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The Girlfriend Experience: Bonus Chapter
🕑 Added 2025-09-22 16:27:08 +0000 UTCOf course I didn’t stop being a ‘girlfriend experience’ girl. I did talk to Jimmy about it. “Are you comfortable with me going out and making some extra cash?” I asked. Of course he asked the predictable questions, like, “Do guys ever try to sleep with you? Do they ever touch you?” And so on…
“No. I literally just sit there,” I said. “Maybe a couple times, guys have put their hands on my thighs, but they aren’t supposed to.” But he already knew that, because before we started dating, he had been hiring girls to sit with him and his friends. I mean—it’s how I met him, after all.
He seemed a bit nervous, but nobody liked money more than Jimmy, so he allowed it. I made more than him, after all.
Though I could tell that he got a bit jealous. One night, while sitting at a table with a young lawyer, I saw Jimmy sauntering by the window. He stopped in to check on me, which I wasn’t entirely thrilled about, but I can’t say I blamed him. He was curious, and maybe a tinge insecure, but I just took that as a compliment.
That particular night, my client wasn’t dining with friends. And I’ll admit that those were the worse gigs. When there were friends, I could feel ignored. I could feel like I was there just to be eye-candy. But when I was alone with a guy, I felt a weird pressure to ‘chat’, even though chatting was kind of a no-no with the ‘girlfriend experience’ gig.
Jimmy didn’t stick around to watch. I think he saw that I was just doing my job, and he went on his way. When I got home, he had a big grin on his face. “How was your date?” he asked.
“It wasn’t a date. And it was fine. He paid me $400 even though it was only an hour and a half.”
His eyes flashed. Nobody loved money more than my Jimmy. “Do you really just sit there?” he asked—as if he wasn’t the one who told me about this whole thing to begin with.
I sighed. “Are we really going to talk about this every night?”
“I have an idea,” he said, grinning. And then he showed me a box.
“What’s that?”
“A toy,” he said. “It’s a remote-controlled prostate stimulator.”
I blushed. “A what?”
“You stick it in your ass, and I can turn it on whenever. It will start to vibrate, making you have an orgasm.”
I could feel my face turning red. “And what… do you want that for?”
He lifted up another box. “This is a remote controlled vibrating cock ring.”
“For you?”
“For you,” he said. “You have that date tomorrow night, right? With those politician guys?”
I nodded slowly.
“I’m going to get a table at the restaurant,” he said, unable to stop grinning.
“You’re going to get me into trouble!”
“Oh, live a little!” he said, waving me off.
I’ll admit that I was intrigued. I liked a bit of naughty fun just as much as the next girl.
So before the date—and before I got dressed—Jimmy unboxed the toys. “Sit down,” he said. I sat, naked on the bed. Then, he got on his knees and took my cock. I bit my lip. He didn’t usually play with my cock; he loved my asshole, and he loved it when I played with his cock, but he never gave my shaft much attention—and I liked it that way; it made me feel more like a girl. But now, he was gently wriggling a silicone ring around my dick.
“It’s tight,” I said.
“It’s supposed to be.” It felt weird. Then, he squished some lube onto the dildo-looking pink toy, which had a butt-plug type base. “Spread ‘em, beautiful,” he said. So I rolled back onto my spine and he gently pushed the thing into my ass. I gasped, feeling the sudden penetration. “It’s cold! You could have warmed it up!”
“Stand up,” he said.
I did.
“Does it feel weird?”
“It feels like there’s a dick in my ass, and someone squeezing my dick.”
“Perfect,” he said, rubbing his hands together. “Tonight will be fun.”
The feeling was weird, but I honestly managed to forget about it over the next hour as I got myself ready in a little red dress and matching red heels. I curled my hair all pretty and made my eyes sparkle. And then I was off to the restaurant. I got a seat between two of the men, who both wore black pressed suits. They started blabbing about work almost instantly.
