She lost her virginity at fifteen to the twenty-nine-year-old leading man of her father’s latest film.
I cried for a week. It was the first time she'd gotten something before me, and it was offensive to my soul. It had taken me a week to work out a solution. After I dried my tears, I fucked her father. Oh, don't look at me like that. Her parents had long since been divorced, and I never told her how I lost my hymen. I'm not a monster.
"Hey, doll," I greet as I settle into the chair being held for me by the Ma?tre d’. "Sorry I'm late.
"No worries, Jenny," she replies. She means it too. She really is that sweet.
"Tragic news," I sigh after we place drink orders and put our menus aside.
"What's wrong? Is your Dad okay?" Darlene's perfect brow wrinkles in concern.
"Dad's as fit as ever. It's Sam. He wants us to be exclusive."
"That's wonderful!" Darlene beams. She just got engaged to an entertainment lawyer. I'm sure visions of sugar plums and joint wedding planning excursions are dancing in her head.
"I'm not ready to give up Greg."
"There is no future in Greg. Sam is a catch."
I shrug. "I like them both."
Darlene groans. "You can't have everything, Jenny."
The waitress places our drinks on the table as I ponder Darlene's words. Why can't I have it all? I deserve it all.
"Why can't I have them both? I want them both."
"Both?" Darlene raises her eyebrows in disbelief.
"Yes." I'm firm. "Sam is the smartest, most successful man I've ever dated. He's the perfect date for public events.”
"And Greg?" she prods.
"Greg's just…" I sigh. "Greg makes me feel like I'm the smartest, most successful person he's ever dated."
"Because you are the smartest, most successful person he's ever dated," Darlene points out with a shake of her head. "So, you're proposing you continue to date them both indefinitely?"
"Together."
"Together?"
"Yes, together."
"You want a relationship with the three of you?" She looks dubious. I'm surprised. She's normally very supportive of my goals.
"Sure. Why not?" I ask.
"Sam and Greg aren't gay, for starters."
"No, no," I interrupt. "I don't want them to fuck each other. I want them both fucking me."
"Oh," Darlene responds, finally getting it. "At the same time?"
I nod.
She looks skeptical again.
"Well, good luck with that," she says, then raises her glass to toast.
I laugh and clink my glass against hers.
Four
The following week, Greg arrives at my door with a six-pack of beer and a hard on. We take the beers outside and open a couple while watching the sunset.
Greg tells me about his lunch shift at wherever the fuck he works, and I tell him about my day of approving designs for the launch of my spring line.
He rubs my feet while we talk, and his touch makes me tingle all over. I can't give him up. I scoot over on the outdoor chaise we're snuggled on and throw one leg over his so I'm straddling his lap. I unbuckle his pants and pull his cock out with one hand while wrapping my other behind his neck.
"I missed you," I tell him, then suck his earlobe between my teeth.
"You just saw me," he replies as he wraps his hand over mine on his cock.
He's right. I did. And we normally only see each other a few times a month, but Sam asking for exclusivity has made me realize how much I'd miss Greg if I had to give him up.
"Are you seeing anyone else right now?" I ask.
"No one serious," he replies. "Are you still with Sam?" He looks curious.
"I am," I say, keeping a firm grip on his cock. I rotate my wrist a little as I slide it up and down, his hand still lightly covering mine.
"Why are you asking?" Greg brushes his thumb along my bottom lip, and I suck it into my mouth before responding.
"I was thinking we could try something new."
He smiles, a dimple appearing on his cheek. "You want to try anal?"
"No. Not with you, big guy." I give his cock an extra firm tug and laugh. "I was thinking the three of us could experiment." I hold my breath, awaiting his response.
"You let Sam fuck your ass?"
That's the detail he wants to focus on?
Greg's hands slip under the hem of my dress and grip my lace-covered ass while I choose my response.
"Baby, you're too big for anal." I decide on flattery as I sit up far enough to slip my panties off.
"What exactly are you asking for, Jennifer? You want to invite Sam over to watch us fuck?"
Greg slides his palms across my ass cheeks and spreads them roughly, then shoves a fingertip inside me.
I love a finger in my ass, but I never encourage backdoor activity with Greg. It's a slippery slope back there, ladies. Admitting you enjoy their finger in your ass quickly escalates to their cocks prodding for entry.
Which, I enjoy, to be clear. As long as the penis isn't super-sized.
But Greg's words excite me, so I slide deeper on his finger as I replay what he said. The idea of fucking them individually while the other watches is downright enticing.
This threesome idea has even more possibilities than I'd even imagined.
"I want to take you both at the same time," I tell him, moving up and down on his finger. I rest my forehead against his and grip his jaw with my hand. "But the idea of Sam watching us fuck sounds fun too."
Greg fists himself and slaps my pussy with his cock. "So, I'd get your pussy and Sam would get your ass?"
I nod. Fuck, I think I'm going to come just from talking about this.
"It would be an awfully tight fit, don't you think?"
"Yes."
"You think you could fit two men inside you, baby? You think you can take us both without tearing you in half?"
"I could try," I manage to respond. I'm having trouble focusing. The pressure between my legs is volcanic.
Greg taps my thigh, indicating I should raise up and allow him access. He guides the head of his cock to my slick opening, and I bob up and down on the tip, teasing us both.
"I love fucking you from this angle. I can see my cock splitting you open."
I whimper, loving his filthy mouth. I place my hands on his shoulders, balancing myself as he uses his thumbs to spread my lips open so he can watch himself slide into me. It's a little humiliating to be treated like his fuck toy, but it makes me wet all the same.
"Fuck, Jennifer. Just talking about fucking two men at once is making you a soaking wet little slut."
I whimper and bite my lip as Greg wraps his hands around my waist and thrusts into me. I mewl as he buries himself to the hilt.
He's deep. Too deep. I need to move, to alleviate the pain of his cock shoved against my cervix, but he's holding me tight. My thighs burn from trying to lift myself while he holds me down.
"Greg, let me move."
"Not yet."
He slides his hands lower, circling my asshole with his fingertip.
I can’t do anything but squirm as sweat trickles from my neck, running between my breasts.
He pushes his finger roughly into my ass.
"You want this, baby? You want both holes filled?"
I nod.
He eases his hold on me, and I grin while sliding myself up and down his cock.
Our tongues battle while his hands are everywhere: pinching my nipples, gripping my ass, wrapping around my neck until I'm lightheaded.
He slams me down on his cock and pinches my ass so hard, I know I'll bruise, but that small bite of pain pushes me over the edge. I come, and Greg follows, muttering a stream of obscenities as he floods me with his cum.
"That was great." I'm lying on his chest, nuzzling his neck and basking in postcoital bliss.
Greg grunts non-committedly and sits forward, lowering my back to the chaise.
His feet hit the concrete floor of the patio as soon as his dick slides out of me. I feel his cum on its way south as he drops to his elbows and covers me with his mouth.
Holy yes. He's never done this before. It's been on my fantasy list for some time, but I've never found the words to ask him to clean up his own mess.
"Fuck, baby. That feels good."
I weave my hands in his hair, encouraging him to continue.