Penny's First Client

Writer's Note: This is a work of erotic fantasy, all characters and events are fictional. This series uses the term "futanari" to describe the main character, as a way of separating her from any real-world identities. The writer condemns the discrimination, tokenization, or fetishization of real-world trans and intersex people.

This is Number 2 in a series -- the Adventures of Penny Thompson -- and while each story is self-contained, they're best read in order.

It was an unseasonably warm Sunday afternoon mid autumn. Penny Thompson skipped down the street, heading to Dr. Grace Fellows' office, for the first day of her internship at the sex therapy clinic.

She was still harboring a crush on Dr. Grace, after her sexual encounter last week. What had started as a routine physical exam had turned into her first handjob, which had turned into her first lovemaking. She had given the doctor the greatest two orgasms of the older woman's life, and had been offered an internship on the spot.

What was wrong with this town? Couldn't a 19-year-old futanari walk down the street without being offered a job?

Her experience last week had been like a power-up for her self-confidence, and she had decided to make a concentrated effort to not hide her body as much. She wore her squeaky white sneakers, but had traded out her former

I-Don't-Want-To-Be-Looked-At

sweatpants and hoodie for a cute green summer dress decorated with little white flowers, which just barely covered her freckled thighs. Her penis -- which she nicknamed "Nine" for obvious reasons -- was currently small and soft, tucked snuggly in her tight little boy shorts.

She listened to one of her favorite songs on her headphones, humming along as she went.

"H-O-T T-O G-O! You can take me hot to go!"

She giggled and skipped up and down in time with the music, making her frizzy red hair dance. Today was going to be so exciting! Oh gosh, today was going to be so scary!

A bell hanging above the door tinkled as she entered Dr. Grace's office.

Mrs. Hamada looked up from the front desk with a broad grin. The receptionist was a chubby Asian woman in her mid-forties, with rosy cheeks and kind brown eyes. She had been reading an old paperback fantasy romance novel, the kind with a busty Elf maiden on the cover.

"Penny! Hi sweetie, we've been waiting for you!"

"Good morning, Mrs. Hamada!" Penny beamed. "How's it going?"

"Very well, thank you! But it's Marci, honey. No need to be so formal, we're going to get to know each other very well here at the clinic." The older woman had on her usual work outfit: A modest brown sweater, black pleated skirt, and a pair of open toed sandals. Her smooth black hair was up in a neat bun. "How is college going so far, dear?"

"Oh, classes don't start until Monday! I'm actually moving into my dorm room tomorrow, which is a little nerve wracking because I haven't met my roommate yet. I'm trying not to think about that too much though, I'm more nervous for my first day on the job here. Nervous, but excited!"

"Oh, we're all excited..." Mrs. Hamada smirked, sucking on the end of her pencil subconsciously. "Now, are you ready for some... hands-on learning?"

Penny nodded eagerly, and felt her penis jump slightly at the implication. "Yes ma'am!"

Mrs. Hamada stood up, her plump round ass swaying under her skirt as she walked around from behind the counter. "Let's see if Dr. Grace is ready for you."

Penny followed her back to Dr. Grace's therapy office. It was a cozy room, painted in calming pastels. There was an impressive hardwood desk with a computer and phone, a couple of comfortable leather chairs, and a King-sized bed in one corner, covered in red satin sheets and piled with pillows. There was another door near the bed, leading to a bathroom with a shower and linen closet.

Mrs. Hamada gently touched Penny's freckled arm, and then turned back to the reception area. "I'll be ready when you need me!" she said with a wink.

Dr. Grace was sitting in one of the overstuffed leather chairs, legs crossed, paging through a large notebook and making notes with a pen. She was dressed in her usual doctor's coat with a gray silk blouse under it, and a tight black pencil skirt with sheer black stockings. She looked up, her reading glasses sliding down her nose as she smiled. "Hello Penny, come on in. Make yourself comfortable, I just need to finish up these session notes."

Penny sat down in the other chair and took off her headphones. She bounced her leg up and down for a couple of minutes, until Dr. Grace closed her notebook and set it on the desk.

"So, Penny, as you know we're looking for your help in our sex therapy clinic," Dr. Grace began. "I have some clients that are not able to reach orgasm, despite intensive therapy, and I believe you could help them. They would be able to experience your body up close and benefit from your unique... gifts."

Penny giggled shyly. "I'm happy to help, Dr. Grace. And I just want you to know... I'm going to be an absolute professional. I'm not going to fall in love with any of the clients, I promise."

