An Erotic Trip to Sydney

I had been in a stable relationship with the feisty teacher from San Remo for almost a year. Dakota was a solidly built blonde with a generous chest and butt. She taught K-12 at school on nearby Phillip Island during the week and took me sailing around French Island every other weekend while I took her to the country and explored the best hidden gems around Victoria on other weekends.

The fun on the land and on the water was matched by explosive action in the bedroom, and other places where our urges overcame of sense. Dakota took to anal sex like a duck to water after being deflowered. Butt fucking was a staple part of every session and when it was at 'time of the month' it was the butt and nothing but.

I would regularly receive spicy pics of Dakota wearing her butt plug that I bought for her first time several months ago. She often spoke about purchasing additional sex toys, but she was too embarrassed to visit a sex store by herself or with me, even though I offered to accompany her. Dakota was reluctant to make a purchase online too for obvious reasons.

We decided on a four-day weekend getaway to Sydney and decided to stay in the party district of Kings Cross, just a short distance from the CBD. After booking into the Holiday Inn, we began exploring the area beginning on 'The Strip'. The Cross at that time was more vibrant that it is today. There were seedy nightclubs, pubs, restaurants and sex shops.

As we strolled past these shops, I noticed Dakota discretely peering into the darkness, her curiosity aroused. Following dinner and drinks at the Potts Point Hotel, we wandered back to our hotel. Passing the sex shops again, Dakota slowed down.

"Do you want to go in?" I asked, chuckling at Dakota's hesitant interest.

Dakota looked around as if our fellow revelers would recognize her. I reminded her that we were in Sydney and that we were in the Cross where nobody cared whether we visited a sex shop. Dakota's mind was made up when another middle-aged couple exited with several purchases, showing no embarrassment at all.

"Okay, let's go," She gushed while gripping my hand tightly.

To Dakota's immense relief, the shop was not as sleazy as she expected. The interior was well lit with rows of toys, lingerie, DVDs, BDSM equipment, Shibani rope, lubricants and magazines. Surprisingly, there were several couples browsing the inventory, giggling and sharing private jokes as they inspected various items. As tends to be the case, the staff were female.

"Look at this place," Gawped Dakota with childlike wonderment, taking in the racks of erotic paraphernalia.

"Can I help you?" Asked an attractive brunette, wearing a revealing outfit that left nothing to the imagination.

Dakota almost shit herself, so terrified was she of this alien environment. She stuttered a reply about browsing for the moment. I laughed internally at her discomfort, especially since Dakota's face turned firehouse red with embarrassment. The brunette flashed a pleasant smile, spun around, and wandered off.

As we slowly perused the aisles, Dakota's anxiety waned as various items took her fancy. She picked up shrink wrapped packages and examined them intensely.

"Do you have an idea of what you want?" I asked.

"I definitely want a vibrator," Dakota whispered, as if someone was covertly listening to us, "And, I was thinking of a larger plug."

"Oh, really?" I asked, surprised about the second part of her reply.

"Yeah, I experience a brief moment of pain, irritation really, when you stick your cock in my arse," Dakota continued, "So, if I had a larger plug that would go away."

What made anal sex great between us was the time we took to prepare for penetration, and that included the douching beforehand. Dakota found a lubricant that was sensitive to her skin, tasted great and relaxed her bung, after some false starts. She wore the plug for many hours before penetration which I played with to heighten her sense of arousal.

"Sounds about right," I smiled, "Do you have an idea of what you want?"

"No, but it's good to look at what's available."

As we browsed, Dakota became more comfortable. We reached an aisle with numerous and exotic types of vibrators and dildos, both big and small and in all the colours of the rainbow. She picked up to vibrators to compare.

"This one will fit in my handbag," She giggled, "But this one looks mean."

Dakota showed a small black vibrator that took an AA battery about 5 CM in length. The other was 30 CM rechargeable purple wand. The latter seemed especially interesting to Dakota. She ran her finger over the contours of the toy, and her eyes dispelled her thoughts. However, once she saw the price tag of $150, Dakota placed it back on the rack.

"I'll buy it for you," I said, grabbing the wand.

"No, it's not what I want at this stage," Dakota said, her curiosity aroused now looking around, "I want a vanilla vibrator for use at home."

Dakota chuckled at her admission and then said she needed the vibrator to keep her company during the week when I was not around. Flicking the bean with her fingers was rapidly becoming old hat.

As we walked up and down each row, Dakota suddenly stopped and grabbed a long double-ended dildo. She examined the toy with a confused look on her face.

"What do you use this for?" She asked.

"Lesbians use it to fuck their pussies and arses," I replied.

"Do guys use it?"

"Not that I have seen."

"Huh," Said Dakota, placing the enormous rubbery toy back on the shelf.

"This is what I want," She crowed and held up a cream-coloured, standard looking vibrator with a smooth tip and ridged body.

