How to Train Your Daughter Ch. 14

Story Info
I help a friend celebrate a special girl’s special day.
25.6k words
4.42
65.8k
36

Part 21 of the 22 part series

Updated 06/09/2023
Created 04/23/2020
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

For Miss E, who is an excellent trainee and a very good girl, and who has inspired more of this little world than she knows. Thank you.

Thank you to all my readers, and please don't hesitate to write me anytime; I love to correspond. Just remember to add your email to the PM if you want a reply; they are anonymous by default :-)

Authors note: This story, like all the chapters of this series, contains graphic scenes of men in sexual situations with their own daughters, as well as some nonconsent/reluctance. I understand completely if these don't appeal to you, so please be warned. All characters are over 18.

* * * * *

The sun was warm and golden in the balmy Indian summer Saturday morning as my good friend Dave Kendrick and I pulled up in front of a lovely old colonial house, whose stone steps ran down the steep hill of the broad, shady front yard to the street.

'Hey, thanks again for helping me with this little project,' he said. 'I know this will be a wonderful memory and a helpful lesson for Emily.'

I chuckled and assured him I was happy to be of assistance, and that I'd been looking forward all week to enjoying the special girl we had come to pick up.

In addition to being a firefighter and owning a small business downtown, Dave was also the girls' soccer coach and the physical education instructor at Stonewall Academy, the high school both our daughters attended.

He'd met Emily Fox last year, her final one at the Academy, when she'd wandered uncertainly into the gym between classes in her schoolgirl uniform and puzzled awkwardly about some of the machines, clearly without any idea how she was meant to use them.

She was a quiet, introverted girl by nature, highly intelligent and academically focused, but she had begun to have misgivings about her body and her poise as her Festival drew near, and despite the intimidating nature of the weight room to the young girl, she had resolved, with her characteristic pragmatism and her faith in the scientific bent of her own capable brain, to figure it out.

Dave had kindly, respectfully helped her learn to use some of the equipment, and she had fallen in love with working out as she mastered the movements and exercises and nutrition; she became a frequent visitor to the gym, and he had continued to assist her with tips and plans that matched her expanding abilities and goals.

She was ecstatic as she felt her strength grow and saw her body change, and Dave was happy to see the once shy, insecure girl walk taller, smile more confidently, and begin to wear clothing to the gym that displayed and flattered her transforming little body, typically doing her workouts now in the tiniest of booty shorts and a little bra that did nothing to hide the curves and features of her pleasantly large breasts.

He was filled with pride at how she had begun to blossom into a strong, self-possessed girl, and it was clear as he described her to me that he was quite taken with her.

She'd celebrated her Festival a few weeks before graduation, and Dave had been delighted to have the chance to fully enjoy the beautiful, strong body she had built with his guidance, and to give her several vigorous, advanced lessons in the weight room and in the girls' showers before she left for summer break, and then on to university.

He hadn't expected to see her again, but a few weeks after the semester started he'd received a beautifully written letter from her, explaining that while she was excelling in her college classes, she was struggling greatly in her sexual training.

She was still painfully shy, and she knew that the men who were training her now could tell how anxious and flustered she got every time they stripped her down for a lesson, despite her earnest and tortured attempts to relax and let them enjoy her naked body to the fullest.

There were still parts of her body that she was enormously insecure about, and which she could do little to change through exercise and good nutrition; she was particularly sensitive about the appearance of her vulva which, because it didn't look like the simple, innocent peach slits she heard men enthusiastically discuss amongst themselves, was a recurring source of consternation for her in the moments when her trainers would peel her panties down her thighs for the first time; and she sometimes had minor panic attacks as she reluctantly let men look at and investigate her vagina, which made it even harder for her to focus and relax in her lessons, unfortunately often leading to the need for her to be disciplined by the men handling her.

Her sensitive temperament meant that her spankings rarely had the desired effect, and generally only exacerbated her insecurities; she knew it was her responsibility to trust her trainers and freely give them her body for their pleasure in whatever way they saw fit, but she was having a very tough time.

