Last year, I went through a brief cougar phase. Fuck, why not? Let’s see what these Millennials can do in the boudoir.
5’10”, a nice, white Minneapolis boy with a wide grin on a wide face, curly hair and beard. Works in the tasting room at a small winery. Just like for Prince, this Darling Nicky was gone after one funky time.
Met on Tinder then at a local bar. Cocktails, convo. Cute, genuine, loved that wide smile.
Walked him to his truck before I walked myself home.
“Thanks for meeting up, you’re an amazing kisser ;)”
“Lol, thanks! I enjoyed grabbing your hair and beard…”
“That was the best make out I’ve had in years. I liked you grabbing a handful of my cock.”
“You have a nice cock, thanks for inviting me to stroke it.”
“Consider it an open invitation.”
A month passes. He writes me to apologize that his life is all drama. (Eye roll emoji)
I casually extend an invitation to hang out again, but care little about the actual outcome.
I’m just not impressed with the Millennials. They have all that 20-something ooey, gooey growing up life mess all over them. Of course, I had it too when I was their age. The sky is falling at every turn. I think I’m an empathetic person, but for this I just don’t have the patience.
“I definitely had fun last time. I’ve thought about it a lot…”
” Really?? I’m glad I made such a good impression.”
“You certainly did! Sexy, charming, great conversation, great kisser…how could that not leave the best impression?”
FUCK! I am so simple I cannot resist the praise.
“Ha! Thanks, you’re a cutie! Well let me know when.”
“Maybe middle of next week? Honestly what I really want is to taste your pussy.”
“Perhaps a drink first?!?”
A month passes.
“Want to grab a drink tonight?”
A month passes.
“Hey! Sorry it’s so late. Would you want to grab a drink Wednesday or Thursday night?”
“Thinking about me in the middle of the night??”
“I might have been recounting our make out session.”
“I like the idea of you fantasizing about me.”
“Just so you know, since we met I’ve fantasized about you a lot.”
“Do you make up more to the story??”
“I do, I’ve thought of a couple different stories about you.”
“That’s exciting. Anything you’d care to share?”
“I’ve fantasized about that night going a little further. About you not just stroking me, but also taking me in your mouth, right there in the parking lot. And after that, you tell me how wet you are and how your house is just down the road…
And I come over so I can repay the favor and taste you.
After that night, you come and see me at work for a tasting, but it’s late on a Saturday and I’m the last one there. You’re wearing a tank top and long skirt. We’re tasting wine at the long wood table in the tasing room and then without warning you sit on the edge of the table in front of me and open your legs…”
“That’s pretty hot! And very doable if you want to make it reality.”
“I just felt a pulse surge through my cock. Damn, you are so sexy. I’m literally rock hard just thinking of you. I get this way every time I think about making out with you. I just wish I had had more time to feel your amazing pussy. I want to use my fingers to make you cum…
I’m glad you think coming in for a tasting at my winery and then having me taste you sounds hot. I’ve thought about it a lot as I’ve been cleaning up at the end of the day.
Two straight guys I was seeing in town individually both expressed an interest in MFM. Well, let’s get this group together for a drink and see what happens, shall we?
Pro was an ex-pro golfer, 5’9″, Irish, early 50s, divorced, no kids, pot head tasting room associate, creative builder, silly, family money, large long cock, voracious consumer of online porn which I also came to enjoy.
Addict was 5’10”, a hidden-away, recovering drug addict from a very prominent family in town, mid-40s, divorced with two teenage girls, loved to cook, we’d make dinner, smoke, drink, fuck and watch movies in his apartment.
We’d arranged for the three of us to meet up at a local wine bar, and if agreeable by all, we’d go back to the Pro’s house just a few minutes drive away.
The Pro texted me about an hour before we were scheduled to meet.
“Mirror selfie for me to wet my appetite.”
I laid on my stomach on the bed and pulled up my dress to reveal my sheer black boy short panties. They hugged my round ass cheeks like second skin, and exposed some of the strawberries tattooed on my hip. I bent my knees, crossed my legs to show my black cowboy boots and white knee-high socks, and snapped a pic from my left shoulder looking straight down my back. The angle accentuated the arch of my lower back which gave way to my tight, round ass.
When I walked in to the wine bar, the two of them were already sitting across from each other at a high table with drinks in hand. I wasn’t sure who to sit next to. I gave the Pro a hug, then the Addict, and then sat down next to the latter.
The Pro was eager to go back to his place. He was a Pro in more way than one, and had had threesomes and foursomes before. The Addict and I were the newbies.
The Addict ordered some cheese and charcuterie. In my nervousness, I drank my bubbles rather quickly, and ordered another.
I have absolutely no idea what we talked about.
I got halfway through my second glass, and the Pro suggested we go. I downed the last bit, and the Addict and I jumped in the Pro’s truck to head back to his house.
He had a small, two-story house where the second floor was one big bedroom. We walked in to a dimly lit living room then he led us immediately up the stairs. There were candles lit all over the bedroom, and porn on the TV positioned across from the bed. A white woman was sucking on a big, black cock.
