A Bend in the Road Pt. 02

I arrived at Paul's apartment on a Friday and planning to stay for a weekend full of sucking and jacking off. Under my clothes I was freshly shaved and wearing white cotton panties with green hearts. I remembered that in grade school green meant horny. I was definitely horny so I'd chosen green hearts.

Paul opened the door in his bathrobe as usual. But instead of making a bee line to his bed like normal, he asked if I'd take a shower with him. I wasn't expecting the request. Paul and I had only showered together once, the time he first shaved my body. I agreed, though, because ... well, why not.

I deposited my clothes with his robe in his bedroom and then joined him in the bathroom where he had a warm shower going. We got in and Paul soaped his hands and started lathering my body. He sort of hugged me so we were chest-to-chest and cock-to-cock, and he soaped my back and then my ass. I wasn't sure what felt better, his cock rubbing against mine or his slippery hands massaging my ass. Then he had me turn around.

After he got more soap on his hands, Paul slid them under my arms and began working rubbed soap on my chest and stomach. Then he soaped his hands again and paid particular attention to my cock and balls. By this point I was so hard I was throbbing.

"Spread your cheeks," Paul whispered in my ear.

That stopped me cold. Did he want to fuck me? We'd never come close to that before. He'd never even hinted that he wanted to fuck me.

Paul must've sensed my hesitation because he whispered, "trust me. Just spread them."

Tentatively I reached back and held my ass cheeks apart for him. Paul gently laid his cock in the crack of my ass and began to gently grind against me.

"Okay, let go," he whispered. I did and my ass cradled his cock as it slid in my wet crevasse. The feeling was amazing. Paul resumed working his hands over my body, one arm stretched across my chest so he could play with my nipple and the other stroking my cock. I was in heaven. I'd never felt such different sensations crashing against me at once. But Paul had one more in mind.

As I was giving myself to his hands and cock, I felt his warm breath and lips on my neck. Paul was kissing me. It was the perfect. I tilted my head the other way, exposing my neck to his mouth and lips. Then I reached back and grasped his hips and pulled his cock harder against me. We both began moaning in time with his thrusts against me.

"Oh, god Paul," I groaned. "I'm gonna cum. Oh god, I'm gonna cum so hard."

"Yes, cum baby," he murmured into my neck. "Cum for me."

I exploded in orgasm. It felt like my cock pumped cum forever, and Paul stroked me through to the very end. When it finally stopped I was nearly spent and Paul was practically holding me up.

Paul's cock was still rubbing in the crack of my ass and I realized that he was still as hard as I'd been moments before. I turned in his arms and dropped down so I was sitting on the side of the tub. I opened my mouth and took him in all the way to the base. I curled my tongue against the underside of his cock and slowly withdrew him before plunging him back into my mouth again. I steadily stroked his entire length with my lips and tongue, sucking him deep and hard. I glanced up to see Paul watching me suck his cock like a hungry slut. I pulled him out and said, "fuck my mouth. I want you to fuck my mouth."

I closed my eyes as Paul's hands held the back of my head and entwined in my wet hair. He held my head still as he began fucking my mouth, pumping his cock in and out. I worked hard to keep contact with my lips and tongue, caressing as much of his cock as I could. Paul was moaning as he pumped his cock in and out of my mouth. I felt like a cheap whore, but I didn't care. I wanted to give Paul as much pleasure as he'd just given me. Paul was grunting now through gritted teeth. He'd picked up the pace and I knew he must be close. Then I felt his fingers grip my hair as he plunged into my mouth one last time and exploded. Cum pumped into my throat as his cock throbbed. I swallowed every drop.

When he'd finished we got out of the shower, dried off, and went to the bedroom.

"I have a surprise for you," Paul said.

"Something more than what we just did," I asked.

"Mm hmm," Paul murmured.

Then he reached under the pillow and pulled out a pair of thong panties. The front panel was purple satin with black lace trim and black straps around the sides and down the back.

"Will you wear it for me," Paul asked. It was a question, but it didn't really sound like a question. It sounded more like "you're going to wear this for me" and "I know you want to wear this for me." None of that really mattered though because I knew I was going to put on the thong a soon as I saw it. I knew what it would mean for Paul and I wanted to please him.

I took the thong from him, slipped my legs through the openings, and pulled it up around my hips. The tiny strap in the back slid between my checks and my cock nestled against the soft satin. As Paul devoured me with his eyes I turned slowly and modelled the thong for him.

