Loving Transwomen 17 - Queenstown

A/N - Hello. There are very few options for where to set a story starting with Q. The only country is Qatar, and that's just a non-starter. So it came to thinking of cities. There are a few in China. There's Quebec, but I've already set a story in Canada. Quito? Set a story in Ecuador already. Then I thought about the country across the Tasman Sea and the town of Queenstown. Yeah, I think that I can set something there.

This is going to be another romance with a heavy dose of taboo though this will be 'alternative'. Come on, you should know by now that I love to write that! If you read the story that I set in Japan, it will be similar to that though will involve both a step-sibling and a step-parent. Only one of the two will be transgender.

A word of warning. The MC has a fluid sexuality, and this story will feature same-sex scenarios (man love).

Submitted so far:

Loving Transwomen: Adelaide (Romance)

Loving Transwomen: Buenos Aires (Alternative Romance)

Loving Transwomen: Cambodia (Interracial Romance)

Loving Transwomen: Dublin (Lesbian Romance)

Loving Transwomen: Ecuador (Group Sex)

Loving Transwomen: Finland (Taboo Lesbian Romance)

Loving Transwomen: Germany (Alternative Romance)

Loving Transwomen: Hanoi (Interracial Romance)

Loving Transwomen: Italy (Alternative Threesome Romance)

Loving Transwomen: Japan (Romance with a hint of Taboo)

Loving Transwomen: Laos (Interracial Romance)

Loving Transwomen: Montreal (Alternative Romance)

Loving Transwomen: Namibia (Switch Romance)

Loving Transwomen: Oslo (Romance)

Loving Transwomen: Philippines (Interracial Romance)

Australian / British standard English. There is a good chance of reading the following: lots of profanity, characters drinking, typos, and bad grammar at times.

Proofreading and editing suggestions provided by OhDave1. Any mistakes are still mine.

Comments are appreciated as always.

Feedback by email is always welcome. Enjoy chatting with anyone who likes my work.

*****

A trip to visit someone special reveals long-dormant feelings.

*****

I'll be honest straight away. I loved my blended family. My parents divorced only a couple of years after I was born. To my surprise, my father fought tooth and nail to gain custody of me, and after it was revealed that my mother was both a drug addict and had been working as a prostitute, the judge readily handed my father full custody with my mother only able to visit me with supervision.

My father was a good man and worked his arse off to support his son. And it was fortunate that his parents were so willing to pitch in and help out when it came to helping with me. My maternal grandparents were similar, disappointed in their daughter and practically adopted my father as their son.

When I was five, my father met and quickly fell in love with a woman named Debra. He took his time introducing me to her and her two children, but on the very first day that I met, I knew that I was a little shy when introducing myself. But my father knew that I was desperate for a mother figure. She was wonderful with me from the start, and it didn't take long before I loved her as much as my father.

The first time that I said I loved her when I was six years old, she burst into tears. I thought that I'd done something wrong as my father walked into the living room to find Debra hugging me as tightly as ever, whispering that she loved me like I was her own. As far as I was concerned, Debra was Mum.

I wasn't sure if I should call her that and I didn't know how to talk to my father about that. I was seven and didn't know how to express myself. They married when I was that age, Dad making sure I looked good in my little suit, and Debra looked... beautiful. It was during the reception that I walked up to her, trying to get her attention.

That's when I called her 'Mum' for the first time. It just slipped out, and when everyone fell silent around me, I thought I'd said something wrong yet again. It made both Mum and Dad cry as they both hugged me tightly.

Debra was Mum, and with Debra came a brother and sister. Claire, my sister, was only a couple of years older than me. It was awkward for me at first as I was used to being alone, but we soon became close friends. Then there was Chris, who was a few years older than me though he was friendly with me from the first day we met, and he would introduce me as his little brother from that first day of meeting.

It's fair to say that I loved both Chris and Claire.

When I was around ten years old, Debra sat me down and said that she had to explain something about Chris. I didn't really understand too much at the time, but she explained that Chris was born a boy, but he had always felt like he was a girl. When I asked if he was going to be a girl, she smiled and nodded.

"You'll see lots of changes in the coming weeks and months, sweetie. And she's no longer going to be called Chris. She wants to be known as Bailey."

I slid off the couch and walked towards her bedroom. She was lying back on her bed, walking in as I always did. "Hi Bailey," I stated.

She was up and off the bed instantly, hugging me as tightly as ever. Mum walked in and joined our hug as Bailey cried. "Best little brother ever," she whispered.

Bailey remained living at home while she attended university, but after she graduated, she sat down with the family one evening and explained that she was moving to New Zealand. It wasn't much of a shock as she'd been there a couple of times already on trips. A friend of hers was already there setting up a business with Bailey moving there to assist in building it up.

"New Zealand is only a short flight away, but I feel this is a fantastic opportunity," she stated.

I was upset that she was leaving but I was now old enough to understand things. The day that she was flying out, Mum made sure I was off from school so I could wish her farewell at the airport. I still had a few years left at school and then university, and with me looking at getting part-time work, I wasn't sure if I'd ever be able to get overseas. Bailey promised that she'd visit whenever she could.

With Bailey out of the house, that left only Claire in the house. As we got older, distance grew simply because we were different people. We attended different schools, moved in different circles, but although there was distance, we always remained friendly. But I probably grew even closer to Mum with Bailey now out of the house. Dad was so busy working that I sometimes only saw him in the evening as he was away for work very early in the morning. Mum worked part-time as Dad was happy to look after his wife and family.

As I got older, I also learned things about myself. One thing I understood was that my sexuality was somewhat fluid. I found myself having crushes on girls and I'd also have the occasional crush on a boy. Puberty wasn't easy and I wasn't particularly impressed that once I hit the dizzying heights of five-eight, I just stopped growing. Considering people seemed to be getting taller, and that even plenty of girls were as tall if not taller than me, I know that I complained to Mum more than once about being short. She'd hug me, give me a kiss on the cheek, and state good things come in small packages.

Yeah, I loved her to bits.

I still had relatively good self-esteem regardless and it didn't put me off attempting to date. I ended up attending the end-of-school function after graduation with a date, a girl that I'd been friends with during most of my time at high school. What surprised me during the night was that she wanted to dance with me all the time, and during one of the last dances, she kissed my cheek and whispered that she wanted to end the night a particular way.

