Six quick months had rushed by since the fateful Halloween when Jan had revealed the wilder side of herself. It seemed, to me, to have always been bubbling beneath the surface. The events of that night changed our relationship, but at the same time didn’t change anything at all. Not knowing it was even possible, we were more expressive to each other and more open. Not to mention, the sex was far more adventurous. But everything else was as it had been.

In the middle of April, we decided that a well-needed break was in order. Work had been stressful for both of us, and it had been nearly a year since we had gone on holiday. We had our list of dream places we wanted to visit, both near and far. While browsing one day after work, I discovered cheap flights to Japan. The Asian country was the number one destination of culture, history, food and downright weirdness that had occupied our mutual “Top 3” lists of destinations for years and years.

Shouting out to Jan, I had already started the booking process for the flights. When she eventually sauntered in to see what all the fuss was about, her face went from tired to excited.

‘OMG. TIGER. YES. DO IT.’ She quickly left the room again while shouting over her shoulder. ‘I’m just going to put in the request for leave.’ Requesting leave was something I didn’t have to worry about as I was self-employed. I did the last few details and made sure all the dates were correct. With a click of my mouse, it was done. Two and a half weeks in Japan were just around the corner. I could hear Jan pacing as she was on the phone with her boss in the other room, followed by a loud, ‘WOOOO.’

That evening, after I made us a light salad and cracked open a bottle of wine, Jan popped her feet on my legs and sighed. ‘Thank you for booking this trip on a whim. Work has been stressing me out, and I can’t wait to get away with you. Think about all the fun we are going to have.’

I chuckled, ‘You’re welcome,’ and started massaging her calves and the tops of her feet. She soon had her eyes closed and was enjoying the sensation.

‘You know. Maybe we can find some more costume or outfit shops in Japan while we’re there. We’re due something new.’

Jan said this so casually it made me smirk.

‘Oh yeah? It sounds like you have something already in mind,’ I asked.

‘Well… Maybe. We’ll see.’ She was being coy, which meant that she was up to mischief. She downed the last of her wine that was in her glass and pushed me so I was lying on my back. ‘Hang on. I changed my mind. I want you on the floor instead,’ she guided. I scooted off the couch and lay down on the floor. Jan wiggled out of her jeans while I lay there looking up at her. Her black lacy boyshorts soon followed. I waited in anticipation as she perched herself between the couch and coffee table and lowered her glistening pussy to my face. I tried to get my tongue to her, but she stopped short. ‘Easy tiger. Wouldn’t want me to think you are too eager.’

I groaned at this, which made her cackle. In a heartbeat, I was being smothered. My tongue crept out and found its way between her folds, which tasted like heaven. Jan had really wanted this as she didn’t last long. This was good because even though she allowed me some air regularly, I was getting tired despite really enjoying myself. I could feel her legs tensing more and more as I lapped away like a dog at a water bowl. Suddenly, my mouth and face were drenched as Jan squirted when a leg-trembling orgasm rolled over her. She cried out, ‘SWEET. JESUS.’

She sat back on my chest while catching her breath, and I caught mine. It had been a long time since Jan squirted on my cock, let alone my face. Thinking back as I caught my breath, it would have been when we first started dating in college that it had happened. Something that happened when Jan was at her most aroused.

‘Glad I could have been of service,’ I smiled.

‘Good boy,’ gasped Jan. ‘Very good boy.’

Since our eventful Halloween night, I became her “boy” whenever we had sex, or I was ordered to please her. Sometimes, however, she would allude to when I was dressed as her “Little Bo Peep” and tease that I should be her good “girl” again. This was usually while I was bent over and being spanked by her soft hands, or she had her harness pressed up against me while her black dildo attached to it was buried inside of me. That night had awoken something in both of us that we never knew we had but realised we both craved.

I was rock hard as she sat composing herself. I had an air of expectancy that I was going to have my own fun. Jan sensed this too, but being an almighty tease, she reached back and grabbed my testicles and gave them a firm squeeze.

‘Oh no, you don’t,’ she exclaimed. ‘Do you think you’re going to have me please you so easily?’

Groaning in frustration, I knew she was going to tease me some more. Her hand continued to play with me while I could feel myself getting harder.

‘Please.’ I whimpered. ‘Ppplease..touch me properly.’

‘I don’t think I heard that,’ she queried. ‘It sounded as though my “good boy” wasn’t being very good at all.’

I squirmed under her. My arms were trapped by my side as her free hand undid my belt.

‘Lift your hips,’ she ordered.

This wasn’t a polite conversation; it was a command. I did as I was told, bracing myself on my forearms. Slowly, she inched my jeans down slightly. My hard cock tenting the fabric of my already-tight boxer briefs. Her palm resumed the torture of rubbing me through my boxers now, shooting bolts of pleasure into my groin with each pass. My breathing became shallow and rapid as I felt precum soaking the front of my boxers. She could feel me tense up ever so slightly under her hand. In just a few short seconds, I could tell I was going over the edge and braced myself for it to explode out of me. I tried to hold back, but it was no use.

‘Oh no,’ I muttered.

Fresh tremors shook through me as I poured thick strands of cum into my boxers. Jan had stopped touching me at this point, and when I eventually opened my eyes, she was looking down at me with disapproving eyes. Sighing, she leant down to my ear and gave it a little flick with her tongue. ‘Shame. I was planning on giving you a blowjob. But it looks like that is out of the question now. Ruined. Just like your boxers.’

Leaning back again, she slowly slid her hand beneath my waistband and softly began to caress me. After a few moments of gentle exploration, she withdrew her hand and looked into my eyes with a stern expression.

‘Now you will learn what happens to the “bad boys” who don’t learn to control themselves,’ she whispered. She then brought her fingers to my mouth and commanded in a low voice, ‘Clean my hand.’

Having never done this before, I was a little bit in shock but found my mouth instinctively opening and being filled right away by her fingers. It wasn’t as bad as I expected, but still unexpected. I could also taste the last of her juices at the sides of my mouth as I cleaned her hands.

‘That’s.. that’s a great sight,’ she panted.

With that, she got up and told me to go shower before bed. I took a moment before following her upstairs and into the bathroom. In the shower, I let my mind wander about the last few months and how comfortable I was with Jan taking control. How much my love for her somehow grew with each passing moment. Although she was taking control, I felt that love back. Never once did I feel unsafe or worried about what might happen. Just comfortable.

Snapping out of my head, I heard Jan coming into the bathroom and telling me she had placed some fresh clothes outside.

Finishing up, I came out and started to towel off. In the corner, on a little stool, were my PJ shorts and a T-shirt. But, resting atop them was a pair of lacy boy shorts with delicate lace trim and floral pattern.

I gasped as I noticed them and called out, ‘Um-- Jan? Was this intentional?’

‘Of course,’ came her reply.

I hesitated for just a moment. Was I ready to delve into the perverted world that Jan had ignited for us even further? I picked them up and enjoyed the feeling of them before slipping the panties on, followed by my PJs. I wondered to myself why I hesitated in the first place. With every movement, the lace grazed against my skin and sent sparks of pleasure through me. After brushing my teeth, I came out and told Jan the bathroom was free, but all I could think about were those soft, teasing panties that had awakened something inside me.

‘No need,’ she replied. ‘I used the guest room bathroom.’

I hopped into bed, and Jan embraced me. Her hand snaked to my ass as she could feel the panties through my shorts. I smiled and returned the hug, also feeling the panties against my skin as we both drifted off towards sleep. In a soft voice, Jan said, ‘I can’t wait to go to Japan and have more adventures.’

This was the last thing I heard before falling asleep deeply.