Neighbors Sissy Son Ch. 06

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Tiffany gets to try out her new equipment.
5.1k words
4.6
62.1k
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Part 7 of the 7 part series

Updated 06/08/2023
Created 08/04/2017
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Editor's note: this story contains scenes of incest or incest content.

*****

Tiffany Charles

My name is Charles Bennings but you can call me Tiffany Charles. If you've been following this story from the beginning, then you know I was born a boy but with my feminine body and face, I easily live my life as a girl. You also know that I make a lot of money doing cam sex shows on the web, money I recently used to pay for a ground breaking new procedure that allows me to enhance my looks at will. That means if I want huge bimbo tits all I have to do is concentrate and will it to be. Same goes for my cock, my lips, my ass and my asscunt. With a thought my asscunt could go from gapping to virgin in a minute.

By now you're either scratching your head wondering "What the fuck is she talking about?" or you're curious to know what I plan to do with my new abilities.

If you're the former, you need to go read chapters 1 through 5.

If you're still here then I'll let you in on a little secret of mine, most of the time I feel like having my boypussy crammed full of fat Daddy cock! I mean nothing is better than feeling my daddy pushing his thick meat pole into my tight little hole and pounding me while his hands are around my throat. Nothing except for when I feel his already fat cock swell even fatter and the head of his cock going from semi hard to fist like because he's about to fill me with is hot cum.

Oh fuck, I think I just made cummies in my panties!

Any who, on the rarest of occasions, I'm curious to know what it would feel like to be the one doing the pounding. Or having someone gagging on my fat meat pole because I was forcing myself down their throat with little or no regard for their gagging and choking.

Sometimes you feel like a nut, sometimes you don't!

So when Dr. Landry offered to make me the first recipient of the new procedure, I was quite grateful.

Since you fine folks stuck around because you read chapters 1 through 5, you know that my next door neighbor, who is my "Daddy" is now my mommies "Daddy" also! It really is the perfect situation since I get to enjoy his juicy 10 inch cock regularly and my mommy gets to have a man in her life.

He's really has her accepting her role as submissive cum slut and cock junkie. There has been many a night where Daddy came over with a few friends and mommy and I were left cum and cock drunk by morning.

My Daddy is so kinky. He taught me how to edge for hours so when I do cum I cum a lot. Even though my new abilities allow me to cum buckets or dribble cummies. Daddy also taught me how to "milk the prostate" which also makes me cum a lot. Surprisingly enough my Daddy likes when I milk his prostate so he can cum buckets. I say surprisingly because him being such an alpha male I would have thought putting a finger or two up his ass would make him feel...girly, I know it makes me feel girly. I guess I'm lucky to have someone like Daddy to teach me these things.

Anyway, I know Daddy likes big tits so, tonight when he gets back from his work trip I plan on starting off at a B cup and graduating to double E before the night is through. He's going to be so surprised, hee-hee-hee!

Carol Bennings

"So how much do you love this beautiful home? Isn't it everything you asked for?" Carol asked hoping to close this deal quickly. It was the fourth home she has shown this couple this week, ninth one in the last two weeks. She was one of the most successful real estate agents when selling to couples and this couple was going to buy a house from her or her name wasn't Carol...

"We'll Take it! It's perfect!" Jennifer Taylor exclaimed. The couple was in their thirties, he a broker her a nurse at the local hospital.

"Yah, it's a twenty minute drive for me and only eight minutes for my wife but what sold us, is the size of the back yard. We like to have friends over and barbeque." Phillip said with his arm around his much smaller wife. He was a big man maybe 6'4" 240lbs. Played a little football in college but as soon as he graduated went right to work for his uncle's firm. His wife much smaller at 5'1" 110 soaking wet and no ass, looked like a young boy with her flat chest and short hair style.

"No wonder he keeps staring at my tits and ass. That poor man must be starving for a real woman." Carol thought to herself as she slyly gazed for the fourth time at his prominent bulge.

After the paperwork was signed back at her office and a twenty percent down payment check was handed to Carol, she handed the keys to the Taylor's and congratulated them on being new home owners.

"I wish you folks the best of luck in your new home."

"Is there a ladies room I can use? Too much coffee I think." Asked Mrs. Taylor.

"Of course, second door on your left just down the hall" Carol said as she walked Mrs. Taylor to the door. When Carol turned around she was face to chest with Mr. Taylor.

