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For the rest of the vacation, Scott and Sarah continued to get it on in every way possible. She even lost her “anal virginity” during the week. After experiencing the butt plug the first night with Scott, a couple of nights later she greenlighted him to lube his big dick up and “get it up on in her;” and boy, did he ever. The butt plug was one thing, but his thick shaft stretching her anus was another thing altogether.
Sarah adjusted quickly to her “first timer’s pain” and then enjoyed the pleasure that followed. She really loved anal and it surprised her. She felt good about having all three of her holes available for Scott to enjoy and cum in.
“I never thought I’d enjoy butt this much,” she mused. “I guess I’m a real cock whore now that I’m sodomized! Bye, bye, miss little good girl!'” She was having so much fun exploring her wild side that had so long been suppressed.
Her favorite thing was to lie back on Scott’s hard chest in reverse cowgirl, his cock deep in her ass, looking at her pussy in the mirror and vigorously fingering her clit. It was so erotic to see her anus full of cock with her pussy available and waiting for his cock to return to it. She got turned on just watching him switch his cock back and forth between her ass and pussy, and she felt really dirty, but in a good way.
At times during anal, Sarah would switch from using her fingers to masturbate and utilize the Magic Wand she’d recently purchased online. The Wand felt especially good on her clit while her ass was being stuffed. Her orgasms from this were intense indeed!
Finally, the vacation unfortunately came to an end. Sarah and Scott had to return to their homes and resume regular life. They vowed to keep in touch, and when Scott’s airline job brought him near to Sarah’s city, they’d get together and “get reacquainted.” Sarah liked the idea of her handsome, wellendowed Captain landing his plane and then taxiing all the way into her waiting, wet pussy.
“Mmm,” she thought, something to look forward to as she slipped her hand inside her thong panties and fingered her slit in the airplane commode during the flight home. “Gawd, I’m so horny!” she mused.
When Sarah returned home, she went over to her mother’s for lunch. Mom wanted to know how everything went, including whether she had any “fun” during her vacation. Sarah knew fun was mom’s code for, “Did you put the condoms to use that I gave you?”
Sarah wasn’t sure how much to tell her mom about her new lover, so she proceeded cautiously, just sharing about the resort and what she did most days there. She finally got around to her meeting Scott.
Mom’s attention heightened. “Ooh, tell me more about this Scott!” Mom cooed.
“Well,” started Sarah. “He’s tall, muscular, handsome man with a great job—an airline captain, in fact.”
“Oooh, making some good money there!” mom chimed.
“We met at the bar my first night at the resort, one thing led to another, and yes… (pause for effect) the condoms were used!”
“Oh how wonderful, honey!” mom clapped. “Was XL the right size for Scott?”
“Yes, mama, he’s a BIG man…biggest I’ve ever been with!”
“Beats that dip you were married too,” mom apologized for calling Sarah’s ex that, but Sarah said that’s EXACTLY what he was, “A prick with a little prick!” Both women laughed.
“Sarah, so happy for you. Is Scott a good lover too?”
“Yes, he’s gentle with me until it’s time to dominate, then he lets his big cock just take over and have its way with me!” Sarah giggled now, getting into sharing more lascivious details of her liaison.
“Mmm, you’re starting to get me turned on just picturing my ‘little girl’ getting dominated!”
“Mom!”
“Well, honey, your mom has some experience in this area, even though it was back before I met your father. Your mother was a little bit of a ‘bad girl’ before she was a ‘good girl.'”
“Really?” feigned Sarah.
“Honey, I had my share of big penises back in the day. I remember one was a white guy named Brad, and the other a black guy named Jeremiah, ebony and ivory!” giggled mom.
“Seriously? You fucked a black man, mom? Really?”
“Yes, really.”
“Oh wow, I’ve got to process that one a bit,” laughed Sarah feeling her pussy moisten at the thought of mom “going black.”
“So, when’s Scott supposed to fly into town?” mom inquired.
“Not sure, his schedule is set right now, and he doesn’t come this way,” Sarah replied. “But when he does, he’ll be laying over for the night, in more ways than one,” Sarah laughed.
“Oh good, will I get a chance to meet him?”
“I think that can be arranged,” Sarah said with a wink.
Meanwhile, Scott was back to flying his regular schedule with his airline. He really missed Sarah, and he couldn’t quite put his finger on why; after all, he’d fucked a lot of women in his twentynine years; and in fact, one of his favorite pussies, Chastity, was on this flight with him. They’d be laying over the night, and it always meant he’d end the evening balls deep in her hot holes.
