Jerk Bros to Sissy Sisters Ch. 03

Some days went by, what was normal was changing around here.

For starters, we felt comfortable enough to walk around in boxers only. We fapped openly, no doors closed, no mute, unless the other wanted peace and quiet. We'd jerk off each other if we felt like it, which we did pretty often. Eating cum was easier. Doing it together made us go through and not lose heart after ejaculation. It also tasted damn good. I liked Greg's a bit more than my own. He said the same for mine.

One day Greg came home and seemed upset.

"Hey man, how did it go?" I asked. He was to see Pam and talk through some things.

He glanced me and sat down on the couch.

"Giving the silent treatment, are we?" I joked.

I got a stare of defeat, disappointment. Then he looked down, and I sat next to him.

"Hey, it's not on you, you didn't do anything wrong."

Slowly he rose his eyes to meet mine.

"How can you tell?"

I felt a strange shock. Looking into them I felt a wave of sadness and powerlessness. And I knew some of it was mine. So many times before I only saw others go through these things, and could never do anything. Just couldn't find something to help with. What was I to do, that would meaningfully impact him?

He is my friend, I thought. And I was his. That had to amount for something.

I reached over and hugged him tight. No words needed. No explanation, simple as.

He stood there a bit, only his chest moving. He then returned the hug. Sobbing followed.

"She- she said I-I ask too much, too much p-perverted stuff. When I can't, I can't even fuck her properly. She wanted a man, n-not a c-confused gay boy."

I was at a loss of words. What do I say now? 'Yeah, you know, jerking with your buddy ain't exactly straight.'?

"You should've talked with each other more. She has her wants and needs, it just looks like you weren't a fit. There is no need for a relationship to go on if you both don't get what you want out of it." I tried consoling him. "Still, she could have laid you down more gently man, she was a bitch from what I could tell."

"She s-said I was a confused g-gay. A-am I?"

I pulled back and stared, a bit confused myself.

"Do you want to be gay?" I asked. He seemed even more confused.

"I...don't think..."

By all means it didn't make sense. When you jerk with a dude and have him suck your dick, that makes you a bit suspicious, you may not be the straightest tool in the shed.

But what if he didn't see it as a guy-on-guy situation? Rather, one of us was a sissy?

What if we both were?

I felt something awful surfacing inside. Did I cause this breakup? Was it my 'experimenting' that triggered it? Watching sissy porn and hypnos together?

"I...I am sorry," my face burning and eyes tearing. "It was my fault."

He looked with disbelief. Hanging from every word.

"If I hadn't told you about the sissy stuff, jerked off together, you'd still be...you'd still be with Pam. "

He stared for a while, not saying a word.

"A-are you saying 'sorry for turning you gay'?" He said dead serious. "Bro that's stupid."

We stood there, silent. Then we burst into laughter.

It went on and on, releasing all the tension, making us slip from the couch, sitting on the floor.

"Seriously though," Greg recovered, "You don't 'turn' gay, as you don't 'turn' straight. Those hypnos just bring out something deep inside you, something that may be repressed. Besides...I really liked what we did together..."

"Yeah, me too...you're right, I feel stupid... Do you not feel gay, because you identify as a sissy?" I teased.

He made a smug grimace. "Are you mocking you sexist pig? Well, you have lost your cocksucking privileges." He laid back and crossed his legs.

"Nooo, pleease, I did not mean to. I am somewhat of a sissy myself." I got on my stomach, getting my face below his glutes, giving a light kiss on his balls through the fabric.

He let a soft moan as I kept kissing them.

"Mmm, I can tell you how much you need this," Greg said dramatically. Although I had a suspicion he was talking about himself. "Go on, beg me for it."

I was getting pretty hot. "Please. Please let me have a taste of your dick. I wanna suck and gobble down your cute prick."

"Hah, hah," he panted. "You think it's cute?"

I nibbed his balls, softly pulling his scrotum. "You are cute." I answered blushing, burying my face in his legs.

He moaned louder, it sounded...girly.

His fingers went under his pants, while he thrusted his crotch upwards to remove them. I helped him left them up and took in his appearance. Almost shaking, naked from the waist down, and barely returning my gaze, blushing.

So fucking cute.

I slowly spread his legs while he lay there, and got down to business. He moaned weakly as I tasted-no, devoured his cock, salivating and slobbering all over it. I wanted it, to keep it in my mouth, play with it, almost choke on it. Greg was a wimpering puddle, melting in my hands like sweet jelly, which I was keen on eating.

