Mixing Business with Pleasure

First time author and would like to thank Lit member Kenji Sato for the amazing editing work, without his help, this story simply wouldn't exist.

Colin was still wearing his three piece business suit, after he'd arrived home from his day job as a high profile lawyer.

He'd dressed me in some light pink see-through panties, bent me over his knee, and started slowly spanking me; massaging my asshole with his middle finger before he inserted it, and tugged on my dark brown ponytail which was in place with a pink scrunchie.

Colin was about 47 years old, and bald in the middle with short trimmed brown hair on the sides. The middle of his head was completely bald and shiny, with a few pock marks and was, by no means, what you would call attractive; he wasn't ugly, yet far from 'handsome'. He looked like your typical high school principal.

I guess this is what made the contrast so eye-catching and hot; that I was an attractive 25 year old, with a fantastic body, pretty facial features and a full head of shoulder length dark brown hair.

He then reached for some hot pink anal beads with silver lining in between each bead. It was a first time experience, felt fun, and I was buzzing with anticipation; my adventurous spirit flourishing, as I began to explore every inch of my sexuality.

Colin paid me two hundred dollars a day to sit around his place while he was at work, and look pretty for him when he arrived home. This was hardly a task, as looking pretty was what I did best.

He likes to sit in his chair and watch me walk a makeshift catwalk, as he smokes his cigar and sips fine whiskey.

The pink stilettos I wear for him make me walk awkwardly and feel 'humiliated'; yet, I find the experience fun, enjoyable, and a major turn-on. He doesn't care that I haven't mastered the art of wearing them yet.

Above, was a set of monkey bars he enjoyed watching me work out on and doing press ups. He enjoyed painting my fingernails and toenails a pinkish purple with sparkles that matched the panties and scrunchie in my hair; as well as, giving me manicures and pedicures.

It felt good to be pampered. I never considered myself 'gay'. I just enjoyed the attention and admiration.

The word 'gay' was just that -- a word -- one that to me, never really meant anything. There was no shameful stigma, or taboo; or better yet, 'sin' attached to it. I was far from indoctrinated by hate-filled hypocritical religion.

Today, Colin had done my hair up in pigtails, with hot pink hair ties; and got me stoned as hell. I smoked a long paper joint of some really strong bud, and there were plenty more of these pre-rolled joints to see out the night. It made me feel more creative, adventurous, and out of body.

He gave me a tight pink top that showed my belly, with the sleeves shorter than mid-shoulder length, barely longer then a tank top. He then took the bottom of the top and looped it through the neck hole and tied it in a knot, as you would a sweater behind your back, except the knot was at the front of the top.

It made me really incredibly 'girly'; yet, ironically, made my cock extremely hard.

I needed to release some tension and gestured to my raging hard-on with my head to Colin.

"Lay down," he said, and directed me to the massage table.

He then unbuttoned his shirt sleeves and rolled them up displaying his incredibly strong forearms that were tanned in colour and muscled like a pitbull. With a manly firm grip, he grabbed my cock and started stroking it.

Colin gave the best hand jobs I'd ever had. He wasn't uncoordinated like a girl; being a guy, himself, he knew exactly how it should be done and pumped my cock back and forth in rhythmic fashion.

He stopped every time he felt I was about to blow and pinched my nipple; knowing the pain shooting through my body, would distract me from the pleasure of my imminent orgasm.

I must have looked like someone on a torture rack -- and cried out like one -- through all the edging. I wasn't fake moaning like I would with a girl, in an attempt to please her. This was genuine sexual frustration and groaning through real pain.

Most of the groaning came from the hot red candle wax he would drip onto me, as the room was lit by candlelight; and before doing so, he loved to oil me up like a gladiator and fashion a lasso styled piece of string around my testicles which put me under a spell of his control as he now literally 'had me by the balls!'

My complexion was slightly tanned in colour, and between the scented candles and oil, along with the musky smell of my dick; there was a delightful aroma in the air.

I wasn't sexually attracted to him like he was to me

But I enjoyed sucking a twelve inch pinkish purple dildo attached to the wall as he jacked himself off. It tasted delicious, as well, like black cherry and I'd savour the flavour and smell it.

