I am in my mid-thirties and newly single, I have done very well in business that has allowed me a very early retirement, I still needed something to set my sights on and invest some of my money into to give me something to do besides the travel I have planned.
I started a marketing group with an ex-boyfriend that grew into a massive business, we ran it together for six years, eating and breathing that business until our relationship fell apart. I came home to our condo to find my boyfriend in our bed with a nineteen year old kid who Rick was fucking while the boy was begging for him to push it deeper, that was it, I moved out that day, going to a hotel for a couple of weeks until I bought my own place.
I still had to face Rick at work every day and it was very uncomfortable, one part of me wanted to pull his cock out of his pants and twist it off and that was the nicer part of my thoughts. I told him that he could buy me out or I could buy him out. The company was worth near thirty eight million, half of which was mine.
If he wanted to own the company fully, he was going to have to pay and mostly for cheating on me. I sent Rick an email to meet me in my office at three that afternoon, I didn’t even want to look at the weasel, I thought we had something special going but I guess he had his eyes on young ass.
Three o’clock came, I was nervous and wanted this over, it had been weeks since I moved out and I needed to remove myself from his life completely.
“Rick, I want out and I want it now, I can’t stand looking at you anymore, either you buy me out or I can buy you out.”
“Look Wes, I’m sorry but we just sort of drifted apart and I needed more.” Rick said.
“Fuck you, you should have tried to work things out and let me know your feelings.”
“Do you want to try again? Come move back in baby.”
“I’d rather take a dull hatchet to your balls.”
“Don’t be so violent and mean, it was not all my fault.”
I just shot him a look and he shut his mouth and took a sip of water, Rick was a sexy looking guy, maybe too good looking, I have always thought that guys that are that hot are not worried about working on a relationship as they can get another guy in ten minutes at the nearest gay bar.
“Look, here’s the deal, I want eighty percent of the money the business has and you keep the business and twenty percent, if you continue running it like we did, you will make millions and millions over the next few years, if you spend your time fucking little slut boys instead of keeping the business running and growing, you’ll go broke.”
“That’s a low blow, and it is too much money you would get.”
“NO, I want that, we built this company, I worked hard to grow it to what it is, you will keep the company which is a cash cow as long as you run it right, I want your answer tomorrow by five, I will have our business lawyer write up the paperwork when you agree and then I am out of your life and the business.”
I got up and walked out leaving Rick sitting in my office. I stopped on the way home and picked up a carry out dinner, I just wanted some peace and quiet for the evening.
My new condo was in a high-rise building that just opened downtown and I was able to pick a prime unit out with a huge master suite and a walk out patio that was big enough for small parties, I hired a top designer to do everything but hang my clothes in the closet, he finished off my home with such taste and flair, I was very pleased with the way it came out.
I had asked the designer if he would be interested in me investing in his business to help it grow, but he was happy with it as it was, not wanting to give up part of his profits. He did tell me of a couple of his friends that started a new fashion company that I might be interested in but didn’t want to go into too much detail and said he could have them call me about setting up a meeting.
I relaxed the next day until I saw an email from Rick, asking me to reconsider the amount I wanted to step away from the company. I sent a reply to him telling him flatly, NO! Unless he wanted to take fifty percent and leave me the business.
“Don’t forget, you got out with the condo too, I didn’t want anything to do with it after seeing how little I meant to you and wonder how many boys you have fucked in our bed that I don’t know about. Fifty percent is mine and the other thirty percent buys me out.”
I was trying not to go onto a rant and vent, I really wanted to keep things business-like and close it all, ending anything to do with Rick. He finally agreed to sign the paperwork and give me eighty percent of the value of the business, our attorney did the paperwork and transferred the money into my account within a month and I was done with him and our business forever.
I got a call a few days later from Jason and Kenny setting up an appointment to sit down with them to discuss joining them in business, I needed something to occupy my time making investments and putting a bit of my money to work.
Jason said they have a new clothing business that is sure to be “the next big thing”. I was a little worried that it was a fad and would be a failing mess but I agreed to meet with them and let them show me what they have in mind.
