A Devil, An Angel, And A Cowgirl Walk Into A Bar

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I’ve never been good with women. If there’s one thing that speaks the most to where I am in my life today, that’s probably it.I’ll admit, I don’t totally understand why. I’m not a bad-looking guy, I’m fit for my age, I have a good job, I’m not wealthy but I’m comfortable financially, I have a little girl, I’m in a rock and roll band–I have some things going for me. You might even say I’m a catch, on paper. But as it happens, women don’t date guys on paper. Well, maybe the ones with a stationery fetish, but that’s beside the point.When it comes to approaching women, I just…don’t. With friends, I’m really comfortable and generally outgoing, but with strangers, I haven’t a clue. I don’t know what to say, where to look, what to do with my hands, whether to address my inevitable erection or just ignore it. If I’m in a crowd, it’s much easier to hide than to engage. So it was with some reluctance that I hit the town alone on the Saturday night before Halloween. My desire to do something for Halloween won out over my desire to stay home porning and avoiding people, and with none of my circle of friends free for the evening, I headed to one of my usual haunts (get it?) and hoped for the best.I try to put myself in situations where, just maybe, if circumstances are exactly right, I can theoretically thrive in social interactions, so this little bar is exactly my speed. There are usually enough people here that the potential exists for interaction, but not so many that I feel overwhelmed.At forty, I shoot for Halloween costumes that allow me to be accidentally handsome, so I came out in my best Lazily Sexy Devil costume. As soon as I came in, I saw her–my perfect counterpart, the Naturally Sexy Angel sitting at the bar. Whoever she was with would probably be along soon, but for now, she was alone, so I took a seat three spots down from her at the bar, hoped my black suit, red tie, and hair-clip horns would be irresistible enough to do my work for me, and ordered a drink. She was stunning, in a white silky dress that might have been lingerie, cut quite low enough to accentuate lovely cleavage, and short enough to reveal that her white fishnet stockings went all the way up. Pixie-cut black hair perfectly highlighted her soft-featured face, subtly decorated tonight with glitter makeup. She was probably around my age, maybe a little older, but her amazing figure belied any aging. Her legs, https://escortium.org in particular, were to die for, and as I noticed her white stilettos, I wondered if she’d keep them on while…well, maybe I got ahead of myself for a moment. Hey, there’s that inevitable erection already!I’ll admit I probably wasn’t terribly subtle in admiring her, and before I could work up the nerve to say something to her, she broke the ice for me.“You couldn’t track down a real party either, huh?” she said with a slight smile, only half-glancing at me without really looking up from her drink. I thought quickly of an answer, as I only do when I’m writing a work of pure fiction and not actually nervously interacting with another person. Scanning the space all around me for a moment, I briefly feigned a puzzled look before looking down dejectedly. “Damn,” I sighed. “Looks like they all left me again.” She laughed softly at that response, as only a lady of my own fictional invention would, and turned slightly toward me, glancing at the two empty seats between us. “I’m not saving these for anyone,” she said, and miraculously taking the hint, I slid down to the spot next to her, hoping I was moving deftly enough that ignoring the inevitable erection would still be an option.What happened next was nothing short of astonishing. We talked, and it was easy, and it felt natural. I didn’t feel intimidated when she led the conversation, I didn’t feel pressured when she laughed at my jokes, I didn’t even feel nervous when she put her hand on my knee and slowly, gracefully inched closer to the bulge in my pants. I felt something, mind you, but it wasn’t nervous.I learned that her name was Casey, and she lived just a couple of blocks from here. She was a teacher, and hadn’t lived in town very long, having only moved here during the heat of covid. She had two adult children, but she started fairly young, which put her just a little older than me. She didn’t look it.I don’t know how long we talked, but I could have kept on all night. The attraction, as far as I could tell, was instant and mutual. Finally, with a sly look on her face, she asked me, “So what are you really doing out alone on Halloween weekend?””Well, Monday is for trick-or-treating, I wasn’t going to miss Adult Halloween, and all my friends had better things to do tonight,” I replied. “So I came here, since I can usually hide in a corner and not be noticed much. What about you? Why are you