She also felt she had trouble with attention to detail about her grooming and clothes, and she was jealous of the girls at school who always seemed effortlessly put-together, and was worried that men care about those things a lot, and in all, she was feeling pretty defeated about most of her lessons.

A young girl's training career was supposed to be an extraordinary journey of discovery and purpose, but poor Miss Emily only felt like she was floundering.

Dave had made a deep impression on her, both in the interest he took in her fitness instruction, and in the way he'd let her express her gratitude for his efforts by giving her strong, trim little body to him in nearly complete abandon, with nothing but encouragement and adoration for her as she worked her hardest to say 'thank you' by giving him the best orgasms she possibly could as he trained her.

She trusted him more than any other man she knew, she wrote in her letter. She said she totally understood that he was already very busy with his training responsibilities and the many girls to whom he gave lessons each week, and that she knew she might not be as beautiful or skilled as a lot of the other young girls he got to handle and enjoy, but she ended by asking him sweetly and respectfully if he would consider being her mentor, even if only for a little while, to help her overcome her fears and do better in her lessons.

A letter like this from a girl was a great honor, and Dave had written back saying that he was delighted to be asked, and that he was more than willing to take her under his wing for a bit as she adjusted both to college life, and to her important and challenging duties as a sexual trainee.

Now they corresponded regularly; he assisted her in picking clothing and underthings that best flattered her figure and made her feel desirable, and she would send him pictures or videos of her naked body and of her outfits before she left her dorm for training appointments, so he could inspect her and ensure she was properly groomed and attired for her trainer's pleasure; and it gave her immense peace of mind to know that Dave approved of the state of her girl bits and her clothing before she met with a new trainer for the first time, and let him handle her.

She would write Dave short, detailed reports of her training sessions, relating what she had learned, and how her trainers had chosen to enjoy her body, and any feedback they had given her on her performance, and she could ask him any questions, or voice any apprehensions, and he'd always calmly assure her she was on the right path, and becoming a better and better girl every day.

She drove back to Stonewall every other weekend to stay at her parents' house, and Dave would spend some time with her reviewing the skills she'd learned from her other trainers, and assessing her developing abilities by putting her lovely little body thoroughly through its paces, giving his frank valuation on where she was improving, and what areas she should spend more effort working on, as she continued to strive to be the best girl any man could want to enjoy—which, after all, she was made to be.

She had made great strides under Dave's firm mentorship, and today was her birthday.

She'd gotten much more comfortable with allowing men to handle her and couple with her, and she'd recently shyly confided a few times to Dave, in sweet moments of quiet, unguarded afterglow, that she'd begun to fantasize about servicing two men at the same time, which flummoxed her.

She'd had considerable difficulty transitioning to even her basic sexual duties after her Festival, and she'd never imagined she'd be the kind of girl who wanted to share her body in that intimate way with more than one man at a time, though it was only a matter of time before some men would eventually select her for such lessons anyway; but as Dave's steady hand and constant encouragement deftly cultivated and heightened her naturally deeply-seated mating instincts, she'd begun to embrace ever more authentically her beautiful, fundamental purpose as girl, which was simply to bring great pleasure to men with her body.

With long practice and trial-and-error, she had been amazed to begin to discover how responsive she was to the pleasure of her handlers; as they became more aroused and euphoric while enjoying the charms of her body, her own orgasms would begin to send her to another place as she embodied her reason for existence as a beautiful vessel of ancient pleasure in the shape of a girl.

Now she was beginning to glimpse how profound a fulfillment of that purpose it would be to offer herself, completely and utterly, as nothing but a naked, receptive young female, for the primal pleasures of two eligible, grown-up men who knew how to make the best use of a girl's willing, fertile body and mind, and she couldn't get the idea out of her head.

She had been a very good girl lately, and Dave knew that she was ready for more advanced lessons, so he had decided to reward her with a birthday surprise; he had told her, to her heart-fluttering, trepidatious delight, to make sure she dressed nicely and groomed herself well this morning, because he was bringing a friend to help teach her to please both of them, together, as part of her special day.

