Chapter 5: Swim Club, Part 2

Will

A couple of hours ago Jasmine called to let me know it’s time to dive headfirst into this Swim Club thing, she’s set up my first paying date with her longtime friend Vicky. Now that Jasmine has added her to the secure Swim Club app, we can communicate to make the arrangements.

I introduce myself, “Hello Vicky, I’m looking forward to meeting you. What sort of fun are you looking for tomorrow evening?”

A brief pause then she replies with, “I want you to fuck me, you should know that.”

“Yes, there’s that, but is there anything else you would like to do?”

“If you’re talking about a fancy dinner and dancing? Nah, not interested. I just want to meet up and do the nasty.”

Do the nasty, sounds like an old-school 80s rap song. “Do you have a preference for a hotel or motel?”

“Anything with a bed is fine.”

“How about the Silver Crest on Route 11?”

“That’ll work and I know where it is. Let’s meet there at 7:00 tomorrow.”

“Perfect! I’ll get us a room when I arrive.”

“Don’t go getting all dressed up on my account or anything like that. Wear your jeans, flannel, and work boots, however you’re comfortable.”

“I can do that.”

“Oh, and underwear like in the pics Jas sent, I like that bulge.”

I have to snicker at that. “Sure will!”

Alright, we have the time and place. I shouldn’t have to make any excuses about being gone overnight since the motel is close and I can be home after slipping Miss Vicky the sausage.

All day at work I keep thinking about how I have my first client tonight. I have a woman paying me to fuck her. I can’t get over that, it’s surreal.

Following a shower, I put on snug boxer brief underwear like the ones I wore in the pics. A look in the mirror confirms I have a nice-looking shapely bulge to show off. Blue jeans and a plain white t-shirt with my red plaid flannel as an overshirt complete the requested look – it’s my everyday look anyway.

At the Silver Crest Motel, there’s an older model dark red minivan in the parking area with a woman waiting, that must be her. She’s in her late forties to early fifties with brown hair starting to gray pulled back and tucked under a trucker ballcap. She’s carrying a few extra pounds and her looks are very typical of an average middle-aged woman. It’s hard to picture Jasmine and Vicky hanging out as friends because they seem so vastly different. This woman is every bit of a tough blue-collar hard worker type that probably spends most evenings shooting pool with the guys at the local VFW Hall and drinking Pabst Blue Ribbon beer. Jasmine, on the other hand, spends the same evenings fine dining at a place like Chez Louis’ Chop House in a fancy Ritz-Carlton Hotel.

“Are you Vicky?”

“Only if you’re Will.”

“I am. It’s wonderful to meet you,” we firmly shake hands. “Let me get our room all set up.”

“You do that. I’ll wait right here.”

In the motel lobby, of course, Betty-Jo Peterson is working again. “Well, well, well, aren’t you the familiar face around here. Maybe you should rent at the weekly rate, it’ll save you money.”

“Tonight only, please.”

Fighting off laughter, Betty-Jo flicks her thumb towards the window at Vicky waiting out there. “Are you doin’ your girl’s mother now, or something?”

“Just ... never mind, it’s a long story.”

“I like a good story,” she grins. “Come on, spill it.”

“Sorry ... no. Not gonna happen.” I grab the room key and rush out.

At first, my thoughts were that Vicky not wanting to be wined and dined would make this date a breeze, she just wants sex, but here we are, two complete strangers sitting on the bed, staring at the wall and wondering what to do next - talk about awkward. Small conversation over pizza or even fast food would’ve helped give me some sort of starting point to work with.

I’m reminded of what Daisy told me about playing the vibe of the room. What I know about this woman is she’s direct and isn’t interested in any cutesy charming fru-fru-ey nonsense. I guess I’ll just get right to the business at hand. Already knowing she wants what’s in my undies, I can be direct as well. Standing up in front of her, I ask, “Do you want to undress me, or have me do it?”

“You take your shirt off.” With a tiny grin, she adds, “But I wanna pull your pants down.”

“Works for me.”

Kicking off my shoes, I remove my flannel and pull my white T-shirt over my head, Vicky nods approval of my naked upper torso. She reaches up, undoes my belt, and opens my fly; I can’t resist pushing my pelvis forward so her hand rubs over my bits as she lowers the zipper. This is becoming a trademark move for me, I snicker to myself.