I drove over to the address I was given, it was a warehouse with a large showroom in the front, nothing very elaborate, Jason invited me to sit while they gave a presentation in front of me, they were aware of the business that I had and the breakup with Rick.
“Wes, what we have created is called a Casual Kilt, it is for men who like to relax with a lightweight garment that does not pull or bind and like a kilt, and you wear what you like under it, but most just want to hang free and relax.” Jason said.
Kenny laid a few of the kilts on the conference table, some were plaid like a traditional kilt, and some looked like a lightweight denim or solid colors.
“The fabric is lighter and attaches with a hook and loop closure at the waist letting you decide how tight you want to wear it.” Kenny commented.
“So what is the difference between this and wrapping a towel around your waist to wear around the house?” I asked trying not to be offensive.
“This is not a towel, and it is not just to wear around the house, we think that guys will wear these casual kilts out in public. Hell people wear pajama bottoms out in public all the time.” Jason said.
“Well, we know how that looks.” I said with a laugh.
“Look, I don’t mean to make fun of your product but I think it is just another of those snugglie things made to sit wound the house in.”
“Those snugglie things have sold over thirty million dollars in product in five years.” Jason added.
“The Casual Kilt is made to wear with or without a shirt, to be worn at the pool, your living room or out at dinner, let us show you a few men we have to model the Casual Kilt for you.”
Jason opened a door and a parade of men walked in and lined up about ten feet in front of me, all were bare chested, there was a variety of men from heavy to slim and young to old, a couple of them were very fit and Jason pointed out how the men can wear the kilt higher on the hips or very low allowing a slight view of the V line that goes from their ab’s to their crotch, one turned showing a hint of ass crack.
“The Casual Kilt has that hook and loop closure that allows adjustment of snugness and also for ease of taking it off.” When Jason finished his words, each guy pulled the closure section at the waist and in one movement and pulled off their kilts and flipped them up and over one shoulder, all of the men were naked and turned to the side and walked back through the doorway, I watched their asses move as they parted my view.
“As you see, the Casual Kilt is a comfortable garment to wear and easy to remove when you want to take it off too.”
“Very nice, too bad you can’t do that on TV, you would sell a million of them in a week.” I said with a smile.
Everyone laughed and the duo started showing me the details of the fabrics and brought out two of the models that had put the kilt back on, one was a young guy that reminded me of the boy that Rick had fucked and the other was about my age who must spend five hours a day in the gym, he had a very low fat ratio to muscle.
Jason pointed out the waist line of the kilt un-fastening it moving the kilt higher and lower on his hips, my eyes caught a glimpse of his cock swinging inside the fabric, I wanted to touch it badly, hell, I was single now too. Jason ran his fingertips along inside the waistband of the kilt.
“Feel the snugness and how secure the kilt fits William’s body.” Jason said.
I reached up and put my fingertips between the fabric and the models hot tan skin. Jason brought the younger model over within a foot of where I was sitting.
“Now, Brett here has the kilt loose and low on his hips and it rides on his hip bones.” Kenny said as he pointed out the fit.
It looked like if the well-tanned boy moved or sneezed, the kilt would be at his ankles. They unhooked the waist again showing how easy it was to make adjustments to the waist while you wear it.
“The eye candy is enough to make me want to sign a contract with you alone.” I laughed.
Everyone laughed and the models vanished into the back room again while we went over what they were looking for financially. I took the proposal and a few samples telling them I would let them know after thinking about it for a few days and let them know soon.
The next morning I walked out of the building to walk a half a block to a café for breakfast when I see the muscular model from the day before, walking down the street wearing only a Casual Kilt and sandals, I called him over.
“Cute, so either you are stalking me or they sent you by for an obvious product demonstration on the streets, how long have you been waiting?”
“My name is William, I’ve only been here about half an hour.” He said shaking my hand.
“My name is Wes.” I said.
“Yeah, I know.” He said with a smile.
“So do you have a shirt with you? You can come to breakfast with me since you have devoted so much time this morning.”
“Sure, it is in my car.” Hs said as he jogged over to his car slipping a pullover shirt on and tucking it into his kilt.
