The First Timers Club
Copyright© 2022 by Alex Weiss
Ten Years Later
Coming of Age Sex Story: Ten Years Later - Ashley and her three best friends are high school outcasts. Four virgin nerds who have never dated or even kissed a boy. At Ashley's sixteenth birthday party, the four girls strike up an unlikely friendship with a new acquaintance of Ashley's parents. A handsome older man with a dark past who agrees to become their sexual mentor. But Ashley's mom has plans of her own for the mysterious new stranger in their midst.
Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa Ma/ft ft/ft Fa/ft Mult Teenagers Consensual Drunk/Drugged Reluctant Lesbian BiSexual Heterosexual Tear Jerker MaleDom FemaleDom Light Bond Rough Spanking Group Sex Anal Sex Cream Pie Double Penetration Exhibitionism First Facial Massage Masturbation Oral Sex Sex Toys Tit-Fucking Voyeurism BBW Menstrual Play
The dull clang of steel on aluminum awakened me. The forty foot catamaran rocked aft to stern like an eager hobby horse as it dipped and rose over a series of large, incoming swells. I crawled from the berth and climbed to the deck, still naked. I almost never wore clothes aboard ship. I mean, what was the point?
Dark clouds and howling winds portended a fierce summer squall. The choppy waters tossing the boat caused the loose mainsail halyard to bang ceaselessly against the towering mast, but a couple quick turns of the winch tightened the sheet and quieted the noise. In the dim predawn light, the enormous tree-covered limestone cliffs of Phuket Island soared high above the turbid waters of Phang Nga Bay, where my catamaran sat anchored to a mooring ball, located roughly mid-shaft on the giant peninsular cock thrusting into the wet folds of the Andaman Sea. A paradisical nub on Thailand’s western coastline.
After securing a flapping tarp corner that threatened to expose the cockpit, I returned to the comfort of the galley to get the coffee going. For some reason, once I’d reached my mid-fifties, going back to sleep ceased to be an option. I fired up the laptop to check the weather service, curious when the storm would pass. I wanted to explore Phang Nga Bay and do some snorkeling, but doubted there’d be much to see today with the churning silt clouding the water.
Oh well, fuck it. Maybe tomorrow.
The modest Leopard sailing catamaran had been home for the past five years, and we’d circumnavigated the globe together nearly one and a half times. I’d sold the apartment and cashed in the investments, buying the boat from a BVI broker and had her refitted in Ft. Lauderdale. I still consulted from time to time, both to pad my substantial nest egg and to keep myself busy during long oceanic passages. An Iridium dish kept me plugged into the world.
While the water boiled, I checked my emails. Spam. Spam. Client. Nope. Non-paying client. Fuck you. Spam. Spam.
I stopped scrolling to stare in disbelief at the next email. I’d almost deleted it and only barely caught the subject line. My pulse quickened.
Subject: The First Timers Club
Sender: ashley.ryerson0315
Sent from a private email server. A flood of emotion swept over me to see her name. It had to be her. The email had been sent days ago. I’d been distracted by other things and hadn’t been keeping up on my inbox. I clicked the link to read the short email.
I’m not sure if this email was sent to the right person. If it’s you, then you’ll be able to open the password-protected attachments below. The password is your full name, all lower case, no spaces. If you received this by mistake, I apologize. It was sent to 133 different email addresses, so I really hope one of them is you!
5 ATTACHMENTS:
ashley.eml
brittney.eml
courtney.eml
isthisyou.pdf
forever.jpg
Ashley. Brittney. Courtney. The First Timers Club. It was her. I covered my mouth with my hand to stifle an emotional utterance that pushed at the back of my throat. I never thought I’d hear from them again. I double clicked to open the ashley.eml file and a password dialog appeared. I typed in my name as instructed and clicked Submit.
ashley.eml FILE BEGINS
Hi. It’s been a very long time, hasn’t it? Do you know what date it is today? It’s March 15th. A very special date, and a very special anniversary. The Ides of March. Julius Caesar. Remember?
Ten years. My god, how did it go by so fast? One day I’m a junior in high school, the next I’m making breakfast for my boys. Yes, I’m a mommy! Two sons. Two and three. I’m married, too. Daniel. Danny. I think you’d like him. He’s a wonderful husband and father and I love him so, so much!
We met in college and we both work in tech. Danny’s a software engineer and I work in cybersecurity. We both work from home most days, so we get to spend lots and lots of time together with our boys.
I’m still a huge nerd, lol! I still play video games and board games and role playing games, but now I get to play them with my husband, which I love! He’s a nerd, too. No, wait! Sorry! He’s a geek! Lol! Omg, he hates it when I call him a nerd by accident.
