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Around this time last year, I lucked into a coveted internship at a top advertising firm in the city. Sure, I had the grades and the resume. But in posh firms like that, it’s all about connections, so it definitely helped that my former sorority sister Jenna had a new stepmom, Gina, who was in charge of the marketing department. Jenna and I weren’t super close as friends; she graduated the year I pledged. But what can I say? The socializing and craziness of Greek life does have a way of translating to professional networking, too. And little did I know, by the conclusion of my internship, I would end up with almost more luck than I could handle — thanks to Gina, or Ms. G as we called her around the office.

Gina was a dark-haired, brown-eyed goddess in her late 40s with the face and body of a woman in her late 20s. Besides being fit and fierce, she had a marvelous rack that filled out her blouses and tight sweaters in an alluring way — never crass, but always sexy. As much as she was a professional mentor, she was also my role model for how a woman out in the working world should handle herself. No one ever tells you how to mix being feminine and being taken seriously. Some people still think you can only have one or the other, so witnessing Gina’s finesse on a daily basis really blew my mind. But my body ached for her, too. At that point, I’d only ever been with one other girl in a drunken hookup way at a party. However, a few weeks into my internship, I was crushing hard on Gina.

I frequently found ways to be around her in the office, and I thought she went out of her way to check on me. But our behavior was all aboveboard. For the months that I interned, I maintained a professional boundary with no antics that could risk our reputations. I figured even if Ms. G remained a secret crush, my feelings were a sign from the universe that I definitely needed to further explore my bisexual side.

Before I knew it, my last day had arrived. Prior to my mandatory send-off meeting with HR, Gina stopped by my desk to say, “Congratulations on a successful internship.”

“Thank you.” I smiled and straightened up in my chair. “I’m really going to miss this though. You’ve been wonderful.”

“No need to flatter me,” Gina teased. “I already wrote you a raving reference.” She paused for a moment before adding, “Have any plans for tonight?”

“Nope, I’m wide open.”

“Great. I hope you’ll allow me to take you out for some celebratory drinks. No business, just fun.”

I could barely contain my excitement as I replied, “Of course! I’d love to!”

She suggested a nearby hotel bar, and we agreed on a time to meet up that night. Then she waved and went on her way.

My cheeks were warm and felt flushed. On the way to HR, I stopped in the ladies’ room to splash my face with some cool water and tend to the needs of my aching pussy.

I told myself to relax. Gina could just be acting friendly. I shouldn’t get ahead of myself and read anything into it. But then, how do girls know how to read anything into anything with other girls? My bi-curious brain was on feverish overdrive, for sure. At home, I changed my outfit three times. I settled on a strapless red dress that hugged my petite figure and B-cup boobs. For an added measure of sophistication, I fashioned my strawberry blonde curls into a French twist.

At the bar, Ms. G was her usual flawless self, of course. But this time, there were no business clothes hiding her curves. Instead, she wore a black slip dress, and I tried not to stare. But I couldn’t look away from the outline of her nipples, which poked against the slinky fabric.

“I’m so glad you could make it,” she said, pulling me in for a hug. It was nothing more than a friendly embrace, but it still made my head spin. “I reserved a booth for us,” she told me, before leading me through the main bar to a roped off private seating area. She slid across the cushion and motioned for me to follow. “Here, sit next to me,” she requested.

There was already a bottle of champagne waiting on ice.

“Wow, this is fancy!” I exclaimed, sitting down.

“Hey, you deserve it,” Gina replied. She poured us both some champagne and offered a toast, “To your next steps.”

We clinked glasses, and then I took a sip. I felt the delicious bubbles tickle the roof of my mouth.

Eyeing me lustily, Gina said, “Now that I’m no longer your boss and not in a position of authority over you, there’s something I wanted to discuss.” She paused. “Woman to woman.”

I took another swallow of champagne and uttered, “Oh?”

Gina pushed her hair behind her shoulders, as if getting down to business, and told me, “My husband and I have an understanding. He travels quite a bit for work, and he knows I get lonely.” She sipped her champagne. “But I have no desire to chase other men. Still, I do sometimes enjoy the company of women, the way I did before we were married.”

