The Right Kind of Girl for Him Ch. 05

After several waves, his orgasm ended and he let go of his knees and straightened his legs. Lindsay had swallowed all his seed. It belonged to her. She wouldn't waste it.

She licked the remnants from his tip like a cat finishing a saucer of milk and then let his cock fall back against his stomach. She climbed up the bed and rolled over next to him on her back. They were both still panting with the exertion, but eventually their breathing returned to normal. Lindsay reached over and guided Tom to roll towards her and rest his head on her chest. He wrapped an arm around her body and she ran her fingers into his hair, feeling the weight of his head on her chest, feeling more content than she could ever recall.

************************************

Lindsay and Tom honed their skills over the next month. There was no hesitation now, no questioning. They both realized that they had touched on something special, an opportunity to reach a level of intimacy and ecstasy that was rare for most mortals.

Lindsay was a determined trainer, and Tom strove to exceed her expectations. He liked how she was the one to shove each new butt plug up his ass as he was bent over her knees. He liked eating her out as he got used to a new plug after it was in place. She had rewarded him with a blowjob after each time he graduated to a larger sized plug. He was anxious to be ready to take her strap-on. He told himself that it was because after that he could fuck her, and while he was excited about that too, he knew it was really a secondary motivation for him. Really, he just wanted to please her and to submit to her in yet another way.

His self-esteem was at an all time high. It surprised him that he not only wasn't ashamed of his atypical sexual perversions, but he wished other people could somehow know about it and be envious. He felt like an experienced sexual athlete. Like most people practiced amateur sex, but he was training for the major leagues. His tongue muscles had gotten stronger; he could now go down on Lindsay for 30 minutes at a time. He'd made her come everyday of the week, sometimes multiple times in one night. His asshole was trained and could accept large plugs with minimal discomfort. He knew it seemed a little perverse, but how many of his friends could regularly lick their girlfriends to orgasm? How many had triggered an orgasm by licking a woman's ass? How many of them would be able to take the butt plugs he could? He knew some would call him whipped, but he knew the voices in his head were just jealous of his experiences. He was living his best life.

There were setbacks of course. When she'd pushed the 4th plug inside him, he'd felt a little itch inside his butt, and when she'd pulled it out later, she discovered that he had a little tear and bled a little. Lindsay felt responsible and guilty and apologized profusely, but he had healed up quickly without issue. After another few sessions with the 3rd plug, he was able to take the 4th.

Last night, Tom had taken the sixth and biggest plug. Lindsay had been ecstatic, heaping him with praise for his achievement. They'd set a date: this Saturday night he would lose his anal virginity. He would spread his legs for her and let her butt fuck him.

Lindsay had made him promise not to cum again until then. He was to call her for help whenever he got horny so she could help him. Today, he'd found out that her help came in the form of taking him over her knee, spanking his ass to a glowing pink hue, while working one then two then three fingers into his asshole. She'd brought him to the edge of orgasm three times before withdrawing her fingers and leaving him wanting like a bitch in heat. "Wait for me Tom. Wait for Saturday. It's important." As she left, she paused at his door and said over her shoulder, "Don't hesitate to call me if you need my help again."

Now as he laid alone in bed trying to fall asleep, he reflected on the day's events. There was a dull ache in his ass and his butt cheeks were still tender from the spanking. He'd found today's scene erotic as hell, she was so forceful, such a powerful dominant goddess, and he was looking forward to Saturday, but a sliver of doubt had begun to worm its way inside his head.

Did he fully understand what he was getting into? Was he in over his head? Was Lindsay a sexual savant dominating him with precision control or was she an out of control predator? Could he trust her to keep them from spiraling into depravity?

With these thoughts rattling around his exhausted horny mind, he fell into a fitful sleep.

In his dreams, he was in a dirty cellar on his hands and knees on a bare mattress. He was gagged, blindfolded, and his wrists were handcuffed through a loop of material holding them tight to the mattress. A thick leather collar clutched him by the throat, attached to Lindsay's hand by a chain leash. She was sodomizing him with a huge strap-on dildo and laughing maniacally. He squealed into the gag and tears fell down his cheeks as she mercilessly pumped her hips to break him in permanently. She told him she couldn't believe he'd actually let her go this far. She'd never imagined he was so pathetic and after she gaped his asshole she'd be leaving him.

He woke up suddenly in his bed, his sheets soaked with his sweat. He tossed and turned after that but couldn't fall back asleep.

As he sipped his morning coffee, Tom told himself that he'd feel better on Saturday. These were just expected jitters before their big event. He trusted Lindsay. He knew he could trust her.

Then he checked his post and found he had a delivery. He opened the cardboard package to find a pair of white satin panties with a bit of white lace along the hem. These were not slutty panties; one might call them beautiful, innocent. He was thinking that they seemed too big for Lindsay when he saw the note in the box.

"I looked for a pair of men's underwear for our special night, but I just couldn't find anything that screamed 'I'm losing my virginity tonight' half loudly as these do. Wear them for me on Saturday night along with the number 5 plug. I made 7 PM reservations at a Michelin star restaurant so be wearing a coat and tie when I pick you up at 6:30. Can't wait, lover! - Lindsay"

Tom looked at the white satin sliding between his fingers and thought of his dream. Before he knew it, he was dialing her number.

"Hey baby!" Lindsay answered her phone with a smile.

"Women's panties! Really?!" Tom snarled into the phone.

There was no response for a moment, then, "I think they'll look great on you. I spent hours picking them out."

"Where is this going?"

Again the silence spread out as she measured his words. "I'm not sure what you mean," she responded. Her voice was clear but there was caution in it now, maybe even fear.

Tom wasn't entirely sure what he meant either, so he didn't say anything. He was scared. He loved her so much he felt like it might kill him.