And that's how I lost my virginity. We were both rather clueless once we were naked, but I think that I impressed her with my willingness to go down on her, and when it came to making love, we eventually figured things out. We knew a relationship wasn't going to form out of that night, but it was the best way to end our time at high school together.

It was only at university that my life would become rather interesting.

*****

I managed to move the strong arm holding me as I carefully slid out of bed. I glanced back to see my lover was slowly waking up himself. He was a mountain of a man, considering he played for the university rugby union side as a flanker. I also knew he was bi-curious, and he wasn't the first rugby player to end up fucking me.

"Where are you going?" he murmured as he slowly woke up.

"I'd better get dressed and go home. I've got some studying to do, and I've got work this evening."

Clothing had been thrown everywhere after arriving at his apartment the previous night. We'd spent the evening with quite a few people at a nearby club, and I knew a couple of his roommates hadn't come home alone either. As I looked around for my clothes, I had to get down to grab something that had slid under his desk. With my arse in the air, well...

I felt a firm hand on my lower back and his thick cock between my cheeks. Given that I could still feel his cum inside me, I glanced back as he grinned at me. With a simple move, he pressed his cock against me and slid inside me rather easily.

"Fuck," I moaned, "Fuck, James..."

With his hands at my hips, he pumped away nice and slow, allowing me to savour every inch of his cock with each thrust. I moved my hips in time, his skin soon slapping against my arse as the tempo picked up. I was soon moaning loudly as I enjoyed hearing his grunt and groans.

"Fucking hell... Such a tight little arse, Sam..."

"Fuck me... God, fuck me, James..."

He ended up mounting me, feeling his hot breath on my neck as he pumped me harder and harder. When he finally came, he reached under and stroked my cock, whispering that he wanted me to cum as well as he was a generous lover. He wasn't wrong about that as I'd ridden him the night before and coated his chest in my cum.

When he pulled out, I turned around and kissed him. He'd been awkward the first time I kissed him, but he now kissed me back, making me smile as I felt his cum start to leak out of me.

"I do really need to go soon," I whispered.

"Couldn't resist with that beautiful little butt in the air." He easily picked me up off the floor and placed me down on the bed, spreading my legs as he easily slid his cock inside me again. "Can't get enough," he groaned, "I stay so fucking hard when I'm with you, Sam."

I held on tight to his muscular form as he fucked me again. It was only after he came inside me a second time that he eventually pulled out and flopped onto the bed next to me. I lay next to him and simply savoured the dull ache as I always enjoyed his cock inside me. If I thought about it, I certainly have had more men fuck me during my time at university than any action with women.

Mum picked me up from the train station, offering to make me a hot drink once we were home. I disappeared to my room to get changed, returning to the kitchen to find Mum wearing one of her silk robes. I carefully sat down on one of the wooden chairs at the kitchen table, Mum smirking as she placed two mugs down on the table before sitting next to me.

"Good night, sweetie?"

"I don't think James wanted me to go. And, well..."

"He fucked you before you left?"

Mum had always been open-minded about sex and although I didn't go into details, she knew that I spent more time with men. She figured out the first time I'd been fucked as I practically staggered in the front door the morning after, and it was obvious to anyone that my arse had received some treatment.

"Twice, Mum," I stated with humour.

She leaned over and kissed my cheek. "I'm glad you're having fun, sweetie. You're at university and it's the perfect time to experiment."

"I'm just glad that no one really gives a shit that I like what I like."

"You know that if you ever wanted to invite one of your friends over that we wouldn't mind."

I felt my face growing warm. "Well, James has his own place with a couple of friends near campus. It's just easier to go there."

"What do you want after university? Settle down with a girl? Kids?"

"I honestly don't know," I admitted with a shrug.

She leaned in closer. "How about an older woman?" she teased.

I looked at her as she smiled at me. "I've never, um... You know..."

"You ever had thoughts about me, sweetie?"

I definitely blushed, but I nodded. I knew she wouldn't scold me for it. "I guess step-family porn is rather popular now, isn't it?"

"I don't watch that. I just... You know... Going through puberty..."

"What about Claire?"

"No. To be honest, I've never thought about her in that way."

"Bailey?"

Just mentioning Bailey nearly made me cry as I missed her so much. I was in my second year at university and had only seen her sporadically over the last few years. We talked to each other on the phone at least once a week, constantly messaged each other, but it wasn't the same as being with her. She was now in her late twenties, and the last few photos that I'd received from her had proven that she'd blossomed into one hell of a beautiful woman.

"I'm always confused about my feelings for her," I admitted.

"I know how much she loves you, Sam. And that love was solidified by how quickly you accepted Bailey as she is. I still remember the day that I told you..."

"I know that I wasn't that old, but I understood the importance of what you were telling me. And I just wanted to make Bailey happy."

We moved into the living room and snuggled on the couch. Mum was shorter than me though only by a couple of inches. She still called me her big, strong young man. She continued to tease me about James and the other couple of guys that I'd occasionally be with. When it came to women, I had plenty of friends of the opposite sex, but my dating record wasn't great. And online dating and apps were even worse for someone like me.

To her amusement, I arrived home after a night out looking like I'd been ridden hard. I practically collapsed onto the couch, Mum walking out with a drink for me before she sat down next to me. She curled her legs underneath her and turned to face me.

"Looks like you had a good night out, sweetie. Feeling a little sore?"

"Might have taken on more than I should have done."

"Oh... Do tell, sweetie."

"Four guys, Mum. Four of them."

She burst into laughter before leaning over to give me a kiss on the cheek. "I'm glad that you're having so much fun at the moment, sweetie. Was James involved?"

"It was him, a guy we met at a club, one of his teammates, and one of his roommates. We didn't finish until early this morning."

"Was it a gangbang, sweetie?" I turned to look at her, Mum returning a face of pure innocence though her question suggested anything but. "What? You think I don't know what that is?"

"Well... I mean... Do you really want to know the details?"

"Only what you feel comfortable telling me, sweetie."

"It was usually both ends while the other two would wait their turn."

She laughed out loud. "My God, I'm not sure if things are different nowadays. Are these other men fluid like you? Bisexual? Gay?"

