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First Times are the Best Ch. 01

By: jx88



This was a fantasy of mine for a long time. I had fantasized about men's dicks off and on for a long time. I even got off on some anal toys eventually too. But I never had the opportunity or knew where to look for a real guy trying to get off. For a while it grew into me fantasizing about men while looking at pictures of hung guys' dicks and guys getting blowjobs from women.

But when I realized there were gay ads on craigslist shortly after becoming single I found my opportunity. I found a simple post with the title "Top needs to get off". The post itself had a picture of a dick, which was about 8", a little more impressive than mine. The description said something along the lines of "Looking to host tonight. Be D/D clean, prefer thin/fem.".

I pictured myself sucking, licking it, etc.,. I figured I'd better go with it and see if I really am missing anything. I e-mailed him with a picture of myself just telling him I was interested. He quickly responded with his phone number and just said to call. I was so nervous I could barely dial the number, but I managed. He said "have you done this before?"

I said, "no."

He continued asking, "are you sure you want to do this?"

I said, "yes." I hardly said anything on the phone. We agreed to meet at 9:00. He gave me his address and told me to call if I get lost or anything.

It was 7:00 now, so I had a little time to prepare. I hopped in the shower right away. I thought to myself I want to be as feminine as possible. My pubic area was already shaven, so I started to shave my legs. It was tougher than I expected, but I got most of it done. When I got dressed I put on a pair of panties that were left at my apartment from an ex. Over that I put on some tight jogging pants from when I was younger and a tee shirt.

I left for his place around 8:15. I knew it wouldn't take that long but I didn't want to be late. I found his apartment pretty easily, which was in a pretty rough area though. I was pretty nervous about the situation. I was thinking of all the things that could go wrong or why I might regret this. I left all my stuff in my car, except for the keys, and locked the door. I knocked on the door gently. He answered immediately, thank God. He had some jazz playing, and looked to be quite a knowledgeable reader judging by the number of books filling all the walls. He introduced himself as Jason. He was a pretty average looking guy, wearing business casual clothes. He asked, "do you want a beer?"

"Sure."

He brought me a Heineken and we both sat down on two separate couches facing each other. He asked about where I'm from, what I do for a living, etc.,. He touched himself now and then during all this small talk. I kept thinking of that picture of his dick. It felt like foreplay to me, but I wasn't sure if it was suppose to be or not. After we finished the first beer, he asked, "so what made you realize you want to try this?"

I quickly answered him something about my fantasizing about it. I was trying to predict where it'd go from here. I asked about him.

He said, "my friend growing up told me he's gay in high school. He sucked my dick and I've been into it since. Are you single?"

I answered, "yes." I wasn't sure if he was considering dating me or what. But I asked, "what about you?"

"No, my fiance lives in a different state. I'm just here temporarily for work. She has no idea. So how about we do this." My heart jumped having heard this. He started undoing his belt. I took this as a cue to get into my position. I got down between his legs and on my knees, kneeling in front of him. He pulled it out. It was already big and hard.

I always pictured my first blowjob to start by sucking the guy's balls, but he had his hand rubbing his so I intended to start with his dick instead. I was still pretty nervous, though excited with all the anticipation. I grabbed his dick and felt the whole thing up and down a couple times. I looked up at him to see him looking down at me. I told him, "I've never felt another guy's dick before, I love the feeling."

He told me, "you'll get used to it."

I finally put my mouth to it. He moaned a little immediately. I felt the head in my mouth and started swirling my tongue over it. Then I started bobbing my head. He guided my head gently. I closed my eyes and put more concentration into it. I tried going deeper in my mouth but I gagged just a little. He said, "hold on."

I removed my head from him as he stood up. He pulled his pants down to his ankles and sat back down in one quick move. He grabbed my head and guided me lower, and told me "start sucking these."

I extended my tongue, and licked between his balls. I tried to get one of them in my mouth, but to not avail. His moans were noticeably louder when I licked them.

I continued licking his balls for a minute or so before continuing on his dick again. He said, "stand up for me."

"OK," I said as I stood up.

"Take off your pants, if you don't mind. Get comfortable."

I started by taking off my shirt. He reached for my chest and felt around. Then I took off my pants with relative ease. I saw him notice the panties, to which he just smiled. He stopped me there, and pulled me toward him. He put his mouth on my left nipple and started sucking. I wrapped my arms around him. He took his hands and put them on my ass. He started feeling up and down.