The doctor rolled her eyes. "Don't make promises you can't keep, young lady. If I recall correctly, you professed your love to me half-way through our first fuck. I suspect you have a lot of love to give."

Penny blushed furiously, but said nothing.

"Now, I'm going to have you work with Marci today. She'll be your... Proof of Concept, so to speak," Dr. Grace said.

"Oh- okay, sounds good." Penny said nervously.

The doctor leaned forward, stretching her arms over her head. The hem of her skirt raised just high enough that Penny could see a little peek of her thighs above her sheer stockings, causing Penny's heart to flutter.

Dr. Grace pressed the intercom button on the phone on her desk. "Mrs. Hamada, we're ready whenever you are." She turned back to Penny. "I know your first time meeting Marci was a bit embarrassing, but I hope that won't prevent you from enjoying your time with her today."

Penny groaned, remembering how the plump Asian woman had interrupted her in the middle of fucking Dr. Grace, and had accidentally been covered in Penny's cum.

"Mrs. Hamada has been my receptionist for many years," Dr. Grace said, "Before that she was one of my clients. She's a widow now, but even when she was married she had difficulty achieving orgasm. To tell the truth, I don't think she has ever truly cum. I worked with her for months, but was never able to help her."

Penny nodded sympathetically, but the ginger quickshot had a hard time imagining what it was like to not cum easily.

"And this is just between you and me, but Marci hasn't stopped talking about you since you left last week. I think she's quite taken with you after your brief... interaction, and is very excited to work with you."

There was a timid knock at the door, then Mrs. Hamada entered. She came over and gave Dr. Grace a big hug from the side, pressing her huge breasts into the doctor's arm. "Thank you so much, Grace! I really appreciate this. Hi again, Penny." She beamed shyly at the young freckled redhead.

Dr. Grace smiled. "My pleasure, Marci. You've been such a good friend to me these many years. I hope we'll be able to return the favor. Penny is eager to give it the old college try."

Penny felt her heart beat faster, as blood began rushing to her nether regions. She stood up, and fidgeted nervously with her hands. Damn her dress for not having pockets!

Marci grinned at Penny, then turned back to the doctor. "So, what do you want me to do? How should we start?"

Dr. Grace chuckled. She stood up and walked over to Penny, patting her on the shoulder. "This is your show, Penny. What did you have in mind for this session?"

Penny's mouth dropped open, as unsure as the proverbial dog that had finally caught the mail truck. "Umm... well... I guess I thought maybe I could... start by giving Mrs. Hamada... Marci... a back massage? Or something? When my mom is stressed out my dad gives her a foot rub, and she seems to enjoy it a lot..."

Dr. Grace smiled patiently. "Oh Penny, I'm still surprised by how someone with such a large cock can be so innocent. That's very sweet, but I think you'll need to take a more direct approach." She kissed Penny on the cheek, and then reached down to rub her cock through her dress.

It twitched and grew with the doctor's touch, creating an obscene tent in her summer dress. "Not every part of you is so innocent, eh?" the doctor sneered.

Penny was a bundle of nerves, but Nine was ready and reporting for duty. She turned away from Dr. Grace and her wandering hand, and made eye contact with Marci. "Okay... Let's do this thing!" she said with what she hoped sounded like confidence.

Marci clapped her hands, her cheeks flushing pink. "Oh, this is going to be fun!"

Penny took a step toward Marci, her hands on the buttons of her green dress. "Would you like to... umm... sit on the bed and get comfortable, while I get undressed?"

Marci nodded eagerly and hurried over to the bed. The short woman sat down on the mattress, her stout, pale legs dangling over the edge. She took off her sandals and flexed her small round toes, watching Penny intently.

Penny began unbuttoning her dress, then shrugged it off of her shoulders, allowing it to fall to her waist. Her tits popped out, perky and pale. They were sprinkled with freckles, and their small pink nipples rising up from puffy pink areolas.

She gave them a quick squeeze, and sighed happily. As an afterthought, she pinched her nipples until they were erect and sensitive, moaning exaggeratedly in pleasure. She tried to bend her head down and give them a sexy lick, but they were too small for her tongue to reach, and she had to give up and pretend like that hadn't happened.

Marci and Grace watched the awkward performance, amused, but aroused by her naïve enthusiasm.

