My name is Michael and when I was 20 I lived with my roomate John and his girlfriend Lisa. John was 30 kind of a douche and a little mean and pretty much ran the house definatly an alpha male he was stocky and much taller than me. He wasn’t the best roomate tbh but he let me move in when I had no where to go. Lisa was in her late 20s and she was very hot and was really nice to me almost like a big sister. I was single and pretty lonely I wasn’t really popular with the ladies I’m too akward and too much of a pussy to ask out a girl and because deep down I wanted to be one. I worked from home so I spent alot of time watching sissy porn and imagining I was in the video getting fucked and sucking cock. I didn’t have my own clothes or make up or anything so while my roomates were away I would sneak into Lisas room and get dolled up. I didn’t really know how to do my make up so I would just kinda slather it on messy and really slutty. Lisa worked late nights at her nursing job and wouldn’t be back home till early morning and John worked nights as well and kinda just did his own thing probably cheating on her tbh. So one night they both were gone and I had my sissy alone time I rush to Lisas room and waste no time Lisa was huge nerd and had a bunch of cosplay outfits and wigs this really worked out well for me I just had to carefully put them back. I picked out a Maid dress it was pink with bows and frills and a cute apron and I went to her panty drawer and got the matching white thigh highs with pretty pink bows on them a nice thick padded pink bra and a cute pink thong that was so small and thin it barely covered my clitty and went deep in my cheeks. I picked out her pink wig with pig tails and pink bows and the last piece to tie it all together these really high 8 inch fuck me heels. I really struggled balancing in these and I’m really lucky to be so small and having the same size foot as her. Im standing in awe checking myself out in her mirror thinking “Damn I look hot I look just like a girl.” I carefully walk over to the bathroom where she had all her make up spread out on the sink. I picked out all the pinkish tones and glittery stuff I can find about 20 mins later and I look like a sparkly princess. Lips pink and glossed up fake long lashes silver mascara pink eye shadow and a glitter finish all over. I go to the front room and hop on the computer load up some porn and start getting so horny. I start stroking but very carefully as to not get pre cum on Lisas outfit. 30 mins go by and I shoot out a load onto a towell and I am getting ready to clean up but then suddenly….The door creaks my heart drops and I freeze and I don’t know what to do. In walks John and he looks up at me and says “What the fuck!” “What are you wearing!” I scaredly respond “Oh shit what the hell are you doing here? I thought you were at work?” “This isn’t what it looks like please don’t tell anyone im begging you!” Im so panicked and I can’t move I start breathing so heavy and I feel like I’m gonna pass out. John replies “I can’t believe my roomie is a faggot ass fairy you like wearing my girlfriends clothes you little bitch? Maybe I should treat you like her.” He pulls out his phone and starts snapping photos and recording a video I’m scrambling around almost falling over trying to cover my face. I start screaming at him “Dude what the fuck don’t take any photos delete them nowww!!!!” He yells back “No if you wanna dress up like a bitch I’m gonna make you my bitch get over here slut or I’ll post these pics up all over your Facebook!” I’m freaking out panic is setting in and I just wanna leave I tell him “What no no please no I’m not gay dude I just like how they feel… come on man that’ll ruin my life my family and friends will think I’m a perverted freak.” He angrilly replies “I don’t give a shit get over here and suck my cock or face the consequences!” Now accepting my fate I reply with tears in my eyes “fine ok just promise not to tell anybody please!” He grins and tells me “ok you sissy bitch just do as I say and it’ll be our little secret.” My heart is pounding and I’m scared but also turned on as I have always been jealous of Lisa having John as her boyfriend I would secretly listen to when they fuck and jack off in my room fantasizing about being in her place and having John dominate me making me feel weak and girly. I nervously tell him “I’ve never been with a guy I don’t know what to do” He orders me grabbing me by my neck “pull my cock out you little bitch!” I do as I’m told “ok now what?” “Suck it slut and call me daddy while you’re at it I’m gonna call you Michelle.” I start sucking but can’t help but immediately start gagging and crying and complaining. John rolls his eyes and scoffs at me “Come on bitch this is what sluts do they suck cock now enjoy it.” Me gasping for air almost puking all over “I can’t breathe this is horrible! Please man why are you doing this?”He yells back to me “Because I like dominating little bitches like you I’m glad I came home early this is gonna be a regular thing so get used to sucking slut!” I gasp knowing his true intentions and I have all these feelings to process I had no idea John had a thing for sissies. I continue sucking him for a bit longer to my suprise he tells me “Alright you can stop now.” I feel a sign of relieve I thought this was over but little did I know we were just getting started. He pulls me by my arm hard yanking me off my knees “Get up! Let me see your pretty outfit.” He spins me around. “I’m surprised you fit in all my girlfriends things you really got into this didn’t you?” “Heels pantyhose bra dress panties and even a wig and make up?” “You’re a full blown little sissy bitch!” “You look good Michelle …damn good… good enough to fuck.” I’m afraid and I don’t want to do this even though it had been my dream to have John fuck me it was becoming a living nightmare I start begging him “No please that’ll hurt I’m not into it just let me suck it until you cum I don’t want your dick in me please no no no!” With no mercy he tells me “Oh no you pathetic pussy unless you wanna be exposed as the little girl you pretend to be you better get ready for daddys hard dick! I try reasoning with him hoping he will cut me break “Please please please man I can’t do this I really don’t want it in my ass I never even tried a dildo or anything.” He devilishly replies “Good then that means its tight as fuck don’t call it your ass anymore as of right now it is a pussy do you understand bitch?

