tagTranssexuals & CrossdressersIt Started As A Golfing Debt Ch. 05

It Started As A Golfing Debt Ch. 05


This is written by me, and can be reproduced for your enjoyment, however not if it is reproduced on an Internet pay site, without compensation for me --- the writer.


This story is fiction. It is meant to be read by adults. Children under the age of 18, please leave. All the characters in this story are of my own imagination, and not real in any sense of the word. Any similarities to that of living people is pure coincidence. This story involves a man & his new neighbors who win a bet while golfing and soon his life is turned upside down. It contains scenes of sexual relief for the neighbors and frustration for the storyteller ‘Chris’. There is some domination involved as well as a bit of wrestling. In chapter 5 & 6 his sexy 19-year-old daughter joins the fun. Comments are always appreciated, but please limit those to ideas & not to just give grief. Sorry for the delay in the story -- there have been many people who enjoyed it and wanted an ending.

And now --- on with the story. I hope you will enjoy.

Chapter 9 Unexpected visitor gets a wild welcome.

Over the next several days I became increasingly more submissive to Karen and she began to seize more control of my life, home, and body. She convinced me that since I had $875,000.00 in securities and 401K accounts that I didn’t need that much money to survive. I was ‘talked’ into giving her an immediate quarter million dollars. She had me bound and stretched out – while she hit me - alternating between a fraternity paddle and riding crop. I surrendered the money to her. My home – well, Dee had convinced Karen to get me to sign over the deed. I haven’t been broken down enough for that to happen yet. Of course, there is always my body. She has had some enjoyment in butt fucking me with a strap on. She got off making me sit down on an enormous greased butt plug. And she has kept me in female clothes for the week.

Karen isn’t acting cruel – she is just doing whatever it takes to get her way. She reminds me how much I ENJOY being submissive --- and how much I LOVE to be her sex slave, and our neighbors Slut. I must admit to myself that her pussy is by far a lot tastier than Dee’s. I haven’t made a fuss over her order to serve in this capacity, but

Karen and Dee had gotten me a few push up bras, half dozen panties of different colors, including one that was crotchless which alloyed my balls and dick the freedom to dangle in a crude way. They had painted my fingernails, and toenails. They pierced my ears, and my nipples. In an extremely short period of time I was reduced to a joke. I didn’t really look good as a woman – not even when they put a wig on me. I couldn’t walk in high heels, and my mannerisms were forced at best and pure male at worst. But I overheard Dee tell Karen several times – I should be punished to keep me off guard. I should be dressed in feminine attire or naked to become more malleable and controlled by my now wiser 19-year-old daughter.

My erection was nearly non-stop as she used her new power to control my ejaculation. I was bound in the new ‘cage bed’ and frequently teased till I couldn’t stand anymore.

But the strangest thing happened the other day. I was inside the house, wearing all sorts of female clothes. I was vacuuming, and cleaning. I had on a white push up bra, and red satin panties. My whole body had been shaved the night before – and Karen had applied some cream that was supposed to help – but it seemed to make me itch even more. I was upstairs when I heard something downstairs emanating from the kitchen or family room. To be more precise, it was SOMEONE in our house. Not Tom, or Dee and certainly not Karen.

“Karen?” The caller yelled into the house. “The door was standing open --- anyone home?”

Oh my – I forgot that I had been out on the patio, and then come in through the garage. I must have left the door open. I was ridiculously dressed and couldn’t dare show my face.

I went to the stairs and heard a slightly familiar voice – Sara; one of Karen’s friends was in our house.

“Karen? Chris? Where are you guys?” She called out. “Is anyone upstairs?”

She was just at the edge of the steps – I don’t think she saw me scurry off to my unusual bedroom.

I heard her walking up the stairs.

I couldn’t think of what to do – so I hid in the closet – and slightly closed the two doors to keep me from being spotted, yet still allowed me to see most of the room.

Sara had apparently wandered into my old bedroom – the Master Suite that now belonged to the new boss of the family – Karen. I heard her exclaim “WOW!”

She must have liked the changes that Karen had made this last week. Lots of furry blankets and pillows across the bed. Safari Designs of Africa – the Sears store look that was quite popular.

A few moments later she entered my bedroom. “What the HELL Happened here?” She mumbled out loud. “PINK WALLS? What in the hell is this?” Sara walked over to the caged bed. “What is Karen up to?”

