Crystal's StorySite
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Mrs. Carmen Sheldrake

by Brian Houlihan

@2006 by Brian Houlihan

All Rights Reserved

brian_houlihan2002@yahoo.com

 

"Do you remember me talking about the difference between a sissy and a real man?"

"Not really."

"Real men have dicks, Precious. Big manly, masculine pricks. You have a baby dickie, a clittie. Even if I did let you into my pussy I'd never feel you, Sissy. Your dick is too small. So that's never gonna happen. This little guy is such a teeny weeny that you're never going to be able to fuck Mommy. Mommy needs Men, Real Men with Real Big Dicks. Understand?'

"Oh you're blushing again, Hon. I love it. I know it seems cruel Sweetness, but that's life. Sissies can be fun, but a woman needs a mancock in her cunnie. And you don't have one. Sissy. Tiny dickie bird girl."

Why did her humilation of me cause my dick to get so hard???

"Aw, baby dickie is all leaky again. Here let Mommy scoop that up. Here you are sissy, lick it up."

She fed me my precum off my hard dick and I licked and sucked it off her finger. And loved it.

"Good girl. Suck Mommy's finger just like a little sissy cocksucker girl. With a lil peeny."

 

I was driving thru my old neighborhood on the South Side of Chicago the other day. I hadn't been back here in years and years. Suddenly, when I passed The Beverly Country Club, a ton of old memories of Carmen Sheldrake, the sexy goddess that I worshiped and obsessed over, hit me like a tornado. I threw a rod that felt like a tire iron in my pants. Such a powerful memory and it happened so many years ago. Then I drove by the Sheldrake's old house. It all came flooding back to me. Worshiping her from afar at the country club pool. Then cutting her grass at her home. Our little "talks" after cutting the grass. And how they became more and more intimate and perverse and wonderful.

I got so excited by these wonderful, hot memories of this mesmerizing woman that my hands began shaking. I stopped off at a 7-11, picked up a six pack of beer and headed to the parking lot at Ryan's Woods. I needed to relax and enjoy myself and savor these hot thoughts and take care of the already leaking iron rod in my pants.

The memory of Carmen Sheldrake stands out like a crater from my other memories of high school. That's when it happened.

 

I was an only child going to an all-boys Catholic high school, Brother Rice. My parents were well-off, my dad was a vice president at a big electronics company. I didn't have any social life to speak of, just hanging out with my friends. Drinking beer in somebody's basement when their parents weren't home. Of course I didn't have a girlfriend and was perpetually horny.

My folks were members of the country club and I would go with them now and then to have dinner. I had to wear a suit and tie. The country club got to be fun in the summer when the pool opened and I could eyeball all the pretty girls sunning themselves.

I remember that the Sheldrakes were not Catholic and I liked that about them immediately. Mrs. Sheldrake stood out immediately from my parents friends because most of them seemed so ancient and unattractive to me. First of all, she was a very tall woman, about six foot, but in her high heels she stood about six foot four inches. But here was a very sexy woman who dressed sexy and obviously enjoyed her sexuality. She had a spectacular figure, big tits, big ass and a slim waist. She had Latin features, jet black hair, big brown eyes, she even had dark hair on her arms. She wore her hair long, always wore form fitting clothes, high heels, which accentuated her very big tits and big ass, and loomed over her husband by a few inches. Bob Sheldrake was a good looking man but rather docile and quiet. I knew her as a goddess from the moment I saw her.

I had met Mrs. Sheldrake a few years earlier at the pool when I was twelve. My mom wasn't much for exercising, swimming or playing golf. However, now and then she would go to the pool and sunbathe. I was a kid and I enjoyed swimming, goofing off on the diving board, and eyeing all the females. So I was delighted when I climbed out of the pool one day when my mother was with me and she introduced me to this very hot looking woman in a bikini.

"Stevie, I want you to meet a friend of mine. Carmen this is my son, Steve. Steve, Mrs. Sheldrake."

She smiled and extended her elegant hand to me, long red painted fingernails. I was thrilled.

"Nice to meet you, Steve."

"Same here, Mrs. Sheldrake."

 

Well it turned out that both women liked to play cards, poker or gin rummy mostly. So they would often play cards together when both would be at the pool. They played for money and there were always some single bills in a pile between them. They also drank while they played. Mrs. Sheldrake smoked too and I liked watching her blow the smoke out of her nose and mouth. She liked her make up and her lips were always bright red, with a dark outline.

They would be having cocktails and having an intense game of cards. I would take a break from swimming and just sit with them for a while, drying off and watching Mrs. Sheldrake and fantasizing about her. She would always give me a mysterious smile. Did she already know what I was thinking? Who knows. But I was already jerking off over her at age 12.

Now and then she would glance over at me and glance down at my crotch. I could never figure out if she did this on purpose. Maybe it was always in my head. But it seemed like whenever I saw her at the pool she would often look briefly at my dick area in my bathing suit. A couple of times she would get up from the table, announcing to my mother that "I gotta go pee!". Then, as she walked by me she would tousle my hair. I loved it. I loved that she felt comfortable enough with me to touch me like that. With affection. I would swoon inside.

My mother would note to me that they were a childless couple. Like that was some sort of disease or something. That made them both more interesting to me. No kids and no defined religion. Good. I wondered what Mrs. Sheldrake's sex life was like. Her husband, Bob, was a good looking but a rather quiet, low-key guy.

 

Nothing really interesting happened with them until I was fourteen. They lived in a big Tudor house about 8 blocks from our house. So one day early in the summer when my mom went to the pool with me, Mrs. Sheldrake was there and she looked hotter than ever. I remember she had on a black skin tight one-piece bathing suit that matched her hair. I was going thru puberty and I was just fascinated by her. I remember trying to discreetly stare at her crotch area of her bathing suit and wondering if she had pussy hair or if she shaved it?

Anyhow, driving back from the pool that afternoon my mom tells me that Carmen (Mrs. Sheldrake) wondered if I might be interested in cutting their lawn for money? Sure. (I would have cut it for nothing, just to be near her.) How much? Ten dollars. This was a fucking fortune in the early 1960s. I felt like running to the Sheldrake's house and beginning immediately.

That night my mom phoned Carmen and told her I was up for the grass cutting job. She handed me the phone at one point and Carmen sounded sexy and sophisticated on the other end.

"Hi Stevie!"

"Hi Mrs. Sheldrake."

"Carmen. Call me Carmen."

"Okay Carmen."

"So your mom tells me you are interested in cutting our lawn?"

"Oh yes. Very."

"Well why don't you work out your schedule and you can phone me at home this week and tell me when you are able to come over."

"Okay. Fine. Thanks Mrs...Carmen."

"You're welcome. Put your mom back on."

"Okay."

 

And that was it. It seemed so harmless. Normal. Put those sex fiend thoughts out of my head. But, as it turns out, she had communicated with my dick and head in some sexual way.

Carmen turned out to be a very good actress. You would never guess she was kinky, muy kinky.

I phoned her the next afternoon. Since summer vacation had just begun and I had zilch going on in my life, I could cut her grass any day of the week. She laughed at this and I remember feeling so proud that I had caused this sophisticated woman to laugh. She said come over Friday afternoon at 2pm and she would introduce me to the lawn mower. Okay.

Of course I began jacking off over her twice as much as usual.

I remember being a bit nervous walking over to her house that day. She was so sexy that she intimidated me.

She answered the door in little tight shorts, high heeled sandals and a red halter top that showcased her big yummy tits. I was having difficulty breathing.

"Wow. You look great Carmen!"

"Why thank you Stevie. Compliments will get you everywhere. Come on in."

They had a very elegant house. Lots of modern art and Oriental rugs.

"Would you like a Coke or something?"

"No thanks. I'm fine."

"All right. Hang on a sec, I'll get the keys to the garage."

 

She went upstairs for something and I just sat there and took in the surroundings. I fantasized about how lucky Bob Sheldrake was to fuck her. Would I ever get to fuck her? Of course not.

Then she was in the living room again.

"Okay Steve, follow me."

 

She walked thru the house and out the back door. There was a small back yard, thankfully. The front lawn was the big lawn area. She unlocked the garage door while I feasted my eyes on her ample ass cheeks encased in those tight shorts.

"There it is, honey."

The manual lawn mower was resting against the wall. It was a two car garage.

"I believe I can operate that."

She giggled at this. I loved getting a reaction from her.

"Okay, Hon. Just ring the doorbell when you're finished."

"Okay Carmen."

 

 

Cutting the front and back lawns took about an hour. I made sure to really clean up the cut grass good. Then I rang her doorbell. She let me in and I had a seat again on her couch, in the den.

"You must be thirsty now, Stevie. A drink? A glass of wine?"

"Thanks Carmen. I'd love one."

"Comin' right up. A working man needs to wet his whistle."

I was very flattered that she was offering me alcohol. My parents were very strict about my not drinking until I was of legal age, 21. This was sooo forbidden at 14!!!

