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The Boarder

“Step in, honey.”

She was holding a pair of women’s cotton panties, pink, open for me to step into. I was naked and trembling. I followed her orders. Frieda pulled the panties up my legs and then fastened them about my waist, stroking my penis and balls and ass several times. “There. Now doesn’t that feel good, honey?”

“Yes Mommy.”

“Ohh your little pee pee and balls look so pretty. Oh someone’s getting a little hard, Sweetness. I guess you like your pretty panties.”

“Ooh Mommy. That feels so good.”

She was slowly stroking my dick and balls. I was on fire. “Oh look, Darling. You’re getting all big and hard. Or at least as big as you get.” (She giggled) ” We’d better take care of that. Or Baby is going to have trouble sleeping later. Go into the bathroom and get the hand lotion, Hon.”

In a boner sex trance, I minced down the hallway and into her bathroom. I opened the medicine cabinent and took out the Jergen’s Hand Lotion container and quickly returned to the bedroom with it. Knowing that she would be jacking my hard dick soon. I was putty in her strong, feminine hands. Willing putty.

It all started when I rented a basement apartment from this middle aged German couple in the Ravenswood neighborhood of Chicago. Werner and Frieda, both in their fifties, did not stand out in a crowd. If you saw them on the street you would probably think them the most nondescript couple of all. That’s the impression I had too, when I first rented the small apartment.

I was at a real low point in my life. I had just split up with my wife, Pat, and she had the old apartment in the suburbs. Now I was on my own in the city, working a clerical job at a film production house downtown. I was approaching forty years old and I just seemed to be adrift. But thank God I had a job when I signed the lease for the apartment. Frieda showed it to me. It was neat, clean, and cheap. Perfect for me. I filled out the application and she seemed pleasant, cordial, but nothing out of the ordinary. As I said, she appeared kind of nondescript. About five six, dyed brown hair, blue eyes, big tits, big ass. Dressed conservatively.

She said she would check my credit and get back to me. Fine. I was staying at a motel downtown. She phoned me that night, which seemed awfully quick. I was approved and could move in immediately. She said she wouldn’t begin to charge me until the first of the month. Since this was the third week in April that was very generous.

My old buddy Ray had a truck and he helped me move. I didn’t have much stuff so it was no biggie. I liked living in the city, as opposed to the suburbs, and went for walks as often as I could. However, the apartment was in the basement and it didn’t get much light. It was dark a lot and kind of gloomy. If I was depressed this dark quality just added to it.

I ran into Frieda one Saturday morning. She was watering the lawn in the back yard. She was wearing shorts and she looked nice. “Hi David.”

“Hi Mrs. Schmidt. You look nice in those shorts.”

“Why thank you! Oh David, Werner and I want you to come for dinner tomorrow night. Seven pm. Upstairs.”

The way she said it, she didn’t even consider me not accepting. I was hesitant. But she was the landlord and I wanted to be on their good side. “Um..okay. Thank you. I’ll be there, Mrs. Schmidt.”

She smiled and continued watering the grass.

Dinner was a bit tense. Frieda seemed to want to draw me out, but she also seemed very nosy.

“Do you have a girlfriend? I would think a good looking man like you would have several.”

“No, not really. I just split up with my wife. But thanks for the compliment.”

“Well I’m sure it’s her loss. You’ll have another one in no time. Probably better looking.”

She kept staring and smiling at me. Her attention made me a bit uneasy.

Werner said almost nothing. Just ate with his head down. But Frieda definitely wore the pants in that family. “Werner, more wine!”

He’d pop up out of his chair, go into the kitchen, and return with a fresh bottle of German wine, which he poured for everyone. I got the impression he worked as some kind of contractor.

“Are you going out to the clubs to meet girls, David?”

“Uh..not that much.”

“Well it’s best to get back into the swim of things. You know, like getting thrown from a horse. You just jump right back on. Don’t let the horse intimidate you.”

“I’m sure that’s good advice.”

They served pot roast and it was delicious. After dinner, we had some brandy in the living room. They had a nice big apartment, two bedroom. “Do you like brandy, David?”

“Oh yes. I love to drink.”

“Ha. Ha. What else do you love?”

“That’s a secret.”

Frieda chuckled and smiled at me. She enjoyed repartee like that. And I was positive she wanted to know all of my secrets. But what were hers?

As I was leaving their place to return to my apartment downstairs, she walked me to the back door and then kissed me on the cheek. That seemed odd. For the first dinner with the new boarder. Oh well. She smelled good and her big tits felt good too.

The following Saturday morning I was sleeping in late. The job was boring and it looked like it might be ending soon. The office gossip was that they were in trouble. Financial trouble. I picked up a bottle of vodka on my way home and drank it in my room.

There was a knock at the door. Weird. I didn’t know anybody in the neighborhood and it wouldn’t be Ray, he would have called me. I got out of bed and opened the door a sliver. It was Frieda. She had on new jeans and low heels. “Hi David. I hope I didn’t wake you.”

She glanced down at my crotch and I realized I was semi hard in my jockey shorts. “Uh no, Frieda. Kind of a big night. What can I do for you?”
“I want you to come shopping with me. Just some groceries. It’ll be fun.”

I stood there for a minute. I really didn’t feel like going. But there was something about her. I looked up again and she glanced at my dick again and smiled. “Throw some jeans on and meet me in the garage in ten minutes.”

“Okay.”

After I shut door, I touched my dick and I was now rock hard, thinking of her smile and her looking at my crotch. Did Frieda want me sexually? That’s the vibe I got. But what about her husband? Hey, she was in charge.

These thoughts ran thru my head while I threw some clothes on and ran an electric razor over my face.

Frieda beamed with a big smile when I arrived in the garage. They had a late model Lincoln Town Car so business must be pretty good for her and Werner.

As we drove to the store I realized I enjoyed being in her company. There was something mysterious about her. What were her motives? I was bored and quite lonely. Didn’t really have any friends in the city, with the exception of Ray. So I was flattered that she was taking an interest in me.

