Sex Adventures with Alisha Ch. 05

NOTE: I am releasing parts five and six at the same time because the two chapters will likely appeal to different sets of readers. For anyone looking for man on man gay sex told from a man's point of view, this is the chapter that you want to read.

For anyone looking for a lesbian story told from a woman's point of view, skip on to Sex Adventures with Alisha part six to hear the story in Alisha's own words.

While this story can stand alone, reading the first four chapters of this series can give the reader some context to make the beginning more understandable.

*****

It was one of those nights. I bent Alisha over and kissed and licked and fucked her cute little ass thoroughly. Of course when I do that, I must bend myself over and let Alisha fuck my ass with her favorite strap on. That's the rule. I don't mind though. I love how Alisha's tight little butthole feels when it grips my dick. And very few things turn me on more than watching my cock slide back and forth between her firm little butt cheeks. Also, unlike Pablo's monster cock, Alisha's strap on is a much more manageable size. It actually feels good when she slides that toy in and out of me. She and I mutually fuck each other's asses about once a week.

This particular night was shortly after Alisha and I had swung with Kerri and Pablo for the first time. We lay back on the pillows after Alisha removed her strap on. My arm was wrapped around Alisha, and her head was in its customary position on my chest.

"Can I ask you something?" I said.

"What, Baby?"

"When we are with Pablo and Kerri, why do I always have to be the bottom?"

Alisha lifted her head off of my chest. "What do you mean?" she asked.

"I mean, why am I always the one getting fucked in the ass when we're with them?"

"Are you saying that you'd like to fuck another guy in the ass?"

"What? No! That's not what I'm saying at all." It really wasn't what I was trying to say. I wasn't interested in fucking Pablo's ass. I was trying to make the point that I wanted to fuck Kerri's ass. Any butt connoisseur who has seen Kerri's ass would know why I wanted to fuck it. It's amazing! Especially when she wears those tight little running shorts. I had tried to give Kerri some anal when we were at her house the previous weekend, but she wouldn't let me.

Alisha wouldn't relent though. "But would you fuck another man in the ass?"

I had to pause for a bit. I hadn't really given it any thought, but now that she brought it up...

"I don't know," I said carefully. "I guess if the opportunity presented itself, I might do it."

"Hmmm," Alisha said. She kissed me on the lips, and then lay her head on my chest again. "Good night, Steve," she said.

I didn't give that question any more thought that night, nor did I give it any thought the next day. I was still trying to figure out a way to convince Kerri to let me do her anally. After all, she had already pounded my ass with her strap on for my birthday. How in the world would I convince her that fair is fair?

Alisha and I prepared dinner at home the very next night. We like to go out to eat as much as the next couple, but we eat at home a lot because we are both really good in the kitchen. On this particular night, we had a roasted pork loin, baby potatoes, and asparagus. Over dinner, Alisha said, "remember what we talked about last night?"

I wasn't sure what she meant. We talked about a lot of things. It's what couples do. I asked her to be more specific.

Alisha took a bite of her pork loin. "You know. When you said that you would like to fuck another guy in the ass."

I couldn't believe that she was bringing this up again. "Alisha," I said, "I wasn't the one who brought that subject up. When I said that I didn't want to always be the bottom, I meant that I want to fuck Kerri's ass."

"Okay," Alisha said. "The next time Kerri comes over here, I'll help you fuck her ass." I felt a jolt of excitement at that news. "But let's get back on my topic," she insisted.

"Okay," I said. Once Alisha promised me that I'd get to fuck Kerri in the ass, I was a lot more willing to see where she was going with this conversation.

Alisha took a sip of wine, gave me a devilish smile, and said, "I've found someone."

"What?" I was shocked. "Last night was the first time you ever said anything about me fucking another man. And now you've already found one?"

"Mm hmm," Alisha said. "You're going to like him too. He's really cute."

I didn't know what to say. "Who is he?" I asked.

"His name is Kyle," she said. "He's a nurse that works in the same office that I work at, and he's a total bottom."

My head was spinning. I was pleasantly surprised when Alisha arranged for me to have a threesome with her and Kerri. I also enjoyed the foursome that we had with Kerri and Pablo. But to set me up with another man? This was a horse of a totally different color.

"Does he know?" I asked.

"Oh yes. I've told him all about you—especially your cock. He really wants to meet you."

"You've mentioned my cock to him?

