The Making of a Sissy!

by Small Penis


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This story contains adult sexual content and should not be read by those under 18, or considered minors in their country or locale. If you are under 18: CLICK HERE

These stories are the artistic expression of the authors who wrote them. The Small Dick Club strongly believes in freedom of speech, and the right of artists to be heard, especially if what they say pushes the boundaries of what is acceptable in society. If you think you won’t like the content of this post, then don’t read it. It’s that simple. The Small Dick Club wishes to advise readers that any similarities in these stories to actual or real people or events is purely coincidental and unintended. That any story marked as a ‘true story’ shouldn’t be taken literally, as we have no way to verify if stories submitted to us are true. The Small Dick Club takes no responsibility for the imaginations and literary creations of authors who post their stories here.
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Six years ago, I was doing well enough to finally afford my dream apartment. It was a studio apartment on the upper side of town. So, I had the job, the apartment, the money… but I was lonely. Very lonely and very horny. Not only would I get all hot and bothered from looking at all of the pretty women at work, but there were also plenty of hot women who lived in my building.

Have you ever seen that show ‘The Real Wives of New York?’ well, that’s the type of breed I had in my new building. All the women were at least 10 to 15 years older than me, all were married or recently divorced… and all were loaded.

Of course, I was always far too afraid to approach any of these women. Sure I’d get glances every now and then, sometimes I’d even smile back but I always knew nothing would come of it. I’m a wimp. I always have been and I always will be. Even though I aspire to be your typical A sexual alpha male, the truth is I’m far from that, in fact I’m quite the opposite. I’m afraid of women, attractive women in particular.

Then one fateful Thursday night, I saw her. It was love at first sight; well it was for me at least.

I was just checking my mail when she emerged from her apartment: Barbara Sheelings.

She was the most beautiful creature I had ever seen. She was an enticing and captivating woman in her mid forties. I was in awe. I stood there like a little boy, staring at her, admiring her beauty. She was tall, very tall, with tanned olive skin, thick jet black hair, high cheek bones, brown almond shaped eyes and a figure to die for. She knew she was ‘hot stuff’ giving out this aurora. She had rich red lipstick on with a short tight black evening dress showing off her impressive muscular and toned swimmers thighs.

I didn’t know what to do. I didn’t know where to look. Whether or not I should smile at her, or whether I should even acknowledge her at all.

Just as I was about to give a friendly neighbourly wave: a tall ruggedly good looking male in his mid thirties emerged from her apartment. She clinged to his arm, looking up at him in admiration.

I looked on with a lump in my throat as they exchanged a passionate kiss. They were lovers, it was all too clear. I could not compete with this guy. He was well dressed, dominant and confident…. They were a good match.

I stood there like a little kid, jealous as they walked on by, passing me.

As she came closer, we made eye contact, just for a split second. I waited far too long to wave my ‘hello’. Her eyes averted my gaze just as I waved at her.

To my relief, she didn’t see that. I’m sure I looked every little bit pathetic that day, standing there with my jaw wide open, staring at her like some pathetic prepubescent boy.

As the weeks went by, my infatuation grew. This festered to the point where it started to affect my work. I was thinking about her all the time. In particular I was thinking about what it would be like to make love to her. ‘What would it be like to make love to a woman like that? To have a woman like that admire your body? To have a woman like that scream your name in ecstasy? To have a woman like that moan your name in pleasure? To feel her warmth beneath you?’ Needless to say, my mind wondered all the time as I kept projecting myself into some fantasy world where I was her King and she was my Goddess. Of course, it was just a fantasy.

It would always be just a fantasy. I was far too afraid to even acknowledge her. Fortunately for me, this was all about to change.

The day the postman mixed her mail up with mine was the day I learned her name: Barbara.

‘Barbara, it seems the postman has mixed up your mail with mine….. oh what a lovely apartment. May I come in?….. Why yes, of course I’d like some coffee…. See your bedroom?…. Ms Sheelings!….’ I tightened my grip around my member as I increased the rhythm, ‘Oh! Barbara! Oh yeah!!! Mpf!!!! Argh!!!’

Even though I had her mail, I did not have the nerve to go to her apartment and give it to her personally.

Then one Friday night, the unthinkable happened.

I was sitting in front of my television watching reruns of Friends, eating my ‘dinner for one’ when my doorbell rang.

I was gobsmacked to see a very agitated Barbara Sheelings at my door. I was lost for words, I began to perspire… I certainly wasn’t dressed for any visitors. I was wearing an embarrassingly old torn dressing gown. I looked like a hobo, nothing like her ‘man’.

“Hi. I’m Babs. I live across the hall. You have my mail” she impatiently held out her hand.

“Oh right, I’m sorry… I, I, I was just on my way to give it to you” I frantically started shuffling through all of my mail to get to hers.

“Why didn’t you just slide it under my door?” she said

“I’m so sorry Ms Sheelings, really.” Nervously, I handed her the mail.

“You know my name?….. Have you been reading my mail?” she asked

“No! No! Nothing like that! No! I just read your…. to see who’s mail it was. Oh god! I’m sorry. I didn’t know, I don’t know what to call you.” I was babbling, rambling on.

Clearly, she thought it was charming. “Just call me Babs kid.”

I wondered why she called me kid. I certainly was no kid. I was in my early 30’s for Christ sake. No one had called me ‘kid’ since I was 19.

“Sure, I will” I said.

Babs smiled at me and walked off

“Bye-bye” I called out.

God! I was so goofy, so pathetic. I had no idea she found it so amusing.

Of course, I thought about her and fantasized about her the rest of the week. Excess masturbation is unhealthy, especially when you base your whole day around it. I was letting my work slide just because I was eager to get home and ‘rub one out to her’.

The following week, I was checking my mail, oblivious to my surroundings. That’s when I heard, “hey kid!”

Anxiously, I turned around to look at her. To my surprise, she was clinging to yet another man: this man was clearly younger, yet he was arrogant and cocky. They were a perfect match.

“err, hi Babs… how are….” My voice trailed off as they walked on by, passing me. It was almost as if she didn’t even care. I could’ve sworn her date chuckled at me as I fumbled with my words.

So, back to the bedroom: my pants around my ankles, my right hand strangling my member, my left hand holding out a folded piece of toilet paper, getting ready to catch the stream of desire. ‘mpf! Oh Babs! Oh Babs!’ I moaned as I jerked off.

I couldn’t distinguish whether or not she actually liked me or whether or not she was merely taunting me. After all, why would she say hello like that? As I ejaculated into the toilet paper I was reminded of the block headed pillar of testosterone that was her date and the fact that he had chuckled at me. It occurred to me that perhaps she was just teasing me, getting my hopes up. Yep, they were probably both having a good laugh about it amongst themselves.

Needless to say, as the weeks went on as did the casual greetings. Sometimes she’d be with one of her lovers, other times she’d be with her girlfriends and other times she’d be all alone.

It was always the same. She’d say “Hey kid” or “Hi sweetie” or “Hey honeybunch” I’d stutter, mumble and fumble over my words. Before I could ever actually say anything it would be too late.

It was a power she had over me. I couldn’t figure out why it was that whenever I was around her, I turned into a stuttering, blushing little sissy.

Furthermore, it didn’t help matters when she called me names such as ‘honeybunch’ and ‘sweetie’. I couldn’t figure out why she was calling me these names. Did she think I was gay? Was she teasing me? I mean, I knew she knew I didn’t get out that much. After all, she lived just across the hall from me.

I was always a lonely guy. I always went to the movies alone, always had dinner for one and sex was more than often a solo activity. Of course I wanted to get out there and have a meaningful experience with an attractive woman, and of course I thought about asking her out. But I was a wimp. She was too attractive for me, too outgoing, too experienced, too intimidating. She would never go out with someone like me. It would be humiliating to be shot down and rejected by her.

