New Town, New Experiences

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A shy guy has his horizons expanded.
3.2k words
4.68
17.2k
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1

Part 1 of the 2 part series

Updated 11/29/2023
Created 10/29/2023
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Carl got home, showered, changed and headed back out before he could talk himself out of his evening out. He was fresh out of college and new in town. New job, new apartment and an old set of fears to overcome. It took weeks to get to this point, but he was determined tonight.

Although Carl was no stranger to female anatomy, he did however lack any confidence in actually getting women into bed. All of his history was based on women pursuing him. He was as handsome as he was feminine and his manhood matched his femininity, but fate was not completely cruel as he was gifted at cunnilingus.

Cunning Carl was the nice name they used for him. Cock-less Carla when they wanted to be mean. He was dating in his freshman year, but by his senior year he was nothing more than an oral booty call without reciprocation. Occasionally, he would get a pity hand job, but nothing more.

Tonight, he would make a change. For the better he hoped, but fate had other plans for him.

He walked out of his apartment building and strode down the sidewalk to the bar he had an eye on for a while.

His nervous energy propelled him the two blocks in no time. He entered the bar and fought the wave of panic that washed over him. The bar had a good crowd, but it wasn't packed.

He calmed himself, ordered a drink and looked around. A lot of couples, the after-work drink groups and a few groups of women. The pack mentality of the women prevented him from just walking up and breaking the ice he thought.

Carl talked himself into staying calm and being patient, but he didn't want to be the creepy loner at the bar. There were three women he saw that were alone. All very beautiful.

'Don't average girls ever go out?' he thought.

His nerves started to get the better of him, but he'd worked up the courage to talk to one. However, he got to the table only seconds before her boyfriend showed up and was quickly dismissed; by both.

Embarrassed he went to the men's room and composed himself for another go. Upon returning to his seat, he found one of the single women sitting in his seat.

"Excuse me." he said politely reaching for his drink.

"Oh, no. Pardon me, I'm in your seat." she replied and started to stand.

"No, no. Please. Stay." he responded. His pulse skyrocketed as his eyes took her in.

She relaxed back into the stool. "Ok, but only if you will."

He nodded quickly and stammered out an OK and then froze. He strained not to stare at her ample breasts that were testing the limits of the buttons on her blouse. Her could not believe this beautiful woman with a stunning figure was hitting on him.

After an awkward moment she let out a small chuckle and held out her hand. "I'm Carmen."

"I'm new in town." he blurted out while shaking her hand, blushing as soon as he spoke. "I mean I'm Carl."

Carmen grinned and guided the conversation from there. Allowing Carl just enough room to try and nose dive the conversation into the ground, only to pull him back out. Eventually, he worked up the nerve to ask her to dance and through his bumbling persistence and her subtle guidance they spent the evening talking and dancing.

Some slow dancing, flirtatious talk and ample amounts of alcohol led to casual touching and eventually an awkward kiss from him.

Carl broke the kiss and waited for her reaction. Praying it wasn't a slap.

"Would you like to go somewhere quiet?" she asked with a coy yet seductive look to her.

"Yes, sure. Quiet. Yes. Um, did you have somewhere in mind?" he stammered. His ears not believing what he was hearing.

"How about your place?" she replied. Her eyes screamed sex, but he was oblivious to her cues.

"My place. OK. . . Wait. . . My place?" he tried to catch himself and calm down. "My place is fine."

"You sure?" she quipped. "You seem hesitant."

"No. No. No! I'm not. I mean, I'm sure."

Satisfied that he'd squirmed and twisted himself up enough she leaned in to him and whispered in his ear. "I could take you to the ladies' room and fuck you there, but I think your apartment would be more comfortable."

She breathed into his ear and took a nibble of the lobe before she leaned out and gave him a wicked grin. He froze for more than a moment, his small dick rising once again to the occasion.

"Well?" she asked.

"Yes. Of course; shall we?" he said, motioning her to the door.

