Tales of Transwomen Tops Ch. 10

Just a warning that the MC is going to be bisexual as having the male always a virgin in a certain manner is something I've done with most of these stories so far. There's going to be some gay themes at the start.

*****

I left my hometown only a couple of months after graduating from high school. It was the sort of provincial town that had few opportunities unless you wanted to get into farming and agriculture, mining, or wanted to drive trucks over long distances.

None of that appealed so I applied to join the army. To young men such as myself, it was probably one of the few realistic avenues to get out of the town.

The night before I left on the train to Sydney, all my friends gathered in one of the pubs in town to bid me farewell. I did have a girlfriend during the last two years of high school, Tamara, but she was off to university, and with me heading away to join the army, we agreed to call it quits the night after our end of year function. We were each other's firsts at the end of that night, and we thought that was a nice way to end our relationship.

"Are you sure you want to go?" my best mate asked. His name was Chris and we'd been friends since kindergarten.

"Army life isn't for everyone, Mark," Nathan added, "Considering what you're sometimes like with authority."

"I'll be fine. You two were smart enough to get into university and get out of here. I can admit I'm not as smart as all of you guys, so the army is the best way out of here."

There were six of us in total that stayed out until the early hours of the night. We met up with people we knew from high school. Earned more than one snog with a cute girl who knew I was leaving. Ended up leaving with one by the end of the night, choosing not to take her home but to one of the hotels on the edge of town. I wasn't the only one to end up there that night with a pretty girl.

Waking up the next morning, she was staring down at me as I blinked awake. "Hey," she said.

"Hey, Belle." I moved to at least be reclined. "Guess we got a little bit carried away."

"You think I regret last night, Mark?" She leaned forward to leave a soft kiss on my lips. "If you think I'm not the only girl who had a crush on you, then you clearly don't realise how much some of us liked you. You were just blind thanks to Tamara and her... assets."

"Yeah, she did have a nice set of tits. But there was more to our relationship that that."

"I know that, Mark. Just teasing." She leaned forward to kiss me softly. "But I wasn't going to turn down a last opportunity to be intimate with a young man I've always held a candle for before you head off."

Thankfully, the XPT towards Sydney didn't come through until afternoon, leaving me enough time to get home to pack what I needed, my parents driving me to the station in the middle of town, my two little sisters joining us. It was a tearful farewell, at least from my mother and younger sisters. They were both fourteen and, despite the occasional clash growing up, they were going to miss their older brother. My father shook my hand before pulling me in for a hug.

I barely returned home over the next five years. After I completed basic training, I was assigned to barracks in the far north of the country in Darwin, where I would have to learn to deal with tropical heat all year around. And despite what people seem to think, the Australian Army is constantly deployed around the globe, generally as part of peacekeeping forces. Even during the festive period, I'd generally stick to Darwin as trying to get home was, putting it bluntly, a major pain in the arse, involving at least two long flights and then a longer train journey. But I kept in touch with home through email and phone calls.

The first time returning home after five years of service, it would only be for a week. Getting off the train, my parents were there to greet me, Mum hugging me tightly for at least five minutes. My father just had this twinkle in his eye that suggested he was proud as punch of his son. Both sisters had headed off to Sydney for university, though when I walked through the door, they were both waiting for me.

Their tears joined those of my mother on my shirt as I hugged them both. I'd expected my parents but having my sisters with me was a pleasant surprise. We headed to one of the best pubs in town that night for dinner.

"Kept in touch with your friends?" my father asked once the meal was over and we were sitting back, sipping at a schooner.

"Yeah. I let them know I'd be home this week but figured most of them would be busy with their own lives."

"I know Nathan came back home after university. Haven't heard about any of your other friends."

"Well, if they manage to get back, I'll try and catch up with them while I'm here."

Time spent my family was a real shot in the arm as I had missed them. Friends that had remained in town and those who had returned got in touch, enjoying a night out with them during the week. Though we'd all moved on, at heart, our hometown would always be home in our hearts.

"Got a girlfriend, Mark?" Nathan asked.

"I'm not in a steady relationship, if that's what you're wondering."

"Playing the field?" Lachlan asked, a smirk on his face.

