First Time with a Man

Jake was a good friend. I was really young and he was middle aged, but we got along well. He started out as the friend of a friend but when I moved to a house down the street from his apartment, we hung out more and got to know each other better.

But in those first couple of years of our friendship, there was obviously something troubling him. I knew he was divorced and he didn't like talking about it. He was single and that seemed to bother him, too.

One day, Jake came over and said, "I want to talk to you. Want to take a drive?" We got in his pickup and drove out to the highway. At first we just chatted and laughed a bit, but then he dropped the bomb.

"I'm gay," he said.

My response was a little dumb, I'm afraid. I said, "That's great!"

Not exactly what he was expecting, but I was sincere.

"Now you can have an awesome sex life," I said.

"You think so?" he asked.

"Well, gay men get laid, right? Straight guys struggle to find a woman who will let them fuck them.. unless you're a rock star. But for most guys, they have to play a lot of games before they can finally have sex. Don't gay men get right to it?"

He laughed.

"Yeah, I guess that's true," he said.

"Did you tell your ex-wife?" I asked.

"Yeah, I did," he said. "She kind of suspected. That's what ended it all, really. I couldn't get it up for her. Now all is forgiven and we're friends again. It's been really positive for me."

I thought about it for a moment.

"Is that why your phone got turned off?" I asked. I knew that six months earlier, his phone was turned off because he hadn't paid the bill. I offered to help out, but I didn't really understand what had happened.

"Yeah," he said and sighed, clearly embarrassed. "I called phone sex lines like crazy, talking with guys. I couldn't get enough. I built up a huge bill and couldn't afford to pay it."

"That sucks, man," I said. "Are you okay now?"

"Oh yeah. Now I find local guys online and we talk and then we hook up."

"You're having fun, huh?" I said.

"A lot of fun. I'm having the time of my life now, meeting guys and finally living out my fantasies."

"I'm jealous," I told him.

"Not getting laid?" he asked.

"No, I'm not," I said. "Remember Kelly? I wined and dined her for months. We kissed a lot, but it was frustrating, trying to get her to fuck. I think she liked leading me on. I got sick of it. I ended up getting online and jacking off all the time, just out of sheer frustration."

"It can be tough," he said. "Honestly, Kelly was a horrible tease. I wish she hadn't done that to you. Why not come over to my team and find out what real sex is like?" He laughed.

"Yeah, that's good advice," I said. I laughed too but I wasn't really kidding. Maybe he knew then.

Over the next few months, I experimented more online. I got some courage and started going to chatrooms that were exclusively male. It didn't take long before I was totally hooked. Those guys were so hot, so horny and they were willing to do everything I fantasized about. My minor fantasies about sex with men blossomed into an obsession. I felt like I was being converted into some kind of shadowy group and I was fully accepting. I loved that these men were seducing me, filling my head with intense fantasies. I got online every night and stroked my dick, typing with my left hand, talking with men who were ready to get into it immediately and do everything they could to make me cum over and over.

Then I started calling guys. I met a few local guys in the chats and they persuaded me to call. They sent me pictures, showing off their bodies and their big cocks. I'd chat with a favorite guy and then give in to his request to call. We'd jack off together and talk about our fantasies. I was completely hooked. I got naked and shot hot cum all over my abs night after night.

One day I couldn't take it any more. I had to do it for real. I called Jake and told him what I had been up to every night. I was nervous but he made me relax.

"Listen, man," he said. "You're going through what every gay guy goes through. You get curious and eventually you know that you need it. You have to get naked with men, suck cock, and you might end up wanting to try anal, too. Every guy gives in to his urges at some point."

"I have all of these fantasies," I said. "When I started chatting with guys, I didn't think I'd want to be penetrated, or fuck a guy. But over time I've gotten really horny about it. I want to try it and see if it's as good as I imagine."

