The Headmaster's Office 02: Fantasy Night

"Oh my God!" Trish blurted. "It's Raw-----." She stopped herself just in time. My heart skipped a beat; she nearly named Rawhide, ending the game and blowing my plan out of the water. I was getting too cocky (pun intended), letting them know I had a strap-on.

"Guess?" I asked Mandy.

"I'm thinking. Get your mystery man to fuck me some more while I think." Brassy! You go, girl!

Obliging, I started stroking back and forth, fucking her doggy-style, the inner dildo squirming inside my own pussy every time I changed direction. It was a wonderful, powerful feeling to be fucking like a man; it occurred to me that no matter whether a woman is on top or bottom – or who's calling the shots – she's still the one getting a fucking, not the one giving a fucking. I was beginning to see the attraction.

I looked back to check on Mr Gallows. He wasn't even watching; his eyes were locked on Rupali crouched next to Mandy. Listening to Mandy and I fuck, she had snaked a hand between her thighs and was rubbing her clitoris; with each stroke her labia opened and closed, showing her wet folds to Mr Gallows. He looked down at me, questioning. I nodded silently, yes, that's for you, be patient.

My own excitement mounting, I pushed forward harder, the cup of Rawhide's base now bumping Mandy on the bottom, deliciously jolting the smaller dildo inside me. I wanted to reach under and rub her clitoris, but didn't dare, I had already way overstepped the line. She stayed silent but I could feel her body tense with an approaching orgasm. Bringing out my inner-caveman, I grabbed her hips tight and thrust roughly all the way into her. She arched her back as she silently came, tendons standing out in her neck with the effort not to make a sound. Good girl. I slid out of her and released her hips.

"Time's up, Mandy," I said.

"Well, I'd guess it was a Strap-On, but I didn't know we had one. So I'm going to go with the mystery-man ... James Bond," she sighed.

"Wrong again. Your turn, Rupali." I stood up and sucked in my tummy so I could step out of Rawhide without unbuckling.

I looked at Mr Gallows; he was just about shaking with excitement from watching me fuck one girl while another massaged her shaved pussy in front of him. I felt his cock, it was hard as stone, pulsing with his raging heartbeat and dribbling pre-cum. I put him silently into my mouth, getting an exciting taste of his lubricating seed.

I guided him into position kneeling behind Rupali and held up one hand. Stay! I crept around in front and crouched down so that my mouth was right beside her ear. I looked up at Mr Gallows and held up two hands, miming a doggy-style grasp. Understanding, he placed his hands on Rupali's thighs and ran them slowly up to her hips, pulling up her nightie, moulding her curves and feeling her firm, smooth flesh. With his hands now on her hips where they narrowed into her waist and that monster nine inch cock poised just an inch away from her pussy, I leaned back towards Rupali's ear and breathed "Fantasy night, Babe. Shall I block your ears? Or do you think your tongue's not up to it?"

She jumped like she'd been hit with a cattle prod, but stayed silent. She lifted the blindfold of one wide brown, flashing, eye and glared at me in terror. I held her chin so that she couldn't look around and leaned in close again. "It's OK," I breathed. "I trust him. You trust me." She stared at me a moment longer, then visibly relaxed, nodded and pulled the blindfold back down.

"I'll have the James Bond treatment too, please Belinda," she said in her rich, musical tones. "I'm looking forward to it." I nodded at Mr Gallows. All clear. He guided his cock into Rupali's steaming pussy and immediately set up a rhythm fucking her with the first half of his massive shaft. Rupali reached forward, feeling for me. She slid one hand between my thighs and grabbed my bottom, guiding my swollen labia to her mouth. She gave me few tentative licks, tasting my juices ... has she done this before? Probably not.

I looked up at Mr Gallows; I wanted Rupali's tongue in my twat, but I absolutely needed to see his weapon in hers. Holding Rupali's head by the ears, I grudgingly pulled her away from my pussy. I guided her up off her elbows and then quickly, silently slid down backwards beneath her, thighs parted around her head. I slid her nightie up to her shoulders to expose her large breasts, the nipples erect and brushing against me. I arched my back and pulled my nightie up to expose my own breasts, our nipples now touching and rubbing against each other.

I looked up to check on Mr Gallows, 6 inches of his iron member now stroking commandingly into Rupali less than a foot away from my face. Rupali resumed her assault on my pussy, sucking my clitoris and pushing her tongue deep inside, trying to fulfil her promise to make me come out her ears. She started rocking back and forth onto Mr Gallows, rubbing her heaving breasts against mine and concentrating her tongue and lips on my burning clitoris while the tip of her nose probed my pussy lips.

