First Times Are the Best

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.