Born Sub Sissy

A neighborhood boy becomes owned by a Couple. Told by wife/Owner.

Timmy lived a few doors down. He was a small boy, very well mannered, shy and quiet. He rode the bus to school with our daughters, and was in many of their same classes thru high school.

Our home was an old estate house, built in the mid 1800's. Timmy began mowing our lawn. As time went by, he took on our household jobs, cleaning the house, inside and out, plus landscaping; it was a full time job.

At 18, our girls went away to college, but Timmy decided to stay at home. He fixed up our old carriage house, and he moved onto our property. His parents moved away, to take care of their parents, so we were his only family.

We traveled frequently, so Timmy played a necessary role as our property Caretaker. We actually put him on our payroll. In addition to the day to day tasks, like bringing in the mail, he kept the house, the pool, and yard, spotless.

He always answered, "Yes Ma'am, Yes Sir," rarely making eye contact, well mannered, but introverted.

When our twin daughters were home, he answered them, "Yes Maggie, Yes Hanna," preferring subordination to them as well.

At every chance, he stole glances at our gorgeous twins, but I also caught him stealing glances at me.

We returned from a trip, and I noticed my lingerie drawer was not exactly as I kept it. I figured Timmy was doing some harmless "investigating", but started keeping an eye on my "intimates".

Both my daughters had mentioned they seemed to be missing panties.

Then I found a panty with cum stains, (or at least precum). It was as if he wanted to get caught. The next day, while he was out, I went into his room. One drawer contained some our panties and lingerie, and a few dildos. I checked his computer history, which he left conspicuously easy to access.

There it was, his entire sexual identity, laid out for me to see. I invited my Hubby Rex to see as well.

Timmy was a total submissive. His browser was full of stories of teen boys being subjugated and owned by a Couple. And many stories of being feminized and trained sex slaves.

We even found a blog, where he laid out his every desire to serve us, and our Daughters.

Rex fucked me with purpose that night. After he came, he smiled, "Perhaps next time we have Timmy lick us clean."

It was early Spring, but a warm, sunny day, and I decided to sunbath. Wearing my tiniest, "come-fuck-me" bikini, and high heels, I strolled out to the pool. My bikini was thin material, and barely covered my (denuded) pussy. I had oiled my body, and the sheer bikini stuck to me like a second skin. The top barely covered my areolas, and my nipples poked thru the sheer material.

I asked him to join me at our pool, and "ordered" him to put suntan lotion on me, "Start at my feet," I instructed.

His mouth was agape, and his eyes wide. He couldn't take his eyes off my body.

He slowly kneeled at my feet. Enjoying the tease in my hot-wife attire, I laid it out, "Timmy, I've seen your computer history. I know you want to be our slave."

He slowed massaging my feet, looking at them intently, and nodded, almost imperceptibly. He was squirming with anticipation.

I thought to myself, "He set this all up. He's willing to risk it; he's fired, or we accept him as our slave."

I asked, "Are you wearing panties under your shorts?"

Yes Ma'am," he answered quietly.

"Show me!"

He stood and off came his top, then down came his shorts, revealing pink panties. Timmy stood before me, naked except for a pair of my daughter's tiny thong panties. He was not hard, and the panties contained his "boy-bump" nicely.

"Put your hands behind your head," I ordered, "On your knees, and tell me everything."

His emotions spewed forth, "I have wanted to serve you and your family for as long as I can remember. It's as if I was born to serve you. My fantasies are exclusively of you and the twins. I am already your slave! Please take me as your slave. I'll do anything, and I'll remain your slave forever!"

He was on his knees, and I held his sexual future in my hand. "Back to my feet," I said, and he kneeled and caressed them, and massaged and kissed them while I pondered my next move.

I asked, "Have you been with a woman yet?"

"No Ma'am."

"Take off your panties," I ordered.

He had just a tuft of pubic hair. I ordered, "Go get a razor and cream...and don't touch your cock!"

Moments later, he stood before me, out by the pool, shaving his pubes. "Now your underarms and legs," I ordered.

As he shaved, I noticed his cock was medium sized, but his balls were tiny. (All the better for wearing panties, I thought).

