Feminizing First Step Ch. 06

(All characters are age 18+)

Today my mom was having her friends over for a pool party in our backyard. They had been here all afternoon --mainly lounging around the secluded swimming pool and patio area. Michelle had been first to arrive. She was my mom's old roommate from university and came wearing a black bikini and floral print sarong. Next was Kendra --a beautiful Asian doctor my mom met through one her feminism-activist groups. She was also wearing a tiny black bikini that matched her jet black hair. And finally there was Brianna, another old family friend. A very Amazonian woman, she was statuesque with a short blonde pixie haircut. She wore a white one-piece that really showed off her well-toned arms and her long, muscular legs. Mom had become friends with her at the gym many years ago. Now, they went to the gym and their yoga classes together almost every day. But, Brianna did not come alone --she brought her daughter Ella.

Ella was not really her daughter. Brianna had run into the same dilemma as my mom --Brianna had really wanted a daughter but instead had an effeminate, submissive son. So as a single mom, she simply decided to feminize her son. Over a period of many years, Ella had been transformed. But based on what I saw, Ella was definitely more of an "advanced" sissy than me. In fact, Brianna may have gone a bit overboard with the feminization.

I stared at Ella as she walked around the pool. She was wearing a skimpy pink bikini with thong bottoms. She practically looked like a super model or something. All of her features had been beautifully enhanced. Her ample breasts could hardly be restrained by her string bikini top. Her lips had clearly been receiving injections. Her bleached blonde hair, belly button ring, and makeup really completed her look. And earlier in the afternoon, Brianna had shown off Ella's new ass --curtesy of some Brazilian surgeon. I was envious. I too was in a skimpy bikini --a sequined red one in fact. But I looked nothing like Ella. Her body looked so perfect. A perfect bimbo doll. She was even smooth down below --I still had a noticeable little bulge in my bikini bottom. All the ladies had been fascinated by Ella as Brianna went over the details of her feminization.

Not to be outdone, my domineering mom had also introduced me to all her friends. They knew I was her sissy son. Michelle and Kendra were particularly fascinated with me. However, Brianna was well aware of my feminization --she had been giving guidance to my mom all this time. My sissy hypnosis training, my former chastity cage, the hormone therapy --they all came from her. Brianna probably saw me as a second project after Ella.

Out by the swimming pool, the women spent the afternoon chatting and tanning. I was tasked with serving them drinks and bringing out food. I tried talking to Ella but she was very shy. Her face was expressionless most of the time --almost as if she was in a trance, just mindlessly gazing into space. I knew I looked the same way after watching too many sissy hypno videos, but it usually went away. I wondered what had happened to her. Was I becoming like her? A mindless bimbo?

It was late afternoon when the excitement started. My mom and Brianna had been talking inside the house for about ten minutes before they came back out to the patio. Both ladies were smiling, Brianna carried a large gym bag with her. They came over to where Michelle, Kendra, and Ella were sitting. I came over and stood next to their chairs.

"Ladies, I know you have enjoyed getting to know our sissies. But now I want you all to see something even better," said Brianna.

Michelle and Kendra looked at each other and smiled. Noticing their excitement, Brianna then walked over to me and put her arm gently around my waist and looked back at the awaiting women. Her fingers played with my thong's side straps.

"I have something extra-special for this sissy to wear. Something that ALL sissies should wear. But something my Ella no longer needs," confessed Brianna.

With that, she reached into her gym bag and pulled out a pair of flesh-colored latex panties. I could quickly tell that something was strange about them. Holding them up high, Brianna showed them off to the gathered women using both her hands to pull the latex garment tight. Now it was clear. There was a fake pussy built into them! Right in the crotch were tiny pink pussy lips. A cute artificial vagina. Totally hairless. I could see my mom's eyes light up.

"Those are adorable! I love them! Where the hell did you get them?" asked mom, practically licking her lips.

Brianna proudly replied, "Oh they sell them at a local sex shop in town. I had to get a pair for my sissy son as part of his transformation. But like I said, he -or rather she- no longer needs them."

"Why?" blurted out Kendra.

"Oh... you'll see why later. But first, I thought this other sissy here could use them..." replied Brianna. And with that reply, she turned towards me. In fact, all the women began looking at me. Even Ella was staring. My mom put her wine glass down and approached.

