tagLesbian SexThe Classified Ad

The Classified Ad

byAnn Douglas©

For perhaps the sixth time that morning, Jackie Esposito reread the bulletin board classified on her computer screen. As she had the previous five times, she slowly shook her head. What had ever possessed her to write such an ad? Silently, she read it again.

"Married White Female - 20. Brooklyn, NY Bi-curious. Looking for an understanding lesbian or bi-woman to help me explore the world of female sexuality. Not looking for a relationship as of yet, just a little fun."

When she had posted that add on the BBS last week, she really didn't expect to get any serious answers. In fact, most if the hundred or so answers had been from men. The latest one, still in her in box, was typical of the lot.

"Yo sexy lady. You don't need all that dyke crap. If you need a little entertainment, I've got 8" of pure delight."

But none of the crude responses bothered her as much as the response she had received yesterday morning. With a trembling hand, Jackie punched it up again and began to slowly take in the words once again.

"Dearest Jackie, I saw your Ad, and while I normally don't respond to such things, something told me I should take a chance and answer yours. My name is Colleen and I'm a 34 year old Lesbian. If you would like to get together and talk, perhaps have lunch, please give me a call. If anything develops, fine. If not, well then that's also fine. If nothing else, it may just give you the chance to get a few things off your chest. My office number is 555-1782. I make no secret of my sexuality, so you don't have to worry about calling my office. I hope to hear from you. Colleen"

Taking a deep breath, the bathrobe clad woman reached over and switched off the computer. Walking back to the bedroom, Jackie reviewed the events that had led her to this morning.

Had it really only been two weeks ago that she'd been to brunch with her friends at Kelly Michaels house. It was a get together they had twice a month, dating back to their high school days. Each member of their little circle took a turn at hosting it. How could she have known that afternoon would cause long buried desires to erupt to new life.

It was your typical brunch, a few snacks, tea and coffee - and of course gossip. That was the real reason they all got together. Nothing was as much fun as getting together with your girlfriends and hearing all the latest dirt - at least that was what Jackie had believed up to that point.

The usual people were there. Kelly Michaels, the oldest of the group at 21. Tall, blonde and blue eyed, she had been Prom Queen at graduation. Still single out of choice, she was already a rising star at the firm she had joined right out of high school. Of course it didn't hurt that daddy owned the firm.

Next came Janet Innis. Almost as tall as Kelly, she had a short curly hair as black as her skin. Already a junior at State, she was the brightest of the group. At the rate she was going, she'd have her degree six months before anyone else in her class.

Rhonda Jo Chambers was next. The second blonde of the bunch, she gave truth to the stereotype of the dumb, beautiful blonde. If it wasn't for the help of the others, she'd have still been in high school. The flip side was that the bombshell had married Carl Chambers, the son of Jimmy Chambers. Jimmy Chambers had opened his first hardware store in 1979. Last week he had opened his tenth.

The baby of the group was Karen Scott. Still 19, the redhead was a student at City University and engaged to be married next year. She also worked nights as a waitress.

The last of the group present was Maria Santiago. The shortest of the group, only 5'2", Maria never the less possessed the best body of any of them. A fact that was never lost on the long string of boyfriends she'd had over the last few years.

Three girls were missing from their original clique. Donna Sullivan, who had moved to California to attend UCLA. Beverly Clark, who was nine months pregnant and not really in the mood for brunch. And the third missing sister was Mary Catherine Murphy. The reason for her absence was the main topic of discussion.

"Can you believe that Mary Catherine left Roger?" Karen said as she sipped her tea. "Who would've guessed that they'd wind up in divorce court?"

"They've been together since freshman year of high school." Kelly commented, twirling her long red locks - a habit she'd had since high school.

"I heard that Roger was bedding one of the women in his office." Maria interjected, a secret smile on her face. It was her secret vice - seducing married men. "And that Mary Catherine walked in on them."

"Oh God!" Rhonda Jo Chambers gasped. "If that happened to me, I'd be reaching for my daddy's shotgun.

"You'd shoot yourself?" Jackie asked unbelievingly.

"No, silly." Rhonda Jo laughed. "Them!"

All the other girl laughed as well.

"Isn't that just like a man." Kelly said. "Here he has a beautiful and loving woman at home and he feels the need to go looking for someone else."

