Tom Learns, Ally Leads Ch. 01

Ally and Tom had been dating now for six weeks. However, they hadn't had sex until tonight. Tom is a 29-year-old virgin, Ally, she is 28 and has a decade of sexual experiences.

Tonight, their usual kissing while laying together on the couch moved on to a grope, then a squeeze, and onto disrobing. Tom cut their foreplay short as he mounted Ally. Their intercourse was short too as a minute after his cock found its way into her, he came.

After an awkward moment, actually thirty seconds of silence, Tom lifted himself up and off of Ally. He looked around, then to her, and apologized.

Ally really liked Tom. She had several reasons, but mainly because he wasn't the usual bar-bum she often attracted. But she had been frustrated by his reluctance to have sex. And then it happened so fast, literally, tonight. Her frustration had been replaced with disappointment in how he fucked her so poorly. No, pathetically.

"What, why are you sorry?" Ally asked, reaching up to caress his neck.

"I know that was bad," Tom answered. "I was just..."

"Tom," Ally interrupted, caressing as if to calm him. "Don't, do not worry about it. It's not like we won't get to try again, right?"

Tom smiled. Ally smiled back and they laughed. They lay their together on the couch, quietly, until she got up to go home.

Ally dressed, and Tom walked her to the door. While they kissed goodbye, she put a hand on his naked cock. He looked into her eyes excitedly.

"Oh Tom," she said, squeezing his fast hardening seven inches. "You seem ready to go again."

Tom smiled, leaning in to kiss Ally some more. She stepped away, grinning.

"No, I have to get up early," Ally whispered. "However, come over to my place after work tomorrow, and we will do just that."

Mid-afternoon the next day Ally texted Tom, "Virgin?"

Tom blushed beet-red in his cubicle. He put his phone down and resumed working. Thirty minutes later Ally texted again, "?"

Tom knew he should reply, and went back and forth in thought about calling Ally. Eventually he texted, "Yes, until yesterday, why?"

Ally didn't reply, and they didn't talk until Tom arrived at her apartment after work.

Ally let him in, allowing Tom a quick kiss as she shut the door. He stepped aside and she moved into the dining room, sitting at the table. She patted the chair beside her. He sat down.

Ally took Tom by the hand and leaned into him. "Why didn't you tell me you were a virgin before we had sex?"

Ally let go of his hand. Tom proceeded to explain he was embarrassed that he is a 29-year-old virgin and hoped his lack of ability wouldn't reveal that he was. She pressed him for why he had never had sex before. He shared that he had never felt this strongly about someone else.

"Bullshit Tom!" Ally said, her face now taught. She appeared irritated.

"Huh?" Tom muttered, uncertain why Ally seemed suddenly upset. "It's true, why..."

Ally held up a hand. "We've never said an 'I love you' to one another, or shared any other seemingly deep affections," she stated. "Please be honest, I'm just curious is all. Just tell me, why does a handsome man like you go almost 30 years without having sex?"

Tom held his hand out, Ally took it. "What I meant to say was I had never felt comfortable like I do with you, Ally. I am shy," he rolled his eyes at this obvious truth about him. "When alone, and close with anyone, I can't. Even kissing, I just get so shy and uncertain."

Ally put a hand on his shoulder. "I can feel that about you, but the way you kissed," she looked up to the ceiling and smiled wide. Her tongue slowly licked her upper lip. "Oh, you convinced me you were not new to kissing, so I had no reason to think that sex was new to you. Until, last night."

Tom sheepishly nodded yes, looking down. He leaned forward and kissed Ally's hand. She let a smile back onto her face, lowering her head to his. Kissing the thick brown hair atop his head, their faces met.

After what was perhaps the greatest kiss they had ever had, Ally turned her head and asked, "How often do you watch porn, Tom?"

Tom pressed in and kissed her hard, hoping the question would go away. But it did not. "Tom?" Ally insisted.

They sat back, and Tom went on to admit that he watches porn on occasion. Ally admitted the same. She asked what he searched for when he watched. He half-answered her question, blushing a barely noticeable amount. When she told him that she searched for cunnilingus and face sitting, his blushed flushed his now fully pink face.

A few more minutes of kissing, seemed to ease Tom, and perhaps give him a boost of confidence. His hand found Ally's breast. She playfully licked nose, "Tom?"

"Yes," he whispered, moving his kissing on down to her neck.

"Your non-answers are turning me off Tom," Ally remarked, pulling back from him. "Tell me!"

Tom looked at Ally, finding her stern-stare odd. One second, she is as passionate as their kiss. The next, she is immediately serious.

"Tom, you can't really be comfortable with me if you can't share your intimate desires without hesitation." Ally said, pulling back even further.

Tom admitted he was particularly aroused by female domination, nothing sadistic or painful. Ally asked for specifics. He went on to describe what is actually more dominant / submissive play.