I was too short to reach her pussy with my mouth so I reached up both hands, massaging her clitoris with one thumb and cupping and gently squeezing Mr Gallows balls in the other.

All this was done in relative silence, maintaining the charade for the other girls that I was kneeling behind Rupali, feeding Rawhide into her pussy.

"I think maybe there's more, Belinda," she asked. "I'd like all of it now, please." Mr Gallows stopped thrusting, keeping six inches in Rupali's twat. He leaned forward a little, slipping another inch in. "Is that all of it?," she asked.

Trish: "What did I tell you about asking that? Guys don't dig it, especially not mystery men like James Bond." If only she knew.

Mr Gallows pushed another inch in, making Rupali gasp in surprise – just one left in reserve now . "Oh my goodness! There is more!" her voice rose half an octave as I felt a shiver run through her body. When I thought she was ready, I increased my grip on Mr Gallows balls and pulled in gently. Following my lead, he leaned forward and buried his entire cock deep inside her hole, pressing hard up against her buttocks. She vocalised a little shriek, then quickly masked it with "Ah yes, I thought that was all there was. Move it again please Belinda, as you did before."

Mr Gallows slowly slid all 9 inches out; Rupali's pink folds tightly gripping his cock as he withdrew, then he plunged strongly back in again, balls-deep. He repeated, thrusting deeply, building up the tempo as I tried to stop his swinging sack from slapping against Rupalis groin. – a sound I couldn't easily explain to the others. She lowered her head back down to my pussy, probing me deeply and grinding her chin into my clitoris. I felt my orgasm building and – still holding Mr Gallows with one hand – I reached around with the other, roughly grabbing Rupali's head and pushing her tongue deeper into my molten core.

Rupali redoubled her efforts, straining tongue flicking and probing deep inside my tight pussy. I tipped over the crest of the orgasm and floated weightlessly down the other side, fireworks of ecstasy exploding in my womanhood, my juices mixing with Rupali's saliva. I wanted to scream but couldn't, so I just held my breath and hugged Rupali – her breasts crushing mine – until I had control again.

Mr Gallows kept pounding his enormous length into her pussy (where did it all go?), pulling each stroke at the last moment and just touching his pubis to her bottom without making a sound. If it wasn't happening right in front of my face, I would never have believed that such a monumental fucking could be administered in complete silence. I guided Rupali up off her elbows so that her swinging breasts would brush against mine, teasing her hard nipples. Then, still cupping Mr Gallows balls – although I was having trouble keeping up with his powerful thrusts – I moved my free hand back to work on Rupali's clitoris, rubbing and gently pinching in time with Mr Gallows' pumping cock.

I felt Rupali's body stiffen as her climax – her second ever and first with a man - approached. She arched and pushed back, raising her bottom and dropping her head back between my thighs. We were close to the end now; Mr Gallows has few sexual weaknesses, but a coming woman impaled on his cock is one of them – if I come first during lovemaking then he will follow seconds later. Even in the silence he would feel Rupali's building climax and would be powerless to suppress his own.

Tremors shaking her body, Rupali wrapped her arms around my raised knees and squeezed them tight around her ears, trying desperately not to scream. On cue, I felt Mr Gallows' balls draw up ready to pump Rupali full of cum. He gave one more deep thrust, pumped his balls, and I felt his semen race past my fingers and through his cock on its long, long, journey to the depths of Rupali's womanhood. He withdrew about half way and then buried himself again, timing each stroke now to the pump of his balls, delivering each powerful jet of cum to the extreme depths of Rupali's vagina.

When their spasms abated, Mr Gallows left his cock inside Rupali and ran his hands over her waist and shoulder blades, then down to cup and squeeze her large breasts, silently thanking her for what they had shared as they basked briefly in the afterglow of sex. The other girls remained blessedly silent; Mandy presumably allowing Rupali to enjoy Rawhide as she had, and Trish trying to decide whether she wanted a fucking from her best friend or just guess Rawhide and end the game. Their patience would soon run out though. I scooted backwards as I guided Mr Gallows' long cock all the way out and wrapped my lips around his softening length, pumping and sucking the last of his semen into my mouth to avoid a cleanup.

Releasing him, I quickly slid all the way out, stepped forward with my lips next to Rupali's ear and breathed: "Rawhide" as I pulled her nightie back down over her bottom.

