tagTranssexuals & CrossdressersIt Started As A Golfing Debt

It Started As A Golfing Debt


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 story teller ‘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. At this moment, the story has 4 chapters and is not complete, so asking how it will end – well, we will just have to wait & see.

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


After being at the pool for an hour, I was contemplating my departure when the chairs just in front of me were claimed by a woman and man I had never seen in our neighborhood. While I was still a bit pale and I wanted to work on my tan during this June afternoon swim; the new couple settling in next to me were both tanned golden brown - the woman was just rippling with muscles. I tried not to stare but I kept my eyes on them as they stripped down to their bathing suits. The woman was most intriguing since she had muscles in places where most women had overgrown baby fat. Her arms were impressive as she whipped off the cover-up top exposing a washboard set of abs, and C cup breasts. Her brown hair cascaded to the middle of her back until she wrapped the strands in a ponytail and then clipped it up onto her head exposing her well-developed shoulder muscles. As she held her hair up – I got a nice profile shot of her breasts – including a glimpse of the large areola and pointed nipple that was peeking outside the edge of her royal blue bikini. I couldn’t tell what to focus on: her amazing body – her fabulous firm flesh surrounding most of her body or the typical female attraction spots I lean toward when I view a pretty woman -- namely her tits and ass.

Her better half who I heard her call ‘Tom’ appeared to be a bit shorter than myself at only 6 foot, was in good physical shape but not a muscle bound man that I would associate being with this awesome woman. His bare but very tan chest showed that he exercised, but not to the extent that she did. He seemed to feel all the eyes watching them as they both settled into the chairs. Mine must not have been the only ones – he glanced around – then smiled to me and politely introduced himself.

“Hi, I’m Tom – we moved in a few weeks ago – but have been getting set up in our home – we haven’t had time to make it up to the pool. Good thing these chairs were empty – I would hate to come here and not have a place to sit.”

“Hi, I’m Chris. It gets crowded in June – but slacks off in July & August.” I informed him.

We chatted for the next hour or two while I took the liberty to stare at his wife. He told me her name is Dee, and she hardly even looked at me. She just drifted off to sleep. Her legs spread two inches open and I could clearly view her pussy lips under her bikini bottom. The way she had scooted down in the reclining chair forced the fabric into her pussy crack. The outline of her lips and escalating wetness evidently meant she was having a delightful dream.

After I learned that they are not just new neighbors, but they are my direct next door neighbors, I wanted to get more acquainted - Tom and I set up a golf date for the next Saturday morning.


On Saturday morning while loading his golf clubs in my car, Dee came out to greet me – or rather to give Tom hell for going out when she was going to be working around their new home.

“If you go – you won’t get any pussy tonight” she threatened him.

I wasn’t sure how their arrangement was – so I tried to just politely smile and keep my opinions to myself.

“How long are you two going to be gone?” she asked

“Five maybe 6 hours” Tom replied.

‘Six hours of playtime with your new friend. What do I get out of this?” She complained.

“You get peace and quiet till the late afternoon.” He tried to appease her.

“I can have peace and quite by gagging you – and still having you here to do your chores.” She threatened him.

He just sort of cringed when she mentioned gagging him.

I wondered if she was for real. I had visions of her being the boss of the house. I had mixed emotions about her I knew why I was attracted to her sexy hard body but another part of me wanted to stand up to her bossy attitude. Tom should put her in her place. What I didn’t realize at that time is that she knew her place. And she knew where her husband belonged.

She wasn’t making any headway with him so she started berating me. “I assume you two are going to be gambling while playing with each other?”

I chose not smart off and rebuke her term ‘play with one another’ instead I looked at him and shrug my shoulders and said “Yes.”

I check with his handicap, and he says 15 (I’m a 32)

Then she wants a bet too – but WITHOUT any handicap “I like to bet the same way I like my men – straight up. The bet is each hole he beats me – I have to help him one hour with his chores.” She informs me.

Although I think she is just kidding, I accept the bet.

She announces that she is letting him spend time with me – and taking time away from being spent with her – that I owe her if I lose.

