Something New: Fuck Buddies

Bobby didn't call right away, but when I checked my messages after my date, he'd finally replied casually to my earlier messages. I replied back, and the next few days passed with regular messages getting increasingly flirtier until they'd become downright naughty. Still, he wouldn't commit to meeting up, and finally I realized that if I wanted to get my lips on his cock again, and maybe even more, I was going to have to take action.

I took Friday afternoon off from work to spend extra time on my preparations. I took a nice, hot bubble bath, then shaved and lotioned every inch of my body until I was smooth and silky all over. I picked out a deep red set of lacy lingerie, which included an open-ass gaff, and I taped my cock down tight; I didn't need that getting involved if things went as I'd hoped. After that, I focused on my makeup, doing my best to shape my already feminine features into something altogether more alluring, and finally topped it off with the same wig I'd worn when Sheila had first met Bobby. Over that I placed a discreet woman's coat and some strappy heels, then sallied forth to go get me a man.

I drove to Bobby's place, but parked a few houses down; I didn't want him to recognize my car. Sheila had an extensive wardrobe and her own phone, but the occasional tip for a dick well-sucked didn't earn me enough for another car. I walked up to his door and knocked, then waited for him to answer.

"Sheila!" he exclaimed when he saw me. I smiled my best smile.

"I got tired of waiting for you to invite me over," I explained. "Now, are you going to leave me standing here, empty handed?" He looked at me long enough that I thought he actually did mean to turn me away, before he stepped aside and opened the door wider.

"No," he said. "Please, come in." The doubt I'd seen in his eyes was slowly fading to desire, and I smiled wider as I sauntered in, and he closed the door behind me. As soon as the door was closed, he dropped all pretense, and his arms went around me, and pulled me in. I raised my head, and our lips met for the first time. I'd already done all of my second-guessing and self-doubt about this, and I knew that I wanted Bobby unlike I'd wanted anyone else, ever. I wanted to please him, feel him deep inside me, and hear him calling my name as he dumped load after load in my ass.

For now though, I was lost in kissing him, his tongue slipping between my lips, and his arms strong around my waist. I ran my hands over his shoulders, down to his ass, and gripped it tightly, pulling his groin into me so that I could feel his cock straining at his jeans. I brought my hands around the front, then slipped one inside his pants, while the other fumbled at his fly. I gripped his dreamy shaft and stroked it gently until the button slipped off, and I was able to unzip his pants, finally releasing it; it was already sticky with his pre-cum, and while kissing him was more than I could have hoped for, I couldn't wait to taste it. Once more, I dropped to my knees before my best friend.

I looked up at him before taking his cock into my mouth, and his eyes met mine as my lips sealed tightly around the head, and I drew it in as deep as I could, until his head bumped my throat. I moaned around a mouthful of his cock, and he threw his head back and his shaft jerked as I played my tongue along the underside, sliding it slowly out until I could lap his pre-cum up with the tip of my tongue before swallowing the whole length again.

"Fuck," he groaned, "How'd you get so good at this?" I moaned with the head of his cock filling my throat, then pulled slowly back until it popped out of my mouth. I kissed the tip of his dick before answering.

"So much practice," I purred, "I love a rock hard cock in my mouth, almost as much as I love riding one. The only thing sweeter than the taste of a thick load is the feeling of it filling me up." He groaned again at my filthy talk, and I went back to work, suiting actions to words, and swallowed his cock once more.

This time though, I paid close attention to his breathing and his reflexive thrusting. While I did love a hot load on my tongue, I wasn't planning on letting him get away this time without fucking me like the dirty slut I was. When his hands came down to my head, I pulled away and stood up, then pushed him not so gently into the living room, toward his couch. Bobby had bragged about this couch on many occasions, talking about the girls he'd railed there, and I intended to be the latest one to take his cock. His curtains were slightly askew, but I didn't even hesitate. I pushed him down, then dropped to my knees once more, sucking his engorged shaft into my mouth and slathering it with saliva, lubing it up for what came next. He leaned back on the couch with a sigh, and I looked up at him as I worked his cock in and out of my mouth a few more times before pulling away again, leaving it slick with my own spit.

I turned around and finally dropped the women's coat, revealing myself in all my smooth glory. I felt his eyes on my back, and I shivered, imagining that his gaze was hands, caressing me, following the shape of my hips, and centering in on my ass. I reached behind me and stroked his cock a few times, ensuring that the lube was nice and thick, before I began to move into position.

"Wait," he said, but I ignored him; he didn't fight me, and when I felt that bulbous head slip between my cheeks to rest against my asshole, his hands came shaking to my hips. I didn't want to take too long, or he might wonder why he wasn't getting to fuck my non-existent pussy; most guys fantasized about fucking a woman in the ass, but most women didn't enjoy it nearly as much as I did. Slowly I pushed back, feeling his head begin to stretch open my asshole, slowly more for the pleasure of feeling it work its way in bit by bit than for any need to relax; my ass was well used to being full of thick cock by now.