"James is pretty much bisexual now. I know he's going to settle down with a woman after all of this, but he does like fucking young men like me. His roommate, Mark, is totally gay and I've seen plenty of young men leaving his room in the morning. He definitely has a preference. The teammate, Craig, was curious though definitely enjoyed himself last night. The guy we met at the club was also totally gay. He was a little older than the other three."

Mum found it rather exhilarating and rather amusing. All she wanted me to be was safe. I admitted that I hated condoms but would get regularly tested, just in case.

For my last year of three at university, I focused on studying and making sure my marks were as high as possible. James had graduated and moved on. To my amusement, within three months, he sent me a message, letting me know that he was dating a woman, but he thanked me for allowing him to explore his curiosity.

It was weird going from having sex constantly to being almost celibate, but I knew it was the right decision for me. The one constant in my life was Mum, and I think we grew even closer after Claire moved out. Even though I was nearing twenty-one, she still mothered me, and I loved it. She was my biggest cheerleader and seemed to just love spending time with me.

To be honest, it did make things a little awkward at times because I still found her so attractive. She had brunette hair that she kept down to her shoulders. Blue eyes that were usually covered by thin black framed glasses. And she had no problem wearing low-cut tops that would show off her cleavage. Being frank, she resumed being one of my fantasies while pleasuring myself.

So, of course, she walked in on me while I was jerking off one afternoon. I preferred to jerk off without watching porn, wanting to rely on my imagination. I had no idea she was in the doorway as I moaned 'Mum' more than once. I only knew she was there when she sat on the edge of the bed. Scared the life out of me as I looked at her face to see her smiling at me.

"Consider me flattered that a handsome young man thinks about me in such a manner," she whispered, leaning down to kiss my cheek, "Finish up and come out into the living room, sweetie."

"Finish up?"

"Make sure you cum, sweetie. I'd hate to be the cause of a case of blue balls."

I could feel my cheeks were burning when I walked out into the living room a few minutes later. I sat down on the couch, and she immediately shuffled closer. "I had no idea you were suffering, sweetie. I know you would masturbate regularly. I do too."

I might have just masturbated, but there was a tent in my shorts immediately upon hearing that. I wasn't stupid; I knew women masturbated. I'd heard Claire more than once though I never interrupted her nor mentioned anything. "I know it's weird, Mum..."

"I know I'm your Mum, sweetie, but... Well, we've always known that you didn't come from me. Being attracted to me..." She paused and cuddled into me. "I don't want to make things awkward. There is one thing that I want to do for you though."

"What's that?"

"After you graduate, I want you to finally head across to New Zealand and see Bailey. It's been too long since you've seen her. I'll purchase the airfare for you. Though I'd like it to be a surprise, I'd rather she be at the airport to greet you."

"I'd love to go. Thanks, Mum."

"You're welcome, sweetie."

I did wonder if she mentioned anything to my father, though even if she did, I don't think he would have mentioned anything to me. Given they had been married for quite a while, I knew passions sometimes cooled over time, though I knew they still loved each other. A couple of days later, I was lying back in bed, reading a book when Mum appeared in the doorway. She closed the door and smiled at me before opening the silk robe to reveal her naked body.

"Now you know what I look like for when you need some relief, sweetie," she whispered before walking over to kiss my cheek, "And if you're a good boy, you might get some surprises on your phone."

"You're serious?"

"It'll be our little secret, sweetie." She stood back and let the robe slip off to stand naked next to my bed. I was rock hard and almost starting to salivate at the sight. I'll be honest, I wanted to touch her and do a hell of a lot more. But I knew that would never happen. "I do love how you look at me, sweetie. Makes me feel wonderful considering I'm over forty now."

"You're fit as fuck, Mum."

For the next few months, I gave no thought to being with anyone else as Mum kept her word. I received a selfie every single day and nearly all of them were of her nude, if not even more risqué. The surprise was when she sent me a video of her masturbating. That was quickly put to use, letting her know the next morning at breakfast that I absolutely loved it.

She also told Bailey about my future visit and to say that my big sister was excited was an understatement. Mum organised for me to head over there for at least a month, and I would be staying with Bailey in her apartment the entire time. When I asked where I would sleep, Bailey made sure to FaceTime me and let me know that she only had a one-bedroom apartment... So I would be sleeping with her.

By the time I graduated, I had a phone full of pictures of Mum and also quite a few videos. And she had grown increasingly upset at the idea of me moving out. The night of my graduation, I enjoyed a meal with Mum, Dad and Claire before heading out with friends for a few celebratory drinks. I arrived home rather late, not surprised that Mum was waiting up for me.

I wasn't too drunk that I couldn't get to bed, Mum following me to my bedroom. She closed the door as she followed me in, surprised that she took off her robe to reveal her naked body. It was only the second time that I saw her naked in the flesh. She helped me undress, and I was blushing furiously when my underwear was removed to reveal my hard cock.

"Well, I've seen that before. Are you hard because of me, sweetie?"

"Yes, Mum... What about Dad?"

"He knows, sweetie. It was our secret, but I needed to tell him."

"And he's okay with it?"

"One hundred percent. Now... Do you want to go to bed and snuggle with me?"

"Mum... I'll probably cum all over you even if we don't do anything."

"And I'd be incredibly flattered. Come on, sweetie. Let's go to bed."

I was achingly hard as Mum snuggled into me. I could feel the heat of her pussy against me as she pressed tightly against me. "Mum... Are you wet?" I whispered.

Her hand moved down, and she showed me her glistening fingers. "I know you loved my videos," she whispered back, "I loved making them for you."

I knew that I couldn't sleep and eventually my hand made its way down to my cock. As I slowly started to stroke off, Mum moved the sheet and blanket off me so I could see her body again. I came so quickly and so hard that most of it landed on her. What surprised me was when she kissed me on the mouth. It wasn't a full-on passionate kiss, but it was more than just a kiss on the cheek.

"Feel better, sweetie?"

"I could probably cum again, to be honest."

"Then cum again. Why don't I give you an even better view?"

And that's how I ended up on my knees with Mum lying back, her legs spread, showing off her gorgeous pussy. When I did cum a second time, all of it landed on her. What kept me aroused was that she rubbed it into her skin and made no move to wipe any of it off. I was spent after my second orgasm, sitting on my knees as Mum gave me a live show. She was so turned on that her orgasm arrived rather quickly, using one of my pillows to dampen her cries.