I give in and just go with the flow and accept my fate as a fuck toy for my new master. “Yes daddy.” John smiles and joyously says “Alright look who’s submitting now bend over you naughty slut.” With no more hesitating and fear I reply “Yes daddy.” I’m now face down on the bed my ass high up in the air John stands behind me and grabs his belt. “I’m gonna spank you maybe that’ll teach you to not touch my girlfriends stuff!” whack whack whack he swings hard at my cheeks. I yell out “Owwww fuck that hurts daddy!” He says to me “I wanna hear you moan and whine like a girl and I’ll keep hitting you with this belt until its convincing now start counting while I make those juicy cheeks red.” Helpless I bury my face in the pillows and start counting out loud “1 2 3 4 fuck owww 5 6 7 fuck it stings please stop 8 9 10 daddy please I won’t touch her stuff again stop spanking me 11 12 13 owwww 14 15 16. I’m trying my hardest to speak in a girly high pitched tone. “17 18 19 20!!!!” My ass feels like its on fire tears start streaming down and I lay there leaking precum. John breathing heavy “Alright that should be enough to teach you a lesson now I’m gonna loosen your virgin pussy right up go head and grab Lisas dildo I’m sure you’ve seen it in her panty drawer”. She had a huge 10 inch veiny thick black dildo that I didn’t dare attempt to try even though it was tempting at times…I respond “No way that is so long and thick its gonna hurt too much!” He loses his patience and goes and grabs the dildo himself. I squeal when he shoves it in he starts inching it further and deeper in and out it hurts yet it feels really good too. John than gets next to my ear and whispers “You like that big fat cock?” “You secretly want it inside you dont you?” I am getting used to the pain and feeling loosend up and horny I let out a feminine moan and say “Mmm yes daddy!” John is pleased and he pulls the dildo out of my lubed up wet gaping pussy. “Thats what I thought faggot now spread your cheeks and beg for it like a good girl.” I do as my master orders and beg like the horny little bitch I am “Please put that big cock in my pussy daddy I want it deep and hard!” John slapping his hard 9 inch cock against my hole “You want me to shove the whole thing in balls deep in one thrust you little whore?”

This is it I will finally know what its like to be fucked by a real man “Yes fuck me like you fuck Lisa.” John than grabs my hips and thrust hard in me all the way “I’m gonna fuck you harder than she would ever let me!”

I scream “Mmm fuck daddy!” I feel like a real woman he starts pounding harder and faster using me like a fleshlight his grunts and feeling him assert his dominace over me have me so turned on and I don’t want it to stop. He tells me “I wanna hear you beg and moan like a little girl while I destroy your hole!” I can’t help but to just lose it “Oh fuck daddy oh oh shit it feels so good I feel my g spot getting all tingly my clitty is getting so hard please don’t stop keep thrusting in me I’m your little bitch fuck my pussy daddy!” He than flips me over putting me on my back grabs my thighs and puts his cock back in me “Damn this pussy is so tight Michelle much better than Lisas I’m gonna shoot my hot load deep in your guts.” I can’t hold off much longer I start stroking my clitty. “OMG YES YES YES it feels amazing daddy I’m gonna cum!” Johns face is red and he is dripping sweat he looks so intense and I know he is almost done he starts choking me with both hands. “I want to see you squirt bitch I’m gonna make you cum like a real girl you ready Michelle?” I’m panting like a dog and stroking so fast. “Show daddy that sissy load.” I moan so loudly “OHHH FUCK DADDY IM CUMMING!!!!” My jizz explodes all over Lisas dress and wig and my face. John is still thrusting still hard and hasn’t cum yet the pleasure is wearing off and the pain is setting in. “I want you to beg for daddy’s hot load earn your reward faggot.” I’m shaking and squriming trying to power through. “Please give me that load daddy I want your cum inside my pussy make me a woman!” John gives 3 hard pumps and he lets out a loud roar “TAKE MY NUT YOU SISSY BITCH!!!” I feel his dick throbbing from inside and he pulls it out and a warm sticky pool of cum spills from my loose hole. I lay there in pure bliss and feeling complete and processing all that had happened. John tells me “Alright sissy clean yourself up and put Lisas shit back.” I get up and throw the dress in the washer and wash all the make up off. Lisa never found out about this and John and I made this a regular thing I lived with him for 2 years until he married Lisa.