A Sissy's First Time with Daddy

I put on the long-sleeve leopard print body suit that went all the way up to my neck. Adjusting so it would contain my penis, while making sure the back still went up my ass. I wasn't entirely sure I'd let anything else go up there tonight. But I did grow to love a thong.

I posed in the bathroom mirror of my hotel room. I looked good and felt better. Then I lifted my right leg onto the counter as I carefully rolled up a red nylon. Repeating with the left and securing them with a garter. The long sleeves and nylon would cover my hairy arms and legs. I wasn't full femme, still appreciating some of my masculine traits. As I could tell from my throbbing manhood, those masculine traits had long been craving some feminine identity.

Then I hiked up the tight red leather skirt, which made my leopard print body suit appear more presentable for the public. This was a good look for a first date, although I'd have to take time after to change into lingerie. Which wasn't a problem. Showcasing more of my wardrobe was part of the point of things tonight.

I looked at my face. I had trimmed my beard and it fit well with the leopard print. Makeup had never suited my face, but I needed something feminine to add to the ensemble. I never felt the need for a wig, although I was bald so I couldn't do anything with my own hair. Luckily, I had recently bought a new red headband with a large, frilly bow on the side. I delicately put it on and felt fierce. It was one step below too much, and I halted my impulses to add anymore decorations.

Final step was sliding into my leopard print high heels. Completing the alternating pattern of animal print and striking red. Despite not being naturally attractive by male or female standards, I felt really sexy. There was a knock on the hotel door. In heels, I carefully walked in my new shoes to open it.

On the other side was my date, Mac. Over twice my age, which was another fantasy to explore tonight. I had long watched old man pornography online. While I initially watched for the women, I grew an appreciation of their aged bodies. Mac was "my type" that I had never acted on before.

He stood there, in a nice black shirt that flattered his enormous width and belly. The shirt was unbuttoned a few notches, showing off some gray chest hair. Beneath a belt, closed at its final loop, was a pair of very tight dress pants. Mac was holding a bouquet of roses.

"For you," he smiled, checking me out. I instinctively took on more feminine poses as I was genuinely shocked by the sweet gesture. He passed them to me, as I accepted a tender kiss on my cheek. During which he pulled me in and I could practically melt in his cuddly, strong body.

Being in a hotel room I naturally didn't have a vase. So I walked to the large bed and delicately placed my gift. Making sure my ass was properly presented to my prey.

"These can hold our place for later." I seductively promised, making my intentions clear. Mac had an enormous smile that I wanted to feel against my face. Ever the gentleman, he held out his arm to assist me in walking to the bar attached to the hotel.

My fears of being a clear man crossdressing raced a bit as we entered the hallway. But Mac's confidence in me began to assuage those nerves. For my first time presenting in public, I traveled to a place where I wouldn't be recognized. Mac was still a stranger I met online, but we'd been flirting enough to make me feel secure.

I won't go into much details about dinner, as that wasn't my primary goal of the evening. But it was important to me. To feel that I was being desired by Mac. To see his interest in me beyond an easy lay. There was a giddiness growing inside of me, as another part of me was also growing in anticipation.

There was also something sexy about watching this heavy man devour his dinner. Being insecure of my own body and identity, I had no interest in dating a perfect body. But Mac was content in his large form. And he was interested in the form I had chosen. Watching him eat also got me heated to grab that enormous belly he was working to increase.

I avoided alcohol as I didn't want to have to also worry about any performance issues, beyond my own inexperience. Which was great as my inhibitions were naturally becoming free. Gradually I lost awareness of our age difference, or my own identity. This felt natural as I instinctively played with his foot under the table.

After dinner, my date pulled out my chair and assisted me to stand. I leaned forward for our first kiss on the lips. He instantly accepted, and pulled me in for another one. More deeply this time. There was no question. He was about to get it.

We burst through the door of my hotel room, having started making out heavily in the hallway. His heavy body felt so good. I loved clasping fistfuls of fat around his sides. I felt like I was going to melt and held myself up with my arms around his neck. He pulled me close, hands strongly affixed to my ass. I could feel his throbbing dick against my own.

Taking a break for air, I pushed him onto the bed. The bouquet of roses bounced off, although we weren't thinking about flowers. I kicked off my heels as I seductively pulled down my skirt, revealing the bottom part of my leopard print bodystocking. My hard cock visible going up towards my stomach.

Mac sat on the edge of the bed and I positioned myself on top of him. Bouncing with excitement. I slowly unbuttoned his shirt between licking new portions of his sagging skin. Once the shirt was entirely off I clawed at his bare torso and stomach. His nipples were begging for me to lick. All while I could feel his hard cock near my asshole. A brand new sensation that was literally growing on me.