Once on the sidewalk she hooked herself onto his arm and pulled him close. He fought the urge to walk quickly and hoped she wouldn't notice his raging hard on. Although he was hard each slow dance they did, she never acknowledged it.

With her heels she was slightly taller than him, but her figure was stunning and a set of what he figured was at least D cup breasts, which were accented by barbell piercings on each that were clearly visible through he tight blouse.

He made small conversation, trying to appear relaxed as he tried not glance at her tits, which bounced ever so slightly as she walked.

His body tingled with excitement as they entered his building. Once in the elevator she spun towards him, pinning him to the wall and kissing him deeply. Her hands finding their way to his ass.

The chime of the elevator and the doors opening broke their embrace. "I can't wait to get inside." she cooed.

He was almost trembling as they got to his apartment.

Once in, he told her to make herself comfortable as he went to make drinks. Without replying she wandered about his place.

He came out of the kitchen to an empty room wondering where she'd gone. He began to wonder if she'd left, if this was a joke on her part when he found her sitting on his bed, topless. A lavender shelf bra holding her gorgeous breasts in place.

"Make yourself at home." he said jokingly as he handed her a drink. He struggled to maintain eye contact.

"I think I will, thank you." she replied with a coy grin and a glint in her eyes. "Care to join me?"

She took a sip without breaking her gaze and set her drink on the nightstand. She then reached up and undid his belt.

"Take your shirt off." she commanded as she pushed his pants and underwear down in one move.

Carl fumbled with the buttons of his shirt and awkwardly ripped it off his arms.

She raked her nails across his skin as he worked.

"Step out of your pants." she commanded.

Carl fumbled and hopped around trying to free himself as Carmen leaned back on her elbows and stifled a chuckle.

"Stop. . . Stop. . . Stop!" she laughed, shaking her head.

Carl froze, half confused and watched as she stood up, spun him around and gave him a playful push onto the bed.

Carmen wore a sly grin and a gleam in her eyes as she worked his pants free. She then pulled him towards the edge of the bed until his ass was at the edge and then pushed his legs apart.

She flicked her hair to one side and reached over to the nightstand and open the drawer.

"I don't have any condoms." he said apologetically.

"You're not going to need one." she said flatly. "But we're going to need this."

Carmen pulled out and shook a tube of lube in front of him before dropping on the floor. She ran her hands up the inside of his thighs.

Up and down, she raked her nails, finally moving up and kneading his balls.

She leaned in and began sucking his balls and slowly pushing his legs up and back towards him. As she did, she began kissing his shaft and licking it like a popsicle.

As soon as his legs were pushed up to his chest, she told him to hold them there.

She lubed up the fingers of one hand and then grabbed his cock with the other.

Carl lay there bent in half, holding his legs up, feeling more exposed than sexual, but as she held his cock up and began swirling her tongue around the head of his shaft he didn't care. No one had ever sucked his cock before and he wasn't about to interrupt her.

"Are you ready?" she half whispered in a sultry tone and wrapped her lips around his head.

All he could do was nod.

At the same time and speed that her mouth engulfed his shaft a finger from her other hand slid into his ass.

"WWWWaaaaaaaaa?" he yelped. Half shocked and half excited.

She worked her finger in and out in sync with her mouth for a few minutes. Then pulled back and out. "Are you ok? Don't you like it? Should I stop?"

Carl's mind locked up. "What was. . . Did you just. . . I?"

"Should I continue?" she asked seductively. Her finger circling and pressing on his ass.

"Yes." he hissed. Confused as to what he was saying yes to.

This time as her mouth engulfed his cock, she slipped in two fingers.

Carl couldn't think straight. The initial shock of the intrusion wore off and now he was wondering which felt better her mouth or her fingers.

Carmen worked slowly and skillfully before stopping once more. "Carl?"

"Please. . . Please don't stop." he moaned. It felt so good. He'd never felt anything like it.

She inserted a third finger this time as she took in his cock.

Carl let out a guttural groan this time.

