Silver Anniversary

"You know the weather is pretty good for this time of year. It could be a lot warmer than it is."

"So, Sailor, what are you in town for?"

"Well, actually I am looking for a teacher."

Now all the women on the corner were looking at Chuck. The first woman continued to speak. "A teacher you say? What kind of teacher are you looking for?" She made a motion to include everyone standing there. "I don't know if any of us would be considered a teacher."

Chuck ducked his head in embarrassment. He decided that the truth was the best way to proceed. "Well, a week ago my wife told me and everyone that had any hearing that I was a dud in bed and couldn't satisfy a woman. She even said that I couldn't find a clitoris with a map. I have studied on this and have decided that I need lessons. For that I decided I needed a professional, one who could take the time to guide and instruct me."

She laughed along with the other women. "I suppose she gave you permission to seek out this education so that she could benefit from it."

Chuck shook his head. "No, actually she announced that, as she also announced to me and family and friends, she had already replaced me in her bed. No, this I want to do for myself and any future partner. So, are any of you interested in taking on the job?"

The woman gathered together and whispered for a short bit. Finally one of the younger girls asked a question. "Where will this education, as you call it, take place?"

Chuck replied that he had a car in a downtown parking structure and that they would go to his motel and named the motel.

They gathered again. Finally one of the other women spoke up. "Look, Slick, you look honest but let's be real. More than one of us has taken a ride in a car and not come back. Washing up on the shore of the lake or being found in the landfill isn't right even if we are whores."

The original woman that had approached Chuck also spoke up. "We ain't got much, Sweetie, but we do have our lives and we don't want to lose that last bit of self."

Chuck pondered that. He could understand their reluctance. "Do you have a pimp?"

They shook their heads. "No, and we don't want one." One of the girls showed Chuck she had a small pistol and another pulled out a switchblade. "This is to keep them away. We don't try to work the popular corners and they don't bother us. There isn't any percentage in it for them. We then pool our money. Someday we will be out of this business."

The older hooker identified herself as Sylvia. She was at least fifty years of age with dyed hair and fake nails. The youngest was Tiffany and had dark hair and small breasts.

Two of the others identified themselves as Mandy and Grace. They were about thirty years old.

Chuck went back to the original question. "Are you willing to help me out or do I look elsewhere?"

They conferred again. Chuck interrupted them. "How about this? I will hire two or three of you as my instructors. I drive back to the motel and you meet me there. Bring whatever you need to teach me everything that a woman might want a man to know and whatever protection that you feel need to be safe with me. I will go and grab some condoms as we need to do this safely."

They conferred again and then agreed. Sylvia would assume the role of primary instructor and Tiffany would be the test subject. Mandy and Grace would provide security from inside the motel room and also outside. They discussed fees and came up with a thousand dollars a night. Chuck put cash on his mental list. The meet time was agreed on and Chuck headed back to his car.

Since it was a Saturday he needed to find a branch office of his bank and quickly. Luckily there was one on his way to his car. He stopped in and requested some cash. While he was there he arranged to open new savings and checking accounts and moved the bulk of their money from the old accounts to the new accounts. He was afraid that the young Casanova, Mr. Andrew Cornings, would get Marcy to give him some money. Chuck left her enough to pay the bills for the current and subsequent month. Her wages should be able to handle the bills after that.

Next stop was at a pharmacy and he picked up condoms and spermicide. He then ate an early meal but kept it light but filling.

At the appointed time there was a knock on the motel door. Chuck opened it and welcomed the four women. Grace went back outside after making sure that there was no one else in the room. She would watch from their car across the parking area from the room. She had the pistol with her.

Mandy grabbed a chair by the table and pulled out the switchblade. She opened it a couple of times just to remind Chuck that they were serious about their security. Chuck had purchased a couple of bottles of cheap wine and used the plastic cups in the room to get everyone something to drink. He didn't know how to proceed and said so.

"Look, girls, I will be honest with you at all times. I have never seduced a woman. As a matter of fact I have only had sex with one woman in my life. We just had our Silver Anniversary celebration when she told me how bad a lover I am. I don't even know how to ask someone out for a meal."

