A New Summer Experience

I could barely contain my excitement. Lana was coming home!

She had skipped the annual camping trip to spend some time with her boyfriend up north. She was almost exactly a year older than me, and my best friend on top of my sister. There were no secrets between us...I knew when she started smoking, and her fling with a female classmate. She knew all about my one experience with sex with a girl, and had barged into my room more than once when I was masturbating. When she did catch me, she just rolled her eyes and left to let me finish.

But she didn't know anything about what had happened to me over the last few weeks, how I'd seen a man getting a blowjob from another man that led to my own cocksucking and getting fucked. That I'd been blowing my boss every night after work, to his and my mutual enjoyment. How much I craved servicing a man, and how much I loved being underneath a man while he pounded the hell out of my ass.

The day she came home, she had her boyfriend Jake in tow. She'd met him at Huntington where they'd shared some classes. He was a senior to her sophomore, and was tall and muscular. If I were into younger guys (well, younger than Paul and John anyway), I'd be attracted to him. I'll admit, though, I had a slight animosity towards him...after all, he was taking up time that I could have spent with Lana.

I didn't get a chance to talk to her privately for another week. She moved into an apartment with Jake, and between work and sneaking over to Paul's house I was busy myself.

The opportunity arose on my day off from Burgerstack. Dad had found a box of Lana's stuff in the garage and asked me if I could run it over to her place. Even though it was after noon, she answered the door in a tightly cinched bathrobe, hair dishevelled like she'd just woke up.

"Where's Jake?" I asked, setting the box down on a cinder-block and plywood "coffee table" and sitting next to her on a couch that they'd obviously scrounged up second-(or maybe third-)hand.

"Sleeping," she said with a grin. "We were up late."

"Good," I said. "I've been dying to talk to you since you got back."

I told her all about the camping trip, and what had happened with Paul and Matt, and what was going on since we'd gotten back. She didn't act surprised or upset.

"So is Paul your boyfriend?" she asked.

"I don't know if I'd call him that," I answered. "I mean, we have sex but haven't like gone out or anything."

"I had suspicions that you might be gay," she said.

"Really? Why? I thought I was pretty much an average guy growing up," I replied.

She grinned. "You remember playing dress-up when we were kids?"

I did. When we were in our early teen's, Mom and Dad had gotten into square-dancing and would go out every Friday and Saturday night. We would dress up in her and Mom's clothes, and she took great delight in doing my face with make-up that she swiped from our parent's bathroom. We would sashay around the house, talking about imaginary boyfriends and laughing a lot. It came to a screeching halt one day when Dad had come back to the house unexpectedly. We didn't get punished for it or anything, but I think that was the reason they stopped going out.

"You took to that easily," she said. "If Dad hadn't caught us, we'd probably still be doing it."

"It was fun," I admitted, "but I don't want to be a girl or anything. I'm a guy that just likes guys."

"We should try it again," she said with a mischevious twinkle in her eye.

I laughed. "What?"

"We should try it again...dress you up and see if you like it still," she said.

"I don't know, sis," I said, still laughing. Surely she wasn't serious?

"C'mon," she said. "It'll be fun. Like old times."

I realized she WAS serious. I frowned.

"I don't think so, sis," I said. "That was just us kids playing. I think we've outgrown that."

She knew exactly how to poke my buttons, and pouted. She'd use that when she wanted to get her way with something. It had always worked for her before, since I never wanted to disappoint my sister. It didn't just work on me either, it worked on Dad too. Mom never fell for it, though.

"No," I said, laughing.

She pouted harder.

"It's not going to work," I said, smiling.

She pouted even harder, tilting her head down with her eyes turned up towards me. She looked like a petulant six year old.

We stared at each other. She rarely got angry with me, but I could sense irritation rising in her. Finally, I broke my gaze.

"Ok, fine!" I said. Anything to stop the pout.

It turned into a smile. "I knew you'd see things my way," she gloated. I rolled my eyes.

She stood up. "Wait right here," she said.

"What? Now?" I asked. "Isn't Jake here?"

She waved my question away. "He's sleeping, and knowing him he'll be sleeping for a while."

I was a little bit panicky. "Shouldn't we wait until he's not here?"

"He's always here," she said. "He's not working this summer and the next semester hasn't started yet. Just sit right here. I'll be right back."