The Pro opened a bottle of Charbono for me and the Addict. We made small talk while we undressed. I could feel myself getting wet catching glimpses and hearing the groaning from the TV.
I was leaning over to take off my boots and socks when the Pro came up behind me and ran his hand over my panties down from my ass and around to my pussy. He rubbed back and forth for a moment.
“So fucking warm,” he uttered.
I stood up as he came around to my front side. He pulled my strapless dress to the floor. The Addict walked up behind me, unhooked my bra and pulled my panties down around my ankles. He immediately planted his hands on my hips, and buried his face in between my ass cheeks. The Pro slid his hands under my jaw and grabbed my head from behind. He pressed his lips hard against mine, and gave me a mouthful of tongue.
My brain was trying to keep up with all the sensations I was feeling. So many hands and lips on me at once was driving me crazy, and made me weak. I felt like I needed to lay down to take it all in.
The Pro must have felt me weaken, stopped, and ordered me to lie on the bed on my stomach. Then he walked up to the edge and thrust his hard cock into my mouth. The Addict climbed on the bed straddling my calves and started running his hands over my ass and thighs.
I arched my back, and the Addict ran his fingers along my ass and started playing with my lips. His fingers pushed them apart and I could feel how wet I was.
I could only take in a small amount of the Pro’s long, thick cock. I took my mouth off of it and put it in my hand while I stroked and leaned down to lick his balls. The Addict thrust two fingers in my pussy and I lunged forward, my mouth pressed hard up against the Pro’s balls.
They both stopped and the Addict turned me around so I could take him in.
The moaning coming from the TV and the heavy breathing from both of them made my widely horny. My pussy lips were tingling and pulsating. I couldn’t wait for one of them to fuck me.
The Pro slipped on a condom and I was on all fours when he moved in between my thighs, grabbed my hips and plunged inside of me. I jerked forward and immediately swallowed all of the Addict’s cock in. It bent to the right so I used my hand at the base to keep it in my mouth while I rocked up and back from the Pro.
I glimpsed the porn behind the Addict, then closed my eyes so I could concentrate on all the noises and sensations. I was over-stimulated. My mouth full of cock. Trying unsuccessfully to moan from the feeling of the Pro inside me.
Selfishly, the Pro pulled out, took me off the Addict’s cock, flipped me over and pulled me by the ankles to the edge of the bed. He knelt on the floor, and started licking my clit. I got excited knowing from previous sessions that he was good at giving me head.
The Addict climbed on the bed and put his cock in my mouth.
Soft, fast circles directly on my clit with a soft tongue. My muffled moans got louder. He finished me off. As I started cumming, my back arched high and the Addict’s cock fell out of my mouth. I screamed.
“Oh my god! Oh my fucking god!”
He came up, and thrust his cock back in me hard. I dripped on to the floor.
He came fast.
While the Pro was fucking me, the Addict was watching, waiting and prepared himself by putting on a condom.
As soon as the Pro finished, the Addict grabbed my hips and pushed me up the bed. He pushed my legs apart and slipped in very easily. The Pro sat in a chair in the corner and watched. I put my legs up and squeezed my ankles around the Addict’s neck while he grabbed my thighs as leverage to get all of his cock inside of me.
I watched the porn behind him. The white woman was standing in a kitchen. She put her left leg on the counter exposing her ass hole and pussy. He came up behind her and entered her. I was moving on the bed in rhythm with her pushing up against the kitchen counter.
The Addict exploded. I was spent, satisfied.
The Addict called an Uber and left. I climbed under the covers with the Pro and passed out.
During our time dating, Nerdie and I have been also been looking for couples and unicorn women to see and “play” with together. The Burning Couple was the first couple we matched with on Tinder.
The Burning Couple because they enjoy the occasional party drug, clubbing and well, Burning Man. Living together for the past two years in SF. Let’s call her Jess: 35, 5’7″ white, medium length thin straight blond hair, blue eyes, cutie, small boobs, just a lil out of shape with thick legs and small belly, never married, no kids. He, Dan, 46, 5’9″ Indian descent, full head of black hair gelled back, pretty big mid-drift, the accent of a SoCal surfer dude, divorced with three kids.
She and I matched, had pleasant intro conversation, and shortly after made plans for the four of us to meet at a bar in the city. Our first date was perfectly lovely. We talked as a group, and broke off at various times to speak individually.
We made second date plans.
As a first order of business from his recent divorce, Dan bought himself the pontoon boat the ex would never let him have. It was parked at the West Sacramento Marina.
We stocked up on snacks and booze, put on our bathing suits and headed out for a day on the water.
Jess met us at the end of the dock wearing shorts and a tank top over her bathing suit. My eyes were drawn to her legs as she led us to the boat.
NOOOOOO, the dreaded cankles! My penis deflated. My face scrunched in pain.
Ok, ok, get yourself together. Looks are always secondary to personality and chemistry in my book. Stop being so mean – judgey bitch. Keep going solider.
