First Time We Met for a Drink
by velvetskin
Copyright© 2026 by velvetskin
Erotica Sex Story: I was invited out for a drink by an online friend whom I had met on a gay dating site, but I was not expecting him to arrive with company.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Ma Mult Coercion Consensual Drunk/Drugged CrossDressing Fiction Gang Bang Group Sex Anal Sex Cream Pie Exhibitionism First Oral Sex .
After we chatted a few times online, you invited me for drinks on a Friday night at a quiet location, assuring me not to worry as it was quite secluded. I had butterflies all week, eagerly anticipating our first meeting. On the day of our encounter, I painted my toenails red and adorned my feet with toe rings. I took a shower, shaved my body completely, and slipped into a pair of sexy panties. On top, I wore loose and comfortable knee-length shorts and brought along my red lipstick and some cash. I didn’t carry condoms with me, as I wasn’t expecting the night to lead anywhere, given that this was my first in-person meeting. Additionally, I decided not to drive, just in case I drank too much, so I opted for a taxi ride.
When I arrived, I noticed that the venue was quite secluded, yet charming. The ambience was created solely by candlelight, casting a warm glow throughout the dimly lit space. I spotted you sitting at a table, but you were not alone; you had invited two of your closest friends to join us. I wasn’t sure why, but I felt a wave of nervousness wash over me. Both friends appeared to be around your age, freshly shaven, and of stocky build. They smiled warmly upon seeing me.
“I hope you don’t mind, but I asked a couple of my best friends to join us for a drink,” you said.
I smiled back, introducing myself as I took a seat. There was a sofa across from where you were sitting, with chairs on either side, so I settled in between your friends. The table was tucked away in a far corner, shielded from prying eyes, adorned with plants and flickering candles. The waiter approached, and you ordered wine and cocktails for all of us, knowing that wine allows me to mellow out. Little did I know, you had already shared details about me with your friends—our online chats, my fantasies (such as painting my toes, wearing micro skirts, dressing up like a good girl, and my desire to be topped by two or men at the same time, all dolled up as a sissy)—and even shared pictures of my body. The drinks arrived alongside an assortment of sweets and finger foods.
Your friends engaged in small talk, and I was uncertain where the conversation would lead, but they made sure my wine glass was always full. The venue was quiet, with only a few patrons scattered around, allowing me to take in the surroundings and enjoy the background music. Gradually, you all began to notice that my cheeks were reddening from the alcohol, and I was smiling more than usual, revelling in the evening and feeling increasingly at ease. They started asking me questions about myself—some general inquiries about life and my interests, while others ventured into more erotic territory, focusing on cross-dressing, sissies, and group sex.
“I really loved this picture of your painted toes,” said one of your friends, showing me a picture I had shared with you. It featured me naked on all fours, facing the mirror.
“Are they painted like this tonight?”
I blushed immediately, as it was the first time someone had asked me that publicly in front of others—someone I had never met or spoken to before. I took a big sip of wine and replied, “Yes, they are.”
“Can we see them?” asked the one opposite him.
I couldn’t believe that your friends were asking me to show my painted toes in public; it was something I had never done before. I felt both excited and embarrassed at the same time. You poured more wine into my glass and smiled at me, encouraging me to relax and embrace the moment.
“Why don’t you take off your shoes and show them?” you suggested. “Don’t worry; nobody is watching.”
I took another sip contemplating the idea of me going ahead with it. As I reached under the table to remove my shoes, I noticed one of your friends reaching for his mobile phone and lowering it discreetly. He intended to capture the moment and I sensed that you were all becoming excited to witness it. He asked if it was alright to record, and I nodded. I took off my shoes and then slowly removed my socks in a deliberately sensual manner. You were gazing directly into my eyes while I caught a glimpse of your other friend becoming aroused as he subtly rubbed the top of his pants. The one with the mobile phone inquired if he could take a picture and share it with everyone, and I nodded again in agreement as he sent it. You all wore broad smiles as you admired my red-painted toes and the two toe rings I wore—one on each second toe. You had mentioned online that you found them sexy, and having two felt more fitting for my fantasies.
“Leave them out in the open until we leave,” you commanded.
I took another sip of wine as you all focused on your phones and my toes, which clearly excited you.
Moments later, your friend to the left mentioned that his back was hurting a bit and asked if he could move to the sofa. He sat down and discreetly began caressing my leg, which distracted me, as it was the first time I had experienced a guy touching me in such an intimate way. He told me that I had very soft and sensual skin, similar to that of a woman, and that it was a significant turn-on for him. He even remarked that my toes and feet were quite feminine and that he liked how they appeared slightly crooked, as if I wore heels all the time. I smiled back, thanked him for his kind words, and felt myself blush. My knee-length shorts were loose, allowing him to slide his hand further up around my thighs before he withdrew it. After taking another sip of my wine, I leaned forward onto the table and felt his hand slip under my t-shirt, caressing my back and moving lower before stopping.
“Are you wearing panties tonight?” he asked.
“Yes, I am,” I replied.