She was kind of amusing in the store. She would pick something out and put it in her basket, then explain why she chose that item.

She lit up in the cosmetics section. “Did you know I dye my hair?”

“No.” (I lied.) “You’re not a very good lair, David. But you are sweet.”

Here she slapped me on the ass affectionately. I got hard. As the day wore on she was touching me more and more. “Ever thought about giving yourself some highlights in your hair?”

“No.”

“You have pretty hair.”

Touching my hair and my neck. I loved her fingers on me. My dick was out and tingling. Could she see it?

“Have you ever thought about shaving your legs?”

“No.”

“You have very nice legs. Womanly. A lot of girls would kill for your legs,” she laughs. I didn’t know how to take it.

She liked to buy all the tabloids too. “I love to read all the dirt and scandals. The more dirt the better.”

Here she slapped my ass again, but this time her hand lingered on it.

When we returned home, I offered to help her put her things away. “Oh no, I’ve bothered you enough. Go chase some girls,” then another swat on the butt.

Returning to my apartment, I had a full fledged, wet hard on. I had had it for half of the time with her. I made myself a drink and began fantasizing about Frieda Schmidt. Did she want to have sex with me? It sure seemed like it. Did she know I was very, very turned on by dominant women? How could she know that?

I took a nap and woke up later with a very wet crotch. I had had a great wet dream about her dominating me. Then I jacked off and had a wonderful cum.

The following week I was let go from the job. Yeah, they were in trouble all right. And now so was I. Now I was really depressed. Of course I was around the apartment now on week days. I would see Frieda now and then and she was always friendly. Thank God she didn’t ask me about my job. That was tactful.

On Friday she knocked on my door and asked if I would like to make some extra money? Sure. She needed her garage cleaned. It was filthy. She would pay me fifty bucks. Great! I set to work immediately. It took me several hours.

When I was finished I was very proud of my work. I had removed about 18 full bags of trash from the place. I thought about knocking on her door and asking for the money. But then thought against that. Maybe she knew I was out of work. That was classy. Why not just wait until she brings it up and pays me?

I must confess here that I was thinking about her a lot and jacking off a lot. She was the main character in my fantasies.

The following Monday she knocked on my door. It was early afternoon. She seemed a bit dressed up, make up and a nice skirt and pressed blouse. The blouse showcased her big tits.

“Ah. You’re in. Good. You did such a good job, cleaning the garage, I want you to come up and have a drink.”

By this time I didn’t even consider turning her down. I didn’t know where this was going. But I was enjoying it. It did not go unnoticed that she didn’t bring this up until she was alone and Werner was at work.

I was dressed casually in jeans. I knocked on her back door and she led me into the living room. There were two drinks on the coffee table. Strong drinks. Manhattans.

She paid me the fifty bucks and handed me my drink. I was semi hard in my pants. I noted the drinks seemed to have no effect on her. She was crossing her legs a lot. Was this a date? With her husband coming home some time? Intense staring at me. Had she been having wet dreams too?

“David, do you ever feel like something is missing in your life?”

“Yeah. Sometimes.”

I noticed her playing with her high heels a lot. Kind of twirling and displaying them.

“You are such a sweet boy. But you seem sort of lost. Without direction.”

I just sat there and took this in, the whiskey burning a hole in my belly. She smiled and poured us more Manhattans from a large pitcher she had made.

“It seems like you just need some discipline, something to motivate you.”

I said nothing. But the word discipline started to get my prick hard. And that intense stare of hers, like a cat eyeing a mouse. A trapped mouse.

Did she know I was into dominant women somehow? How? Now she was rubbing my leg. Cast iron boner. I couldn’t believe she was being so intimate. I hadn’t had sex with anybody in ages.

“Do you mind me touching you, David?”

“No! it’s nice.”

“Good hon. I like you. And I like touching you. Do you like me?”

“Yes Mrs. Schmidt.”

“Frieda.”

“Frieda”

“That’s better.”

Now her hand was rubbing my mid thigh. My dick was punching my pants. “David, I want us to be close. I think it will be good for both of us.”

I was stunned. I didn’t know what to say.

She leaned over and kissed me softly on the lips. Then her tongue entered my mouth. Boldly roaming around and then sucking my tongue. Her perfume smelled nice. She was wearing more of it than usual. Squeezing my leg. She sipped her drink and just stared at me. Then another long, sexy kiss, rubbing my leg.

“Stand up, hon.”

I stood up. What now? Did she have some kind of plan? She seemed bold. I was a bit scared. She just smiled at me as she sipped her drink. “Take your pants off, honey.”

I just stood there. Was she serious? “Well, do it! Go on! Don’t just stand there!”

Her voice was suddenly bossy. Trembling and very nervous, I undid my belt and attempted to remove my pants. It was very awkward because I tried to take the pants off over my shoes, but it wouldn’t work. So I had to sit down and unlace and remove my shoes. My hands were shaking. I was under her spell. She just sat there sipping her drink and smiling, as if she was quite used to this.

Finally I was standing in front of her in my jockey briefs and a t shirt. My dick was rock hard. And wet. “Down boy!”

With that she slapped my dick. Hard. I doubled over in pain. “Bad boys get hard without permission.”

Now I was getting frightened. “Come here.”

I stood in front of her. She pulled me in between her legs. She was still smiling at me and rubbing the backs of my legs. “Such a pretty girl.”

The next thing I knew I was over her lap. This was taking on a dream like quality. Then she pulled down my jockey briefs. Then she was stroking my ass cheeks and my upper thighs. The air was electric with sexual tension. I was almost afraid to breathe. But I did savor her being in charge, Frieda making all the decisions for me.

“Just relax hon. Momma’s gonna give you a good spank and you can have a good cry.”

Now I was scared. It was all like a strange dream. But my dick was harder than ever. Crack! Crack! “Ow!”

“Shhh. Quiet baby. Don’t be a bad girl.”

