A Pink Jewel Buttplug— Part 1

This is the story of how I lost my anal virginity. It all started to happen at a fancy dinner with his parents.

One summer while home from college I began fucking one of my friends that I’ve always been a tease towards. This story takes place in July, about a month after the first time he fucked me.

Pink Jewel

Tyler is skinny, shy, and easy for me to push around a little. I’m average height, brunette with shoulder-length hair, with small but perky C cups, a tiny waist, big eyes, and hourglass hips, with a big ass for my frame.

(I’ve been told I look like Mary Elizabeth Winstead if that helps you picture me.)

Tyler’s parents were rich, and always inviting me out to do things with them. They either thought Tyler and I were together or wanted us to be, so I was always his “date” for fancy parties and dinners and stuff like that.

This particular time, they were going to a really nice, set-menu French restaurant, the type that costs hundreds a person.

I got ready for the night, curling my hair, doing my makeup, and picking jewelry. I picked out these matte black three and a half-inch heels, putting me a little taller than Tyler with them on. I also found a bright red dress, as short as you can get away with this kind of restaurant. It was flowy, but you could make out what my body’s shaped like without too much imagination.

As I got ready, I found a cute little Victoria’s Secret thong that I hadn’t worn for too long. It was pink and meshy, transparent all around, with some lace edges.

While I stood at my underwear drawer, something from the back of the drawer caught my eye:

A pink jewel buttplug.

Without even thinking about it, I made a decision, sucked on it for a second, added enough lube, and stuck it in my tight little asshole. I slipped on the thong over it, snapped a quick pic for later, and got dressed.

Hi,

I showed up to Tyler’s parents’ house, looking my best, and said hi to his mom and dad. Tyler came down, and I immediately ran up and hugged him, making sure to press my breasts into his chest so he knew I wasn’t wearing a bra. I took his hand in mine, and we all headed out to the car.

They ordered an Uber Black and I arrived right on time. His parents got in the first row of a fancy SUV and the two of us got in the back row.

They spent the drive talking to me about how college was going, but they didn’t look back much. I told them about my classes and how I liked the area my school was in. Meanwhile, I moved Tyler’s hand onto my thigh. As I caught up with his parents, I slowly moved his hand up my thigh.

“Stop,” he whispered under his breath.

“Don’t be a baby, Tyler,” I whispered back.

I let his fingers brush up against my pussy the slightest bit, then let go, giving him his hand back. My panties felt wet from the plug thrusting into me with every little bump on the drive.

We got to the restaurant, sat down, talked for a while.

With the softness of the booth, the plug actually felt comfier than I expected.

Finally, they asked about us. This was the first time they’d seen me act so flirty and touchy around Tyler, so they must’ve figured we were dating. I made eyes at Tyler and said,

“Go on, tell them, baby.”

We weren’t dating, but putting him on the spot was so fun.

“We’ve started going on a few dates,” he said, lying and blushing. All we’d been doing was fucking.

“Looks like you owe me a few dates,” I texted him from under the table.

“Not in front of my parents, please,” he texted back. I replied,

“Oh okay. Try your hardest not to picture my lips around the head of your cock.”

I turned back to his parents and kept chatting as he squirmed.

After appetizers, I said that I needed to run to the restroom.

I got up, setting my hand on his thigh as I did. I let the backs of my fingers graze against his hard cock through his dress pants.

“I’ll be right back baby,” I said.

I popped in the restroom and fixed my makeup and hair. I went into a stall and pulled out the plug to reapply some lube from my purse. Once I slipped it back in, I pulled down my dress halfway and licked my fingers and circled my nipples gently, until they both perked up, as hard as I could get them. I immediately headed back out.

I came back to my seat, a little bit of an extra sway in my step, with my nipples clearly poking through the thin red fabric of my dress. I noticed both Tyler and his dad staring at me, his dad stopping mid-sentence for a second before catching himself. I leaned into Tyler and whispered,

“Aww, are you gonna cum in your panties again?”

and kissed him on the cheek.

Pretty soon after I sat, the main course arrived. I had drunk a few glasses of red wine in my already, and torturing Tyler like this really turned me on.

As we ate, we all fell silent, digging into the food. I subtly reached down and slipped off my heels. I ran my big toe all the way from Tyler’s foot up his calf and the inside of his knee, and then across his thigh as slowly as I could.

I reached his cock, still hard, and rested my foot on it, feeling it throbbing. I sat across from him, and the tablecloth gave us plenty of cover, but it still felt like we were going to get caught any second.

I stroked up and down, gingerly, across the whole length of him, clenching my toes around his shape a little bit. He felt bigger than the seven inches I was used to, and it was easy to feel his heartbeat.

“How’s your food, baby?” I asked.

He glared at me and squeaked out,

“It’s good,” sounding out of breath.

“Oh, are you okay?” I said.

“Yeah, something down the wrong pipe a bit,” he said, struggling for the words.

I moved my other foot into his lap, using my toes to hold his cock in place while I stroked harder and faster with the first foot.

My nails were painted red from a pedicure a few days ago, which I know drives him crazy.

He let out a small moan, and I set my feet back down. He grabbed some water and caught his breath. Seeing him like this, combined with the sensation of the plug inside me, made me soaking wet.

We finished up the meal and I decided it was time to ramp things up. I sent him the picture I took earlier of the jewel of the buttplug peeking out the side of my thong, along with a text,

“Hope you aren’t getting too hard next to your parents.”

He peeked at his phone, then his eyes shot up to me.

They looked like big puppy-dog eyes, pleading with me to go easy on him. I made a show out of readjusting how I was sitting and bouncing up and down on my seat, staring him dead in the eye the whole time. His breathing got faster as he watched me.

As his parents made small talk with me, I reached my hand under the table and rubbed my fingers around my pussy. They seemed clueless, as I told them about how my parents were doing and my plans for an apartment for next year, but Tyler knew exactly what was happening.

I was so horny, and it felt like electricity every time I touched my clit.

The waiter walked up with desert, and so while everyone was distracted, I slipped my panties off, down to my feet, the wet seat right up against my toy and my pussy.

As he took his first bite,

I used my toes to drop my panties right in Tyler’s lap. I did it lightly, making sure not to touch him. I ate my souffle slowly, making sure Tyler watched my lips.

He reached down into his lap for his napkin and felt my panties. They were soaked all the way through, and his eyes flashed to me briefly. He fiddled around, presumably sticking them in his pocket.

As everybody kept eating, I licked some chocolate off my finger and moved my hand to my lap.

• I ran my fingers in circles around my clit, and brushed my lips, growing fuller with each touch.
• I stuck my middle finger inside myself and eased it in and out, back and forth. I stuck in my pointer finger, rubbing up against the top wall of my pussy.
• I gently pressed my toy in deeper with my other fingers.

After Tyler took his last bite, I pulled my hand out and said,

“Babe, you’ve got a little something on your upper lip.” He wiped,

“Did I get it?”

“No, here,” I said.

I took my soaking wet fingers and lightly brushed them over his lip, right underneath his nose, letting him smell me right in front of his parents.

“There, got it,” I said, as he quickly wiped his mouth again.

I slipped my shoes back on and we stood up. I made sure to leave my napkin on the seat, covering up the little wet spot I made. I made sure there was a slight sway in my step again.

Tyler’s parents were pretty drunk by this point, and I’m sure they hadn’t noticed anything, but Tyler was still a nervous wreck. We got another Uber Black and headed back to his parents’ house.

I moved his hand up my skirt right when we got in, and guided his fingers to graze up against the base of my plug. He pulled his hand away and we sat there quietly, as I felt myself clench with every bump on the road.

Part 2:

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