"This will be the only time," she whispered before I heard her sob. I hugged her close and felt my own emotions bubbling up. "You make me feel so good, sweetie. You have for so many years. I love your father, but the fact that I got to have you in my life for so long... I love you so much, sweetie. The only small regret is that you were not from me... Although that would have made what we just did..." She trailed off and giggled. "Well... Who knows what goes on elsewhere..."

Waking the next morning with Mum in my bed was weird at first. She was spooned back against me with my erection pressing against her. She woke up and rolled over to face me, kissing me on the lips again. Her fingers caressed my cheek as her eyes glistened. "Your father is understanding though..."

"I wish we could make love, Mum," I whispered, "But I'd never do that to Dad. Just having you here like this feels... not wrong, just..."

"He knew that I would be here last night. It would have been a step too far. But part of me wishes that we could as well, sweetie."

Then she clutched at me, holding each other for quite a while before we had to get up. It was the weekend, and Dad was at the kitchen table when we walked out. I felt awkward considering that I walked out with his wife. Mum kissed his cheek before she started to make breakfast. Dad was reading the newspaper and eventually glanced my way.

"Son..." I met his eyes, continuing to feel awkward. "I love her, but you are one of the best things that's happened to her. Trust me, I know. I know how much you love each other. Last night was a gift to you both."

"I don't know what to say, Dad. It's just... I mean... We didn't..."

He looked at Mum before he returned his eyes to me and smiled. "She's a beautiful woman, Sam. I wouldn't have blamed you if you did."

I didn't really understand why he was so okay with it, and I didn't feel confident enough to ask. Mum placed plates down a few minutes later and we ate in silence. Dad eventually got up and started getting ready for his regular golf game on a Sunday. Before he left, he popped his head into my bedroom and told me to look after Mum. Hell, I was almost left thinking he was telling me to 'look after' her.

Though we remained closer than ever, I didn't see Mum naked again, at least in the flesh. But she did continue to send me pictures.

A month after graduation, we were at the airport as I was finally flying over to New Zealand for the first time. Mum, Dad and Claire were with me, Claire hugging me tightly and wishing me a good time before she walked away with Dad. Mum hugged me tightly and made me chuckle when she made sure that my hands cupped her lovely butt.

"Give Bailey my love though I think she's going to be too distracted by you being there," she said softly, "I'm going to miss you so much while you're away."

"I'll miss you too, Mum."

Of course, just holding her in such a manner aroused me and she soon felt me pressing into her. Her eyes met mine and there was a mix of amusement and arousal. "The joys of a young man," she whispered, "I want you to have all the fun possible with Bailey. I know she's missed you so much, Sam."

"I've missed her just as much, Mum."

"Then make sure that you cherish every second while you're over there. Now I'm going to let you go; otherwise I'm going to start crying and just make things awkward." She left a kiss on my lips. "I love you, sweetie."

"I love you, Mum."

The only flight that I'd taken before was one up to the Gold Coast when I was younger. This would be my first international flight. Mum made sure that I was flying a good airline and Dad made sure that I was in Business Class, so I got the best service possible. The flight landed in Queenstown in the late afternoon, passing through immigration and then grabbing my bag before walking out to meet Bailey.

"Samuel!" I heard someone squeal, turning my head to see Bailey running towards me.

"Holy shit!" I muttered to myself. I'd see photos of her, and I'd seen her during our video calls, but seeing her in person was something else entirely. Blonde hair. Blue eyes. Fantastic body. Long legs. She was a walking wet dream.

I knew that I was in trouble. Not only did I still nurse a massive crush on my stepmother, one that would never become physical, but I'd always had a great depth of love for Bailey. I walked towards her, dropping my bag before I found myself crushed against her chest, my head nestling just above her breasts. They were larger than I thought, suiting her frame perfectly.

When she leaned down to kiss me, it was immediately on my lips. I was surprised at first but she leaned back just enough to stroke my cheek. "Still my cute little brother," she whispered before she hugged me again. That's when she took a few moments to release some tears, "I'm so glad that you're finally here. My God, Sam..."

"I've missed you too, Bailey."

"True, but I know Mum has been keeping you happy." That had my head jerking back as she met my eyes and there was a playful smirk. "Do you think she wouldn't let me know?"

"I know Dad was told..."

"I just know how much Mum loves you, Sam. To be honest, I'm surprised she didn't take you to bed and make love."

"Yeah, but Dad... Although he didn't mind that Mum did come to bed with me one night."

"And she got naked for you... And you masturbated together... So hot, Sam..."

"Really?"

"I just think it's so naughty and I know Mum was ever so happy. Anyway, are you ready to go?"

She had a small car and drove me around the town, showing off the main sights, before we parked up outside her apartment block. She was on the highest floor, providing fantastic views of the surrounding area. I was standing on the balcony when I felt Bailey's presence behind me, her arms wrapping around my chest as I felt her breasts against my back.

"I'm so happy that you're here that I still want to cry," she whispered.

"You have no idea how much I've missed you, Bailey. It's been too long since your last visit."

"I do want to come home more often, but I've really made a life for myself here."

I turned around and wasn't too surprised that she leaned down to kiss me again. The surprise was how passionate it was within a few seconds, and when her tongue slid into my mouth, I moaned softly as I found myself pressed back against the railing. When she pulled back and smiled at me, I felt my heart thundering in my chest, her fingers stroking my cheek again.

"My little brother is still incredibly cute," she stated softly, "We should head inside. I'll start making dinner. I want to hear about all your stories again."

"Even the naughty ones?"

"I always loved the naughty ones. I'm glad you found yourself at university, sweetie."

Bailey proved that she had learned how to cook as the meal she put together was delicious. We sat together at the small kitchen table as we ate, Bailey opening a bottle of wine to share as we shared stories. She had been interested in my stories about James and other men during previous conversations and seemed to be aroused by those same stories again.

After we cleaned up, we sat together on the couch. She turned on some music as we continued our conversation, Bailey eventually shuffling closer, resting a hand on my chest before she kissed me again. It didn't take too long before it was hot and steamy. I eventually had to break the kiss to gaze into her eyes. I was feeling a little confused.

"Bailey... You know how much I love you but..."

"Does this feel wrong?"

"It feels so right that it scares me."

"I'm a little scared too. That's what will make it so good."

