Throughout my childhood and adolescence I had one friend above all else; Alex. We were neighbors when we were five and first met, doing normal kid things. When we hit middle school our bodies and personalities started to change. I started getting muscular and tall, he grew little height ways and his muscles seemed to slender out. I started getting a lot of attention from girls and Alex always seemed to just tag along. Still there was nothing that had really changed, we were just as inseparable. With high school though came a whole mess of change that could have stressed our friendship. I had continued to develop into nothing short of a mixture of a Calvin Klein underwear model and a NCAA linebacker; I stood six foot flat and 215 lbs of muscle. As the school’s champion wrestler, my sculpted body and massive cock was on display for all to see in my lycra singlet. Alex became an athlete himself, even at only five feet four inches he had taken swimming and become lean and slender with firm, if not overly impressive muscle, however his speedo also showed off assets, or lack thereof. I’d never have made fun of him for it but he had to have close to the school’s smallest cock. Every coach said if he’d had a couple more inches he’d be setting state records instead of placing 5th, By this time though Alex’s femininity was starting to come out. He had a soft voice, almost girlish and really just beautiful features, with pouty lips, deep blue eyes, and surprisingly long blonde hair for a swimmer. When our senior year came around he unsurprisingly announced he was gay. I loved him as a brother and hung out with him just as much. Bullies at our school started picking on him and even threatening him, I stuck up for him at every turn. Then the bullies started making comments to him about his obvious love for me or even that I fucked him whenever we spent the night at each other’s house. This was of course untrue, we had never done anything and he had never even made a move on me. I approached these guy’s and reminded them that if they didn’t shut the fuck up I would do one of two things: either beat the living shit out of them (which I was fully capable of doing), or that I’d remind them of my heterosexuality by fucking their girlfriends (which I was also fully capable of and often did), they would promptly shut their mouths or say they were only joking around. Alex thanked me more times than I can remember, I told him to forget it and just be the happiest little fruit that his heart desired. We’d laugh and carry on our friendship.
Alex’s parents were as supportive as he could have hoped to be. His mother accepted him fully and loved him the same (she even seemed a little proud), his father was less thrilled but he seemed okay with it too, he was mostly to busy making piles of money on the stock market. My parents were a little wary of what they pictured as the world’s most perfect son spending most of his male bonding with a gay kid, but they had known Alex for so long they couldn’t be but so insensitive (besides they saw how many insanely hot girls I went out with on any given week they figured I probably wouldn’t be giving up that much ass for a childhood guy friend).
Alex became the hottest gay guy in town and dated his share of guys, mostly small slender fellas like himself, and I continued my march through the counties women. We would talk of our sexual escapades whenever we hung out, mostly about me and the girls though. I’m not sure if it was because he didn’t think I’d want to hear about him and his guys, but it seemed more like he was really interested in hearing the details of my latest sexual conquest. It was almost like he was trying to pick up pointers on how the women responded. He was especially interested in hearing about the girls giving me head, what they did, what felt best, how deep they could take it. When I told him how this one girl had almost taken my whole ten inch cock down his eyes bulged and he said “Wow, I probably could only take half of that!” “If that much!” I laughed, it was the first time he had ever even inadvertently mentioned a sexual situation between the two of us. This wasn’t the first thought I’d had of sex between the two of us, what with all the rumors that idiots spread around school that he was me secret bitch or something, it couldn’t help but to have crossed my mind. But the mental image of my cock shoved half way down his throat did take a minute to clear out of my head. I had had previous girlfriends raise the question of whether there was anything between us, when I affirmed to the negative most would say something along the lines of “thank god”, but there were a few who said they thought it would have been hot if it was true, which made me wonder.
