I couldn’t help but be curious. “John, don’t take this the wrong way… but why didn’t you never remarry? I mean, you’re a good-looking guy and have money. I’m you could have any girl you want.”
He gave a half smile. “She was a one of a kind woman, Ken. Barbara wasn’t just some good luck charm. She was my soulmate.”
That reminded me that I was still wearing his dead wife’s clothes. My new look was no longer some disguise. It felt just as natural as my own skin. Taking it off felt like shedding an integral part of me.
There was no longer any going back to being Ken the casino employee.
I poured myself another glass. “Well, you’ll have money to keep yourself happy. My advice is to call it quits and swear off the slots. No one gets that lucky twice.”
“I can’t imagine tearing myself from those machines,” John laughed, helping himself to another glass as well. “It’s the only thrill in my life now that Barbara’s gone.”
“Just take it easy, John,” I replied, sounding a bit sterner than I had planned. I had seen too many people go broke chasing jackpots. “It’s hard to win a buck in this city but it’s easy as hell to lose it.”
“How about you?” he asked. “Do you have a special someone in your life, Ken?”
I shook my head. “I’ve been working so much that there isn’t much time for me to do anything else.”
He patted my back. “You won’t have to worry about money ever again.”
Remembering that I was due a clean million, I gave him an incredulous look. “Are you sure you want to give me a part of your winnings?”
John helped himself to some gourmet cheese and crackers. “My beautiful lucky charm deserves her fair share of the score.”
Despite the night’s events, I felt like a bundle of energy. I guessed winning a small fortune did that to your nerves. “You know I’m actually starting to love looking like this.”
He smiled. “I knew you would come around to it.”
“It’s an acquired taste,” I said, eating a bit of cheese. I could get used to living a life of luxury. “This new look I mean, not the cheese.”
John stroked his chin and spoke after a pause. “You know, you’re the first person who took me up on this offer.”
I laughed. “I guess they weren’t as desperate for a quick buck as me.”
“There’s no rule about how a man can’t enjoy being a woman,” he replied. “Hell, I think you look as beautiful as Barbara.”
I couldn’t help but blush. “Really?”
“I’m serious,” he said with a grin. “You were attracting quite a bit of male attention down at the casino. I can’t remember the last time I saw so many men offer to buy you a drink.”
My cheeks still burned. “You really think I’m beautiful? Looking like this?”
Looking spellbound, he nodded. “Those clothes are yours to keep. You look gorgeous in them.”
“I can’t!” I protested. “They’re your wife’s. You’ve already given me more than I know what to do with, John.”
“It’s better than keeping them mothballed in a closet, Ken,” he said adamantly. “I can tell that you love dressing up like this.”
I looked away. “Do you think it’s weird?”
“Barbara always said being yourself was the most important thing in the world,” he replied, staring off into the distance. “I always thought I was born to be a gambler. Losing my wife made me realize that I loved her rather than the actual gambling. It was the journey that mattered, not the destination.”
“Does that mean you’ll give up gambling?” I teased. “Those slot machines will be lonely without a man like you.”
He chuckled. “Let’s just say I’m taking a break.”
“What will you do now, John?” I asked. John had changed my life forever but I didn’t know the first thing about him. “Do you have a job? Other than robbing casinos blind?”
“I used to have a corner office at a top law firm in New York City,” John answered. “Now, I’m just a consultant. It lets me travel since I do work over the phone.”
“Did you miss having a cushy gig in a Manhattan high-rise?” I asked. “Or do you like working a block away from a casino?”
“I’ll admit that’s a bonus,” he replied before turning serious. “But I wanted to give Barbara around the clock care when she got sick…”
John wasn’t some crazy person going around making people dress up like a woman. His wife must have gotten sick with something fatal. It was no wonder doing the same things he did with her brought him some semblance of peace.
Chapter 4
I decided to change the subject. “What will you do now? You’ve got more money than most people know what to do with.”
“Look, I was already well off from my old job,” John said, a soft smile on his lips. “I make good money from consulting fees as well. I just want to enjoy my time on this planet. Life’s too short to live with regrets.”
I nodded. “Words to live by.”
“How about you, Ken?”
“Me?”
He laughed. “Are you going to change your life with your share of the winnings?”
“I hadn’t actually thought that far ahead,” I admitted. More than money, I enjoyed the attention I had received with my new look. “I know that I’m still going to dress up like this. I’ve always been treated like crap my entire life. Wearing makeup and a dress makes me feel like an entirely new person.”
“Would you like another drink, Ken?” he offered, shaking a near empty bottle. “I can order another bottle if you like.”
I shook my head. “I’ve had one too many. I can’t believe I guzzled down a few hundred dollars’ worth of alcohol!”