To Colin, though, it just appeared I was savouring and smelling the taste of a real dick, as he must have visualised me sucking him.

I respected Colin because he'd provided great financial security to my life, and a sense of stability. He could hook me up with anything on a whim; hence, I obeyed his every demand. I made him the number one priority in my life; even more important than the occasional hot date with cute girls I met. He introduced me to the good life, as well, and even lent out his second black Mercedes to me to drive intending on me to keep it if our friendship lasted twelve months, and I visited him once a week.

One particular evening, I arrived and he provided me with an outfit. It was so exciting and fun to hang around there, knowing he was going to make me dress up. He made me feel like a kid again at Christmas.

On another occasion, I was to wear a tight pair of black leather pants, and rainbow jockstrap with the waistband displaying above the pants. Colin loved this look, as the top of my ass crack was always on display along with my 'adorable back dimples' as he put it. He'd even had them pierced with diamond dermals.

Most of the time, in between playing dress up, he'd prefer me just laying around his place in nothing but a jockstrap; there were so many of them to choose from, he had such a wide collection.

Tonight's outfit made me feel fresh, as Colin had recently trimmed my locks an inch straight across at the ends, and had my hair up in a short ponytail, displaying my white neck that had been shielded from the sun. I had the 'fresh feeling' of a new trim, along with a black sports bra and a skimpy black cotton thong; the outfit matched my dark hair and big brown eyes.

I loved how skimpy the thong felt whilst putting it on, and the fact it barely covered any part of my package, with my nine-and-a-half inch uncut cock fully erect, only turned me on even more. I liked the feeling of it sliding, as well. It was a sporty, black G-string designed for women. Colin had bought me a two hundred dollar pair of black Adidas jogging styled sneakers and matching socks which completed the sporty look.

He'd recently pierced my sexy innie styled belly button, as well, with an expensive diamond, which again made me feel 'feminine' -- just another fake word created by society.

I felt sexy and fit and completed some jump rope for him until I'd worked up a sweat, at which point, he began to smell my arm pits and ass; and provided me with a refreshing cranberry juice with ice and a lime wedge.

He'd adorned me in jewels like Lucifer, pretty matching diamond studs in each ear and a matching diamond butt plug which is always visible through the skimpy black thong. A taboo to toxic 'masculinity', another fake ideology created by society, which I revelled in going against.

I was the true bad ass with balls, unlike the fake males with their fake personas of today and yesteryear. Sometimes, I'd only wear one stud in the right ear since 'that meant gay', as I loved going against all stereotypes and dogma and revelled in my individuality and 'hell-bound' tag, according to dogmatic religion.

My mind and soul were truly liberated and I never once felt I was flirting with danger. I just enjoyed the tag being some 'devilish sinner.' How ironic, that religion's threats towards me, only made me hornier.

I enjoyed mocking it for the joke that it was, and pitied such small and corrupted minds, who were influenced by it.

I'd often wear the leather jacket Colin gave me, displaying one clean shoulder, and so forth.

I commented on how pretty the jewels looked over my body, and the sparkles he'd applied over my high cheekbones.

"These are my favourite jewels" he said, as he felt my nutsack and jiggled it like one would a sack of coins in medieval times.

He made me feel so special and beautiful.

He'd had my ass and ballsack freshly waxed, and Colin shaved my chest and underarm hair, himself; of course, with a pink razor. Those places, along with my thighs and legs, to which he'd apply moisturiser afterwards, allowing them to take on a more feminine look.

They'd always remind me of my current place, whenever I felt them.

My thighs were strong, milky white, and smooth; with calves that were beginning to look more defined from catwalk ventures in stilettos, plus my constant workouts.

I smelled of expensive designer aftershave, nothing womanly about my scent. The cool spray felt amazing on my neck; he also applied it to my ribs, which provided a tickling sensation making my cock twitch in agreement.

Later that evening, Colin revealed some 'Thai sticks', an extremely potent strain of marijuana, he'd had shipped over through one of his friends in high places. He rolled the most amazing cone shaped joints dipped in a wax substance, and I felt myself getting ripped after two drags. The strain created a borderline out of body experience and got my creative senses flowing, as I began to analyse everything in fine detail, and started slightly 'tripping', but not to the point I was paranoid.

