I’ve always considered myself to be a decent looking guy. Never a real whiz with the ladies but I did alright. Spent 10 years in a train wreck of a marriage, just didn’t matter what I did, I couldn’t please her. Everything was wrong all of the time and I finally had enough and filed for divorce. Now in my late 30s I found myself on the singles market again.
During my marriage I had become comfortable and had let myself go. I developed the typical “dad bod” with a somewhat larger belly than I should have at my age. Oh well, I’m single again which means I’ll have time to hit the gym more often and lose the gut. The years of a stressful marriage and job have also grayed my hair in places, which kind of gives me a distinguished gentleman look I think. That actually used to be one of the few compliments my ex would give me, she said I looked good with the gray temples and salt and pepper look.
Anyways, after the divorce I decided I needed a new town for a new start. So I put in my notice and headed to the Florida Keyes where I found work as a deck hand on a sport fishing boat. The pay wasn’t great, but I’d earned enough during my last job and got enough out of the ex wife during the divorce that I didn’t need a whole lot to survive on anymore. Plus the work was enjoyable and it gave me an excuse to work on losing my beer belly. I found a studio apartment over a rich couple’s garage and settled in for a quiet life.
One thing about the Keyes is there is a very active night life, something I’d missed out on during the last decade. I’d been in my new setup for about a week when I finally decided to go out and explore the night life. I hit up a few different places and finally wound up in a small seaside bar next to the docks. It wasn’t very big, just a bar along one wall and a few tables in the room. There weren’t many people inside and as I always kinda liked quieter bars this one seemed like it had the potential to be my new “spot.”
I ordered a beer and sat at a corner table and surveyed the rest of the crowd in the small dimly lit room. There was a younger couple at one of the tables, a pair of older ladies at another and a few old men talking quietly at the bar with the bartender. In the corner opposite me was a guy sitting by himself, younger, maybe around my age, just sipping a drink and idly shuffling a deck of cards. I finished my beer and flagged the waitress for another. As she brought it to me I heard, “mind if I join you?”
I looked up to see the man from across the room standing beside my table. Now that I could see him clearer I could tell he was maybe in his late 20s, a little taller than myself with broad shoulders and thick arms. He obviously worked out and kept himself in shape, which somehow made me self conscious about my own lack of being in shape. He had short black hair, neatly trimmed above blue eyes and a wide, friendly smile. I had never looked at men in that way, but I would assume he would be what women would call dashingly handsome. I invited him to sit down and he did, extending his had as he did so, “Jon,” he said.
“Stan, nice to meet you.”
“New around here?”
“Yes,” I replied, explaining that I’d just moved here and was working for the sport fishing company down the beach. Jon had moved here about a year ago and was working for the local bank as a loan officer. We chatted for a while, buying each other beers as the night passed. I couldn’t explain it, but there was something a little off about Jon, just could not quite put my finger on it. He asked if I was married and I explained about the divorce and how that was what had led me to relocating in the first place. He was recently out of a long term relationship himself and said that he was just looking for new friends to hang out and socialize with. It seemed like I had just found my first friend in my new town. Little did I know just what kind of friendship it would be.
We got so wrapped up in conversation that we didn’t realize what time it was until the bartender announced that it was closing time. Looking around we could see that we were pretty much the last ones in the bar as well.
“Damn, when did it get so late?” I asked jokingly.
“I know right?” Jon replied. “Got so wrapped up in the conversation I lost track of time.”
“Yeah, I kinda hate to end it,” I said with a laugh.
“We don’t have to,” he said, “my place is close by and you’re welcome to come have a few more drinks if you want to.”
I thought about it and said what the hell, I didn’t have to work the next day and it had been years since I’d been out until the wee hours of the morning, or had such a stimulating conversation as the one I was currently in. Can’t explain it, but Jon was super easy to talk to and I felt some kind of a connection with him that just made me feel like I could tell him anything at all. So I agreed to accompany him back to his place for a night cap or two.