"It is," he said. "You're about to have some amazing experiences, feeling what men can do with each other. At first, I wasn't one hundred percent on bottoming or fucking a guy. But I've done it a lot now with a bunch of guys and it's an incredible feeling. You're going to love fucking men."

"Wow," I said. My dick was so hard. "I'm going to do this, aren't I?"

"I'll find the right guy for you," he said. "What kind of guys turn you on?"

"Oh that's easy. Mature men, middle aged guys who are really fit and handsome. I watch a lot of young-guy-older-guy videos, watching these daddys seduce horny college boys. That's my favorite."

"I think I know just the right man for you," he said. He paused for a moment. I thought we were going to start jacking off together.

"You know, I'm a middle aged guy," he said. "And you're college age. You're a hot man, too. I've always thought you were really attractive."

I was stunned, but what he was saying made my dick leak.

"Oh fuck, Jake," I said. "I don't know."

"That's cool," he said. He laughed a sinister laugh. "I'll have you some day."

He told me he'd get in touch soon.

"Don't get too nervous about this stuff," he said. "You're about to do something that's going to make you really happy. I know from my own experience, when you finally take the plunge into real man-on-man sex, you never regret it. In fact, it's going to make you even more hungry for it. Now get back to your computer and your phone while I find the right man for you. Let those guys know you're about to fuck for real. And don't stop with the phone calls. Call those guys every night and stroke and have fun. Tell them you're playing with your ass while you're talking. They'll love it."

"Okay," I said.

"Do you have a dildo? Have you taken that step yet?"

"No, not yet. If I had a dildo, I'd probably wear it down to a nub."

"You're so hot, man," he said. "I'm glad we've got you on our team now. Do you send pics to these guys? Do you show off your dick?"

"I have a few dick pics. I've gotten some really flattering feedback. I need to get a pic of my ass or maybe my abs drenched with cum and send that to my favorite men."

"Damn, you're a sexy guy," he said. "I'll get back in touch soon."

The next day he sent me a message. "Cum over to my apartment now. I found the man for you. His name is Alan."

I went to his place immediately. I walked in and saw his sly smile.

Then he did something that caught me totally off guard. He wrapped his arms around me and gave me a deep tongue kiss. After a second of shock, I got into it. I couldn't resist.

"Oh wow," I said. "That was nice."

He led me to his computer room and sat me down. I watched the screen while he clicked the mouse and brought up pictures of Alan. Alan was so hot, with a perfect body and nice beautiful dick. Jake clicked and the images came up. There was Alan in a swimming pool, naked. Then he was sitting on the couch in shorts with a bulge. One picture was just his face, smiling. He was on a beach.

"See that?" Jake asked. "Look closely."

In the background of the beach picture there were naked men.

"That's Alan at his favorite nude beach, in Florida," Jake said. "He looks really happy, doesn't he?"

I couldn't speak. I was entranced.

"He's local?" I asked.

"Yeah," Jake said. "He's local and he's ready for you to come over."

"Does he live alone?"

"He does. It will be just the two of you."

Then Jake clicked one more time. A video popped up. The screen was filled with Alan naked and rock hard. He started stroking. He smiled and then he closed his eyes and pumped harder. He groaned a little bit and then he shot a huge fountain of cum. He covered his fist and his dick with semen and relaxed. He put his wet fingers in his mouth and smiled, licking up a few drops.

That made me crazy.

"When do I get to meet him?" I asked. "I think I might have to go home now and jack off. Can I have these image files and the video clip for my computer?"

"I'll send them to you," Jake said. "But you're going to taste that cum soon so you won't be needing videos. You get the real thing."

I rubbed my dick through my jeans.

"Is he top of bottom?" I asked.

"He's everything you want," Jake said. "He'll make your fantasies come true."

I was feeling crazy. Jake watched me rub my cock through my pants.

"I'm going to call him," he said. He got the phone and called while I clicked on the video clip again. I heard him say, "Hey man, it's me. I've got your new lover right here. Want to talk to him?"