"I was hoping she would need the bathroom giving us a little alone time. You are one fine piece of ass!" Phillip Taylor said as he wrapped his arms around Carol's waist and pulled her in for a crotch grind.

Carol being caught off guard didn't resist quick enough and felt every inch of the huge hard cock being pressed up against her undefended pussy.

"Mr. Taylor! What would your wife think? Nnggaahh let me go."

Struggling only added to the friction her now wet pussy was experiencing.

Phillip knew his wife would be in the bathroom for at least 10 minutes so he worked quickly. Having Carol pinned up against the door he knew this slut could feel his 11 inch cock, the same cock she's been trying to catch a peek of all afternoon.

"You feel that up against your pussy making you very wet? That's an 11 inch fat cock that wants to fuck you but first."

And with that said he easily pushed Carol to her knees and said,

"Take it out I know you're dying to see it."

Carol didn't want to admit she was trying to get a look at his crotch all afternoon. Her daddy was two states away because of work and she hadn't been fucked in over a week. She was extremely wet right now so wet she could feel her panties sticking to her cunt lips. With trembling hands she reached for his zipper and pulled it down then looked up into his eyes as she reached in and fished out a cock bigger and fatter then Greg's. She knew she was going to suck it she was just delaying the inevitable and time was not on their side so she opened her mouth an took in about 5 inches of man meat.

"Uuuummm...uuumm...um." Was all she got out with her mouth full, until she took him deeper to the back of her throat and felt her gag reflex kicking in.

"GLUK GLAK GLUK GLAK GLUK!" as she bobbed on his pole. Carol was in her zone. This is where she was at her best, on her knees in front of and sucking on a huge cock.

"That's it slut, suck my fucking cock you whore!" Phillip demanded as he squeezed and twisted Carol's fat tits.

Carol love it when a man force fed her cock while calling her nasty names, it got her juices flowing and right now they were flowing right down her thighs. Which gave Carol an idea. She reached up her skirt and moved her panties to the side and stuck her index finger all the way to the third knuckle. When she removed it she reached around Phillip with her slimy digit and shoved it in his ass hole, again to the third knuckle.

"Holy mother of God! You bitch, I'm cumming fuck!" Phillip all but yelled.

Carol feeling his huge cock get even bigger and harder before he unloaded a torrent of cum down her throat which triggered her orgasm because nothing made Carol cum faster than a big fat cock cumming down her throat!

Phillip removed his cock from the sluts throat, quickly tucked it back in his pants and straightened his shirt and tie. Carol got up off her knees and straightened herself up, just in time to see Mrs. Taylor return from the bathroom.

"Wow that coffee always does right through me. Anyway thanks for all your patience with us. I know it started to look like we were never going to buy a house." Jennifer said while putting on her coat.

"I understand, these things take time. I hope you'll recommend me to your friends." Carol said hoping her cum breath wasn't too obvious.

Phillip winked at Carol and said "Don't you worry I plan on telling all my friends about you and your excellent...service!"

Minutes later Carol was closing up for the day and heading home. Tonight Daddy comes back from his trip so her neglected pussy was finally going to get some attention.

Greg aka Daddy

Sitting in the back of the Uber that picked him up at the airport, Greg thought about his sluts Carol and Tiffany. He was still fucking both of them but had to admit he was getting emotionally attached to Carol.

At first he thought that would create problems but Tiffany was okay with just being invited in to his and Carol's bed every now and then.

In fact the more he thought about it the more he realized Tiffany always seemed to have something going on that she was keeping to herself. On the nights when she was invited to join him and her mother in their bed, she would be insatiable but as soon as it was over she didn't hang around and get clingy. She would run off to her room lock the door and not come out for hours.

"God I hope she's not doing drugs!" Greg thought as the Uber pulled up in front of his building.

Once in his apartment, he headed straight for the shower, traveling always made him feel so dirty. While in the shower his thoughts returned to Tiffany.

"Now that I think about it, she always seems to have money to go shopping so it can't be that she's doing drugs." He realized.

He shook his head thinking there was no sense trying to see a problem where there wasn't one.

Bennings residence

Carol was just finishing up Greg's favorite meal when Tiffany got home. As soon as she walked through the door Carol new something was different about her.

"Oh shit! You got lip injections! Your lips look so much fuller." Carol exclaimed. "Daddy's going to love them!"

"I hope so but to tell you the truth I didn't get them for Daddy, I got them for me... but he's aloud to enjoy them and so are you." Tiffany said as she hung up her jacket.