I switched to wrapping my lips around his head, his shaft, his balls, fondling with my hand the part that felt left out at any time. I even tried a bit deepthroating. The warmth and pleasure I got from keeping his prick buried inside my throat were immense. I wanted to swallow it like that bitch never did. To protect it from anyone who'd harm him.

"Hnnnyaaah." Unmistakably girly.

He came hard inside my mouth, shaking like never before, thrusting up and down unvoluntarily. His dick popped out and kept cumming, pooling cum on his belly.

I realized I were watching him squirm with tongue hanging out and sperm dripping, glazing his penis. Why was I letting it go to waste?

I promptly swallowed his load, savoring it, then got down on his cock, licking it clean.

"A-ah, Stan. I'm still sensitive."

I smiled while going on with my business. Greg could easily pass for a smug guy, hiding behind a cocky attitude and humor. When with me, he had a more dominant role, but it was really ease to melt it all away. To bring out the sensitive side of his, the vulnerable, the raw. You poor pretty thing, I thought, while softly lapping his tasty cum, leaving kisses on his cute belly.

He pulled me up from the shoulders, so I was on top of him, and we stayed there for a while, cuddling almost. Rising up and down, feeling our breaths, the shared warmth of our bodies.

Not sure how much time passed before he broke the silence. "Well, I'm gonna take a bath."

"Yeah, same," I replied.

He got undressed and got in, then turned to me, "What are you waiting for? Hop in."

I stood there, a bit baffled.

"Dude, I've seen you naked, god, you gave me the best blowjob of my life. Don't just stand there covered in dry cum, get in."

I suppose he was right, it felt a bit weird, is all.

I got in and we found the best temperature for both, literally hot stuff. The shower was pretty small, so we had to keep close to stay under the water.

"Hey, how come you don't shave all over?" I asked. It was only his crotch that was smooth.

He briefly looked away then responded. "Uh, well, Pam didn't like it. She said it was too...effeminate. I liked it though, it felt like I was taking care of myself."

"I like it too." I assured him."...Hey. wanna shave now?"

He looked surprised. "Now, now?"

"Yes, start fresh and authentic." I stepped out and picked up two razors and cream.

"And I'd like to try it too."

He lit up and got right to it.

God it took long.

It wasn't unpleasant, but the sheer volume of hair to be removed made the shower lengthy. He shared tips throughout, how to not irritate skin, and use the blade effectively.

We got each other's backs, literally. Along with any other difficult-to-reach places, like behind knees. Something about this, the steamy water pouring down, his hand spreading the cream on my shoulder blades, his warm breath on my neck...It all felt so serene. I loosened up and just stood there, embracing the moment.

"Stop smirking back there," I reprimanded. I could feel his grin widening.

"All done here," he said under his breath, "Turn around."

I did as instructed, and he kept shaving my chest. His hands were skilled and delicate, taking care to not discomfort me. He put a finger on my nipple and lightly tugged the skin to get the hair on the areola. I breathed slightly heavier. I noticed his face now, better than any other time, smooth and clean, his gaze focused intently on me. Such tasty lips.

I leaned closer, my eyes meeting his. He slowly closed them, as did I, and we kissed. It felt like the softest hurricane blowing us away. My hands moved around, fondling and caressing our smooth, lean bodies. It felt like many minutes we shared breaths, rubbing our legs, arms and torsos together. A small jolt fired across my chest, as our hard nipples brushed against each other. I broke away from the kiss unhurriedly, smiling.

"We're gonna melt in here if we don't get out," I stated.

"Yeah, I guess. Hang on, missed a spot."

He kneeled and turned me around, shaving a spot on my ass I may have neglected. Getting those crevices, he brushed his finger on my asshole, eliciting a soft gasp. He kept going, placing his thumb on it, gradually pushing the top inside.

"Hey don't squirm, I am holding a sharp instrument."

I tried to stand still, but this new sensation was foreign and bizarre. His finger in my ass was accessing my core being, teasing what he could do.

We did not go further than that today. Greg started gathering some of Pamela's stuff to return them to her, mainly clothes. We ordered food and watched a movie. It was so strange now, shifting around and walking, feeling the fabric on the skin so intensely. It rubbed so smoothly and effortlessly, like my skin itself was velvet.

