From straight to sissy cumslut:
I dated girls all through high school and partly into college, and never thought I would do what I’m about to describe. One night after my girlfriend went home from the bars I stayed behind to finish my drink. A tall, dark and handsome man came up to me and offered to buy me a drink. Everything told me to say no, but I’d never had someone offer to buy me a drink so I accepted. We struck up a conversation I can’t even remember, but one drink turned into 2, turned into 4 and then closing time. Something about him made me feel more drawn to him the more we talked.
He asked if I wanted to keep the conversation going and that he lived close by, I said sure and followed him. After 5 minutes we got to his door, and for reasons I still can’t explain, I leaned in and started kissing him. He pulled me in for a deep kiss and squeezed my ass, making a soft moan escape from my lips. “Oh yea” he said, “I had a feeling you might be down”. He guides me to his bedroom and I immediately get to work fishing his dick out of his pants.
I had never been with a man before, so I started doing what my girlfriend did. Licking the tip, slowly working my mouth around his cock while looking up at him. I did the corny thing you see in videos where girls compare it to their arms; he was over 12” long and thick as a beer can. I couldn’t get all of his dick in my mouth, so he started to push my head down until I felt his balls under my chin. I came up for air and told him I’ve never done anything with a man before.
He told me to lay on my back and he would make sure I was ready for him. He put something cold in my ass, I saw it connected to a small hose with a ball on the end. He squeezed the ball and I instantly felt full and moaned. I began stroking him off while he slowly inflated whatever he put in me. After about 10 minutes he took it out, it looked like a balloon with a small dildo on the end. He turned me to face his big mirror on the end of his bed and I saw it, my ass gaping wide open.
He opened a bottle of lube, massaging my now loose opening, and positioned himself at the entrance. He pushed all the way in me in one motion, making me gasp and scream in pain. He held himself there as my insides rearranged to accommodate his massive size. He slowly began to pull out and push back in, making my belly area bulge with every push. The pain quickly turned into pleasure as I told him to fuck me between moans.
He said his girlfriend was out of town for a few weeks and he hadn’t gotten off in a while as he began to slam into me, making me reflexively wrap my legs around him. He picked me up and began dropping my full weight onto his dick, then flipped me on all fours and began to fuck the living shit out of me. After a while he began to pant and I knew he was close. He asked me where I wanted it, I said to cum inside me. He didn’t have to be told twice as I felt an eruption inside me.
What felt like gallons of cum flooded my insides, to the point it began spilling out onto the bed. He held himself there before slowly pulling himself out, a trail of cum following behind him. I had no idea what I had just done as my girlfriend slept across town. I told him I was in a relationship too, but I might be up for more if I was able to. He kissed me and said “oh baby, we’re just getting started”.
He locked the door, drank some water, and I watched as his dick got hard again within minutes. We fucked 4 more times that night, with each round getting kinkier. He started using toys and, by the last round, I was so loose and used he was able to fit a dildo inside me along with his dick, permanently stretching my hole. It looked like a pussy by the end of the night: slick, pulsing and with cum dripping out.
He asked if I was gay, I said no and he said there’s no way I could do what I just did and not be at least bi. I laid there thinking about what this meant. He said that was the sluttiest sex he’s ever seen and asked if I might be interested in testing my limits. I said I’d have to think about it.
I went home after swapping numbers (and another kiss ;))and didn’t know what to think. But I knew I had to tell my girlfriend about it. Weirdly enough, she wasn’t upset about it. She said she didn’t think I was gay but was definitely bi, which was okay with her under one condition: we open the relationship and I can only get fucked by a man if she’s watching.
She then asked to see the aftermath of “the sluttening” as we called it, so I showed her my new pussy. Blaming curiosity she inserted a finger, then 2, then worked her way inside until her whole fist was inside me. She was impressed and said she wanted me to set up another session with Mr. TDH. I texted him and he said he’d only fuck me again if he could invite some friends. The thought scarily excited me and I told him my girlfriend wanted to watch. We set it up for later that night.
My gf and I arrived at Mr. TDH’s house later that night and walked in to see him and 6 other men in the living room. I take a seat carefully, my ass still sore from the brutal fucking the night before, and carefully take in the scene. Mr. TDH says “well get to it slut, just because we have all night doesn’t mean you can put this off” and has me kneel in the middle of the room.
All 7 men surround me, pants down and I see all 7 dicks. 3 are about average size, 2 are quite big about 10”, Mr. TDH whips out his monster and the last guy somehow is bigger than him. I instinctively reach up and grab 2 of the dicks at random and start stroking while Mr. TDH puts his in my mouth and I begin to suck. I look over at my girlfriend sitting on the couch, an equal amount of shock and curiosity spreading across her face as I see her hands drift to her crotch.
Oh god I think, is this turning her on? I only have a minute to think about this before Mr. TDH begins fucking my face and I feel someone start feeling around my ass. “Damn this still looks used, you weren’t kidding man you tore this pussy up” I hear behind me as he pokes around my still recovering hole. Every brush of his fingers around my exposed ass makes me moan around Mr. TDH’s dick.