Alisha took another sip of wine and giggled. "Of course I did, silly. When we girls get together, we always talk about our men's cocks. You didn't know that?"

I protested: "But Kyle's not 'one of the girls.'"

"He might as well be. He's a gay man who loves cock as much as we do."

I was flabbergasted. "So when is this supposed to happen?"

"Tomorrow night."

"Tomorrow night! And he's up for this?"

"Oh yes," Alisha said. "He's just had a nasty breakup with his last boyfriend, and he's going crazy. He's even talking about trying to get back with his ex just so he can have sex again. His ex is a real asshole, so I can't allow that to happen."

"So your solution is for me to fuck him so that he doesn't go back to his ex."

"Trust me," Alisha said. "He doesn't need to go back to that prick." I wondered if Alisha gave that double entendre on purpose. "But Kyle does need a good fuck. You'll be helping him out by giving him one."

I knew Alisha well enough to know that telling her "no" wasn't an option. "Alright, I said. If you want to watch me fuck another guy in the ass that badly, I guess I'll do it for you."

"Oh. I forgot to mention," Alisha said. "I won't be there."

"What?! You don't want to participate?"

"Oh, I do want to participate," Alisha said. "Believe me, Kyle's really cute, and I think that it would be hot to watch you two having sex. But Kyle would never go for it. He wouldn't want me there."

"Are you kidding me?" I asked. "You're beautiful! Why would any man not want you to participate in a sexual encounter?"

"Like I said, Kyle's a total fag. Plus, he's already told me that I'm not allowed in the room with you two. But, you can tell me all about it when it's over."

I sighed in exasperation. "All right. Fine. How is this going to work?"

"I'm going to give you Kyle's address," Alisha said matter of factly. "You're going to go over there at about 6:00. Kyle should already have some pizza ordered by then. You two can eat, get to know each other, and then"—she waved her hand in the air— "whatever happens happens."

I was still looking for an out. "I don't know," I said. "I would hate to think of you sitting here all alone while I was off fucking some guy."

"I won't be alone," Alisha said.

Uh oh. I didn't like the sound of that. "Who's going to be here with you?"

"No one," Alisha said. Pablo's out of town this week, so Kerri and I will be having a 'girls' night out' for some drinks."

"Just drinks?" I asked.

"You know me," Alisha said with a mischievous grin.

So, the next day I went to work. I got home that afternoon at about the same time that Alisha did. We cleaned up and got ready for our respective dates. Alisha looked hot in the midriff baring top and the micro skirt that she chose to wear over the bar that she would meet Kerri at. It made me uncomfortable to think that she was going out dressed like that. The men at the bar were going to all be trying to take her home with them. Plus, I really didn't want to go to some guy's house. I wanted to stay home and rip that outfit off of Alisha and have my way with her right then and there. She wasn't having it though; her friend Kyle needed a man that night, and Alisha was in the mood to eat some pussy. She did tease me relentlessly though so that I was horny and frustrated when I went over to Kyle's apartment.

I was a little nervous as I knocked on the door to Kyle's apartment. I looked around, hoping that none of my students lived in the complex and would see me entering a gay man's apartment for a tryst. Luckily, I didn't see anyone else around at all.

Kyle opened the door and let me in. Alisha was right. He was cute. He was probably mid to late twenties, with curly blonde hair and piercing blue eyes. He had a slight build, and when he turned around to escort me into the kitchen, my eyes stole a glance at his butt. It was cute. I still wasn't sure if I was going to penetrate it or not, but if I was, then at least it would a cute one to look at.

Kyle led me to his kitchen table. The pizza was already waiting for us. Kyle ordered a half and half. I am a meat eater, so Alisha told him that I like the meat supreme pizza. Kyle is a vegetarian, so he had a vegetarian order on his side of the pizza. I couldn't help but to take note of just how different Kyle and I were. He even committed the ultimate pizza sin—he had pineapple on his side of the pizza. Yuck!

Kyle and I talked and got to know each other a little bit as we each ate a slice of pizza. He had been working with Alisha for about two years at the doctor's office. He said that he thought that Alisha was, as he put it, "adorable," but he simply isn't into girls at all sexually. He's gay, proud to be gay, and he has never even tried to have sex with women—not even adorable ones.

After just one slice of pizza a piece, Kyle stood and walked over to my side of the table. Slowly, he bent towards me until our lips met. It was a gentle kiss at first, and I could taste pizza on his breath. While we kissed, his hand ran up the inside of my thigh until it rested right on the bulge that was forming in my pants. I kind of liked his hand there as I kissed him back.

