I'm a server at a high-end restaurant. A customer paid me to kiss her virgin son. What happened next changed my life forever.

*Everyone in this story is 18+ and fully consenting.*

Sophia handed me a towel that was softer and more fluffy than any towel I had ever used in my life, and I dried myself with it while she did the same with her own towel.

For the first time of the evening, she almost seemed hesitant before speaking. “Um, may I inquire whether you’re… protected?”

Her manner of speaking was sometimes overly formal, but it only took me a few seconds to realize she was asking if I was on birth control.

“I have an IUD,” I said simply.

She nodded knowingly. “Ah, very good. Thank you. I can assure you my Kenny hasn’t been with other women, so I want to know, are you currently entangled?”

*Entangled*? I smiled now and she realized how weird she was sounding. She added, “Sorry, I know sometimes my speech is too formal. What I’m asking is–”

I interrupted, “I don’t have a boyfriend right now, and it’s been months since I last had sex. I don’t have any STIs, Sophie.”

That took *her* aback, and I felt proud of myself because I didn’t think I would ever get this woman on her back foot.

This time she laughed. “Well, then, that’s perfect. Then are you okay if we don’t use condoms?”

Again with that weird ‘*we*,’ like they were going to fuck me together. But, I thought it over and since she was going to be in the room and watching, this was indeed a ‘we’ thing.

“Honestly, I hate condoms. I hate them so much. They feel so artificial. It’s the main reason I got my IUD, with the other reason being super-light periods,” I answered.

Her expression was filled with understanding. “Oh my god, I remember when I got my first IUD in and how much easier my periods were. They were basically nonexistent. Most of the time I had a tiny bit of spotting and that was it. The worst part was putting the damned thing in. It hurt so fucking much!”

We commiserated a little more about the sad state of women’s healthcare until she started walking towards the door. She said, “Shall we? I hope he didn’t jerk off first.” We both laughed.

While she was walking toward the door to her bedroom, she made a detour to her large king-sized bed and slid open a nightstand drawer. She retrieved a purple wand toy and turned back to face me.

“Do you have a Lelo wand? It’s my favorite toy.”

I laughed a little and said, “Um, I only have a cheap silicone dildo and a Satisfyer Penguin. I wish I could afford a Lelo wand. How is it?”

She was already walking toward me. “A penguin satisfier? I’m not sure I know what that is, but it sounds interesting. I must get you a Lelo. Here, hold still.”

Before I had time to explain about the Penguin toy, she clicked her Lelo on and pressed a button to speed it up a little. She put her arm around my back and pressed the Lelo right to my pussy, knowing I would need to be held to remain standing. An intense pleasure explosion rocked my body, causing me to loudly gasp. I sucked in a breath loudly and cried out, “Oh my god! Oh shit!”

Instead of letting me continue towards my inevitable orgasm, she took it away and clicked it off. I looked at her like she had just shown me Heaven itself and then snatched the vision away just when I was about to arrive.

She giggled and said, “That’s how it is. Maybe we’ll play more later, but right now, Kenny’s waiting.”

I took a deep breath and nodded, following her down the hallway.

Sophie knocked softly twice on Kenny’s door, not waiting for a response before swinging the door open.

Kenny was lying on his bed under his covers and scrolling on his phone. He looked up and saw his naked mother standing in his doorway and said, “Oh shit, Mother! What are you doing?!”

Somewhere in the back of my mind, I wondered if he always called her ‘Mother,’ but that thought was fleeting as he noticed the Lelo wand his mother was holding. He quickly added, “Wait, you want to watch us have sex, too?”

Her voice was soothing and manipulative. “If you don’t mind, Honey Bear, Mama would like to see you become a man. After everything I’ve given you and done for you, including bringing you Lexi tonight, don’t you think it’s not that much to ask for me to sit there in your chair and watch and have a little fun myself?”

Kenny didn’t resist nearly as much as I would have. “You don’t think that’s a little weird?”

From where I was standing, it was clear that he was looking directly at her tits, and it gave him away. Sophia knew it too, and she used it to her advantage.