For some reason, I felt very comfortable with John. There was a kinship I felt that I didn’t share with my coworkers. He was someone I could trust rather than some guy I could have breaks with in between work. Hell, I felt happier with him than any of the girl I had dated.
It was strange to have these feelings about another guy. I always thought myself as a red-blooded member of the home team. Then again, I had been dressing and acting like a woman for the past few hours. It wasn’t a stretch to say that I had a woman’s desires as well.
John noticed the change in my demeanor. “Something wrong, Ken?”
Feeling embarrassed, I tried to play it off. “No, it’s just that no one has ever treated me out for a dinner like this. I feel so lucky.”
I wondered if I was really falling for a guy I had just met. Something about dressing up as a woman had awakened a wild side to myself. John was good looking for an older guy.
“No, I’m the one who is lucky,” he replied, leaning in closer to me. “Lucky to have met you, Ken.”
He punctuated his statement by placing his hand on the back of my neck. His fingers massaged my soft skin. More out of instinct than anything else, I rubbed my foot against his. John replied by placing a hand on my thigh.
I smiled in approval. “I’d say you just hit the jackpot.”
I lifted my leg hair and exposed more of my skin. I had never made love to a man before. This encounter felt all the more thrilling due to my inexperience. The mere thought of fucking John sent adrenaline pumping through my veins.
On the other hand, John.
In any case, I was more focused on John’s hand trailing up under my skirt. My erection had risen under the confines of my panties. I was already wet down there with pre-cum. I gave him a moan of approval. The man could do whatever he liked as long as made me feel this way.
His cool fingers tingled my hot skin. I felt his hand rub my erection through the thin fabric of my panties. I wanted him to explore every inch of my body. “Please, touch me everywhere…”
John obliged by kissing me deeply. His hands cupped my ass as his tongue probed my mouth. His kiss was fiery as if I had swallowed a shot of vodka. I never felt such passion while making love to a woman. This man was awakening something deep within me.
He began to undo the straps of my dress. The soft fabric come off and exposed my bare skin to the cool air of the room. John smiled when he saw my padded bra. It gave the illusion of cleavage. My cock stirred from the mere thought of what he would do to me.
Thankfully, John was too skilled and patient to rush things. He embraced me so that my fake bust became pressed against his chest. His hands kept fondling my clothed ass. Then, he hooked his finger around the band my panties and pulled them down. My erection immediately rose up now that it was free.
He took my hand and led me into the lavish penthouse bedroom. It had a lot more space to play around with. I decided to undo my bra and reveal my flat chest. The sight of my exposed body brought a smile to John’s face. “Damn, you’re beautiful.”
I blushed as he placed the flat of his hands against my chest. His fingers flicked my stiff nipples as I moaned. Goosebumps spread across my body like wildfire. My cries of passion echoed throughout the penthouse. He played with my supple body and embraced its warmth.
I decided to repay the favor by reaching between his legs and cupping his clothed crotch. John groaned as I teased his balls through his pants. I knew that he was just as hard as I was. For that matter, I knew his prick needed to come out sooner or later.
John took charge by pushing my back onto my back and spreading my legs wide. It gave him a good view of my shaft. Rather than repulse him, the sight of my groin brought a smile to his face. He tenderly touched my erection with the back of his hand. Soon, his fingers touched my downy patch of pubic hair.
I watched as he undressed before joining me again in bed. John was in great shape and I could make out the musculature of his body. Being a widower hadn’t stopped him from hitting gym and keeping in shape.
Or learning how to make love to another man.
Dropping to his knees in front of me, John brought his hand between my thighs. I felt his tongue gingerly lick the soft underbelly of my erection. His touch was equal parts warm and moist.
I never thought I would find myself in this position when I first took up his offer. It was supposed to be a milk run. I was supposed to stand around in a dress and look pretty for a couple of hours. The only thing that mattered was my payment.
Falling for John wasn’t part of the plan.
I couldn’t help but be drawn to the man. He was reeling from the death of his wife. Rather than wallow and weep, John tried to channel his energy by still doing same things he did with his late wife.
I was so lost in my thoughts that I didn’t notice John swallowing my cock. The feel of his hot lips around my shaft was overwhelming. He was no stranger to sucking cock. I wondered where he had acquired such skill and knowledge. Nevertheless, it was a thought for another time.
“Yes!” I hissed. His tongue knew all the right places to touch. Of course, it helped that it was one guy doing it for another. “That’s it… AH!”
John licked my balls as they were a source of ambrosia. I was unsure of what to do other than to lie down and enjoy the world class blowjob I was receiving. I couldn’t remember the last time I had been treated to such a skilled performance. Most of the girls I dated were eager to get me off so they could go back to sleep. The man between my legs was giving me his undivided attention.
