The Second Time

The Second Time

By Randomguy664

Tags: Transhet, anal, 69, public masturbation

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Despite the professor's best efforts, Valerie was in a different world than the world of anthropology. The college sophomore was distracted. Joel Harris with his broad shoulders and short brown hair, was sitting in front of her. She could smell him from this close, the faint smell of sweat and deodorant almost felt like intoxication. Her eyes did not leave his back.

It was only a week and a half ago that they went on their first date. They went bowling, in which we both did terribly. It didn't matter, they couldn't do anything but laugh when they got gutter balls three times in a row. It was awkward since it was her first date as a woman and she was afraid her voice training would fail her. It did not though.

The same night they went bowling, they went to his place and had some friendly drinks while talking about stupid stuff. When they got tipsy, he pinned her against the wall and (with permission) started making out with her. His lips were aggressive, but tender. One thing let to another and they had sex, passionate sex.

Valerie was a bit worried though. A few days later, things were the same as before. They chatted, sure, but didn't flirt much. She was pretty sure he hadn't asked her out again. Just some conversation, ending always with 'see you later.' It left a fear in her mind that she was in the early stages of being ghosted.

Thoughts of getting ghosted went by quickly though, replaced with the admittedly hazy memories of getting plowed by him. She reminisced and slipped a finger underneath her skirt. It pressed against her half-hard cock. Even in it's partially erect state, it strained her underwear. Like she scratched an itch, she just used one finger for now.

She thought of his gentle touch, his fingers had touched her neck and back with a feather touch. Like it did back then, Valerie shivered as she stroked herself with her finger. She wanted him to touch her again.

She thought of his passionate kisses, his lips pressing against hers and her body. She stroked while remembering the feel of his lips against her flesh. She wanted him to kiss her again.

She thought of his thick cock, filling her mouth and her ass. She stroked while remembering the taste of his cum and her ass having been filled. She wanted him to fuck her again.

In her absent-minded fantasies, she had taken her six inch cock from her panties and began to use her full hand to stroke it furiously. Her breath was almost ragged. She licked her lips, eager for cum, his or her own.

The woman to her right spoke and brought Valerie back from fantasy. "Are you okay? You're looking red in the face."

She turned to the woman, her cock still being stroked and filled with thoughts of Joel. "Its nothing. Just... recovering from a cold." She shook her head, her blonde short hair becoming slightly disheveled.

Mostly satisfied, the woman turned back to making notes.

Following suit, Valerie pretended to take notes and put her head low. To masturbate in a public setting like this would have left her embarrassed were it not for the erotic thoughts that filled her head. Her hand would not be stayed with such a minor thing as embarrassment.

There was soft, slick sound coming from her cock, but fortunately the professor's droning voice blocked it out, hopefully. She stared at the back of Joel, wishing he would just turn around and take her right then and there. He could hold himself above her and fuck her hard and fast, slow and rhythmic. Then hold her afterward in a gentle embrace while they drift asleep together.

Her legs buckled and twitched as she came, leaving a mess on the floor. Thankfully, she was near the back, so it's doubtful anyone could have saw or would step in the mess. The force of the orgasm was great enough that she feared she might have gotten some on Joel's back, but it did not.

Horny brain quickly took it's leave like a swift wind and the doubt filled her mind in a miasma again. Dreadful thoughts followed. Maybe her and Joel's sexual encounter was a mistake? Maybe this ghosting was just the aftermath of regret of drunken actions? Maybe she was just a warm hole for a drunk college guy? He didn't react much or at all when she told him she was trans. Didn't even touch her dick, at least that's what she recalled.

When the class ended, Valerie was afraid of the answer she might get, and shirked away when Joel tried to speak with her. What he was about to say could be devastating, so the only thing she could do was flee to her room.

* * *

A nice shower is often the cure for what ails a person. This was no exception. Wash away the doubt with hot water and suds. Valerie's room was a mess, and the towel was quickly added to it by throwing it into the laundry pile. It went exactly where she wanted it, even if the outside eye would be boggled and see nothing but chaos. Nude as the day she was born, albeit with a few additions on her chest compared to her at birth, she threw herself onto the bed.

She sighed as she looked up at the ceiling. The fan rotated slowly, matching the mood of a lazy summer day after classes. Her modest chest continued to rise and fall in a measured pace. Valerie tried to move on from the doubts she just rinsed and scrubbed of, let it wash away like footprints in the ocean's waves. In the vacuum left as she emptied her mind, idle thoughts floated in.

