tagLesbian SexPenny’s Initiation

Penny’s Initiation

byChristina Samuels©

The following is a fantasy requested by one of my readers. Hope you enjoy it!

* * * * * * * * * *

Penny sorted through the mail. The usual lot: bills, catalogs, applications for credit cards. She was about to toss it all aside when a smallish envelope with very flowery handwriting caught her attention. She opened it and read: 'You are cordially invited to a Lady of the Night lingerie party at the home of Kimberly Morgan, this Saturday, the twenty-first at one PM.'

Penny stared at the invitation. She read the name once more. 'Kimberly Morgan.'

Again. This time, aloud. "Kimberly Morgan."

She made the connection. 'Miss Dean's ballet class!'

Less than a month earlier, Penny's daughter had begun taking dance lessons at D & J Studios, and had become fast friends with another newcomer: Heather Morgan. Kimberly was her mother.

"Yes." Penny almost purred. Images of her hostess dressed in a barely-there outfit slowly filled her thoughts. "Kimberly Morgan."

A spark kindled between Penny's legs, as memories of the first time they'd met took over. How embarrassed she'd been when she was caught staring at Kimberly's long, sexy legs. How wet she'd become wondering what it would be like to suck, lick, kiss, tease the slightly older miss' rather smallish breasts. How dizzy; at the thought of moving down. Lower . . .

"Come on Mom! Time to go!"

Her daughter's not-so-patient call brought Penny back to reality. Her face was flushed, and her pussy craving attention. She wanted nothing more than to grab her favorite vibrator and let it work its magic right then and there, but . . .


With a sigh, Penny returned the invitation to its envelope and tucked it in her purse.

* * * * * * * * * *

It was a little after noon when Penny finished dressing for the party. (White blouse; flowered skirt that fell mid-calf; sandals. No bra. No panties.)

"What time will you be back?" her husband, Mark, asked.

"I'm not sure." Penny answered, "I don't want to be rude and leave early, so I guess I'll stay till everybody else is ready to leave. I don't know. Three, four o'clock. Why? You planning on having an orgy or something while I'm gone?"

"Never can tell."

"If you are, have everybody out of here by two thirty, that's when Hannah gets back from the birthday party."

"Doesn't give me a lot of time."

"Such is life."

* * * * * * * * * *

The drive to Kimberly's house was a short one. Penny pulled up in front of the nicely-restored Victorian, and turned off the motor. As she did, another car arrived, and two women in summery dresses got out. Her imagination began to run wild as visions of them modeling thong panties and lace push-up bras took hold. She shook it off, then got out and followed them up the walk.

Kimberly answered the door. "Joy! Kathy! Hi! I'm so glad you could come. Penny! Hi!"

The two women turned in Penny's Direction.

"Joy, Kathy," Kimberly said, "I'd like you to meet Penny. Her daughter and mine are in the same dance class."

"Nice to meet you." Penny said, as Joy and Kathy gave her the same lusty inspection she had given them.

"Let's go in." Kimberly said, "Nancy's just about set up."

Joy and Kathy went inside. Kimberly subtly blocked Penny's way. "Penny," she said, "I have a favor to ask."


"Normally, when Nancy does one of these parties, her sister Elaine models everything, but she just called to say she can't make it. So I was wondering . . . since you and Elaine are about the same size . . . would you be willing to fill in?"

The question caught Penny off guard. She thought for a brief moment, then heard herself answer: "Sure. Why not!"

* * * * * * * * * *

Kimberly lead Penny down the hall to a small bedroom where Nancy was waiting.

"Good news." Kimberly said, "Penny agreed to fill in and be your model."

Nancy gave Penny the once over twice. "That's great!" she said.

"I must warn you," Penny said, "I've never done this before."

"I bet you can't remember the last time you said that." Kimberly said with a knowing wink.

"You're terrible!" Nancy said.

Kimberly smiled and shrugged. Penny glanced first at Nancy, then at Kimberly trying to figure out what was going on.

"Ignore her." Nancy said, turning her attention to Penny, "She's just jealous." She turned her attention back to Kimberly. "Now; if you'll leave us alone so we can get the show on the road?"

"Alright. I'm going." Kimberly laughed as she pulled the door closed behind her.

"Have you ever been to a lingerie party before?" Nancy asked.

"No." Penny replied.

"Okay. Here's the crash course." Nancy said, "It's girls only, and the first thing I do is hand out catalogs to everyone. Now, don't get me wrong, the catalog does a good job of showing you what everything looks like; but just about everyone needs to see it on a live model before they can make up their mind before they're willing to buy. That's where you come in. As my deal closer.

