Captivating Older Men Ch. 02

Headmaster drew the other nipple into his mouth to suckle. 'Cum for your Headmaster, Jordi,' Maddi urged, cupping the freed breast and rolling the moistened nipple between her thumb and finger.

I felt the stirrings of an orgasm in the depths of my pussy, budding and spreading with the threat of engulfing me. I moistened my dry lips and began to pant in anticipation. The nipple slipped from Headmaster's lips and Maddi's other fingers pounced on the discarded flesh.

Headmaster held my enraptured gaze. 'Do you like being a naught school girl?' he asked.

I had to remind myself to breath. 'Yes . . . Sir,' I gasped hungry for air.

'Teasing me the way you're wearing your school uniform?' Headmaster continued.

'Yes . . . Sir,' I gasped again.

Every part of my being was caught in a tidal wave of tortuous pleasure, surging towards a climax. I could feel the pressure building inside me and my heart was racing.

Every thrust against Headmaster's groin brought me closer. 'Who am I, Sir?' I muttered breathlessly.

'You're a naughty school girl,' he answered.

My trembling body was pleading for release. 'What am I doing to you, Sir?' I grimaced as I teetered on an edge.

'Riding your Headmaster,' he grinned teasingly.

I used what little self-control left to prolong the ecstasy. 'Dirtier. Tell me!' I shrieked.

'Fucking your Headmaster's cock, you school girl slut!' he exclaimed.

My mind and body couldn't hold back the illicit thrill cursing through me with the obscenities. I was gone, my pussy convulsing around Headmaster's cock. My eyes firmly shut and mouth wide open and gasping for air, I rode out the sensation until the climax finally subsided. I collapsed against Headmaster's chest, panting for breath and cradled in his arms.

'Go to my desk and bring me one of the boxes in the top draw, child,' I heard Headmaster instruct Maddi.

That wasn't in the emails! I watched as Maddi returned with a long and narrow box, intrigued but also a little concerned at the change of plan. 'Here, Headmaster,' she said sitting on the couch and handing it to him. Surprisingly, Maddi appeared unfazed.

The fantasy seemed to have a life of its own as Headmaster opened the box and removed a double-ended dildo! My mind processed the options. Was it going to be school girl and school girl? School girl and Headmaster and if so, who? Was it Maddi or me? My mind frantically searched for any other possibilities.

I soon had the answer with a return to the plan. 'Do you like my tits, Sir?' Maddi grinned starting to unbutton her blouse.

'You're well developed for a school girl. Beautifully, actually,' Headmaster replied.

Button by button, Maddi's ballooning breasts nestled in her white lacy bra were revealed to Headmaster's gaze. 'Would you like to cum on them, Sir?' she teased, sensually biting her lower lip.

Maddi unclipped the bra and peeled open the fabric to release her full and rounded breasts, formed tightly at the chest and tipped with large rosy-red nipples. 'Yes child,' he simply exhaled before handing me the dildo and a tube of lube.

I took a moment to compose myself as Maddi shimmied down the couch on her back and Headmaster straddled her waist. 'Lube up, Jordi,' Maddi chuckled over Headmaster's shoulder with him bent over her.

'Should I end the fantasy?' I pondered to myself.

I took a deep breath and decide to go with what was unfolding. 'It's not me that's going to need the lube,' I grinned slipping the dildo into my moist pussy.

I squirted a generous amount of lube onto my hand and stroked the cock hanging between my thighs. 'Don't want lube on your academic gown, Sir,' I chuckled, lifting it out of the way.

Headmaster flinched with the cold sensation of my finger applying lube to his asshole. 'Relax Sir. Just a little lube,' Maddi teased and giggled.

I caressed the head of the dildo around Headmaster's asshole, spreading the lube around. I'd never done anything like this with anyone. My first tentative toying of my pussy was the only experience I had to draw on. I eased the head past his sphincter, forcing a low groan of pleasure as I eased the dildo inside. The fit seemed to loosen as my hips established a gentle rhythm.