Down go my jeans and I step out of them, the whole time her gaze never wavers from my bulge. “Ah, you’re a good boy, Will. This is exactly what I wanted. I’ve always had a thing for guys showin’ off their bulges.”

At the risk of being a bit cocky, I push my hips forward. My cockiness pays off as Vicky grabs my waist to pull me the rest of the way, smashing her nose into my squishy genital pillow. Rubbing her face left and right, up and down, mashing in and drawing back, she’s deeply enjoying my hot place. To her, it’s as if I’m fresh catnip to a ravenous kitten indulging for the first time. Her lips are opening and closing on my front swell as she’s exploring the tubular shape of my dangler and the spongy roundness of my bean sack. It’s a real turn-on watching her fascination.

Keeping within inches from my protuberance, she slides the stretchy waistband all the way down to closely inspect my private anatomy. Lifting my semi-soft cock, she asks, “Can I put this in my mouth? I loved to do that when I was younger.”

“Sure. Whatever the lady wants, the lady can have.”

She instantly makes it disappear. Latched on and sucking, I quickly grow fully hard. Her lips are like supple satin enveloping my manhood as her tongue dances over and over on my sensitive spot. I’ve had my cock sucked a lot these last few weeks and I’ve learned that an awesome mouth massaging is something I’ll never tire of.

Reaching behind my knee, she coaxes me to put one foot up on the mattress. This is a trick I know well because it puts my pelvis at an optimal height at her face. With my legs parted, she can easily reach up to play with my balls and maneuver herself to suck at all kinds of interesting angles. Vicky is really having fun; I love how she’s enthusiastically gobbling and learning every millimeter of my penis. And not just my penis, she’s getting right down in there to open her mouth on my balls for plenty of licking and sucking on them too.

Such eager oral fun means a particular certainty is eminent - a gentleman always asks first. “What about when I need to cum?”

“Then cum! Throw your head back, howl like a wolf, and empty your nuts!” she laughs. “I can take it.”

“Okay,” I smirk.

She takes my hands and puts them on her head wanting me to hold her face fixed to my crotch. “Ah, that’s it. My mouth is yours, use it, fuck it, fuck it good.”

Gyrating my hips fore and back, I push my cock in thrusting motions, slow at first, then speeding up. My hands keep her head steady as my shaft pistons in and out. She puts her hands on my ass cheeks and pulls me forward on my drives to assist me having sex in her mouth – fucking it, in her words. A few drives go too deep making her fight the urge to gag, but she’s not wanting me to ease up or stop in any way whatsoever.

Counter matching my forward-moving hips in what at first appears to be a mistime, she also moves forward causing my entire cock to jam all the way in. She grips my ass tight to let me know this is her intention and to hold my position. As we’re paused, the deep recesses of her mouth relax and open allowing me to push even further in. Holding her to my pubis mound with her nose buried in my fluffy hair, I can feel the super-smooth surfaces of her esophagus surround and accept my glans. She has my entire erect pussy-poker inside her mouth. After a moment, she pinches my ass cheek signaling me to slip back and allow her a needed breath.

“Yes!” she coughs, “I’ve still got it! Did you feel that? Did you feel it push down my throat?”

“Yeah, I did! That was awesome!”

“I haven’t done that in years! I figured I would have forgotten how.”

How’s this for a unique snapshot of my current crazy life? I’m standing here naked with my saliva-shiny hard-on sticking in this woman’s face, a woman who’s old enough to be my mother currently congratulating herself on how she just deepthroated every inch of it.

Opening wide to take it back in, she tells me, “Try talkin’ dirty to me like I’m a naughty girl.”

I’ve never done the dirty talk during sex thing before, so this will be new - here goes nothing. Pushing my penis in, I say, “Okay, you bad girl, suck on this. How do you like my dirty boy cock?” Oh jeez, how corny-sounding is that? I’m gonna need to work on this.

“Oh, yes!” she thumbs up, “That’s it, keep going like that.”

Pulling her to me and jutting my hips forward so her face presses to me, I let more obnoxiousness out of my mouth. “Here you go, eat me! Does my cock taste good?”

“It does!” she happily mumbles over her mouthful. Encouraging me to keep going, she’s loving this. Repeatedly driving my hips forward, I fuck her mouth as she wants me to.

“That’s it, suck my cock, suck it good!”

“Mmmm ... hmmm.”