Over breakfast I asked him about the comfort of the kilt, he said it was like wearing nothing at all, and maybe one would like to wear underwear under it during a breezy winter day but he liked going without. He explained that he was a model hired by the Kilt guys for the demonstration but today he said he was not being paid, he said he wanted to meet me and thought it was the best way to get my attention, wearing the kilt he was given by Jason.
“So you were out there waiting to meet me and not paid by Jason?”
“Yeah, I truly was sort of stalking you.” William said with a smile.
“So you don’t feel self-conscious wearing that in public? I asked.
“No, I really don’t, I have no doubt that I get stares but I take it as a compliment.”
I looked at his muscular thighs vanishing up into the kilt as he sat there, I wanted to see beyond the kilt and I think I was staring a little, he reached down and gave his crotch an adjustment through the fabric.
My heart pounded a little, Rick and I had been together for years and this was my first time with a guy that was even remotely romantic. We ate and talked about daily life stuff, he was easy to laugh and very easy on the eyes.
“You look like you would be a natural wearing a Casual Kilt, you should give it a try, you know, out in public.” William said flashing me his sexiest smile.
“I’m not sure I am cut out for it myself.”
“Well, they gave you samples, let’s go back to your place and get you into one, what do you say?”
“Alright.” I said as I stood up from the table.
We walked into my condo and I went into my bedroom returning with two kilts to show William.
“Blue or brown?”
“I think blue, it goes well with your eyes.”
I walked back to my room to change, but did not close the door, I stripped everything off and wrapped the kilt around my waist fastening it snugly.
“Wes, it looks hot on you, but..”
“Well did you go naked under it or you wearing undies?” William asked with a giggle.
I momentarily lifted the front of my kilt exposing my shaved hairless crotch hanging loose in front of my house guest.
“I feel like I am wearing a skirt, like something is wrong and I should not go outside wearing this.”
“Nonsense, you look great.”
I grabbed a polo shirt and slipped on some tennis shoes before grabbing my keys, signaling the fact that I was ready to go out into the world wearing this man skirt.
We walked down the streets, and William peeled off his shirt and was again bare chested. I was beginning to feel more comfortable with my attire and the feeling of being naked under the kilt was refreshing, sort of like I was walking around naked with the breezes blowing over everything.
A few people looked at us like we were crazy and a couple of guys stopped us and asked about them and did we like wearing them, it was good research and was helping me make a decision about joining the business.
William and I walked back to my condo, I grabbed a couple of beers and sat next to William on the couch, looking at William’s jawline I traced down his shoulders with my eyes, I wanted to nuzzle his neck and smell his scent so badly.
We sipped the cold brew and talked for quite some time and the topic came back to the kilts, William played with the hem of his while he talked, exposing more and more of his hairy thighs.
“Well, the kilts are sexy if nothing else, they make us want to see more of what is under them.” I said.
William eased the material up higher towards his waist.
“How much do you want to see?” He asked.
I smiled as I reached over and lifted his kilt up, folding it back, his soft cock lay on his balls that were mostly between his thighs. I reached over and ran my fingers over his cockhead making it swell under my touch. I leaned in and kissed one of his nipples gently, while his hands roamed across my shoulders and back. I licked my finger tips and rubbed them across his shaft to the head, his cock stiffened more and more until it was standing almost straight up.
I pulled at the fastener of the kilt loose and flipped it to the side, William was now sitting here naked beside me. I took his thick and shaft in my fist and gripped it tightly, he leaned back resting his head on the back of my couch, his legs spread wide with his nuts that begged to be touched.
Looking at William anyone could see that he was a model, he had the looks for it and kept his body toned to be used in advertising anytime he could. I lifted his balls with my fingers, feeling the weight of them, they were soft and William was groomed but still pretty hairy.
His body seemed near perfect, far from the normal guy I would pursue but he seemed more than the superficial arrogant type I might suspect a hot guy that looks like him to be.
