Seduced by an Experienced Woman Ch. 11

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Ann needs an assistant coach.
3.2k words
4.48
11.5k
3

Part 11 of the 12 part series

Updated 06/09/2023
Created 02/02/2019
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Try as I might, Ann ignored my attempts to let her know how uncomfortable she was making me.

Caitlyn called to her roommate, "Branna, come to the door, Ann wants to talk to us!"

"The lady who's dating our neighbor?"

"That's the one."

"What does she want to talk about?"

"Just come to the door."

She came to the door barefoot, wearing a t-shirt & daisy dukes. "Branna, this is Ann and our neighbor Frederick, you remember him don't you?"

"I certainly do!" She looked directly at me and said, "I'm still wondering about what Ann said the other evening."

I was embarrassed and it showed.

Ann spoke up, "Do you ladies have a couch or some chairs. Freddy only has one easy chair and I'm loaning him this rocker. If you have a place we can all sit down I'd like to explain and answer your questions and then there's a favor I'd like to ask."

"Sure," Branna said, "Caitlyn and I would love to hear more, I for one have been dying of curiosity."

"Me too!" Caitlyn agreed. "We've got a nice sectional and if you bring that rocker in we will all be comfortable."

"Come along, Freddy dear, bring the chair with you."

I couldn't find the courage to object so I did as Ann asked.

The girls apartment was a mirror image of my own. The door was in the middle with a small closet just inside on the right. Their kitchen was on the left. When you walk into the living room there is a sliding glass door on the far side that went out onto a patio that was enclosed by a wooden privacy fence. The apartments are all identical, the only difference being a left or right handed floor plan. "Freddy dear, put the chair by the door." The girls had a three piece sectional; Ann sat on the little "leg" of the sectional. Caitlyn sat on one of the two pieces facing the door. Branna asked, "Would you care for some lemonade, I just made it."

"That would be nice," Ann responded, "What about you, Freddy, would you like some lemonade?"

My mouth was dry, "Yes please," I nodded quietly.

While Branna poured the lemonade Ann quizzed Caitlyn, "Are you ladies students?"

"We are." Caitlyn beamed. "We're both scholarship students in the nursing school."

"That's wonderful!" Ann grinned, "First year?"

"Oh no, sophomores," Caitlyn explained. "Freshmen aren't allowed to live off campus."

"Very nice." Ann grinned, "Don't you agree, Freddy?"

I just mumbled looking down, "Yes, ma'am it is."

Branna returned with the lemonade and Ann continued, "How did you two meet?"

"We're on the volleyball team so we've spent lot's of time together both in class and after." Branna explained.

"That explains why you two are in such good shape." Ann complemented. "Don't you agree, Freddy?

"Yes," I answered sheepishly.

"Don't be so bashful, Freddy," Ann needled. "These girls know why boys like to look at their legs." She managed to embarrass all three of us!

"So, ladies! Where should I begin? How about this. Frederick got out of the Army a few weeks ago and he is my real estate agent. That's how we met. We have a rental property under contract right now."

"Not yet." I corrected her, "We just made an offer; it won't be under contract until it's accepted."

"Minor detail." She conceded, "Where was I, oh yes, anyway, Freddy was such a sweetheart about working with me that I invited him over for dinner with my two daughters."

"How old are your daughters?"

"Leanne is twelve and Joanne is ten." Ann explained proudly. "After dinner the four of us played "Sorry" and then after the girls were safely tucked in bed I seduced Freddy." She was almost emotionless as she recited the details of our first evening together.

"You did!" Branna exclaimed and I started getting red again.

"Ladies. I was horny as could be." Ann clarified, "Freddy was too much a gentleman so I didn't want to wait for him get a clue."

"But," Caitlyn wondered, "you're quite a bit older than Frederick!"

Ann turned to me, "Does that bother you, Freddy?"

"No, not at all!" I stammered.

"You see girls," Ann continued, "When you get to be my age and I'm almost twice as old as you it can be mutually advantageous for a woman to have a nice, handsome young man as a friend with benefits!"

"Friend with benefits?" Branna puzzled.