Besides being Dan’s second time taking the boat out and literally running into boats on his way out of the marina, we had a grand ‘ole drunken boating time. Music, swimming, sunning, chatting, river peeing. It became quite clear to both me and Nerdie, they were much more about us whereas we were still in the examine-n-baby steps mode.
We got the boat back into the marina without much fanfare despite being way more drunk. After safely parking, I took Jess out for a test drive and made out with her a bit while the boys watched. Good enough kisser, and it was fun to feel like the man since I had to bend down so far to get my smacker on hers. Note to self about liking feeling manly.
Ok, some recovery there.
We planned a third date. Six Flags.
Meanwhile, there were a lot of group texts and a lot of texts from her to me asking about our every feeling, thought and desire past, present and future. A little much, but I appreciated the openness. Better to over-communicate when you are trying to get a four-some together. Plus there was some interesting sex reports.
“He fucked me 3x this morning, and I’ve never been so tired in my life. We broke personal orgasm goals with more of the night to go!!!”
“So you came 3xs today??”
“Had 4 sessions, 3 in the morning with 15 orgasms and just now 5 more. He had 4 in total.”
Jess then sends a dark pic of them having sex. He’s taken it looking down himself while she’s on top, folded over him, sweaty belly rolls…yes sweaty…thighs squished. Faintest site of his penis in her following his round, dark haired belly.
It looks like the Stay Puffed Marshmallow Man is mounting the end of a half-lit NYC streetlight pole.
They aren’t unattractive people, but come on – know your audience! Bad angle, bad lighting, bad position. Bad sexting, bad!
Six Flags day arrives. Perfectly fine, lovely time riding rides, eating, drinking, chatting. So much amusement wiped us out so we peeled off in the late afternoon.
Then I moved, it was summer, he’d got kids – weeks go by.
Nerdie and I talk. It’s luke-warm from us at best, but he lets me take the lead. I’m trying because they are nice, easy-going, and newbies too, but I’m also trying. So I try.
“Nerdie and I were talking more and wanted to ask you guys about getting together for some fun times – start out by just having play time with our respective partners in the same room. Kind of like live action porn…would you be interested in that?”
“Sweet! Dan and I would be interested.”
“Cool – we think it would be fun! However scheduling might be an issue for the next few weeks…”
“No worries! The next two weeks may be tough for us too. Let me sync with Dan tomorrow on schedules.”
“I thought you guys lived together??”
“We do, but he splits his time in Sac with his kids.”
“Aww, all alone in the big city??”
“Haha, for a bit, expecting Dan around midnight.”
Hmm, my devil horns become erect. I always enjoy a lively sexting session, but never have I with a girl before…shall we?
“I just thought you might like to sext a bit…I’ve never done that with a girl before…”
My first shot was me with folded legs under my ass pushing that nice round booty out. It was more than two hands could hold. Wearing a white lacy thong running from my ass up the small of back. Curving high around my hip, hugging it tight, disappearing as the lace bent back down in the front toward my pussy. Beautiful colorful garden of tattoos displayed below, above and under the lace. Strawberries, butterflies. Shadows capturing the arch in my lower back.
She returned. Stretched out naked on the bed. Took the picture above and to her right with no face visible. Just a straight shot down her body. Large, suckable, perky brown nipples, round belly and right leg folded to cleverly cover her pussy.
“Your dark nipples are fantastic!!”
“I love your tan lines, so hot!!”
“I think you know mine are pink.”
Front on pic of my bare left breast prominently pouring out of a grey tank top. Large, round, stiff nipple accentuates a small breast begging to be cupped and sucked.
“Yum. Of course they are hot, especially with your beautiful artwork…very sensual!!”
“I’m sexting with Nerdie with now too. He just sent me a pic of his hard cock, and told me how he loves when my pussy grabs his cock when I cum. Ok your turn for the next pic…”
And then…in a millisecond that followed growing excitement…building pleasure…the first reach down my pajama pants…
I was scared straight.
“What would you do with this in front of you?”
I was frozen. Staring. Blank face. Completely immobilized.
Run far, far away – that’s what I’d do!
It was literally the ugliest pussy I had ever seen, could be seen, was ever seen??
I texted Nerdie for advice. I was simultaneously laughing and stunned, and had no idea how to react to this terrible site. Ehhhh….??
“I love it bald!”
That’s all I could come up with quickly. How could I tell her I’d eat it? Finger it? Fuck it? Ask Nerdie to fuck it? Finger it? Eat it? I’m a terrible, terrible person. The worst.
“You didn’t answer the question.”
OMG! How can I exit this convo ASAP?!?
We had a few more exchanges so her pussy wasn’t on my phone screen anymore. I didn’t have to view it while texting her back. I tried to be nice, however, luke-warm and playing along until I found my escape hatch.
“Lick that clit gently at the top, soft swirling.”
“Would you like any whipped cream or honey?”
“Mmmm, honey would make it that much sweeter…”
“And then? Ha, don’t tell me you’re done, haha!”
I just trailed off into the night…never to return…
No, not really. We exchanged texts for a few more weeks, and then eventually I just said Nerdie and I weren’t feeling it.
Scared straight. That’s how you get scared straight.