When we graduated high school it became apparent that Alex and I would be going to the local college in the heart of our neighboring city. We decided to rent an apartment together rather than go for the normal rinky dink freshman dorms. His rich father paid for over half of our pretty nice place and my scholarship to compete for the school along with student loans paid for my share. Living together was really awesome; we got to hang out constantly and he helped me tackle my school load which was tough to balance with my training and competition. Alex would come to all my meets and would usually sit next to whichever girl I was currently boning. Sometimes it would be hard to tell which one cheered louder for me. Sometimes I’d sit at home after a workout in just my briefs on the couch in front of the television. During these times Alex would always sit on the chair that was sort of opposite to me, I figured it was cause it might be a little awkward if he was sitting right beside me with my huge cock only a fabric away from being exposed, or it might have been so he could have stole little glances my way. There were also times when his boyfriend would come over to pick him up and I’d still be sitting there in my undies, muscles still taunt from my work out, when Alex would rush his boy out before he said something lewd, though I didn’t mind I usually found them funny. Our rooms were side by side so there were definite times when one of us could hear the other one fucking, or on a few occasions both of us were getting down. The sexual tension was building even if only a little.
Alex began to wear more girlish clothes around the end of our freshman year. He started wearing tight little shorts that girls wear with juicy or whatever on the butt or daisy dukes and tank tops. He also seemed to have an affinity for knee high socks. What with his hair and his clothes he was starting to look more like a particularly flat hot girl than a boy. This is the time that we both discovered the wonders of alcohol and on one night where we were especially drunk I brought this up. He was sitting sideways in his lazyboy with his cute little legs pulled up to his chest and his blonde hair laying across his shoulders sucking down the beer in his hand. I was sitting per usual on the coach this time with only a pair of sweat pants on, my cock outlined perfectly along my left leg.
“You know, I’m not sure if it’s because of the beer or what but you really look like a girl tonight. No offense…” I slurred, not sure if that might be insulting
He laughed “none taken and you look especially like a man today ha “Then he set his drink down and turned to me with a more serious look on his face. “But seriously do I look like a girl to you?”
“Hmm,” I tilted my head and scratched my chin. “How bout you stand up and give papa a turn so he can give you his full opinion haha.”
Alex stood up a little shakily and set his beer down and struck a pose then gave me a twirl. He stopped with his back to me, stuck out his ass and arched his back, then bit his lip and looked at me over his shoulder. I reached over and slapped his ass, it felt great, really plump and looking really fuckable.
“Well hey there lil missy what’s your name and what’ve you done with my friend Alex?” I joked.
“No seriously!” he blushed and stifled a giggle. He turned around, hands on his hips and tapped his foot.
“Seriously? If you had make up and some tits you would probably fool me” I said earnestly. “You really think so?” “Yeah why though? Do you wanna become a girl or something?” “Well…sorta. Not full on just you know some implants and I’d start dressing like a girl every day.” “Is that so…” “You don’t think it’s a dumb idea or anything do you? Like I’d make an ugly chick?” “Hell no! Shit I’d probably fuck you…that is if I didn’t know you or anything” I hastily added feeling very drunk and stupid.
“Oh…well thanks” Alex gave me a soft smile. I got up and mumbled something about being to drunk and having an early morning class. Alex whispered night and I shambled off to bed.
The next morning Alex wasn’t up yet when I left for school, and I felt really dumb for what I had said the night before. I spent the whole day thinking about my gaff from the night before and was hoping we could just forget about it. When I walked through the door to our apartment I was greeted by Alex in full make up, hair in a pony tail, earrings, a short skirt, a tank top, and her usual high top socks. I was a little taken aback.
“Afternoon stud” he (…she?) greeted me. “Hey, uh babe? Ha” “You have a good day?” “Sure did. So uh you’re going through with this whole transformation thing I take it.” “Sure am! I’ve even talked my dad into paying for breast implants so this summer don’t be surprised if you walk in and find me with a nice rack haha” “That would certainly be a surprise haha. He was really okay with it?” “Yeah well I reasoned with him that it’d be like getting a daughter since I know he’s never been totally okay with me being gay. But I know he loves me all the same and mom won him over. Besides even if he’s not, according to last night I have a new papa haha” I had almost forgotten my comment from last night, I laughed and apologized again but she waved me off.
That night we settled into the nightly routine of drinking and watching the tv, this night though Alex sat on the couch with me, curled up on one end with her cute butt pointed at me. Everything was going normal except maybe I was a little tenser. I had opted this night for a wife better and some briefs, my cock as usual very prominent. I wasn’t talking as much, and I think Alex noticed.
