Captivating Older Men Ch. 02

A change of plan

Jordyn's shared a revelation about her partner in her previous story. She had fallen in love with Lloyd but celibacy was never part of Jordyn's plans. Wanting to help, Lloyd found professional assistance. But counselling alone wasn't going to satisfy Jordyn's need. What her charming new doctor prescribed was more tempting than shocking. I seemed the perfect solution. Jordyn returns for follow-up therapy and encounters more naughty surprises.

The counselling was great. The therapy even better! Jordyn.

*

Every visit promised another level of pleasure. I was brimming with anticipation at what Maddisyn and I had planned, a cocktail of excitement, arousal and nerves about today's therapy. I entered the wrought iron gate and paused under the veranda with its lovely heritage tiled floor and smiled at the brass sign that simply said 'Doctor Love's Practice'.

The exclusive medical centre specialises in woman's health and wellbeing. It was Lloyd's discovery. He said I deserved the best and thought counselling for my sexual frustration would help. After a couple of sessions my new doctor prescribed sexual therapy. I wasn't under any delusion as I contemplated having sex with him under his warm sensual gaze. I shouldn't have made the appointment. But I like doing things I really shouldn't.

I first met Lloyd at our annual principal's conference six months ago. I'm the association's executive officer and Lloyd had recently become headmaster of a private girls' school. The first thing I noticed was how Lloyd's smile lit up when I met his gaze. Blessed with naturally curly long blonde hair, full and firm breasts and legs that looked great in a dress and heels, I'm use to attracting such attention. But I'll never forget that first smile he gave me.

I felt a definite attraction unlike any man, or woman, before. Lloyd's gorgeous smile and his old-fashioned charm were a pleasant distraction. I've never enjoyed our conferences so much. I easily found reasons to see more of Lloyd. We soon became friends and started dating. Well, that's what I thought until inviting him to stay the night after an evening out. A stunned silence filled the air between us when Lloyd told me he was gay. I had no idea.

I rang the bell on the large stained-glass door and soon recognised the distinctive sound of high-heels approaching. 'Hello Jordyn,' Maddisyn greeted with a hint of eagerness. 'Can I take the clothing bag?' she added, my nervousness evaporating with her infectious smile.

'Thank you . . . Maddi,' I replied, emphasising her nickname. 'I thought you'd call me Jordi,' I added handing her the bag. They were our fantasy names we thought would add a little more fun.

Maddisyn's eyes widened suggestively with my humour. 'We're not dressed for the roles yet,' she softly laughed.

Maddisyn's more like a friend to her Guests than the Practice manager. She's a tall and attractive brunette in her mid-20s with loosely curled hair cascading to her shoulders. She provided a tour of the Practice a few weeks ago and I couldn't help noticing her gorgeous legs in a short skirt and heels. Maddisyn made deciding to register as a Guest a little easier.

My pussy throbbed and moistened as the images in our emails entertained my mind. 'Thank you for your help with the emails,' I grinned as we moved towards the Sitting Room.

'It was my pleasure. I enjoyed the planning actually,' Maddisyn replied and her smile turning a shade playful.

The Sitting Room is lovely for relaxing before an appointment. I enjoy sitting on one of the matching couches in front of the white marble fireplace. A chandelier is suspended from an ornate ceiling and the room feels warm and cosy with pastel colours, soft cushions and fine lace curtains at the bay window. The period furniture and furnishings are stunning.

'Would you like any refreshments?' Maddisyn offered as I took a seat and melted into the luxurious fabric of the couch.

'The white wine I had last time was lovely,' I answered returning her smile. 'Will you have one?' I added.

'I don't usually but I might be naughty,' she giggled and the innuendo not going unnoticed.

I began reflecting on what has prompted me to attend the Practice as I gazed at Maddisyn's swaying hips going to the kitchenette behind her desk. That evening at the restaurant seemed to bind us even closer. I told Lloyd that I was bi-sexual and hadn't met anyone as lovely as him. I eventually moved in with Lloyd and months later the evening became known as our 'coming out dinner' instead of going out for dinner.

Our relationship is a unique situation. Lloyd being much older is an obvious difference and yet uncomplicated, unlike or sexuality. Lloyd's kind, caring and affectionate and he loves me in all but one sense of the word. I just don't ignite that sexual spark. I must have been naive thinking celibacy wouldn't be an issue. Self-pleasure is frustratingly never enough. Our distressing attempt at adult role-playing brought the issue to a head. Darling Lloyd would have made a wonderful headmaster for my naughty school girl fantasy.

