A Sissy For Mom And 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.