"How true." chorused a few of the girls as their laughter rose in volume and went on for the longest time.

"Actually, that's not true." Janet said in a quiet tone.

"What's not true, Jan?" Kelly asked. "That men aren't like that?"

"No." the tall black woman said. "That Mary Catherine walked in on Roger and a honey."

The last remnants of laughter faded right away as all eyes turned to Janet. A wide smile filed her face. That kind of all knowing look that said..."I know a secret that you don't"

"Actually, it was Roger who walked in on Mary Catherine." Janet said, every woman there hanging on her every word.

"You mean Mary Catherine was getting it from someone else?" Susan asked. "I can't believe that."

"She never seemed the type." Kelly said. "I mean I never even saw her look at another guy."

"That's right." Rhonda Jo agreed. "Remember how we used to joke that if she didn't marry Roger, she'd become a nun. She even had the perfect name already."

Jackie hadn't said a word, she was too busy looking at Janet. She still had that same knowing smile, there had to be more to the story.

"Are you sure about this?" Karen asked. "My husband heard the story from Roger himself."

"Well, I think that maybe Roger would rather people think he'd got caught screwing around than let them know about Mary Catherine's affair." Janet responded, her grin now spread from ear to ear.

Varied looks of confusion filled the faces of the four women. This was the best gossip Janet had heard all year, and she wanted to really enjoy telling it. She let a few more moments pass before letting out her secret.

"I never said that it was a guy that Roger found her in bed with." she said.

"Omigod." was the collective response.

From that afternoon on, Jackie couldn't get the image of Mary Catherine in bed with another woman out of her mind. Mary Catherine had been one of her best friends since high school. Back then she'd been Mary Catherine Lewis. She and Roger used to double date with Jack and her. It fact it was Mary Catherine she'd turned to that night when she'd discovered that she was pregnant during the last month of senior year.

Now to discover she was into women. While the other women in their little social circle were very loud in their expressions of disgust, Jackie felt herself filled with a very different emotion - that of envy.

It'd been quite of few years since Jackie had entertained the idea of sex with another woman. All through high school, she had found herself with the desire to touch another girl - and to have them touch her. Many a night she had laid in bed, remembering what the other girls had looked like in the shower -and had masturbated to those images.

What she lacked in those days was the courage to act on those feelings. So Jackie had buried her feeling and followed the role everyone thought she should be. Honor student, cheerleader, girlfriend of a football star. She remembered all too well the scorn and isolation heaped on poor Dotty Myers who all the other girls assumed was a dyke. Dotty was somewhat plain and highly athletic, a real tomboy. Since she also wasn't what you would call socially active - the other girls had automatically hung the "lesbian" label on her.

Dotty proved them all wrong when she married Clarence Oswald. Clarence was a male version of Dotty - the stereotype nerd. He was also the founder of Startech - now one of the fastest growing software companies in the southeast. The last Jackie had heard, they already had three kids, a girl and twin sons.

Jackie's marriage to Billy Espositio on the other hand had been far from ideal. Married at 18 in a race with the stork to the altar, it had degenerated into two strangers sharing an apartment. Jackie had suffered a miscarriage a month after the wedding. She had never forgotten the look of relief that had appeared on Bill's face when the doctor told them that she'd lost the baby. Or the way he'd so casually accepted the later verdict that she probably wouldn't have kids at all. Despite that, they had been married and she tried so hard to make it work.

But it took two to make a marriage work and for the longest time, Jackie knew she was in this fight alone. They still lived in the basement apartment of his parent's Bensonhurst house. Billy still spent his days at his family's lumber yard and his nights at the local bar. Or the bowling alley, or the pool hall. Those few nights he did spend at home, were spent glued to the front of the television.

In fact, the only time she really felt that he even acknowledged her existence, was those nights that he suddenly felt the need for sex. That was another thing that hadn't gotten any better since high school.

The response to her ad had brought it all to a head in the last twenty-four hours. Deep in her heart she knew it was now or never. As late as last night, she'd tried to have a serious talk with Billy about their problems.

"Billy, we need to talk." Jackie said to her husband who as usual was in front of the television watching Sportschannel.

When no response came, she repeated her statement.

"You say something, baby?" Billy replied, his eyes never leaving the screen which was showing the finals of Woman's Volleyball from California.