"It's not too tough. All you need to do is go around the room once letting everybody get a good look; up close and personal. If you get my drift. Then . . . just strike a pose. Like I said: not too tough. Think you can handle it?"

"I think I can handle that." Penny said, trying to sound confident, "No problem."

"Good. Now. Time to take of your clothes, and get to work."

Penny began to unbutton her blouse. As she did, it suddenly occurred to her that she had on nothing underneath. She hesitated for a moment, somewhat embarrassed by her choice to forgo her 'undies', while attending a lingerie party. With no place to hide, she drew a deep breath, then quickly took off her blouse, and slid down her skirt.

"Going commando, I see." Nancy said.

"I was in a bit of a rush." Penny said, "I . . ."

"Don't worry about it. I do it too, from time to time." Nancy confided, before quickly changing the subject back to business.

"The first item I want you to model is on the bed. Hurry up and put it on. I'll be waiting in the living room."

Before Penny could think of anything more to say, Nancy was gone.

* * * * * * * * * *

The outfit laying on the bed was a rather modest, passionate-purple corset, with matching stockings, and a pair of 'dainty' slippers. Penny eyed the ensemble, then quickly dressed. Much to her surprise, it was all a perfect fit. With a mix of vanity and amusement, she studied her look in the mirror. After a moment or two, like a silly teenager, she giggled.

"I can't believe I'm going to do this!" she said.

The image reflecting back was one Penny scarcely recognized. Although she did own a couple pieces of lingerie (far more revealing than this), she had never had the guts to wear them anywhere beyond the bedroom. And to let anyone but Mark see her in them?

She turned to face the door. Her confidence began to fade. She took one, then two tentative steps. Her heart was pounding and her palms sweating. She reached for the knob and turned it.

"Here goes nothing!"

* * * * * * * * * *

The living room was spacious, brightly lit, and dripped with Victorian touches. Joy and Kathy were seated on a period love-seat in front of a large bay window. Kimberly: in a matching chair alongside. Nancy was standing next to the fireplace opposite them.

Penny stepped inside and struck a pose.

"This number," Nancy began, "is our best selling corset. Page three of the catalog, item number three A: a taste of Venice."

Remembering Nancy's instructions, Penny slowly strutted around the room, giving each of the women a chance to look her over.

"It has hidden under-wire cups with removable push-up pads," Nancy continued, "and a spandex back with hook and eye closure. The garter-straps are adjustable for a perfect fit; and are removable. The matching low rise booty shorts are included, but the stockings and slippers are sold separately."

"Penny? Would you come back over here a minute?" Joy asked.

"Certainly." Penny replied.

"Nancy," Joy began, "you said something about under-wire cups. Don't they hurt?"

"Feel for yourself."

"Do you mind?" Joy asked.

"Not at all." Penny said, caught-up in the moment.

Joy ran her hands over Penny's double D breasts. Tentative at first, then bolder. Her fingertips: pressing; exploring. "I see what you mean."

"Let me feel." Kathy said.

More than a little; turned-on, Penny stepped to the side, and invited Kathy's more investigative touch. "You're right." Kathy said, "I can barely feel the under-wire at all; but it sure does a nice job supporting her boobs!"

Kimberly was next. Like Kathy's, her hands examined every covered inch of Penny's barely-covered breasts. "What I like about it," she said, "is that you can't tell where the padding leaves off and the real thing begins."

"Penny?" Nancy interrupted, "Why don't you go put on the next outfit while we discuss the merits of this one? It's hanging on the closet door."

Not really ready to give-up the arousing attention, Penny reluctantly turned and made her exit.

* * * * * * * * * *

Penny started back to the make-shift dressing room. As she walked, her heart raced, and her pussy burned with desire. She played the events of the last ten minutes over and over in her mind. It was like waking from a dream. Desperately, she tried to make sense of it all. Her pace slowed. She stopped dead in her tracks. The improbability of this fantasy-cum-true settled in.

'What are the odds?' she thought, 'I barely know Kimberly, but she didn't hesitate to ask me to fill in on a moment's notice. How did she know I'd do it? How did she know everything would fit like it were tailor-made? And all the touching. How did they know that's what I wanted and that I wouldn't freak out?'

Slowly, Penny continued down the hallway. It bothered her that these total strangers seemed to know about her dark desire. But . . .

She continued to wonder: 'Had they been tipped-off? Had she been set-up? Did it really matter?'

