As I lie in bed, blinking away the bleariness of a deep slumber, I slowly came to awareness. I was at home, in bed-as to be expected-and I was feeling... I scanned my body for soreness and tightness. Besides my typical stiffness, I felt my thighs, jaw and... I grinned sheepishly, my butt hole were quite sore. With the awareness of my anus, I recalled the happenings of a couple nights before. I relished the memory with my morning wood in hand, stroking as I reflected.
It started three days ago. My phone buzzed, I looked at the screen and saw that I had received a text from my friend Braxton. Braxton was a fairly new friend, he and I had met at my place of work while he was looking for a new IPad. I had helped him find one that fit his preferences and budget. During the conversation, I could tell he was trying to prolong our interaction by asking about my interest in electronics. I could tell he was probably gay. He had been staring at my ass when I had bent over to grab things to show him. I wasn't gay, but I was single and did enjoy riding a cock here and there(more on this later). I decided to throw him a bone, wink wink, and told him I had to get to other customers and he could hang out for an hour while I finish my shift.
After my shift, I found him in the gaming department. I tapped him on the shoulder and asked him if he'd like to go grab some ice cream. The reason I gave him a chance was because of his body. He had thick legs, huge calves and bulky thighs. His ass was plump and round on somewhat wide hips. His stomach was what caught my attention, chubby, like a beer belly, but soft and round. He wasn't so big that his belly hang over his belt, but he was large enough that he filled out a XXL shirt. His chest had nice, small man boobs, and, I was hoping, with nicely sized areolas for licking and sucking. his arms were typical of a fat man, large biceps with no definition, and surprisingly large forearms. He had a handsome face, pleasant smile and a good head of short cut hair. In other words, this man was a chub and my type for a good fuck.
As we sat down and ate our ice cream, we started talking about ourselves. Our likes, dislikes, interests, goals, past, all the normal stuff new people talk about. He told me he was actually looking for a friend in the region. His job took him all over the place staying in hotels that he managed. This meant that he never had much to do in his free time so he sat alone in his hotel room most nights. I, being a fairly friendly person, offered to hang out if he wanted. I said we could find things to do. At no point did he ask me about my sexual preference and I was feeling shy about that because, well, what if I was wrong about him? Some straight guys even stare at my ass, so maybe he wasn't gay. Anyway, We exchanged phone numbers and I told him to hit me up when he was free and I'd try to work with his schedule. He texted me later that night:
"Hey Sean, thanks for hanging out with me today. It was nice to connect with someone here in town. And thank you for understanding my situation, most people think I'm Just trying to hook up with them."
I replied, "no prob, brother. I'd hope someone would do the same for me in your situation."
"Would you have time to hangout tomorrow again? I'll be done with work around 3pm and be bored." He asked.
"Sure," I said. "My friends' family has a nice pool we could relax in for a little while if that sounds interesting to you."
At this point, I was thinking I hope he's gay, otherwise I'll have another friendship to maintain. I wasn't really wanting anymore friends, I was only in the mood for people I could mess around with. I was a horny little fuck. I wanted to see him naked, hence the pool, and this was the easiest way to get him almost there. At least, I'd be able to see his nipples and find out if he was furry, smooth, or somewhere in between. I wondered if there was a way to get him naked without making it obvious I wanted him to fuck me, but couldn't come up with anything fool proof. So, I settled with just making it a hang out with a friend.
"That sounds great! I don't like sharing the pool at me hotel with my patrons, so being in a private pool would be amazing. Text me the details and I'll see you tomorrow. Have a good night."
He included a couple sleeping emojis and a smiley face emoji. Well, if he isn't the "fuck-a-guy-in-the-ass" kind of gay, then he was definitely the other kind of gay.
Either way, I sent him the details and went to bed fantasizing about him sucking my dick and pounding my ass. I figured, in the morning I'll do some anal preparation just in case this guy turns up to "turn me out". My cock was so hard and throbbing just thinking about it. I took off my shorts and underwear, then my shirt. I stroked myself furiously, imagining him deep in my ass, or sucking my dick, or even having his cock in my mouth and making me swallow his nut. I didn't last more than a couple minutes. I was extremely aroused. As I imagined him cumming in my ass, I exploded all over my stomach and face. Now I was a mess. I dipped my finger in my cum and brought it to my lips. I opened my mouth and sucked my jizz off my finger. Nope! I don't think I'll ever like the taste. As I cleaned myself up with my shirt, I remembered at one time I wanted to be a perfect little cum slut. That dream was dashed when I first tasted cum and immediately threw up. So I decided some cum in my ass would have to suffice. Besides, guys love breeding my ass. With that, I fell asleep.
