Hot for Teacher

I finally faced up to reality and ended my toxic relationship with my sexy but volatile next-door neighbour, Sasha. I lasted maybe a month living in my house in Pakenham, barely able to put up with the outrageous antics occurring over the fence and made the difficult decision to move back to my townhouse in Melbourne.

The decision was predicated on reducing the daily commute from over an hour each way to 15 minutes. Additionally, the house in Pakenham was too big for me, and I seemed to rattle around in it, and I could not be bothered fully furnishing the place. By contrast, the townhouse was cosy and within walking distance of pubs and restaurants.

There was a significant drawback to these changed circumstances, though. I was further away from my new girlfriend, Dakota. She lived in San Remo, which extended my drive by an extra half an hour. However, we managed it, and the reduced commuting for work greatly refreshed me when I drove down for a weekend together. On alternate weekends, Dakota stayed with me in my townhouse.

I met Dakota one weekend when I went to Phillip Island to catch a band I liked. The night before was one of those rough encounters that became unbearable with Sasha, whose drug use and descent into madness were rapidly increasing. It felt great to get away even for one night, and running into Dakota and her friend was luck personified.

Dakota was everything Sasha was not. The former was educated and taught K-12. She was financially independent, sensible, and goal-orientated. Never married, unlike me, she had limited relationships, but they were long-term. Visually, Dakota was a stunning blond, not as tall or slim as Sasha, but the beauty came from her personality, which was kind, generous, empathetic and thoughtful. We hit it off immediately, and the sex, when it came, was ferocious!

After a time, the long-distant arrangement suited us both. Yes, we missed each other greatly during the week, but we made up for lost time on the two-and-a-bit days we enjoyed together. The sex was intense: long sessions in the bedroom, other rooms, in public places, wherever the urge arose.

We shared lots of interests outside of the bedroom. The main one was sailing. Dakota was an ardent member of the Newhaven Yacht Squadron. While not a sailor myself, I am a keen maritime historian, and we talked long into the night about various ships, boats, and other watercraft. Soon after meeting, we sailed around Western Port regularly, weather permitting. Other interests include visiting wineries, exploring the countryside, catching live bands, and shopping. We strove to do new things each weekend we shared, and it was exhilarating!

One evening, Dakota and I were catching some live music at the Rosstown Hotel, a short distance from my place. The interior was dark and intimate. We sat at a table towards the back of the pub, where the music allowed us to talk. Dakota stroked my leg and, not so accidentally, raked a fingernail across my crotch.

"Can I ask you something?" She asked with a sneaky smile.

"Sure."

"It has not gone unnoticed that when we play together," Dakota began, "You've been paying a lot of attention to my arse."

We both chuckled.

"Yes, I have," I admitted, "It's beautiful. Do you like it?"

Dakota thought for a second before conceding that she did. Mostly during foreplay, I tickled her brown eye with my tongue and probed the opening with a digit before focusing on different erogenous zones. When fucking doggy style, I would spit on Dakota's wrinkled hole and attempt to insert my thumb. She never objected to this, nor did she encourage me further.

"You want to fuck me back there, don't you?"

"The thought had crossed my mind."

"Mine too," Dakota smiled, "Never done it before, but your tongue and fingers feel good there."

"Maybe we could try?" I asked, hopeful.

"I'm nervous," Dakota admitted, "Because I think it will hurt."

"With proper preparation and a go-slow approach, there's no reason why it should hurt," I replied.

Several years ago, when I lived in Western Australia, I had a sexual relationship with an older and experienced lady that taught me the secrets for making anal sex an enjoyable experience. While together, we followed her preparation plan meticulously and subsequently had anal sex that rivalled the nastiest scud videos available anywhere on the interwebs.

"What's involved?" Asked Dakota, intrigued.

"Firstly, you need to douche your back door with warm soapy water," I said, "Get's your arse nice and clean."

"I wonder what that feels like?"

"I'm told that it's a pleasurable experience," I replied, "There's a sensation of being full followed by relief as you expel the water."

"Interesting," Dakota smiled, her eyes ablaze, "What's next?"

"You need to choose lubrication that relaxes the muscle before penetration," I replied, "One that doesn't irritate the skin."

"Good point," Dakota acknowledged, "Because my skin is very sensitive."

"Then we get you ready for anal sex using fingers, tongues and toys."

"Toys?" She asked with some surprise, "Like a vibrator?"