His tongue lapped away at my erection. I didn’t care where he had learned how to do this since I was having the time of my life. John further surprised me when he used his hands to stroke me. His mouth swallowed the bulbous head of my cock while his skilled fingers rubbed the rest of my shaft.
I was moaning like a broken opera record. “Yes, that’s it! AH! AH! AH!”
John expertly used his tongue and hands to drown me in bliss. I felt utterly helpless before him. I wanted him to go on and on until I reached orgasm. However, he didn’t want to me to go off just yet.
Thankfully, we graduated to another position. John got off of me and made me stand up. The man went behind me and placed his hands on my nipples. He gently squeezed the hard nubs between his fingers. I couldn’t help but turn around so he could lick them. I moaned in appreciation as he flicked his agile tongue over my chest.
Tired of the one-sided encounter, I decided to return the favor by licking his nipples in return. I applied what I had learned by rubbing my tongue across his hard nipples. John groaned as I lit a fire in him. My tongue shifted back and forth between each erect nipple. I was completely new to making love to another man. Thankfully, my instincts guided my hand.
And my tongue.
I worked my way down until I was in-between his thighs. John got the idea and sat back down on the bed. Marveling at his massive erection, I spread his legs so I had more space to maneuver.
First, I grabbed the base of his erection and began pumping him. I didn’t have John’s skill or rhythm but I managed to get a solid grip on him. The hard flesh pulsated against my hand. Then, I planted a soft kiss on its tip.
I stroked the entire length of his shaft. The friction between our bodies was unbelievable. It sent waves of ecstasy through both our bodies.
My lover smiled as pleasure pulsed through him. “That’s it… Ken… kept it steady… it’s not a race… Ah!”
I took that as my cue to suck him. I immediately tasted the salty tang of his skin. I heard him gasp when my mouth engulfed over half of his prick.
His cock was warm as I suckled him. My lips took in more and more of his lengthy prick. I loved every inch of his soft flesh. I was only apply the lessons I had only learned a few minutes ago but John looked like he was enjoying this.
John locked his ankles behind my back as if to keep me trapped here forever.
I didn’t mind the thought.
Chapter 5
I knew I wasn’t the first man to blow him. I wanted to give him a great performance more out of a need to pay him back instead of anything else. I needed him to forget anyone else other than me.
Despite my inexperience, I had taken to sucking cock like a fish to water. I knew the skills I was learning would serve me well throughout life. Indeed, I felt the tell-tale pulse of an orgasm within John’s erection. He brought his hands behind my head and coaxed me. “Yes, suck me down!”
John was hard as a stone pillar. Unlike his earlier performance for me, I was in a rush to get him to climax. The man was unusually talented at holding back his orgasm. I had to dip into my innate talent to get him to go off.
I began by running my tongue up and down his entire length. I teased the tip of his shaft with the underside of my tongue. I took more and more of his prick deep into my throat. A groaned from above was all I needed to know that I was on the right path. The only way to go was forward.
I reached down to cup his balls and massage the delicate flesh. I figured he would enjoy a good contrast between my wet mouth and dry hand. My lips and fingers worked with a steady rhythm. Whenever my mouth slowed down, my hand played with him more quickly and vice versa.
I resisted to urge to play with my erection. I wanted to give John my full and undivided attention. I began to moan from the pleasure I felt from sucking his cock. However, my cries of passion became muffled due to the massive prick between my lips.
John’s face looked like he was ascending into some erotic afterlife. I was afraid that man was going to pass out. However, he was too experienced to submit so easily to a novice like me. I watched as he relaxed and placed a hand behind my head. It helped guide me as I bobbed over his erection. I increased my speed as his hand coaxed me onward.
I kept suckling him for a good minute. My tongue swirled every which way. My taste buds sampled every inch of his hard prick. I didn’t care if he unleashed his load inside me. I just wanted to keep on sucking him.
However, we were both nearing our limits John came hard in my mouth. I sensed his heart race like a trip hammer. I sucked him faster and harder as his climax built uncontrollably inside of him. The man knew his orgasm was close at hand. “Ken… I’m going to cum!”
Soon, his cock
spurted its seed deep within my throat. The man thrust forward as the tip of his prick exploded with a powerful force. It was the physical manifestation of his feelings for me.
He didn’t pause to give me respite. I savored every second of it. John closed his eyes and tossed his head back. His cock kept doing what it ached to do. I had no choice but to relax and enjoy it.
I held onto his cock and balls. I treated it like a controlled explosion. I had power over the flow and duration of his orgasm. I coaxed my prize out of him. I loved swallowing spurt after spurt of his hot seed. It felt like having my favorite dessert.
The Trans Ultra Collection Vol 3 Page 29
