A Sissy for Mom & Sister Ch. 04

Chapter 4

My female hormone treatment for my condition had finish. A few weeks later, my little ball sack stopped hurting and I started to get some little erections again, and a LOT of precum. Convinced I could prove Doctor freeman and mom wrong, convinced I could reverse all of this, I start practicing nightly, stroking my tiny, shrunken penis with a finger and thumb, with hope that it will help it to start growing again.

Why could I lay here, distracted by my video games, stroking it for hours at a time, but when someone else touches me, I would quite literally explode? Why couldn't I handle any sexual thoughts without premature ejaculating? If I had any chance whatsoever of having sex with a girl, I had to try and train myself to last longer. I feel an overwhelmingly desperate urge to be intimate with someone, but finding someone accepting to do it with, is extremely difficult.

My mind drifts off and I almost gaze through the tv, as the mental image of my sister getting pounded by that big cock, creeps it's way back into my head. I immediately squirt up my belly.

"FUCK IT. Fuck's sake." I let out, looking down at pool of clear liquid on my belly. Frustrated, I clean myself up, put an oversized t-shirt on, and walk down to the kitchen.

"Good morning, Sweetie, how are you feeling today?

"Mmmm, yeah... Mmm, fine mom," I grumble, grabbing a glass of water.

"Woah, what's up with you today? That time of month, is it?" Carly chuckles.

"You're so annoying Carly, you know I'm... Ughh," I snap.

"Carly, he's right, you know. He's a bit hormonal and sensitive at the moment. Let's ease up on the jokes, can we?" Mom says, rubbing me on the shoulder.

That isn't what I meant, but I try to give mom an authentic smile, as if to say thanks for the support. She was right, though. I had been so up and down lately. It had been weeks since I'd stopped the hormones, and just as long since mom & Carly let me be an adult again.

Was the big decision plaguing my every thought? Or was this a comedown from the high of being on the hormones? Or both? I Know mom has been waiting patiently, but she will want an answer soon.

I want to tell her there is no way I'm continuing any treatment, that I want to only dress in boy clothes, that I want to give it another shot, but it is just so damn confusing how I will actually make that physically happen. If I'm being honest, I didn't feel too bad towards the end of the hormone treatment. Now I just feel unhappy and confused all the time.

I look down at my weak, unmuscular body, and as baggy as my t-shirt is, I see the slight outline of the small amount of breast tissue I have grown. Down further, I feel the skin from my tiny nub brushing against the material of the long shirt, reminding me how pathetic, small and useless it is. It seems like an impossible task to make this work, but I have to at least try.

"Sweetie, why don't you come and sit on the couch next to me. Let's have a bit of a chat," mom says in a most comforting voice.

There it is. She wants her answer. I didn't have to wait very long at all.

I sit down next to mom, making sure the bottom of the shirt is covering my parts, and feel her hand rest gently on my thigh.

"Honey, you don't seem so happy at the moment. Is everything ok?

"Yeah, I'm.. I'm ok, mom. I've just been feeling a bit... funny sometimes," I reply.

"Aw sweetie, are you worried about making the decision on how you'll move forward? Let's not dwell on it any longer. Let's try and put this to bed so you can put your mind at ease," Mom says, kissing me on the head. "So, are you ready to make your choice to be a big boy or big...."

"BOY! Definitely boy," I say in my deepest voice. "I know you and, well, everyone else won't agree with my decision, but I am a boy, mom, and that's what I'll try my hardest to be!"

With a pained look on her face, mom says, "Ok Sweetie, what I want is for you to be happy. Carly and I will support any direction you want to take, as long as you're sure?"

"Yes, 100 percent, well... ninety... five," I reply. "Close to 100."

I see mom glance over at Carly with a grimacing look on her face, Carly shrugging her shoulders in reply.

"Ok, so it looks like we're doing this! First things first, we need to buy you some more clothes that fit. We threw out most of your clothes after your accident," Mom starts. "We're also going away on holidays soon, so you're going to need a full wardrobe. Your sister is watching a movie with her boyfriend this afternoon, so we might meet her at the department store afterwards," Mom informs.

I feel very relieved about this, like a weight has been lifted off me. Hopefully I could follow through with it!

--

Mom and I walk into the men's section of the department store and find plenty of small athletic t-shirts, shorts, jeans and the like. I grab some small men's briefs and start heading to the change room with my bundle of clothes.

"Sweetie, they are little bit..... big in the pocket at the front. Do you think?" Mom tells me, trying to be nice, but honest.

Satisfied with my haul from the men's section, I take her advice and follow her to the boys section, grabbing a few pairs from the available sizes, hanging them up in the change room, ready to try.

"That all looks good Sam, we'll get all of those shirts and shorts," Mom says, looking through the curtain. "Good Job Sammy. Can you just pull your shorts down a little, we'll just check that your underwear fits. I'm not spending money on things that don't fit, as they have a 'no returns' policy here."

I reluctantly slide the shorts down, revealing the loose briefs that almost slide down with them. I notice there is also lot of loose material in the front pouch.

"They didn't have many sizes, these aren't.... too bad, are they?" I ask.

"Sweetie, I'm not trying to embarrass you, but you do know you are very small down there. Surely you can see that they don't fit," Mom says, putting a hand down the side of the briefs to show me the loose waist band.

I frown, but nod in agreeance, removing the pair I had tried on.

"Look, you've got PLENTY of boy clothes to wear now, I'll just very quickly take you to the ladies section," Mom starts. "We'll find some plain, very neutral underwear without a pouch, ones that will fit you. No one will even know once you put all your baggy clothes over the top."

The old me would've freaked about this. As long as they're plain, I guess I can probably handle it.

"Ok, let's do it quick," I reply, and we head down to meet Carly at the ladies section.

"Hey bro, want to get matching thongs again like last time? No squirting this time hehe," Carly says in an annoying voice.

"No Carly, I mean, he can if he wants, but I think he wants more neutral underwear. Remember me asking you to ease up on the teasing?" Mom says in a supportive voice. "We'll just get some plain black panties that look similar to some of the ones he tried on in the boy's section, ok.

"We're going to support him with this Carly. I know he's worn them before, but thongs might be a bit too girly and embarrassing," Mom says, quite a bit louder than I'd like.

I see Carly roll her eyes and walk off ahead.

We all settle on the same, matching plain black panties, and some plain white cotton ones. Besides the ever-so-slight skimpy cut at the back, they look very neutral, almost boyish. The three of us try them on together this time, without anything remarkable happening, obviously buying one size down from my sisters for mine, and a larger size for mom.

Success! This feels nice, having mom so supportive of me! For some reason it feels kind of nice that we all have the same underwear, too, but I don't tell them this.

The three of us leave the store happy, heading for home to pack our new clothes for the holiday.

--

I help Carly unpack our suitcases from the cab, and onto the airport trolley. I struggle to keep up with Mom and Carly on the way to the check-in terminal. Security is pulling people aside randomly for body searches, and I worry as we get close that I'll be getting searched. I worry that it'll be just my luck to be searched, standing there in my black panties while they search me. Would they be able to tell?

We're next, and the guard calls us over.

They're just black and plain. No-one will be able to tell which section they're from, I tell myself.

"Passport please," the guard says, and with a quick check and a smile, "Have a nice holiday, I hope you get some nice weather."

Wow! After the events of the past few month's, I'm feeling quite lucky today!

It is a long flight to our tropical holiday destination. After a couple hours of flying, Carly offers me a sleeping tablet, which I take, and drift off into a deep sleep.

"Sweetie, wake up," I hear mom say, tugging at my arm. "You've been asleep for 8 hours now, and... I just noticed. Don't panic, but you've had a really small accident down there. But don't worry, it's hardly noticeable."

I look down and see a couple of tiny spots of moisture on the front of my pants. I dab my hand on there and decide I'm not too worried, it's just in my underwear, not my shorts. I should be able to hide this.

"That was lucky," Mom says with a smile. "Sweetie, just grab a fresh pair from your carry-on and get changed."

"I didn't bring any spare clothes in my carry-on, Mom. I didn't think I'd be needing it..." I reply, thinking of what I can do.

"Carly," Mom whispers. "Can you grab a spare pare of your panties from your carry-on for Sammy please? He's had a tiny accident while he was sleeping, nothing too bad though."

"Sure, but I ah.. think I only have a thong. Will he wear that?" Carly whispers looking in my direction.

With a slightly disappointed look on my face, I give her a shrug, knowing that's my only option. I'm not going to let this ruin our nice holiday. They're only clothes, it's not who I am, I tell myself. Carly hands them to me, along with her toiletry bag.

"Put the panties in there, and hold that in front of your pants. No-one should be able to see then," Carly whispers, handing me the small bag. That is probably the nicest thing she has ever done for me.

I make my way to the plane bathroom and change into Carly's black cotton thong. I've worn worse, I tell myself, pulling my pants up. I throw my slightly wet, plain black panties in the bin, and hold the front of my pants up to the drier. The two very small spots disappear.

I make my way back to the seat, just in time to order a coffee, and listen to Carly speaking of her excitement about her boyfriend coming and staying with us.

"Sam, you and I are sharing a double bed, but you have to sleep in mom's bed for a couple of nights when Brad stays, ok?"

"Yeh that's ok.... OW, FUCK!" I jump to my feet and yell.

