Life's journey

Homeless to Houseboy

“Melbourne here we come!” I said to myself referring to this weeks first interstate work trip since the onset of COVID. Having avoided the virus till now I was a little nervous around airports and flying etc, but hey you gotta live and it had been so long since I had caught with my Melbourne based colleagues.

It would be a 3 night stay over in the CBD and as with all business trips, long days in the office followed by lonely nights. Thankfully after the first day  the office the tea took me to a Malaysian restaurant in Chinatown.

On the second night I took myself one of my favourite old inner city pubs, which thankfully was still in business for one of their famous “burger and beer” deals.

I headed back towards hotel in the cool night air around 8.00pm thinking I would have a wine or two in the hotel lounge and watch whatever was on the big screen.

As I got almost to the lobby of the hotel I heard a ‘Please help me sir’ come from a homeless man cuddled up in a sleeping bag on he pavement. It wasn’t’ the first time tonight, the number of homeless people in the streets had increase hugely since I was hear last.

For whatever reason I don’t usually respond to such request but this came from what sounded like a young voice, I stopped and look-down, all I could see was his face, we wore a “beanie” and was tucked into his sleeping bag.  “Please help me sir” he repeated.

“Come with me” I said, signally for him to get to his feet and follow me into the hotel. He grabbed all his stuff from the pavement and followed me through the lobby to the lifts. “Thankyou, thankyou” he said as the lift doors closed.

At this point I still had no idea what I should or would do but was thinking fast. Opening the room door I let him through first and told him to take a seat.

“I can give you a full stomach, a shower and a warm place to sleep tonight” I said as I searched for the in-room dining menu. “Anything, anything will be appreciated” he said politely. “I’m John” I said putting my hand out to shake his. “Aaron” he replied placing his bone cold hand into mine.

“Let me know what you want from the menu, then gimme your clothes, I will get them washed overnight and jump in the shower to warm up” I said grabbing a robe from the bathroom and throwing it across the room to him.

I rang his and my order through to room service as he turned his back to me and started removing his clothes. It was impossible not to notice that after he removed his hoodie, t-shirt and tracksuit pants that he was wearing women’s lingerie as under garments. Both panties and a bra. Saying nothing about that I said I would call the laundry service and arrange for it all to be washed along with his sleeping bag. “Thankyou, thankyou” he said again.

Not surprisingly he had a very long shower, probably gathering his thoughts as the same time. He came out wearing just the robe looking a lot more refreshed than when he went in. His dinner and my coffee arrived and I let him eat in peace.

“What now” he asked. “I am here tonight an tomorrow night then return to Adelaide the next day, you can stay hear till them and we will work something out in the meantime” I replied. “Thankyou, thankyou” he said again.

“What’s the go with the women’s underwear?” I asked. He looked rarer embarrassed. “I like to cross dress in private, it is all I had when I left” he said going on to recite how he managed ton find himself on the streets. I accepted what he said on face value, no value in otherwise at this point.

I told him to make himself comfortable while I went down to the corner 24/7 to get him some supplies, toiletries, toothbrush, toothpaste, deodorant etc.

“being a cross-dresser, what is your sexuality?” I asked on my return. “I am gay” he said adding “An you”. “I am gay as well, rest assured however you are completely safe with me” I added. “This is safer than the streets” he said showing a smile for the first time. “We will sleep either side of the bed (it was a king size) with pillows between us if that makes you more comfortable” I offered. “No, no its fine” he said “I am sure we can be adult about this”.

Aaron had just turned twenty, had messy light brown hair, a small amount of facial growth having not shaved, was slim with not a lot of body definition. He took up my offer to use my shaving gear, returning a much better looking guy.

We jumped into bed around 10.30pm, he had no pyjamas, I didn’t bring any so both nude it was. I took no notice o his body as I turned the light out and rolled onto my side facing away from him.

I laid there thinking what I would do when I returned to Adelaide, I could not really just chuck him back on the streets, should I try to find him accommodation, give him money or even take him with me?

Aaron was quite restless in bed constantly moving around trying to find a comfortable position, maybe he was asking himself the same questions I was asking myself.

I felt his body come close to mine, his chest again my back, an arm came around me. “Hope you don’t mind, need to feel safe and secure, don’t sleep on the streets” he said. “It’s fine, glad you feel safe here”.

He pulled me closer to feel my warmth, I could feel his cock resting against one of my butt cheeks. I rolled onto my back, putting my arm round his shoulder and held him tightly as he placed his head snuggly on my chest.

“Sleep well” I said closing my eyes again and trying to turn my mind off.

Aaron lay peacefully, I thought he had drifted of to sleep until I felt his free hand wander up and down my chest. “You got a nice body for a guy your age” he said. “Too funny” replied. “Would love a Daddy like you” he then added. I said nothing in response as his hand started to get closer to my cock.