After pleasuring his small shaft for a minute or two she pulled her head off his dick with an audible slurp, but continued to finger his ass.

She worked her skirt and panties down as she continued. "Do you like it, Carl? Does it feel good?"

"Oh, yes. Yes, it does." he hissed and it did feel good he thought. Unlike anything he'd ever felt.

"Of course, it does Carl." she continued to finger him and then sucked him again a few times. She held him in her mouth briefly as she got herself ready.

Carl pulled his legs up further and began to writhe as she tried to spread her fingers apart inside of him.

"I want you, Carl. Can I have you?" In and out.

"Yes."

"Do you want me, Carl?" In and out.

"Yes. Yes."

"Tell me." In and out.

"Yes. I want you. Please."

"Let me have you Carl." In and out. "Let me take you."

"Please Carmen. Take me."

"Yes Carl. I want that. I want to take you." In and out. She rotated her finger so she could probe around for his prostate.

He let out an audible gasp. "Oh fuck."

"Yes Carl. Let me make you feel good. Let me fuck you. Can I fuck you?"

"Please. Yes."

"Tell me Carl." In and out." "Tell me what you really want?"

"I want you." Carl moaned as she worked her fingers around.

"How do you want me?" In and out. "Use your words, Carl."

"Ahhhh. . . I want you to fuck me. Fuck me. Please Carmen. Fuck me."

"Yes Carl. Yes. I want to fuck you too. Are you ready? Tell me you're ready."

"Yes. Yes. Yes. Please. I'm ready!"

Carmen stood up and put her hands on the back of his legs, pushing them into his chest.

Carl then felt something press into his sphincter. He lifted his head and looked at Carmen, who returned his gaze with a devilish grin.

Carl tried to process what was actually happening. It couldn't be he thought. He was sober enough to understand what was going on, drunk enough to not stop it and horny enough to want it.

She pushed her hips forward, gently. The head of her shaft easily piercing his clenched sphincter, then pausing for a moment.

Carmen lowered herself down until his calves rested on her shoulders and their faces were just inches from each other.

"Don't fight it, Carl. Embrace it." she whispered. All he could do was look up at her and nod.

As she began a slow and steady push into him, he matched it with soft erotic moan, his arms falling out, perpendicular to his body. His hands clasping the bedding as his eyes fluttered.

Carmen pulled out just as slowly, holding the head inside him and then pushing back in.

Carl could not believe how something so taboo could feel so good. Perhaps that's why it's taboo he thought. His ass was streched further than he thought it could be streched and the well lubed friction was a pleasure he'd never imagined possible.

In and out she worked his ass.

Staring into each other's eyes.

Carmen was purposely quiet. Waiting for Carl to express himself.

He, however, was completely taken aback by how good it felt. No pain, just pleasure. The most perverse and strangest of pleasures. He wanted it more and more with each thrust. A want, no a need, building inside him he thought.

In and out she worked herself. Carl would flinch and moan with excitement with each thrust that filled him. A pleasure previously unknown to him, but he knew now it was one wasn't going to be able to live without.

Carl grabbed her arms and ran his hands up to her shoulders. His mind a blur of emotions as he tried to make sense of the pleasure of being violated. His heart pounding.

"Oh Carmen." he croaked. Finally breaking the silence.

"Do you like it, Carl? . . . Being taken." she whispered back. "Can you feel me inside you? . . . Making you mine."

"Please." he choked out between his moans. His pleading eyes looking up to her.

"Please what Carl?" she whispered. Her voice calm and composed.

In and out. Slowly. Methodically.

"Carl. . . Use your words Baby."

He wanted to, but was afraid of what he wanted to say. However, pragmatism was outnumbered and it caved in to the pressure of intoxication and hormones.

The last bit of resistance in his head was drowned out by the words he spoke.

"Faster please." he hissed as she thrust into yet again. He didn't know why he said it, but his body did.