Sylvia took over. "We won't fix that right now. I believe we should concentrate on how you excite a woman and then take it from there. Let's start with you and Tiff on the loveseat."

Chuck and Tiffany moved to the loveseat and sat down. Tiffany was comfortable with sex so she appeared relaxed while Chuck looked like he could jump right out of his skin if someone said "Boo."

Sylvia had them kiss. Tiffany said it felt like she was kissing a wood doll. They worked on it for a while and Chuck started to relax a little and the kisses became better. Tiffany even looked pleased as they drew apart. Sylvia asked, "Did you use your tongue, Chuck?"

Chuck shook his head. "Good. Tongue action may be good but you have to respond to your lover. If her lips are still a little compressed then don't push your tongue in there. As her lips part then you can paint her lips with your tongue. If her tongue comes out and meets yours then you can go further. Let her decide the pace."

They kissed some more. Both agreed he was improving. Then came necking instructions. Tiffany and Chuck nuzzled each other and kissed and nibbled each other's neck. While they were engaged Sylvia was discussing erogenous zones and how to tell. Chuck realized that Tiff shivered a little when he nuzzled her ear. He came back to that area again and again but at Sylvia's urging made sure to not tarry too long there as it might become irritating.

Tiffany told Chuck that he was doing well. All could see that his cock was responding to Tiffany so they didn't comment on his response. After all, a blowing wind can get a guy going.

They progressed to caressing. Sylvia and Tiffany guided Chuck in how to place his hands. They showed him how to slowly work his way to the woman's breasts after reading her physical responses. He remembered those early fumbling dates with Marcy and how she had responded to what he was doing. It made more sense now. Why hadn't someone told him then? He came to the conclusion that he had been the product of the times.

After an hour they took a break. All had another drink of the cheap wine. Mandy also gave her critique of how Chuck was doing. For his part Chuck was frustrated that he didn't see how he was improving his lovemaking. All of the women immediately jumped on him and told him it was all part of lovemaking. If he didn't do this part well enough his partner wasn't going to be magically turned on.

Sylvia put it best. "Chuck, everyone hopes that their partner is so turned on before any lovemaking starts she is ready to climax just from the first touch. That seldom happens. Look at us. We stand there on the corner all day. We are thinking about sex. Who is going to stop? What sex act is going to be requested? Will his cock be large, small or in between? Does he know how to use it? But, we are not turned on at all. The johns just want to get their rocks off. We moan and groan and think about shopping, our last good fucking, our kids, our grandparents, whatever it takes to keep from thinking about what is going on since it is demeaning and just pays the bills."

"If any of these guys were any good in bed we probably wouldn't have a job to perform. Their wives or lovers wouldn't let them out of their sight if they knew what to do with their cock other than jump on, pump and spurt and then fall asleep." This came from Tiffany.

Chuck hung his head. It sounded just like him. He nodded his agreement.

Sylvia lifted his head. "You and I are products of our generation. There was no sex education, no easily obtained magazines, no decent contraception. We can be excused for our lack of knowledge. This younger generation can get education in school, can buy condoms without embarrassment, has the pill for almost foolproof contraception but still are ignorant of how to make love."

She bored into his eyes. "We can all become educated."

They then all started again. Chuck and Tiffany began kissing again but needed less prompting and direction. The kissing went well. Now they interposed some necking techniques and then gentle caresses. Chuck was learning quickly. He could now gauge Tiff's response by her sighs and gentle moans. He forced himself to keep the touches light and varying in location. He could feel the shivers when he hit a good zone and a lessening when he strayed from the zones for too long.

He felt her hair. He traced her lips with his. He kissed her nose and her chin. No suction was applied except on her neck for a few moments and then on to the next spot. He felt her nipple harden under his hand. Sylvia then told him how to stimulate the nipple more. After a bit he was directed to remove his shirt. Tiffany helped. She told him how she liked that he had not let himself become a fat slob like so many others. She traced his pectoral muscles and rubbed his deltoids as he continued to caress her breasts, arms, and back. Because of their guidance he did not try to touch Tiffany's vagina, at least not until her body language told him to.