Yet on a cold night in January, my phone rang.

“Sweetie?” It was Babs

“y,y,yes. Babs! Oh! Hello, my how are you? I’m fine, how are y,y,you?” gosh I was pathetic.

I could hear her chuckling on the other end, “I’m fine honeybunch, just fine. Thank you for asking…. Look, I have a free night tomorrow, I just wanted to invite you over for dinner.”

I couldn’t believe it. Was this really happening? Was the woman of my dreams asking me out? To her place??? I could not believe it. It sounded too good to be true. “Dinner? Tomorrow night? With me?” I asked.

“You like Italian?” she asked.

“Yes, yes I do.”

“Great, come around eight. Okay sweetie?”

“erh, yeah sure I’ll be there mamasita” oh boy! Did I just say mamasita? She laughed on the other end before hanging up.

To say that I was walking on air after that phone call would be an understatement. This gorgeous creature was asking me out. How wonderful. My fantasy mind went into overdrive.

The next day I called in sick to work. I know it sounds a little crazy, but I spent the whole day preparing for my date with Babs. I bathed for hours, I shaved, I wore my best shirt, I bought her a bunch of wild orchids… this was going to be ‘my’ night. Finally I was going to be ‘the other guy’. The guy I always envied. The guy I was always jealous of.

At eight o’clock I stood at her door, rehearsing what I was going to say, ‘Hello my dear, you look enchanting tonight. I’m in awe of you’. I wanted to be charming, I wanted to be classy. I wanted to impress her.

But when she opened the door, I turned into that blubbering, sputtering idiot. She was looking better than ever. She was wearing an alluring ensemble with a plunging neckline, short black skirt, seamed stockings with stiletto heels. “Hi, erh Babs. You look, erh…. I’m a lovely lady.” I didn’t know what I was saying, it just came out. It didn’t even compute at first.

She arched an eyebrow, “Yes you are” she teased.

“Awww, are those for me?” She took the orchids from me, “they’re beautiful. You are such a little sweetie!…. well, come in!” With that, she ushered me in.

Despite a shaky start, the evening was well underway…

Her apartment was quite impressive. It was at least three times larger than mine. It was tastefully decorated with modern art and eclectic furniture, complete with classic and contemporary pieces. It was clear that a great deal of care and attention had gone into designing and decorating this lavish apartment.

She excused herself for a few minutes as she tended to the flowers, putting them in water.

After what seemed like an eternity, she emerged from the kitchen.

That’s when the worst thing that could ever happen on a first date happened. I had nothing to say. I was drawing a blank. I desperately searched my mind trying to come up with something to say, about anything.

We just stood there in awkward silence, looking at each other.

“So, you didn’t go to work today?” she asked.

“How did you know that?”

“Silly billy! I live across the hall from you.” She teased.

“Oh…. I called in sick.”

“You don’t look sick”

I was desperate to change the direction of this conversation; I sure as hell didn’t want her thinking that I skipped a whole day of work just to prepare for our date.

“I love your apartment. It’s just divine.”

“awww! Thank you sweetie. Let me give you a little tour.”

With that, she extended her hand to me. I swear I felt a spark. It was electric, this was pure bliss. For the next fifteen minutes she gave me the tour of her large apartment. It seemed like every sculpture and every piece of art had a story behind it.

The sheer size of this apartment astounded me. It was in fact a three level apartment. Complete with formal lounge, formal dining, a home cinema, a large kitchen and meals area, four bedrooms, five bathrooms, a gift wrapping room and a library. I felt bad for her maid, who ever she was.

Eventually, she led me up to her bedroom: the most lavish room of all. The magnificent view of the city all too clear below. This room was absolutely breathtaking.

“And lastly, this is my bedroom”

My eyes were drawn to the large king size bed, adjourned with pink silk sheets. I began to wonder what type of shenanigans had gone on in this room and if I would ever be lucky enough to revisit this room in different circumstances.

“Just amazing Babs. It’s quite large, your cleaning bill must be astronomical” I joked.

“Well, when I was married my husband would do all the cleaning, it was so convenient.”

“Wow! He cleaned all this? Why did you two break up?” I asked.

“Let’s just say he couldn’t handle it. He lives with his mother now, the fucking looser” she burst out into laughter, “I’m joking Frankie, lighten up!”

I laughed along with her, not quite understanding the joke.

She made a lovely three course meal. The appetiser was a light pumpkin soup, the main course was a fillet minion with baked potato and for dessert, a home made triple chocolate mouse complete with whipped cream. It was a meal fit for a king.

So there I was, having dinner with the girl of my dreams as we talked about our families, our careers and our ambitions.

After a good hour or two, we were seated in the formal lounge in front of a roaring fire sharing a bottle of Merlot.

Eventually the conversation died down and once again, we were plagued by awkward silence. To say I was nervous was an extreme understatement. I simply didn’t have anything else to say. I desperately wanted to tell her a funny joke or an amazing story…. alas, I had none.

Suddenly she broke the silence, “So, why isn’t a good looking guy like you married?” she queried

“ahh, oh boy! That’s a good question. I guess I just haven’t found the right girl yet you know…”

“Can I ask you a personal question?” she asked

“Sure. Go ahead.” I said taking another sip of wine.

“Are you gay?” she asked.

I almost chocked on my wine. I couldn’t believe that after all of our conversations and my blubbering that she thought I was gay. Needless to say, it shattered my confidence and I immediately went on the defensive.

“No, no, I’m not. I’m not gay. Why? Why would you think that?”

“It’s okay to be gay. Don’t get upset” she said.

“But I’m not gay. Absolutely not gay, seriously”

“It’s just that, I never see you with anyone.” She responded.

I could see how easy it was for her to make that assumption about me. Unfortunately, it was an image I was determined to shake.

“Yeah, I know. I just moved here four months ago. I’d like to meet more women,” which wasn’t entirely true, as long as I had her, I didn’t want to so much look at any other woman.

“awww! I know what it is, you’re shy. That’s so cute!” she chuckled.

“Yeah. I kind of wish I wasn’t. I sometimes wish I was like those guys I see you with.” I admitted.

“Oh? Really?….are you sure you’re not gay?” she teased

“No, no, I’m not. I just…. see you with them and I’m jealous of them. They are so confident and out there. They can talk to you and not get nervous.”

With that, she reached out, grabbing the back of my head, pulling me into her face, kissing me hard on the lips. This happened so suddenly and so unexpectedly, I didn’t know what to think. Then, just as suddenly as it happened, she broke contact, forcefully pushing me back.

“Babs, that was ama—”

SLAP! She smacked me across the face hard. I fell back clutching my face, looking up at her like a frightened turtle. ‘what kind of sick game was she playing?’

To my surprise, she started to laugh. A playful, innocent laugh.

“I like little sweeties like you. So docile and easily manipulated…. Honeybunch, I’m going to devour you tonight. I hope you’re ready”

Before I could respond, she reached out once again and aggressively, pulled me on top of her. She caressed my hair with both hands as our tongues played tag; her right knee was digging into my crotch, rubbing the growing bulge in my pants. “What’s this??…… awww, you like me don’t you sweetie?” she teased.

She proceeded to unbutton my shirt, slowly running her left hand inside, rubbing my hairy chest.

“A nice hairy chest. I love hairy men. So manly. All real men have hair.” She exclaimed.

I was so completely lost for words, that I said the first thing that popped in to my head “You, you’re amazing. I dream about you. I dream about touching your tits and sucking on them, they are just so—”

Out of nowhere, Babs broke out into uncontrollable laughter. This went on for several minutes as I sat there, feeling every little bit silly and pathetic. After what seemed like an eternity, she stopped laughing, composing herself.

