Neighbors Sissy Son Ch. 04

Authors note:

All characters are 18 and older. This is a stroke story about a transgender boy as he transitions into a girl and the mischief she gets into along the way. It's not meant to be a "how to". It's strictly fantasy. I hope you enjoy and cum lots!

*****

It's been three months since that fateful day Tiffany's mother Carol became aware her son was having sex with their neighbor Greg. The same day Carol herself became Greg's new fucktoy. Since then Greg has fucked Carol or Tiffany or Carol and Tiffany, every night and Carol couldn't be happier!

And on the nights Greg fucked them both, Carol's son Tiffany would leave to go sleep in his own bed so Carol and Greg could have some private time. In fact he seemed to be in a rush to get to his own room which is surprising seeing how eager he was to join them in the first place (If you don't know why Tiffany made a hasty retreat that's because you didn't read the first three chapters). But Carol wasn't complaining, she was falling in love with her new neighbor and his 10 inch cock. She would do anything for him as long as he kept her pussy and ass satisfied, and that he did.

Yes life was good in the Bennings home everybody was well fucked.

Charles (Tiffany) was also in a happy place. Getting big fat Daddy cock on the regular and not having to hide her sexuality from her mother was fabulous enough but on top of that her video sales were through the roof! She was making five grand a week between video sales and cam shows! And since all the actors were unaware of them being recorded Tiffany didn't have to pay anyone.

With her closing in on $100,000 saved, it was time to fulfill her life long dream of becoming a real girl! So with visions of new tits, ass and lips, Tiffany went to one of the best plastic surgeons in the city, Dr. Alan Landry for a consultation.

Sitting in the waiting area Tiffany looked around at the other girls waiting to see the doctor. Some where very flat chested and obviously just wanted to improve there looks so they can level the playing field. Others looked like this was not their first time here and wanted to go bigger or maybe just wanted some touch ups.

Feeling a little self conscious, Tiffany wondered if she was the only boy here! Looking for signs of gender amongst the other patients, she realized she was the only one who was transgender. Deep in thought Tiffany was a little startled when she heard her name called.

"Tiffany, Tiffany Charles...' the nurse called using the name Tiffany goes by on her cam shows.

The woman calling her name must have been a client as well as the nurse because she had the fullest lips a women could have with out looking like a freak. She also had what appeared to be extremely firm double E breasts with fat long nipples that poked through her nurse's uniform and begged to be sucked. Underneath her tits was a 22 inch waist line which flared out to a 38 inch hips.

Being a little distracted by the stunning bimbo nurse, Tiffany sighed and whispered "Goals".

She heard her name called one more time. "Tiffany Charles?"

"That's me." She said getting out her seat taking one last look around before following the nurse into the exam room.

Once behind closed doors, she was given a robe and told to change. After she had the robe secured Tiffany was asked to hop up on the exam table.

"Just relax, the Dr. will be in shortly," the nurse said as she left the room.

Tiffany waited no more than 2 minutes before the Dr. entered the exam room.

"Jesus fucking Christmas he's delicious!"

Standing around 6'2" he must have weighed around 175lbs of pure muscle. Guessing him to be around 40-45 years old, her girlie cock got all hard and drippy and she mumbled "Daddy cock!" under her breath

"Tiffany Charles?" he asked while looking at a clipboard.

"Yes Dr. Landry." she answered in a dreamy trance. His damn lab coat was blocking her view of his crotch. But judging by his hands, Tiffany was willing to bet he was packing.

"So I was going over your chart and I see you're looking to get breast implants as well as lip enhancements and ass implants, correct?"

"Yes Doctor. As you know I was born a boy but have been living my life as a girl for a few years. So now I think it's time to take it to the next obvious level and get some improvements." She said as she cupped my little tits.

"Well I must say I really think you're sexy just the way you are but if it would make you happier to have these changes then I won't try to talk you out of them."

Did he just say I was sexy? I mean I know I'm sexy but I would have figured he was super straight. In fact I'll bet he's fucking that hot nurse!

"You think I'm sexy?" Tiffany asked while her head was lowered staring at the ground? Then she felt his presence as he walked up to her and lifted her chin with his long fingers. As he was smiling and looking straight into her eyes he said. "I think you're hot!" and then he lowered his lips to Tiffany's and kissed her loosely on the mouth for a few seconds before his tongue entered and searched for hers After a minute or two she felt him twisting her little nipples, not hard but just enough to make her gasp. Tiffany felt her clitty begin leaking through her panties and down her thigh. Tiffany reached for his crotch and that's when she found out how wrong she was. He wasn't big, he was huge he had to be in 12inch range and thick as a soda can.

That's when the nurse re-entered the room.

"Dr. Your next appointment just cancelled, something about a family emergency. So I rescheduled her for next week."

"Thank you nurse. But while I have you, could you come here for a moment? I want to show Tiffany something. Looks like we have some extra time!"

What did the Dr. want her to show me? Tiffany wondered. As the nurse came alongside the Doctor he told her to open her uniform up and show her tits. Which she did without hesitation! They were huge and her nipples looked like little cocks needing to be sucked.