My clit pulsed, and my head spun. Was this really happening?

Gina leaned closer and touched my arm as she continued, “Obviously, I wanted to be respectful and professional while we worked together. But now that you’re moving on, I was wondering how you might feel about us having a little fun — and hopefully a whole lot of pleasure?”

I couldn’t speak; I just drew in a deep breath and nodded enthusiastically.

“That’s the response I was hoping for!” she gushed.

“I — I…Oh my God,” I stammered. “I’ve, like, had this girl-crush on you since, like, forever,” I confessed. “I figured I’d made a fool out of myself more than once.”

“No, no. You were cute — and sincere,” she assured me. Under the table, she rested a hand on my thigh. “And I like that very much.” With her other hand, she played with a stray curl of hair hanging by my ear, and then she caressed my cheek. I instantly felt chills and a rush of juices down below.

As horny as hell and suddenly confident, I leaned forward and brushed her lips with mine. To my delight, Gina returned my curious but hesitant kiss with a confident one. Below the table, I felt her hand slide up my thigh and reach my soaked panties. As we kissed more intensely, her finger darted beneath my undies and stroked my clit. Calling the moment electrifying would be an understatement; as she pulled away, I was breathless and my ears were ringing.

I watched in a stupor as she licked my juices off her fingers and washed them down with more champagne.

“I’m leaving a room key on the table,” Gina said as she caressed my face again. Then she stood up and added, “If you’re certain you want more tonight, follow me up in a few minutes.”

Every ounce of me wanted to just go at it right there at the table, but I followed my mentor’s classy and discreet lead. I sat at the table and savored the last sips of my champagne, then I took her key and headed upstairs.

Gina met me at the door to her room with another wet kiss, and she immediately led me to the bed.

“I want to go slow and enjoy every inch of you,” she whispered, gently taking out my hairpins.

With my curls free and unfurled, the rest of my body followed. I hadn’t bothered with a bra. So after my dress was on the floor, all that remained was my drenched thong, which she quickly slipped off.

“You’re exquisite,” Gina said, stroking her hands down to my thighs and planting a kiss squarely in the middle of my stomach. “Have you done this before?”

“No, not really,” I confessed.

“Nothing beats a sexy first-timer,” Gina said in a breathy voice. She stood back and let the top of her dress fall, revealing the breasts I’d fantasized about for months.

“Wow,” I said.

“I must give credit to both nature and a gifted surgeon,” she joked.

Gina reached around and unzipped the remainder of her dress. Her sheer mesh panties did nothing to hide her full bush and pussy lips.

I reached over and cupped her breasts, taking one nipple in my mouth and then the other. They were like soft gummy candy on my tongue.

While I savored Gina’s tits, I slid her panties down and reached around to grope her delicious derriere.

“Mmm, that’s very good,” she said, gently playing with my hair.

Next, Gina guided me down onto the bed, maintaining her sensual touch.

“Such creamy, peachy skin. I love it,” Gina whispered. “Now, let me get to know your beautiful pussy.”

Before I could say anything, Gina dove in tongue-first, and I draped my legs over her shoulders. I bit my lip and squirmed as I felt her tongue probe my pussy and, shortly thereafter, hone in on my throbbing clit. Each lash of her tongue sent me spiraling toward a deeper level of pleasure. I felt two of her fingers slip inside my tight entrance, twisting and moving inside me, while she kept working my clit.

“That’s too good!” I groaned.

“I was going to say the same thing about you,” she teased.

I’d never before experienced ecstasy of that kind with a partner. I felt so sexy and so alive with Gina as I experienced my first-ever head-to-toe orgasm. As I lay there panting, she eventually came up for air and kissed me again.

“Don’t worry, there’s more where that came from,” she assured me before reaching for a pink case on the nightstand. From it, she pulled out a strap-on harness — with a dildo attached. 

My cunt was still so soaking wet that we didn’t even need any extra lube! Using the fingers of one hand, I parted my pussy lips and said, “Then don’t make me wait.”

A woman of her word, Gina fucked me over and over until the sun came up.

When her husband leaves town next month, we’re going to have a whole weekend of fun.

