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.
Tag: Humiliation
[M] (18) dirtiest thing you will read on here.
Pre-read: Innocent attempt, turns into my worst nightmare…but I kind of like it.
Kinks used: blowjobs, deepthroating, rim job, toilet play, toilet humiliation, foot fetish.
Story:
I’m usually into women. I’ve had a couple of girlfriends in the past. But there is a part of me that is attracted to men. This part of me comes out only once in a while. However, the last time it did, things got a little out of hand.
I decided to give it a try and meet a man on here. I’m 18 so I wanted someone around my age. It was simpler than I thought, all I had to do was post on a few subreddits that I am looking for someone to try it out with. I got plenty of responses. At random, I picked one and begin talking. The guy seemed pretty interested and happy to see my post. We decided on a date and time and decided to do it at his place. It was clear in my head, I’ll go over, I’ll blow him, he’ll blow me, maybe try a bit more and we’ll never see each other again. Although, things turned out to be a bit different.
Breakfast is Served [FM][FDom][msub][chastity][denial]
Inspired by a post from/u/taco_kitten. Link in comments.
Today is the day; the day you promised; the day I have spent these months waiting for; the day which has filled my every waking moment ever since That Day…
…That Day, yes. I suppose that’s the place to start; the Day everything changed.
I’m a successful businessman, running a small property agency with a few branches across the country. From the one property I started with, I now manage a portfolio of over a thousand properties, worth over a hundred million, and turning over more than ten million a year, as well as sales and rentals on behalf of clients. I don’t say this to boast, at least not anymore, merely to give you an idea of me, and how easy it is for me to have anything I want. I live well, play hard, and fuck; or at least I did.
On That Day I was in my office just as any other. Business was good, there was little for me to do these days; I was preparing to head home for the afternoon. There came a knock at my door, my assistant stuck her head in; “there’s someone here to see you, Sir. I know you weren’t expecting anyone, but she insisted.”
Emmy’s Iron Maiden Glory Hole [Msub, Fdom, anal, exh, huml, swing, voy]
This is a continuation on from the ‘A Surprise Ass-Fucking in Panties’ and ‘Emmy’s games’ stories.
Previous stories:
A Surprise Ass-Fucking in Panties sexystories/comments/26myqy/a_surprise_assfucking_in_panties_msub_fdom_anal/
A Surprise Ass-Fucking in Panties part 2 sexystories/comments/26qic1/a_surprise_assfucking_in_panties_part_2_msub_fdom/
A Surprise Ass-Fucking in Panties part 3 sexystories/comments/26tgta/a_surprise_assfucking_in_panties_part_3_msub_fdom/
Emmy’s Games Part 1 sexystories/comments/276k8w/emmys_games_part_1_msub_fdom_anal_mast/
Emmy’s Games Part 2 sexystories/comments/27c2q7/emmys_games_part_2_msub_fdom_anal_exh_huml_swing/
Breakfast is Served [MF][FDom][msub][Chastity][Denial][Tease]
Inspired by a post from /u/taco_kitten, link in comments
Today is the day; the day you promised; the day I have spent these months waiting for; the day which has filled my every waking moment ever since That Day…
…That Day, yes. I suppose that’s the place to start; the Day everything changed.
I’m a successful businessman, running a small property agency with a few branches across the country. From the one property I started with, I now manage a portfolio of over a thousand properties, worth over a hundred million, and turning over more than ten million a year, as well as sales and rentals on behalf of clients. I don’t say this to boast, at least not anymore, merely to give you an idea of me, and how easy it is for me to have anything I want. I live well, play hard, and fuck; or at least I did.
On That Day I was in my office just as any other. Business was good, there was little for me to do these days; I was preparing to head home for the afternoon. There came a knock at my door, my assistant stuck her head in; “there’s someone here to see you, Sir. I know you weren’t expecting anyone, but she insisted.”
[mf] oily FISH
Sticky salty sweat dripped down my back, I felt trickles of sweat fall from the top of my thighs down past my ankles.
The humidity was intense even at 4am as I strolled through the square of the sleepy town of a pathetic population.
This was the only time my anxiety was asleep inside my body.
I walked around the shops and restaurants, past the funeral homes, through every dark dirty poorly lit alley.
As lights approached from the distance I would pretend they were coming for me and hide myself in the darkness watching as the car slowly passed by, I enjoyed being unseen when I chose to be.
