Author: Storiesfromthediary

My flatmate turned me into his Sissy Crossdressing Slut (Part 4) [24] [MM] [Bi]

Its the next day. I wake up, smelling feminine still wearing my flatmate’s girlfriends lingerie under my pyjamas. I feel slutty and ready for the day. I woke up early, before anyone else and ensured that whatever was going to happen today, I was prepared. I took off the lingerie and neatly lay it on my bed. I showered, cleaned inside and out and trimmed my hair. I smelt and felt good. I returned to my room after breakfast and completed any outstanding work for the day.

Hours pass. I already put the lingerie on, awaiting what could happen next. My flatmate and his girlfriend were awake, talking and laughing. I was getting annoyed, but horny at the same time. I wanted his cock. I wanted to be his sissy slutty bitch on demand. My ass twitched and my cock got hard thinking about all the future sex to come with my flatmate. Outside my door, I hear my flatmate leave with his girlfriend. Read more »

My flatmate turned me into his Sissy Crossdressing Slut (Part 3) [24] [MM] [Bi]

*Thanks for all the feedback so far, many more stories to come!*

I’m lay on all fours, ass in the air, dressed like a slut, about to enjoy my flatmates meaty girthy cock deep in my ass when the front door is being unlocked. I couldn’t believe my luck. Its twice now that I’ve been interrupted during some of the hottest, dirtiest sex of my life. He pulls his cock quickly out of me as we both hear it. Its a feminine voice, echoing up the stairs, shouting out for a name…my flatmate. The very flatmate who seconds ago had his cock deep inside me, making me wear his girlfriends lingerie. The very girlfriend about to walk the 15 seconds it takes to make it upstairs. He panics and shoves all the things from his girlfriends bedside back into the draw. I leap, carrying my clothes out the room and dash into mine, closing and locking my door behind me, still wearing his girlfriends lingerie. She continues walking upstairs as I hear her reach the landing and walk towards my flatmates room. Thankfully the stairs and landing area has a blind spot, allowing me to dash out without anyone seeing me. She walks uninterrupted towards his room as I listen to the conversation. “I’ve had a shit night out and I wanted to stay here if that’s ok?” She says to her boyfriend. “Sure, don’t worry about it!” My roommate replies. My naughty, slutty streak returns. Imagine if he’s still wearing the condom? The very condom that’s been in my ass, wrapped tightly around his big cock, tucked into his pants. My cock gets hard again as my lubed up ass twitches to be filled. I walk over to my bed, quickly shove a buttplug inside me to quell my cock desire. I lie down in bed, refusing to take the lingerie off. I smell so slutty, so feminine. I smell of her and I loved it. I lie in bed, lights off, slowly pleasuring my wet pre-cum soaked cock and ass. I hear my flatmate talking next door, nothing of interest. Read more »

My flatmate turned me into his Sissy Crossdressing Slut (Part 2)

*Please read Part 1 if you haven’t already*

I leaned over my shoulder to see what he was doing on the bed. He was stroking his cock, getting it fully erect for the moments to come. He grabbed a condom, rolled it slowly over his thick meaty hard cock. He popped the top off the lube on the bed and began to smother it over his cock. I was attracted to it and he knew it. Read more »

My flatmate turned me into his Sissy Crossdressing Slut (Part 1)

Weeks have passed. My first experience having gay sex still protrude my consciousness and I’m still aching for more cock, more experiences and being more submissive than ever before. It taught me that having sex with a man isn’t just something I like. I needed it. My flatmates had returned from the extended holiday period. I lived with 5 others, all studying a variety of courses with little overlap. We were all a little different, but we got on, and that’s the most important thing.

I’m still haunted by the thought of being caught having sex with another man. Did my flatmate hear it? Did he hear me? Did he hear me getting fucked? Moaning? Did he hear me wanting to suck cock, get fucked? Did he hear me acting slutty?

These questions ring around me head. His room was next door to mine. And I know the walls are thin. Like really thin. If he’s talking to someone in his room, I can here it. Which means only one thing. He could hear me…

The smirk he gave me on the day I had sex for the first time was ingrained into my vision. Did he know something? Did he enjoy it? Or was I just being paranoid? Read more »

Getting fucked and creamed at the Cinema (Story) [M24]

My university town was tiny and had a small cinema alongside a more popular chain which 99% of people went to. I discovered that the cinema was a hotbed for cruising due to its small foot traffic. Great I thought. I wanted to cruise and get fucked. I was craving cock that week and decided it was a good idea to visit. Even if nothing happened, at least I tried right?

Viewing a few public forums, the cinema was in disrepair. Missing seats, terrible audio and little variability in film choice. Seedy was an understatement. But I didn’t care. I wanted cock. Lots of cock.

Tuesday arrived. I decided this was the day to go. Was this even a cruising spot anymore? The website suggesting it was was old, outdated and there was little evidence people even go there anymore. I prepare like normal. Clean myself inside and outside. Place condoms and lube in my pocket. I was ready. Worse comes to worse? I get to watch a new film. Read more »

From Straight to Curious (Full Story) [M]

(I posted this story and others a while ago on another account but deleted it all (mental health is a bitch), Anyway I’m back and I’m reuploading it all. Enjoy!)

Hi. From the age of 19, I’ve always wondered what it would be like to have sex with another man. I considered myself straight, having several girlfriends and always believed that this was me until I eventually met “the one”. When I moved to university, it was a chance for me to explore myself, seek goals and opportunities I didn’t have back home. I could be a new me.

My university was around 60 miles away from home. Far enough to seek new opportunities, but close enough to return at anytime. In my second year, I developed a relationship with a girlfriend which was fun, but not fulfilling. This eventually broke up badly leaving me in quite a bad place mentally. But I was free…free to explore.

I decided since I was single to explore the sexual side of myself that always scratched the back of my head. I wasn’t physically attracted to Men, but I always enjoyed the thought of being submissive to one. Why, I don’t know. Perhaps I just wanted to be dominated, the thought of being owned. I wasn’t sure at the time, but I knew that this might have been the only opportunity and period to explore in my life. Read more »