I always felt comfortable in his presence, knowing there were no strings attached.

Colin led me to a walk-in wardrobe in his bedroom. He had a beautiful king-size waterbed which I loved relaxing on whilst he was at work, as I was minding his place awaiting his return.

On the hanger was a tight white singlet with a set of light purple, white, and pink fairy wings along with a ballerina's tutu, some white stockings, and a tiara.

This would be this evening's outfit.

Due to the high levels of marijuana in my system, I looked at the outfit and was lost for words. I just stared at it for a moment; bowed my head, feeling slightly embarrassed, and felt my cheeks blush.

"You're cute when you're stoned," said Colin. "You'll look even cuter in this," he implied.

I continued to stare at the outfit mesmerised, and visualised myself wearing it, before Colin demanded, "I want you to strip for me."

I was already semi-naked as it was, wearing the black G-string, black sports bra, and black Adidas sneakers.

I sat down on a chair and Colin knelt down before me and began to remove my sneakers and socks, whilst smelling my feet and sucking every last one of my toes. No girl had ever been into me enough to do that; they were all so prudish, regardless of how 'freaky' they made out to be. It felt nice to have someone who was so into me, and I enjoyed all the new experiences and sensations.

This is what life was all about!

I always had a sense of superiority to Colin, as he was much older and bald; whilst I was young and attractive with a luscious head of hair. It gave me a sense of empowerment, which I enjoyed.

Before long, I was dressed as a fairy ballerina.

Quite fitting. I enjoyed being a 'fairy' for Colin; breaking, yet, another stereotype down.

My nine-and-a-half inch uncut, tanned cock was enough to make a mockery out of the outdated beer-bellied micro-penis having 'men' which dared to use such an 'insult'. I had the balls to become everything they secretly, and most likely, admired themselves; yet, out of a false sense of pride and immaturity, would never admit.

Colin and I, then moved into the lounge room where he asked me to sit on his lap. He began putting my hair into small bun styled pigtails, massaging my shoulders, and feeling my nipples from behind.

I felt so free and vulnerable wearing the tutu with no underwear, and my cock became extremely erect.

He brought up the reference I made to Lucifer previously in the evening, and asked if it was okay if he renamed me, 'Lucy'. He felt it was really cute, and it made me feel 'girly' once again.

I could become the creation Colin wished me to be -- and I wished to be!

He asked me to stand up in front of him. He took out a body pen that released a grape flavoured purple glitter and began to write the word 'Lucy' on my raging erection. I became harder and harder, as he began to tease me and blow cool air from his mouth onto my cock which made me jerk in delight.

"You like that... don't you, slut," he responded, tongue in cheek.

I didn't have to say a word, as my cock twitched in agreement.

To which he said, "I thought so," as I just grunted and smiled moaning with pleasure.

Colin then suspended my arms with some leather bracelets to the monkey bars and placed the light pink stilettos upon my feet. It might sound like an oxymoron, but the sensation of the silky white stockings sliding effortlessly into the laceless stilettos felt extremely comfortable and I enjoyed the feeling.

I was completely outstretched, to the point I felt what was similar to growing pains in my shins; from not only wearing the stilettos, but also by the way I was being suspended. The pain I felt through my legs and arms, a slight burning sensation was becoming pleasurable, in a strange kind of way. I felt an extremely 'tight' sensation through my core area and it made my stomach look more defined and flatter than usual, further turning me on more.

It got my senses going, feeling a mixture of such slight pain along with the pleasure from the occasional stroke of my cock from Colin, who then released the suspension from my arms to a more comfortable level; but, I was still very much restrained, I became weak in the knees.

He then produced a feather and began lightly stroking my balls with it until my cock stood up and jolted further out, like a cobra would under threat, which made me quickly stand upright. He took the feather and brushed it over my rib cage area and underarms, to which I groaned and giggled like a schoolgirl.

Thank god, his walls were soundproof, so we could make us much noise as we liked without disturbing prying neighbours.

He took the feather and dabbled it over the end of my cock and the tip of my foreskin which was no longer covering my sexy knob; but began retracting itself until half of it was on display.