Having successfully brought him to share this desire, she took his hand. "Go on, tell me more," she said firmly.

"I don't know," Tom stammered, not knowing what else Ally wanted him to say. "I don't know how to do, I mean perform. So, I find excitement, I guess, in being shown. I suppose. Can we..."

Tom was about to ask Ally if they could 'go' again. She smiled and kissed him. They stood up together, still kissing.

"Being shown?" Ally asked between kisses. "Or, being told?"

Before Tom could form a word Ally pressed one hand on to his lips and the other atop his head.

"Let us find out," Ally said directly. "Kneel!"

Tom instinctively dropped to his knees. Ally's hands remained in place, following him down. He looked up; she gave him a short nod of approval.

"Now," Ally moved back and unzipped her jeans, sliding them off. "I want to see," she slid off her panties too. "No, I want to feel how well you please with your mouth."

Tom looked at Ally's trimmed bush, a perfect narrow but thick rectangular tuft sat above her slit.

"Tom," Ally spread her legs. "Do you want to lick my pussy?"

"Yes, yes," Tom replied, leaning forward to begin. His progress stopped when Ally moved a hand to cover her pussy.

Ally lightly took hold of Tom's hair, and then turned his eyes up to hers. "Only when and as I say, Tom." she released his hair. "Slowly, you may begin." He went in, tongue first.

For thirty seconds Tom licked up, down, all around. Ally found it amusing he had little clue what to do. His hungry tongue felt good, but this was not going to do.

Ally gently moved Toms face away from her pussy. "Wait here," she said as she stepped aside and went down the hall, leaving Tom there on his knees.

Ally walked back, a big smile on her face as she dangled a long black satin cloth for Tom to see. "This my friend," she held it up to her eyes. "This will help your tongue focus on what it is doing. Your eyes, they are increasing your excitement. Which is distracting you."

Ally placed the satin cloth, a waist wrap from one of her robes, over Tom's eyes. With it tied securely in place, she gave him a single pat on the head.

"You may resume," Ally instructed. "Let your tongue find its way, slowly!"

Tom leaned forward, found Ally's wet pussy and began licking. His licks were slower, but still all over.

"Tom, I'm going to help you," Ally whispered.

Confused, Tom pulled back. "Help me?" he asked.

"Yes," Ally said with a giggle while placing a hand on each side of Tom's head. "Stick out your tongue, relax your neck," Ally continued instructing.

Slowly Ally guided Tom's face towards her, until his tongue met the lowest part of her slit.

"Good," Ally praised. "Slowly, lick upwards."

As Tom licked, Ally gradually tilted his head upwards.

"There, that speed," Ally praised some more. "Up to the top, now STOP, right there," she held his head firm as his tongue came to rest on her clit.

Tom pulled his tongue into his mouth and took a breath. Whap! Ally lightly tapped his head,

"Tongue out!" Ally snapped. Tom complied. "Find my clit again."

Tom quickly brought his tongue forward, pressing it against her clit.

"Now," Ally said, pulling Tom into her a bit more. "When your tongue gets there, lick around it a couple times and then, lick back down."

Tom did as he was taught.

"Good. Repeat that, over and over, repeat that Tom" Ally said, a slightly sinister grin on her face which he couldn't see. "Let your tongue see the way."

For nearly ten minutes Tom licked Ally's pussy as instructed. Twice along the way she told him to lick just a bit faster.

"Now just lick my clit, Tom, just my..." Ally moaned as his tongue hit the mark. "That, right there. Don't, stop."

Ally pulled Tom even tighter into her as she neared orgasm. He gasped a bit but kept his tongue on the mark. "Oh, oh yes, yes...," Ally let loose her orgasm.

Ally screamed, grinding in even tighter. Tom gasped, then started to gag. She held him in place until she finished, and then pushed him away. Collapsing backward into her chair.

Ally caught her breath. Tom rested on all fours, catching his. He removed the blindfold, looked up, and smiled at her. The sight of her body, limp except for her chest heaving for air, told him he probably did well. His eyes told her that he really wasn't sure.

"Tom," Ally said, taking a big breath.

"Yes dear," Tom answered.

Ally giggled at the word, 'dear'. They hadn't used such words with each other before. She liked the sound of it. "You did very well, Tom."

Tom's smile grew. He pulled himself up into the chair next to her.

"I thought so, tried" Tom said, reaching out for her hand.

Ally took Tom's hand. "You have much to learn," she said plainly.

The deep sigh from Ally all but erased the smile from Tom's face. She held out her other hand, he took it, and stood up with her as she got up.

Ally pulled him in close, they kissed. Her kiss moved to his cheek. Kissing her way to his ear, nibbling it playfully for just a moment.

"Go to the bedroom," she whispered. "Get naked, I'll be right there."

Tom, smiling once again, went in for another kiss. Ally turned towards the kitchen.

"No, go wait for me, Tom," she barked, walking away.