Total Woman Requests 05

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Freewill Weekend: Coaching.
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Part 5 of the 8 part series

Updated 06/09/2023
Created 01/02/2013
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Mrs. Rush reviewed the TWR Final Request Voucher. It looked to be in order: the Pledge Contributor's Requested Scenario, TWA Security's Clearances for Scenario Participants, Electronic Funds Transfer Authorization and the Confirmed Venue Schedule.

All Total Woman Academy Pledge Contributors (PC's) had discretionary use of the Total Woman Academy Graduate Network. TWA graduates donated their time and talents to events that contributed their earnings to the TWA Alumni Fund. The graduates volunteered for assignments at exclusive TWA Health Clinics and Resorts. Total Woman Requests offered the graduates additional volunteer assignments in unusual places and settings. All assignments offered abundant opportunities for graduates to refine their unique talents.

This Pledge Contributor had requested a special exception for his friend to attend a Freewill Weekend at the Total Woman Academy.

Mrs. Rush scrawled her approval on the Voucher form and handed it to her secretary. The fantasy was underway.....

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Edwin tried to look poised as he promenaded the pool deck at the Total Woman Graduate Academy. His friend and client had arranged this Freewill Weekend visit as a thank you for 'services' rendered. The services were not wholly legal and a money trail was not preferred. Enough said...

On arrival, Edwin's TWA Free-Will Weekend Orientation emphasized that all interactions must be safe and consensual to both parties. No undue force was allowed. Edwin would have unlimited access to all Academy facilities and a special coaching suite had been set aside for his exclusive use. He was expected to fulfill the role of a guest coach trainer, providing real tutoring to the students. Therefore, if Edwin had a particular sexual expertise he wished to explore, the student was expected to comply un-hesitantly with his instructions, even in public.

Edwin was encouraged to give the students constructive feedback during and immediately after the lessons. Otherwise easy to use checkbox and fill-in-the-blank forms were required for later review by staff with the students. Variety was compulsory. If he dwelt too much on any one student, his freewill selections would be restricted. He would be delegated to a roster with a randomly assigned schedule of students to tutor. 'Spread the wealth around' was the mantra for Freewill Weekend.

The students were aware a special visitor would be attending this weekend and there was a buzz of excited anticipation in the air. It was a great opportunity to get intimate familiarity with diverse males' desires and responses.

Edwin was getting his first look at the glorious smorgasbord of nubile flesh that was his obligation to tutor. And the women were getting a first look at him. All the women were at least topless, many wearing nothing at all. They were playing in the pool, sunbathing on lounges or sitting at umbrella tables savoring drinks or snacks. Edwin's boner was already obvious, even inside his baggy board shorts.

Edwin paused at the edge of the pool. There were several naked nymphs playing a game of tag and splash. He watched as they jumped, laughed, dunked and porpoised. Wet tanned skin contrasted with the sapphire tint of the pool bottom and the clear water.

Edwin looked over to the far edge of the deck at a shaded lounge draped by a curvaceous naked blonde. He strolled that way. She spied his approach and levered up her sunglasses. She smiled cheerfully, meeting his gaze with obvious welcome. She stayed attentive as he neared. When he sat on the lounge next to her, she rolled to give him a full frontal exposure and extended her hand.

"Hi, there. My name's Carol."

"I'm Edwin."

"Are you this weekend's guest trainer?"

"Yes, I think so. Were you-all expecting someone?"

"Oh, yes. I thought it might be you since I haven't seen you here before. I know most of the regular guest tutor PC's. We heard someone special was coming this weekend and I guess that's you. Everyone is dying to meet you. We heard you will be tutoring us with your distinct penchants that will add new topics to our current curriculum."

Edwin felt his dick twitch and his face begin to flush. He had come here for a little rest and recreation but these women seriously expected to learn from him.

"I hear the TWA curriculum is pretty thorough. I can probably offer some coaching and tune up of what you already know. How much do you know already?"

Carol stroked her finger tips along his inner thigh.

"I know that I want some expert coaching. I know that the weekends can be short so it's good to start early. I can see by the lump in your shorts that you are also ready for an early start. I know I want to be first in line. And I know that there's no time like the present to begin."

"I like the sound of your knowledge so far. And, yes, there's no time like the present to begin."

