Roger

So, just to establish who and what I am, I'm a 52 year old real estate agent in a small town. Standing a very average 5'9", I weigh 170 pounds, with thinning salt and pepper gray hair. I'm bi-sexual, which in my case means that while I'm attracted sexually to both men and women, on an emotional level I only connect with women. I'd been curious about sex with men since high school, but my first sexual encounter with a man didn't happen until my mid 40s. After that, things were sporadic until my marriage failed 3 years ago. One the divorce was final, I was free to indulge my needs, and I did so, with the help of online sites where a guy could locate other men with similar desires. Right away, I learned that I was a bottom, liking how a hard rod felt up inside me, and I was lucky to meet another bi fellow who was an eager top. He was married, but we still managed to hook up fairly often. We explored the full gamut of positions and sex acts, from blow jobs, to rimming, to bareback fucking. He had a nice 7" cock of decent thickness, and once I was broken in, he could enter me with ease. Unfortunately, he suffered a heart attack while working in his garden. After his recovery, they moved to Arizona.

That had been 3 months ago, and I hadn't been motivated to find another partner. I was also between girlfriends, so my sex life was at full stop. A Saturday morning found me at work, clearing up paperwork, when I heard the door to the outer office open, so I got up and walked out to see who it was. To my great surprise, it was a guy I'd known years ago in high school. Roger had been 3 classes behind me, and had an older brother that had been my teammate in football. Unlike his brother, Roger gravitated towards marching band and drama class. Later, when I was in college, A friend told me that Roger had gone gay. We shared a laugh over it, and I forgot about it. Years later, I heard he was living with a guy. Now, he was standing in my office, and looking pretty damn good. He was shorter than I by a couple of inches, and stockier, with his blonde hair cut short. His eyes were gray, over top of a thin mustache colored same as his hair.

"Roger, how are you? What brings you back to town?" I stuck out my hand, and received a firm handshake in return.

"Oh, I need to get something done with my aunt's place. I'd like to list it with you, and let you take care of selling it. I'm too far away, and too busy to do it myself." We talked for a few minutes about what he'd hope to get out of it, then spent a while catching up. He worked for the postal service in the city where he lived, and casually mentioned Doug, the guy he lived with. He had heard about my divorce, and seemed curious that I wasn't seeing anyone. When I said that I was keeping my options open, he just gave me a funny smile. I had to admit, I found him very attractive, and if the opportunity came up, I was going to say yes. It came sooner than I expected.

"You know, we should hang out sometime, over a drink, get caught up on what my classmates around here have been doing. You ever get over to the city?" There was my opening.

"Yes, we have several properties listed there. I actually need to go and get some pictures of a new listing. I'd planned to do that later today. Too soon?" His face lit up with a big smile.

"No, no, not at all. In fact, my roommate is away for the weekend, so the timing is perfect. After you get your pictures, send me a text." We exchanged numbers, and he left. Later, while driving to the city, I thought about what he had said, about his roommate being gone. Maybe Roger had something more in mind than drinks? I sure hoped so. After taking care of business, I sent him a text, and he responded with an address for a bar. I found the place, parked, and walked in. At first, it looked like any other bar, just a few guys sitting at the bar and tables having drinks and chatting. But, after I ordered a beer and sat down, I took a closer look, and saw a poster for a Gay Pride event. Other things like the pictures on the wall clued me in, I was in a gay bar. Oh well, no one knew me, so I relaxed. Roger arrive a few minutes later, got his drink, and sat down next to me. We had a nice conversation, and ordered another round of drinks. He sat back, and looked me with a thoughtful expression.

"You seem pretty relaxed, Stan. You know this a gay bar, right?" I knew he was looking for a reaction, and perhaps an opening, so I gave it to him.

"When I got here, I was pretty sure it was. It's cool, I don't mind." I smiled at him, and he nodded.

"And you know I'm gay, right?" I sat down my glass, and looked at him.

"I had heard that, yes, but until you told me I wasn't sure. But, it doesn't matter, I'm open minded." I wanted to say more, but hesitated. He must have sensed it.

"How open minded are you?" There it was, and I decided to go for broke.

"More than most, I'd say. I've had sex with men several times, if that counts?" Roger's eyes widened, and he didn't say anything for a minute. Then he smiled, leaned forward, and put his hand on my arm.

"Yeah, that is definitely open minded." We looked at each other, and broke out laughing. The ice was broken, and I decided to press, just a little.

"So, you said your roommate was away. I've heard he's more than your roommate, which is fine by me. Can I ask, what the boundaries are in your relationship with him?