"You like," I asked.

"God yes," he murmured. "Lie down."

I made a show of crawling onto the bed on my hands and knees so that he got a good look at the thong in my ass crack. Then I languidly laid on my back and tried to look as sexy as I could. Paul was rock hard again and I wasn't far behind him. He climbed on the bed and I expected that he might give me a blowjob, which he usually did when I wore something new for him. But he didn't. Instead he laid his body on top of mine, his hard cock rubbing against mine with only the thin satin between us. Paul looked me deep in the eyes and then he kissed me.

It was gentle at first, but the hunger grew quickly and his tongue pushed into my mouth to tangle with my own. After he'd kissed my neck in the shower I couldn't say the kiss was completely unexpected, but the newness of the sensation of kissing Paul caught me off guard. I tensed at first, but Paul kept kissing me and I eventually relaxed and kissed him back. I wrapped my arms around him and snaked my legs around his. We were grinding our cocks against each other and the passion and intensity built steadily. Paul stopped kissing me and moved back to my neck. He kissed a line down my neck and onto my chest. He stopped at each nipple and slowly sucked each one until it was a hard point. Then he kissed down across my stomach. He shifted to lie between my spread legs and kissed up both of my hairless inner thighs from knees to my balls. Paul began kissing my raging cock through the thong, starting at my balls and kissing slowly up the length of my cock to the soft skin under the head that was now exposed above the black lace. He took his time kissing that sensitive spot and teasing it with the tip of his tongue before going back to my balls and starting over.

As I laid there enraptured by the sexy sensations Paul was giving me, I realized something had changed. In all our prior encounters we'd had sex. We'd jacked each other and sucked each other, but every time it was just to get the other person off. It was just a partnership of convenience. We were both willing and, at least in my case, desperate. But this was different. Paul was making love to me. He'd already made love to me in the shower and now he was doing it again. We'd crossed a line, or rather Paul had led me across a line. I didn't know how or why, and at the moment I didn't care, but we'd definitely crossed a line. And as I felt Paul pull down the front of the thong and place my cock lovingly in his mouth, I realized that I desperately wanted Paul to make love to me and I wanted to make love to him too.

It didn't take long before I exploded in Paul's mouth, filling it with cum. He swallowed it all before releasing my softening cock and smiling up at me.

"Oh my god, Paul. That was amazing," I said softly.

"Mmm, I'm glad you liked it," he said.

Paul got on his knees between my spread legs and started stroking my thighs. I could see his hard cock pointing up between us. His eyes wandered from my thong-covered cock up my body to meet my eyes. As I looked into his eyes I knew what he wanted. I wanted it too and I nodded to him.

Paul leaned over me and reached for the drawer in the bedside table. He pulled it open and withdrew a full tube of lube. Paul squeezed a generous dollop into his hand and began applying it to his cock. After he'd thoroughly coated his cock with lube, he reached his fingers between my ass checks and pull the thong to the side. Then he smeared some lube around my anus. Paul then put his hands under my knees and pushed them up toward my chest, which angled my puckered hole up at him. As I held the position, Paul aimed his cock head at my virgin back door and gently pressed it into me. He went slowly, pressing and releasing, over and over. It gently stretched and relaxed my ass until finally the head slipped in.

It hurt a bit at first, but Paul waited while the pain subsided before pushing more of his cock into me. Paul took his time, but soon he was buried in my ass to the hilt. Paul leaned down and kissed me. When he broke the kiss I looked him in the eyes and said, "fuck me, Paul. Take my virgin ass and cum inside me."

Paul groaned as he started slowly withdrawing his cock and pushing it back into me. He began a slow, steady rhythm. As he gently fucked my ass, I enjoyed a whole new set of sensations. His cock sliding in my ass felt incredibly intense. Paul was enjoying it too as he picked up the pace and began fucking me in earnest.

"God your ass is so tight," Paul groaned.

"Take it, baby. Take my virgin ass and make it yours," I said back. "I swallow your cum. Now I wanna take it up my ass."

Paul slammed into me a final time and groaned. I felt his cock spasm inside me, another first sensation. I knew he was filling me with his cum.

"Yes, Paul, fill me," I said. "Fill me up with your cum."

Paul laid forward on top of me and began kissing me again. I wrapped my arms and legs around his back and held him while he came down. When he finally slipped out of my ass and rolled off of me we curled up together enjoying the afterglow of our first fuck. Paul fucked me several more times that weekend as we explored missionary and doggy-style. On Sunday I rode him reverse cowgirl, letting him relax and watch his cock sliding in and out my ass.