He turned me around and pulled the panties down to my knees. He said, "you have a nice, feminine bubble butt," he said. If you come over again, we'll go a little further." He then stood up, and I felt his dick between my ass. "Go back to what you were doing before."

I felt dirty but pretty turned on having the panties around my knees at this point. I kneeled in front of him again. This time I licked his balls right away. His moans gained some momentum, and then I went to bobbing my head on his dick. This time I tried doing it with much more confidence. I went faster and a little deeper. I tasted the saltiness of his pre-cum.

He said, "lick my balls again." I complied eagerly. He stroked his dick for a minute or two while I was doing that. I was really into it at this point. He whispered, "I'm going to cum!".

I wasn't sure what to do! I hesitated and felt a little get on the very top of my head. I opened my mouth wider and got into position to catch it in my mouth. I felt several large spurts of cum land in my mouth. I had the urge to swallow it right away. But I tried waiting until he was completely done, to show it all off to him as a badge of honor that I am swallowing all his cum. I looked up at him and smiled with a huge gulp. I ran my fingers through my hair to taste the little bit that escaped. I licked the length of his dick a couple times, which made him moan.

When I felt him go completely soft I stood up. We both got dressed. He asked, "how was it?"

"That was great. I wish I didn't wait so long to experience that." I went home, very content with myself.

First Times are the Best Ch. 02



I had recently given my first blowjob to another guy. A few days went by of me playing the whole thing in my head, fantasizing about it going further. I kept fantasizing about the feel of his dick in my hand, and then the taste of it in my mouth. I wanted him to know how much I cherished that taste. I knew he knew my phone number, but I didn't know to call him or wait for him or what.

As the weekend approached, I got a text message from him that made my heart race. It said, "Hey boy. You ready to come over today?"

I responded, "Sure. What time?"

"Any time after 6." I felt that same nervousness I did the first time, but this time I was full of eager anticipation having a good idea of what to expect.

I had plenty of time to get ready, but of course it was hard to contain myself. I went straight into the bathroom. I figured I must've looked alright last time for him to call me again. So I wouldn't deviate from that routine much, if at all. I hopped into the shower. My face and legs were pretty smooth, but I decided I better shave everything again just to be as smooth as possible for him. My face, legs, and most especially the area between my legs, I made sure were exceptionally smooth. I put on the one pair of panties I had, and used two mirrors so I could see how feminine I looked from behind with them. After being satisfied with that I put on a tee shirt and some jeans. I felt like it wasn't the right thing to wear, though I wore something similar the first time I saw him. There was no 'right' thing to wear for something like this.

I got into my car. This time I knew where to go and headed straight there. I knocked, and he discretely let me in. He had a tee shirt on and some boxers. He said, "looking good."

"Thanks."

"So you like it? I mean obviously if you're coming back for more," he said.

"Definitely, I wish I had that experience sooner." I felt shy around him, but I was still able to open up to him that much.

"Good. Do you think you're ready for anal?" he asked.

"I guess. I've been fantasizing about it a lot."

"Lets get started." He pointed between his legs as that was my cue. I kneeled there between his legs. I pushed them apart slightly. He grabbed his dick and pulled it out of his boxers. I moved my head towards it and licked the tip. He grabbed the head and held it upwards, so I licked up and down his shaft. When He released his dick from his hand, I immediately put my head on the head. I grabbed it from the base and started bobbing my head on it. I felt much more comfortable with it than the first time.

His moaning became louder and more frequent. He lifted my head up and pulled me into his bedroom. He started pulling his clothes off, so I did as well. We faced each other. He put his hands on my ass, and slid a finger up and down the middle. Once it reached the center, he circled my hole with it. He asked, "are you sure about this?"

"Definitely."

"It will hurt a little, especially in the beginning."

"That's all right," I said.

He grabbed a towel and placed it on his bed. I stood there watching him, until he told me "lay down on your back on it." I laid there, right on the edge. I lifted my legs into the air as I saw him move his head to my ass. I felt the wetness of his tongue on my ass. He moved it around the center but swirled it closer and closer. It helped ease the tension out of me. The tongue provoked a lot of sensations in me, but ultimately it was a tease.

