Looking back on it, I should’ve seen it coming. When I was feeling up Gail with trembling hands in her room that day, it didn’t feel the way I did with Cassie. Of course it was exciting and made me hard as a rock, but it was… different.

An ignorant part of me still persisted: “I’m feeling up a REAL girl’s tits, this was so much better than it was with Cassie”. It wasn’t the truth of course, but I made myself believe it.

Gail and I never had sex that day. She was way too nervous to have sex, but I got the opportunity to explore an actual vagina. I’ll never forget the sweet memories I had with Gail that day. She taught me a lot: spots to pay attention to, how to finger a girl, and a ton of foreplay.

They say you never forget your first, but I still always feel like I remember a little too much detail. I remember what she was wearing as she was laying on the bed spread before me: a hot pink camisole, a white training bra (she was a particularly late bloomer) and pristine white cotton panties. I remember thinking how bizarre it was that she smelled almost… spicy.

“That… that feels good.” She breathed as I dragged my forefinger down her labia.

I won’t lie, her pussy intimidated me to no end. So many curves and folds to memorize and manipulate, I was a bit overwhelmed. Somehow, I almost preferred Cassie’s penis to this enigma. But Gail showed me endless patience. I dipped my finger into a deep valley and she tensed up.

“That’s my… my…” She trailed off in a series of moans as I finger fucked her. She gripped the sheets tightly as I inserted another finger. The texture inside was odd. I remember the inside of Cassie’s ass being almost smooth. The inside of Gail’s vagina was different: soft wrinkles and crevices that rubbed and milked my fingers. I yearned for my dick to be inside there, but Gail didn’t want to go that far, as Cassie predicted.

My briefs were perpetually sticky and getting crusty due to the fact that I’d cum so much in them. She ended up giving me a handjob, which I don’t remember as vividly as other sexual moments in my young life. And that was the entire evening in a nut shell. When things calmed down, we ended up watching some reality show on TV. I had to leave early because my underwear was beginning to chafe me.

We remained fairly close until high school. On rare occasions we would indulge in masturbating each other for about a year, but it never went beyond that. It turns out Gail was a lesbian and that’s why she never really “felt it” with me. I never felt it with her either though, so I wasn’t too put off.

——-

During my year with Gail, Cassie and I didn’t do anything. I felt a huge shift in our dynamic actually. It began to shift that very night I came home when Cassie poked her head in my room.

“Blue balls?” She grinned evilly.

“Not too bad…” I had taken a shower to get all the cum off my manhood, but not before jerking off twice. Although Gail had given me a handjob, I still needed my sack emptied a few more times.

“Did you fuck it up royally? Did she make fun of your millimeter peter?”

“Shut up.” I snapped, and then added smugly, “She jerked me off.” Somehow I felt that was a victory I could rub in her face.

Cassie seemed… disappointed? Upset? Sad? The corners of her mouth drooped and gave a slight twitch. She shifted her weight on her other leg and crossed her arms in front of her chest. I couldn’t help but notice a hard nipple poking out of her shirt before hiding it with her forearm. “Whatever floats her boat,” Cassie spat before scoffing and adding, “Or rather, what DOESN’T float her boat, I doubt she could ever be satisfied with that thing.”

I wanted to say something like “It was good enough for you” but I realized how weird and awkward that would be. Cassie and I had never really talked too openly about our sexual escapades. Not in-depth anyway. That first time she made me suck her dick was the first time we’d ever even acknowledged it. But what I found odd is that Cassie seemed sharper with her humor than usual. Sure, she could be vicious, but it still had a level of playfulness and frivolity in her voice. There was no hint of playfulness in her voice this time, it was flat and cold.

“Whatever.” I mumbled. I didn’t know what else to say, and Cassie was already halfway out the door anyway.

Everyday thereafter felt relatively normal, only like I said, the dynamic changed. Before we had roughhoused all the time, now it was only teasing verbally for the most part. Physically, things toned down a lot. Sometimes we’d push each other and give each other wet willies, but that’s pretty much as far as it went.

In retrospect, maybe because it felt like Gail and I were kinda dating, even though we weren’t. We were exclusive to each other for no particular reason and Cassie recognized that. No matter how much of a bitch Cassie was, she would never want to jeopardize any of my relationships. She cared for me, even if she had an extremely odd way of showing it.