“oh my! Do you want to see my breasts honeybunch?” she teased

“Oh god yes! really?? Yes, yes I do!” I must’ve sounded like a teenaged boy.

“Well, that’s a right you have to earn.” She said with a serious tone.

With that, separated herself from me, sitting on the other side of the couch.

“I hope I didn’t say anything wrong” I said

She took a large swig of wine before shooting a look at me.

“Get undressed.”

I looked over at her in terror, ‘did she just say what I think she did?’ She was so straightforward, so in charge, so dominant. This was her show, she was the boss. She stared at me and assertively, she continued…

“Didn’t you hear me kid?”

Nervously, I arose from the sofa standing before her.

“Go on” she cooed me on, taking another sip of wine.

I proceeded to remove my shirt, placing it on the sofa beside her. Then I unbuckled my belt and unzipped my pants, letting them fall to the ground. I stepped out of them, one leg at a time, folding them, placing them on the sofa beside her.

I stood before her in nothing but briefs, and socks.

She was assertive without even saying anything. The look in her eyes said it all. I must admit, I was afraid of her, petrified.

Slowly, I reached into the waistband of my briefs and in one swift motion, I slid them off.

There I was, completely naked before the woman of my dreams.

Her eyes were transfixed on my stiffy, Babs took one final swig of wine, clearing the glass.

Slowly her eyes peered back up to me.

She arched an eyebrow as a sly smirk appeared.

Suddenly, her hand shot out, roughly grabbing a firm hold of my penis.

“Well no wonder you’re not married. You have the dick of an eight year old,” she said in such a tone that sent shivers down my spine. I gulped in utter humiliation. This was not at all how I wanted this to happen. I knew I was small, but I didn’t think she’d call attention to it, at least not like this.

“Such a shame. You looked just like a man. But you are not a man, you’re a little sissy. Just a dickless sissy,” although she was playfully teasing me, I detected a sense of disappointment and disapproval from her end. No one had ever called me a sissy before. I always imagined a sissy to be a feminine male and that just wasn’t me. No way, no sir. It wasn’t me at all.

“Babs, please don’t call me a sissy. I’m not a sissy. I’m a man” I protested.

“No you’re not. Men have penises. Low, thick hanging flesh muscles that can please a woman, that can take a woman where they are trying to go every time. You simply don’t have that. You have a little itty bitty worm. It looks like a coat hook……. But, you’re so hard!” she looked up at me in disgust, “you like this? You like me telling you how small and silly your little clitty is?”

A smile slowly formed in the corners of her mouth, “You like me telling you how pathetically small you are?”

Her tone of voice became softer as she looked up at me with those big brown eyes. She continued to fondle my privates, almost whispering at me.

“You’ve been teased before, haven’t you? Haven’t you?” she asked

At this point, I was so humiliated, I was almost on the verge of tears, “Yes, yes I have.”

“What happened? Tell me about it Sweetness”

“Not much to tell. I was on holidays in Greece and I was on the beach. I met this girl and we hit it off. After a while, she wanted to go skinny dipping. When she saw that I wasn’t packing, she, she, she told me to get lost.”

“She was right to Frankie. She could never want you, real women want real men. And you aren’t a man. Not with what you got dangling between your legs. You don’t even deserve to be called a man,” at this point, Babs tightened her squeeze on my member, looking down at it she started to giggle, noticing my pre cum.

“Oh! Look at that! You’re leaking. This is really turning you on isn’t it? Yeah? You sick little faggot,” she teased.

I could feel it gathering in my loins, this was working. I was nearing the edge, I was almost there. It’s not quite what I had in mind, but at least she was tugging on my raw wiener. That’s when she asked me something that took me completely by surprise.

“How about guys? Guys have laughed at it too, haven’t they?”

“In high school, yes.” I responded.

“Did you like it? Did you like being teased in school?” she asked

“mph! yes. I did.” I admitted

Babs started laughing, “I knew you were a faggot! Did they call you names?”

“Yes Babs, they did.”

“What did they call you?” she asked

“They called me baby dick. And not just in the locker room, out in the field, out in the hall, in front of girls. It was a name that stuck.” This trip down memory lane had taken it’s toll, like a tonne of bricks I started to sob in despair. “They ruined me. It was horrible”

“Well, in all fairness, I’ve seen babies with bigger dicks than you” Babs started laughing once more. She didn’t seem to care that I was sobbing like a little girl. “Look at you, crying like a sissy” she added. “How can any woman respect someone like you? A little, stuttering, crying, sissy, masturbator!”

Perhaps to taunt me, Babs slowed down her pace, right down. This in turn denied me any pleasure, ending my impending explosion. Through my sobs, I grunted in sheer frustration.

“You want to sneeze don’t you?” she asked

At the time, I didn’t understand what she meant, “Sneeze?”

She explained, “Real men cum. Faggot sissies with girls dicks, sneeze….. Did all the girls in high school laugh at you?” she asked

“Yes, I told you, they all laughed at me. I would walk by a group of them and hear them giggling. They knew. They all knew. Needless to say, I wasn’t popular in school. I was so lonely… maybe that’s why I am the way I am today” I bit my lip in embarrassment as my cheeks turned three shades of red.

“So when I asked you why a good looking guy like you isn’t married, you should have told me the truth. You should have said, ‘because I have girls dick. It’s the cutest little thing. It’s good for nothing.’ That’s what you should have said. That’s what you should have told me. Cause it’s the truth. Isn’t it?”

“yes, yes Babs, it’s the truth. I have a girls dick. It’s the cutest little thing and… its good for nothing.” I said

“and you’re a sissy” she added

“and I’m a little sissy” I repeated

“good girl!” Babs burst out laughing once more.

I looked down at her with pleading eyes, not sure if she was being serious or if this was just a game. I could not tell what was going on through her mind. But I could tell that she was enjoying this. She was getting off on teasing and humiliating me.

That’s when Babs told me what I didn’t want to hear, “I’m sure you know by now that we’re not going to be having sex… ever. This body is off limits to you. You don’t deserve it. No sex, no kissing, no touching… this isn’t for you. This is for real men only and you; you are not a real man. You are a sissy. Sissies are only good for one thing; cooking and cleaning”

Babs arose from the sofa, keeping a tight grip on my little boner.

“Faggot sissies like having things shoved up their ass, boy have I got a treat for you!!” With that, she led me upstairs to her bedroom by my erect member.

Once we entered her room, she started barking orders at me.

“Get on the floor!”

I complied, getting down on my knees before her, not sure what to expect.

“On your hands and knees!” she barked.

I complied, getting down on all fours, like a dog.

With that, she pressed her right heel against the back of my head, “kiss the floor!!” My face was forced down onto the hardwood floor as I puckered up. “keep your ass up and your head down!”

I could hear the ‘clickety-clack’ of her heels as she walked off into the bathroom. I didn’t move, I stayed down in that position not wanting to further disappoint or upset her.

I waited patiently until I heard the ‘clickety-clack’ of her heels once more. She walked over behind me. I could hear a weird fumbling rubbery sound… almost as if she were putting on a condom. My mind wondered as I pictured her putting a rubber on a dildo.

I squinted as I waited for the inevitable, the unthinkable. The deflowering.

I couldn’t have been more wrong.

In fact, she was putting on a pair of surgical gloves. “Honeybunch, now were going to see how much of a sissy you really are…. This is called, milking the prostate”

Before I could react, she had shoved two fingers deep into my anus.

“Feel good in there faggot? You like that you sissy?” she asked.

I grunted in pain and… oddly enough, in pleasure, “oh! Babs!”