Penny pulled her dress down past her hips, letting it fall to the floor. She wore a snug pair of white boy shorts, now tented with her growing cock. She looked nervously at Marci and said, "I guess you want to see Nine, huh?"

Marci blushed and nodded, suddenly shy. She held her hands on her lap, her arms squeezing her ample breasts through the fabric of her sweater. Her huge nipples were starting to poke through, and Penny realized with a jolt that she wasn't wearing a bra underneath, and must have taken it off before entering the room.

Dr. Grace rolled her eyes and said, "Of course she wants to see your cock, you silly little futanari!" She relaxed back into her leather chair and folded her arms across her chest and grinning. "Now hurry up before I come over there and rip those shorts off of you myself."

Penny squeaked in fear, then took a deep breath. She reached down and gripped the waistband of her shorts at the hips, then slowly inched them down her lower belly, pubic mound and thighs, revealing her growing erection. The length of her cock was pulled down with the shorts, until its head cleared the stretchy fabric and sprang to attention, slapping her stomach with a smack. She kicked the shorts away, then stood straight up and allowed her cock to point proudly in the direction of the other two women.

Her private parts were hairless, save for a patch of curly red pubic hair that she kept above the base of her cock. She breathed heavily as it grew to its full nine inches, and slowly approached the king-sized bed.

Marci gasped and timidly reached her hands out. She stroked Penny's cock with one hand, her other hand lovingly caressing the girl's freckled hip. "You are so pretty," Marci breathed.

"Y- you really think so?"

Marci looked up at Penny's freckled face, and took in every detail. Her bright green eyes, her button nose, pouty lips, her endearingly large ears that poked out from her mop of frizzy red curls. "So cute," the older woman murmured. "Like an elf....An elf with a giant cock, that is!"

Penny giggled girlishly at the compliment. "R- really?"

Marci nodded. "Yes, really. I wish I was younger. If I met you when we were both in high school, I would have asked you out."

Penny giggled again, feeling a warm surge of happiness and gratitude. This plump little woman was so sweet and kind...

Uh-oh,

she thought to herself,

I promised not to fall in love with my clients! Pull it together, Thompson! You're going to do your job and fuck this MILF silly!

The Marci continued to stroke Penny's cock, who moaned in appreciation. A drop of precum formed at the tip, then slid down her shaft in a steady stream of clear lubrication that coated Marci's hand. "I don't think I'll be able to last for long if you keep doing that," Penny breathed.

She grabbed Marci's hands and pulled them away. "May I kiss you, Mrs. Hamada? For a little while?" she asked. The older woman grinned and nodded.

She pushed Marci gently down onto the bed and climbed on top of the older woman, the way she'd seen actors in steamy movies doing. The older woman reached her arms up around Penny's narrow waist, and they began to kiss. Marci tasted like mint, and her plump lips were soft and sweet. She flicked her tongue into the young girl's mouth, making Penny moan in surprise.

Penny felt a stab of imposter syndrome -- the only two people she had ever kissed romantically were Marci and Dr. Grace, and both so much more mature and experienced than her. She would have to be a fast study!

She reached up under Marci's sweater, running her fingers over the warm soft skin of the older woman's stomach. Then she moved her hand up to feel her enormous tits. They were supple and yielding, but her nipples were large and firm, bigger than the tip of Penny's thumb. She imagined what it would feel like to bite and suck on them, and her cock twitched and released a little squirt of anticipatory precum.

"C- can I take your shirt off, Mrs. Hamada?" Penny asked hesitantly.

Marci nodded enthusiastically, and began tugging up on her sweater. Penny reached down to help her, and soon the chubby older woman was topless. She had the largest tits Penny had ever seen, clothed or unclothed. Her areolas were huge and pink, with little bumps surrounding her big nipples. Penny felt a rush of saliva in her mouth, she was nearly drooling at the sight.

The nubile redhead leaned down to take one of Marci's tits into her mouth and began to suckle on her huge nipple like a baby with a bottle. The chubby older woman moaned and reached down to squeeze Penny's tight little ass, causing the girl's cock to press into her soft belly, leaving a slick trail of precum. Penny licked Marci's nipple and bit it gently with her teeth. The older woman arched her back, pressing her big tit up into Penny's mouth.

Penny reached under Marci's skirt and began to feel her way up her plump thighs. The older woman wasn't wearing any panties, and Penny could feel her wet tangle of pubic hair and smell her musky scent. Penny grabbed two handfuls of the skirt's fabric, and tugged them down from Marci's round bottom. Marci lifted her ass off of the bed so that Penny could pull her skirt off completely.