We drive off - I politely ask Tom if she is always that fussy.

Tom answers that “She is Bossy, Dominant, and Bitchy but I wouldn’t call her f u s s y. But she is really into sex and I love how she can make me feel.”

Being a widow, I feel a little envious.

He goes on to say that although he’s dominant with others – he’s very docile (Tame) with her.

We let the subject of Dee disappear as we play golf where I proceed to lose 14 of 18 holes straight up.

After having a few beers in the clubhouse, he calls her to say we’re on the way home. I hear him say that he won $5.00 from me playing with handicap, but won 14 holes straight up for her. She tells him that he will get sex after all. He hands the phone to me – and she says she will start to get things ready for my servitude.

When I ask him what this servitude is all about - he merely shrugs his shoulders and says, “You lost -- Fair and square. I guess you’ll just have to pay up and help me with whatever chores she has.” Then he laughs – “Besides, she said I get sex for beating you. If you act like a good boy – maybe you’ll get real lucky too.”


When we arrive back at his home, I ask to use the bathroom and she directs me toward their master bath. Walking beside me in the hallway, she tells me to strip, shower, and then put on the panties laid out on the bed.

Entering their bedroom, I see a light pink lace set of panties on the bed.

“You’ve got to be kidding ---- Right?” I asked with a raised eyebrow.

“Nope. You wear panties to work around the house.” Dee folded her arms under her C cup breasts just daring me to challenge her authority.

She informs me that I kept her hubby away from her for 6 hours while we played golf. She says she has me for 14 hours – but most likely we can split it up into 2 groups of seven hours each.

I exclaim “I won 4 holes – shouldn’t that deduct from the 14 Tom won?”

When I convince her that it should be 10 hours of service, she agrees. Now I just have to convince her that the panties are a bad idea. She now stood firm with her hands on her hips and a determined look on her face. Her tan skin was remarkable against the black sports bra and short red silk shorts she wore. Her hair was pulled back in a ponytail but the look on her face was pure determination. She won. It was a bet. They are new to the neighborhood, but they would quickly decide who was going to associate with them – and who was not. She also said that word would get around that I Welsh (Cheat) on my bets.

“You can’t be serious about the panties. I am not a wimp who you can put into your panties. This is a joke right? OKAY ----- I’ll help Tom with his chores, but you don’t expect to make him wear panties – do you?” I complained

As they both stood between me, and escape through the bedroom door. “What? You think only wimpy guys would stoop to wear panties? Real men don’t wear panties or female clothes when a woman tells them to? You don’t think I keep my man in panties?” She moved intimidatingly close to me and pointed to her side. “Tom step closer and drop your shorts.” When he did, I was shocked to see him wearing a pair of white satin panties. His cock lounging to one side as it filled the material in the front.

Dee gently guides my hand to Tom’s thick member inside the panties. “Is this the cock of a wimpy guy? Does the fact that he’s wearing panties under my direction make him any less of a man?”

I am impressed by the girth that I can feel behind the slick fabric, but still bewildered about their relationship. It obviously shows on my face, and Dee calmly explains that he doesn’t wear the pants in the family. He wears the panties. “Did you think he was any less of a man when you were out playing golf with him?”

“NO.” I answered. I didn’t pull my hand away from his crotch. I was just in awe of what was happening around me.

Still using my hand to stroke his penis she pointed out “He’s quite impressive for a man – even if I keep him in panties.”

I agreed. The blush on my face showed my embarrassment. I looked up at Tom to see him nodding his approval.

“OKAY. I’ll get a shower, but can’t I wear something more than just panties?”

She agrees and says by the time I come out of the shower she’ll have something more for me to put on. Then gestured toward the bathroom. I knew she wanted me to obey her.

In the shower I was awash with thoughts – I had been a widow for 4 years. In that time I had dated women off and on – with a few of the more exciting women being a bit on the aggressive side – but nothing compared to her. I barely knew her. It was Tom I had talked with at the pool - Dee ignored me completely. I had played golf with Tom – and he had told me that she was domineering and bitchy. Still she was one fine looking woman – bitchy or not.


