Getting Coached by Mr. Hawkins Ch. 04

"Shhh, baby," Mr. Hawkins whispered as he brought his hand to my face to muffle the sounds I was making. "We don't want any more unwanted attention, do we? Kylie's got to be quiet while she takes Daddy's cock."

As hard as it was, I did as I was told. Normally Mr. Hawkins would fuck me a bit more gently, real slow and steady, but right now he was going all out, his dick coming almost completely out of my ass and back in with each thrust. As he rocked me up against the side of the boat, my own dick was dripping with precum and getting excited by rubbing up against the edge of the rail. After only a few minutes of this, I started to cum, unable to hold anything back.

"Ohhhh, ohhhh, ahhhh, yeah," I moaned, shooting ropes of cum off the boat and into the water. The force of my orgasm had caused Mr. Hawkins' dick out of my ass, and I soon him grunt that he was cumming as well. Warm cum sprayed down my back and all over my freshly fucked hole. Mr. Hawkins grabbed my shoulders with his strong hands and turned me around.

"Clean me off, slut." I did as I was told, dropping to my knees and gobbling up the rest of his seed as I caressed the cock that had just been deep inside me. After I'd finished polishing him, Mr. Hawkins fetched a towel to wipe both of us down, and we headed back to the cabin.

Upon our return to the cabin, we both needed a good rest after our afternoon activities. Mr. Hawkins threw on some athletic shorts and I slid into a pair of pink cotton panties before we laid down to spoon in the master bedroom. It didn't take long for me to fall off to sleep -- I don't know if Mr. Hawkins had slept at all, but when I woke up the sun was already starting to go down, and I felt extremely groggy. I glanced at the bedside clock and saw that it was 7 o'clock, so I must've slept for about three hours. There was no sign of my man, but then I noticed an outfit laid out on a chair across the room. There was a ginger wig, a matching black bra, thong, and thigh high stocking set, plus a light blue floral print dress. I put everything on, admiring myself in the mirror as my bulge became more apparent under the dress. The dress barely covered my ass and I loved how on display I would look for Mr. Hawkins. I gave the mirror one last mischievous grin before I headed for the kitchen.

As I walked in, I could smell the pasta that Mr. Hawkins was making, and his back was to me as he attended to the stove. As quietly as I could, I snuck up behind him and grabbed Mr. Hawkins around the hips and made a move for his crotch.

"Whoa! You startled me there," he exclaimed as some of the pasta water spilled out on the stove. He feigned anger, but as he turned around to greet me I could tell he was excited by my playing dress up. "You're looking pretty good there, darling. I guess you didn't mean to startle me like that, so I don't need to punish you too hard," he purred, grabbing my ass firmly.

"Whatever it takes so that I learn my lesson, daddy," I replied, staring up into his blue eyes.

"Well in that case..." Mr. Hawkins reared back and slapped my behind a few times, each one adding to the sting I felt, yet somehow getting more pleasurable. I moaned for more, but he held back.

"I think we need to eat our food before it gets cold," he said, leaning in to give me a soft kiss on the lips. "But if you still need some punishment, I'll make sure you learn your lesson."

We sat down for dinner, making conversation about how the next school year looked for both of us. I could tell Mr. Hawkins was trying to keep me relaxed by talking about normal things. Although we'd already had sex a handful of times, and I'd been roleplaying as a girl most of the day, something about this experience made me feel like I was completely submitting to a new way of life. And yet, the lingerie and women's clothing that I had on felt so good, so right, that I found myself getting horny again.

"Kylie," Mr. Hawkins interrupted, bringing me back from my internal thoughts. "Honey, your pasta's getting cold. You don't like it?"

"Oh, sorry daddy, no it's great. I'm just..." As I trailed off, I found myself lifting my stockinged leg up to his crotch and massaging it. He flashed a grin.

"I see, you're just ready for dessert. Well we can always put the rest of it away as leftovers. Why don't you just be a dear though, and clean up in the kitchen. I'll just, uh, do some other work around the house."