It was a beautiful summer afternoon in Napa. I was enjoying a beer with Nerdie at an outdoor table on Main Street. We were cracking jokes, laughing and flirting.
We starting talking about his roommate who has the uncanny ability to get girls, and get them into bed fast.
I witnessed this firsthand, repeatedly. One Friday night, Nerdie and I were sitting on his couch watching Hulu getting high using our individually preferred methods, when we heard a knock at the door.
Roomie, let’s give him a name…Slayer, comes down the hall, to the front door, opens, greets her, and starts walking back with her to his bedroom. He introduces us, we barely turn to say hi, and everyone carries on with their business.
On one such occasion that exact greeting scenario was happening, only this time we say our half-hearted hello, and she responds,
“I’ve been here before.”
Oh shit! Slayer brings home so many girls that Nerdie didn’t even recognize her…hilarious!
Now I’m skeptical about his prowess. Slayer is about 6′, 28 years old, messy as fuck with a dog and a cat, decent job, slim but not fit, 420, pointy nose, blond hair, plays D&D, endearing dorky laugh, loves black girls.
Ok, he has some charm to him, but WTF?!? How in the fuck does he get first dates to not only come to his apartment, but right to his bedroom? What the hell does he say on POF (his preferred dating app)?
I wanted to investigate.
So laughing and pondering over this conundrum on that sunny afternoon at that Main Street bar, Nerdie and I come up with a masterful, pause…fucking masterful plan.
CATFISH SLAYER ON POF!
We go back to my place and put Nerdie in my white skinny jeans. Baby’s “back” does rival mine…mmm hmmm!
He sticks it out to the left. I snap a pic. And we are off!
But wait…what should our profile name be? Well, something to attract Slayer of course. Nerdie slam dunk!
Next decision point…headline.
Hot Coffey looking for some creamer
Nerdie crushes the 3-pointer!
She is 23, black, from Santa Rosa, 6′, smokes occasionally, has an athletic body type, is non-religious, and is seeking a man for dating. Her profession is ‘bud tender.’ She has a Bachelors degree, doesn’t do “drugs,” has a car, no kids, makes $50-75k, does not want to date someone with kids, is ambitious and has no pets. She wants to date but nothing serious, and her longest relationship was under a year.
Smoking weed and hanging with my friends. I work hard and play even harder.
The politics and social climate we find ourselves in today.
The internet just officially broke – our inbox quickly fills to 99+ messages!
While we try to find Slayer’s profile, let’s have a little fun, shall we?
I can be your creamer. Promise you won’t be disappointed with my attributes.
I got creamer and weed.
You ever find that creamer? Let’s smoke!
Wassup wit u?
I ain’t creamer, but can I be the hot fudge to your sundae?
On the floor. Tears rolling down our faces. Stomach pains. Faces hurt.
Our only profile pic is Nerdie’s ass so quickly we start getting requests for face pics – fuck!
We both start trolling for black girl face shots on the internet. Not too slutty. Not too pro. Wholesome, but with a look in her eye.
Found it! She’s in the car, light-skinned, black long-sleeved sweater with U-shaped collar. Cute, short, straight hair. Tasteful, if not just a little big, diamond earrings. Simple make-up. Clear, beautiful skin. She’s grinning politely, no teeth. Has her left hand tucking her hair behind her ear.
The internet births an A-bomb. 99+ becomes 99+ no matter how many we view.
So we both start responding for shits and giggles while we hunt for the Slayer.
Mmmm, I like sweets.
I’m still looking for my creamer, is it you?
Tell me about those attributes…
Hot fudge where?
This goes on for weeks. The app is on Nerdie’s phone so anytime we are together, I grab it and start searching, and sending stupid ass messages back to these stupid ass 20-somethings. God I’m glad I’m not my nieces! Fuck that noise as Nerdie would say.
Then one day I’m searching away and just like that, I hit the lotto…Slayer’s profile. Insert image of heavens opening with angels singing.
His profile pic is with his dog…ok, cute.
But the words…OMG the words. Long, rambling, bad grammar, misspelling, lots of words that together say nothing notable. Hanging with friends. The outdoors. 420.
And my dick goes soft. What? That’s it? I thought we were going to get the secret sauce recipe. Now I’m even more confused then when this all started.
But fuck, was that fun…and still is! I downloaded the app for my phone, signed in with Nerdie’s account, and when I’m bored some nights I go on and fuck around some more with the 99+ messages that are always there.
And that’s how my BFs ass broke the internet. I bet you saw this video coming from a zillion miles away…
Ever since I had a two week affair with the neighbor two doors down from my family’s beach house in NC two years ago, I’ve had a thing for older men. I mean older.
6′, white balding hair, British Canadian from Montreal, retired banker who still dabbles, not too big of a belly, flat ass, old man cologne, divorced, no kids, building a home in VT, globe trotter.
When I saw his picture on Tinder, it took me a minute to swipe right. This dude looked OLD…but my curiosity got the better of me. What would it be like to date someone who could be my dad, literally?
We matched. After some very proper introductory conversation via text, he invited me to dinner up valley. I felt compelled to wear something more conservative than usual to our first date.
