Double Pleasure

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A woman explores her sexuality.
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Ollegio
Ollegio
52 Followers

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Four Years Earlier

On her second visit to the new gym, Jackie met Cathy. Both were late 20s, single and unattached, and they hit it off immediately. They began coordinating schedules so they could work out together, chatting about nearly everything while they did so.

"Wow! She's gorgeous!" Cathy said, tipping her head in the direction of a woman working out nearby on one of the weight machines.

"Yes she is," Jackie replied. "She's wearing a wedding ring so apparently spoken for."

"Damn shame," Cathy stated. "I'd love a shot at that!"

"Umm, Cathy, are you gay?"

Cathy laughed and said, "I thought you'd have figured that out by now! Actually, I'm bi but I favor women. Just not adverse to the occasional cock."

"Sheesh! I had no idea! Guess I don't have very good gaydar!" Jackie blurted out.

"Does it bother you?"

"No, it's fine. I've just never wanted to be with a woman so it didn't occur to me that you might feel differently," Jackie said.

"Well, maybe I can change your mind someday," Cathy replied with a sexy smirk.

A couple of weeks later the two decided to go clubbing on Friday night. After meeting at a mainstream club favored by folks their age, they had a few drinks and each accepted a couple of invitations to dance, though never more than once with any one guy.

"I'm getting tired of being hit on by every guy here," Cathy said. "This has become nothing but a meat market! C'mon, we're out of here!"

She opened the ride share app on her phone and booked a car. The app said it would be at the club in eight minutes. They both stopped in the Ladies' Room to freshen up and exited the club just as the ride share arrived.

Fifteen minutes later they arrived at the club Cathy had chosen. After paying the cover charge they entered to a scene that seemed, on the surface, much like the one they had just left. It took Jackie a couple of minutes to realize she didn't see any men in the entire place, with the exception of the doorman/bouncer and a couple of bartenders.

"Cathy, is this a lesbian bar!" she exclaimed.

"Yup! At least here if we get hit on it will be by women! But don't worry - just act like we're a couple and it should be fine."

They found a vacant two top table and claimed it. A waitress appeared and greeted Cathy, "Good to see you again, hon. The usual?"

"Yes, and make it two," Cathy replied.

"So who's your friend?" the waitress asked.

"Oh, Belle, this is Jackie. We met at the gym a few weeks back. Jackie, this is Belle, best waitress in the city!"

"Nice to meet you, Belle."

"Likewise, Jackie." Turning back to Cathy, she said "I'm getting strong hetero vibes here, Cathy," with a smile.

Cathy laughed and said, "Yup, she's straight. So far at least!"

After ordering a second round twenty minutes later, Cathy grabbed Jackie's hand and stood up. "C'mon, hon, let's dance! I'll even grab your ass so you can close your eyes and pretend I'm a guy!"

Jackie laughed, partly because the song playing was a fast one with no real opportunity for grab ass. But when that song ended the DJ spun Boyfriend by Dove Cameron. Cathy immediately wrapped her arms around Jackie, pulling her close.

Surprised at first, Jackie almost pulled away. But then she noticed every couple on the dance floor consisted of two women. She relaxed, determined to enjoy herself and new experiences. It did feel strange to have her 32B breasts pressed tight to Cathy's 34Ds, but it was a good strange. So much different than a guy, she thought to herself.

True to her word, Cathy let her hand slide down the small of Jackie's back and not grab but caress her round ass cheek. Jackie initially tensed up but then forced herself to relax. A couple of the guys at the last place did the same thing but Cathy knows how to be much more tender, Jackie thought.

The next song came on - Can't Sleep Love by the Pentatonix. Half the dancers switched to a fast dance style but the remainder, including Cathy, held onto their partner and just moved a bit quicker.

Next up was Norah Jones' Turn Me On. Slowing their pace to match the tempo of the song, Cathy held Jackie close. Jackie was now completely relaxed, letting her body mold itself to Cathy's

As the song ended, Cathy continued holding Jackie but leaned her head and shoulders back so she could gaze into Jackie's face. She saw a look of contentment and curiosity there. Silently praying that she wasn't making a mistake, Cathy leaned in and pressed her lips to Jackie's.

At first Jackie didn't know how she should react, so she did nothing, letting Cathy keep them together. For her part, Cathy took this as at least partial consent. She slipped her tongue out and used the tip to trace first the upper than the lower lips of her dance mate. After circling three times she ran her tip across the seam between Jackie's lips. As she did, Jackie opened the up, allowing Cathy to enter her mouth.