The experienced lover leaned back on the bed, and I bent over to continue making out. Fuck, his large body felt amazing. Next I worked on undoing his belt, freeing the entirety of his fat. I moved off the bed, pulling off his pants as my tongue ran down his leg.


Standing up, looking down at this silver stud, I was pleasantly surprised to discover he was wearing tight pink lace panties. He noticed my reaction.

"I love pink." Mac smiled.

"Is that right?" I asked, kneeling on the floor as I examined his delicate lace with a cock firmly pushing against it. "Could you wait a second? I want to slip into something pink for you to love."

Mac grinned and nodded with excitement. I crawled on top of him and tongued him deeply. I was loudly moaning and I grinded against his already sweaty body. Getting up, I paused crouching with my ass facing him. He dutifully spanked it as I skipped to change in the bathroom.

As soon as possible, I exploded out through the door wearing my brand new hot pink lace garter lingerie set. My neck was contained by a choker strap and leading down to a bralette. That was attached to a garter belt, leading down to straps around my legs. I didn't bother with this underwear. Mac looked excitedly at my hard cock.

I approached him by crawling on the floor and removed his panties with my teeth. I licked my way back up his legs and started exploring his saggy balls with my mouth. His manhood was only slightly bigger than mine, with my penis only being about average. Finally, I put my very first cock in my mouth. I moaned as I clawed at his fat rolls. I licked and sucked his hard cock as if it was second nature.

Mac moved me up to him on the bed, deeply kissing me as he gave me a serious handjob. I returned the favor. We were both rock solid and close to exploding.

"I like the way you lick me." Mac whispered into my ear between kisses. "Could I turn over?"

I pushed him onto his side and put my head against his ass. It was enormous and I buried my face while moving my tongue around his asshole. He moaned in delight as he continued to keep his dick hard for me.

There was an unmistakable sound as Mac stood up. He was ready and I fell to the floor, landing with my mouth back on his cock. I sucked like crazy while fondling his balls. He soon went off like a rocket inside my mouth. I clenched to his meaty thighs as my mouth was stuck on his cock like a rider staying on a bucking bull. My cheeks expanded with his huge load. I sucked up and down, licking up as much as I could. It dripped out of my mouth, as I coated my beard with the jizz still on his cock.

Mac collapsed satisfied onto the bed. I looked up with excitement as I played with his cum in my mouth. There was so much that I drooled down onto my chest. I was all smiles as I licked my lips and swallowed what was left.

"Thank you." I said with a huge smile. Not a normal response after sex, but I had felt truly grateful.

"Would you like to return the favor?" Mac requested, helping me stand up. I wasn't sure what he meant, but he nodded down at my cock that was still hard. I couldn't believe I forgot about my own completion. I was so satisfied by his.

Mac laid down with his head on the foot of the bed. I stood over him as he pawed at my cock, nearing ejaculation. I bent slightly as he licked it. Quickly, I positioned myself so I could shoot it into his open mouth. He took it gracefully without flinching. I collapsed next to him and his large fists cleaned up the remaining jizz off my satisfied cock. He rubbed it around his chest as we looked each other in the eyes.

"I can't believe I finally did this." I admitted without worry. Mac pulled me toward him and kissed me on the neck.

"Would you do it again?" Mac asked with his eyebrows raising? I nodded as he got up to get us water.

After more fooling around, we cleaned each other up in the shower. Which is another amazing experience for another time. I completed another wardrobe change into a pink silk nightie. Lying in bed together I spooned my new lover. His large body was so comfortable and cuddly. We kissed once more deeply before sleeping together.

In the morning, Mac woke up before me. I didn't notice until he returned to the room, holding a gift bag.

"Where did you go, babe?" I moaned, still somewhat sleepy.

"I had to get something out of the car for you." He said as he sat next to me and pulled me towards him for a good morning kiss. I immediately sat up, excited. "Are you awake enough to premiere it for me?"

I nodded vigorously and exchanged a kiss for the gift bag. Bouncing out of bed, my lover spanked me as I pranced to change in the bathroom.

In the mirror, I viewed myself in my newest sissy clothes. A pink bikini with the words "Come Here Daddy" on the front of the top. On the front of the bikini bottom it said "Please". Turning around I caught a glimpse of the back of the bottom which said, "Yes, Daddy?"

It felt amazing. I didn't even miss the feeling of a thong in my ass. The words on my body felt even better. This was the start of something new, and I couldn't wait to see where things would lead with Mac.

Exiting the bathroom, I leaned against the wall as I posed for my sexy daddy. He was wearing a black speedo. I stood in awe of his glorious mountain of a body that I couldn't wait to climb again. But first, we held hands as we felt each other on the way to the hotel pool.