She enrolled us in a mixed-gender aerobics class and required me to wear tight shorts that revealed how poorly endowed I am. Several of the men were openly gay and all of the men were better endowed, so the humiliation of knowing that the other women in the class were comparing me unfavorably to them aroused me and motivated me to work harder. After each session, I was also required to thank our instructor, Mistress Sandra, which she seemed to think was the natural order of things. My first two sessions had me pretty exhausted, so I actually looked forward to a relaxing weekend of being Hannah’s slave full time.
When I got home from work that Friday, Hannah became Mistress Hannah and sat me down in front of the mirror and instructed me on how to apply makeup that complimented my pale complexion and eye color. We had gone clothes shopping and had received several packages during the week, so I wasn’t caught completely by surprise when she started to dress me. Because of my 5’10” height, I didn’t think I could ever pass for a woman, but because I have a slender build, she was able to give me some shape.
My ass was naturally feminine, but I needed some tricks for my legs, waist and of course my chest. I put on a red garter belt and black stockings that slimmed my ankles and knees while rounding my calfs and thighs. Next came pale pink panties with a matching bra over a false chest with very realistic breasts. Over all this, I wore a dark blue dress with a belted waist and a wig of long curly blond hair. When I was totally transformed, she had me stand in front of a full length mirror to see the results. I looked surprisingly sexy. When I was finished admiring myself, she told me that tonight, I would learn how to suck cock.
I waited patiently but with trepidation while she changed into her outfit. It was my old high school basketball jersey and shorts with a much more pronounced bulge than I ever gave them. She ordered me to kneel and “gimme a hummer, bitch.” I silently objected to her tone, but realized it was exageration. I never treated her like that and I doubt any other guy had, but I knew that many women were degraded with much worse comments so I played the resigned submissive role. I knelt in front of her and pulled her shorts down. Next came my old jockstrap and when that came down a big tan rubber dong popped out into my face. It was about an inch longer than my extension, but not as thick. I carressed her ass cheeks as I licked down along the side of her cock.
“Yeah, that’s it. Lick it bitch,” she said. She kept up a steady patter as I slowly progressed to sucking it. With my mouth and one hand, I tried to do to her cock the same things I like done to mine. I even tried to swallow it but I must not have been in the right position because it wouldn’t bend down my throat. With my other hand, I eased two fingers into her pussy and placed my thumb on her clit, rubbing it the way I knew she liked. She was wet and ready. It didn’t take very long and she was thrusting and coming.
At first, I thought she was going to ignore my now raging little hardon, but she pushed me backwards onto the floor and lifted my legs back onto her shoulders. She pulled my panties aside and eased her mouth down on my cock. After a couple of strokes on it, I felt something wet against my asshole and thought she was going to penetrate me with the dildo, but she just eased a well-lubed finger in and then another and then another while she continued sucking my cock.
She moved her fingers around a lot as she sucked me, sometimes spreading my hole wider by separating them and sometimes rotating them. In short order, my cock pulsed and she lifted her head and stoked me into a powerful orgasm, letting my cum spurt all down my smooth belly and into my dress. When my orgasm subsided, she rubbed my cum all over my belly with her free hand, then ordered me to lick her fingers. As I licked them clean, she pulled her other fingers from between my ass cheeks and wiped them on a towel. I then had to launder the towel, my panties and my blue dress before I could shower and join her in bed.
“Well,” she said, “that went pretty well. I think you’re very good at sucking cocks. You are such a good little sissy boy. Tomorrow is going to be so much fun for me.” I went to sleep hoping it would include what I suspected was coming next.
The next morning, I cooked breakfast. I wore only an apron and my buttplug. Mistress Hannah told me that I needed the “barefoot in the kitchen” experience to appreciate the meaning of being her little sissy boy. After cleaning up the breakfast dishes, she told me to spend the day preparing the house and myself for a date with her that evening “Just like a lovesick girl would do”. She wanted me to make myself beautiful for her. She handed me the enema bottle and said she wanted me to be clean inside and out. By the time four PM rolled around, I had the house in pretty decent shape so I started on getting myself ready by first giving myself three enemas and then showering.
When I came out from the shower and sat down at her makeup table, I was surprised how much I remembered about makeup. I did what I thought was a pretty decent job and remembered to check my nails and put perfume behind my ears. Mistress Hannah watched with an occasional approving nod and sometimes a smirk. When I was finished with everything I could remember, she inspected me and said, “Very good, but we have one more finishing touch.”
She required me to kneel on all fours on the bed and with a red wide felt-tipped permanent marker, she began to write on my ass. On my left ass-cheek she wrote “FUCK” with an arrow beneath it “===>”. On my right cheek she wrote “HERE” over “<===”. In between the arrows was my virgin rosebud. “Someday maybe we’ll have this tattooed permanently. It would be so fun to watch you thank Mistress Amy afterwards.” She smiled deviously when she saw how hard that comment had made me.