The dam burst and their two tongues began playfully wrestling with each other. The kiss became stronger and deeper, and both began breathing much more deeply.

When they broke apart, Jackie looked at Cathy and said, "Your place or mine?" Cathy laughed, and Jackie added, "Too corny? Major cliche?"

"Nope, perfect question. Mine's closer, okay?"

Jackie nodded and they reluctantly broke apart and flagged down Belle. Once their tab had been settled and another ride share booked, they walked out to wait, hand in hand.

Once inside Cathy's apartment, she fixed them each another drink and they headed to the bedroom. "Nervous?" she asked.

"Yes. You know this is my first time. I'm worried I won't know what to do to please you," Jackie replied.

"The nice thing about being with another woman is she most likely enjoys the same things you like done to you. So just follow your instincts. Start by undressing me - I'll go first so you don't get embarrassed."

Jackie removed Cathy's clothing piece by piece. When she was clad only in a lacy, skimpy pair of panties, Jackie lowered herself to her knees. With her nose perfectly aligned with Cathy's pussy, she could smell her arousal. Jackie put her right hand on Cathy's right thigh and slowly slid it up. When the side of her finger touched the cloth of the panties she confirmed that Cathy was extremely wet.

Jackie put the first two fingers of each hand inside the waistband of the panties, one hand on each hip. Cathy spread her legs just slightly and Jackie pulled the panties down her legs until they fell to her ankles of their own accord. Cathy lifted first one then the other foot, and flicked the panties across the room.

Cathy stepped back and asked, "Are you okay? Or do you want to stop?"

"No, don't stop. Please undress me," Jackie replied, wondering if she really meant it.

Cathy undressed Jackie in much the same fashion. When she was on her knees to remove Jackie's panties, she too could inhale the aroma of her soon to be lover's pussy. When she had the panties around Jackie's ankles, instead of standing up, Cathy leaned in and gently kissed Jackie's labia. Meeting no resistance or shock, she ran the tip of her tongue up her slit until she reached the clit. Cathy was thrilled to find it erect and protruding from the clitoral hood, signaling Jackie's sexual excitement.

Cathy stood up and gently directed Jackie to the bed, where she lay down on her back, legs just slightly parted. Cathy lay next to her and began kissing her passionately. She reached out with one hand, caressed the side of Jackie's face and moved down over her neck until she found her breast. She first cupped the breast, squeezing softly until she heard and felt Jackie moan into her mouth. At this, she redirected her attention to the nipple, taking it between thumb and finger pads.

This elicited deeper, louder moans, encouraging Cathy on. Breaking off the kiss, Cathy slid down until she could take the other nipple in her lips. Nibbling gently she flicked her tongue rapidly back and forth across the tip of the nipple. "Oh god," Jackie cried, "that is so great!"

Cathy reluctantly removed her hand from the other breast and moved it down, across Jackie's stomach. She paused to play with the neatly trimmed pubic hair then continued her southernly voyage. Jackie had shaved her labia completely and with her arousal wetness Cathy easily ran her fingers over each.

Fingers naturally lubricated, she reached down between Jackie's thighs and tickled her perineum. Jackie moaned again as Cathy's finger pulled up her slit to the opening. Cathy inserted her middle finger into her, being rewarded by more, and more strident, moaning. She slipped a second finger alongside the first and found Jackie's clit with her thumb.

With two fingers pumping in and out of her pussy, another rubbing her clit, and Cathy's lips still working on her nipple, in only a few minutes Jackie screamed, "I'm going to cum!" She lifted her hips off the mattress, seeking to impale herself on Cathy's fingers as she came violently. Cathy continued everything, maintaining Jackie's orgasm until she could no longer stand it. Jackie reached down and grabbed Cathy's hand, forcibly yanking it off her clit and out of her pussy before dropping her hips back down in exhaustion.

After several minutes of deep breathing, Jackie finally managed to slow her heart rate to something approximating normal. Sitting up against the headboard, she reached over for her drink and forced herself to sip it slowly. Cathy moved up next to her and grabbed her own drink.

"Was that okay, hon?" she asked.

"Oh my god! I don't think I've ever had an orgasm as intense as that! If I had known, I'd have been gay years ago!"

Cathy laughed and responded, "I suspect part of that had to do with the novelty of the situation. Let's see how we do tomorrow, and Sunday."