“Deepthroat me and take all of my ... my,” I know I’m supposed to be play-acting here, but this seems so ridiculous and I’m about to crack up trying to think up dirty ditties she wants me to belt out. “Take it, take all of it! You can’t live without my super stiff pole of steel. Oh, and suck it too!” Silly utterings aside; Vicky complies and performs more of her first-rate deepthroating. I love feeling her oral recesses kissing every surface of my bulbous head.

Relaxing and letting the moment guide me as she sucks, and sucks, and sucks some more, I realize I’m probably overthinking what to say. I’ll simply go with genuine, in-the-moment, observations. “Ah, yeah ... just like that. Suck my cock ... ohhh, yes ... that feels so good!”

“Mmmm,” she nods. I’m getting a better sense of this now.

With a pelvic push, I say, “I love how you love my cock. Suck it ... Suck it all day for me.”

“Oh, I will,” she mumbles in return. I’m finding this does have its own unique appeal and dirty brand of fun. I’m also finding myself getting close to my apex.

“Get ready, I’m gonna cum.”

“Oh, yesss...” she murmurs, never unlatching, “Feed me!”

Looking up at the ceiling, I yowl, “YeeeaaaAAHHhhh!” and let my sperm fly. Out it shoots with velocity and volume; her humming becomes quite pronounced as I give her multiple stringy streams.

It’s a good thing I’m holding her head, it’s helping me to keep my balance while cumming standing up. I’m going to have to master my vertigo for the sake of future clients who want to suck it while I stand.

Vicky pulls off once my ejaculation runs its course. Keeping my semen in her mouth, she gives it a thorough tasting before swallowing. “Ahhhh,” she announces, “That was refreshing! I haven’t had a young man in such a long time ... too long of a time.”

I flop on the mattress to recoup my breath as Vicky takes off her clothes and flops down next to me. Her boobs hang and sag a little, and she has a bit of a belly, but she’s not in bad shape. Her skin is smooth and soft, any man would be lucky to have her alongside him.

“How did I do with the dirty talk?” I ask. “That was a first for me.”

“I could tell,” she laughs. “We need to work on that, but overall, not terrible. Once you stopped pretending you were auditioning for a low-budget porno flick, it got better. Just keep workin’ at it, you’ll get it.”

“Women really like that sort of thing?”

“Sure, some do. I like it.”

“How long has it been since you’ve done anything like this?” I know escorts aren’t supposed to ask clients a lot of questions, but I sense Vicky wants to tell me things if I ask.

“Well, it’s been several decades since I’ve had a hot hard stud like you, but my last was probably ten years ago. His name was Reggie, a regular down at the local bar in Hudsonville. He and I got drunk a few times and we fooled around; it was nothing special.”

“Well, for the time that’s passed, you did great with me!”

“And I made you cum!” she beams. “Suckin’ you made me feel like I was a teenager again draggin’ a boy I fancy up to the hayloft.”

“Did you used to do that? Have sex in haylofts?”

“Sure! Everyone growin’ up around farms does. Or is that not a thing anymore?”

“Oh, it is. I lost my cherry in a hayloft.”

“Oh, did you now!” She looks at me with the broadest smile of interest since we met.

“Yup. And believe it or not, I lost it to that girl working at the front desk of this motel.”

“Why aren’t you with her? A pretty and young pussy your age must be much more attractive than an old woman like me.”

“You’re not that old and, despite what you may think, you’re not unattractive. That girl in the lobby may be pretty on the outside, but on the inside, there’s not much there. Trust me on that.”

“I typically don’t do well with flattery, but that’s mighty nice of you to say ... your momma raised you right. Jas has been bellyaching about takin’ me for a make-over for years now, but I don’t know ... I’m afraid of how much she’ll want to change me, and I won’t be ... me ... you know.”

“Do you like you?”

“Of course, I do ... well...” she sighs, “I guess some things could ... improve.”

“Why not give it a try?” I shrug, “I think Jasmine has your best interests at heart, she won’t steer you wrong.”

“I know ... but I can’t see myself all gussied up in expensive clothes, high heels, and make-up like she does. I’m a ratty jeans and t-shirt, go to work in the garden, kinda gal.”

“A makeover can be whatever you want. No one says you need to wear make-up and high heels in the garden.”

“Oh, Will,” she laughs, “you make too much sense. Tell me about the hayloft, you and that girl in the office doin’ the nasty.”