Twentytwoyearold Chastity was one of those flight attendants who really loved her job. She had a way of connecting with passengers, especially the male passengers. Before each flight, she liked having her hair and makeup done professionally, if at all possible; and with the various hairstyles and lipstick shades she sported on flights, they alone were enough to make men up and down the aisles rock hard.
However, Scott got to experience what the male passengers did not, and that was having Chastity leave lipstick rings—red, pink, purple—lined up and down his swollen shaft after one of her heavenly blowjobs. Miss Perky, Friendly Flight Attendant was actually an incredible cock gobbling whore.
It also didn’t hurt that Chastity had one of those slim, yet curvy figures men loved: firm, goodsized breasts; tight, round ass; and long, shapely legs sheathed in y thigh highs that were part of her flight attendant uniform. Many times, Scott had after landing and getting to the hotel, just fucked her while she was still in uniform, unbuttoning her shirt, pushing up her bra, unhooking her skirt, sliding her panties to the side, and inserting his big cock in her waiting slit. He’d lost count how many times he’d pounded her senseless like that. Tonight was just going to be another one of those nights stuffing Chastity.
In the hotel room, after some foreplay and straight in missionary position, Scott shifted Chastity into doggy and gently pressed her face down on the mattress. He then raised her tight, round ass high in the air as he got ready to drill her soaking wet cunt, which he then proceeded to do with vigor. Chastity’s moans filled the hotel room.
He was just about to pull out of her pussy to insert his cock in her anus when his cell phone vibrated on the nightstand. The name of “Sarah” flashed across the screen. He was glad Chastity was too lost in her pleasure to notice. He quickly got his dick deep in her ass while she moaned heavily, and then he went to work her ass turning the moans to groans.
As he began to fuck her harder, Scott subtly slid the phone off the nightstand. It was a pic of Sarah’s pretty face with her tongue suggestively sliding along her lips with the caption, “Thinking about you tonight!” It made him even harder as he pulled out of Chastity’s ass to resume pounding her tight pussy, all the while pretending it was Sarah’s cunt instead.
He laughed to himself, “Chastity will never know the difference,” as he slid all the way in and began thrusting hard. Chastity confirmed he’d hit the right spot with her moans and groans, and also her pussy making that loud “fapfapfap” noise with each hard thrust, just like Sarah’s did during the vacation.
Scott pulled out of Sarah’s pussy, er Chastity’s, spun her around so her open mouth was close to his engorged cock, stroked it, and unleashed a torrent of cum into Chastity’s mouth. She gagged as it filled her mouth and spilled out over the corner of her lips, then smiled at him with her eyes and swallowed the prize.
“Fuck, Scott, that was a lot of cum. My god, I couldn’t keep it all in my mouth! You were Mr. Manly Man tonight!” as she wiped the residue from her chin with her fingertip and then swallowed it too. “I’m glad you didn’t cum in my pussy or I’d definitely be preggo after that gigantic load of semen,” she giggled.
As Chastity got up from the bed to go clean up, Scott noticed that she had runs in both legs of her thigh highs, apparently from placing his hands on her calves during their rough doggy while he was thinking about Sarah.
“Well, that had to be a first; never seen that before,” Scott mused to himself as he watched Chastity’s tight ass meander it’s way to the bathroom.
It was then that his phone vibrated a second time, it was Sarah again. Same pic, but a full body shot this time. She was wearing a thong panty with her hand slid down the front of them. “Wow!” thought Scott as his erection returned with a vengeance.
Phone quickly buzzed once again, a third pic, this time the thong was pulled to the side, and her gorgeous blonde pussy was exposed. Scott quickly grabbed his huge hard on and started stroking it. As he was putting the phone back on the nightstand, Chastity walked back into the bedroom area, this time completely nude with her ruined stockings in hand.
“Ahem, rough man, you owe me a new pair, and I’d like some just like these, same shade and all.” However, when she saw his massive erection, she set the nylons aside and coyly said, “Looks like you’re ready for round two, Captain!”
She paused by the bedside to quickly finger her slit to wetness, then jumped on the bed, grabbing his throbbing penis in her hand and guided it into her very wet, very ready pussy. She mounted and slid right down to his balls, slamming on top of them, and moaned, then started riding him hard.