Everything seemed to be changing. I didn’t really see too much of Cassie during that year anyway as our mom bought her a junk car for her 17th birthday in honor of her getting her permit. I was impressed – our mom must’ve scraped together for quite some time. Cassie was always out somewhere, and even managed to get a weekend job at a nearby restaurant. They also changed her hormones to injections instead of just the gel she was taking, and she injected it in her fat instead of her muscles which diminished her mood swings greatly. It turns out, her moods and tantrums were off the charts because her hormones would rise and fall so sharply. Now that they were stabilized and level (for the most part) she seemed a lot more level-headed and calm. Our encounters seemed to become more rare though, and our fights pretty much non-existent. We were growing up, becoming more mature, and realizing that it (at least for a short time) might not be a good idea to fuck each other right now.

By the time I turned 16, Cassie was 18 and nearing the end of her growth spurt. I had flourished myself: my voice had dropped like crazy, I could grow a wispy goatee, and I had a little more meat on my bones. People were already mistaking me for a 20 year old, which excited me to no end. By now I very rarely saw Cassie, as she was in college now and commuting every day. Between college and work, which she was now doing full-time, I caught her maybe once a week if that. I was busy myself between school and actually having some sort of social life. Oddly enough, I didn’t date all that much. There were a few girls I had had sexual flings with, but nothing too serious. I even got a job working at a local grocery store.

When I had just turned 17 and Cassie was 19, she gradually began to take more online courses until she simply switched to a fully online schedule. This puzzled me, as I thought she enjoyed being on-campus. She told me she even met a couple other intersexed and transgender people. She jumped into LGBT politics and seemed to love the experience. But I noticed she was slightly more withdrawn. She still went out and had a healthy nightlife, but the move still confused me.

Then it happened. It was my 18th birthday – my buddies brought me out celebrate: strip clubs, gambling, and of course some fake IDs so we could get boozed up. Around 2AM I decided to call it quits, against the wishes of my friends, to walk off my current drunk state and get some sleep. As I was walking home down the streetlight illuminated road, I saw a pretty dingy club up ahead. The neon sign read “The Rock” and occasionally flickered slightly. I knew it well. It was one of those skeevy clubs where the druggies go to shoot up and grind on each other. It’s on the news every once in a while, and of course it’s always a negative story. Though I’ve never been there, Gail said she went there once and told me to stay clear of it after a knife fight broke out pretty close to her.

As I tried to walk as quickly as possible past the building, I heard some sort of struggle. I peeked over really quick, not wanting to get involved at first, but I did a double take.

Cassie!

She was wearing a maroon dress and some kind of matching funky girly shoes with straps everywhere. Her tits were amazing, full, pushed tight against the material of the dress. They looked like two luscious scoops of vanilla ice cream and I damn near drooled on myself staring. If she had on make-up, it wasn’t much, but her lips were slick and shiny with gloss. She definitely wasn’t a tomboy anymore. She was with an extremely muscular guy. Even from across the street, and in the dark, I could see his arms bulging out of his rolled up sleeves. He seemed to be kinda backing her down the alleyway near the side of the building.

Cassie seemed irritated with him, and I swore I saw them exchange some mild pushes. Not nearly to the point of abuse, but I was still livid. I could barely make out what they were saying; the loud booming music echoing through the streets, muffling their voices. I quietly walked across, my heart pounding in my chest, my hands shoved into the big front pocket of my hoodie. My ears were being filled with the shitty club music as my nose as being filled with an unpleasant odor not unlike gym socks. I slowed down my walking as I stepped onto the curb and in slightly to the side of the club doors.

“…yeah but not THAT far.” Cassie was complaining about something but I could only hear the end of it. The powerful bass vibrated my chest somehow making me even more nervous. I sidestepped to the corner of the building and stopped just before hitting the alleyway, taking out my phone in the process. I pretended to toy with it while listening to their conversation. Thankfully, they didn’t go too far into the alley and the narrower space made it easier for me to hear their voices.

“Cassie, come on.” He cooed. The voice of his voice made me bristle. I heard the sound of slapping skin and I guessed she was struggling against him.

The intoxication still blurred my vision, my legs were wobbly, and my hands were shaking. But the alcohol gave me courage to peek my head into the alley. He was trying to reach under her dress. The huge bulge in his tight dress pants gave way to his intention as he was now more forceful. He shoved her against the brick wall of the club. The muffled chorus of “The Bad Touch” filtered its way out of the building, giving a hint of irony to the situation. I didn’t know what to do. I froze completely and could only watch the horrific scene play out.

“Fuck, come on. Come on!!” He suddenly shouted. His calm demeanor faded away completely. He began lifting her dress. She struggled as hard as she could but to no avail, as strong as she was he clearly overpowered her. She began to sob. Between the alcohol and my anger, my senses kicked into overdrive. My head pounded, my hands were clammy, and my sneakers screeched against the pavement as I turned into the alley. But it was too late. He had dropped her panties and then frozen in place. Shit, here it comes.

