The Bulge

"What's up Ms. Martinez, Connie in her room?" I asked with a charming smile.

"Si," the tired-looking, middle-aged woman responded with no emotion. Connie's mother was only in her late 40's, but the years had taken a toll on her. "Another day of video games, internet and wasting time?"

"That's right Ms. M!" I gleefully replied to her sarcastic comment, "it's our therapy, you know that. We are still working through it all!"

"The marijuana too, that's part of your therapy too, I suppose?" Ms. M. quipped back.

"The most important part!" I answered smiling as I sprung up the steps to Connie's room.

Connie and I were both 25 and went to High School together. We weren't best friends back then but often wound up at the same parties. Connie was a hot Columbian chick, but she was the school pump, catering mainly to the black population. I was the starting QB for our very competitive Staten Island school. I dated whoever I wanted and never pursued her or frankly noticed her much back then. We recently reconnected under difficult circumstances that created a strong bond. Our relationship remained strictly platonic, although I won't lie, I wanted to fuck her. Day-after-day we sat in her room with her voluptuous breasts straining the tight tank tops she wore.

So how did we reconnect and become so close? Well about a year ago we were at the same in-patient psychiatric care facility in Manhattan. Both of us had flunked out of college, done our fair share of drugs and battled crippling depression for the majority of the seven years since graduation. The pandemic was no help and arguably, the breaking point for both of us. When we first saw each other in a group therapy session, we pretended not to recognize each other, and prayed the other one actually didn't. But that, luckily, became unrealistic in the small, intimate environment, and we've been inseparably even since. We made a conscious choice not to fuck, as we were both doing much better and didn't want to fuck up our friendship.

I opened the door to Connie's room that morning without knocking as usual. I always hoped to catch her naked, but remained unsuccessful in doing so. That day however, I got a little thrill. Connie was organizing her room and had her fuck-me lingerie spread all over the bed. She was scurrying to pick it up as I entered, but she only could grab about half. I smiled, jumped on top of it and immediately grabbed a sheer black thong. "Get out!" Connie exclaimed as I held the clean pair of panties to my nose and inhaled with a smirk.

"Stop, you dick, I'm putting this away!"

"Whoa, whoa," I responded, "let's have a little look first."

"Dick, get up, I mean it," She ordered with authority.

"I think, hmmm, lemme think, I think I'll get up, but I think a fashion show is in order! And here I thought we were just going to smoke a bit and play some vids."

"In your dreams perv," Connie barked in her trashy, slightly Spanish, slightly Staten Island accent. "Get off my shit so I can put it away."

"Common, let me enjoy it! I haven't gotten laid in over a year. You can at least let me look!" I pleaded, still smiling.

"Don't even. Get up or..."

Or?" I inquired.

"Just get up yo, it's embarrassing. Stop being a dick Jesse."

"I'll make you a deal, model one outfit and I'll get up and let you put it all away," I said in a serious tone, knowing full well there was no chance. "Damn girl, your ass would look bumpin' in these!" I continued holding the black thong on my extended finger by the crotch.

"Jesse, don't even, I'm not playin' no more, I'm serious. Get up and let me put my shit away."

"Connie, seriously, all day we play video games, fuck around, this is fate that I came over at the exact moment you're rearranging your panty draw. It's like it was meant to be! Now show me what you got girl!"

"I told you I'm not playin'. I'ma put on show for you?" Connie said ending with a 'pfft' sound, "fuck off and move!"

"A'ight, how ' bout this, one outfit and I'll show you my dick," I suggested with a straight face.

Connie burst out laughing, "your dick? You'll show me your dick?" Stressing 'your dick'. "Why I want to see your scrawny-ass dick?" She asked finally cracking a little smile.

"I told you it's not scrawny! It's not huge, but it's a nice dick, I'll jerk off for you too," I offered still knowing I had no chance.

"Dude, GET UP, NOW, I'm done playin'","she emphasized.

"Common, there's gotta be a deal to be made here, what do you want?"

"For you to get your skinny white-ass off my shit so I can put it away!"

"Common," I continued to plead incessantly, "just one outfit, just a few seconds, a quick spin around, I'm so fucking horny now! I need something to jerk off to besides my phone tonight!"

"Dude, seriously, get up. I'm done. It's not funny anymore," Connie said growing impatient.

"There's gotta be a trade here. You haven't gotten laid in forever either. I'm not asking to fuck, but anyone with this many, whatever you call these things has gotta have a kinky idea or two to make the day interesting."

"I ain't been fucked? You don't know shit!" My friend blurted out defiantly.

"Please, we've spent basically everyday together in this room since we got out. Stop fronting', you ain't gettin no dick."

"'Stop Frontin'? Please, you such a white boy. A'ight," Connie said with a little attitude change. My eyes lit up with anticipation as she continued, "tell me somethin' you ain't never told anyone before. Something you plan to take to your grave. If it's good enough, I'll think about putting' on one outfit."

"Now we're talkin', little truth or dare action," I answered, still a bit shocked she entertained the request. As I through my list of exploits, the first thing that popped into my mind was my big secret. I'm talking a confession that would require her to try on every sexy ensemble in the room, but I wasn't giving that up. I thought long and hard and finally selected a good one.

"A'ight, so I tell you a secret sexploit and you give me a show, right?"

"If it's good enough."

"Fair 'nough," I said. "You remember Miko, the half-asian chick that came about half way through senior year?"

"Yeah, scrawny bitch in all the honors classes," Connie confirmed.

"Well, the summer we graduated, I drove her home and her cousin from Japan was visiting. Her parents were out..."

"Let me stop you right there. This ain't no locker room. I ain't listenin' to no threesomes with Asian chicks, cheerleader hoes or any of your frat boy shit. You want a show, gimme something real, something you planned to never tell nobody."

Like I said, I had something real. Something I planned to always keep secret. But I wasn't ready, even as much as I trusted Connie, man I couldn't share that. Or could I? It would be amazing to talk about it with someone. To share it. If I ever told anyone, it would be Connie. And I was horny as fuck and wanted to see that plump but fit fine ass in some of these thongs.

"I got something Connie, but I gotta know. You ain't never gonna tell NO one, no matter what happens, right? And no judgements."

"Shit, this sounds fo' real!"

"No doubt, and you best hold up your end..."

It all started walking to Staten Island's lone subway line about two years ago. It was about a year before I checked into the hospital. I recently moved back in with my mom and she made me get a shitty job at a grocery store. I got to the platform and there was this hot ass Spanish chick making out with some Puerto Rican dude.

I didn't want to stare, but I kept sneaking peaks of the bottom of her fleshy cheeks, which her Saran Wrap-like pink booty shorts squeezed out of the bottom. Her ass was so fat, it was driving me crazy. She had a thin waist and was wearing a tight, white mid-riff t-shirt that contrasted starkly against her deep olive skin tone, and no bra. I was waiting for a turn-around as I knew her certainly dark brown nipples would show through. It struggled to corral her large breasts, of which I enjoyed a clear side-view despite how tight he held her. Her blonde hair was short and straight, styled in a bob that was certainly a wig.

It was her femininity that turned me on so much, but even from behind, I was pretty sure she had an extra measurement. I'm not gonna lie, I'd watched a bit of tranny porn in my day, okay, a bit more than a bit, but I never took the plunge or really considered it. She just piqued my curiosity, you know, you don't see them everyday, at least not hot ones. There were a lot of tell tale signs. She stood remarkably tall, nearly 6-feet, and her slender yet toned arms hung from her shoulders that were sorta too wide and straight to belong to someone with a vagina. Her legs went on forever, smooth, tanned and sexy as hell, but a bit muscular.

My dick tingled as I snuck a few peaks at the couple. I could tell the man was gently caressing and squeezing whatever she had under the front of her shorts, and a desire for my hand to grab whatever it was crept into my thoughts. I'd never done anything remotely gay, except maybe dabbling in some slight anal stimulation by shoving a few household objects up there while masturbating. However, as the train pulled-up, the anticipation of seeing her face became uncontrollable, and I was fantasizing about her pulling her dick out to show me.

I got on the train and strategically hurried to a seat on the far side of the car near the door. I figured I'd get a clear look as she entered. When I sat down, I saw her walking alone to the train and was struck by her beautiful face. Her beautiful, yet classic tranny looking face confirmed what the gods bestowed upon her birth. As I gazed into her wide-set dark brown eyes, my peripheral vision confirmed that her puffy lips and unnaturally high cheek bones were clearly botoxed. The blonde bangs of the bobbed wig framed the sexiest face I'd ever seen, I was mesmerized.

She entered the train just as the doors closed behind her. I knew deep down I wouldn't have the balls to speak to her, but euphoria flooded my body as her friend was just dropping her off. You know, hope springs eternal! And I could more comfortably sneak peeks! I looked up and down the car to address the other concern straight guys have when even the slightest of gay thoughts enter their mind. You know, no one can know! Not even a stranger! There were only two other men in our car, which was good to look but too many to strike-up a conversation with my desire dream girl.

The woman peered straight ahead; not looking at me once. Disappointing? Sure, it always hurts the ego, but I provided an opportunity to gawk more comfortably. Amazingly, She didn't take a seat in the near empty train. Instead she remained standing, leaning back on the doors after they closed, allowing me to take in all of her beauty. Eventually, My eyes traveled down to her skinny neck and prominent Adam's apple before stopping at those buxom, perfectly-shaped fake titties.

I stared at her tits for the briefest of moments before something caught my eye. Something huge. To this point, I discretely stole glances, but when her package caught my attention, I stared intently. Her fully erect tremendous cock bulged from her tight velour shorts, pointing to the side and extending about an inch past her hip. The light pink fabric provided a perfect outline of every inch of this world-class erection. Her large sack was basically camel-toed, and her shaft was nearly the same thickness from base to tip. What struck me most was the thickness, I swear if I wrapped a dollar bill around it, it would reach just a bit more than halfway, and it had to be over eight inches long, if not more.

I don't think I ever saw anything hotter in my life. I was floored. Tranny thoughts crossed my mind before, but I always controlled the urge. I couldn't control this, I had to see that cock, explore it, do, I don't know, but I needed to talk to her. Frustratingly, despite the fact the fact I never wanted anything more in my life, I sat frozen because other people were around! Fucking strangers! But you have to understand, in the early days of tranny chasing, it's a problem even if one stranger notices you approach a person born with a dick.

As we approached the next stop, the woman turned around giving me another glimpse of her supple ass cheeks. Seeing those fleshy rolls of ass where the cheeks meet the upper-leg, that was the key! She was clearly getting off, and I had to act fast. When the doors opened, I sprung to my feet and followed her. I kept a distance, furiously thinking about how to approach her, making sure to stay far enough back to maintain plausible deniability in case I chickened out. We left the platform and continued about another half-block when she finally addressed me. She turned around with a scowl and abruptly asked, "what do you want?"

I was about 10 feet from her and she took me completely by surprise. I stuttered and stammered for a response before I uttered the only thing that came to mind, which was exactly what I wanted, "um, I uh, I want to be with you."

Like I said, I am hot and got laid all of the time, so I am confident with the ladies. I wasn't surprised at myself being so direct. But what i agreed to surprised me a bit, as I never had to pay for it before. She simply stated, "200."

Like I said, I agreed willingly and asked if there was an atm close-by. She told me to follow her and she would point it out. We walked another block or two, not saying much at all. I was a bit freaked out walking with a shemale in broad daylight in public, so that was making me more nervous, especially as we approached a commercial street. All you self-perceived straight tranny-chasers know exactly what I mean. Luckily, the atm was right on the corner and she pointed out her apartment and told me to ring buzzer number 2 when I had the cash.

As I took out the money, I couldn't believe what I was about to do. I was fully erect and ready to make out, play with a dick and suck cock for the first time. I really wanted it up the ass, but I figured I wouldn't do that the first time. I was so nervous and excited as I reached for her buzzer, again, all you shemale lovers know that extreme butterflies in the belly sensation.

When I went upstairs the front door was open and so was her bedroom. I walked in and she was naked with her back turned to me. I did want to slowly pull those shorts down and see that big cock spring from them into my face, but looking at her voluptuous backside was nearly as exciting, not to mention when she turned around and her now flaccid, uncircumcised huge dick hung down between her legs. I asked her name and she just told me to take off my clothes.

As I disrobed, she told me her name was Maya. She turned back around and I could see her putting some make-up on in the mirror. My average-sized dick was hard and as I sat down on the bed I continued trying to make small talk, you know, where you from, how long have you been in NY. She largely ignored me, grabbed a condom from an open-draw and turned towards me. Even though her dick had softened, it was so big and beautiful. I watched it swing side-to-side between her legs as she approached me. It looked just as I imagined while I was staring at her bulge on the train. It was dark brown and soft must have measured six inches at least.

