How Nick became Nicki A sissy story
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How Nick Became Nicki. A Sissy Story free porn video
This is the story of Nick. Nick was straight.
It was Friday night and she was getting ready to go out, she had something special planned tonight. She had her favourite pair of red and black lace lingerie on, the panties cupping her round smooth cheeks, her light blue pencil dress that hugged her figure and gave her a passable cleavage, white heels that make her look sexy even though they squeezed her toes and rubbed her heels and she had barely got the hang of walking in them. She had done her make up too, as well as she could, a little eye shadow and a cherry red lipstick. Her stomach was aflutter with butterflies and she was nervous. This was a big step, there was no doubt it turned her on, the throbbing between her legs was proof enough of that, but could she go through with it…
Let me explain the lead up to this.
The thoughts had been going round in Nicks head for a while at this point. He couldn’t remember quite when they had started but it had to have been at least 2 years, it hadn’t been a quick process. It had started off, like most people, as just regular porn, petite girls getting ploughed, that was exciting back then.
Over time however he had started to look for something a bit more exciting, bigger cocks, more of them, larger facials. This was no problem and was getting him harder than ever. Months passed, things were getting a little stale now, no matter, he’d simply have to find something a bit more exciting, not a problem, he asked and the internet delivered he stumbled into shemale porn half by accident, they are called traps for a reason, recoiling in preprogramed disgust when he saw what was hiding under that beautiful girls skirt, the tab was closed and he retreated back to the comfort of 5 guys cumming all over Riley Reid.
That session had obviously sparked his intrigue, and the next time he pulled up his laptop and entered incognito mode he decided to just take another look at what he’d seen last time, what harm could it do. A little searching a he soon had a few videos of these new, exciting chicks with dicks and without even thinking he had his cock in his hand jerking, harder than he’d ever been.
Another few months passed, now girls barely get a look in, crossdressers are on the menu now, it looks like fun, not something he’d ever try but some of them certainly did look good. Reading the comments on the videos made him laugh, all these gays saying how beautiful the guy was. Time to make an account, join in for a laugh. He began agreeing with a few comments throwing in the odd “yeah” or “me too” but soon got into the swing of things dropping compliments over a few videos and albums. He liked the excitement of it all, the anonymity, he was just a blank profile somewhere on the internet. He got his first comment back, “thanks”, so simple but so exciting, a real life crossdresser commenting back to him.
More months passed, sissy hypnosis, bi conditioning and CEI now fill his favourites. His tumblr account was flourishing, a dashboard full of gifs of bimbos, shemales, sissies, crossdressers and big cocks. Of course it was still all just fun at this point, he was still straight, he’d gone back to straight porn to prove it to himself, watching those big fat cocks pump in and out, in and out, the girls moans from pleasure and those big sticky loads all over their faces. Yeah, he was still straight. He just popped onto the photos section for a little look before he went to clean up. That’s when it happened. He opened up a gallery of one particularly large white cock, long 7 or 8 inches by the looks of it, veiny, a bulbous head and a thick shaft, scrolling down to check the comments he thought he would throw his own in for fun “mmmm looks so tasty sir”…just for fun. Simple as that.
It had been two days since that comment, all but forgotten in his head, he had been busy on assignments for uni and hadn’t had a chance to jerk off at all. He logged in for a quick one before bed and found he had a couple of messages, he had a look through them, one was from some spam account looking to pay her rent by selling nudes, not very interesting, the other from a user he didn’t recognise, the message read “Are you a sissy”… he gave a little smile and replied “yeah sure”, why not, he had a spare hour for some fun and after a quick browse through the mystery users profile he recognised him. This was the cock he had commented on the other night. 1 New Message
His alarm rang, he looked around with surprise, 7:30am, he was sat, dick in hand, naked on his bed still chatting with the mystery man…only now the mystery man was Master. Fuck…he had been talking all night and hadn’t slept. This was the first of many nights like this.
Over the following months, Nick Drew became Nicki Sweet and, after one fateful trip to amazon.com he realised that there was nothing stopping him anymore.
The advert was on the homepage, 50% off women’s wear. Something clicked in his head. He could have anything he wanted delivered to his door, anonymously. It would just be a box, he would just be a credit card number. He could be…her. His basket filled quickly some panties first, then two pairs of panties, then bras, they were all so pretty he didn’t know what to get first, so he got them all. She browsed for hours through the cute dresses and tops, tight jeans and short skirts. She discovered the world of false silicon boobs, the bought a pair, she would be able to pull off all the clothes she had bought. Jerking the whole time she clicked into the sex toy section buying a 9 inch flesh coloured dildo and a small vibrator and a gag. Horny beyond belief and excited she confirmed her address paid the £8.99 for next day special delivery and hit buy. Her fingers slipped into her ass pussy then and she came the hardest she ever had that night.
Skip a few weeks, Nicki learnt to dress, to take her dildo into her ass, to do her make up, then she learned something extra special…the location of a local glory hole…she had stumbled across it quite by accident but there is was as she sat to pee in some public toilets on her way home. Her heart fluttered and she stayed in that cubicle for an hour waiting and jerking. She soon realised that 1pm on a Wednesday afternoon was not the time anyone would be using a glory hole so she resolved to go home and return that Friday night.