She walked over to the side of his bed and even leaned over a bit, putting her boobs directly in his view. Watching his eyes become glued to her was a little funny, but at the same time, I honestly couldn’t blame him.

“Maybe a little weird, but you do get to look at two beautiful naked women, so what’s the downside?” she pushed.

She turned slightly and gestured to me, standing there watching them. “Don’t you think she’s beautiful, baby?”

Kenny looked past her to me and I immediately put on a sultry expression, trying my best to look sexy. I stood tall the way she had told me to before, thrusting my boobs out as much as I could. Putting the cherry on top, I turned and let him see my ass, and I knew it was the right call because he softly said, “Fuck… Yeah, she is.”

I joined her by the bed and she pulled me into the spot where she had been standing, and then walked over and sat down in the chair that was closest to Kenny’s bed. He had three really nice chairs in his room, and it made me think about how I could barely squeeze in around the sides of my queen-sized bed back at my apartment.

That was my signal to get started, and since it didn’t seem like Kenny was going to take charge, I decided to.

“How about we kiss some more first,” I suggested.

From the chair, Sophia got up and came over to the bed. At first, I was confused. Was she about to join in or something? “Don’t mind me, I just need a blankie,” she said, being very cute. She tugged at the comforter on Kenny’s bed and dragged it behind her back to the chair. We both watched her butt as she walked, and she noticed, of course.

Pulling the comforter off of the bed had the probably-intended side effect of exposing Kenny’s naked body, and it made him immediately pull the sheet back over him.

“Don’t be shy, baby. She’s going to see it anyway,” Sophia said.

I wanted to see *it*, too, but I was okay to wait a little more. I laid down next to him and we started kissing again.

I didn’t want to rush his first time. I remembered back to when I was sixteen and lost my virginity to a clumsy high school kid who had no patience, expecting me to be instantly wet and ready for him to stick his dick into me without any foreplay.

Back then, I wasn’t comfortable advocating for myself and so I just let him do whatever he wanted, and it hurt, made me bleed, and he finished in about five thrusts. At that moment, I wondered what the big deal about sex was if it was like this. It took a good five more boyfriends until I found one who took his time and actually made me orgasm. That was when I had that “aha!” moment and knew that sex could truly be something beautiful and connecting.

We continued kissing for a while, and it was nice, but he wasn’t touching me very much. I broke the kiss, and took his hand and placed it on my breast. “It’s okay if you want to touch me,” I said comfortingly.

He softly moaned and now his hands started roaming over my body. I encouraged him with some genuine moans and told him, “Just go slow; we have plenty of time.”

He looked into my eyes and I could see some relief. I don’t think he knew exactly what to say because he came up with, “You’re really nice.” That made me smile.

“Tell her how sexy she is, baby,” Sophia chimed in.

Kenny shook his head in kind of an annoyed manner, but he recovered quickly. “You really are sexy, Lexi.” He laughed when he heard himself say the words out loud and added, “Has anyone ever called you Sexy Lexi?”

I laughed and so did Sophia. I lied, “Maybe once or twice.” I have actually been called that a *lot*.

He kept looking at my boobs and so I offered him one. I said softly, “Go ahead, you can suck it.”

Feeling his tongue on my nipple reignited my arousal instantly, and I felt my clit tingling. From behind me, I heard Sophia moan as well, and she turned on her Lelo. Hearing the low rumble turned me on even more. Apparently I enjoyed being watched, at least by her.

Kenny was now devouring my nipples. Just to encourage him further, I caressed his hard cock over the sheet, causing him to suck on me even more firmly and moan into my skin. It was at that moment that I felt myself getting really wet. I was really needing to be filled up now.

Sophia increased the speed on her Lelo a bit as I moved to pull the sheet down, revealing Kenny’s hard cock. Looking at him, I couldn’t understand how this guy could possibly be a virgin. He was maybe a little overweight and had pretty pale skin, but nothing too crazy, and his dick had to be at least seven inches, and, more importantly, it was nice and thick. I felt my mouth start to water as I imagined having him in my mouth.

