Part 6: Casandra
Giving my boyfriend a treat, a cute red headed treat
For the next month and a half after the sex party things fell back into our usual routine. I told Blair how much I enjoyed watching the paganistic, otherworldly orgy centered around the woman tied to the specially made table while I was being fucked by, and fucking Ed. The result was him being as turned on as I’ve ever seen him. I dry stroked him while I talked, he was positively groaning with need as I made him wait until my story was done, and I did not rush through the details. When I was finally through using my mouth to tell my tale I wrapped my lips around his cock and within a few strokes I was swallowing his cum, which flowed out of him so hard and fast I could barely keep up. This is my literary prize for a well-told story. Pity I haven’t found away to display his orgasm on a shelf above my writing desk, but I am proud as can be of my achievement none the less.
Then we both got busy with our careers and we settled back into our old schedule of saving Wednesday night and all day Sunday for each other. There was more of this dirty talk, based on things that actually happened and on things that could happen. I saw Ed on the train, and he even got off at my stop one morning and joined me for coffee. Crystal, my favorite barista who often flirts with me, lifted her eyebrows at the handsome man who insisted on paying for my cappuccino. Ed was the perfect gentleman; he made himself available, cheerfully, and didn’t press for more than he was offered.
I was glad to have these weeks to confirm my connection with my boyfriend, not that we needed to, mind you, but it felt good just to focus on each other for a bit and confirm that our relationship was as secure as ever. Then one Wednesday evening I casually said to Blair over pizza and red wine, “You know, I’m one up on you. Would you like a hall pass?”
“Well, that’s an interesting idea. But, honestly I’d rather have another experience with you.” he answered.
“Do you have anything in mind?”
“Well, I was definitely hoping to get some pizza and wine in you and then bend you over the couch.” he replied.
“Well, that’s easily fulfilled. Anything more exotic you might like to try this weekend? Some fantasy fulfillment?”
“Hmmm, you know I do better with multiple choice. Can you present me with a few options?”
“Well, I could dress up for you. I mean, really go all out, Marilyn Monroe, Dominatrix, Marilyn Monroe dominatrix? Princess Leia, sexy librarian, oh I know, how about a sexy nun! You grew up Catholic right?”
He laughed at this, but he did not jump at any of these suggestions. “I did hear about a bar we could go to, just for drinks and possibilities.” I added.
“Drinks and possibilities, ay?” he replied, sounding interested. Ed had told me about a bar in the village where, as he put it, ‘ ‘adventurous types’ went to drink and ‘make friends’.
“Yes, possibilities. It’s not a sex club, just a low key hang out where people who are into having fun, well, hang out.”
“I like possibilities. Will you go to this bar dressed as Princess Leia, and I’ll wear my geekiest Star Wars t-shirt?”
“No, no I will not. But I will dress to impress, and Blair, even if I’m not going to be your space princess in public, this night is all about you.” I fixed him with a very serious look for this last line and was glad to see a grin spread across his face.
I straddled him on the couch, and we made out, pausing now and then to put more wine our mouths. Wine soaked kisses are a delight. I rode his cock right there until I came, and then I led him to the shower where I put him in front of me and let the water beat upon my back while I reached around, and jerked him off until his cum hit the wall of the shower. We soaped each other up, washed one another’s hair, and then crawled between the sheets naked, and fell asleep in each other’s arms feeling happy, and loved, and satiated.
I told Ed that I was taking Blair to the bar he’d recommended. I half wondered if he’d invite himself to come by and I wasn’t sure if I wanted this or not. As much as Blair had enjoyed sharing me, and would likely enjoy it again, this still felt like a very me centered experience, and I was looking for something to focus solidly on him. Ed told me he was sure we’d enjoy ourselves. He had a photoshoot in Miami and would be gone all weekend. I was mostly relieved. This was probably for the best, I thought to myself.
Sunday arrived at last, and I put on the very short satin slip dress I’d bought for the occasion, with thigh high stocking that didn’t quite reach the hem of the dress. My heels were strappy and tall, and with my hair freshly cut and styled, I was feeling sexy, far too sexy for taking the subway, even with a light tailored coat over my outfit. I ordered a car. Blair looked handsome in a blue dress shirt and darker blue slacks, both just tight enough to show off his good build without crossing into that too tight midlife crisis look.
Blair asked the driver to stop a block shy of the bar. “I want to watch you walk in public in this outfit.” he whispered in my ear, and I was glad to see he was embracing this evening being about his pleasure. I walked like I was on a runway, several feet in front of him. I was checked out, smiled at, one man looked up from his phone and nearly fell on his face seeing me walking toward him. I felt incredibly sexy with so many eyes on me, and Blair’s eyes especially, seeing me and seeing other’s react to me. I wondered where this evening would go. It felt so wide open, anything was possible.
