Cassie Ch 02 Cassies New Friend

Since my last birthday, the sex between Cassie and I has been amazing. We talked about that night each time we made love, wondering how much further we could've taken it, dreaming up all sorts of scenarios and plot twists. Cassie's imagination seemed focused on the kiss that woman gave her, wondering what else they might have done together if we'd only had more time.

It was several months later before we had another night to explore our naughtier side again. We decided to head back into the city where we'd be less likely to run into someone we know.

This time out Cassie wore a little black dress, coupled with sheer black back-seamed stockings and red stilettos. My once conservative and reserved wife was now eagerly dressing to tease me (and please me). The keyhole dress highlighted her magnificent cleavage, and left her shoulders bare, which was quite sexy. The bottom of her dress hugged her ass like it was painted on.

Not having any specific plans, I suggested we stop into a bar for some liquid courage, and mentioned to Cassie that maybe she could find another woman to fool around with. I said this in jest, but her eyes lit up as she smiled her approval and I realized that she had taken that notion much more seriously than I had.

We walked into the first bar we came to and settled in at a high-top table against the wall. Our waitress promptly came over and introduced herself as Olivia, and proceeded to take our order. Her jet black hair was up in a bun and she had big rimmed glasses like a stereotypical librarian might wear. She was definitely younger than us, probably in her mid thirties with a studded nose piercing. She wasn't petite but she wasn't heavy either, she was just really curvy... in all the right places. It almost looked like she had a corset on as her waist seemed so tiny compared to the rest of her "proportions".

But what stood out most were the enormous tits that her T-shirt was barely containing. Cassie couldn't help but comment on their size the moment Olivia left our table, wondering aloud what it would be like to "bury your face between those babies". Cassie was clearly enamored with this woman's chest and I was happy to encourage her.

Olivia quickly returned with our drinks when I saw her glance down below our table and tell Cassie how much she just loved her stockings, causing Cassie's face to turn crimson with embarrassment. I could've swore she gave Cassie a once over as she chuckled at her innocent embarrassment, before leaving us to ourselves.

We sat there enjoying our drinks and watching the rest of the patrons, looking for the mystery female that Cassie might approach. I kept brushing my hand on her thigh under the table, gently feeling her soft silky stockings, while slowly trying to push up her dress as she scanned the room.

To be honest, it wasn't the kind of bar we had hoped for, there were TVs on the walls, and most of the clientele appeared to be business guys bitching about work or the ball game. There was music playing, but no one was dancing. We took our time scanning the room as people came and went, but no one seemed to grab Cassie's attention. I was grazing Cassie's tits and caressing her thighs every chance I got while she continued searching for her elusive prize.

I think Olivia may have noticed my wife watching all the women, because she approached our table with a raised eyebrow as she inquired if we needed refills. Maybe it was my imagination, but each time Olivia passed our table I swear I'd catch her leering at Cassie's crossed legs in her stockings and heels.

I told Cassie I thought our waitress was checking her out and she should try flirting with her, but she just laughed it off and said "What am I supposed to say, my husband wants to watch me fool around with another girl?" We both chuckled at how ridiculous it sounded and agreed it probably wasn't a great pickup line.

Olivia returned once again as we were finishing our 2nd round and mentioned that her shift was ending. She politely asked us if we wanted to cash out now, or leave our tab open for the next server? I told her we'd be happy to cash out now, and as she went to fetch our bill Cassie went to the ladies room to freshen up.

I settled the bill with Olivia, and deciding to take a gamble said "I hope I'm not being too forward here, but my wife and I are going to check out the bar across the street to see if it isn't better suited to a good time. If you're interested in joining us for a drink I know she'd welcome the company". Before giving our waitress a chance to reply or reject my offer, I got up and met Cassie as she came out of the bathroom. That relatively innocent offer seemed like such a small thing, yet my heart was racing, had I really just invited another woman to fool around with my wife?

