Deflowered in Darkness

Jessie Anne waited eagerly on the bed, the scent and touch of which was pleasantly unfamiliar. Her naked butt was high in the air, and her face was buried into the mattress. She was nervous, for sure. Her hands dampened the comforter as she grasped it. But her heart was pounding with excitement.

I guess it’s true what they say, she thought to herself. The thing you want most is often the thing you’re most afraid of. There was no turning back now. Well, technically there was…she could simply use her safeword. But if she did that, all of the preparation and anticipation would be for nothing: the exquisitely tied knots that bound her wrists and ankles to the bed frame, the enema Beverly had given her, the arrangements Beverly made to find the perfect partner. It wasn’t easy to find a man that would be willing to do to Jessie Anne what she desired. But somehow Beverly managed to find someone that Jessie Anne knew personally, and yet was willing to never reveal his identity, or utter a peep during the act, which would give him away. He was to remain silent as he performed. She was blindfolded.

She heard the front door open and shut. Was it Beverly? Or was it him? She couldn’t hear anyone’s voice, only footsteps, the clanking of glasses, the opening and closing of what she could only assume was the liquor cabinet, and after a while, some faint whispering. She was suddenly more aware of her nakedness. A cool breeze came in through the window, whisked around her thighs, and filled the spaces between her legs and her butt cheeks. She heard the footsteps and whispering become louder. She took in a sharp breath. The bedroom door opened. She turned her head toward the sound but it was only a reflex…she could see nothing but darkness behind the blindfold.

Beverly lay beside her and planted a kiss on her cheek. “Are you ready sweetie?”

Jessie Anne nodded. “I’ve wanted this my whole life!” she said with a sigh. “Can you give me a hint?”

“You know him from school,” Beverly whispered as she continued to plant tender kisses on her friend’s face.

“Student? Professor?”

“All you need to know is that he is tall, handsome, and is rock hard already.”

Jessie Anne could hear the sound of a belt unbuckling, then the rustling of clothes. Beverly reached between her friend’s thighs and began to pleasure her gently.

“Ohhh sweetie, you’re dripping onto the comforter,” said Beverly. “That is not allowed. I think we should have our friend here give you a good spanking.”

Jessie Anne felt a sharp, sudden sting across her right butt cheek. She jerked forward and squealed.

“I’m sorry Bevs!” Jessie Anne blurted out into the darkness. “I’ll buy you a new bedspread, I promise!”

“No need for that, love. I’ll be using my hand to take it out of your hide before you go to bed tonight. But for right now, I think it’s time you fulfilled the terms of our agreement.”

Jessie Anne let out a ragged, breathy sigh. “Yes, ma’am,” she said, with resignation.

“Good girl,” Beverly whispered. “Now why don’t you tell our friend here what our arrangement is and why he is here tonight. You may address him as Sir.”

Jessie Anne took another deep breath before she spoke. “Sir, Beverly is my best friend and also my mistress. She has agreed to be my mistress only under the condition that I give her my virginity, not for her to take herself, but for her to give away to whomever she pleases, in whatever way she pleases, wherever, and whenever she pleases. She chose you, to do it tonight, here in this…hotel room? I’m guessing?” She turned her head to Beverly. “Is that where we are? In a hotel?”

Beverly chuckled, “Ohhh sweetie. That’s for me to know and for you to never find out. Just like you’ll never know who you’re losing your virginity to tonight. Jessie Anne, why don’t you tell him why you gave me your virginity to give away as I please?”

“As proof of my love and obedience to you.”

“That’s correct. And you are proving yourself wonderfully, sweetie. Now here’s what will happen. Our friend will enter you from behind and give you no more than three pumps deep into your pussy. That way we can say with confidence that your virginity has been taken. After that, I will lube him up and he will put it in your butt, and he will fuck you until he comes inside of it. I will be here right beside you, fingering myself and watching the whole thing while I plant kisses all over your body. Now how does that sound to you?”

“Sooooo good!” exclaimed Jessie Anne under her breath.

Beverly gave her friend a long, wet french kiss. “Go ahead, baby. Tell him.”

“Sir,” said Jessie Anne. “My innocence is yours to take. You may begin to claim it.”

She heard him inch closer and his breath quicken. The warmth of his thighs met hers and she felt the sudden opening of her loins as his naked shaft poked inside. She imagined him as Beverly described — tall, handsome, kind, and strong. In the next moment she felt him fill her up completely, just as she’d imagined he would. She had no idea how big he was, but inside of her, he seemed enormous.

Just as promised, he thrust three times — slowly, and deliberately. As the last pump slowed to a halt, Jessie Anne could feel his hands roam across her back, then around to fondle her breasts. He remained inside her as his hands moved slowly across every inch of her body. Then, without warning, she felt his fingers inside of her as he pulled himself out from behind.

“Go ahead sweetie,” whispered Beverly. “Tell him what to do next.”

Jessie Anne was moaning softly from the warm, expert touch of her lover’s fingers. But she managed to speak between gasps. “Ohhhh, Sir! Please make the taking of my innocence complete. Please…put it in my butt! Every inch, again and again…until you come inside me!”

She heard the pop of a plastic bottle, followed immediately by the warmth of jelly between her cheeks, and then the warm breath of her captor against her ear.

He whispered, “Ohhh Jessie Anne, if you only knew how long I have wanted to do this very thing to you. It has filled my thoughts and my dreams for as long as I have known you. Now do you promise to take it like a good girl?”

Jessie Anne nodded, and gasped as she felt him poke into her. She buried her face into the bed and moaned in a high-pitched voice.

“Yes!! Yes, Sir!”

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