Maddisyn soon returned with the wine and a selection of cheese and fruit. 'I thought you may like something with the wine,' she smiled placing it on the antique side table.

'Thank you. It looks lovely!' I exclaimed, enjoying being a Guest.

'I've placed you clothing bag in the Guest Lounge next to mine,' Maddisyn mentioned.

I smiled in appreciation. 'Thanks, Maddisyn. I can't wait to see how you look,' I replied, the anticipation obvious in my voice.

A smile played on Maddisyn's lips with the comment. 'Let me know when you're ready,' she mentioned before returning to her desk.

The lounge is off the Sitting Room and ideal for preparing for an appointment. There's a lovely white antique dressing table and mirror for grooming and makeup with luxurious cosmetics provided. I realised why Guests would want to look their best the moment I met my new doctor. My thoughts drifted to my earlier sessions as I relaxed with my drink.

Doctor Love is so much like Lloyd, just several years older and in his late 50s. They're strikingly handsome for older men and with a charming and statesman-like charisma I find sexually arousing. My new doctor obviously likes the company of attractive younger woman. I've noticed his eyes roaming and enjoyed the attention. 'Maybe I have a thing for captivating older men,' I thought to myself.

The initial counselling was wonderful. I actually felt an emotional burden lifted from my shoulders as we discussed my intimate issues. l would have told Doctor Love anything gazing into those sensual blue eyes. I've never enjoyed a doctor's appointment so much as I shared my naughty headmaster fantasy. After a couple of sessions, things started getting even more exciting.

Doctor Love recommended sexual therapy as if it was common practice! It was obvious what he was offering me. It was wrong for so many reasons but the thought of illicit sex was more thrilling than it was shocking. I knew counselling alone wouldn't satisfy my need. My naughty doctor even suggested Maddisyn join us! My arousal must have been obvious to a sex therapist. The sex was amazing and I jumped at the chance of today's follow-up therapy.

'I'm just going to use the Guest Lounge to get ready,' I mentioned, attracting Maddisyn's attention.

We made our way to the lounge and unzipped the clothing bags. 'It's a shame they're not the same,' I sighed as Maddisyn removed the girl's uniform she borrowed from a Guest.

'I'm from another school and we got caught together a lunchtime,' Maddisyn reminded me.

Doctor Love had proposed role-playing therapy for today's session and suggested Maddisyn and I share some ideas in emails. 'Yes of course. Let's stick to the plan,' I smiled nervously.

I took a deep settling breath and we both stripping down to our white lace underwear. 'Wearing front opening bras was a good idea of yours,' Maddisyn grinned at me.

I shimmied into the school skirt and just managed to do up the button-down blouse. Fortunately, I'd kept the uniform that Lloyd brought home from his school for our misguided attempt at adult fun. Maddisyn had similar difficulty squeezing into her uniform. Being much too short and tight made it even more thrilling wearing them.

I felt incredibly sexy admiring my uniform in the dressing table mirror. 'What do you think about the length of the skirt?' I asked turning around to see my reflection from behind.

'Let's tuck it up a little more and undo a couple of buttons,' Maddisyn answered.

'The dress code developers would have a fit,' I laughed as she made the adjustments.

We check ourselves out again and smiled at our enticing cleavage and breasts straining against the tight blouses. Our long and shapely legs looked gorgeous framed between tall white socks and the short pleated skirts. Just walking in our plain black flats risked flashing a little white lace.

'Oh Jordi, you're such a slutty school girl,' Maddisyn sniggered, impressing me with her immature tone of voice.

'Who had her hand in her panties when we were caught, Maddi?' I mocked just as childishly, causing use both to giggle as if already in character.

We sat in front of the mirror to do our makeup and hair. Maddisyn couldn't help laughing at my futile attempt to pull the hem down after crossing my legs. We had fun laughing and smiling as we went over what we had planned.

Maddisyn set my long blonde hair in a high ponytail with a cute red bow and left a few loose curls to frame my face. 'What do you think?' she asked looking pleased.

'I look like a teenager!' I gasped at our reflections with Maddisyn enjoying my reaction.

I moistened my lips feeling my nipples pushing into the soft fabric of my bra. 'We shouldn't keep headmaster waiting . . . Maddi,' I grinned at her reflection, her arousal also obvious.

We left and made our way to the consulting suite at the back of the building. Doctor Love and I usually sat on the matching couches in front of a lovely open fireplace. I wasn't sure what to expect as we approach the closed door. I glanced at Maddisyn and smiled nervously before I timidly knocked. I only just heard the command to enter over my heart thumping wildly in my chest. We went in and Maddisyn shut the door behind us.