“Just relax. Enjoy this feeling in your man pussy.” Babs had made it deep, deep into my asshole. She started to rotate and twist her hand in a clockwise motion, massaging my prostate. The sensation was so incredible; I can barley think of the words to describe it. Suddenly, I felt it again; that familiar feeling, gathering in my loins.

“You’re such a sissy, you like things in your sissy cunt? Huh? Don’t you? You like things in your cunt hole? In your man pussy?? Don’t you?” she laughed

“mph!! yes! oh god! Oh Babs!” I grunted

“And to think I was going to let inside me…. At lease one of us got fucked tonight, right?” Babs added.

With her free hand Babs reached across, grabbing a tissue.

As she pounded my ass, she began to wrap the tissue around my little penis, firmly holding it in place ‘milking’ me as she continued to finger fuck my tight little asshole.

In a matter of seconds, this was all too much. This had taken it’s toll. I let out a girlish screech and an audible groan as I climaxed, ejaculating into the tissue.

“Aiiiee!! Mpfgh!! Arhg!!! Oh yes! Oh god! Yeah! Mpft!!!” I guess I was a sissy. After all, what ‘man’ would let a woman do this to him?

“Good girl! That’s it. That’s a good little sissy” Babs chuckled to herself as if to say ‘job well done’.

Slowly she extracted her fingers, and then the tissue.

At that point, I was so exhausted and spent that I collapsed to the floor, panting and exclaiming in disbelief. ‘Had I just been violated by the girl of my dreams?’

“So tight. So very tight….. faggot,” Babs continued to laugh as the humiliation, embarrassment and guilt had sunk in. I literally began to cry at that point, the lowest I had ever been.

“aww! Is the little sissy crying? What’s wrong sissy?” she was mocking me.

Babs sat on the edge of her bed, looking down at my pathetic display. “You’re such a looser.” With that, she pat her legs motioning for me to get up on top of her. I looked up at her with confusion.

“It’s time for your spanking. All sissies deserve to be spanked.”

I don’t know what came over me, but oddly enough I found myself conforming to her demands. Submissively, I arose from the floor and without question; I laid over her nylon clad legs on my stomach. I was her bitch. I wanted this. I wanted her to use me.

“This is going to hurt you… oh, so much” With that, she grabbed a fistful of my testicles, squeezing the life out of them as I screamed in horrific pain.

“Oh! Mpf! What are you doing?? Oh gawd!!!” I pleaded.

With her free hand, she proceeded to slap my bare ass.

CRACK!

CRACK!

CRACK!

Like thunderclaps. Powerful, slaps to my ass. She was incredibly strong.

In desperation, I made a stupid attempt to get off her lap. This in turn caused her to tighten her grip on my testicles.

“No! No! Stay! Bad sissy girl! Bad sissy!! No!!”

CRACK!

CRACK!

CRACK!

Tears streamed down my cheeks as I literally balled my eyes out, crying like a little baby.

“Oh god! stop! Please! Babs! Pleaaaaassee!!!”

CRACK!

CRACK!

CRACK!

I pleaded with her once more, “For godsake! At least let go of my—

“—your little eggs?” she teased.

“D,d, do you have any idea how much it hurts??!?” I whimpered.

CRACK!

CRACK!

CRACK!

“Still hurt?” she mocked.

“Yes! Please!!” I pleaded. It was no use.

CRACK!

CRACK!

CRACK!

CRACK!

CRACK!

“How bout now? Hurt still?” she teased

I knew what she was doing. The more I resisted, the worse this would be for me. I decided to play her game, “no, no Babs. May I have another?”

“Good girl. Now, no more crying, okay?”

CRACK!

CRACK!

CRACK!

After a good fifteen minutes, my ass had taken a good hard beating. It literally felt like it was on fire, but I wasn’t fighting her. I had given up, I had completely surrendered and she was going crazy. She loved it, she loved squeezing my balls and slapping my ass. The ultimate humiliation.

And then, all of a sudden, she stopped. “There you go. All over babygirl… that wasn’t so bad now was it?” she said.

“No Babs. No.” I was still sobbing at this point.

“Stand up honeybunch.” She ordered.

I climbed off her lap in a daze; my eyes were red as I’d been crying so damn hard. Babs looked down at my flaccid little member and smirked once more.

“I think you’re ready now” she said standing before me, “Follow me.” I followed her into her walk-in wardrobe. This wardrobe was massive, equally the size of my whole bedroom.

She led me through a labyrinth of her fancy frocks and casual outfits. “Stand here.” she said, motioning for me to stand before a mirror.

There I was, completely naked: my ass pelted my eyes red and my flaccid little member completely introverted. She stood behind me, completely dressed, perfect make up, perfect hair, confident, strong and dominant. She began to rub my shoulders, slowly making her way over to my chest.

“Look at us.” She said as I looked up at our reflection.

“I see me and my sissy maid.” She smiled at my predicament as I looked up at her with fear and uncertainty.

She continued to rub my chest, “You don’t need all this hair. Real mean have hair and you aren’t a real man. You don’t need this hair…. In fact, that’s your assignment for me. I want you to shave your chest when you get home. Okay?” she said.

I nodded, ‘yes’.

She continued, “While you’re at it, shave your legs and your pubes. I want you clean. Got that?” she said.

I nodded once more, ‘yes’.

“Mmmm, good girl. Now wait here, I have something for you.”

Babs wondered off, leaving me there all alone, standing before my reflection. She had this power over me; I would do anything she asked of me, with no hesitation. Just to be in the same room as her was a dream come true. Despite the fact that things did not go as planned, I did spend the night with the girl of my dreams…. But things were just about to take a sharp turn in a completely different direction.

Several minutes passed before Babs came back. The look on her face was all too clear; she was excited and overjoyed about something. I knew she had something in store for me and I was more than happy to comply, whatever it was.

She held a scrunched up ‘pink’ outfit and a leather duffel bag. “You’re perfect Frankie. The perfect one. I’ve been waiting for someone just like you.” She said with such enthusiasm.

“I want you to put this on,” she said as she unruffled the pink outfit. “It was my husbands. You see, he used to be my sissy maid. It was our little arrangement and it was perfect. However in time, he got jealous and acted out of line. In the end we ended up getting a divorce. I got the cars and the apartment, and now he lives in his mothers basement” she burst out laughing, “he’s probably more pathetic than you.”

She held up the outfit beside me, I turned three shades of red.

It was a short cotton Gingham Sissy Maids Outfit. Complete with a white frilly apron, a blue ribbon tie and a frilled lace hem. This was the ultimate emasculator.

“Y, you what? You want me to put that on?” I asked nervously.

“If you ever want to see me again dear” she replied.

She watched with wide eyes as I subserviently stepped into that humiliating little maids outfit. Needless to say, it was tight: very tight and short: very short. She gave me a helping hand as she proceeded to do up all the zips and ribbons and buckles.

“Awww!!! Don’t you look adorable!!” she said

“why do you have this?” I asked

“It was my sissy ex husbands… now, it’s yours.”

With that, she opened the duffel bag “Its not complete yet.”

To my horror, I was forced into a white garter belt, white stockings, white silk gloves and a long blonde wig. Yep, I sure as hell looked the part. “Oh my god!” I said in astonishment as I caught a glimpse of myself in the mirror. I was a sissy. A complete and utter sissy.

“Just one more thing,” she said reaching into the duffel bag.

She pulled out a pair of 10 inch stiletto heels.

One by one I was forced into these small, uncomfortable shoes. I looked up at the ceiling in utter humiliation as she buckled me up when all of a sudden I heard a ‘click’.

I looked down and to my horror; she had ‘padlocked’ my right shoe on. The leather strap wrapped around the shoe was not coming off, which in turn meant that the shoe was not coming off. These shoes were not coming off until she said so.

“What are you doing?? What is that??” I asked in desperation.