My heart raced as I stood and leaned over him, touching his lips with my fingertips at first then kissing him so lightly our lips hardly touched. I kept kissing but each time our lips would touch the urgency would grow causing me to gasp for breathes between kisses. I straddled his lap, my kilt pushed back and I felt his hard cock pushing at my ass as I lowered myself onto it. William spat onto his hand smearing it onto the knob of his dick before he guided it into my hole, I took my time but within a moment or so I was butt cheeks deep on his cock and kissing his lips frantically.
I had no idea how this all happened so fast, I don’t usually throw caution to the wind and have sex within a few hours of meeting a guy but this one was different, maybe it was my newly found freedom or maybe it was something more but I wanted to keep him deep inside me in a bad way.
I rode his rock hard shaft with my hands on his shoulders while his held my hips, I could feel his warm breath against my neck. He reached between us and grasped my hard cock, squeezing it tightly, I almost shot my wad right then.
“I’m cumming Wes” William moaned as he tilted his head back and closed his eyes.
I shifted my weight on his shaft pushing it off to one side just a bit making him go wild, his breathing hastened to the point that he was panting and yelled out as he shot his man juice into my ass. I continued riding him until he rolled me off, his cock was very sensitive by then.
William got to his knees in front of me and pulled my very stiff shaft into his mouth, bobbing on it he took it deeper and deeper into his throat, it did not take me long before I held his head and pumped my hips forward riding his lips until I shot until I filled his mouth with my salty cream.
Later that week I signed a deal with Jason and Kenny on the Casual Kilt business but my mind would always come back to William, I wanted to see his smile and taste his lips. I was not used to dating and the lust was stirring inside me, I needed him, he was all I could focus on, maybe this was more than lust, more than a fleeting sexual encounter, I had to shake these feelings and concentrate on the business profits and loss statements, I needed to help bring in more profit while increasing sales, this is what they needed me for, my marketing sense.
I called William and set up a dinner date for this evening, I worked on media advertising for the Casual Kilt for a few hours before showering and getting ready for dinner with William, I almost wore the kilt just for fun but figured that I would wear jeans and a sport shirt instead.
I drove over and picked him up, he leaned in and kissed my cheek as he belted in to his seat, we chatted on the way to the steak house, I wanted red meat, and then sex, I seemed to crave both today. Inside we sat on opposite sides of the booth and grinned at each other between conversations, William had kicked his shoe off and was running his foot up my leg toward but not quite reaching my crotch, but still got me hard.
After dinner I drove back to William’s home and could not wait to get inside to get my hands on him, he got drinks for us and we cuddled on the couch and it only took moments before my hands were all over him, I unbuttoned his shirt while he unbuttoned mine, we peeled them off tossing them aside, our chests bare, my lips went for his nipples sucking and chewing them making them hard causing him to squirm some.
We stood up and peeled off our shoes, socks and pants while hopping around still trying to touch each other while doing it. I smacked him on the ass, and what an ass, his butt cheeks were well rounded and tight, they made me want to bite his firm mounds of flesh. William pulled me over the couch, he sat and I straddled his legs while he glided his thick prick into my ass after he lubed me up, I rode up and down on his rod while it stretched my butthole out and made it burn like it was on fire.
With my hands on William’s shoulders, I was looking into his face while I bounced on his cock, his hands roamed my sides and my hips. I leaned in and kissed his lips just before I went wild on his prick, I moved left, then right and wiggled my ass around as he shot his load into my stretched hole.
William pushed me back gently off of his cock and onto my back, he leaned in and put his face to my crotch inhaling deeply taking in my crotch scent. William surrounded my cock base with his thumb and middle finger squeezing it tightly causing the veins to stand out on my rod before taking most of my shaft in the first gulp.
I leaned back and let this man do what he wanted, it all felt insanely wonderful, he would stop long enough to lick and suck at my balls before going back to cock sucking. I blew my cock shake down his throat and across his tongue while he gulped it up. William put his head on my navel and rested, my wet cock at his chin.
“I have a great idea, I want you to be the model for the Casual Kilt advertising, and you believe in them and look hot and sexy in our kilts.” I said.
“Yeah? I would love to, I mean, if you are serious that is.”