Mom and dad are still together. Whatever was going on back then, I guess they worked it out. Dad apologized to me for the things he said that day in your apartment. We didn’t have the best relationship for a long time, but once the boys were born, things got better. They love their grandkids, and I’m the only daughter who’s given them any. So far. We’ll see if Chelsea ever settles down with anyone.
I think about you a lot. I missed you so much when you left. We all did. I tried to call you, but you blocked our numbers. I understand why you did that, but it still hurt a lot.
Do you remember my tails? LOL! Oh wow, I just remembered them right now thinking about you. I don’t have them anymore. I think my mom might have them or something (yuck!), but I remember loving them so much back then.
I haven’t done anything like the stuff we did in your apartment that last day. That was so crazy! I do still have my thigh highs and bustier, tho! Somewhere in the garage, I think. I wore them for Danny a couple times, but he isn’t into the Mistress Ashley stuff so much. But he goes along because he knows it turns me on. Plus, I’ve got a mom bod now, lol! My butt is still big, tho. Just in case you were wondering ;-)
I still talk to Brittney sometimes. Courtney less. Mostly on social. They both live pretty far away, and I haven’t seen either of them in a couple years. We used to meet up every year on this date to reminisce, but then we stopped and it never happened again. I haven’t spoken to Kay in years. She went to college in Oregon and we all lost touch with her. She talked about moving to Alaska or something crazy like that.
I don’t want to say too much about them, tho, because Brit and Court wrote to you too! I’ll include their emails as attachments to the main one, plus a couple other things I thought you might like.
I hope this message finds you well. I know how hard you struggled, and the demons you fought. I can’t begin to express how grateful I am to have known you, and to have had that wonderful experience with you. I’ll always cherish it.
I’d love to hear from you, but I understand if you don’t reply. Knowing you, you’ll probably delete this before reading it. If you ever do want to talk, tho, just reply to this email. I have it in my queue to monitor, so I’ll know the moment you send something.
That day in the pool, when you asked to be my friend, was one of the best days of my life. You were my first male friend, and even tho I only knew you a week and we haven’t seen each other in a decade, you’re still my friend and you always will be.
Love and best wishes,
Ashley Mitchell Ryerson
How could anyone ever be as sweet as her? Jesus, I cried like a little schoolgirl. I hadn’t thought about them for years, and reading her message brought back such a flood of memories. Her tails. How could I have forgotten her tails?
Cybersecurity. Figures. I hadn’t exactly been hiding, but being off the grid for five years tends to disguise one’s digital footprints pretty well. She’d found me though, so I guess she was pretty fucking good at her job.
The shifting, swirling winds, and a passing superyacht going way too fast, churned up a massive wake that pitched the catamaran around like a rubber ducky. I held onto the edge of the table until the waves calmed, then rose to get a cup of coffee.
While I poured hot water over the course coffee grounds in the French press, I absently scratched my stomach, now a washboard of abdominal muscles. I’d lost twenty five pounds, eight of it muscle, but enough to finally expose that final lower two-pack. I didn’t run or lift weights anymore, but life aboard a tiny boat in the middle of the ocean tends to keep you active and wiry. I’d never been in better shape in my life. I’d even quit smoking and drinking, though I still partook of the occasional hallucinogen from time to time.
I took the press and a mostly, pretty much clean coffee mug back to the table and opened Brittney’s email.
brittney.eml FILE BEGINS
I don’t even know how to begin. Every time my fingers touch the keyboard, I start crying and I can’t stop until I walk away. Oh god, how can I still feel this way after so long?
First of all, I’m a mom. Yay! I had a baby last year. A little girl. Her name is Emma and she is such a little cutie and I love her so much I can’t even stand it! We live with Emma’s daddy in Arizona. It is so damned hot here, and you know me. Pale as a ghost.
I never got into medicine like I wanted. I ended up majoring in English instead for some reason and went to work at a cement company. Can you believe that? I handled logistics and dispatching for them, which I never even knew was a thing until I started working there, but it was such a cool job. I really loved it and there were always tons of hot guys around, but more on that later :). I had to quit when I got pregnant and now I’m a full time mom. No hot guys anymore, but at least I have Emma!
I gained a lot of weight when I got pregnant. Like, almost a hundred pounds. I felt disgusted with myself, to be honest, but I’m working on it. I started walking with the baby in the morning before it gets too hot and I’m trying to eat healthier. I’m already down 30lbs! My goal is to get back to my high school weight by the end of this year (wish me luck!).
There were some benefits to getting pregnant, though. My tits and ass are fucking huge now, lol! I remember you had a thing for big butts, so let me just put that image in your mind...
Oh god, I’m so nervous. I’m so scared Andy (Emma’s dad) will wake up and find me writing this. That would be so embarrassing! He’s a little jealous of you. I think I talked about you a little too much. Woops!
