. Then his pubic hair appeared. He stopped for a second when the elastic of his shorts reached his penis, forcing it further downward. He looked again for a reprieve. Seeing none, he pulled the elastic out, letting his half-hard penis spring out. It pulsed and in spite of his embarrassment began to grow. Suddenly it was pulsing up and down with his rapid heartbeat. Then he bent and pulled his shorts from his feet, relieved that he was covering his excitement from her view, if for only a moment. He stood back up and held his shorts modestly in front of him.

The doctor stared at him and remained silent.

Finally Ryan sighed and pulled the shorts from his front and tossed them onto the sofa.

The doctor's eyes stared at the boy's throbbing penis and she tried unsuccessfully to keep a professional demeanor. There was an excited glow on her face. "You have nothing to be ashamed of Ryan. In fact, you have one of the best bodies I have ever seen on a young man... or an older man for that matter. You should be proud."

Ryan was proud of his body but this was quite different. He could feel the flush from his face flow down his neck and across his chest.

"Turn around."

Ryan obeyed. He could almost feel the doctor's eyes on him... on his muscular back, moving down to his trim waist and across his strong buttocks. He squeezed his cheeks, almost as a reflex, emphasizing the muscles running down his buttocks and across the backs of his thighs. Then he remembered her finger and a shiver went through him and his penis throbbed.

"Very nice," the doctor said, a little breathlessly. "You can take your seat again." As Ryan reached to pick up his shorts, the doctor added, "And leave your clothes off please."

He looked at her in surprise but then sat down. The leather sofa felt cool to his now very heated body. His penis was throbbing at full mast.

Suddenly, there was a tap at the door. Before Doctor Billings answered, it opened and Ms. Baker looked into the office. "Oh, I'm sorry," she said but stepped into the room anyway.

Ryan sat with his face beet red and his hands trying unsuccessfully to cover his throbbing penis.

"I am going out to the market and wanted to know if you wanted anything special?" Ms. Baker asked the doctor but she was looking at Ryan.

"Yes, I have a list of supplies for the party next week. You may as well get some of the things now." With that the doctor got up and went over to her desk.

Ms. Baker continued to stare Ryan, her eyes on his hands as he vainly tried to cover his excitement.

Suddenly, some of Ryan's confidence came back. He figured if these ladies wanted to look at him, then why not. He glanced at the doctor and saw that she was bent over with her back to them, looking for the grocery list on the desk. With that, he moved his hands from his groin and allowed his penis to spring into the air. The large head was now almost purple and there was a steady stream of pre-cum juice running from the slit. Boldly he opened his legs, exposing his swollen testicles as well.

The look on Ms. Baker's face turned from a smile to clear excitement.

As Ryan stared at the woman, he wrapped his hand around his shaft and began to stroke it. He could almost see her tremble. When a large drop of clear juice bubbled from the head and began to run down the shaft, he saw her lick her lips. A tremor of excitement ran through him at the look of lust on her face. Then, when he saw Doctor Billings start to turn around, he placed his hands over his groin again and closed his legs.