Just like he did when he got a pity hand job from an emotionless chemistry major at college. She had worked very slowly, gauging his expressions. As if he were one of her experiments. He remembered begging her to speed up, but his pleas falling on deaf ears that night. Just like then his body knew why.

"But Carl; faster means harder." Carmen replied coldly. "Do want me? . . . Harder?"

"Harder. . . Yes. Please." he moaned. His hands slid up to her neck and ran his fingers through her hair. Pulling her closer.

She leaned down and kissed him deeply. Long and passionate. "Say it, Carl. Say it like you mean it." she breathed into his ear before biting it playfully. "Say it like your life depends on it."

"Please fuck me, Carmen. Fuck me hard!" he half-heartily commanded.

She pulled out and quickly thrust back in.

"I said fuck me!" he said again. His voice cracked and croaked in desperation.

Again, she pulled out and thrust in, a bit harder. "Tell me Carl. Make me believe you."

"Fuck me. . . Harder. . . Fuck me harder!" his voice echoed through the room.

She slammed her cock into him two good times. This slapping of her body into his excited him.

"Like that Carl?" she shot back.

"Yes. Yes. Harder. . . Faster."

Slap. Slap. Slap.

"There you go Carl." she responded. "Is that good? . . . Do you like it rough?"

Slap. Slap. Slap. Slap.

"Yes. Yes. Rough. Fuck yes. Fuck me. Fuck me good. Good and hard." he said. Possessed. "Good and hard!" he grunted behind clenched teeth.

The smacking of flesh filled the room.

She pushed back and grabbed his ankles, spreading his legs slightly and increased her tempo.

"Harder!"

Smack. Smack. Smack. Smack.

Although his cock was utterly flaccid and ignored; his body swelled with excitement. He drank in the sight of this heavenly goddess panting and grunting as she slammed into him over and over. Her breasts swaying back and forth.

"Yes. Fuck me good. Yes. Yes. Fuck me hard. Harder!!" his voiced echoed through the room and out the window.

"Tell me. Tell me you love it, Carl."

Smack. Smack. Smack.

Slap. Slap.

Smack. Smack. Smack.

Slap. Slap.

"Yes. Yes. I love it!" He felt an energy surge within him. "Harder. I love it; rougher!!"

As her thrusts grew faster and harder, he felt that burning sensation deep within him. It burned stronger with each slap of her hips into his ass. A sober Carl would have been perplexed as to how this was happening, but right now he wanted nothing more than to cum and she was going to make it happen.

Smack. Smack. Smack.

Slap. Slap.

Smack. Smack. Smack.

She grunted and groaned above him. Her thick shaft jackhammering his well lubed hole as he begged and pleaded for her to fuck him.

Carl grabbed his own head and let out an animalistic howl as his limp dick spurt cum onto his belly. His body burned white hot and his nerves rippled across his body.

His eyes fluttered and rolled back. A combination of alcohol, hyperventilating, and sexual release was too much for him. Carl blacked out moments before Carmen let out her own howl as her throbbing cock pulsed and she shot her load deep inside him.

The morning light finally brought Carl back to reality. He lay there for a moment. Trying to bring himself around. Slowly the nights activities began to surface. Piecemealed.

'Was it true? Did I dream it?' he thought rubbing his head, trying to shake the cob webs. He blinked his eyes open, trying to adjust to the light.

He flung the throw blanket off him and sat up. As he stood up, he realized he was still naked.

Carl streched and took two steps and stopped dead in his tracks in front of the mirror a top his dresser. If it wasn't the dried pool of his on cum in his belly button or the mix of lube and cum starting to leak from his ass then it was the phone number written in lipstick across his chest that confirmed to him what had happened last night.

He stared at the reflection for a moment. A flurry of jumbled thoughts flooded his head. Snippets of his time with Carmen.

Carl looked around for his phone and stored the number. He set his phone down and reflected again on the previous night as his leaking ass told him it was time to clean up.

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1 Comments
FailedscoutFailedscout6 months ago

Great story!

Thank you for writing and posting here.

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