* * * * * * * * * *

The next outfit was a white satin Merry Widow, with matching, lace evening gloves and high-heeled sandals. Penny stared at it. She closed her eyes and imagined all those exploring hands touching and testing. She smiled in anticipation.

As quickly as she could, Penny stripped off the first, and donned the second. With a little more flourish than before, she headed down the hall and made her entrance.

* * * * * * * * * *

"This number," Nancy began, "is another of our best selling items. It's on the bottom of page six, item number six D."

As before, Penny paraded around the room, doing her best imitation of a Victoria's Secret Angel.

"This Merry Widow, also has hidden under-wire cups with removable push-up pads. It is front closure, using more hooks and eyes. The garter-straps are adjustable for a perfect fit; but are not removable. The matching bikini-style panty with rear peek-a-boo cut-out is included, as are the elbow-length gloves. The stockings and sandals are sold separately."

"How hard is it to open all those hooks and eyes?" Kathy asked.

"Why don't you show her?" Nancy said.

Penny hesitated for a moment, then began to work open the first clasp. "It's a little easier without the gloves." she said.

Kimberly got up from her chair and walked over to Penny. "Here. Let me."

Penny moved her hands away. Kimberly smiled, then set about her task. Almost instantly, it became obvious that this was not the first time she had offered such assistance. And judging from Penny's ragged breaths, even more obvious that her expertise was having a very; arousing, effect.

"As you can see," Nancy said, "an eager lover should have no trouble at all getting to the object of his or her affections."

Kimberly's feminine touch caressed the material aside. Penny shuddered as the cool room air danced across her nipples.

"I'm intrigued by the 'bikini-style panty with rear peek-a-boo cut-out' panties." Joy said, "Could I get a closer look?"

A flushing heat; down there, gave Penny pause. 'What if she sees how wet I am?' she thought. 'What if she does!'

Penny walked over to Joy, and struck a nearly-pornographic pose that placed her scantily covered pubes at eye level.

"Turn around." Joy said, "I want to see how much; or how little is exposed."

Penny spun on her toes, then looked back over her shoulder. Joy reached out and lightly traced the heart-shaped cutout that began just above the cleft of Penny's butt cheeks, and came to a point half way down.

"Sexy." Joy said.

"How far down does the cutout go?" Kathy asked.

Penny stepped in front of Kathy and struck another nearly-pornographic pose.

As Joy had done, Kathy traced the cutout with her fingertip. More brazen than her friend, when she reached the bottom, she eased her middle finger inside the silky material, and slid it down until her nail rested just above Penny's puckered hole. Seductively, she drug it back up and out.

A soft sigh slid passed Penny's lips.

Kathy stood, then reached around Penny's waist and began to mate the hooks and eyes. "I want to see how easy it is to fasten." she said.

Penny closed her eyes and tried hard not to think about how erotic it was having Kathy's sensual touch on her breasts as the final clasps were hooked.

* * * * * * * * * *

The third outfit Penny modeled was even more revealing than the last: a see-through chemise, with a pair of six inch stiletto-style heels.

* * * * * * * * * *

"This number," Nancy began, "is part of our barely-there collection. Page seven, Item seven A."

Penny stood in the middle of the room and struck a pose reminiscent of a street-whore trying her best to attract a John.

"This smooth and silky chemise," Nancy continued, "has tantalizing open sides, adjustable straps, and a sleek fit. The material is a soft silk chiffon. The matching g-string is included; but the stilettos are sold separately."

Penny wet her lips, then gave each of the women in turn the most beckoning look she could. To her surprise, the looks returned were cold and analytical; like they were trying to decide if she was worthy of the title: 'Slut Mom of the Year'.

"I like the way you can see her nice hard nipples." Kathy said.

"I like the way the g-string nestles between her butt cheeks." Kimberly added.

"I like the way those heels make her legs look." Joy chimed in, "Draws your eye right up to her sweet little pussy."

"So we're in agreement?" Nancy said, "This outfit puts it over the top?"

The comment caught Penny off-guard. 'Puts what over the top?' she thought.

"I think we need to see the last one." Kimberly said.

"I agree." Kathy said.

"I'm with Nancy." Joy said, "But what the hell! Let's see the last one."

* * * * * * * * * *

Penny stepped into the make-shift dressing room and began to take off the chemise. As she did, she tried to sort-out this last go-around. To explain-away the explicit remarks about the way you could see her 'nice hard nipples'; about the way the g-string 'nestled between her butt cheeks'; about how the heels made her legs look, and how they drew your eye 'right up to her sweet little pussy'. About the cryptic vote as to whether she need model the last outfit.