So here she was, Friday night in her room, her favourite lingerie on, cutest dress, the best she could do with her makeup and the butterflies in her stomach. Her cock was raging between her legs, so hard and swollen she thought it might explode, she couldn’t pull out now, she was ready. She grabbed her big coat to cover herself as best she could and she headed out.
She walked into the toilets rushing past a man who stunk of alcohol who was pissing against the wall next to a urinal. “block it out” she thought as she hurried into the cubicle from Wednesday and slammed the door sliding the lock across. The stench of the place suddenly hit her as she took her coat off, the tang hit the back of her throat and she felt dirty, the place felt dirty, she looked around, the place was dirty, but there was that hole in the wall, that hole in the wall that made her cock harden. She lowered herself to her knees and knelt on the wet floor, her dress absorbing the foul liquid, the smell filling her lungs and a deep burning lust and desire washing over her as she knelt. Waiting.
An hour passed and her knees ached so she retired to sit on the toilet lid and wait. This wasn’t how she’d imagined it, a few people had come in, a couple had even come in the cubicle next to her, she had hopped straight to her knees in anticipation, heart racing, but to no avail, these men did their foul deeds in the toilet next door and left. Disappointment. Maybe there was something she didn’t know, maybe this was an old hole that no one used, maybe it was the wrong day, maybe…the door to the toilets swung open and someone squelched in whistling. Nicki’s ears pricked up, but she wasn’t expecting much after her hour of waiting and disappointment. The mystery man slipped into the right cubicle, Nicki’s heart sped up. There was a moment of silence BANG BANG, two sharp knocks erupted on the adjoining wall of the cubicle and Nickis heart nearly leapt out of her mouth, blood was thumping in her chest and false breasts we being moved by the v******e of her excited heart galloping in her chest. BANG BANG another two knocks “Someone in there?” two thick fingers searched through the hole. Nicki swallowed and tried to reply, no words came out, but she knocked shakily on the wall and grasped the mans fingers in her smooth hand. She lowered herself to the piss covered floor and stared through the hole, the saw some faded blue denim drop and two tick legs covered in coarse black hair, and there it was, between them, 5 inches of semi hard, real life man cock. A chapped hand that matched its stubby thick fingers grasped the shaft and slipped it through the hole. It was time to start.
End of part 1.
Did you enjoy it? Should I bother writing part 2 or maybe another story all together? All feedback welcome.
It was Friday night and she was getting ready to go out, she had something special planned tonight. She had her favourite pair of red and black lace lingerie on, the panties cupping her round smooth cheeks, her light blue pencil dress that hugged her figure and gave her a passable cleavage, white heels that make her look sexy even though they squeezed her toes and rubbed her heels and she had barely got the hang of walking in them. She had done her make up too, as well as she could, a little eye shadow and a cherry red lipstick. Her stomach was aflutter with butterflies and she was nervous. This was a big step, there was no doubt it turned her on, the throbbing between her legs was proof enough of that, but could she go through with it…
Let me explain the lead up to this.
The thoughts had been going round in Nicks head for a while at this point. He couldn’t remember quite when they had started but it had to have been at least 2 years, it hadn’t been a quick process. It had started off, like most people, as just regular porn, petite girls getting ploughed, that was exciting back then.
Over time however he had started to look for something a bit more exciting, bigger cocks, more of them, larger facials. This was no problem and was getting him harder than ever. Months passed, things were getting a little stale now, no matter, he’d simply have to find something a bit more exciting, not a problem, he asked and the internet delivered he stumbled into shemale porn half by accident, they are called traps for a reason, recoiling in preprogramed disgust when he saw what was hiding under that beautiful girls skirt, the tab was closed and he retreated back to the comfort of 5 guys cumming all over Riley Reid.
That session had obviously sparked his intrigue, and the next time he pulled up his laptop and entered incognito mode he decided to just take another look at what he’d seen last time, what harm could it do. A little searching a he soon had a few videos of these new, exciting chicks with dicks and without even thinking he had his cock in his hand jerking, harder than he’d ever been.
Another few months passed, now girls barely get a look in, crossdressers are on the menu now, it looks like fun, not something he’d ever try but some of them certainly did look good. Reading the comments on the videos made him laugh, all these gays saying how beautiful the guy was. Time to make an account, join in for a laugh. He began agreeing with a few comments throwing in the odd “yeah” or “me too” but soon got into the swing of things dropping compliments over a few videos and albums. He liked the excitement of it all, the anonymity, he was just a blank profile somewhere on the internet. He got his first comment back, “thanks”, so simple but so exciting, a real life crossdresser commenting back to him.