Over the next few weeks Paul and I bought more thongs and crotchless panties, which I wore whenever we were together. I started wearing them even if we weren't getting together. Paul loved getting selfies of me in panties, especially when I could take them at work. I'd often get a short video back of him jacking off.

One day I was surfing through an online when I found a crotchless teddy. It had a red satin and black lace front and a sheer black back. And of course it was crotchless, giving Paul free access to my cock and ass. I knew he'd love it, so I ordered it. When it arrived I tried it on and got so horny I nearly came without touching myself. I sent Paul a text telling him it was finally time for to surprise for him and that he'd get it on Friday night. I got a boner emoji in return.

I arrived at Paul's wearing my teddy under my clothes. Paul met me at the door naked and hard as a rock. I could tell he was really horny, not just from his erection but the look on his face. He looked like a little boy on Christmas morning. I led the way back to his bedroom and turned to face him. I kicked off my shoes and socks before dropping my pants. I was hoping he would think I'd bought a new pair of crotchless panties. Paul was staring hungrily at my cock poking out from the red satin and black lace as I began unbuttoning my shirt. That's when Paul noticed that the sexy material didn't end at my waist. His eyes went wide as I finished taking off my shirt and dropped it to the floor.

"Holy shit," he mumbled.

I did a little turn for him, letting him take in the teddy from all sides. Paul caught me while my back was to him and pulled me in. He ground his cock against my ass and kissed me neck as his hands explored the front of the teddy.

"I take it you like your surprise," I asked.

"You have no idea," Paul said.

"Oh I think I have some idea," I said as I wiggled my ass against his cock.

"No, you don't understand," Paul chuckled. "I'd already gotten as surprise for you, too. I was going to wait to give it to you, but this teddy ... it's just too perfect."

With that, Paul went to his closet and got a shipping box. He laid it on the bed and I opened it. I pullout out a package of sheer black thigh-high stockings and a shoe box with 3-inch black patent leather pumps.

"Oh my god, Paul," I breathed.

"You see," he said, "they'll look so perfect with your teddy." He paused and then whispered, "Please tell me you'll wear them."

I turned and kissed him hard before opening the stockings package and carefully pulling them out. I'd never worn stockings, but I'd seen my ex do it, so I had some idea how it worked. I knew to bunch them up down the toe and then slowly and evenly work them up my legs. I don't know that I did it perfectly that first time, but I got the job done. And I did without running the hose.

I took the heels out of the box. They were the classic black pumps that appear regularly in every guy's fantasies. I warned Paul that I wouldn't be able to walk in 3-inch heels right away, but he chuckled and said we wouldn't be doing much on our feet for a while.

I slid the heels on and they fit perfectly. Paul must've checked my shoe size and then found a size conversion. I stood carefully and tried to pose and model the ensemble for Paul. I can't say that I was graceful, but he didn't care. He was devouring me with his eyes and I was sure that I was fulfilling a fantasy he'd been hiding in his mind. I was also sure that I was about to get royally fucked.

I gingerly tripped to the bedside table to get the lube. I squeezed a generous dollop onto my hand and began rubbing into on Paul's raging cock. Then I crawled on the bed, laid on my back, and pulled my stocking-covered legs to my chest. Paul knelt below me and positioned his cock at my ass. Then he leaned forward and entered me in one strong thrust. Once he was buried in my ass he stopped and gazed at my body again. He ran his hands down the front of the teddy, across my bare upper thighs, and down my stocking-covered legs to my ankles. He held my ankles and gently placed them over his shoulders. He leaned forward, pressing my legs toward my chest, and kissed me hard, pressing his tongue into my mouth where it entwined with my own. Then he began fucking me with long, steady strokes. He plowed deep into my ass, giving me his full length on every stroke. His pace steadily increased until he was pounding me, his hips slamming into my upturned ass. He was grunting with effort and I was moaning with pleasure. As hot a fuck as it was I knew he wouldn't last long. And soon I felt the tell-tale throb in my ass before he stiffened and pumped his cum into me.

I stared up at the exquisite expression frozen on his face. Next to his fact I saw ankles inside sheer black stockings and feet inside black patent leather pumps. Those are my ankles and my feet, I thought. How did I get here? How did I become another man's gay, crossdressing lover? At that moment I didn't really care. I was happy and content and I wanted more.