I look up and see my gf fingers deep in her own pussy as she yells out “well come on then, fuck him!” The man behind me doesn’t need more encouragement as I feel lube drip into my ass and he enters me fully, bottoming out as I moan loudly. Mr. TDH cums in my mouth, holding his dick in place as I swallow every drop. I don’t have much time as another dick soon takes his place and I once more look at my gf.
She’s done fingering herself and now instead has a camera focused on what’s happening in front of her. I figured if she’s going to record might as well put on a show. So I start pushing my ass back onto the guy behind me, making him hit my g spot with every thrust. Not too long after the men I’m stroking off cum all over my hair, back and face, and the man pistoning inside me unloads his seed deep into me.
As he pulls out I feel another dick entering me, longer this time and a bit thicker. I reach back to spread my ass as the man bigger than Mr. TDH smacks my cheeks with his dick. I open my mouth and take in his monstrosity slowly. The new guy behind me doesn’t last long as I feel another load of cum inside me.
This continues, one after another load, until I see Mr. TDH make his way behind me wearing a glove “time to clean this pussy out” and without warning he shoves his whole hand inside me, scooping out the last 2 loads and smearing them on my back and around my hole. He then slams his full length into me as I scream in pleasure around the monster dick in my mouth.
My girlfriend is still recording but I see her positioning herself on the couch so one of the guys can start fucking her. “Might as well get in on this too right?” she says before moaning as she starts getting fucked. Mr. TDH is fucking me like a wild animal, my insides on fire from this new assault. He grunts as he breeds me, holding me in place as he sprays his cum in places I didn’t know existed.
The guy with the monster dick I was sucking pulls out of my mouth and I can see his dick next to Mr. TDH’s, he’s easily over an inch longer and somehow even thicker. “You’re not ready for this, bitch” he says as he flips me onto my back. He pushes on my stomach and a flood of cum rushes out onto the floor, I feel my ass squelch as it pours out of me.
Then he does what I’ve only seen in porn, he places his dick on my stomach and I can see how far inside me he’ll be going. Now fully enamoured with his size, I wiggle my hips and pick up my legs. He starts to enter me slowly at first, snaking his way inside me as I feel myself stretch beyond what I thought was possible. He stops halfway and I moan in protest, trying to take more of him.
He takes the hint, pulls out almost completely before slamming his entire dick into me. I see stars and almost black out from the pain. My gf walks over, camera in hand and face full of cum herself and kisses me. This snaps me out of my stupor and I see my belly bulging with every thrust.
She positions the camera just above my eye level and says “I’m recording this so we can watch this again together, so we can remember just how much of a slut you’ve become”. I moan in agreement as I feel the monster ravaging my ass begin to pulse. He roars as I wrap my legs around him and he fills me back up with cum. My body is in shock as what feels like a never ending stream of warmth keeps flooding me.
He finally pulls out, leaving a gaping mess where my ass once was. My gf gets an up close shot of my entrance before Mr. TDH says “and now for the main event. I broke your bitch of a boyfriend last night and tonight we test the slut’s limits. If he can do what we have planned next he’ll be a full sissy slut”.
My gf gives her approval and I’m ordered to get on top of the man that just turned my ass into a cum deposit. He’s somehow already hard as he guides my ass to his dick and I sink all the way down with a plop. I start riding him instinctively but Mr. TDH tells me to stop. My gf is back to filming as Mr. TDH walks behind me, smacks my ass and I feel something poking at my already full hole.
“Stop” I say “I can’t take you both. You’ll rip me in half, I’ll never be the same again”
“That’s the point” Mr. TDH says as he starts forcing his way inside me. All I feel is pleasure as he grunts and pushes inside me, eventually bottoming out as I feel his pubes against my ass. I’m moaning like a whore as the 2 of them take turns thrusting in me, feeling stretched and used as I look up at my gf filming me.
“Okay baby, I think after today we can no longer call you a man. You’re a sissy now, with a pussy to match. What’s your name?”
Between moans I manage to say “Nicole, call me Nicole”.
“Okay Nicole, I think these 2 gentlemen are ready. Let them breed you, make you a cumslut aching to be used like a fuck toy”
At hearing this I scream out a moan as I feel them, one after another, unleash another torrent of cum into me. I pull off of them, my ass now several inches wide and spilling out cum. By this point the others had left, I hadn’t even noticed. Mr. TDH stands up and kisses me saying “Nicole, tonight you became what you were always meant to be. You’re a cumslut, and you love it.”
He looks at my gf and says “is this okay with you?” She looks at me, cum soaked and used, and says “I’ll have to get over him being turned into a girl but I think I can feminise him. I still love him, and if this is the life he wants I’ll support it”.
That night, Nicole was born. My gf helped get me started on HRT right away and got me set up with some great hypnosis videos and gym training plans. Within a couple of months I was talking and walking like a girl. After 6 months I noticed my breasts started growing. We still had sex on occasion, though usually after having me slut myself out for her entertainment.
2 years, a boob job and several plastic surgeries later, Nicole was ready and came out to the world fully. I still think about that night sometimes, how one free drink started the wildest and freakiest chapter of my life.
