After I'd divorced my wife of 10 years, I moved into a condo while she and the kids lived in the house. We'd parted amicably, but I was still pretty hurt by the whole process and the things that we'd said in court. Luckily, she wasn't able to take me all the way to the cleaners, so I was fairly well off even with the alimony and child support I had to pay.
My condo was nice, on the fifth floor. A two bedroom with a little balcony that overlooks the river. I'd settled in and started to think of it as home after about a month.
One day, I was sitting on my balcony having a beer and watching the world go by when my neighbor came out on to his balcony. I said hello and we talked for a bit. His name is Chuck and he seemed nice enough. He was about my 6-foot height, but probably only tipped the scales about 30 pounds less than my 185. His skin was deep brown and he had a wide smile. We made idle chatter for a while and then he went inside.
Several days later, I'd come home from work and headed out to my balcony for a beer. Chuck was on his balcony, so I invited him over. We sat out on my balcony drinking beers and getting to know each other for several hours. The conversation moved on to sex, as most inevitably due after I'd remarked about how pissed I was that the local baseball team's pitcher got shelled the night before.
Chuck remarked, "Yea, he's never been the same since we broke up. I guess I broke his heart after all."
I replied "Wait. You DATED him? Like dated, dated him?"
Chuck then told me how they met at a local bar and slept together that night. Their relationship progressed to where the player moved in with him a week later. Chuck went into very gory detail about their sex life: how he used to beg Chuck to fuck his ass, how he loved it when Chuck came on his face, and other intimate details. I sat there listening in disbelief.
"THAT guy is gay?!?!? Seriously? I can't believe he's gay!"
Chuck said "Oh, he's gay alright. You'd never know it, but he is. One of the reasons we broke up is because he didn't want anyone to know. When we'd go out, it was always made to look very platonic. I couldn't deal with it anymore so I broke up with him. We were together about a year, I guess. "
"Wow, I'm dumbfounded. Hell, I didn't even know you were gay either."
Chuck said "All my life! How about you? I saw the pictures when I came in. I see you have kids. You married?"
"I was. We divorced about 6months ago. It was hard, but I think I'm much happier now. "
Chuck asked "So, you got a girlfriend or anything?"
"No," I said. "I think I'm kind of 'A-sexual' now. I just don't have any desire to get into a relationship at the moment."
"So, you're just jerking off every night now?"
"Pretty much," I said. "When I'm horny, there's a little Korean massage joint a mile or so away. I get a massage and a hand job. It's ok."
When Chuck asked me how much that cost, I said "It's $120 for the massage, but I give a $50 tip for the handy. The massage is OK but I'm not allowed to touch her during the hand job. I need to find a place that's a little more 'interactive', I think."
Chuck said "Hell, for $100 I'll give you a massage and a hand job. I love giving massages."
I looked at him and thought he was joking. "Right. I'll keep you in mind should my Korean chick break her hands."
"Seriously," Chuck said. "I guarantee I'd give a better massage than some Korean chick. I was with a professional athlete, for Christ's sakes! I used to give him a massage and happy ending damn near every day!"
"Thanks, Chuck," I said. "But I think getting a hand job from a guy would be a bit more strange than I could handle. I've never done anything like that with another dude. "
"Well," Chuck said as he stood up. "Think about it. I'm right next door if you change your mind. I'm headed home, so we'll see you around. Thanks for the beers."
Chuck left and I finished my beer and headed off to bed. As I laid there in bed, I couldn't help but think about Chuck and his offer. He was a good looking guy, for sure. I had to admit that I was a little curious, but wasn't sure if I could actually do it. I drifted off to sleep, but couldn't quite stop thinking about what it would be like to have Chuck stroke my cock.
Weeks went by. Chuck and I would hang out every few days, drinking beers on one of our balconies. He'd broach the subject occasionally of a massage, usually asking how my Korean chick was doing. I always assumed he was still joking about the whole thing.
One day, as I pulled into the parking lot of my massage place, I saw 4 or 5 police cruisers in front. I quickly spun around and acted like I was just turning around. Judging by the looks of things, I'd narrowly missed a raid of some sort.
I was as horny as I remember being, so I headed on home to take care of things myself. As I was getting into the elevator, Chuck came through the door. I held the elevator for him and we rode up to our floor.
Chuck asked me how things were and I told him about the raid on my massage place.
"No shit!" he said. "They got raided? You're lucky you weren't there already!"
"No kidding," I said. "I don't know what I'm going to do now. That was the only sex I was having!"