Shrugging, I sipped at my bottle of beer first. "Nothing like that. I guess I just haven't found the right girl yet. I do date a bit and have been in involved in a few friends with benefits deals, but I haven't met someone who has captured my heart."

My friends all shared glances. "You've gone bloody soft on us, mate!" Nathan exclaimed as they all chuckled.

"One person I don't hear from much is Chris. You hear from him lately?"

They all shared glances again. "To be honest, we haven't heard much from him since he left for university. Sends the occasional email, but we're left thinking he's moved on with his life. Kind of leaving this life behind," James replied.

"You heard from him much, Mark?" Nathan wondered.

"Not really. Same as you, the occasional email, but he must have changed his number as the last time I tried to call him, the number was disconnected."

"I spoke to his folks a couple of years back," Adam added, "And they don't really speak to him much either."

"Hope he's alright," I muttered, "Do miss the big oaf."

"He's just done what many young men and women do when leaving this place for the final time. They never look back and probably just try to forget," Nathan suggested.

Spending most of my time with the family, I did catch up with my friends one final time before I had to return to Darwin. There were plenty of hugs and handshakes, promises to keep in touch. We'd managed to do so for the last five years so I saw no reason why we couldn't keep that going. To my amusement, I ran into Belle that final night. She'd been off to university but chose to return home to help her family run their business. We didn't fool around though I did enjoy reminiscing about our shared experiences. Before she left, I did receive a soft kiss on the cheek and a whisper that, maybe next time, we could catch up in a more intimate manner.

I served for another three years before I grew bored with the service and thought about transferring my skills towards the civilian sector. I was also sick and tired of living in Darwin. I had no plans on returning to my hometown, and with Sydney the largest city nearest, I figured moving there would do me the world of good. I knew a couple of friends who had moved there so that would help.

Letting my family know my plans, I did visit them first once I'd been given my papers. I already had a job lined up though they were not expecting me to start for at least a month, giving me plenty of time to move to Sydney, set myself up in a new apartment, and organise my life before I started my new career.

"So you still don't have a long-term girlfriend or possible wife?" Mum asked over dinner the second night of my time at home.

"No, Mum. I did manage a two-year relationship, but she spoke about moving to Perth, so she was closer to her family. I wasn't interested in moving to Perth at all, close to her family or not, so we agreed to end the relationship. That was six months ago."

"He's only twenty-six, Mum. Plenty of time yet," Emily stated, she was the oldest sister of my two siblings.

"Plenty of fish in the sea too," Erica added, younger of my two sisters, "And Sydney will probably be a dating mecca. Get on one of those dating apps, Mark."

"Anyway, have you got a place organised and everything?" Dad asked.

"I'll be bunking with an old friend for a few weeks while I look for an apartment. My job is in the city and, from what I've been told, there are plenty of apartments in the inner-west. I'll probably look for something there and hope it's reasonably priced. I left the army with a nice little nest egg considering I lived in barracks the entire time."

"You will get married at least one day, won't you?" Mum wondered.

"If I meet the right girl, then probably. Hoping for grandchildren, Mum?"

"I would like to hold the child of one of my children in my arms at least once before I die." I chuckled and shook my head. Mum had barely turned fifty and kept herself fit and healthy, much like my father. They both had many years if not a few decades ahead of them.

I understood her concerns about me though. I guess they were worried about me being lonely, maybe even depressed if I found myself alone in the big city. The one thing I knew I'd miss from the army would be the comradery. Many friends I'd made had left the service before I had, and I knew of a few that probably wouldn't last more than a couple of years longer before they chose to do something else.

Boarding the XPT as I didn't mind the long rail journey to Sydney, my family all saw me off again, promises again to keep in touch and visiting when possible. During the journey, I kept in touch with my future roommate, a guy I'd served with five years previously. He lived by himself and had told me that he was homosexual, asking if that bothered him. I assured him I didn't care, and I was looking forward to living somewhere different.

Mike met me at Central Station to escort me on the correct line towards the suburb and address I would be calling home from now on. It was one of those new apartment blocks that he explained had been springing up recently. Being a gay man, he added that he'd chosen to live in his current suburb as it was a place that he felt there was safety in numbers.