I recap my story about the party after the Homecoming dance at the Peterson’s barn, the makeshift bedroom all set up, and how my confidence was crushed after I made a fool of myself not knowing where Betty-Jo’s hole was, and, on top of that, me cumming too fast.

Vicky agrees with Daisy that Betty-Jo was being a cunt to me about it. “She should have known things like that can happen to guys on their first time, especially if she’s invited so many up to her little fuck haven in the hayloft.”

“One would think so, huh?”

Thanking me for sharing, Vicky tells me about her first time. “When I was sixteen, I was working part-time at a local farm to save money to buy a car. I had the biggest crush on the farmer’s son, Jacob was his name. He was my age and such a handsome boy. I was rather tomboyish and surely not the prettiest girl he knew, but he seemed to like me well enough. He would always stay to help me with my work even when he was done with his, he was nice like that.

“One day we finished our work, and it started downpourin’ really hard. We waited in the barn figuring it would pass in fifteen minutes or so. Smitten with him, I had a crazy idea come over me and told him I dropped my house key up in the hayloft. I asked if he could help me find it. He agreed. Once we were up there and looked around for a spell, I pulled it out of my pocket acting all ditsy like, oh silly me, haha, I had it all along. He laughed and called me a doofus. It was now or never so I pulled him to me by the collar and kissed him right on the mouth.

“He put his arms around me and the next thing I knew we were rolling around on a pile of hay letting our hands roam and explore inside each other’s pants. Our clothes came off one article at a time and we had the sweetest sex.

“I’ll never forget going home later that day and finding hay between my ass cheeks from the pile where Jacob made me a woman. Sounds silly, but I kept it in a shoebox with other keepsakes as my secret little souvenir of losin’ my cherry ... still have it somewhere. We did the nasty several more times in the hayloft that summer, although there was never anything nasty about it, not sure why people call it that. With Jacob is when I learned how much fun it is to suck, his cum was every bit as sweet as yours.”

Listening to her story is making me hard.

“Those hayloft romps went on until the end of the harvest season and the weather got too cold. Eventually work slowed for winter and my job was over. Jacob went to a different school than me and back in those days, we didn’t have all the fancy social media you kids have to keep in touch. Over time, we lost track of each other, and that was that.”

“Wow, it sounds like you had a much better hayloft experience than I did.”

“Yeah, looking back, I probably did. Jacob was such a nice guy ... you remind me of him.”

“Did you ever see him again?”

“We’ve run into each other here and there a couple of times. He married after college and had two or three kids with his wife, they’re probably all grown now. Last I know, they have a farm over by Muskegon.”

Noticing my pole standing proud, she spreads her legs and motions for me to get in between, “I think it’s time for you to put that thing in here.” Her pussy looks nice. Her folds are as vibrant pink as a twenty-year-old and her mature flower is every bit as inviting. I catch a sweet whiff of her womanhood; the smell of pussy is such a primal trigger and turn-on.

“Would you like me to wear a condom?”

“No need at my age, sweetheart, plus I had my tubes tied back in the nineties after having twins.”

“I always check first.”

“Good on you for that.”

“Damn...” I mutter, “I forgot to bring lube.”

“Just spit in your hand and smear it on yourself”

“I’ve heard women think that’s gross.”

“I just drank your spunk, kid,” she laughs, “what’s a little spittle goin’ in my pussy gonna do?”

I laugh with her, spit in my hand, and slather it on my boner. At her entrance, I poise for entry.

“That’s it, push yourself up in there really good and hold still, let me feel ya and get used to ya.”

“Gotcha,” I nod and ease forward.

“Ahhh...” she closes her eyes, relishing every nuance as I sink myself in. When my pubic hair presses to her mound, she lets out a shivery sounding, “OH-oh-OH-oh-OH...”

“Is everything okay?” I pull back a bit.

“Oh, it couldn’t be any more okay ... this is fantastic!” she says in a dreamy state of bliss. “You feel so good! Your cock ... it’s so warm ... and smooth ... and hard ... Twitch it, let me feel you moving inside me.”

I tense and release my pelvic floor/perineum muscles to make my shaft flex. “Like this?”

“Yes! Ah, yes, that feels so good! I’m so used to my vibrators, but they don’t come close to having a real one ... a live one. I can feel your pulse and your blood pumping ... oh fuck me, Will, fuck me good!”

