Sissy Humiliation


This is a story about a young student closet sissy who got humiliated by a much older man.


I was 22 years old, married and in grad school, my wife went home occasional weekends and I would stay on campus. We were newly married and she loved to show off her body in sexy lingerie and outfits, her favorite was a schoolgirl uniform complete with plaid skirt, white stockings, white panties and white shirt. Since an early age I’d experimented with cross dressing and I had a thin and somewhat girly physique. I was 5ft 9in and about 130 pounds with a round butt.

When my wife would go home for the weekend I would wear her little schoolgirl outfit and find something to use as a dildo, more often than not I used my fingers and could get 3 in pretty deep. I became obsessed with cum and I would always finish on my back in the pile-driver position so I could cum in my mouth. I would think about this during sex with my wife as it was my favorite thing to do. I would always think that a man was fucking me and then cumming in my mouth.


After a few months, Craigslist Personals became more common knowledge and I started looking at older guys in the area. I would jerk off looking at their cocks and thinking about them fucking me, it wasn’t long before I posted an ad of my own. I was careful to hide my face and I made sure I was wearing the schoolgirl outfit for all to see. I specified that I was a young anal virgin that was looking for an older guy to teach me some things. I posted my ad as soon as my wife left on the Friday, within an hour I had over 20 replies, so many horny daddies!

I engaged in a lot of dialogue, but ended up focused on a guy called, “The Professor,” he was in his 50s and 6ft 2in with a very heavy build. I don’t know why I was attracted to this, but I was. He told me he was discrete and he lived alone, his address was only 2 miles away, close to campus. We arranged to meet up Saturday at 12pm at his house, I told my wife I was going to the library to study on Saturday afternoon. He gave me the safe word, “Banana” and told me that he was going to lead everything and I could stop if things got too rough. I was really turned on and I brought lube, condoms and of course wore my schoolgirl outfit underneath.


When I turned up, he greeted me with a smile and he was a lot fatter and taller than I had thought, I initially didn’t find him attractive. I walked in nervously and apprehensive and he told me to get upstairs and put my outfit on, he told me the master bedroom was on the right, he said I had 5 minutes. I quickly got upstairs and removed my clothes and looked in his mirror, I wasn’t sure I wanted this anymore, I was a little disappointed in his looks. For some reason this didn’t stop me and I put on the white stockings, plaid skirt and white cotton panties, I then put the white shirt on an placed the lube and condoms on the side of the bed. I got on the bed and my cock started to harden, putting on the uniform always did this to me, my erection was bulging through the skirt.

I heard him walking up the stairs and I looked at the door, waiting for it to open.


As he walked in he was completely naked and his gut was hanging over but I could see his hard cock protruding, it was about 8 inches and thick, I was excited to see a cock that was clearly bigger than my own. “Hi Baby, are you ready to be owned?” “Yes Daddy, I’m ready to be your anal whore!” I don’t know why I was going along with this, I felt like I was acting and didn’t really want to be with him. He got on to the bed and quickly grabbed me, I was on my back and he was on top of me, kissing me passionately. I couldn’t stop and he was really strong, I kissed him back and I could feel our cocks touch each other, both rock hard.


He pulled back slowly and asked, “Are you ready to be my whore?” “Yes Daddy, I’m all yours,” to my surprise, I sounded pretty effeminate. I was expecting his cock in my mouth any minute, but instead he turned around so I could see his huge flabby ass, he started moving backwards and I tried to speak, “Mmmmffffkkkk!” His ass was pressed into my face with his crack right against my mouth and nose, I was not expecting this at all. “Lick that ass you dumb cunt!” He pressed fairly hard and sounded very assertive, I did as he requested. I put my hands either wide of his ass and started licking, it didn’t taste too bad, not much worse than my wife’s. “Oh yeah you whore, that’s good, lick Daddy’s ass!” This continued for a few minutes and then he turned around so his hard, thick cock was next to my mouth. I didn’t need to be told what to do and I opened my mouth and took as many inches as I could.


His cock filled my mouth and he instantly grabbed the back of my head and started thrusting into my mouth. I had to fight the urge to gag, this was more than I could really handle and I wasn’t enjoying it. His balls were hitting my chin and my face would hit his fat, hairy gut each time he thrusted, I though about using the safe word. He forced his entire length into my mouth and I gagged, he pulled his cock out and laughed. I chocked and started spitting, I went to say something but then he grabbed my head and forced his cock into my mouth again. This caused the same reaction and he pulled out again, laughing and mocking me, “Poor little whore, don’t you like Daddy’s big cock, is it too big for your slut mouth?” He did it again, this time holding it for a few seconds while I screamed inside for him to stop, all my screams were muffled. He pulled out again and I choked and started to crawl across the bed to escape.


He grabbed my legs and pulled me back so I was underneath him and face down, his entire weight pressed me down and he was really hot, I couldn’t move. We stayed like this for a few seconds and then he turned me over so I was on my back, he started talking to me, “I can’t keep out of your hot little ass any longer baby, I’m going to fuck you really hard in whatever position you like. We can do missionary, prone, doggy or you can ride me, you decide!” I hadn’t considered that I would get this choice and so I got into the doggy position and said in a girly voice, “You better fuck my ass hard Daddy, I’ve been a very bad little girl!”


With that he grabbed my panties and pulled them down to my knees, he grabbed the lube, got behind me and squeezed a glob onto my bare ass. His fingers started entering my ass and I focused on letting him in, I tried to relax as much as possible. Having someone else’s fingers inside me was a new sensation and really enjoyable as I couldn’t predict what he would do next. Within a few seconds he had three fat fingers inside me and was finger-fucking my ass. I wondered if I would just come from this, it was really good and didn’t hurt. “Yeah, fuck me daddy, yeah!” I was saying dumb stuff and enjoying it.