She handed me a glass of cold white wine, in a wine glass.

"There we go. You won't tell your mom on me, will you?"

"Of course not, Carmen. That would just be cutting my own throat."

Here she giggled again.

"Good analogy."

"Thanks."

She was sitting right across from me.

"I decided to join you. Here's to a job well done Stevie."

We clicked our wine glasses and each had a sip.

 

Then, with an actresse's touch, she reached into her halter top and adjusted her tit and withdrew a ten dollar bill.

"Here you are."

"Thanks. I like your wallet."

"Ha. ha. I thought you would."

"You can read my mind."

"Sometimes I'm good at that."

"I believe you."

 

Talking to this beautiful woman in her den, drinking white wine, I felt like an actor in a very sophisticated play. When I finished my drink she offered me another but I begged off. I didn't want to over stay my welcome.

Well I just about floated home. I kept smelling that ten dollar bill to see if I could discern some kind of mature tit odor but of course I couldn't.

 

I cannot begin to describe how exciting this was for me, at age fourteen. I had never had a girlfriend before. I didn't have a driver's license yet. And here was this gorgeous woman treating me like an equal. It was so wonderful and empowering.

Of course I soon began to fantasize about her 24 hours a day. My life would be built around the day that I would cut her lawn and get to socialize with her. And look at her, and be in her presence. Did she purposely put her money in her tit to excite me? Of course she did! And I loved her for it. What else would she do, down the road? How far would she go with me?

This same ritual went on for a few weeks, climaxing with Carmen taking her money out of her tit and paying me. However, she upped the ante a bit on about my fourth visit.

 

 

When she greeted me at the door she again had on very tight shorts and a skimpy halter top hugging her big tits. But she was friendly and giggly right away. I got the impression that she had had a few drinks prior to my arrival.

After I had cut the lawn and was sitting on her couch again and we were having our white wine together, suddenly she nonchalantly reached her hand into her shorts, not the pockets, but down into the middle panty area, digging down into her crotch, giggling. She removed a ten dollar bill from her sacred cunt area to pay me. I was thunderstruck by this boldness. My hand was shaking as I accepted the payment.

"Why Steve, your hand is shaking. Do I make you nervous?"

"A little bit. To tell you the truth Carmen, I'm very attracted to you. And kind of intimidated."

"Oh you darling boy!"

Here she stood up from the couch across from me and came over and embraced me.

"Oh Honey, that was so courageous of you to tell me that."

My face was mashed against her big tits. Her perfume smelled divine. I could have died there and been happy.

"I absolutely ADORE YOU FOR TELLING ME THAT STEVIE. Thank you so much Honey. You are such an interesting young man."

She slowly attempted to draw me out about my girlfriends. I didn't have any. Why not? I don't know.

"You're a very good looking young man, with a charming personality. I'm sure you'll have no trouble getting women."

"Thanks Carmen. I sure hope you're right."

This time I accepted her offer of a second glass of wine. My dick was hard ever since she put her hand into her shorts to get the ten dollar bill.

When she came in with the second glass of wine this time she sat down next to me on the couch. This was a first.

"I'm becoming very attached to you, Stevie. I'm alone here a lot and I just enjoy your company so much. I get lonely sometimes. I love our little chats when you come to cut the grass."

"Me too."

She smiled broadly at this.

At one point she put her hand on my knee.

"Do you ever think about me when you're alone?"

"Do I ever!"

 

She put her arm around me.

"Tell Mommy. What do you think about?"

"It's probably too weird."

"Tell me anyway. I'll still like you Stevie."

 

I didn't know what to say. I couldn't tell her about jackin' off all the time thinking about her.

Suddenly her hand was on my dick. I had a hard-on and she was squeezing it.

"I thought so. You're hard. Why is your dick hard, Stevie?"

God was I nervous! Suddenly it was Twilight Zone time. No human being had ever touched my penis before. I was so stunned I had a very hard time talking.

"I..I'm attracted to you."

"Good answer. Take your pants off."

"What?"

"You heard me. Take your pants off, Steve. Right now. Get these pants off!"

 

Her demeanor had undergone a sea change. Before it was sweetness and informality. Now bitchy and demanding.

Shaking, very nervous, I had to take my tennis shoes off first in order to get the jeans off. She had kind of a frown on her face. I remember wishing that I had had about four glasses of wine before she pulled this. She was not making it any easier. Finally I was standing in front of her in my Jockey shorts. Hard with a cum stain at the tip.

She reached out and held my dick in my underpants.

"What's this?"

"Mmm my dick."

"No shit. Why is it all wet?"

"B..because I got excited."

"Good boy. You should always tell the truth around me, Stevie."

 

Then she slowly pulled my underpants down. I just about shit right there. And evil smile spread on her face as she revealed my dick and balls.

Her elegant hand was squeezing my hard dick.

"I knew it! There's our little friend. He's not very big, is he?"

That was true but also humiliating.

"No."

"You've got a sissy dick Hon. Sissy size. I knew it! I got a sissy girl vibe first time I saw you. I could never even see your dick in your wet bathing suit. Has anyone else mentioned this? About your small size?"

This was no doubt the first time I ever even heard the word "sissy."

"Oh you're blushing! I love it!"

"Uh..just some guys at school."

"How do you feel about being tiny there, Stevie?"

She was still holding it and looking right thru me. It seemed so unfair that I was naked and hard and she was fully dressed.

"Well, not good. But there's really nothing I can do about it, really."

"That's a good attitude, Honey. But do you feel kind of envious when you see the bigger dick boys in the shower?"

"Yes Carmen, I do."

"Mommy. Call me Mommy."

"Yes Mommy."

 

A tornado of emotions ran through me.

She was smiling wickedly. Still holding my dick.

"Are you enjoying this, Honeybun?"

"Uh..kind of."

"You're not sure? Don't you like being naked and hard in front of Mommy?"

"Yes, Mommy. But.."

"But what, hon?"

She was still holding my dick and she was fully clothed.

 

"I..I dunno. Just seems kinda weird me being nude and you with all your clothes on and stuff."

"I know, hon. But Mommy's in charge. And you're the sissy. That's the way I like it."

"Okay."

"Now where were we? Lil dickie man. Not very big, is him?"

"Huh?"

"Is he?"

SLAP.

She slapped me right in the nuts. Hard. I saw stars and doubled over.

"When I ask you a question, young man, you answer me right away. Got it?"

My nuts had a dull ache from the hard slap.

"Yes Carmen. I'm sorry."

Now she was scaring me.

 

"Let's try this again, hon. Your dick is not very big, is it?"

"No, Mommy, it isn't."

"Now say, 'Mommy my dickie bird is small. I have a small penis.' "

"Mommy my dickie bird is small. I have a small penis."

"Good girl. I like when you obey Mommy's orders just right. Like an obedient sissy."

 

 

Here she stood up and kissed me. Right on the mouth, my mouth was forced open and her tongue darted in. Then she was sucking my tongue. I was her pawn. Her adoring slave.

She broke the kiss.

"That was for a good girl. A pretty girl with a tiny dickie bird."

Why was she calling me a girl?

 

"You're leaking, Stevie. Let's spread this around."

My dick was still hard and she was spreading my pre-cum around the top of it. I felt like I was on Mars.

She pulled me down on the couch with her.

"Do you masturbate when you think about me, Stevie?"

"Oh God do I!"

"Ha ha. Good boy. Mommy loves when you tell her personal stuff like that. Do you need another wine?"

"Oh yes, please, Car..Mommy."

She went and got me another glass of wine which I downed in two gulps. It helped.

She was sitting next to me on the couch now. I was still naked and hard and very nervous. She was still dressed and giggling.

She smiled at me and tousled my hair.

"You are such a cutie! Mommy loves seeing you hard. It's very flattering, actually. How are you feeling Honey?"

"Uh..kinda weird...Mommy."

"Okay, here."

She stood up in front of me.

"Undo my shorts and take them off."

 

With shaking hands, I unbuttoned her tight shorts and drew them down her slender, tanned legs. She stepped out of them.

She was wearing semi-opaque white panties. I could see a thick bush of black pubic hair beneath the panties. They were wet.

"Is this a little better, Hon?"

"Yes Mommy. Thank you."

She sat back down next to me. She caressed my hard on again.

"You know, Stevie, I've thought about you when I'm alone too."

"You do?"

"Oh yes. And I masturbate over you too."

"Wow. What do you think about?"

"Kissing you. Playing with you, like this. Fucking you."

 

"Oh God! This is great."

"You like that, huh? Little dickie boy!"

"Yes Mommy. Thank you for telling me that."

"You're welcome. I want to spank you now."

"What?"

"Don't play dumb, Stevie. Get over Mommy's lap right now."

 

The whole scene seemed like some surreal dream. But I was going to do whatever she wanted. She was hot!

On wobbly legs, I stood up next to her. She was still sitting on the couch. She quickly grabbed my arm and pulled me to her right side. Then suddenly I was over her lap.