When she realized he wasn't going to clarify, she continued, "Look if you don't want to wear them, don't wear them. I just thought they would be...festive." Lindsay thought that sounded lame, so she tried again, "I know you're scared, Tom. You scare me too. I don't know what I'd do if I lost you. I promise you I'm going to make you feel so good on Saturday and I'll make sure you don't regret it." Her voice was raw on the verge of cracking with emotion. "Trust me, Tom."

When he still didn't say anything, she changed the subject. "How's the no-orgasm challenge going?"

"I haven't cum," he said defensively.

"That's good, Tom," she said, trying to discern his state of mind. "I haven't either actually. I thought earlier about calling you over to lick me out, but I determined that would be hypocritical." She thought she heard him chuckle softly on the other end of the line.

Finally, he said something. "So what kind of Michelin star restaurant did you book? Thai?"

Of course, she had not booked Thai.

On Saturday, when she picked him up, she was dressed for the Oscars. She was poured into an elegant backless dress. He wondered if she'd had her hair and make-up professionally done. She practically glowed.

He suddenly felt underdressed despite his suit and tie, and he was glad he had the white satin panties on under his pants. He hadn't told her whether he would or wouldn't wear them. They hadn't spoken of it again. Tom wondered if she'd guessed he would wear them after all.

It was the nicest restaurant he had ever been to. Lindsay had chosen a booking with wine and cocktail pairings. As they enjoyed the complex flavors, Tom felt pleasantly buzzed and content. He felt honored that she was treating the evening with such respect. The fancy restaurant, the dress, the hair, the make-up, but he felt most honored by her manner. She seemed uncharacteristically nervous, and it touched him.

After the last course, she reached her hand across the table, and he slid his hand into hers. "I love you Tom. I've known for a while now. I'm never going to let you go. I'm going to make you so happy that you'll never want to leave." Her eyes glistened in the candlelight as she spoke.

Tom squeezed her hand, lowered his eyes, and said softly, "I'm yours, Lindsay."

They said nothing as they rode in the backseat of the Uber on the way back to Lindsay's place. They stared at each other in anticipation, undressing each other in their minds.

As soon as the front door closed behind them, Lindsay pushed Tom against the wall, her kisses hungry and demanding. He kissed her back with equal need.

By the time she pushed him into the bedroom, he'd been stripped of his coat, his tie, his shirt, and his socks and shoes. She dropped to her knees now, tugging furiously at his belt. As she did, she noticed a bit of white lace sticking up over the top of his pants. She stopped and looked out at him, her face lit up with pleasure and surprise. He smiled back and looked away, still a little embarrassed. Lindsay squealed with pleasure and resumed stripping off his pants, then pushed him back onto the bed wearing only his panties.

Tom propped himself up on his elbows as he watched her take off her dress. She undid the tie at the top and started sliding it down her body. She hadn't been wearing a bra, and now her bare nipples poked out proudly atop her full breasts. As the dress fell to the floor, she revealed a black lace v-cut thong topped with a garter belt that held up her thigh high stockings.

Her sexuality was powerful and dangerous, and she knew it. She smirked at him as she retrieved her harness from her bedside table and strapped on her cock. She tied her hair up in a ponytail and moved onto the bed.

Tom playfully retreated away from her, shimmying backwards with his hips and elbows to the top of the bed.

Lindsay closed the distance quickly. Pushing between his legs, she put one hand on his hip and the other behind his head as she drew him into a deep kiss. She ground her pelvis against him, her rubber dick pushing against his throbbing cock, separated only by the delicate white fabric.

She pulled back and shared a hungry look with him before slowly and meaningfully hooking her thumbs under the upper hem of his panties and tugging them down. After they cleared his buttocks, she pulled the straight up, bringing his legs high into the air to slip them off completely.

Lindsay looked back down at her now nude submissive man, and as if he could read her mind, he pulled his knees up on his own and spread his legs in offering. The butt plug was lodged firmly in his rectum as requested, and she grinned as she slowly eased it out of him.

She took her time lubing up her strap-on as well as his anus, happy at how easily her fingers slid in and out of his slippery hole. Neither of them had said a word since they had entered the apartment. It may have been the longest period of silence during their entire relationship, but she couldn't think of anything to say that was worthy of this moment.

He kept his eyes on hers as she shuffled forward and brought the head of her dick to his virgin asshole.

Lindsay kept watching his face as she penetrated him and smiled at what she saw. He looked so slutty with his mouth hanging open, his eyes unfocused, his voice making little moans, his dick throbbing in her hand. She arched her back pulling back a half inch before thrusting her dick deep into this ass.

He was struggling a bit, she could tell, but he'd struggled before and knew how to deal with it. He took slow deep breaths through pursed lips and focused on surrendering his body to her completely.

Lindsay paused once she was balls-deep inside him. She brought his lips to her breast to nurse while she gyrated her hips slowly. She felt his cock get even harder between their bodies and sent a hand down to stroke him and get him close. She looked back up to his face to find him biting his lower lip, staring at her as he tried to deal with all the sensations in his body.

She squeezed his rod in her grip and began fucking him outright. He squealed as his asshole gave up and let her girlcock slide in and out of his body. They were both moaning like pornstars when his dick seized up and spewed hot cum between their bellies up under her tits. She kept up her thrusts as his moans became higher pitched and he emptied his balls completely.

Catching his breath in the afterglow of the most powerful orgasm of his life, Tom gazed into Lindsay's eyes. "That was amazing, Lindsay."

He had done it. He chose his next words carefully, "I can handle this, maybe even as often as you want. But this...this is as kinky as things are going to get, right?"

Lindsay gave him a naughty grin. "Oh Tom! You're so cute!"

The End