We walked out of that bar still excited about the possibilities ahead, but a little discouraged with what we'd found so far. We stood on the corner deciding what to do as I held Cassie tight and kissed her, while palming her round ass cheeks over her dress. I suggested we visit another bar just across the street that had much better reviews. She didn't seem interested at first, but perhaps this fantasy of another woman was still bouncing around in the back of her mind, because she eventually replied "I guess another drink wouldn't be a terrible idea" with a mischievous wink.

We crossed the street, walked into the bar, and immediately noticed how packed it was. The place was full, there were no TVs or sports memorabilia, and people were dancing to the lively music. There was no place to sit initially, so we walked up to the bar to try and order some drinks. It was so tightly packed around the bar that you could barely move, Cassie spotted an opening at the end and we made our move.

The gentleman sitting on the bar stool to our right had his back to us, and Cassie was in front of me trying to get the bartender's attention. Realizing no one could see me, I lifted my hand under Cassie's dress to cop a quick feel when I discovered she was once again without panties. She looked over her shoulder and blushed at my realization. When I touched her tender opening, she was soaking wet. I effortlessly slid my middle finger all the way inside her juicy pussy on the first go.

I don't know if it was my constant fondling, or her thinking about hooking up with other woman, either way my finger slipped into her tight cunt like a hot knife through butter. I watched her in the mirror over the bar, and I saw her mouth drop open in disbelief as I penetrated her, but no sound came out. I stood there as if I was just waiting my turn to order, but secretly I was thrusting my finger in and out of my wife's drenched pussy while we were surrounded by strangers.

Suddenly, the bartender seemed to appear out of nowhere and asked Cassie what she was having, I watched her struggle to form a reply. After a prolonged pause she eventually said "mmmmmmmm, ugh, how's about a margarita and a Blue Moon?"

While we stood watching the bartender get our drinks I kept drilling her pussy mercilessly with my middle finger, you could practically hear how wet she was over the loud music in the bar. I leaned closer and kissed her neck softly as I whispered in her ear "I love my slutty little wife". I felt her tremble as I said that, I don't know how close she was to cumming, but she was clearly enjoying herself.

Finally our bartender returned with our drinks, and I reluctantly withdrew my finger from her hungry twat. I wrapped my arm around her waist as we walked around looking for a place to sit. She held my arm tightly as her legs still seemed unsteady from the treatment I'd been giving her at the bar.

Before long a small table for two opened up and we jumped for it. Cassie propped herself up on the bar stool and I sat in the other right next to her. I had my arm around her, squeezing her close and whispering naughty things in her ear as she enjoyed her drink and scanned her new prospective targets. I teased that she should cross and uncross her legs to give a show to anyone who might be looking, but she just blushed and refused.

We sat there enjoying our drinks while the whole time she was eye-fucking all these unknown women. I think it was probably just the pressure of the moment, because there were plenty of attractive women here, and several appeared to be by themselves, but for whatever reason she didn't want to approach any of them. I kept telling her what a naughty girl she was, and how hot it would be to watch her eat another woman's pussy. Her breathing increased and her eyes became glazed with lust, but the reality was a stark contrast to her fantasy. Fair enough, perhaps she was just playing along to tease me, and never really intended to do anything about it.

Just as Cassie was finishing her drink I noticed Olivia walk into the bar, my heart immediately started beating faster. Oh my god, what had I done asking her to join us? If Cassie was just teasing me about wanting another woman this could get awkward quickly.

Olivia looked quite different than she had before. She had changed into a red Lycra mini dress that practically looked painted onto her voluptuous body. I wasn't sure if she saw us as she headed to the bar to get herself a drink, but as she turned her back I couldn't help but notice that she too had changed into high heels and sexy stockings! Perhaps she also had a stocking fetish, I mean she had been starting & commenting on Cassie's legs earlier. Just as Cassie said we should probably call it a night, I motioned towards the bar and said "look who just walked in."

Cassie made an audible gasp when she noticed Olivia standing at the bar, and asked "I wonder what she's doing here?" Figuring I'd be found out either way, I confessed that I may have mentioned to Olivia that we were coming here and that she was welcome to join us if interested. Cassie's eyes lit up as she leaned closer to me and gave me a big kiss, then whispered into my ear "Do you want to see your wife acting naughty with another woman?" as I choked on my beer.

