During my first week as her new slave, Hannah decided that I was too hairy for a little sissy boy, so I had to begin removing hair from the tip of my nose down. The mustache went first. It really was kind of pathetic anyways. I actually got compliments from some of the women at work about how handsome I looked without it. I had grown it because I had a "baby face" and I wanted to seem manly during college, but now that I had a good career, I guess it was okay to look "cute".
Hannah also scheduled a piercing appointment for me. I went straight from work one day and met her at the piercing parlor. Hannah had requested a woman to do the piercing and the young woman who served us introduced herself as Amy. She was a little surprised when Hannah specified how I was to be pierced and asked when I would be able to switch to rings and chains. I think Amy noticed my tiny hardon poking straight out in my pants and that seemed to explain everything to her, because instead of talking to me, she directed her comments to Hannah.
"Tell him to keep them clean and make sure he does. He must use rubbing alcohol. It will sting him, but it's important." She continued talking to Hannah, but looked straight into my eyes and smirked after each penetration. When she was finished, Hannah ordered me to thank "Mistress Amy".
"Thank you, Mistress Amy." I'm sure I was blushing a deep red when Amy giggled and told me to enjoy my new life.
I left the parlor with studs in both ears and horizontal bars in both nipples. Of course, there were bandages taped over my nipples to protect my shirt, so I was glad my chest was already shaved. Hannah complimented me for my performance but added that when thanking a Mistress, I should add what I am thanking her for. The women at work thought the studs in my ears were "sexy". I didn't tell them about the nipple piercings. I work in a pretty casual office environment so the ear jewelry was not a problem, but if word got out that my nipples were pierced in the submissive direction, it could hurt my career.
By Friday night, I was shaved smooth from my ears to the tips of my toes. We had followed up the shaving with a chemical hair remover and body lotion. Hannah had helped with the parts I can't reach. I also kept Hannah's pubic area silky smooth, though she preferred to continue to shave her own legs and underarms. When we went out to dinner, I wore my pink panties under male clothes and I was pretty hard the whole time. After dinner, we went to a mall and bought some sexy undies in my sizes. It was embarrassing to even be in those aisles in the store, but Hannah also made me purchase everything with a credit card. The girl at the register was clearly enjoying my embarrassment and I almost came as I signed my name to a receipt for panties, bras, stockings and garters that were clearly a little too large for the woman I was with. Hannah read her nametag and ordered me to thank "Mistress Anne".
"Thank you for your kindness, Mistress Ann." She giggled and turned almost as red as me.
When we got back home, Hannah introduced me to enemas. I had written about them, but never really experienced one. She had me kneel "doggy style" and inserted the tip into my rectum. Then she raised the bottle and drained it into me. For the third rinse, she had my lie on my back and hold my legs over my head while she drained the bag into me. After I had expelled for the third time, I actually felt much better and of course, my cock was hard. She jerked my cock into my "old" panties for the last time before they became hers again. I licked her to orgasm and we slept.
On the first Saturday morning, Hannah told me it would be a very special day. We were going to see how I "measured up". She gave me another enema and had me shower. Then she taught me how to prepare and paint my finger and toe nails. She selected her brightest sluttiest red nail paint for me. She also applied bright red lipstick to my lips and then she presented me with a new pair of sexy pink panties and told me to wait in the bedroom. She had received and sent several text messages during the morning so I was very curious about what would happen. I sat on the bed reading a magazine and when I heard the door open, I looked up to see a very sexy well-dressed redhead woman come in, with Hannah right behind her carrying a video camera. I was stunned and extremely embarrassed, but the stranger acted like walking into a room and seeing a shaved man with painted nails and lips and wearing pink panties was an everyday thing for her.
"You may call me Mistress Bella. Stand up and let me look at you," she ordered. When I hesitated, Hannah told me to obey all of her commands or I would be punished. I stood and Mistess Bella looked me over. "I'm here to see where you are in the inadequate male spouse ranking. Nice panties, by the way. Now, hands and knees on the bed."
With great trepidation, I complied as she reached into a small duffle bag that she had brought and removed a pair of rubber gloves, which she pulled on with a professional snap. She told me to face the wall as she positioned herself behind me and pulled my panties down enough to expose my balls. She pulled my ass cheeks open with her thumbs and complimented me on the cleanliness of my asshole. I then felt a cold wet sensation on my rosebud as she applied some sort of gel. A cold object that felt like metal was then pressed against my tight hole. It wasn't large and it slipped in pretty easily, but then it started to expand. She kept twisting something and it kept expanding until finally I gave a little whimper of pain. "You've been sticking things in here. It's obvious that you're already stretched." She then made a note in a notebook. She decreased the size of the hole stretcher and removed it, but she quickly replaced it with what felt like a hard rubber plug. Then she pulled my panties back up and told me to lie on my back.