After circling my groin area for a few minutes, he then rang one finger along the length of my soft cock. “Love Daddy cock too” he said. Again, I did not respond as I tried to work out what was going on.

My cock naturally grew hard with this attention and before long he was slowly jerking me off then without warning slid under the covers and took my cock into his mouth and began sucking it. God it felt good having it in his warm mouth, this clearly not being the first time he sucked cock.

It had been a long time since I had blown simply by having my cock sucked, this seemed to be the night however, maybe the situation or his youthfulness or words had got to me and my cock.

He took every last drop of my cum into his mouth and swallowed it accordingly.

“Let’s get some sleep” I said rolling away from him onto my side.

By time we woke the next morning, Aaron’s clothes were sitting in bag outside the room door, we went downstairs for breakfast before leaving him with $50.00 for the day as I headed to work.

My concentration levels were not as they should be during the day as I continued to work through what I should do with Aaron when I returned home.

At lunch time I rang Sam and “C” and put a proposal to them – that being that Aaron would come and live with us as our paid “houseboy”. I said that I had not yet established what he was into sexually other than being a ‘cross-dresser’ and good cocksucker. Obviously, Aaron needed to be a bottom to fit in with us and considering he was clearly into daddies odds are he was.

Sam and “C” we OK with the idea, “C” off-course wanted assurances that his privacy would be respected. I told him that before I agreed to anything with Aaron the rules would be laid out clearly.

Aaron was still there when I got back to the hotel, there was that sight fear that he might have taken all my belongings an run off but that proved not to be the case.

We went to an Italian restaurant that night where I went through my living arrangements with Sam and “C” before putting my proposal to him. “So no expenses, get paid to do the housework, and can cross-dress” he repeated back to me. “Yes” that’s correct I said adding “plus on-demand blow jobs” laughingly.

Before shaking hands on the deal Aaron did confirm that sexually he was a bottom and that he would be happy to service the 3 of us, with a disclaimer that he had to actually like Sam and “C” – fair enough too!

“Let’s get you some stuff then” I said as we left the restaurant and walked to Kmart that was open till 9pmm being a Thursday night. Some $500.00 later we had a suitcase, shoe and enough clothes (socks, jocks, pants and tops) for the short term at least. “And these too?” Aaron asked holding up a matching set of women’s bra’s and panties. “May as well” I confirmed as he made it three sets, two in black the other white.

“How does this look” Aaron asked back at the hotel room having out on one of the black sets of women’s lingerie. I must admit he did look pretty sexy, definitely suiting his feminine like smooth body.

I hit the shower before bed, on my return Aaron was laying  on top of the bed, just wearing that lingerie, rubbing his cock through the panties and seductively licking his lips. Removing my towel, I stretched his legs out wide, sat between them and caressed his cock through his panties till it was rock hard, then slipped them off past his ankles.

His cock was around eight inches, cut, completely shaved (he must have spent his time alone today grooming as his legs were now also minus coverage). I licked the entre length of his cockshaft, followed by the cock head, back and forth before taking it into my mouth.

This was the youngest cock I had tasted since I was twenty myself and whilst it was not virginal still had that youthful taste and feel to it. I reached up taking his nipples into my hands and starting pinching them. He started thrusting hi cock in and out of my mouth, I felt the head of his penis hit the back of my throat.

Not knowing how long it would take him to cum, I wanted this time to last as from tomorrow 1:1 time would be harder to find.

I rolled onto my back, pulling him on top of me and starting to work his ass over with my hands, so soft and smooth, he stretched his legs wide and entered his anal are with my fingers, rubbing the outside of it, then slowly and carefully pushing one finger in I started to finger fuck him. With his head on my shoulder, I felt his breath starting to quicken up, the odd moan of pleasure between.

“Want to ride me?” I asked. Without hesitation he got onto his haunches took y cock in his hand and directed it into his ass. I reached around and undid his bra, throwing it on the floor beside.

Just like he knew how to suck cock well, he sure knew how to ride cock well, it was almost dance like the way he went about it, like he was putting on a lap dance for a crowd. As he rode, he attended to his own nipples, continued to lick his lips and he looked me straight into my eyes. It was such a turn on, his guy was seriously erotic. Aaron’s cock slapped against his stomach every time he went deep on my cock, taking it into my hands I started to jerk it.

He took one hand off his nipple, putting it behind him on the bed for support as he started to ride me harder, I started to feel my juices rising, “crank my cock hard” he said, to which I duly responded until his cock let go a couple of weeks’ worth of hot cum that landed on my chest. This sight was enough to take me over the edge, I felt my cock harden one final time, I tried to hold on but could not, my juices exploding into his ass one thrust after another.

Aaron leaned forward and kissed me on the lips. “I think we are going to have good times together” he said with a sexy smile.