Chapter 2 My Big Mouth

Me and my big mouth – I wanted more clothes - I ended up with a black and white maid outfit of frilly construction. It was made of cotton and taffeta and it actually fit in a perverted way. It had some push up kind of bra that squeezed my chest just under my arm to appear as girls’ cleavage. The flared skirt came 2 inches past the top of my legs, barely concealing my crotch. I looked ridiculous in this outfit – and I felt inferior. The smirks on my new neighbors’ faces proved that I had capitulated to their whim and forever would be trapped in their little game.

We were both ordered to clean the bathroom I just had used. Since I was the last to use the tub, I was nominated to clean it. Tom was busy doing the sink and mirror. Dee would check on our progress and correct the way I was cleaning. Instead of telling me how she wanted it done – she kept telling Tom to show me. If being in this getup wasn’t bad enough – being referred to like you’re an object not a human was worse.

“Slave, show our new maid how to properly clean the tub.” Dee ordered Tom.

Tom stepped into the tub and told me to climb in so I can reach the wall and use more elbow grease to clean the corners.

I started to display my method and he told me to kneel down and clean the corner (which is where I was working before – only I was outside the tub leaning over to reach the corner). I sank to my knees in the cold wet tub and began to rub the wall with my sponge, when Tom straddled my knees and showed me how Dee wanted her tub cleaned. He stood and started rubbing the same corner I was working on – except when I looked up at him – I had a close up view of his panty-covered crotch. I tried not to gawk so much but I felt a thrill since it didn’t seem like an obvious attempt to trap my body below his.

I went on and finished the tub. He did the toilet and we were done in the bathroom.

Dee called us and told us she wanted the kitchen floor cleaned.

Handing me a bucket and scrub brush Dee told Tom “Have our new maid scrub the floor while you mop it up” and proceeded to hand him the mop.

Again I was on my knees while Tom and Dee were standing. And again, she didn’t address me – she went through Tom. Something erotic about being used this way but I couldn’t put my finger on it. As long as she was treating him as a slave, I felt like we were in the same boat. But I got the distinct feeling that her slave was a step or two ABOVE my position as a Maid.

Dee was in the next room working out with her free weights; I couldn’t help admire her impressive bulging biceps even from this distance. When I thought she was out of earshot - I made the mistake of sarcastically commenting to Tom “Gee with muscles like hers, you would think SHE would be the one on the floor scrubbing away. She could get a workout and be productive while we sit and watch TV drinking a beer.”

Tom started to laugh – not just a quiet – private snicker; but a gut wrenching laugh. He was about to agree when he looked rather nervous – almost petrified. He gave me a slight wave of his hand to get me to shut up but I was oblivious to his gesture. I continued to mock Dee. “I thought you said you were going to get some sex for winning at Golf – It looks like she forgot about that part of your bargain. She could work her muscles fucking us both and I wouldn’t complain a bit!”

Just at that moment Dee stepped to my left and announced “Tom has ONE muscle I make good use of – his huge cock. You have one muscle I will make use of later – your MOUTH.”

I cringed because she had overheard my rude comments.

She pointed her finger in Toms face and started to reprimand him like a little schoolboy “Now you TOLD our new MAID that I was giving you sex for winning at golf?”

“Yes Ma’am” He admitted. “But only because you said so.”

“This is how you train our new MAID – to smart off to obvious authority figures” She admonished Tom “You are doing a lousy job of training her – perhaps you need to be punished.”

I took offense of Dee calling me a ‘her’ just cause I wore a female maid outfit, but was too stunned to say anything to defend Tom or myself.

Dee continued to berate him and in the process get her digs on me. “I go to the trouble to bet for you – and you don’t use this to your advantage – you should be swatting the little slut on her ass, and making her kiss your feet for forgiveness toward slandering me.” She pointed at me while continuing her tirade “This maid needs to be shown who is boss in this house – and you let her badmouth me. With this little bitch at your feet – your chores would be over quickly; then maybe you would be my fucktoy.”