The jacket, which was a three quarter length, once removed exposed her new B cup breast and her new J-low ass!

"Charles Bennings! What did you do to your body?" Carol only called her by her boy name when she was very angry.

Tiffany flinched and then remembered she was 19 years old and didn't need permission to do what she did.

"Mommy you know I've always said if I have the money, I'm going to get breast implants and get my lips done. Well I've saved up the money and found an amazing surgeon and...well the results speak for themselves." she said while striking a pose.

"Look I'm not angry, I'm just caught by surprise, you could have told me, I would have went with you. How did you recover so quickly?"

"I got it done two days ago and I've been recovering in my room" Tiffany lied not yet wanting to give her secret away.

"Sorry baby I have been so caught up in selling a house to that couple, that I've been neglecting to pay attention around here." Carol said just as there was a knock at the door.

"Daddy is home, yay!" Tiffany shrieked and ran to answer the door. She swung the door open and leaped into Greg's arms wrapping her little legs around him.

With kisses all over his face and then a tongue down his throat, Tiffany was the happiest little tranny in the world.

Greg was expecting something like this. What he wasn't expecting was the soft feel of breast against his chest, or the fat ass in his hands as he held her up. So though he was enjoying the affection, he broke off the kiss needing to investigate.

"Tiffany why is your ass fatter and your tits...you have tits! Jump down let me see." He said helping her down off his waist. Tiffany always ready to get naked, pealed off all her clothes before any one could change their mind. With hands behind her back Tiffany thrust her brand new tits out towards Greg.

"Do you like them daddy? They're magic tits go ahead suck my nipples." Exclaimed Tiffany.

Greg never one to miss out on sucking some nip, bent low to take in the small but erect nipple on her left breast.

"Mmmmm...Mmmm..mm.." he hungrily sucked like it was his last meal, mean while he grabbed her right nipple and twisted it.

Tiffany closed her eyes and imagined her nipples growing to an inch long and half inch thick.

Greg was really getting into the nipple sucking and tweaking when all of a sudden they began to grow. Like little cocks they became longer and fatter. It was the most amazing thing he's ever experienced. Reluctantly backing off he asked,

"Tiffany, how is that possible?"

Not ready to give away her secrets just yet, she lied. "It's a new type of hormone treatment that enhances the breast without surgery and the only side effect is long, fat, hard, nipples when I'm excited." She continued to play with her nipples hoping to entice Daddy to pick up where he left off.

Tiffany was convinced to put her clothes back on, which she reluctantly did and they all sat down to dinner. Carol and Tiffany asked Greg questions about his trip and he asked Carol about work and Tiffany about her enhancements.

What was really on their minds was the after dinner fuck fest that was inevitable. Once the plates were cleared from the table Tiffany volunteered to do the cleaning up while mommy and daddy went upstairs and got started.

"Hurry up though, because I want both my girls tonight." Greg said as he headed to the master bedroom with Carol.

With the "grown ups" gone Tiffany sprang into action. She ran to her room and pulled out some shopping bags she hid in the back of her closet and started going through them. In the first bag she pulled out a black latex corset with half cups for her new breast. The next thing she pulled out was black latex thigh high boots with 5 inch heels. In the second bag she pulled out long black latex gloves, that when worn reached up past her elbows and then fishnet crotch-less pantyhose. She pulled one more bag out the closet and it was the biggest one yet. Out of this bag she pulled out a black latex hood mask that had two holes at the top for her two pigtails. Next came out a small black latex whip attached to a 10 inch black dildo.

With everything laid out Tiffany got dressed. She put on the fishnets with her little cock and balls hanging from the crotch. Then the corset with her new B cup breast sitting in the half cups. She put the mask on last after the boots and gloves. She finished off the outfit with the 10 inch dildo in her asscunt with the whip hanging like a latex tail. In that last big bag contained the last two items. A black pacifier that had a 3 inch dildo to suck on instead and a black latex teddy bear that had a six inch strap on. Outfit complete she stood in front of the mirror and thought. "Wait till they get a load of me!"

Looking at the clock, she realized she's been in her room for a half hour getting ready.

"That ecstasy I slipped in their food should be kicking in right about now!" so she took a deep breath and headed to her mother's room.

Carol's room

"Daddy your cock taste sooo good and it feels so sexy in my mouth. I never noticed how delicious it was before tonight." Carol said influenced by the ecstasy.