As we Sat in the Taxi to home after flying back to Adelaide Aaron mentioned how nervous he was in meeting Sam and “C”, hoping they would like him and that he would fit in. I put my hand on his leg assuring him that all would be fine and knowing that whilst “C” was a little conservative sexually that Sam would be devouring him daily if not more often.

Both Sam and “C’s” cars were in the drive when we arrived which was good news as only one set of introductions. They were playing their usual afternoon Xbox when we walked in. Introductions done I showed Aaron to his room where he unpacked then joined the lads on the Xbox.

Dominoes Pizza’s were ordered for dinner, the four of us enjoying them as we chatted and got to know each other in the lounge room.

After cleaning up Sam set the agenda for the evening to follow. “So, show us what you got Mr Aaron” he said.

Needing no further encouragement Aaron got to his feet, walking to the middle of the room and seductively took off his shorts then unbuttoned his shirt, letting it fall open so we could see his lace white bra and panties beneath. He turned a full 360 degrees giving us all a full look as he slowly removed his shirt, then eyeballing Sam said, “do you like what you see Sammy?”

“I do, I do indeed” responded Sam gesturing for him to move closer to him. Aaron sat on Sam’s lap facing him, giving him an old-style lap dance before lifting his shirt off over his head and kissing his way down Sam’s chest stopping at the top of his jeans. He jumped of Sam and sat on his knees between Sam’s legs and buried his head in Sam’s crotch kissing his cock through his jeans before unbuttoning them, unzipping his fly, pulling out his cock and taking it into his mouth. Sam threw his head back in pleasure, Aaron then pulled his jeans and underwear off to give himself better access and continued to devour his cock.

Aaron looked up at myself and “C” instructing us to “sit beside Sam and get ready for your turn”. We duly stripped naked, “C” positioning himself fat the end of the couch and myself in between the two of them.

Once he could we had arrived at the party Aaron moved himself on the floor to between my legs and took my hard cock into his mouth. I looked either side to Sam and “C” who were both jerking their cocks and exchanged kisses with them.

Aaron then moved onto “C” devouring his cock, the way he sucks cock “C” was not going to last long, Sam sensed the same, jumped to his feet, lifted Aaron into his arms and carried him to the bedroom and positioned Aaron so that his ass was on the edge of the bed, put a pillow behind his bed then asked, “Who wants to go first?”

“You it” I responded. Sam lifted Aarons legs either side of his body and slammed his cock into Aaron and immediately started to fuck him hard. “Join in boys” Aaron invited. “C” laid on his side next to Aaron on the bed and started playing his cock while I got behind hum knees either side of his head and pushed my cock into his mouth. “Welcome to the family” Sam said playfully to giggles all round. Just like out first night in Melbourne, Aaron took my cock deep into his throat, I felt like he was going to swallow me completely.

I signalled for “C” to get into the same position as me but at right angles, my cock was feeling so amazing I needed more, I pulled “C’’s” chest against y side and began to kiss him, with one free hand I grabbed one o his buttocks, the other one of his nipples. Aaron took “C’s” cock into his hand while continuing to suck me. Sam took “C’s” place jerking Aaron’s cock. This was about as close to heaven as it was ever going to get for the four of us, each having multiple parts of our bodies pleasured at once.

Sam was at the point of cumming, he let out some load groans before letting his cum go inside Aaron, within seconds of that “C’s” cock duped its load over Aaron’s face. I pulled my cock from Aaron’s mouth and took over from Sam, who with a bigger cock than me had opened up Aaron beautifully and I just slid in like a hand in glove. Sam got down and started kissing Aaron while “C” resumed jerking his cock.

As “C” bought Aaron’s cock to orgasm, I felt his ass tighten around my cock which bought me to the same state, I pulled out and we both came simultaneously over Aaron’s chest.

Sam and “C” headed for the showers while I cleaned up Aaron. “How are you enjoying your new life and home?” I asked cheekily. “It has been a whirlwind couple of days, 48 hours ago I was trying to keep warm and find food on the streets and tonight I am having the most amazing sexual pleasures” he responded as I took him to his bedroom, tucked him into his bed and gave  kiss good night.

I entered “C’s” bedroom on my way back to mine, he seemed upset. “What’s up?” I asked. “I am just so embarrassed how fast I cum compared to you guys” he said, adding “I feel like I am missing out on the longevity of the pleasures”. I put my hand on his bare chest to comfort him before replying “don’t be embarrassed we can help you improve that, we can do some 1:1 edging sessions and work on your breathing which will make a massive difference”.  “I will do anything to last longer” he said.

 I kissed him on the forehead before leaving the room and returning to mine where Sam was laying in bed. “Impressions of Aaron?” I asked. “He can stay, we have found what we needed, plus he is a good lad”.

“Just go easy on his ass and leave some for us” I chucked.