She laid out my clothing and jewelry for the evening on the bed and told me to change into it while she used the bathroom to become a man. “And when I come out,” she said, “I want you to be a cock-worshipping slut who’s very happy to see her man.” I recognized similarities to one of my stories that she had found in my computer’s porn stash. She was using my fantasies to learn my darkest secrets and it was clear she was excited about humiliating me with them.
I pulled on black thigh-high stockings and then strapped on my fake chest. Next came a red bra and pink panties. Then I put on a plain white blouse and a pleated blue jumper skirt that made me look like a sexy schoolgirl. I topped it off with a long natural redhead wig. I looked at myself in the full-length mirror and even though I looked a little ridiculous, I was getting kind of turned on.
When Mistress Hannah came out, I put on my best sex-kitten act. I rushed up to her like a flirty girl and said, “Oh, I’m so happy you’re here! I’ve been thinking such naughty thoughts about you, all day!” I put my arms over her shoulders and pressed my boobs against her as she put her arms around me and started fondling my buns. “Ooh, it feels like my ass is gonna be the scene of the action tonight.” I squealed, “I can hardly wait! Would you like me to suck your cock up nice and hard first?”
When she said yes, I dropped to my knees. She was wearing my shirt and pants so I undid the belt and dropped the pants. There was a big bulge inside her boxer shorts, so I opened the flyhole and her big tan dildo popped out. I tried to be brave as I said, “Wow, looks like you’re planning on giving me a big stretch.” She must have seen the fear on my face when I looked up at her, because she gave me an evil grin and said, “Go big or stay home”.
“How about I take this off so you can see my tits?” I said as I dropped the jumper shoulder straps and wriggled out of the blouse. My fake boobs jiggled nicely in the bra, and she carressed them as I pulled her boxers down, lifted her cock and slipped it into my mouth. I noticed that the straps were a little loose so I tightened them. Then my fingers found her wet slit.
Mistress Hannah told me to get on my hands and knees on the bed as she stepped out of my pants and boxers. I was surprised how horny I was becoming. At first, she positioned herself beside me and bumped her big dong into my leg and butt a couple of times. She put her hand on my lower back and felt my ass through my skirt. Then she delivered two sharp smacks onto my ass, one on each side. I Knew from my story that spanking would be included, so I played along. “Ooh! That’s making my ass so warm and tingly!” She put her hand back on my skirt and then continued down my thigh. It was clear she enjoyed the feel of the skirt and the stockings on me. She slid her hand back up my leg along my inner thigh and up under the skirt.
When she touched the bare skin above the stockings I got goosebumps. She rubbed myinner thighs and then my crotch through the panties and then gently squeezed my buns. She pulled my skirt up and held it up with her other hand. Suddenly, she delivered two very sharp smacks to each pantie-covered ass-cheek. These hits really smarted, but I think her own hand must have hurt almost as much. “Oooch!”, I said, “You’re making me so horny. I’ve just got to have that cock inside me. Please fuck my ass.”
She moved around behind me and I suddenly felt really vulnerable. “your ass looks really beautiful”, she cooed,”Pink is definitely your color.”
I didn’t know whether she was talking about the panties or the glow from the spanking, but a compliment is a compliment, so I replied with, “You say the nicest things to a girl.”
She rubbed her hand over my warm buns and thighs and then pulled the pink panties down over the thigh stockings. She reached between my thighs and stroked my cock a couple of times and then slid her hand back and gave my balls a little pinch. She was letting me know that she was in control and I knew she was enjoying the power she had over me. She spread my cheeks and I could tell she was looking right at my asshole as she said, “I’m going to love fucking that tight little hole.” She released my cheeks and said, “Just relax”, as she lubed her rubber cock.
I tried to relax and open my anus a little, but suddenly, something hard banged against it three times and I clamped it shut. “Oh, look at that,” she giggled. “It’s alive, it’s awake and it’s afraid.” This definitely didn’t come from my story and now I was all tense. She pushed a larger buttplug than I had ever tried against my tight hole and said, “This will help prepare you for the big guy. Now just relax.” I did my best and it slipped in. Then she started to rotate it and ease it all the way out and back in. She kept this up until my hole fully relaxed and I could barely feel a difference as the widest part of the plug slipped past my sphincter. She pulled the plug all the way out and said, “It’s good and relaxed now. It’s just gaping wide open waiting for my cock.”
I began to worry that my stretched hole would close again, but as I looked in the mirror, she grasped the dildo just behind the head and slipped it in. She let out a long low quivering moan and I knew that moment was very special for her. I realized I had just lost my anal virginity to her.