Mistress Bella ordered me to keep my hands behind my head as she removed her top and bra. Her breasts were very nice and she told me to look at them as she pulled my cock from my panties. Her nipples were full and vivid pink and also pierced with bars in the dominant position. She used a short dressmaker's tape to measure the length of my erection. "Three", she chuckled. Then the circumference. "3-1/4, pathetic". She wrote the numbers in her book. She started a stopwatch and started stroking my cock with her hand. which still had the rubber glove on it. After a pretty short time, my cock started spurting and she kept up the stroking even though she had clicked the stopwatch. "45 seconds," she informed as she wrote in her notebook. "I've seen quicker, but most last much, much, *much* longer." She smeared my cum like skin cream all over my belly and chest, then removed her rubber gloves and climbed onto the bed and laid back. "Now, lick my pussy," she ordered. I crawled between her freckled legs and noticed that instead of panty hose, she wore thigh-high stockings but no panties under her skirt. Her pussy had bushy red hair and very pink lips. I leaned down into it and began to lick her clit as she started the stopwatch. She was wet, so I figured it wouldn't take very long, but she clicked the stopwatch several times and after about two minutes, told me to stop. She wrote some notes in her notebook and climbed off the bed.
Mistress Bella then pulled a DVD from her bag and told me to watch it through Chapter One. She and Hannah left the room after they verified that I had started it. The video started quickly with a title that made me cringe. It was called The Clueless Wimp's Guide to Pussy Licking. It spent about 15 minutes explaining all the mistakes I had made within the first two minutes. After seeing it, I was surprised that I had ever managed to get Mistress Hannah to orgasm by cunnilingus. When Chapter One was finished, I stopped the Video. Mistress Bella and Mistress Hannah came back in soon after. Mistress Bella said, "Now let's try that again as she laid back on the bed and spread her legs. As the video had shown, I spent at least two minutes kissing my way down her thighs and she cooed in delight. When I first reached her pussy, I started near the bottom and slowly licked my way into and around it, before finally finding her clit with my tongue. She was much more aroused this time and she stopped the stopwatch and surrendered to the pleasure I was giving her. "Oh, yes! Lick me you little sissy. That's much better. You're gonna make me come this time." I soon had her moaning with pleasure and brought her to a nice orgasm as Mistress Hannah watched with approval.
When she had regained her feet, Mistress Bella continued making notes, consulting several times with Mistress Hannah as I was under her orders to stand in the corner with my back to them and my panties around my knees. When she was done, she tore a list out of her notebook and handed it to my Mistress. She thanked me for getting so much better so quickly and told me I was a promising cuntlicker.
"Thank you for your kindness, Mistress Bella," I said. This seemed to please both of them and I was glad I took the initiative this time. It may not seem that Mistress Bella was all that kind to me, but I was learning to appreciate that kindness comes in many forms. Her brutal honesty mixed with sparse comments had already made me a better lover.
Mistress Bella left the DVD with Mistress Hannah with some comments about my continuing study. Then she bent and kissed me on each nipple and wished me luck. I thanked her again and Mistress Hannah showed her to the door. When she returned to the room, she showed me the list of comments and recommendations.Overall cleanliness and appearance
- good, needs professional manicure and pedicureHair
- hopeless, wig recommendedChest
- recommend breast enlargement pumping (not large, just obvious). Replace the nipple bars with rings and a chain. Use a false chest for realism when dressed up in publicEars
- will look good with earringsFace
- pretty mouth, consider electrolysis for additional smoothness.Ass
- very nice, can currently accept large intruder, but not much thicker than the plug, work it larger slowlyCock
- the obvious weak point, pathetic, it is smaller than 98% of adult white males and quicker than 87% of adult males, maybe a cockring and some enlargement would help, try weights and pumping, but an extension that stays hard after ejac would be fastestBalls
- cute, not too large, maybe add some jewelryBody tone
- needs more exercise with emphasis on sexual performance, enroll in aerobic trainingCunnilingus
- initially pathetic, but great improvement with just short study, which shows interest in improvement, encourage the study and practice and enjoy it, it will add redeeming value.General
- recommend increasing feminization of looks and attitudes, he's a natural sissy-boy
After I finished reading, Hannah asked me what I thought of it. I felt very humiliated at seeing myself reduced to those few comments but I knew they defined me pretty accurately. "It looks like an opportunity for more shopping," I replied.