Tiff's blouse joined his shirt on the floor. Her breasts were so small that she didn't need any bra. Her nipples were distended and seemed to be very sensitive. Chuck again forced himself to lightly touch. Sylvia was next to his ear as she suggested ways to make Tiff respond and give indications she was getting turned on. Chuck had the thought that Sylvia might actually be a lesbian as she breathed into his ear exactly what to look for in Tiff's responses.

The kept kissing and slowly moved to where there was the need to get rid of the rest of their clothing. Now Sylvia directed Chuck to slowly pull off Tiffany's jeans. He tried to do it without breaking the mood. They laughed and struggled to get her naked. Chuck used the opportunity of the exposure of her legs to caress those legs and try to keep the feelings high. Sylvia praised him for his ingenuity.

Soon she was in her tiny thong panties. Now she attacked Chuck's jeans. She didn't spend much time exposing him. She didn't need to. He was anxious to get to the next stage. Maybe that was the true lesson. Women took longer to get to where men started. Men just needed to learn that one lesson. It began there.

Soon his erection was rampant in his briefs. Sylvia quickly talked about briefs versus boxers and why some women liked each kind. He would have to learn to read his partner's response and change accordingly. The same for little things like flowers, small trinkets, warm fuzzy's, whatever it took to romance the woman.

Chuck now realized that Marcy was giving him hints all along. Her silences concerning making love, the buying of magazines such as Cosmopolitan later and even the books on sex that came out and she read but he wouldn't bother to read as though it would be an admission of ignorance and something less than macho.

Why did she not trust him enough to at least talk about it? He would have responded in some positive way, that he was sure of. He loved her. They could talk about anything except John.

With that revelation facing him his cock wilted and he quit trying to make Tiffany ready for sex. He sat back on his haunches and cried in front of the women. They immediately enveloped him in loving embraces while he went through the grief of love lost. It was some of his own fault but the real fault was the lack of trust, of faith, and love from Marcy that allowed their relationship to die its sudden death on their silver anniversary.

As he regained control he found that his head was cradled on Tiffany's miniscule breasts but his mouth was on her nipple and he was gently suckling just like a baby. Tiffany was giving out encouraging sounds intermixed with the moans of an excited woman. Sylvia was stroking his head and Mandy was stroking his cock. His erection had resurrected and was rampant again.

Sylvia noticed that he was again with them and directed him to move down Tiffany's body. He was now ready to learn fully. He kissed, licked and suckled his way south to her tiny thong. Pushing it aside he then looked at a bare pussy for the first time ever in his life. Sylvia continued talking but now was giving an anatomy lesson. She had him pry the labia majora apart and he could see the hood of her clit and her tiny urethra below it. As he moved lower still he could see the vaginal opening and the moisture there.

He put a finger into the small opening. Again a first for him. His finger was damp as he pulled it back. He could detect the faint fragrance of aroused woman. He looked at his finger then licked it. It didn't have much of a taste but decidedly wasn't the fish smell of legend. He touched her clit and Tiffany jumped at the touch. Chuck jerked back in response.

Sylvia gave out a little laugh. "Yes, you found it and without a map. How about that? Your wife was wrong."

She went on to discuss how sensitive the clit could become. Direct stimulation might be almost painful. Again the man needed to watch for his partner's responses and adjust accordingly.

Chuck wet his finger and lightly stroked Tiff's little man in the boat again. This time she didn't jump but wiggled a little at the touch. "Now use your tongue, Slick. Taste her at the source. Move up and down her slit and get her excited. You shaved today but have a little stubble so be careful how you rub your face against her most tender parts. This is not an exciting stimulation when you give whisker burns. As a matter of fact shave before every date even if you only shaved a few hours before. Your woman deserves it."

Chuck nodded his understanding. His mouth was dry as he contemplated the splayed out woman in front of him. Tiffany was making sure that she was open and ready for his oral advances. Chuck was trying to overcome a lifetime of indoctrination against real men eating at the "Y".

