Something New: Worlds Collide

They say that all good things come to an end. Maybe that's so, but it didn't seem like it would be coming to an end any time soon for me. I'd expanded my sex dates beyond the weekends, and was getting railed three to four times a week by different guys most nights, with the occasional repeat customer. I also cultivated a friendship with the virgin cocksucker from my threeway, and taught him the ropes of crossdressing and the continuing joys of sucking cock and getting fucked. He chose the name Tammy for when he dressed, and we had a couple double dates that were amazing.

One day, I got a message from my buddy, Bobby, that took me by surprise. I'd just gotten home from work, and was taking the night off after an all-night fuck session the night before when my phone chirped.

"Hey, man," the message said. "Wanted to say I'm proud of you, and a little surprised."

"What are you talking about?" I messaged back. He responded quickly enough.

"Heard from a neighbor that you've got different girls coming in and out of your apartment at all hours of the day," it said. "Good to hear you're back on the horse and making up for lost time." I made a joking reply, and said we should hang out some time before letting the conversation drop, but it left me cursing myself. I thought I was being discreet enough, but I guess I'd gotten sloppy. Still, at least whichever of my nosy neighbors was talking, they'd gotten the wrong idea, rather than the right one. I resolved to be a little more careful, but at this point, I was too addicted to regular cock to even think about slowing down.

So things continued for another week or so, until one fateful night, I was headed down to the gloryhole for a night of cum guzzling. I'd had a TrapFinder date lined up, but he'd had to cancel last minute, leaving me with nothing better to do on a Friday night. I opened the door on my way out for the night, and was surprised to find Bobby standing there with his fist raised to knock, and a six-pack of beer in the other hand.

Normally, this wouldn't be a problem, because I tended to dress at the hotel when I had dick appointments, but for the gloryhole, that wasn't an option; I was slutted up to the nines in a slinky black dress, stiletto heels and curly auburn wig. His surprise turned quickly to appreciation as he looked me up and down.

"Well, shit," he said with a leer. "Guess I shouldn't have dropped by without a call. Guess you're keeping him busy tonight?"

"He's not home," I blurted out, barely remembering in time to pitch my voice to Sheila's dulcet tones. Shit, that was a stupid thing to say...

"Is that right?" he replied. "Well, how's about I leave this sixer in his fridge, and you two can enjoy it. Call it my contribution to the night's festivities."

"I guess that would be okay," I said, stepping back from the door to allow him entry. He walked in and made his way into the kitchen, with me following behind. "Should I tell him you dropped by?"

"Yeah," he said as he opened the fridge and put the beer inside, but not before pulling a couple out. He handed one to me, and cracked the other one open, then took a long swig of it. I hesitated, then grabbed a bottle opener and helped myself as well; an ice cold beer sounded pretty good right now.

"I'm glad to see you," he admitted in conspiratorial tones. "It's good to see that he's dating again, after his divorce." He grinned and took another swig from his beer. "Kinda hurt he didn't mention a hottie like you, though." He thrust a hand out, and I took it gingerly.

"I'm Sheila," I introduced myself, then took another drink of my beer. "It's good to meet you."

"Uh huh," he responded. "You hoping to get serious?" he asked, then continued without enough time for me to respond. "I hear that he's playing the field a lot, got women in and out of here all the time."

"Oh, it's purely sexual," I heard myself say, and I found myself returning his frankly admiring gaze. Oh shit.

"Is that right?" he said, echoing himself. "I'll bet you're a hot one in the sheets." I couldn't help but smile as flickers of my many liaisons passed through my mind.

"I've never had any complaints," I said, my gaze idly wandering down to his groin. I could clearly see the outline of an erection pushing against his jeans, and I wondered how big it would be; Bobby was always bragging that he had a monster cock, but I always blew it off to the sort of bragging men always did. It certainly wasn't a modest size, judging by his bulge. I pulled my eyes back to his face, where his smile told me that he'd noticed my attentions. Against my better judgment, I smiled back. "You know, he won't be home for a while yet."

Bobby's eyes passed over me lustfully, and I saw his erection twitch, and I knew that I wanted this to happen. His eyes came back to mine, and I nodded; he nodded as well, and that was all I needed. I set my mostly empty beer aside and dropped to my knees, my hands quickly going to his button, and then unzipping his jeans as he shucked them down, and his cock finally sprung free, inches from my face.

He hadn't exaggerated much; I'd had bigger, but not often, and not much bigger. It was thick and veiny, with a glistening drop of pre-cum already pearling in the slit. I quickly licked it up with the tip of my tongue before playfully swirling it around the head, drawing a shuddering groan from my friend. "You don't pussyfoot around, do you?" he asked me.

I didn't answer with words; instead I engulfed the head of his cock, applying suction and stroking his shaft with my hand while licking the slit, causing him to jerk and shiver. I continued to tease his head until he couldn't handle it anymore, and his hands came down to grip my head, and he pulled my lips down the length of his shaft, then held me there while he started to slowly, insistently fuck my face. I continued to stroke and twist the shaft, supplying as much saliva as I could, and I angled my head so that the head of his cock bumped the back of my throat with each firm thrust; I wasn't worried about my gag reflex, as I'd trained myself out of that months ago. I moaned whenever he filled my throat, letting the vibrations add to the sensation, and before I knew it, he'd shoved his cock as deep as it would go and shivered as two loads shot down my throat. I caught the third on my tongue as he relaxed, and the last few dribbles on my lips as it slipped from my mouth. I waited until he looked down before I smiled, opened my mouth to show the cum pooling on my tongue, and promptly swallowed.

Bobby gasped and shuddered once more before he pulled up his pants hurriedly and mumbled something before he almost ran for the door. As the door slammed, I was still on my knees in the kitchen where we'd been talking, surprised by what had happened. That was Bobby, and I'd just swallowed his cock in my own house! I knew that if he hadn't fled, I'd have done a whole lot more, too. I sighed, disappointed, but I realized that I still had plenty of time to get to the gloryhole. I smiled at the prospect, but I realized it was only a consolation prize; what I really wanted was Bobby, eight inches deep in my ass, pounding me like the slut I was.

Bobby called a couple days later, on my public phone. I'd sent him a couple messages from Sheila's number, but he hadn't answered, so I was surprised and a little apprehensive to see his number pop up on my caller ID.

"Hey Bobby," I said, masking my nerves. "What's up, man?"

"Heya buddy," he replied. "Listen, I think we need to talk. The other day, when I stopped by your house-"

"Sheila told me," I interrupted. "It's fine, man, really. You're not the only guy she's been with, and I'm perfectly fine with it."

"Really?" he asked. I smiled, and felt a flush coming into my face.

"Really," I confirmed. "She told me she really enjoyed it, and... well, to be honest, I'm thinking about getting serious with someone, depending on how they feel about me." I hadn't intended to say that, but I realized it was kind of true; only the person I was thinking about was Bobby. "I think Sheila'd love to see you again."

"Fuck, man," he said. "That's surprising as hell, not at all how I expected this conversation to go."

"It's fine if you need time to think about it," I said. "This isn't really anyone's idea of normal, but I'm pretty happy with how my life's been going lately. Give her a call, if you decide you want to, seriously."

"I'll think about it," he said, and my heart soared.

"Great," I said, as casually as I could. "I gotta go though. I've got a hot date tonight." After I hung up the phone, I did a little dance of happiness. I'd been thinking about Bobby's meaty cock for the last two days, and the thought of it being inside of me made me positively giddy. But I hadn't been lying when I hung up the phone. I checked my makeup in the mirror, then headed out to meet my latest TrapFinder date.