Neighbors Sissy Son Ch. 01

Hello everyone. This is a long overdue rewrite of my very first story, 'Neighbors sissy son' the story that started it all. Some readers felt I wrote Greg's character as a harsh asshole and maybe they're right. But the real reason for the rewrite is because I felt that the original story was not my best effort. So you don't have to read the first one to enjoy this one. But if you do, I'd love to hear which one you preferred.

Tags are as follows:

#sissy #femboy #mtf #transgender #big cock #older male #anal #neighbor #submissive

Hope you enjoy it. All characters are over 18 years of age.

Neighbors sissy son ch 1

When I moved into this condominium three years ago I had no idea there were so many single divorced women that also resided here. I always had a thing for the newly divorced due to their not wanting to get into a complicated relationship after just leaving one, especially those with a kid or two. Getting dick but not having to cook and clean for it, well that's a win in their book!

That's why I was grinning ear to ear looking out my window at the M.I.L.F and her teenage son that just got out the car behind a moving truck. With no man in tow, I rightly figured her for divorced.

But before I get into that, let me tell you a little about myself. My name is Greg Hampton. I'm 40 years young, in great shape due to daily workouts and I'm lucky enough to be able to work from home. A lot of people have tried and failed at this working arrangement. Seems that without a boss or even a supervisor, most folks slack off and get next to nothing done. But that's them, not me! I learned early on that it's all about time management.

I have a daily routine that I rarely detour from and it leaves me with more than enough free time. There's even a gym in this building for residents so It's easy to stay in shape.

As I lusted after the hot mom, I was surprised to see one of the Mexican movers grab the son's little butt when said mom wasn't looking. Even more to my surprise, the boy turned and blew him a kiss.

Now mind you, all of this went unnoticed by his mother. For me this was an interesting turn of events because I always fantasized about fucking a cute femboy. And this boy was really cute! He couldn't weigh more than 120 lbs and was not much more than 5 feet tall.

I was already picturing him in a cheerleader outfit as he deepthroated my 10 inch fat cock.

His mother was built like a pornstar, big fat double D's, juicy ass and a hip to waist ratio that had my mouth watering.

Now, I was fantasizing about a three some with mother and son serving as my personal sluts.

Suffice it to say my dick was hard and leaking so I pulled it out through the zipper and was slowly stroking it till everyone was off the street and in the building.

I happened to know that there was only one condo vacant in my complex and it was down the hall from mine so I hurried over to my front door, looked through the peephole and watched them exit the elevator as they headed for their new home. Once the last of their possessions were brought in, my new M.I.L.F neighbor gave each of these guys a soul sucking kiss as their hands freely roamed her hot body.

"That little slut must have gotten railed by all three of the Mexican movers, my kind of woman! Come to think of it, I think the son might have gotten some action of his own."

Once they left and she went inside, I retreated to my living room and started formulating a plan to get both mother and son on the end of my cock asap!

I think the key is that mommy dearest doesn't know her son is attracted to men. Which means 1: she's naive and that could be useful. And 2: the sissy is hiding his proclivities from his slut mommy so that is something I could definitely use!

What I'll need to do is watch them for a couple of days so I can learn their schedules. I want to catch the sissy boy when his mother isn't around.

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Charles (aka Tiffany) was laying in her bed contemplating her transition from awkward femboy to confident woman. Being she was home alone Charles was dressed in a black micro mini skirt that barely covered her pink panties and a pink spaghetti strap tank top with a training bra. She had already decided that some plastic surgery was in order and saw herself with huge tits and a fat ass. The petite teen just knew once she had the body of her dreams, men would trip over themselves to get to her. She was willing to go to great lengths to earn that attention.

Charles even gave herself a girl name that only her other sissy friends called her by, 'Tiffany Charles'.

"One day my body will match my name!" Tiffany claimed.

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I watched the new neighbors for a full week and learned that the slut mommy was out the door around 7am and didn't return until 7pm that evening. It also happened that her sissy son got home from school around 2:45. And being new to the area, he didn't have any local friends yet. So on the following Monday at exactly 3pm I marched over with an apple pie I bought just for the occasion and knocked on the door under the pretense of being the welcome wagon.

After knocking, I was very surprised to see a hot, teen girl answer the door. She looked a lot like Jenna Ortega, just with pale freckled skin. Shit, was I slipping? Did the milf also have a teen daughter?

I wondered where her brother was but more importantly I needed to compose myself after this curve ball so I carried on with my plan not sure how to play this.

"Hello Miss, is your mother home? I'm Greg Hampton from just down the hall, we're neighbors so I thought I'd welcome you folks to the neighborhood." I said as I tried to look past her into the apartment.

"Hello Greg I'm Tiffany and sorry to say, my mom is at work and won't be home until later." She said while eyeing me up and down like a piece of candy until her eye's settled on the bulge in my pants.

I was about to make a retreat back to my place when she boldly swung the door all the way open and invited me in.