Sitting on my ass, I could feel the dildo more, because it was being pushed in harder. But it wasn’t too distracting. After all, I let Jimmy fuck me in the ass whenever he wanted to, and he was bigger than the toy.
I ate my dinner. I got my dessert. I had a drink. The men kept talking. I forgot all about the toy in my ass until suddenly.
“Oh my God,” I gasped.
The men all looked at me as I tensed up.
“Are you… okay?” one man asked.
Deep in my ass, the toy was buzzing. I blinked a few times, and then smiled and nodded and forced myself to settle back down. “That dessert was just… so good.”
They went back to their chat. Then, the vibration became more intense.
I bit hard on my tongue, stopping myself from making another noise.
But Jimmy was determined to make a fool of me. He hit another button, making the ring around my dick start to gently vibrate.
I gasped, getting a look from one of the men, but I smiled and acted normal.
They kept talking.
Jimmy turned up the power.
In my ass, the vibrating was intense, sending pulses of warm euphoria through me. The ring around my cock pulsed harder, and it suddenly started to feel tighter.
I quietly looked down and saw the growing bulge. “Asshole,” I whispered. I looked over and saw him at his faraway table. He smiled at me.
I wanted to beg him to stop. It was a bad time—right before I was going to be paid.
I sipped my drink—a pina colada. I tried to steady my breathing.
But the buzzing intensified. My knees closed hard together. I bit my tongue. I felt my eyes rolling back. The men eyed me again. I made a smile—surely an awkward, crooked smile. “Good drink,” I said.
My cock was pulsing now. I was so hard. I don’t think I’d ever been that hard before.
Jimmy was fucking me with his toys from across the restaurant.
I tried to drink my drink, but nearly dropped it, so I set it back down. My hands were shaking. My legs were shaking. It felt so, so good.
Then, I let out a sound. “Fuck!” The men looked at me. I gripped the table. I opened my mouth and took a sharp breath in. Then, I managed to say, “This drink is so good,” with a strained voice.
They looked a bit annoyed. I wasn’t supposed to be talking. But they went back to their chat.
And I felt it gushing. My cock was unloading under my dress. I didn’t want to ruin the dress and have an awkward wet spot, so I managed to pull the skirt up without the men noticing. But my cock was so hard that I had no control over it. It sputtered everywhere, all over the underside of the table, the floor, and even the bench we were sitting on. It was a big mess—cum everywhere. I’d never ejaculated so much cum before!
I knew I had to create a cover, so I purposely spilled my drink. “Oops!” I cried.
The men looked over again, now more annoyed than ever.
The man to my left lifted his hand. “It missed my pants,” he said. “But it’s all over my hand. And it’s warm. Why is it so warm?”
I blushed. I looked at his elevated hand, which was dripping with my sticky cum.
“It was warm,” I said. “But it was good.”
“Apparently,” the other man said. “It’s fine. The waitress will come clean it. Just… be more careful, please.”
I nodded, obediently. We all got out from the table while the waitress came over.
“I got it on my hands too,” another man said, using a napkin to wipe the cum from his fingers. “It’s so sticky.”
“It’s really sticky,” said his friend.
I just stood there blushing, praying they wouldn’t smell it and realize they were both covered in my cum. And the poor waitress, scrubbing it all away, wondering how the spill got on the underside of the table.
I eyed Jimmy, who couldn’t stop laughing. Asshole. He was lucky that it felt so good.
I was better behaved for the rest of the night. The men paid me well and didn’t mention the incident. But that wasn’t the end of the night for me. Apparently, watching me cum all over myself had Jimmy ruthlessly turned on, so he wanted to fuck me as soon as I was home—so I let him. He got me onto my hands and knees and penetrated me deeply, thrusting hard into me until he was filling my hole with his seed.
“We should do that again,” he grinned.
“No!” I said. “You’re going to get me intro trouble. It’s not funny. Stop laughing.”
“You have to admit that it’s a little bit funny.”
He was lucky he was cute.