Carol moved her hand higher under Edwin's shorts. He watched good-naturedly as she sat up and smoothly began unfastening his waistband and lowering the zipper. As he stood up, her hands cradled his tumescent shaft and balls as the shorts dropped to his ankles. His thick dick was level with her face and she leaned in to kiss his tip. She eased off her lounge onto her knees and guided him to sit again.

Carol looked up at Edwin. "Please teach me what you like and how you like it. I will try hard to learn to do whatever you want. I want to absorb anything you care to offer me."

Edwin was a little surprised at her eagerness.

"Okay...use the tip of your tongue to stimulate the underside V of the corona...Ooo Ooo, that's right...then the flat of your tongue on the tip...try some different angles...oh, yes..."

Carol swiveled her head to get her tongue on all sides of the knob and shaft. Edwin sat still and mused on her techniques and this unbelievable setting. His cock throbbed with fullness.

"That's enough foreplay. Deep throat me; all the way."

Carol kneeled up, faced straight down and sank his cock to the back of her mouth...and beyond. His cock head popped into her throat as the passage brushed his crown. Edwin moaned. Carol took note and rubbed the corona little by little back and forth across the narrow gullet channel.

Edwin's thermostat was in the red zone; he was ready to flare into her his first load of the weekend.

Carol heard him wind up and grunt loudly. She felt the pulses run up his shaft. Three shots of semen pumped out and collected in her mouth. She bobbed and swallowed. The fourth and fifth shots took up the newly empty space. Edwin placed his hands on her head to slow her pace and eventually stop altogether. Carol swallowed the accumulated sperm.

Carol stayed in place as the man meat shrank in her mouth. Before it completely deflated, she opened and lapped up the errant cum dregs lingering on his skin.

A shadow fell across Edwin's face and he looked up to a smiling topless brunette.

"Carol, you sure are the early bird that gets the worm." Her tone was playfully sarcastic.

"Cheryl, I like being the early bird. And this mighty muscle here is a lot more than a worm."

Carol held Edwin's still fat shaft across her palm for the new-comer to see.

"This is Edwin, our Freewill weekend guest coach trainer."

Edwin raised a hand and politely took Cheryl's proffered hand in greeting. Cheryl held his hand and didn't let go.

"So, Edwin, as you can see, we are all anxious to acquire your experience and expertise this weekend. Can we do anything to get you comfortable? Your work here may become arduous. We want you to stay strong and virile so the most students possible get ample tutoring during the short time available. Carol, let's show Edwin the amenities we offer our guest coach trainers."

Carol rose, naked, and stepped into her low heeled clogs. She took Edwin's other hand and the pair guided him to a main building side entrance off the deck. They entered the pool's locker room. A few other guest coach trainers and their initial selection of student trainee for weekend were milling around paying Edwin and his tour guides little attention. Edwin's trio found their way to the sauna.

Edwin lay prone on a broad towel-draped cedar bench with Carol and Cheryl lay out beside him. The timer let them swelter for 20 minutes before clicking off the heat. Edwin laid quiescent, eyes closed. He felt hands creeping up his thighs and fondling his limp cock. It didn't stay limp for long. The hands took turns sliding up and down the shaft. When Edwin was erect and pointing northward, Cheryl leaned up on an elbow.

"Please, sir, what can I learn from you right here and now?"

"Hand grasp and control are always a useful skill."

Edwin put his hand over hers, guided her pace, adjusted her grip and showed her his favorite finger strums beneath the corona. Cheryl followed his every instruction, noted his facial expressions during her movements and adjusted her efforts to prolong his pleasure. His exhilaration level rose to a crescendo.

Edwin gusted and sprayed his cum all over his abdomen and Cheryl's hand. She held him gently as he came down from his orgasm. When calm was restored, Carol awaited Edwin signs that he was ready to get to his feet.

Carol and Cheryl led Edwin to the group shower room. The women took positions aside Edwin and soaped him down under the warm spray. Edwin got squeaky clean. Carol gave Edwin a fond kiss 'adieu' and departed. She was eager to mingle with the other guest coach trainers and maximize her ration of tutoring.

Cheryl toweled him down and wrapped the terrycloth around his waist. Taking his hand, she led him through the hallways to a room marked 'Guest Coaching Tune-up Suite'.

"These are your private quarters for the weekend. They are fully equipped with a large bed, floor matted yoga and exercise areas, massage table and private garden tub bath. Cabinets and closets contain sex toys, costumes and assorted training aids. You can bring a student here that perks your interest or have your selection from the pool of available students delivered at a scheduled time. Room service meals are served ensuite or you can partake of our gourmet cuisine in the dining room. Any questions?"

