Annalise and the Anaconda

I feel like I’m in my prime right now. My body is more curvaceous than when I was in my twenties, and I’ve really got my act together with my career. I wouldn’t want a fella who didn’t put as much work in as me, which means I travel a lot and often read through client briefs in bed.

Still a gal’s gotta have some fun, right? I’m not looking for a partner, just someone to rumple my sheets sometimes!

My besties Aaron and Wayne invite me to all the parties and shows, everywhere they go, and always make me feel like a royalty. Perhaps that’s why I get picky with the guys I meet on dating apps. Nobody fusses over me like Aaron or Wayne, and I seem to have lost the will to stroke a guy’s ego.

Anyhow, I was checking my notifications and swiping left on most of them, but this fella’s profile made me pause. He had a nice body and dressed well, but his dimples and grin grabbed my attention, little lines fanned out from his eyes, so I concluded this guy smiled a lot.

I swiped right. What the hell.

I sipped my Prosecco and kicked off my sandals, pushing aside my plate. The velvet voice of Mr. Michael Buble crooned from my iPod, and I only had one pitch to look through tonight. Maybe I’d have an early night with my Satisfyer.

I was absorbed in the paperwork I’d brought home, when my phone pinged. I picked it up and saw that I had a Tinder match. It had to be Mr. Smiley. I decided to open a conversation. Thank goodness I didn’t have much work to do, or perhaps that’s why I let it get so intense, but we had a divine evening; vanilla fact gathering became flirting, until soon he was texting outrageous things that made my fanny flutter.

“Can I send you a dick pic?” he asked me, which nearly brought things to a halt.

“I never accept dick pics,” was my response, “and any sent unsolicited results in an instant block.”

“I suspect a woman of your discerning taste needs a sample of the goods,” he persisted.

“Well darling, if you’re so determined, why don’t we arrange to meet?”

Then I actually held my breath.

I was getting to like Mr. Smiley, but so many men fell at this hurdle. They’ll happily spend the evening sticky texting, as I call it, then put their best foot forward and meet up for a date.

“I’d love that,” he responded. “You say where and when.”

I had a business trip the day after next, and Mr. Smiley had his own commitments, so we finally agreed on a date that was a couple of weeks away. It was frustrating, but I’d warned him I take my business seriously, best to start as I mean to go on.

That night, I used both my Satisfyer and my dildo with a suction base. I got myself in the mood by lying in bed with my legs spread, playing insistent, flutters of air that I can pinpoint on my clitoris, until I was climbing the walls with arousal. Then I stood in my shower with the dildo fixed to the tiles, bent forward and backed up onto it.

“Michael Buble!” I exclaimed excitedly, as I sheathed my soaking pussy around the dildo to its hilt.

It fills me so well. Immediately I began thrusting my backside towards it, working up a rhythm that matched my thirst. I had my Satisfyer with me too, which I kept hovering over my clitty, until I was whooping with the delicious agony it can bring. Soon, my body tightened all over, my legs, my belly, my nipples were hard enough to cut glass, and my mouth fell open, gasping for air.

“Fuck me Dave,” I cried out.

Surely you’ve given your dildo a name?

Then I was climaxing, a leg shaking, body melting, kaleidoscope swirling finale of an orgasm that I rode like a surfer rides a rip curl. I was a shuddering hot mess by the end of it, but a happy one. I took a shower to clean myself up, then slipped bonelessly into bed.

The day of our date came around, and I’ll admit to feeling excited about it. We’d enjoyed flanter since that first night, and that had led to more instances of self pleasure for me. I couldn’t speak for Mr. Smiley, but knowing men, I’m sure he’d done the same.

I put on a nice navy dress, plunging at the front, wrapping over in the skirt, it gave pleasing glimpses of both cleavage and legs. I’ve still got it, so why not flaunt it? I gave Wayne and Aaron a sneak preview of what I intended to wear, and they were all for it — Wayne said I should leave my hair loose and waved, but Aaron suggested an up-do was sexier. It was a warm night, so I put it up to keep my neck cool.

I’d invited Mr. Smiley — whose real name was Simon — to collect me from my house.

Wayne and Aaron were going for a drink in the pub nearby, and would call me every half hour, until I gave them the signal that I felt comfortable for them to stop.

My downstairs windows were open, so I heard the crunch of gravel as Simon pulled up on the drive. I checked myself in the mirror before opening the door.

Michael Buble! He stood there stark naked, wearing the cheesiest grin.

What a body Simon had. He’d mentioned he liked to keep fit, but he’d been underselling it. He had sculpted abs and firm quads. and those pecs and biceps were bulging. But damn he had a cute dick, I’m sure a snapshot would not have done it justice.

“Hi Annalise, you refused a picture, so I thought I’d show you in person,” Simon chuckled. “I hope you’re not offended.”

“Not at all,” I smirked back, “and it would seem you’re quite pleased to see me.”

The cutest pearl of pre-cum quivered at the shiny tip of his helmet, and his cock had swelled rapidly in length and girth since I’d been standing at the door. Simon’s hands were behind his head like he was in a Mr. Universe competition.

“You’d better come in,” I laughed, “there’s a strict dress code where we are going, and that outfit does not comply.”

Simon picked up his black sports bag and stepped inside, but not before I noticed a shocked face at the window of the house opposite.

Well good, a nosy neighbor couldn’t hurt. After all, I still didn’t know if Simon was a good guy. Only time would tell.