I walked in to the bar and spotted him standing at the end looking like, well, a grandpa. We made eye contact and I walked over. As soon as I got close enough, I smelled stodgy old British man cologne. Yes, his teeth were f’d.
What the flying fuck am I doing?!?
He was drinking a lovely $20+ glass of Chablis. I ordered the second most expensive Zin.
I can only describe our initial conversation as exchanging pleasantries. But there was something there. My mood pivoted from dread.
We moved to a bar table for dinner. I ordered whatever the fuck I wanted. $14 cocktails. Sweetbreads. Lamb.
He had the waiter open and decant the 1995 bottle of Grand Cru Bordeaux he brought.
Ok, maybe I’m easily persuaded by expensive food and drink, but the conversation was on point. We clicked. We talked about great wine, great food, great travel. I was actually having fun.
Uncharacteristic of me, I accepted an invitation for a nightcap back at his house. He lived just around the block in what he dubbed, a “bungalow.” A $1.6M 2 bedroom, 2 bath house with a small guest house and garden in the back, which he had gutted and completely remodeled after his divorce two years earlier. The inside looked like no one lived there. I was afraid to touch anything.
He opened a bottle of vintage champagne. We talked through that entire bottle.
It was late and a “school” night, so he walked me to my car. Standing next to the driver’s side door in the blue moonlight, he went in for the first kiss. Very respectable, slightly opened mouth, no tongue effort.
We went on a few more dates. Some lunches during the week. Some dinners. It was going swimmingly and I loved being spoiled so much. He texted me love notes all the time. It was too adorable.
“I am a truly romantic man and hope to convince you of my attributes one of these days!”
“Yes, I was thinking about the weekends and maybe kidnap you once we get to know each other better and head up or down the coast.”
“There is no greater high for me than to make love to a woman you adore and spend long days and nights together enjoying laughter, great food and wine and unending passion!😋”
“I would like to kiss you well into the wee hours!💋💋💋”
The night before my birthday he invited me to a home-cooked meal at his house.
“Thinking rack of lamb, truffle mashed potatoes and green beans and you for dessert.”
He had chilled champagne and a handsome array of cheeses for me to nibble while he finished cooking dinner. We ate dinner at a very properly set dining table. He even got me a birthday card with a lovely handwritten note.
We moved back to the kitchen bar stools for strawberry shortcake, Sauternes and espresso. He moved his stool close to me and moved his hand up my thigh under my dress leaned in and gave me a long, deep kiss. It sent tingles all over my body that settled in my pussy.
I stood up and moved in between his legs. He surrounded me with his arms and hands moving them up and down over my back, ass, thighs.
He met my lips with his, and I could feel his cock getting hard against my thigh. It was full and long. He put his hand through the back of my hair.
Then I chickened out.
Oh, god, I can’t fuck a grandpa!
I made my excuses of work in the morning. It was a Tuesday after all.
“I’m home darling 😉 What an exceptionally fun evening, thank you!”
“Glad you are home safely. I want your affection and was afraid I pushed the limits a bit tonight!”
He called my bluff.
“I really wanted to take you to my bed and undress you slowly as I enjoyed every inch of you and then…”
I marinaded on the idea for a few days, and thought WTF. Maybe he’d be an amazing lover. Experience, focus on pleasing me, what more could I want?
We had another lunch or dinner or two, but alas he faded away.
I saw him recently at the bar of a restaurant where I was meeting a donor for lunch. I gave him a hug and smooch, and then rushed off to meet her.
I had hoped he might text me after that, but no. Guess I’ll have to keeping dreaming of grandpa.
He and I chatted over the next few months. About a cocktail I was trying to make out of a Thai Chile Jelly I made. About the “Ethical Slut.” He was a good fairy to me.
I told him about this blog. The first guy I had felt comfortable to tell.
“I am sex positive and if you had a different partner every night I would celebrate it! I have negative jealously.
Ok so first off, I really enjoy reading your sex stories. Not jealous in the least bit. They turn me on, and even more so because I’ve been with you. My gf and I tell each other stories like those about our other escapades in detail like that all the time and sometimes in even more detail. Second off, I have a bunch of notes and critiques and suggestions about the writing, you personally, and the blog in general, but maybe we should do that in person as there is a lot to go over. Third off, after reading that you got me hard as a rock right now. You have me imagining my own story with you. I’m lying here naked in bed imaging me ripping off your panties and pushing you down on your bed and pressing your face in the pillow as I fuck you from behind.”
We had a second date, again in Napa, about six weeks later to continue the conversation.
“Italian food will hit the spot, but honestly I have been craving the taste of you all day.”
“You remember what I taste like??”
“I do 100%. You’re fucking delicious.”
We talked about monogamy. About what I was reading in the “Ethical Slut.” About the acronyms on “Feeld.” WTF is “soft swap,” “full swap,” “GGG”? It felt like the first day of school. He was a patient and interested teacher.
I had gotten so worked up at all the sex talk I could feel my wet panties.
We went right back to my apartment and jumped on each other. Rushing to unbutton, unzip, untie.