I was a little worn out after travelling so Bailey suggested that we head off to bed rather early. She disappeared to the bathroom to get changed. I undressed and wasn't sure if I should keep something on. In the end, I stripped naked and got into bed. Bailey appeared in the doorway of the bedroom, wearing only a pair of panties, the bulge prominent. I was hard immediately as her breasts were perfect, her tummy toned, and she was just... beautiful.

Then she smiled at me before joining me in bed. She felt my nudity and smiled at me before kissing me again. I moaned into her mouth as I felt her hands on my back, moving to my arse. I felt her body up at the same time. When one of my hands cupped her breast, she broke the kiss and smiled. "You like them?"

"Fuck yes," I whispered.

"Good. I wanted to be sexy, but I always hoped that you'd find me sexy as hell."

She removed her panties and showed them to me before flinging them onto the ground. As our bodies pressed together, I felt her cock pressing against me. I knew she was going to be larger than me from the large bulge. We made out for a few minutes before I rolled over and spooned back against her, feeling her arms holding me tightly. I heard a sniffle more than once as she occasionally squeezed me.

"I love you so much, Sam," she whispered, "We're going to have so much fun while you're here... You really think I'm sexy and beautiful?"

"Like a goddess."

"And you don't mind that I have a big girlcock?"

"I think that just makes you even sexier."

"I haven't had sex in so long, Sam..."

"Been quite a while for me too, Bailey... Do you want to have sex with me?"

"God yes."

I turned my head to look at her. "I've fantasised about you for years, Bailey. But how do you... I mean..."

"I want to fuck my little brother," she admitted somewhat shyly.

"Good thing is that I loved being fucked. And I would love my big sister to fuck me."

I slept like a log that evening, only waking up when a naked Bailey joined me on the bed, leaving a big, wet kiss on my cheek that had me slowly waking up. Seeing her completely naked was one of the most arousing sights of my life, and Bailey smiled as I couldn't take my eyes off her. I got out of bed as naked as she was, following her pert little butt towards the kitchen. It was a simple meal of toast and coffee.

We showered together, Bailey making sure that my hands explored every inch of her body, including her girlcock. I could feel it throbbing with her excitement as I stroked it. When she returned the favour, I nearly came so quickly that it would have been embarrassing. After we dried off, Bailey remained naked as she led me back to the living room, sitting back before I straddled, feeling her hard girlcock resting between my cheeks.

"One thing, Sam. I have many trans friends, but I have absolutely no interest in sharing you. You'll find many of them gorgeous, but I've already warned them that you're mine. Is that okay?"

"I don't want anyone else," I whispered, those few words almost making her start crying again.

"Part of me wants to take this slow, but I get the feeling that we really need to make love. Would that be correct?"

"I can go as fast or as slow as you wish, Bailey. I already know this is the right thing for both of us. The only thing is... What do we do after I go home?"

"I was hoping that... I was hoping that you might stay here with me. I know you haven't got a job sorted out yet."

"It's something to consider... I'd hate to leave Mum alone though."

"I know. I miss her too. She was always so supportive once I became Bailey."

I ended up on my back as we continued to make out, feeling Bailey's girlcock resting on me and occasionally pressing against my rosebud. I would happily have her slide it inside me there and there, reaching down more than once to give it a gentle stroke and she did the same to my cock in return. What I didn't expect was for her to kiss down my body, smiling up at me before she took my cock in her mouth.

I lasted two minutes before I came so hard that I almost passed out from the sheer bliss of the moment. Bailey swallowed my load before leaning up to kiss me again. I wrapped my fingers around her girlcock and stroked her a little faster. She moaned softly before she lifted herself up, the head of her girlcock on offer for me to take in my mouth.

Savouring the taste of it, I managed to take a couple of inches as she moaned even louder. We eventually moved so I could kneel on the floor with Bailey relaxing back, my head bobbing up and down as I swallowed as much of her girlcock as possible. I wanted to draw out the blowjob as long as possible, using my experience with James and others to bring her to the brink more than once before I backed off.

Pre-cum leaked out of the head as I ran my tongue up and down her thick shaft. Her groin area was completely smooth, spreading her legs wider so I could move down to lick her balls as well. I knew she was getting close to orgasm as I swallowed her girlcock again.

"Oh Sam," she murmured, "I'm so glad that you love my big girlcock."

"I love all of you," I replied, my tongue circling the head of it, "But I know that I'm going to thoroughly enjoy this part of you."

When she was ready to cum, Bailey was polite enough to warn me, my lips wrapping tightly around her shaft as I waited for that first spurt of her cum. It was warm and pleasant enough to taste, swallowing down each spurt as she moaned loudly, her fingers gripping my hair to keep my head in place. Her girlcock continued to throb after she had no more cum to spurt, only releasing her girlcock so I could run my tongue up and down her shaft a few times.

Lifting myself up to sit on her lap, we shared a passionate kiss before she was happy to just cuddle me for a few minutes. "Well, it's fair to say that you know how to suck girlcock," she stated with humour.

"I'll do that whenever you want. I fucking loved it, Bailey."

We finally got dressed and headed out for a couple of hours. There were plenty of things to see and do in and around Queenstown though I was happy to just spend time with Bailey. She had taken the entire month off from work while I was there, though I knew that I'd end up meeting some of her friends and co-workers over the coming weeks.

Queenstown sits on the shores of Lake Wakatipu, walking hand in hand as we did our best to stay warm. It might have been summertime, but it was a hell of a lot cooler than the weather back in Sydney. In the near distance were some spectacular mountain ranges. Bailey had told me that Queenstown was incredibly busy throughout the year, though particularly during the winter as people came from around the world for the ski season.

Bailey wanted to return to the apartment and change before heading out for dinner. She wanted to take me to one of her favourite restaurants. I'd brought along some appropriate clothing, and Bailey was impressed with my shirt and trousers ensemble. She looked spectacular in a dress that was high up her thigh and showed off some tasteful cleavage.

I enjoyed having her on my arm as we strolled into the centre of the city. I could see people gazing in her direction as I knew how beautiful she was. The restaurant she selected was fantastic, sitting at a table that allowed for plenty of privacy. We kept the conversation flowing through the three-course meal though when I asked about what we would be doing after dinner, she took my hand in hers and squeezed it.

"We're having a second dessert back at the apartment," she said softly.

