A Day on the Water Pt. 03

Hello everybody! Mia back. This is part 3 of my story. Click on my profile to read parts 1 and 2.

I'm a 19 year old trans girl with a less-than-accepting family. However, my dad's friend Mike has become...unexpectedly supportive. The following is the continuation of my affair with Mike.

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I spent the next week in a daze. Texting Mike, thinking about Mike, trying desperately to resist the urge to cum. Mike had asked me to restrain myself.

"One more thing, Mia. Don't cum until we see each other. Can you do that for me?" He had messaged.

"Of course! Anything for daddy ;)" I had replied immediately, but now I was starting to regret it. I was so smooth and I could feel my hairless little cock stiffening at the mere thought of the boat trip.

I imagined how my little bottom must have looked poking out of the water and stiffened up. I imagined the moment when Mike slid his bathing suit trousers down, revealing the largest cock I had ever seen. My own little member, tiny in comparison, throbbed, threatening to orgasm at the slightest touch. But I resisted.

Instead, I prepared.

I used my vacation days to take the weekend off work at the cafe.

I told my dad that I was going to a sleepover at a friends house on Friday night. I got a grunt in response, which was about as much as I could ever get from him these days. It was my mom that surprised me. She slipped into my room at night with a little brown bag.

"For your sleepover," she said with a wink. I looked inside and saw a box of condoms, some lube, and a little note that said 'Be careful! Call me if you want to come home!' I almost cried it was so sweet.


"How'd you know?" I asked her after my dad had left for work.

"It's written all over you! You're practically glowing you're so excited. It must be a very lucky boy." She said, raising her eyebrows. I grinned in response. I didn't know how she would handle the truth, but I appreciated her so much in that moment.

"Thanks Mom," I said, giving her a big hug.

All that was left was to shower, go over my body again with a razor to ensure I was silky smooth, and plan an outfit. I decided to go with a blue pleated skirt and black tank top. Nothing too crazy, but I hoped that Mike would like it. For underneath, I was a little more daring with the skimpiest black underwear I owned. The back was just a string that hid nothing and the front was a little lace patch to keep my little member under control.

Mike lived kind of out in the countryside and his driveway had a gate out front. It was open, and I drove up to his house. As I parked, Mike was outside in bluejeans and a black t-shirt.

"We match!" I exclaimed, gesturing at the colors of our outfits. Truth be told, the butterflies were back and I had never felt so nervous in my life. Was I really about to let a man...have me? Put his penis inside me? Even thinking it caused my face to blush.

Mike looked at my outfit and split into a grin. "I'm gonna go close the gate. Go inside and make yourself comfortable."

I grabbed my purse from the car, with the little brown bag my mom had packed for me inside.

I went inside and made myself a glass of water. I'd been here before, of course, but never alone with Mike. And never with such slutty intentions.

Mike joined me a minute later.

"How are you, Mia?" He announced.

"I'm great, Mike," I replied, almost saying daddy but catching myself. It was a little bit awkward, to be honest. I did swallow his cum a week ago, and now I didn't even know what to say. I looked down at my bare feet.

Luckily, Mike had a plan. "I made reservations for Sonato, downtown. It's an Italian restaurant. Real fancy." He said, "I even bought a dinner dress for you wear, if you'd like."



"That sounds really great," I murmured, feeling my expectations shift uncomfortably from a private evening with Mike to a crowded restaurant.

"Or, I can cancel the reservation and we can watch a movie. Plenty of choices and the living room is all set up," he said, gesturing towards the couch where there was a neatly folded blanket and a bucket of popcorn.

"Movie!" I said, enthusiastic again. "But just watching a movie?" I asked, innocently biting my lip.

"Well," Mike said, shifting a little bit where he stood. "We could also talk. See where the night takes us?" He added tentatively.

"I'd like to see." I replied with a wink. "Want to see something cool?" I asked, changing the subject. Mike nodded and I got out the brown bag from my purse. I showed him the contents and he grinned.

"Went shopping, huh?" He asked.

I shook my head. "From my mom."

Mike opened his eyes in surprise. "She knows about us?" He asked, shocked.

"No don't worry. She just knows that I found a special someone. Don't ask me how. I asked and she said she could just see it on me!"

Mike laughed. "She is a special woman. That's fantastic, Mia. I'm happy for you." I jumped forward to give Mike a hug, feeling like everything was right in the world.