I finished first and laid naked on my back on the bed. He stood at the side, grabbed my calves, turned me toward him and pulled me to the edge. With my legs dangling on either side of his, he grabbed my ass and thrust in to me. The feeling of his hard cock inside me surged an electric pulse of pleasure from my pussy, up my legs, over my chest and arms and to my brain. I arched and gasped.
Again, he finished first, withdrew and got on his knees at the bedside.
The next morning he left early.
“Your body is fucking sexy btw it’s just on my mind driving home.”
We texted periodically over the next three months trying to coordinate a time for the three of us to get together again. My work sent me to a two-day conference in Sac so I reached out again.
“Hey, I’ll be in Sac for a conf mon and tues…are you and your lady free for a drink or dinner mon night by chance??”
“Yes, we’ll take you to dinner!”
“Should be a fun night!”
“She is still able to join us for dinner, but she has a late appointment afterwards. ☹️ We will see you soon!”
That’s curious. What could she have to do after dinner on a Monday night? And I guess a threesome was out for the evening…fuck!
They were late. I was at the bar when they walked in. He looked his normal self. Well-groomed. Casually well-dressed. Wide grin.
She looked like a bag lady. Literally she had 3-4 shopping bags, stuffed with shit. Her clothes, hair, face, and mannerisms were all disheveled.
We sat at a booth. Me across from them. Her on the outside.
I order Pinot. He a cocktail. Her a double gin and tonic. Her bags piled up some between them, some on the floor under the table.
We ordered dinner, and started casual conversation catching up on the past few months. They went to Idaho to visit family over Christmas. Yada, yada, yada.
All the while I was distracted by her behavior. Nervous. Twitchy. Like she had never sat a dinner table in public before.
She got up, grabbed her bags, and moved toward the ladies room. He and I continued chatting, and chatting, and chatting. Probably 15 minutes went by. Dinner arrived and she was still in the bathroom.
She came back in different clothes. Then she dropped the bomb.
He asked her to talk about her experiences with polyamory. She pulled out her phone, opened an app, and showed me her profile. I didn’t recognize the app. Her pics were pretty well naked, and there were a lot of acronyms. And a rate.
She said this was the second app she was on. The first one was shut down.
I held the phone and my wine glass in opposite hands. I stared at the screen. It got blurry as did their words. I didn’t want to look up.
She was a mother fucking prostitute!
My face was straight, but my mind was silly string.
It all came together, and I was pissed. I can’t believe I fucked this bastard twice, trusted him with the contents of this blog at the time, and he didn’t have the fucking pussy to tell me his gf was a prostitute. Did he think I was going to be sex positive now?
She ate her food like a horse. I maintained my composure and sat politely through dinner. She said she needed to go, took her food in a box, and he rushed to pay.
Outside the restaurant, I talked before they could. I said thank you, gave her a hug, and then him before he could suggest we go for another drink or back to his place or my hotel.
On the way to my car, I was saddened. Maybe she really did love it, and maybe they enjoyed telling each other about they sexcapades. Guess I was blind.
However, my mood quickly turnaround after realizing both times with him I played it safe and that my last battery of tests were clean. On to the next fairy.
I’ve come to call some of my first dates fairies. It has nothing to do with their sexual orientation, but rather that they fly in, sprinkle some pixie dust of insight or knowledge, and then I let them flutter away. It’s usually not their physical appearance that attracts me, but rather something about their life experiences urges me to see them in person.
This is exactly how it was for my first fairy.
38, 5’10”, lives in Sac, widowed with a gf in an open relationship, dark skin, thick dark hair and eyebrows, sultry eyes, big wide smile, was a bartender for awhile, now in tech, possible photoshopping on his sexy pics cause his real body looked like he had once been fat.
He was one of the first dates I went on with a guy who had a gf in an open relationship. We made plans for the two of them to come to Napa for dinner. I was nervous and excited about the possibility of my first threesome.
“I have bad news. We have to cancel for tonight. She had an appointment she had forgot about and it is something she can’t miss. I apologize. It sucks cause I’ve been excited about it. BUT we promise we will make it up to you. Actually we are both on very flexible schedules so if there is another night that will work let us know.”
“Ok no worries, hmm well I’m guessing it would be hard for you guys to come to Napa during the week?”
“Well….since she has her appointment tonight I have no other plans. Want to still go out?”
“Sure! If we click we can talk about having having her join too or not, whatever feels natural is fine with me.”
We met for drinks and snacks at a casual restaurant in downtown Napa. His face was wide and dark. He was quick to laugh and that, plus his wide smile, made me feel comfortable immediately.
He told me about his wife dying in their early 30s. How much she was his soulmate and partner. How lost he had been for so long until he found his current gf, who was no stranger to open relationships. She had lived most of her adult life that way. He felt like he found home with her. Always having the idea in his mind of being free to love many people in many ways.
He told me about Feeld, a dating app for couples and kinks. This is where I ended up meeting The Worshipper and The Couple.
He also told me about “The Ethical Slut”, a book about navigating open relationships.
Fairy dust ball.