The selected toy was more moderately priced at $25. Dakota's shopping cart consisted of two items now, and she went on the hunt for a third item, an upgraded butt plug. This last item took some time to procure but eventually, Dakota settled on a toy that she gushingly admitted closely represented the size and girth of my tumescent cock.

"You need any lube with that?" Asked the sexy brunette, whose bust almost spilled from her lacey top.

"Nah, we're good," Squeaked Dakota, almost dying from embarrassment at having to answer such a question.

With the toys packed into a paper bag and the money exchanged, Dakota almost pulled me out of the shop. Blushing and hyperventilating, I was dragged along Darlinghurst Road towards the hotel.

"That was a humiliating experience," Dakota chuckled, "But my panties are soaked."

"Do you want to pop into Woolies and grab some batteries?"

"Not right now," Dakota hissed, dragging me by the wrist, "I need to fuck right now."

We could not get into our room fast enough before ripping our clothes off, kissing wildly as we fell on the bed. Dakota reached into the bag and fished out the enlarged butt plug.

"Use this on me," She breathed, before sliding off the bed to retrieve the bottle of lube from the suitcase.

Since the toy was shrink wrapped, it was not easy to extract the butt plug from the packaging. I had to use the complimentary corkscrew to pierce the plastic and remove the rubber toy. After handing the toy to Dakota, she fell on the bed, laid on the bed, scooted to the edge and pulled her legs back. I dropped to my knees, grabbed Dakota by the hips to bring her love holes to my face.

While deepthroating the new toy and moaning erotically, I licked her clit, pussy and arsehole in succession before focusing on the bean while fingering Dakota's holes. After she shuddered to a banging orgasm, Dakota begged my to rim her arsehole hard. The fingering has certainly relaxed the O-ring but was it enough to accept to new, larger toy. As I rimmed Dakota's wrinkled rosette which she winked her hole against my tongue, she smeared her favourite lubrication across the saliva-dripping butt plug.

"I think I'm ready to try this new plug," Dakota breathed, her body shuddering from the sensation of my tongue, "Go slowly, my love."

I grabbed the greasy toy and gently placed the head against Dakota's twitching shitter while I kissed and tongued her pussy. Applying the minimum amount of pressure, I pushed the plug inside Dakota's arsehole.

"Oh, oh, oh!" Repeated Dakota as she felt the intrusion open her most taboo entrance, "Feels so big."

"Does it hurt?"

"Surprisingly no," Hissed Dakota, "Just massive stretching."

Dakota handed me the bottle of lube and begged me to apply more grease to the toy. I applied as much as needed to easy entry. The additional oil certainly helped and I felt her muscle relax and open up reluctantly. My girlfriend was breathing heavily, her pendulous breasts rising and falling. As we reached the widest part, Dakota snaked a hand down her taut body and delicate fingers circled her clit.

"Fuck!" She repeated over and over as I pushed the toy deeply inside her dirt box.

Pop! Dakota's muscle suddenly swallowed the massive intrusion with much anger and reluctance. At the moment of acceptance, Dakota's pussy released a sudden stream of fluid into my mouth. The squirt was a verboten subject that Dakota seemed reluctant to discuss, even though I reveled in the act and eagerly swallowed her gift.

"Fuck me!" Dakota demanded as I wiped my mouth on the bed sheet.

Dakota's pussy was super tight without anything in her butt. With the original plug, I had to enter slowly and with a lot of lube despite her pussy bubbling with arousal. With the larger toy, I needed additional caution and the last of the grease to ensure I did not hurt her.

"Fuck!" She yelled, "I'm so fucking stuffed!"

"You okay?" I asked nervously.

"Give me a second," Dakota panted, seemingly in some pain, "I never knew I'd be opened up this far."

"Take your time."

Dakota's hands covered her eyes and her ample chest heaved as her brain willed the body to accept the expansion. Slowly, the breathing normalized and I felt a slight relaxation down below. The constriction and heat were unbelievable, and I doubted my staying power. Literally, her love muscles could have willed the sperm from my balls by sucking it out of me.

"Go slowly," Dakota begged and placing her hands on my hips, "Don't rip me apart."

"Of course, I won't, my love."

I rocked my hips slowly to generate some movement and Dakota sucked in a breath. Her eyes were glued to the ceiling but were unfocussed. Her brain was processing the sensations running up her nervous system as I eased my throbbing cock in and out of her volcanic cunt. The overuse of lubricant certainly helped and soon I was rocking back and forth easily much to Dakota's vocal approval.

Several months ago, we unlocked a secret to orgasmic bliss when using the plug while I fucked her pussy. When I reached behind me and tugged on the toy so that the ring stretched on its widest part while pumping her cunt, Dakota came savagely. With a larger toy stretching her bung, the resulting orgasm ought to be stronger.

Once I settled into a mutually agreeable pumping rhythm, I started toying the plug. Of course, I could not see what I was doing but given Dakota's body movements and vocal encouragement, I hit the sweet spot on multiple occasions.