"Like a vibrator," I said, "Or a dildo or butt plug."

"Yeah, I've seen those used online."

"Online?" I asked with some amazement, "You mean porn?"

"Of course, I mean porn," Dakota chuckled, "A girl has got to have something to watch during the week."

"I'd love to view your browsing history," I smiled lasciviously.

"Pornhub, big deal."

"No, it's more about the nasty videos you click on," I pressed, "Is there a particular category you search for?"

"I just browse whatever is on the home screen," Dakota replied, "And click on whatever looks interesting."

"You have a favourites list?"

"Now, that would be telling," Dakota laughed, "Maybe one day, we'll browse together."

"Our sex is way better than anything online!"

After exchanging a brief kiss, Dakota agreed. It was hard to deny the intensity of our sessions together. We fucked long and hard in every position imaginable. My orgasm was limited by the fact that Dakota was not on any birth control, and so I had to pull out every time. Her favourite splatter location was her generous breasts. She hated receiving any sperm on her face but was not averse to swallowing me whole when blowing my cock to climax. For her part, Dakota came often and loudly. She squirted a lot and was always extremely slippery, sometimes resorting to a panty liner to her from "sliding off the chair" at work.

"I've noticed that anal sex videos are ubiquitous these days," Dakota observed.

"Yes," I agreed, "What was once a taboo sex act has become mainstream."

"Was it taboo?" Dakota wondered, "I never thought about it before, and when I saw it, I looked interesting but never deigned to try it, and no previous boyfriend ever went there."

"Until me?" I joked.

"Indeed, you've shown a lot of interest in my bum."

"Because it's beautiful!"

"I'd like to give anal a go," Dakota said, "But I don't have an enema bottle, don't have the first clue about lubrication, obviously, and have no toys."

"Well, we could get them," I said.

"From where?"

"Either in person," I said, "There's a sex shop on Glen Huntly Road, just down the road."

"Or?"

"Online," I replied, "But you won't know if what you buy is right for you."

"I don't know if I could go in person," Dakota chuckled, "I think I'd die from embarrassment."

"We'll be together."

"That won't help," She said, "I've never been to one before as they all look so sleazy."

"Some can be for sure," I agreed.

"I'd prefer to buy these things online," Dakota decided, "You know what to get."

"Happy to offer you some suggestions."

Dakota retrieved her phone from her handbag, fired up the browser and searched for 'sex shops'. Unsurprisingly, a gazillion options were available. After searching, we settled on local options and searched their product catalogues.

"This lube here is one that a previous lady friend recommended," I pointed out, "It did the relaxation thing, and she said it tasted sweet."

"Tasted sweet?" Asked Dakota, her nose wrinkling, "What has the taste got to do with it?"

"Well, she liked to do ATM or arse-to-mouth when changing positions," I said, "Like how you like to lick my cock when it comes out of your pussy."

"ATM, did you say," Dakota asked animatedly, "Sucking your dick after it's been in my arse?"

"Yes."

"I've seen that online," Dakota said, "It looks disgusting. I mean, your dick would literally taste of shit."

"That's why you douche beforehand," I explained, "No poo during anal sex, just sweet-tasting lube on a hard cock."

"Huh!" Dakota said, acknowledging a new fact, "That changes things, I guess."

"Would you be up for it?"

"Maybe, just maybe."

Dakota's face showed her mind mulling over this new information and, because she was sexually adventurous, leaning toward trying such a common anal-related act. Confirmation came with the lubricant added to the shopping basket. Next, we selected two enema bottles with a soap solution.

"What's best?" Dakota asked, after scrolling several pages of toys, "A dildo, vibrator or plug?"

"It's best to start small and work up," I said, recalling female words of wisdom from years ago, "Perhaps something like this?"

I pointed to a slim, black rubber plug whose widest point was roughly 1.5 human fingers. It was also reasonably priced, not that Dakota was short of a dollar.

"The advantage a plug has over the alternatives is that you can wear it all day in public!"

"Oh!" Dakota's eyes widened, instantly grasping the possibilities, "I like the sound of that."

The plug was instantly added to the shopping basket, and Dakota checked out. The package was addressed to my place, and I was instructed to bring it down to San Remo next weekend.

We finished our drinks and walked back to my place, horny as hell. That night we fucked harder than ever, with Dakota encouraging and demanding that I please her virgin arsehole with my fingers and tongue. She willingly accepted a finger and thumb fully inside her most intimate hole but stopped short of inviting me to deflower her. The session ended with a massive load of boiling sperm across Dakota's big titties.