After the movie ended, Greg got on his phone to relax before sleep, while I took the cups and dishes to the sink. I stepped on a piece of cloth, which appeared to be Pam's jeans. Ah well, I picked it up and tossed it along with the others, but something slipped from inside, something purple. Curious I walked closer and picked it up too. It was her panties.

I froze for a second, I should put them in the pile, but he wouldn't wanna see them. I should wedge them among other clothes. What if it slipped out the same way? I should put them in a pocket or some-

"Hey man, did you want any help getting the stuff?" Greg asked walking inside.

I hastily turned and placed the panties in my pocket.

"Heeyyy, nooo, all done." I scrambled suavely.

He glanced at the dishes and approached me.

"I'll wash them tomorrow." he said. "Hey, thanks for everything today." He hugged me tight and I returned the hug, painfully aware of the contents in my pocket.

"Imma drop now, I feel like a rug. Goodnight." he left me.

I waited until he went through the door, pulled out the panties and went for the pile. Just gonna place them somewhere in there. Just gonna-

Shit, I took a step and as my leg moved in my pants I felt this euphoric caress on my smooth skin. My fingers wrapped around the fabric of the panties, i was so soft and tender, I wonder-

No, that's just wrong. I advanced towards the pile, two more steps.

Fuuuck... it just felt so good, it would feel incredible in this. I stared at the undies.

Now I got a better look at them, my mind wandered in other places. Greg must have kissed them. He gave Pam oral all the time, he must have. I hunched over them, closed my eyes and gave a little kiss. So soft. Like Greg.

I rubbed my chin and cheek on the fabric. Damn, it was so thin and silky. I placed the panties with shaking hands into my pocket and went to my bed, holding my breath. There I got under the wraps, quietly lowered my pants and boxers, and started putting on the panties. The sensation was indescribable. It raised waves of pleasing shiver up my body, hugging my legs and glutes tightly. I pulled it up shaking a bit. What little fabric there was, wrapped around my hips, brushing my asshole. Everything was so sensitive now, deprived of hair, my sensations were heightened. I gasped softly.

It felt so naughty, wearing my buddy's ex's panties. Getting a raging hard on too.

I touched my penis over the fabric, I didn't want to grab the shaft, as I would have to pull the panties away. I wanted them to cover me, well, as much as they could anyway. I grabbed the top of my dick with the tips of my fingers, rubbing the head with my thumb. It felt amazing. The thin layer was a pleasant, almost non-existant barrier, hindering nothing.

I kept panting, shifting under the covers. Everything felt so velvety, my ass on the bedsheets, my legs on each other. I was ecstatic. The covers rubbed my legs and hard nipples. My whole body was an erogenous zone. My other hand moved upwards, caressing my stomach and pinched a nipple.

I moaned softly. A bit...girlish. The moan itself made me feel even hotter. Another moan, louder. I was a squirming mess now. What was I becoming? Was I really a sissy?

Every moan was an admittance of my sexual nature. I was panting and moaning like a girl, sucked dick and swallowed cum like a girl. I even rubbed my dick like a girl, or should I say clit?

My hand lowered from my chest, started squeezing my ass. I was panting like a bitch in heat.

I rubbed my asshole and cautiously prodded a finger inside.

If this was only scraping my insides, I couldn't imagine the sensation of something...bigger...

These panties. These panties were pushing me further. How much deeper would I fall into this rabbit hole? Would I even want to get out?

These panties were the ones Pam wore. The panties Greg pulled aside to stick his cock insi-

"Nhhaaaah"

I bit into the pillow to muffle my voice. I hadn't realized I let it rise so high.

I didn't move, only breathed, completely silent, trying to see whether he had heard me.

No response, or perhaps he didn't want to let me know. I was too tired to deal with this, my eyelids were heavy. This whole day was taxing, but wonderful. I drifted off, in my cum-soaked panties. They aren't really mine though, was my last thought of the day.

The next morning I awoke lazily by Greg on my bed. He was slowly pulling my covers.

"H-hey, that's too early pal," I complained.

My eyes adjusted to the dull morning light, seeing him grin hungrily.

"Ooh, what's the matter, haven't had your morning skincare routine? Don't worry, I won't judge." He couldn't pry the covers from my hands, so he changed tactics and pulled up the side of my legs.

"Greg, no!" I pleaded too late.

His expression changed the moment he saw my undergarments. His jaw clenched, casting on me a wave of embarrassment and guilt, prickling under my skin.

"Why are you wearing that?" He asked carefully. I didn't know what to answer honestly.