" />

Cougar Love

  • 2

Storyline

Around this time last year, I lucked into a coveted internship at a top advertising firm in the city. Sure, I had the grades and the resume. But in posh firms like that, it’s all about connections, so it definitely helped that my former sorority sister Jenna had a new stepmom, Gina, who was in charge of the marketing department. Jenna and I weren’t super close as friends; she graduated the year I pledged. But what can I say? The socializing and craziness of Greek life does have a way of translating to professional networking, too. And little did I know, by the conclusion of my internship, I would end up with almost more luck than I could handle — thanks to Gina, or Ms. G as we called her around the office.

Gina was a dark-haired, brown-eyed goddess in her late 40s with the face and body of a woman in her late 20s. Besides being fit and fierce, she had a marvelous rack that filled out her blouses and tight sweaters in an alluring way — never crass, but always sexy. As much as she was a professional mentor, she was also my role model for how a woman out in the working world should handle herself. No one ever tells you how to mix being feminine and being taken seriously. Some people still think you can only have one or the other, so witnessing Gina’s finesse on a daily basis really blew my mind. But my body ached for her, too. At that point, I’d only ever been with one other girl in a drunken hookup way at a party. However, a few weeks into my internship, I was crushing hard on Gina.

I frequently found ways to be around her in the office, and I thought she went out of her way to check on me. But our behavior was all aboveboard. For the months that I interned, I maintained a professional boundary with no antics that could risk our reputations. I figured even if Ms. G remained a secret crush, my feelings were a sign from the universe that I definitely needed to further explore my bisexual side.

Before I knew it, my last day had arrived. Prior to my mandatory send-off meeting with HR, Gina stopped by my desk to say, “Congratulations on a successful internship.”

“Thank you.” I smiled and straightened up in my chair. “I’m really going to miss this though. You’ve been wonderful.”

“No need to flatter me,” Gina teased. “I already wrote you a raving reference.” She paused for a moment before adding, “Have any plans for tonight?”

“Nope, I’m wide open.”

“Great. I hope you’ll allow me to take you out for some celebratory drinks. No business, just fun.”

I could barely contain my excitement as I replied, “Of course! I’d love to!”

She suggested a nearby hotel bar, and we agreed on a time to meet up that night. Then she waved and went on her way.

My cheeks were warm and felt flushed. On the way to HR, I stopped in the ladies’ room to splash my face with some cool water and tend to the needs of my aching pussy.

I told myself to relax. Gina could just be acting friendly. I shouldn’t get ahead of myself and read anything into it. But then, how do girls know how to read anything into anything with other girls? My bi-curious brain was on feverish overdrive, for sure. At home, I changed my outfit three times. I settled on a strapless red dress that hugged my petite figure and B-cup boobs. For an added measure of sophistication, I fashioned my strawberry blonde curls into a French twist.

At the bar, Ms. G was her usual flawless self, of course. But this time, there were no business clothes hiding her curves. Instead, she wore a black slip dress, and I tried not to stare. But I couldn’t look away from the outline of her nipples, which poked against the slinky fabric.

“I’m so glad you could make it,” she said, pulling me in for a hug. It was nothing more than a friendly embrace, but it still made my head spin. “I reserved a booth for us,” she told me, before leading me through the main bar to a roped off private seating area. She slid across the cushion and motioned for me to follow. “Here, sit next to me,” she requested.

There was already a bottle of champagne waiting on ice.

“Wow, this is fancy!” I exclaimed, sitting down.

“Hey, you deserve it,” Gina replied. She poured us both some champagne and offered a toast, “To your next steps.”

We clinked glasses, and then I took a sip. I felt the delicious bubbles tickle the roof of my mouth.

Eyeing me lustily, Gina said, “Now that I’m no longer your boss and not in a position of authority over you, there’s something I wanted to discuss.” She paused. “Woman to woman.”

I took another swallow of champagne and uttered, “Oh?”

Gina pushed her hair behind her shoulders, as if getting down to business, and told me, “My husband and I have an understanding. He travels quite a bit for work, and he knows I get lonely.” She sipped her champagne. “But I have no desire to chase other men. Still, I do sometimes enjoy the company of women, the way I did before we were married.”