We soon had a mutual deep penetration, sharing the dildo and the same source of pleasure. 'Ooh yeah. I love fucking your ass, Sir,' I serendipitously moaned with the sensation.

I draped myself over Headmaster's back to place his cock between Maddi's breasts. 'Cum on her big school girl tits, Sir,' I urged, my slippery hand pumping the hardened flesh.

My hips thrusted into Headmaster's ass as my grip pistoned through the tight cleavage. 'Cover them with cum, Headmaster,' Maddi giggled.

'Is this what you want, child?' he uttered, his seed then hitting Maddi on the neck and a stream of sticky wet cum meandering across her chest.

More droplets added to the cum seeping into Maddi's cleavage as I milked Headmaster's cock dry. 'Oh Sir! What a load! Thank you, Headmaster,' Maddi grinned.

I pulled the dildo out and Headmaster climbed off the couch, struggling to stand up with his trousers still around his ankles. 'I've never met such naughty school girls,' he gasped.

'And you're a naughty Headmaster, Sir,' we both giggled, signalling the end of the fantasy and the three of us softly laughing.

Maddisyn stood up clutching her breasts to contain the flow of cum. 'How about a shower to get you cleaned up?' I suggested. 'I'll return the favour from last week,' I added smiling knowingly.

'Use the ensuite. I'll collect your clothing and leave them in the bedroom,' Doctor Love suggested.

Last week's shower sex wasn't the only thing on my mind as we went to the bedroom off the suite. 'Did you know about the dildo?' I grinned at Maddisyn.

'No, but I wasn't surprised. Doctor Love sometimes includes clinical procedures that provide therapeutic benefits for Guests,' she replied, sounding plausible and without the slightest hint of anything wrong. I almost believed it for a minute as we entered the ensuite.

I took a moment to bask in the wonderful facilities as Maddisyn adjusted the shower. The patterned heritage tiles and contrasting antique brass tapware looks lovely and the white roll-top bath with claw feet is amazing. The old-fashioned white dressing table has a beautifully decorative mirror frame and a gorgeous selection of cosmetics.

We stripped out of our uniforms and the steam embraced us like a warm cloud as we stepped into the wonderful shower. 'I'll soon get you clean,' I smiled working gel into my hands as the warm water cascading over our bodies.

My palms roamed over Maddisyn's soft and youthful skin, coating her neck, shoulders and arms in a lather of fragrant white foam. I loved the feeling of my cleansing palms and fingers then gliding over the curves of her breasts and exploring the depths of her tight cleavage.

Our eyes locked as a hand swept over a hardened nipple. 'It seems a little unfair that I had most of the fun,' I teased.

'What are you suggesting, Jordyn?' she grinned with an eyebrow curiously raised.

My finger returned to circle the aroused flesh sprouting through the soapy suds. 'I don't remember the therapy ending before you helped me shower last week,' I flirted.

My hand teasingly following the stream of bubbles flowing between Maddisyn's breasts to coat her stomach before running over her mound to cascading between her thighs. 'You know I enjoy providing Guests what they like,' she finally replied holding my gaze.

Maddisyn rolled in her lower lip as my cleaning palm caressed between her thighs. 'What would you like?' I asked noticing her breasts starting to heave excitedly.

Suddenly, I shrieked playfully as Maddisyn pulled me into her embrace. 'The same thing you like,' she giggled at my reaction.

Our bodies clung together, the softness of our breasts pressed against each other as Maddisyn wrapped her arms around me. Our kisses were tender at first and then increasingly passionate and demanding as our lips moulded into each other.

Maddisyn parted her legs invitingly as my fingers teased her pussy lips. 'Oh Jordyn, just finger me,' she gasped drawing breath.

I grinned watching Maddisyn's exaggerated eye roll as I inserted two fingers. She returned my grin before capturing my lips and working a hand between my thighs. Our locked lips stifled our moans as we finger fucked each other with the water streaming down our bodies to flow through our stroking fingers.

