*CH8. The Double Date
Our destination was Carte Blanche, a hotel restaurant considered best in the city. As Vanessa and I walked in, her in a blue cocktail dress, me in the pink summer dress, everyone was staring. It was normal for her, but for me, an entirely new experience. I looked at the ground and focused on walking in the heels, my face burning with embarrassment. Could they tell I was a guy? Would I see someone I knew? I followed Vanessa and the host to a booth against the far wall, and what I saw hit me like a gut punch.
It was Jeff.
He was wearing an expensive grey suit and stood up to give Vanessa a hug and kiss on the cheek. "I didn't know you were bringing a friend! I'm Jeff, what's your name doll?" He reached out his hand and I glared at him, not sure what to do. Then a smirk flashed across his face, and he pulled me into a tight, unwilling hug. "You look real sexy Paula," he whispered, and his hand grazed over my ass.
Jeff insisted we sit on either side of him, and then put his arms around us like we were prostitutes. I tried to pull away, but he yanked me back in. "Careful baby, we don't want you to get hurt like last time." Jeff ordered three bottles of red wine, and then we drank, and ate, and talked. I learned that Vanessa had called him to arrange our date, and had explained that I would be coming as a girl, and that Jeff was ok with it. "More than ok" he said, and reached over to squeeze my thigh. I slapped his hand away. "I get it" he said. "It's our first date, and you're not that type of girl."
My meal was actually incredible, and after a fourth or fifth glass of wine, I was pretty buzzed. The liquor made me feel a lot more confident with the way I was dressed, and I even went and used the ladies room. When I got back Jeff and Vanessa were making out in the booth, his hand under her dress. Then he started getting fresh with me too. Brushing back my fake blond hair, he leaned in to kiss my neck and snuck a hand between my legs. As I pushed him away, his hand brushed against the cage. "What's this?" He looked surprised. I tried to pull his arm back but his hand stayed, exploring the little plastic encasing. "She locked you up, huh?.. That's really sexy Paula." He withdrew his hand from my dress and announced that it was time to do some cocaine. We followed him towards the lobby.
Jeff had a suite on the top floor. After taking a mirror off the wall, he emptied out a huge pile of white powder and lined up 6 skinny trails. Normally I don't do coke but Vanessa was adamant so I snorted one. And then another. My body felt really good, and looking down at my dress and pink nails, I felt like I was in a dream. Jeff put on some music and then carried a chair into the large bedroom so he could "watch his girls make out." Vanessa and I took off our heels, got on the bed, and started kissing. She smelled like flowers and tasted so delicious I lost myself in the moment. I unzipped her dress and ran my hands all over her supple little body. After a couple minutes we were both naked, except I still wore the bra, and my cage of course, dangling just below the white bandage. Our tongues swirled and we pressed our bodies together urgently. Then Vanessa flipped over to sixty nine, her lips just above my face. I licked and sucked on her pussy while she gave the cage little kisses. I couldn't feel them, but I was beyond horny for her, and my dick raged against its confinement.
It wasn't until I saw Jeff's long shaft pass over my face that I even remembered he was there. I stopped licking and watched the huge purple head push against her tiny lips, and then pop inside, just above my face. Her pussy strained around the thick shaft as his balls dangled over my eyes. Vanessa grunted "Lick my clit you little bitch" so I went back to kissing and sucking as he fucked her hole just above. Every so often my tongue made contact with his genitals. After a couple minutes, Jeff ditched the pretense and dragged his balls directly across my tongue. I sucked on them gently, tasting the salty, coarse skin. Then he shifted forward, hovering. I knew what he wanted, so I lapped at his crinkled hole. He sighed, contently. "She's eating my asshole Nessa." They both chuckled. "Here's what you really want though." He pressed the head of his penis down into my mouth. It felt very different than the dildo; warmer, softer, and had a ripe musky taste.
For the next half hour Jeff alternated between fucking Vanessa and fucking my mouth. After she orgasmed Jeff mostly penetrated her ass, stopping every so often to push his cock between my pink lips until bottoming out in my throat. Finally I saw Jeff's balls tighten and he growled at me. "Put your tongue in my butt, I'm about to come." Just as I poked into his hole, he roared and shot a huge load all over Vanessa's blown out asshole. "Ok." he panted, admiring his work. "Eat your dessert." He lifted my head up towards the white globs dripping from her gaping rectum. I started licking and sucking it off. Once it was all gone Vanessa rolled off and we all lay resting on the bed, listening to the soft music drifting in from the next room.
---
Thirty minutes and ten lines of coke later, Jeff was ready to go again. He was naked on the bed, leaning back against the headboard and stroking his dick. I sat on the chair in my bra and cage, high as a kite. "Come here Paula." Jeff patted the bed. "Time to make you a real girl." I was pretty fucked up, but even so, I definitely wasn't doing that. I shook my head and Jeff was displeased. "You don't really have a choice. Come here." I glared at him. Lots of what had happened was on the edge, over it even, but this was going way too far.
"I'm not gay." I said softly.
"I know," he smirked. "That's the best part."
I didn't move, so he continued. "Ok, I'll make you a deal. If you come sit on this, we'll take off your little cage there."
Vanessa, topless in her panties, left for a moment and then came back and set the key on the mirror. I looked at it, and then back at Jeff on the bed. His rigid penis stood straight up like a fire poker. I couldn't. But I really needed the cage off. Badly. I stood up.
"Atta girl" Jeff said.
As I climbed on the bed Vanessa took her phone out to record. He wanted me to ride it while facing him, so he could see my face as I "became a woman." It was an awkward posture, and holding the thick shaft I struggled to position the head at my hole. Finally in the right spot, I sat down, but the wide head pushed futilely against my anus, going nowhere. Jeff recommended I use my spit as lube, so I rubbed some on my butthole, and at his urging, gave his cock a few slobbery kisses.
The second time, with a flash of searing pain, the head slipped past my ring. Jeff moaned in satisfaction, "Ahhhhh I love virgins." My ass burned, but I was determined to get the cage off, so I sank down until it hit the bottom of my stomach. Jeff was loving it, and I felt his dick pulsing as he groped at my flat chest under the bra. He began lifting me up and down, sliding my asshole along his shaft. Then he grabbed the back of my head and forced his tongue into my mouth. His face felt like sandpaper as he lifted me up and down. Up and back down. This went on for about fifteen minutes.
Then, keeping me impaled, he spun me around to face Vanessa, and told her to unlock me. She grabbed the key and went to work on it while he continued penetrating me. When she finally pulled it off, what I saw was alarming.