She left down a short hallway to her bedroom, returning a few minutes later carrying a bunch of clothes.

"Strip," she commanded. Hesitantly, I pulled off my clothes until all I was wearing was my underwear.

"Tighty-whiteys, too," she said.

"But.." I said.

"I've seen your dick before, remember?" she said, cutting me off. "Get them off."

Reluctantly, I pulled my underwear off and they joined the pile of my clothes on the floor. I stood in front of her, covering my groin with my hands.

She handed me a pair of panties, which I quickly put on to cover my nakedness. Then she handed me a pair of shorts. They were tiny.

"These are too small for me," she said. "They should fit you, though."

They fit, barely. I had to suck in just a litle bit to get them buttoned. I could feel them ride up my ass a bit, and felt cool air on the bottom part of my asscheeks.

Lana looked at me critically, then moved next to me. She unbuttoned the shorts, and I yelped in both surprise and a little bit of pain as she shoved her hand in the front of my shorts to push my dick and balls down. When she was done, she'd damn near shoved them under me between my legs.

She rebuttoned my shorts, and looked me over. "Better. You had a little bit of a bulge showing."

"You could have let ME do it," I said, accusingly. I was shocked that she'd touched my dick.

Grinning, she handed me a bra, and showed me how to put it on by fastening it in the front then spinning it around. After the bra was in place, she gave me a sleeveless black blouse. Once that was on, she looked me over and said, "You need tits."

She went back into her bedroom and came back with two pair of socks. I didn't understand what they were for until she pulled the front of my blouse open and inserted them into the cups of the bra.

"Better," she proclamied. She took my hand. "C'mon."

She half led, half towed me into the bathroom and told me to sit on the toilet. Over the next 20 minutes, she made up my face.

The memories of doing this when we were kids came flooding back to me. I particularly enjoyed it...not as much because my face was being made up, but rather the attention Lana was paying me. I basked in it, smiling a bit as she said things like "pucker your lips" or "close your eyes."

"There," she said. "All done. You look cute."

I stood up, and moved in front of the mirror.

"I look like a guy with make-up on," I said.

She frowned. "It's the hair. It's not long enough to do anything with." I had longish hair, like every other young man in the late 70's, but it barely went past my collar.

"We could cut it and give you a pixie look?" she suggested.

"Uh, no thanks, sis. We're not cutting my hair," I responded.

"Well, you need to grow it out some then, so there's something for me to work with," she said.

She took my hand and led me back into their living room. She told me to sit, then stepped back into her bedroom. I was a bit confused...I had the clothes and the make-up. What else was there?

My heart raced in fear as she stepped back out of her bedroom with Jake, only wearing boxers, behind her. He looked like he was still half-asleep, and his eyes widened in surprise as he saw me sitting on the couch. I wanted to curl into a ball or hide...what the hell was she doing???

"You haven't met my sister, Will...ma," she told him.

"Wilma?" he snorted. "Are Fred and Pebbles coming over later too?"

She slugged him in the arm. "Wise-ass. But she's hot, isn't she?"

He ignored her question. "Why is your brother sitting in our living room, dressed like a girl?" he asked.

"My SISTER," she insisted.

"Okay," he said slowly. "Why is your sister, who's really your brother, sitting in our living room dressed up in your clothes?"

"My SISTER," she replied, "is just visiting. And she likes boys as much as I do."

He gave her an angry glance. "Can I talk to you alone?" he said, then spun on his heels and stomped off.

"Don't move," she said, then followed him. They were gone an agonizing ten minutes, and I had a almost-overwhelming urge to flee. I couldn't make out what exactly they were saying, but their voices were raised and I distinctly heard the word "fag" several times.

When they did come back, he had an irritated, resigned look on his face and she was smiling. I knew that smile...that was her "I'm getting my way" victory smile.

"Sorry," she said to me, then took my hands and pulled me to my feet. She looked at him and said, "Well? No blowjob, no ass."

Disgruntled, he shoved his boxers down to his ankles, then stepped out of them and flopped on the couch.

I turned to Lana. "What's going on?" I hissed.

"I wanna see you suck his dick," she giggled. "He's been trying to fuck me in the ass, and I told him if he let you blow him he could have it."

"I'm not blowing your boyfriend," I said, shocked. "He's not even my type!"