The lady in front has jacked her chair violently back, causing my coffee to spill over my shirt, shorts and legs. I Yelp some more as it burns me slightly on my thighs.

"OW, Jesus!" I yell.

I go to sit back down and realize my shorts pocket, and shirt, have been caught on the arm rest, causing my shorts to rip from the pocket, around the side to the back, and under towards the front. My shirt also torn up the side seam.

I immediately sit down, furiously trying and pull the material together.

"Sorry," the lady in front offers, not realizing the drama she's caused.

"Mom, shit, what will I do? We're landing in 20minutes," I say in a bit of a panic. "My shorts are torn to shreds!"

"Here, use these to hold it all together until we get back to the resort, we can help you if you need," Mom says, handing me a handful of safety pins.

I busily clip them all together on my shorts, making sure there's no gaps. The shirt, a ride-off, but I'm not too worried about that.

I check out my handy work. Phew, crisis averted.

We wait patiently for everyone to get off the plane, and I walk between mom and Carly, somewhat shielding me. It's nice that they're thinking of me, protecting me.

The three of us then walk through the arrivals and jump in the resort minibus without much fuss. I spot some of our luggage being loaded into the other resort minibus, before it speeds off in front of us.

"That could've been really bad, back there," I say, relieved. "Do you think anyone saw anything?"

"It all happened so quick, Sammy. I wouldn't worry about it," Carly replies.

--

In no time, we are checked in, and Carly & I follow mom through the gate to our private villa.

"Wow, look at this place! See, that wasn't too bad honey," Mom says reassuringly.

"I Know right, that could've been much, much worst," I reply, holding my clothes together. "And now to get changed out of these rags, phew," I joke.

I walk through the villa, looking at mom's room, and see it has a large bed and a very nice bathroom. I continue into mine and Carly's shared room. It has the same bed with Carly's suitcase sitting on it.

"Oh well, at least our bed is pretty big," I let out, as I look around the room and the bathroom, trying to spot my luggage. "It's nearly big enough for three," I joke, suddenly realizing what she might make of that.

"Sammy, you are definitely in mom's bed when my boyfriend get's here! You dirty minded.. boy," Carly laughs.

"Er.. I.. I didn't really mean it like that," I say, embarrassed. That joke certainly backfired. What would I possibly do in the bed with those two anyway? I mean, I'd probably like to watch, to you know, get tips and the like.

I glance around the rest of the villa and can't seem to find my suitcase.

"Mom, have you seen.." I start to say, as I notice mom talking on the phone. She looks over in my direction.

"Yes, ok that would be good, thank you," she says. "Sam, that was the resort, there has been a mix-up and they could only find 2 suitcases out of our three to bring here. They've got someone checking now to see where yours is."

"What? Where are they checking? The airport? Or has it just been taken to the wrong villa here?" I snap.

"They're not sure sweetie; it was a bit hard to understand her accent, but from what I gather, I don't know if they saw it at the airport."

I slump down on the chair feeling like I've been broken in two.

"Hey, hey, hey, hey, let's just wait a bit before we get all upset, Sam. We're all tired, and starving, so why don't you have a nice shower while Carly and I go for a walk and bring some food back," Mom says, looking down at the shreds I used to call my clothes.

"Here, just wrap this around yourself for the time being, and stay put until we get back," Mom finishes, handing me a thin floral sarong.

I nod and tell myself: I'm not going get upset, I'm on holidays, we'll work it out. They will probably find it and all will be good. Just be positive, Sammy!

I look down and see my ripped, coffee-stained clothes fall apart as I take them off. I take my sisters thong off, get under the hot steam, and have a relaxing shower.

I guess I'll have to put the thong back on for the time being. So, after doing so, I start to wrap the thin, silky sarong around my lower half, spotting my reflection in the mirror. I can see the thong clearly through the thin material that covers my legs. I glance up towards my chest, and notice my nipples seem slightly larger and puffier than normal. Such soft, pink looking skin.

Has the shape of them changed? Or are they still growing? I decide I am probably looking too closely, but think it's probably best to keep covered up anyway.

"I'll definitely be wearing a shirt at the pool and the beach!" I say out loud to myself.

I pull the sarong off and re-wrap it, higher around my chest. It hangs just low enough to cover Carly's thong. I walk around checking out the villa for some time, and stumble upon the hot tub. Deciding to take a dip, I jump in wearing only Carlys thong, spending 20 minutes relaxing in the warm water. I run my hands around the thong, adjusting the string that is tucked tightly between by butt cheeks. I briefly think of rubbing myself to orgasm, but decide instead, to lay down and get some sun in our private courtyard instead.

I wake to a knock on the gate to our villa. how long was I asleep for? Realising I'm only wearing a thong; I quickly and loosely wrap the sarong around to cover myself. Probably only mum and Carly, I think, as I open the gate.

"Good Evening, Miss Rogers," the resort worker says in his heavy accent. I feel a strong need to correct him on this, but decide it will almost certainly be lost in translation.

"I'm sorry to inform you, your baggage hasn't been located. It didn't get put on the plane, and its location is currently unknown," the resort attendant tells me. "We are working our hardest with the airlines to find it, and will let you know as soon as we do."

I feel a sinking feeling in my stomach and am lost for words, as I try and work out some sort of plan in my head.

"Please accept this all-inclusive day spa voucher for the 3 of you. It is a full body pampering package, including a 2-hour massage each."

"Oh... Ok thank... you." I guess. I mean, I could do with a massage, I am feeling quite stressed and anxious about my luggage. I take the voucher, and walk back inside, wondering why my back feels so hot.

Not long after, Mom and Carly return with some food. I tell them about the luggage and voucher, then we try to make a plan for what I'm going to wear for the next two weeks.

"Can we go shopping in the morning for some clothes?" I ask Mom.

"We already knew about the luggage Sammy; that's why it took us so long. We looked everywhere for a clothing store, but couldn't find a single shop, other than a 7-11. There's literally nothing on this island," Carly says.

"Our best bet is the markets in 6 days' time. We also tried finding some things to repair your torn clothes, but no luck. I'm so sorry Sammy," Mom says, giving me a hug.

"Well, what are we going to do in the meantime? I'm not leaving the house in just a thong and a thin, almost see through wrap!" I bark.

"Sweetie, Carly and I know how sensitive you are at the moment, but there doesn't seem to be a lot of options here. We will go through our luggage," mom says, before I cut her off.

"NO! I am not spending two weeks wearing..." I try and say as my voice squeaks.

"Sweetie, pause for a second, let me finish. Carly and I will go through our clothes and find a couple of VERY neutral outfits between us, outfits that no one will know the difference. I'm thinking some plain linens and plain t-shirts. Surely, we will find something that you're comfortable wearing, while we sort this out," mom says, wrapping her arm around me a bit tighter.

"Just take it easy honey, we'll work it out," Mom says. "And honey, why are your shoulders red?"

"Oh, I fell asleep outside, waiting for you guys. I think I'm a little bit sunburnt," I reply, patting my back and feeling some discomfort.

I feel like my holiday is ruined and we're right back where we were months ago. Why is it so hard for me to just have a normal, boyish time?

"Here, what do you think of this?" Mom ask's, in an upbeat tone, passing me a red t-shirt from Carly's bag.

I hold it up. "No, it barely comes up to my belly button," I reply, frowning.

I try on the exercise singlet Carly hands me next.

"No! Well, It fits ok, but has a ladies brand name... I'd prefer not, but it's not a definite no," I tell them.

"Here! Beige linen shorts and a plain white t-shirt, no brands," Carly says, handing me the clothing from her and Mom's suitcases.

I try it on, she's right, it looks very neutral.

"This might actually be... ok. I don't... I don't think anyone will suspect anything, will they? I ask, trying them on in front of Mom and Carly.

The Shorts maybe a little bit tight, they're probably very tight on my sister, but a much looser fit on me. I look in the mirror and see mom's white t-shirt hanging off me.

"Ok. Ok, this will probably do for tomorrow," I tell them, with a relieved smile. "Thanks guys."

--

Later that night, I feel particularly horny and flush in the face for some reason. I see Carly has our bathroom door shut with the shower going, so I walk outside, notice mom is in the hot tub, then decide to use her shower. I wash myself for a few minutes, running my soft, soapy hands over my body.

This soap feels so nice and silky on my skin. I wonder if we can buy this brand at home? I feel a little shiver as I soap around the soft, sensitive skin on either side of my chest. I run my soapy hands down over my little penis, as I watch it disappear behind the bubbles I make.

Feeling this turned on, I would should be getting at least the start of an erection by now. Confused, I rub some more. It feels really nice, but nothing much is happening down there.

Stepping out of the shower, I glance down at something on the floor. A pair of mom's red lace thongs are laying in front of me and catch my eye. I feel another wave of horniness flood over me, and look down to see my first decent, but small erection, for a long time.

I wonder what they smell like. Why do I feel compelled to do this? Am I a sicko for wanting to do this? I slowly bring the soft material up toward my face.

"Sweetie?" I jump at the sound of mom's voice, drop the thong, and out of sheer surprise, bang my elbow on the shower screen.

"Do you need some panties?" She asks, looking down at my tiny, but firm erection.

"I... I.. was.. I just.. lo.. looking... well you gave me some clothes, but I don't really have any... any panties to wear," I studder. "That's why I was looking."