"So you really want to do this?" Mike asked, holding both my shoulders.

"Do what, daddy?" I asked, playing coy again and feeling a stirring in my panties.

"I'm serious Mia. Do you want me to take your virginity? I need to know you want it."

I smiled back at him. The moment of truth. Do, or do not. Was I really going to let a man as old as my father take me for the first time? I didn't even have to hesitate.

"I want you to take me." I replied and I could almost instantly see the lust in his eyes. I felt my own stomach twist a bit when I said it. It was true, but speaking the truth can be a scary thing. As I said it, I pressed my body up close to his, one hand snaking down to feel the hardness beneath his jeans and the other wrapping around his shoulder. I moved my face close to his and he moved in for a kiss, his tongue opening up my mouth.

"I can see you're eager," he said, my hand still rubbing his hard length through his pants. I blushed.

"Yes, daddy," I replied. "I want you so badly. How do you want to take me, daddy?"

"You like being submissive, don't you?" He asked, not answering my question.

"Oh yes. So much."

"Tonight you're going to be mine. You'll do whatever I ask without hesitation." He just said it. No questions. I felt my little penis grow impossibly hard in my panties.

"Whatever you want, daddy." I replied.

"Go sit on the couch. We're going to watch a movie." He said, pulling away from me and leaving my hand empty. I frowned. Not what I expected, but I had agreed already so I went to the couch and Mike joined me. He sat next to me, our shoulders touching.

The movie started. Some romance flick. I couldn't pay attention at all because I was constantly stealing glances at Mike. What did he want me to do. After a few minutes, he must have noticed my inattention because he looked over at me with a frown.

"You don't like the movie?" He asked.

"It's not that. I'm just...you know."

"No, I don't know. Tell me."

I felt my face going red again. "I'm...horny."

Mike frowned as if he was disappointed. "Did I do something wrong, daddy?" I asked, trying to look innocent and cute, hoping this would lead into the steamy sex I was craving for.

"Sit up on your knees. Next to me." He said. Again, I was confused, but I did as he asked.

"Like this, daddy?" I asked. I was now next to him on the couch, half-kneeling on my knees with my butt touching my heels. My skirt fell over my feet, affording me some modesty.

"That's right. Now pull up your skirt." I did, robbing myself of my own modesty and exposing my lacy black panties.

"Did you wear those just for me?" He asked, looking over at my bottom and reaching one hand out to stroke my cheeks.

"I did wear them for you." I said with some trepidation.

"Don't be embarrassed. It's natural. Tell me why you wore them."

"I wore them so..." I stammered, "I wore them so you would be turned on. I wore them so you would fuck me." My face was crimson.

He chuckled. "That's a good girl. I know it took courage to say that. I'm going to give you a reward." He took his big hand off my butt and moved closer to my face. "Lick my fingers. Don't worry. They're clean."

I did like he asked, licking tentatively at first and soon sucking with abandon, wishing I was sucking on his cock. I licked each finger, and when I got to his thumb he pushed it against my throat, causing me to gag and spit a little extra on it.

"Good girl," he cooed, "now keep that skirt up." I had never let it fall. My own little penis was making a tent in my panties but you couldn't see it beneath the bunched up skirt.

His hand moved to my bottom and pulled the panties to the side, letting the cool air hit my asshole. He rubbed a single wet finger up and down my crack and I moaned. "Nice and smooth down here, too," Mike laughed. "You really do want to get fucked, don't you."

"So much, daddy," I whimpered, using one hand to reach for his crotch but he slapped it away.

"Not now. Daddy's watching the movie. You just relax and let daddy make you feel good."

I did as he asked and soon I felt that slimy thumb pressing against my tight hole. He made circles at first and then gently pushed into me. I moaned involuntarily and stuck my ass out further to allow him easier access. He let his thumb sit there, pleasantly filling me for a moment, and then began to move. He didn't really move in and out, but instead sort of massaged my insides with his large digit.

The feeling was incredible. Like the most relaxing massage combined with a rising heat from deep within my belly. Soon the room was filled with my squeals and moans of delight and I was clinging to my skirt with both hands, determined to follow his instructions.

"Does that feel good baby girl?" He asked.

"God yes daddy. Don't stop please." I begged.

"Are you gonna cum for me?" He asked.

"I don't know," I gasped, "I don't know. Just please don't stop."