It was a short walk off the beach to a small studio apartment not a whole lot different than the one I was renting. He invited me in and I sat down on the couch as he poured us each another drink. Maybe it was the booze talking, but I started to get the feeling that he was hitting on me. Nothing obvious, just subtle little hints in the way that he said things, or like how when he handed me my drink his fingers trailed across mine in the way that my ex’s used to when she was trying to be seductive. He sat down and his leg touched mine in a somewhat suggestive manner. Maybe it was the alcohol, maybe it was the fact that my ex had shown so little affection the last couple of years, but I felt myself enjoying the small touches here and there. I blinked my eyes a few times to clear my head, what the heck was happening to me? I didn’t like guys, I was straight, why would I enjoy the touch of another man?
I got caught up in these thoughts and I completely missed Jon’s very forthright question. I blinked again and said, “huh?”
“Have you ever thought of being with a man?” He asked again.
I just looked at him stupidly and blurted out, “what?!? No! Of course not!”
He chuckled and said, “I didn’t think so. But you’re an attractive guy, the dad bod look with the salt and pepper hair is a good look on you.”
My brain was moving slower than normal and it took a second to process what I’d heard. He was definitely hitting on me, the little vibes I’d been picking up were correct. I wasn’t sure how I should feel about it, offended? Flattered? I certainly wasn’t ready for the conversation to take this turn.
“Ever thought about kissing a guy?” Jon asked.
“Nope,” I said honestly, “never thought about doing anything with a guy at all.”
I finally realized that his hand had been gently rubbing the inside of my thigh, just inches away from my crotch. I couldn’t explain it, but I was actually liking the caressing of his hand. Fuck, had it been that long since I’d been touched that I was actually enjoying the touches of a man?
I didn’t make any effort to stop him and he continued on in a voice smoothe as silk, “I can tell it’s been a while since you’ve felt the gentle touch of another person.” I nodded agreement. “It’s been a long time since you were shown any kind of affection at all hasn’t it?” Again I nodded agreement. “I can give you that if you want, I can give you some of the affection you’ve been missing for so long, and that I can tell you are craving.”
I didn’t say anything, just sat there stupidly staring into his blue eyes, almost locked into a trance if you will. As I sat there motionless, he continued the caressing motion of his hand, gently rubbing the inside of my thigh. The sensation was intoxicating and I didn’t want it to end. What the hell was wrong with me? Even as I sat there staring into his eyes he leaned into me and ever so gently his lips touched mine.
What the fuck! A guy was kissing me! On the lips! And I wasn’t even making an effort to pull away or stop him at all! What the fuck was wrong with me?
His first kiss was just a soft, gentle touching of the lips, but it lingered a second or two. He pulled back and looked me in the eyes again and he smiled, a soft and warm smile of an understanding soul. He leaned forward and his lips met mine again. This time I felt his lips part slightly, felt a little more passion to the kiss, felt myself gently return his kiss. He leaned back once more, again searching my eyes for a sign that he needed to stop. I couldn’t give him one. I was frozen, enchanted by his gentle touch and tender kiss. I realized that I had a hardon, stiff and raging in my jeans. What the fuck!?! His hand ever so gently slid up the inside of my thigh and came to rest in my crotch, gently stroking my stiff dick through the fabric of my jeans. Getting no resistance he leaned in and kissed me again, this time his lips parted and his tongue slid into my mouth. I hesitated only an instant before massaging his tongue with mine. His left hand continued to rub my cock through my jeans and his right hand he reached up and cradled my face as he deepened the embrace.
I was powerless, locked into an embrace with this man. His deep and passionate kiss had me completely enthralled, and I eagerly returned it, soaking in the affection I had missed for so long. His hands moved to my belt buckle and I froze as he undid it and worked my zipper down. His right hand came back to my face as his left slowly slid inside my boxers and I felt the first strangers skin on my cock in a long time and I couldn’t help but let slip a low moan into his mouth. Oh God it had been so long since anyone else had touched me, my body was hungry for the touch, desperate to feel some affection. But wait! This was a man! I wasn’t gay, how could I be having these feelings?