"Sweetie! You know, you are allowed to say you like them. I don't mind. It's not bad or wrong. Is it because they're nice, soft, lacey panties?" Mom asks, with her head slightly tilted. "Or is it because mommy has worn them? Or a bit of both?" Mom questions, as she stands in the doorway.

"I can see you're VERY excited, would you like to try them on?" she asks, picking them up and handing to me.

I feel so much precum building in my tiny penis. Do I lie to Mom and pretend I don't want to?

"Um.. Ok, I'll just see if they fit," is all I manage to get out, fooling no one.

I grab the soft, red thong from mum and slide it on. I see her looking down at my chest as she helps pull them up to the right spot. Embarrassed, I cover my chest slightly with my arm. The thong feels very nice, but a little big for me.

In my head, I question why I'm shielding my chest from mom, as I come to the realisation that I'm standing here, wearing her thong that she just took off. I feel a slight wet spot in the gusset touching my little bump. She must have not long taken them off. God, I'm feeling horny tonight! What will I do now though?

This is awkward, I don't want to tell her I like it, but I don't want to take them off.

"Thanks mom, goodnight," I say in a haste, putting her shirt on and walking to mine and Carly's room.

Exhausted, I climb into the large bed, wearing just moms lace thong and her t-shirt, with a little erection that is starting to subside.

I feel the bed moving some time later, and Carly climbs in, cuddling me from behind. With her perky breasts pressed into my back, she rubs a hand up and down my leg before playing with the waist of mom's thong.

"Oh, what are these, Sammy?" Carly says with a giggle, tickling the skin around the hem of the panties.

"Please, Carly. I don't really have many options right now, and I wasn't going to sleep naked next to my sister."

"So, you decided to wear this lacy number instead?" She asks, in weird tone, creeping her hand towards my tiny erection.

"OH, you're a little bit excited, aren't you? I'll tell you a little secret, Sammy. I'm incredibly horny right now, too. If only you had a proper, man-sized penis, I'd probably let you have your way with me."

I offer no answer, and struggle not to enjoy her rubbing the font of my thong, feeling some pre-cum slowly starting to soak into the material.

"Or," Carly says, gripping me by the hips. "Does little sissy want to try taking it from behind?"

My sister replaces her fingers on my small erection, with mine, guiding my hand to make circular motions. I feel her firm hand move, and grab my hip, and her body gently thrusting toward me.

I'm not answering that, partly because I don't really know what she means, but I'm so desperate to get off, so I start rubbing the firm bump in the front of my panties vigorously, while my sister slowly, sensually, sticks her tongue in my ear, holding a firm grip on me from behind.

I know what she is trying to do, but I can ignore it because I NEED to get off. I need a distraction; I need an orgasm. She is trying to desensitise me to these... things. Trying to train me for, for whatever reason. I try and block her words out, and imagine smelling the wet patch left behind in mom's panties.

My sister's other hand slides gently down to the area between her pussy and my backside. I feel her hand rubbing up and down on her pussy, while thrusting her hips toward me, making a slapping sound as she collides with my bum.

Remembering the feeling in the shower, I reach my spare hand up, starting to squeeze and pinch at my sensitive nipples. A wave of goosebumps appear on my body as I discover a new kind of pleasure. It kind of stings, but in a very enjoyable way.

I smell the unmistakable aroma of my sister's juicy pussy, and some increasingly heavy breathing from behind me.

"I'm going to.... ugh," I let out, humping my two fingers, while she humps me from behind.

"Cum for me, Sammy. Shoot your tiny little load into mom's panties," she whispers in my ear.

Tensing my legs, pointing my toes, I close my eyes and make a large wet spot in the front of mom's panties. I mix my clear, sticky fluid with the fast-drying wet-spot, created by mom earlier in the day.

I hear her breathing speed up behind me, matching the pace of her thrusting. It must be her turn now, I think to myself, instinctively arching my hips back, giving her something firm to grind against. Her strong hand pulls me very firmly into her body, as she gives a couple of last jolts towards me.

"Oh. OH. Fuck, Sammy," Carly struggles to get out. "Oh, that felt good," she whispers, her body still shaking.

Her breathing slowing down, I feel Carly's hand reach around into the front of mom's soaking panties.

"Wow, it seems like little sissy enjoyed that," she whispers in my ear.

After making a few swirling motions on my small nub, and the previous wet-spot on the panties, she slowly brings her fingers up to my lips. I hesitate at first, eventually letting her wet fingers force their way into my mouth. I notice the strong smell of what must be the sticky juices of three people, while gently licking, then sucking on my sister's fingers.

Like most guys, I had always been a little curious about how my ejaculation tasted, but I had never felt like going through with it after having an orgasm. This was slightly different. It was my mom's pussy juice, combined with my sister's, mixed with own stream of clear, sticky ejaculation. My mind drift's off into the taboo thoughts of alternating between licking my sister and my mom.

"Did you like that?" My sister's voice snaps me back to being present.

"Mmmhm, it was ok," I reply, suddenly, feeling some shame creep in.

"It's not the worst thing in the world, is it?" Carly asks.

"I don't.. I... Yeah, whatever. It's fine I guess."

"A real man's cum would be quite different though. It's a lot.." Carly trails.

"A lot what," I snap. "Some of that was "man's" cum, wasn't it?"

Carly giggles, "No, Sammy, you have a lot to learn. You're cute when you're naïve, but a real man's cum is a pearly white, thick and potent paste. Not your clear, watery, prostate fluid hehe."

"Huh, what do you mean? I know I am pretty... small down there, but I c.... cum the same as normal guys! Don't I?" I tell her, somewhat confused. "Are you just being mean? Or do you know this for a fact?"

"I'm not TRYING to be mean, Sam, I just thought you should know. I've had my fair share of cum, and it doesn't look anything like that. You do know the clear stuff isn't sperm, right? It's just clear prostate fluid," Carly informs. "The sperm is the white stuff that comes from... properly developed testes. Yours is more like a little bit of lubricant the helps it on it's way.

"But don't worry, it will still feel nice for you! My pussy is the same, I get really excited, then it gets nice and wet with a clear, sticky liquid. Everything just feels nice when you're excited and wet," Carly finishes.

Embarrassed, I feel my mind start to race. Why had no one told me this before? Is that why my ex-girlfriend, Jenny, was so disappointed when I 'came' like that on the outside of her pussy, twice! What did a man's cum look like in real life? Is it really so different?

I found myself intrigued with thoughts about what it looked, smelled, felt, and I guess... probably tasted like.

"I.. I had no idea," I stutter. "I thought it all came from... my balls. What's the prostate? I've heard mom and Dr Freeman talk about it."

"Oh, it's ok, Sammy. You're so very naïve and inexperienced, it's kind of cute. I'm MORE than happy to help if you want to learn. So, anyway, it's a little gland that's conveniently about a finger length inside your anal canal, and it can be the source of IMMENSE pleasure, and orgasm's for people with an open mind," Carly says, sliding a moist finger between my bum cheeks.

"Oh, it's ok. I don't...." I trail, feeling her finger slide inside my clenched opening.

"Just relax, Sammy. You've done this before, you know, without realising how it works. Let me show you." Carly says, sliding another finger inside me.

She must be talking about the milking we had to do. Was that just an orgasm? Why didn't they explain it to me then?

"Do you feel where I'm pressing, right.... There," Carly says.

"Oh. Mmm. Yeah," I manage to mumble in reply.

"Just take in some big breath's and try to relax. Breathe, exhale, then relax," she tells me, rubbing her fingers firmly, towards the front of my belly.

Instantly, I feel myself dripping into mom's panties again. Slightly at first, then more and more, as I relax onto her heavenly fingers.

"Oh. Oh, that's... I think that's it. Right there. I can feel it!" I whisper. "Oh, Carly. That's... That's... OHHHH."

I feel the insides of my body clench and spasm around her thrusting fingers. My hips involuntarily pushing back for more pressure. Moaning and whimpering through an intense orgasm, I flood the inside of my mom's red, lacey thong with my sticky, almost girly liquid.

After a few moments, I regain my senses, grabbing her hand to signal that I'm all done.

"So, you liked that, did you?" Carly giggles.

"Is it bad that I kind of liked it?" I say sheepishly. "It felt.... pretty good."

"Only pretty good?" Carly replies, kind of sarcastically.

"Well, ok, I admit, I liked it a fair bit. What did you do differently from when mom massaged me?" I ask.

"Oh, not much at all, Sammy. I think the difference was, you relaxed and had an open mind, allowing you to enjoy it. Pretty much what mom and I have been trying to get you to do all along," Carly exclaims.

"It makes that big of a difference?" I ask. "I felt like a wave of pleasure swept over my body, I couldn't breath at one point."

"Was is it THAT good? Have you ever heard of pegging? Or strapon sex?" Carly asks, with a giggle

"No! Wait, is that where you tie someone up and tease them, you know, sexually?"

"HA! Are you serious? You really are clueless when it comes to all of this, aren't you Sammy? Oh my god, you're a noob," Carly says, shaking her head. "It's getting late, I'll tell you another day. Brad is coming tomorrow night, let's get some rest."

"Can you please tell me what it is?" I ask.

"NO, Sam."

"Please, Carly? I'd like to know," I beg.

"Oh, I have a feeling you'll find out soon enough, ha. Go to sleep Sammy!"

My mind halfway between asleep and awake, I wonder what it could possibly be. Carly gently strokes my sensitive nipples, while I snuggle my back into her body, eventually drifting off to sleep.

"Rise and shine everyone," Mom says. "We're heading down for a day at the pool, quickly get ready and let's go!" she says excitedly.

I bounce out of bed and realise I'm still wearing mom's white t-shirt and thong. I think about asking her for a new pair of panties, but after our interaction in the bathroom, decide to avoid the embarrassment, and put my sister's linen shorts on over the top. I look in the mirror with some confidence, taking in my neutral-looking outfit.

It looks fine, I tell myself, adjusting the back of the thong slightly, before making my way to the pool.

There are only a few people about, how good! Mom finds us a nice spot, lays down on a day bed, while Carly and I run and jump in the water. We splash, play around, and chat in the deep end for some time.

"Carly, can I ask you something? Are you and mom actually supportive of me trying to... you know, get back to being normal, like a normal guy and stuff?"

"Oh, gee. I um.. Look, we'll support you whichever way you want to go, but.." Carly says.

"But what? Tell me please," I beg.

"It's just... We're not sure that you're equipped, or naturally suited to that, I guess. We're worried that you're trying to be something you're not, because you think society wants everything to be 'black and white'. If we get a bit pushy, it's because we're just trying to show you there's another way. That there are shades of grey, and a lot of other colours in between black and white. But hey, they're just our opinions." Carly says honestly.

I float in silence as it takes a few moments to let that sink in. I find myself lost in thought. Lost, thinking of how I could make this work. Am I just a pathetic joke to everyone?

"Helloooo, earth to Sammy!" Carly says, snapping me out of my trance. "Can we talk about this later maybe? I think mom is waving us in to put some sunblock on.

As I walk out of the pool, I notice it is starting to get busy with people. I stand out of the way of their way, next to a wall of tinted glass, waiting for Carly to follow.

"What a view," I yell in Carly's direction, pointing across to the beach. I look over towards Mom's daybed to show her, but notice that she has sat up and is now waving vigorously at me to come over.

"What's up with her?" Carly asks, noticing mom's body language. "She looks angry or something."

Something was up, so I quickly look around to see what the problem could be.

"I don't know, what's she doing?" I reply, quickly walking over to see what's going on.

"Sammy," Mom starts. "Would you like to lay down next to me and put a towel on? Just... Just cover yourself up a bit, could you?" She asks.

"Yeah sure, what's up mom?" I reply, confused.

"I don't want you to freak out honey, but there are a lot of guys in the gym looking at you from behind that glass," Mom says, handing me the towel.

I squint to try and see beyond the dark tinted glass. I feel a little day-blind, but after refocussing, I see a heap of guys in there. They're looking this way, all laughing a making crude gestures.

"What are they doing mom?" Carly inquires.

"Sammy, your shirt... Your shorts... They've gone a bit.. transparent in the water, honey," mom says in an alarmed tone.

I look down and see that the water has made the thin, white t-shirt, stick very tightly to my body. I can clearly see the puffy pink color of my nipples, the slightly raised shape of them, and a very small shadow below them.

Shocked, I look down further and see the bright red lace of the thong, sitting up on my hip on one side, and rolled over the top of my shorts on the other.

My face instantly turns beetroot red. I hastily grab a towel and wrap it around my whole body, jumping on the daybed between mom and Carly to hide.

"CARLY! Why didn't you say something!" I yell; Tears almost welling in my eyes.

"Sorry, Sam, I couldn't really tell from in the water, I only kind of noticed your clothes as mom called us over," Carly says sympathetically. "I didn't even see those guys."

I feel a couple of tears running down my cheeks from sheer embarrassment.

"Sweetie, it's done now. Let's just... We'll let them leave, then we'll go back to the villa, and we'll all relax in the hot tub," Mom says. "I do think we might need to have a little chat about your body though,"

"What do you mean?" I ask, looking down at the towel.

"Well sweetie, you know the hormone treatment has caused your body to go through some changes over the past few months. It seemed like it was a gradual change over time."

"YES, I'm VERY aware of those changes. How could I not be?" I bark back.

"Well, it looks like they're starting to speed up a bit honey."

"But I have stopped the treatment now, shouldn't I go back to how I was? I'm even starting to get some little... erections again," I lean in and whisper.

"So I've noticed sweetie.... Although you may have stopped, they've triggered something in your body. Have you wondered why you've been forming little breasts and larger, more sensitive nipples lately honey?"

"Um.. Y.. yeah, a little bit," I reply.

"Everyone's body reacts differently, but it seems the hormones you took, have finally triggered puberty for you, where your body now produces its own hormones to keep that process going," Mom explains.

"What...?" I say, confused, shocked. "I've stopped though Mommy. It should all be stopping. I don't want it to keep going!"

"Now I know at 20 years old, it is not the type of puberty development you were wanting, but it is a puberty nonetheless. Sam, you might be finally growing up!" Mom says with almost an air of accomplishment in her voice.

"But I don't understand. Why is my body doing this? I don't want this. Why me?" Wiping a tear from my cheek.

"Sweetie, the doctor said that your hormone levels were already quite high to begin with remember? I know we tried the other way, but it just didn't work. It was a disaster really," Mom explains. "When you started the estrogen injections into your little... balls, the doctor thinks it's possible, that it could have raised them up past the point of no return.

"The doctor told me all of this a couple of weeks ago, that's why we booked this holiday, to try and let you down easy. Relax, have a good time, and get your mind off it," Mom says squeezing my shoulder.

"No, the doctor is wrong, the hormone levels are wrong. I'm a boy and a I feel like a boy," I sob. "It's my body, and I know some things are growing, but I think it'll stop, they'll go back to how they were. I think they're wrong. It HAS to go back to how it was."

"That's fine sweetie, you can exist and be however you like. I am just telling you what the doctor said. Look, there's always a chance he could be wrong, I suppose, but I just want you to be informed and happy. We will support you as much as we can. However, you should really put some thought into it, keeping an open mind. There's no judgment here.

"But for the time being, Carly and I both think you need to cover up a bit more. I think it's a bit too obvious for you to walk around in just a t-shirt, especially a wet one," Mom says sympathetically. "I think we probably need to get you in some little crop tops like your sister used to wear, when she was starting to grow breasts. You don't want guys easily seeing the shape of your little boobs and nipples, do you?" mom asks.

I give an upset nod. As much as I want to fight this, deep down I know she is right about that part. But the rest of it, that's a different story.

"Let's leave it there and we'll walk back to the villa," Mom says.

I walk back dazed and confused, with so many thoughts rolling around in my head. What can I do about this? Is there nothing I can do? Almost every part of my body wants to fight this, but there is a very small part that thinks, would life just be easier if I gave in? Would I be less conflicted if I just did what everyone is suggesting?

"Have your shower sweetie, I've found another shirt and a pair of more comfortable panties for you to sleep in. You can sleep in my bed tonight if you like," mom says quietly. "I think Carly's boyfriend has a late flight over, and anyway, I think you could do with a cuddle."

I offer no words and drift through the shower, getting dressed in mommy's clothes after.

"Sweetie, I really do feel for you. We'll call in the morning about your suitcase. And um.... I'm looking at how loose my panties are on you. They are probably fine for bed, but you might have to borrow some of your sister's tomorrow," Mom says thoughtfully.

I look down at the panties I'm wearing, then glance up at mom with almost a look of disappointment on my face. I look down at her pile of worn swimmers and panties on the floor, then return my gaze back to her.

"If you want.... I guess... You can still sniff mommy's panties and masturbate your little penis, but they don't really fit you sweetie," Mom says. "They're a bit too big."

Wow, it's like she can read my mind. Any distraction is welcome, but did she really just say that? Why is it so hard to block out thoughts like this. No wonder mom and Carly see me the way they do. I'll do it once, tonight, then it stops, I tell myself.

"Go on, pick whichever ones you like, Sweetie. I wore those ones to bed last night," Mom tells me, pointing to a pair of green satin panties. They have smooth satin around the front and thin, see-through lace on the sides and back.

"Pick them up, Sammy. I can see how excited you are," Mom says, looking down at the tiny bulge in the front of my panties.

I bend down to pick them up and feel some small streams of pre-cum coating the soft material inside the pair I have on. I feel so nervous doing this. I had only ever done it when I knew, for absolute certain, that everyone was out of the house. It felt so wrong. So taboo. So exciting, to do this with Mommy's permission.

"Come to bed Sweetie, let's see if we can cheer you up a bit. Take your mind off things," Mom, signalling me to join her on the bed.

My heart races as I lay down next to mom wearing nothing but her t-shirt and panties, holding the worn pair in my hand. I reach out to turn the light off and feel Mommy's much larger and more powerful body move in behind me. I press my soft bum back towards the top of her legs, and she wraps an arm around me.

"Its ok Sweetie. Bring them up to your face while I 'relax' you down there. It'll be ok Sweetie," Mommy whispers in my ear.

I bring the panties up and take in the first smell of her leftover, musky scent, feeling mommy's hand reach down between my legs. She slides her fingers into the front of my panties and gives a few pinches at the loose skin, then decides to press and rub with two fingers instead. I can feel my stickiness on her fingers as she rubs my tiny penis in small, circular motions.

It feels so nice, I can't help but moan in a slightly high-pitched tone. I close my eyes and gently touch my tongue on gusset of the worn panties.

"Oh, Honey, it's going to be ok," Mom whispers.

Moaning more, I feel my hips rocking back towards her, then forward to meet her fingers rubbing me.

"Uhuh... YES," I murmer, holding my breath and feeling a large stream drip onto my mom's fingers.

"That's it, Sweetie, let it all out,"

I let out a big sigh of relief as I feel a few more streams of wetness dribble onto mommy's fingers.

Mommy rubs me gently a few more times before bringer her fingers up, under my shirt, towards my large, pink nipples. With gentle swirling motions, mom massages the sticky mess I made on her fingers, into my chest like an ointment.

I start to feel very relaxed and sleepy suddenly. That is, until I realise what I had just done. Feeling incredibly disgusted at myself, I throw the panties onto the floor, trying to forget about what had just happened. I snuggle back into mom, comforting me, stroking my hair while I drift off to sleep.

--

Waking thirsty, I walk out to the kitchen for a drink. I hear the familiar sounds of my sister having sex with her boyfriend again. Curious, I peek through the slightly open door and watch, as he is pounding her again.

I watch him dominate her body, pounding his big cock in and out of her for a couple more minutes, until I see his body, and balls, tense up, cumming deep inside her. I quickly turn to walk back to mom's room, forgetting I need a drink, and am terrified when I see mom standing behind me in the hallway.

"Sweetie, come back to bed," Mom whispers. "Let's not make it too obvious that you like watching them."

With my sister's semen-filled womb on my mind, I talk to Mommy about how I would really like to try sex again.

"I want to try again, but I'm still a bit scared to meet other girls, in case the same things happened, like when I was with Jenny."

"So, you like watching your sister have sex with guys?" Mom asks, changing the subject slightly as we get back into bed.

"I... I ah.. yeah I think so," I say ashamedly.

"What do you like about it," Mom asks.

"I... I know it's wrong to watch, and I know you don't think I could, but I'd like to do that. I wish I could do that; he really dominates her, and it looks like she really likes it," I let out.

"Are you suggesting you want to have sex with your sister sweetie?" Mom asks, with a curious look on her face.

"Um... no, no, no... NO... no.. not.. really," I let out.

"Are you sure? Knowing your sister's high sex drive, and after your little games in her room, I'm sure it may have ran through her mind.

"Even If that's the case, I'm very sorry to say, you can't do that your sister, just in case your clear ejaculation gets her pregnant. The doctor says you're sterile, but we can't take any chances. Anyway, she probably would want to do it a bit differently with you," mom says.

Confused, I let the last bit slide.

"Is that really the part you like watching, the part you wanted to try?" Mom asks inquisitively.

"Well... Yeah, I suppose, why do you ask?" I say defensively.

"No reason sweetie.... Anyway, your sister has a boyfriend to do that for her. You've seen them have sex a few times now, how does his cock compare to your little one?" Mom asks, slowly reaching her hand over to rub my penis.

I instantly feel myself squirt a tiny bit of precum.

"Well yeah, I guess he's much, much bigger," I say, thinking about the comparison.

"That is an understatement, sweetie. Is that the first cock you've seen in real life?" Mom asks.

"Y... Yeah, it looked really big. So big, that I thought he was hurting her the first time I watched. She seemed to like the way if felt A LOT, though," I tell Mom.

"Well, you should see mommy's kind-of-boyfriend's cock then, it is simply huge. He is a huge man, and my GOD does it feel good!" Mom exclaims.

I feel some more throbbing between my legs, as I see Mom's free hand slowly work its way down between her legs.

"I... I didn't realise you see anyone like that mom?" I say with almost a jealous tone in my voice.

"I've just, never brought them home because I don't want to upset you and Carly. But I guess you're starting to get to an age where it might be ok. You know, with your dad and all that business."

I hated my dad, but strangely, I'm feeling a little jealous for some reason, thinking about what this guy gets to do.

I bring up the topic of trying to have sex again. "I really want to do all those things too Mommy, I want to.... Have sex with someone," I say, as she notices my eyes glancing down between her legs.

"What about...... No don't worry," I finish saying.

"What is it sweetie? Tell me," Mom asks.

"What if I try it with you mommy?" I say with hope. I'm also shocked at the words coming out of my own mouth.

"Hmmmmm I really don't think that's a good idea sweetie. I don't.... No."

"Pleeease Mommy? Can we just try it once?" I beg.

"Look, I really don't... do you really think you could... make it work? I'd... I can't believe I'm even entertaining the idea. Sweetie, it's been a while for me, and I REALLY want dick, don't get me wrong, but yours is so incredibly small honey.

"I think if we did it, we are both going to end up being really disappointed. Maybe we think of something else," she says, making circular motions again on my little penis to distract me.

"Mom, please! I really want to lose my virginity. I want to more than anything! If I have a chance at being dominant like that, it might help reverse some of the... hormones," I blurt out.

"Sweetie...." Mom says, pausing a little. "That's not how it works. It won't change a thing. I really don't know if there are any positives to be gained from this.

"If... IF, I was to do this for you... you're not going to get all upset and depressed if it doesn't work, are you?"

I shake my head, feeling my heart beat a little faster. I am so excited that she's even considering it. Would she really let me? Hang on a minute, should I be doing this? What would other boys my age do? I think I have to, I may not get another chance.

"Well... I'm almost positive that you won't be able to, sweetie... but... alright, we'll give it a go, just for you," Mom says, slowly getting up on the bed. Mom gets down on her hands and knees in the doggy style position, as if to display her openings to me. "This is probably the best position to try and get some penetration."

I see a slight hint of curly hair running from the sides of her pussy, up and around the outside of the wrinkled skin of her anal opening. I notice a small glistening spot between her lips, this must be where I need to get to.

Oh my god, my mom's pussy is open in front of me, I am so excited, she's the greatest, I think to myself, as I get behind her.

I pull my panties down, and I feel mommies hand reach between her legs and grab my small, throbbing penis with her finger and thumb. She slowly guides me between her moist pussy lips. It feels so smooth and wet and nice. She must be turned on by this! Maybe she'll like it?

I start to thrust my hips backwards and forwards, my pelvis bumping all the way forward into mommy's curvy butt cheeks. I feel like I'm not quite inside her yet. I thrust some more while she lines me up with her finger and thumb. I feel her wetness again, and wave of pleasure sweeps over my body, so I pull back a little so I can push my little penis all the way in.

Pulling back a little too far, "Oh fuck!" I whisper under my breath. I fall out of the position between her outer lips. I squirt all over the outside of mommy's wet pussy.

FUCK! I must have been so close to getting it in. Hopefully she lets me try again.

"Sorry Mom... It... It feels really good down there," whispering, squirting the last of my clear liquid on her outside folds. I immediately start trying to thrust again, until I feel moms hand grab me and stop me.

"Sweetie, I think that's all we can do," Mom says, sounding sympathetic.

"But Mommy, I was so close, I think I'll be able to do it. Just let me try one more time please, please," I say with desperation in my voice.

"I really don't... Ok, one more, then that is it ok? Just so you know, you were only just sitting inside my labia lips sweetie. You were still a long way off penetrating me," Mom says as nicely as she can.

For the next 5 minutes I desperately hump, grind and stab at her wanting pussy from behind, trying, willing myself in. I'm desperate to slide my little penis inside Mommy, but I just don't have the size, or firmness. I can see she is starting to get a bit annoyed.

"OK sweetie. Let's pause for a second. I'll give you 2 more minutes, and if it doesn't work, can we give up this whole dominant fantasy... And go with your other..... more passive instincts? I've done this for you to be nice, if this doesn't work, can we think about trying some different things? Can you do that for me?" she asks nicely.

Mom strokes my dick between her finger and thumb, while sliding two fingers in her pussy for me to see. I try and direct all my strength into my tiny penis to somehow penetrate her. Mom removes her wet fingers from her open pussy, and guides my baby-sized penis in to replace them. The first thrust goes in. The second thrust, I fall out and slide up near her clit.

I fall back on the bed panting, disappointed, upset.

The two minutes isn't even up yet, but that was my very best shot. I know there's no way I can get it in, I think, deflated and little sad.

"Sweetie let's try something that you and I might both like. Something a bit easier, something interesting. A bit of a test. I have a bit of an idea," she says with an interesting tone, and reaches for her phone.

"This is John's cock," she says, showing me photos of her lover on her phone. "This is a real man's cock, not a tiny little penis."

I instantly feel some blood heading in my small penis' direction. My little nub sticks up and some pre-cum drips out. If Carly's boyfriend's cock was big, this was enormous!

"Unfortunately, this is the sort of cock that most women want, and yours... we really shouldn't even call that a cock, I'm sorry honey. It is a tiny, useless, sterile penis. And his, his is huge, thick and virile, which is why it feels so good."

I feel my tiny nub swell up and stick out further than it has for a long time. Am I getting turned on from mom belittling me, humiliating me? Or is it something else?

"I can see why it excites you; it's a very good dick. I haven't had it for a while, but this is the kind of cock I crave.

"I find it interesting that your little nub couldn't get hard when given the opportunity to have sex with a woman, when I was right in front of you, but it gets firm and sticks up when you see pictures of the huge, black cock that gets to fuck, and please mommy," Mommy whispers seductively in my ear.

With the thought of that huge black cock pounding mommy, I find myself wondering, what did it feel like for her, sliding in and out, giving wave after wave of pleasure? What positions feel good for mommy? What positions does she get in to please that big cock. I start to feel a bit funny when I think of seeing a big cock like that up close in real life. It weirdly, makes me feel very submissive even thinking about it. It makes me feel inferior and strips me of any thoughts about being dominant.

"Tell me you like the look of his big cock," she whispers. "Tell me you like having a small penis and being submissive. Tell me you want to see mommy's face when she feels a real man's cock, and strong body behind her. Not your tiny, little penis, and sissy physique. Tell me you want to try being mommy's passive.... little girl," she whispers in my ear.

I try and block mom's hand from touching my hard little penis any further, but I squirt up her arm, I squirt on the bed, and then up my belly. I can hardly breath as I have a huge orgasm. I feel both on top of the world, and like I'm falling off a cliff, as I hug into mommy's chest, tears of confusion in my eyes.

I come to the realisation that there is just so much difference between the guy mom describes, and myself. No matter how much I try, I simply cannot see how I can fulfill that role.

I cannot deny it any longer and she forces me to admit that I like being submissive. She forces me to acknowledge that, while feeling deeply embarrassed about it, I am a little bit feminine, a little bit passive.

What does this mean, though? Were the hormones making me this way? Or was I like this already?

"Why don't we just give it a try for a little bit honey? You need to try being a little more open-minded about it. You've lived a lot of your younger life like this, and didn't think anything of it. There's no use fighting it all the time," mom states.

"I.. I'm scared... I'm not sure it's what I want. D... do... you think I could try it just for a little bit first maybe? And if I don't like it, I can stop? I'm so scared mom, It's not normal, and I just don't want to be judged and called a freak," I say softly.

"Aw sweetie, I tell you what, lets just try it a little bit while we're here on holidays, and see how you like it. We don't know anyone here, it's just going to be Carly and I that know about it. We'll help you get dressed up in some nice clothes, and try just going for a quick walk along the beach. I'm sure with the right clothes, no-one will even be able to tell. You are naturally, very feminine looking sweetie, with the temperament to match," Mom tells me.

"But what about those guys near the pool, at the gym? They were teasing and making fun of me mom! That's what I worry about, people laughing and calling me a freak," I explain. "I don't... no, I don't think I want to do it!"

"Oh honey, they weren't making fun of you. They were being incredibly crude, and making vulgar gestures of what they would do to you. They were very obviously perving on you; Your see-through top, your perky nipples.... That's why I wanted you to cover up. I don't think they had a clue," mom insists with a chuckle.

"Really? They wanted to..." I let out, flabbergasted.

"Yes, really. I think your sister may have even been slightly jealous of the attention you were getting," Mom says reassuringly.

"I don't like to pressure you into anything, but sometimes you do need a little nudge, Sammy. What I think would be a great idea, you should commit, with an open mind, to try it out for the next two weeks while we're here on holidays. Just think of it as 'role play'. If you like it, I'll leave it up to you to decide if you want to resume it and, possibly, your 'treatment' when we get back.

"After a while, probably not even Carly and I will be able to tell. And no-one will actually care sweetie. If that is what you would like to do? it's not uncommon at all these days." Mom tells me, in a positive tone.

"mmmm.. I really don't know about that. I don't think... Let's just try some 'role play' tomorrow, and if that goes ok, I'll think about the rest of the trip. Happy now?" I ask. "Ick, I feel sick in the stomach."

"Yes sweetie, terrific! It's a big step, but I think you will really enjoy it. Anyway, let's not talk anymore about that until the morning.

"I've just thought of something else that might cheer you up!" Mom says with a mischievous smirk. "I know that your little thing didn't work before honey, and you're interested in sex, so instead, would you like to watch Mommy have sex with a real man?

"Oh." I say, shocked.

"Maybe... you could lay underneath the bed that mommy and her lover are using, and watch for a bit," mom asks. "You can hear the sounds that mommy makes when a big cock is pounding me."

Oh god, I'm nearing exhaustion, but I feel another little erection forming.

"Now that you are starting to develop and mature, I agree with you, that we might need to try a bit more of a hands-on type of approach to your sexual experience. I can tell by your little throbbing nub that you absolutely love this idea!" mom says, while making slow circular motions on her pussy.

"Um.. I guess that would be g.. good," I say nervously. It's not exactly what I had in mind, exciting nonetheless.

I watch mom grab a familiar looking pink item out of her makeup bag. It starts to make a buzzing noise when she turns it on. She then rolls over onto her front, placing the pink thing between her pussy and the bed.

"mmmm, have you ever licked a pussy before Sammy?" she asks in a seductive voice.

"Y.. yes.. I.... Carly made me do it one day," I stutter. Oh god, I can see she's enjoying this, but is mommy really going to make me lick her pussy? Would I do that?

"What about ass honey? Have you ever licked that before?" I hear mom say, her voice slightly muffled by the pillows.

I feel some clear, wet liquid escape my little penis. I offer no answer, as mom uses her spare hand to grab, and slightly spread one of her plump ass cheeks.

"Why don't you come here and try eating a little ass, while mommy uses her vibrator to have an orgasm? A special treat for you and me. I'm so, so horny tonight too. Why don't you be a good sissy, and help mommy for a little bit," she says in between the subtle moaning.

I know how deeply wrong this feels, but my heart is racing. I look down and see mommy spreading herself for me, and decide to go for it. She moans deeply as I trace my tongue up her pink and slightly hairy hole.

"That's it, sweetie, this really pleases mommy," she lets out.

I lick up and down a couple more times before deciding to spread her cheeks open with my hands, pressing my tongue into her tight sphincter.

"Oooh sweetie... Oh that feel soooo goood," Mom moans.

I run my tongue up and down in a bit of a rhythm and I taste her pussy juices on the downward journey. After a few more laps, I feel a hand reach back and rest on the back of my head, pushing my face in deep between her cheeks, my tongue forcing its way deeper and deeper into her relaxed asshole.

I smell a mixture of pussy and ass juices, and feel her start rolling her hips backwards towards my face, encouraging me to slide my tongue as deep as it can go.

"OH. OH MY GOD, OOOOOH Sweeeeetie," mom moans. I feel her body tense up and start shaking. Mom collapses on the bed under me, and I continue, changing to long, gentle strokes with my tongue, from her pussy opening, all the way to the top of her ass cheeks.

"That felt so good honey. You really made mommy feel good," Mom whispers, while drifting in and out of consciousness.

"I might organise John to come over when we get back sweetie, would you like that?" mom asks, looking for my reaction.

"I think I would mom," I nod.

"You're still very excited honey; I can see your little nub leaking onto the bed," Mom tells me. "I was thinking, because you squirt almost instantly from any movement on your little peeny, maybe you should learn how to masturbate it differently. Somewhat like a clit? It might be a more consistent way to get off for you baby," Mom insists.

She reaches over and starts rubbing in a circular motion, her two fingers pressing against my small, clit-like penis, using my precum for lube.

"After your sister went through puberty and turned 18, I bought her this same vibrator to practice with. Would you like me to buy you a matching one too?" mom asks, moving her pink vibrator over to touch the skin on my little bump.

"Oh," I can only moan to answer.

"Men always think about their cocks, it's so one-dimensional, and that's fine. But now that you're trying to be a little bit more fem, you should start thinking like along the lines of one," She says, gently pressing the vibrator against me. "You know there are other parts of your anatomy that you can receive pleasure from, other than your tiny little peeny," Mom says in my ear, in a bit more than a whisper. "Close your eyes sweetie and just try and enjoy it. It's time for you to learn."

Mom slowly slides a finger, and then another inside me while pressing the vibrator on what looks like my swollen, oversized clit. She leans down and starts whispering in my ear.

"I want you to imagine watching your sister having sex with a real man again. I want you to see what it's like to be fucked. Watch and learn how to move and moan, with a dominant man's big cock inside you," Mom whispers, while curling two fingers up towards my stomach.

I close my eyes and focus only on mom's words and the pleasure I'm receiving.

"One day, when you're a bit older, you'll be ready to lose your virginity, just like your sis did. He will hold you down against the bed, slide his big, thick cock inside you, stretching and pleasuring you," she continues, thrusting her fingers more firmly.

Oh shit, I'm not sure that's how I want to do it, but with mommy whispering it in my ear, holding the vibrator on my little dick, and massaging my tight little passage, it is certainly helping me to think about it.

What was she doing to me? Is she trying to plant ideas in my head? Is she trying to desensitise me to all of this. Oh Shit, oh shit.

I squirt a little up my belly in excitement, as it builds to an intense feeling in my whole body. "Good girl, that's it. Move your body back and forwards on my fingers. Such a well-behaved girl. Is it ok if I call you that?" Mom whispers softly.

I start thrusting my hips harder towards mommy's fingers. Oh, there's just so much happening.

"Mhhmm... Mhhhmmmm," I moan, as I begin to squirt more and more. "Mmhh yes Mommy," I manage to get out before going limp on the bed.