“Jesus! You’re a tranny!” He recoiled in horror, leaving her bare ass exposed, her small cock and balls dangling there for the world to see.

“Get the fuck outta here!” I tried to yell, but it didn’t come out as soft as I intended it to be.

“Fuck it, fuck it. I’m horny.” He either completely ignored my presence or simply didn’t care. He began to drop his pants as Cassie desperately tried to put her panties back on.

I lunged. My eyes were closed, I didn’t even know what I was doing, and I lunged. I lunged with all the might of a scrawny, drunk, and tired 18-year old. I knocked against his torso and grabbed his legs firmly. Taken by surprise, he stumbled backward before falling down completely. His side hit the pavement and he yelped in pain.

“Touch her again mother fucker!” I screamed, my voice hoarse and my speech slurred. His first instinct seemed to be to beat the crap outta me, but then he regarded me coolly. “Get the fuck of here kid. You ain’t no god-damn hero.” He spat and kicked me off him. It might have not been intentional, but his boot made contact with my chain, busting my lip open and sending a searing pain through my jaw and face.

I stumbled back but jumped on my feet quick. Cassie looked bewildered at the turn of events, but was quick to get her panties back on. The guy just stared at us, his cock still hard, his shirt rumbled and dirty. “Lucky I’m on probation or else I woulda fucking killed both of your asses. Especially you, tranny trash.” He pointed at Cassie furiously as he said the latter. Her mascara streaked face could only watch as his fist flew and punched me in the gut. Before I could even double over in pain, he retracted his arm and swiftly punched my face. All I saw was black.

——-

The first thing I felt was my lip pounding mercilessly. My other senses began to catch up, and the intense smell of coffee wafted through my nostrils. My throat was dry and I could tell I had a little bit of a hangover. I opened my eyes and was confused at first as to why I was at home on the couch instead of on the ground near the club. Was everything a dream?

“I never in a million years thought I would meet a real life guido.” My sister said and someone laughed. It was a girl. Actually, it was Gail. Now I was REALLY confused.

I sat up slowly and felt a ton of aches and pains firing in nearly every part of my body. I cried out in pain and heard the scooting of chairs from the kitchen. They rushed over and Cassie sat next to me while Gail stood in front of me with her arms crossed over her chest.

“You ok?” Cassie asked. Her voice was soft and gentle. I nodded.

“Yeah. What the fuck happened?” My voice was barely above a whisper.

Cassie and Gail exchanged confused looks.

“You don’t remember?” Gail asked, apparently puzzled by my answer. I shook my head and she pursed her lips. Cassie cleared her throat and rubbed my back.

“You texted Gail before you decided to save the day, apparently. After that scumbag punched you, you said you were fine and came with us here, where you passed out on the couch.” Cassie explained, looking at my bewildered face.

“I don’t remember coming with you guys, or texting Gail.” I whispered, my voice unable to go any louder. My head was swimming, even my damn teeth hurt. Gail showed me her phone for further proof, even though I hadn’t requested it.

Right there, plain as day, the text stared at me: “come 2 teh rock now maybe ven the cops cassies getting raped”

Spelling errors aside, I had enough sense to know what the guy was going to do, or at least that there was going to be trouble and texted Gail, who I knew was a complete night-owl and was usually out clubbing herself. I don’t even remember doing it though, I must have done it subconsciously when playing with my phone to seem unsuspicious. I mentally excused myself for thinking it was kinda funny that I casually texted with such an emergency (I’ve always had a pretty dark sense of humor.) I had to give myself credit though, even while drunk I had a fairly good head on my shoulders. Well, sometimes. Cassie seems the always be the one to fuck me up inside.

I leaned back into the sofa, and somehow, I instantly fell asleep. I was notorious for falling asleep just about anywhere if I was tired enough.

When I woke up again, my body felt a little less battered at least. I opened my eyes but immediately snapped them shut. The sun was out. I rubbed my aching neck and turned my head from aside to aside in an attempt to make it feel better. The smell of coffee was gone and I could only hear the clanging of dishes in the kitchen sink. I stood up and attempted to stretch: success! Though it hurt like hell, I stretched thoroughly before wobbling to the kitchen.

Cassie was in some loose fitting yoga pants and a t-shirt tight enough to show that she wasn’t wearing a bra. The morning light filtered in through the window, covering her in this angelic glow. I could see the tiny hairs of her arms and her face as the light gleaned off them, accentuating them. I couldn’t help but think how her arms might be as dark and hairy as mine right now if she hadn’t taken estrogen. The shirt was snug around her hips and dipped in where the small of her back was. Her hair was up in a messy bun and bounced around every time she sidestepped to put a dish in the drying rack.