Bailey must have been horny through dinner as by the time we were through the front door of her apartment, I was down on my knees as she shut the door behind her, lifting her dress and freeing her girlcock. She grabbed my head as her girlcock slid down my throat, Bailey moaning with each thrust of her hips as my lips and tongue worked their magic. Unlike my blowjob earlier, this was simply about getting Bailey to cum as quickly as possible.

"Yes, sweetie," she moaned loudly, "Oh fuck yes, Sam. Suck my girlcock."

All I could do was moan as she was relentless. I didn't mind such treatment as I'd had a few guys grab my head and pump their cocks into my mouth and throat. It was just hotter that it was Bailey doing it to me. When she came, her knees seemed to go weak as she was barely able to remain standing after I swallowed her load, eventually dropping down to join me on the floor so she could give me a soft kiss.

"Such a good little brother," she whispered.

She stood up and helped me to my feet, leading me to the bedroom where we slowly undressed each other. By the time I was naked, she smiled sweetly at me before helping me up onto the bed, getting me into the position that she wanted, which was my arse in the air, my head resting on a pillow. Feeling her tongue start to work on me had me moaning softly as I'd always enjoyed being readied in such a manner. And Bailey seemed to love it.

"Do you wax your butt?" she asked.

"Yeah. I started doing it after I started having sex with guys."

"I love it. Keep doing it. And my little brother does have a sexy butt."

I savoured the feeling of her tongue working me before I felt her apply some lube and start to finger me. Once I assured her that I felt ready, I rolled over onto my back as I watched Bailey lube up her girlcock. When she was ready, I pulled my knees back as I spread my legs as wide as possible, feeling the head of Bailey's girlcock against me. She leaned down to kiss me before I felt her push forward.

"Fuck," I moaned as her girlcock was bigger than anything I'd had inside me in a long time. There was only one guy that I could remember who came close. Even James wasn't as long or as thick as she was.

"Fucking hell," Bailey murmured, "I'm going to cum so fast, Sam."

She took her time burying her girlcock, savouring every inch that slid inside me until we were completely joined. She leaned down to kiss me softly as she ever so slowly started to thrust. It quickly had me whimpering each time. She wasn't moving too fast; it simply felt far too good. I watched her face in return, the feelings that she was experiencing expressed in more than just her eyes.

We made out constantly as she gently fucked me, eventually releasing my legs and wrapping them around her, my hands on her back, fingers caressing her soft skin. As she slowly picked up the tempo of her thrusts, she made me moan and whimper a bit louder.

"Oh God, fuck me, Bailey," I moaned loudly.

"I love you, Sam," she whispered as her head ended up next to mine, "I love you so much. Missed you just as much."

I wrapped my arms around the back of her neck. "Love you too, Bailey. Always wondered what it would be like for my sexy older sister to fuck me..."

She pumped me faster and faster, and I'll admit that I urged her on as I was used to being fucked hard. The only difference this time was that it was Bailey, and her girlcock was big. Really big. I absolutely loved it, her girlcock hitting places inside me that few people had. And as she pumped me faster and faster, I felt my cock erupt between us.

Bailey lifted her head and smiled as I moaned constantly during my orgasm. I loved having an orgasm without touching my cock. It meant whoever was fucking me was doing a bloody good job doing it. She moved her hands to rest behind my knees, and in those last couple of minutes, she fucked me senseless.

When I felt her finally start to cum inside me, her lower lip trembled even as spurt after spurt of her cum filled me. She leaned down again after releasing my legs and kissed me hard, whimpering as she really thrust into me hard a few times before she finally stopped, her girlcock remaining buried inside me. Her eyes gazed into mine and a sweet smile formed.

"I don't know about you, but that's a fantasy of mine fulfilled," she whispered.

"Trust me, it's definitely one of mine. I've always thought you were beautiful, Bailey."

She pulled out, lay on her side and pulled me into her chest. She released a few quiet sobs as I knew how much my words meant to her. But I also knew that she'd missed me terribly, and that she hadn't lied about how much she loved me. Stepsister or not, I had no problem admitting that I loved Bailey more than anyone.

I think that I surprised her by eventually rolling her onto her back and moving down her body to take her girlcock back into my mouth. I moaned and hummed as my head slowly bobbed up and down on it, gazing up into her eyes to see her looking lovingly back at me. I smiled as I savoured her girlcock and I knew that I was going to do this every single day for the rest of my life, if she let me.

Lifting myself up so that I was straddling her, I applied a little more lube to her girlcock and then my arse before I slowly slid down it. My face was a picture, at least according to her as she chuckled at the reaction I made as I made sure every single inch was buried inside me.

Leaning forward, the feelings that I experienced for the next few minutes were wonderful. Bailey's hands rested on my arse as she let me retain control. My cock was soon hard again and Bailey loved watching me stroke myself, having me sit back and when I felt her soft hand take over, the whimper I made had her chuckling again.

"I have soft hands," she stated, "Soft hands but a big old girlcock."

"I have a lot to think about, Bailey... But if we can enjoy this every single day and night going forward, I'd love to stay here with you."

I eventually came all over her chest, watching her use a finger to scoop up my cum and taste it. She then pulled me forward so that my head was just above hers, feeling her hands grab my arse tighter before she started to pump me nice and hard. The only sounds that followed were my moans and grunts, and her groans of delight as she pounded me harder and harder.

"Gonna cum," she finally grunted, "Gonna fill your tight little arse to the brim, Samuel."

"Love feeling it already," I managed to state, "So fucking good."

We agreed to shower afterwards as it was definitely needed. Bailey had a lot of fun washing me up and down. My hands caressed every single inch of her body in return. She chuckled as I spent a lot of time soaping up her breasts. When it came to soaping up her girlcock, she didn't get completely hard, but she eventually moved my hand away, suggesting that going to sleep would probably be best for the both of us.

After breakfast the next morning, Bailey took me out into Queenstown as she organised a few things for us to do during my visit there. It was a busy day as there was a ton of things to see and do in and around the town. We only slowed down in the late afternoon, stopping at a place by the water to enjoy a drink.

"We'll meet our friends tonight," she told me, "Most of my friends are just like me."

"That's not a real surprise. I assume that you find safety in numbers?"