The bar was long and narrow, with two rooms. Half of the front room was occupied by the bar that ran the full length of it. All the bartenders were dressed in typical upscale restaurant server attire, but with accessories added, like a leather dog collar on one gentleman, or a tight corset and ruby red lipstick on a woman expertly mixing cocktails next to him, her long shiny black hair pulled back, with a few tendrils hanging down to frame her face, and dramatic bangs spanning between them.
The back room, separated by thick red curtains held open with velvet ropes, had several small tables and at the back of the room a stage that would just barely hold a four piece band.
I was far less conspicuous in the bar than I had been walking there. Everyone was dressed up in sexy outfits, running the full spectrum from looking ready for a ren-faire to full latex fetish body suits that made me think of the Matrix. I saw light petting, and maybe a teasing kiss on a neck, or the inside of a wrist. I got the feeling there was an understanding that this was a place to meet partners to play with but not a playroom.
We ordered drinks, and then found a table. A well curated selection of hair metal and glam rock played quietly enough to allow conversation. This was the perfect environment to enjoy sugary rock pop like Def Leopard and Motley Crue, music I would almost never choose, but that I was quite enjoying here just for the ridiculous excess of it.
Blair and I people watched, whispering to each other when either of us had our interest grabbed. A tall blonde walked in with a muscular man at least a half foot shorter than her. They talked to another couple, a redhead and her handsome hispanic boyfriend with a shaved head, and well trimmed beard. The blonde then left with the redhead’s date, and a few minutes later the the redhead left with the blondes date. We saw two men welcome a third who asked if a seat at their table was available. The flirting was obvious from across the room, and then the three of them left together, walking quickly. We sipped our cocktails and noticed a few people checking us out here and there, and then we met Casandra.
She was shorter than me, and a bit curvier, with long red hair piled up high on her head. She wore a sports bra and sparkly hot pants with nylons and platform sneakers. She had an early 90s Madonna kind of vibe. I’d guess she was in her early thirties. She grabbed a chair from the table next to ours, thanking the couple seated there without asking them if they could spare it, and took a seat with us, right as Barracuda by Heart came blasting over the speakers.
“Hi, I’m Cassandra, not Cas, Cassy, or Sandy, Cassandra. First time here? You have that look. It’s not a bad thing. You’re fucking gorgeous.” she talked fast and sharply. She gave us her name, asked ours, and told us this was her favorite bar. She looked us both over constantly and conspicuously, bit her bottom lip, stroked our hands while she talked to us, and managed to be charming even while coming on incredibly strong. “I like you. I think we should go back to my place, just a couple blocks from here, and have some fun.” she said, after about fifteen minutes of conversation that mostly consisted of her talking. “You’re a couple. I see that. You’ll want to talk about this. I’m gonna go to the bar, drink a shot, and then I’ll come back to hopefully lead you home.” She leaned forward and to us both, in a remarkably loud whisper, said “I promise you, I will make him cum harder than he’s ever cum.” and then as suddenly as she’d arrived, she was gone and we were at our table alone.
“Wow, I um, I like Cassandra.” Blair said.
“Do you?” I asked, with a small smile. “She’s quite sexy.”
“She’s incredibly sexy. The big hair, the aggressiveness, her cute, petite curviness.”
I have never been a girlfriend who requires her man to pretend he doesn’t have eyes for anyone else, but Blair was generally very reserved. A goddess could walk past and if I said ‘Wow’ he would acknowledge with a disinterested sounding “Yes, she was very pretty.” I very much enjoyed seeing him so smitten and turned on.
“Let’s go with her.” I said. “This night is all about you, and you obviously would like to gobble her up. Let’s do it.”
He hesitated. I could see the wheels turning behind his eyes. And then, “Okay. Let’s do it.”
Two minutes later as we were finishing our drinks she came back to the table. “Okay, follow me.” she said, as if it were a given that we’d decide to take her up on her offer. Of course, she wasn’t wrong. We did as we were told.
We grabbed a cab, though it was only a few blocks, and in the back seat, she kissed me softly on the mouth. She moved her lips to my ear and whispered, “I have a little surprise for him. I’m gonna blow his mind.”
“Good. Please make tonight all about him.” I whispered back, and then I kissed her, sliding my tongue between her lips. I abruptly stopped kissing her and sat back with a smile. She took the cue to give Blair a deep passionate kiss. I noticed the driver watching us in the rearview mirror.
At her place she led us into a small lobby and we took the elevator up to a one room studio apartment. “Make yourselves at home.” Cassandra said, having a seat on her bed. I sat on a loveseat next to an end table with a collection of vibrators on it. The room was dimly lit by small lamp on a night stand. Two walls held well done collages made up of vintage postcards.
“Come here, you.” she directed Blair. She lifted his shirt, and kissed and licked his stomach. “Is it your birthday or something, handsome?” she asked.
“No, I’m just a very lucky man.” he answered, and smiled at me.
“I’ll say you are.” She started unbuttoning his shirt. “Help me out here, would you?”
Blair quickly undid the rest of the buttons, and pulled it off, followed by his t-shirt. Cassandra slid back until she was seated at the head of her bed, her back to the wall. “Damn.” she admired. “You are a work of art. Come kiss me.”