She looked at me quizzically. "You have a type already?" she asked.

"Well, yeah," I said. "I like older guys."

"He's older," she said. "Older than you, anyway. And he's got a really nice dick. Look at it," she said.

I glanced at his crotch. His dick was completely soft, but even then it was about 4" long and kind of thick. Without intending to, I imagined what it'd look like hard. I also felt a pang of lust that I didn't expect.

"Are we going to do this or not?" Jake asked crossly.

Lana grabbed my shoulders and turned me to face Jake, then gently pushed me down onto my knees. I still wasn't sure about this, but I was getting hornier the more I looked at Jake's cock. I gingerly reached out and took his cock in my fingers, leaned forward and slid my tongue across the head.

I normally got a reaction from John and Paul when my tongue touched their dicks. Not from Jake, though. I took his cockhead between my lips, and sucked gently at first then harder. Still no reaction from Jake.

Suddenly determined to get something out of him, I took his whole soft length into my mouth then slowly pulled my mouth off of him, sucking stronger as I did.

His cock twitched in my mouth. Finally!

I repeated the motion and was rewarded by his cock thickening a bit. I also heard an appreciative sound from him. I continued doing that, stroking his ever-hardening cock with my mouth and tongue. Fairly soon, he had a full-blown hardon. NOW I had something to work with!

Hard, his cock was as thick or thicker than John's, and longer than Paul's. I took him really deep, gagged a little when it pushed against the back of my throat, then pulled off and ran my tongue around the head again. I could taste a little pre-cum from him.

I was determined to take his whole length. I wanted it, needed it. I took him deep again, this time controlling the gag reflex and held him against the back of my throat. His pubic hairs tickled my lips, but I didn't have him completely in my mouth yet.

I pulled back, took a deep breath through my nose, then tried again. His cockhead shoved up against the back of my throat, and I felt a little pop as it slipped into my throat.

"Fuuuuuuuuck," I heard Jake moan. His hand moved the back of my head and pulled me harder against him. My lips pressed against the flesh of his groin.

I started sucking him in earnest, my mouth flying up and down his shaft then taking him into my throat again. I could feel his cock throb. He was getting close.

I didn't want to choke on his cum if he got off when he was in my throat, so I didn't go as deep but sucked harder, faster.

"Getting there," I heard him say through gritted teeth. I couldn't go any faster than I already was, or suck harder, so I just kept it up. From behind me, I heard breath explode loudly out of Lana as I felt Jakes cock swell in my mouth and a sudden flood of his cum sprayed into me.

I swallowed, and swallowed again. Jake produced more jism than Paul or John...maybe more than both of them combined. As I consumed his juices, I felt his hand relax on the back of my head, then fall away.

I sucked him gently until I felt the last throb of his cock, then slowly pulled my mouth off of him. I saw a stray glob of cum on the side of his shaft, and my tongue darted out and scooped it up.

"Jesus," Jake groaned and I looked up at him. He had a half-smile on his face.

"He's better than you," he told Lana. He slid away from me and stood up, putting his underwear back on.

Still on my knees, I looked over at Lana. Her robe was open slightly. I could see the swell of her breasts, and that her hand was in her crotch. Was that loud exhalation I heard from her cumming?

"That was fucking hot," she said, her fingers still moving against her pussy.

I wiped my lips and slowly stood up. Now that I had gotten Jake off, I was back to being a bit nervous about the whole situation. Jake didn't say anything, just walked out of the living room and back into their bedroom.

Lana jumped up and I got a glimpse of her pussy as she did. I don't know if it was because she's my sister or that I'd lost interest in girls but seeing it didn't do anything for me. "I'll be right back," she said, rushing into the bedroom after Jake.

I waited a minute, then took the time she was gone to go to the bathroom and scrub the make-up off me, then back in the living room to take her clothes off and put mine back on. I folded her clothes up and left them on the arm of the couch, and was about to leave when Lana came back out of the bedroom.

"Everything ok?" I asked.

She frowned. "Ok, I didn't expect that. He's worried he's 'a fag' now," she explained.

"Why? He didn't suck MY dick," I said, confused.

"Well, I asked if he liked it, and he said it was the best head he'd ever gotten. But he's all upset that he did like it," she explained.

"Well, that's awkward," I said.

