(This is my first story so please leave comments and feedback. Enjoy!)

It had been two years since the tragic passing of their father. Two years however, can be seen as a long or short period of time depending on the people involved. For James it was difficult to watch, firstly because he watched his best friend fly away with his sister and mother. They were only a two hour flight away but compared to living in the same street as him, it felt like another continent.

James was now 18 but you wouldn’t have guessed it when you looked at him. He was 5ft 9’ and rather thin. He had quite a feminine physique which he hated. His best friend, Jack, however was a different story. He was 6ft 3 and built, many days spent at the gym and buffed up into a hunk of a guy.

Yet despite these differences, they were best friends and spent almost every waking minute together. They were a perfect team, Jack defended James from any harassment and James helped Jack with his school work. However it all changed when Jack fly north away from his best friend thus ending their strong bond.

James always had a secret desire for women’s clothing since he was 16. He would sneak into his sister’s room and put on her bra and panties with the occasional dress and make up touch. When he turned 17 became bolder with his ambitions as he would lie on her bed and pull out her dildo, she was never good at hiding it, and fuck his ass with it while stroking his cock furiously until he came, which was either on his chest, face and even straight down his throat.

He loved the taste, the feeling of his hot goodness dripping off his body like the slut it made him feel. He had always fantasised about having a real cock to suck dry, to be fucked by until he passed out. However no one, not even his best friend knew of his fetish. It was his little secret.

It was time for James’ visit to see Jack and he couldn’t have been more excited. He got to spend two weeks with his best friend, for the first time in two years and his amazingly hot sister and mother, whom he had cum over so many times in the past. Jack’s sister, Rebecca, was 5ft 5 with all the right accessories. At just 16 she was something to behold. She had 36D breasts that were made to look even bigger in her skimpy outfits she always wore.

Her long days spent by the beach made her skin a wonderfully tanned tone and finally her ass, it was just breathtaking. James had been caught on numerous occasions staring at her luscious curves, making him hard almost every single time. Jack’s mother, Crystal, was just as if not more sexy than her daughter. Crystal was 38, with 36DD breasts and an ass stuck out begging to be fucked. She had long blonde hair and dark tanned skin like her daughter, they could easily be mistaken her sisters.

James was greeted by his new family for the next two weeks with open arms and the rest of the afternoon was spent catching up and down at the beach for the summer. Crystal and Rebecca decided it was ‘perfect conditions’ to where their new two piece bikinis. Rebecca’s was pink with flowers on it but despite the colour and playfulness of it, it screamed nasty girl.

Crystal’s was black and was definitely too small, much to the delight of James and embarrassment of Rebecca and Jack. She pushed her breasts higher and her bottoms were so tight it made them look like a thong. The rest of the day James spent trying to hide his throbbing erection, mainly by going in the surf. The coolness of the water helped bring his manhood down however see those two lovely girls bounce and jiggle about got his blood rushing yet again.

After heading out her dinner the group decided to head home and watch some TV. Rebecca had school the next morning and decided to call it a night, while Jack was going to the gym early so he called it a night too. This left James with his best friend’s hot mother whom he couldn’t keep staring at. Crystal had decided to at least wait for the right man before she went dating yet again so this left this her hot and horny almost all the time and watching James stare at her only made her hornier. Crystal moved closer to James, his eyes widened as he she placed a hand on his thigh.

“Do you mind if I lie on you?” Crystal asked fluttering her eyes. James almost came then of course he didn’t fucking mind.

“Not at all,” he replied nervously as he raised his arm so she could slide underneath and boy what a view he received.

A clear view down her top to her amazing breasts, James couldn’t control himself. His cock began to twitch and it didn’t take long till he was fully erect, praying she hadn’t noticed.

“Someone is in a good mood," she smiled, and James swallowed.

“Don’t worry, so am I,” and with that she grabbed his cock and began stroking it up and down.

James was lost in ecstasy at the feeling. He didn’t care if they were caught or that it was his best friends mum it was amazing. She then mounted him and kissed him passionately, eagerly wanting more as their tongues battled in each other mouths. She removed her tight fitting tank top to relieve no bra and her 36DD breasts that James eagerly took into his hands and then mouth, sucking on them for all they were worth. She reached down and unbuckled his jeans and took them off, stroking his cock through his boxers with precum oozing through the material.

“Perhaps we should move to my room,” Crystal winked sexily, James couldn’t his luck.

He was going to fuck this amazingly hot MILF.