He stood back up, and I watched him put on a condom. "You ready?" he asked.

"Sure," I said as I grabbed my legs tighter. My ass was at the edge of the bed in anticipation. I watched him grab a bottle of something, I assume was lube, and he rubbed it on his dick.

He moved so that he was facing towards me now. He leaned in, with his dick in his hand, and I could now feel it stabbing me. At first it was some pokes in vain, giving a little sharp pain. I tried to relax myself now, putting my trust in him. I felt it enter finally. I moved myself closer to the edge as I wanted all of it in me. It slowly went deeper until I felt his body pressing against mine. He pulled it out halfway, slowly, and went back all the way in me. This happened several more times, progressively faster. After a minute or so it was at full speed. I was hungry for it, and getting it was everything I was craving. He thrusted in me harder and harder. He leaned over on top of me and kissed my neck.

My legs were over his shoulders. For a moment I became aware of how glad I should be to be flexible enough for that. I put my hands on his ass to pull him closer in the closest point of each thrust. Sometimes he would slow down for a minute and then speed up again.

After some time, which I have no idea how long it had been, he started going much faster and harder. I was moaning with all the thrusts.

"I'm going to cum," he said.

I thought if there was something I'm supposed to do at that point. But ultimately I let him continue while trying to pull my legs closer to me. I felt a warmth through the condom. First it was one big burst of warmth, and then several smaller bursts of warmth after another. It wasn't quite as it was when I had swallowed, but I did feel a certain honor in him having his way with my ass.

He pulled it out slowly. It popped out like a cork from a wine bottle, it fit so well. He asked, "how was it?"

"Great," I said, as I watched him leave to throw away the condom in the bathroom. For a second I thought to myself of asking for the condom, so that I could swallow the cum from it. But it was just a fleeting thought, or at least I chickened out not wanting to appear 'too kinky' with all this being still new to me. When he came back from the bathroom though, I grabbed his dick and licked what cum remained smeared all over it.

"I see that," he said.

I left glowing that night. I know I didn't get off, and I often wondered if I'm only interested in being the bottom then when will I get off? But I was content. I had no desire to get off by cumming. Having a man's dick inside me, penetrating me, got me off. Having a man shoot his sperm while inside me got me off.



First Times are the Best Ch. 03



I've had a couple gay experiences now. Whereas before I had fantasized about doing it but didn't know if I'd actually like it, now I not only crave it but had experiences to re-live in my head while anticipating my next adventure.

I answered a phone call from my ex girlfriend Liz. "Hello."

"What's up?" I asked.

"Bored, watching TV. Anything new with you?" she asked back.

"No," I answered.

"Why don't you get a pilot's license or something so you can tell me something excited," she said while laughing.

Liz was a very dominate girl, who required someone more dominate than her. We didn't work out well in a relationship, but as friends we got along great. In retrospect, maybe that was a hint of possible gay experiences to come. Anyways I could trust her. "Well all right. I'll tell you something good if you don't tell everyone you know or whatever." I felt nervous and kind of regretted it.

"Goodie! Tell me!"

"Well, to put it simply, I've realized I'm bi. And I've acted out on it."

"Really? You? Acted it out, how?" she asked.

"Yeah, well I've had two experiences so far. First time I gave this guy a blowjob," I told her.

"What?!" she asked, shocked.

"Yeah, and he did me. It was great." All the nervousness left my body now and I was able to say that out loud calmly.

"Did you fuck him back?" she asked.

I thought to myself for an instant how less manly that makes me look to her, and even though I kind of wanted her back still just one more time I knew it was hopeless. "No. I don't really care to fuck a guy. I just like being on the receiving end."

"Wow, I can't believe you. I would have never guessed. How big was he? Have you been with anyone else?" she asked.

I responded, "no, just him. He's slightly larger than mine."

"How did it feel inside you?" she asked curious.

"It was great. He wore a condom but I could still feel the warmth from his cum in it."

"When you sucked him, did you swallow?" she asked.

"Most of it yes, a little got on my face." I was kind of turned on just talking about it all.

"I hate when a guy cums on my face. It's so humiliating and degrading," she replied.

I didn't want to admit it, but the thought of a guy intentionally shooting his whole load all over my face turned me on. I accepted I liked the humiliation aspect of it, if that's what it was. I merely replied with "well it's not a big deal to me."

