Sally: My Slutty School VP

The sight of Sally's sexy white buttocks sent a jolt of excitement through me and I eagerly reached out. First, I collected some cunt-cream with a fingertip and smeared it all over her tiny brown rectum. Sally has a super-sensitive anus so it trembled visibly as I gently rubbed the warm slick pussy-juices around it. Once my finger and her asshole were slick enough, I began preparing her tight butthole for the first fuck.

I knew there was no way Sally could take my fleshy stiff dick inside her tiny rectum. So, I began by stretching it a little. I poked my long forefinger inside and watched it disappear inside her taut-clenched asshole. I kept pushing it till it was buried to the knuckles. Sally stood frozen in position, but her big fluffy butt-cheeks clenched shut around my hand, so I told her to grab them and spread them. Sally did as told, eager to have something to distract her from the pain.

Then, I pulled my forefinger out and joined it with the middle-finger before steadily pushing both inside Sally's little anus. My huge hard-on jerked excitedly at the way my two fingers stretched her tiny asshole wide apart.

"OW! Ssshh!" Sally cried aloud in pain before she suddenly realized and hissed to overcome the pain in her butt, "Ooh. Aaah. Ooh. Aah." She began groaning and moaning as I started to gently thrust two fingers in and out of her tight-clamped anus.

At the same time, I placed my other hand palm-down on her creamy cunt. I pushed a thumb in her slick pussy while rubbing her taut clit with my palm. This seemed to get Sally aroused and she soon overcame the pain of having her ass finger-fucked. Her slim white fingers clasped her large soft ass-cheeks tighter and her body quivered with excitement. This made me continue to finger her ass and pussy till she had another small orgasm.

"Oh! Oh! Oh! Aahhhh." Sally gasped quicker before she exhaled long and low as the orgasm hit her.

Sally instantly jerked upright in the excitement of her intense orgasm, immediately pulling my fingers out of her tight-clenched asshole and creamy cunt. I stood up and grasped Sally from behind comfortingly. I was afraid she'd forget people could still hear us and cry aloud in her super-excited state. But Sally kept control over her voice and only mewled softly, and bit down on her knuckles as the sensual orgasm made her tremble.

My huge slick dick bumped and brushed on her fluffy big bare buttocks, making it jerk with increasing anticipation. Sally felt it too, and quickly positioned herself once more, leaning on the table and resting her forearms on the table.

"Okay, fuck my ass, Ali." Sally said softly and arched her back to push her huge round ass-cheeks further out.

I glanced at her wonderful wide apple-shaped behind as Sally bravely prepared to get ass-fucked for the first time.

I quickly stepped close behind her. Sally's crotch was level with mine as she stood bent over the desk, thanks to her high heels. I didn't even have to bend my knees to put my swollen cock-cap on her slick tight asshole. I told Sally to take a deep breath and exhale slowly and watched her obey. Sally's small brown butthole clenched tight as she took a deep breath in. I squeezed my engorged dickhead to make it smaller. Then when she exhaled, Sally's tiny asshole was pushed out. At this, I immediately thrust my slick round knob in Sally's tight asshole.

"Mmph!" Sally's painful groan was muffled in her arms as my huge cock-cap stretched apart her tiny butthole and pushed through, "Ooohhh." She groaned long and low in agony when I steadily pushed my huge hard-on deeper inside her dank warm anal-canal.

I practically trembled with excitement at the incredible sight and sensations.

I held Sally's wonderful wide hips from behind and began was fucking her ass steadily from behind. The view of Sally's small anus over-stretched and clinging tightly to my huge brown hard-on was incredibly hot. I loved the way her tiny asshole kept clenched tight around my fleshy stiff dick. I had to strain considerably to push it deeper inside, as her small rectum clung tighter and tighter with each inch.

"Mm! Mmh! God! Oh fuck! Aah! Ouch! Ow! Aah!" Sally soon began groaning and swearing a little louder as I slowly, but firmly fucked her tight ass.

My hips moved back and forth slow and steady, as I forced my huge hard-on in and out of Sally's lovely little butthole. I felt a thrill of excitement run up and down my thick dick every time I thrust it all the way in, making Sally groan with agony. There was a strange powerful feeling that took hold of me, and the image of fucking my strict sexy vice-principal in the ass in her office was incredibly arousing.

