Toby was in a bit of a state,he couldn’t face work today but had resigned himself to do so,knowing that to not turn in would only further his problems.
Just turned 19 he had been at his current job for just over a year,it had taken years of hard study at sixth form college to achieve the grades necessary to be excepted into the renewable energy engineering program.
He loved his job and the challenges that each day brought,still very much a novice of his craft.
Working with over 70 people meant he had a large number of colleagues whom he had become close with and classed them as close friends,it was one of those friends that had talked Toby in to work today,Josh was his closest mate of all,they had grown up together and chose the same career.
Josh couldn’t bear to see Toby so torn up,but he knew it would only get worse if he messed up his employment.
Toby had just broken up with his girlfriend Chloe,they had been together since school,lived together for the past year,Toby had found out she was sleeping around and was totally devastated,he had moved back to his parents house,which he absolutely hated,he loved his freedom away from them,not that they were bad to him or each other,he just felt like he was regressing.
Toby was a gentle soul,very polite and quiet,hardly ever swore,Josh knew his friend was wounded deeply,he’d never heard him swear so much.
“I can’t Fucking believe she would do it to me”
“I know pal,there’s nothing we can do to make it better,only time can do that,you coming to the canteen for a brew”
It was break time,but Toby couldn’t face the hustle and bustle at the moment
“No bud,I’m going to sit outside and search the free adds for some place to live,can’t stand living under my parents much longer”
“Ok pal,just try keep your chin up”
Josh wondered off towards the canteen,which was currently in a container as the building was having a large extension to accommodate more office staff and a new canteen,it was then it hit him,looking at the builders going about their work,his uncle was a very successful builder,he now buys and rents out houses,Josh couldn’t change what Chloe had done to his mate hut he could try and help him move on.
Toby scrolled endlessly,looking at properties he couldn’t currently afford,it was hopeless,he put his phone down and sighed deeply staring at the floor.
He wouldn’t have made it back inside if Josh had came back to startle him out of his reverie.
“Oi,you can’t stay there all day pal,come back inside”
“Shit,yeah coming,thanks bud”
Josh could see the distance in his friend,he hoped his news will cheer him up a bit.
“So,I’ve just got off the phone from my uncle Cliff,he has a few properties he rents out,he is currently doing up some flats above a row of shops and takeaways,wont be ready for a month or so but he says you can have first choice if you like,he will look after you on the price to.
“Oh that’s brilliant Josh thank you”
“Don’t mention it,that’s not even the good news”
“What do you mean?”
“Well i told him you where keen to get moved out asap,so he said you can move into the annex next to his,it was his mum’s house and the converted the double garage into a small living space for her when she became to ill and couldn’t make it upstairs anymore,she’s gone now bless her,but he says you’re welcome to move in this weekend if you like”
Toby couldn’t believe it,a glimmer of light in his currently dark world.
“Are you sure,is it a bit weird moving to your uncles ?”
“Don’t be daft,not like you will be in the same house as him,and it’s only temporary,if you want ill take you there after work to have a look and meet my uncle,well you’ll be driving but you know what i mean”
“Yes definitely,thanks bud”
It was first time Toby had genuinely smiled in a while
The day flew by and after work they both hopped in Tobys little Vauxhall corsa,Josh directed him to a village about ten minutes away from work,they pulled up in front of a fairly large detached cottage with an ample front garden,the annex was set back slightly from the house,as they got out the car,the front door opened and out stepped Cliff,he was well over 6ft,greyish hair,strong looking from years of building and skin like a leather arm chair from to much sun.
“Hello Josh,hows it going?, Im guessing this is Toby?”
He extended his hand to shake Tobys,nearly crushed it with his strong grip.
Cliff towered over Toby,he was only small and slim,just over 5ft
“Hi yes im Toby,nice to meet you,are you sure you don’t mind?”
“Nonsense lad,plus you haven’t even seen it yet,come on follow me “
They walked to the front of the annex which had double glazed windows and door,he opened up and in they went,it was pretty self contained,in one corner was a double bed next to a wardrobe and bedside table ,with an electric hoist fitted above on a track which went into another room,a small kitchen area in the other corner,a sofa and an arm chair with a coffee table in the centre and a large tv on the wall.
“Its not much but it has everything you need,the bathroom is through there”
It was where the electric track hoist led,used for helping his mother into the shower/bath,it was a complete wet room,with a shower and a walk in bath with a chair in the corner.
“If you want to you can bring your stuff this weekend,and as soon as the flats are done i will let you have a look see “
“I don’t know what to say,thank you,if you are sure i will bring my bits on Saturday morning”
“No worries,here take this key,say £80 a week,all electric,water,gas and internet included,ill give you the wifi once you are in”
“Oh my god are you sure “
“Just no loud music or parties”
“Oh Im not like that,you won’t hear a peep from me”
“See you on Saturday then”
They hopped back in The car and drove off.
“Thanks for this Josh,i can’t believe it”
“No problems pal”
“Is Cliff married,does he have a missus that is going to mind?”
“No he got divorced years ago,never re married,don’t think he wants to get stung again,likes his money to much”
The rest of the week flew by,and just after 9 on Saturday morning,Toby pulled up outside his new little abode,he didn’t have a lot to unload,a few suitcases of clothes,a few pots and pans,his laptop and PlayStation.
