tagTranssexuals & CrossdressersIt Started As A Golfing Debt Ch. 02

It Started As A Golfing Debt Ch. 02

byStryWrter7©

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 these chapters 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.

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


Chapter 5

Over the next two weeks Tom used my tongue as his hefty prick’s personal massage unit. Dee used my tongue several times – only experiencing the awesome orgasm once, the other times – she said I didn’t do well enough.

Tom and I played golf again each Saturday. Once I won 6 holes against him, and the next time I only won 1 hole. Losing 17 holes to him was bad, but he told me that if I lost all 18 holes – all hourly bets would be off and for 24 hours a day for two months I would become his slave. I thought things couldn’t be worse than being his and Dee’s maid (bitch) for 6 hours one week and 16 the next. At the golf game when I lost 17 holes, Tom taunted me though out the day. He told me things he was going to do – and it certainly affected my play. I missed putts I normally make. I hit shots into the woods and out of bounds on almost every hole. He got under my skin from the first hole. When we rode in the cart he would pinch my nipples or even worse – grab my crotch in between holes or when he was positive no one was watching. Knowing that he was doing it when no one was watching didn’t put me at ease. He owned me, and I felt inadequate in his presence.

Dee on the other hand was warm and inviting when Tom was not around. I was right about her. Once she had established her complete dominance of me, she eased up. I was not a threat to her. I had been emasculated and completely subdued by both her physical strength and her raw beauty. I helped clean their house, and yard. She wasn’t into sex as much as Tom, so I didn’t seem to be at her crotch all the time. Thankfully she preferred to be licked – and once I showed her how it feels to have peppermint Altoids in my mouth when I licked her – I became her favorite pet. She only took my ass two more times with the huge rubber dildo – and both times it was cause Tom asked her to. She was easier to get along with when Tom wasn’t there. He liked to instigate things – and make me suffer. Who knows, maybe now that there was another guy with a dick she could humiliate, maybe she left him alone without making him wear panties.

Speaking of panties – he only seemed to wear them 3 times in the last two weeks. Each of those times he was so humble – so very polite it was like he was another person. He was quiet, obeying her every command. When he wore panties to suit her – he never once tried to molest me. We weren’t equals – but he was a lot more bearable.

But it didn’t last.

I was at home and Karen came in from working out at the gym. She told me how a pretty young body builder lived next door and while at the gym she had been most helpful. She told me that Dee had taught her several new exercises to shape up her butt, and she told me that Dee had given her several massages while they both were in the sauna.

My face was white as a ghost. I wasn’t prepared for her to really meet the neighbors. Since Karen was busy all the time, I didn’t think they would find the same interests. I had done my best to not let Karen catch me going to their house all the time. I wanted to keep Tom and Dee away from my daughter.

Karen was 5’ 4” tall, 108 pounds, blonde hair (dyed) a very narrow waist and extremely large DD breasts. Since she grew up in my house and her mother had large breasts, I always assumed that since they didn’t happen overnight – they were indeed real. Karen had a typical dark tan – seems like most college students want that ‘healthy look’. Her hair was usually pulled back in a pony tail and she liked to wear a ball cap with it coming out the other end. She was a wet dream come true. She was a lot like her mom except with one thing: SEX. It seemed that she got her sex gene from me. She was willing to try anything once – and providing she wasn’t going to get hurt or leave permanent mark – she wanted to be an expert in the sex department.

Her mom (Debby) died 4 years ago – by a drunk driver at 6 am one Saturday morning. Debby wasn’t a prude when it came to sex – but she wasn’t into much. We did it missionary most of the time. She just wasn’t kinky. When I would suggest something kinky – Debby would think I was just being a typical male – wanting what I didn’t already have. She used to warn me occasionally that I should watch out for the kinky stuff I wanted because I might find out that I couldn’t get hard without it. When I suggested that she tie me to the bed and have her way with me – she just reminded me that she didn’t need to tie me up – I already did what she wanted in bed. She seemed pleased with sex with me. She didn’t want any new adventures. Now that she wasn’t around I could become as kinky as my hearts desire. The only trouble is – I missed her type of sex – where I am a MAN with her. Now with Tom and Dee – I am their slut, bitch, or maid; but certainly NOT a man.