Her pussy feels great, it’s warm, wet, and wraps around me perfectly. Call it my own immature ignorance and inexperience, but I figured older women would be looser and flabbier. Not the case. Vicky feels as nice as any woman should. Granted, she’s not as snug as Daisy, but that’s understandable, Daisy is a very petite nineteen-year-old. In a blindfold test, Vicky’s pussy could easily hold her own against Lily, Rose, or Heather who are all in their twenties.

There’s a great idea for our next group sex event; Daisy likes to play stack ‘em and fuck ‘em, how about a new game of guess the pussy? We could blindfold a guy and then guide him into various pussies to guess whose pussy is whose. It works the other way around too; blindfold a girl and play guess the cock. Heather likes that sort of thing and would probably be very good at it.

Vicky pinches my ass cheeks signaling me to start the motions of lifting my hips and lowering, pulling back, and pushing in. On my in-strokes, I curl my hips forward to drill myself a little deeper by that extra tiny bit each time.

Keeping her hands on my ass, she’s grasping, grabbing, squeezing, even pulling on my cheeks. “I love this ass of yours, Will. It’s so firm!”

“Thanks! I, uh ... I like it too,” I snicker unsure what else to say.

Picking up the pace and thrusting repeatedly, I work it in and out, in and out, pull back, push in, pull back, push it in. The more I fuck, the more Vicky is vocalizing her ecstasy. She’s loving this so much and I’m thrilled to provide this pleasure for her. She had the right idea of sucking me first, this way I can last longer. Even if I do cum before her, I can stay hard and keep going to make sure she has hers.

“Faster, Will ... Fuck my pussy!” I increase the speed of my shaft appearing and disappearing into her wet hole which brings loud and deep guttural yowls from Vicky, “OHHhh gauuwwd! Ohhh! ... Ahhh, yeah! This feels so good...”

Lifting her head and looking past me, she’s noticing something. “What’s there? What do you see?” I ask while keeping my momentum.

“In the mirror over the dresser, I have a perfect view of your ass rising and falling between my legs. I love it!”

I look over my shoulder and confirm the splendid view of me performing. “It sure is a great view.”

“A hot young guy fucking my tired old pussy ... never thought I would see the day.”

“Your pussy isn’t tired and old; in fact, it feels great.” Slamming in some really hard thrusts, my movements are making the whole mattress shift on the bed frame.

“Keep talking and fucking like this and you’re gonna make me cum.”

“That’s what I’m hoping for,” I smirk.

“Pound my pussy! Just like that, pound my pussy!” Putting her hands behind her knees, Vicky pulls her legs, lifting them and holding them up into the air. This allows me to push it deeper and deeper. “Ohhhh, gawddd,” she moans, “Give it to me! Drive that man cock! You’re so fucking hard and feel so good!”

With that, I feel her lower body tense as her pussy grabs around my shaft squeezing it, squeezing it so tightly I must slow my drives and let her ride out her sweet moment. She’s squinting, shaking, sweating, and breathing heavily through her mouth, moaning high and low pitches of euphoria.

When reality returns and she can think clearly again, we stay connected and she pulls me down on top of her. “Oh, Will, you are really something. That’s an itch I’ve needed scratched for a loonngg time.”

“I’m happy to help with that.”

“I’ll bet you are!” she laughs, “Now fill my pussy, fill it with your hot stuff, I wanna feel you doing it in me.”

Pumping full-length thrusts, my drives resume to rhythmically plunge my cock into her chamber. Knowing how much she just enjoyed the nice orgasm I gave her is reassurance that all is going well tonight.

With a squint and a body-tensing grunt, I fulfill Vicky’s request of pumping my cum deep into her pussy. In one of our many conversations about sex and the details of what women like, Daisy once told me that a woman likes to feel her man ejaculating inside them. At this very moment, I’m sure Vicky is feeling me ejaculate; for added measure, I accentuate my spurt-twitches by flexing my perineum muscles.

“Ohhh,” she moans, lifting and pushing her pelvis to me, “I can feel you ... I can feel it shooting. That is so nice.” She drags out the word nniiiice into a long hum of euphoria. When I’m done, I pull out and drop down between her thighs. Seeing what I’m about to do, she starts to say, “Oh, you don’t have to—” My open mouth cups her mound, my tongue tickles her clit, and she inhales a sudden deep breath of appreciation. “Oh, you-dirty-boy-you! Yesss ... Yes, lick me in there!”