Out loud, I said: "How about a guess Rupali? What's Up Doc?"

"Well," she began slowly, "I don't agree with Mandy's mystery man idea because I don't believe God ever blessed a man with a cock quite like that." Giggles from the gallery. As she spoke, I backed Mr Gallows to the door. "So that means it was definitely a strap-on. I have looked through the toybox a number of times and we do have one down at the bottom. I'm sure I heard one of the girls name it as I inspected it. Is it ...Rawhide?"

I picked up Rawhide with my foot, jingling the buckles to make some noise as I made a grab for it and waved Mr Gallows out. For a big man he could move like a cat. "Ta da!" I sang as the door softly snicked shut. The girls removed their blindfolds and I held rawhide up for inspection, still wet with Mandy's juices. It might have been my imagination, but Trish looked a little disappointed. Maybe she wanted a turn? It would have to wait; Rupali was about to start leaking cum all over the carpet so I needed to get the others out.

"That's one turn each," I said. "And I need to get to sleep so I can dream about mystery men sneaking into my dorm to shag me blindfolded."

"If he does, can you send him to our room when you're done?" Trish joked. "You got me started with that thing, now I'm going to have to dig Leroy out of the toybox and finish the job." I opened the door and the girls filed out to the sound of muted giggles.

When I turned around again, Rupali was blotting cum from her labia with a tissue. She turned her eyes up to me, looking through long black lashes. "If I ask, you won't tell me, will you?"

"Nope," I smiled.

"Good."

I tidied the pillows, picked up Rawhide again and was walking to the door to wash him and put him away.

"Wait," Rupali whispered. "You're not done."

"Yeah, I am," I reassured her. I stepped in close and put a hand on her arm. "You did me." I blushed, feeling embarrassed, grateful and emotional all at the same time.

"That's not what I meant" she said softly. "What happened ... what he did ... it was exactly as I described it. It was my fantasy. Why would he do that?"

"It was his fantasy too," I said truthfully. "And mine, just to watch. To .... ," I groped for the right words – a lump rising in my throat, "... to see him use ... you know ... all of it." Tears were welling in my eyes now.

She pulled me closer and held me, towering over me, my ear pressed against her soft breasts. "He can't do that with you, can he? He's too big?" I shook my head in her tight embrace, my tears wetting the front of her nightie.

She held me quietly for a few moments. "That's your fantasy, isn't it?" she said, more of a statement than a question, as if she could see into my mind. "You want him balls-deep inside you."

I was crying openly now, no use pretending. Sobbing and hugging her tight, as she hugged me. "Yeeeeees," I cried. "I want to be completely joined; to crush our bodies together; to have nothing between us."

"Shhhhh, babe," she soothed. "I know, I know." She held me close and stroked my back until the crying subsided. Then changing tack: "You fucked Mandy, didn't you?" I nodded. "I thought so." She fell silent for a bit longer. "How did it feel?" she asked curiously. "You know, to have a cock and to just ... fuck someone with it?"

"It felt amazing," I recalled. "Powerful, liberating."

"I want to," she whispered.

"Me too," I whispered back.

She bent her knees and lowered her tall body all the way down until we were face to face. She kissed me; open mouth and soft lips pulling at mine. I opened my mouth to her and kissed back. Her tongue touched my lips, testing to see if I wanted more. I did; our tongues met and danced in the arena of our open lips.

Rupali lifted my nightie over my head, breaking our kiss, her long soft fingers caressing my curves, lingering over my breasts, touching my nipples with her thumbs and setting off electric sparks of excitement. I slipped the thin straps of her nightie off her shoulders and it fell to the floor pooled around her ankles.

I passed Rawhide to her and climbed into bed, watching as she turned it around and unbuckled it, working out how to put it one. She discovered the inside dildo and – realising what it was – looked up at me, dark eyes flashing in surprise and pleasure. I was entranced; she stood there in front of me, 6'1" tall, beautiful and utterly naked; glossy black hair cascading over one shoulder and framing a full, perfect breast as she ran her fingers over the short inner-dildo. I shivered with desire. She stood with legs apart and moved the tip to her pussy, sliding it all the way in easily. She held the leather cup to keep it inside as she arranged the straps and tightened the buckles.

Ready now, she looked up at me. She struck a Marylin Monroe pose: turning side on, one hand on a hip the other patting her hair, head turned back over her shoulder looking at me through long eyelashes. Long limbs, brown skin, ripe breasts standing out in profile ... and a thick 7" cock pointing out and up from her crotch. She was perfection. "How do I look?" she asked.