"This is the best blowjob I ever got. I feels like my cock is all the way down her throat and sticking out her ass and if that's the case then Tiffany needs to hurry so she can suck the part sticking out. OMG a double blowjob!"

The ecstasy kicked in unnoticed about 10 minutes ago and the blowjob became a whole new experience. Greg was just about to tell Carol to stick her finger up his ass when the door burst open and Mistress Tiffany entered the room.

"You sluts have been very bad and you need to be disciplined!" said Mistress Tiffany. She placed the strap on teddy bear on a seat and strutted over to the bed. Carol stopped sucking Greg's cock and sat up.

Tiffany grabbed her mother by the hair and forced her to her knees in front of her hard four inch cock.

"Suck it slut. Get it nice and wet because it's going up your ass!" Mistress Tiffany demanded shoving her little hard cock as far in as it would reach.

"You Daddy slut, fuck this bitch, stretch her out for me. NOW!"

"Sure baby cakes, I could do that. Why am I stretching her out again?" Greg asked not sure of his orders.

"So I can fuck her with my huge fat cock. Now hurry!"

Greg hopped off the bed and knelt down and holding his still slippery cock at the base, he pushed the fat helmet passed Carol's anal ring. In the back of his ecstasy clouded mind he wondered what she meant by "huge fat cock", since her cock couldn't be more than 4 inches at best.

As Greg shoved 6 inches more into Carol's ass, she moaned on her sissy son's cock. Greg heard her moaning and forced the rest of his fat Daddy cock all the way in.

Tiffany thought this was the perfect time to try out her new cock so she closed her eyes and imagined her cock slowly growing to 9 inches and thickening to 2 inches.

Carol's first inclination that something wasn't quite right, was when the cock in her mouth started tapping at her throat. She wanted to pull off and see for herself what simply had to be impossible but Tiffany had her hands on the back of her head, holding her in place, face fucking her.

Greg was in his own world, oblivious to the situation going on in Carol's throat. After bottoming out in Carol's tight ass, he would pull all the way out until all that remained in her hole was the tip and then slam back in to the hilt. This steady ass reaming had Carol and Greg on the verge of cumming soon.

"Daddy slut, I can tell by the look on your face that you're about to make cummies in mommies asshole. When your done cumming I want you to come around front and have this cock slut clean you off, it's what cock sluts are for." Mistress Tiffany demanded.

Carol hearing every word, couldn't believe her sissy son was being so...dominant and forceful. It was bringing her closer to orgasm. "Did Tiffany's cock get bigger? I don't remember it being this big and fat. I can't even deep throat it any more." Tiffany was now at 11 inches and 3 inches thick with a head the size of large kiwi.

"OH FUUUCKK I'M CUMMING! SHIT...FUCK TAKE IT YOU FUCKING WHORE!" Greg shouted as he filled Carol's convulsing anal canal with hot Daddy juice.

Mistress Tiffany having seen this, ordered, "switch now Daddy slut!"

Tiffany shrunk her cock back to normal size, so her secret remained just that and pulled out of Carol's throat to switch places with Greg.

Carol, confused about what she saw come out of her throat thought "I think I'm going insane.

When Greg settled in front of her she hesitantly grabbed his cock and asked Greg, "is this real?"

Mistress Tiffany was by this time really feeling her role as Dom Mistress, pulled out the dildo whip in her asscunt and lightly gave her mother's ass a couple of test lashes. It was hard to tell if Carol's moans were from sucking Daddies semi limp cock or from the lashes so she gave her a few more harder lashes and got her answer.

Carol removed Greg's cock and claimed. "I'm such a bad slut and I need to be punished. Please Mistress Tiffany, I was sooo bad today. I sucked a married man off while his wife was using the bathroom in my office. I know it was wrong but I couldn't help myself, I'm such a slut cock junkie. I need more punishment, please... just do it." Carol begged while stroking Greg's Daddy cock.

Greg couldn't believe what he was seeing or hearing, between Carol's revelation and Tiffany's new attitude, his girls made his cock hard all over again.

Tiffany looked at Carol and didn't see the mother that raised her or bought her presents on her birthday or Christmas. No she saw a bad mommy slut that needed to be punished and taught that there were consequences for such behavior. So she gave her ten more lashes leaving her fat ass red and soar. Greg shoved his hard cock in her mouth to quiet her screaming.

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