The package of anal sex tools arrived as promised, and I sent Dakota photos of the contents. I doubted she would go for any backdoor action but would want to test the package, and that, in and of itself, was an exciting prospect.

After showering, I jumped in my car and drove to San Remo after the working week finally ended. At 7 PM, I parked in Dakota's driveway. She was sitting on her porch rocker, waiting for me with a glass of wine in hand.

When we broke our embrace, I sat next to Dakota and downed a welcome glass of wine. The evening was balmy but chilled by a breeze from the nearby sea, and the light was fading fast. From inside the house, soft music wafted across the air. As we rocked gently together, I handed Dakota the package.

With childlike wonder, she carefully examined each item in minute detail. Dakota opened the bottle of lube and the enema soap deeply inhaled their respective fragrances positively. Next, she unwrapped the modest butt plug which I suggested and ran her finger and thumb across the contours of the toy, eyes widened, wondering whether her tight hole could accept such an intrusion.

"Are you happy with your purchases?" I asked.

"I think so," Dakota stammered, attempting to contain her nerves, "I'm not sure."

"No pressure," I reassured her, "Take your time. We'll do this together."

"I am curious to try this," Dakota said, holding up one of the two enema bottles.

"Now?"

"Sure."

We walked into the kitchen. Dakota switched on the light, and we studied the instructions. After adding the requisite amount of soap to the bottle, I warmed water from the tap to a temperature that, from historical experience, seemed appropriate and filled the bottle.

"What...what do you do next?"

"Let's go to the bathroom."

Grabbing Dakota's hand, I led her to the bathroom and embraced her. After kissing her deeply and lovingly, I bent Dakota over the basin. Hiking up her skirt and tugging her sopping G-string down her shapely legs.

"Spread your arse," I ordered.

Having never been asked to do such a thing, Dakota clumsily attempted to part her cheeks. I replaced her hands closer to the butt crack and forced those fleshy globes further apart, exposing her pink rosette.

"Oh, I love that," Sighed Dakota as my tongue lapped away.

Pussy juice quickly began leaking down both of Dakota's inner thighs as my tongue stabbed deeper inside that dirty hole. The aroma and the texture were intoxicating, and I quickly became rock-hard.

"Let me feel it," Dakota pleaded after an unknown length of time had passed as I continued rimming my girlfriend's arsehole.

"You like that?" I teased after I pulled my head out of her butt and slapped her left cheek hard.

"Hm," Dakota giggled, "I'm loving it more and more."

Grabbing the bottle of lube, I smeared a generous amount across Dakota's cheeks before zeroing a digit on her twitching starfish. With my finger coated with the fragrant grease, I pressed gently against her tight aperture. Surprisingly, there was little resistance, and Dakota's virgin arse allowed the alien intrusion.

"Oh," Groaned Dakota, her body going limp.

"So fucking tight!" I marvelled as Dakota's O-ring gripped the flesh of my finger; the heat was unbelievable.

Slowly, I withdrew my finger and re-inserted it as Dakota purred like a kitten. It took a while, but the lube, my determined penetration and Dakota's increasing level of arousal resulted in a loosening of her dirty hole. The relaxation allowed for the easy insertion of the nozzle of the enema bottle.

"You ready?"

"Uh huh," Dakota released her cheeks, and they snapped together with a satisfying smack, "It's so slippery back there."

"Yeah, you're lubed up good," I joked, "Get down on the floor."

Dakota complied after undressing completely, and I manhandled her into a position where her pucker had a slight elevation.

I carefully inserted the nozzle into her loosened arsehole and squeezed the body of the bottle, forcing the warm soapy water deep into Dakota's bowels.

"Oh, fuck!" Hissed Dakota, "That feels fucking weird."

"You want me to stop?"

"No," She panted in response, "Keep going."

Squeezing the bottle some more, Dakota tensed and flopped in turn as she struggled to process the strange sensation of the enema. In a few short moments, the contents of the bottle had drained.

"How do you feel?" I asked nervously.

"So fucking full," Dakota squealed, "Feels kind of nice though."

I gingerly withdrew the nozzle and told Dakota to tighten her pucker to prevent fluid loss. Several dribbles of liquid escaped her arse and pooled with the pussy slime that was actively running down her inner thighs.