She told me, "you're fucking with me aren't you?"

"No, I don't know if I should have told you or not in the first place so if you don't believe me then that's all right."

"I gotta see you do it," she said.

I was instantly turned on by the thought of her watching it happen. I didn't know if Jason, the guy I had all these experiences with, if he would mind. I told her though, "all right well I'm looking forward to it."

"I gotta go," she said and quickly hung up.

A day went by. I checked my phone around the afternoon, and saw a text message from her saying, "get your ass over here."

She lived about 10-15 minutes from me. I drove to her house, just casually without a thought of yesterday's phone call.

I got out of my car and knocked on her door. She answered in a large tee shirt and a pair of panties. "Hi."

"Hi," I responded kind of shy, not that she was some sort of stranger, but I just realized I had no idea what she was planning.

"All right be honest with me. Were you serious last night?" she asked.

"Yeah, why?"

"I want try some things with you."

"Like what?"

"I want to fuck your ass!"

The bluntness eased the nervousness I had. I laughed, "with what?"

"A dildo. I can't fuck you with my pussy obviously. Come, I'll show you."

I followed her to her bedroom. She reached into a shoe box under her bed and grabbed a red penis shaped dildo. It was about the same size as me, maybe slightly thinner.

She turned on her computer monitor. She said, "first I want to get into the mood." She opened up a web browser, and went to some porn site. She asked, "do you like gay porn?"

"Not especially, I like watching regular sex. Well mainly anal or oral, because I like picturing myself as the girl in those videos." I was completely honest with her and so turned on being able to talk about it openly with her.

She clicked a video of a guy getting a blowjob from a sexy Latina looking woman. I told her, "that's the perfect sized dick to me right there."

She got on the bed and laid down. I laid down next to her. She said, "you really are all about dick aren't you?"

"I like it all," I mumbled.

"Take off your clothes," she said.

I did as she said. I felt mildly comfortable at this point. "All right. I just have two requests. I want to start off by sucking it and I want to wear something girly if you have anything." I felt kind of embarrassed asking this but she said nothing and got up and went to her closet. Fortunately for me, even though now she's a skinny girl that's a lot smaller than me, she used to be larger and still had some larger clothes that could fit me.

She came out with a long dress, a skirt, a pair of panties, and a shirt. "Is there any certain kind of look you're going for?"

"Like a dirty slut," I shyly said.

She threw the skirt and panties at me. She went back in the closet and grabbed a different shirt. It was all black. I thought to myself wearing the dress would have been pretty lame. I put the stuff on real quickly. I felt odd wearing her clothes but I tried to ignore that and embrace being feminine as much as I could.

"All right, lets see you suck it," she said. I got on my knees, but she quickly injected, "just lay down."

I did so. And she laid right beside me. She took the dildo in one hand, and put it over my mouth. She asked, "how much can you take?"

I didn't say anything, and she started to put it in my mouth slowly. She pulled it out all the way, and looked at me closely. I lifted my head up to get it back in my mouth as a signal for her to continue. She dipped it back in my mouth, a little faster. And faster, and faster. She tried going a little deeper too, each time. I started to gag but I didn't resist.

"Is that all you got? You're only about halfway." I really wanted to get all of it in my mouth but I couldn't.

I gagged a little harder after putting more effort into it. She withdrew it. "Lay on your stomach," she ordered.

I felt eager to obey. She rubbed my ass through the panties some. She spanked my ass a few times. Each spank was harder than the last. She finally moved the panties between my legs to the side just enough and slid her fingers up and down.

"Very smooth I see," she noticed.

"Yeah, it makes it better that way."

She became quiet again. I felt her probe around my ass with the dildo. She came across the entrance and slid it in, just barely. She pulled it out and ventured back in just a little more. She repeated this several more times. I reached for my ass and spread it apart. I wanted it to happen so bad, even if it wasn't a real dick this time.

She finally managed to get it all the way in me. "How does that feel?"

"Great," I said as I moaned softly.

She sped up some. After a few minutes, she was going faster than the guy was who pounded me. It was still that wonderful sensation however. I lifted my ass higher to get more of it. My dick came out of the panties and she gripped it with her other hand. I felt like I was in her mercy now. She was moving the dildo really fast, and started stroking my dick at the same time. It didn't take long until I shot a large load onto the bed. It was intense and happened with no warning. After a moment I felt bad having done that right on her bed. I felt her pull the dildo out of me one last time.