Jake handed me the phone and he left the room.

"Hey, son," Alan said.

"Oh man," I said. "It's great talking to you. I'm watching this video of you and I saw the pictures. You're a really hot guy."

"Jake says you're ready now. Is that true?"

"Oh yeah."

"And you're into middle aged men? I'm not a young buck like you."

"You're the perfect age," I said. "The kind of man I fantasize about. I go to chatrooms a lot and go to the room where mature men meet young guys. I love it."

"Those older guys send you pics?" Alan asked.

"Some of them have. Then I send images to them of my hard cock, ready for their mouths."

"What do you think of anal sex?" he asked. "Is that something you want to try? Jake said you mentioned it to him a few times."

"I want that really bad. I want to feel a guy inside me and I want to get him on all fours and grab his hips and slide into his hot ass."

"Wow," Alan said. "You're definitely ready for this. I'm going to make you feel so good, son. Better than you've ever felt. Have you heard of poppers? Amyl nitrate?"

"I've heard about it but haven't tried it."

"You'll try that, too," he said.

"You're driving me crazy talking like this, Alan. I need to stroke with you right now."

"Get naked for me, son. No clothes. Not just your pants around your ankles. I'm getting naked, too. Daddy's going to make you feel good. Everything you've dreamed about."

I took my clothes off, spat in my palm, and stroked my big cock.

"I'm doing it for you, daddy," I said. "Guide me anywhere and I'll follow."

He moaned quietly. "I'm stroking, too. Where did Jake go?"

"I'm not sure." I got up from the chair and took a step out of the room. I could see Jake in the living room wearing nothing but shorts, on the sofa. The TV was on. I sat back down.

"He's in the living room. I think he's watching porn."

Alan laughed. "Sounds like my Jake. He can't get enough of that stuff."

We stroked silently for a moment, savoring it.

"Listen," he said. "I'm coming over there right now. Tell Jake, okay?"

"Okay," I said.

Jake's eyebrows lifted when I stepped into the living room naked, with my dripping penis in my hand. I saw the TV screen where there were a couple of sexy young guys fucking.

"Alan says he's coming over," I said.

"That's good," Jake said. "I'm going to get out of here so you can be alone together."

"Maybe you could stay," I said, with visions of a threeway in my head.

"No, it's going to be just you two for your first time. I think that's the best way to do it."

I went back into the computer room and sat down.

"Get over here, daddy," I said into the phone. "He's leaving."

"Okay," said Alan. "I'm on my way."

Jake didn't leave immediately. First he went into the bathroom where I think he orgasmed and cleaned up. He got dressed and grabbed his truck keys. Then he stood in the doorway and looked at me.

"Alan's going to want to play with your ass," he said. "You're a virgin and that really turns him on. He was my first for anal sex and he knows how to make it amazing for a first-timer." He paused for a moment. "You look so good, sitting there naked with that fat dick in your hand. Alan's a lucky guy."

I spread my legs and stroked for him. Our eyes locked while I did it. Then he left, quietly closing his apartment door.

I didn't wait long. Alan walked in the door right away. I walked out to meet him in the living room. He closed the door.

"Hey, son," he said.

"Hey dad. I'm ready for you."

"I can see that. Sit here on the couch."

I sat down. He took off all his clothes in front of me. I could barely resist the urge to drop to my knees and take his dick in my mouth. He sat next to me, then leaned over and we kissed. He touched my penis while our tongues wrestled, wide open mouths. I could feel his hunger.

He got his fingertips wet with saliva. His dick was throbbing.

"Spread your legs for me, okay?"

I spread them and he reached down and rubbed my balls. Then he went further and started to massage my asshole. I moaned and spread as far as I could. While he explored my ass with his fingers, I reached over and grabbed his asscheeks. I didn't even realize I was doing it at first.

"It's so good," I mumbled, eyes closed and feeling myself completely give in.