"I agree with Brianna. My sissy would look great in them." My mom put her hand on my waist and stared down at my bikini with its tiny bulge. Now she and Brianna were standing on either side of me.

"Now kitten, stop embarrassing me and pull your bikini down. Let's see how they fit on you."

"Do I have to do it now mom... in front of everyone?" I nervously asked.

"Come on. Don't be shy. Nothing we ladies have not seen before," said Brianna as she gave me a light, playful spank on my ass.

This was like déjà vu all over again...but not wanting to upset them, I pulled down my sequined bikini bottom and let it fall to my ankles. My little cock and balls sprung free and dangled in front of every one. I honestly expected more laughter at the sight of my hairless, tiny appendage, but Kendra and Michelle just giggled and whispered to each other. Brianna didn't say anything, but I could see a big grin on her face. She and my mom knelt down and pulled the tight latex briefs apart next to my feet.

"Step into them dear. We'll help you put them on," said mom.

It was only when I stepped into the outstretched leg openings did I see the surprise waiting for me. Built into the panties were two hollow, rubber tubes. One tiny one and one large one. Before I could ask, the women quickly pulled the panties up my legs --the latex squeaked as it moved into position. Before they got the flesh colored garment in place around my tiny waist, the two women repositioned themselves.

"Here, I'll get the back tube, you get the front one," said Brianna as she reached her hand into the panties.

"Ok. Right... I see how this works now," replied my mom.

In the back, Brianna slowly inserted the large hollow tube into my ass. I could feel the flexible tube slowly work its way inside me --thankfully it was only a few inches long. Meanwhile, in the front, my mother slowly inserted the tiny rubber tube into my penis --a sort of miniature catheter I suppose. I felt a little pinch as the lubricated tube slid into my penis, but the pain went away immediately and I was left with a strange tingling sensation. Satisfied that both hollow tubes were inserted into my orifices, both women pulled the latex panties up even further. They were going to be tight! When released, the panties snapped loudly into place around my groin. The flesh colored material was thin and contoured perfectly to my petite body. The color tone was a near match as well. When I looked down, my hormone-shrunken sissy clit was gone --replaced by an artificial pussy with its own clit. My heart began to race. I finally had a pussy! Something the sissy hypnosis tapes kept conditioning me to want and desire...

The two women stepped back to admire their work. I could tell from their faces, both seemed very pleased with their handiwork.

"Wow! They fit perfectly on him!" said Brianna. She crossed her arms and nodded with satisfaction.

My mom agreed. "Yes they do. Finally, his gross boy parts are gone. In seconds, they accomplished more than months of this onerous hormone therapy. Should have done this sooner. But you live and learn."

Kendra mockingly asked me, "Aren't you happy to finally have a pussy? Now you're just like us!"

"Uh... yes Miss Kendra, it's just...how long do I have to wear them mommy?" I asked.

Mom turned to Brianna with an inquisitive look on her face. Brianna understood and replied, "He can really wear them for days. He can satisfy all his bodily functions while wearing them. Well...apart from one." She made a jerking motion with her hand. The ladies laughed. Little did they know that I couldn't really do that anymore anyways.

"For days? Really?" asked mom.

"Yeah! You will have to take them off every now and then and do a thorough cleaning. When Ella wore them full-time, I would let her shower in the mornings without them. It's no big deal. Your sissy's clit is impotent, right?"

"Yes of course."

Brianna continued, "Perfect! Then no worries. It's really that simple. The tube in the back allows your sissy's ass to be open and available at all times...if you know what I mean. The panties will not get in the way of a good ass fucking."

"Ha! That's a relief! Did you hear that girls?" asked mom as she turned towards Michelle and Kendra.

"Delicious!" said Michelle.

As the ladies continued to talk, my hands had begun to explore my new predicament. The latex felt cold to the touch. I could barely feel my cock under all the compression. The new pussy looked so real! I couldn't help but stare down at it in fascination. My first pussy. Part of me hadn't wanted to resist putting these on. Part of me wanted to have a pussy. And now I did... in a way...

With the demonstration over for now, the party resumed. I wasn't allowed to put my bikini bottom back on, so I spent the rest of day wearing just my red bikini top.