"Girls," Ann chuckled, "I've gone through half a dozen boy friends, two or three that got a little serious, and one husband. I know things. I know things that it will take you ages to learn by yourself! Freddy lacks experience but has stamina. It's beneficial for each of us. Don't you agree, Freddy?"

"Yes, ma'am." I confessed.

"That brings me to that thing the other night."

"You mean...?"

"Yes, Freddy and I have agreed to be faithful to each other, that means no sex with others. Kind of like going steady but not engaged."

"So, you're a couple?" Branna wondered.

"We're not dating in the usual sense. We don't go to movies or shows but we do have sex, lot's of sex! Right Freddy?"

I was embarrassed by her candidness but agreed.

"Tell these nice young ladies what rule number one is, Freddy." Ann smiled and coaxed.

I looked at Ann sadly, pleading for mercy.

"Go on Freddy, you can do this."

I closed my eyes and bit my lip, took a deep breath and blurted, "I am not allowed to masturbate by myself!"

The girls giggled and whispered to each other and then asked, "By himself, Ann?"

"Have you ever watched a guy jack off? It's fascinating!" "But let's be serious, ladies!" Ann admonished, "I expect Freddy to be faithful to me and that includes having sex by himself. That's reasonable; don't you think?"

They looked at each other. Finally Caitlyn agreed, "Very reasonable." I think they were amused and confounded all at the same time.

"I can see you are wondering why I would share such intimate details to basically complete strangers."

"Well, yes." Branna agreed. "Why on earth would you tell us this stuff and embarrass Fred."

"I need your help." This was news to me.

"Whatever for?"

"I belong to a small group of like minded women. We are all in our mid thirties or older. We are all successful professionally. We all have friends with benefits. Well, that's not true exactly. Two of us are in committed relationships. That's not accurate either, we're all committed but two of us are actually married and once a year we have a dance where we have a little contest just for fun."

"So...?"

"We have a cum shooting contest." Ann explained like it was a natural as taking a walk.

"A.. what..?" Branna gasped.

"I said, a cum shooting contest." Ann reiterated slowly.

"This is getting interesting!" Caitlyn blurted. "How would you need our help?"

"Well, like any athletic contest there is a certain amount of training involved."

"Oh, pa.. leeese! You've got to be kidding," Branna mocked. "Guys don't need to train to jack off!"

I was getting redder by the minute.

"Branna, sweetheart," Ann reminded her, "You wouldn't need to train to go on a jog but if you want to compete in a 5k race you would train wouldn't you?"

"Well... I guess I would," she reflected.

"And you know all the drills coach has us do?" Caitlyn reminded her, "That's all so we'll do better when game time comes, practice makes perfect, right."

"I suppose..."

"So the bottom line is: I need help training Freddy. Would you girls help me please?"

"I'm in!" Caitlyn chortled, "What would we have to do?"

"There are certain exercises that promote stronger ejaculatory response. I need an assistant coach to observe and verify that Freddy is doing the exercises correctly and in the proper amount. Would you be willing to help with that?"

"There is no sex involved, right?"

"Absolutely not!" Ann affirmed. "Strictly forbidden, while he's in training he's not allowed to jack off at all. You can tease him a little if you like. I think he's been admiring more than your legs. I only want you to observe his exercise sessions in the morning and evening when I'm busy and can't do it myself."

"What's in it for us?" Caitlyn wondered.

"What do you think, Freddy? Maybe you can do a little housework for them. Clean the kitchen or bathroom? Would that be fair?

I just looked down at the floor.

"I'm guessing that is a yes!" Ann proclaimed. "It will take some time so the least he can do is help you out a little."

"Sounds good to me! Caitlyn bubbled excitedly. "What do you say. Branna?"

"Why not?"

"I'm glad that's settled, thank you!" Ann smiled wickedly. "Now tell them what rule number two is, Freddy."

"What do you mean?"

"Don't be shy Freddy, we will have to abide by rule two so your coaches can properly observe." Ann stressed.

"You don't mean...?"

"Yes I do, Freddy!" Ann chastised, "Ladies, when Freddy visits my apartment and the girls are not home he must be nude at all times!"

"You're kidding! You can't be serious."