My heart skipped a beat. She just looked so perfect. What was in between her legs didn’t matter.

Slowly, without warning, I wrapped my arms around her waist. She stopped abruptly and felt tense: I’d surprised her. After a moment she relaxed and let me just hold her. In fact, she put her arms over mine and laid her head back onto my shoulder blade. My body still ached but I could stand it for a few more minutes of this. I could feel the wetness on her shirt from the water she’d used while doing the dishes. I discreetly inhaled the scent of her: she smelled like body wash. That was something I’d always loved about Cassie, she never ever felt the need to cover her body with various artificial scents, perfumes, or fake smelling lotions. The only scent she carried was her natural odor, and her soap which smelled like a mix between almonds and oatmeal. She’d always been fond of the brand ever since we were teenagers.

I don’t know how long we stayed there. All I know is that I knew this was another change in our relationship. I just wasn’t quite sure in what direction yet.

I didn’t want to break the silence, but I needed to ask, “Is mom home?”

She shook her head. “No… and thank you.” She whispered quietly.

“No need to thank me. That guy was a dick.”

“You got hurt.”

“Yeah well… small price to pay.” And it was true. When we were younger and kids bullied Cassie for being transgender, I couldn’t really stand up to them. I’ll never forget that day when she came home crying her eyes out and I laid down with her to comfort her because I felt it was the only thing I could do. I was smaller and younger. Though I wasn’t too much bigger now, it was the first time in my life that I actually helped her out. And it felt great. She felt great. This… this felt great.

And there it went. I cursed myself mentally a million times over: I was starting to get hard.

I could feel my shaft pressing against my slacks. Fuck. Cassie had almost gotten raped and here I was getting hard. I tried to pull away, but Cassie kept me there. She snuggled against me harder, her hands pressed into my arms and wouldn’t let go. I was surprised but instinctively bent my head down and kissed her neck gently, my lips pressed against her soft smooth skin. It kinda hurt since my lip was still sore from when that dickhead kicked me. Cassie let out a cute sigh.

“Alright knob, let me get back to these dishes.” She said, though her actions betrayed her and clung even tighter to me.

She had caught me off-guard in two ways. One was that she hadn’t called me knob in years and it gave me pause to hear one of her devilish nicknames again. And two, there was definitely something in her voice. I recognized it immediately: lust. Desire. Horniness. Whatever you wanted to call it, it was there thick as ever.

“Fine, Assie.” I teased back and I could sense her smiling. Slowly, I pressed against her harder and began slowly grinding up against her ass. Just like old times, I mused thoughtfully. She gripped the kitchen counter, began to grind against me, and looked back at me as if to say “Come on, do it.” I suddenly realized how insane this was. Cassie and I hadn’t done anything sexual in years, yet coming back to it was so… incredibly natural. I wasn’t a kid anymore though. I had stamina and perseverance… and a bigger cock.

I spun her around and she let me. She looked so cute, even in her “lazy clothes”. We looked each other in the eyes as I undid my belt.

“I’ve gotten bigger, you know.” I warned her.

She looked at me skeptically. “We’ll see, knob.”

I let my pants and boxer-briefs hit the floor. Deliberately, not breaking eye contact, she got on her knees. Suddenly I had a thought that maybe we should’ve taken it slow after last night. I felt pretty insensitive to want to fuck her after what had just happened. But all of those thoughts were shattered in an instant.

“Oohhhh fuck.” I moaned.

I nearly stumbled backward as she held my dick in her throat. I ignored all the tender bruises and sores on my body – surge of adrenaline maybe? She was amazing; her entire body seemed to be working toward one goal: to expel my seed. Her firm yet pliable tongue gently moved back and forth along the underside of my cock. I could even feel the slight bumps of her taste buds massaging my dick, each one eager for the taste of my cum. She sucked her cheeks inward, enveloping my dick in warm wet flesh. The tip poked the back of her smooth throat as it was held there steadily. I didn’t move. In fact, I could barely breathe. She finally drew back, the sensitive cleft on the underside of my cock gliding along her tongue, sending jolts of pleasure throughout my nether regions. Only the head remained in her mouth, which she lapped with her tongue. She reached up cupped my balls, caressing and kneading them gently. Her other hand went to the base of my dick, encircling her index and thumb around the girth and jacked off about half of my cock while keeping the head in her moist mouth. She switched between this and deep-throating me.

My thighs were trembling from the intense pleasure I was receiving. I felt like grabbing her head and just face-fucking her, but I composed myself. I didn’t want to treat her rough after what happened last night. It was also because I’d always had this immense guilt about being rough with her the very first time we tried anal. But I was a stupid kid back then: thoughtless, horny, and hardly even a speck of willpower.