Putting their drinks down they embraced and kissed yet again. With Cathy on her back, Jackie looked down at her and said "I hope it's okay, but I need to start with the main event." At that she moved down the bed and got between Cathy's legs. She placed her nose just below her clit and inhaled deeply. She tentatively pushed her tongue out and tasted another woman's juices for the first time. While it had been a while since she'd licked her own fingers after masturbating, she thought Cathy tasted very similar to herself.

Pushing her arms beneath Cathy's thighs she lifted them, bending Cathy's knees and exposing her womanhood fully. She mimicked Cathy's early finger exploration substituting her tongue. She first licked the perineum then slowly traced her slit upward. Pausing at the opening she thrust her tongue in as deeply as she could. She quickly suspected that, while this might feel pleasant, she couldn't get far enough in nor was her tongue substantial enough to likely cause much true pleasure. But she was enjoying exploring, so she pushed her tongue in and out until the muscles tired.

Wanting badly to give Cathy as much pleasure as she had received, she moved up until she could take her clit between her lips. She nibbled very gently, fearful of hurting her partner. "Harder, please," Cathy called out. Biting a little harder she heard Cathy start to moan. She added her tongue flicking across the clit and the moans increased.

Without stopping her oral activity, Jackie shifted position just enough to allow her hand access to Cathy's pussy. Following Cathy's earlier lead, she inserted two fingers and pumped them in and out as she continued working her clit with her mouth. Cathy's hands grabbed the sides of her head and pulled her even tighter to her pussy. Her breathing became shallow and rapid as her moaning went deeper and louder.

Two minutes later Cathy came with a scream. Her grip on Jackie's head was so tight Jackie feared she wouldn't be able to breathe much longer. She continued working on Cathy's clit until it reached the point of painful ecstasy and Cathy pushed her away.

"Damn girl, for a rookie you sure know how to hit a home run!" she exclaimed.

They reclaimed their drinks and sat up once again. "So how do you feel, now?" Cathy asked.

"I liked it! When I was going down on you and finger fucking you, I swear I could feel everything I did to you in my pussy!"

"I get that. I often have the same sensation. It doesn't always happen but once in a while I can actually cum myself by making a woman cum."

"Mmmm, that would be incredible!"

"Let's get some sleep. I want more of you tomorrow!" Cathy declared as she turned off the lamp and rolled over to spoon Jackie from behind, reaching over to cup her breast.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Cathy woke first, still spooning and holding Jackie's breast. She slowly fingered her nipple causing it to stiffen. Jackie moaned softly and opened her eyes to see Cathy's face next to her own. Twisting her neck until their lips met, Jackie kissed Cathy deeply.

Moving back, Cathy pressed on Jackie's shoulder and Jackie lay over onto her back. Cathy had planned a slow, progressive seduction but was suddenly overwhelmed by her desire to taste her new lover once again. She positioned herself between Jackie's legs and hungrily licked her slit, bringing forth a deep moan.

Cathy pushed her tongue into the wet, eager pussy before her and stroked it in and out. But Jackie was just as eager to participate more actively. She rolled onto her side and slid down until Cathy's pussy was before her face. Taking hold of her ass cheek, she pulled Cathy onto her side, bringing them into the 69 position.

For the next ten minutes or so Jackie precisely mirrored every move Cathy made. When Cathy licked her slit, Jackie did the same. As Cathy's tongue slid into her pussy, she returned the favor. When Cathy took her clit between her lips and flicked the tip of her tongue over it, Jackie moaned deeply and then treated Cathy's clit to the same. It took only a minute or two for both to cum. As their orgasms coursed through their bodies both instinctively squeezed their legs together until their clits became too sensitive to continue. Breathing deeply, each relaxed their legs and fell back, exhausted but satisfied, at least for the moment.

Two weeks later

"You realize that you've spent every night here since we got together, right?" Cathy asked Jackie one morning over coffee.

"I know," Jackie smiled back.

"I would love it if you would move in with me," Cathy said.

In lieu of a spoken answer, Jackie leaned over and kissed her lover. "I'll take that as a yes," Cathy whispered. "And I want to show you something else. Give me a few minutes and I'll let you know when to join me."

Cathy rinsed her coffee mug and set it in the sink to wash later. Entering what was now their bedroom, she stripped completely and opened the drawer on her nightstand. A couple of minutes later she called Jackie in.