Unexpectedly, the door opened, and Nancy stepped in.

"You've been a big hit." she said.

"It's been fun." Penny said, trying desperately to hide her true feelings.

"The only question, is whether or not you're ready." Nancy said, her tone serious.

"Ready for what?"

"The last outfit you will be modeling is a sexy stretch lace trim set that features an open cup bra top and matching open crotch thong." Nancy said, switching to her presenter's voice, "It includes a matching stretch lace trim collar and fur-lined handcuffs."

"Fur-lined handcuffs?" Penny questioned somewhat fearfully.

"You do want to join our group, don't you?" Nancy asked, "That is why your husband, Mark had me arrange your invitation, isn't it?"

"I . . . I . . .He what?"

Penny's thoughts were spinning out of control.

"Arrange your invitation." Nancy said in a matter-of-fact way, "He said he wanted to help you explore your bi side, and that he thought our little forum would be just the place for you to see if the reality of making love with another woman lived up to the fantasy. Judging from how wet you are, I'd say so far so good."

"Mark said all that? Did this for me?"

Penny couldn't believe what she was hearing. It was a dream come true!

"He did." Nancy replied, "Now. If you want to back out, that's okay. But if you want to experience what we have in store for you, put on the outfit – along with these hooker heels – and then I'll help you with the cuffs. Take a couple minutes to make up your mind."

"No need." Penny said, enthusiastically, "I'm ready."

Nancy smiled a lustful smile, then leaned back against the door as Penny slipped on the skimpy panties, and even skimpier bra. Her smile broadened, as Penny stepped into the high-heeled pumps. "Let me adjust things so your boobs are a little more covered." Nancy said.

It was all Penny could do to keep from laughing aloud. By design, the only 'coverage' the open cup bra top provided was in the form of two strips of lace that formed the top edge, and were barely wide enough to hide her rather large areolas. Still, she stood patiently as Nancy's soft, sensual touch manipulated the fabric.

"There!" Nancy said with pride, "Now for the collar and cuffs."

A sense of uneasiness enveloped Penny as Nancy fit the lace collar in place. Nervousness, as she nestled the weighty silver chain beneath it. Apprehension, as the padded handcuffs were locked behind her back and connected to the dangling end of the chain.

"Show time!" Nancy whispered.

* * * * * * * * * *

Nancy lead Penny passed the living room and down a short flight of stairs to a dimly lit room. In the center was a large, round bed. Around the perimeter: a half dozen overstuffed chairs.

"Your last chance to back out." Nancy said.

Penny shook her head and smiled a nervous smile. As if on cue; Kimberly, Joy and Kathy made their entrance. Naked; each and every. Nancy turned, closed and locked the door. "Let the fun begin." she said.

Penny's eyes darted from woman to woman.

Kathy approached, and placed her hands on Penny's shoulders. Gently, she guided her near the edge of the bed, then lightly kissed her cheek. "This is going to be fun." she whispered.

Joy was next. She stepped-up, then raked her nails over the sides of Penny's breasts. A quick kiss (to the lips) followed. "When we're done with you . . . Ooooooo." Her breath singed the side of Penny's neck.

It was Kimberly's turn. Without saying a word, she reached between Penny's legs and arranged her pussy lips so that they were centered in the opening of the thong's crotch. "You think you're wet now? Just wait."

Nancy bumped hips with Kimberly: moving her aside. Now naked as well, she stood directly in front of Penny, and reached around to cup her butt cheeks. She squeezed; moved in closer, and pressed her bare breasts hard against Penny's. "You belong to us."

Kathy approached again. This time from behind. As a tease, she ground her bushy mound against Penny's shackled palms. "Have you ever been fucked with a strap-on?" she asked.

"No." Penny replied softly.

"Would you like to be?" Nancy asked


With Nancy and Kathy's help, Penny sat on the edge of the bed. Kimberly and Joy moved in and stood in front of her. Their breasts were at eye-level. Or better said: mouth-level.

"You know what to do." Joy said.

Penny closed her eyes and opened her mouth. A stiff nipple (Joy's) brushed her lips. She embraced it and began to suck. Far too soon, it was withdrawn: replaced by (Kimberly's) thicker, though less erect one. Again; she began to suck. Again, a switch was made.

"Ahhh." Joy cooed.

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byChristina Samuels© 4 comments/ 109016 views/ 26 favorites

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