Before I say anything else (because this email is going to get really steamy in a minute) I want you to know that I haven’t cheated on Andy. Not yet, anyway. He’s taking care of me and Emma until I can go back to work, and I appreciate that, but sex with him is just not that good, to be honest. He tries, though.
Working at the cement company was a real eye opener for me. It opened up a lot of other things too, if you know what I mean, lol! The guys there were obsessed with me! I fucked so many guys there, you have no idea. I even got my foursome! Three guys at the same time. It was fucking mind blowing. I couldn’t stop cumming, and you know how loud I get. I think I scared them!
I tried being careful. Condoms and birth control and all that, but I ended up getting pregnant anyway. Like Ian Malcolm says, “Life, uh ... finds a way,” right? When I found out I was pregnant, I just knew I wanted to have her and, thankfully, Andy stepped up. We’ve been exclusive ever since, but let me tell you, my sex life went from a 9 out of 10 to a 2 out of 10 real quick! :(
[Ash and Court: everything after this is private. Please respect that.]
I’ve thought about you every day since that very first night in the pool when you kissed me and I made your cock hard. You are my everything. You are the love of my life. My first kiss. My first lover. Not a day has gone by that I haven’t thought about you. Kissing you. Fucking you. Your perfect mouth and your perfect cock.
I masturbate to you all the time. Constantly. At least once a day. In fact, you’re the only person I ever think about when I masturbate. I dream about sucking your cock and drinking your cum. I imagine you fucking my tits. I can still feel you inside me. Fucking my ginger pussy. Fucking my tight little asshole. Oh my god! I would give anything to have your big cock in my ass just one more time.
I bought a dildo and named it after you, lol. It was the closest thing I could find that was your size. I fuck myself with it daily, but it’s not the same. Your cock was so warm and smooth and of course it was attached to your sexy body. The dildo is cold. I sometimes soak it in hot water, just to feel the warmth of it in my pussy and ass, but it’s just not the same. The dildo doesn’t clutch my hips and crash against my ass the way you did. It doesn’t kiss me and look into my eyes and tell me I’m beautiful and sexy. It’s just a dildo, and that’s all it will ever be.
I asked Andy to double fuck me with it. He did a couple times, but he always felt intimidated by it, lol! He’s also not that into anal, which blows my mind because I thought all guys wanted that. Turns out, quite a few don’t and a lot of them think its gross. After our first “accident” he said he didn’t want to do it again. I always remembered your advice. If a guy won’t give me what I want, I should move on. And I always have. Maybe I will this time too. Of course, I had to get pregnant by the one guy who doesn’t like anal. FML.
I walk around the house naked a lot when Andy’s at work. Sometimes I wear high heels too. I have a butt plug that I wear way too much. When I’m alone in the house and Emma’s asleep, I fantasize that you come over after Andy leaves and we fuck all day. When I’m in one of those moods, that dildo gets a lot of action, believe me. I fuck my ass and pussy with it, just going back and forth between my tight little holes, then suck on it before I do it all over again. All three holes with my fingers on my clit. I wish we would have done that. I would have loved to have had your cock moving between my pussy and asshole and mouth. God!
Sometimes, I go outside in the backyard and masturbate there. We have this elderly couple who lives next door, and whenever I hear the husband start up the blower, I run outside, get on my hands and knees, and fuck my ass with my dildo. He can’t see me over the fence, but I know he’s there, and the thrill that he could peek through the fence slats at any time to watch me gets me off so fast.
Remember when we were all dirty talking that day and I said all those sappy things to you and cried? Oh god, I cringe every time I think about that, but you were so sweet to me. You didn’t make me feel bad about it. Oh god! Why can’t I stop thinking about you? I’m so hungry for your cock. Ugh!
Anyway, I want a redo. I’m going to give you the dirty talking I wish I would have given you that day, only updated a little to account for my new MILF status. I desperately hope you think about it the next time you stroke that big, beautiful cock of yours.
You’re naked. Your huge cock throbs, dripping with precum. Every muscle in your strong body is flexed and you glisten with sweat. You point to the ground in front of you.
“Get on your fucking knees, you fat slut!”
I do it. Immediately. You grip my red hair and I open my mouth for you and you shove your big cock inside. The taste of your cock is like ambrosia. It’s my whole world (I wish I could have deep throated you even just once!). You fuck my mouth, using me like your little whore, because that’s what I am. A dirty little ginger whore who only exists to be used by you.
You pull out of my mouth and I gasp. I want your cock so bad, but you want to fuck my tits now. My huge tits full of mother’s milk. I wrap them around your cock and you fuck them. I pinch and pull on my pink nipples, milking my tits and covering you in my milk.