More months passed, sissy hypnosis, bi conditioning and CEI now fill his favourites. His tumblr account was flourishing, a dashboard full of gifs of bimbos, shemales, sissies, crossdressers and big cocks. Of course it was still all just fun at this point, he was still straight, he’d gone back to straight porn to prove it to himself, watching those big fat cocks pump in and out, in and out, the girls moans from pleasure and those big sticky loads all over their faces. Yeah, he was still straight. He just popped onto the photos section for a little look before he went to clean up. That’s when it happened. He opened up a gallery of one particularly large white cock, long 7 or 8 inches by the looks of it, veiny, a bulbous head and a thick shaft, scrolling down to check the comments he thought he would throw his own in for fun “mmmm looks so tasty sir”…just for fun. Simple as that.
It had been two days since that comment, all but forgotten in his head, he had been busy on assignments for uni and hadn’t had a chance to jerk off at all. He logged in for a quick one before bed and found he had a couple of messages, he had a look through them, one was from some spam account looking to pay her rent by selling nudes, not very interesting, the other from a user he didn’t recognise, the message read “Are you a sissy”… he gave a little smile and replied “yeah sure”, why not, he had a spare hour for some fun and after a quick browse through the mystery users profile he recognised him. This was the cock he had commented on the other night. 1 New Message
His alarm rang, he looked around with surprise, 7:30am, he was sat, dick in hand, naked on his bed still chatting with the mystery man…only now the mystery man was Master. Fuck…he had been talking all night and hadn’t slept. This was the first of many nights like this.
Over the following months, Nick Drew became Nicki Sweet and, after one fateful trip to amazon.com he realised that there was nothing stopping him anymore.
The advert was on the homepage, 50% off women’s wear. Something clicked in his head. He could have anything he wanted delivered to his door, anonymously. It would just be a box, he would just be a credit card number. He could be…her. His basket filled quickly some panties first, then two pairs of panties, then bras, they were all so pretty he didn’t know what to get first, so he got them all. She browsed for hours through the cute dresses and tops, tight jeans and short skirts. She discovered the world of false silicon boobs, the bought a pair, she would be able to pull off all the clothes she had bought. Jerking the whole time she clicked into the sex toy section buying a 9 inch flesh coloured dildo and a small vibrator and a gag. Horny beyond belief and excited she confirmed her address paid the £8.99 for next day special delivery and hit buy. Her fingers slipped into her ass pussy then and she came the hardest she ever had that night.
Skip a few weeks, Nicki learnt to dress, to take her dildo into her ass, to do her make up, then she learned something extra special…the location of a local glory hole…she had stumbled across it quite by accident but there is was as she sat to pee in some public toilets on her way home. Her heart fluttered and she stayed in that cubicle for an hour waiting and jerking. She soon realised that 1pm on a Wednesday afternoon was not the time anyone would be using a glory hole so she resolved to go home and return that Friday night.
So here she was, Friday night in her room, her favourite lingerie on, cutest dress, the best she could do with her makeup and the butterflies in her stomach. Her cock was raging between her legs, so hard and swollen she thought it might explode, she couldn’t pull out now, she was ready. She grabbed her big coat to cover herself as best she could and she headed out.
She walked into the toilets rushing past a man who stunk of alcohol who was pissing against the wall next to a urinal. “block it out” she thought as she hurried into the cubicle from Wednesday and slammed the door sliding the lock across. The stench of the place suddenly hit her as she took her coat off, the tang hit the back of her throat and she felt dirty, the place felt dirty, she looked around, the place was dirty, but there was that hole in the wall, that hole in the wall that made her cock harden. She lowered herself to her knees and knelt on the wet floor, her dress absorbing the foul liquid, the smell filling her lungs and a deep burning lust and desire washing over her as she knelt. Waiting.
An hour passed and her knees ached so she retired to sit on the toilet lid and wait. This wasn’t how she’d imagined it, a few people had come in, a couple had even come in the cubicle next to her, she had hopped straight to her knees in anticipation, heart racing, but to no avail, these men did their foul deeds in the toilet next door and left. Disappointment. Maybe there was something she didn’t know, maybe this was an old hole that no one used, maybe it was the wrong day, maybe…the door to the toilets swung open and someone squelched in whistling. Nicki’s ears pricked up, but she wasn’t expecting much after her hour of waiting and disappointment. The mystery man slipped into the right cubicle, Nicki’s heart sped up. There was a moment of silence BANG BANG, two sharp knocks erupted on the adjoining wall of the cubicle and Nickis heart nearly leapt out of her mouth, blood was thumping in her chest and false breasts we being moved by the v******e of her excited heart galloping in her chest. BANG BANG another two knocks “Someone in there?” two thick fingers searched through the hole. Nicki swallowed and tried to reply, no words came out, but she knocked shakily on the wall and grasped the mans fingers in her smooth hand. She lowered herself to the piss covered floor and stared through the hole, the saw some faded blue denim drop and two tick legs covered in coarse black hair, and there it was, between them, 5 inches of semi hard, real life man cock. A chapped hand that matched its stubby thick fingers grasped the shaft and slipped it through the hole. It was time to start.
End of part 1.
Did you enjoy it? Should I bother writing part 2 or maybe another story all together? All feedback welcome.
Charlize
- 10.10.2021
- 10
- 0