"Tiffany I want you to feel nurse Lisa's breast. Don't be shy, she's loves having strangers feel her up she's quite the slut!" He said as he guided young Tiffany's right hand to the nurses left breast.

Nurse Lisa moaned and shivered slightly at the thought of being offered up like a piece of meat! Tiffany gave the extra large breast a good squeeze which earned her another moan and shiver from the sexy nurse. It was firm yet soft and when she cupped them from underneath they felt heavy, she couldn't even find any scars. Tiffany was starting to think they were real. So she asked

"Are they real? They feel real?"

The nurse who was breathing heavy and crossing her legs, stopped momentarily and said "No but everyone that sees them...or feels them thinks they are!"

"Nurse Lisa open your uniform all the way and pull down your panties!" the Dr. demanded. "Yes sir." She said. She was starting to look a little flush. Tiffany was starting to think nurse Lisa was a little bit submissive and an exhibitionist, because of how eager she was to comply. All this was obviously having an effect on her.

After opening her uniform she proceeded to pulling down her panties when to young Tiffany's surprise out popped a six inch semi hard uncircumcised cock.

Tiffany was shocked. How did she miss this?

I usually can tell when I meet another transgender woman but Nurse Lisa had me fooled completely. "How is it you look so feminine? You're completely passable, the best I've ever seen!"

Nurse Lisa blushing thanked Tiffany and explained.

"Dr. Alan really is the best. He gave me these beautiful breast, padded my ass and even laser removed all my facial and pubic hair. But the most amazing thing he did was my nose, cheek bone and jawline reconstruction. It was very expensive but when the doctor found out I was a registered nurse, he hired me right away explaining that my job will require me to...perform duties outside the normal activities of a standard nurse. Having a living example of his finest work on display does wonders for the business. I love working here he's very good to me, plus there are some perks."

"Well as you can see Tiffany what you're looking for isn't that uncommon. Since you already have extremely feminine features, your procedures won't be as invasive."

As Dr. Alan spoke he noticed Tiffany staring at Nurse Lisa's cock which had grown more erect being exposed in front of a stranger.

"You could touch her if you'd like. Stroke her cock and suck her nipples, she wouldn't mind!"

Tiffany, finally able to get some of the hot nurse didn't hesitate grabbing her fat girl cock and stroking it from tip to balls.

Nurse Lisa started moaning as her cock leaked pre cum. Reaching up with one of her free hands, the sexy nurse took hold of Tiffany and guided the young femboy to one of her oversized nipples. "Mmmm yes!"

Dr. Alan thought it was time to move things along. "Why don't you get on your knees and taste her!" It was more of a demand than a request, since the doctor grabbed Tiffany by the back of the neck and guided her to her knees.

As if in a trance, Tiffany complied and swallowed all 8inches.

Nurse Lisa held Tiffany's head in both hands and started plunging her fat cock down Tiffany's throat. The nurse must have been edging because she blew her load before Tiffany was ready.

Starting to gag Tiffany pulled back a bit so she could stop choking as well as taste some of her delicious cock cream. Tiffany's mouth filled quickly and fully, forcing her to swallow.

Once she finished Tiffany licked her cock clean.

Nurse-cums-a lot was still shivering from her orgasm.

Never one to miss a opportunity, Tiffany, still on her knees turned slightly to her right and started caressing the good doctor's package. Not waiting for permission Tiffany untied the doctor's scrubs and watched them drop to the floor. She took in a sharp breath when saw the column of cock inefficiently hidden behind the doctor's briefs. Tiffany couldn't help but rub her face all over the cock behind the curtain and began purring like the little slut kitten she was.

Nurse Lisa dropped down beside her and started sucking on the head through the briefs while Tiffany was sucking on the balls, also through the briefs.

The doctor, not wanting to soil his only pair, reached inside and whipped out his meat pole and stroked it a few times between the two girls.

"You go first sweetheart, I want to see your sexy little mouth handle that monster cock." nurse Lisa offered. She then proceeded to get behind Tiffany and reached around into the robe and fished out her little girl cock.

Tiffany wasting no time began licking the huge fat cock in front of her, knowing it would need to be lubed if she had any chance of getting it down her throat. As she licked it seemed to have gotten harder more steel like. The helmet got so swollen she wondered if she would get it in her mouth. So she started at the top and got as much of the head as she could in her mouth jabbing her little tongue in the pee hole. This got the doctor so hot his fat cock started leaking copious amounts of pre cum which helped Tiffany get four thick inches in her mouth.

Excited about having a mouth full of cock Tiffany started moaning and salivating which helped her get two more inches of cock inside her tight throat.

Mean while nurse Lisa decided only one hand was necessary for such a small cock so with her free hand she squeezed Tiffany's ass cheeks then slipped a finger between her cheeks and fingered her boy cunt. First with one, then two, then three fingers, amazed at how loose the little slut was.

"Dr. Alan you simply must fuck this ass pussy! It's so ready for a big cock like yours." The whore nurse announced.

"Tiffany is that true? Have you been fucked by a big cock before?" the doctor asked.