The thought of food was the first idle thought in line. "I feel like having a doughnut. Maybe tomorrow." The urge was powerful enough to fill her mind with a cascade of the fried goodness. But she suppressed the urge for now and tried to empty her mind again. The round shape remained, and the hole of the last remaining donut in her mind winked at her.

The donut in her mind was licked first, savoring the pink frosting and sprinkles. Curiously, her asshole twitched and something sent a shiver down her body. Her hands were idle, and idle hands were the hands of the Devil. They slid down her slender body along the curves. She absentmindedly started to stroke herself again. "Ugh." She groaned. "I just got out of the shower." Valerie gave into her idle hands' wanderlust, despite the annoyance of making a mess of herself just after washing herself.

Her legs lifted into the air to give her hand free access to start to finger her donut as her right hand started to massage her dick. She mimicked what she wanted someone to do to her and gently touch her in her most sensitive spots. Fingers, thicker than hers, could spread her open and invite their tongue. The mind focusing on the donut changed to imagine her ass getting licked. The skillful tongue prodding and rimming her.

Valerie's right hand had awoken her member from slumber and started to move up and down. Her imagination didn't yearn for a tender hand, but an enthusiastic mouth. The mouth would suck, blow and slurp her six inch rod hungrily. The madman would not be satisfied just licking her cock, but eagerly doing everything possible to drink her girlcum.

"Please..." Words escaped her lips as her fingers went from a tender probe to a spreading of her asshole. She wanted more, more than just fingers. She wanted someone to pin her down and just take her. Someone to push themselves inside of her tight hole and scramble her brains with forceful thrusts.

She could do not but whine as she played with herself and was lost in her imagination of being fucked and sucked. She twitched and winced with every imagined thrust or bob of someone's head on her lap. Her breath was rapid. Her toes curled. Her legs twitched.

"Cum inside..." Her voice trailed off and only mouthed '... of me." Her hands worked their mastubatory magic in a blur as it brought her closer to orgasm.

"Uh, bad time?" A man's voice from inside her room broke her imagination.

"J-Joel?" Valerie said as the spell was broken and her eyes darted toward the door. Sure enough, Joel stood in the doorway in a grey and black polo and shorts. In the blink of an eye, she spun and wrapped her sheets around in. Her nudity was hidden, but her lustful intent was certainly clear to him, she had just been caught after all.

"Bad time?" The tall man said as he turned his head and averted his eye. Like any self-respecting man, he wanted to memorize the picture, but modesty overpowered base desire.

She was a deer in headlights and panted heavily.

Joel's eyes turned back toward her, a pretty girl naked in her bed and panted heavily. He stepped closer, a smirk on his face. The invitation was clear to him.

But the invitation was not an invitation, and she let him know when he touched the blanket wrapped around her and she sobbed.

Joel jumped back and put some distance between them. "I'm sorry!" He exclaimed in surprise. "I-I though it was an invitation." A foolish thought brought about by unrealistic fantasy. His eyes against averted away from her in embarrassment once again.

Valerie was able to catch her breath again. "Just... startled." She looked him up and down, definitely noticing the tight polo and muscle underneath. "Just... conflicted."

He noticed the softer tone in her voice as she spoke and leaned back against the door. "I should go. Made a mistake."

"No!" Maybe she was still horny-brained, but she didn't want him to leave. He was the closest thing to her fantasy, but she also yearned to talk to him, to hear something from him.

After a nod and a deep breath, he asked the first question on his mind. "Do... do you want me to leave so you can get dressed?" When she has shaken her head, he again nodded. "Okay... you want to talk about something?"

Still wrapped up in her bedding, as much armor as she could muster, she asked the question that wracked her mind before the shower. "Are we okay?" It took her entire breath to have said it and she felt deflated after she said it. She girded herself for the inevitable rejection. She's a transwoman and they were drunk after all. It must have been a mistake.

But it never came. "Yeah" he said softly, "as far as me, I'm okay with us."

Her heart rose in her chest, but it wasn't a complete feeling of relief yet, just a glimmer of hope. "You didn't treat me any different. You didn't talk about it, about us afterward." She bit her lip before she continued. "Didn't pursue me any further. We were drunk" She looked away. "Didn't react when I said I was trans."

