Despite doing the sucking, I felt like I was in charge. As a man, I never felt in control of anything. As Ken the woman, I felt as if John was clay in my hands.
Soon, his cock lost its hardness in spite of my efforts. I greedily suckled his prick as it grew soft between my lips. I had drained nearly every drop of come inside of it. After I cleaned it up with my tongue, John’s shaft slipped out of my mouth as he took a moment of rest. “That was amazing, Ken! Did you ever do this before?”
I blushed. “It’s my first time.”
I felt my cock stir at the thought of impressing a man like John. I wasn’t just roleplaying as a woman. I truly believed that I was one. I wanted to make him happy any way I could with my body.
Dressing and undressing as a woman had lit something within me. It had begun as a spark before growing into a fiery conflagration. This wildfire had spread across my body. I didn’t plan on dousing it any time soon.
After a brief respite, I joined John on the bed. He wrapped his arms around me and pulled me into a tender embrace. I couldn’t help but smile and tell him. “This feels great.”
John responded by kissing me. Our tongues spent a good minute tangling. Then, he requested. “I want to make love to you, Ken.”
“Fuck me first,” I replied, feeling a shudder down my spine. “Then make love to me.”
John lit up like a Christmas tree. “Yes ma’am!”
I took the initiative by sliding my hand down his body to his cock. It was semi-erect and still trying to regain its hardness. I decided to give it a little bit of help by cupping his balls before grasping the base of his shaft. A few strokes helped him rediscover some of his earlier rigidity.
With his cock recovered, John ran his hands up and down the sides of my body. Together, we explored each other’s nooks and crannies until we found the most sensitive spots. It was like discovering his body all over again.
The feel of his warm fingertips against my soft skin was equal parts stimulating and refreshing. Despite the air conditioning, beads of sweat dripped down our bodies. We should have been utterly exhausted from the day’s escapades but something compelled us to go on and on.
We kissed each other with more and more sensuality. I rubbed my palms across his chest and felt his skin rasp against mine. My fingers stropped to tease his nipples. I had gained enough confidence to clamp down a little harder. John groaned when mercifully teased his hard nub.
“You like that?” I taunted, relishing my power over him. I stopped just short of causing him any damage. “Do you?”
He chuckled at my enthusiasm. “I love it!”
I decided to heat things up by reaching down to rub his cock and balls. It was a bit more forceful than usual. Nevertheless, John was appreciative of the deliberate pressure I applied to his balls. His cock was back to full fighting strength.
He returned the favor by cupping my ass cheeks. His hands spread them so he could tease my asshole. He began by rimming me with a finger before finally penetrating my asshole.
I yelped as he worked his finger in and out of me. “AHHH!”
John entered even deeper and asked. “Does my little girl enjoy it?”
“I love it!”
I never thought this day would end with me dressing up as a woman and having another man finger my ass. I didn’t know why I was enjoying having someone finger fuck me. John was hitting all the right places. It didn’t matter why as long as I was enjoying it. With time, I got used to being penetrated. However, I wanted something bigger inside of me.
Thankfully, John had similar thoughts. I was disappointed, at first, when he removed his finger. However, he began to stroke his erection to get it back to its maximum hardness. I decided to help by squeezing and suckling his nipples. Soon, his cock was as tall as a spire.
I kept sucking his nipples as I reach down to help stroke his prick. I moved my head back and forth between each nipple as I used both hands to stroke him. Together, we worked in tandem to prepare his erection for my ass.
Finally, John took control and guided me onto the bed. I lied flat on my stomach as he positioned himself above me. My body stiffened as I felt his cock brush against my bare buttocks.
He sensed my apprehension and began to plant soft kisses on my ass. That helped me relax and submit to him. John began to rim me with uncanny skill. His lips and tongues worked their magic on my asshole. I cock grew hard and became trapped against the bedding and my body.
I felt his tongue penetrate me. It darted in and out of me with blinding speed. I could have climaxed from just this talented appendage. Thankfully, John mercifully removed his tongue and prepared his cock. Whatever vitality he had lost earlier had come back with a vengeance.
Looking over my shoulder, I spread my legs in an inviting fashion. I watched in anticipation as John grasped the base of his cock as if it where the hilt of a sword. With his free hand, he spread apart the folds of my ass cheeks. He placed the tip of his prick against the rosebud of my ass but didn’t enter me. The man was trying to milk the tension for all it was worth.
He succeeded. “Please, fuck me! I want your prick deep inside of my ass!”
I kept watching over my shoulder as he moved his body on top of mine. I felt the head of his cock dig deeper between my ass cheeks. He used a hand to guide his prick deeper into me. It was well lubricated by now. All he had to do was thrust.
“AHHHH!”
I shut my eyes as pain and pleasure reverberated throughout my body. I shivered with feverish delight as John entered deeper into me. I saw his manhood disappear between my ass cheeks. He filled me with his titanic length and width.
John groaned as the walls of my ass converged on his shaft. He dug deep into me until he hit an impasse. Then, he pulled out before thrusting back into me with even more fervor. He repeated this motion over and over again like a machine.
Together, we fell into a comfortable rhythm. John fucked my ass at a steady pace that wasn’t too quick. It gave me time to enjoy each movement to its fullest. With each thrust, my body pushed back to meet his action with an equal force. The pain subsided and I felt an overwhelming rush of pleasure in its place. It made me feel a little lightheaded but John’s pumping motions kept me awake.
We cried in unison as he fucked me senseless. My cries of passion spurred him to go faster and harder. I shuttered under him as his thrusts wracked my body with pleasure.
His movements soon became a blur. He pumped in and out of me like clockwork. The look on his face was that of pure bliss. It was like he had just won the jackpot all over again.
We stroked the fire in the other’s heart. Whatever doubts I had about being a woman washed away in this downpour of ecstasy. The death of his wife may have left a hole in him but I had filled it up. It didn’t hurt that I had a primal hunger for his cock.
“Oh, yes!” I moaned in delight. “Fuck me with that tool of yours!”
John stopped his thrusting and just pumped deep inside of me. I felt the tell-tale sign of an orgasm in his rock hard phallus. “Ken, I’m going to come!”
It sounded more like a warning than a statement.
He came inside me as I experienced an orgasm myself. His cock shot its load into my ass while I came on the bedding. His climax ripped through me like a hurricane. My ass tightened around his erection like a vice. I wanted to milk every drop of semen out of him. I felt his cock coat the walls of my ass with his seed.
After a good minute of coming, we were both completely spent. John collapsed on top of me before rolling over to the side. He kissed me tenderly and said. “Ken, I knew you were the right woman for the job.”
I giggled and snuggled against him. “I’m good at helping my men to hit the jackpot.”
“Are you up for making this a regular thing?”
I couldn’t believe what I was hearing. John had already changed my life by giving me a share of his winnings. I would never have to work again. Now, he wanted us to be lovers.
I knew my answer.
“Are you talking about dressing up as your good luck charm?” I teased. “Or fucking you?”
He grinned. “Both.”
I didn’t know who had won the bigger jackpot. “Done.”
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The Trans Ultra Collection Vol 3 Page 30