It instantly prompted me to fuck Sally's ass harder. So, I began pulling my huge hard cock out slowly before plunging it suddenly inside her tight-clenched anal-canal. Every thrust sent a jolt through Sally which made her white fluffy ass-cheeks wobble wonderfully. My big ball-sack also slapped against her creamy sensitive cunt every time, which had Sally aroused and excited too. The only sound was the loud sudden slapping sound as my bare crotch smacked hard on Sally's large soft buttocks from the back.

"Mph! Mm. Mph! Mmm. Ungh! Mmm. Uhh! Mmm." Sally continued to grunt with pain at each thrust and moaned in relief when I pulled out faster and faster every passing minute.

All of this ultimately got me closer to my own climax. I could hardly hold back now, especially with her way Sally's lovely tight butthole clamped and quivered, stretched taut over my thick hard cock. Thanks to her cunt-cream, my huge hard-on slid a little easier inside Sally's warm butthole. I enjoyed the way her soft sides felt in my hands and watching her lovely large ass-cheeks jiggle hard with each thrust.

"Oh," I gasped aloud, "I'm gonna cum." I warned in an urgent whisper.

"Come! Come in me. Aah!" Sally managed to gasp out before crying aloud in pain as I instantly shoved my entire thick dick in her tight little anal-canal.

"Aaaaggghhh!" I growled long and low and froze in place as I came hard in Sally's sexy ass.

I felt my throbbing climaxing cock pump out sticky hot loads of semen deep in her warm dank rectum. My balls quivered as they shot out their load every second. My eyes snapped shut and my mouth remained open in a silent moan of sensual ecstasy as I kept coming in Sally's slick tight anus. Slowly, and gradually, I leaned over and plopped down on Sally's back, pressing her on the desk under my weight as the throes of the incredible orgasm became too much to handle.

"Mmm. Mmm. Hmm. Mm." Sally kept moaning and mewling softly beneath me, no doubt feeling the messy gooey cum filling her anal-canal completely.

I laid still on Sally's back for a minute or more. Once I could open my eyes and my breathing got back to normal, I slowly stood upright.

"Sorry, Ma'am." I apologized for having almost crushed her under my weight, "I didn't even know when I fell on you, the orgasm was so incredible!" I gasped and explained.

"Ow!" Sally cried aloud as I pulled my slippery softening cock too quickly out of her tight-clamped asshole, "Ohh. It's perfectly fine, son. Wow! You came a lot, didn't you?" She exclaimed next as she stood upright.

I saw my sticky hot semen dribbling out her quivering asshole and running down the insides of her stocking-clad thighs. Sally quickly reached into her handbag on the table and grabbed a couple of tissues. She hurriedly placed the tissues deep inside her ass-crack to catch the flow of my gooey cum from her butthole. Then, she passed me some tissues to wipe my messy thick cock.

Once I had post-nut clarity, I was thankful that no one had caught us. Now that I was satisfied and sobered up, I suddenly realized the incredible consequences. We could still hear the kids shouting and screaming excitedly watching the kite competition in the football-fields, through the window. A few teens were playing on the basketball court right below the office. Thankfully, they hadn't looked at the window to Sally's office and we managed to fuck successfully.

It was nearly 4 PM when Sally and I were ready to leave. She unlocked the door and opened it an inch to peek out. There was no one out in the corridor, so she signaled me close, hugged me tight and bid me goodbye, with a promise to fuck soon.

I managed to walk down to the parking-lot without being seen and rode out, full of excitement and thrilled at the foolish but fantastic fuck at school.

So, this is how Sally and I fucked after a long time. Over the next few months, Sally and I only fucked only a few times whenever I came home. This was till May of 2009, when Sally conspired with Cherry to give me one of the best surprises of my life.

Sally's Threesome with Cherry

(Sunday, 3 May 2009)

In April 2009, Cherry had resigned from the school and moved to Mumbai. She'd found a job as a teacher at a popular school on Vashi, New Mumbai. She had invited me over the weekend after she settled in her small cozy 1-bedroom apartment in sector-1, right near the highway. Though I was living-in with Dee, I rode a few times to Vashi from Pune for a few hours of fun with Cherry.

Then on the first Saturday of May, I got a call from Cherry. She sounded more cheerful than ever and invited me over the next day. I didn't have any important plans with Dee, so I agreed to come. At this, Cherry got even more excited and told me that she had a surprise for me. I was already thrilled to meet Cherry, but got even more interested when she mentioned a surprise. As Cherry and I had a pretty wild sex-life, I was always excited about her presents and surprises.