"Don't think I can hold it," Dakota hissed repeatedly as I helped her to sit on the toilet.

"There we go," I said, "Now, relax and let it go."

With her legs spread, Dakota looked at her pussy and the bowl beyond. At first, nothing happened, and she groaned uncomfortably, the liquid stubbornly refusing to exit her body. I placed a finger on her clit and gently massaged it.

Suddenly, I heard a hiss followed by the unmistakable sound of two liquids colliding. This was followed by a satisfying groan from Dakota that seemed to originate from the depths of her soul. There were several more spurts as she gladly forced the warm soapy water from her shitter.

"How does that feel?" I asked, watching the contents float in the water below.

"It actually feels amazing," Dakota admitted, "I'm going to come!"

With the response of a cat, two fingers darted towards Dakota's engorged clit, forcing me away, and a few chard tugs later, she let out a high-pitched shriek, and her body thundered to an orgasm, the first of a type Dakota had ever experienced.

"Fucking hell, that was strong!" She said as her body slumped back against the toilet's cistern.

"Is it all gone?"

"Yeah, I think so," Dakota replied, gingerly rising to her feet and grabbing a wad of toilet paper.

"So greasy back there," She said, wiping her butt.

"You see," I said, pointing to the contents of the bowl, "That's why it's important to douche before anal sex."

Dakota understood the significance immediately and reiterated that the enema was a strange but ultimately pleasurable experience.

"You want to try the plug now?"

"Sure, let's do it."

Dakota leaned over the basin again and offered me her luscious buns. After lubing the plug, I pressed it against her wonderfully clean and sweetly aromatic pucker. The hole was relaxed now, and the toy was eagerly accepted until we reached the widest part, where I experienced some resistance.

"Oh, gentle, gentle!" Dakota implored me.

I tenderly pressed the toy against the muscle, willing it to be accepted. Dakota was determined to take the foreign object inside her arse, but the sensation was uncomfortable but not unacceptable.

"Fuck!" Dakota shrieked, "Is it in?"

"All the way, baby," I said proudly as I pressed the base hard up against her butt hole, "How does it feel?"

"Fuller than before," Dakota moaned, reaching around and fingering the base of the rubber toy, "But not bad. Such a different type of sensation."

"Well, stay where you are," I said, dropping my jeans and whipping my cock out, "Because I'm going to fuck your pussy."

Dakota had no time to protest as my cock made its way urgently inside her tight sopping cunt.

"Fuck!" We both moaned in unison when I was balls deep.

Administering an enema and then patiently inserting the butt plug had brought me to a fever pitch of arousal. After placing my hands on Dakota's hips, I slammed her pussy like a possessed demon.

An orgasm was not far off. Dakota had an innate sense of when I was close and ordered me to spray her tits, or she would blow me to a climax. Tonight, it was the latter. I sat on the edge of her bath with my legs spread, allowing her to crawl between them. She took my pussy-stained cock in her mouth and proceeded to blow me to heaven.

"Shit, here it comes!" I bellowed.

At that moment, she took my full spasming length down her throat just as my balls unleashed. My hands gripped the side of the bath so tightly that my knuckles turned white to prevent me from falling in. In the fog of pleasure, I vaguely felt Dakota's throat twitch as she swallowed thick ropes of salty semen, much to her approval.

As my orgasm subsided, Dakota slowly massaged my dying cock with her lips which immediately elicited a secondary round of pleasure darts.

"Jeez, that was amazing," I shuddered when her mouth released my deflated stick.

"Extra spicy tonight," Dakota grinned and showed me her empty mouth.

We stood up and kissed passionately. I asked Dakota if she wanted me to remove the butt plug, but she cheekily demurred, telling me she wanted to leave it in a while to get used to it. Over the next two days, we practised with the enema and toy several times, with each session ascending to greater heights of sexual pleasure.

During the next week, Dakota practised with the enema and the butt plug on her own. When she visited me that weekend, I played with her arsehole using my tongue and fingers, which culminated in fantastic sex. However, she failed to pull the trigger, and no anal sex occurred.

Early that next week, there were hints that Dakota was ready for an anal deflowering. The text conversation was incredibly risqué during the day and downright X-rated in the evening.

"I have a question to ask?" Dakota tapped.

"And that is?"

"What's the best position for me to take you up my butt?"

"Doggy appears the most common," I said, "But if you rode me on top, you'd have more control, especially since it's your first time."