I [f] wore a buttplug to a fancy dinner with my best friend’s [m] family, teased him all night, then let him take my anal virginity [fm]

Some of you might remember Tyler from [my story](https://www.reddit.com/r/gonewildstories/comments/hi4wnq/i_f_took_my_best_friends_m_virginity_after_making/?utm_medium=android_app&utm_source=share) I posted about making him cum in his pants and taking his virginity. For those that didn’t see it: 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 August, about a month after the first time he fucked me.

So that you have an idea of what we’re like. 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 hourglassy 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 at 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.

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 us 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 in to 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.

Once we got to his house, Tyler had been sitting there stewing in his own horniness for a while. We stepped out of the car and I could see how hard he was through his thin little dress pants. I stepped in front of him, barely brushing my ass against his cock, and headed inside. We said goodnight to his parents and they went off to their bedroom to watch a movie, and we headed to Tyler’s room. The second the door closed, he turned to me.

“Why would you do that?” he said. “I’m sorry,” I said softly, smirking a little, walking closer to him and laying my hand on his chest. “You aren’t!” he said. He looked so hot, as if maybe he was on the verge of crying. “It couldn’t have been that bad, Tyler,” I said. “What if my parents figured out what you were doing?” he asked. “Umm, I wasn’t the one moaning at the table. Maybe you should learn to control yourself,” I said as I walked up to him and grabbed his cock through his pants.

Tyler stared at me for a while. “Just don’t do that again, okay?” “Fine, I’m sorry,” I said as I slipped my dress’s straps off of my shoulders. It billowed down to my feet, and I stood there naked in front of him. He looked my up and down, looking at my red toes, and the drops of wet dripping down my thick thighs. Looking at my little waist and my perky tits, nipples still hard. He looked me in the eyes, then gazed at my red lips and my brown hair bouncing down around my shoulders. “You forgive me, right?” I said. He nodded. “Good.”

I walked up to him, grabbed his jaw, and kissed him, shoving my tongue into his mouth from the first kiss. I let my teeth catch on his bottom lip a few times, then moved down to his neck and started biting and sucking, giving him a hickey. I backed him up to the edge of his bed, pushing him down, and crawled on top of him, me completely naked, him fully clothed. I mounted him and bit at his ear before moving back to his mouth. I grinded my pussy up against him, then sat up.

“You haven’t had a good look at it yet, have you?” I said. I turned around, put a knee on either side of his body, and backed my ass down right into his face. “Oh my god,” he muttered, inches away from the shiny pink jewel on the end of my plug. “I’m such a mess, clean me up,” I said. He started licking at my thighs, working his way to my pussy. Once he got there, I shoved myself down onto his face, riding his lips with my lips, letting his face press into my cheeks. As he thrust his tongue into me, I let my weight down onto his face, sitting on him. He grabbed my thighs and dug his nails in.

“You like that? I bet so,” I said, “God, you’re just such a stupid little slut for me aren’t you?” I leaned forward, pressing my clit onto his tongue, and started undoing his pants. I licked at the tip of his cock, just teasing, while he ran his tongue in circles around the outside of my clit, swiping across every now and again. I wrapped my lips around the head of his cock, and swirled my tongue around for a second. As I came off for a second, my teeth light grazed him. He moaned, and I could feel the sound vibrating my pussy. “I love it when you moan into me.” I started sucking on him as he lapped at my vagina.

I rolled over and moved up to kiss him. “How does my cunt taste, princess?” I asked, kissing him before he could answer. I moved a hand to his cock to keep teasing his head while we made out. I sat on him and let his cock press between my folds, not inside me yet, but rubbing up and down his length with the sleek area between my lips. I spun the plug around inside me to make sure the whole area was wet, then pulled it out. It felt so good to finally take it out, and I began to clench over and over, hard.

I looked Tyler in the eyes and brought the toy up to my lips. It was clean, so I gave it a little suck for show. “Do you wanna turn? I know you do. Be a good boy,” I said as I moved in towards him with it. He swallowed, looking hesitant. Right as he opened his mouth, I pulled back and set it on his nightstand, laughing. “Were you really going to suck on my buttplug for me? You’re such a nasty little whore,” I said, still giggling. I rolled back down and cuddled up next to him, “You know what I do want you to do? I want you fuck me in the ass. Do you think you can handle that? Not too scary?”

My ass was still completely lubed up from last time I adjusted the plug. I laid down, face down ass up. He took off his pants and positioned himself behind me. He slipped inside my ass and thrust in deep. I gasped under my breath. It felt so good, but I grunted out, “Is that all you’ve got? Fuck me like a man.” This did something for Tyler, and he dug his fingers into my sides, grabbing me and throwing me onto himself as hard as he could, hitting me in some deep spot that felt amazing.

I had fucked myself in the ass with toys plenty of times, and always liked getting rimmed, but I had never actually let a guy into my ass. It felt too intimate for the slutty hookups I was used to. Tyler didn’t know this, though, and it was fun not letting him know yet. I made sure that every time he got deep, I clenched hard and gently let go as he slid out, so it felt like I was sucking his dick with my ass.

He pulled out of me and flipped me over. “Oooh look who’s in charge now. What a big boy,” I said. He slipped back inside me, pressing my legs into my body, curling me up into a little ball. It felt incredible, even though there was a little throbbing pain from it. I had never felt something quite like that before. Every time he would thrust in, a little moan would come out, getting louder and louder. “You have to stop, my parents are in the other room,” he said. “Make me,” I growled at him. I took a deep breath and started yelling, but before any sound could come out, he pressed his hand down over my lips and smothered me. “I can’t believe you’re making me do this,” he said. He kept fucking me, then began to move his hand off of my mouth. I got a millisecond into an ecstatic scream before his hand came down on me again.

“You’re such a bitch,” he said, thrusting into me as hard as could. I moved a hand down to my pussy and fingered myself while he fucked my ass. I could tell he was getting close, so I started trilling my finger on my clit. I came through my whole body, clenching him, my legs shaking. I moaned under his hand, and I squirted all over both of us. I don’t usually squirt, but it happens occasionally, and the anal made me so sensitive. The second my squirt hit him, Tyler groaned out, “I’m gonna cum,” letting go of my mouth. “Creampie my ass,” I demanded. He started cumming, with me squeezing down on him. He pulled out, a string of cum hanging off the tip of his cock. I leaned down and gave him one sensual suck of his cock, licking up all the cum on the tip, a little of it dripping down my lip.

I cleaned up for a second, so did he, and we laid down together. I cuddled up with him. “I hope I didn’t go too hard on you,” I whispered. “I can take it,” he said, smiling. “You know I really like you, right?” I asked. “I like you, too,” he whispered back. “I have a confession,” I said, “This is actually my first time ever doing anal.” “How was it?” he asked. “You were amazing, I said. I gave him a few passionate kisses, then laid with him while we listened to music, running my fingers through his hair, and we fell asleep, still naked, lights on, for the night.

Source: reddit.com/r/gonewildstories/comments/hqk0xe/i_f_wore_a_buttplug_to_a_fancy_dinner_with_my