Sara looked around the room – not paying much attention to the closet or me hiding. She examined the bolts that screwed into the wood. She saw the cuffs that were tied to those bolts. She found the huge dildo that was in my ass the other night. (Thank god I cleaned it) She found one of the better (and bigger) vibrators that Karen has used to make me squirt. This was an erotic dream come true for a submissive person or a dominant ruler. Anyone in between these two extremes would not have been the least bit comfortable in this room.

Sara looked comfortable. In fact she looked around to see that no one was watching, and flicked on the vibrator – and brought it to her left breast followed by her right breast. I could see her nipples poking through her light bra and T-shirt.

Perhaps I should describe what was in front of me. Sara is Karen’s age at 19, but she doesn’t look as athletic as Karen. She has a fuller body - very large tits, and a bubble butt – that I always found attractive. As a real fair skinned strawberry blonde, she never took to getting too tan, and this summer wasn’t any different. I remember she use to tease – ‘that if she tans, her freckles just run together’. Her hair had gotten longer since the last time I saw her. Now it was to the middle of her back. And for the first time, I saw a tattoo on the base of her back and another around her ankle. As I watched her become fascinated by the toys lying around the room I realized she had moved the vibrator to her crotch. She was buzzing the damn thing through her shorts.

Damn, I had an excellent view. I could see her whole backside and butt as she sort of swayed to some imaginary music while she rubbed the buzzing vibrator against her crotch. The full sized mirrors we had recently put into Karen’s bedroom gave me ample view of her front side too. Sara then saw another toy inside the cage on the bed. She went into the cage and checked it out. She still held the vibrator in her hand but she looked at a double plug that I know Karen had used the other night. Now lying back on the bed Sara must have wondered about the various sets of restraints all around the cage area. Some were attached to the side others to the headboard area while still a few dangled down from the roof of the cage. I watched quietly as she slid her hand into the one of the manacles hanging from the roof. She closed the Velcro band around her wrist and then yanked downward to see how much strength it withstood – testing if it would hold her.

Then as if this was a dream Sara unbuckled her shorts and spread them out of the way while she used her free arm to hold the vibrator against her sex. The girl must have been imagining what it must be like to be bound and brought to orgasm. From my vantage-point I couldn’t see her as well as before, so I let the closet door slide open just a fraction of an inch more. The first thing I noticed was the pointy eraser tips of her nipples. Sara was very excited. I realized she was slowly closing her eyes – and thrusting her crotch outward to meet the buzzing toy.

Just then – before she could cum, I heard a CLICK. Sara heard it too, for she opened her eyes wide in fear and bolted upright in the bed. She dropped the vibrator and was trying to get her shorts closed but was restricted to only one hand – and there was NO WAY those tight shorts were going to get buttoned and zipped up with only one hand. Out of my line of sight was something that made Sara afraid. I could sense the fear in her. She stammered out “I looked for you – um, the outside door was open. I called and no one answered. Then I saw what you had done to your room – and sort of --- well, got carried away.”

My god – Karen must be in the room. But she didn’t say anything back to her friend.

Sara getting more embarrassed shouted out “Say something. What is all this? Are you turning into a pervert? What’s the idea of this stuff – if it’s not to be fucked with?”

Karen entered my line of sight --- “Looks like we were playing with the toys huh?” She teased her friend. “Go ahead and finish what you started”

I watched Karen come into my line of sight. Her hair was up in a bun, her tight halter shirt – didn’t halt very much, and her red shorts didn’t cover more than two inches beyond her crotch. Karen was tapping her sandal covered feet – waiting for her friend to finish playing with herself.

“Get me out of here!” Sara complained to Karen. “While you are getting me out – why don’t you begin telling me what you are doing with all this stuff.”

Then Karen told Sara “I’ll let you out. And I will tell you all about what is going on this summer. But first, you have to do two things for me.” She paused for an acknowledgement.

“What?” Sara curiously asked.

“Strip naked, giving me your clothes, and then make yourself cum with the big tan vibrator over there” Karen smirked pointing at the monster 14 inch industrial sized vibrator lying on the bed.

“You’re joking – right?” Sara nervously asked.