alone tonight?”Honey,” she said with a serious look. “What makes you think I’m alone?”Well of course you aren’t alone! I yelled to myself inside my head. Don’t know how your fella is gonna feel about how close your hand still is to my cock, but of course you aren’t alone!Casey shot a glance over my shoulder in the direction of the door, and before I could berate myself any further, an equally stunning blonde approached us and took a seat on the other side of Casey. Sexy Cowgirl had been her go-to costume choice, with cutoff denim shorts that showed off her boots and killer bare legs, dirty blonde hair pulled back into a messy ponytail under a straw cowboy hat, and a plaid snap-front western shirt that was currently laboring not to unsnap in the bust. She wore a silver sheriff’s star, and even with Casey right next to me inching her hand even farther up my leg, I couldn’t help but think for a moment how much I’d like to let her friend…handcuff me, to the…barn, or whatever. I don’t know, something an old west sheriff might do. She was really sexy is all I’m saying.I guess Casey must have had a similar thought, because she turned to the sheriff and kissed her deeply, leaving my jaw very nearly on the floor. Her hand finally reached its destination on its trip up my leg, and she lightly squeezed my throbbing cock through my pants as their kiss lingered not nearly long enough, if you ask me.”This is my roommate, Becky,” Casey said. “Kyle, close out your tab. You’re coming home with us.”I put a twenty on the bar and hoped I’d be able to walk when I stepped down from my seat.***The walk back to their house only took about ten minutes. I didn’t recognize the street, but that didn’t surprise me–I really didn’t know the neighborhoods this side of downtown very well, and I was currently so fixated on the prospect of fucking my two new friends that I wouldn’t have recognized my own name, much less some street I was unfamiliar with. “Kyle, I’ve wanted to do this since you walked in tonight,” Casey said, setting her keys on a table by the front door as we walked into their house. She closed the door, then pinned me against it and kissed me hard. It was a hungry kiss, not devoid of romance but by no means tender, a kiss that said she intended to use me but in a way that we both recognized and both wanted.”Now you,” Casey said, breaking our kiss, and pulled Becky to me. Becky kissed me with the same whirlwind intensity as Casey had, the only noticeable difference being the taste of their lip gloss–Becky tasted like strawberries whereas Casey tasted like a peppermint lifesaver. As Becky kissed me, Casey reached around her from behind and ripped open the snaps on her shirt (as it turns out, the sheriff in this town didn’t wear a bra) then unbuttoned her denim shorts and slid her hand inside (no panties either).I kissed the front of Becky’s neck as Casey went to the work on the back, and Becky closed her eyes and tilted her head back with a soft moan as Casey’s fingers went to work slowly and deliberately inside her pants. My kisses trailed down Becky’s chest, and I massaged her breast as I sucked her nipple into my mouth. My cock throbbed inside my pants as the three of us began to give ourselves over to passion, and I wanted nothing more than to take either of these women from behind as the other watched.Just as I felt we were all beginning to lose control, Casey pulled her hand from Becky’s panties, ran her fingers down Becky’s back, and softly pushed Becky away before giving me a quick kiss.“Okay, let’s slow down,” Casey said with a giggle. “I think we’re getting ahead of ourselves. Upstairs.” With that she took my hand and led me up the flight of stairs in the foyer. I didn’t know quite what these girls had planned for me, but I couldn’t imagine saying no to anything at this point. Becky followed, grabbing my other hand and bouncing playfully along behind me. At the top of the stairs, Casey glided through a door into her bedroom (their bedroom, perhaps) and led Becky and me along with her. When both ladies let go of my hands, I started to slip out of my shirt and move to the bed. Casey stopped me with a finger on my chest. “Not so fast, Lucifer,” she said with a sly grin.Becky guided me a few steps backward and pushed me into a large red upholstered chair facing the bed. “For now, you just watch,” Becky said, and kissed me softly but playfully on the cheek. “And don’t touch anything until we say it’s okay.”I took this as a playful tease, but I was quickly corrected. Casey led Becky to the bed, lightly pushed her to a seated position on the edge of the bed, and moved to her knees in front of her. Casey began to slowly, softly kiss Becky’s inner thighs, starting just above the knee and inching her way closer to Becky’s pussy. My pulse pounded, and I squeezed my throbbing cock through my pants. 

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