When Jackie entered the bedroom she stopped instantly. Cathy was standing at the side of the bed, completely naked except for a strap on with a very realistic cock attached. "I thought you might be missing a good fucking, since you were completely hetero only a few weeks ago. You know I'm bi so I enjoy both using this on a partner and having them use it on me. Are you game?"

Instead of answering, Jackie walked over to Cathy. Reaching between her own legs, she rubbed her juices on Cathy's lips. "What do you think?" Jackie told her.

Over the next few hours, Cathy fucked Jackie in every position they could think of - missionary, doggie, cowgirl, reverse cowgirl and more. A devout vibrator user, Jackie had never used a dildo before. The artificial cock never went soft and she finally had to call a stop to things after many more orgasms than she could keep track of. Her pussy was actually sore!

"God, that's intense!," Jackie said. "But what about you?"

Cathy smiled and said, "Here, let me show you a secret." Unstrapping the harness, she slid it off her legs and handed it to Jackie. Jackie immediately saw that it was equipped with not only the dildo that had ravaged her pussy but also a clitoral vibrator on Cathy's side. "It's wireless remote," Cathy explained, pulling the controller out from under the pillow. "When it gets to be too much I shut it off for a while."

"I'm done in," Jackie said. "Let's grab a shower and then some dinner. But tomorrow, I'm wearing that!"

Cathy laughed, and said, "You're on, or should I say in...me!"

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Two years later

"Cathy, we need to talk," Jackie said.

"Uh oh, that sounds ominous."

"You know I adore you, although neither of us has ever used the L word. I think we're great friends and lovers, but not in love."

Cathy was silent as she pondered this. "I agree. I love being with you and having sex but I'm not in love with you either."

"Well, I've met someone who I think might be the one," Jackie said, tentatively, unsure of what Cathy's reaction might be.

"Innie or outie?" Cathy asked.

"He's a guy. Honestly I can't imagine being with any other woman besides you."

"So what now?" Cathy asked.

"Well, he knows about you and I've told him that even if we get married I reserve the right to get together with you occasionally, if you'd want to."

"Wow, marriage! Has he proposed?"

"Not yet but we've talked about it and both of us seem to think that's where this is heading," Jackie confessed. "How does that make you feel?"

Cathy took Jackie in her arms and said "Hon, I'm thrilled for you! I want you to be as happy as you possibly can be, and if this guy can do that I'm all for it! By the way, what's his name and when do I get to meet him?"

"It's Tripp. Why don't the three of us go out to dinner tonight and see how it goes?"

"Okay," Cathy replied, "I really am happy for you. Are you planning to move out right away?"

"I can if you like - Tripp has asked me to move in with him while we look for a house. But I can also stay here, or split my nights between both places."

"Let me think about it for a while. We can talk more before we meet up for dinner."

Later that evening, as they got dressed for dinner, Cathy said, "Hon, I've thought it over and here's what I think. You should move in with Tripp right away. But I'd like it if you would spend one or two nights a week here with me, assuming Tripp would be okay with that. I'm just not ready to go cold turkey from Jackie just yet!"

Dinner went remarkably well. Tripp was charming and relaxed, completely accepting of the fact that his future wife had been in a lesbian relationship for two years and would likely continue it on some basis. When Jackie told him of the living arrangements Cathy had requested he immediately agreed. "I would rather share you than not have you," Tripp told them.

"So, Tripp, do you have dreams of threesomes in your future?" Cathy asked.

Tripp laughed. "Every guy dreams of threesomes and sometimes moresomes. I've had a couple, satisfying my curiosity, so it isn't anything I would ever pressure either of you for. But I will ask where Jackie wants to sleep tonight."

Turning to Cathy, Jackie said, "Hon, Tripp and I have never made love. I didn't feel it would be right while I was with you - it would be cheating. With your approval, I would love to change that tonight."

"Really? You're planning to move in together and buy a house and you haven't fucked yet? Girl, get your ass over to Tripp's place tonight and fix that!" Cathy almost shouted, completely forgetting where they were.

"Thank you, sweetie! You're a darling!" Jackie exclaimed. Looking at Tripp for agreement, she told Cathy, "I'll be back Friday night for the weekend. I need to pack my stuff as well." Tripp nodded, letting them both know that he was comfortable with their arrangement.

"And you better know I expect a complete blow by blow description of tonight and every night until Friday!" Cathy insisted.

Ollegio
Ollegio
52 Followers
12