"I, I wanted to see how it'd feel. You know, on my...shaven legs."

Took him a while to respond.

"Take them off," he ordered. "I don't want to see you in them." His face softened. "I'm not mad at you, I just don't like these ones."

His fingers pulled down the panties, over my legs, freeing my cock, which wasted no time rising. I rubbed my knees together, he noticed I got hard.

"I'm gonna head out, give Pam her stuff, and...and I've got an idea. You said said shaving would be a fresh start and then joined me. Well, let me take the next step." He got up, picked the package for Pam and left the house.

I was confused, didn't know what to expect. Guess I'd see when he came back. After a few hours he arrived with another package.

"Come open your gift," he demanded, looking...excited.

It seemed like a bag from a clothes' store. Took it in my hands and froze. Inside were 2 sets of female underwear. A simple white bra with light blue stripes, and matching panties with a tiny ribbon at the front. The same set was also in white and pink stripes.

"What do you think?" he asked blushing. "I believe the pink one suits you better. You choose though, and I'll take the other one."

I brought the pink pair closer, running my fingers on it. It was soo soft, and cute too. Greg was right, this was a step even deeper into where we were going, one we wouldn't back away from easily.

Would we want to?

I leaned closer and kissed his blushing face.

"Thank you."

We washed the undies and could hardly wait for them to dry. Not that we would sit doing nothing, we didn't do anything frisky today though. Greg had officially broken with Pamela today, so he needed some time to let it pass. We sat on the couch, watching a series we enjoyed.

The next morning we hastily grabbed the clothes. I dragged down my boxers, standing completely naked in my room. With a thumping heart, slowly pulled up the panties, my panties. The freshly washed fabric hugged my ass cheeks and hips tenderly. My dick, -shouldn't I call it clit?- was a twitching bulge on the front, the ribbon made it look adorable.

Then it was the bra.

I placed the cups on my chest, -shouldn't I call them breasts?- and passed the straps over my shoulders. God, it took a good few minutes to fasten the clip behind my back. I've been developing a deeper appreciation for the struggles women go through on their daily basis.

The view below me was of a flat chested woman, with only my bulge betraying the image. It did look like a woman's body nonetheless, slim and hairless. The pieces of cloth barely concealed my skin, they only accentuated what was there. It was weird, I felt just as naked wearing these. Also, the slight tightness, this feeling of pleasing restraint. It was like a harness, hugging my core, liberating me.

I got out of my room, looking for a mirror to admire the form a bit better, when I heard Greg's grunts of discontent.

"All ok in there?" I asked outside his door.

"Nnn uuh, yeah, just the, can't get the, thingie, on my back." sounded like he struggled.

I pushed the door gently. His back facing towards me, he really looked hopleless fiddling with the bra. My gaze went lower, to his delicious looking butt, he must have wiggled a lot, 'cause his blue striped panties were wedged between his cheeks.

"Here, let me get it for you." I pulled the pants up, giving him a wedgie and receiving a startled yelp. I fixed the clip, rendering his attempts futile in under 5 seconds.

"Thanks," he muttered slightly annoyed and flustered. "I had it you know," and turned around.

We were speechless.

Greg looked so feminine and precious I wanted to scream, he also, seemed captivated by my looks.

We approached each other and began exploring our bodies again, now in a different light.

We kissed and caressed, focusing on the areas covered by our clothes. He laid his hands under my panties and began kneading the flesh of my cheeks. I let a small moan between our kisses, this feeling of emptiness in my mouth returned. He quenched it by shoving his tongue deep inside. We run our tongues together, slobbering the insides of our mouths, while our cocks- no, our clitties- rubbed, twitching desperately. I got mine out. I couldn't take it anymore, I wanted him. I wanted to make him mine, brand him. I needed to cover him in cum and lick it from all over him, then take his cum on my slutty face, bra and panties, like the needy whore I felt.

I was jerking so furiously I could only wimper and moan continuously, almost hanging off of him. He could see the mess I was, he gave me a horny smile, grabbing the back of my panties, and pulled fiercely.

I came harder than ever before, my legs giving up on me. I fell on my knees, while Greg grabbed the side of my head and ejaculated all over my face, rope after rope. I could only accept his offering with eyes closed, grateful. He fell on his knees too, out of breath. We rode off our orgasms panting and moaning, tongues out. He started licking the cum of my face, cleaning me like a cat, as I kissed his, again and again.