Still having only uttered her name, she finally said something when she reached me sitting on the bed. She asked me for the money. I got up and went to my pants and pulled out the 200 bucks. She took it and went to dresser to put it away. I sat back on the bed and she walked back to me and began to open the condom. That beautiful cock was inches from my face and I put my hands on her hips and began to caress her soft skin.

She didn't allow me much time if any to appreciate her beautiful feminine body. She began to stoop to her knees and planned to put the condom on to suck my dick. At that point, the mood changed a bit. She had not been friendly at all, but that was my tipping point. I stopped her from putting the rubber on my erection and said:

"Maya, this is uh, my first time, can we go a little slower?"

"What do you want to do?" She answered curtly.

"I don't know, kiss, you know, play with you a bit, take it a little slower."

"I don't kiss, and you didn't pay for a flip. You can suck, and then I suck and if you like you can fuck my ass."

I have to say she was very direct. I was a little disappointed, but I was still so turned on I didn't ask for my money back. She stood back up and that's when I reached out and touched a penis for the first time.

Her big cock was so soft to the touch, her skin that is, and warm. I fiddled with it for a minute or so, probably less because she rushed me again. I got her mostly hard and then wrapped my hand around the base of massive member, with her balls resting on my palm. I looked up at her face, which looked disinterested and then back at her scrumptious erection. Before I put it my mouth she asked me if I wanted her to wear a condom.

This was another turn-off and I told her that I was okay blowing her raw. I was so excited to suck that big dick though, I psyched myself back up. I puckered my lips and began to kiss the tip. I then spread my lips, wrapped them around her shaft a few inches below the tip and rested the underside of her penis head on my tongue. I couldn't believe I had a dick in my mouth!

"You a cocksucka!" Connie interrupted, mouth agape and a shocked laugh. To this point, she had listened intently, knowing where it was going but patiently waiting for it to get there. "Fuck, I didn't expect that!"

"What the fuck Connie?" I replied a little pissed. It seemed judgie and I really didn't like her tone.

"Nah Boo. That's hot, go on. I ain't judging' you."

Back to Maya's massive she-cock in my mouth. As I said, her uncircumcised shaft was nearly as thick at the top as it was at the base. I struggled at first the get it sloppy and wet and tried to get as much of it down my throat as possible. It was so taboo, I temporarily overcame the bad vibes she gave off to that point. My tongue and upper-lip were ultra-sensitive to the rim of her bulging tip under the foreskin each time they passed over it as I bobbed my head back and forth along her extra appendage.

I moved my hands from her hips to her soft-to-the-touch but firm and muscular buttocks. I opened my puckered lips wider and began to pull her pelvis forward, forcing her now fully erect member down my throat. I wanted her to put some effort in, to aggressively fuck my face, but I was still a cock-novice. After all, I'd only been a dick-sucker for about 90 seconds.

Instead of fucking my throat, Maya extracted her impressive specimen from my mouth and started to push down on my shoulders. "Lie down," was all she said. I complied but started to get annoyed again as she walked back to her vanity and grabbed a bottle of lube. She looked incredible standing over me, her legs spread, slightly squatting. She spirited some gel onto her finger tips and planned to apply it to her asshole by sticking her arm through her legs. "Wait," I said. I had enough.

"Yo," I continued, "this is my first time, I thought I had an hour?"

"You're not my boyfriend baby," the 'baby' said very unaffectionately, "do you want to fuck or not?"

"Listen, it's my first time with; you know. Let me get my money back, or at least $150. It's not what I expected."

"Fine," she said in a pissed-off tone. "You fucking faggots are such bitches," she complained as she swiftly moved to the drawer where she put my money. "Get out."

I got up and started to get dressed...."

"Wait," Connie interrupted again, "that's it?"

"Relax, there's more," I assured her.

As I hurriedly got dressed feeling disappointed and vulnerable, Maya first sat at a desk near the window facing away from me. I needed to get out of their quickly. I felt awkward and confused enough having just had my first sexual experience with a biological man and a pro. White boy novices like me are so worried about getting caught by the cops or having anyone, even strangers know your a cock-craving deviant. Then there's the safety issue too. You wouldn't want to fight back if anything happened as that would increase the chances of you getting caught or worse.