The two spanks were hard. My ass was stinging. But god I was excited. “Such a pretty girlie ass and asshole.”

Her fingers playing on my ass, then in my crack, then probing my anus. Had she planned it this way? CRACK! CRACK! CRACK! CRACK! CRACK! She was incrediby strong. It hurt. I was crying already. “Ow! Oww! Frieda no, that hurts!”

“Shh. Quiet baby. Momma loves you. This is for your own good.”

I could hear myself crying and sobbing. Like a child.

Her fingers on my ass, then on my balls, thighs, then squuezing my dick.

She knew it was turning me on. CRACK! CRACK! CRACK! CRACK! CRACK! Next thing I knew I was bawling my eyes out. Wailing loudly. Then she’d be stroking me again.

“Shhhh. Moma’s here honey. It’s all right.”

Then I could feel her finger going into my asshole. Just a little. Then a little more. Then she pulled her finger out and grasped my rock hard dick. “You little whore!”

CRACK! CRACK! CRACK! CRACK! Wailing some more, hiccuping and shaking with fear. “Almost finished baby. Almost over Precious.”

I could hear myself crying loudly. Then it was quiet. Then she was touching my dick again. Slowly jacking it. She must have known exactly how close I was. Suddenly I went over into this dreamlike cum, my dick kept pumping and pumping and pumping, with her help. I shot a big load right away. I seemed to just keep cumming for a long, long time and then she kept jacking me after I came. Long after. It got painful. “Ow! Frieda! Stop!”

“Shhhhh.”

My face was soaking wet from crying. It was like I had reverted to childhood or something. Thirty nine years old and bawling like a baby. Post orgasmic euphoria. My dick and balls felt drained and wonderful. Now she was stroking my ass again and my thighs. “Good girl. You are such a good girl.”

I seemed to cry and heave for a long, long time.

Then a long silence while she stroked me.

“Stand up honey.”

Finally I stood up. On wobbly legs. In a dream. My dick was soft. There was a puddle of cum on her carpet. My jockey shorts were in a heap on the floor. As I stood there I realized that that was easily the best orgasm I had ever experienced. She was smiling at me. Beaming. Her face was wet and disheveled.

“Such a pretty girl.”

Then she was up and embracing me, kissing me, her tongue in my mouth, sucking my tongue, in control, stroking my ass, whimpering with pleasure.

“That was wonderful. I knew that’s what my baby needed. And now I’ve got a present for a good girl who took her first spanking for Momma.”

Frieda picked up her skirt and removed her panties. They were full cut cotton, purple colored. They looked very, very wet. She smiled at me and then held then open for me. “Don’t just stand there, Stupid. Step in.”

I stepped into the soiled, wet panties of this in charge woman and she pulled them up my legs and smoothed them around my very spent dick and balls. “I want you in panties whenever I see you David. Did you hear me?”

“Yes Frieda.”

“Mommy. You call me Mommy now.”

“Yes Mommy.”

She kissed me on the lips and patted my hair, like I was a pet that had performed well.

“Okay Precious. Get dressed and get out of here.”

In a total sex daze, I got into my clothes. As I was about to leave, I picked up my jockey shorts. She grabbed them out of my hand. “Give me those. Girls wear panties. Not this shit. Understand?”

“Yes Mommy.”

She swatted me on the ass. “Now scoot.”

That was the begining.

Well of course I began jerking off about three times a day just remembering, reliving that incident. What was next? She was calling the shots and I was loving it.

Two nights later I came home from a job interview and there was a note pushed under my door. In Frieda’s printing. Dinner upstairs at 7. That’s all it said. Not asking me. Telling me. I got hard thinking about it. How friendly would she be in front of her husband? I was sure to wear her soiled panties under my pants. You never know what she might have planned. I had been sniffing them and jacking off to them several times a day.

I knocked on the back door at seven and she took her time answering the door. When she opened it she just smiled as if I was a member of the family who was always expected. I sat down at the table across from Werner. He poured me some wine and then Frieda joined us with a big bowl of salad.

Things were normal for a few moments while we started to eat. Then Frieda acted like she had forgotten something. “Oh, David. Come over here.”

I got nervous, but pushed my chair out and walked over to her. Werner was chewing his food and looking at us. Frieda unbuckled my belt and pulled my pants down. I couldn’t believe it. She lit up when she saw that I was wearing her panties. “Good girl! Look Werner! Good girls obey their Mommy.”

This was too weird for me. I stood there, sort of paralyzed. Frieda was rubbing my dick thru the panties and acting like I was her prize poodle.

Her touching was having the desired effect. I got hard. “Look. He’s small. But cute.”

She had actually pulled down the panties and was displaying my dick and balls to her husband. He looked fascinated. “Turn around dear.”

I turned around and now she was showing Werner my ass. He got up out of his chair and was softly touching it. “Ach! Ooooo.”

“See. I told you. She’s precious.”

Then she pulled the panties back up. “David, take off your shoes and pants. You can eat in your panties.”

The weird thing was, my prick was rock hard. I was embarrassed but so turned on.

I sat back down on my chair and quietly removed my shoes and pants. They continued eating, as if this were the most normal thing at dinner. When we had finished our meal, I thanked Frieda and told her it was delicious, which it was. “Thank you sweetie. We’ll have our brandy in the living room, then I’m going to run your bath.”

My bath? What now?

I was sitting on the couch in the living room. Werner was sipping his drink and looking at me hungrily. Frieda sat next to me and was touching me a lot. I could hear the bath water running. “Frieda, why are you giving me a bath?”

She frowned and pinched my thigh. Hard. “Ow!”

“Mommy. Not Frieda. Mommy.”

“Yes Mommy.”

“I am running the bath because I have to shave my girl’s legs. That’s why.”

Oh. Where was this headed? She would get up now and then to check the temperature and level of the bath water. My dick was hard in my ps.

“Okay hon. Let’s go. In the tub.”

