College girl is hot to fuck, but inexperienced. "It won't fit!"
43. A Scared College Girl
My stop at the marina on the Intracoastal Waterway had been fun. I had sampled a BDSM devotee and spent some time with two of the trashiest, nastiest dive bar whores on the planet. In hindsight, I should have taken better advantage of both encounters. My perverted mind flowed to things I would have liked to have done. But, alas. It was time to move on.
Fortunately, it was high tide as I cruised out of the marina and reconnected with the Intracoastal. I didn't scrape bottom once. Heading north on the protected waters of the ICW, all I had to worry about were the numerous bridges and their inconsistent opening schedules, other boats and getting bored silly.
For those of you who have never traveled the Intracoastal Waterway (the "ditch", as it is called) it is varied. At some points it is wide, in excess of a mile or more. In other areas it is less than a hundred yards wide. In some sections, the banks are undeveloped. No buildings, just marsh or scrub or mangroves. In others there are concrete seawalls on either side, lined with houses, mansions, condominiums, each with their private docks.
North of Miami, in the Ft. Lauderdale/Palm Beach areas, the ditch is lined on both sides with enormous mansions, each with a mega-yacht at the seawall and most sporting "Trump" signs. This is the epicenter of Trump country. An embarrassment of obscene wealth on full display. The farther north one goes, the smaller the houses, the smaller the boats and there are fewer Trump signs.
But I digress. My challenge was to avoid hitting other boats, stay awake and find safe places to anchor. Along about midday, I turned a bend in the channel and saw a draw bridge about a mile ahead. Shit! It was just closing! My reference charts indicated that it opened on a half hour schedule. Fuck! I missed it by minutes! Damn. That means I had to either drop anchor for a half hour or try to remain in position against the current. Dropping the anchor is dicey because of all the small power boats zipping past. Sitting mid-channel is not ideal in such a situation either. Neither option is good.
Then I saw an out. There was a small restaurant on the starboard bank on my side of the bridge, with docks for passing boaters to stop and have lunch. Being midday, this was perfect. I could stop, have lunch, then time my exit with the bridge raising.
I pulled into an open slip. There were two problems. First, it was rather shallow and I bumped bottom. Second, the slips were all designed for boats much smaller than mine. With my boat pulled fully into the slip, my ass end stuck out about 15 feet. Not my problem I thought. I tied off and went to the hostess station to be seated.
An attractive college age beauty greeted me. "Welcome, Captain. Everybody was watching you dock, wondering how you were going to fit your big boat into such a small slip. We all agree that you did an excellent job."
"Why, thank you. I've been boating my whole life. There's not much I can't handle. And compliments from someone as attractive as you are always welcome."
Her cheeks flushed at my reference to her beauty. "Would you prefer to sit outside or in?"
"Wherever I can keep an eye on my boat. And you."
She seated me outside at a table right next to her station. I gave the menu a quick once over, then turned my attention back to the hot young hostess. She was adorable and easily a 9+ on a 10 scale. I couldn't take my eyes off her and she noticed.
Standing about 5'6", her honey blonde, shoulder length hair was pulled into a ponytail. Her almond shaped face was enhanced by pretty, wide set eyes, hazel in color. She wore a loose fitting blouse with no bra. The top few buttons were stylishly left open allowing an occasional glimpse of her firm breasts. The material was very shear. As she moved, her large, dark areolas pressed against the fabric showing themselves to the world.
She wore a short, tight skirt. When she dropped her pen she didn't crouched down to retrieve it. No, she bent at the waist giving me a clear view of her finely shaped bottom and the G-string she wore as "underwear." I got the feeling that she was either showing off or flirting with me.
After I placed my lunch order she answered that question. She would catch me staring at her and give me a knowing smile. She knew that I was mentally undressing her and she liked it. Things kept "accidentally" falling from her hostess stand and she kept flashing that tight, nicely rounded ass at me. The G-string was pulled tight between her pussy lips, splitting them and putting her generous labia on display.
Eventually she struck up a conversation. Initially it was inane drivel, meaningless small talk. I started asking more invasive, personal questions. "You’re obviously very attractive. Don't you get tired of guys hitting on you constantly?"
"Well, thank you for the compliment and, actually, no. It helps me overcome my negative self image and insecurities. I've noticed you watching me. I like that. It makes me want to get to know you better."
"Well, honey, I'd love to get to know you better, too. But I doubt your boss would like my boat sitting here for more than an hour. Plus you're working. Looks like we'll have to be content just staring at each other."
She gave me a wry grin and a look that signaled victory. "Actually, my dad owns the restaurant. I have him wrapped around my little finger. After you finish eating, if you want, we could go talk. I have my own apartment upstairs over the restaurant."
I haven't eaten a fish sandwich so fast in my life. Seeing that I was finished, she disappeared inside. In a few minutes she returned with her replacement. She tossed her head, indicating that I should follow her. She led me around back. As I followed her up the stairs, the view up her skirt was erotic. She had removed her G-string. There was no hair, just her young slit and protuding pink labia.
The apartment was tiny, basically one room and a bath. She kicked off her sandals and released her ponytail, bending her head and tousling her hair. It cascaded around her face. This new frame made her even more attractive. She dipped her head making her pretty hair spill across her face. Her eyes adopted a sultry tone.
In a soft but husky voice she said "I don't normally do this but you are a magnet. All I can think of is having you fill me with your cock." She moved closer, unbuttoning her blouse as she narrowed the gap between us. In one smooth motion she leaned in to kiss me and grabbed my wrist, guiding my hand to her bare breast.