"Yes I am! How else will you be able to see if he is doing each exercise correctly?"

"So... you're saying that Fred will be naked when he's exercising and doing housework?"

"I don't know?" Caitlyn admitted.

"I think we should give it a try." Branna urged.

"Well remember, I will teach you." Ann stressed, "We can start now! Freddy."

"What?" She startled me. I was almost in a trance not believing what was happening.

"You know what. Don't make me spank you!"

"You spank him?" Branna inquired.

"Not yet, but if it becomes necessary I will!" Ann looked at me and encouraged, "Just take a deep breath, Freddy, stand up and do it."

I took off my shoes and socks, stood up and as the three women smiled began to strip.

Caitlyn broke the silence, "You still haven't explained your rocker."

Ann responded with a question, "Do either of you know what queening is?"

They looked at each other and shook their heads no.

"You girls have a lot to learn, maybe I can coach you, what do you think?"

My shirt and t-shirt were folded and on the seat of the rocker. "What are you waiting for, Freddy? Be quick about it.

As I stepped out of my trousers Ann continued explaining, "You see ladies, Freddy is just learning to be comfortable around clothed women when he is naked. Isn't that right, Freddy?"

"Yes, ma'am."

"So there are two ways you will be helping me. One is to help Freddy become comfortable being naked in the presence of new and different women including having or not having an erection."

"This is getting better by the minute," Caitlyn chirped. Branna just stared, slack jawed as I obediently stepped out of my Jockey shorts. My penis was only slightly swollen. My head was spinning; I barely heard them speaking.

Caitlyn and Branna leaned back silently smirking and watched me intently as Ann continued to explain. "The exercises I mentioned are called Kegel exercises; Are you familiar with them?

"I am," Branna piped up. "I come from a large Irish/Catholic family. My mom was explaining them to my aunt after she had her first child. They help a woman control peeing and tighten the muscles in her pussy after childbirth."

"No need to be vulgar," Caitlyn chided her room mate, "You are a nursing student you know!"

"No need to be stuffy either." Ann defended Branna. "In fact, I prefer using common terms like dick, prick or cock when you talk to him about his penis. You can call it anything you want! The more he hears you talking about his penis, the more and different terms you use the better he will be able to control himself!"

"By control do you mean stay soft?" Caitlyn wondered.

"Heavens no!" Ann laughed, "As a group we are fond of seeing men with nice hard erections."

"Freddy isn't very hard." Branna observed.

"He hasn't been properly trained yet. That's why I need your help. I've only got forty-eight days to get him into game shape. I was going to skip this years dance but Freddy found out about it and insisted we should go. Isn't that right, Freddy?"

It wasn't; I'm sure I never insisted on any such thing but I didn't contradict her.

"So, about those exercises, there are Kegel exercises for men too. They are helpful for older men to control incontinence and for younger men they are useful in preventing premature ejaculation."

"They should start teaching the boys in gym class!" Branna blurted.

"I should say so!" Caitlyn agreed.

"Well, they don't. Sex education is sadly lacking in American schools. There's all kinds of talk about doing it but nothing about doing it right." Ann lamented. "But, I digress, we should get started."

Ann stood up. "Let's start with the way the ladies greet the men. This can be for the first time or at any time after they have become acquainted. The ladies exchange a quick hug and a little peck on the cheek. If there is only one man present the greeting goes like this, "Branna, I'd like you to meet Freddy." Branna would hold out her right hand and as I say, Freddy, this is my friend, Branna. Freddy would take your hand and give it a little kiss. Branna, you would place your left hand on his hip draw him close to kiss his cheek and at the same time you could hold his balls if you wanted."

"So, wouldn't Freddy get a hard on? Caitlyn asked.

"I think that's the point!" Branna mused.

Ann smiled, "Yes ladies that is the point! With training a man should be able to get himself hard without touching himself, maintain his erection for a few minutes and then relax for a few minutes. If he can do that in a social setting imagine what he can do in bed!"

"Last more than a minute or two? That would be nice!" Branna snickered.

"Well," Ann concluded, "They can and they do with proper training. The problem with most women is that they know what they want but they don't have the foggiest notion about how to get it!"