Talk about reverting to childhood! Frieda sat on the edge of the tub and removed my panties, then helped me into the water. Thankfully it wasn’t too hot. I sat down and she proceeded to wash my hair. “We’re going to have to touch this up soon.”

“Yes Mommy.”

Then she thoroughly washed every part of me with a washcloth. She seemed to concentrate on my dick and balls and asshole. Then she shaved my legs of hair. Then she even shaved my dick and balls of hair.

All the time acting as if this was the most normal behavior for the landlord of a 39 year old man. “Okay, Precious. Let’s go.”

I stepped out of the tub, devoid of any body hair save for that on my head and eyebrows. She enveloped me in a large fluffy bath towel and dried me off. Then I noticed she opened the medicine cabinet and took out a container of Jergen’s Hand Lotion. She took my hand as if I were a little girl and walked me into a bedroom. I noticed a pair of panties on the bed, and a woman’s skirt.

“Sit down David.”

I sat down on her bed. My dick was semi hard again. She sat down next to me. “Such a pretty girl. Looks so much nicer without that nasty old leg hair.”

Here she ruffled my just washed hair and kissed me on the mouth. A deep soul kiss. Her hand on my dick, fondling me. I was loving it.

After a long time, her whimpering, she broke the kiss. Now my dick was brick hard due to her ministrations. Then she took the Jergen’s hand lotion and poured a generous amount on top of my hard. Then, smiling happily, she began to slowly jack me off. But it wasn’t going to take long since I was so keyed up and excited by this bizarre family. “Yeah. Davia’s got a big old hard. She’s all excited for her Mommy. Huh? Isn’t she? Davia likes Mommy touching her dickie bird. Huh? She’s gonna shoot a nice big load for Mommy. Cause Davia is a good girl. Isn’t she?”

“Oohhhhhh f uuuuuuuk.”

A geyser of jizz shot out of my overheated prick. A big smile came over her face but she just kept jacking that dick. “See! See! Yeah. Davia’s a good girl. She knows how to shoot a big load for her Mommy! Huh? Huh, Baby.”

I was in a trance. Heaven. After I shot for a long time, big ropey strands of sperm all over my stomach and her arm and hand, Frieda leaned over and kissed me again. Then she efficiently took out some tissues and cleaned us off.

After she had me all cleaned of jizz, she had me don the panties (cotton, full cut, white, soiled by her, as I later determined from sniffing them when I got home) and then the skirt, about mid thigh. She had to pin the skirt at the waist and hem but otherwise it didn’t look too bad. I looked at myself in the full length mirror and I liked what I saw. “Thank you Mommy.”

“You’re welcome Precious.”

She put my pants in a bag for me and I put my shoes back on. Then she walked me to the door. A chaste kiss on my cheek. Was this weird or what? At home in my room I sniffed her cunty white panties. This was weird but so fucking sexy. Now I couldn’t get her out of my head.

After that things began to change. Seeing her around the building. Always a smile for me. Touching my hair, my neck. I’d get excited immediately. Sometimes she would glance at my crotch while chatting with me and rubbing my neck. I was definitely in her thrall.

Naturally I spent a lot of time jerking off in my room thinking about her and wondering what were her plans for me. I was working a temp job for the next few weeks.

Then I come home one day, unlock the door to my room. Shock waves. Frieda is sitting in my chair reading my porn books. B and D. Drag queens. Spanking books. Had she been here before? She certainly didn’t look nervous. You could cut the sexual tension in the air with a knife. She just smiled at me. There was a very pregnant pause. “Hello Davia.”

“Hi Frieda.”

“What’s my name?”

“M..Mommy.”

“That’s right. I was just looking over your little library here. Very interesting.”

She stood up and came over to me. Intense stare. I was shaking with fear. She began running her fingers thru my hair. “I want you to come upstairs in about ten minutes. Have a drink with me. Then I’m going to punish you And wear your skirt when you come up.”

She kissed me on the cheek and exited. I was truly terrified. The thought of complaining about her snooping around my room and invading my privacy entered my mind but only for about a millisecond. She was in charge. I was like a moth to the flame. I sat down on my bed to try and regain my composure. What to do? What could I do? I was completely in her power. I would do whatever she asked.

I glanced at the mags she had been looking at. Severe spanking with big red welts on the butts on the men being spanked. By dominant women. Whippings. Stuff I could never take but had fantasized about. Men in drag. Feminized. Humiliated. By women. Very bossy women. Stories of slaves and mistresses. Slaves. Was that me?

I donned the skirt she had given me and looked at myself in the mirror. I looked femmy but certainly not enough to pass for a woman. I looked like a femmy man wearing a skirt. And a man’s short sleeve shirt.

Trembling I made my way upstairs to her back door and knocked. Hoping none of the neighbors would notice me wearing a skirt standing on the back steps of my landlady’s apartment. Frieda took her time answering the door.

She greeted me in a few moments. She was wearing the same outfit, medium length skirt, dark blouse, low heels. No wait, the shoes were different. She had on high heels now. To punish me with? She was smiling. “Come in dear. Join me on the sofa.”

She went and fixed me a drink. I couldn’t stop shaking. “Here we are.”

She hands me a drink. Manhattans. Her drink. “To us.”

“To us..Mommy.”

“Good girl.” Frieda smiles and touches my face. I swooned inside. I loved making her happy. My mystery mistress.

Her enigmatic smile. “Why, Davia. You’re shaking. You must be exited. Or scared. Ha . Ha.”

I remained silent, sipping my drink. She seemed to be glowing with happiness. Rubbing my leg, maternally. “It’s okay, dear. I think we’re both making progress.”

She fixed me another drink. I began to relax a bit, as much as possible under the circumstances. “Are you looking forward to your spanking?”

“N..not really, Mommy.”

“Well I am!! Ha. Ha.”

Rubbing my leg. “I’m loving this. Can’t wait to touch your pretty ass again.”

Pretty? I was always being called pretty by Frieda.

I was almost finished with the second drink.

“Well I’ve think we’ve waited long enough. Finish that, honey, then take off your shoes and skirt.”