Back to my daughter – I found out she was promiscuous when she was only a junior in high school. I tried to convince her to wait – but she told me that it was so difficult for kids her age to wait, especially when they looked like her. By the time she got to college, she was trying lots of things. The one thing she didn’t like trying was drugs and alcohol. She said it dulled her senses and she didn’t enjoy her orgasm as much that way. It was always strange to have my gorgeous daughter talk this way with me, but as she pointed out – she doesn’t have a Mom as a roll model or confidant.

“I think my body building friend Dee likes me. I think she is trying to come on to me, but just hasn’t gotten up the courage.” Karen startled me out of my train of thought.

“What makes you think that?” I quizzed her.

“Well, in the sauna when we were alone, she was giving me a massage and her fingers accidentally got too close to my sex. She pulled back when I propped myself up and looked at her. She then went for my boobs saying that she wished she had a set like mine, but that bodybuilding has kept them smaller than they might be if she quit. She was stroking my breast and my nipples got all hard with her touch.” Karen brazenly told me.

“Then what?” I asked.

“Then I told her no.” Karen stated.

I was relived hearing that – because now that Karen is legal she has been more prone to be open when it comes to sexual talk.

But Karen continued the story from the gym. “Dee looked depressed that I stopped her, so I calmly told her that maybe we can get together in a more private setting some other time.”

I cocked my head to one side showing unspoken thought ‘why?’

“Dad, it is not like I haven’t had sex with a woman before.” Karen plainly stated.

“But dear, I have met the neighbors, and they are in their late 20’s and you are barely 19.” I tried to reason with her.

“Dad, if it makes you uncomfortable to hear about my private life, I won’t tell you anything any more and just keep it private. But if you’re dating and you are in your 40’s – it’s not like there is a rule you can only experience life with someone within 3 years of your own age.” Karen smartly replied.

“I just turned 40, thank you.” I promptly corrected her. “But just how much do you know about this woman before letting her paw you?”

“Dad --- listen to me. She’s into bodybuilding. I like to be in as good shape as her. She is married and doesn’t have any kids. She told me that she has her husband and few friends wrapped around her little finger. She explained that it is what women who know their body do best.” Karen explained. “I told you we didn’t do anything. She didn’t go down on me, and I sure as heck haven’t gone down on her. I just think she wants me is all.”

“Ok dear, I won’t judge what you do – I think you make some excellent decisions in your life. We have an extremely uncharacteristic bond – you and I. Most fathers could not handle their teenage daughters telling them sexual things they do with other partners.” I backed down.

“Mom told me when I was just 14, and beginning to attract boys by the handful – not to make a mistake of never trying sex before marriage. She told me not to be a slut, but not to be afraid to try sex when my heart and mind tell me it is OK. She didn’t want me to settle for the nice boy down the street and then not know how to satisfy him – and keep him in line. She said she didn’t want me to have a partner who’s not good in bed.”

“I didn’t know that – You mean she didn’t think I was good in bed?” I questioned my daughter about my wife.

“No, Dad. She told me you were perfect for her. I just think she wouldn’t want me to end up with a guy whose dick didn’t satisfy me.” Karen explained.

I cringed.

“Bigger is not everything.” I tried to rationalize with her.

“The only people that try to perpetuate that lie are guys who are not adequate. This is not so – Dad. Bigger is better. Especially if they know how to use it.” Karen admitted.

I wanted to end the conversation.

“Dad, you and Mom wanted the best for me. Girl – Guy it doesn’t matter as long as I am happy right?” Karen asked me

“Of course dear.” I declared.

“Well, you wouldn’t want me to do a guy with a tiny – or insignificant body part, when it is so important to a woman.” Karen clarified her perception of the right guy for her.

“No dear. I guess that wouldn’t be right for you.” I stammered an answer.