After a few more minutes of very passionate kissing, I took the initiative again and moved down his body, slowly kissing my way down. I even sucked and bit on his nipples a bit, which while he didn’t have a big reaction, he still made cute little ‘hmmm’ sounds to show he liked it.

Finally, I had arrived at my destination. Kenny’s thick cock had a thin sheen of precum leaking from it, and I wasted no time in licking it from his tip. His cock instantly reacted and he moaned really loudly. From the chair, I heard Sophia let out a breathy ‘ohhh’ sound, which was hot.

I had a thought and climbed over him so I was on the opposite side from where Sophia was sitting, giving her a completely unobstructed view of what was happening. I made eye contact with her and took her son’s thick cock into my mouth. In response, she closed her eyes and moaned louder.

Fuck, his cock felt so good in my mouth. It was so good to finally feel it inside my body, even if it wasn’t in my pussy yet.

I had a thought and asked, “Can you usually go again pretty soon after you come?”

Kenny opened his eyes to look at me and nodded, which was great news to me. I wanted to taste him. I proceeded to give him what I assumed to be his first blowjob, and even if not, hopefully the best one he’d ever had.

It took an exceedingly short amount of time before he was raising his hips off the bed and thrusting his cock deep into my mouth, trying to penetrate my throat. He was a little thick to get it in and I was out of practice, but it didn’t matter. In what had to be less than two minutes, he lost it and began shooting jets of hot cum into my mouth.

He came a lot, and I let it all fill up inside of my mouth while moaning loudly. I slowly blew out a breath, made sure to control my gag reflex, and then swallowed all of his cum at once, and nearly came myself. It had been much too long since I had sucked a guy’s dick, and it turned me on like crazy to do it. I continued sucking his cock for another minute until I had all of his cum inside of me where I wanted it.

From the chair, I could see that Sophia was having an orgasm too, but she was trying her best to not make too much noise. The loudest sound she made was a kind of breathy “hunnhh” sound. Hearing and watching her masturbate had my clit screaming for release, but I didn’t dare touch myself.

Sophia couldn’t help herself. She turned off her Lelo, got up and came back to the side of the bed. She asked Kenny, “How was that, baby? Did it feel good?” She started stroking his face and hair, and even leaned over and kissed his forehead several times. It was pretty cute.

She surprised me when she turned to me and said, “Thank you so much, Lexi.” She smiled widely and then quickly moved in and gave me a sloppy, open-mouthed kiss. It caught me off guard at first, but I didn’t pull back and instead kissed her back with passion, trying my best to match her energy. She even sucked my tongue and I sucked on hers. I couldn’t wait until we could have a proper makeout session later.

On the bed, Kenny could only say, “Fuck, that’s so hot!” He was right.

She broke the kiss and looked back at him. He said, “It was the most awesomest thing ever, Mama.”

I smiled to myself as my question about ‘mother’ had been answered.

Sophia said, “Sorry, I shouldn’t have interrupted. Go on.” She went back to her chair.

It was time to test Kenny’s refractory period, and he wasn’t wrong. It only took him about ten minutes before I had him nice and hard again using my hands and mouth.

“Do you want to try being on top?” I asked.

The rumble of the Lelo had returned and I glanced over and saw Sophia’s eyes locked with mine. I looked back at him and he was already getting into position.

I said, “Hold on, you need to get me wet on the outside. Can you lick my pussy a little before you fuck me?”

From the chair, Sophia moaned again with an “ohhh” sound. I was really enjoying having an audience. I never would’ve imagined I would like that.

Kenny did as he was told and used a good amount of saliva between my outer labia, causing me to moan loudly. I said softly, “That’s good, mmmm.”

He only did it for a few seconds, but it was enough. He moved up and I looked into his eyes. “Ready? Now get yourself wet too. It’ll help it slide in easier.”

“Oh god yes, slide it in,” Sophia moaned and increased the speed of the Lelo substantially.