Kyle broke off our kiss. "Enough small talk," he said. "We both know why you're here." He took my hand and led me to his bedroom. For a totally feminine gay man, he sure was aggressive, I thought.

Kyle had a queen sized bed. It would certainly be sufficient for the both of us. Kyle and I each undressed ourselves, and then Kyle had me sit on the side of his bed. He kissed me gently on the lips, and then moved downward. He kissed my neck a little, pausing at the base where my neck meets my collarbone. Then, he moved down a little more. He kissed and sucked on my right nipple. He chewed on it a little bit with his teeth, then, he moved over to my left one. After giving it a little attention, he kissed his way downward a little bit, slowly, but still making a bee line for his ultimate target.

Soon, he got there. I was already semi hard from his attention. He took my cock into his hand and started admiring it.

"This is way nicer than my ex's cock," he said.

And before I could respond, he had my cock in his mouth. I had heard rumors somewhere that gay men give the best blow jobs. I don't know about all gay men, but Kyle definitely knew what he was doing. He used the right amount of spit, suction, and depth to have me rock hard in under a minute. I was afraid that I was going to cum in his mouth, but he seemed to know just how much attention to give to my manhood to keep me on the edge. I watched his lips suck on my cock for a bit, and then I just closed my eyes and enjoyed the sensations that his mouth was causing my cock to experience.

When Kyle had enough of blowing me, he stood up, kissed me, and whispered, "I want you to fuck me now."

He turned and crawled onto the bed on all fours with his ass pointed straight at me. He looked over his shoulder and said, "There's lube on the nightstand."

I took the lube and opened it. I have had enough lube poured onto my asshole lately that I knew how to apply it to Kyle. I squeezed it directly on his butthole and rubbed it around. As I gazed at Kyle's ass, I noticed that it looked more like a woman's ass than a man's. I was expecting it to be all hairy and big, but it wasn't. As I was rubbing the lube into his ass, I noticed a little stubble, so clearly, Kyle likes to shave his asshole. I decided that I was definitely going to have to get Alisha to do that to mine. Kyle's ass was nice and smooth. It was firm and felt good under my hand as I was rubbing it.

I placed some lube onto my fingertip and poked at Kyle's back door. He moaned in approval as I slid my whole finger into him. I knew that I liked to have my prostate massaged by Alisha, so I searched for his and found it. He hissed in pleasure. I pulled my finger out and lubed it again, along with a second one. When I slid two fingers into Kyle's rectum, he moaned some more. "That's it," he said. "I like that."

When I felt like Kyle had been lubed up enough, I withdrew my fingers and applied the lube liberally onto my cock. I then scooted up behind Kyle and rubbed my cock up and down his butt crack. He wiggled it a little bit, desperate to be penetrated. "Stop teasing me," he begged. "Fuck me."

I aligned my cock up with his asshole and slowly started pressing in. Little by little, I felt Kyle's asshole open up as my hard cock slid into it. My head popped past his sphincter, and in yet another first in my life, one of the many that I've been experiencing lately, my cock was buried in another man's ass. As I looked down, I was amazed at what I saw. Kyle's ass was so cute that if I was just looking at the ass and didn't know that it was attached to a guy, then I could easily have mistaken it for a woman's.

I fucked Kyle's ass slowly at first. But soon, he started bucking back against me—a sure sign that he wanted me to fuck him harder. I took my cue, grabbed his hips, and started really pounding Kyle's ass. He kept saying things like, "Yes, just like that," and "Your cock feels so good!" His encouragement spurred me on. The combination of Kyle talking dirty to me, the sight of my cock parting his cute ass cheeks like the Red Sea, and the pleasurable sensations going on in my cock had me on automatic fuck mode. I kept fucking him until I felt the cum boiling up in my balls.

I announced, "I'm going to cum!"

Kyle responded. "Yes! Cum in my ass. Shoot your cum inside of me."

Once he issued that command, I did exactly what he demanded. I stiffened up, my cock throbbed, and then I felt jet after jet shoot through my shaft as I pumped Kyle's ass full of cum. I don't know how long I kept cumming, but I didn't think I would ever stop.

Once I was spent, I noticed that Kyle was furiously stroking his own cock. I pulled out, rolled Kyle over onto his back, and said, "Let me help you with that."