Crystal shoved him onto the bed and mounted him as they continued kissing each other, sucking on each other tongue and neck. Her mouth made her way down his down, licking and kissing as she went. She grabbed his boxers and tugged them down, revealing his 7 inch fully erect manhood.

“Mom I’ve waited so long for this,” Crystal took him in her mouth, immediately deep threading until she gagged. She loved his cock, sucking him deep down her throat, licking the top as well. James was in heaven

“Holy shit that feels so fucking good,” she smiled up at him while she continued sucking him hard and fast. A couple minutes had passed when he could feel himself Cumming.

“Oh shit I’m about to cum,” but instead of letting off she forced herself deeper on his cock as his head expanded and exploded deep down for throat, and she swallowed it all.

“Mom tasty.”

“Fuck that was amazing, your turn now.”

It seemed the animal inside James was unleashed as he tossed her over and pulled down her tight shorts to reveal no panties and a bare pussy. He didn’t waste a heartbeat and started licking all around her goodness, getting his tongue deep inside her pussy.

“Oh shit James fuck, you know how to get me going!”

“Yeah baby you taste so good,” the smell of her juices was intoxicating.

James didn’t even bother to think as he kept lapping up her juices with glee. James started to insert two fingers into her pussy and that pushed Crystal to new levels.

“OH MY FUCKING GOD!” she screamed as her orgasm was approaching.

James inserted another finger as he finger fucked the daylights out of his best friends mum. She began to buck violently as he pounded her pussy with his fingers.

“FUCCCCKKKKK!!!!” she screamed as she started to cum.

James didn’t miss a heartbeat and went straight back down on her and tried to swallow as much pussy juice as he could. He loved being squirted all over by this beautiful woman. He didn’t even release his own member was awakening yet again.

“I haven’t cum like that in years, thank you so much James.”

Crystal mounted James as they began to make out again. Hands were everywhere as they rolled around, Crystal even inserted a finger into James ass and he moaned softly into her lips from it. Crystal had an idea and stopped making James little concerned and disappointed.

“I use to do this with my husband and I’ve been dying to try it on you.”

She came back with a matching black bra and thong, bright yellow sundress and blonde wig. James’ erection throbbed even harder, making it slightly painful.

“Put these on! We’re going to have some fun,” she winked at James and he jumped at the opportunity. He loved the feeling of the silky fabric sliding up his ass crack and the tightness of the bra around his body. Crystal returned with a strap on attached and smiled at him.

“I know you love to wear women’s clothing you sissy. I’ve even seen you cum into your own mouth before,” he couldn’t believe she knew, but how? It seemed Crystal read his mind.

“Oh I know don’t you worry but tonight imp going make you feel like woman. Suck my dick!”

James leaped onto the bed where she was lying and swallowed her plastic cock whole. He was going hard at it, loving every second of his not so secret desire. He licked the head, deep throated and was even mouth fucked by Crystal.

“Turn over sissy it’s time for you fucking!”

Cum was leaking out of James’ thong at the excitement as Crystal pulled almost half a tub of jelly to his ass. She inserted one finger, then two, three and finally four as she finger fucked him hard. James moaned loudly.

“You moan like a sissy too!”

Finally she stopped and mounted him, doggy style. She inserted the head, it went in easily enough then with a big thrust, she was balls deep. James cried out in pain, it was a whole new experience to his sister’s dildos. Crystal started with long slow thrusts, waiting for his ass muscles to relax and expand. After a few minutes she was fucking him hard and long.

James was in a new a whole new world of pleasure as he was fucked from behind. He decided to move his hips and ass in sync to the thrusts for maximum pleasure as she fucked him for a good ten minutes. She flipped him over and raised his legs over her shoulders and started fucking him missionary. James was stroking his cock furiously as his ass was being pounded. He could fill his cum building up and she saw it in his face.

“Do it! Cum in your mouth, you sissy! Let me see you drink your own cum.”

That pushed James over the edge as shot after shot of cum burst from his cock onto his face and down his throat, it was the most he had every cum and he couldn’t swallow all of it. As Crystal slowed down on James’ ass they heard a short moan, just long enough to be heard. They looked towards the door and saw Rebecca, in just her bra and panties, one hand on her tit the other rubbing her pussy.

“Well well well isn’t this something,” Crystal started.

James was frozen with fear as was Rebecca. Crystal removed her cock from James’ ass and walked over to Rebecca, who was still petrified at being caught. Crystal grabbed her hand from her panties and brought the fingers to her mouth and sucked on them slowly. Rebecca watched in shock, but Crystal smiled seductively back and grabbed both hands.