“Good, I am so glad we cleared that subject up.” Karen flatly stated.

Chapter 6 Serving a dinner party

On Friday that next weekend, Tom and Dee instructed me to be at their house. I was to be their maid. I didn’t know that they planned on having company.

Dee and Tom got me into the maid uniform and then added a leather hood to my face. It was snug over the back of my head and only had openings for my eyes, nose and mouth. The opening for my mouth was short lived since they stuffed a ball gag into my mouth and buckled the leather straps behind my head. I was told that I wouldn’t need my mouth at this time – I was going to be a maid and serve them and their guest dinner. I was not to do anything without their permission, nor was I to make too much noise while I was gagged.

I felt silly but looked absolutely worse. I heard the doorbell ring – Dee answered it and invited their guest inside. I stayed in the kitchen until instructed to bring out the food. The minutes ticked by and I was frightened. No one had seen me as his or her maid before, so this was going to be a new experience. I could only remember the instructions that Dee had given me – with the leather hood and female maid uniform, no one will know who is their slave – that is unless I do something stupid. Then all bets are off.

After awhile they settled into their spots at the dining room table and I was called to bring out the salad.

I entered carrying a tray and nearly dropped it when I saw who was their guest. KAREN!

She nearly choked on her drink when she saw me. I thought that for sure Karen recognized me.

Dee spoke first. “This is our maid. We took the liberty of putting a hood over her face so she would perform her duties without any distraction or embarrassment. We have her services every so often, but this is the very first time she has exposed her true nature to someone of such beauty.”

I wanted to stop them from inviting my daughter into their web, but I was deathly afraid that when Karen learned that it was her father who was behind the mask in the maid outfit – that she would lose all respect for me entirely. Being gagged came in handy cause I wanted to scream out and make her run away.

“You told me that if I joined you and Tom for dinner – that I would experience something new. I had no idea that y’all were into something so kinky.” Karen politely stated. “I must warn you that I don’t believe in bondage or S&M until I am much more comfortable with my hosts. I hope you didn’t think I would participate in this game.”

Dee comforted Karen by explaining “Don’t be afraid of our maid. She is trained to obey both Tom and I – and will not be participating in anything we have planned tonight. That is unless you want her to.”

“I like trying new things. It is just that this bizarre attire caught me off guard.” Karen told her hosts. “What is she called?”

“If you named her - What would you call her?” Tom asked.

“Slave, Servant, or Maid – I guess” Karen suggested.

“Those names are good – but we tend to call HER – Bitch, Slut, or Pussy” Tom proudly replied.

I didn’t miss the fact that they were calling me a ‘HER’ and not exposing my true sex to my daughter.

I was instructed to bring out the main course, and when I returned I heard Karen answering a question that one of them must have asked. Even though I didn’t hear the question, the answer she was in the middle of giving left no doubt its nature.

“… There were 3 guys and another girl – we played a game of trivia and the winner got to choose something for the losers to do. We had just finished dinner at my friends’ apartment, and were about to have desert. There was one question that I got wrong, and up to that point I had been pretty good at this game. Mark, one of the guys present, said that I should strip off my top, another told me to strip off my bottom the third guy wanted me to spread myself out on the dining room table. I did. Then Pam walked back into the room with ice cream and chocolate syrup and said that I was going to be the plate for desert and they all were going to eat off me. Ice cream melted and the chocolate syrup was everywhere while 4 tongues licked me. I but it was by far the most original and kinky thing I have done with more than one person at a time.”

Tom assured her – “Someday you will look back on tonight and say it was the most original and kinky time you have had with more than one person”

A discerning smile spread across Dee’s face.

The dinner went without any problems, and Karen didn’t realize I was in the room with her. I was ready to die – I was so frightened. At one point during dinner I spilled a few drops of water when I was filling Dee’s glass. It really wasn’t anything to be concerned about, but Dee made sure that Karen got the full treatment.

“Pussy, can’t you do anything right – you spilled some water. What do you have to say for yourself?” Dee taunted me.