“NO. Its not like I haven’t seen you naked – and its’ not like you haven’t seen me naked. But I have always wanted to watch you have an orgasm – especially after how much you used to talk about it in high school.” Karen explained to her trapped victim. “By the way – you haven’t seen my dad – anywhere – have you?”

“Chris?” Sara asked. “Does he know what you have done to your bedroom?”

“Sure – he and our neighbor Tom helped build it.” Karen smartly replied. “He didn’t put you in here did he?”

“NO” Sara indignantly shot back. “Chris has ALWAYS been a gentleman around me – I can’t imagine him being part of something so obviously naughty as this.”

“C’mon, start stripping and I’ll fill you in.” Karen laughed at her own pun.

“You always liked to boss me around --- just wait – one day I might have some pretty good influence on this family – and Chris may just lock you in here and throw away the key.” Sara tried to intimidate her friend.

“Ahhh, right – You and my Dad – that’ll be the day” Karen smarted off.

“Don’t laugh – one day I might be your step-mom!” Sara shot back. “Then I’ll be the one bossing you around!” Sara had gotten her hand free from the cuff and now was standing by the cage opening --- pushing and pulling on the wood realizing it wasn’t going to fall apart.

“Oh my gosh, Sara, I forgot all about how much you had a crush on my Dad. That’s right – I remember you spending the night when we were 8 years – no, 9 years old. You told me that you thought I had the very best dad in the world. He was sexy, and made you quiver when he looked your way. Then I remember after my mom’s funeral how you came over here to visit me – always wearing something short and sexy to attract his attention. And your big ol’ boobs – you used to laugh when your big nipples would get hard and poke through your bathing suit or tee-shirt any time he was around.” Karen reminisced. “Just like they are doing right now!” Karen teased her friend, “Do you still dream of getting him in the sack? I’ll bet I am right - your nipples still harden when he walks into the room?”

I could see Sara’s shirt – her nipples were indeed hard. They were little nuggets poking through her shirt.

“Go ahead and strip – the sooner you are naked the sooner I can get you out of there.” Karen toyed with her friend – knowing that she had the upper hand.

Sara looked around – then yanked off her top revealing a lacy black bra that barely concealed her full globes. She had quite a bit of cleavage with those large breasts; it looked sexy against her flat stomach. It was quite a turn on for me standing in the closet watching her obey Karen. Sara reached behind her to unsnap the black bra, letting it fall to the floor in one quick movement.

“You always did have nice boobs.” Karen complimented her friend – no doubt licking her lips like was seeing her milk filled tits. “Great big areola with huge nipples – just the way I like women!” Karen laughingly teased Sara.

“I don’t feel like taking off my panties right now” Sara pleaded

“Why not – afraid to show me how wet you are?” Karen quizzed “Guess since you didn’t quite cum when I entered the room – I am sure that you at least got the juices flowing.”

“You promised to tell me what is going on --- you start talking & I’ll finish stripping.” Sara negotiated with Karen.

“Okay, since you asked. Our neighbors are quite the erotic types. Tom is hung like a horse, and Dee is a bodybuilder who can offer fabulous sex. Tom helped Chris to build this little cage – plus make a few other changes here. The cage you are in – wasn’t meant for a real woman like yourself – but it is being used by a cross dressed man who wants to be a woman. Dee is into domination. She is helping me get some things that I always wanted. Namely: Sex, money, & power - all the evils in our world.” Karen started explaining. “Now Tom’s dick is so big and thick it not only has me all hot and bothered – but it has my Dad on his hands and knees begging to suck it.”

“That is so perverted!” Sara disagreed. “You are just saying that to make fun of me. Chris is NOT gay!”

“I never said he was. This isn’t about you at all – unless you want it to be? This cage is for him. This pink room is for him. He’s become a bitch in heat. He dresses as a woman. He sucks cock like a woman. He’s even submissive like most women. I don’t particularly like that trait in my men – so I have taken over the family – his money – this house, and even his puny cock. I say when he can cum.”

Sara stared in shock.

“You haven’t seen Chris yet – have you?” Karen asked.

Sara shook her head no.

Karen left the room without saying where she was going.

Sara yelled out “Hey – Wait – I – Um – You aren’t going to leave me here are you?”

Karen didn’t answer.