"That's a pretty thorough introduction. When would you like a tutoring demonstration?"

Carol was thrilled at the invitation. "I am free right now for your choice of lessons. What would you like me to teach me?"

"Let me think a moment. I think better with my hands occupied."

Edwin reached out and fondled Cheryl's left boob. She stood stoic and watched as he manipulated her fleshy mass. Edwin engaged both hands with both tits and continued his kneading. Looking around, he spied the straight back wooden chair. Edwin drew Cheryl along to the chair using her nipple nubs as mini-leashes. Edwin sat as Cheryl stood before him.

Edwin tapped the globes, not so gently, and enjoyed the jiggle.

"Nice tits. How's your boob-job skills?"

It was a rhetorical question. Cheryl knew her own opinion didn't matter. She would get Edwin's opinion and feedback after he tried her out. Really, that was all that mattered.

Cheryl asked permission to get some lubricant from the bathroom. When she returned, Edwin spent some time working the lotion all over her tits and cleavage and in the process most of her chest. Satisfied with his handiwork, you pushed down on Cheryl's shoulders, signaling her to begin the task before her.

Cheryl used her hands to compress her impressive rack around Edwin's prick. Edwin guided her pace and stroke length with hands and words.

"Nice long ones now...all the way uuppp...and downnnn...that's nice...hold and flutter your tits in counter-rhythm...good...long ones again...can you kiss the tip when it emerges...yes,yes...like that..ohh, that's good..."

Cheryl intently followed his directives and Edwin thought she was performing well. He liked the way her wavy full head of hair bounced gently as she moved her upper body. His growing muscle tautness constricted his throat. He was unable to speak and when she looked up at him, he smiled and nodded his encouragement to her. His heat was up and he was nearing the end.

Edwin heard a knock at the door. Cheryl didn't falter her pace. Despite his clogged throat, he found enough voice to croak out a reply.

"Come in."

A buxom Oriental female pushed a room service cart into the room and went about setting up the lunch. She wore an abbreviated version of the French maid's costume: heels, thigh high hose, and thong panties, a velvet bustier with lace bodice unable to conceal her half-cupped breasts and nipples.

The visual treat brought on Edwin's finale. Edwin blew his load on Cheryl's neck and chin accompanied by a long groan of ecstasy. As he collapsed against the chair, Cheryl followed his movement and held his cock between her warm boobs while his prick shrank and his mind melded again with his body

The black haired service cart attendant took a few steps towards the weary couple and paused attentively in case Edwin had any requests for assistance. Cheryl looked over and saw her there.

"Cinou, please prepare a bath. We need to get Edwin cleaned up before he can dine properly."

Cinou disappeared into the bathroom and the sound of running water filled the background. In short order, Cinou reappeared.

"The bath is prepared. Please tell me if I have done anything incorrectly or if you prefer something different or added."

Cheryl helped Edwin to the tub. She climbed in and they played with soap bubbles degreasing their recently buffed body zones. Cheryl climbed out and Cinou held a large fluffy towel for Edwin. Wrapping it around his waist, Cheryl and he toddled to the lunch table where Cinou performed waitress duties for them. Despite being faced by Cheryl's magnificent pair of tits throughout the repast, Edwin kept taking opportunities to caress Cinou's bare rear, thigh or arm. When Cinou leaned in to refill his glass, his hand followed his gaze down her open top. He fingered the pert nipples and admired the stiff resilience of her erect nubs.

When the food was finished, Cinou repacked the cart. Edwin decided to change venues again.

"Cheryl, would you remove the cart? Cinou will be staying here with me, probably all night. And there was a lissome redhead playing tag in the pool when I came in this afternoon. Have her sent here later tonight."

Cheryl agreed to advise Administration of Edwin's latest selections and choices. They would arrange the logistics and schedules accordingly. She wheeled the food cart out of the room and the door closed to leave Edwin alone with Cinou.

Cinou stood passively beside Edwin as he rubbed her well exposed ass cheeks.

"Turn towards me, please."

Edwin's fingers walked up the laces closing the bustier. Finding the bowties at the top, he pulled them and proceeded to free the laces downwards. The bustier bloomed open like a flower from top to bottom. Edwin removed the garment and tossed it in the corner. He fiddled with the side ties to Cinou's thong and it joined the bustier in a heap.