"There we go. Mommy's got her little dickie boy just where she wants him."

Giggling again. I feel her hand yanking on my dick between her legs. I'm so nervous.

"There's Mommy's friend. Mommy loves you obeying her."

WHACK! WHACK! WHACK!

Lightning bolts hitting my ass. She was very strong.

"Ow! Ow! Mommy that hurts!"

"It's supposed to hurt, Sissy!"

WHACK! WHACK! WHACK! WHACK! WHACK! WHACK!

"Owww m.Mommy!! Hurts!"

It did really hurt and I was beginning to cry.

WHACK! WHACK! WHACK! WHACK! WHACK!

Then it stopped. I could still hear myself crying.

She was stroking my ass and legs.

"Such a good girl to take her first Mommy spank. All over, Honeybun. That was just a little taste of Mommy fun. You are so pretty and fun to spank on your cute ass."

Silence in the room. I was breathing very hard. She was kind of humming to herself and stroking me. Then her finger at my asshole. Pushing into it a bit.

"Such a pretty pussy. Mommy's going to want to fuck you there."

She just let that hang in the air. Fuck me there? How? I just lay there, still in the weird dream.

Then I feel her kissing my ass cheeks.

"Mmm such a pretty little dickie girl. Pretty sissy ass. You can stand up now Stevie. That was fun."

I was standing in front of her naked. My ass was still stinging with pain. My eyes were blurry from crying but my dick was rock hard.

"Why did Mommy spank you?"

"Because I didn't answer you?"

Here she took my hand and looked deep into my eyes. Teaching the child.

 

"Correct. But also because Mommy loves to spank naked men over her lap. Especially young tiny dicked sissy boys. Like you. With very small pee pees. You're blushing. Honey, I love to see you blush. And cry for me. And hard and leakin' in your little baby weiner. Be right back."

She returned a few moments later with something in her hand.

"Sit on Mommy's lap, Hon."

Still naked, I climbed on to her lap. She had this beatific smile, as if she had just seen God or something. Then I noticed she had a container of Jergan's hand lotion in her hand.

"You were a very good girl for taking your first Mommy spank. So now Mommy is going to reward you. Good sissy girls get rewards."

Everything was happening so fast. My ass still stung and she kept calling me a sissy and a girl. ???

Here she squirted a big dollop of lotion right onto my hard dick. Then she began massaging it in.

"Ohhhhh."

"Feel good, Baby?"

"Oh yesss Mommy. Thank you."

"We can have lots of fun together as long as tiny dick girl obeys Mommy all the time."

She was slowly jackin me off as she talked to me. She talked to me as if I were a little infant.

"You like Mommy jackin your little weiner?"

"Oh yes."

"This is probably like one of your fantasies come to life."

"Exactly. This is just like one of my wet dreams about You Mommy. Extra vivid."

 

"I dream about you too Sweetness."

"About what?"

"Stuff like this. Jackin your lil pee pee off. Fingering you in the ass, your boy cunt. You eating my cunt for me. Takin' a piss on you."

"Ohhhhhhhhhhh fuuuuuuuuuckkkkkk!!!"

"OH MY GOD! What a big girl load for such a little pee pee on her. Stevie shot a big load of jizz for Mommy. Didn't him? Huh, Babygirl? Ohhh look! You're still shooting, Sweetie. Mommy loves to see her little girl shoot her lil pecker off. Wow. Look at all that jizz. Awwww Stevies little pee pee is all tuckered out now, huh? Huh Babygirl?"

"Ye..yes Mommy. Thank you."

"You're welcome Sweetheart. Mommy loves to see her little man shoot big loads."

She kissed me on the side of the face.

"Get up Baby. Mommy has to clean you off."

In a post-orgasmic euphoria, I stood up. I felt like I had just run a mile race. But I was also ecstatically happy and sublime. This was by far my greatest orgasm thus far in my short life. There was cum all over her hand and my legs.

Carmen went into the bathroom and I could hear water running. She returned, smiling, with a warm face cloth. Then she lovingly wiped up the jizz from my explosion.

"There we go. Did that feel good to shoot your little weiner off, Stevie?"

"Oh yeah. It felt fabulous Mommy. Thank you."

"You're welcome. Mommy loves to see you shoot big loads."

She did a very thorough job of wiping up all the jizz from my dick and balls and legs. She also turned me around and wiped me between my ass. Weird.

I adored her wiping me up, treating me like her little baby.

"Look what you did to Mommy, Stevie. You made me cum. Got me all wet in my cunny and my panties all wet. Look."

She was displaying her wet panties to me. They were soaked with cum and smelly. I could see all her hair in there. Then she whipped them off and suddenly shoved the sopping wet panties into my face.

"Smelll! Sniff Mommy's wet cunt panties Sissy!"

I did and they smelled heavenly.

 

"I told you I got excited around you. You get Mommy's cunt all wet Stevie. Do you like to smell Mommy's cunt panties?"

"Oh yes, thank you so much Mommy."

"You're welcome Little Pee Pee Girl. Here, I want you to keep these as a souvenir. And think of me when you sniff them and jack off your sissy weiner."

Here she put the wet panties into my pants pocket.

"You can get dressed now, Sissy."

Still in a daze, I struggled into my clothes. A changed man.

I could see her thick black pubic bush covered in moisture. Cum. I made her cum.

 

 

 

"You better go now. Thank you for confiding in me. I love it when you tell me your secret thoughts. Then Mommy rewards you, if you're a good girl. Are you going to always be a good girl?"

"Oh yes Mommy. Always."

"But this has to be our secret Hon. Just you and Mommy. Understand? If you ever tell anyone that will be the end of our friendship. Understand?"

"Yes Mommy. Thank you."

"We can have lots of fun together as long as you're a good girl and obey Mommy."

Here she hugged me and then kissed me right on the mouth. Breaking the kiss, she smiled at me and then took a hankie and wiped her lipstick off of my face.

She opened the door and then I was somehow walking home. From Mars. Or The Planet Mommy. Flying home, was more like it. I could not believe what just happened. But the best part was that I had proof. Her wonderful sacred cunt scented panties. Soaked with her mature female cum.

 

Naturally my fantasy life went into overdrive now. Plus, I had her stinky cunt panties to fuel my fantasies. I was jacking off about four times day over it. And loving it.

I phoned her the following Tuesday afternoon and asked when she would like me to cut the grass again.

"Come over tomorrow at two o'clock."

"Okay Carmen. See you tomorrow."

 

No mention of our kinky fun last week. Which I liked, I adored having a secret with this beautiful woman. I felt like a counter spy in some espionage movie.

When I came over on Wednesday I went thru the same grass cutting routine. When I finished up, I rang her doorbell. She opened the door and led me into the den again.

"I'll get our wine. Get undressed Sissy. I want you naked."

Nervously I undressed again. Of course I was rock hard as usual.

When she returned with the wine she had a big smile for me.

"Follow me Hon. I want to have our wine in the basement.."

I followed her down the stairs into a big basement. Lots of notty pine, linoleum floor, and sectional sofas.

She sat down in the middle of the sofa.

"Sit next to me Stevie."

I followed her directions.

She handed me my wine and then proposed a toast.

"I had so much fun with you last week Sissy. Here is to our new fun friendship."

We click our glasses and sipped the wine.

Then her hand on my dick.

 

"There's my little buddy."

"Ohhhh.."

"You like Mommy touching your dickiebird?"

"Oh God do I!"

Her soft elegant hand enlcosed my hard.

 

"Stevie, Hon, I brought you down here today because Mommy wants to spank you hard and I don't want anyone to hear us playing. Do you understand?"

"Y..yes Mommy."

"Mmm I love you nervous and hard. My little leaker. How do you feel about that?"

"I'..I feel good Mommy. But I'm a little scared. Mommy spanks hard."

"Yes I do Sweetness. But it's important for the Sissy to understand that Mommy needs to spank you hard. That gets Mommy excited. That's why you're here. Mommy likes to spank hard and hurt the sissy. When you start crying that gets Mommy cumming in her cunny. And that's what you want, isn't it?"

"Oh yes, Mommy. I'm just not used to it."

"I know, Hon. Mommy's going to work with you on this. But the harder Mommy can spank you the happier Mommy is going to be with your visits. And you liked your reward, didn't you?"

"Oh yes Mommy. So much."

"Good girl. Let's finish this first drink and then Mommy will start the spanking."

Time seemed to stop for me. This gorgeous woman was smiling at me, while I was sitting next to her naked, as she calmly described how she enjoyed hurting me. And how much it turned her on.

She was obviously anxious and just about chugged her wine down.

Then she stood up in front of me.

"Okay baby dick, undress me. Take everything off but my shoes."

I was shaking like a banshee and I could tell she loved that I was scared and nervous.

She was smiling and petting my hair as I undressed her.

"Mommy so loves spanking you hard and hearing the baby dick sissy cry for her."