"Would you like to come in for a cup of coffee? My mother would be disappointed in me if I wasn't hospitable. I see you brought a pie, is it a creampie? I just love a creampie don't you?" She brazenly said.

'Holy shit! The little vixen was flirting with me! And the comment about loving a creampie was too spot on not to be an innuendo. Well fuck, I could play this game as well.' I thought.

"I do wish it was a creampie, I'm sorry to say It's an apple pie. But I promise the next time I'll 'give' you a creampie. Would you like that?" I parried which earned me a cheeky smile.

"I think we're going to be good friends and great neighbors, Greg. Why don't you take a seat on the couch while I go pour us a cup and put the pie in the fridge." Tiffany said before heading off to the kitchen.

I watched as she walked away with an exaggerated sway to her slim boyish hips. And that's when the building fell on my head and woke me up. 'Holy mother of god...that's not the daughter, I think that's the femboy son in drag! In fact I'm absolutely sure that's who it is. I formulated a new plan on the spot. I got up off the couch and went into the kitchen where I found the petite little tease at the counter reaching up for a cup that was just out of reach. Standing behind 'her' I offered my assistance and as I slowly reached for the cup my erection made grinding contact with her sweet little ass.

She was startled at first but then began pushing her behind back at me.

"Oh Greg! I can feel it! Nnnnggg! Your cock is so big! But there's...but I have to tell you something first. Please don't be angry with me. Oh fuck your making my asshole twitch." Tiffany barely got out.

"Don't bother, I already know your secret. I know you're a boy when your mother is home and a hot little cum slut when she goes to work. And I intend on keeping your secret safe! As long as you do as you're told." I threatened.

Reaching around with both hands on her thighs, I slid them slowly up and under her skirt until I reached her thong and cupped her tiny balls. All the while I ran light feathery kisses up and down the nape of her neck causing her to shiver. She turned her head to meet my kiss and swooned when my tongue invaded her mouth in search of her own. The kitchen was filled with the sounds of muffled moaning and wet lips smacking. All her bravado disappeared only to be replaced by a desperate need to be lovingly taken.

Breaking the kiss was hard for her but she did and turned to face me with adoring eyes. With me being a foot taller than her, Tiffany had to look up to me. Playfully biting her bottom lip as I lifted her up onto the counter, Tiffany was ready for whatever I wanted from her so I stepped between her thighs.

"I live in apartment 3B. When your mother leaves in the morning I want you to come to me and be ready to do as you're told. You're to keep yourself clean for me. I don't like shit on my cock. And I don't want you fucking random guys. If I have a friend over at my place and I tell you to service him, you don't hesitate. Is that clear?" I asked.

"Oh god yes daddy! I'll do all that you tell me to. And I'm always clean and ready. I'll be your good girl, I promise. You're such a sexy daddy I can't believe how lucky I am that we moved here." Tiffany promised.

"Good girl! I think it's time for some proper training. We'll start with your oral skills. Once you're able to take me completely down your throat, we'll move on to anal training." I informed her.

"Now why don't you be a good girl, drop down to your knees and show daddy what you can do." I suggested.

Tiffany didn't waste any time doing just that. Before she retrieved my hard leaking cock Tiffany rubbed her face all over my crotch sensuously while she purred like a little kitten. Then using only her teeth, she pulled down my zipper.

Once open her tongue found its way inside and began licking the hard column of cock that was encased in my briefs. Yeah this girl had a lot of style for someone barely 18.

"Now take it out and get it nice and sloppy wet like a good little slut my kitten." I commanded. Calling her kitten brought a smile to her face so I decided that would be my pet name for her from here on out.

I watched as Tiffany fished out my shaft and took a moment to admire it's size. Using two hands she began stroking me, mesmerized by the copious amounts of pre-cum leaking from my swollen cock head.

Leaning forward my little kitten began licking up and down my veiny column, collecting my juices from one area only to deposit them in another.

She placed the head in her warm wet mouth and looked up into my eyes as she began taking more of me in. As my new slut filled her mouth, she began sucking my fat veiny daddy cock in earnest.

"Fuck that's how you do it! Now take as much as you can in your throat." I requested to see what her capabilities were. Taking about 6 inches of a 10 inch cock told me there's room for improvement. She was moaning in her desperation to please me, which caused vibrations to ripple up and down my shaft. Tiffany took this moment to pull off the dick and go for my balls, bathing them in saliva and whatever pre-cum still in her mouth.

I could tell she was working hard to get me to cum so I stopped holding back, moments later I felt I was getting close to going over the edge and started moaning myself. Upon hearing this change in my demeanor, Tiffany looked up at her new daddy and ramped up her efforts.

"Oh fuck! You little slut! You're going to make me cum. Yeah baby here it cums. Fuck! Shit! You fucking whore drink it all down." I announced as I pumped a pint of thick cock juice into her mouth and down her throat. Like a seasoned professional, not a drop was spilled.

Tiffany, sucking the last remnants of my orgasm, pulled off my softening cock with a loud pop, looking up at her new daddy and asked innocently, "did I do good daddy?"