I froze staring wide-eyed at Doctor Love sitting at his antique desk with an academic gown over his suit. 'Are you the two children who were . . . um, carrying on in the school yard?' he inquired, seamlessly commencing the fantasy.

'Yeah,' Maddi sniggered disrespectfully, worthy of an acting award. 'We were told to report to you,' I added with a look of teenager disinterest.

'Call me Sir or Headmaster when speaking to me!' he reprimanded, stirringly displaying the air of authority and position that had inspired the fantasy.

What was unfolding was such a turn-on. 'Sorry Sir,' we answered in unison with our best impression of frightened young school girls.

I felt my panties dampen as Headmaster's eyes lazily drifted over our uniforms. 'Come here children,' he eventually commanded with a beckoning finger.

We apprehensively approached his desk. 'What's your name and what school are you from?' he asked running his gaze over Maddisyn.

'Maddi. Asquith Ladies College, Sir,' she sheepishly replied.

'Asquith has the same uniform standards as our school,' Headmaster commented in a tone matching his displeased expression.

Headmaster's attention turned to me and the trickle was becoming a flood. 'You, young lady need reminding of them,' he said, his gaze having license to roam over my body. 'Your name?' he eventually added.

'Jordi, Headmaster,' I answered, fidgeting with the hem of my skirt.

Headmaster placed a thin wooden pointing stick between my legs and slowly caressed up my inside thigh. 'Skirts come to here,' Headmaster instructed pausing well below the hem.

My heart was slamming against my chest as the pointer continued sliding up. 'Your skirt is here,' Headmaster frowned, the pointer tapping tantalisingly close to my saturated panties.

I took a shaky breath. 'Sorry, Sir,' I gasped.

Headmaster placed the pointer tip in Maddi's cleavage and she breathed in sharply. 'You both have too many buttons undone!' he scolded.

The tip pressed into the smooth yielding skin as Headmaster traced the opening of her blouse. 'Sorry, Sir,' Maddi gasped, her breasts heaving in her exposed bra with every rapid breath.

'Please take a seat on the couch, children. There are some things I want to discuss with you,' Headmaster firmly instructed.

I enjoyed the softness of the upholstery on my backside as we took a seat on the couch, my school skirt refusing to cover hardly any of my thighs. 'Now, what were you two getting up to?' Headmaster asked as he got comfortable on the couch opposite us.

I inwardly smiled noticing Headmaster glimpsing at our cleavage and white panties while feigning being discrete. 'Jordi! Keep your legs together,' Maddi chuckled mockingly.

I crossed my legs and attempted to pull the skirt down my thighs. 'Oh sorry, Sir,' I giggled noticing a slightly devilish smile on Headmaster's lips with my mischief.

Headmaster's roaming gaze was as thrilling as any caress. 'Now, tell me what you two were up to?' he inquired with little concern at being caught.

Maddi and I glanced at each other and chuckled. 'Just kissing, Sir,' Maddi giggled, mindlessly parting her legs to flash a little more lace.

'Yeah, Maddi was all over me like a slut,' I laughed, taking a surprising hit of adrenaline at the crudity.

'Was not!' Maddi shrieked, her legs widening as she turned to scowl at me.

I uncrossed my legs and cool air played on my sodden panties. 'Yes, you were!' I shot back.

'Well, you weren't fighting me off,' she replied with a smirk.

'Girls, girls, please!' Headmaster exclaimed. 'Maybe a demonstration would help,' he added.

Maddi leant into me and kissed me briefly on the lips. 'Is that it?' Headmaster asked, seemingly disappointed.

Maddi looked at me and covertly rolled her eyes. I don't know how I held it together before she wrapped me in her arms and kissed me deeply. The kisses became increasingly passionate, needy and demanding with our heads tilting one way and then the other. Maddi grabbed a breast causing me to moan into her mouth. Our meshing lips opening wide, sucking at each other's lips and allowing our tongues to probe and play.

My body tingled with the sudden caress of Maddi's hand gliding up my thigh as we kissed. 'See what I mean, Sir?!' I squealed before pulling away from Maddi.

I stood up, flicked off my flats and curled up on the couch next to Headmaster. 'She can't keep her fucking hands out of my pussy or hers, Sir,' I teased at Maddi, enjoying the ripple down my spine at hearing the dirty words effortlessly flowing.

'I can't help being horny,' Maddi pouted, lowering a hand to cup her pussy.

A bulge pushing against the fabric of Headmaster's trousers attracted my attention as I turned to look at him. 'Like another demo, Sir?' I asked with a gaze of innocents.