"That's a good answer, slave. Now you can show me what you've learned today. Undress me."
I started by helping her out of her T-shirt. Ordinarily, I would have kept undressing her, but I knelt on the floor and lavished her breasts with attention from my hands and tongue. I licked, kissed and nibbled each of her pale brownish nipples until I got a contented sigh from her before moving on. I unzipped her jeans and removed them and her panties. She stepped out of them and laid down on the bed, bringing her knees up and holding them together. Ordinarily I would have just pulled them open, but instead, I just kissed them while sliding my hands down her outer thighs and then up along the backside until she slowly eased them open. I kissed my way alternately down her inner thighs until she willingly spread wide for my face to enter her crotch. Her clittie was erect and protruding from her pussy lips and ordinarily I would have begun to suck it like a small cock, but instead I temporarily ignored it as I focused on her slit and brownish pussy lips. I started at the bottom and poked my tongue deep inside her, barely nudging her clit with my nose. When she started to moan, I moved up to her clit and circled it with my tongue. "Oh boy," she gasped. "This is different. This is good. Oh, yes. Like that. Uh-huh. Lick that. Oh, yes. Now suck it. Suck my little dick. Mmmmmmmmmm! Uhhhhhhhhh! Oohhhhhhhh! Ahhhhhhhh! Yes! Suck me! Oh, I'm coming. Ohhhhhhhhh! Ahhhhhhhh! AAAAAAAHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH!"
For the first time ever, her pussy gushed as she came, coating my smooth chin and draining down her ass-crack. When her breathing returned to normal, she said, "That was wonderful. That earned you a present."
She got off the bed and pulled a bag from the closet. "I already knew some of what Bella was going to suggest, so I bought these. Now frankly, I barely feel your dick when it's inside me. It's just too small. I don't think it can be improved much, but here's what we can do for you. This is a suction pump. We're going to use it to make your boobs bigger so you look more girly, but with this attachment, we can gain you some cock length and maybe some extra thickness. You'll still be pathetic, but at least you'll be bigger and pathetic. You can use this as much you can stand but I want those boobies to grow, too. Now this other package is a weight system. When you're sitting watching TV during the week, you attach it and dangle it and this will stretch your cock. Don't use it for too long or it will cut off the circulation you need to inflate your little wang."
Finally she pulled another box from the bag. "On the weekends, I'll be the man and you'll be my bitch, but during the week, I need a man." She pulled a strapon dildo out of the box and it was not what I would call super big. It was about seven inches long and less than 2" thick, but she turned it to show me the backside and there was a tubular hole in it. "You'll put your little cock in there and even if you come real quick, you can keep fucking me until I come. Try it on."
She squeezed a little gel from a tube and rubbed it onto my cock, which immediately got hard. Then she helped me strap my new cock around my waist and slip my dick into it. She pulled the crotch straps on either side of my balls and up through my ass crack to buckle them to the waist strap. They rode right across the flange of my buttplug. Then she laid back, spread her legs and said, "It looks good on you. Take it for a spin."
It was like a magical experience for me. I suddenly knew what it was like to have a normal sized cock and I couldn't wait to fuck her with it. I slipped it into her wet pussy and started fucking her and I could tell that she could actually feel it inside, because she started to thrust against me. I pumped my cum into it within two minutes and I fucked her for another two before my arms and thighs got too tired and I collapsed onto her. I felt really low and I said, "I'm sorry."
To my surprise, rather than being upset at my failure, Hannah consoled me and told me that she didn't expect miracles on the first try. "We'll build your stamina and don't forget, that we have other positions that don't require so much strain on you. Now that you have something worth fucking, I can climb on and ride you cowgirl style and since you'll be a man, you can do me doggy and I won't have to worry about your little pecker going soft. But I want you to gain some control over how quick you come. So when you can fuck me three consecutive times and make me come before you, I'll give you an extra special treat. I'll let you fuck my tight little asshole with your real cock."
I am such a lucky guy to have a woman who knows how to motivate me.
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<a href="https://www.lushstories.com/stories/crossdressing/mistress-hannahs-pathetic-husband-part.aspx">Mistress Hannah's Pathetic Husband Part 2</a>