"Not bad for someone so young! So tell me, have you had anal sex yet and if so how much?" I asked.

"Yes I have but not much. In fact the only 'real man' to fuck me so far was one of the movers. And that was only last week. Other than that, I have a few dildos but none as big as your fat daddycock." Tiffany admitted with a smile.

"Okay, if you have a butt plug, start wearing it 24/7, your training will go a lot smoother if you stay gapped!" I advised.

Without saying a word Tiffany went over to the kitchen table and bent forward to drape her upper body across the top while lifting her skirt with one hand and pulling her thong to the side with the other. I was a little surprised to see she was already wearing one. The little tease knew the effect it would have on me seeing her on display like this. I was getting hard already even after just cuming minutes ago.

The plug had a red jewel sticking out so I took hold of it and slowly pulled on it. I watched as her tight little hole opened up around the plug until it finally passed the widest point. Once removed, Tiffany's asspussy only gapped slightly, indicating more training was necessary.

I decided to pull her little pink thong down her legs to about mid-thigh. Once done I took a step back to admire the view.

Tiffany had delicately thin legs with just enough muscle to not appear sickly but slim enough to accentuate her hips and tiny peach of an ass. Her tiny balls were too small to hang so they sat right up against her very small penis that looked just like a large dangling clitoris.

I moved close enough to take hold of her hips letting both thumbs caress her soft ass cheeks. Bending over, I took a long tantalizingly slow wet lick up her right thigh and kissed her balls when I reached them. I repeated the move with her left thigh only this time I didn't stop until I reached her tight little hole and aggressively shoved my tongue into her depths. This earned me a moan and an 'Oh daddy!'

Alternating between her juicy hole and her tight little balls, I quickly had her begging for more.

"Nggghh! Oh daddy that feels so good! Fuck yes make me ready! Spit on my boypussy daddy, your cock is so big I need to be prepared. Nnnggghh! You're making me so ready to get fucked! Please daddy fuck me with your big beautiful daddycock. Breed me like a slut whore! Make me a real girl please! Make me your real girl!" Tiffany begged and pleaded as she shoved her hole onto my invading tongue.

I knew she needed more preparation so I replaced my tongue with my thumb and applied pressure. Between the plug and my oral attention, my thick digit slipped in working her hole, stretching it, and that earned me some more moans. I removed my thumb and spit on her hole before returning my digit to finish the job of stretching her out.

After a short while I was able to include my other thumb and really open her up for what was to come. With both thumbs inside her abused asshole, it looked like I was splitting a peach. I worked her boycunt till I felt she was ready and placed the head of my cock against her asspussy, teasing her opening until she and I couldn't take it anymore.

I pushed in slowly thinking there would be plenty of opportunities for hardcore fucking. But for now I fucked her at slow steady pace, feeding the little slut about 5 inches of cock on every stroke.

Truth be told, I wasn't surprised when the little minx started begging me to go harder.

"Fuck me daddy! Oh god fuck my hole harder daddy! I need it! Take me and ruin my hole! Own it daddy, it's what I need! It's what you want! Nnnggggggghh! FFFUUCCKK! OH GOD YES JUST LIKE THAT!" Tiffany screamed that last part as I picked up the pace and made deeper strokes.

After all that preparation, she was still very tight and I wasn't so sure how long I was going to last. So to distract myself from cuming too soon, I started talking trash to my newly acquired slut.

"You're mine, you hear me slut? I own you now! And just so you know, I'm going to fuck your mother just...like...this! "I proclaimed and smacked her naked ass twice so she'll know I mean business.

Hhuu...Hhuu...Hhuu...Oh fuck! Yes daddy! I'm so yours! Please own me and my mommy. Nnnggghh...she needs it too! She's a good slut also, she just needs someone like you to show her! Ooohhh! FFFUUCCKK you're fucking me so good! My pussy is on fire! Yes daddy it's your pussy whenever and wherever! Oh shitttt I'm cuming! My little clitty is making cummies for you daddy! Give me your cum daddy...please! I need you to breed me so I'll be a real girl! Ffffuuckkk!" Tiffany submitted.

When she came, her assgasm sent ripples up and down my fat cock pushing me over the edge! I bottomed out and held that position as my orgasm took over me. I felt light headed as my cum rocketed out of my pulsating cock painting Tiffany's insides with my potent seed! After about 7 ropes of my thick lumpy cum filled her to capacity, I pulled out and marked her with 3 more equally impressive ropes aimed directly at her gapping used hole. My cum was running out and down her leg as I turned her around and ordered her to clean my cock of both our juices.

She quickly got to her knees and swallowed all 10 inches of my semi hard cock, sucking me clean.

I used this time to deliver one more order.

"Tomorrow, my place, 3pm don't be late!"

She stopped what she was doing just long enough to reply.

"Yes daddy, I promise!" Then she went back to worshiping my soft cock with little adoring kisses.

To be continued!