"Sure, you can ask, and I'll tell you. He and I are in a relationship, have been for years. As far as boundaries, I assume you mean do we ever include others when we play?" I nodded, and he continued.

"Sometimes we do, although it's been a while. It's always been having a third join us for some fun as a threesome. Since you are asking, does that mean you are interested?"

"I've never been in a threesome, but I'd be willing to try. But didn't you say your roommate is gone for the weekend?" He looked at the ceiling as he thought about something, then looked back at me.

"Yeah, he is. Look, if you're game, we can go to my house right now. I'll have to tell Ben when he gets home, but that's not your problem." He was leaning in close to me now.

"I'm game, let's go." We left the bar, and I followed him to his home. it was a very nice place, in an upscale neighborhood on the edge of the city. Once inside, we went straight to the bedroom, where Roger grabbed me, and kissed me. I kissed him back, rolling my tongue round and round with his, feeling his cock harden and press against mine.

"Mmm, I can't believe you're here with me. I always thought you were so hot in high school." he said after breaking the kiss. He unbuttoned my shirt, and ran his hands over my chest, flicking his thumbs across my nipples.

"What would you like to do?" he said in a husky voice. I shrugged out of my shirt, and started to undo his belt.

"Let's have a little nice foreplay, then we can get down to business. You like to top?"

"Oh, hell yes, I love to, just don't get to that much." I unfastened his jeans, ad tugged them down, revealing purple briefs, with a big bulge in front.

"This is your lucky day, because I love to take a cock up my ass." I stuck my hand in the band of his shorts, and pulled out his meat. It was a nice one, around 7 inches like mine, with a sexy up curve to it. I went my knees, and sucked in the head. Roger steadied himself, holding onto my shoulders, and moaned when I lapped my tongue around and over the flaring head. He let me suck on him for a couple of minutes, then pulled me to my feet. We hurriedly got out of the rest of our clothes, and got onto the king bed. Pushing me flat onto my back, he got on his knees next to me to take his turn sucking on my cock, and soon had me twitching and jerking with pleasure. I felt around, and found his, giving it several strokes with my hand while he continued to suck mine. It felt great, watching this thick-bodied stud go down on me, and I couldn't wait for him to fuck me.

He must have had the same thought, because he stopped, and looked up at me.

"You want me to fuck you?" I nodded, still tugging on his cock.

"Okay if I go bare?"

"Yeah, if you're clean."

"I am, we get tested monthly." He found a tube on the table next to the bed, and had me get up on my hands and knees. In that position, he put a liberal coating of lube on my wrinkled hole, shoving some in with his finger. Then with his cock greased up as well, he got into position behind me, and pressed his cock against my hole. After a moment of resistance, it surrendered, and he slipped in, going to the base in one move. I gave an involuntary gasp, that initial entry always takes my breath away, and felt his hands grasp my hips. Holding me, he started to fuck me in a nice rhythm, long smooth strokes that ended when he would smack into my ass each time. I closed my eyes, and focused on the hard shaft as it slid in out out, making the nerve endings tingle and precum dribble out the end. It had been awhile for me, and it felt amazing.

It must have felt good for Roger too, because he picked up the pace after a minute or so, pulling me back as he pushed forward, his hips slapping against my ass. My cock was waving around under my, flinging precum around as it did. He gave it to me fast for about 20 strokes, then suddenly pulled me tight against him as he injected his hot cum into my bowels. After he was spent, he dropped down onto the bed next to me, and we spent a few moments in silence as we recovered.

"Wow Stan, that was awesome!" he said after he'd caught his breath.

"Yeah, it was, it really was. I haven't had a cock for several months, it was just what I needed. I just hope this doesn't get you into too much trouble." He frowned, and shook his head.

"He won't like it, but he'll get over it after he pouts for a while." Then he grinned, and looked at me. "Of course, if I tell him you'll come over and let him have you too, then it might smooth it over for me." I chuckled, and agreed to let Ben have some fun, if it would help. Roger told me Ben was my height, but broad through the shoulders, tapering to narrow hips. He was smooth, with very little body hair, and was nicely hung. As he described Ben's cock, it was longer than our, about 8 inches, and had a shaft thicker than the head. He said Ben was a great lover, and liked to have sex in a couple of positions before cumming. It all sounded like a lot of fun, and I told Roger I was looking forward to it. Ben would get back in a couple of days, and Roger was due to fly out the next day, so he would have Ben text me.

I spent the night, and in the darkness of early morning, I sat on Roger's cock, and rode to him to another orgasm. This time, he jacked me as I slid up and down on his cock, and the feeling of cumming with a thick cock in my ass was incredible.