“Now for the rules.” She said ignoring my last question.

“Rules? What rules??” I asked.

“Rule number one: you don’t speak unless you are spoken to. Rule number two: you are here to serve me and only me. Rule number three: you must do everything I say no matter what. This may include, cooking, cleaning, washing my clothes, driving me to the mall, serving drinks to my guests or…. pleasing my lovers.”

I didn’t know what to think, I didn’t know what to make of all of this. But that crazy look in her eye got my blood racing. Before too long, I was sporting a modest little erection.

She noticed instantly, “oh, and no erections unless I say so” with that, THUMP!! she punched me in the balls with all of her might.

I collapsed to the ground, cupping my crotch, coughing and gasping in pain.

“Now, get up and do the dishes.”

Of course after the pain subsided it was a breeze. It was even a little exciting. I was her sissy maid. I couldn’t believe it. This was the most intense and erotic thing that had ever happened to me, I wanted to prolong it.

Alas, this wasn’t what I had in mind.

For the rest of the evening, she ignored me.

First, I washed the dishes, then I sweeped and then I did her laundry. After that, I scrubbed the windows, cleaned the toilets and cleaned the showers. Needless to say, it was a very tiring evening. It was also a very uncomfortable evening, given the fact that I was wearing an outfit three sizes too small and shoes meant for a teenage girl.

At around 1:30am, she told me I was done for the evening.

“I want you back here tomorrow night at 8pm, sharp so you can do the rest of your chores,” she said.

“Yes Babs.” As I started to remove my outfit, she stopped me.

“What are you doing?” she asked

“huh?”

“You are my sissy bitch. I want to see you like this always. You will enter this apartment dressed like that and you will leave this apartment dressed like that!” she said.

“But, but, what if someone sees me in the hall—?”

“— Are you complaining??? Cause if you are, there’s the door. But if you leave under those circumstances, don’t ever expect to see me again.” She said.

I hung my head, defeated. She was right, more than anything I just wanted to serve her. “Sorry Babs…..” I then remembered the lock on my shoes: I had to work tomorrow! I needed to get these shoes off! “Can you at least take off this padlock?” I asked.

“Why?”

“What about…. If I have to go out? Or go to—”

“—then you’ll go in your sissy shoes.” She was actually serious! I couldn’t believe it.

“Now, scram. I’m tired and I have a busy day ahead of me tomorrow.”

So, I was forced out into the hall, dressed in my sissy outfit. It would have been embarrassing if I was caught like this, very embarrassing indeed.

As I reached my door, I came to a shocking realisation….. my keys were in my trousers back at her place. I couldn’t get into my apartment! What was I to do?? This was quite a predicament I had gotten myself into.

I returned to her door, ringing her bell…. No answer. “Babs! I need me pants! I cant get into my apartment! Babs! Please!! Babs!!” I pleaded. Hell, even if she was awake, she wasn’t going to answer. This was her game and she was serious. Deadly serious.

So I was locked out of my apartment on a cold night, dressed in a little itsy bitsy pink maids outfit. I weighed my options, thinking of the least embarrassing way to get access into my apartment. ‘I could run outside and climb up through the fire escape, or I could run outside to a payphone and call a locksmith, or I could—‘

Just as these thoughts were racing through my mind, the elevator doors flung open; filled with five middle aged cougar divorcees, all coming back from a night out on the town: Ms Bourke, Mrs O’Leary, Ms Diablo, Mrs Preston and Ms Guerra. They were all gobsmacked to see me standing there in the hallway, dressed like that. Dressed like a sissy faggot.

I started to explain, “I was locked out of my apartment, if I could use a phone that would be—”

This was too much for them as they all burst out into uncontrollable laughter. “I, I was at a costume party!!” I pleaded with them. In turn they took out their phones and started snapping photos. To my horror, this attention got me hot and bothered and soon, I was sporting a modest erection. I squeezed my legs together and cupped my crotch…. I must’ve looked so pathetic! I’m sure they all knew I was sporting wood, it was obvious and it was so damn humiliating. I had never been so embarrassed in all my life.

They were all laughing so hard, they were in tears “Please! I need to get back into my- please, I need to use a phone!” I pleaded once more.

An hour later, I was sitting in Mrs O’Leary’s apartment waiting as she spoke with the locksmith outside, posing as the tenant of my apartment. Mrs O’Leary found it hysterical and assured me that ‘my secret would be safe with her’. I’m pretty sure she thought I was queer. All things aside, I didn’t care. I was glad she helped me out. “Well, well, well, no wonder I never see you with a woman!” she teased. I was too exhausted to explain, I just wanted to get out of those humiliating clothes.

Before too long, I was in my apartment desperately trying to remove my shoes. Yet no amount of trying was going to get me free. The shoes were not coming off. The leather strap wrapped around my right shoe was thick and tight, the padlock itself was a heavy duty model. ‘No amount of trying was going to get these damn shoes off’. I was stuck with them and I had to go to work the next day! This was quite a predicament I had gotten myself into.

The next day, I called in sick… yet again. My boss was not happy, not happy at all. I assured him that I was violently ill and promised that I would have a doctor’s certificate to back this up. ‘How the hell am I going to do that?? I don’t even have a doctor in this town! I’m screwed!!’

I spent the whole day in my apartment, wishing for some type of miracle. Of course, I kept trying to get out of the damn shoes…. but with little luck. All things aside, I did manage to ‘learn’ how to walk in heels that day. Furthermore, I followed her orders and shaved my chest and my pubic area. I was hairless, I was clean. I was hoping that she’d reward me in one way or another.

At around 6pm, my phone rang “Honeybunch! I need you to come over a little earlier tonight. I need you, I need you bad!” Babs said on the other line.

Her game excited me; I couldn’t wait to see what she had in store for me. I kept thinking in the back of my mind that eventually she’d drop the charade and let me sleep with her. I was praying for that.

So, I got ready in that humiliating outfit and wondered over to her apartment. I rang her doorbell and waited patiently…. When her door flung open, I was pleasantly surprised.

She was dressed in a nightgown, but with perfect makeup and high hair. She was stunning. Obviously getting ready for a night out on the town. “Come in sweetie”

“Where are we going?” I asked.

She arched an eyebrow and started chuckling, “Oh that’s so sweet! You think I’m dressed like this for you?…. awww! That’s adorable!!” she teased, “You are so sweet! I have a date tonight honeybunch. I need you to clean up for me. I can’t bring home company to this pigsty!!!”

“Oh!” I said in defeat. It felt like someone had reached across and ripped my heart out. I almost felt like vomiting.

Soon thereafter, I was ushered into the kitchen where a pile of dishes awaited. “As you can see you have allot of work to do tonight”

I was feeling small. Here the girl of my dreams was making me clean her house while she was getting ready to go out on a date! It was unfair! I wanted to be that guy!! Not the sissy cleaning her apartment.

“Get to it sissy!” she said pointing at the unusually large pile of dirty dishes.

For the life of me, I didn’t know why she was doing this to me and I didn’t quite understand why I was so weak as to let her do it. But I just had to be with her. No matter what she asked, I would comply without question, no matter how bad I felt inside.

As I cleaned her dishes I could hear her in the other room, watching television… it was as if I wasn’t even there. I was being used… and I liked it. Yes it was emasculating, yes it was shameful but I wanted it. In fact I wanted more; I wanted to push the envelope.

As soon as I was done, I decided to ‘test’ her, breaking rule number one ‘don’t speak unless spoken to’. I slowly approached her in the living room, “Babs, I’m finished.”

Babs proceeded to check the cleanliness of the kitchen, a stern look on her face the whole time. I stood in a corner, watching her with wide eyes, every little bit nervous and perhaps just a little afraid.

