So, this week I ended up staying at my aunt Lucy’s for some family reasons. She was the type of woman that looked like she was in her mid – twenties, even though she already well into her forties. Needless to say, I’ve always found her to be very attractive. One the second day I was there, when everybody had left the house,I couldn’t help myself, so I made my way to her room.
At this point I guess I should mention that I’m a closet sissy. I’ve always been on the more feminine side ever since I was young, and I’ve always had a submissive nature. Gradually at some point I started dressing up, wearing make-up, bras, panties – either brought discretely online or from a family member. And soon, I had bought my first toy, and my collection increased from then onwards. I eventually became so heavily dependent on my toys until I can barely ejaculate without anal stimulation (i.e. without something up my ass), I also often walked around with a buttplug firmly lodged between my cheeks, and a chastity cage on my already really tiny penis (barely even 2.5 inches hard).
So anyways, I dug through her wardrobe and started dressing up in her clothes – she had this really cute pair of matching cotton panties and bra, which smelled really good. Just the smell alone was intoxicating. When I looked at myself in the mirror dressed up in drag again, I felt a bit ashamed and disgusted at myself, but that only made me more aroused and stimulated – I could feel my blood rushing to my head and my heartbeat getting faster and faster. When i finally took them off, I found that I ended up leaking precum all over them, and some parts of it were soaked through. I ended up placing them back to their original places without cleaning the precum off, and it was then that I noticed that she actually had a shoebox carefully hidden underneath a pile of clothes. I opened it to discover that it was full of toys – dildos, vibrators beads… you name it she had it all. It kind of surprised me, because i had always thought of my aunt as someone clean and pure, and I had absolutely no idea that she was into things like this. I almost wanted to slap myself silly at that point, because I felt so repressed for the past couple of days, (due to being unable to cum without anal, and I had no toys on me…) and there was actaully everything that I needed right here. But I knew that my aunt was likely to be back soon, so I had to painfully give up on the opportunity at the moment.
I was pent up for the rest of the week – the only thing on my mind was revisiting the same experience again with the added anticipation of finally getting to cum, while using that huge dildo of hers I had my eye on. I didn’t really get the opportunity until yesterday night when the house was empty again. I raced up to her room, and immediately dug out her treasure trove of toys, before picking out the largest dildo among the lot. I had my eyes on this really sexy Victoria Secret thong that I noticed last time, and i immediately put it on. I had no idea where the lube was (even if she had any), so I started sucking on the dildo and lubing it up with my saliva. After a really sloppy job, I slid it up my ass, which was almost twitching in excitement. The instant it went in, I felt a jolt go through me, it felt soooooooooo good to have something fill me up again after what seemed like god-knows how many days of pure suffering. I placed it up straight and started bouncing on it like my life depended on it. Soon, my aunt’s scent started making me fantasize about her – that she was pounding me with a huge strap-on. I began to lose myself in the pleasure, and started moaning really loudly “Ahh.. yes.. urrg, fuck me harder aunt Lucy! oh yes…”
And… right when i was almost to climax, was when everything went to shit.
The door to her bedroom swung open, and I could feel the blood in my vbeins freeze over. There she was, my aunt Lucy standing here, wide-eyed in shock, staring at the abomination that was in front of her. In her eyes, I could see a mix of shock, anger, but mostly disgust. I could see her eyes sweep across me, and when it landed on the pathetic excuse of a thing I call a penis, my arousal hit its peak and I couldn’t help but cum. I came right in front of her, squirting all over the place. Some of it even landed on her clothes. I could feel my butthole spasming and contracting on the dildo, and my whole body was quivering.
She just looked at me, and her shock soon all turned to disgust, which turned to rage. She just screamed at the top of her lungs “GET OUT!!!” and pointed at the door. I knew that I really fucked up this time, and I fumbled out of the room as quickly as I could. I ended up tripping over halfway due to the thong that was still between my legs, resulting in a sort of half-crawling, half-running as I tumbled out of the room, with the dildo still dangling out of my ass. I made my way back to my room as fast as I could, and bolted the door tightly shut, before collapsing on the ground. The only thought going through my head back then was that I was screwed. Royaly screwed. However, my heart was still pounding like crazy, and the arousal and excitment had not died down the least.
That night, I came harder than I ever came before. That was arguably the best orgasm I have ever had in my life. I write this as I prepare to depart back home. It turns out last night was too chilly and she came back for a coat. Thankfully, it seems like she has yet to tell anybody else of what has happened. However, when I think back to the events last night, and the look in her eyes, it sends shivers down my spine and I could feel myself wetting the underwear I’m wearing. I could almost picture her thinking to herself, “What a fucking sissy faggot”. I’m not really sure what propelled me to share this, but I find myself unconsciously looking forward to the humiliation and disdain that others might have for me, the thought of others reading what has happened makes me feel both extremely excited and disgusted at myself. I really regret what I did, and sometime I feel like if I was better looking, or if my tiny penis wasn’t so small, I’d have the confidence to be a real man. What do you guys make of this all?
TLDR: I had always been a closet sissy. For one week, I was staying with my aunt. I dressed up in her underwear, took her dildo, and started fucking myself with it, and she walked in on me. The look of disgust on her face just made me cum so hard, I could feel myself spasming on the dildo. I’m ashamed of myself, but not sure what to make of the whole thing.