Sara grabbed the biggest dildo to extend her reach in a futile attempt to get her bra that she had inadvertently kicked out of the cell when she was stripping for Karen. I meanwhile got a really good look at her boobs as they hung nearly down to the ground as Sara bent over. Karen has nice big tits – it has always been her best attribute – but Sara had those tits beat by a landslide.

I quietly tried to unfasten the push up bra I had been forced to wear today. I slipped the straps off my shoulders and inhaled slightly as the confining garment had been successfully removed from my chest. I then decided that I must get out of the red panties. This way if I sneak out of the closet and get caught by Karen or her friend Sara - I won’t have the additional embarrassment of being in female panties & bra. I figured no one would notice my toes that were painted the same color as the panties. I got the panties down to my knees and was bending over to pull them the rest of the way down when I heard Karen come back into the room.

Sara said, “What kind of costume is that suppose to be?”

As I tried to look between the crack of the closet door I lost my balance and banged my head against some empty hangers. Cling!

Hearing me, Karen quickly yanked open the closet door.

I was naked – and tripping over the panties that were around my ankles.

My attire & lack of it astonished Sara too.

“What do you think you are doing in there?” Karen scolded me. “Get out of the closet at once!”

I meekly obeyed my daughter – not because I had been trained to do it yet. But rather because she had an air of authority in her eyes, and her posture as she stood in black leather skirt, a tight white top that molded to her full breasts and in right-gloved hand – she had a riding crop.

Karen berated me with her questions. “What have you been doing hiding in that closet? Were you trying to seduce my friend?” Then looking over her shoulder at Sara who was staring wide eyed at the weird scene in front of her “Was this your idea? Did I catch you before you could fuck him?”

Before I could answer – Sara said “I didn’t do anything with him.”

Karen continued to reprimand me like an inferior little boy who got caught displeasing an instructor. With each direction from her – I made the appropriate and obedient action to please her. “Remove your hands from your crotch. Get down on the floor - like you are suppose to. No one said you could stand in my presence. No – spread your legs wide -- Knees wide apart – head down.” She barked at me, snapping the crop on my naked flesh for both quicker response as well as authority demanding.

So there I was naked – kneeling at my daughter’s feet bowing my head and mumbling “Yes Ma’am” to all of her directions. Sara couldn’t see my painted toes – I was kneeling on them. She also didn’t realize quite how small my dick is because it was fairly bloated watching her strip and Karen command. It wasn’t quite a hard on – but it wasn’t its usual small self either. Although I was on my knees like a trained animal doing whatever Karen ordered me – I didn’t feel quite so feeble in front of Sara. After all, I just found out that Karen’s friend: Sara had a crush on me. I didn’t want to look totally like a cross-dressed fool in front of her. At least not yet!

Karen wasn’t going to let me keep any dignity. “What is your new name?”

“Slut – Bitch – or little boy – depending on who is addressing me.” I meekly answered.

“What is your new roll in this house?” Karen asked.

“To obey you. Obey Tom. Submit to Dee whenever she demands it.” I humbly replied.

Just then Dee and Tom entered the bedroom. I blurted out – “You called them again?”

“Yes – I called them. I didn’t know where the fuck you were. I wondered if they came and got you. I sure didn’t give you permission to leave.” Then with a very evil smile spreading across her angelic face Karen said, “Besides, another toy has entered our new cage. We must all enjoy her.”


Dee and Tom were introduced to Sara who by this time was only wearing her panties. Sara meanwhile wondered where all this would lead – would she get fucked? Would she enjoy herself? Would she get her clothes back and be released from the cage? Tom was instructed to cuff my wrists to the bar that was hanging from the roof of the cage. Karen unlocked the cage while Sara made no attempt to exit and Tom roughly persuaded me onto the bed in a kneeling position. From there, my wrists were gathered behind my back as the Velcro cuffs were wrapped around them. Each cuff was attached to opposite ends of a broomstick handle. It is amazing what you can do with a few simple household items. Rope had been connected to the center of the broom handle by a hole that we drilled, while the other end went through a pulley that was bolted to the roof of the cage. Then the entire wooden handle was lifted up toward the ceiling causing me to bend over and my outstretched arms to be lifted up. I found myself with my face directly at Tom’s crotch as he was standing on the bed adjusting the height of the broomstick. Tom took a perverse delight in pointing out were my mouth was.

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