He laughed again. "Just enjoy it baby girl, no pressure." I nodded in eager agreement, now sticking my ass out as far as possible without falling off the couch.

The feelings were driving me crazy. It was like an itch that grew in intensity the more it was scratched. The heat was building and building and I thought for sure I was going to come but I didn't. Soon I felt like I couldn't take it any more.

"Please daddy, I can't take it anymore," I begged, tears of pleasure and frustration beginning to run down my face.

"Uh, uh, baby girl. Tonight you're mine. Whatever I want, and I want to keep going." He replied calmly, not slowing down for a moment.

The feeling kept building and now I was whimpering with the occasional cry of delight and pain. I wanted to cum so badly I was shaking, pushing my ass up and down on his thumb to try to get it deeper.

And then I felt it. Like a fire coming from deep within my groin, burning through all my desire to the end of my rock-hard little penis. I was cumming. I came for longer than I have ever come and my vision went black. I came and came and could hear the moans and cries fill the room. I wanted them to be sexier but I wasn't in control. I was just riding the wave of the most magnificent orgasm I'd ever had.

Gradually, slowly, It subsided and Daddy's thumb slipped out of my ass. I collapsed back into the couch, my panties still pulled halfway down, a wet spot forming from beneath my skirt.

Daddy let me recover for a moment. "Show me." He said, and I looked over at him with bleary eyes. Too weak to resist, I lifted my skirt and showed him my mess. My panties were bunched up but still around my cock and all over the place was my cum. Leaking through the lace and out from under my hairless balls. My cock had gone soft now, hardly taking up any space.

"Stand up." He told me, and I stood. "Take it all off." I did, feeling the shame of being exposed as I let my skirt fall to my knees and then slipped my panties off to join the skirt in a pile at my feet. I took off my tank top too, exposing my small breasts, and tossed it on the couch.

I stood like that for a moment, the movie ignored in the background. Mike just sat and looked me up and down.

"Did you like what I did for you?" He asked, and I immediately nodded. "I can see that," he continued, and reached out to stroke my smooth crotch, now slimy from my earth-shattering orgasm.

"So smooth and small." He murmured as he stroked around my crotch, exploring my smoothness. I felt my penis unbelievably start to twitch again as he stroked and said those words. "So eager," he chuckled, and I flushed red. He saw it too.

"But you're all a mess. Go change in the guest room. I laid out some clothes for you. Pick whatever you like."

I did as he asked and saw on the bed some outfits laid out. There was an elegant black dress, which I guess would have been used if I took him up on a dinner date. Then there was a pink and see through nighty, a purple leotard, a little cheerleading outfit, and a range of lacy panties in several colors.

I noticed a closet and looked inside there, too. Inside was a full collection of girls clothes. Every outfit imaginable and I grinned and had an idea.

Wearing only a pair of fairly modest cotton purple panties, I went back to the living room. "Would you like a fashion show?"

Mike grinned and the television flicked off. "Yes I would." I bounced off to his bedroom, feeling Mike's eyes on my rear end.

I went back to the bedroom and closed the door, noticing the mirror hanging on the other side. What outfit to wear first. I had a look at myself in the mirror. A little bit frazzled from Mike's 'treatment' of me earlier, but still pretty. I did a few poses sticking my butt out and soon my little penis was bouncing around as hard as a rock. I rolled my eyes, went into the adjoining bathroom, and freshened up, including splashing some cold water down there to get things under control.

With a deep breath I slipped on the black dress. After getting it on, I realized that there was a slice taken out on the side that ran from underneath my left breast to my hip. Quite stylish, Mike! I did a spin in front of the mirror. There were some heels in the closet, but I had always preferred being barefoot.

I smoothed my hair and walked out, feeling nervous again. I scolded myself internally. The man had just made me cum in my panties with his thumb up my ass! And I was nervous about showing him a dress. Abandoning my reservations, I walked out where Mike had pulled out a chair to sit facing me.

"Beautiful!" He exclaimed, "I'd hoped to get to see you wearing this tonight. Does it fit?"

"Perfectly," I replied, "and quite stylish!"

Mike grinned and pressed a button on a remote which started some music. The sounds washed over the room and I did a little dance in front of him. I'm sure I looked silly, but I felt right in the moment.

Soon I felt Mike's hand delicately trace up and down my back and I moved a bit closer, allowing him to trace the bare skin exposed by the cut of the dress.

"Naughty, naughty," I mocked, "I'll be back!"