"Extraordinary," I croaked. I slid back and ran a hand down the bed sheet beside me.

Rulpali came to me and slid into bed, slipping one long arm beneath my neck and the other behind my back; pressing our bodies together, her full breasts pushing against mine. We kissed again, more hungrily this time. I put my own arms around her, feeling her long, soft curves, kneading her bottom and pulling her closer, feeling the thick, latex cock pressing against my mound and my tummy.

I rolled away, holding Rupali's hips, encouraging her to follow. She rose onto her elbows above me; I opened my legs and she moved between them, resting lightly on top of me, poised on knees and elbows. I reached down to feel for Rawhide, preparing to guide it to my wet centre. Wrapping my hand around the thick shaft, I could not quite touch my thumb to my middle finger tip – a good indication that it would be a very tight fit inside my tiny vagina. Would Rupali take it slow? Her need was as great as mine and she was no expert at handling a monster cock ... or a miniscule pussy for that matter.

I broke off our kiss and looked into her eyes. "It won't fit," I whispered, frightened now.

She kissed me again, "It will, we just need to take it slow."

Relieved that she understood, I breathed "Take me!"

She reached down with one hand and guided Rawhide into me. I was still lubricated and a little stretched from wearing Rawhide earlier and felt no discomfort as she pushed the first few inches inside, stopping when she reached resistance at the untouched depths where the inner-dildo and her own tongue could not reach. She pushed gently forward, stretching my pussy and causing some pain. She saw the look on my face and stopped. "I don't know how to do this," she apologised. "I have to push a little bit, or it won't go in at all."

"Just fuck me with that much; slowly though! And give me more every now and then," I instructed.

She withdrew but – Rawhide not being her own cock – she couldn't tell when to stop. It popped out of my pussy and slapped wetly against her belly. We were watching each other's eyes; I held focus for a moment and then saw a smile curling the corners of her mouth. We both burst into gales of laughter at the same time. I reached down and repositioned the thick shaft at my entrance. With mock seriousness I looked at Rupali and said "Now be careful, young lady. You could take an eye out with that thing." We both giggled some more, breasts bouncing pleasurably against each other.

Getting her length, Rupali set back to work, learning how to wield this wonderful weapon. She established a slow rhythm, withdrawing almost to the tip – careful to avoid a repeat of earlier – and then driving back in powerfully, but only to the point of resistance and no further. With each stroke I loosened a little, allowing her further access. Her superior height brought her breasts all the way to my chin. I took the opportunity to taste them – like low hanging fruit – licking and sucking one to a hard point and then repeating with the other.

Rawhide is thicker at the base that at the tip; so by the time she touched down in the innermost depths of my vagina, my pussy was stretched so wide that the thick shaft was in constant contact with my buzzing clitoris. I was going to come too early. I lifted my ankles up over her shoulders to change the angle of entry and to give her cock – for that is how I had come to think of it - the deepest possible access to my vagina. I looked up into her eyes, frantic and pleading. "Finish me," I whispered.

And she did. In a single fluid movement, she withdrew all the way back to the tip again and rammed her thick cock home, sending out a shockwave of pleasure as her pubis slammed into me. Again and again she pounded me, each stroke setting off a larger explosion as her body crashed into mine, the waves of ecstasy overlapping and building to a shattering orgasm. I called up a mental image of her cumming from this beautiful cock, emptying her load into me, filling me so completely that cum sprayed out around her pounding cock, soaking my thighs. I erupted, pushing down with my heels on Rupali's shoulders I lifted my bottom, straining against our connection, pushing Rawhide down against me but up against Rupali, grinding the inner shaft into her clitoris. Still pumping into me, she pushed back and I felt her body stiffen and convulse with her own climax. I dropped my legs back down and held her tight, deep inside me and our bodies pressed together as the last spasms contracted in our muscles.

We rolled onto our sides and held each other that way, neither wanting to be the first to break contact, until I heard her breathing deepen into sleep. I gently slid her cock out of my pussy and backed out of bed. Kneeling beside her sleeping body, I pulled back the covers and unbuckled Rawhide, and pulled the inner dildo gently out of her pussy without waking her. I left the room to wash Rawhide and return it to the toybox. When I came back Rupali was still in my bed; I slid in beside her and folded into her naked embrace like a Russion doll. One hand slid up to cup my breast and I heard her whisper in my ear "Thank you. I love you."