After clearing the table and putting leftovers in the fridge, I set about washing our dishes and the pots used to make the pasta. I actually got so into cleaning that I almost forgot I was in costume, and when I glanced down to see I was still in a dress, I realized I was perfectly playing the part of a housewife. After a few minutes I was starting to get a little sweaty, when from behind I felt two firm hands grab onto my shoulders.

"Mmm, daddy likes seeing his girl so eager to clean. Stay right there and finish up, and I'll do some cleaning of my own."

Wanting to follow his commands, I stayed standing right in from of the sink, scrubbing the last pot I had to do. I felt his hands work their way down by back, massaging as he went, before lifting up my dress and exposing my ass.

"Oh what a pretty little peach this is. Think I've found what I'm having for dessert."

With that I felt my thong being pulled to the side, the kitchen air hitting my sensitive asshole. I needed this. Suddenly I felt a sensation of wetness, Mr. Hawkins spitting on it before circling with his tongue, probing me, teasing me. The entire area around my asshole was now covered in saliva, and the tip of his tongue was lightly trying to work its way inside me. His hands dug into my cheeks, rubbing them as he continued to tease my hole. By this point I couldn't concentrate on cleaning and was simply bracing myself against the counter trying to keep myself together. I was fully hard, my cock now making a tent in my dress, and I could feel precum leaking into my lace panties. I began moaning, my legs quivering. Mr. Hawkins brought his hands to my hips and stopping rimming me.

"Looks like you're having trouble concentrating on what I asked you to do. I think I need to punish you for that."

Mr. Hawkins stood up and dragged me by the arm towards the bedroom. He had never been this rough with me before, so I didn't know how far he was going to take it. Upon entering the bedroom, he sat down on the edge of the bed and motioned for me to get on his lap. I started to swing my leg over his to straddle him, but he stopped me with his powerful arms and forcefully moved me so that I was sprawled out across the bed with my ass right in his lap. Mr. Hawkins reached up into my dress, peeling my thong off, and I could hear him sniffing it.

"Mmm, tastes good." He leaned over towards me and grabbed me neck to face him. "If you're going to cum in these panties, you're not going to waste it."

He brought his finger to the spot where my cum had stained the thong, before sliding it into my mouth. It was sticky and salty, and I loved it.

"Yeah, you like that, don't you?"

"Mm-hmm."

"Then you'll want to keep that taste in your mouth, won't you? Keep these here while I finish punishing you."

With hardly any warning, the thong was stuffed into my mouth, the taste of cum and fabric enveloping my throat. I gagged a little on it, but tried to maintain my composure in order to please Mr. Hawkins.

"Yes, Kylie, that's a good girl."

He readjusted his position so that my ass was once again square in his lap. He brought his hand back, and I felt a gust of air as he slapped down on my bare buttocks. I cried out in pain, but the sound was muffled by the panties in my mouth. Again and again he did it -- crack! crack! crack! I was feeling equal amounts of pain and pleasure, the endorphin hits being interrupted by the sting of his manly hand. He slowed his pace down, beginning to alternate rubbing my cheeks in between spanks. I could feel my skin starting to turn red and raw, and I needed something else to distract me from the stinging feeling. I spit out the panties onto the bed.

"Please, daddy," I panted, "I need your cock."

"Oh, really?" I glanced back and saw him reply with a smirk and raised eyebrow. "Do you think you deserve that? You think you've learned your lesson?"

"Yes, daddy, I promise to follow your instructions. And I won't flirt with any other boys, your cock is the only one for me. I'm your personal slut."

"Good girl," he moaned, "I suppose you've taken your punishment well. Now get that mouth over here.

With the same ease that as he had thrown my upper body towards the end of the bed, he now brought my face back to his crotch to meet his dick. I immediately started licking the underside of his shaft, eliciting moans that made me feel like I still had a little bit of power over Mr. Hawkins. I could fit the head of his cock in my mouth, though not much more thanks to its girth, but gravity forced me further down than I could comfortably handle. I choked a little, which brought great enjoyment to him.