"Yeah," she said worriedly. "I'm gonna have to convince him that it's ok if he liked it. After all, a mouth is a mouth, whether it's a guys or a girls."

I didn't respond. I didn't know what to say.

"Um, you wanna hang out here? I may be a while in there with him," she asked.

"I'd better bail," I said. I was still really fucking horny and getting hornier by the second.

She kissed me on the cheek. "Ok. Come back by later, or tomorrow?"

"Sure," I smiled. I walked out of her apartment as she went back into the bedroom, and headed straight to Paul's house. I needed a hard fuck, and Paul was the man who could provide it. Luckily for me, he was home.

When he opened the door after I knocked, I breezed in and immediately dropped to my knees behind him. He closed the door and turned towards me. "What's up?" he said, confusion in his eyes.

I didn't say a word, just fumbled with his pants until I got his dick out and went to town on it. He was hard in a matter of seconds, and I made sure it was dripping wet with saliva.

I stood up, dropped my pants and turned away from him, putting my hands on the back of his couch. "Fuck me," I moaned.

My need must have been obvious enough to affect him. I felt his cockhead press against my asshole, and he shoved himself into me in one motion. I yelped at the pain from his violent entry, but didn't stop him. In seconds, he was pounding me hard, his cock pistoning in and out of my ass.

I stroked myself as his hands gripped my hips painfully hard, his cock pounding me fiercely. It took no time at all before I came, ropes of cum shooting out of me harder than I'd ever felt before, leaving trails of white on the back of his couch.

He kept pounding me, shoving himself into my ass hard enough to raise my heels up off the floor. I heard him grunt, felt his cock swell and throb inside me. I swear I could feel his cum blasting out of his cock into me and the mental image of his cum filling me almost triggered a second orgasm.

His motions slowed, then stopped. Gingerly, he pulled his cock out of my ass and I felt a flood of his cum seep from my ass. He took my hand and led me to his bedroom. I made a side-trip to the bathroom to clean his cum off of me, then undressed and slid myself against his nude body in the bed.

"So, what the hell was that about?" he asked with a smile.

My hand found his half-hard cock and stroked it while I told him what had happened at Lana's apartment. By the time I was done explaining he was hard again and I straddled him, sliding my bruised asshole down his turgid shaft. The mixture of the ache from the violent fuck I'd just had, and the pleasure of being stretched open again was...is there an adjective that was stronger than "incredible"?

I rode him until I came a second time then he urged me off of him, saying that he probably wouldn't be able to cum again for a while. I snuggled up to him, my head on his shoulder.

"You're not going all girly on me, are you?" he asked. There was a note of concern in his voice.

"I don't think so," I replied. "Why, would it bother you if I did?"

"Well..." he drawled out. "I'll just come out and say it. If I wanted to fuck someone that looked like a girl, I'd fuck a girl," he said bluntly.

While what happened at Lana's was pretty much her idea and being dressed in her clothes wasn't a particularly exciting thing for me, his words irritated me a bit.

"Lana asked if you were my boyfriend. Are you?" I challenged him.

He pulled away from me and sat up in bed. "Look, I love what we do together," he said. "But I wouldn't go that far to describe our relationship." I sensed a hint of callousness in his voice. I wasn't seeking out a relationship, but after all the times we'd fucked I thought there was something growing between us...besides our dicks, of course.

"So do we need to cut this off before it gets a bit too serious?" he continued, frowning.

I didn't respond. As I said, I wasn't seeking out a relationship, but I realized that I did want more than just jumping into bed with him. At the same time, I didn't want to give up on sex with him. I loved his cock pounding into me.

"I mean, it's not like we're exclusive like Matt and James, right? You've got that guy at work and your sister's boyfriend, and I'll admit I see other guys on rare occasions," he said, quickly. I got the impression that he didn't really want to give up fucking me, either.

"No, I guess not," I admitted. I got out of his bed, and put my clothes back on. "I'll see you later?" I asked.

He didn't answer, just nodded. I left, and my mind raced on the drive home. I didn't want a boyfriend, right? I realized I was turning into quite the slut which frightened and excited me at the same time. I liked John's dick, and Jake's was even better. But Paul...he was something special, and the only guy that fucked me.

Halfway home, I turned and headed to Lana's apartment. I needed to talk to someone, someone that I trusted that could help me sort everything banging around in my head.