Olivia got her drink, quickly spotted us and approached our table saying "what a coincidence" while laughing. We invited her to join us and formally introduced ourselves to her. I got up to let Olivia have my stool, and took in the sight of her gorgeous legs in those sexy ass stockings.

This time it was Cassie who commented how much she liked Olivia's stockings. They both blushed this time, while Olivia confessed that she has always found stockings to be a huge turn on. While I did find Olivia attractive, this was Cassie's fantasy, so I tried to stay in the periphery as much as possible. Besides, standing beside Cassie gave me amazing views of both their tits and legs as they talked, which I was thoroughly enjoying. Olivia caught me peeking multiple times, but just smiled knowingly.

It felt like they clicked with one another immediately, quickly realizing they shared a lot in common. Not the least of which, that they were both self-confessed book worms with a strong preference for smut. They talked about all different books they'd read, best and worst, and in no time seemed to be finishing each other's thoughts. I stood, enjoying my beer and rubbing Cassie's back, just listening in as their conversation included the occasional sexual innuendo.

Olivia got up to excuse herself to the restroom, and with a sly grin asked Cassie to accompany her. Nothing unusual, I mean girls always go to the bathroom in pairs, right? While they were gone I started day-dreaming about what might be happening behind closed doors.

I didn't have to wonder for very long, because they came back out a just few moments later. As they approached the table I noticed Cassie had unbuttoned the top two buttons of her dress, and was showing significantly more cleavage than before. As she got closer I almost spit out my beer when I saw that her nipples were fully erect and poking through her dress, clearly indicating she was no longer wearing a bra. They both just looked at me as I stood there with my mouth open, finally Cassie said "it was Olivia's idea, I mean we're out to have a good time, right?" They both giggled as I was now the one struggling to put together words.

The drinks and conversation flowed easily until a song they both loved came on, so they both headed out to the dance floor. The alcohol was clearly having its effect. They weren't dirty dancing, but when they were facing each other they were close enough that they kept "accidentally" bumping their tits into one another. And when they'd turn away from each other it was their asses accidentally grinding on one another. I was in heaven watching this. They were whispering to each other on the dance floor and occasionally looking back at me. I don't know what they were saying, but it certainly looked like they were plotting something.

After a couple of songs they finally had had their fill, and returned to the table with the hardest sets of nipples I'd ever seen, I was dying to reach out and pinch each one. But I noticed that an awkward silence had suddenly come over the both of them. While they were talking non stop before they got up to dance, now they both seemed unable to speak, they both just sat there staring back at me with sheepish grins. Finally I broke the silence and asked "what's up with you two all of a sudden?"

Cassie complained (an obvious excuse) that the bar was too loud to carry on a conversation anymore, Then Olivia quickly replied that we could head over to her place to continue their conversation if we were interested? I pondered briefly what had just been offered, then glanced over at Cassie who was staring at me with pleading eyes, just begging me to agree. I'd have to be a fool to turn this down, so we collected our things and headed for the door.

Olivia said her apartment was just around the block so we went on foot. I followed behind the two of them watching their gorgeous asses swaying back and forth as these unbelievably sexy women strutted their stuff down the street. I swear they were exaggerating the sway of their hips just for my benefit, the back and forth sway of those cheeks was almost hypnotic.

They walked arm in arm the whole way there, it was clear they were both pretty excited about where this might be headed. When we got to her building Olivia began digging through her purse for her keys. While she was doing that Cassie leaned in and gave me a deep passionate kiss right in front of Olivia, then silently mouthed "thank you" to me.

When we got in to her apartment Olivia told us to grab a seat on the couch while she went to fix some drinks. When she returned the two of them continued talking about random subjects, eventually Cassie asked Olivia if she was in a relationship. Olivia told us she had just gotten out of a long term relationship with a guy, but was thoroughly enjoying being single at the moment. Having been quiet for some time, I chimed in and told Olivia "it can't be very hard meeting men when you dress like that!"