My heart was pounding wildly. She just sat staring at me, benignly. I stood in front of her. Smiling warmly, she slowly removed my (her) panties. I wore nothing but her panties now. She pulled them all the way down. “Step out dear.”

I did. Naked in front of her. She smiled at me. My dick seemed so tiny. “Go into the bedroom and wait for me. Stand in the corner you naughty girl.”

I followed her instructions. It was about a ten minute wait. Now I was semi hard. The silences were scary. What was coming? What was she thinking? Remembering how I broke down in front of her last time. The humilation. My stinging ass. How hard would she be this time?

Now I hear her entering the room. Sitting down, bedsprings. Silence. I think she really enjoys the game of it. I know I do. Shaking with fear and anticipation. She’s probably staring at my ass now. Ice tinkling. Her drink. “Alright Davia, come over here.”

I turned around and walked over to her. I immediately noticed a thick wooden paddle next to her on the bed. It frightened me. She quickly took my wrist and pulled me over her lap. I actually realized I liked being there, over Mommy’s lap, with her in charge. She moved her legs a bit and my dick and balls were inbetween her legs. Stroking my ass. “Such a pretty ass on a such a pretty girl.”

CRACK! CRACK! CRACK! CRACK! They were very strong, hard spanks and they really hurt. “Ow! Mommmy!”

CRACK! CRACK! CRACK! CRACK! CRACK! “Ow! OWEEE! Frieda stop!! STop!! It hurts.!!”

I tried to protect my ass with my hand, but she just twisted my arm and contined.

Then silence. Can hear myself crying. Is that me? Like a little girl? Softly rubbing my ass. “What’s my name, Davia?”

“Mommy.”

“Don’t you ever, EVER tell me to stop!”

“Yes Mommy.”

CRACK! CRACK! CRACK! CRACK! CRACK! My ass was on fire. It really hurt! I was blubbering and screaming with all my might. Tears were streaming down my face.

Silence. She had stopped. I was heaving and sobbing and bawling. I could feel her hand on my numb ass. I was terrified. A crying ball of jelly. Time passing. Still sobbing loudly. “Davia, I want you to get up and to stand in the corner. Put your hands on top of your head. And don’t you dare touch your ass!”

I slowly got off of her lap and followed her instuctions. I was sure my dick had shrivelled into a little scared dot of nothing.

So weird. A dream like quality. My fantasy coming true. I was still crying loudly. Couldn’t stop. God my ass stung. Numb. But the pain was going down a bit. My ass sort of tingled. Then after a few minutes, I could feel my dick relaxing a bit. Can still hear myself crying and sobbing. Like it’s coming from another room. But it’s me.

Suddenly she was behind me. Stroking my back, my neck. “We are making progress, Davia. But you’ve been a very bad girl and you’ve got to be taught. You’re getting a harsher punishment today because..because I think you’re ready for it. But you are a very bad girl.”

Why was she calling me a girl? “From now on I want you to show me any new magazines you buy. Understand, Davia?”

“Ye..yes Mommy.”

“Good girl. You may read them for one day, by yourself, then you must show them to me.”

“Yes Mommy.”

Silence. She seemed to have left the room. Moments pass. I’m still blubbering uncontrollably. Trying to calm down. Can hear her making herself another drink in the kitchen. My ass pain is diminishing. Don’t seem to be sobbing aloud any more. God she really lit into me. How am I going to be able to take the paddle? But somehow feel lthat I will.

She was back in the room. Hear the ice tinkling in her glass. Time passing. My arms on top of my head. Getting a bit tired. She’s staring at me naked in the corner, my red beat up ass. What is she thinking? “All right Davia. Time for round two, honey.”

In a trance I returned to her lap. Glanced up at her face briefly. She was actually smiling broadly. She looked quite happy. Well at least she was enjoying this.

Scared. Her hand rubbing my ass. Is that the paddle? “Your ass has nice color Davia. But we’re going to change it a bit. It’s going to be kind of a deep purple after this. Heh. Heh.”

WHAP! WHAP! WHAP! WHAP! WHAP! Again I was screaming and bawling like a little baby. Twisting my arm. God she was strong. Those blows really, really stung. Now rubbing my ass. I’m crying and screaming full force now. She’s twisting one arm behind my back. Then rubbing my legs. Long pause. Was it over? WHAP! WHAP! WHAP! WHAP! WHAP!

It seemed to go on for a long time. Bawling and screaming my lungs out.

But that had no effect on the punishment. If anything, that seemed to encourage her.

Then I realized she had stopped hitting me. Her hand was on my ass. The paddle rubbing my torn up ass. Still screaming and sobbing and heaving and hiccupping. Is that me screaming? Like a little girl? I had no control over myself. Took me a long, long time to calm down. My breathing was very loud and labored. Still her hand now on my ass. Paddle gone. I lay there crying for the longest time. “Good girl. You did good, honey. Now stand up and go back in the corner.”

Shakily I got to my wobbly feet and made my way back to the corner. My ass was way beyond numb. A flashbulb. Sounds like a Polaroid camera. Developing. Silence. She left the room. Time passing. Trying to catch my breath. A sobbing little baby girl. I’m still crying. Tears streaming down my face. Her making a drink. Bedsprings. She’s sitting on the bed. Staring at me. Suddenly standing next to me. Softly rubbing my back, my thighs. Now very maternal. “Did that hurt, honey?”

“Ye..yes Mommy.”

“Good. It was supposed to. Are you going to be a good girl now?”

“Yes Mommy.”

“Good. Come over to the bed. I have a present for a pretty girl who took her spanking well.”

I walked over to the bed. I stood in front of her. She was smiling more than ever. “I am so proud of you Davia.”

“Thank you Mommy.” Then I kissed her hand. “And thank you for spanking me Mommy.”

“You’re welcome sweetheart.” (She patted the spot on the bed next to her.) “Sit.”