He let out a big breath in a sigh. "Lot to take in." He figured the best place to start would be the immediate present. "Well, we arranged for another date..."

Just then Valerie's phone rung, beeped and vibrated. She apparently forgot the alarm.

"I guess I made a mistake and came too early." Having walked in on her masturbating was a pretty good sign he was early. "I mean, I had a good time. I had fun with you. Would like to continue to go on dates with you."

"But what about..."

"Thought it was hot. You were just a smoking hot... er, beautiful girl." It was his first time with a trans girl, but didn't care about it in the moment or even after reflection. A pretty and fun girl is a pretty and fun girl.

Her tight grip on the bedding relaxed a little, baring a bit of shoulder to him. "No regrets"

"Nope."

"Didn't think it was weird?"

"A pretty and fun girl is a pretty and fun girl." He said, vocalizing his earlier thought.

His words and sentiment made her relax, and she noticed she was still frustrated and aroused. "We... we could do it again now. Now that we're not drunk. Just to make sure." Even after his reassuring words, there was still a shred of doubt in her. There's no guideline for when or how to ask for a second time after all.

He smiled, as simple of an answer as could be.

Valerie loosened the sheets from her grip and exposed her shoulders in a Victorian-era scandalous tease that few men could resist. "Well, get over here."

His undressing was not quite as erotic as he got rid of his clothes in a hurry, not before locking the door to her dorm. After the click of the door's lock and the hurling of his underpants, Joel put his hands on the bed's headboard. "So...?"

"How about sixty-nine?" Maybe it was still a tiny, part of a shred of doubt in her that pushed her toward this. Same time, few would turn down a blowjob. Valerie shifted on the bed and patted on the mattress, inviting him to lie down. After he did, she swung her legs over him and planted herself above him, his manhood in front of her face.

The sixty-nine is kind of awkward. It seemed half-assed. She knew though how awkward most things in life were. To ask for a second time was awkward. "No time like the present." Her hand carefully gripped the present before her: a nice fat, juicy cock. Her first blowjob was a sloppy, amateurish performance. Hopefully number two would be a stronger showing. A few teasing kisses were the starting point.

Face to cock was an unusual situation for Joel. It's only fair though when going out with a transwoman. After a deep breath to prepare himself, he wrapped his lips around her tip. His movement was stilted and arrhythmic, but he was learning on the job. It tasted nice, clean and slightly perfumed.

There is scarce a person that good at a blowjob naturally, but oneself is as important of a part in the blowjob as the giver is. Valerie yearned for more, so her hips started to do work on her end, slowly pushing in and out of his mouth. Never had she ever gotten head, but she was enjoying it. His tongue wrapping around her dickhead was enough to send a chill down her spine.

Joel became reassured, assertive and aggressive after feeling her shiver. He started to find a smooth rhythm and would pull out to kiss her balls occasionally. When suckling and kissing her balls, her ass was all that he could see, and he was reminded of how good her ass felt. He could feel himself throb in her mouth.

Valerie relaxed her throat and attempted to take him as deep as he could. Her gag reflex was suppressed successfully. She only took down the throat for a few moments before pulling back and kissing his member. There was a reason that Valerie could not concentrate on the deepthroat as much as she wanted: her own dick was starting to twitch.

It happened in an instant: Joel's mouth filled up with her white hot girlcum. The feminine and slick fluid dripped from the corners of his mouth onto his chin. He pulled it out of his mouth, swallowing some and keeping the rest in his mouth. With a pat on her hip, she rolled off of him onto the other side of the bed.

"I'm sorry! Did you choke on it?" She was in a slight panic, but he shut that down by kissing her after he turned around on the bed. "Mmph!" She eeked just before his tongue and her semen went into her mouth. With no way to spit it out since his lips were locked with hers, she swallowed her own cum.

"How does it taste Valerie?" He said with a mischievous smile.

"How did it taste for you?" She responded, morbidly curious.

After a moment of conversation, both agreed her semen was mildly bitter, but not unappetizing.

"With that out of the way" Joel nodded down and gestured at his still hard and slick cock "we should get to the main event..." He was about to ask for her opinion, but she was already lubing up her asshole for said main event.