I felt a spark when our lips touched. Her tongue searched for mine and her hand found my growing penis. She was super attractive, an excellent kisser and wanted to fuck me. That's a trifecta in my book.
We kissed as I fondled her tit. Our lips and tongues rubbing against each other got me started. My hand, squeezing her breast, while my fingers rolling her hard nipple had my dick fully engaged. As we continued kissing, she unbuckled my belt letting my shorts find their own way to the floor. Her hand was now stroking my cock, rubbing the precum around the tip.
She broke our kiss. Through slow, heavy breathing she quietly said "I want to ride this handsome cock. Would that be okay?"
Every fiber in my being wanted to scream "YES!!! HURRY!!!" Instead, I calmly replied "I want you to suck him first." I lay on her bed and she crawled between my legs. My rigid dick was standing upright, throbbing with excitement. It wanted to feel her wet mouth surround him. I wanted to see him disappear into that pretty face.
She hesitated. "I'm not that good at doing this. I've only tried it a few times. And yours is bigger and fatter than any I've tried before." She bent down and tentatively kissed my glans. She put just his swollen mushroom head between her lips. It looked big for her mouth. She tried to take more of him inside, but you could just feel that she was tentative and scared.
"Don't be afraid. He won't hurt you." With that I grabbed her head and pushed 3 inches into her mouth. She tried to pull her head away but I held it firm, pushing another couple inches in. She kept her mouth tight and I was feeling it. Still holding her head I stroked what she had in her mouth in and out, pushing her head down on him. Once she realized that it wasn't as bad as she feared, she loosened up some. I took advantage by seeking greater depths, finally getting about 6 inches sliding in and out. Her mouth was sloppy now and I'd let her pull off to spit her drool. Then right back on him.
Watching her pretty face devour my dick was a big turnon. Hoping to give her some encouragement and confidence, I spoke up. "That's it honey ... take that cock in your mouth ... it feels so fucking good ... just keep him in there ... you're doing great honey ... damn that feels good ... rub your tongue on the underside ... yes, like that ... oh, shit ... that's wonderful ... you're a natural honey ... you're good."
As pretty as she was, I'm surprised that sucking cock wasn't her speciality. She was obviously a rank amateur, yet it felt good and the visual was worth a mediocre blowjob.
She was now bobbing her head up and down on my cock on her own, stopping now and then to release her pent up drool. At one stop she looked up at me. Her eyes were asking if it was okay to stop, if I was satisfied. I said "Okay, honey, now let's try that sexy, tempting cunt of yours. I've been staring at it since I met you. I want to find out if it fucks as good as it looks."
She climbed on top. Reaching between her legs she rubbed him between her swollen pussy lips. She was wet. Very wet. I let her control his entry into her young cunt. She lowered her pelvis very gently, very tentatively, getting him inside her lips but just to her vagina. "Oh, shit ... Goddamn ... I don't think he's gonna fit ... shit, shit, shit ... he's too fat ... he'll never fit in there."
With her sitting upright on me, I saw near terror in her beautiful face. It was all scrunched up as she tried to get him in, pushing until it hurt. I grabbed her tits, kneading them, pinching her hard nipples hoping that would help. She was struggling, obviously afraid of having my fat dick inside her pussy.
I saw no other way to get to pound this lovely young thing than to just take her. I put my hands around her slender waist pressing my dick upwards slightly right at her hole. Then I simultaneously thrust upward and pulled downward. She was wet enough, he pushed right into a swollen, tight cunt. Goddamn it felt good!
When I impaled her, she squealed "Whoa, fuck! Oh, my God! Motherfucker! He's so fucking big! Jesus! I can't take it!"
As soon as I started rocking my hips, sliding him up her pussy, her protests turned to groans of delight. "Oh, damn ... oh, I like it ... I can feel him stretching me wide open ... shit yes ... yes ... fuck that's feeling fine."
She took over and began bouncing on my cock. Her hands on my chest, she raised up, then slowly relaxed downward. But she still wasn't getting all the pleasure my dick has to offer. She was only taking about 4 inches. I'm a greedy bastard and I wanted my whole cock to enjoy this lovelies tight, still swollen cunt.
I pulled her forward pressing her glorious boobs against my chest. As I began thrusting him in deeper and deeper, her gasps grew louder and louder. As I slammed my dick all the way in, balls deep she grunted "uh ... unh ... uh ... oh, Jesus ... unh ... unh ... shit ... it's so hard so deep ... uh ... uh ... it feels so good ... but ... unh ... uh ... you're stretching her so wide."
I was hoping for a squeal of delight as she reached nirvana. It never came. So I finished getting myself off inside her fuck hole. I jackhammered her tight pussy, hearing her groans, until my cum blanketed her insides.
When my spasms stopped, she rolled off. In one last attempt to elicit an orgasm from her, I rolled on my side and put my hand on her clean shaven fuckbox. My cum was still dripping out and she was breathing hard.
My cum lubed fingers found her engorged clit. It was big but not huge. I worked some magic on it with my fingers, massaging it and squeezing it. I ran my fingers in circles around it, batting it side-to-side. She responded with appropriate oohs and ahhhs. As I increased the pressure and intensity, her hips started twitching and bucking.
When I pushed two fingers up her cunt and started a fast finger fuck, that did it. Her hips bucked up wildly, she squealed with delight, and her pussy juice mixed with my leftover cum.
"How’s that for getting my big boat into a tiny slip?"