I imposed, "I expect you to be shaved at all times."

"Yes Mistress," he answered, which I liked; his "Mistress".

"You understand, Rex already knows everything. You will be his slave as well."

"Yes Mistress."

"As for Maggie and Hanna, You desire to be completely submissive to them as well?"

"Yes Mistress."

"I'll see how they feel about it. For now, Rex and me only."

"Yes Mistress."

"Follow me." We walked into the house, and into Rex's office. Rex smiled when I walked in, my daughter's panties dangling from my finger, and Timmy, shaved and naked, mincing in behind me.

I put my hands on my hips, "Back on your knees. I want you to stroke yourself, but don't cum. Now, tell us everything while you stroke yourself."

He gushed, "From my earliest memories, I knew I was submissive. When I first met you and the twins, I looked no further. I was first attracted to the twins, when we were just kids, and eventually even more attracted to you. I have never even thought about any women except you and the twins."

Rex smiled, and motioned me to sit on his lap.

I sat with my back to Rex, and facing Timmy, kneeling before us,

Rex's hand traced to my crotch, and I spread, and he stroked my pussy thru my bikini.

Timmy's eyes went wide when I spread, as Rex stroked thru my thin bikini. His other hand teased my hard nipples thru my bikini top.

Rex spoke, "Is this what you had in mind?"

Timmy answered, "Yes Master."

"You understand you'll serve me too?"

"Yes Master."

I stood up and Rex slid off his shorts, then he slid down my bikini, and Timmy's eyes went wide. Rex pulled me back to his lap and said to Timmy, "Get me hard."

I brought my feet up and placed them on either side of Rex's thighs; my pussy wide open.

Timmy was already on his knees, and crawled and took Rex's cock into his mouth, his eyes on my shaved, gaping pussy, just above.

Rex asked, "Is that your first cock?" Timmy nodded while he sucked.

"That's enough. Slide my cock into her pussy," said Rex, and Timmy put his hand on Rex's cock, and slid the head up and down my pussy, and then slid the head into my dripping pussy.

Sitting on his lap, I worked my hips on Rex's cock, while Timmy watched, totally enthralled. I ordered Timmy, "Lick my pussy."

He dove in! He put his hands on the sides of the chair, and licked. When he found my clit I said, "Right there. Keep your tongue working right there!"

Rex was still, and I slowed my rocking, and just enjoyed Timmy, as he feverishly worked his tongue over my clit. No one had tongued my clit like this; it was divine! I laid back and just let it go on and on! I loved the sensation, having a cock inside, and a tongue on my clit!

Timmy worked and worked; his tongue clearly was exhausted, but he intensely worked his head in short jerks, which was even better! I'd not cum from oral in years, but it was immanent.

I said to Rex, "I'm about to cum!" "Me too," he replied.

I grabbed Timmy's head and crushed him into my clit and held him tight as I shuttered into a massive orgasm, which caused Rex to blow his load into my pussy. I eased Timmy's head away, and he remained quiet and still, as Rex and I drifted into afterglow. I relaxed, releasing Timmy's head, and he remained still, just inches away from the cock and pussy that now owned him.

In a few moments, Rex's softened cock slid out of my pussy, and I merely looked at Timmy, and he opened his mouth, and began tonguing Rex's cock, then taking it all into his mouth, licking his balls, and making sure his Master was clean.

Then, with no instruction, he started on me. I slid forward and Timmy licked Rex's cum as it flowed from my pussy.

I inquired, "I read on your blog that you wish to be feminized. Would you like us to help you?"

"Oh, yes Mistress!"

"I saw in your blog, your femmy name. Say it. Say your femmy name."

He blurted, "Tammy! I want you to call me Tammy!"

I slid forward a bit more, "Straddle me, and cum on my pussy, and be prepared to lick it off."

Timmy/Tammy was up in a flash, stroking his/her rock hard cock. It was spewing precum. I put a dollop on my finger, and stroked his anus/pussy. His eyes closed and he literally swooned.

"We'll be allowing you to cum frequently, but you will NEVER masturbate without permission. You will always ask permission, and often, you will do it in front of me or Rex. Understood?"