My clit pulsed, and my head spun. Was this really happening?

Gina leaned closer and touched my arm as she continued, “Obviously, I wanted to be respectful and professional while we worked together. But now that you’re moving on, I was wondering how you might feel about us having a little fun — and hopefully a whole lot of pleasure?”

I couldn’t speak; I just drew in a deep breath and nodded enthusiastically.

“That’s the response I was hoping for!” she gushed.

“I — I…Oh my God,” I stammered. “I’ve, like, had this girl-crush on you since, like, forever,” I confessed. “I figured I’d made a fool out of myself more than once.”

“No, no. You were cute — and sincere,” she assured me. Under the table, she rested a hand on my thigh. “And I like that very much.” With her other hand, she played with a stray curl of hair hanging by my ear, and then she caressed my cheek. I instantly felt chills and a rush of juices down below.

As horny as hell and suddenly confident, I leaned forward and brushed her lips with mine. To my delight, Gina returned my curious but hesitant kiss with a confident one. Below the table, I felt her hand slide up my thigh and reach my soaked panties. As we kissed more intensely, her finger darted beneath my undies and stroked my clit. Calling the moment electrifying would be an understatement; as she pulled away, I was breathless and my ears were ringing.

I watched in a stupor as she licked my juices off her fingers and washed them down with more champagne.

“I’m leaving a room key on the table,” Gina said as she caressed my face again. Then she stood up and added, “If you’re certain you want more tonight, follow me up in a few minutes.”

Every ounce of me wanted to just go at it right there at the table, but I followed my mentor’s classy and discreet lead. I sat at the table and savored the last sips of my champagne, then I took her key and headed upstairs.

Gina met me at the door to her room with another wet kiss, and she immediately led me to the bed.

“I want to go slow and enjoy every inch of you,” she whispered, gently taking out my hairpins.

With my curls free and unfurled, the rest of my body followed. I hadn’t bothered with a bra. So after my dress was on the floor, all that remained was my drenched thong, which she quickly slipped off.

“You’re exquisite,” Gina said, stroking her hands down to my thighs and planting a kiss squarely in the middle of my stomach. “Have you done this before?”

“No, not really,” I confessed.

“Nothing beats a sexy first-timer,” Gina said in a breathy voice. She stood back and let the top of her dress fall, revealing the breasts I’d fantasized about for months.

“Wow,” I said.

“I must give credit to both nature and a gifted surgeon,” she joked.

Gina reached around and unzipped the remainder of her dress. Her sheer mesh panties did nothing to hide her full bush and pussy lips.

I reached over and cupped her breasts, taking one nipple in my mouth and then the other. They were like soft gummy candy on my tongue.

While I savored Gina’s tits, I slid her panties down and reached around to grope her delicious derriere.

“Mmm, that’s very good,” she said, gently playing with my hair.

Next, Gina guided me down onto the bed, maintaining her sensual touch.

“Such creamy, peachy skin. I love it,” Gina whispered. “Now, let me get to know your beautiful pussy.”

Before I could say anything, Gina dove in tongue-first, and I draped my legs over her shoulders. I bit my lip and squirmed as I felt her tongue probe my pussy and, shortly thereafter, hone in on my throbbing clit. Each lash of her tongue sent me spiraling toward a deeper level of pleasure. I felt two of her fingers slip inside my tight entrance, twisting and moving inside me, while she kept working my clit.

“That’s too good!” I groaned.

“I was going to say the same thing about you,” she teased.

I’d never before experienced ecstasy of that kind with a partner. I felt so sexy and so alive with Gina as I experienced my first-ever head-to-toe orgasm. As I lay there panting, she eventually came up for air and kissed me again.

“Don’t worry, there’s more where that came from,” she assured me before reaching for a pink case on the nightstand. From it, she pulled out a strap-on harness — with a dildo attached. 

My cunt was still so soaking wet that we didn’t even need any extra lube! Using the fingers of one hand, I parted my pussy lips and said, “Then don’t make me wait.”

A woman of her word, Gina fucked me over and over until the sun came up.

When her husband leaves town next month, we’re going to have a whole weekend of fun.

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