I sat down next to her, still sobbing a bit. She was softly rubbing my leg and smiling at me. Then I noted her unbuttoning her blouse. Then taking it off. She had on one of those big old fashioned fifties type of bras, with lots of stitching. Her tits looked huge. I sat there in awe of them. Then she unsnapped the bra and suddenly they were exposed to me. They looked magnificent. “Good girls who take a good spank get presents from Mommy.”

She put her hand at the back of my head and just pulled me into her chest. I began suckling one of the huge breasts in my mouth. I could hear kind of a keening low wail coming from her as I sucked her big tit. I felt like I had come home somehow. Her other hand ran through my hair while I contentedly suckled at her chest. This went on for a long time. Now and then she would gently move my sucking mouth from one tit to the other.

“Okay. Break time, Baby Girl. Did you like your feed from Mommy?”

“Oooh yes Mommy.”

Her hand on my rock hard dick. “Well I guess you did. Your dickie bird is all hard again, Sweetness. Yeah, baby likes her feed, huh? All big and hard for Mommy. Go and get the hand lotion, cupcake.”

In another dream like trance, shaking, I went and retreived the hand lotion from the medicine cabinet. Then handed it to her. “Just stand there, Baby.”

I was standing inbetween her legs. Her exposed chest looked huge. Then she took hold of my dick. “Oh, look. Baby’s got a present for Mommy.”

I looked down. There was a small drop of sperm at the top of my piss slit. Frieda bent over and licked it off. Then looked up at me, lasciviously.

“Having fun, Davia?”

“God yes Mommy. So much.”

“Good girl. I’m having fun too.”

Here I watched as she squirted a large dollop of cream on top of my dick, then began massaging it in. Wonderful feeling. But I was so excited already I knew it wouldn’t last long. Then I felt her finger in my asshole. Halfway in. All the way in. “Ohh.”

“Yeah, Davia likes Mommy in her pussyhole. Huh? Huh, Babe?”

“Y..yssss Mom..mommmmy. Ahhhhhhh!”

Cumming. Hot jizz flying out of my dick. “Thas right. Shoot it out, honey. Shoot your cream, for Mommy. That’s a good girl. Yeah. Davia’s got a big load for her Mommy. Huh? Huh, Babe?”

I collapsed in her loving arms.

When I woke up I was in her bed and apparently we had taken a nap. Frieda was beaming at me. Playing with my hair. “You awake now, Sleepyhead?”

“Yes Mommy.”

“Good. You shot a big load for Mommy. Guess you got all tuckered out after your spank.”

“Yes..Mommy.”

Her chest was still exposed and I was drinking it in. She got up off the bed and was walking out of the room. “Come into the living room, hon.”

Naked, I followed her into the living room. My ass was still sore but I was still tingling from that incredible orgasm. When I reached the living room Frieda was removing her skirt. She had white cotton panties on and her pussy looked very hairy under it. Then she removed the panties and sat down. I just stood there gaping at her bushy black haired cunt. “You like looking at Mommy’s pussy, hon?”

“Oh yes.”

“Good. Kneel down Davia.”

I followed her instructions and kneeled down in front of her. She scooted up on the edge of the couch. Suddenly she hauled back and slapped me in the face. Hard. It stung! She was smiling. Then she slapped me twice more. “Why am I slapping you, Davia?”

“I..I don’t know Mommy.”

“Because I feel like it. It gets my pussy wet. Smell.”

She shoved my face into her steaming, wet cunt. Her pussy smelled really rank and excited. Another slap. Then pulling my hair. “Eat me, you little whore!”

I proceeded to eat her cunt for about an hour and a half. Frieda slapping me whenever the mood struck her. Which was quite often. “Yeeeeahhhhh. Suck my cunt, you bitch. Suck it! Suck it! Suck your Momma!!!”

She was very passionate and had several long cums, squeezing my head, pulling my hair and slapping my face hard. I loved it.

Before letting me dress and return to my apartment, Frieda told me that we had an appointment to buy some “girl” clothes the next day at 4 PM. She wanted me in my skirt on her back steps at 3.30 so we could have a drink before driving over to the store. She said her friend owned the store and we were going to have a lot of fun.

Of course I wasn’t sure about the fun part for me. This would be my first trip out in a skirt. I was obviously a man wearing a skirt. But the sex with Frieda was so great this was a small price to pay. Or so I told myself. I just prayed that it wouldn’t be too embarrassing.

The next day I was on her back steps at 3.30, in my skirt. I kept telling myself it was worth it. The sex was wonderful. I kept repeating it as sort of a mantra to get over my nervousness at what was going to happpen. Out of the corner of my eye I saw something. I glanced over. It was the next store neighbor, guy named Ed. He was looking at me curiously. I had seen him outside several times and we always said hi to each other. Now I just tuned him out. Praying for Frieda to hurry up and open the door. Finally it opened. I darted inside and turned around and saw Frieda wave at Ed. Wonder what he was thinking.

Frieda was more dressed up than usual. More make up, nice sexy teardrop dangling earrings. Very high heels, seamed nylons. I was impressed. My drink was waiting for me on the table. She was scurrying around the apartment. Putting stuff in her purse. I gulped down my Manhattan. “Let’s go honey.”

I stood up. She kissed me on the cheek. “I am so proud of you Davia. Just one thing. Olga is an old friend of mine. Don’t embarrass me.”

“Yes Mommy.”

We exited the back door and walked through the yard to the garage. Sure enough, Ed was still standing in his yard staring at us. I kept my head down.

In the car, on the drive over, Frieda explained that Olga was a very old friend and that this was an upscale lingerie shop. It was in the Old Orchard Shopping Center, in Skokie. It was quite lux as suburban malls go. We had to park pretty far from the store and I got several stares from people in the parking lot. But Frieda was holding my hand and I kept repeating my mantra, the sex is great, it’s worth it for the sex.

The store was very fancy, lots of gold carpeting, chandeliers, mirrors everywhere, baby dolls and bras everywhere. I had a semi hard as soon as I walked in. Anticipating something. But fearful too.