After an hour or so of unpacking he heard a tap at the window,it was Cliff,casting a large shadow on the wall,Toby opened the door and asked him in,they chatted for a good while,about life and how they had both been screwed over by the opposite sex,Cliff made a fly away comment about not needing a woman
“Im not getting involved again, id rather have a wank or fuck a tranny lol”
He slapped Toby on the back in jest as he said it
Toby laughed as Cliff got up and left
The last of his things where in a rucksack,tucked in the side pocket was a pair of his ex girlfriend’s pink knickers,a pang of sadness struck him as he retrieved them,he had taken them to wank with,but he wasn’t in the mood right now..
After around a week or so he had settled in nicely,he had only seen Cliff a couple of times since.
It was Friday night and Toby had decided to go out for a couple of drinks,by 11 he was pretty sloshed and decided to head home,his mates continued on to a club.
Toby got out the taxi and tried to be as quiet as possible so he didn’t disturb Cliff,he didn’t want to become a nuisance.
Once inside his little abode he decided to make himself a quick sausage bun before bed,he put on his mini grill and then got out of his clothes ready to put some shorts on for bed,thats when he remembered his ex girlfriend’s knickers he’d taken,he fished them out and put them to his nose and had a deep inhale,he could just smell her musky scent,his cock twitched and began to grow,he wasn’t very big,he began stroking himself thinking of her wet cunt,he sat down and for reasons he couldn’t explain he decided to try the knickers on,something he had never done before,he liked the smooth feeling of the material against his tiny cock,he laid down to pleasure himself,that’s when the room began to spin,he thought he may throw up,he kept his eyes closed to try and stop the spinning and within a minute he was fast off.
The grill was heating up and it began smoking rather badly,after five minutes a very loud alarm began sounding,Toby didn’t hear a thing,two more minutes passed,Cliff came striding through the door with in his dressing gown looking half asleep and annoyed, until he saw Toby laid sideways on the bed in a pair of pink knickers,his arse pushed out looking better than most females,Cliff quickly shut off the alarm and turned off the grill,he turned to admire Toby,his cock growing under his gown,he took out his phone and snapped several pictures.
He lent over Toby,shook his shoulder to rouse him,after a few tries Toby finally awoke,he wondered what was going on,he sat upright on his bed to see Cliff sat beside him,Cliff quickly explained about the alarm and grill.
“Oh god i’m so sorry, don’t normally even drink,i i i i …l
“Don’t worry about it,these things happen” Cliff replied gently
It was then that Toby realised he was sat in a pair of knickers,he turned bright red in embarrassment
“Oh my god I’m sorry i erm….”
“Its fine lad,they look good on you”
Toby went to get up but Cliff put his hand on his leg.
Toby sat with his head down and noticed the bulging under Cliffs gown.
“Honestly they look good,you would make a cracking Tranny”
Toby chuckled awkwardly
“Have you ever played with a guy?”
“Erm no never,never even had a thought about it,I’m not gay”
“Me neither lad but i like tranny’s and crossdressers”
“Ok,well what ever floats your boat”
Toby smiled,Cliff took this as a good sign and parted his dressing gown,his bare cock sprang out,it was big and fully hard, a good 8-9 inches,his foreskin half way down his helmet,thick veins pulsing down the side.
Toby was stunned,his heart raced like never before,his own little cock began to twitch,he was so confused,why was this arousing him,he never thought of guys in this way.
“You can touch it if you want”
Toby hesitated for an age,Cliff took his hand and placed it on his meat,it felt so big in Toby’s hand,he just held it for a spell,his heart thumping,then he slowly began to pull down and up,Cliffs Foreskin pulled fully back exposing his big glistening purple head,he let out a slight moan as Toby got slightly faster,he couldn’t believe what he was doing,Cliff leaned back on the bed.
“Suck it”
Toby paused,could he,it felt so wrong but at the same time he was extremely horny,he lent forward and placed Cliffs head between his lips and began to suck,he didn’t know what he was doing but he just went for it as fast as he could,Cliff pushed his head down which caused Toby to gag,he pulled away,Cliff apologised and then pulled his head down softly as Toby began to suck again while playing with his own cock,Toby wanked furiously as he sucked his first cock
He knew he was about to cum and couldn’t control it,he squirted all over the place as Cliff to began to climax while still in Toby’s mouth,wave after wave of thick ropes of hot salty cum hit the back of his throat,Toby spluttered and coughed it out as Cliff moaned loudly,Toby pulled away,cum covering Cliffs big cock,slimy and wet with saliva too.
“Fuck me lad,that was good,are you sure you’ve never sucked a dick before”
“No never,i don’t know what came over me”
“I did “
They both laughed.
“Oh I’m going to train you good girl,you’ll be taking cock deep in both your holes in no time”
“What,girl,erm I’m not……”
“Im gonna make you my sissy sex toy,i can tell you like it,don’t worry,i promise you’ll enjoy every second, i will train you up good and proper”
“Oh I’m not sure,it’s probably because Ive had a tipple,not normally like this “
“When I’m done with you,you will be craving cock 24/7”,now I’m off for a shower and bed,i will see you in the morning to discuss this more,in the meantime,why don’t you watch some sissy training porn so you can see what its all about”
“Erm ok,night then”
Toby jumped in the shower himself after Cliff left to wash himself down,he couldn’t believe what he had just done.
He had know idea about the journey he was about take……..TBC
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I hope there’s more to cum 