"I want to see you jack off," Alan said. "Show me."

He continued to finger me and I stroked. I loved putting on a show for him. Right away, I shot sticky cum all over my bare chest and abs. I made a mess.

"Don't stop, okay?" I said.

But he did. He stopping rubbing and penetrating me.

"Time to hit the shower," he said. "Let's do that together."

We left the living room and went into the bathroom, then we got into the shower together. Our erections bumped against each other in the hot water. Alan cleaned me up. Then we started kissing. I don't know what it was, but somehow that moment ended any second guesses I might have had. I felt more comfortable and more alive than ever before. I knew something was changing in me.

Alan reached down to the tile floor and got a rubber hot water bottle. It had a short tube and a ribbed nozzle at the end. He filled with warm, soapy water and told me to bend over. Then he gently slid the nozzle in my ass and got me completely clean. It felt good. I grabbed the bottle to return the favor but he said no.

"Not yet, okay? This first time we're going to explore your virgin ass. But I love bottoming with men, so don't worry. You'll get your chance."

I agreed with him. I would have agreed to anything at that point.

We got out and dried each other off with Jake's fluffy towels. Somehow, we both got the giggles for a moment.

"Let's go," he said.

We went into the bedroom and sat on the edge of Jake's big double bed, naked and hard. We kissed and Alan stroked me a little, lightly.

"You love this daddy-son fantasy, don't you?"

"It's kind of taboo, I think," I said. "I guess incest fantasies are not okay for some people. For me, that fantasy has always been a big part of my life."

"Did you dream of fucking your dad? Or him fucking you?"

"No," I said. "There wasn't any attraction there at all. He was an ugly, mean dude. I did have an uncle who everyone in the family whispered about secretly being gay. He was a really hot guy and I had a good relationship with him."

"Maybe it's not incest," Alan said. "Maybe it's just that you're into mature men and you get off calling them daddy."

"That's probably it. The taboo is a big part of it. That gets me going."

"Yeah, you grow up dealing with gay sex fantasies and you get an erection thinking about the sex you're not supposed to want. You must have grown up in a pretty closed-minded place."

I leaned over and gave him a long kiss.

"I'm in a better place now," I said.

He stroked my dick. Precum was bubbling out and he got some on his fingers and tasted it. He smiled.

"Son, get on all fours for me. Daddy needs that ass."

I got in the middle of the bed on all fours and lowered my head and closed my eyes. Alan got behind me and dragged his wet tongue down my shiny clean crack. He buried his face in my ass and started eating me out, rimming my tight asshole and drooling so much I felt his saliva drip off my balls. He grabbed my asscheeks and dove in deeper, devouring me. I had never felt anything like it. It was incredible, and I could feel him gradually lose control. I begged for more. I was shaking all over.

I was out of control and I broke away from him, moving around the bed, forcing him down on his back, and taking his penis into my mouth. I bobbed my head and shoved it deep, gagging on it. He couldn't hold back either and he moaned my name and started cumming in my mouth. I tried to swallow it but I just couldn't take it all. I ended up with a mess of semen on my chin.

We both laid back on the bed, breathing heavy.

"You're making me crazy," he said.

Then things got even better. The apartment door opened and we heard Jake come in. After a moment, he was standing in the doorway. He smiled.

"This is what I like to see," he said. "A couple of cum-hungry guys in my bed." He laughed. I watched him undress. He was hard and he looked really good. I felt like maybe they had planned this. Maybe they both wanted to eat my ass and fuck and feel me cum and this was the scheme they came up with. If that was true, they succeeded 100%.

Jake got on the bed with us, on his knees. I admired his dick. It was perfectly shaped and a little bigger than medium-sized. For a moment, I thought about how many asses and mouths that dick had been into. When we met, he wasn't so experienced. But now my old friend was a veteran.

"Alan, are you seducing another young guy? You should be ashamed of yourself, corrupting the youth like this."