Olga was a dish. To say the least. She was an attractive blond with big tits in a pointy bra. Breathtaking. Intimidating. She looked like a bit older version of that actress Charleze Theron, the one in the recent King Kong remake. The type I would never have the guts to approach. She wore a matching beige outfit of long skirt and sweater with a plunging neckline that showed off her formidible cleavage.

She ran over and hugged Olga, then seem to take me in. They were speaking in German. It was weird. I could tell that Frieda was very proud of her little pet. Me.

As I glanced around the store it looked like there was only one other customer in it, with what looked to be another salesgirl, a young red head. Next thing I knew Olga and Frieda had taken me into a back room. “Get undressed, Davia.”

I stripped down to my panties under their watchful eyes. Olga seemed fascinated by me. Like I was some sort of new hybrid person she had read about. Then I was standing before them in just my panties. I was very nervous.

Frieda reached over and pulled down my panties. I was mortified. She was handling my dick and balls, sort of displaying them to Olga, who was all eyes. Then they were both checking out my ass. I could feel both women touching me. Still chatting away in German. At one point I heard the name ‘Werner’ out of Frieda’s mouth and they both giggled. Then Olga disappeared. Frieda was beaming. Rubbing my back. “Such a pretty girl. You’re going to be so beautiful.”

Olga returned with several pairs of panties and some bras. I tried them all on and they kept commenting in German. After a while they had me just standing there naked. Olga took hold of my prick and was softy stroking it. Like I was a pet she wanted to have.

“Davia has a pretty little prickie.”

“Thank you.”

Then the redhead walked in. “Jane. Look.”

Olga was still handling my dick. I was hard now. Jane walked over and was fascinated. They didn’t bother to introduce me. I was just a commodity. “He’s hard. That’s it. Go ahead. Touch it.”

Jane eagerly took hold of my stiff dick. With her other hand she fondled my balls.

“Feel good, honey?”

“Yes. Thank you..”

Then her hand was in my ass. Poking my asshole. God they were pushy. “She’s tight.”

“Yes, Davia has a tight pussy. That’s what I told Werner.”

That cracked up Olga and Frieda.

The day seemed to breeze by in a hurricane of trying on and modeling clothes in the back of the store. Panties. Bras. Breast forms. Garters. Seamed hose. Even some low heeled shoes. I don’t know where they dug those up, but they were just slightly big. It was fun. But weird. When I was trying on the bras they insisted I keep my panties off. Both Olga and Jane liked touching my dick and getting it hard. Olga liked holding it as she talked about the bras to Frieda and Jane. My dick began to leak some jizz. Olga noted this and wiped it on my balls and ass. I kept repeating my mantra to myself. Olga was so gorgeous I’m sure she wouldn’t even give me a second glance in the street. Now she was holding my leaking dick.

Toward the end of the day, at about 5 PM, Olga served cocktails. We were all drinking vodka and tonics and the women became much giddier and bolder touching me. Jane started to finger my asshole a lot. They loved watching me model my outfits, with a hard on. Kept calling me “Slut Girl” .

Then trouble. I was sitting in a chair, with a bra and breast forms on, no panties, when Olga came out of somewhere wearing a strap on dildo. It looked scary to me but Frieda and Jane thought it was a riot. At one point Olga came over to me and attempted to get me to suck it. “Suck it, Davia. Eat some dick!”

She was poking it at my mouth. I didn’t like it. Suddenly Frieda cracked me in the face with an extremely hard slap. It literally knocked me off the chair. Her face was livid. I was on the floor. “How dare you! How dare you embarrass me in front of my friends!”

Two more very hard slaps. I was crying. Olga and Jane was mesmerized. “Now suck that dick or you’re not going to leave here alive, you cunt!”

Olga walked up and shoved the dildo in my mouth and I sucked it as best I could. Her eyes bore right through me.

I glanced over at Frieda. She was still mad. My face burned from the slaps. I was crying and sucking. “Yeah. She’s sucks dick good. Werner will love her,” Olga said. She was running her beautiful hand thru my wet hair. Holding my ears. Pumping the plastic dick lewdly in and out of my mouth. “Suck it Slut Girl. Eat my dick!”

Olga soon tired of this and removed the dildo.

Then I got a shocker. Frieda was sitting in a straight backed chair. With her wooden paddle in her hand. Grabbing me roughly by the hair, she pulled me over her lap. She then proceeded to paddle the shit out of my poor beat up ass. It went on for a very long time. Screaming and wailing. Then I had corner time. As I walked on weak wobbly legs to a corner I noted Jane and Olga openly masturbating. They were loving this. I stood there naked and sobbing for about fifteen minutes.

I could hear them whispering and giggling about me. “Alright Slut Girl, round two.”

Back over Frieda’s lap. More whaling and screaming. I could hear myself bawling but it sounded like a different person. Hiccuping and screaming. Bawling like a baby. Then silence. Just me crying. Still on her lap. Deathly silence. “Okay Babygirl. It’s all over. Just relax. We’re gonna go home soon. Calm down Davia. You had a good spank and a good cry.”

It took the longest time to calm down. I was sure the other two women were still watching me being punished. “Sssh. It’s okay Baby. All over babygirl. Catch your breath. Momma’s got a present for a good girl.”

Finally after about another fifteen minutes of just attempting to regain my composure over Frieda’s lap, she had me stand up. Then she had me sit on her lap. What now? I looked around the room with hooded eyes and sure enough Olga and Jane were sitting nearby in chairs masturbating to everything. They looked enthralled by our little psychodrama. I’m sure Frieda felt like a great German film director.

“Okay. It’s all over precious. Now we’ve got a reward for our babygirl.”

She was starting to pull on my dick. I was hard in no time. Then she had the Jergan’s lotion in her hand. (Had she planned this all out, with the wooden paddle and the lotion?) Squirting it all over my dick and balls.