He closed his eyes and let his tongue guide him. He touched her vaginal lips and then moved back and forth across her pussy learning the contours. He wasn't trying to arouse right now, just learn the lay of the land. He didn't know if every woman would feel exactly the same but doubted it so he wanted to learn Tiffany right now.

Apparently this was not a wrong thing to do. By doing so he teased her. After exploring with his tongue along the edges of her labia then he dove to her clit and gave it a couple of licks before moving down past her urethra to the vaginal opening. He had explored with a finger so he now explored with his tongue. Her taste was sublime. He savored it as he had the exploration of her labia. Again he reasoned that women would taste different one from another so he was resolved to commit Tiffany to his taste buds as the first pussy he had ever tasted. If they were all as good tasting as she then she was destined to be the first of many others he would taste.

He dipped, he wiggled, he curled his tongue and tried to capture more liquid. He came back to her clit for a minute at a time and thrashed that little bud back and forth. It grew rigid under his tongue so he sucked it a little. Since he had no idea if every woman's clitoris was the same size he learned this one. He listened to Tiff's moans of excitement and changed as she changed. He tried to anticipate her moves as her excitement grew.

Sylvia was right next to him telling him that he was doing good. She suggested changes that he tried. Some worked and others not so much. He filed them all into his memory for future reference.

Sylvia directed him to slide a single finger into Tiff's wet pussy while he was tonguing her clit. He would withdraw when he went back to her pussy for some deep tonguing. Back and forth he went and Tiff was getting louder in her climb to climax. Soon he had three fingers in her pussy, stretching it nicely. Sylvia was telling him a little stretch was good but a lot was reserved for when the woman really was hot and horny and begging for a super thick fuck. Again, he was to listen and respond.

As he drew back for a breath he opened his eyes, the first time in many minutes. Tiffany was supine with a clearly excited look on her face. She had her legs spread and pulled back to give him as much room as he would like. This tilted her pelvis so her pussy was further up in the air and her thin little buttocks were not really touching the bed. Her little rosebud of an anus was moving in and out with her excitement.

Sylvia pointed that out to him. "Baby, most of us, men and women, really like it when our lover is confident and competent to lick that little aperture. It is full of nerve endings and when clean has no taste. Can you do it? Can you be man enough to give her that pleasure?"

Chuck first shook his head as he slowly moved his fingers in and out of the juicy pussy right in front of him. He was not going that far, at least not today, until Tiff whined. "Please, Chuck, please tongue me there. It has been so long since someone has done that for me. I love it. I will return the favor when it's your turn."

Because she asked so nicely, but not because she promised to return the favor as he wanted no one near his tight little rectum, he went ahead and bent down a little more. He had to move his fingers out of the way. He now had his eyes wide open as he stuck out his tongue and touched her little rosebud. She immediately let out a long satisfied sigh and her anus quivered under his tongue. It tickled him a little but he laved the area again and again. Tiff's little cries let him know how much she enjoyed it.

Suddenly her rosette dilated open and his tongue penetrated. He almost pulled back gagging but realized that there was no different taste so he tongued her deeply. As an afterthought he also used his forefinger to stroke her clit after getting a little liquid from her core on it.

Tiffany suddenly grabbed his head and slammed him into her ass. Her muscles strained and became rigid as she screamed her sudden climax. A small amount of fluid came out where his nose was buried in her sloppy pussy and almost shut off his air. His head bobbed up and down as he was taken along for the ride as her pelvis jumped up and down. She shook and cried as her orgasm completely drained her.

Finally she relaxed and let her legs down on Chuck's shoulders and she let him have some air. He gulped huge breaths as he fought the dizziness from almost suffocating in her ass and drowning in her pussy.

As he pulled back he could feel the wetness on his face. Who knew that a woman could get that wet? Apparently anyone who could learn what making love to a woman really was. He was saddened that the love of his life had never felt that way with him.

Sylvia and Mandy were praising him for his success. After Tiffany got her breath back she echoed their praise. Chuck felt proud of himself. He could actually learn and maybe would no longer be the dud in bed.