"I said that....." she began for the third time before getting cut off by a shout from Billy.

"What a shot!" He yelled as one of the big breasted blondes on screen scored a point.

With a sigh, Jackie knew she was wasting her time.

"I said that the paperboy is here." She lied. "Do you have five dollars to pay him or should I just blow him as usual?"

"What's that, honey?"

"The paperboy......" she repeated.

"Oh, take care of that for me, will ya." he replied as the game resumed.

"Sure, no problem." she concluded in a defeated tone. "Maybe he'd at least have appreciated it."

So here she sat, staring at the phone. Since she only worked part time, she had the whole day free.

"I'm going to do it." Jackie said out loud to then empty room.

As soon as the words left her lips, she felt greatly relieved. Of course an hour from now she could loose her nerve again. Before she did, she started dialing the phone.

"Doctor O'Connor's office." said the voice that answered on the other end of telephone.

"Is this Colleen?" Jackie asked.

"No, this is Martha." the voice replied. "Colleen's in with a patient right now. Who may I say is calling?"

"She's a doctor." Jackie said to herself. Somehow, that made her feel better.

"Could you tell her that Jackie called." she answered, wondering if fate was giving her a chance to quickly back and that maybe she should take it.

A few seconds passed. Seconds during which, Jackie would later learn, Martha was checking a short list of names in her desk draw. Jackie had come in on the doctor's private line. A line that bounced back to the front desk if she was in with a patient. The receptionist stopped with she came to the name Jackie penciled in at the bottom. Since she knew Dr. O'Conner gave the private number to women she met, rather that use her home number, finding only a first names wasn't unusual.

"If you can just wait a moment, I'll see if the doctor can pick you up." Martha said.

Martha was totally heterosexual, but there were times, after nearly thirty years of marriage, she was really curious about the concept of lesbian sex. That and the women the doctor dated. She had never actually met any of them, they were just voices on the phone.

When Colleen had hired her, she had told her right off the bat that she was a lesbian and asked if she had a problem with that. If it had made her uncomfortable, as it did to the last three woman who'd applied for the job, Colleen would understand.

Martha had replied that what the doctor did in her own bed was her own business - no one else's. Truth be known, some of the games the 48 year old and her husband played between themselves would seem strange to many people as well.

"Sure, I'll wait." Jackie said without thinking about it. Now it would be rude to just hang up.

"Hello, Jackie?" said a soft melodious voice a minute later.

"Hello Colleen."

"I'm so glad you called." Colleen said. "But I'm afraid you've caught me in the busiest part of the day."

"Oh, I'm sorry." Jackie answered. "I guess I could call back another time."

"No, there's no need for that." said Colleen." "I can spare a few minutes."

The two woman traded pleasantries for a few minutes. Jackie never realized how hard it would be to talk to someone she didn't even know over the phone. It was so hard to read the person on the other end of the receiver.

The sound of a buzzer in the background interrupted Colleen. She excused herself for a moment and then came back on the line.

"I'm afraid I've already backed up the appointments." Colleen said, indicating that she would have to cut it short.

"I understand." Jackie said. "I really have enjoyed talking to you."

"Tell you what," Colleen said. "I really meant what I said about getting together for lunch. My last appointment is for noon. Would today be good for you?"

"Today?" Jackie repeated.

"Yes, unless you already have plans."

Jackie looked at the clock. It was nine thirty. There was absolutely no reason she couldn't say yes. No reason but her own fear.

"Jackie?" Colleen inquired. "Are you still there?"

"Yes, I was just thinking." came the reply.

"Of course, I understand if you'd rather....."


"Excuse me?" Colleen said.

"I said yes, I'd love to meet you for lunch."

"Wonderful!" Colleen beamed. "I'm in Brooklyn Heights, is that ok with you?"

Only a half hour away by subway but a world away as far as any of her friends were concerned. To Jackie, it was perfect and she quickly said so. The two then exchanged a few more details on where exactly to meet and how they would recognize each other. Then Colleen said good-bye and that she was looking forward to meeting Jackie. For her own part, Jackie echoed the sentiment.

Jackie found herself staring at the phone for at least five minutes after she had replaced the receiver on the cradle. She had actually done it. In less than three hours, she had a date with another woman.