In no time she was naked except for her high heels. She sat down and then I was over her lap.

WHAP! WHAP! WHAP! WHAP! WHAP! WHAP! WHAP!

Pretty soon I was crying and screaming and bawling. She just seemed to hit me harder. I attempted to ward off the blows with my hand. but she quickly caught my arm and twisted it behind my back. It went on for a long time.

I could still hear myself screaming and bawling my eyes out. Then it dawned on me that she had stopped hitting me. I was still crying loudly and sobbing over her lap. She released my arm. I kept crying it out.

Her hand on my schribbled up dick. Slowly yanking on it.

"Shhhh calm down Baby. Shhhhh calm down. All over Honeybun. Mommy loves you. You were such a big girl sissy for Mommy. Mommy loves to spank her tiny dick sissy hard. All over Sweetness."

It had lasted a long time. I couldn't believe she got off on being so cruel to me. But she obviously did. And I must have been very loud screaming. It certainly sounded loud to me.

Her soft hand caressing my hot ass.

"Okay Sissy, Mommy wants you to stand up now and walk over to the corner over there. And put your nose in the corner. Can you do that for Mommy? And just think about what just happened and why Mommy has to spank her baby dick sissy so hard? Go on Little girl."

On wobbly legs I walked to the corner of the room, still sobbing loudly, and put my nose in the corner. It was all so surreal and wonderful.

After I had my nose in the corner for about five minutes I felt her come up behind me and begin petting my hair.

"That's right. Good girl. Mommy loves when the sissy follows orders."

Then her hand was caressing my frightened dick. I started to get hard again.

"That's right. There's Mommy's friend."

And then she was gone.

I stay like that in the corner for about twenty more minutes. It was deathly silent. Was she masturbating, looking at my beat up ass? I couldn't tell. But I knew I was a convert to this strange religion. I wanted her to be proud of me. I wanted to be Mommy's Good Girl.

"Okay Sissy. Corner time's over. Come and join Mommy on the couch."

I turned around and she was sitting on the couch, naked except for heels, smiling at me. As I walked over to her, I noted that she had put two fresh wines on the coffee table.

As soon as I sat down next to her, she embraced me and tongue kissed me for a long time. I adored her.

"Sissy I am soo proud of you. For taking that hard spanking. I love to hit you hard, hear you moan and cry. You gave Mommy a big cum in her pussy. It was wonderful. How are you feeling?"

"Much better Mommy. Just..not used to you hitting me so hard. Sorry."

"It's okay Sweetness. But that's what Mommy needs. To beat the sissy hard. That makes me cum. We'll work on your pain tolerance Hon."

I gulped down my wine. Everything happened so fast with her.

"How is your little biddy weiner?"

Here she wrapped her hand around my hard dick.

"Well your sissy clittie seems to have recovered. I love that you get hard so quickly."

"Ohhh feels good Mommy."

"Baby I have wanted to spank you like that ever since I first saw you at the pool."

"Really?"

"Yes. I fantasized about scenes just like this. Something about you just screamed SISSY! to me. I knew it."

I gulped more wine and just enjoyed her praise and her touching me there.

"Stevie Mommy had the best cum beating you hard. The best. I want you to get down on your knees and just put your nose in my pussy hair. Do it."

I followed her instructions and got down on all fours. I noted that her pussy hair was glistening wet.

"Just smell it first sissy. Sniff Mommy's excited pussy smell."

It smelled divine. An intoxicating aroma. Very strong and funky.

She had a big bush of thick black pubic hair. I was losing myself in it.

"You like that smell, Sissy?"

"Oh God yes!"

"Good girl. Mommy loves you making her cum so hard when you take your hard spanks. Now lick it. Lick and suck my cunt like the sissy faggot you are!!"

Her right hand was behind my head and suddenly my face was being mashed into her wet bush.

"Yeah, thas right. That's where the faggot sissy goes. Take care of Mommy's wet cunt."

I spent the next hour down there. Now and then she would pull my hair hard, and then let go. This just seemed to spur me on.

"Yeah, suck that cunt faggot boy! Make Mommy cum!"

Suddenly she slapped me in the back of my head, hard, three times in a row.

"Thas right. Little dickie faggot loves to eat his Mommy, huh?"
"Oh yes Mommy! So much. Thank you."

 

"Ohhhhh My God!!!!"

Both of her hands on the back of my head, pulling me into her.

"I'm coming so hard! I'm coming so hard!!"

She worked thru about five cums, pulling my hair, twisting my face into her smelly, hairy mound, wrapping her long powerful legs around my neck squeezing very hard. But I knew enough not to stop, no matter what.

After about an hour, and lots of moaning from her, she pulled my face off of her by my hair.

"Okay Sissy. That's enough. Break time. Come sit."

I managed to get off my knees and sit next to her. Suddenly I was very tired.

She kissed me on the side of the face.

"Thank you Sweetie. Made Mommy cum so hard, so fuckin' hard. You are an excellent cunt sucker. A natural. Just like a natural sissy girl."

I just sat there for a long time, sipping on my wine and taking it all in.

"You've got pussy juice all over your face, hon. I like you like that. Do you like having Mommy's juice on you?"

"I love it Mommy. Thank you."

"Welcome Precious. That cum was so gooood. You are such a talented peeny girl."

This was like some wonderful porn movie that I was starring in. I watched her walk upstairs to refill our wines. What a gorgeous sexy woman. And I got to eat her cunt!!! And she said I was good at it!!

We just drank and kind of murmured to each other for a while. All the time she was touching my dick and balls. Of course I was rock hard again.

"Stand up Sissy. Stand in front of Mommy."

I quickly obeyed her."

 

She smiled at me, then dipped her head and started sucking my hard dick. It felt out of this world. I had my hands on her head. Felt like I was going to fall over. She was moaning loudly, like she really liked sucking me.. Suddenly she was yanking on my balls, hard. I came in a torrent of cum.

"MMmmmmmmmmmm grggllllllllgggggghhhhmmmmm."

I came for a long time and finally I finished shooting. I had to pull her head off of my dick.

Then I just collapsed on the couch.

"MMm that was lovely Stevie. You are delicious. For a little pecker you sure shoot a lot."

It took me about twenty minutes to recover from my massive orgasm. She just sipped her wine and smiled at me.

Then I got dressed and was walking home again. Seeing her just got better and better. Kinkier too, but so sexy and exciting.

Before I left she gave me the ten dollars and a present of her panties again.

"I want you to wear Mommy's panties whenever you come over. Don't wash them. From now on. Understand?"

"Yes Mommy. Thank you."

"You're welcome Sissy. And tell Mommy about how you sniff them in your room at home and jack off your lil weiner while you smell Mommy."

"I will Mommy. Thank you."

 

Something about her giving me orders and instructions to follow made it kind of a fun game. A game that only we knew about.

 

 

Pretty soon I was going over to her house two or three times a week. And I didn't even have to cut the grass. And she always paid me.

Every visit was full of surprises and strangeness.

She loved having me recite certain phrases to reinforce the fact that I was a sissy with a small penis.

One day we were down in the basement, having some wine. I was naked and she had me strip her down to only her shoes. I was fascinated by her thick black bush of pussy hair. It seemed to always be wet.

"You like lookin' at Mommy's pussy?"

"Oh yes, I love it Mommy."

"See it's all wet, Sissy. Why is it wet?"

"Cause Mommy's excited?"

"That's right. Mommy gets wet around her sissy girl. But why can't Stevie fuck Mommy there?"

"Cause I only have a sissy size dickie bird. I have a small pee pee. Mommy wouldn't even feel it in there."

"Thas right. And what does Mommy need in there?"

"A mancock. A big dick, like a man has."

"Good girl!"

Here she kissed me on the mouth and we made out for a little bit. Then she broke the kiss, and tousled my hair.

"You are so adorable. Mommy loves it when you know the right answers, sissy answers."

"Thank you Mommy. I love being around you."

"I can tell. You're lil peenie is all hard and wet again."

Here she caressed my dick and began playing with it.

 

Fucking The Sissy Pussy

 

 

"Honey, today Mommy is going to work on your boy pussy. Your cunt. We have to open it up. Stand up and face that wall, Sweetness."

Of course I immediately followed her instructions. She moved one of the pillows on the couch and there was a big jar of Vaseline that she took out. I watched her smear her middle finger with Vaseline.

"Face the wall, Faggot!"

I did.

"Now just relax, Hon. Mommy is going to touch your pussy."

 

I could feel her coating my asshole with the Vaseline. Then a little pressure on my asshole.

"Thatta girl. Just relax. Mommy needs to go in here and work on the sissy girl's cunt. So Mommy can fuck you down the road and make you a real sissy. Who takes dick up there. In her sis cunt."

I remember I was scared for some reason but it really didn't feel bad. Her slender finger was about halfway up my asshole. And it didn't feel bad.

"That's my good girl. You are being such a good sissy. Now Mommy's gonna go a little deeper."

More pressure and her finger was going deeper.

"Mommy is so proud of you, Sissy. Can you feel Mommy's finger up your cunt?"

"Y..yes Mommy. It feels kinda good."

"You're going to love it. You just have to get used to it, Precious."

Pretty soon she was finger fucking me in my cunt. It felt very good.

"Now tell Mommy why you can't fuck her in her cunt. Like a man."

"Cause I'm just a sissy with a sissy size dick. I'm way too small for Mommy to ever feel me there."

"But you like Mommy in your pussy right now, don't you?"

"Oh yes, Mommy. Feels goood."

"Look, Mommy has another treat for her sissygirl. What's this?"

I looked down at her left hand and she had donned some kind of furry mitten.

"A mitten?"

"Sort of, honey. But for you, this is going to be the pussy that sissy gets to fuck. See, look."

Here she wrapped the mitten around my hard dick.

"Okay. Now fuck the pussy, Sissy. Fuck it with your lil weiner."

I obediently began pistoning my dick into the furry mitten. As I did, she would finger my asshole.

"Good girl. What is Stevie fucking?"

"The pussy. The special pussy for a baby dick sissy like me."

"Correct, Sissy! And while you're fucking the special sissy pussy, Mommy is fucking you in your boy cunt. Do you like Mommy fucking you in your sissy ass?"

"Oh yes Mommy. Feels good."

"Good lil peeny girl. Now the harder you fuck the sissy pussy, the harder Mommy is going to fuck you."

Following her suggestion, I began to fuck the furry mitten faster and faster. She kept up the pace by pistoning in and out of my asshole faster and faster.

"Ohhh Stevie likes to fuck the sis cunt, huh? Stevie fucks the furry pussy hard, huh! And Mommy likes to fuck her sissy in the cunt hard, too. Like this, nice and hard and deep in her hot cunny hole!"

"Ohhh Momeeeee!!!!"

"Yeah, yeah, atta girl. Shoot it out, Faggot! Shoot that lil baby weiner off! Thas right, shoot your little boy load for Mommy! Oh My God, look at all that cream. You are such a jizzy lil sissy, aren't you? Get it all out, faggot, Shoot that dickie off! Good girl. All over, Precious. You did good. Mommy likes to watch you fuck the sissy cunt and fuck you in your asshole too. You did good, babe. Calm down. All over."

The vigorous erotic stimulation of my prostrate had given me a fantastic orgasm. She slowly removed her finger from deep in my asshole and then embraced and kissed me. As if I had passed another test, which of course I had.

I remember laying down on the sectional sofa, catching my breath. I felt out of this world happy. Then she returned with a warm washcloth and slowly and lovingly cleaned up my dick and balls and asshole. And wiped up the jizz off the floor and off of the furry mitten, my new sissy cunt to fuck for Mommy.

After she cleaned me off, we had some more wine. Later, she sat me on her lap.

"Stevie, I am so proud of you. I love working on your sissy cunt hole. Mommy wants to fuck you in there someday. Soon. But we have a lot of work to do. Now Mommy wants you to nurse and just calm down."

Here she fed me one of her lovely large pendulous breasts. I took to it like a real infant. It was heavenly. She cooed to me like a baby and lovingly ran her pretty fingers thru my hair as I nursed on her big tits.

"Yeah, atta girl. Mommy likes you to nurse after a good lesson. A good sissy lesson. Helps calm the baby dickie girl down. And Mommy likes it too. Helps relax me, Baby."

It was another wonderful, fun day at Mommy's house. Before I left we made out for a while and of course she paid me the ten dollars. I was getting paid to have sex with her and I loved it.

 

As time passed, fucking the furry mitten/pussy got to be a frequent ritual. By this time, she had worked up to finger fucking my boy cunt with two fingers in there. Then one day, before I left, she gave me a small butt plug and showed me how it worked. Greasing it up good and then inserting into my asshole. It really did feel good.

"Mommy wants you to wear it a lot at home. In private, in your room. To work on your sissy cunt, to open it up for Mommy. So Mommy can fuck you there soon and take your sissygirl cherry. And make you a real sissy. Will you do that for me?"

"Of course, Mommy. I love you."

"That's my good sissy. And you want Mommy to fuck you there, don't you?"

"Oh yes Mommy. I want to be Mommy's real sissygirl."

"You are doing fine, Precious. But we need to get to the next level. Mommy's been wanting to fuck you so bad!

"Will it hurt, Mommy?"

"Just a teeny bit the first time. But the more you work with the plug the easier it will be to take Mommy up there. You'll be spanked very hard that day, to take your mind off of your cunt."

I just stood there, trying to take this in.

"I want you to wear it all the time when you are alone in your room thinking sissy horny thoughts of Mommy. Will you do that for Mommy, Precious?"

"Oh yes Mommy."

"Good girl. And I want you to always be plugged in your sissy cunt when you jack off from now on. So the sissy gets used to having a dick up there when she cums. Okay Baby?"

"Yes, Mommy. Thank you."

 

Here she would give me a deep French kiss while squeezing and twisting my dick and balls. I lived for her touch.

Then she gave me another pair of her wet, soiled, cunt scented panties.

 

Then the first thing she would ask me when I got inside her house was, "Have you been working with the plug?"

"Oh yes, Mommy."

I would be stripped nude by this time. First, displaying her dirty panties that I was wearing, then removing them. Then she would test my progress by greasing up her fingers and inserting them into my a hole.

"Good girl. Feels like you're getting bigger. You like Mommy in there?"

"I love it Mommy."

"Look sissy! There's the furry pussy for Sissy to fuck for Mommy."

Suddenly she had the furry mitten on and was holding my dick with it. As she finger fucked my pussy. One, two, then three fingers.

"Good girl! Mommy's got three fingers up her sissygirl's cunt. Keep workin' with the plug Darling. Your cunt's gettin' nice and big in there. You like Mommy deep in there? Huh, Baby?"

"Uh...yeszz Mommy. f..feels soo good in my cunt."

"Atta girl! Stevie likes Mommy in her sissy cunt, huh?"

"Hooooohhh!!!"

"Oh My God, shoot it sissy! Shoot that cream for Mommy. Atta girl! Get it all out, hon. Sissy likes Mommy in her cunthole, huh? Huh, Babygirl? Ohhh all over, Honeybun. Stevie got all excited with Mommy in her cunny hole, huh? Mommy got three fingers in there and Sissy Stevie went crazy. I guess Stevie girl needs some dick in there? Huh? In her sissy cunt, huh?"

I just came and came and came. Like some strange porn movie. Starring my small dick and her three fingers up my asshole. She drove me crazy. Just seemed like the combination of her dirty baby sissy talk and her fingers touching me drove me wild.

After she took her fingers out of my boycunt, I collapsed on the sectional sofa. She went and got a warm wash cloth and cleaned me up.

"Oh sissy you got Mommy so fuckin' hot. I came watchin' you shoot your lil peenie weiner off. My cunt is soaking wet with cum, sissy. I'm going to sit on your face for a bit, to calm us both down."

And she just plopped her gorgeous cunt down on top of my face as I lay on the sofa. She was facing my feet. I was enveloped in the dark nether world of her super funky cunt. Full of this mature Latin woman's cum dripping on to my face. She was absolutely quiet and just sat there for a long time. I never wanted her to get up. This was Heaven.

 

She asked me to come over to "visit" her again the next day. My sissy training sessions were getting more intense.

The next day, after I had stripped down for her downstairs in the basement, and slowly removed all of her clothing except for her heels, we were both standing up facing each other.

"Stevie hon, I am so proud of you and how quickly you are picking up your sissy training. Now I want to show you something."

Here she took my face in both hands, smiled at me, then hauled back and slapped me in the face, very hard! I was in total shock. I burst out crying. She was smiling at me, as if this was great news. Then she did it again. Harder! Twice. Now I was bawling my head off.

"Oh Baby!"

She embraced me in her loving arms and hugged me as I bawled my eyes out from the shock and pain of her slapping me in the face very hard.

She kept hugging me until I slowly stopped crying. Then she held my arms and pushed me back to arm's length.

"Stevie I am so proud of you. I have been wanting to face slap you hard for so long. I love the look of shock on your sis face and you bursting into tears. I came watching you cry and bawl for Mommy. Thank you for allowing Mommy to slap her tiny dickie girl very hard. Mommy loves that."

She was smiling at me and tousling my hair.

"Mommy is going to want to slap you hard in front of someone else, one day. Mommy will be so proud of you to take Mommy's hard face slaps Precious."

I could still feel the sting of her three vicious slaps to my face. But of course my dick was brick hard.

Carmen seemed pretty giddy and goosey that day. She had probably had a few drinks before I arrived. We sat on the couch in the basement and made out for a bit. Her hand squeezing my dick the whole time. We had our first glass of wine.

"Give me your hand, Precious. I've got a surprise for you upstairs."