“Sure, I don’t know why not, no sense in going out to do a search for a model elsewhere when you are right here.”
“You are just saying that because I suck your cock so well.” William said as he burst out laughing.
“No, but that is a great side benefit.”
“I will arrange a photo shoot within the next few weeks then.”
“We need to seal the deal then.” William said.
He moved back down and lifted my cock with one hand and sucked it back to life again he worked it into a throbbing wet pulsating unit that was going to the hilt down his throat and after a few minutes I was about to cum again and just as it started he jammed a finger into my ass making me shoot a very intense second load of jizz into his mouth.
We snuggled some before getting into the shower together, I washed his backside and he washed me all over, front and back. I treated William to dinner even though he wanted to cook dinner for us, we went to a popular steakhouse where they treat you like royalty, and everything was perfect.
I had a steak with huge coconut shrimp that came with this sweet and spicy pineapple dipping sauce while William had a T-bone steak, I was really enjoying William’s company so much. I watched his lips as he ate his dinner, they were thick and dark red and seemed to suggest to me that I kiss them.
William looked up and noticed that I was staring at him, he simply smiled and bumped my foot with his and he seemed very relaxed with me and smiled before holding his fork un and dropping it to the floor under the table.
“Whoop’s, I dropped my fork.” William said.
“Well, just ask the waiter for a new one.”
William grinned and lifted the tablecloth and disappeared under the table, the next thing I know, William is at my crotch unzipping my fly, I looked under the table at him as he pulled my cock free from my pants.
“Dude, you are gonna get us thrown out of here.” I exclaimed.
I leaned back into the booth and let the man do his thing, William worked my cock into a stiff shaft of meat that he was swallowing as much as he could due to his position under the table.
“Is everything okay?” the waiter asked as he walked by.
“Yes, it is better than you could believe, please bring us a couple more drinks.”
The tablecloth did not come completely to the floor and I could see that at least one guy a few tables away was watching with interest, I smiled at him but he did not look away.
The waiter brought the drinks to the table about the time I was shooting my load, he must have thought I was having a seizure, I pushed my back into the booth and thanked him while my legs jerked around from me trying to hold back from crying out as I shot my jizz into William’s mouth.
William popped back out from under the table and slid up into the booth seat looking around like nothing had just happened.
“You are a very bad man!” I said softly.
“I am very good, and I think you loved every minute of it.”
“The guy in the light blue shirt over there was getting an eye full, he would not look away no matter what.”
We sipped our drinks and talked for a few minutes before I paid the check and we went back to my place. We stripped and lounged on the bed snuggling and watching TV, William’s body was so perfect and crazy hot but it was his personality I was loving, I wanted to be with him always.
I reached into the nightstand and took out a not too large dildo with “balls”, I turned on the vibration and William grinned in anticipation. I lubed it and his ass moving him to a doggy position before slowly pushing it into his ass I loosened him up before I moved into place and slid my cock into his ass alongside of the vibrating dildo. I could feel the vibration against my prick while I fucked him in the ass, it felt amazing and I didn’t hear any complaining, just a lot of moaning and groaning.
I reached under gripping his cock, it was hard as a rock and dripping pre cum, he was definitely getting off being double stuffed. William began convulsing and crying out, he was cumming and no one was even touching his cock, he was shooting all over the sheets, I started blowing my third load of the evening and this dildo was sending me over the edge.
William fell off to the side and pulled me close to him, he started laughing and kissed me on the lips.
“What is so funny?” I asked.
“Nothing really, I’m just feeling so good and at ease with you I could not hold back.”
“Never hold back with me, always be yourself, that’s who I want to be with.”
We jumped into the shower and changed the bed sheets before laying down again, I pulled William close and kissed the side of his face as he lay his head on my shoulder we drifted off to sleep.
William became the main model for the Casual Kilt and the first six months after I signed on we had a fifty percent increase in sales but me being semi-retired it allowed me plenty of time to spend with William. We went on a vacation to Europe for three weeks and am thinking about asking William to move into my condo with me, I never get tired of seeing him shirtless wearing only a kilt.