Suddenly Maddisyn began gasping for air, her body trembling against mine as my fingers worked her to the verge of ecstasy. Then her stomach convulsed uncontrollably in my embrace as she rode out the climax, whimpering and sighing until the very last wave of pleasure subsided.

Our lathered palms roamed over each other's soft and silky-smooth skin, both of us smiling and laughing as we tracing the curves of our bodies. Finally, raising our smiling faces to the stream of warm water and allowing it to cascade down our bodies to rinse the foamy suds away. We dried ourself and sat at the dressing table in white cotton bath robes and slippers smiling, laughing and talking about the role-playing as we did our hair and makeup.

Maddisyn went to the bedroom to collect our clothing bags. 'I'll leave you to get dressed and continue the consultation,' she smiled, handing me my bag.

I got dressed and returned to the suite. Doctor Love was sitting on the couch and obviously writing up my case notes. 'Could you mention I enjoyed helping Maddisyn with showering?' I asked, imagining her smile when typing up the notes.

A smile slowly crept across his face. 'Yes, certainly,' he replied.

'I'm sorry for swearing. It's so unlike me,' I apologised sitting down on the couch opposite.

'You seemed to find it . . . stimulating,' Doctor Love commenced counselling.

'It wasn't my only surprise,' I answered with a coy smile.

'Tell me your thoughts on the therapy?' he continued.

'You both made it so realistic. It was amazing,' I replied, the excitement obvious in my voice. 'Enjoyable as well,' I added raising my eyebrows and grinning.

Doctor Love smiled at my reaction and paused thoughtfully. 'What makes it so exciting?'

'The immoral situation, skimpy uniforms, teasing you and taboo sex,' I answered without hesitation.

It's easy talking with Doctor Love and sharing what turns me on, our sexually charged discussions often as exciting as they are enlightening. He just seems to guide the conversation with skilful prompts and questions. What we started unpacking was amazing. There was obviously more to my fantasy that some sexy fun.

'My headmaster and student thing is probably obvious give my work,' I contributed.

'Others like different scenarios, usually involving abuse of authority or trust and exploiting vulnerability. Age differences can emphasis the disparity in power and control,' he explained so articulately.

'I seem to have a thing for captivating older men with a presence,' I replied, causing an acknowledging smile.

'I observed some personal traits that gave insight into why you find the fantasy erotically arousing,' Doctor Love mentioned. I just sat there as he continued to amaze me.

It wasn't just the inappropriateness of what we were role-playing. 'You experienced the thrill of being helpless and intimidated. But even more arousing was overcoming the imbalance of power and authority,' Doctor Love explained.

Doctor Love continued to astound me with his perceptiveness. I loved the thrill of exploiting my body's sexual allure, seizing back control over headmaster's abuse of authority and a position of trust and using him for my own sexual pleasure. It all seemed so obvious after our discussions.

'I don't condone what we acted out. It's just a fantasy,' I said with a tone of concern.

'Perfectly normal adult fun when confined to the bedroom,' he smiled reassuringly.

Discussing the role-playing and listening to his analysis, I was starting to wonder if Doctor Love actually believed in sexual therapy. Maddisyn said last session that other Guests benefited from the therapy. She also mentioned earlier that Doctor Love sometimes includes clinical procedures for Guest's therapeutic benefit.

'I was also surprised with the change of plan, the sex toy?' I commented giving him a teasing look from beneath my eyelashes.

'Role-playing is also an opportunity to experiment and having new experiences. May be something to share?' Doctor Love replied with a not too subtle hint.

'It was surprisingly pleasurable,' I answered with a grin creeping across my face at the possibility.

I recognised the subtle smile that always forms on Doctor Love's face when his thoughts we proven correct. 'I have another unopened box you can have,' he offered before going to his desk draw.

'You think of everything, doctor,' I smiled as he handed it to me.

'Email Maddisyn how things work out. We'd both love to hear,' Doctor Love smiled, accompanying me out like a perfect gentleman.