“Good girl,” he said, as everyone smiled.
“Have you tried any of these sweets? They are really delicious. Would you like to try one?” asked the one sitting to my right.
“Sure, I wouldn’t mind tasting one,” I said.
It was covered in syrup and resembled the kind of treat any grandmother would make. He then shifted slightly and moved to the right side of the sofa, so we were all sitting opposite you. He picked up the sweet and brought it closer to my mouth but then paused.
“Open your mouth slightly for me,” he said.
My cheeks were already flushed from the wine, but they turned even redder when he said that. Trembling, I slowly opened my mouth as he brought the sweet closer and rubbed it around my lips, coating them in syrup. The rest of you were watching intently, and all three of you moved closer to prevent anyone else from seeing what was happening.
“Now lick your lips slowly with your tongue,” he instructed, and I complied.
“Good girl,” said the one to my left.
I blushed once more, yet simultaneously felt more at ease. Your friend to the left, who had been gently caressing my lower back, had now taken my hand and placed it on his bulge. I could feel the heat and firmness of his arousal, which was clearly much larger than I had anticipated. My hand barely covered his size. He was moving his cock ever so slightly against my palm as he and the rest of you were smiling. You poured more wine in my glass as your friend on the right moved closer to me as well.
“Have another drink baby,” and he picked up my wine glass and held it to my lips.
You all enjoyed seeing me become more mellow as he made me drink more than just a small sip this time. I nearly spilled the wine all over me but he enjoyed watching me become submissive to his demand which was to take larger gulps than just sips.
At the same time, he took my right hand and placed it on his bulge. I couldn’t believe what was happening as both my hands rested on their cocks, even over their trousers. You held your phone and lowered it under the table to record a video of my actions.
“Do they feel good, baby?” you asked.
“Yes,” I replied.
“Do you want to feel them directly in your hands?”
“Yes,” I responded.
Part of me knew it was mostly the wine talking but I also felt so comfortable and at ease.
Each of your friends lowered their zippers and revealed their impressive sizes. The friend to your right picked up my wine glass once more and said, “Drink.”
He was aware that I could easily become tipsy, and I sensed that he wanted me to let go of all my inhibitions tonight. My hands began to explore their girths; both were uncircumcised and had large, rounded heads.
“Do you want to taste them?” you asked.
“Yes,” I replied.
You were sitting across from us, observing the scene and smiling as your friends returned the gesture.
“It’s a nice night. Want to take a drive in a little bit? We can get some fresh air and then head to a nice secluded area I know just outside the city, where there’s a beautiful view of the city lights. We could pick up some drinks on the way; it will be more relaxing without anyone else around. We can play some music in the car and dance a bit in nature. What do you say?”
“That sounds nice.”
I was already feeling the wine dancing through me and some fresh air would be good.
The waiter brought the bill, and you took care of it. I had to put my socks and shoes back on, so standing up was manageable, but I could definitely feel the buzz. Fortunately, I didn’t embarrass myself, and your friends had their arms around my waist, ensuring that I was okay. One was even gently caressing my back while the other’s hand ventured lower. I didn’t flinch at all.
The walk to the car was short; you had a large SUV with tinted back windows and plenty of room in the back seats. You had all arrived in that car, so I sat in the middle, flanked by your two friends as you drove off.
“Let’s go pick up some more drinks before we head out.”
The cold air outside was refreshing, but I could still feel the effects of the wine, especially from the last few sips your friend made me take. We stopped at an open supermarket, and only you got out. Nobody could see us in the back from outside, which was reassuring. You returned with a couple of cartons of wine, more alcohol, cigarettes, some baked goods, and a few other items in a nylon bag. You placed everything on the seat next to you. As you drove off again, we began to leave the busy streets behind and headed out of the city onto the highway.
“We have some time until we arrive, so why don’t you relax a bit? Take off your shoes, socks, and shorts too; show us those lovely feet and slim legs, baby. You’ll feel more comfortable as well,” I heard you say.
My thoughts were suddenly distracted by your request. Your friend on the right asked, “Would you like us to help you?” asked your friend to the right.
“Yeah,” I replied softly.
Without further notice, both of your friends removed my shoes, socks, and lowered my shorts until they were completely off. As they took off my shorts, they discovered my lipstick inside the pocket. One of them took it and instructed me to turn toward him while he applied some to my lips, achieving his desired effect. My lips became redder than my cheeks and complemented my painted toes quite nicely. They then placed everything in the back of the car. One hand rested on my left thigh while the other was on my back. I was half-naked in a car with three men for the first time; something I would possibly never had done on an ordinary day. I felt both shy and aroused, especially with my red-painted toes on display.
“Spread your legs a little and show us those panties you’re wearing.”
At that moment, I felt my face flush deeper than a beetroot. The wine was clouding my thoughts, making it difficult to concentrate. My small soldier had shrunk, as it often does when I’ve had a few too many drinks. Your friends gently spread my legs and took more pictures of me, wearing only a t-shirt, my panties, and my painted red toes. You had tilted your rear view mirror slightly downward to get a better view as well.
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