Holding hands we walked upstairs to the master bedroom. It was a big room with a large double bed. I noted a massage table in the corner.

"Okay, lay down on the bed, on your back, Sissy."

I followed her instructions. The next thing I knew she had tied both of my arms to the bed posts, so that my arms were spread out.

Then she smiled at me, then left the room for a moment. Of course I was scared. She returned carrying a long wooden paddle. Then she was on the bed next to me and quickly gathered my legs up, wrapped her left arm around them and leaned against them, effectively pining me down.

WHACK! WHACK! WHACK! WHACK! WHACK!

WHACK! WHACK! WHACK! WHACK! WHACK!

The hits with the paddle stung like thunder. I was screaming and crying at the top of my lungs, which only spurred her on. I was a bawling, screaming mess. I couldn't believe how hard she was hitting me. It went on for a long time. She was very strong and cruel.

Finally it was over. I was screaming my lungs out. It was all very hazy, a terrible, terrible nightmare. Crying and blubbering and hiccuping. I remember after a while she finally, finally released her iron grip on my legs and I just lay them down on the bed. Still sobbing and crying. Then she was between my legs and sucking my shribbled up dick. Then finger fucking my pussy. I got hard quickly and came very quickly.

"Mmmmmm ggggggglufffffffmmmmmm," she murmured as she devoured my load. It was all so sick. She was like some evil animal.

I must have passed out after that. When I woke up on the bed she had untied my arms and was sitting on the bed smiling at me. Sipping a wine.

"Hi Sissy. How are you?"

I didn't know what to say.

"M..Mommy that hurt."

"I know it hurt, Sweetie. Mommy likes to hurt you. That was probably the best cum I ever had. I absolutely love to beat you."

"I know Mommy, but..it hurt."

Here I started to cry. I couldn't help it.

She lit up at this. Next thing I knew, she was carresing my head and petting me, like a favorite pet.

"I am so proud of you Sissy. We just have to work on your pain tolerance."

My ass hurt very, very much. Then, like it was in slow motion, I watched her get up off the bed and then squat and sit on my face. Darkness of being surrounded by her very wet and funky smelling cunt and ass. Her pussy had never smelled this rank.

"Smell me faggot. See what you do to Mommy?"

I didn't answer. I was just kind of in shock by the whole thing. She quietly sat on my face for a long time. Then, unbelievably, I suddenly felt her pissing on my face!

"Ohhhhhh My God!!!! You little faggot!"

Apparently she was orgasming over this degradation of me.

"Yeah! Yeah! Mommy pisses right on the tiny dick fag!!!"

Finally, after remaining on my face for a long time after she urinated on me, she got up and stood next to me.

"Meet me downstairs in the living room, Hon."

It took me another ten minutes to gather my strength to get up off of the bed. I went into the bathroom off the master bedroom. It had a full length mirror on the door. I could see and smell the sheen of her piss all over my face. I turned around and looked at my beat up ass in the mirror. It was a deep blue color. I wondered how much further she would go. And how much more I could endure?

When I walked downstairs into the den she was sitting on the couch, naked, sipping her wine. She put her wine down and stood up and embraced me. Like I had just returned from a war or something. Then she was kissing me, deep frenching me. It was lovely.

After the long kiss, she sat back on the couch and signaled me to sit down next to her.

"You look worried, Precious."

"I am. That was horrible, Mommy."

"For you maybe, it was spectacular for me. I love beating you faggot. And taking a nice long piss on you was divine."

I just sat there and sipped my wine.

"M..Mommy you are starting to scare me."

"Good. I love to scare you, faggot. Tiny dick sissy."

 

We seemed to be polar opposites. Although I had a wonderful cum with her blowing me, I was still very shell shocked by all the violence. She, on the other hand, looked blissfully happy.

We drank in silence for a long time. I gulped my drink down and she quickly refilled it. Then I gulped that down too.

"Get dressed Sissy."

I quickly dressed and she kind of brusquely showed me the door. No kiss goodbye. Was she mad at me? Nothing about when to come over next time. My ass still hurt. Bad.

 

I did not hear from her for about a week and a half. Agony.

 

Finally she phoned me one weekday afternoon.

"Hello?"

"Stevie?"

"Carmen?"

"Yes, dear it's me. I want you to come over for a visit tomorrow at 2pm. Will you do that?"

"Yes, Carmen, of course."

"See you then."

 

She could be so mysterious. No explanation as to why she hadn't had me visit for so long. Was she mad at me? Nothing. But I was so happy to hear from her, knowing we would be playing again soon. My dick was brick hard ever since I heard her voice. I jacked off about three times in a row.

 

When I arrived at her house the following afternoon she greeted me in jeans and a halter top. We sat in the den and she brought out some wine for us.

"M..Mommy were you mad at me?"

She smiled at me and ran her fingers thru my hair.

"Yes, Sissy, I was mad at you. Sometimes you don't seem to appreciate what a lucky sissy you are. Mommy lets you eat her cunt and even blows you, but you still complain about how hard she hits you. That makes Mommy mad."

"I'm sorry Mommy. Please forgive me."

"Mommy loves to hurt you and make you cry. You know that."

"Yes Mommy. I'm sorry."

She took my chin in her hand.

"Are you going to be a good girl? And promise not to complain about Mommy hitting you hard?"

"Yes Mommy. I promise. Thank you for giving me another chance. I won't complain any more Mommy."

"Good girl. I hope you don't."

We drank our wine in silence.

"Get undressed Precious. I want to see your baby pee pee. Then undress Mommy."

Of course I immediately obeyed her instructions. Then we were both sitting in the den naked.

"There's my little friend," she said, closing her hand on my hard dick.

"Has your lil bitty weiner missed Mommy?"

"Oh yes, Mommy. So much."

 

"Stevie, Mommy has another surprise for you today."

Here my heart sunk, terrified.

"No Honeybun, I'm not going to hurt you. Mommy wants to baby you. I don't have any children, as you know, Sissy. So I want you to be my little baby. With a baby size dickie bird."

"Okay."

Here she reached out her hand and hand-in-hand we walked up the stairs to her master bedroom.

When we reached the bed I noted a large diaper already spread out on the bed.

"There is your first diaper Baby. Sit down on it."

I quickly obeyed her.

 

"But first Mommy wants to check your baby pussy."

She lifted my legs and squirted my ass several times with a bottle of Johnson's Baby Oil. Big smile.

"Now Mommy's going to check the lil baby's cunt."

I threw a rod immediately.

Slowly she inserted her pretty finger into my cunt. Deep. Then she took it out of my asshole and then put two fingers in there. Deep.
"Yeah, baby dick sissy Stevie likes Mommy in her cunthole, huh?"

"Oh yes, Mommy, I love it. Love Mommy in my sis cunt."

"I can tell, sissy, your little bitty weiner is all hard and saluting Mommy."

She finger fucked my cunt for a long time. The silence and sexual tension was very exciting.

"Yeah Mommy loves finger fucking her lil babygirl. Now Mommy is going to baby oil the baby. We don't want her getting a rash, do we?"

"No Mommy."

Here she began squirting lots of baby oil all over my dick and balls and down into my ass crack. Then she was slowly jacking my hard dick and smiling down at me.

"Yeah, sissy Stevie likes Mommy jackin' his lil weiner, huh?"

"Oh God yes Mommy. I love it."

Then she fastened the large diaper around me, using the adhesive straps provided.

"Stevie, why does Mommy have you in diapers?"

"Because Mommy wants a baby?"

"No sissy. When Mommy, or anybody else asks you that, you say, 'I have to wear diapers cause I only have a baby size pee pee and Mommy likes to keep me in diapers. Cause I only have a baby size penis."

This was humilating to hear. But also very exciting.

"Oh, the lil dick baby is blushing. I love it. Now why are you in diapers Sissy?"

"I have to wear diapers cause I only have a baby size pee pee and Mommy likes to keep me in diapers. I have a very small penis."

"Good girl. Mommy is going to want to hear you say that a lot. That's good for a tiny dick sissy to say that. Out loud. So she knows who she is, and where she belongs."

It was wildly kinky to be walking around her house in diapers. Of course I was rock hard. She took me into the kitchen and opened the frig for me to look in.

"Look Sissy. Mommy bought two six packs of beer. She wants her new babygirl to drink lots of beer so she can go pee for Mommy in her didies."

She opened a beer for me and then fixed herself a gin and tonic. We sat on the couch in the den and she kept squeezing my dick thru the diaper. I was rock hard and loving the odd diaper feel on my hard dick and balls.

 

There was heavy sexual tension in the air, a fear of her hitting me hard at any moment. But she just kept feeding me beers.

"I know it's hard to pee in your diaper the first time. You're not used to it, Sissy. But Mommy will be so proud of you Stevie girl."

"I find myself masturbating all the time now, thinking of spanking you, making you cry. I love to see you bawling and screaming for Mommy. That makes Mommy cum hard. In her hairy cunt. Where Sisssy Stevie likes to go."

"Oh yes Mommy. I love to kiss and smell you down there."

"I know. Mommy loves it too."

After my sixth beer, I finally had to piss really bad.

"I have to go pee pee Mommy."


"Go ahead faggot. Pee your diapers for Mommy."

Then i just let go.

She was enthralled, watching my clean white diaper turn yellow at my crotch area.

"Atta girl! That's my baby dick sissy girl. I love this. Love watching baby go pee pee for Mommy."

 

She really did look happy. We made out for a bit on the couch. And then Mommy was changeing my diaper. She checked my pussy first.

 

And so one more ritual was added to my three to four day a week tiny dick sissygirl training. And I ate it up, of course.

It was about two weeks later. I remember it was a Monday afternoon. When she answered the door she was in her typical outfit of halter top and shorts and heels. But giggling. She yanked me inside the door and closed it. I could tell she had been drinking. What did she have planned for the sissy?

She took my hand and we walked downstairs to the basement together.

Then we sat on the sectional sofa. I noted that she had our white wines set up already.

"Get undressed Sissy. Then undress Mommy. Have you been working with the plug?"

"Oh yes Mommy. Every night."

"Today is a very Special Sissy Day."

 

Of course I was very nervous around her as usual and quickly followed her orders.

"There's Mommy's Lil Friend."

She exclaimed as she wrapped her pretty hand around my hard prick as I stood naked in front of her.

"Here is a toast to Us Sweetness. And to your rapid progress for a tiny dickiebird girl."

We clinked our glasses.

And drank from our wine. Then she stood up and kissed me on the mouth, with lots of tongue.

"I'll be right back, Baby. Don't go way."

I watched as her lovely ass walked up the stairs in heels.

It was always so exciting being naked and hard around her. I was very turned on, as usual. What did she have planned?

When she came back down the stairs she was smiling widely. But I immediately noticed two things. She was wearing some kind of harness device around her hips that was holding a small dick, about 5" in length. It looked very intimidating and masculine on her. I also noted that she had a leather whip in her hand.

I got scared. This was going to hurt. A lot.

She was beeming at me, as if we had won the state lottery or something.

 

"Today is Sissy Graduation Day Stevie. Mommy's going to take your sissy girl cherry. By fucking you hard in your sissy cunt."

I just sat there on the couch, in shock. Of course I knew this day was coming, eventually, but it seemed to arrive so soon.

"I know that you're scared, Sissy. But that turns Mommy on all the more, as you know."

"But.."

"I know, Honeybun. I've never whipped you before. But I have spanked you very hard and long with the paddle, so Mommy knows you can take a good sissy spank. Today Mommy is going to whip you hard, because I have to take your mind off of your cunt. 'Cause Mommy's going to fuck you there."

The words I could hear but they weren't registering. Next thing I knew, she had refilled our wine glasses and was toasting us again. I gulped mine down in fear.

Then it gets hazy. I was bending over the back of the sofa and she began whipping me. It fucking hurt! The more I screamed and cried, the harder and faster she whipped me. I remember at one point I couldn't take it any more and I ran into the corner. I was hiding in a dark corner crying from the shock and the pain. She let me cry it out for a bit.

"Sissy I know that you're scared but this is your Big Day, The Day That Sissy Gets Fucked Hard. We have to do this, Stevie. Now get back over the couch and let Mommy finish."

I remember trying to reason with her that it was just too painful and she kept smiling at me and petting my hair and touching my dick and balls, which were all shriveled up and scared. And then I was back over the couch being whipped hard again. But, thankfully, it didn't last very long. I guess she just had to prove a point.

Then I was in the master bedroom laying on my back on the bed. I was not tied up.

Now I was really frightened.

"Hold your legs up for Mommy. Put your arms behind your knees. I need to get at your ass. Atta girl!"

WHACK! WHACK! WHACK! WHACK! WHACK! WHACK!

She was whipping my ass and legs with the whip. And it fucking hurt!!! The more I cried and screamed the harder and faster she whipped me. It went on for a long time and I was bawling and screaming. Of course I tried to escape but I couldn't. Several times I put my legs down to protect them and she just whipped my dick and balls and stomach.

I remember crying and crying and bouncing up and down on the big bed.

Next thing I knew. My legs were drapped over her strong shoulders and she was fucking me in my pussy. It didn't hurt a bit. It felt dreamy. I was so happy that she had stopped whipping me.

Her eyes were riveted on mine and her mouth was wide open, as if in a trance. She was grunting a lot as she dicked me.

"Yeah, Mommy dickin' her lil dick sissygirl. Right in her tight sis cunt. Ho Ho Ahhhhhhhhhhhh fucking faggot! I'm cumming so hard. Cumming so fuckin hard. In your hot sissy cunt. Ho! Ho My God!!"

She fucked me for about 12 minutes. Then she just collapsed on top of me. The strap-on dick still in me. I was rock hard and very happy. I made her cum again. Job security.

After catching her breath, she got back on her knees and slowly withdrew the strap-on from my boy cunt. She lay down on the bed next to me.

"Oh Darling I am sooo proud of you. That was so hot. What a great fuck toy you are. Made Mommy cum so hard."

We lay there for a long time, trying to compose ourselves.

Then she was blowing me. Taking my whole hard dick in her pretty mouth while staring at me with a feral hungar. Then her two fingers in my pussy again and I shot my load right away.

"Mllllllmmphhhhhhhh."

She swallowed every drop. I was drained. What an exciting woman.

Then she got up and went into the bathroom. Then I could hear her in the bathroom, running water. I was in a fog. The bed was soaking wet from my terrifying whipping.

She emerged from the bathroom and greeted me with a big smile on her face. As she lovingly wiped off my dick and balls and asshole, very thoroughly.

"Congratulations Darling. You are a true sissy now. Mommy took your cherry. Did you like that?"

"You whipped me so hard Mommy. That fucking hurt! I was scared."

"Good girl. It's good for the sissy to be scared. Especially when Mommy fucks her for the first time."

We had two glasses of wine each, in the master bedroom. She was still wearing the strap-on dick. It was wet. It gave her a very masculine appearance.

At one point, she stood in front of me next to the bed.

"Okay, Sissy. Now clean off Mommy's dick for her. Show Mommy you appreciate her dicking you deep in your sissy cunt."

I licked and sucked her fake dick. It was humiliating but also a big turn on.

"Yeahhhh. That's my little cocksucker girl. Get Mommy's dick all nice and clean. Yeah. Stevie looks pretty with a nice hard dick in her faggot mouth. Don't you?"

"Yes Mommy. Thank you for fucking me and letting me clean you up."

"You're welcome Sis. Gave Mommy such a big hard cum. I want you to clean Mommy's dick up every time I fuck you. That's a sissy job."

"Yes Mommy. I'll be happy to clean you off."

 

Then she was sucking my dick and fingering my cunt. I came very quickly.

"MMmmllllglllllll ulp..mmmmmm."

She was moaning while she swallowed my cum. Savoring every drop of my 14 year old boy cum.

Light years later, Carmen was walking me to the front door. She turned me around and embraced me and tongue kissed me for a long time.

"Thanks so much Sissy. Mommy is so proud of you. I'm going to want to whip you and fuck you all the time now. Can Mommy do that?"

"Oh yes, Mommy. I love it."

 

It was Fall now and I loved playing the baby diaper games, the whipping and the fucking me in my sissy cunt. The whippings still stung but I seemd to be psychologically accepting them now. In my head, it was already a fait accompli, since I was so anticipating my reward of being fucked by Mommy. And maybe blown by Mommy. Just being next to Mommy was divine.

I would stop off at her house after school got out two or three times a week. The days dragged until I got to her house and then they zoomed by.

When I wasn't actually with her, I was at home jerking off to thoughts of being with her and what just happened. I would put her dirty cunt scented panties over my head, the crotchband directly over my nose, and just envelope my face in her intimate odor, while I jacked off furiously.

She bought me a shirt for Christmas, a normal shirt, and a bigger plug for my butt. I was filled with love and lust for her.

She just loved watching me piss in my diapers. She would hold my dick while I peed for her. It felt very erotic. Everything about her was erotic.

Now that I wasn't cutting her grass, I was still visiting. I loved the whole game of having a secret with this lusty, kinky Goddess. The espionage movie. I was a double agent, sworn to secrecy. Some of my classmates would ask me to hang out after school but I could always put them off for the next day. My parents were never curious about how I spent my time. I guess they just assumed I was with friends.

One afternoon when I came over to her house, we drank our first wine in the basement naked. Then Carmen refilled our glasses. It was unusual for us to drink this much before spanking or sex. Something was UP.

Then she was spanking me with the paddle while I was over her lap. It seemed extra hard. I was sobbing, but trying to control myself. Then tells me to bend over the sofa. First the paddle, then she switched to the whip. A hard whipping. By now I was crying and screaming for her to stop. But I don't move away. Mommy doesn't like that.