Blair crawled up the bed to her and they started making out hard and heavy. She was thrusting her hips, grinding against him, and her hands were all over him. She was every bit as aggressive in the bed as her personality suggested she would be, and I enjoyed watching my usually slow and steady lover not only keep up, but respond to her. As I’d learned with Ed, the different can be a big part of the turn on. I was getting turned on in my seat watching as they began to peal each other’s clothes off until finally they were both on their knees, Blair behind her wearing nothing but one sock, and her in her panties. She pushed her ass back against his hard cock, and he ran his hands over the front of her body. He was enjoying her gorgeous C cup tits, with big erect nipples.
“There are condoms in the nightstand drawer.” she said, as she pressed her chest against the bed, and slid her panties over her ass which was raised, just begging to be mounted.
I slid my silky dress up to my belly and reached my hand into my panties to finger myself as I watched my boyfriend unroll the condom over his lovely hard cock, which he then slid into the beautiful, curvy redhead’s pussy from behind. She kept her ass up and her chest and head down at first, as he thrusted his hips and drove his cock into her. I was taking my time more than these two, slowly, gently sliding my finger up over my clit, down and around my vagina, and back up again.
Cassandra lifted herself onto all fours. God her tits looked amazing, and I was half tempted to join Blair in fucking her. With one hand supporting himself he cupped one of her breasts with the other, and as he squeezed, I saw a drop of milk fall from her nipple, then another. She plopped forward, Blair’s cock coming out of her.
On your back, she commanded. When he’d followed her order, Cassandra mounted him and began to ride up and down on his cock. She had both of her hands on her breasts, squeezing, and now drops of milk fell steadily from both nipples. The site of this made my man, moan out loud and I wondered if he’d be able to delay cumming as well as he usually could. “Goddamn, that’s hot.” he said aloud, and Cassandra replied by leaning forward and putting her left breast in his face, her nipple in his mouth. He sucked at her, as he continued to thrust his cock into her. Then she sat up right again, and pinched both nipples. The milk sprayed from her perfect full tits onto his face and chest, as he was thrusting hard and fast.
I was so turned on at this, I had to slide my panties down my thighs, grab one of the the vibrators so thoughtfully displayed right next to my seat, and press it against my pussy. I pressed the button and it whirred to life. God bless a woman who keeps her vibrator’s batteries charged. I pressed the length of it against myself firmly and thrust my hips to slide it along my pussy. It felt so good vibrating against my clit.
With milk spraying all over him, and the gorgeous red head with the lovely curvy hips and tits riding his cock Blair came, and he came hard, and long. She knew exactly how to move, and freeze, and move and freeze to keep him cumming without pushing him over into too much. People say men don’t have multiple orgasms. These are people who’ve never met Cassandra.
As Blair finished and she raised herself up off of his cock she turned immediately to me, seeing me fucking myself with her black cock shaped vibrator. “Grab the pink vibrator for me and let’s cum together.” she all but barked at me.
I did so, and as I reached the bed she pressed her mouth to mine, and kissed me as we both used one of our hands to keep the vibrators pressed against our pussies and the other hands exploring each others bodies. We came together and by the time we were done, Blair was growing hard again from watching us.
“Tonight’s all about him?” she asked. I confirmed again, that yes, tonight was about showing my man a good time.
“Let’s get on our knees and suck him off together.” she suggested, and since I agreed this was a capital idea, we did so, taking his cock back and fourth between our mouths, kissing each other, and his thighs, and his balls, until finally I felt him heading to that point of no return and I took him into my throat. She stood and kissed his mouth as he came in mine. For a second round, he came a fair amount. We all collapsed onto the bed when I’d swallowed the last of it.
“I’d invite you to stay the night but this bed is too small to sleep three comfortably and I really value my sleep.” she said. I told her that was alright, and thanked her for such a lovely time.
“I truly think we showed him the time of his life.” I said, as I got dressed. She pulled on her panties and her bra. She squatted on her bed and said,
“Take a picture to remember me by, though I definitely think we should get together again, either all of us, or just two of us. You two are delicious.” she spoke in the same fast, confident, almost manic way she had when we first met her such a short time earlier that felt like ages ago. She reached over and turned off her lamp. “Use your flash. its dramatic.” she said.
Just as we had all night, we did as we were told. She kissed me good bye, and pressed three pills into my hand. “These will make you lactate, if you feel like doing the milk trick.” she said to me. “Thanks for letting me be your treat.” she said to Blair before pressing her tongue into his mouth, and then biting his bottom lip.
We rode home in silence, showered together, and then started giggling which turned to laughing as we crawled into bed and reflected back on the tornado of a sex kitten we’d just gotten swept up in.
“I like Cassandra.” Blair said for the second time that night.
“I like Cassandra, too.” I replied, and we fell asleep smiling.
Read more: Parts 1 / 2 / 3 / 4 / 5
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