Her soft round stomach was exposed, revealing pale stretch marks along her flank and a faded cesarean scar low on her belly. Penny had never seen a mature mother's natural body so up close and personal before, and found it to be primally, intoxicatingly feminine, like an ivory carving of an ancient goddess.

She bent down and kissed Marci below her bellybutton, tickling Marci and making her giggle.

Both women were now completely naked, Marci's soft pale flesh contrasting with Penny's coltish, freckled body.

"Oh wow... you've got me so turned on!" Marci moaned, reaching up to run her fingers through Penny's frizzy ginger hair. "I haven't felt like this in years. And now I want to feel your amazing cock inside me."

Penny scooched back and then lay down between Marci's spread thighs, her 9-inch long cock resting on the plump woman's belly, arms supporting. Her moist little pussy ground into the older woman's hot wet cunt. She looked at Dr. Grace, still seated in the leather chair and enjoying the sight of the two nude women. "Is it okay... if I make love to Mrs. Hamada now, Dr. Grace?" she asked.

The doctor nodded, observing with intense interest. "This is your session, not mine. But in my professional opinion, I have never seen two people so ready to fuck." She idly ran her hands over her own breasts, rubbing her nipples through the fabric of her gray silk blouse.

Penny beamed with excitement, and turned back to Marci. She reached down between her thighs, and pressed the tip of her cock into the chubby woman's tight cunt. Marci moaned and squirmed under her.

"Oh god, it's so big... please go slow, Penny," She pleaded.

Penny nodded and pushed in with agonizing slowness. Her cock began to feel the pressure of Marci's tightening walls, and she panted excitedly. Penny's hips began to roll up and back, thrusting her cock slowly in and out of Marci's warm pussy, achieving slightly more penetration with each thrust.

The plump older woman grabbed the girl's bottom, urging her on. "That's it... oh yes, yes!" She began to pant raggedly. "Just like that, dear... a little faster now."

Penny whimpered and thrust deeper, gasping in surprise when Marci's tunnel stretched to accept seven inches of her cock. Marci's juices were flowing freely now, and dripped from her pussy onto the bed sheets, making a slippery mess. Penny leaned forward, and let her weight push Marci back into the mattress.

Marci reached up and grabbed Penny's small tits in her hands, squeezing them and pinching her nipples, causing the girl to shudder and whine. "I love your perky little nipples," she moaned. "Oh my god, they're so cute, like candy." She began to squirm and buck under the young redhead, urging her to move faster. "Please, I need it deeper..."

Penny began to pull out slowly, feeling Marci's tight walls gripping her shaft like a vice. She pulled back until just the tip of her cock was inside the woman's pussy, then she plunged her cock back in forcefully, making Marci scream with pleasure.

"Oh yeah! Like that, fuck me hard!" Marci yelled. "Harder, Penny, please!"

Penny began pumping Marci's cunt faster, moaning loudly as the older woman clutched at her small tits, squeezing and kneading them in her hands. Penny could feel herself approaching the point of no return, but focused on her breathing and tried to do math problems in her head, so that she could hold out a little longer.

"Use your fingers," Marci begged. "Play with my clit while you fuck me!" She lifted her thick legs off the bed and wrapped them around Penny's back, urging the girl's hips to pump harder.

Penny reached down and began to rub her swollen clit. Marci wailed with pleasure, reaching her own hand down to help. She grabbed Penny's hand and pressed it against her clit, grinding it into herself, moaning, "Oh god, something is happening..."

Penny plunged two fingers of one hand into Marci's cunt, feeling the woman's powerful walls squeezing around them as they slid alongside her cock. She pinched and twisted Marci's angry clit with her other hand and felt it begin to swell, until it throbbed under her fingertips.

Marci arched her back off the bed, her whole body trembling, then she let out a loud scream. "Oh my god... oh fuuuuck!" Her vaginal walls tightened and released, tightened and released, squirting a jet of feminine fluids onto Penny's groin with each contraction.

Penny held on for dear life as Marci's orgasm rolled on for what felt like an eternity, the older woman howling with animal joy. The pressure, the wetness, and Marci's cries of passion all served to push Penny over the edge. She moaned loudly, her nine-inch cock spitting a massive load into Marci's quaking cunt. Her cum shot deep into Marci's womb, then overflowed, oozing out around the chubby woman's round ass.