"Mmm, yeah, when you choke on it, that makes the best lube."

As I continued sucking Mr. Hawkins, he leaned over to the bedside table and opened a bottle of actual lube, squirting it on his hand before parting my ass cheeks with his middle finger. He started to work it in little by little, meeting resistance from my hole but maintaining pressure to slowly open me up. I pushed out, doing my all to accept his finger. Finally my resistance was broken, allowing the finger to enter me fully, and as he worked it in and out, I felt like my hole was gaping.

"I'm ready, daddy," I whispered.

Mr. Hawkins slid his finger out of my asshole and lined me up so that I was face down with my head on a pillow at the top of the bed. I arched my hips back in anticipation. I heard him open the bottle of lube once more, the cool sensation giving me chills as he applied more to my hole.

"Oh, this pussy looks good," I heard him moan, starting to work his cock into me. Even having been loosened up by his finger, I still had to adjust to his cock head, and I pushed out in order to overcome the resistance. Normally Mr. Hawkins would go a bit slower, but this time he was pressing down on me with more of his body weight, forcing himself inside my boy hole. We both moaned in unison, he in extreme pleasure, me feeling both pleasure and pain, and muffling the sounds in the pillow. He eased his weight off of my backside, bringing most of his cock back out, before slowly easing back in.

"Mmm, that's it," he groaned, "that's a nice pussy." I could feel my ass clapping against his torso every time he bottomed out in me. I was still lying prone when he lifted me off the bed and had me support myself with my hands, in more of a regular doggystyle position. He brought his hands around to find my nipples, massaging them in a circular motion and he continued to slowly fuck me. It felt so good.

Next Mr. Hawkins slid out of me and repositioned us so that he laid down where I had been, motioning for me to start riding him. I climbed aboard, easing his cock back into me, despite gravity wanting me to take it all at once. Once I was comfortable I started bouncing up and down, my own dick showing its excitement my continuing to leak precum.

"Oh wow, look at how wet you're getting, babe."

"I'm so wet for you, daddy."

"And your little clit isn't so little, it's so big and swollen."

"Your big cock just turns me on so--ahhh, ahhh, oh that's good, oh I love your cock!"

In one motion he took me in his muscular arms and flipped me onto my back, staying inside me the entire time. At this point he was really able to jackhammer me with his powerful hips, filling me up as deep as my ass could take. I wouldn't be able to last much longer.

"I'm getting close, Daddy. You're going to make me cum so hard," I panted.

Mr. Hawkins simply smiled devilishly, before he began lightly touching my cock head. It only took a few strokes to put me over the edge, as spurt after spurt of cum came flying out, covering my chest and even hitting me in the face. As my orgasm tried to push Mr. Hawkins out of my ass, he pushed back in, continuing to stretch my quivering hole. As he leaned in to kiss me again, our chests met and my cum caused us to stick together. We sloppily made out, and he licked his own cum off my chin as we swapped it back and forth in our mouths. Suddenly I felt Mr. Hawkins start to tense up, and he moaned uncontrollably.

"Oh Kylie, oh baby, I'm gonna...I'm gonna fill you up baby!"

Cum flooded my asshole as he orgasmed, seeming like it would never stop. After holding his dick inside me for probably 20 seconds, he slowly eased out, and the pleasure I'd felt while getting fucked started to turn into pain and soreness. He had wrecked me. Little by little the cum started to drip back out of me, and Mr. Hawkins ran to get a washcloth to help me clean up the mess.

I managed to make it to the shower to wash off all the accumulated sweat and cum, and stumbled back into bed. Mr. Hawkins held me in his arms, and within a minute I was fast asleep. I needed to recharge for the rest of the weekend, but I knew my first day as a crossdressing girl had gone pretty well.