“Do you think your girl friends will get jealous of you living with a tranny now?” She asked me randomly. I looked over and met her deep blue eyes and saw she was serious.
“I hadn’t really thought about it but, it doesn’t really matter though you’ve been my best friend for like 15 years now who cares what they think?”
“Yeah they probably wouldn’t even think of me as a challenge for your affection, I’m not pretty enough” she turned to the TV with a sad look on her face. I slapped her ass, letting my hand linger a little longer.
“Oh stop it you’re sexy, and just wait till you get some tits you’ll be knocking those boys out” She giggled and punched my shoulder playfully thanking me between laughs. I slapped her ass again and she bit her lip. We let the moment pass. As the night wore on and we started slipping into sleep I sprawled out on the couch. I woke up at around 3 am lying full out on the sofa with Alex asleep on top of me. She was curled up with her head laying on my abs and one of her hands on my thigh, dangerously close to my cock, which I noticed was poking out the bottom. I got up gingerly and picked her up in my arms like she was nothing. I took her to her room and tucked her in. I stood there a while then leaned forward and kissed her on the forehead and whispered goodnight. I heard her whimper goodnight back.
We settled into a new routine of waking up on the coach together and me carrying her and tucking her in usually with a midnight kiss on the forehead. I started dating again and bringing girls back usually meant I had to explain our living situation to them. Unlike high school very few thought it’d be hot if we fucked and more seemed skeptical and jealous of this “lil tranny slut” that I lived with. I told them time and again that there was nothing going on and that Alex was my best friend, if they couldn’t deal with that then maybe we shouldn’t date. Alex seemed pleased that she was considered competition; she even liked her nick name. She’d joke every time I brought a new girl back asking “Is this one jealous of your ‘lil tranny slut’?”
Alex started dating more straight guys around this time and sometimes I would get a little jealous, which I think she could tell. She’d dress really slutty and tell me not to wait up with a wink. My response would be a firm slap of her ass and a warning that they better treat my lil tranny slut right. She loved it.
When summer time came I told alex I’d be gone for a week to visit a relative out west. She said she’d miss me and gave me a kiss on the cheek telling me she’d have a surprise …or two for me when I got back. I was a little taken back and reacted instinctively by my usual slapping of the ass, this time however I cupped it and squeezed it sort of lifting her up. She released a gasp of shock and I dropped her with a quick I’ll miss you too babe with a wink.
I spent the whole week at my uncle’s thinking of Alex and her surprise, more than my then girlfriend Devon. I talked to both on the phone every day and found that I couldn’t wait to get back to my girls. When I got back I noticed Devon’s car parked in front of the apartment along with Alex’s in her normal space. Devon was probably the coolest girlfriend I had when it came to the whole Alex situation, they were regular bosom buddies. I would frequently come home from class to them chatting away, so it was no surprise that she was there with Alex waiting for my arrival. I walked in and announced my presence with a loud “Where’re my girls at?”
Devon greeted me with a big hug and a kiss. “Wait till you see Alex!” she giggled. “Why? What’s u- woah!” Alex had just walked in from the kitchen where she and Devon had apparently been making a welcome home dinner. What had shocked me was that besides the huge grin Alex wore on her face she had a pair of huge tits displayed well by a low cut top with her daisy dukes. “I think he likes them!” Devon giggled. Alex let off only slightest of blushes and giggled as well.
“Well enough staring at Alex’s new rack lets get dinner started” Devon interrupted. I shook my head and tried to clear my thoughts and keep my eyes above neck level. Just as we were sitting down Devon got a call from work and she had to go in. Suddenly her mood seemed to change; it was like she was fine joking about Alex’s tits until she had to leave me alone with this new bombshell. She shook it off and told us no titty fucking while she’s gone jokingly.
So Alex and I sat down to dinner and she told me how she had had the surgery during the week and how Devon had taken care of her while she healed up. She said they had become closer and talked a lot.
“Oh yeah? What about?” I asked trying to keep from staring directly at her tits.