As Jon’s tongue caressed mine and his hand gently stroked my cock I had to admit he really was a good kisser. Was I actually enjoying this? I shuddered at the thought and my mind fought against the feelings I was having. I was straight. I wasn’t gay. I couldn’t be enjoying what was happening to me right now! Jon kissed me deeply and squeezed my cock and I moaned again. This was all wrong, but I WAS enjoying this!
Jon pulled my boxers down enough to completely free my cock. It sprang up to its full 6 inch length and he stroked it gently, yet firmly. He broke the embrace then and looked down at my uncut dick in his hand.
“Mmmm, nice!” He said as he squeezed again, sending a shiver through my body. He gave me another kiss, sending his tongue back into my mouth, before sliding off the couch and between my legs. I watched, complete frozen as he lowered his head to my lap, watched as he extended his tongue and flicked it across the head of my cock, making me flinch. He grinned up at me before licking the entire length of my shaft, never breaking eye contact. He ran his tongue around the head of my dick before taking it into his hot mouth. I closed my eyes and groaned as he took my whole cock down his throat in one smooth, fluid motion. God this felt amazing! My ex had hated giving blow jobs, only ever doing it when she was really drunk. And on her best day she could never come close to what Jon was doing.
He expertly worked his mouth up and down my shaft, working his tongue on the underside and around the head. This was the best blow job I had ever received! He continued to blow me, never taking his mouth off of my dick, and he pulled my shoes off my feet, followed by my socks. Then he hooked his fingers in the waist of my jeans and boxers and started to pull them off. I had to loft my hips to assist and when I did he deep throated my cock. It felt so amazing, and then he slid my jeans and shorts down my legs and tossed them aside onto my shoes.
He continued his pleasure assault on my raging cock with his mouth, reaching up with his left hand to stroke my belly and chest thru my shirt. With his other hand he gently cradled my balls and softly rolled them in his hand. I was in ecstacy! I could feel the pressure building in my balls and I knew I wouldn’t take much more of this.
“OH fuck,” I groaned, “you’re going to make me cum!”
He quickend his pace, bobbing his head up and down and working my shaft with that expert tongue. It wasn’t even 60 seconds later that I felt my balls boil and a rush of cum flooded up my cock and into his hot, eager mouth.
“OH fuck!” I moaned in ecstacy as I came harder than I’d ever cum before. My cock continued to pulse, shooting streams of cum into his mouth and he swallowed it all, not spilling a drop. As my orgasm subsided he let my softening cock slip from his mouth ND he sat back on his heels, catching his breath. I was working on getting my breathing under control when he smiled at me.
“Somebody really needed that,” he laughed and I couldn’t help but nod my head in agreement. He leaned forward and gave my dick a peck on the head. Then he began kissing my stomach. His hands slid my shirt upwards as he kissed up my stomach. He drew circles around my nipples with his tongue, sending more shivers down my spine. He pushed up on my shirt and I leaned forward, extending my arms over my head so he could slide it off of me. I leaned back now, totally naked as he began kissing my chest and neck. My cock was springing back to life as his lips found mine again and he again kissed me passionately, our tongues dancing together in our mouths.
He broke the kiss and smiled at me again. He stood up then, standing between my legs, his crotch just inches from my face. I knew what he wanted, but no! I couldn’t do that! This has gone too far, I’m straight dammit! Ok kissing him had been really nice, and the blow job was amazing, but I liked women! I couldn’t give him a blow job, that would make me gay and I wasn’t gay!
Even as my mind was screaming these things at me I felt my hands start to move. In a trance like state I watched as they reached his belt and undid his buckle. Completely fixated, I un fastened his button and slowly slid his zipper down. Stop! What are you doing?!?! My brain screamed as my hands pushed his pants off his hips and let them fall around his ankles. He was wearing red and white polka dot bikini briefs and there was a sizeable bulge in the front as his cock was straining against the thin fabric.