Valerie leaned over and placed her hands on the edge of the bed. She honestly didn't remember much of when he fucked her except some moments of anal ecstasy from underneath him. But here she was, taking the plunge again, sober this time, with Joel. The moment of reminiscing, as well as the teasing and lubing fingers earlier excited her and caused her to twitch down there.

He was slightly surprised at her excitement. Not displeased though. With a step forward, Joel took a firm hold of her hips and aligned his pole with her hole. After he told her relax, he pushed himself inside of her for the second time in their lives. A little worried about hurting her since he was possibly a bit rough when drunk, he took it slow for his girlfriend.

Steady breaths were all that left her lips. Relaxing as he filled her ass with his fat cock was her goal for now. But as time went and his hips fell into a slow rhythm, she found herself wanting. He might have been a bit rougher and while she appreciated his consideration, she yearned for more. She wanted a more passionate intercourse.

He noticed her steady breath turning into whines as he gently fucked her. An idea struck him. His right hand left her hip and ran a index finger lightly against her vertebrae. "Use your big girl words..."

Valerie shivered at his touch. "M-more..." She pleaded in an utterance.

Having seen her reaction may have unlocked a kink for him. He felt proud of her. "Good girl." He returned his hand to her hips and his started to move faster and his hips knocked against her ass with increasingly loud plaps.

To get plowed while sober was even more exciting than her fantasy could dream. He filled her, took away her breath and gave him his heat. She became more confident as his cock thrust in and out and her own cock bounced to and fro.

"Let's not ignore this..." Joel leaned forward and whispered in her ear and held onto her cock. "Can't let this just bounce around unattended." He stroked her in sync with the increasing pace of his hips.

His increasingly bestial sounding grunts and moans bounced between her ears. Her button was getting pressed repeatedly and with force. Valerie mewed from the pressure against her prostrate and shivered. "Just like that..." She managed to squeak out as she held onto the bed to maintain her weakened balance.

It was then that Joel slowed down back to the pace from when they started, but this time with longer and deeper thrusts. His big hand followed suit, slowing down the stroking of her dick to a snail's pace. Not just to tease her, but that was a big thrill. When she whined for me, it brought a sadistic smile to his face. "You want even more?"

Valerie bit her lip, mildly frustrated. She told him in her big girl words for 'more' and now he's holding back. A teased cat will bite back. "Don't slow down now you asshole!" Were she in a different position, she might have scratched or bit him for holding out on her.

He had a reason for slowing down. Valerie's slick asshole was trying to wring the cum out of him like if his cock was a toothpaste tube. To keep at the pace he was at was going to have him finish in a hurry. Her verbal snap back was responded with honesty. "If I don't slow down, I'll cum..." A man's pride is a thing rarely relinquished and he didn't remember much of the first encounter, so he wanted to impress.

She responded with a sigh. She spent a while as a guy, so she kind of could understand, but it was still a pretty stupid thing. "That's the point of sex." She pushed his cock as deep in her backside as she could and growled loudly. "Just do it!" All the anxiety from before the second time was forgotten in the midst of the second time. All that pent-up frustration and anxiety was going to be washed away by his hot load in a few moments. "... please."

Not one to turn down a lady, Joel stopped trying to hold back, and came inside of her with one last thrust. Going faster was not necessary at all. The force of the load coming from him was almost enough to cause both of their knees to buckle.

The wish of getting a creampie from her earlier mastubatory fantasy was fulfilled as her arms collapsed her onto the bed, her ass still in the air. The same ass was filled to the brim with the frothy mixture of semen and lubricant. Her asshole was filled, her mind was empty. Her member on the other hand (his), was ready to release from the prostrate pounding and the hand that stroked her.

His cock was pulled out without fanfare, but cum started to drip down her leg in a slow trickle. It certainly made round 2 tempting, but his flesh was weak and spongy after ejaculation.

With one last twitch from her dick, she had been completely and utterly drained. There was a happy haze in her head as her knees feel to the ground into a kneel. She smiled.

A few moments passed before he caught his breath from the torrid sex. "Whew..." He said as he stumbled across the room to his pants and pulled out his phone. "We... we still have time to catch that movie." He had this date she forgot about all planned out, but didn't expect or plan to have sex at all today. "... we'll have to skip lunch though."

Finally getting to her feet, she nodded. "Yeah... I'd like that." Whatever movie it was, it was not important, the important thing happened already. Anything else was just a treat.