Tiffany reluctant to take the huge cock out of her throat, did so and said "My Daddy has a fat ten inch cock and he bought me a super sized 14 inch dildo that's as thick as yours so I'm more than ready. Why, are you going to fuck me now?"

"Stand up and come over to the exam table. I want you to stand on that step stool, that will bring you to the right height to lean forward on to the table...yes like that. Now nurse strap the little slut in while I take my scrubs and briefs off."

First she strapped her wrist to the far end. Then strapped her waist.

When they were done the doctor stepped back and kicked the stool out from under her feet so they would dangle ten inches off the ground. Satisfied with the position he had Tiffany in he opened a draw and pulled out a tube of lubricant and handed it to the nurse who applied a fair amount to Tiffany's hole. Then she turned to the doctor's 12inch meat pole and applied some there as well.

Knowing he had patients in the waiting room doc Alan wasted no time and placed the tip of his long fat cock at Tiffany's ass cunt and pushed and pushed until his fat helmet pop passed her anal ring.

Tiffany yelped.

"Tiffany are you okay up there?" he asked

"Yes sir, I can take more. Just go slow...at first. My pussy feels sooo good!"

Seeing his patient was ready for more, the doctor started feeding Tiffany's boycunt inch after inch after inch, until there was only three inches left. He notice that gone was the confident fucktoy and in her place was a whimpering, drooling, lust filled sissy that was trained not to complain.

"Nurse take out your butt plug and put it in Tiffany's mouth. I'm about to give her the last three inches and we can't take any chance that she might scream."

Nurse Lisa reached between her ass cheeks and pulled out, after some effort, a five inch long, three inch wide butt plug out her sissy hole and stuffed it in Tiffany's mouth. The first two and a half inches went in fine but at the widest point it took some effort on nurse Lisa's part. When it finally popped in, doc Alan slammed his three remaining inch's in and held up right there!

Tiffany saw stars!

Her body was bucking, her eyes rolled to the back of her head and doc Alan felt her asscunt pulsing and contacting. It could only mean one thing...

"She's cumming hard, I can feel it all around my cock! Fuuuckk that feels sooo good! Her ass feels like virgin pussy cumming for the first time!" and that said he began to fuck Tiffany like he meant it.

He would pull out half way and slam it home again. Repeating this over and over.

Tiffany was still riding out her orgasm when a second wave hit her causing her to go stiff from head to toe. Nurse Lisa seeing this bit her bottom lip and reached back to the empty hole where her plug was and shoved all her fingers in to the third knuckle. She began wiggling her digits around like she was trying to find her car keys.

"Ohhh Daddy I want some too! That is so hot! Look at her she's so small and your cock is so big. Oh my God it's making me so hot!" Not willing to be left out anymore, nurse Lisa leaned over Tiffany's ass and started licking the part of the doctor's cock that would be exposed on the back strokr, every now and then spitting at the area to provide lubricant only to lick it all up again. She was loosing it fast!

The doctor seeing this knew he had to do something quick before she started getting too jealous. So he grabbed his nurse by the hair dragged her face up to him and shoved his tongue in her mouth. The hot slutty nurse responded by sucking on his tongue like it was a small cock.

Meanwhile Tiffany was starting her third series of orgasms which was the strongest one yet. Sending her into convulsions. Her ass tightened so much it squeezed all the lubricant out from between her ass and the doctor's cock like a fountain. It looked like she anally squirted. It actually got all over the doctor and his nurse.

"Holy shit the little bitch squirted from her ass! That is so hot! Nurse Lisa said as she grabbed her cock which was rock hard and with just a few strokes came hard all over Tiffany's ass and legs.

Between witnessing what truly looked like an anal squirt, seeing how it affected his nurse and Tiffany's convulsing asscunt, doctor Alan was about to experience the biggest orgasm of his life.

"FUUUCKK I'M CUMMING OHHH FUUUCKK! TAKE IT YOU LITTLE BITCH! TAKE IT IN YOUR TIGHT LITTLE ASSCUNT!" And the doctor started filling up Tiffany's ass canal with literally a pint of thick hot cum.

Tiffany feeling her ass being filled up had her fourth and final orgasm. Though not as hard as the previous three, it still curled her toes!

Then she felt the massive cock pulling out of her boypussy until the head popped out leaving a huge gap.

Nurse Lisa wasted no time and got down and sucked the fresh hot anal cream pie like the needful slut she is, moaning and slurping until there was nothing but empty hole. Then finished by licking her own girly juices off of Tiffany's ass and legs.

"Nurse, please release Ms. Charles from her restraints."

"Yes doctor"

First she removed the but plug from Tiffany's mouth and placed it back in her ass. Then she released her from her constraints.

Tiffany's legs were a little wobbly but she was able to start getting dressed.

"Thank you doctor that was the best fucking I've ever received, your cock is magical!

And you too nurse Lisa thank you for lending me your plug, if you hadn't I would have scared off all your patients with my screaming."

"My pleasure sweetie!" she said as she moved her butt plug in and out of her asscunt.

"Yes nurse thank you. Schedule an appointment for tomorrow for Ms. Charles! Make it for five o'clock so she'll be my last patient for the day, I have a feeling we are going to need the extra time." He said with a lusty grin.

To be continued.