F27 I made a surprise during the date
I've been seeing a guy for a little over a month, we've had several dates, but we hadn't gone beyond a few kisses. He's a very kind, polite, and fun guy, as well as very attractive. On our last date, we almost had sex in the car, the kisses were hot, his penis was throbbing under my thighs, I sat on his lap with more weight to feel that erection, but unfortunately we were interrupted by a group of people passing by on the street, so we decided to go home.
When I got home, I couldn't hold back, I went to bed and masturbated until I was exhausted. I spent the night thinking about him, I planned another date, but this time with the intention of ending in sex, he was very respectful so I decided to take the initiative, I couldn't wait any longer.
I have an anal plug with a heart-shaped base, I spent days thinking about whether I should wear it to this date, I was afraid he wouldn't like it, or that he would think bad things about me. I decided that I would go plugged in to this date, even though I was worried about his reaction.
The day before the date, I wore the plug for a few hours to prepare my butt. I didn't want to feel pain less than an hour before the date and have to take the plug out. So I put the plug in and went to the beauty salon. I stayed there for more than 4 hours. Sometimes the plug hurt, so I would go to the bathroom, take it out for a few minutes, and put it back in. I felt like I was ready to wear it throughout the entire date.
On the day of the date, I was so anxious I couldn't breathe. The closer the time got, the faster my heart raced. My outfit was already ready: a black dress with a beautiful neckline, fitted at the waist and flared at the bottom. Underneath, I wore a black thong. I put the plug in my bag along with a small bottle of lubricant.
We were going to a very nice restaurant with soft, yellow lighting. When we arrived at the restaurant, my legs were sweating, my hands were trembling. I told him I was going to the bathroom, grabbed my bag, and went. I went into the bathroom, opened my bag, and took out the plug. I lubricated it well and inserted it. My whole body shivered, I felt a huge chill in my stomach, but I didn't give up. I adjusted my thong to hold the plug in place and went back to the table.
The food arrived, and we ate everything. I had even lost my appetite from so much nervousness. When we finished, we ordered a bottle of wine, which was exactly what I needed. After two glasses, I started to feel lighter. We were at the back of the restaurant, with our backs to a wall. I pulled my chair up and placed it next to him. The restaurant wasn't very crowded. After a few conversations, I lifted my dress slightly, just enough to show my thong. I did this only to see his reaction. If he had a negative reaction, I wouldn't even show him the plug. But his reaction was the best possible. He smiled, kissed behind my ear, and then ran his hand over my vagina. That's when I realized I could tell him about the plug. I got very close to his ear and whispered, "I'm hiding something under my dress." He looked at me confused, so I took his hand, placed it on the chair, and sat on it. The plug was perfectly positioned in his palm. I could feel him gently pulling on it. He looked at me surprised and asked, "Is that a plug?" I nodded. He raised his hand and called the waiter over, clearly in a hurry, the bulge in his pants was visible. The waiter brought the bill, he paid quickly and thanked him, took my hand and led me to the exit. When we were near where the car was parked, he ran his hand over my butt, holding the plug again. It was the first time he had been so bold. When we got in the car, he asked me to show him the plug. I got on all fours on the seat and lifted my dress. He looked and squeezed my butt, then I felt him run his tongue over it. When he did that, I froze. That shy and respectful young man had just licked my pussy.
He started the car and drove off. I thought we were going to his house, but he stopped under several trees on a completely deserted and dark street. He pulled me close and started kissing me. Before I knew it, I felt his hand pushing me towards his lap. I didn't waste any time; I pulled his penis out of his pants and started sucking it. Finally, I was satisfying my desire to suck that penis. After a few minutes, he put me on his lap and put his penis inside my vagina. The plug was making my vagina so tight that his penis could barely enter. I started riding him, his penis pushing the plug until I managed to expel it from my anus. He asked if he could put it in my anus. Even though I was plugged, I had never done anal before, but I was so horny that when his penis entered, I hugged his head tightly, almost suffocating him with my breasts. I let out a loud moan, but slowly I started riding him. I felt more pleasure than I imagined; it felt so good. After a few minutes later I felt him hug my waist tightly, then his cock started throbbing in my ass, when suddenly I felt something warm inside my butt, it was strangely good, I never imagined that was the sensation. I got off him and put my panties back on, I felt the liquid running from my ass, but I didn't say anything. He took me to my house and we finished that date better than I imagined.
Sorry for the long story, I didn't want to split it into two parts.