From a distance, I was seemingly naked from the waist down as I served the women at the party. I got drinks, hors d'oeuvres... anything they wanted. As I walked around, many wanted to have a closer look at my new vagina. Michelle got a kick out of sticking her fingers in it. In no time at all, the panties felt like they were a part of me. Almost like a second skin. Deep down, a piece of me never wanted to take them off. Something just felt right.

After a few more hours by the pool, I thought the party was about to be over. Turns out, it was just getting started.

I was sitting in a wooden Adirondack chair, adjusting to the new intruder in my ass when I noticed Brianna get up from her beach towel. Motioning towards the women, Brianna said, "It's getting late... I think it's about time... gather around girls, my darling Ella has something to show you all. A little sissy surprise before the night festivities begin!"

The other women started gathering by the patio chairs. They made themselves comfortable on the cushioned seats and poured themselves more drinks. I knelt next to my mother's chair as directed by her, eager to see what Ella had to show us. I knelt on a towel so the concrete wasn't too painful on my knees. Again, I felt something shift in my panties and tried to discreetly readjust them. But no luck.

The show was starting. Brianna took Ella by her hand and had her stand in front of the semi-circle of chairs and waiting ladies. Satisfied that her sissy son was now the centerpiece of the party, Brianna sat down herself and grabbed a glass of champagne. Ella stood before us in her glimmering pink bikini and nervously played with a strand of her blonde hair. I was falling in love. She really was beautiful. Her plastic surgeon was very gifted.

"Now you girls know that my daughter has been a bit of a "project" for me. I mentioned some cosmetic surgeries before... but I have something else to show you! Something I know you will appreciate," bragged Brianna.

Looking back at Ella, Brianna pointed to her daughter's tiny bikini bottom and dropped her finger, motioning towards the ground.

Ella was well trained. She dutifully obeyed this command, and with her thumbs prying at the bands of her thong, she leaned down and pulled her tiny garment down to her feet. She kicked the pink thong to the side and remained standing in front us with her hands at her hips and legs spread shoulder width apart.

I gasped at the sight of her. She was just like me! Or really... a more "enhanced" version of me. Her little sissy clit was on full display. I almost "oohed" and "aahed" like the other ladies. Ella playfully smiled back, unashamed at her nudity --almost taking pride in it.

Her cock was just a little nub. I had never seen one so tiny! She was even smaller than me. But something was off...something was missing. Wait! Where were her testicles? I wasn't the only one to notice this interesting development...

"Oh my god! What a sight! I would never have guessed!" Michelle blurted out.

"I suspected something. But still...oh my god!" agreed my mom.

"But where are her balls?" asked a clearly stunned Kendra.

Ella's mom made a snipping motion with her fingers. Some of the women started giggling, others clapped.

"No way! Really!?" cried Kendra.

Brianna, with a mischievous smile, replied, "Absolutely. I had her castrated last year."

"At the same time you had her butt implants done?" asked Michelle.

"No. No. A different time. I had castrated at home actually. It really was not a huge procedure or anything. In fact, we just used local anesthetics... I wanted her awake for the whole thing."

"I'm sure you had your reasons Brianna. But still... why?" asked Michelle again.

"I just got tired of the endless hormones and injections and pills. It was never ending. This makes life so much simpler for her and for me. Just a little snip and she is my ball-less sissy forever. Should have done it years ago. And I really should have invited you over to watch. It was a beautiful ceremony. Just me and the nurse and Ella," Brianna proudly stated.

"I wish I had been there. But I agree. Ella is so much better off without them. She looks adorable. Right Ella?" teased Kendra.

"Yes Miss Kendra. My sissy clit looks so much better without those gross boy parts," replied Ella. Ella then shifted her stance, causing her surgically enhanced butt to jiggle ever so slightly.

Brianna looked at Ella and proudly added, "See, that's a good girl! Mommy's castrated sissy. And I have more in store for you..."

I was watching in a mix of envy and fear. Part of me was envious of Ella. Deep down in me, something yearned to be just like her. My cock getting hard in its confines. I could feel my little nub straining against the latex. Did I want to be castrated too? My heart was racing. I nervously swallowed and tried to calm my breathing. But my mother had noticed me practically panting at the sight of Ella. She couldn't resist letting everyone know.

"My kitten is getting all hot and bothered! I guess she is having penis envy!" she blurted out.

All the women laughed. My face must have been bright red. Even Ella was giggling!

Brianna then said, "Are you planning to have her "fixed" soon? If so, I can recommend an excellent nurse practitioner from the city..."