“oh this and that mostly she kept going on about how great your body is and how huge your cock is” she said coyly. I laughed “Oh yeah haha what’d you say?”
“Well I said you’ve always had a great body and that your cock was the stuff of legend around the school but I didn’t know personally or anything.”
“yeah you’ve only been using it as a pillow every other night haha.” She got a kick outta that one and nearly choked on her wine with laughter. Dinner went on as normal and as the wine kept flowing my gaze went further and further south till I was practically staring at her tits at the end. We cleaned up the table and there was a moment when she was bent over the table and I had to squeeze by I purposely let my cock brush against her ass and used my hand on the small of her back as if I needed support. “A little tipsy are we?” “Just a bit babe”. I went to my room and changed out of my clothes, feeling adventurous I chose to go no shirt and only sweatpants this night. When I sat down on the couch Alex was nowhere in sight so I figured she went to change as well. Alex came walking out of her room looking like the hottest little slut I had ever seen. She had done her hair in pig tails, her usual knee high socks, a pair of tight pink little “boy shorts” underwear that showed the curve of her ass perfectly, and a sports bra that could barely contain her new huge tits. She plopped down on the couch beside me and snuggled in close. I kept stealing glances down her bra and she caught me every time.
“Well do you wanna see them then or just stare at my cleavage the whole night?” she giggled.
“Sure bust those bad boys out ha”. At this she faced me and pulled her sports bra up and out popped a pair of perfect c cup tits. They looked so real you’d never have guessed they were fake. Her nipples stood erect and welcoming, begging to be sucked. “Those look amazing!”
“do they really?” “Fuck yeah they do.” “Here give them a feel,” she said as grabbed my hand and brought it to her right tit. I was shocked that she would be so forward, but all I could really think about was the amazing tit I was currently groping. I gave her nipple a pinch and brought my other hand up to feel both at the same time, she bit her lip and closed her eyes as I continued fondling her new tits. “Feel good huh?” “Oh yes.” She opened her eyes and glanced down at my crotch, stifling a giggle. “It looks like it feels pretty good for you too. Hehe.” She said pointing at my stiff cock which had crept up the left side of my leg and was forcing the material up to about my knee. “Whoops ha yeah I guess it they did feel a little too good,” I said as I removed my hands from her and pushed my cock down. She giggled and covered herself back up. She stood and walked into the kitchen. “I’m getting a snack, do you want anything?” “No I’m good.”
I heard her rummaging around in the fridge as I closed my eyes and mentally willed my erection down, thinking of baseball, puppies, and old people. I felt my cock easing up a bit as I fought the image of my incredibly hot tranny best friend/ roommate out of my mind. Upon Alex’s return from the kitchen my cock had gone to about half mast and I felt confident enough in my ability to handle my horniness at the moment. When I opened my eyes again I saw Alex had decided on her favorite treat, a Popsicle. As I watched her suck on the popsicle I felt my cock stirring back to life. She was sucking the popsicle in the most obscene way possible. She licked it erotically and then softly sucked on the end before slowly pushing the frozen treat down her throat. She was essentially giving it a full on blowjob, all the while staring innocently ahead as if she wasn’t doing anything in the least bit inappropriate. She turned to me with it still in her mouth, pig tails bobbing, looking like the naughtiest little girl this side of a cheap porno.