His apartment was fantastic, light and airy, and my room was enormous. Having been used to living out of a footlocker or a rather small room, it was a mansion compared to what I was used to. I didn't bother packing anything away, Mike asking if I wanted a beer.

He sat on the couch as I took my place in one of the comfortable armchairs.

"Miss the service?" I had to ask.

"Well, for one reason. All the hot, muscular guys."

"I'm sure you must see plenty around here though."

"Yeah, but army guys were happy to just fuck. No commitment or anything. Just no holds barred sex."

"I heard rumours, but I heard some stuff did go down occasionally. That true?"

"You mean like group sex and gangbangs?" Nodding my head, he returned a knowing grin.

"So it did happen?"

"Fuck yeah, of course it did. I was gangbanged more than once, arse just full of cum by the end."

"Transfer that sort of thing to the civilian world?"

"Sort of. I'm not in a relationship though I do have a few lovers. What about you?"

"Single."

"Still straight?"

"Pretty much."

He smirked at me. "Well, if you find yourself horny and want to fuck someone..." Laughing had him chuckling too. "While I am joking, you're a handsome guy, Mark. I'd have to worry if I took you to the sorts of bars I frequent. I'm thinking a young man of around twenty would want you to take them home and show them a good time."

We enjoyed a couple of beers, cooked dinner together, before I headed off to my room to unpack my shit and relax. I heard him on the phone chatting away to someone, not surprised by a knock at the door a few minutes later. Calling him in, he opened it as his eyes immediately went to my shirtless torso, looking me up and down more than once.

"We're going out on Friday night. Wondering if you'd like to join."

"Sure. I don't know anyone here except you. What's the plan?"

"Start out at a pub or two, grab a bite to eat on the way, then head to a club. Just a warning that'll be my sort of club."

"I won't see anything there I haven't walked in one before?"

He opened the door and leaned against the frame. "Walk in on something more than once?"

"Guys sucking cock. I just shook my head and walked on by. Walking in on two or more guys fucking was... interesting. I'd generally just turn around give them privacy until they were done."

"Never thought about joining in?"

"I have a feeling you're going to be teasing me a lot, Mike." He suddenly looked worried. "Don't worry about it, mate. I know it's all in good fun. Don't ease me in gently, just let me know what you're like straight away."

"You don't mind if I have gentleman callers or anything?"

"Nope. Might make a friend or two from the guys who want to fuck you."

As I didn't have to start work for a couple of weeks, I had more free time than I knew what to do with. Mike gave me a few suggestions of things to go check out, including the harbour area, but there were plenty of things to see around the CBD and even further to the west. I was every night as Mike had already proven a dab hand in the kitchen, and I didn't mind joining in to help.

On Wednesday night, he did have a gentleman caller, keeping to myself as I gave them privacy in the living room. I'm not sure if they were trying to be quiet or not but there was no missing the two were fucking nice and hard when they went to bed. Mike and his lover were both quite vocal until they stopped around midnight.

I'll admit that I was a little turned on by it. I guess it just showed that I was a dry spell of my own.

Enjoying breakfast at the counter the next morning, he walked out looking rather happy with life before his face fell slightly. "Ah, shit, I was caught up and forgot I now have a roommate. Sorry..."

I waved off his apology. "Don't worry about it. Sounds like you were both having a good time."

He leaned in close. "He's got a very thick cock," he whispered.

Laughing to myself, I shook my head and finished my breakfast as Mike prepared something for himself and his lover. There was no visitor on Thursday, Mike admitting that his friend the previous night didn't visit often as he was usually on the road. "Still coming out tomorrow night?" he wondered.

"Sure."

I dressed like I normally would for a night out on Friday. Mike and I enjoyed a couple of beers before heading out, arriving at the chosen pub after a couple of his friends had already agreed. After handshakes and introduction, another couple of people arrived. I was quickly picked a straight man out with his gay or bisexual friends, not that I minded. I figured I'd still be in for a fun filled night.

After visiting a couple of pubs, enjoying a quick meal and a few drinks, we headed off to one of the many clubs around the inner-west that attracted clientele such as Mike and his friends. Heading inside, it was like any normal club except men danced with men, women with women, and there were all sorts of alternative lifestyles on display.