It’s not too late, my mind yelled, you haven’t crossed that line, you’re still straight. You can get up and run out now, you can preserve yourself! As my mind cried out in protest, my fingers slid into the elastic of his bikini briefs and slowly pulled down. His cock sprang free and rose to its full uncut glory, at least 8 inches long and thick. The tip glistened with precum and I was staring in awe at the specimen before me.
He flexed it up and down, snapping me out of my trance. “Go on,” he said gently, “touch it. It won’t bite you.” Gingerly I reached my hand up and slowly encircled his thick shaft. It felt rigid as steel, yet warm and soft at the same time. I gently ran my fingers up the length of it and then slowly back down again. God, it was so much bigger than mine was.
“Kiss it,” he encouraged, “taste me.” I leaned forward, extending my tongue as I did so. I took a deep breath and slowly touched it to the head of his cock, tasting his precum as I did so. It wasn’t at all what I expected, salty, a little bitter, but not bad at all. Slowly I circled the head of his cock with my tongue, parted my lips, and brought the head into my mouth.
What the fuck was I doing? I had a cock in my mouth! I had crossed the line. I was gay, a cock sucker, I could never undo this. Ever. I resigned myself to the fate I had chosen and began to slowly work more of his dick into my mouth. As I sucked his cock and began to take it deeper he placed his hand on my head and started to move his hips. No, I gently clamped my teeth causing him to pause. I was going to be in control of this, not him, this had become my choice now and I would run the show. After he paused I began to suck again, taking his cock until it hit the back of my throat making me gag. I eased off and pulled back until just the head was in my mouth, swirling my tongue across the crown and into the slit.
Starting back down the shaft he again started to pump his hips and I again clamped down, forcing him to stop. I was in control dammit, this was my blow job and I was going to direct the pace of it. I put my hands on his hips and sucked him back into my mouth. When I hit the back of my throat I gagged again. I eased off, forced my self to relax, and worked the muscles like I was swallowing food. The head slid into my throat and I worked it down until I had all 8 inches in my mouth and his balls were resting on my chin. I did it! I deep throated him the way he had done me, I had all of his cock down my throat. I couldn’t explain it, but I felt an odd sense of pride at what I had just done.
I eased his dick back out until just the head rested between my lips before taking it all back down my throat again. Jon moaned his pleasure and I again felt pride at what I was doing. I lost track of time then, bobbing up and down on his cock, running my tongue across his ball sack when I’d get him all the way down my throat. His moans of pleasure told me I was doing a good job and that made me happy. If I was going to do it, I wanted to do it well.
It wasn’t long before his breathing quickened and he warned me he was about to cum. Was I ready for this? Did I want to become a cum guzzler too? I had gone this far already, no sense in stopping now. I pulled his cock out of my throat and sucked the head hard while stroking the shaft with my hand. Jon groaned and said, “oh fuck, I’m cumming!”
I felt the first blast hit the back of my throat and it made me gag a little, the second landed on my tongue and I could taste him, salty, a little bitter, but not a horrible taste at all. I swallowed as much as I could but he kept pumping shot after shot into my mouth and it began to leak from the corners and run down my chin. After what seemed like forever his orgasm finally subsided. I sucked the remaining cum from his dick and swallowed it down, finally releasing his cock with an audible pop. My jaw was sore and I could feel the stickiness of the cum on my chin. I wiped it up with a finger and licked it clean, beginning to enjoy the taste.
“There’s no way that was your first time,” Jon said while trying to catch his breath.
“It certainly was my first,” I chuckled.
“Well you’re the most natural cocksucker I’ve ever encountered then, and I’ve had more than a few conversions.”
I just chuckled and said thank you. Jon pulled his shirt off, revealing his toned abs and built chest. He leaned in and kissed me again, deeply, his tongue darting back into my mouth. He wrapped his arms around me and pulled me close, straddling my legs and sitting on my lap. I could feel the warmth of his chest against mine, that closeness of skin on skin contact that I had missed for so long. I placed my hands on the small of his back and pulled him into me, embracing his warmth, soaking it up. I kissed him back more passionately than I’d ever kissed anyone before I think.