"Oh god," he muttered, feeling my heat engulf him, until finally it had fully filled my ass. I let it sit a moment, glorying in the feeling of my best friend fully impaling me, and feeling more like a woman than I ever had in my wildest days of debauchery. For the first time, I felt myself hoping that this would become a regular thing. I began to lift up, feeling his cock sliding out of my ass, the emptiness left behind both sweeter and more desolate than ever before. I brought him fully out, then slipped back down again, slowly filling up again.

"Mmm," I moaned as his cock stretched my hole, "Your cock is amazing." Once more I slowly pulled away, then just as deliberately rode his cock back down until my ass rested on his lap.

"You're incredible," he panted in reply. "I've never fucked an ass like yours before." I knew he wasn't exaggerating; for one, he'd almost certainly never fucked a crossdresser before, and certainly not one as enthusiastic as I was. I began a steady lift and drop, slipping his cock in and out of my asshole, and began to slowly quicken the pace.

I knew what I was doing, but this motion, as fantastic as it felt, wasn't going to get me off. I guess that was okay though; I was his woman, and all that really mattered to me right now was that he came inside me. He was thrusting to meet me, his hips slapping into my ass audibly, but while each jolt sent waves of pleasure through me, it wasn't as good as it could have been. After a good couple of minutes like this, it seemed like he sensed what I was feeling, because his hands came to my hips, and he turned forcefully, taking my balance and making me fall sideways onto the couch with a stifled scream. Instead of his cock popping out, he turned with me, riding me down so that I was laying on the couch with him coming to kneel behind me, still impaling my ass on his impressive shaft. From there, he took over while I wriggled onto my back, so I could see him fucking me.

Once in control, he wasted no time, leaning down to kiss me as his hips began a slow, rhythmic motion, drawing out slowly just to slam back forward, filling me and rocking my whole body with each thrust. I moaned with each thrust, his lips covering mine until I couldn't any longer, and I threw my head back and let my voice rise higher with each impact. Bobby kissed and nibbled at my neck, never slacking, but instead beginning to increase the tempo without letting up on the force of his thrusts. I was sure I was going to feel sore tomorrow, but for now it was the most glorious feeling as my whole body shook each time his cock slammed deep inside me. I could feel myself nearing the edge and I let him know how good it felt with uninhibited moans which only seemed to encourage him to try to fuck me even harder than he already was. Finally, I could take no more as the most amazing orgasm ripped through me, and I felt my trapped cock spilling my sticky load inside my panties. Bobby never stopped though, even as I fought to stay conscious, until finally he groaned and slammed in one last time, and I felt his hips buck once, twice, three times as he filled my ass with his hot, creamy cum.

He gave me a few more slow, languorous pumps, and I felt his cock twitch with each before he finally pulled out, leaving me feeling empty, but thoroughly fucked. I rolled onto my back, dropping my feet but keeping my knees up and wide; I felt his cum dripping out of my asshole, and hoped he'd enjoy the sight of his handiwork as much as I enjoyed it. I watched him as he started to pull his pants back up, only to shake his head and kick them the rest of the way off. He sat down on the couch next to me, and reached over to fondly stroke my thigh.

"I hope you enjoyed that as much as I did," I told him. "I hope there's a lot more where that came from."

"It was incredible," he said, turning to look at me. "You're amazing, but-" he broke off, and I felt my hopes start to die, if only a little.

"Don't worry about it," I started to say. As much as I wanted to feel his hands on my body and his cock in my ass, I wasn't exactly hurting for options. I'd be fine. His next words took me by surprise, though.

"I know who you really are, man," he interrupted. "Your wig slipped after the first time you gave me a blowjob." He smiled, but his hand never left my thigh.

"You knew?" I asked, almost letting my voice slip back down to my normal range. "Then why didn't you say something? Why did you invite me in?"

"It was the best blowjob I've ever had!" Bobby exclaimed. "No woman has ever enjoyed it that much, and it really shows."

"So, what then?" I felt hope and fear warring inside me. I never wanted my two worlds to collide like this, but it's not like I didn't make it happen, willfully.

"I guess it depends on you," he said. "It didn't feel right not to tell you I knew, at the very least."

"I still want to continue," I replied. "With you, I mean. Yours is one of the best cocks I've ever had."

"I dunno, man," he said, rubbing the back of his neck. "I mean, I want to fuck you, but I'm not gay."

"It's okay," I said reassuringly. "When I'm dressed, I'm not a man. And honestly, as amazing an experience as this was, I'm not really trying to lock myself down with one guy, either."

"So fuck-buddies?" He laughed when it struck him how literal that phrase was.

"Any time you want," I said. "As often as you want."

"Any time?" His eyes met mine, and he smiled.