"What will you do?" Mike asked.

"Park my arse at the bar and people watch. Should prove rather interesting."

Though they were off dancing and having a good time, one of them would return often to buy drinks and shots. I'd always take a shot, but as I wasn't moving, I guess the drink hit me more than I realised. I vaguely remember chatting with a few guys, even getting up to dance a few times, feeling the presence of many bodies around me. It must have been heading outside that caused that feeling of being blacked out.

Waking in the morning, I felt a dull ache and turned onto my side to see a man lying next to me, fast asleep. Clearing my throat, he slowly opened his eyes and smiled at me. "Um... Who are you?"

Turning onto his side, he was rather muscular, similar to myself in many ways. Resting his hand on my hip suggested a familiarity already. "I'm Ben. We met last night at the club. Then we returned here, enjoyed a drink, before, well, we ended up in bed."

Feeling between my cheeks, there was definitely a sticky residue I knew well. "We had sex?" I asked.

"We sure did, Mark. You were really into it. For a straight guy, you certainly loved it when I slid my cock inside you, and that was only after you'd happily sucked my cock until I came down your throat." Then he paused before asking, "Don't remember?"

"I am drawing a bit of a blank after leaving the club."

"Oh..." He cleared his throat. "You're not... um..."

"Angry? No. A little confused more than anything. What did Mike say?"

"He was encouraging you, Mark. Wanted you to try something new." His hand moved to my cock, which was hard as it was every morning. "I mean, if you're now sober, we can try again... If you'd like..."

A couple of minutes later, I was resting on my knees and elbows as I felt Ben slide his thick cock inside me. Fuck, it felt good. Really good. And when he started to fuck me, it felt even better. No wonder Mike loved being fucked! Ben soon had a hand on shoulder as he really started to drive his cock inside me. He lasted longer than I expected before I felt his cock throbbing and a warm feeling as he unloaded his cum inside me, feeling him lean forward and his hot breath by my ear.

"Better when you're sober?"

"Fuck, that was fantastic. No wonder so many guys in the army were fucking."

"Well, if you want to hook up again, you just let me know."

Heading out to the kitchen, Mike was already up and about, glancing my way and grinning broadly. When he hugged me, I did hug him back for a couple of seconds. "So proud of you, Mark. Been with me barely a week and already sucking dick and being fucked," he stated, "How was it this morning?"

"Honestly?" He grinned at me before I added, "Really fucking good."

"Totally hot. The guy I brought home is still asleep. Fucked me for what felt like hours. You guys hungry?"

"Starving," Ben replied as he stood behind me, feeling him wrap an arm around me, his cock against pressing against me. When I pushed back, he chuckled. "Someone's eager again."

"You guys want to fuck here, I won't mind," Mike said with humour, grabbing a bottle and sliding it over, "There's some lube for you, Ben."

Within thirty seconds, I was moaning again I felt that thick cock slide inside, burying it nice and deep. "Fuck yeah," I groaned, "Holy shit..."

"Good, isn't it?" Mike asked.

"No wonder you make so much noise, mate," I moaned as Ben started pumping me. He was still fucking me when Mike's partner walked out, completely naked, thick cock hard and swinging. Taking one look at my face, he smiled in my direction.

"Damn, wasn't expecting a show," he stated.

"Breakfast is nearly ready though I guess we're waiting for Ben to dump another load in him."

"I'll be a few minutes," Ben grunted with both hands now on my shoulders while I stroked my cock, "I only came a little while ago."

Mike leaned against the counter next to me as his friend, who introduced himself as Peter, fucked him next to me. Mike leaned closer and I had my first sober kiss with another man. It was... rather nice, to be honest. "Totally hot," Mike moaned, "Love being fucked next to a friend taking a big cock at the same time."

We were both fucked until another load of cum was dumped in us, then the four of us sat around the table as we enjoyed breakfast. After finishing, Ben and Peter enjoyed a shower with their lover, and once his cock was clean, I fell to my knees and sucked cock sober for the first time. He was very complimentary, considering I didn't remember blowing him, and when he came in my mouth, I didn't mind the taste at all.