On Sunday, I got up early. Dee also woke up but stayed in bed, as she wanted to sleep more. Dee and I had an understanding that I could sleep with multiple partners, as long as I fucked her whenever she wanted. Dee actually found it hot to hear me describe how I fucked other fuck-buddies. So, she didn't object when I told her I was going to Mumbai to hook-up with a fuck-buddy.

Dee affectionately kissed me on the lips, wishing me luck and making me promise to tell her everything that happens.

As it was May and the peak of summer, I wore a plain grey T-shirt with black jeans over black boxer-shorts and matching black sneakers. I had my cell-phone, wallet, bike-keys, lighter and half-pack of Classic Regulars with four thick long joints. It was after 9 AM when I rode my motorcycle.

The 120-km stretch of highway seemed long in my eagerness to meet Cherry. I rode pretty fast, and only stopped once for a pee, and to have a cup of tea with a cigarette. All through the ride, my mind kept drifting and I wondered what kind of surprise could Cherry have for me now. We'd already tried several extremely kinky things together. Cherry seemed to come up with some of the weirdest yet hottest fantasies and I enjoyed every bit of it.

It was nearing 11 AM when I reached Cherry's apartment building. It was a small three-story building. It was wide, squat with wide windows, same as the others that surrounded it on two sides in the well-designed pattern you see in New Mumbai. I had to park the bike and pause for a few seconds to subdue the semi-erection I had by then.

I called Cherry on her cell-phone and she picked on the first ring. She told me to come straight up and ended the call. I was pumped as I ran up the staircase, taking two steps at a time to the third-floor. Cherry's apartment was the last of four that branched out from the landing. I noticed the door was slightly ajar and quickly walked into the darkened living-room.

I sensed Cherry standing behind the door and pushing it close as I looked around the large living-room. The door to the kitchen and the bathroom was across the room. The bedroom was through another doorway on the wall to the right, which also had a sliding door opening into a small balcony of sorts. The living-room only had a large wooden couch-cum-bed with a small coffee-table and a few chairs around it. Though the door was closed, I was quite familiar with Cherry's new bedroom. It was around 15-feet long with wide sliding windows on the outer-wall. The room was furnished with a large queen-sized bed, a wooden wardrobe, TV-trolley and the desert-cooler.

"Hey, honey!" Cherry whispered from behind and came to stand in front after locking the door.

Even though the room was not quite dark, the light coming through the curtains of the balcony was enough to make out Cherry's sexy black outfit.

Cherry looked incredibly hot in the short tight black dress. It was practically see-through and hugged her sexy curves like a second skin. It was stretched taut over her large white boobs which stood out proudly without a bra. Her large light-brown nipples made dents in the slinky fabric of her dress. It outlined her sexy slim waist and wide curvy hips clearly. I could imagine it being stretched thin by her large 40-inch ass-cheeks behind her. The matching black stockings and 4-inch high heels made Cherry look extremely enticing.

"Wow!" I gasped out in wonder and eagerly moved close to hug and kiss Cherry.

"Mmmm." Cherry moaned lustily in my mouth as our lips met, and I distinctly smelled wine on her breath.

We hugged each other hard and kissed even harder, making up for the lost time since our last meeting. Cherry embraced me with her soft smooth arms wrapped tight around my neck, while I held her curvy side and pulled her close with a handful of her lovely large ass-cheek. She leaned over on me, and lifted her left foot to brush her shapely stocking-clad leg. She swayed a little so I held up upright with my hands on her buttocks.

Cherry and I hugged and kissed this way for over a minute, and enjoyed every second of it.

At the end, I had a semi-erection in my pants as we stepped away.

"So, how was the ride, sweetheart?" Cherry asked, making small talk and leading me to the large couch.

"It seemed very long, since I couldn't wait to meet you." I replied and we laughed together.

Cherry made me sit in the middle of the wide-cushioned sofa and went to stand behind me. I noticed the half-empty bottle of red-wine and a half-full glass on the low rectangular coffee-table. I didn't comment that Cherry was visibly tipsy.

She leaned over me from the back and made small talk for a minute. While talking, she gently caressed my cheek and smiled along with me. I leaned back and raised my face to look at her and replied, but enjoying her warm soft hands on my face more. Her hot wine-scented breath was strangely intoxicating and arousing.

"So, are you ready for the surprise?" Cherry asked, her voice a mix of enthusiasm with a hint of nervousness.

I noticed it, but ignored it.

