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Falling for Zak

"A young man let's himself go to another man's desires"

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I hadn’t noticed the time, and I’d missed the last train home. The student party was fun, but I was in a bit of a panic not knowing what to do. People were leaving, and the crowd was thinning out. If it had gone on for several more hours, I would have stayed there and taken the first train in the morning, but that didn’t look likely. The hostess was already clearing up. I figured she’d be dropping hints at the last remaining people to go home soon.

“What’s up?” said Zak, looking at me with genuine concern.

“I’ve missed the last train. I guess I’m going to have to sleep in the park or something.”

“Maybe under a bridge?” he grinned. “Or in a doorway?”

“Something like that,” I replied, sighing. “I don’t know how I let this happen.”

“It’s ok, Buddy. You can stay at my place.”

“Are you sure?”

“Of course. Jessica’s out of town. It’ll be just the two of us.”

Zak was part of the reason why I’d lost track of time. He was a charming guy, just a couple of years older than me, of athletic build with short light brown hair and blue eyes. I’d only just met him that evening and was intrigued by his stories. He’d lived in several parts of the world and encountered so many different experiences that he made for easy listening. His soft spoken voice drew my attention to the point where I’d felt a little sexual tension at times and had to avert my eyes. A few times during our conversation he’d patted my leg to get my attention. While it wasn’t overtly flirtatious behavior, it did make me feel strangely excited and wanting for more, but I knew he had a girlfriend and was probably just being friendly.

---

We didn’t talk much while he drove us back to his place. I found myself thinking about what might happen. I’d only ever had girlfriends before and didn’t consider myself gay. Still, there was something about Zak that attracted me. I had to keep telling myself that it was probably just my imagination.

---

Once we got into his apartment, he offered me a nightcap which I gladly accepted. We sat in the living room sipping at our drinks, not talking. The Zak I’d met at the party seemed quite intense. He looked at me as though he wanted to speak, but the words weren’t coming out. I wasn’t much of a conversationalist so I just smiled at him whenever our eyes met. I felt there was something going on in his mind, which became very apparent when he finally opened his mouth.

“Have you ever tried on dresses?”

“What do you mean?”

“Dresses. You know, ladies clothing.”

“No.”

“I think you would look good in a dress.”

“Really?”

“Yes. You’re cute. I think it would suit you.”

“Thank you.”

I felt myself blushing profusely. I didn’t know what to say. It was obvious that Zak was testing the water for some further action. I could feel my cock swelling at the thought of him touching me. If that meant wearing a dress, then I would do so. I couldn’t believe that I was feeling that way. It felt good. I sat there, anticipating the next steps. He stood up and walked off down the hallway.

---

“Here, try this white one,” he said, coming back from the bedroom.

He held up a beautiful white lace summer dress with a little pink flowery pattern and a sheer tulle ruffled border. I felt the material. It was silky and soft. The touch of the fabric between my fingers was making me rock hard. My face was as red as a beetroot as I took it from him. My heart was pounding, and my head was spinning.

“And these,” he said, handing me a matching set of white stretch cotton panties and bra with pink bows.

“Can I change in the bathroom?” I asked.

“Of course. I can’t wait to see how you look.”

---

I went into the bathroom and quickly got undressed, stripping naked before putting on the panties and bra. I assumed they belonged to Jessica, but I didn’t want to ask. For now, I just wanted to go with the flow. Zak had impressed me with his stories and equally with his ability to make me feel comfortable with the situation, despite my confused state of mind. I looked at the bulge in the panties, feeling excited at the sight of my shaft pressing hard against the soft material.

I slipped the dress over my head and looked at myself in the mirror.

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“Zak was right,” I thought, “I do look good in a dress.” I was ready for the next step. I brushed my hair across my face, mimicking a side swept fringe.

---

“You look gorgeous.”

“Do I?”

“Yes. Come here.”

I stepped forward and felt him put his arms around my waist. He pulled me toward him and kissed my neck, running his hand gently through my hair. It was at that moment that I felt certain I would let him do anything. He had captured me, and I was a willing prisoner. I wanted him to enjoy me as much as he wanted.

As I stood there feeling helpless, I felt his strong hands lift up the bottom of the dress and stroke my bottom through the panties, squeezing my cheeks in his hand. He ran his hands up my back while his hot breath tickled my neck.

“You’re such a sweet girl,” he said.

“Thank you,” I gasped.

Within moments, I felt him dipping his hand down the front of my panties. He took hold of my shaft and started stroking it gently, rubbing his thumb over the head of my knob. I almost came at the thought of standing there dressed up like a girl, with a man fondling me.

I watched as he knelt down and popped my knob over the top of the panties before engulfing my cock inside his mouth. The sight of the dress material, its lacy edge and my rock hard dick being swallowed were exquisite. He tickled my balls while swallowing me, to the point where I had to pull away, for fear of cumming hard in his mouth.

He stood up and took my hand, pulling me into the bedroom and practically throwing me on the bed like a rag doll. Within seconds he had dropped his pants and pulled out his thick throbbing member.

“Suck me, darling,” he said, pulling me toward him.

I’d never had sex with a man before, and no experience of giving blowjobs. Still, I wanted to try, so I kissed his knob for a moment before I felt his hand on the back of my head. He pushed my face down until I had several inches of his cock in my mouth. I licked his shaft, hoping that I pleased him.

“Hmm, that’s nice,” he said, confirming that I was doing okay.

He guided my head up and down, sliding his rod in rhythm while I sucked and lapped ferociously, feeling his member getting stiffer and stiffer. I wasn’t afraid of him cumming in my mouth. In fact, it’s what I wanted. I wanted to serve him and please him. I wanted to feel his hot sticky stream spurting into the back of my throat. Instead, he pulled out just when I thought he was about to cum.

He pushed me over onto my back and grabbed at the panties, pulling them down swiftly before kneeling between my legs. I knew at that moment that he would penetrate me. I was slightly afraid, but I wanted it anyway. He lifted my legs and press his knob against my anus while grabbing a bottle of lube off the bedside table. He poured some of the liquid over the end of his knob and on his fingers, which he then proceeded to rub into my hole. I looked up at him and smiled.

“How are you doing, baby?” he asked, smiling back at me.

“I’m fine,” I replied.

He pushed gently, easing his cock inside me. It hurt a bit at first, but after a minute or two, I felt more comfortable as he slid his rod in and out of my ass. I watched his face while he rode me, feeling the intensity of his actions. I wondered if he’d done this before. I thought he probably had, but I wasn’t bothered. I was happy to be his conquest for that night. I think he felt that admiration.

“You’re a damned fine girl,” he said, “And so pretty, too.”

He took hold of my shaft and stroked it in unison with his pumping action in my ass. Within just a few moments I felt him swelling up inside me, followed by the feeling of warm liquid filling my loins. He moaned out loud as he pumped his seed into me, causing me to cum, too, the ejaculate dripping over his fingers as my balls were drained.

---

I felt ecstatic, even though somewhat confused at my own sexuality. I’d never really thought about being with a guy before, and especially not being with a guy who likes guys dressed as girls. But Zak had changed all that. In just a few hours he had seduced me and made me feel good about myself.

---

We got washed and ready for bed. Once again we didn’t speak, but there was an understanding between us. Zak produced a beautiful pink silk nightdress which I wore to get into bed. I turned my back to him, and he put his arm around me, spooning me until I feel asleep.

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Written by LarsKaiden
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