Then you grip my hair and throw me down onto my hands and knees. My huge tits sway and my big ass waits for you. You line up behind me and I can feel the heat radiating from you. Your lust and desire, and I want it. I want all you have to give.
You slide your huge cock into my tight little pussy (my pussy really is so fucking tight still, I promise!) and you fuck me. Hard. You slam into me, again and again. I cry out because I love it so much and my cries make you fuck me harder and faster.
You spank my ass. My huge, fat ass (my ass is so fucking big now. Like huge!). You spank it so hard I scream. Over and over until my big, fat ass is red. Then you stick your fingers in my ass while you fuck my pussy. Two fingers. Then three. Then four! You’re trying to put your whole fist in there, and I want that! I would let you fist my ass all the way to your elbow if I could!
And then it’s time. You pull your huge cock from my sopping wet pussy and you press it against my tight little asshole and I can’t wait. The anticipation of it makes me shiver. You push it in and I can feel my asshole expand as you go deeper and deeper inside. You’re all the way in there, and my pussy fucking tingles because your big, thick cock in my fat ass feels so fucking good.
You fuck my ass like an animal. You don’t hold anything back. My huge tits fly back and forth as you pound me from behind. Buttfucking me. Buttfucking my dirty little shitter like the anal slut I am. Your fat little butt slut. I want your hot, sticky cum in my ass and I cry out for it.
“Cum in my big, fat ass!” I scream and you spank me so hard I can’t even breathe. You grab my hair and yank my head back and you’re fucking me so hard that sweat pours off you onto my back and I love it. My huge tits flop back and forth until they hurt from the force of your anal pounding, but I don’t care. I love the pain. I love it so fucking much! I could never get enough!
“Fuck my ass!” I scream. “Fuck it! Get your big cock deep inside there and fuck the shit out of me!”
You can feel your orgasm coming. So hard and so fast, it makes your eyes water. It’s going to be the biggest load of cum you’ve ever had. Your big balls ache because you need to cum so bad.
“Cum in my ass!” I scream, and you do. You fill me up with so much cum it flows out of my ass, past your cock, dripping over my slutty pussy and down my thick, chubby thighs.
Then you pull out and turn me around and I suck your big fat cock straight out of my ass, licking and drinking your cum along with my dirty ass juices. I want every drop of cum you have left. Everything you have to give, I want it all. You even scoop the cum dripping from my ass and feed it to me and I fucking love it because I’m your fat little anal butt slut cum whore and you could do anything to me and I’d beg you for more.
Then maybe you spit in my face or piss in my mouth and make me drink it or something, I don’t know. Ooh! Maybe you piss in my ass? What do you think about that? I’m still working on it.
Whew! I had three orgasms writing that, lol! My tight little pussy is so god damned fucking wet right now. Dripping. I have my feet up on the desk and the chair is soaked with my pussy juices. Can you imagine that? Can you picture me with my legs spread, my wet pussy dripping, fucking myself to orgasm after orgasm while milk leaks from my big tits? I hope you can. I hope you dream about that tonight.
Alright, I have to go to bed now. Emma will be up in a couple hours to nurse and I have to get some sleep. My huge fucking tits are so full of milk right now they hurt. I really wish you were here to suck on my nipples and help me! Oh god, I would love to nurse you while I jacked you off. Or I could be on top of you and you could fuck my ass while you sucked my nipples. Fuck! One more orgasm, then bed.
Here’s all my contact info:
Brittney Hughes
cell: 578-737-1904 (Private. Andy never sees this)
email: bigbuttgingerslut@spectralitenetworks.com (I set up this email just for you. Totally private.)
mail: 13949 St. Rt. 97 box 4232, Mercury, AZ, 85670 (my private post office box)
social: @brittneyannehughes
Call or write me anytime. I don’t care when. If you call at 3am, I’ll pick up. And if you ever want to get together, I’d love that. I would die just to see you.
I love you. I love you. A million times I love you. Kisses, hugs, and wet sloppy blowjobs!
- Brittney
PS: I’ve never forgotten what you said to me the day we first had sex. You told me that if I wanted something from you that I needed to beg you for it and you’d do it. You said you would fuck me any way I wanted. You told me to give myself to you and be your little slut. Do you remember that?
The biggest regret in my life is letting you go. I should have told you how I felt and what I wanted. I should have grabbed you and taken you. You told us that we only regret the things we didn’t do, and you’ll never know just how right you were.
So, this is me telling you that now. Snap your fingers and I’m yours. If you ever want to know what it’s like to buttfuck a 6 foot tall, 285 pound big titty MILF with a huge ass, I’m open and ready for you.
[Ash and Court: If you guys read this part, please never, ever mention it to me or anyone else. If you’ve ever loved me, then you’ll never bring it up. These are my personal thoughts and feelings and fantasies. I love you guys.]