Next thing I know he had grabbed more lube and was rubbing his thick cock, I looked over my shoulder and smiled at him, “Good little whore,” he said. I felt his thick cock press into my tight ass, it didn’t go initially and I could feel a stinging sensation as he started to push. “Oh fuck!” I said. “Take my cock you little bitch!” I focused on relaxing as he slowly pushed into me, the thickness was a little too much, more than I’d taken before. Suddenly I felt the pressure and his thick cock entered me, filling me up and touching my prostate, it was intense and I yelled, “Oh fuck daddy, that’s big!” He slowly pulled back and then thrusted slowly back, I was gasping with each movement. This continued for a few seconds.


“Okay Baby, Daddy is really turned on I’m going to pound you now, I’ve been waiting for this!” I prepared as he grabbed my shoulders and started thrusting deep, hard and faster, “Oh oh oh ohhhh, Fuck me Daddy, Fuck me!” I felt like I was falling into a dream and I could barley get a word out from this hard pounding. I was moaning loudly and the pleasure was incredible. Every thrust was bringing me closer to orgasm and I couldn’t believe what this overweight older guy was doing to me. We’d probably been fucking like this for a few minutes when he leaned forward and pressed me down with his full weight on top of me and his cock buried in my ass. The shock of this sent electricity running through my body and he started to pound me while pinning me down. I couldn’t take any more and I knew an orgasm was coming. I started to yell, “I’M A FUCKING WHORE, I’M A SISSY, FUCK….” I was coming uncontrollably into my plaid skirt, I was in heaven, I’d never felt so good in my entire life.


The Professor was still fucking me and I could feel the wet cum against my still hard cock, I knew he wasn’t wearing a condom too, I should have said something. He was out of breath and struggling, his body was hot and wet, I was pinned down with his cock in my ass, still thrusting hard. He started to kiss my neck and I got worried in case he left a mark, he was whispering int o my ear, “Good little whore, Daddy’s little anal princess, do you want Daddy’s cum?” “Yes Daddy!” He turned me onto my back and put his knees either side of my head, I opened my mouth and stuck out my tongue as I waited for his hot load. He had his hand on his cock and was moaning. He let out a loud, “Fuck!” as his hot white cum pulsed into my mouth; 4 full spirts coated my mouth and landed around my lips and nose. I hungrily swallowed the familiar warm, sweet and salty cum and licked my lips.


He fell on the bed beside me and started breathing heavily and getting his breath back. I looked at him lovingly and smiling, this wasn’t so bad! As he caught his breath he said a few words to me, “We have all afternoon together, things are going to get a lot harder and nastier from here on in, are you my fuck-doll?” I kept smiling and answered, “Yes Daddy, I’m all yours!”

 

I met a man on Craigslist and agreed to meet at his house and to bring a school girl outfit with. He wanted to measure and compare dicks with me and whoever is the smallest has to wear the school girls outfit and actually act like a girl and had to get on top the other one and give their boi pussy to him. I knew I'd be wearing the outfit cause I have a really small dick. Maybe 4 inches when fully hard but usually it don't get hard let alone fully hard. I get there and go in. We have a drink and as we do I see the outline of his dick and its huge. When drink is finished he says let's go to the room and as I stand to go he smacked my ass and says oh nice and firm. We get in the room and he strips off and then grabs a tape measure and measures his dick. With a big smile says 8 and a half soft. Then says ok strip now. I do and when I take off underwear he laughs and says no need to measure that tiny thing but I'm going to. He laughs the whole time he measures it then says 1 and a half inches. He laughs hard and says wait let's stretch it to measure I'm sure it's close and laughs. He grab with finger and thumb and pinch hard and then pulled really hard. When I wince from the pain he laughs slaps my balls laughs and then measures my tiny dick. He laughs real hard says so close almost 3 inches. Damn I seen clits bigger than this puny thing. Well we know who the bitch is. At least you have a really nice ass. Then says but first as a man then laughs says kneel dude and suck another man's dick and laughs hard as I kneel. When I'm on my knees he says and play with that puny thing as you suck a real dick. He laughs as I rub my dick and start sucking his. After a minute he says stop but stay like I am but move hand. When I move hand he does two quick hard kicks in my balls and dick and I fall over. The kick made my cock go in me and stayed. He made me stand and dress in front of him and then we made out with him rubbing between my legs like it was a pussy. Then he lay me on my back and took panties off. I thought so he could fuck me in my ass but I was wrong. He put his dick where mine went in me and pushed till two things happened. One I hollered like a girl and two the head of his dick went in too. Then he fucked me like that a while as he says you're welcome for making a pussy for you. He fucked it so long and deep that the whole time I rode his dick and he fucked my ass which was almost 3 hours and all the way home which he made me wear school girl outfit home and the whole shower and rest of night till almost 4 pm next day my little dick did not come back out. For 3 hours he fucked me in every position he could think of and pounded it the entire time.

 

Luv having my tight sissy pussy used and fucked like that. And omg i luv a man pulling his thick, hard, sloppy cock from my asshole and stuffing it into my whore mouth. Blowing his nut down my throat and feeding me.

 

My best friends dad forced his BBC down my throat when I was a young teen...

 

I'm definitely bisexual

 

Hot. Hot. Hot

 

So fucking hot…I’ve only imagined how it would feel to be totally and completely dominated!!

 

Great story! made me shoot Mmmmmmmmm

 

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