"Well," Chuck said as a sly smile crossed his face. "My offer still stands. I'd be happy to take care of things for you." He looked me up and down a few times and then straight into my eyes. "I guarantee it will be the best massage of your life or your money back!"
My horniness got the better of me so I said "Why not, Chuck? Are you available now?"
"Sure! Let's go to my place."
I followed Chuck down the hall and to his door. He turned to me as he opened the door and said "Welcome to Heaven!"
"Very funny, " I said. "Where should we do it?"
He smiled and said "'Do it', huh? Why don't we 'do it' in the bedroom. This way..."
I followed him to his room. He had a very large, four-poster that had to be larger than a king size. His room was also meticulously clearn.
"Wow," I said. "That is a huge ass bed!"
He walked over to his nightstand as he said "Biggest one they make. Getting sheets to fit is nearly impossible though." He pulled a bottle of massage oil out of his nightstand and then turned to me and said "Well? Come on. Take off your close and get on the bed. Face down to start."
"Oh, right," I said as I started to strip. Chuck just stood there and watched me as I disrobed. I half expected him to turn his back, but he didn't. He just stood there watching me as a peeled off my clothes with a sly grin on his face.
I became a bit self-conscious as I dropped my pants to reveal that I don't wear underwear. The fact that I was standing there naked in the middle of the day in another man's bedroom got the better of me and I could feel my erection building. I stepped out of my pants and walked over to the bed. "Which way do you want me to lay?"
Chuck looked down right at my growing cock. "Well, somebody's excited! Why don't you lay across the bed."
I did as I was told and I could feel Chuck get up on to the bad and then straddle my naked ass. He was wearing jeans and I could tell that they were probably going to be chafing on my bare skin. But for now, I didn't say anything.
Chuck warmed his hands and then began massaging my shoulders. He rubbed the oil over my back and then continued with my shoulders and upper back. It felt fucking amazing! He had very talented hands and his technique was better than any massage I'd ever had. I just closed my eyes, smiled, and enjoyed it.
After a few minutes, Chuck asked me if the pressure was ok. I told him that it was fine, but his jeans were starting to rub my ass raw as he moved. He asked me if I'd be more comfortable with them off. I told him "Sure. I think that will be fine."
I felt him get up and he asked "Are you sure you're not gay? Having another guy sit on your ass in his underwear might cross your hetero line somewhere."
I smiled and said "I don't think I could be gay. I like tits too much."
Chuck said "Well, there are advantages to being gay that you don't get with a woman."
I asked him to explain and as he peeled off his jeans and shirt he said "Well, familiarity with the equipment, for one. You'll see when I'm getting you off. Knowing your own cock means you can take care of another better. "
"I see," I said, still with my eyes closed. I could feel Chuck get back up on the bed and straddle my ass again. This time, I didn't feel his jeans, but I could feel his bare skin. I opened my eyes, looked back at him and said "I thought you were going to keep your underwear on?"
Chuck said "I did. See? " and he stood up where I could see him. Sure enough, he was wearing some sort of black thong.
"Oh," I said. "Ok. That's not much in the way of underwear."
"You don't wear any underwear, so what's the point? Just relax, will you?" he said as he sat back down on my ass and started my massage again.
I closed my eyes and relaxed. So what if he's practically naked while sitting on my ass, rubbing my shoulders? He's going to be jerking me off anyway. What does it matter?
Then I started thinking: What if he gets hard while he's doing it? Every time I've given a massage to my wife, I always got an erection. A little voice in my head said "Yea, you didn't exactly think this through, did you?" Shit. What was I going to do when I turn over to get serviced and there he is: His black cock sticking out from the top of his underwear?
Chuck continued to work his way down my back to the top of my ass. As he did, he slid off my ass and down my legs. He moved my legs apart and kneeled in between them while he rubbed oil on my ass and rubbed it into my skin.
"The ass is the most misunderstood part of the body, I think. Since it's where the shit comes out, people think it's dirty. There's so much pleasure to be had in the ass. Your prostate gland is in there, for example. Have you ever had your prostate massaged, Mike?"
"No. I didn't know you could massage that."
"Well," Chuck said. "You have to go through the anus to get to it, but by rubbing the prostate gland, you can induce an orgasm." I could feel his hands all over my ass. Spreading my cheeks apart, he lightly ran his hand down the crack and across my asshole. A shock ran through my body and I so desperately wanted to moan.
"Really," I said. "I'd never heard of that before." I tried to remain calm, but my heart was pounding. He was running his hands all over my ass again. Squeezing gently and rubbing the oil in.
"Oh, sure," he continued. "It's very intense. But there are other things too. Have you ever had your asshole licked?" I heard the massage oil container open.