After what seemed like an eternity, she leaned in to me and gave me a peck on the check, “good girl, very clean.”

I sighed in relief. “Come! I need you to help me with my outfit” she said.

“Outfit?” I asked

“Yeah, I really want to turn this guy on! And you’re my outfit tester!” This was indeed emasculating; being referred to as an ‘outfit tester’. For the life of me, I had no idea what that meant, but I was soon going to find out.

She ushered me up to her bedroom once more and forced me down on the edge of her bed. “Wait here” she said, walking off into her wardrobe.

I anxiously waited for her to return with a knot in my stomach, “Are you really going out on a date tonight?” I asked.

“Yes, of course!” she responded, “It’s Friday night!”

I hung my head in shame, “Oh, uh, I thought that we—”

Before I could finish my sentence, she emerged from her wardrobe, completely nude. “You thought what?” she teased.

To say I was intimidated would be a gross understatement. She had the body of a goddess: muscular swimmers thighs, a flat toned stomach, large C cup breasts and a firm, shapely upper body. She was flaunting it before me. She was teasing me. It was as if she was saying ‘take a look at what you wont ever get to enjoy’.

Trying to find the appropriate words, I stuttered, embarrassed.

She found it amusing, “aren’t you a little sweetie!”

With that, she grabbed a hold of my right hand, slowly placing it on her pubic mound. “I like you Frankie, but not like that. I have real men for that.”

These words were hard to swallow. I’m ashamed to admit that at that point, my eyes welled up with tears as I was overcome with a sudden case of loss and extreme sorrow.

“shhh, don’t cry honeybunch…. Look at me” she said.

“Know your place. You are a sissy. Okay?….. I have a hot date tonight and I need your help.”

I nodded ‘yes’ indicating that I’d help her ‘test’ her dress out, whatever that meant.

Much later, we were both in her wardrobe, standing before her mirror. She was slipping into a skin tight red cocktail dress. I was standing behind her, zipping her up. “mmm, I look hoooot!” she said to herself, striking a pose.

“How do I look?” she asked me.

I was lost for words, “erh, you look amazing! Your date is such a lucky guy”

She smiled in appreciation, “get my stockings” she ordered.

Babs sat down on her bench, waiting patiently as I fetched her stockings “go on, put them on!” she said extending her long legs before me…..she had opted to forego the use of underwear. In other words, she wasn’t wearing any panties and I could see her honey pot. Needless to say, I started to get aroused.

I knelt down before her and one by one, I slowly started rolling the stocking up in a ring, carefully encasing each leg in the black silk. My hands were trembling as I adjusted the black seams straight and clipped the garter belt to her lacy tops.

“Good little bitch…. Go get my shoes” she ordered.

As I rose to my feet, she stopped me, “wait! I want you to crawl! Crawl on the floor like a little gay doggy!” she giggled.

I sank back down to the ground, proceeding to crawl over to her shoes. As I did so, Babs was on the verge of laughter, chuckling ever so loudly. Not hiding the fact that she found my pathetic display amusing.

As I crawled, my dressed hiked up, exposing my bare ass to her “Wiggle that ass! Like a dog!” she ordered. As I did, she started laughing out loud in hysterics, “Oh god! You’re pathetic!…. bark for me! Go on! Bark!”

I swallowed my pride and began to “WOLF! WOLF! WOLF!”

“No, no, no! You’re a girl dog! Bark like a girl dog!” she said.

“YIKE! YIKE! YIKE! YIKE!” I yelped like a poodle.

Babs was laughing to her hearts content. This went on for a good several minutes. “Okay, okay, that’s enough. I’m going to be late! Hurry up! Get my shoes bitch!”

I reached for a pair of 4 inch ankle strap stiletto heels, sexy shoes…. Yet not quite as sexy as mine. I slowly crawled back to her feet as she watched with wide eyes, grinning from ear to ear.

She extended her left foot as I submissively proceeded to slip the heels into place. Firstly grabbing a hold of her left foot, buckling the little ankle straps into place. As I started slipping on her right heel, Babs leaned back, propping herself up with her arms. She smiled at me, knowing that I was under her spell. I was her bitch. She knew she could make me do anything. It was the look in her eyes that said all of this.

Once the deed was done, she crossed her legs and stared down at me, “stand up” she ordered.

I jumped up to my feet anxiously.

“You like dressing me up don’t you honeybunch?” she teased.

I nodded ‘yes’ submissively.

Playfully, she started tapping my raging hard on with the toe of her right patent high heel.

“I bet you feel so inadequate right now. Real men get to fuck me; little sissy boys with no balls get to fist fuck themselves.” Forcefully, she started to press harder on my penis with her heel. “You’re a good little outfit tester. I look hot don’t I?” she asked.

This was far too much for me. I lost all control as I suddenly spazamed, ejaculating all over myself, making a mess of my cute little dress. I hung my head in shame as the humiliation and guilt came rushing through me.

Babs shook her head in disapproval.

“Get the fuck out of my house. I’ll call you tomorrow.” She said.

So, once again I was forced out of her apartment, dressed in that humiliating little maids outfit. I spent the rest of the night reflecting on the events of the last few days. Of what she’d made of me, of what I’d become.

I slipped out of that embarrassing little outfit and proceeded to clean my cum stains out of it. Unfortunately, due to the padlock around my right shoe, I couldn’t get out of the stockings. So, there I was in my bathroom, wearing nothing but 10 inch stiletto heels, stockings and a garter belt cleaning sperm off a pink frilly maid’s outfit which I was forced to wear. I cried upon realising what I had become, I started to cry in shame. I knew I wasn’t a man, at least not in the traditional sense.

Later that night as I tried to sleep, I could hear muffled sounds coming from across the hall: the tell tale sounds of hot heavy sex. Obviously, Babs had a successful evening. Her date had gone well and that night, she was getting her brains screwed out by an able a-sexual alpha male: something that I wasn’t and something that I could never be. ‘Why the hell was she doing this to me? To torment me? To mind-fuck me?’ I knew she was doing it on purpose, and it drove me wild.

Due to the fact that I was unable to get out of my heels, I kept calling in sick to work. It was my only option. Babs sure as hell wasn’t going to give me the key and no amount of trying was going to free me from those god awful shackles.

It took a whole week before Babs called me again and it was just to ‘clean her dishes,’ something quite casual. Although I didn’t know it at the time, I was her slave. She got me into this routine. She would usually phone me a night ahead to alert me to do her dishes and clean her apartment. She often pretty much ignored me, talking on the phone or watching television.

Whenever I was done, I’d approach her “finished Babs”

“Good girl… you can go now” dismissed, just like that! It was an emasculating process, yet I was driven to her. I looked forward to it. I centred my whole week around my visits to her place. I wanted to be used by her. I longed for it.

Babs had refused to remove the padlock from my right shoe, no matter how many times I asked her. Therefore, I was stuck with it. Needless to say, I hadn’t been out in public for a whole month. In hindsight, I didn’t really need to, Babs was my world. Everything was centred around her. Nothing else mattered. Before too long, my employment was terminated and I was merely living off my savings, which were quickly eroding.

As the weeks passed, Babs grew tired of me and my visits became less frequent.

On one Tuesday morning, I was out of my apartment, collecting my mail… dressed in a long dressing gown, concealing my undergarment and my stiletto heels. Suddenly, I heard a shuffle nearby, only to notice Babs exiting her apartment: hand in hand with another man; kissing and giggling like most lovers do.

I looked on, jealous, embarrassed with a knot in my stomach.

As I made eye contact with her, she looked away. She was no longer interested in my shenanigans. It stung. It really hurt. It was clear she had gotten tired of me, but I couldn’t understand why.

A few more weeks passed before she called me again. It was a Saturday night, “I’m glad you’re home, sweetness. I need you. Come over right now!”