And he did. He had a little trouble finding my hole, but I guided him with words and told him when he was at the right spot, and when to push it inside of me.

It was his turn to groan and let out a breathy “ohhhhh wowwww” sound now.

For me, I pulled up my legs to my chest and felt his cock bottom out in me. I could feel his circumcised head just barely bumping against my cervix and felt bliss as I was finally being filled up properly.

This whole night had been sexually charged, and I had been aroused for so long now that it wasn’t going to take much more to get me there, and as Kenny thrust into me, gently at first, but quickly gaining momentum as he found his stride, I started to feel my orgasm beginning to take its familiar shape.

I’d had my eyes closed up until now, but I opened them to look at him to see his face when he came. He had his eyes shut tightly and was going at a perfect pace for me. I turned my head and looked at Sophia.

I made eye contact with her for a moment, but when she dropped the comforter to show me she was spread-eagle on the chair, seeing her pussy and her aroused expression sent me over the edge and I started having a full-body g-spot orgasm. I could feel my vagina rhythmically squeezing around Kenny’s cock and I started moaning really loudly. All of a sudden, I felt Kenny’s cock swell and get even harder, and I knew what would happen next.

The squeezing must have been too much for him because his eyes flew open and he announced loudly, “Oh fuck, it’s coming! I’m coming! I’m–”

From the chair, Sophia started having another orgasm while her son was pumping his load deep inside my pussy, filling me up, making me have yet another smaller orgasm, and for a perfect moment, everyone in the room was moaning in intense pleasure.

Sophia started saying, “Oh god, oh god,” and then moaned really loudly and closed her legs tightly around the Lelo and slumped forward on her chair. She was having what looked like a very powerful orgasm now, one that was way bigger than the apparently smaller ones from before.

Even though Kenny had come, he was still slowly thrusting into me. When his mother had her really big orgasm, he looked over at her and I felt his cock spasm several times. He was definitely reacting to her coming, and that turned me on all over again.

Nothing can last forever, of course, and after another long moment everyone calmed down. Kenny collapsed on top of me, kissing me deeply and thanking me again and again. I told him it was my pleasure, literally, and that made Sophia giggle.

She also thanked me, and then came over to the bed and sat next to us. She rubbed his back lovingly and asked him if his first time was as good as he had dreamed about.

It surprised me a little when he lifted himself up and repositioned so he could pull her into a tight hug. There they were, mother and son, naked and tightly hugging each other. It was at once erotic, beautiful, loving, and a little weird.

He didn’t really answer her question directly. He didn’t have to because she understood immediately that he’d had an amazing experience. He did say, “I love you, Mama.”

Both Sophia and I simultaneously said, “Awwwww,” and she hugged him even tighter. “I love you too, my sweet Honey Bear.”

He laughed and said, “Maybe don’t call me that in front of Lexi. I’m not five anymore.”

I said, “I think it’s adorable. I don’t think less of you, Honey Bear.” My eyes sparkled, I’m sure.

At that point, we all laughed loudly at my little joke. Sophia looked down at me and said, “Come here, Sexy Lexi. I need a hug from you, too.”

I laughed and took Kenny’s place in his mother’s arms. We embraced tightly and I said softly, “Thank you for tonight. This was so special.”

“For me, too. Thank you for agreeing to come to a complete stranger’s house and for making my son’s first time perfect.”

She looked back to him and said, “It wasn’t so bad having me watch, was it?”

He laughed and said, “I mean, I guess. It was fine. Weird. Yeah, really weird. But still fine. I guess.”

Everyone laughed again as he stumbled through his word salad.

Sophia said, “I’m going with ‘it was fine.’ For now, Lexi and I have a little date in the shower. You should shower again, too.”

Kenny collapsed on the bed and said, “I’m pretty tired; I think I’ll wait until later. I don’t mind having Lexi all over me.”

He looked at me and smiled, and I kissed him. “You’re so sweet. I like having you all over and in me, too.”

After a little more small talk, Sophia and I got up and headed back to her bedroom. I wasn’t sure what she had planned next, but I was nothing but ready to find out.