"Not just that. Girls like me share a lot in common. We share details of our journey and we understand everything that we've been through. Not all girls are like me, in that they don't mind having a girlcock and love to fuck cute young men." That made me blush, earning a giggle from her before she kissed my cheek. "Do you know much about trans issues?"

"I try to keep myself informed because of you."

"Knew you would. So, you would know that a lot of girls like me don't like having a girlcock. They want to look in a mirror and basically see a female although... Well, biology and all. It's why we want to at least be seen as women. I am a woman in every way possible except that I don't need to lop off my girlcock, and I'll never carry a child."

"What about your friends?"

"I'll let them tell you their stories. They're going to absolutely love you, Samuel." She kissed me softly on the lips. "But remember, you belong to me."

"Always will from now on, Bailey."

She sighed before kissing me again. "Part of me feels bad for Mum. She loves you so much. And I have a feeling that there is a part of her that... wanted to give in to temptation..."

"What would you have thought if I told you that happened?"

"Would have been so fucking hot to imagine. Mum loves you as much as I do. And you've owned my heart for a very long time now." Hell, that almost got me going, needing to glance away and clear my throat. She wrapped an arm around me and pulled me closer to her. "Just telling you the truth, Samuel. I want you to stay here with me. I want to get married, be your wife, and live our lives together."

"I had no idea your feelings were so strong."

"My feelings were confirmed as soon as I saw you in the Arrivals Hall. I knew that I had to keep you here with me."

After returning to her apartment, she showered and started to get ready before I showered and did the same thing. I went with a simple pair of trousers and relatively nice shirt. She walked out and I couldn't help the whistle that escaped me. She looked fantastic in the short skirt, tight sleeveless blouse, and the heels added even more height. She'd spent time styling her hair, and the makeup only accentuated her beauty.

"Wow," I finally whispered, "Do we have to go out?"

"Yes. A night out in Queenstown is always good fun. And given how tolerant Kiwis are about anything to do with the LGBT community, I've felt safer living here than even back in Sydney. No one gives a shit here. It's very much a live-and-let-live sort of society."

We met up in a pub in the downtown area. I was introduced to five of her closest friends, including the friend with whom she'd started her business. After introductions, I was surrounded by six absolutely stunning women, and they quickly figured out that Bailey and I were far closer than simply stepsiblings.

"You're fucking!" Kendra exclaimed, "Don't deny it. Body language is everything, Bailey."

She wrapped her arm around me and gave me a big, wet kiss on the cheek. "I love him so much. I'm hoping that he'll stay with me. Or, if he goes home, that he'll come back to stay."

"The only thing that I have to think about is work."

"I'll look after you. I'm very successful, Samuel. Not saying that you shouldn't find work, but trust me, I'm very comfortable here. We all are."

It was a fun night as it was obvious the six women took me under their wing. We eventually hit a club that catered to all sorts of lifestyles and there was no judgement about anyone who walked in. Hell, the more outrageous you were, the more popular you seemed to be. I spent most of the time being dragged up to dance by Bailey or one of her friends. And her friends spent a lot of time teasing me relentlessly. It had me laughing, blushing and feeling rather aroused.

Bailey had warned me about Kendra most of all as she was just like my stepsister. She loved to fuck men and, well, Kendra wasn't shy in whispering into my ear that she'd love to share me with Bailey for an evening or ten. But she also knew that Bailey was monogamous and didn't share, so she was just going to spend a lot of time teasing me instead.

"Kendra wasn't shy," I stated when we arrived home sometime the next morning. Not late enough to see the sun starting to rise, but we were both exhausted.

"I knew that she'd love you," Bailey replied with a smile, "To be honest, if you were not who you are to me, I would recommend that you were to date Kendra. A lot of her personality is a front. She comes across as supremely confident, but like a lot of women like us, it does hide some insecurities at the same time. She's a real sweetheart when you get to know her." Bailey paused and pulled me onto the bed to snuggle with her. "I'm glad that my friends loved you so much. And I guess you loved them in return."

"The main reason to come back is you, Bailey. But I think that I'll have some very good friends too."

"You'll have me as your lover, and you'll have five sisters look after you."

It was Sunday when we woke up and Bailey suggested that we spend the day just relaxing. Of course, in between the relaxing would be a lot of fooling around. My stepsister learned just how much I loved giving blowjobs as I must have given her five of them by the time that we headed to bed that night. And Bailey was more than happy to return the favour. If it wasn't blowjobs, we were fooling around and making love. I honestly couldn't get enough of her, and we did end up christening various rooms around her apartment during the day and into the evening.

Bailey had taken time off work so she could play tour guide. We headed west to Milford Sound via the town of Glenorchy before heading to Te Anau and Fiordland National Park. We headed somewhat north to check out Mount Cook, making occasional stops on the way to look at the scenery and stopping off in provincial towns for a wander about. She told me that Dunedin was a great place to visit, a reminder of Scotland according to the guidebooks.

But to be completely honest, Queenstown had more than enough going for it that we didn't really have to leave. And the most important thing for me was simply spending time with Bailey. I assured her that she didn't have to drive me up and around New Zealand to keep me entertained. Simply spending time with her was all I wanted. Of course, that made her cry and we ended up in bed together as although I made her cry, she also loved that I was honest in what I really wanted with her.

I had only planned to stay ten days, and the second weekend with her would also be my last. She knew that I would need to head home to organise my life going forward. I also wanted to talk to Mum and Dad about the idea of returning to New Zealand. I'd called Mum a couple of times while I was away, and I think she'd already figured out that something had happened with Bailey.

"Mum will support us, no matter what," Bailey assured me as we snuggled in bed on Friday night, her cum still leaking out of me after we'd made love for a couple of hours, "Hell, I think she'd convince your father to move over here if it meant she could be closer to us."

"And Claire?"

"Oh, she's always adored you, Samuel. But her life is over there. She's very much doing her own thing now. We talk all the time, and I honestly don't think she'd give up the life that she's made for herself to follow Mum over here. That's if Mum were to come over here..."

Saturday night was spent with Bailey and her friends once again. For the first time, I found myself on my knees before her in front of people, taking out her girlcock and I didn't hesitate in giving her a blowjob. Her friends all cheered me on as I happily bobbed up and down, Bailey smiling lovingly down at me as she knew how much I loved pleasuring her.