A girl's birthday called for dressing up of course, and we had both chosen some of our nicest suits; I wore a dark blue check with hints of purple that flattered my athletic frame and long shock of blonde, and Dave cut a dashing figure in an urbane cocoa that set off his well-groomed red fireman's mustache and twinkling green eyes perfectly, and he grinned in anticipation as he turned off the ignition and we strode up the stone walkway to the door of Emily's parents' house, and Dave knocked.

A trim, reserved man opened it and invited us in with a smile, shaking Dave's hand warmly and introducing himself to me as Emily's father, Dr. James Fox, before calling up the stairs to his daughter to let her know we were here.

'She should be almost ready,' he explained. 'She just got back from the gym.'

Just then we heard a door open above the landing, and dancing down the stairs came one of the prettiest little creatures I had ever seen, throwing herself into Dave's arms with a joyous cry, kissing him deeply and kicking up her feet behind her as he hoisted her easily into the air with a booming laugh.

'Dear Miss Emily, you look marvelous—happy birthday,' he said.

I was even more glad that I'd accepted Dave's invitation upon seeing his trainee for the first time; she was quite petite, with dark shoulder-length hair she'd gathered back into a charming little ponytail clasped by a yellow ribbon, and gentle brown eyes, adorned with just a modest sweep of mascara on her long lashes (the only makeup that she wore, aside from a demure touch of lip gloss), that shone from behind a large, fetching pair of glasses perched on her defined nose.

Beneath her excitement at seeing her mentor, she possessed the serious, matter-of-fact demeanor of an intellectual girl; the care and precision of every aspect of her dress and grooming, while excellent, also hinted at the effort and practice that had gone into her appearance, and she struck me as a girl who was generally most at ease tucked away in a hidden corner of the library with a messy bun and an oversized sweater, her pencil nibbled gently by her teeth. She had clearly committed herself to expanding her horizons, however, and she was lovely.

She was dressed simply but adorably in a flouncy white-and-yellow floral sundress that tied in the front between her breasts, and that just managed to be long enough to keep her pert, sculpted bottom mostly covered, and made no effort to disguise the fact that she was braless; her generously proportioned breasts, comfortably filling the low-cut neckline of her dress, were all the more impressive for the diminutive, shapely body they adorned.

Her father leaned close to me as we watched his daughter greet her mentor after their two weeks apart.

'Thank you for doing this. Dave has been so great for Emily—she's a changed girl since she started working under him, and it means a lot that he's taken such an interest in her growth and training. I'm glad he decided he wanted to be the one to teach her how to serve multiple men, and I know you fellows will make this a great birthday for her.'

I said the pleasure was mine, and that Dave had only ever spoken warmly and fondly about Emily, and seemed quite proud of her hard work and dedication to her training. I thanked him for raising such a lovely daughter, and assured him I was very much looking forward to enjoying her body, and was happy to teach her anything I felt would be good for her to learn.

Dave lightly set her down in her white strappy heels with another kiss and stepped aside, gesturing to me with an open hand.

'Emily, this is Mr. Stevenson,' Dave introduced us. 'I brought him to help me celebrate your birthday like I promised—Robert, Miss Emily Fox.'

Emily, still with her hand affectionately resting on Dave's chest, noticed me for the first time; her quizzical expression froze briefly as she took me in, and the meaning of Dave's words fully dawned her, and she realized she was getting her first glimpse of the second man who would be training her today.

Slowly her eyes widened and a delighted, disbelieving smile danced on her lips, and she looked from me to Dave, and back again.

Dave chuckled, his big hand resting warmly on her small shoulder.

'Well, sweet thing, do you like him? I picked him out just for you,' he teased with a wink.

I'm not a small man; I'd spent my earlier years in personal training and construction, and at a little over six foot, I wear most of my two hundred twenty-odd pounds as muscle, and my blue eyes smiled at Emily from behind my rich blonde beard, their twinkle of appreciation for her gentle, sensible beauty perfectly complemented by the Milanese cobalt of my fitted suit.