Anxiously, I proceeded to dress up. Tonight I was determined to reassert myself as part of her life. I wanted her to need me, to want to use me. I was determined to show how much of a sissy I could be. I just wanted to be with her. I put on my little pink outfit, my silk gloves, my blonde wig and I even applied a generous amount of make up: complete with rich red lipstick, blush and eyeliner. I was determined to please her.

I stood outside her door, rang the bell and waited anxiously.

She was a sight for sore eyes.

She was dressed very elegantly in a white blouse with tight jeans and knee high black leather boots. She was actually taken back by my feminine appearance, “Wow! Look at you!! You look very pretty. Come on in!”

With that, she ushered me in.

To my absolute horror I soon learned that I was not her only guest. In fact, she was in the middle of throwing a casual get together with some of her closest friends. Some of whom lived in the building.

As I was ushered into the living room, I yelped in fright. My cheeks turned three shades of red as I did my best to cover myself. Of course, this pathetic display caused all of her guests to erupt in laughter.

Her guests included: Mrs O’Leary, Ms Diablo, Ms Hernandez and Babs’ lover Thomas Cannon.

“Come-on Frankie! Don’t be embarrassed! Calm down!” She said.

Mrs O’Leary couldn’t contain herself, “Oh honey! Look at you! You like dressing up like a girl? I knew you were a closet faggot!”

Babs was also laughing along with them. This was simply too much for me; I started to pant in embarrassment. “Ladies and gentlemen, this is my sissy: Frankie, say hello Frankie”

I swallowed my pride, “Hello everyone”

More fits of laughter followed. I can hardly believe I had been so stupid as to walk into this humiliating trap.

Thomas leaned into Babs and whispered something in her ear, which caused Babs to giggle like a little school girl, “yes he does” she said to him.

After the laughter died down, Babs started to further taunt me, “Frankie, why don’t you get my guests some drinks? Make yourself useful. You know where I keep my liquor.”

So that was that. There I was, serving her guests. I didn’t think things could possibly get any worse. As I proceeded to make my way over to her liquor cabinet, all I could hear were muffled giggles. It was horrible. But what could I do? I complied with her every demand.

As I proceeded to serve her guests, every one of them had a ‘smart’ remark to make about my attire.

“You look very pretty honey!” Ms Hernandez said.

I was far to embarrassed to say anything. I just kept my head down, staring at my feet. Babs didn’t like this. No, she didn’t like this at all.

“Faggot! Where are your manners?? Ms Hernandez just gave you a compliment!!” Babs said.

Pouting, I responded “thank you”

This wasn’t good enough, “Look at her when you talk!” she ordered

At this point, my eyes were red from crying. I slowly looked up at her, “Thank you Ms Hernandez, thank you.” I said sobbing.

Of course, this just caused more outbursts of laughter.

“Frankie has a little secret! Can any of you guess what it is?” Babs announced.

I didn’t know what to expect. I didn’t know what she was doing. This was torture! Ms Diablo pointed at me, laughing, “Oh my god! look at him! He’s blushing!! This must be a good one!!” more laughter followed.

Thomas leaned forward, “Let me guess, he’s wearing a butt plug?”

All of them screamed with laughter. Insane laughter. Thomas looked at me dead in the eyes and shook his head at me. What a jerk! This was the guy ‘sticking it to’ the girl of my dreams! I wanted to get out of there! I didn’t deserve this.

“Good one, Stud. But that isn’t it. Anyone else?” Babs asked.

Ms Diablo leaned forward staring me up and down, “I bet he has a really tiny dick. Is that it?”

Knowing where this was headed, my face went bright red. My ears were burning, my eye brows arched. I started to shake with embarrassment. It was all too obvious.

“Very good!” Babs said.

More laughter followed.

“Show them sissy.”

I didn’t know what she wanted me to do; I sure as hell was reluctant to expose myself to a bunch of strangers, “Babs??”

Assertively, she repeated, “show them!! Lift up your dress and show them your little sissy stick!”

With that, all of her guests leaned forward, waiting for me to expose myself. I was violently shaking out of fear, embarrassment and I’m afraid to admit from excitement.

Slowly, I reached down, lifting up my dress, exposing my flaccid little pecker.

Audible gasps filled the room.

Smugly, Thomas leaned back smiling.

Ms O’Learly’s jaw was wide open in astonishment.

“Oh my God! He’s soo tiny.” Ms Hernandez said.

“Yes she is. A liddle baby dicklet” Babs added.

More fits of laughter followed as I stood there looking every little bit ridiculous, holding my dress up before a pack of strangers as they laughed at my soft little penis.

“Its sooo cute! I actually like it. Can he fuck?” Ms Diablo asked.

The humiliation was too much for me. I never imagined that I would ever be in such a situation. They continued to speak amongst themselves for a while as if I wasn’t even there.

I stood there, not moving, still holding my dress up as they all took turns taunting me.

“I don’t think he can fuck” Babs said.

Babs looked directly at me and smiled, “I don’t think he ever will”

“Aww, poor baby dick Frankie…Shame, it’s such a pretty little dickie.” Ms Hernandez added.

“Frankie? Do you want to see what a real man’s penis looks like?” Babs asked me.

I was in shock, I couldn’t believe it. Before I could answer, Babs turned to her lover and said, “Tommy boy, show him.”

Thomas arose, taking his place beside me. With that, he began to unbuckle his pants, letting them drop to the ground… he wasn’t wearing underwear. ‘faloump’ his flaccid eight inch cock hung down, low think and heavy. He smiled proudly.

All of the ladies gasped in approval. Some licked their lips, others started to chuckle noticing the obvious compassion between the two of us.

There I was, before a group of horny middle aged women, with my little pecker which looked like an extroverted belly button on show, standing next to a freak with a cock that looked like an elephant’s trunk.

“oh my god! wow” Ms Diablo exclaimed

“You’re a lucky girl Babs” Ms O’Leary added.

Babs proudly smiled, “Frankie, take a closer look” she said to me.

Deep down, I knew where this was headed. She wanted to put me in my place. To remind me that I wasn’t a man, no matter how hard I tried. That I would never have her.

I looked down at Thomas’ cock monster in envy.

“I want you to say; I’m just a tiny dicked sissy and I appreciate being around a real man with a man sized dick.” Babs declared.

I swallowed my pride and repeated, “I’m just a tiny dicked sissy and I appreciate being around a real man with a man sized dick.”

Babs smiled at me, “Are you looking Frankie?” she asked me.

“Yes, Babs. I see it” I replied.

“Look! Look at how big he is. Much bigger than you!” she said

“Yes. Much bigger than me.” I added.

“Now look at your dick.” She demanded.

Slowly I looked down, in comparison.

“See the difference?” she asked.

“Yes. I see the difference” I replied. I was docile, I had no fight. I never did.

“Touch it!!” she demanded.

Slowly, I grabbed a hold of my flaccid member, holding it with my thumb and index finger.

“No! No! Not yours! His!!!” she said.

I suddenly felt weak at the knees, letting my dress fall back down. I began to sob once more, “Please Babs! Don’t make me do this! I’m not gay” I cried.

She meant business, “Do you want me to force you? Trust me, you wont like that.”

I pleaded with her, “Please Babs. Don’t make me do this”

At that point, she literally shouted at me, “TOUCH IT!!”

I had no choice. Slowly I reached across, grabbing a firm grip of Thomas’ large veiny cock. I could feel it pulsing as it slowly inflated in my hand. The ladies gasped in astonishment. The humiliation was far too much for me.

“Aww! Look! He’s crying!!” Ms Hernandez pointed out.

This caused everyone to once again, erupt in laughter. My humiliation was complete.