That book was a revelation, helping to solidify my muddy, pre-formed thoughts about love and relationships that continue to evolve. More on that in another post.
The intellectual connection I was having with him was amazing even though the physical connection was just so-so. But I was so turned on by the conversation I invited him back to my apartment. I also wanted to take him for a test drive before meeting the gf, so to speak.
He took me from behind as I lay flat on the bed. Pushing my hands up against my headboard. Pushing repeatedly. My ass smashed by his lower stomach as his cock slid out and all the way in, as deep as it could go. It slid easily through my wet cunt.
I turned my head to the side so I could see him thrusting. I not only felt his tight grip on my hips, but now I could see his fingers digging in to me, pulling me back and forth over his hard cock.
He came and collapsed on me. Turned me over and immediately went down on me.
It didn’t take me long to follow. Literally dripping wet, his tongue glided over my clit. As soon as he started making light, fast circles over it, I went over the top.
“Oh my god! Oh my godddd…fuck me…mmmm…oh my fucking god!”
We fell asleep almost instantaneously. He left in the morning. An hour later even before I got out of bed.
“You are awesome! That was awesome. You looked so hot when you came. I wish I was still touching your body right now. We will need to do it again soon.”
“Thanks! And thanks for coming to Napa and treating me to a fun night!”
I met The Couple on Feeld. If you are unfamiliar with that dating app and need a refresher, read the first few paragraphs of this post.
Like other singles and couples I had been matched with, it was just a lot of kinky chatting. These folks were the first ones to invite me for a drink.
He was 6’3″, scraggly beard, large pointed nose, slender if not a little wiry, great wide smile. She was 5’2″, dirty blond hair, long and straight, adorable laugh, slender, quiet.
They lived two counties over so we found a mutually agreeable dive bar to meet in the middle on a Sunday late afternoon.
I arrived first, bellied up to the bar with two other stools, and ordered a tall frosty one. They came in a few minutes later and we exchanged hugs and greetings. I found them both attractive right away. Their body language toward each other and me said fun, confident, and sexy. I was in!
We arranged the stools close together in a wide V with her in the middle. The conversation flowed easily around the usual topics of work, family and lifestyle. There wasn’t a shortage of cheesy jokes, subtle sexual innuendos and smiles across the board.
He was a criminal litigator working on building a political board game around the 2016 presidential election. She was a governmental employee of some kind making a long commute into the city daily.
They were newlyweds and had met and had an affair when they were both married to other people. Umm…ok, a sensitive topic for me. A definite flag on the play, but ok let’s see where this goes.
They figured since they had both been unfaithful before that in this marriage they should open it up to include other people. They were both free to sleep with anyone else at anytime, or with someone/people together, as long as they were practicing safe sex. Ok, the logic is there, I guess I’ll give them that.
During the discussion, mostly as I reflect now as the beers kept flowing, he began to get a just a wee bit assertive about sex.
“Well if we go home tonight…”
“You’d really like it when we…fill in the blank sexual act…”
After the third beer, unsolicited, he announced that he thought the three of us were having just a swimming time and why don’t we go to dinner?
Perhaps it was my naivety in my first date with a couple, but I was feeling a little bit uneasy, yet, also still extremely curious to see where this would go. I suppose if I stuck to my own car, major roads and public places I’d be right as rain so I proceeded.
We found a casual Italian place in town and drove separately there. They were busy for a Sunday night so we tucked tightly into a table for two with me and her on the bench close together.
We ordered wine, then an appetizer, then entrees. As he kept drinking the comments moved from assertive to aggressive, and my mood from open-minded to closed.
“I can’t wait to watch you two.”
“How do you want to fuck us?”
Well, buddy, you just turned my semi into limp.
The bill came, he pulled it toward him, as I thought he should since he invited me to have dinner with them, and then said this.
“We’ll divide it three ways, and I’m only paying for the bitch I get to take home.”
I sat there stunned, and I know I don’t have a poker face so I’m sure it reflected my inability to know what to say or do next. I put down my card, signed the receipt. I didn’t intend to make a scene, just to leave and get away as fast as possible.
I made all the niceties in the parking lot – hugs and thank yous. Looked over my shoulder as I walked to my car, and thanked the lord they didn’t know where I lived.
For a brief time I created a profile on Plenty of Fish, an unremarkable dating app that seemed wholly focused on “Netflix and chill.”
I started texting with a guy, Creeper, that quickly became sexting.
46, 6′, short dark hair, fit but not ripped from the pictures I saw, great cheek bones, square jawline, events manager/contractor in the East Bay, total slut.
I told him I was interested in exploring my sexuality with girls. He told me about the young women he was hooking up with. Many in their 20s. The pictures he sent me of them were way past tastefully, thoughtfully or discretely done.
A full on nude, with full face, of a 20-something standing in a brightly-lit, pink bathroom littered with clothes and towels on the floor and make-up and other girlie accessories all over the counter top.
Another was an extreme close-up of a razor-burned pussy. No idea if it was the same girl.