Emily looked back up at Dave, her eyes wide and full; though whether it was from her excitement at seeing me, or from trepidation at the knowledge that today she would be handled by two men for the first time in her life, or from some potent combination of the two, I wasn't sure, and I could just make out her stumbled, whispered response to her mentor.

'Yes, sir, Mr. Kendrick—oh my gosh, he's...really...handsome—thank you, sir! Thank you so much...I didn't think you were actually going to do it—oh my gosh, I'm so excited, Mr. Kendrick!'

I chuckled to myself at her discombobulation as she realized how completely Dave was committed to her success as her mentor, and how seriously he had taken her birthday training, and of the new, somewhat frightening experience that awaited her today, which she found herself inexplicably longing for despite her shy, innocent misgivings.

Dave laughed again, and patted her on the behind.

'Well, remember your manners dear girl, and go introduce yourself to him.'

She composed herself for moment, smoothing her sundress and pushing her glasses up her nose and clasping her hands behind her back like a good girl before walking across the room to me, a bright smile on her lips, and politely offering her breasts to me in greeting as she said it was good to meet me, and that she was looking forward to sharing her body with me later today, and that she hoped I would enjoy handling her.

I found myself falling under her spell. She was delightfully sweet and earnest in her efforts to be a well-behaved and desirable girl; and my smile softened as I realized how hard the shy little creature must have worked to become this brave and confident, as she maintained her composure beautifully while presenting herself as an obedient, willing vessel of delight to a man she'd never met, and who, at the direction of her mentor, was going to challenge her body and mind today in ways she'd never before experienced.

Dave and her father looked on approvingly as I expressed my pleasure at meeting her with a warm, courteous smile and a gentle, slow, introductory kiss, and softly caressed her breasts over the thin cotton of her sundress.

She was well-endowed, though not disproportionately so, and her breasts rested pleasantly in the hands with a palpable weight to their full undersides; her nipples were clearly well-developed, and even the tight confines of her sundress, struggling somewhat to contain her generous bosoms, were unable to mute the prominent, insistent efforts of her nipples to make their presence known through the thin fabric.

Her dress was in fact light enough that I could clearly see, to my delight, that she possessed lovely, large areolas; and though she had elected not to wear a bra, the dark silhouette of her panties flitted enticingly beneath her short skirt.

I continued to enjoy the feel of her breast in my hand, and I brushed her nipple with my palm and tested its sensitivity with a few progressively firmer squeezes between my thumb and finger; as I reached her first pain threshold, she gasped silently, admirably maintaining her composure and fighting the urge to flinch or shrink away as I took her gently by the chin and tilted her head to one side so I could examine her delicate profile, and the exquisite lines of her jaw, and the long, elegant muscles of her throat and neck, where her heartbeat visibly pounded beneath her soft skin as she submitted, breathlessly trembling, to my first inspection of her little body.

'What a good girl,' I said quietly, kissing her again with a smile. 'Dear Miss Emily, I am very much looking forward to spending your special day with you and Mr. Kendrick. He's told me a bit about you, and how diligent and committed you are in your lessons, and I can say right now that I am already very impressed with you. I think you're going to be a pleasure to train this afternoon.'

She beamed, ecstatic that her long, hard training from Dave was paying off.

'Thank you, Mr. Stevenson. I will try my very best for you, sir, I promise.'

Dave spoke up, satisfied that I had decided his adorable little trainee was worth spending my time handling.

'One of Emily's biggest battles has been understanding that her body in general—and especially her vulva—are beautiful and desirable to the men who select her for training, and a lot of the work we've done is to help her feel more comfortable with being looked at while she's naked, and having her cunny viewed and touched without losing her nerve, and instead working on helping her feel excited and receptive when asked to show men her girl-parts.'

Emily blushed as she listened quietly, and father nodded appreciatively.

'Like I said, Dave has really helped her turn things around—she used to get so anxious just knowing a man had reserved her for a training session, let alone some of the issues she'd have while he was trying to enjoy her body. I'm super impressed with how she just greeted you; I always knew she could be a great trainee, and it just took some good guidance from a strong, trustworthy mentor.'

123456...8