Headmaster nervously cleared his throat. 'Well . . . it might help,' he replied masking his obvious interest.

Maddi's hand slipped down inside her panties to strum her clit beneath the fabric. 'Both hands,' I encouraged.

Maddi rolled in her lower lip as her other hand disappeared into her panties. 'I'm so wet. Listen, Sir,' she moaned with the sound of slippery masturbating fingers disturbing the tranquillity of the suite.

I stretched out and palmed Headmaster's cock bulging in his trousers. 'Oh sorry, Sir!' I shrieked with mocked surprise. 'Maddi's not the only one excited,' I added fluttering my wayward hand to my chest for effect.

I tentatively lower my hand and pressed my palm against the swollen outline. 'Maddi, it's throbbing!' I shrieked again.

'I think Headmaster wants more than a demo,' Maddi managed between gasps and moans.

I unbuckled Headmaster's trouser belt and released the catch. 'You shouldn't be doing this,' Headmaster protested but his voice was dry with arousal.

'What have you got in there for me, Sir?' I grinned, unzipping his fly and then reaching into his underpants.

'Hey, Maddi! Look what I've got!' I shrieked excitedly pulling Headmaster's cock out of his pants.

Headmaster softly moaned as I curled my fingers around the hardened flesh and its sculptured veins and started stroking. 'Like that, Sir?' Maddi teased, watching him squirm with pleasure.

'Yes, but . . .,' he muttered trying to keep the longing out of his voice and his resolve weakening.

My other hand burrowed into his pants and cupped his sac. 'You're a naughty girl,' Headmaster moaned as my moist lips slid over his cock's meaty head.

Headmaster's ass writhe against the couch as my tongue flicked across the tip, tasting the oozing pre-cum. My ponytail then swung wildly as I started bobbing my head back and forth. His moans grew louder as I built up to taking all of his cock while playing with his balls.

Suddenly, my eyes widened with the thrill of my fingertips detecting a tingling sensation. 'Naughty girl,' Headmaster groaned as his cock pulsated against my lips and cum flooded my mouth.

I swallowed and sucked his cock dry before licking my lips clean. 'Oh, wow! I've never had Headmaster cum before,' I giggled at Maddi.

Maddi left the couch to joined me and stared at Headmaster's cock. 'Hey Jordi, look how big and hard it still is!' she exclaimed. 'Nothing like the boy's cocks,' she added chuckling.

'Come on, give me a hand,' I grinned before reaching inside Headmaster's academic gown to grab his trousers.

'Girls, girls, that's enough,' Headmaster pleaded as we pulled his trousers and underpants down his legs.

'We can never get enough, Sir,' I giggled.

I extended a knee over Headmaster's hips and lifted his erection from his stomach. 'It'll never fit,' Maddi gasped.

I pulled the crotch of my panties aside. 'I'll make it fucking fit,' I grinned, feeling his cock twitching against my palm as I aimed it between my thighs.

My eyes widened as Headmaster's bulbous head stretched my pussy lips. 'Oh fuck! Fuck! Fuck!' I cried out with the fullness and friction as his cock pushed deeper and deeper into the sensitive internal flesh.

I tentatively rocked my hips adjusting to the tight fit. 'Oh Sir, that feels so fucking good,' I moaned, taking another hit of adrenaline.

Maddi wrapped her arms around me to unbutton my school blouse as I ground my pussy against Headmaster's groin. 'I've noticed you looking at Jordi's big tits, Sir,' she childishly laughed releasing the strain on the first button fighting against my heaving breasts.

I held headmaster's gaze as each button was released and the blouse eased out of the waistband of my school skirt. I smiled watching him moisten his lips as Maddi unclipped the front catch of my bra and finally peeled the fabric open to allow my breasts to spill free.

'Aren't I a naughty school girl?' I teased, wiggling my breasts at Headmaster.

'I know what naughty school girls want,' Headmaster moaned before grabbing a breast and devouring as much as he could stuff into his mouth.

I moaned feeling the hard nipple throbbing against his probing tongue. 'Oh yeah, suck my tits. Suck them fucking hard, Sir,' I groaned, arching my back to offer more flesh.

I grimaced with the perfect balance of pleasure and pain as Headmaster's lips locked onto the nipple. He then forced a loud moan from me as his mouth pulled, drawing the breast back and tugging until allowing the captured flesh to slip from his lips.

'Is my school girl pussy nice and tight, Sir?' I moaned, grinding my mound into his groin.

'Oh yes, child,' he simply moaned, adrenaline to surge through me with our immoral words.