He started a group chat with the dirty bathroom girl. We all exchanged pics, and talked about hooking up. Her tits were young and beautiful, round, perky, motorboat-able. Her hair was long, fine, dark and straight down to her ass.
He said they were meeting up on Saturday morning for playtime. Weird timing, but ok. I asked if he would send me a picture.
At 10AM I got a video.
I could see they were in the back of an SUV, parked god knows where in broad daylight. The shot was her on all fours with her right hand reaching between her legs touching her clit.
Creeper! Who are these low self-esteem girls who fuck you?? My interest in actually meeting him had seriously fell off, but ok, let’s see where this goes.
I hit play.
The camera pans up over her ass to highlight her deep V from shoulders to narrow waist. Sweetheart ass exposing her asshole. Long dark hair cascading over her pale white, narrow shoulders and back.
“Put your head back a little bit for her, baby. Show her how long your hair is. Mmm…watch this, Adrienne.”
The camera pans down to his hard, naked cock. With one hand on her ass, the other filming, he slowly pushes his cock inside her. I watch her take it all in. She gasps and in a high-pitch, lackluster voice she must have learned from watching a lot of porn…
“Oh yeah. Oh my god. Fuck that pussy.”
“Oh my god. You feel so fucking good.”
Shaky camera work gets close-ups of ass, cock, long brown hair, the back of her head. His cock sliding in and out of her smoothly and easily, her pussy devouring it whole, bumping that perfectly smooth, shiny, round ass over and over.
I had no time to play that morning as I was on a tight schedule to get to the winery by 11AM, but I was so turned on. I could feel my pussy pulsating in my panties as I was watching what was a :43 second video.
I jumped into the bedroom, pulled up my dress and down with my panties. I tapped my clit with my right index finger and could feel it was already swollen.
I ran my first two fingers down inside my lips and I was soaking. I moved back up, found my spot pushing the flesh on the outside of my clit over to the left and pressed my fingers in hard.
I went fast thinking about the head of his hard cock pushing her pussy lips open to take it in. Thinking about her pussy swallowing it. Hearing the repeated bump against her ass once it was all in. Hearing her sticky wetness as he pushed in and out.
I went back to my computer after I finished, and there was another video waiting.
He’s lying on his back. She’s reverse cowboying with the camera close to the action. Her pussy is again swallowing his cock. I can hear that gooey, wet pussy slide up and down.
“Mmm, baby, you’re fucking amazing. Oh, you look so fucking good. Give me that pussy. This is the reverse cowboy position, Adrienne.
Sit up and show her your beautiful hair, baby. Show her how sexy you are. Look at that.
She’s riding my cock, Adrienne.
She wants to kiss you right now, Adrienne.
Yeah, I think she wants to lick your pussy while I fuck her like this.
She wants to get with you soon so let’s make it happen. Tell us if you like it, Adrienne.”
Ok, no denying it was hot as fuck, but what girl gets fucked in the back of a car in daylight on Saturday morning and it’s A-OK that he films it and talks to another girl during?!? Strictly masturbating material…thanks, guys!
I fell back asleep after she left. When I woke up, I found her diamond earring and a pair of shorts she wore under her jeans on the floor. I sent her a pic of me in the shorts pulled halfway down with my left tit and stomach exposed.
“You secretly wanna see me again, you can’t deny it! Or at least half your wardrobe did…”
“Some time this week?”
“Honestly I don’t feel safe right now. I don’t want to spiral out of control playing games. I need to be someone’s #1. I am tired of feeling insecure.”
“I figured you might go that way. I’m sorry to hear it cause I had fun with you and wanted to see you again.”
“Do you know a good civil litigation attorney in Napa?”
OMG! What washed over me when I read that text was fear that she knows where I live, a tug at my heart because I can feel she is a good person who just had a shitty childhood and most likely a really tough time growing up as a lesbian, and curiosity all the same.
“Not really. The lawyers I know do things like estate and tax law…sorry. I’m driving to San Rafael later this morning and could come through Vallejo if you want help.”
“When do you get back? I may be in Napa to file paperwork in the courthouse.”
“I’ll be gone for the day. Seeing a friend in Oakland after a stop in San Rafael to check out futons.”
“Ok, some other time then.”
Two hours later.
“I am stressed out.”
Oh god, what have I started getting myself in to? I want to be nice and sympathetic, but this is getting clingy and weird. I try to be helpful as I start to open the door to leave.
“Why? Is the courthouse and lawyer stuff about that crazy neighbor you were telling me about?”
“I don’t know what I’m doing. I feel weak and stupid.”
“Why? Cause of what happened with us? I had fun.”
“I am scared to go to jail. I promised myself I would never go back.”
“You gotta find a lawyer then.”
I had no idea what the fuck to say to all this. How can I be nice and helpful, and also keep my distance and exit this connection?
And oh god, oh god! I slept with an ex-con, and she has my number and knows where I live. Oh god, oh god!
“I sucked in school. I am dyslexic. I made my money the hard way. I feel inferior to the establishment because I am from the streets. I can’t speak English like real white people. I am different.”
“It’s perfectly fantastic to be different. You have challenges, we all do. Nothing to feel bad about.”