Then she showed up.
I never had seen her before atleast what I could make out from her features in the darkness, but she definitely was unwelcome in my time of solitude.
Sure it was selfish of me, and childish, but fuck, give me this one single joy and don’t spoil it.
She was undeniably ugly but I didn’t care, her ass was narrow, but I didn’t stare. Her Breasts were small, exactly how I liked them. If I could put in a female request like a food order I would have the tall vanilla milkshake with caramel sauce hair with an apple bottom glass ass and inverted tits.
[MF] Becoming My Landlord’s Pet (Part Nine)
I pumped my freed puppy cock into Michelle as hard as I could manage. My elbows were crying out in pain, so when my weight was placed entirely on my landlord, my cock drove deeper than before.
I growled into her ear from behind my puppy hood, lustful moans as I played up the part of puppy even more. My animalistic thrusts and barks drove her mad as I took her from behind like a proper dog. I still remained in total darkness, the humiliation still prevalent.
“Breed me you bitch, drop your fucking load in your owner’s pussy!” she demanded, and I gave in. Blowing day’s worth of stored come into my landlords pussy took little more than ten seconds. She commended me for being obedient, being a good little puppy, *her* good little puppy. I didn’t want to pull out and end this particular sexual encounter. I wanted to keep pumping my cock into my landlord.
I was exhausted, covered in sweat and sex, I can only imagine how good the fresh air would feel upon my face once this hood was off.
Ariel takes on four [Group]
Four cocks, six loads. Four whiskey slaps. Two Andrews.
But let’s back up.
It took a long time to arrange this. At one point, we had an entirely different group of guys. I’ve posted about Ariel twice now – we’ve been getting together regularly since mid-September. We’ve had two threesomes (both MFM) and are now looking to cross my fantasy (FFM) off the list. However, in between these, I wanted to treat her to a gangbang.
Group sex is hard to organize. Getting responses is tough in the first place. I’m well aware my own local subreddits either hate me because I’ve been successful in meeting women, or they believe I’m making everything up. Which, sure, I can understand how someone’s good fortune may be frustrating. I like to write about my adventures because in a lot of ways I’m an exhibitionist. I’m terrified of being recognized by colleagues or friends, so I keep myself unidentifiable in photos (tattoos and a scar make it hard) but stories give me a lot more freedom. That being said, they’re absolutely 100% true. And if Brian, Andrew, or Andrew want to chime in here, they’re welcome to!
So yeah, finding participants is tough. Some guys hilariously send a message simply saying, “Tits?” Yes, dude. She has tits. Next!
Girls Night In – Part One [M][F]
Two weeks had passed since that dreadful, wonderful, night at the pub, Melody’s large and curvy bottom was back to its original smooth creamy complexion. Keeping it a secret from Steve had been a real effort but lots of lights off fucking had done the trick.
‘They won’t call me’ Melody said under her breath, trying hard to convince herself as she did the washing up while Steve was watching T.V.
She’d even seen Sue in the supermarket, while shopping with Steve, and there had been no mention of the happenings in the pub. Just a nod and quick hello, nothing out of the ordinary.
‘No’ she went on to herself ‘they had their fun and that would be an end to it’ somehow though her thoughts rang hollow.
A Midwinter Day’s Dream [tgF/M, Consensual, Romance]
Johanna sits next to me, her thighs sat folded. But her upper body crushes into mine. She breaks the kiss, the taste of her throughout my entire mouth and nose. I lick my lips, accidentally swallowing a drip of her saliva from her drooling kiss. Her eyes stare deep, as if trying to see inside my soul. Our foreheads touch, and her fingers run through my afro, as if she’s barely keeping it together. She then pulls back, stopping. Embarrassed. I recompose myself too.
“Sorry…I didn-”
“Heh, it’s okay… I liked it.”
“………………………..Can I show you my house?”
“Sure….. Wait… this is YOUR house?”
“Uh huh!”
She jumps up, patting down her dress, and clenching my hand like last time. I try my best not to swagger and lumber, as my world spins like a dreidel. I jog behind her, as she yanks me towards the big house. The sky is dark blue now, the setting sun and the moon the only light. Francine and Lamarr don’t even seem to notice us.
We hit the back door, and I find myself yanked inside. The house is huge. Massive. Magnificent. I find myself gasping as I look around. She tries to act as if she’s showing me around, but she looks shy and nervous.