"It's my specialty," Alan said. "Once I've had them, they never go back to women." He reached over and squeezed my nipple. "This one is a keeper."

I guess I was a little bit overwhelmed. This was going beyond my fantasies. Alan and Jake knew what I craved even more than I did.

"Do I play the daddy or the uncle?" Alan asked me. He rubbed my chest while Jake reached out and grabbed my cock.

"I don't know," I stammered. "Just let me be the young virgin." I started stroking Jake. His dick felt so good and I felt my lust increase. My need for cock was getting even stronger. Maybe I had wanted Jake all along, from back to when we first met.

"This is a nice cock, Jake," I said.

"Let's see if it fits," Jake said.

He put me on my back and held my ankles. Alan grabbed two pillows and positioned them under my tailbone. Jake forced me to spread wide while Alan held Jake's swollen dick.

"And now you find out what it's like to be a man," Alan said. He guided Jake's cockhead to my soaking wet, slick asshole. Jake started pushing in and I begged him to give me more. It felt amazing, taking it inside my ass. Alan had me all loosened up, ready for it. I gasped as Jake pushed all the way in, a little rough. He couldn't hold back and he wasn't going to be too gentle.

He pumped in and out of me while I moaned. Alan moved over on the bed and straddled my chest. He put a pillow behind my head, leaned down to kiss me once, and proceeded to fuck my mouth. He shoved it in deep. I took it all.

Jake started to moan louder, telling me he owns my ass. He let out a gasp and started unloading into me. It was a huge load, filling me up. Alan pulled out of my hungry mouth and stroked. He rubbed his big dick on my face. Then he started cumming, shooting on my lips and chin. His body shook and he said something about loving me until he finally relaxed and collapsed on the bed.

The three of us laid together, totally spent, just breathing. I was sweaty and sticky. I could feel cum dripping out my ass.

Jake got off the bed and stood up.

"Hey Alan," he said. "Did you let him fuck you before I came back?"

"No," Alan said. "This guy's special to me. I'm taking it slow. We have time for more."

"Some other day," Jake said. He leaned down and tried to clean my face. "Alan and I love to bottom for young studs like you. He pretends he's a top, but I know how bad he needs to get fucked every once in a while. You haven't done it all. Did you eat Alan's ass?"

I told him I hadn't had the pleasure yet.

"That's okay," Jake said. "We're going to keep coming back to you. Old Alan here tends to fall in love with guys like you. We're both going to want more, a lot more. We'll introduce you to a few friends, too. They're going to love you."

"Time to clean you up," said Alan. He led me to the shower. All three of us crammed inside and held each other in the water. Jake left early so Alan and I could make out. It was such a perfect moment, kissing after such a hot time on Jake's bed.

We got out and dried off, then we got dressed.

"You're going to think you fell in love after this," Alan told me. "That's okay. All kinds of ideas are going to pass through your mind after something this intense. You might even have a moment where you think 'Oh no, what have I gotten into?' Some gay men who have their first real sex try to get back in the closet because this new identity is a lot to deal with. So just go slow, okay?"

"I will," I said. "I'll probably call you and talk about how I feel. Is that okay?"

"Yeah, you should do that. I'm here to talk about anything. We're going to hook up again, and soon. Jake was right. You're my kind of man. Your incest fantasy makes me horny, too. We can explore that more, if you want."

"I'm ready to do that," I said.

We held each other and, reluctantly, I left. I went home alone and it felt terrible. I felt lonely. But I called Alan late that night and we talked for a long time. We got together the next day to pick up where we left off. We knew Jake was going to be back and we could resume our threeway. Alan told me about a lot of other things we could do together, like go to the park late at night at the spot where local guys meet for anonymous sex. We talked about visiting his favorite nude beach in Florida, too. I hadn't penetrated a man yet or rimmed a guy, so we put that on the top of the list of new experiences I needed to explore.