Mommy turns off the vibrator and slides her two fingers slowly out of me.

"Looking at that little mess, I think it's safe to say that any idea of losing your virginity with a girl has now been put to bed, don't you think?" A statement, not a question.

Exhausted, I find myself obediently nodding and agreeing.

Wait! What am I agreeing to? Did I want this? I'm only trying to wear some clothes for a day, not all this. She keeps saying 'like a girl', I know I'm not exactly oozing testosterone, but I'll never be a girl. Why is she constantly pushing me further and further?

Those thoughts aside, it does feel good having someone pay me sexual attention. Lots of attention, and affection. I crave it. Maybe I'll say yes, just to keep this going. Not like I can get it anywhere else. I do enjoy pleasing mommy too.

"I think I'll order you a vibrator online now. Carly's boyfriend is going tomorrow. Tomorrow night, when you're back in her bed," Mom starts. "Would you like to borrow my vibrator, while she uses hers? You can watch her and learn a different way to do things, how a fem-boy can do things. I'll let you borrow mine until yours gets delivered. She usually rubs her clit with her fingers and slides the vibrator in and out, I think, but she can teach you."

I nod again obediently.

"I'm so excited for you to enjoy being more fem, and I have to admit, I really do like the thought of having two girls in the house. Even if it's just a bit of role play to start with, I'm so happy that you're just starting to realise what Carly & I have always known."

--

I wake up naked, wrap the sarong around me, and look down at my puffy, pink nipples in mirror.

"Morning, sweetie. That looks cute to wear around the villa sweetie, but we need to at least borrow a crop top from Carly," mom insists.

With that, and realising Carly's boyfriend has just left, Mom and I go to Carly's room.

"Morning, how are you feeling today, after your big night? Can we borrow some clothes for Sammy? They... can be whatever clothes you think Carly. Sammy has agreed to do a bit of 'role play', so we're going to dress Sammy up, and the three of us are going for a walk. JUST for today, as three... girls." Mom tells.

"What's happening? What's going on?" Carly asks, with a confused look on her face.

"Sammy has come to the realisation that he is naturally a bit feminine. He's being very brave and is just going to try being a sissy for the day, you know, to see how 'she' enjoys it. Isn't that great?" Mom cheers.

I feel my cheeks burning as they talk about me.

"We had a big chat last night and worked out a bit of a plan... and long story short, Sammy is going to be more open-minded to some things. As a start, we've ordered a matching vibrator to play and learn from you, Carly.

"I might be looking a bit far down the track, but all things going well, I think we probably need to start getting Sammy ready to lose.. to take the next step," Mom explains.

"Wow, go Sammy! You may as well, It is NEVER going to work with a girl, you can trust me on that," Carly says with a giggle.

I feel humiliated, but at the same time, I know there is some truth in her statement. But how could I wrap my head around swapping roles completely? How would I ever be ready for that?

"Oh Yay, this is so fun Sammy! Let me find an outfit. Would you like to wear some little gym shorts and a mid-rift top Sammy? It'll look good on your body shape. I can wear one that's similar, if that will make you feel more comfortable," Carly says, upbeat.

"Ah, whatever you think," I reply

"We'll need a crop top or a little training bra too for those puffy nipples hhehe," mom laughs.

"Oh, here you go, try this one on." Carly says, handing me the dark green training bra, matching gym shorts, and a very small shirt.

"Carly, um... can I please wear a pair of your panties too? Mom's... Mom's panties don't fit me very well..."

"Oh, sorry, I only have one fresh pair left and I'll be wearing them. Ah... here, you can wear... these I guess. I only just put them on before when Travis left. They should be ok," Carly says with a funny look on her face.

I take the sarong off as Carly removes her small, purple thong. I start trying them on and notice they're very damp with some white marbly liquid in the crotch.

"Carly... they have some... stuff," I trail off.

"Hehe, oh whoops, Travis just came heaps and heaps in me before he left. It's been dripping out of me for the last twenty minutes. I'm sorry, all the other ones are with the laundry lady," Carly says.

Embarrassed as much as I am shocked, I pull the panties up. Does it really just stay in there and drip out like that. How long does it hang around for? And how much 'mess' did a normal man produce compared to me? So many questions.

"It'll be fine sweetie," Mom starts. "Not a bad thing to get used to walking around like that, sooner or later it could be your panties dripping with semen hehehe."

Mom and Carly laugh while I let out a rather embarrassed giggle. I pull the thong up, nice and firm, feeling the silky wet spot against my tiny ball sack.

I can't believe I'm wearing my sister's panties, soaked with her boyfriend's cum. I shake my head at how crazy my life is right now, and start to pull the tight gym shorts on. In the mirror, I can just see my perky cheeks sticking out the bottom of the shorts. What's left of my little balls, travel up inside my body and sit inside the skin either side of my little, squashed up nub.

"Sammy, I don't think you have to worry about how they look, it almost looks like you've got a puffy camel-toe hehehe," Carly jokes.

"Oh my god, it does too," laughs mom. "So cute. Let's put your little training bra on, and t-shirt, and see how it all looks."

"Maybe tomorrow you can borrow my one-piece swimsuit, and we can try going to the pool again," Carly giggles.

"Come on, Lets go girls, let's seize the day," mom says.

I give myself one 'last' check-over in the mirror. Self-doubt is starting to creep in, was I really going to do this? Was I really going to walk around outside, dressed fully in my sister's underwear and tight gym clothes? I'm very aware of the need to cover my swollen nipples; there's no denying that, but should I really be giving into this 'trial'? This 'role play'.

What if I hate it? Will Mom & Carly keep putting pressure on me to continue? Could I manage to walk around for a couple of hours and not get a little stiffy, knowing I'm wearing Carly's worn panties, with cum and pussy juice all through them? I'd have to distract myself.

I decide I need a cap and some sunglasses, and scurry around my sister's clothes to find some. I put my white sneakers on and walk over to the full-length mirror near the kitchen.

I see a petite, feminine-looking figure looking back at me. She has smooth, toned legs, a soft, flabby-ish butt, and nothing at-all-obvious in the front of the tight gym shorts. I can see a training bra with some small shape to it, under a very small t-shirt, and below that, a smooth and exposed mid-section. Turning around, I see the faint outline of the thong she is wearing, and a hint of butt cheek peeking out below the shorts.

Could I actually pull this off? My heart races as I walk outside to meet Mom & Carly at the gate to our villa.

"Sweetie, you look so good, so cute," mom says, pulling me in and rubbing my shoulder.

"Oh, and I'm kind of jealous of how good your butt looks in those shorts, Sammy. Borrowing my clothes is one thing, but looking better is just hurtful, heh," Carly giggles.

I manage a wry smile and set off walking through the gate. I reach down and run my fingers over the front of my little gym shorts. It feels smooth and bump-free, and how do I feel? Exposed, scared, extremely nervous.

--

"Phew, I'm glad to back," I say, relieved to be walking through the gate to our villa. "That was so nerve racking. I feel like I've been walking on the edge of a cliff for two hours."

"You did so well Sweetie. SO WELL! Your sister and I are very proud of you. I know you DID NOT want to do that, but you pushed through anyway. Great work," Mom tells me, upbeat.

"Yeah, Sammy, you have our full support if you want to do more of this," Carly mentions, kicking off her shoes. "Let's have drink in the hot tub together, just the three of us."

With that, I see Mom and my sister stripping down to their panties and bra's. I follow suit, and wearing only the small purple thong and a training bra, I walk inside to grab us some towels and drinks. I notice a small damp spot where my little, squashed penis is, but decide not to dwell on it. It could be sweat from our walk, right?

I can hear mom and Carly chatting and laughing in the pool, while I make my way back carrying three margaritas and some towels.

"Oh, wow Sammy, such a good servant, they look great," Carly says, reaching for a drink. "We should get you a maid's outfit when we get back, ha."

I notice Mom and Carly are sitting in the tub with their tops now removed. I squirm a little in my panties at the sight of their curvy boobs in the water.

"That... that's not necessary. I... I don't mind serving you though," I say sheepishly. "I feel a bit more... likely to do some things if you tell me to, rather than giving me a choice."

Wait. What was I saying. Are they going to get carried away with this now?

"Like, within reason. I... Don't... I think... I..." I say as I am cut off.

"Oh, Sweetie, we know what you mean. You have a very submissive personality. We have known for the longest time, I'm glad you're just starting to realise this. Now, why don't you take off your training bra and join us in here, it's such a nice temperature," Mom says, taking a sip.

"I'm not sure about that, Mommy. Isn't it best I keep, you know, covered up?" I ask, checking to see how private our courtyard is.

"Honey, it'll just be us three in here, and besides, it's uncomfortable keeping them squashed up all day. Let them out Sweetie," mom directs.

I listen to her direction and put my drink down, turn my body in the other direction, and start to pull the firm bra up. I feel the tiny shape of my breast tissue and nipples pop out below the elastic.

"Kids, has anyone thought about sunblock? We're in direct sunlight here, and I'm not going anywhere for a while," Mom enquires. "I don't want either of you getting burnt."

"Sammy's back looks like its burnt, mom," Carly replies.

"I'm sorry Mommy, I must've gotten burnt bad the other day," I say apologetically.

My back still facing towards them, I slide the back of the thong down with two fingers to reveal the extent of my sunburn.