“Now let’s show Frieda’s friends what a good girl you are and what a big load you can shoot for Mommy? Have you got a big load for Mommy? Huh? Is Babygirl gonna shoot some cream and make Mommy proud of her?”

“Awwwhhhhhh!!”

Cumming and cumming and cumming. All over my stomach, dick, and Frieda’s pumping hand. It went on for a long, long time. I must have built up all this tension and now it was finally being released. “That’s my babygirl! Atta girl! Shoot that cream for Mommy!!”

I glanced over at the other women. Both looked like they were cumming.

When I woke up the next morning I couldn’t believe I had actually done that. What a strange day. My dick was rock hard. I didn’t have a job but I sure had a hard dick. I just couldn’t believe I let myself be punished in front of those women like that. But I did. And I was sure that I would jack off to the memory several times. A knock at the door.

I hopped out of bed. Opened the door. Frieda in a housecoat. She smiled and glanced at my hard dick in my pants. She touched it. “Good morning Davia. We’re having dinner tonight at 7. Don’t be late. Look sexy. I’ve got some good news.”

Then she swatted my hard on and left.

That night I wore the lacy black bra with the breast forms, my skirt, garters, seamed hose and the low heels. I looked quite sexy. Still not good enough to pass, but if you were horny…

Frieda let me wait on the back steps for a good period. But I really didn’t care who saw me. I looked sexy, felt sexy, and knew I would be having sex soon, what form that would take with Frieda I never knew.

She greeted me at the door with a kiss on my lips. Werner was just sitting down at the table. “Oh Werner, doesn’t Davia look lovely?”

“Yes. Very!”

“Thank you Werner.”

“Your welcome.”

“I’ve put your plate right next to mine, Davia. I want you right next to me tonight.”

“So what is the good news, Mommy?”

“Hush. I’ll tell you in a little while.”

She had fixed bratwurst and German potato salad. It was good, as usual.

“Look Werner. That’s what happens to bad girls.”

She passed him a Polaroid picture. I knew right away it was the one she took of my beat up ass during a beating. He seemed fascinated by it, glancing from the picture to me. Meanwhile Frieda was playing with my dick under my skirt. The dinner continued in this fashion. I got hard immediately. My dick trained to her touch.

I could see Werner touching his dick as he looked at us and then at the picture of my beat up ass. “Ohh Davia’s all excited tonight. I guess she liked getting her new clothes.”

“I love them Mommy. Thank you so much.”

“Your welcome darling. Davia, Werner has a present for you. Werner show Davia your present.”

He stands up and walks over to me. Undoes his belt, pants fall down. Boxer shorts. I can see he’s hard. It looks huge. He pulls down his shorts. A very big dick. Terrifying. ” Well?”

Frieda sounded like she was getting irritated. I just sat there, in a trance. Werner was slowly jacking his big penis in my face. I could smell his manly, musty odor. Then he placed the tip of it on my lips.

“Kiss it Davia. Don’t act stupid.”

I kissed it. “Uhhhh.”

Werner was very into it.

“Lick that big prick, you dirty whore!”

I followed her instructions. I loved her telling me what to do. “Don’t embarrass me you cunt.”

She was pulling my hair, hard, as I licked her husband’s massive prick. Werner was grunting and staring at me. “Suck that beautiful dick and give him a big cum. Or else I’ll whip the shit out of you right here and now. Do you understand me, young lady?”

His dick was in my mouth. Filling it. It was huge. I felt like I was sucking on a building.

Frieda was twisting my balls. It hurt! “Answer me young lady!”

I nodded my head and moaned yes, and kept sucking his dick. “Allllwwww fuuuuuukkkkKKKKKKKKKAAAAAAA ohhhh ” “That’s right, cunt. Swallow that cream. That’s good for you. Cocksucking whore!”

Then, to Werner, “I told you she was a natural, didn’t I? Look at that whore. She was born to it. This is christmas for her.”

Every word out of Frieda’s mouth just got me hotter. Werner had his hand on the back of my head. Suddenly he shot his load and my small mouth was full of jizz, his copious man cream. It was dribbling out of my whorey mouth.

“Oh fuffuuuk that was sooo goood. God what a cocksucker!!!”

Werner staggered back to his chair. “Clean him up, Davia. Finish him up. You want him to come back, don’t you?”

I knelt in front of Werner and licked him all over. He was petting my head like a puppy.

“Now what do you say, Davia?”

“Thank you Werner. Thank you for letting me suck your dick.”

“Good girl. I’m proud of you. Now take care of Mommy.”

I knelt down in front of her and ate her for the next half hour. Her cunt smelled so funky and powerful. It was intoxicating. At one point I could hear Werner jacking his dick. Ready to shoot again. Frieda came about ten times. I had the heel prints in my thighs to prove it. She loved to grind her heels into my legs as she orgasmed. After she was satisfied she slapped me in the face, hard. It hurt.

I glanced up at her. Frieda sat in her chair with a glazed look in her eyes. Sated. I just stayed kneeling in front of her. After she had regained her breath, “Okay Davia, show Werner what a big girl you are.”

I stood up and began jacking off in front of Werner but it only took a few minutes and I was shooting cum all over the place, in fact a lot of it got on Werner. He didn’t seem to mind.

The evening continued like that. We took a long break and had fresh drinks. Frieda had me take my skirt and blouse off. Now I was in black see thru panties, black bra with cool breast forms, garter belt, seamed nylons and low heels. I felt incredibly sexy. I realized I loved making these two cum and then cleaning them up. It brought out the woman in me.

Later on, Frieda told me her good news. She would be renting me out as a maid/cleaning woman to Olga and her friends. Apparently I had made a very good impression at the lingerie store. The only scary part was that they were also allowed to spank and beat me after I had cleaned up their homes.

Well at least I had a job.

 

by Brian Houlihan

4.5/5 - (18 votes)

2 thoughts on “The Boarder”

  1. How absolutely wonderful to be hired out by Mistress Frieda to her friends as a fully fledged feminised maid and to also have the delight of being punished by them as well

    Reply

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