Cinou stood before Edwin with arms down. Her nipples were dark and large, with the nubs still erect from Edwin's furtive fingering during the meal. Edwin pinched and rolled them. Wearing her heels, Cinou's breasts were eye level with the sitting Edwin. Cupping one breast, he tasted the other. Edwin lapped the whole areola and sucked the nub. Switching sides, he gave her other boob the same treatment. His dick was becoming firm from the activity.

Edwin palmed Cinou's ass as he rose and lifted her up, hugging her against his body. Cinou steadied herself with her own neck hug. Edwin's waist towel dropped away. Edwin straddle walked Cinou to the bed and jumped in, landing with her under him. He angled her around until they were aligned in the middle between the head and foot boards.

Cinou stroked her inner thighs along Edwin's outer thighs, planting her heels on the mattress and positioning her legs and hips to the best angle for Edwin's looming lunge into her small, tight snatch. Edwin captured her mouth with his for a tongue engaged kiss. In a synchronous move, he pushed his tongue into her throat as he pushed his cock into her cunt. The dual penetration was bewitching. Edwin began an even stroke for this first vaginal sex this weekend. Cinou sucked his tongue as she rolled her hips in time with his cock thrusts.

Edwin noted how Cinou took the initiative to supplement his moves. She was vigilant and enthusiastic about delivering his utmost pleasure. Her devotion to Edwin's desires boosted his hunger for her. His blood rushed faster through his head; his quickening heartbeat thrummed his eardrums. Edwin released her mouth to get more air. He was pounding away wildly into her slick, tight pussy. This was his first real coitus today; the previous sessions he considered only foreplay.

Cinou was breathing hard, hoping that Edwin would reach his summit soon. She would stay focused no matter what but, as his passion built, he squeezed her tighter. Cinou's body was constricted by his fervent embrace. Despite the mild discomfort, she was close to her own climax. She wanted to hold out for coincident orgasms that she understood were favored by the male sex companions.

Cinou felt Edwin's body stiffen and then the warm milky liquid rocketed into her womb. She mentally freed her body to burst forth in its orgasmic convulsions. Her ears were filled with Edwin's roar. Her heels enfolded and hauled firmly on Edwin's ass, seizing him in a desperate attempt to hold his cock inside her and prolong both their ecstasies.

Edwin was still erupting jets in her womb as he collapsed on Cinou. Drowning in her carnal stupor, she was further submerged beneath the bulk of her spasming male tutor. Sentience dawned slowly for both of them. Petite cheek rubs were followed by neck pecks. Edwin raised his head just enough for nose rubs and sugar kisses.

When his energy returned to the bare minimum, Edwin rolled off Cinou and lay on his back. Cinou pulled a sheet over them and snuggled her boobs to his side. She would wait until after Edwin was rested before asking him to evaluate her performance. They dozed off.

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A lightening of the room stirred Edwin awake. The suite door was open and faint hallway illumination silhouetted a nude female. His redhead had arrived. He beckoned her to the bed, lifting the sheet so she could crawl underneath. The door swung shut and the room returned to darkness. He put an arm under her red haired head and his next student trainee settled in opposite Cinou and emulated her snuggle. Edwin palmed each woman's outer boob and fondled his way back to sleep.

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Dawn broke. Edwin woke feeling revived and refreshed from his deep slumber. The girls were already awake; such was expected from them as eager-to-learn trainees. They held Edwin's cock in alternating turns, giving soft caresses and brushes. Edwin let them play while he thought through his next lesson plan. He was rested and ready for more fucking. And he had this new redhead co-ed with unknown talents to augment. He was ready to explore and evaluate.

With the next lesson's plan elaborated mentally, Edwin stretched his arms and arched his back where he lay. He removed his arm from beneath Cinou and used both arms to prop up the redhead astride his thighs. Both girls continued taking turns stimulating Edwin's growing cock.

Edwin folded his arms under his pillow and addressed the redhead.

"Cinou will help you mount and then you will work me until I cum in your cunt. I want you to orgasm a couple times before I do. Men appreciate a female who expressions her genuine lust for the selecting male. Show me how much you lust for a robust fucking."

The redhead nodded, fluttering her long straight tresses that fell almost to her waist. Cinou sat up, ready to assist. The redhead lifted her hips and shuffled her ass and cunt forwards to Edwin's stiffened cock. Cinou raised Edwin's erection to vertical and the females carefully lined everything up for a smooth male entry. Contact established, the redhead tapped...tapped...tapped until Edwin was crammed deep in her pussy.

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