"Yes, I am." I replied eagerly, "But what is it?" I asked, getting more impatient by the second.

Cherry didn't reply but covered my eyes with her soft hands. Then I heard the bedroom door open before I heard the click of high heels on the tiled floor. I suddenly felt nervous, wondering who was there. Cherry kept me blindfolded but the sensual excitement overcame my fears and I grinned in anticipation. I heard Cherry and someone else giggle softly before Cherry suddenly let go of my face.

"Surprise!" Cherry and Sally cried out together gleefully and I opened my eyes with a huge grin.

"Well, hello." I quipped and eagerly looked at Sally, who stood posing with a half-full wine-glass in a sexy white outfit.

Sally looked extremely hot in the tight white knee-high dress. It had a plunging neckline, which showed off her deep white cleavage. The see-through dress exposed her soft round saggy tits and long brown nipples clearly. The dress hugged her wide curves and showed off her shapely legs clad in sexy white stockings and matching high heels. Sally's sensual pose and lusty hooded eyes made her seem even more inviting.

"Hello, Ali." Sally quipped back and smirked.

I was suddenly very excited and confused too, so I looked from Sally to Cherry with a questioning look.

"Do you think this is a weird idea?" Cherry asked, getting a little nervous as she pointed to each of us, clearly indicating a threesome.

"What?" I asked, incredulously, "I think this is a great idea!" I replied hurriedly to reassure her, "I was just wondering whose idea was it?" I said and grinned playfully.

Sally and Cherry both laughed at this and came to sit on each side. They sat close to me, and Sally made me turn to her. As soon as I turned in my seat, Sally caught my hair and pulled me in for a sudden sloppy kiss and felt my firm chest with the other hand. I immediately gave in to her silent sensual demand and kissed her back. I began sucking her plump lower lip and let her run her tongue all over my soft pouty lips.

At the same time, I put my left arm around Sally's wide curvy waist. I pulled her close before reaching around to fondle her lovely soft bra-less boobs. She rubbed her thick stocking-clad thigh against me. This prompted me to squeeze her smooth soft thighs while kissing her for nearly a minute. I felt Cherry's warm soft hand rubbing my back encouragingly, as she watched me kiss her best-friend.

"Muah!" Sally quite kissing with a desperate noisy one and leaned back to look at me, "It was my idea." She replied and grinned.

I looked around at Cherry and she grinned and shrugged, indicating Sally was telling the truth. Cherry then offered me a cigarette, and I remembered the weed. So, the three of us began smoking a large doobie each while Sally and Cherry took turns describing how things turned out to this moment.

I smoked the strong weed and immediately felt its effects. I listened with growing arousal as my sexy ex-teacher and vice-principal turned lovers recalled their discussion.

Schools were closed for the two-month long summer vacation so Cherry had invited Sally to Mumbai for the weekend. Sally remembered that I lived in Pune, which was not very far. Cherry mentioned that I had come over a few times since she moved in last month. Sally wondered aloud if she could meet me and fuck me, since it had been a long time. Cherry, the horny divorcee, and Sally, the lusty cuckold talked began eagerly discussing the possibilities.

As they talked more, they finally decided to try a threesome. It was the first time for both, but they were pretty excited.

You see, Sally and Cherry were extremely progressive and intensely kinky, as I'd often experienced first-hand. So, they had frequently wondered about fucking each other. But they hadn't got an opportunity like this, and decided to grab it. That's when they made a plan to surprise me. Knowing me as well as she did, Cherry was sure I wouldn't say no to fucking her and Sally at the same time. This was true since it was Cherry who had convinced me to fulfill Sally and her husband's cuckold fantasy in the first place.

As we continued to smoke the weed, the three of us got progressively high and horny. The talk soon turned to sharing experiences. Sally and Cherry eagerly related some of the more memorable sex-sessions they'd had with me. They were both pretty shocked, especially since they had never discussed me, despite knowing well that I the other was fucking me regularly too. So, some of things came as a shock.

During this, Sally and Cherry were sitting extremely close to me, on each side. Their soft mature boobs kept frequently rubbing my arms and chest, as they leaned over me often. I enjoyed casually caressing their smooth stocking-clad thighs while listening to them talk brazenly about their sexual exploits. The super-strong weed and the intoxicating company of two bold MILFs on each side had me aroused.

By the time we finished smoking the joints, the three of us were high and horny!

Sally and Cherry were nearly stoned, since they had been sipping wine while smoking the joint. I was pretty high myself but extremely excited too.