I could not answer. My eyes got as big as saucers. Up to this point I had not raised my eye lids very much for fear that Karen would see behind the mask and know it was me.

“Bend over!” Dee commanded.

When I did – she swatted my behind once.

“Go to Tom and bend over so he can punish you too – and then do the same to our guest. We wouldn’t want her to be left out of the fun.”

I went around the table and bent over next to Tom. Swat. He smacked my panty-covered ass.

The hard part was stepping over to my daughter and bending over for her to hit me.

“Spilling your host’s water is a serious offense. Do you really think one smack should be sufficient?” Karen slyly suggested.

“Why no, my dear guest … one from each of us is not enough. How many do you suppose we should administer?” Dee beamed.

“Twenty would be suitable.” Karen proudly announced.

“Twenty for spilling a few drops of water?” Dee raised her eyebrows at the aggressive nature their sexy young guest was exhibiting.

“My father raised me right. If he were here he would tell your slut that she would remember it more if she gets 20 swats. She won’t forget to mind her manors.” Karen arrogantly exclaimed.

Tom nearly choked at Karen’s words and it looked to me like Dee was kicking him under the table. I recognized what my daughter was doing. She knew her hosts were into a bit of S & M and she wanted to establish herself on the giving rather than receiving end.

I bent over next to her chair and she swatted my behind 10 or 15 times before she ‘accidentally’ got one of her smacks to my butt a bit too high between my legs. I wiggled a bit to keep myself from being smacked again – close to my balls.

“What the hell?” Karen was dumfounded. She reached between my legs and gripped my panty-trapped manhood and nuts. Her bewilderment was short lived when she squeezed my nuts in her hand.

I yelped in surprise and fear, but nothing came out of the gag other than a grunt.

“Your Pussy maid is nothing but a sick drag queen.” Karen was overwhelmed by this erotic turn of events.

I could feel her fingers squeezing my poor nuts and the pain from her delicate hand was nothing compared to the shame I had behind that mask. My daughter is revolted by my appearance as our neighbors’ maid. Yet she hasn’t even discovered that I was in this taffeta maid uniform. She re-composed herself enough to respond “I think the remaining part of the spanking ought to be done on a bare ass, so I know what I am hitting.”

“Why – how delightful.” Dee gladly spoke up.

Karen yanked my satin panties down my legs till they bunched at my ankles. “Step out of them and spread your legs wide… then bend over!” she commanded.

I tried my best to obey. Tears were soaking inside my hood. My hands were shaking as I complied with her instruction.

My own daughter Karen was administering a spanking on my bare behind. When she finished swatting my butt she took her finger and flicked my ball sack sending a jolt of pain. Lucky for me Dee had shaved my balls, chest and legs only a few days earlier saying that her maid looked ridiculous with hair there. If it weren’t for my mask and the less obvious differences Karen might have recognized me as her loving father.

The worst part about the night so far was Karen’s next rude but deadly accurate comment. “I guess we should put back on your panties now – I seriously doubt anyone will want to use such a tiny dick for their pleasure tonight.”

OUCH!

That stung worse than the spanking or the flick to my unprotected balls! I acknowledged I was not hung very well. Tom found my weakness and has exploited it to his best advantage for several weeks. With Tom & Dee’s persistence I had admitted how inferior I was to them and that I somehow deserved their relentless manipulation. Debby loved me, and never made me feel any less than a perfect man. However, since my wife’s untimely death, the women I dated never seemed genuinely satisfied in sexual intercourse with me. Each time that Tom smacks my face with his bloated flesh, or makes me beg for his large and potent dick – I sink deeper into self-realization that I am less than adequate.

Pulling up my panties, and slinking out of the room – I went off to the kitchen to clean up.

After eating, everyone adjourned to the family room and Tom had asked Karen to stand on the coffee table. I was called into the room.

“I want our she-male maid to undress you – and you can be desert for us.” Dee told Karen. “Slut, you are to undress our very sexy & delicious desert – but don’t let your hands wander into her private parts. I know how much you want to. But they are for the Master and Mistress of the house.”

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