She blushed at my comment and said "what, this old thing?" I confessed my attraction to women in stockings and heels, and she said she suspected as much given my wife's attire. She said "I've always found stockings to be so sensual and sexual, its a shame more women don't wear them these days."

Then she walked over and sat down next to Cassie on the couch, lightly touching her knee. Olivia slowly stroked Cassie's thigh and purred "they just feel sooooooo good against your skin, don't you think Cassie?" Cassie seemed to panic as her breath quickened. Olivia sensed her apprehension and quickly shifted gears, asking Cassie about another book to prevent scaring her off. But as the conversation continued it once again progressed into tales of sordid events each had read about, and then to those that they had personally experienced.

Finally Olivia chuckled aloud and said "look, I've just gotta ask, are you two swingers or something?" Both our faces turned beet red from embarrassment. I clarified for Olivia that we were most certainly not swingers. I told her we'd been happily married & monogamous for over 20 years. Cassie seemed content with that clarification, but then I decided to push the envelope a little and told Olivia that Cassie had recently voiced her curiosity about being with a woman.

Olivia cocked an eyebrow, and said "curiosity, huh?" Then she leaned closer to Cassie stopping just a couple inches from her face and slowly said in a syrupy voice "so, what exactly are you curious about?" Cassie's face flushed and she seemed to freeze.

Fearing Cassie would regret missing the opportunity, I spoke up and said "I suspect she wonders what it would feel like to kiss another woman". Olivia looked over at me with a hunger in her eyes, she looked like a predator stalking her prey.

Olivia slowly leaned in and planted a soft tender kiss on Cassie's lips. "Like that?" she asked innocently. Cassie was practically vibrating, she looked like she was equal parts terrified and turned on, she didn't know whether she should run for the door or attack this woman in front of her.

So I took the lead once again and said "she still looks undecided to me, perhaps another will help her make up her mind?" And with that, Olivia leaned in a second time for a kiss. This time Cassie summoned her courage, brought her hands up to Olivia's face as this kiss lasted for mere seconds before quickly evolving into a pretty heavy make out session.

I sat back in awe as I watched my beautiful wife finally go for it. The two of them looked so gorgeous, embracing as they made out on the couch in front of me. They continued making out non-stop, with the two of them slowly caressing each others arms while rubbing their nylon-encased legs against one other. As Cassie rubbed her legs between Olivia's she paused briefly and whispered huskily "these stockings do feel pretty amazing."

As they continued kissing, Cassie brought her hand up until it was resting right beside one of Olivia's enormous tits. Olivia tilted her head to the side and said "I bet you're curious what these feel like as well, don't you?" as she nodded her permission to Cassie. Cassie began gently fondling Olivia's big tits over her skin tight dress, caressing and kneading each breast as they continued kissing. Now Olivia was the one breathing faster, as she too began groping at Cassie's tits.

Just as things were starting to really heat up between them, Olivia sat back and said "I think I could use another drink, anyone else want one?" Cassie happily accepted the offer, and as Olivia walked towards the kitchen she looked over her shoulder and said "John, why don't you keep your lovely wife company while I fix us a drink."

Now Cassie and I were side by side making out like teenagers on the couch, and I began feeling her bra-less tits through her dress, while she massaged my cock over my pants. Somehow simple kissing and petting felt so much more erotic with another person in the room, it was so exhilarating.

Olivia returned with their drinks and sat down on the other side of Cassie while we continued going at it. Olivia whispered into Cassie's ear how hot we looked together, and said "don't stop, I want to watch" as she began running her hands up and down the back of Cassie's legs.

I could feel Cassie whimpering with lust as this woman caressed her legs while she continued making out with me. Then Cassie started moaning softly as her inhibitions began to break down, and her legs slowly began separating for Olivia's adventurous hands. Olivia noticed, and continued slowly running her hands up and down Cassie's legs, reaching slightly higher with each pass. When her hand finally reached the skin above Cassie's stockings she whispered in Cassie's ear "you look so fucking hot, I'm just dying to touch you."