"Oh, shit, Sammy. You have a thong tan! When did you get that?" Carly enquires.

I explain how I fell asleep in the sun on our first day here, waiting for them to come home.

"That's a bit naughty, Sammy. I might have to bend you over my knee and spank your bum if that happens again. Alright, well you want to serve us? You can start with getting in here and rubbing sunblock all over us. That will be a great help," Mom says firmly.

I feel a tiny stiffy forming in my moist panties, as I slink into the warm water. I start with mommy's back, running my hands down her neck and shoulders, working the cream up and down her middle section. She then turns around. I know what I am expected to do here. I squirt more cream on my hands, and gently cup mommy's boobs, making circular motions with my hands. The big, firm breasts are such a nice feeling on my hands, and I can tell by Mommy's subtle moans, that she doesn't mind it either.

I start to think about sucking them again. I'm happy to have moved out of that stage, but I actually missed sucking on mommy's nipples. I wonder if she'd let me do it again, sometime.

I feel streaks of precum escaping my tiny nub, but I am not worried because my lower half is underwater. I move over towards Carly and give her the same treatment.

Her much smaller boobs and perky nipples feel very different in my hands. I'd been avoiding the thought, but I start wondering what small, puffy ones like this would feel like, and more specifically, massaging cream into them. My thoughts roll back to mommy making circular motions on mine, with my little mess last night. I feel like a storm is starting to build inside me and struggle not to slide my hips back and forth on Carly's knee where I'm perched.

"Oh, Sammy is turned on from serving us, mom," Carly mentions, running her hand up the front of the bump in my panties. "I bet I could make your pathetic little peeny squirt in the hot tub."

I roll my hips forward to meet her hand, desperate to get off. Desperate for her to rub me until I release.

"Now, now, you two. Mommy is going out later, why don't you save it for when I'm gone. You're back in Carly's bed tonight honey, and I'm sure she will have some fun activities for you."

I feel a sharp pinch on the skin of my tiny penis, and decide to finish rubbing the cream into my sisters boobs, then I sit down in the spa between her and mom. My tiny little balls aching inside my sister's thong from so much stimulation. I sip my drink and ride out the pain.

--

"Bye Carly, by Sweetie," I hear mom say, walking out the door. I step out of the shower and dry myself off. I can only imagine what Carly has in stall for us tonight. Besides the rubbing and massage a few nights ago, It had been some time since she'd forced me to do things in her bedroom. I wonder if she'll make me eat her pussy again. I wonder if she'll let me.... No, probably not.

I walk into our room and see some clothes folded on the bed. There is a pair of white cotton panties with pink stitching, and a pale-pink, cotton crop top. I look up and notice Carly wearing an identical outfit already, and realise this has been laid out for me.

Feeling so sexually frustrated, I'll do anything she tells me in order to have an orgasm. I dress myself in front of my sister, and she gives me a pinch on my sensitive nipples through the soft material of the crop top.

"Are you going to do as you're told tonight, little sissy?" She ask's, making me squeal a little. "Are you going to show me your appreciation for borrowing my clothes this week?"

"Yes, big sis," I reply, hoping she'll let go of my soft skin.

I look at the two of us in the mirror. If my hair was longer, I'd very much look like her younger sister. We have almost the same body shape, with only her boobs being a bit larger, and her body looking slightly stronger than mine. Were the hormones making me change, or did I always look like this? I find it hard to picture what I used to look like, while standing here in this feminine crop top and panties.

"You can go and grab mom's pink vibrator now, little sissy," Carly directs, pointing to the doorway. "Actually, bring me the whole bag, and keep your eyes off the other 'things' she has in there."

I do exactly as I'm told and feel a wave of excitement over my scantily clad body, reaching in to grab the toy mommy was using last night. I take a moment and wonder where it had been, and how I would feel about owning one.

"OK, on the bed with you," Carly says, pushing me on my back. She then stands over top of me, and lowers herself down towards my face. I feel her guide both of my hands above my head, pinning them down with her knees, causing me to let go of the vibrator.

God, she is being rough tonight. I'm feeling a little nervous as I'm pinned against the bed. The faint smell of her wet pussy reaches my face and I lean forward to nuzzle into it.

"Not yet, you eager little sissy," Carly says, pulling slightly away. "I want you to beg for it."

"Please, big sis. Let me lick your nice, smooth pussy," I beg, as she lowers herself towards me again. "I want to please you; I'll do anything you want."

I feel the slightly wet material of her panty gusset, rubbing on my lips and nose, then back down. I squirm under her weight, desperate to lick her, desperate to touch myself.

Carly grabs mom's pink vibrator and slides in into the front of her panties, and with a click, I hear it buzzing against her wet pussy. She slides it up and down a few times, as if to lubricate it, then pulls it out. I can see the buzzing toy glistening, as she grabs my panties and pulls them slightly down.

Moaning, I move my hips up in anticipation of her touching my tiny, sensitive penis.

She does not. Instead, I feel the moist, buzzing wand slide down towards my tight entrance.

"Relax, little sissy. Relax and let it slide in. I promise you'll be enjoying this in no time," Carly whispers.

This was not what I was expecting or what I wanted. I wanted to taste her pussy and shoot little streams of clear liquid. The vibrations cause me to squirm as she slides the 6" toy almost half way in my tight entrance. I moan in shock, surprised to feel a small stream of pre-cum leak out. I struggle against her weight as she slides it in further, and then after a few pumps, all the way in. I feel my panties pulled up against the base of the toy, as if the hold it in place.

My eyes closed, with my focus on the electric feeling pulsating inside me, I feel my sister's covered pussy press against my face once again.

This time I hear her moan, as she grabs a handful of my hair, and pulls my face firmly into her moist panties. I start licking, desperate to please her, desperate for her to climb off me so I can orgasm. She starts humping at my face, while I start humping my hips in the air at the same time.

"Does sissy like a little bit of anal play?" She asks. "You don't have to answer, I can already tell. You're making a wet spot in your panties.

"Let's see if we can make you squirt your useless seed into your panties, without even taking them off," Carly giggles, as she reaches for another item from mommy's bag.

It is also pink, but a very different shape. It has buttons up the shaft and a kind of 'nozzle' off to one side at the end. It makes a kind of humming, or sucking noise when Carly turns it on. I feel the waist of my panties being pulled out, and suddenly, an intense, pleasurable feeling as the toy sucks itself onto my small parts.

"This is a clit stimulator, Sammy. It is supposed to suck onto a clit, but I can see it has swallowed your similar-sized penis," Carly says with a giggle. "This is going to be your new best friend."

My bum, hips, and whole body, for that manner, squirm as waves of pleasure build inside me. I tense my tight butt around the toy and feel Carly's hand grip my hair even tighter. She starts to fuck my face, tongue and chin, so much that I struggle to breath.

"Good girl. Good little sissy. That's it, cum in your panties for me. Shoot your useless streams from your tiny, little, girly-penis."

Was I tasting only my sister's juices through her panties? Or was there some of her boyfriend's cum left in there as well?

"That's it, little sissy. That's... Oh Fuck. Oh FUCK," Carly moans.

I feel my sister's body stiffen slightly, as I let out muffled, high-pitched moans under her body weight. She bogs down all her weight on my face, making small jerking movements with her hips. The wave of pleasure causes me to reach breaking point. I feel stream after stream flood out the tip of my tiny penis, rocking my hips to squeeze the vibrator for more.

This clit stimulator was something else!

It takes a few moments to collect myself, and I notice Carly hasn't let my arms free, or released any of her weight off me. I start to panic and struggle as the buzzing inside me, and on the tiny head of my penis doesn't stop. I squeal into her pelvis and try to push her off, as the intense feeling makes me feel like I'm being electrocuted.

"Try to relax little sissy, another one will come," Carly whispers, ensuring I'm fully pinned down.

I hear my own heart beating in my chest, my heavy, muffled breathing, as my hips, without my consent, start thrusting into the air.

Oh god, oh god, I can't deal with this. I feel like I'm going to pass out. I wriggle my arms, but realize I'm too weak to push her off. I taste her silky juices as she grinds her pussy very firmly on my face.

After what seems like five minutes, my body starts shaking uncontrollably as I have the most intense orgasm, while pinned below my sister. I'm not sure if I ejaculated anything, but it was one of the most intense feelings I've had in my life.

It is such an incredible feeling, laying there, pinned against my will, while feeling so much pleasure. Should I just give up and go with this? Would it be the worst thing in the world to do this all the time? To be a slut for my sister and mom?

--

My suitcase and clothes never did turn up. I spent the rest of the holidays dressed in my mom & sister's clothes, going on short trips out of the villa during the day, role-playing and exploring at night. Mom and Carly made sure I was rewarded after every nerve-racking trip out in public, turning it into a very positive experience for me. For the two weeks we 'role played' at the villa, I was a sissy for mom and my sister, and I think I liked it.

It was now time to make the trip back home, the trip back to reality. Would I continue this 'role-play' and acts of servitude when we arrive back home, or continue to fight?

-------

Thanks for reading everyone. I'm really enjoying writing this story. Once again, happy for any feedback, suggestion or constructive criticism.

This chapter feels a bit longer than the previous ones, and another subtle notch in the MC's path of least resistance and discovery.

Let me know what you think!