"I honestly had never really considered it till now. I mean... maybe? I don't know. My sissy son has made so much progress from where he started..."

"Oh come on! Just do it! I should have done it years ago. Trust me, you won't regret it."

My mom relented, "You're probably right. Tell you what, I'll text you later about this. Okay?"

Brianna nodded in approval and took a sip of her champagne. I knelt there silently, wondering what was in store for me and my poor sissy balls. The other women were busy refreshing their drinks, but I could tell they still had questions about Ella.

Michelle playfully raised her hand and looked over at Brianna and said, "I have a question, Brianna"

"Ask away dear," Brianna replied.

"Can she still cum? Like a boy?"

"Great question! Ella, can you still have boy orgasms?" Brianna mockingly asked Ella.

"Yes mommy. I can still have boy orgasms. But...but I prefer my sissygasms."

Michelle didn't miss a beat and asked, "And what are those exactly?"

Brianna replied, "She means orgasms but with her ass. Analgasms I guess? Doesn't matter. Ella has been trained to only cum with her ass. Using dildos, real cocks, buttplugs... no preference."

"Really? That sounds hot! I bet she does enjoy a good ass fucking!" added Michelle.

"Does she ever! Seriously, it's a bit of a problem. I may have gone a bit overboard with the sissy hypno videos and mental conditioning. Ella can be a horny little slut."

Ella was nodding in agreement! She wasn't embarrassed at all.

Brianna continued, "But like Ella said, she can still cum like a boy. But I honestly can't remember the last time... I think we tried it once shortly after she was 'snipped'. I wanted to see what would happen. It took a while but she eventually did a little squirt for mommy."

My mom was now curious and asked, "What did that look like?"

"Well, it's kind of hard to explain..." Brianna looked up, trying to find the right words, but when she glanced back down, her eyes landed on me and lit up. Brianna smiled and clasped her hands together.

"I think Ella can demonstrate for us right now," she said. "But first, I think she will need a little helper."

Brianna gave my mom a look. The next second, I found both of them staring at me. Their minds had been made up. The women worked quickly. In no time, Ella was sitting in one of the patio chairs, legs spread wide and tied to the chair legs. I found myself kneeling on the ground in front of her --her tiny cock right in my face. Around us sissies stood Michelle, Kendra, Brianna, and my mom.

"I must confess my sissy son is a bit of a blowjob virgin," said my mom.

"What a coincidence! So is my mine! Unfortunately for him, he was still a virgin when I had him castrated... but oh well!" confessed Brianna.

"Mind if I film this?" asked Michelle. She was already reaching for her phone.

"Go right ahead," said Brianna. "Just remember to send me a copy. Something for the scrapbook."

With my face between Ella's outstretched legs, I could see her cock up close. A tiny pink scar was visible where her scrotum once was. I was breathing heavily. Her perfume was intoxicating. Something else was making me salivate. This would be my first blowjob --something I never knew I wanted... until recently. Reinforcing images from the sissy hypnosis tapes and videos began to flood my mind. Something began to pulsate in my latex panties. The urge was too strong. I wanted this more than anything.

Tired of me delaying, someone put a hand on the back of my head, pushed me forward, and yelled, "What are you waiting for!? Suck it sissy slut!"

Moving forward, I opened my mouth and took in all of Ella's miniature cock. It was only five centimeters or so in length. And it was only semi-hard but I didn't care. It was more like an erect nipple than a cock, but it made no difference to me. I was in subspace. Bobbing my head back and forth, I could hardly notice the photos being taken or the words of encouragement from my audience. My tongue lashed out around the tiny cock head, swirling back and forth. I looked up at Ella at one point --she was gazing right back in complete ecstasy. She was losing her virginity too. This thought snapped me back to the real world and I could hear the women talking.

"She's a natural!"

"More like a bitch in heat."

"Definitely has a real talent for it. I could put her to good use at the club..."

"Yes! I should introduce her to some of my special friends."

Without bothering to look around, I remained fixated on my task. I began to taste precum in my mouth --delicious! This caused me to salivate even more. I was practically drooling all over the place. I didn't want to stop. And after about a minute more, I began to notice a change. Ella began to moan and tense up in the chair --pulling against her leg restraints. Her cock became stiff in my mouth. I couldn't stop now... I wanted more.