so, full disclosure: half of this took place over a month ago when all of this shit was still legal and the other half is purely masturbation. I hope someone can get something out of it
He wanted to meet for oysters.
A quaint little spot near the university, I’d passed it longingly for years, eager for the day my driver’s license and income would warrant my entrance. It’s green aluminum bars stools and herringbone-patterned tile floors made it an easy ogle; one almost didn’t have to be interested in the food to want to dine there. And I wasn’t interested in the oysters either: I’d come for aged peppered sausage.
We’d been talking for days, sometimes innocently, and sometimes not. He was married, happily, with two kids. He and his wife had been open since the beginning of their relationship and she was excited for him. Meeting a happily married man for a proper date? Gee whiz, times were wild.
I walked to the bar that day, hurriedly, talking to my sister nearly the entire walk. I struggled to catch my breath as my nerves cascaded down the hill with every step. For a second, I was worried. Shortness of breath was one of the symptoms to be wary of for coronavirus. “Chill, it ‘s just nerves, walking too fast, and talking at the same time,” I reassured myself.
He texted me about ten minutes before I was set to arrive.
“Made it here and in killer time and got a parking spot right out front. Managed to grab us seats at the bar. I’m the tech daddy that’s sitting by himself :)”
Music to my ears.
I could see him sitting at the bar through the glass door as I approached. I opened the door, and he looked back, expecting someone, and smiled.
He was exactly who he had said he was, which was both a rarity and a delight given my past experiences with online dating. He was taller than I had expected, my chin barely clearing his broad, plaid-clad shoulders.
“Something to drink?” the bartender inquired, not knowing who to direct the question to?
“Something with gin.” He remembered my affinity for gin martinis from my profile.
“And for you?”
“I’ll have the same, thank you.”
“I got here in 22 minutes and parked out front–craziness,” he commented, noting the difference in traffic due to the initial phase of companies instituting work-from-home policies.
We got our drinks.
“To…coronavirus? I’m kidding.”
The bartender next asked if we wanted oysters, which seemed like a silly question at an oyster bar. I think I was more nervous about properly downing the oyster than I was about the rest of the date.
It was nothing out of the ordinary for a first date, though I think he noticed how my gaze drifted away from his from time to time. I eyed the sculpted shoulders that laid beneath that green and grey plaid shirt.
“Is there anything else I can get for you two?
“No, I think that’ll be it.”
I didn’t want to seem too forward, but I wanted to keep talking to him more. What was the deal with his wife? Would she ever want to meet me? Had he had younger girlfriends before? Did their kids know about this? So many questions remained, and I still couldn’t take my eyes off those shoulders.
“Do you have to get home, or can I make you my speciality cocktail and continue this conversation at my place?”
“I don’t have anywhere to be.”
He walked me out to his dark blue Lexus that he had indeed parked right in front of the restroom. He opened the door for me, much to my surprise and delight.
“Here’s to classy cocktails in a not-classy setting,”
It didn’t take long before we went back to my room. I lit a candle and turned on my dimmable lamp. Now I just needed to add music.
He looked around my room before complimenting it, making me feel like the dumpster-dive version of Martha Stewart that I was.
“Thank you… I take ambiance very seriously,” I said as I winked at him.
“It’s the ambiance that makes me want to come over here.”
Before I could even look up from lighting the candle his hands were on my hips and his lips were affixed to mine. He didn’t hesitate before moving to my neck, my god, how good that felt.
“Is one side more sensitive than the other?”
I hesitated, not knowing the answer and also, surprised, having never been asked that before.
“Or should I just find out for myself?”
Yes. That. That was the answer.
I was only getting more and more worked up. I could feel my pussy throbbing, drenched, as he continued to pleasure me. But at the same time I faced an inner struggle: I knew we weren’t going to fuck, because I had practically begged him not to let me. I had been touching myself in the week leading up to this date, I knew that by the time we were behind closed doors I’d be all over him. But I knew he’d hold me to my word, so I just got to be teased, and teased, and teased.
I tried to rub his cock as he pleasured me, hoping that I could at least give him something in return. I knew he appreciated it, because he just kept talking to me in daddy talk. Fuuuuuuuck I wanted him. He took his beautiful cock out of his soft cotton briefs and laid it on my stomach.