I had to disagree. “Hey, wait a minute – I know that y’all are into this female drag thing – and I got conned into playing along – but I am not anyone’s little bitch!” How much authority does a guy have when he’s on his knees, wearing a female maid outfit sandwiched between the cabinets to his rear, his new neighbors standing in front of him.

“Shut the fuck up – Bitch.” Dee slung her open-faced palm – smacking my right cheek.


I was in awe of the force of her smack. I cower at their feet.

“See how disobedient she is?” Dee warned Tom

This time I didn’t question her use of the word ‘her’ when she referred to me.

“You need a spanking – for her insubordination.” Dee proclaimed.

“NO – please – not in front of --- not here – not now.” Tom whimpered

“Spread your legs and bend over toward the cabinets.” Dee instructed Tom.

Dee picked up a wooden spoon off the counter and proceeded to smack his ass with it.

After 10 swings, he was trying to adjust himself to better accommodate the punishment. I was trapped between his legs and the cabinets behind me when Dee ordered “Bitch, it is YOUR fault he’s being punished. You need to hold his legs wide open.”

I spread out my arms pushing against the inside of his thighs. My face was eye level with his panty-covered crotch. Each time she hit him – he pushed a little bit further toward my face.

After the 30th stroke she asked him if I was going to obey? I decided to try to stop this punishment. “Tom didn’t do anything – I was the one who said something about your body.”

“That costs you 10 more” she threatened him.

“WHY?” I implored her.

“There is another 10 – why don’t you do something?” Dee intimidated him to stop me from talking.

“Keep quiet – Chris. Every time you open your mouth – I get more spankings.” Tom tried to warn me.

To Dee’s sly enjoyment “I would shove something big in her mouth and gag the bitch – if I were you. I know you’ve got just the thing to keep her quiet.” Then went on delivering the next 20 swats.

I was silent. I held his legs open by kneeling between them. I couldn’t help seeing her swing the wooden spoon all the way back and then forward again until it collided with his unprotected butt. Inches in front of me his throbbing dick was what I assumed she meant to gag me with. I could see a small bit of pre-cum staining the satin panties where his cock head was located. This was an entirely different view than I have ever had of a man. His panties didn’t do much to cover his excitement as his cock filled with blood and started to pump and twitch in front of me. He was getting hard while he was getting spanked. I had mixed emotions – erotic thoughts of being forced to suck him – to kiss her feet – to submit to them both. But I was not the one being punished, yet I was fearful to confront Dee again.


When she was done, she turned his ass around to face my kneeling form and yanked down his panties. His butt was RED. There were marks all over it. Dee told me it was my fault for his punishment and that I should kiss it and make it better.

“I don’t like seeing him get spanked by you, but I don’t think me kissing his ass will make him feel better do you?” I pleaded.

“You are right.” Dee grinned at me and then turned Tom around to face me. “Kiss this – I know it will make him feel better” She said as she stroked his throbbing manhood.

My eyes were the size of saucers as I glared at his thick tool. His veins were pulsating the blood to his mushroom shaped head and it didn’t need any help getting hard – but her fingers were encircling his shaft aiming it toward my face. I looked at her and she just smiled.

“Go ahead bitch, I know you want it. Who could resist a huge cock like this?” Dee taunted me.

I tried to back away from his threatening manhood, but there was no place to escape. I was trapped by them both.

I am told that HE took the spanking for me – I should be grateful. How should I show my appreciation for his suffering. What can I do to give him some pleasure?

She already freed his cock out of the panties and aimed it at my face. I tell her I have never sucked a cock before, and I really don’t want to be forced to do it now.

“Forced? No – You will do it because next time I might not take it easy – I might be spanking YOUR butt for his infraction. He knows what infractions set me off – so he could make your little fanny quite red. You’ll suck him because you want to – because you adore his size – because it is your way of showing what a panty maid should do.” Dee let me think for a moment then offered “Do you really think it is right that he get punished for your offense?”

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