Then she takes my hand and is walking next to me up the stairs to the bedroom. I am still sobbing and moaning from the pain. Hoping that it's over.

"Lay down faggot!"

I follow her orders and soon she is fucking me hard, in my cunt. It feels wonderful. Especially knowing there will be no more pain today. My legs over her shoulders and she has an angry look on her face as she pistons the big strap-on in and out of my cunt. It is very hot and exciting.

"Tiny dick sissy. Loves Mommy in her cunt, huh?"

"Y..yes Mommy."

"Why can't you fuck mommy?"

"Cause I only have a baby pee pee. I'm too small. Mommy needs a mancock in her cunt"

"Haaahhhhhhh fuuuuuuuuckkkkking faggot!!!! I'm commingggggg!!!!!

Her body was spasming like crazy.
Then, wonder of wonders, I came too. Waves of jizz shooting out of my lil weiner. Over and over again. It seemed to go on for a long time. My dick just kept shooting and shooting. She was watching me shoot and it just seem to goad her on. Fucking me hard in my cunt.

 

Then she collapsed on top of me. I was filled with the most post-euphoric after cum feeling. Sublimely happy and sated in my dick and balls and faggot girl pussy.

 

Afer a bit Carmen slowly removed the strap-on from my ass and put it up to my face. It was coated with Vaseline and sweat from my ass.

"Clean Mommy's dick off, Faggot. Say Thank you to Mommy's dick for fucking your sis cunt."

I obediently licked and sucked it clean.

"Mommy I came while you fucked me."

"I know Sissy. Look at your cum all over my belly. Lick it clean faggot. Clean your cum off of Mommy."

Obediently I bent my head and licked all of my copious cum off of her stomach. Carmen was stroking my hair like I was a puppy.

"Thatta girl. Clean all of that sissy jizz off of Mommy."

Still floating with that wonderful just fucked feeling.

After I cleaned her off, we both just lay on the bed together, savoring what just happened. Quickly her head turned to face me and she had a huge Cheshire cat grin on her face.

"I have one more surprise for you Stevie."

I couldn't begin to imagine what this could be.

 

Carmen got up off of the bed and walked over to the closet. She was giggling now. She opened the closet door.

Shock Theatre. There was a woman her age standing in the closet. I couldn't believe it! She was about 5'9, with red hair, nice tits, in black top and short skirt, dark nylons, high heels.

I was so embarrassed.

"Stevie dear, this is Maizie. I've been telling her about you and she's been wanting to meet you."

"Hi Stevie."

"Ahh hi."

"Ohh he's blushing. Adorable."

"Did you have a nice cum Maizie?"

"Oh My God Yes. Hearing you whipping him and then fucking him. I came about twelve times."

I had completely forgotten about her whipping me hard downstairs. Of course Maizie could hear my screaming and bawling.

I felt such a sense of betrayal. But it also turned me on in a strange way.

"Such a little cutie, with a little prickie on her," Maizie was petting my head, like I was the family pet.

"Sissy let's go down into the living room. Fill some wine glasses for us."

 

This was really trippy and surreal. In a trance, I walked downstairs into the kitchen and filled three glasses with wine. Then I took them out into the living room. Mommy and Maizie were sitting on the couch whispering.

"Here's our lil dick sissy."

I handed them their wine and Mommy gestured for me to sit inbetween them. Maizie was still dressed while Mommy and I were naked.

"Carmen you are soooo lucky. He is adorable."

"I know. And she sucks pussy like a dream. You'll see. Sissy, tell Maizie why you have to wear diapers for Mommy."

"I have to wear diapers cause I only have a baby size pee pee and Mommy says it belongs in diapers."

Carmen lit up at this rote memory recital. While Maizie's mouth fell open and she openly masturbated to my reciting these little tiny dick sissy affirmations.

"Sissy, why can't you fuck Mommy in her cunt?"

"Cause my dickie is too small. I have a small penis, sissy size. Mommy wouldn't even feel it. Mommy needs a man cock."

"Here, Maizie, look!"

Carmen took my head in her hands and then hauled back and slapped me very hard in the face.

"Oww...Mommy that hurt," I exclaimed.

Then she did it three more times. I was bawling and screaming. But I knew not to move. Carmen was beaming.

"I love to slap her. She is such an obedient sissy."

Then her hand was on my dick and I was soon rock hard.

"Such a good peeny girl to let Mommy hit her hard. Yeah, that's my good sissy. Lil sis weiner is all hard now, huh?"

"Yesss Mommy."

"Stevie, get down and suck Maizie's cunt for her. Make our guest feel at home."

Here Maizie lit up and spread her legs wide for easy access. She pulled her black lace panties aside for me to get at her shaved cunt. I dived into her very funky cunt. Sniffing and licking and wiping my face in her intoxicating pussy scent.

"Oh My God!!! She is wonderful!"

"See? I told you. Doin' good sis. Show Maizie what a good cunt lapper you are."

This was so hot and exciting. Eating this strange attractive woman's funky, excited cunt. I was down there eating away for about an hour and a half.

"Pull her hair! Hard. She likes that."

And Maizie would gleefully follow Carmen's instructions. A couple of times Carmen leaned over and slapped me in the back of the head as I ate out her friend.

"Yeah! Yeah!! Atta girl. Eat that cunt for Mommy!"

After Maizie had cum about 15 times, Mommy told me to stop and take a break. I gratefully sat back on the couch in between them.

"Did you enjoy that, Sissy?"

"Oh yes Mommy. Thank you so much."

"You're welcome faggot. Thank Maizie now."

"Thank you for allowing me to eat your pussy Maizie. You have a lovely cunt. I loved eating you."

"You're welcome Stevie. I loved it. You are very, very good at it. I hope you can do it a lot more for me, in the future."

"Me too."

 

We had some more wine and rested for a while. Then Maizie asked if she could blow me.

"Of course. She loves that. Sissy stand in front of Maizie."

Maizie just about devoured me. She seemed ravenous and so excited about sucking my young dick meat. After a while, Carmen helped out.

"Here, I'm gonna pull on her nuts. She likes that."

She began yanking on my ball sack, hard, and I shot a huge load.

"Ohhhhmmmmmllllm mmmmmm" Maizie growled with my dick shooting off into her wet mouth. She stayed with me until my dick went soft. What a day!

 

I soon got dressed. Just before I left, Maizie took off her dirty panties and gave them to me.

"This is for a good Sissy. Carmen told me how much you like wearing her soiled panties. I want you to have these and think of me when you sniff them and jack off in your room."

"Oh I will. Thanks so much Maizie."

"You're welcome. Tiny Dick Faggot."

 

Carmen paid me my ten dollars and I was on my way. She instructed me to phone her tomorrow afternoon.

 

I was still in shock over Carmen sharing our secret with her friend. But I had to accept it. Mommy was in charge.

I was seeing her about two or three days a week now. Maizie would be there every third or fourth visit. Carmen really took pride in showing me off and exhibiting my sissy skills. She loved spanking and whipping me hard in front of her friend. Then encouraged Maizie to spank me hard too. I had built up my pain tolerance and became more used to it. Knowing that I would be rewarded with good sex after a hard beating.

Carmen loved diapering me in front of her friend and they both loved watching me pee my diapers in front of them. Carmen liked to put her hand inside my diaper and hold my little weiner while I peed for her into my diapers. Strange, erotic feeling.

Both women loved fucking me with the strap-on, both could cum hard fucking me in my cunt, and I often came from it myself.

 

At fourteen and then fifteen I was in a sexual wonderland. Fall came and went and then another Christmas. Both women bought me normal clothes as Christmas presents, a shirt, a sweater.

However, toward the end of the second summer of our friendship, I began to see her less and less. I was terribly hurt but I couldn't complain. That wasn't my sissy place. Shortly after the second Christmas season I was only seeing Carmen about once every other week.

Then by mid January I suddenly did not hear from her again. The deprivation I felt was enormous. Like having to go cold turkey after a very heavy heroin habit.

I was so desperate that I finally swallowed any remaining remnants of pride, and phoned her at home one afternoon. I told her that I missed playing with her very much.

"I've just been very busy Sissy. I will call you."

I was crushed. Of course she never did. But she has fueled my sissy fantasies ever since. I would purposely befriend the gay guys in high school and would soon inveigle my way into blowing them in private somewhere. Just to be doing something sissyish, forbidden, something Mommy would like watching or hearing about The gay guys were often surprised by my advances but loved that I was bi and still in the closet.

I sought out dominant girlfriends but without much luck.

I've been searching for a woman like Carmen, sexy, maternal, dominating, and cruel, ever since.

 

In my last summer of high school I drove by her house one day, hoping to maybe spot her walking to and from her car or something. There was a young guy of about 15 cutting her grass in front. My replacement. He had a slightly femmy look, if you were looking for that. I knew she had moved on.

What a woman!

 

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