I moaned so loudly he knew I’d felt it.
“I didn’t put it in you, it’s just on top of you,” he reassured me, reiterating that he hadn’t forgotten the initial request.
I looked down at my stomach to see a beautiful, meaty, cock that appeared to be aching for my attention.
“Can I put my mouth on you, daddy?”
“It can wait.”
Fuuuuuuck. He wasn’t desperate. Which made me want him even more.
“As much as I’d love to do this for, like, three more hours, I should really get going.”
I understood, I probably should have thought about being responsible too.
I walked him out and got back to work…on myself. I couldn’t help but be so frustratingly worked up.
I stripped before tucking myself into bed and beginning to stroke my wet pussy. It took me a few minutes before I decided just where I wanted to devote my energy. I could think about where the night could have gone had he let me fuck him, but that seemed too easy.
Instead, I chose to think about our next date. Perhaps it was in the middle of springtime, before we knew that no one would be out during the springtime because there would be a global fucking pandemic that ruined everything. But, for now, on March 11th, the world was right, and springtime would come into bloom just as it would any other year.
I am wearing a white t-shirt dress with buttons along the front. I’d picked it out knowing how much I’d love to see you undo it, button by button, hole by hole, just as I’d hope you’d tackle me.
We’re walking along 15th, maybe we’d made out in Volunteer Park or gotten handsy at the lookout. All I knew was that I wanted you, badly, and that I wasn’t far from home. The whole time we’re walking I can’t stop thinking about how much I want your hands up my dress, onto my fair, sun-deprived skin, and into my daddy-deficient pussy. I can feel, in anticipation, the desire I have for you, building, overwhelming, and distracting my senses. We’re just on a walk, enjoying the neighborhood, and all I can think about is how much I want you to daddy me so hard.
We finally get back to my place and you can’t help but be so damn polite. Fuck. You say hi to my roommate, take off your shoes, and generally act like a good guest. But then I remember that’s what gets me so worked up about you. How you can be the perfect gentleman in one moment and the most sadistic of daddies in the next. You may be on your best behavior now, but I know that only means one thing: that I have it coming for me.
You loiter, talking, being kind and thoughtful, like a nice guest . But I just want you inside of me.
“Jason, come to my room, I want to show you my new plants!,” I exclaim, knowing very well that nothing has changed.”
You come in and pretend to act surprised. “Wow!”
I stop you before you have to feign interest,
“I don’t have any new plants, I just really wanted to kiss you.”
You don’t hesitate before grabbing handfuls of me with your greedy daddy hands, scooping up my ass and breasts as if they were toilet paper on a grocery store shelf, in short, and unknown supply.
Fuck, you made me feel wanted.
I remembered that you liked white underwear, you’d mentioned it on our first date. Something about looking innocent for daddy. I was anything but innocent for daddy, but I’d be damned if I didn’t at least try to make him happy.
You push up the dress to reveal the lacey white thong I’ve worn just to make you tingle. Afterall, I just want to make you happy, daddy.
“That’s my good little girl.”
“Raise your hips.”
I glare at you, incredulously, wanting so badly to be used but unwilling to give up my brattiness.
“Raise your fucking hips or I’ll make sure you regret not doing so.”
That was just the type of coercion I needed.
I raised my hips and you slide the panties off of me, nearly ripping them in your ravenous attempt to consume me. You affixed your mouth to my throbbing, drenched pussy, promising not to stop until I begged you to.
I don’t remember much except that your delicious lips felt even more magical against my soft, eager pussy. I didn’t have to tell you anything, you just knew how to please me. You’d said that you had a magical tongue, but so did every guy. But you weren’t lying. I wanted to hold your head down against my pussy for as long as I needed until I was aching for you to penetrate me.
“Daddy, no more,” I cried. “I want you inside of me.”
You didn’t hesitate before ramming your hard cock inside of my pussy, pounding into me like each thrust was going to be your last. I couldn’t help but come and come and come. Penetration didn’t typically do it for me but you’d worked me up so well I couldn’t help but convulse every time our hips met.
Source: reddit.com/r/gonewildstories/comments/g2vzw7/sugar_daddy_dilf_date_and_mastubration_sesh_f21