I did reach down to brush the hair out of her eyes as her mouth bobbed on my dick. She took my dick out of her mouth for a moment to take a few gulps of air before gently lapping at my tightening balls. She traced her tongue over the seam between my nuts and planted small kisses over them. She let out a long and needy moan and closed her eyes as she cupped my cock against her face and rubbed her cheek against it. She then dragged her tongue along the length and looked up at me once more with a fierce hunger in her eyes. Seeing her love my cock, worship it, utterly and desperately want it… it took every ounce of willpower I had not to bend her over, rip her clothes off, and fuck her senseless until I passed out from exhaustion. Thankfully, she stuffed my dick back in her mouth with a hastened pace. There is no way to accurately describe the waves of intense and endless pleasure, but suffice to say I felt an aching and intense orgasm building. I felt the intensity building up behind my balls, even near my asshole, and through my cock that Cassie was so expertly servicing. I heard myself moaning constantly, lost in the sensations, but I had enough sense to cry out and warn her, “I’m cumming!”

My body went stiff, my balls were tight, and Cassie seemed ready. Her eyes remained locked her eyes on mine and she picked up the pace as I pumped sperm.

And pumped, and pumped, and pumped.

Every jolt of my body sent another spurt inside her eager mouth. The fact that her eyes were on mine the whole time just made the experience even hotter. After a few moments, I reached the plateau of my climax and held the back of her head as I pounded her mouth. I’d spent the last of my willpower stopping myself from fucking her brains out and couldn’t help but fuck her mouth (as gently as I could manage though). She didn’t mind, and in fact seemed to encourage it by gripping my ass and pulling me against her. I grunted as the last of my cum dripped out and directly into her throat, causing her to sputter a little. She recovered quick and nursed my deflating cock, suckling gently on the tip and careful not to overly stimulate my sensitive glans. I pulled it out reluctantly, the cool air hitting my wet dick instantly. I felt dizzy and unable to move.

Cassie lovingly, gently, pulled up my underwear and pants. Adjusting my cock inside the underwear, she zipped up my slacks and pressed a hand to the front of them. She appeared thoughtful for a moment before admitting, “You’re right, you’ve gotten bigger.”

I had to chuckle.

She stood up and wrapped her arms around me. My hands traveled down her back and into her loose yoga pants. I felt along her smooth skin, underneath her panties, and grabbed a handful of her firm ass. Her cheeks flexed and a moan escaped her lips. I REALLY wanted to fuck her, but I didn’t think she wanted to. After all, she must’ve put my dick back in my pants for a reason. She was probably still reeling from last night. Instead, my other hand reached down the front of her pants and awkwardly clenched her semi-hard penis.

“No.” She suddenly whimpered.

I froze. “I’m… I’m sorry.” I sputtered but she shook her head.

“No, it’s not… I just… the hormones… my stuff is kinda… atrophied.”

“Huh?” I was really confused now, “What does that mean?”

“It means… well it means it doesn’t really work that great sometimes.” She explained, her face flush though I wasn’t sure if it was from excitement or embarrassment, “It used to be 100% functional but after all these years of hormones, sometimes it doesn’t work as well. The other way still works though”

It took me a moment to register, and when it did, I felt a stir in my pants.

“You mean anal.” I clarified bluntly.

She nodded, but quickly and firmly stated, “And I don’t really want that right now.”

I removed my hand from the front of her pants and went back around to massage her ass. She didn’t seem to mind that at least. She continued to moan and stir as I rubbed her smooth cheeks, feeling the firm muscle underneath the warm skin, spreading them apart and pushing them together, squeezing them rougher with each passing minute. I’m not sure she did this intentionally, but she spread her legs slightly. I took a chance and slid a palm down her crack, my other hand still massaging her ass. My fingers reached her taint and, surprisingly, she moaned loudly and spread her legs a bit more. She bent over very slightly to give me easier access. It was a little awkward, and part of me felt like we should lay on a bed and do this, but I didn’t want to sully the mood by breaking contact. My fingers managed to touch the bulb of her penis, but she didn’t respond as well, so my fingers simply traced up and down her perineum.

She seemed to enjoy it and began rocking her hips in order to make my finger rub against her taint faster. She suddenly stopped and her asscheek clenched in my other hand. She shuddered and gripped me tight, her manicured nails digging into my flesh. She gasped and jolted a few times before relaxing and falling against me, gasping and fighting to catch her breath. When she did, she pushed away from me and grinned.

“Now let me do the dishes, knob!”

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