Suddenly, Dakota exploded. An enormous stream of female squirt shot out of her pussy, arced in mid air before splashing across her tits and stomach. Then another and followed by a third. Her face flushed and she swore like the sailor Dakota was descended from. The stream of invective and violent spasming of her body was a scene to behold as it was unlike any previous orgasm I witnessed.

"Oh, fuck!" She repeated, "I'm sorry. I pissed myself. I could not hold it in."

"You came," I said, balls deep inside her spasming pussy, "It's a normal reaction and I love it."

"You do?" Asked Dakota, shooting her an earnest stare, "I was told that it was disgusting."

"By an ex-boyfriend?"

"Yes."

"You were told wrong," I reassured my gorgeous girlfriend, "I love it and I know you've tried to stop it but your body is always right."

"You seriously like it?" Dakota asked, unsure of the sincerity of my words, "I try so hard to stop it happening."

"I know you do," I chuckled, "Just let it go!"

"Okay," Dakota said, a little bemused but somewhat relieved, "I felt so embarrassed when it happened."

"No need," I said, leaning down to kiss her lips, "I encourage it."

"You know what I want now?" Dakota asked, rhetorically.

"Some butt action?"

"I want you to fuck my arse and fill me your seed," She said, "Because I love you so, so much!"

Before Dakota lost her anal virginity, she allowed me to fuck her pussy before demanding I came on her breasts, which she pushed together for the perfect target. Often, I would be so turned on that my violent ejaculation propelled my swimmers to wild acts of gymnastics. Initially, Dakota recoiled at having sperm land on her face or in her mouth, but gradually came around to it after she learned that my explosion was a result of how effectively she turned me on. It was not uncommon for Dakota to blow me to climax and swallow the lot.

Since Dakota discovered anal sex, I was sometimes invited to cream pie her backdoor. Tonight was one of those times. Dakota signalled that she wanted a hard back door pounding. This was when she reached peak arousal. There was no light touch, no going slow, but an all out anal assault as seen on Pornhub. ATM, gaping and prolapse were on the menu as I ploughed her shitter before letting my balls pin cushion her guts.

As Dakota was lying on her back with her gaping hole hanging off the edge of the bed, missionary position was the logical starting point, and I jammed my raging cock deep inside Dakota's pooper.

"Oh, yeah," She groaned, "That's what I want. Fuck me hard!"

With no warmup time, I was free to smash her back doors in a way I rarely experience but relish when allowed. Dakota played with her tits, clit and fingers her sopping cunt, moaning and spewing gibberish as she regularly climaxed.

"Fuck me. Fuck me. Fuck me!"

From missionary, I buggered Dakota's butt hole mercilessly in both cowboy positions, side saddle and finally busting my nut from the doggy position, unleashing an equally profane stream of invective as her abused hole throttled my shaft.

"Fucking hell!" I yelled as my cock spasms came to an end, "You're fucking wild."

"You're pretty good yourself," Dakota giggled as she shook her booty while my cock began deflating, "Look below."

I pulled out of Dakota's O-ring with a satisfying plop and looked underneath her. There was a massive puddle of girl squirt on the bed sheet. I complimented her on her orgasmic talents.

"You came a lot," Dakota teased, reaching around and fingering her impressive gape, "You want to see my cream pie."

"Of course," I chuckled, wiping my sweaty brow.

Dakota walked into the shower cubicle, leant by the tap mixer and spread her cheeks to reveal a busted arsehole bubbling with come. When she pushed, the worn muscle expanded, and stream of noxious fluid of sperm and lube streamed down her legs and pooled on the sink. While she was a wild ride, tasting that mixture was a stretch too far.

Next day, we took the ferry to Manly. After enjoying an excellent seafood lunch, we strolled to the beach. Holding Dakota in my arms, I asked her for her thoughts.

"Naughty thoughts," She giggled, "Some butt stuff."

"Oh, do tell."

"Well, you know how you like to lick, finger and fuck my butt?" Dakota asked, "Well, I was wondering if you want me to do that to you?"

"I love being rimmed and occasionally fingered," I replied, "But I've never been fucked."

Okay, that last comment was not technically correct, but Dakota did not need to know about my history, just like I did not need her history.

"Would you like me to do some of that?" Dakota asked, somewhat redundantly.

"Of course, what made you think of that?"

"I was thinking about the double dong that we looked at yesterday," She replied, "In fact, I can't stop thinking about it."

"And?"

"I was picturing us using it together," Dakota whispered, her cheeks reddening, "Butt to butt."

"Kinky!"

"When I pictured it in the shower this morning, I creamed myself."

"Nice," I said, impressed with her devious imagination.

"Would you be up for it?"

"I'm open-minded," replied, "But what's the quid pro quo?"

Dakota cottoned on immediately and agreed to let me "wet her". I asked her if she wanted to go back to the sex shop, and the answer was yes. On the ferry back to Circular Quay, we found a discrete locate that allowed me to finger-bang her dripping pussy to climax. Both of us eagerly awaited the fun and games that were likely to follow as soon as we got back to our hotel via the Kings Cross sex shop.