"How was it?" she asked.

"That felt awesome."

"Great. Now you can do me a favor." She got off the bed, and I just watched her. She pulled off her panties, and got back on the bed. I knew what she wanted now. She straddled my face. I reached up to her clit and licked it some. She was very clean, and I loved eating her all out. I licked it, flicked it around some, and tried fingering her while doing it as awkward as it is while being straddled like that. She reached her climax quickly though and got off.

"I still want to see a guy fuck you, you know?"

"All right, just find a guy," I said.

"Oh don't worry I already know someone. He's Keica's friend. Last night I told her and she told me her friend Chris is into guys. He's seen a picture of you already and thinks you'd be some good ass."

"You told someone else about me?!" I asked, mildly upset.

"It's only Keica, I had to tell someone, and I tell her everything." 

I felt compelled to ask more details about him but I didn't. I left her house with that in the back of my mind.

A couple days went by. I wasn't sure if she was serious about watching me or what. But I received a phone call, "can you come over?" Liz asked.

"Sure." She never had these things planned in advance, it was always now or never. "Should I be expecting something when I come over?"

"Yeah, a big dick," she laughed.

I heard a masculine voice get on the phone, "do you suck dick?" It must've been Chris.

"Yeah, and swallow," I said, surprised by the bluntness.

"Cool," he said. I kind of wondered where they found this guy.

Liz got back on the phone, "all right come over!"

So I took a shower, shaved myself very thoroughly, and went over there in casual clothes. I met Chris. He was a tall, skinny guy. Liz looked flustered the whole time and was constantly in the middle of everything.

"What's up?" he asked.

"Not much."

"All right, lets get started." Liz was always impatient with these things. "I know you like being girly or whatever so I have something for you to put on on the bed."

I immediately went into there and changed quickly. It was a green dress, just low enough to reach the bottom of my ass. I went along with it. When I was just about finished Chris and Liz came in.

They sat on the bed next to each other. Liz pulled Chris's head to her breasts as he reached up and squeezed one. He then slid his hand under her shirt and lifted it. Then he proceeded to put his mouth on her breasts. I sat there watching, kind of confused whether I was suppose to be watching this for foreplay or what. But she interrupted him and pulled his sweat pants down just enough to pull his dick out and aim it towards me, as a hint.

I got on my knees while he returned to smothering his face with her breasts. I took his dick in my hand and put my mouth around it. It was the biggest one I've had yet, not that I was well experienced or anything. It really was quite impressive though. I saw out of the corner of my eyes Liz open her eyes real wide and stare with her mouth wide open. I kind of ignored that though, and just started licking up and down the length of his dick.

I started bobbing my head on it. He lifted himself off the bed a little, just enough to pull his pants all the way down. I used this opportunity to lick his balls some, which I saw Liz noticed that too.

They started moving around some, so I stood up. Liz commanded, "bend over on the side of the bed."

I did so, while she climbed onto the bed. She took her tight black pants off, and spread her legs around my face. Meanwhile Chris was behind me. I felt him put his hands on my hips. I knew where this was leading.

I saw Liz's pussy right in front of me, but I felt Chris's dick begin to penetrate me and I had to wait for him to enter before I could begin to concentrate on eating Liz all out.

But Liz being Liz, she pulled my head towards her forcefully anyway and I stuck my tongue out. Chris entered me at the same time, and began thrusting away. It was a little more painful this time, and also the first time I was going bareback. Feeling him in me was awesome though. This was the best of both worlds.

I squeezed Liz's ass and pulled her close to my face. I felt the pounding getting harder and harder. Liz's breasts were bouncing as I was being pounded. I think it may have contributed to her experience. Chris had one hand feeling around the dress, which made me feel like a slut being used. And I loved that feeling. I felt his dick push deep into me, real fast. After some time went by, he gave me warning, "I'm going to cum" with some groaning.

I felt the squirting in me. Liz looked up at us with curiosity. After Chris was done, she put her head back down and I went back to eating her all out, with more concentration this time. Chris pulled himself out of me, and got dressed quickly. When Liz reached an orgasm, I laid on the bed, relieved. I felt the cum in me, leaving me with a sense of euphoria.