Colin then reached out and retracted it fully with the feather alone. It only took a minor touch and basically retracted on its own to display my well-defined, pretty penis; making me feel like a real man, displaying the most beautiful part of my body. Feeling the cool air over it, I was basically dripping with pre-cum; Colin wiped the tip of my cock with his index finger and sucked it.

"Mmmm, you're leaking," he said, as his eyes slightly rolled whilst savouring the taste. "You're turned on, aren't you?" he implied once more.

I just ground with pleasure.

"You're a bad boy," he said once more, as he slapped the side of my cock.

Colin then undid the button on his white shirt sleeve and rolled it up half way displaying his well defined forearm and grabbed my cock firmly and slowly began stroking it.

I felt myself about to climax, when he pulled out a decent-sized, brand new black chalkboard and said he wanted me to ejaculate over it, as he was wanting to make an art piece out of my cum. The black chalkboard was exactly the right colour to display the pearly white cum. After I ejaculated an enormous amount, he laid it horizontal to dry like glue.

Over time, we would continue to work on the art piece; much to my delight, he would display it proudly in his bedroom and every time he produced it, the board contained more and more of my cum.

He would say, "Look how much I've pleased you."

After I ejaculated, the fantasy died down a little and I began to recuperate. Colin allowed me to rest in a spare room he prepared for me, as I enjoyed my own space until I was 'in the mood' again.

I would find out months later, the room and ensuite bathroom had secret cameras where he would watch me masturbate, shower, and use the bathroom. He also had my phone bugged and knew my browser history and every kink I had. Most of my fetishes were young guys with older men along with lots of straight stuff, as well.

I was into all kinds of things from dirty anal whores to science fiction and anything in between, I considered myself incredibly open-minded. I identified myself as 'bi', if there ever was a word. However, my 'bi' side was strictly sexual and I much preferred the company of women. I could see myself settle down with the right girl one day; but, I would always have a wild adventurous side, most of it remaining unfulfilled fantasy.

Colin told me he would get his rocks off over watching me in my natural environment and not playing it up for the camera. I thought it was very intrusive to my privacy; yet, it turned me on, nonetheless.

Colin had also fashioned an elastic-styled cock ring, that I was to wear even out of his presence. It was designed to stay tight, even when flaccid; so, whenever I received a text from him the cock ring would vibrate and turn me on.

He was working on a butt plug device, which I further looked forward to.

It would serve as a reminder of what was in store and made me incredibly excited.

After I finished my shifts at the holiday park I worked, I would speed around to Colin's place in the black Mercedes he lent me, and wait there for the two hours it would take him to return from work.

He would leave raunchy notes all over the place, and made me feel like I was on a treasure hunt. Most nights had a different theme and there was always some kind of surprise in store, and a gift laying around.

Due to the high amounts of money he was paying me, I was beginning to dress really nice and eat only the best. I started to acquire lots of nice appliances around my home, and was well on top of any bills, providing perfect peace of mind. I'd even cut down on shifts at work, now working part time hours just for something to do as a side hobby, as I never really need it for the money anymore; Colin was providing plenty of that.

The work week flew by and Colin had buzzed me earlier in the week and organised a dinner party with some high-profile friends of his. I never asked any questions, and he never provided any further information; only that it was take place at 6:00pm.

It was only 4:30pm when I arrived at Colin's. As I was approaching the security gate, I entered the code, then continued down the drive and entered the enormous underground garage. It made me feel like Batman. Maybe because he'd dressed me up as Batman in full latex a few weeks prior, but there was something about the black car and bunker-styled garage, that reminded me of the Batman movie. The underground garage also served as a winner cellar; I never drank wine, but it added to the class of the place.

I locked the Mercedes and climbed the spiral staircase from the driveway which led into the dining room. The dining room window was made of cinema-sized styled smart glass which displayed an impressive view of a rock pool, complete with spa and rainforest-styled garden.

I enjoyed going skinny dipping some evenings, while Colin watched me through his bedroom window which also displayed a view of the pool.

it made me so horny that this dirty old man enjoyed masturbating over me, it made me feel beautiful.