The next morning I got to work. I called my friend's mom and asked if I could use her pool and bring a friend over. She said that'd be fine and that they weren't gonna be there until later that night so I was to be careful. She always worried about people in the pool, regardless of age. I thanked her and started prepping for an impromptu anal invasion.
By 2:30pm, I was cleaned up, in my swim trunks, and sitting poolside. I decided to get to the pool early to make sure my friend's parents weren't home after all. The house lay empty.
At 3, I received a text from Braxton.
"On my way" was all it said.
I'm not sure what else I was expecting, but I guess I was hoping for something a little more flirty. So, I replied with a thumbs up. Simple.
Twenty minutes later, I heard him pull up. I walked outside the gate and showed him where to park. He got out and was in regular shorts and a t-shirt. this was disappointing. I was hoping he was gonna change and swim with me, otherwise this will be a bust for my lustful side.
"Hey, Braxton!" I said with a smile, "need a place to change?"
I was hoping he had brought a change of clothes for swimming, that way I could fawn over him and admire his body.
"Well, um, I was hoping you wouldn't ask. I didn't think you'd want to see my fat body, so I decided just to dress comfortably." He said with a shy, downward gaze.
I'd played this game before. He looked up into my eyes and I saw that small glimmer of hope that I would accept him regardless of his appearance. He had no idea that I accepted him because of his appearance. So, I played the obligatory accepting friend.
"Why would I have an issue with your body? If you're self conscious about, then you can stay in the clothes that make you feel comfortable, but you have no need to worry about judgment from me. All I know, is that swimming isn't as fun in those clothes, so if you brought some swim trunks, feel free to change and join me. Besides, I have a fun game we can play, but it requires us being in the pool."
"Well, we just became friends and I'm not sure I'm that comfortable around you yet."
"Exactly, we are friends. Tell you what, let's hang out and if you change your mind then you can go change."
"Sounds good."
I was a little surprised at his reticence to change into swim trunks, but this was just another sign this guy was gay. He was just too worried about his appearance, and he showed another sign of being into me by being concerned about my opinion. Well, I figured it was gonna go my way as long as I played my cards right and took it slow.
"Well, how about with start with a game that doesn't involve the pool?"
"Okay, but if you want to get in the pool, please do. I don't want to keep you from having fun."
"Thank you, but I think swimming is boring unless there are others to play with. So, I have a game called Flex, where all the rules change depending on the cards we play. Sound interesting?"
"Yeah, I've played it before. Which version do you have?"
"I have, Batman, pirates, zombies, or regular. Your choice."
"Pirates, sounds fun. I haven't played that one."
As we played, I could tell he was getting more comfortable with me and he started to relax in his chair. Eventually, he played a card that ended the game. It was a short first round, so we played again. I made a joke about the possibility of other versions of the game.
"Could you imagine if they made a version of this game called pirate booty?" I said laughing.
He laughed, "yeah, and one of the rules says you have to plunder the loser's booty while talking like a pirate."
I laughed so hard at his joke. It was genuine. He shocked me with that overt of a gay reference. I looked at him after wiping tears from my eyes.
"Well, you seem pretty comfortable with me now, are you ready to play the pool game or do you want to stay in those clothes?"
"I think I'm ready, but I didn't bring my swim trunks because I didn't think I would actually get in."
"That's alright, I think my friend's dad has a pair that will fit you."
He looked at me with hesitation and a heavy laden "um."
"I'm just kidding, dude. That would be weird. Just go in your underwear and we will be fine."
"But then I'll be wearing even less than you, that doesn't seem fair."
Now he was starting to get flirty. I could see lust in his eyes. He wanted to see me naked, but didn't want to go too far and scare me away. So I thought I'd push it a little further just to see what he will do.
"Hmm, I didn't bring underwear. So, I guess I'll just get naked?" I half asked half stated with a shrug.