As Chastity rode, Scott was picturing Sarah on his cock, same position, with her blonde bush glistening and big titties bouncing up and down just begging to be fondled and sucked.
Chastity felt Scott’s cock swell in her cunt, a clue he was going to unload jizz in her soon. Not wanting him to cum in her pussy, she reluctantly dismounted and jacked him hard. She leaned over with her mouth open and tongue out as he exploded. His second ejaculation of the night was astounding!
“Wow, you’re quite the sperm machine tonight, Captain Cockeroo!” She giggled.
It left Chastity wondering, “What am I doing so differently to turn him on like this? This isn’t our first rodeo, like this.”
Being a flight attendant, she ran her mental checklist and concluded, “Not sure what I did; maybe he was just super horny tonight, needed pussy really bad? Don’t know what my “secret” was, but I sure did enjoy it, and he obviously did too!”
The couple lay next to one another, kissing deeply as Scott’s cock resumed its flaccid state. Chastity felt like she’d been a “wellfucked” whore, er woman tonight, and that her pussy and ass had given his cock a great workout in return, judging by the huge amount of cum. They cuddled for a bit then contentedly fell asleep wrapped in each other’s arms.
Meanwhile, back in her hometown, Sarah couldn’t get her mind off Scott. She’d tried going on a couple dates off dating apps, but they fell flat. The guys just couldn’t compete with Scott. They were nice and all that, however, if she had to use one word to describe them, it would be that they were boring.
She’d lost interest almost the minute she met them in person and would inevitably end her evening returning home and masturbating with her Wand or vibrator, all the while picturing Scott’s big cock pounding her. At one point she got a great idea and looked online at dildos to see if she could find one that resembled Scott’s penis. She did, it was some porn star she’d never heard of, but it seemed fitting, and she had a good laugh about it when she ordered “Mr. Big.”
Sarah loved to suck on Mr. Big, aka Scott, while she “Wanded” her pussy. Her orgasms were always intense, and it made her long for Scott’s real flesh and blood cock all the more. The imaginary cocks had their limitations, namely they weren’t attached to her man.
“God, when was Scott going to get here?” she dreamily mused after an intense cum session with her trusted Wand. “I need my pussy fucked so badly! I need a real cock!” as she drifted off to sleep.
Scott checked his flight schedule, nothing going near Sarah’s city. He’d just have to wait for a new schedule or a change in the current one.
In the meantime, Chastity was keeping him busy, as was another flight attendant named Megan. She was Scott’s MILF, a divorced thirtyeightyearold, brunette hottie with a large rack. She had what Scott described as “torpedo shaped tits” with large, darker colored areola. Her big, beautiful tits hung down low and swayed when he fucked her, especially from the backside.
He was always pleased when Megan flew with him, and they laid over in a city so he could get laid and play with her titties. The was always intense, and tonight was no exception. Funny thing though, just like with Chastity, Scott’s mind kept going back to Sarah while Megan.
Megan was riding him as usual, her large bra and y panties lying on the bed where he’d removed them, tits swaying all over the place and all he could think about was Sarah. He felt almost guilty as he pounded Megan’s soaking wet cunt. While he fucked a moaning Megan hard, he pictured being deep in Sarah’s blonde pussy. When his ejaculation erupted all over Megan’s tits, she looked astonished as he thoroughly coated both her breasts to the point cum was rolling down over each nipple, sliding down each big boob and dropping on her chest. She grinned and hungrily lapped his sperm up and swallowing it in one gulp.
As Megan was cleaning up in the bathroom, Scott grabbed his phone and noticed and email from Sarah. It had a couple of attachments. He opened up one was a closeup selfie of her glistening blonde pussy. Scott’s tired, flaccid cock sprang to life. In the second attachment, she’d inserted a finger deep in her pussy. The attachments were simply entitled “Thinking of You, Captain! I think you need something like this hot, wet blonde pussy in your cockpit!” followed by heart emojis.
Megan returned, saw his huge erection, and just stood there for a moment.
“I’m getting tired, Scott. How about I just jerk you off and we call it a night?
Megan sat by Scott on the bed and gave him a heavenly hand job while he was thinking of Sarah. When he was ready to cum, Megan put his throbbing cock in her mouth and brought him to orgasm once again, then swallowed his load for a second time tonight.
A big goodnight kiss followed, and she said, “Okay, enough for tonight, Mr. Cumalot, we have to fly again tomorrow. Let’s get some muchneeded sleep!”