A few days later, I was at my desk when my phone buzzed. I saw I had a new message, and when I opened it saw it was from an unfamiliar number. It said 'Hi Stan this is Ben'. I replied, and we sent messages back and forth for several minutes. As Roger had predicted, Ben had been initially upset with him, but became intrigued when Roger told him I wanted him to fuck me too. I made it clear that Roger was correct, I'd have sex with him, if he was interested. Well, he was interested, and we made plans for that evening. When he opened the door, I was greeted by a very hot and well built man. He had very broad shoulders, narrow waist and hips, and muscular legs. His hair was pulled back into a man bun. He had a strong chin, a long tapering nose, and piercing brown eyes. We went straight to the bedroom, and he looked even better with clothes off.

We started off with a 69. Right away, I could see this would be a new experience, his cock was thicker than any I'd encountered. I did the best I could, and was rewarded with heavy grunts and groans as Ben sucked on me. Next, he asked me to rim his ass. He was very clean, and smelled of body soap, so I was happy to tongue his puckered hole, licking around it, over it, and even poking the tip of tongue inside. I stroked his cock between his legs, and felt it grow harder.

"Oh man, stop, or I'm gonna blow," so I stopped, and stretched out on the bed. We made out for a couple of minutes, Ben stroking my cock, and slipping his hand under me to finger my hole.

"Mmm, that feels nice. How do you want me?" I said in a low voice. He gave me a deep kiss, then looked at me.

"How about you get on your stomach, and I'll lay on top of you?" he replied in a whisper. It sounded great, so I kissed him back, then turned over, spreading my legs to give him room to do with me as he wished. After lubing up my ass and his cock, I felt him push it between my cheeks, and bump against my ass ring. The head pushed in without trouble, but as the thicker shaft followed, I felt a stretching that I hadn't felt in a long time. My ass burned as he continued to plunge in, stretching me more and more, until he finally stopped. I gritted my teeth, wanting the massive thing out of me, but I was trapped under him, and at his mercy. Lucky for me, he knew what his cock did to guys, so after he bottomed out, he immediately pulled out, slowly. When he pulled out, I felt the cool air enter me, it felt like my asshole was a foot wide. Before I could move, he pushed back in, slowly, and I noticed it felt much better. Still a bit of a burn, but I could handle it. He did this twice more, then let his full weight down on me, his fat cock buried up to the base inside me. With his arms wrapped around my chest, he cocked his hips, and started fucking me with slow and shallow strokes.

As the pain subsided, I began to enjoy the powerful fucking he was giving me. I liked how he had me pinned to the bed, impaled on his cock, unable to do anything but take it. Every few strokes he would speed up a little, until he had the bed bouncing as he drove it in and out of me. My cock was grinding into the bed sheet under me, and I could feel the warm buzz as my inner muscles tensed, ready to force out the gobs of white cum. Ben was breathing hard from the effort, and I wondered if was going to go all the way on my back. Just as I was ready to blow, he raised up off me, slipping his thick cock out of me.

"Roll over," he said in a hoarse voice. I did, my cock twitching and drooling a bead of cum.

On my back, I lifted my legs, which Ben put over his shoulders. On his knees, his pushed his cock back in and resumed fucking me, this time faster than before. I ran my hands across his chest and down over his belly, while he took hold of my cock and began to pump it. About 5 strokes, and I shot all over my belly, a big ,load of 4 big spurts, and a few lesser ones. This seemed to spur him on, and he gripped my legs tight against his chest while fucking me at a furious pace. Then he threw his head back.

"Ooooooooh...fuuuuuck!" he cried out, thrusting his cock deep as it could go, unleashing a huge load of cum. Five times he cocked his chips and drove into me, then just he just held on as the last dribs spewed out.

After he let go and pulled out, he helped me up and I wobbled to the bathroom. Cum ran out of my ass for a long time, until I was able to wipe off the last of it. My hole felt stretched beyond repair, and I knew it would be a couple of days before it felt normal. He was spread-eagled on the bed, his cock laying over on his leg. Since it was a week night, I couldn't stay, so I dressed. Ben walked to the door, and kissed me before I left, thanking me for a great fuck. I replied in kind, and went home. The next day, I was sore, but like I thought, it went away, and my asshole returned to a near normal state. I sent Roger a text, telling him I thought Ben was no longer mad at him. he called that evening, and jacked off while I described how Ben had fucked me.

When Roger returned, I went to their house again, and experienced my first threesome, getting fucked by Roger first, then by Ben. Since then, I see one or both of them once a week. I get all the cock I want, and they now have some variety in their relationship. Truly a win-win.

The End