She eased the cock in slowly, backing it out a little bit and pushing in a little further each time until finally, she eased the last half inch of her ridged rubber snake into me. Just before then, I thought my ass would split from the stretching. I don’t think she wanted me to feel much pain and I didn’t want to spoil her fun, but her cock felt so big that I couldn’t help but let out a small whimper. Just then, she gave a short thrust and I felt the fronts of her thighs against the backs of mine and the straps around her hips against my still stinging ass cheeks. My crack was wide open and her balls were now rubbing mine. Knowing it was all in, “balls deep” made it easier to bear and I felt a little proud for having taken in the whole thing.
She slowly pulled the dildo all the way out and I felt the head as it exited. “Your cunt is gaping much wider now.” she said as she added more lube to the dildo’s head and shaft. She slipped it back in and once again worked it all the way in until her hips touched my butt cheeks.
It was then that she leaned over and I could feel the weight of her boobs on my back. She reached her left hand around my waist and began to gently stroke my cock and with her right hand, she began squeezing my fake boobs. Then she started to speak very matter-of-factly into my ear.
“You’re a male and you’re submitting to being fucked up your ass by a woman who is wearing a cock that’s much longer and thicker than yours. I said a male and not a man because you’re wearing a sexy little schoolgirl outfit, you have a nice set of boobs and what you’re doing is very feminine. Real men don’t wear dainty frilly girlie things, especially those pretty little panties. Pink panties are for naughty girls who are going to have a stiff cock stuffed up one hole or the other. That’s why I wear them and that’s why you’re wearing them. Now you know a smidgeon of what it feels like to be a woman. You participated every step of the way in inviting my cock into you, just like women do. You made yourself presentable and you presented yourself. You sucked my cock like a pro and you even tightened the straps so I would be able to fuck you good and hard. Your ass cheeks are a beautiful rosy red from the spanking I gave you as you pretended to be my slut girlfriend. I forced open your tight virgin asshole and it stayed wide open just waiting for my cock. You now have all of my cock up your ass and you took it like a real butt slut. Even with all of this humiliation, your cock is hard and obviously you’re enjoying this. We both know that all of this is true and that makes you my butt slut. I will never again think of you as a man. From now on, I own you and I want to hear you admit it. Tell me that you’re my butt slut!”
“Yes, I’m your butt slut.”
“Are you my bitch?”
Yes, yes, I’m your bitch.”
“Good, bitch, that’s what I like to hear. Now stroke your puny little pud for me. That’s it, bitch, stroke your teeny weinie while my cock fills your ass. Now bitch, call me ‘Sir’ and thank me for everything I’ve taught you tonight.”
“Thank you Sir. Thank you for everything.”
“Now, tell me you love my cock.”
“Oh, I do Sir. I love every inch of your cock.”
“Now, beg me to fuck you.”
“Oh please, Sir, please fuck me. Please fuck my ass hard with your big cock.”
She leaned back and dribbled some more lubricant down my crack and onto the strapon. Then she started to give me long hard strokes while rolling her hips gently and I could tell she was grinding her clittie into the base of the strapon. I watched in the mirror as the long thick cock thrust in from different angles – hammering my tender ass while I stroked my cock. Her thighs, hips and balls each made distinct slapping sounds against me as she bottomed out with each stroke and my boobs began to jiggle around from the rythmic thrusts. I guess I shouldn’t be surprised, but it started to feel real good. Soon, I was rocking back, trying to meet her thrusts – willing her cock to stretch my hole wider and to penetrate my ass deeper, her balls to smack mine harder. My own pathetic cock got harder than it has ever been and I could not help but moan with pleasure.
“Ohh, Ohh, Ohh, Yesss!”
“Don’t come, bitch. Wait for permission,” she gasped. “Ohhh, this is good! I love fucking you. Keep begging.”
“Please fuck me! Please fuck my ass!”
“Ohhh, this is so good! I love seeing your rosy red ass with my cock plunging between the cheeks and into your pink hole!”
“I’m your butt slut! I’m your bitch! You’re the man! I love your cock! Please fuck me, Sir! Fuck me!”
“Ohhh, this is gonna make me come. Don’t come yet bitch! Ohhh, ohhh, ohhhhhhhh, okay now bitch, come! Come for me while I fuck your ass! Ohhhh, yes, that’s it, come with my cock up your ass!” Ohhh, Ohhh, Ohhhhhhhhhhhhh!”
My load pumped out onto a pillow as Mistress Hannah slammed her last few thrusts into me. As our breathing returned to near normal, she slid a finger into the gob of cum on the pillow and held it to my lips. “Lick this up, bitch.”
I licked her fingers clean.
As I watched in the mirror, she watched my ass as she pulled her cock out, catching a little dribble of lube on a towel. She crouched down and watched as my hole slowly closed. “That was just so sexy,” she said.
And this was only Saturday night. She informed me that my weekends of slavery would include Sunday night starting the next day.