I felt him fumbling for something beside the couch and broke the kiss to see what it was. He had a bottle of lube in his hand and he grinned at me. “Might as well go all the way,” he said teasingly and I felt a twinge of fear. Was I ready for that? Could I do THAT? He stood up while squeezing the lube into his hand. Reaching down he began to stroke my dick, which had come back to life again, lubing it up good. Next he put some lube on his fingers and reached under his balls, lubing his asshole. Then he grinned at me again and straddled my lap, lowering himself onto the head of my dick. He guided me to his hole and I felt a brief resistance as my head pressed against his sphincter, then it gave way and I was inside him.
He worked his hips back and forth until I was all the way inside his boi cunt. It felt great as we slowly began to fuck. He moved his hips back and forth and groaned in pleasure. I closed my eyes and pulled him into another of those deep kisses I’d come to enjoy. The feelings were overwhelming my senses right now. The warmth of his ass on my cock, his smooth chest pressing against mine, his hardening dick pressing into my stomach, his tongue massaging mine as his soft lips were locked against my lips. It was all so much and it wasn’t very long before u felt the pressure building in my balls. I grabbed his hips and started thrusting harder, quickening my pace. It was building, I was going to cum. Jon sensed it and wrapped his arms around me, pulling me close, deepening the kiss we shared. With a final thrust I buried my cock as deep in his ass as I could and moaned as I began to cum, shooting streams after stream into his ass. Jon moaned back into my mouth and ground his hips against me.
Finally my orgasm subsided and I collapsed back against the couch, totally exhausted. Jon smiled and gently kissed me again as he stood up. His beautiful dick standing at full attention inched from my face again. He picked up the lube bottle again, a devilish gleam in his eyes. I knew what was coming now, and it scared me a little. Jon sensed my unease as he lubed his cock and said, “it’s OK, I will be very gentle. Just try and relax and I promise it will feel amazing.”
I was scared. His dick was a lot bigger than mine and I knew it was going to hurt when he entered me. Jon lubbed my ass, slipping a finger inside me to work in the lube. He slowly fucked me with his finger, stretching me out some, then he slipped in a second, and eventually a third finger. Once I was thoroughly lubbed and stretched a little, Jon lifted my legs and pulled me to the edge of the couch. Slowly he guided his dick to my hole and pressed the head against it. “Relax” he said softly and pushed forward. After a brief resistance I felt my sphincter give way and his head popped into me. The pain was intense and I cried out but Jon just held still as my ass spasmed around his dick head. After a minute he slowly started working his his, moving a little deeper inside me, taking his time, allowing me to adjust to his cock as he penetrated me.
After what seemed an eternity he had all of his cock inside of me. He slowly pulled it out until just the head remained, then gently slid all the way back in. He repeated the motion slowly, gently fucking my ass. I moaned as the pain turned to pleasure. Jon grinned and kissed me again. I was really starting to love his kisses. He gently fucked me for what seemed like forever, and I moaned as he slid in and out of my hole. He laid me on my back on the couch and mounted me missionary style, shoving his cock to the hilt. I groaned and wrapped my legs around his back, pulling him into me. We locked lips in a passionate kiss and he drove his cock in and out of my ass, quickening his pace as he neared orgasm. Finally he thrust all the way into me as he groaned and started shooting his cum into my ass. I wrapped my legs around him as tight as I could and held him there until his orgasm subsided and he fell limp against me.
Jon rested his head on my chest, catching his breath as I held him in my arms with my legs still wrapped around him. I had missed the intimacy for so long that I didn’t want this moment to end. Eventually he gave me a quick kiss and stood up.
“That was amazing,” he said. “You’re a really good fuck.”
“Thank you,” I replied, “you’re the best sex I’ve ever had.”
He smiled and took my hand, pulling me to my feet. He wrapped his arms around me and kissed me again, our semi hard cocks bumping against each other. He broke the kiss and turned around, my hand still in his. He led me to the bed and we layed down together. We spent the rest of the night kissing and fucking each other until we eventually passed out from exhaustion and I went to sleep cradled in his arms, my head on his chest.