Ann went through the formal greeting process with both girls and then went on, "If you have been already been introduced then you can just approach them, say hi or something, give them a quick kiss on the cheek and squeeze their balls."

"What if we were at a store or just walking down the street?"

"Everything is the same except you're dressed and so is he."

"Even squeezing his balls?" Caitlyn laughed.

"Of course, just don't be too obvious about it." Ann giggled. "Now the second part of training is improving performance through exercise. We have a very short time before the dance so I want to concentrate on just two of the many possible exercises. The first is called a flutter. A man tightens and releases his pelvic floor muscles very quickly ten times and then rests for thirty seconds. Repeat the exercise a total of ten times. If a man is doing this exercise properly you will see his penis rise and fall quickly, hence flutter! Once the set of ten is completed there should be a ten minute rest period."

"Can Freddy demonstrate?"

"I haven't even taught him yet, sorry! But you heard my explanation, Freddy, can you do it? Just squeeze your anus and make your dick bounce!

I must have been red as could be, it certainly felt like it. But I squeezed and my dick bounced. "Do it again!" Again! Again. See that's not difficult is it?"

"What should he do during the rest period?" Branna asked.

"Whatever you want; vacuum, dust, wash dishes. It's up to you!"

"Sweet!"

"For starters Freddy should do no more than three sets of ten but as he gets stronger he can work up to ten sets."

"What is the second exercise?" Caitlyn inquired.

"When Freddy has worked up to a minimum of five sets he can start on the squeeze and hold exercise. He will clench his sphincter and hold for two seconds, release and relax for five seconds and then squeeze and hold again for two seconds up to five repetitions. As he gains control and strength he should be able to hold as long as ten seconds."

"How can we tell if he is holding long enough?"

"You will need a latex glove. With a finger inserted in his anus you will be able to feel it!

"We've got plenty of gloves! We use them everyday in school."

Throughout Ann's explanation I stood quietly with my eyes closed unable to look the girls in the eyes.

"Don't worry, Freddy, Branna and I will be gentle." Caitlyn reassured me in a voice that clearly amused by my plight. "Isn't that right Branna."

"Oh yes! Of course we will be very gentle, don't you worry!' Branna agreed. "I do have one request though, Ann."

"What would that be, Branna?"

"If we are in charge of the training I think we should also be able to observe your practice sessions so that we can determine how effective the exercises are."

"That's a marvelous idea! Don't you agree, Freddy?" She didn't wait for my response. "I'll prepare a practice schedule for you. I hope you realize that part of the training is orgasm denial so it will only be two or three times a week but you should be able to fit one or two sessions into your schedule."

"Great! But you still haven't explained about the rocker."

"I'm sorry, I thought I did, Branna. I told you it was a queening rocker didn't I? Don't you know what that means?

"I've never heard the term."

Ann explained, "To be queened is when a woman sits on someone's face."

"Someone?"

"Of course, it doesn't have to be a man. The rocker is just a way for a lady to relax and have a glass of wine while her pussy is serviced!" Both girls blushed, if they weren't lesbians they were at least bi.

"Where did you get it?"

"I belonged to my grandmother."

"No way!" Caitlyn exclaimed, "You've got to be kidding!"

"Sex wasn't invented last week, sweetheart." Ann chided, "I don't know for sure but it might have belonged to her mother."

Branna interrupted, "I don't mean to be rude but we have shopping to do."

"I'm sorry girls, I didn't mean to take so much time. Can you start training tomorrow morning?"

"We have classes starting at eight, will six-thirty be good for you, Freddy?"

Ann responded, "He'll be ready, he doesn't have much to do except shower and brush his teeth! Just knock on his door.

Ann opened their apartment door and look outside. "The coast is clear, bring the rocker Freddy!" I piled my things on the seat of the rocker and followed Ann to my apartment. She let me stand naked in the hallway while she fumbled with my trousers to find my keys.

"See you soon, Freddy!" Both girls were giggling as they closed their door.

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AnonymousAnonymousover 2 years ago

Was brilliant 👏

Shame it's drifted away from Ann's continued training . Also the Ashley element needs more work

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