Kyle moved his hand, and I replaced it with my mouth. I was surprised at how easily I was able to get my mouth around Kyle's cock. The only cock I had ever sucked before this night was Pablo's, and I damn near had to dislocate my bottom jaw like a snake in order to fit it in. Kyle's penis, on the other hand, wasn't a struggle to get into my mouth at all. Kyle has an average sized six-inch penis, and I was almost able to swallow it all in one gulp. Kyle's manly scent mixed with the scent of the soap that he had bathed with combined to arouse my libido. I also found that I liked having Kyle's cock in my mouth. It felt comfortable on my tongue, and it tasted pretty good too.

Kyle didn't last long. He was already worked up from being fucked in the ass and using his fist to masturbate. I formed a seal around his cock with my lips, and bobbed my head up and down as quickly as I dared. In less than two minutes, I heard Kyle say, "I'm going to cum!" I kept my mouth on his cock as I felt it swell up and then pulse as he filled my mouth with his cum. I did the best that I could to hold it all in, but I'm not a very experienced cock sucker, so some of it came out of my mouth and soaked his dick. I did keep my mouth on it until I felt him stop cumming. Then, keeping the cum that was in my mouth there, I licked what had escaped off of his cock and ball sack. I then moved up, and Kyle and I swapped his cum back and forth in our mouths until we swallowed it.

Kyle and I lay back on his bed for a few minutes as we caught our breath. Kyle then suggested that we go back into the kitchen and eat some more pizza. I agreed. We ate two slices a piece, and then we started feeling a little frisky again We went back into Kyle's bedroom for the second round.

When we got back in his bedroom, Kyle had me lie on my back so that he could suck my cock back to life. His mouth worked magic on me, and I was back to being hard in no time. When it was ready, Kyle came up on the bed, straddled my hips, and lowered his butt down to the head of my cock. This was new for me. Alisha likes to get on top and ride, but it had never occurred to me that a gay man would do the same thing. Yet here was Kyle, lowering his ass until it was touching the tip of my cock. Kyle was facing me, so I could see that his cock was already hard. Slowly, I watched my cock disappear into Kyle's ass as he lowered himself onto me completely.

Once I was all the way in, Kyle gave a moan of satisfaction. He sat still for a moment while he adjusted to the feeling of my cock in his ass, and then, he started moving up and down on it. I watched as my cock would emerge from his ass as he moved up, and then disappear as he allowed his weight to slide down it to the hilt again. Just above the junction of my cock and Kyle's ass, Kyle's cock was hard. It bounced up and down a little as he rode me, but it was hard enough that it wasn't flopping around like one would expect.

Kyle braced himself by placing his hands on my shoulders as he bounced up and down on me. I was pinned to the bed, but I found my hips thrusting up to meet his motions. Soon, we got into a good rhythm. We kept that up until Kyle decided that he was tired. He got off of me and laid down on his back. He spread his legs to invite me to fuck him in the missionary position. I grabbed the lube, slathered it on my dick and his asshole, positioned my cock at the entrance to his ass, and slid into it with one smooth motion.

Looking down while I was fucking someone and seeing a cock attached to them instead of a pussy was a new experience for me. I pounded Kyle's ass in that position as his legs were splayed on either side of me. Once we really got into it, Kyle reached down and started stroking his cock while I fucked him. We continued on like that for a few minutes—me fucking Kyle's ass while he stroked his cock with his hand.

I heard his breath start to shorten and knew that he was about to explode. I was close myself and announced that I was about to cum. When I did, Kyle said, "cum all over me."

"You mean in you?" I clarified.

"No," he said. "Pull out and cum all over me."

Reluctantly, I pulled out and started jacking my own cock. Kyle screamed, and cum started shooting out of his dick, all over his abs and chest. I started cumming just after he did. It was an amazing sight to see my cock and Kyle's cock shooting our cum all over him simultaneously. The two loads got mixed together as they splashed on his stomach, his chest, and some of my cum even got on his neck and chin. We both fired off shot after shot until we were spent. With a squeeze and a shake, the last of my cum oozed out of the head of my dick and landed just below Kyle's belly button.

Once we were both done cumming, Kyle started rubbing the cum into his skin, mixing it together into one cum cocktail. He seemed to be enjoying himself. Then, he scooped some of the mixture up with two fingers and stuck the gooey mess into his mouth. He moaned in approval. He looked me in the eye. This tastes good, he said.