"Yes Mistress. Yes Master!"

I stroked his hole, "And this will be your sissy pussy?"

"Oh, Yes Mistress!"

And then he came, squealing little femmy chirps, he shot spurt after spurt as I stroked his sensitive sissy pussy. His cum was hot on my body, from my pussy to my breasts.

Timmy almost collapsed, sliding to his knees, his head fell in my lap. It was a tender moment. Years of energy had been released. We all were quiet, and I stroked his hair.

I asked, "Have you swallowed your cum before?"

He replied, "I've only tasted it, but I have always dreamed you'd force me. If I ever became your slave for real, I knew I'd always lick up my cum."

I smiled, and he began licking with enthusiasm.

As he licked, I said, "Remember, we'll allow you to cum often, but you always must ask first. Also, your apartment will be fitted with cameras, so we can observe you any time we want."

I continued, "For the time being, if you are wearing male clothes, we'll address you as Timmi, female clothes, it's Tammy."

As he finished licking, I said, "Let's get showered, then I have the perfect little bra and panty for you."

Rex was in and out of the shower quickly, while I let Timmi soap me up and wash my entire body. I sat on the shower seat and he kneeled before me and literally worshiped my breasts and nipples. Aside from his head, Timmy was 100% hairless when we exited the shower.

I put on a bra and panties, and dressed him (her) in and old pink "starter" bra of the girls, and tiny pink panties. He sat on my makeup stool, and I began his transformation. His neck was naturally long, with no adams apple. I styled his thick, longish hair, combed and held back with plenty of product. Then I painted his hand and toe nails a matching pink.

I thinned his eyebrows, and started with makeup. His skin was exquisite; makeup was an easy task. His eyes looked like a model. With highlighted cheeks, and glossy pink lipstick, and he was beautiful young girl. Last were pink high heels; they'd been too big for me, but fit Timmi perfectly.

Timmi was transfixed by my breasts and bra, as they were so close; he could simply lean and kiss them. He knew better, of course. I smiled to myself, he'd just cum, and worshipped my breasts in the shower, but he was an insatiable teen. His cock thickened in his panties. For the first time in his life, he was realizing his feminization fantasy, and typical man, he was entirely focused on my breasts.

Finally, I pulled down my bra and he locked onto my nipple. I let him suck a moment, and then said, "Come with me."

I laid him in our bed, on his back, and straddled him. His cock was rock hard, and I slid him into my pussy. He was no longer a virgin. Having cum an hour ago, I hoped he'd last a few minutes. He played with my breasts while I rocked on his cock. He was not as big as Rex, but quite enjoyable.

I had not fucked another besides Rex in many years, and here I was, looking down at his feminized, made up face, fucking a sissified teen, who was getting ready to cum inside me. I moved up onto his face, "Lick your Mistress!" I was in charge; I fucked him, he didn't fuck me. He came when, and if, I decided.

It was quite satisfying. He licked and licked, giving me a nice orgasm, and then I laid to the side. He asked, "Mistress, may I cum?"

"Straddle me. Cum on my pussy, then lick it up," I coolly replied.

His makeup was mussed, and we went back to the vanity, re-feminizing his pretty face.

The transformation was consummate; even his own family wouldn't recognize him. We strolled into Rex's office, and Rex couldn't believe his eyes. He exclaimed, "I can't believe it's you!"

"Tammy" was so cute and shy, mincing around, not quite sure what to do with her hands.

We took Tammy out for a photo session. We own a high quality, commercial grade camera. On "portrait", the shots were unbelievable!

Outside, under trees, with the sun filtering thru, Tammy posed. Hands above her head, pouting, kissing, ballet, various poses. Our "subject" was the perfect young "boy in drag", wearing the sheer starter bra and panties; some shots in heels, some bare foot.

Then we went up to our attic. The dark, dusty wood contrasted with bright skinned young girl/boy, light filtering thru the dormers, and we had magazine quality soft core porn shots. Lastly, Rex got naked, and Tammy kneeled. I took closeup shots, of Tammy's glossy lips on his cock. I kept only Rex's torso in the shots, no facial shots, which kept our privacy, (and all the focus on sissy Tammy).