With that, Thomas pushed me out of the way, pulling his pants back up, “Maybe next time you can suck me off like the little fairy faggot you are!” he teased as more fits of laughter followed.

After what seemed like an eternity, Babs started barking orders at me once more, “Don’t just stand there sissy! Make yourself useful!!”

“Uhh.. yes Babs. Anyone’s drinks need re-filling?-” I asked

“Gosh you’re stupid! You just brought us drinks!……sweep!!” she said.

I was dumbfounded, “Sweep?”

Babs pointed to the corner of the room, where a broom was waiting for me.

Submissively, I huddled over, taking the broom. For the rest of the evening I swept as the group of them continued to laugh at me and tease me. It was so demeaning.

I almost fell over twice because of those stupid high heels. Of course, they laughed and laughed until they grew tired of me. Soon enough, it was as if I wasn’t even there. They were all ignoring me. This went on for a good few hours.

Eventually all of her guests started to leave… all but one: Thomas. Of course I didn’t stop with my chores, I merely kept at it hoping that I’d be rewarded one way or another.

That’s when I heard it: smooching sounds. I looked over in their direction only to notice that Babs and Thomas were deep in a heavy make out session. I was overcome with extreme jealously as I stood there, watching in awe.

Unfortunately this caught the attention of Babs herself and she didn’t like it. She didn’t like it one bit, “So not only are you a sissy dicked fag, you’re also a pervert?”

Submissively I hung my head in shame and returned to my sweeping as their make out session continued. I felt so powerless and belittled, so terribly emasculated. I heard muffled giggling and groans, typical sounds that lovers on heat make.

I heard the sound of a zipper, “Wait, wait. Do we have to do it out here? I feel kinda strangewith this freak staring at us,” Thomas said.

As best as I could, tried to block it out. I kept sweeping, hoping that they’d ignore me as I had ignored them. In the corner of my eye, I caught a glimpse of Babs leading the way, with Thomas following her upstairs into her bedroom… followed by a loud THUMP! as she slammed the door shut behind her.

In my own world, I continued to sweep for several minutes. I tried to block out what was happening upstairs, but it was no use: I could hear sounds of pleasure coming from her room: heavy panting, groaning and moaning. I could hear Babs screaming in pleasure, “ARGH!!! OH TOMMY BOY!!” she screamed.

I set aside my broom and, with a knot in my stomach and waves of envy, I approached her room, standing by her door, listening to their sounds of sex. I kept thinking, ‘Why couldn’t that be me? Why? It wasn’t fair! It almost was me! Almost!’ As the sounds got louder, I could hear bedsprings screeching and a steady humping rhythm which was steadily intensifying. Needless to say, this whole scenario had taken its toll and I was sporting a modest little erection.

There I was, standing outside her door, dressed in a humiliating little maids outfit, masturbating underneath my dress as Babs was getting her brains screwed out by an able macho man. I desperately wanted to watch. I wanted to see Babs’ face as Thomas pounded her with his large appendage.

Suddenly, their pace quickened, they got louder and louder as Babs screamed at the top of her lungs, “Oh god! Oh yes! Oh! Argh!!! Ahh yeah! Ahh yeah! Pound me! Pound me! Yeah! Ahhh!”

Thomas was getting in on the act too, she was screaming out, “Enjoy! Enjoy! Enjoy! ARGHH!! ENJOY!”

I tightened my grip around my eager little soldier as I yanked myself for all I was worth until….. I ejaculated all over my pretty little outfit. God I was pathetic.

Guilt took over as my little guy slowly retracted back into me…. oddly enough, Babs and Thomas were still going at it. In fact they were getting even louder and faster. This Thomas was one hell of a lover!

Their love making lasted until the early hours of the morning. It was absolute torture. I stayed the whole night, sweeping, listening in envy to their love making.

At 6am I heard a little bell ringing. It was coming from Babs’ room. “Sissy! Get in here!!” she shouted at the top of her lungs.

Submissively I approached, standing before the two of them. The room was an absolute mess! Sheets and clothes were everywhere. Babs had this almost ‘drunk happy’ look on her face as she lay in her ‘mans’ muscular arms, her head resting across his pecks. He had a smug grin on his face and he had every right to, for he had just shagged like a prince.

I hung my head in shame, tugging at my dress, “Yes Babs?” I asked.

“Make us breakfast. I want oatmeal, Thomas wants bacon and eggs… and make us some coffee!” she ordered.

So I took to it like a good little sissy, making them their breakfast and their coffee, serving them and waiting until they finished so I could tidy up her bedroom.

When they were done, they both retreated to the shower as I continued my job: tiding up her room and ensuring that everything was in pristine condition. It took me a good half hour. Those feelings of envy returned however upon hearing them fornicating in the shower…. They were going at it once again. God this was bad.

After that, we pretty much both got into a standard routine.

Babs knew that I was unemployed and out of money, so she offered to take me in. But this would mean that I would be her full time sissy maid. This also meant a few things: I would always wear that sissy outfit, I would not interfere with her life, I would not speak unless spoken to, I would amuse her when ever she wanted, she could use me in anyway and I was to sleep downstairs in the closet…. for I was not worthy of a room.

She would continue to flaunt her lovers before me and parade me around like some sort of gay sissy freak, this was all to completely crush and destroy my spirits… and it worked. I was a shell of a man; I only lived to serve her and to clean her clothes, dishes and her apartment. I was her slave and I was never rewarded.

I’d often make up for it by finding ways to reward myself. Whenever she was out, or out of earshot, I’d sneak in a quick ‘rub and tug’. Of course, this was forbidden but it was something I absolutely had to do due to my extreme frustrations. After all, I am still a man, and all men have needs.

I’d usually sneak into her room, find a pair of her silkiest panties and fist fuck myself silly until I filled them with my warm goo. I knew it would be the closest I ever got to her pussy.

This worked for a while, and due to the fact that I did all of her laundry she never found out.

Every night, as her lover pumped her for all she was worth, I was in the downstairs closet, pounding my pathetic little pecker into her silk panties. Gosh! I was so pathetic.

Then, morning would come and it was always the same “Make us breakfast sissy! Clean this mess!” I’d take to it as her lover often chuckled at me from a far. It just wasn’t fair, no it wasn’t fair at all.

Then, on one October morning, I was caught pleasuring myself, masturbating into a pair of her cotton panties. God it was so silly. I thought she was out.

There I was with my skirt hiked up around my chest as I masturbated with a pair of her cotton panties. Of course, she hit the roof. I had never seen her so upset. I was convinced that she’d toss me out on the street.

“What the hell are you doing?!!? So this is what you do when I’m not here??? You sick freak!!! How dare you!!! How dare you!!! Argh!!! You sick freak!! What the fuck is wrong with you???? You fucking pervert!!! You’re disgusting!!! Ugh!!!”

I fell to me knees and begged for her forgiveness, I pleaded for her mercy and tried to explain myself, “you’re just so, and I…”

“b..b..b..b… can you even speak?” she teased, “God! You stuttering little pansy ass loser!!! Sometimes I wonder why I even keep you around!! Get the fuck outta my room sissy!!! GET OUT!!!” she was angry. I had never seen her so upset.

As a result, she administered another ‘spanking session’ as punishment, which seemed to go on for hours. Not only that, she squeezed my nuts to oblivion. After that, I couldn’t sit for a whole week and the pain in my stomach prevented me from getting aroused for quite a while.

Furthermore, my workload increased. In fact, she pushed me to the limit, “This is dirty! Work faster! Get the car! Get us drinks! Clean the toilet with your tongue!!!”

She had turned into this horrid tyrant and I was petrified of her.

So, here I am mopping the dirty bathroom floor on a hot summer’s day in July, waiting for her unprecedented return… I wonder what she has in store for me today???

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