She pulled it out making an exaggerated popping noise “What?” she asked ever so girlishly. “You are such a little cock tease!” I said giving her a light push. Laughing she said “I have noooo idea what you’re talking about.” With this she began to give the popsicle an even more erotic sucking closing her eyes and making love to the flavored ice with her mouth. “You’re sucking that popsicle like the thousand or so dicks you’ve sucked please it’s so obvious! Haha” “I have not sucked thousands of dicks!” “Okay the hundreds of dicks haha.” “Well you’ve got me there hehe” she said with a wink. “watch how good I can deepthroat!” she again slowly pushed the popsicle all the way down and then began moving it back and forth, picking up speed. I could see its outline in her throat as she fucked her mouth with it. Then she pulled it all the way out with another wet popping noise and a satisfied look on her face. “See, I’m a champion dick sucker!” “That was pretty impressive, but again like I said all those years ago you still couldn’t deepthroat my cock.” I said with a smirk as I grabbed my cock through my sweats and shook it back and forth. “I dunno I think I could…””Not a chance babe””Yes huh! I bet I so could!” She sounded like a little girl whose daddy had just told her she couldn’t take care of a puppy. “I’ll take that bet” I said with another smirk as I pulled my dick out. It stood a foot long, throbbing in its massive thickness. I got up and stood directly in front of her, her eyes bulging as a wicked smile erupted on her face “Deal.” She leaned forward mouth opened wide at the ready, but I pulled my cock away. “At-at-ah. And if you can’t get it all the way down you’ve got to finish what you started.” “Okay that’s fair, what if I’m right though and I can do it?” “Whatever you want.” “Deal!”
I pushed my cock back in front of her face, she leaned forward maintaining eye contact as her lips slowly engulfed my head. She pulled my dick back out and began licking every centimeter of it, drenching my cock with her tongue. She spit on it and worked her hand up the entire length to spread her salvia. With my cock fully lubed up, she returned to the task at hand and engulfed me once more working her head back and forth going deeper each time. I felt my head hit the back of her throat and let out a moan as her real test began. She pushed but it wouldn’t budge, and I watched her eyes as they narrowed in concentration, then I felt it. My cock had been forced into her throat and the excitement in her eyes played out to my delight. “Atta girl keep going only 8 more inches to go haha!” I cheered her on. She looked up at me and her eyes smiled in away her stretched lips could not. She worked my cock further down, back and forth her lips and tongue raked my cock with pleasure and then it seemed she simply could not force any more down. She pulled back all the way out gasping for breath. “Not bad you got over half way! But that wasn’t the deal babe…do you give up?” Still breathing heavily she managed “Never!” and attacked my cock with gusto reaching her previous depth but again unable to go any further. “Here baby lemme lend you a hand.” I grabbed the back of her head in my hand and pushed her forcibly down, she struggled a bit but more with my cock than with me. She reached the last 3 inches but could go no further. As horny as I was, I restrained myself from forcing her the rest of the way down out of fear of seriously choking her. “Oh you’re so close!” I removed my hand and she fought on but gained no ground, finally she relented and my cock rushed out of her mouth with a satisfyingly wet pop. I hung before her dripping wet as she looked up at me and pouted “I can’t do it..” “I know baby, I know but that was a great try!” “I wanted to do it so bad, make you proud of me..” “that’s alright baby, but a deals a deal you’ve got to finish what you started” I pulled her off the coach and onto her knees and put my cock back to her mouth, she happily opened up and began to bob and twist her head, working her tongue and fist back and forth as her other hand groped at my enormous balls. I grabbed her by the pig tails and fucked her mouth in rhythm with her sucking. I was in true ecstasy for a half hour and would’ve spent the rest of my life in that tranny’s hot mouth but all the sexual tension from the years had built up and I was about to cum. “Look at me baby” She looks up at me with those same sweet blue eyes that I’ve know nearly my whole life and she knows I’m about to cum. She pulls me out of her mouth long enough to gasp “I want it now baby” before plunging my cock back in her sweet mouth. She pushes me over the edge with this and is sucking for all her worth. I can feel her pouring her love for me from her mouth to my cock and I finally explode. Her cheeks practically fill as I empty my load all over her tongue and the back of her throat. She swallows it all down and continues to suckle at my cock as every drop is pulled out. After a few more minutes I can take it no longer and pull it out. “Damn that was a good lil girl!” She smiles at me and shows me her tongue, showing that she took it all down. “Thank you daddy” she giggles. I pick her up in my arms and we drop on the couch. I stare at her and finally do what I’ve wanted to ever since Alex first went from a he to a she. I kiss her on the mouth and we embrace for what seems like an eternity. Our lips break apart and she nuzzles into my chest. Soon she has dropped off to sleep and I am not far behind. We drift into deep slumber still in each other’s arms on the same couch as we have many times before only this time everything has changed.

More to come?

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