With that, I turned and retreated into the bedroom again. I again stripped naked and put on a sexy red thong first. It barely covered anything up front and was just a string in the back. I stood on my tiptoes and checked out my ass. Firm!

Next I slipped on the cheerleader skirt, which was embarrassingly short and complemented it with a top that left my belly exposed. I quickly tied my hair into pigtails. They were a bit sloppy, but I didn't want to make Mike wait too long for me.

When I walked out, I did an exaggerated 'cheer' combo and then collapsed giggling.

"Didn't take you for a cheerleader!" Mike said, laughing with me. "But I can see it now. Can I see you a bit closer, Mia?"

I nodded and approached him in his seat again, letting those big hands run up and down my smooth legs.

"I love your hands so much," I said, and it was true. They made me feel like I was floating away.

"Thanks for doing this for me, Mia." He said, "It's like a dream come true." His hands were just below my butt cheeks and he looked into my eyes when he said it.

"I have something special underneath the skirt. Would you like to see?" I asked, feeling a surge of slutty hormones.

Mike nodded. "Show me, Mia."

I stood in front of him and lifted my skirt up to reveal the red thong. My little penis had slipped out from the fabric and was poking out to one side. Mike reached out and rubbed the sensitive head and I gasped, half in pain and half in pleasure.

"Are you sure you like it?" I asked? "It's not very big."

"Oh Mia, it's perfect!" Mike exclaimed. "Now turn around and show me the back."

I did as he asked and exposed my pale white bottom to him, gasping again as those hands slapped on my cheeks. I felt his hot breath on my ass and he rubbed his rough mouth against me. Again, I felt weak in the knees.

I had to have him. I turned and kneeled in front of his chair between his legs.

"May I please suck your fat cock daddy?" I asked. Was I really saying those dirty words?

Daddy leered down at me. "Tell me what happened earlier. How did you cum?"

"I came...from your hand. Your fingers." I said. It was true, but maybe not the whole truth.

"Where was my finger?"

"In my bottom," I replied, looking down at floor between his legs with my hands on his knees. "Your finger was in my butt."

"That's right. So you came just with my finger in your tight little ass, huh?"

"Yes daddy. It felt so good." My face burned red.

"Look at me," he said, and I did. "Good girl. Never be ashamed of who you are. Now go try on another outfit for me. I'm loving this!"

I stood up and scurried back to the bedroom. I still hadn't even seen daddy's dick! I chose my next outfit carefully. I had to choose a good one to make him lose control and stop teasing me.

It was a black and yellow leotard, like the one dancers wear. I stripped naked before putting it on with no panties and trotted back out to Mike.

"My god!" He said, leaning forward in his chair.

"What do you think Daddy?" I did a twirl.

"Magnificent! Come and sit on daddy's lap."

I happily obeyed, planting my little ass on his lap and beginning to grind around. I could feel his firmness underneath me and couldn't wait to get it out. "Ooh daddy I can feel you. I haven't gotten to play with you yet." I moaned while I gyrated my hips and tried to get his cock in between my butt cheeks. His hands were all over me, even slipping beneath my leotard to tweak my nipples. I moaned in agreement and lifted myself off him to kneel between his legs again.

"Please daddy," I pouted, "let me see it?"

Suddenly he reached out and grabbed my head, pushing it into his crotch. I could feel the heat and strength from his erect cock underneath his pants, and the sudden act of strength and domination shocked me but I felt myself twitch in the leotard.

"I have to make sure you're ready, first." He said, still holding my face to his crotch. "Go into the drawer to my left and get out the purple butt plug you find there. Will you do that for me?" I nodded my muffled agreement.

He let me go and I did as he asked, finding a moderate size butt plug with a furry tail on one end. I held it up to him with an eyebrow raised.

"Put it in." He said, and I turned to go to the bedroom to do as he asked, but he stopped me. "No. Here. Put it in. There's some lube in the drawer."

I flushed red with humiliation. He was going to make me put in right in front of him? I turned away, letting him see my butt but at least avoiding his face.

"No," he said again. "Face me." Damn it, I thought, but I did as he asked. I squeezed a dollop of lube on my hand and pulled the leotard to the side as I reached behind myself to rub it on my hole, still a bit sore from Mike's finger earlier. I used the rest of the lube to rub on the metal butt plug and held it up to gauge its size before reaching back to push it in. All while making eye contact with Mike!