We took various shots of Tammy serving her Master's cock, with the spooky attic background, the effect was dramatic! (I made a mental note to order a collar for Tammy). Finally, Tammy sat back on her haunches, mouth open, as Rex jerked his load onto her face.

Afterward, Rex took shots of my torso, standing in my bra and panties, feeding her Rex's cum with my finger. I pondered some bondage shots in the attic, but that would have to wait.

We downloaded the photos, and the best shots went on the internet. As expected, Tammy has many fans.

I texted Hanna, "Timmi" is easing out of closet, so to speak."

She replied, "He's gay? He's never been able to keep his eyes off me and Mag."

"Not gay," I replied. "I'd characterize him as a submissive sissy."

"OK. That's what we figured. How'd he come out?"

"I simply confronted him, and it gushed out of him. He's been obsessed with us for a long time. Would you like to see a photo?"

"Sure."

I sent a fairly tame shot from our recent photo session.

"Oh Wow! What a doll-baby he is! He's a cuter girl than boy!"

I replied, "Didn't want you to be shocked when you get home. I'll tell him you girls already know about him. We're having him set up cameras in his apartment. We'll be able to observe him any time."

"Send us the access code! Can we watch too?"

I replied, "Ok, but be discrete."

She replied, "OK. See you in a few weeks. Love you."

Tammy's sex was on overdrive; (we knew it would be). We wanted this to be a positive experience. Tammy frequently texted, "May I?" And we always granted permission, watching on the cameras, as he/she laid back, wearing a dainty camisole, working a dildo in her "pussy", and another in her (lipsticked) mouth, and lasting only seconds before blowing. Always onto a plate which she licked clean.

Tammy was thrilled about openly dressing femmy. She quickly learned how to apply makeup. She essentially lived full time in femmy mode.

Sometimes she'd be cleaning the kitchen in heels, and a bra and panty only, and I'd be nearby, and her sexuality literally engulfed the moment, to where she'd just drop to her knees and exclaim, "Mistress, Please, may I cum!"

I smiled, "Of course Dear." I sat and said, "Kneel at my feet." Wearing only her bra and heels, Tammy kneeled before me. I sat and spread my legs, revealing that I wore no panties.

Tammy's eyes lit up, "Please Mistress, may I kiss your pussy. I love your beautiful pussy!"

It felt so regal, looking down at my little fem-boy as she worshiped me, stroking her cock.

"Look at me as you cum Tammy," and with half-lid eyes, she came with unbridled passion. On a typical day, Tammy enjoyed these orgasms three or four times daily; a privilege reserved only for youth.

When the girls came home from school, they'd seen Timmi, (that's how they spelled it), experimenting with femmy-dress, (and seen him masturbate with a dildo in his rear), and they were in full support.

They hung out in Timmi's space, playing dress-up, all three in bras and panties, which always made Timmi hard, and they playfully teased her "big, hard, clitty".

They all slept together, where, best we could tell, Timmi fucked one twin, then in only minutes of recovery time, he'd fuck the other. (Dark, and under covers, we couldn't be sure). All satiated, they'd sleep for hours and hours, entwined like kittens, and have sex again when they awoke.

We didn't want to pry, but the few times Rex and I checked the cameras, it got us going, and our sex life also got a nice boost. Timmi/Tammy remained our femmy sub-maid/caretaker, but Rex and I suspended sex with Tammy when the girls were in town.

Timmi cherished our beautiful twin daughters, and treated them like queens. The girls helped Timmy with the yard work, all three dressed in little bikinis. Sometimes they'd drop what they were working on, and disappear to Timmy's apartment for a while.

The next semester approached, and they made plans to get together often as they could, but Timmi was sad. The girls left, and I let him mope for a day, and then like our first day, I strolled out to the pool in my same bikini and heels, clinging to my pussy and breasts like a second skin, and Timmi knowingly smiled, and dropped to his knees, "Oh Mistress! You are the sexiest woman on the planet!"

As before, I coolly ordered, "Start at my feet."