She gave me quite the load as always, keeping it in my mouth and showing it to all her friends before I closed my mouth and gulped it down. I smacked my lips and smiled, hearing them chuckle as I got to my feet and left a soft kiss on Bailey's lips.

"Delicious. I think your cum is going to be a small food group in the future."

We didn't stay out as long as we did last time as she was eager to get home so we could make love. I would be leaving in a couple of days, and we wanted to spend as much time being intimate before I flew home. Making love was as wonderful as ever, Bailey's girlcock being thrust nice and deep every single time. The look on her face was one of pure love for me and I knew my eyes would have reflected those feelings back at her.

I flew home on Monday after spending all day and night Sunday together with Bailey at the apartment. We mixed making love with lots of cuddling and kissing. Bailey needed a little cry every now and then our time together drew to a close. I was sad to be leaving her behind as I hadn't felt such intense feelings for any previous lover compared to what I was feeling for Bailey.

The drive to the airport didn't take too long, Bailey holding my hand the entire time, and she continued to hold it as I checked in and handed in my bag. We waited by the security gates, sharing one last very long hug. The last kiss we shared was simply the best way to express our genuine love for each other.

"I don't want to make any promises, Bailey, but I can't think of too many reasons why I'll want to stay over there," I said.

"No pressure, Sam. But you know how much I love you. And if we were to live together here, it would be so easy to simply live our lives without any judgement."

"To be honest, the only person that I don't want to leave behind is Mum. But we'll see how things go."

She hugged me tightly one last time. "I hope you come back," she whispered, "And I'm going to miss you terribly while you're not here."

"Going to miss you too, Bailey. My bed is going to feel very empty."

"Hope you're ready for lots of nudes and videos of me masturbating."

"I'm going to love all of them."

The flight back to Australia was peaceful as I was again in Business Class. I told myself not to get used to such treatment, figuring that my next flight to Queenstown would probably be on Jetstar and it would be a typically ordinary experience.

Mum was waiting for me after I grabbed my bag and walked out into the Arrivals Hall. Her face simply lit up upon seeing me, making me blush as she didn't hesitate to leave a soft kiss on my lips. Holding my hand as she led the way towards the car, once we were on the motorway heading west, she amused me by unbuttoning her dress to reveal her naked body.

"I missed you, sweetie," she stated, "All the teasing and sending you pictures." She pulled the dress off so that she was sitting next to me naked. With her foot on the accelerator, she spread her legs enough that I could just about see her pussy. "And I'm so wet just seeing you again."

"You're such a tease, Mum."

"When we get home, I want to hear about everything with Bailey. We'll go to your bedroom and snuggle together. I know that just thinking about Bailey will make you nice and hard."

"Mum... Are you okay with what happened?"

She took my hand and squeezed it. "Absolutely. I know how much you love each other. And if you think that going to live with her is the best thing for you both, then you have my support."

Mum did put on her dress once we made it home, following me to my bedroom. I put all of my clothes in the wash as I hadn't bothered doing too much of that while with Bailey as we were focused on other things. When I returned to my bedroom, Mum was lying back on the bed without a stitch of clothing. After I stripped off, I lay down next to her as she snuggled into my side.

"Tell me everything," she whispered.

It took a while to explain what I'd been doing with Bailey. I told her how much I just loved going down on Bailey, worshipping her big girlcock, taking her all the way to the base, and that I just loved swallowing down her cum. How wonderful it felt whenever she slid her girlcock into my arse, whether I was lying back as we made love, or I'd be on my knees and she'd pound me hard from behind. I also loved riding her as it meant I could stroke myself off far easier. I made her chuckle as I told her that we spent a lot of time christening her apartment, and that I also met her friends, adding that her friend, Kendra, was rather eager to fuck me as well.

"Do you want to go and live with her?" she finally asked.

"I do, Mum," I replied quietly, "I love her so much. And if I were to move over there, living together as partners won't raise any eyebrows. Everyone here knows Bailey as my stepsister, and even though we're not related by blood, it could still cause problems. People would ask questions, and it might prove somewhat awkward."

"The most important thing is that you love each other, sweetie. What anyone else thinks doesn't matter."

"What about you, Mum? I don't like the thought of leaving you behind."

"What about your father?"

"I love Dad, but you've always been special to me, Mum."

She kissed me softly. "You're just saying that because I'm naked on your bed. Do you still want to slide that lovely cock of yours inside me?"

"Hell yes, Mum. But Bailey... Well, she said that she won't share."

"I bet if I were to call her and tell her that Mummy wants to fuck you, I'll bet she'd agree because I'm her mother and she knows how much I love you."

Over dinner that evening, I was honest with my father about everything that happened with Bailey. To my surprise, he laughed and assured me that he knew about my feelings for Bailey, had always known how close we were, and wasn't surprised that our relationship had been intimate. When I told him about Bailey's offer to go and live with her, he suggested that it might be the best thing to do.

I called Bailey the next day and we discussed our options. I told her that both Mum and Dad were supportive, and that if her offer was still available, I'd pack up my life and move to be with her.

That made her cry happy tears.

Only three weeks later, I was back at Sydney Airport with a bag of most of my worldly possessions. I didn't really need to send anything else. Bailey's apartment had everything that I'd need, so my bags were full of clothes, mementoes and other little things that I'd need. Mum and Dad both came to the airport to see me off. Dad shook my hand before giving me a hug. Mum was crying nearly the entire time, and our last hug lasted for what felt like half an hour.

"Going to miss you so much, sweetie. My little boy is now a man."

I wasn't hers by blood, but I'd always been her son in her eyes, as much as she'd always be Mum. "Hope you come over and see us soon," I said softly.

"If I do, I won't want to leave. But I now have an even better reason to fly over more often."

Bailey greeted me at the airport. What made me smile was that all of our friends were there to greet me too. Bailey could barely stop crying as she hugged me tightly before I found my face covered in soft kisses. It made me laugh before I was hugged by all of our friends, many of them also releasing a few tears, never blind to how much they all adored me.

We all returned to what could now be called our apartment, dumping my things in our bedroom, before we all gathered in the living room. There was a small celebration of my return before our friends made themselves scarce. As soon as the door to the apartment was closed and locked, we wasted little time undressing and heading to bed.

It was the first day of the rest of our lives together.

*****

A/N - To be honest, I don't think this needs an epilogue. Sam and Bailey are together. And that's the important thing.