"Oh god, what do I wear?" was her first thought.

It'd been a very long time since Jackie had dressed to impress someone. As far as Billy was concerned, she could just go naked. At least that was the only time he seemed to pay attention to her.

Already Jackie had pulled out and then rejected a half dozen outfits. Should she wear something sexy, or would that be too trashy. Or would Colleen expect her to dress conservatively. After all, she was a doctor. It would be a good assumption that if she was coming from the office she would be wearing something traditional. Or were the rules different for lesbian doctors?

After all, to her knowledge, Jackie had never actually met a lesbian before. Unless you counted Mary Catherine that is, and she really didn't think that she was a good model to chose from. In fact, aside from the famous lesbians you always heard about - sports stars and models and such, she had only one other image to follow. A few months back, she'd seen a tape on cable of the gay pride parade in Manhattan. It was filled with lesbians, some of them who acted more masculine then men and paraded topless. That had been a little hard for her to take. What if Colleen was like that?

"Only one way to find out." Jackie said as she finally settled on a yellow and blue sundress. "If worse comes to worse, I'll just make up a story about having to cut lunch short and get the hell out of there."

Having laid out her clothes, Jackie stepped into the bathroom and turned on the shower. It would've been nice to run a bath instead but she wouldn't have the time. Placing her robe on the door hook, the brunette took a moment to admire her naked form in the mirror. Her breasts were a firm 36C and she worked out to keep her waist the same as it had been in high school. As a result of many afternoons sunning topless in the privacy of their backyard, her normally pink nipples were a dark brown and the rest of her a nice golden hue.

Running her fingers down across her breasts and stomach, Jackie stopped at the large dark bush of hair between her legs. She wondered if she should shave it. Billy had suggested it a few times after he had seen it in a porno movie. After the second time he brought it up, she had offered to shave it if that meant that he would go down on her more often. An activity that even after two years of marriage occurred once in a blue moon. Billy then stopped asking.

"Maybe another time." Jackie mused as she dismissed the idea.

Stepping under the warm rain of the overhead shower, Jackie closed her eyes and allowed the bright droplets to splash against her skin. The gentle touch was like a warm massage, causing her mind to drift. Unbidden, the dream of long ago days, a dream that had again worked it's way from deep within her memory, flowed through her mind.

Her eyes still closed, Jackie could tell that the light blue tiles of her shower had turned to a bright white and the shower itself was now more than four times as large. Shutting off the valves for the showerhead, now only one of a dozen that lined the walls, Jackie could hear voices from the adjacent room. She looked for a towel to wrap herself in, but all the hooks on the far wall were empty. With a shrug of her shoulders, she walked into the other room - still dripping wet and naked.

Stepping into the brightly lit room, Jackie immediately recognized it. She'd seen it so many times before. It was the locker room of Bishop O'Mallory High School. The exhibition playing itself out before her eyes however was not something she was used to. Spread out across the room were her closest friends. All were as naked as she was - and all were deep in the arms of Sappho.

In the center of the room stood Kelly, her left leg propped up on one of the locker benches, both exposing the thick red patch between her legs and giving full access to it to the girl kneeling beneath it. It took Jackie a moment to realize that the girl on the floor was Donna Sullivan. The dark haired girl had her tongue stretched up and inside Kelly's pussy, working it up and down furiously.

Standing alongside Kelly was Rhonda Jo, trading deep kisses with the redhead and playfully caressing Kelly's bouncy breasts. Donna also had two of her fingers deep inside Rhonda's cunt, duplicating the action of her tongue on Kelly's.

To their right was Maria and Beverly Clark, locking in a tight embrace, each girl's mouth glued to the sex of the other. Both seemed oblivious to the action around them, enjoying the favors of the other.

The biggest surprise was the spectacle on the left. There was Karen Scott, spread out on the floor on all fours, her perky little breasts bouncing back and forth. Kneeling behind her, with a firm grip on her hips was Janet, pounding away at the young girl like a man. Strapped around her crotch was a long, dildo, as black as her own skin. With increasing speed, it disappeared and then reappeared as it penetrated Karen again and again. Much to the pale-skinned girl's delight.

Report Story

byAnn Douglas© 16 comments/ 22836 views/ 31 favorites

Share the love

Report a Bug

5 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: