Closing the Loop

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First gay experience.
1.7k words
4.13
35.2k
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I'd fantasized about playing with a guy since I was 26. But my conservative Catholic upbringing had been enough to scare me away from trying anything, even if I had found the right guy. I left my fantasies alone, got married, and fathered a child. Yet my curiosity still got the best of me. I knew I needed to find a guy who was every bit as curious and kinky as me.

After meeting and chatting with many guys online, I finally met Randy. He wasn't like the other guys who just wanted to meet me for a blow & go. He seemed bright and articulate. Most of all he was willing to be patient and let me take things at my own speed. While he was 21 years older than me, he didn't have too much experience with other men-just enough to help me make my first time enjoyable, I hoped. He was a little taller than me at 5'9", a bit chubby but still a handsome guy. Most of all I couldn't get the image of his smooth body out of my head. Clean-shaven penis and scrotum, and a nice curvy ass. Seeing his intimate parts covered in the pink lace of his wife's panties drove me insane with hunger to slurp his clean shaft between my wanting, hungry lips.

My wife was away for three weeks visiting family, so I thought it would be the perfect time to meet Randy over drinks at the local bar. When I arrived, I sent a text to the phone number he gave me during our last chat. After waiting a nervous minute, he replied that he'd already been seated.

I took a deep breath before looking around the bar to spot Randy. A shudder went through my body. Was I really ready to cheat on my wife with a man? I noticed my own cock getting chubby, and I really felt like I was about to explode! Instead, I blew all the air out of my lungs, spotted Randy, and took the seat across from him.

We said our hellos as the waitress came by to take our drink orders. I ordered a Blue Moon and Randy got a Sam Adams. We talked about our families and working as engineers as we finished our cold pints. As the buzz slowly built up in my head, I started to feel relaxed enough to take our casual meeting to the next level. The waitress came by with the check, and I reached for the pen to sign the receipt after she swiped my credit card. The sweat from the beer glass was enough to make my hands slick, and the pen slipped from my fingers to the floor.

"Here, let me get that," Randy offered. As he leaned down to pick up the pen, his tee shirt slid up his back, revealing the black waistband of his Victoria's Secret panties protruding from his jeans. My dick was solid by this point. As I signed the receipt, I slid my receipt copy to Randy. As he flipped it over to read the writing on the back, he silently read my address and the note "Get your sexy ass over here in an hour." We said our goodbyes and headed for the door, exchanging a glance and a wink as we left the bar. In my buzzed, horny state, I had the courage to explore my most taboo sexual fantasies and not worry about what my wife would say about it.

Randy was prompt, ringing my doorbell exactly one hour after we left the bar. As I opened the door for him, his eyes were greeted with the sight of me, freshly-showered, wearing my white terry bathrobe.

"Well come on in," I said with a grin.

"What do we have here," Randy said, tugging at my belt. I grabbed his hand and held it at his side for a moment.

"I think I could go for a little foreplay first," I said. My hand swiped across the front of his jeans and slowly worked their way under his shirt before pulling it off. My fingers then softly traced a line down his chest to his waist, pulling the zipper on his jeans down. The black VS panties I glimpsed in the bar were made from lace mesh, barely concealing the smooth outlines of his penis & scrotum. I could see Randy's manhood growing chubbier with excitement.

"Alright Buddy, it's time to stop being a cocktease," Randy said. Playfully he grabbed the belt of my robe and gave it a yank. As the terrycloth fell to the ground, my young flesh was on display for this older, fatherly figure to whom I had trusted with making my first male-on-male experience special. My stiff cock was concealed only by a pair of white, lace-mesh panties.

"So who does your panty shopping?" Randy asked.

I replied, "This was the pair my wife wore on her wedding night, the night we took each other's innocence."

"A great choice," he said. "This afternoon, a boy becomes a real man."

"I can hardly wait!" With that, I turned around and started shaking my panty-clad ass. I ran through my bedroom door and flopped, my back slapping the comforter. Randy was right behind, getting on all fours on top of me and covering my body with little bites. He kissed my cock through my panties as they stretched down my shaft, unable to contain my bulging manhood any further.

Sliding out from under Randy, I got behind him and started rubbing the panty-covered curves of his glorious ass. My hand reached between his legs and slowly started to massage his balls, before I used my thumb and index finger to rub up and down the sides of his shaft, The rubbing was enough to cause his black panties to slide down to his balls.

After several minutes of lying on our sides and stroking each other, I got up and pulled Randy's panties completely off. Finally I got to see his cock in its full glory, fully erect. It was about 5 1/2 inches, cut, and average girth. Not enormous, but the perfect size for being the first dong I ever played with.

"Oh Randy," I said, "My lips hunger for your manhood."

He flipped me a condom. "If you're gonna suck me off, let's be safe about it." I nodded and put the unwrapped condom on the tip of his cockhead. I puckered my tips into a kiss on the tip of his dick. Opening my lips some more, I hugged the condom and slid it down his smooth shaft as my throat took his entire length. As my head rose and I coughed and gagged, I told him that the condom wasn't terribly tasty.

"Then maybe it's time for plan A," Randy said. "Plan Anal." He grinned, leaned over, and grabbed me by the ankle, pulling me onto the bed.

"Let me lay on my back," I requested. He was happy to oblige as he completely removed my panties, letting them dangle around my left ankle. I grabbed the tube of astroglide from the bed and rubbed a blob up and down Randy's condomed cock. As i held my knees to my chest, Randy put a blob on his own finger and rubbed my anus with it. I could feel his finger slowly probing my anus, making a come-hither motion. As he withdrew I felt lucky to have voided myself ahead of his arrival.

"Feels like you're ready," Randy told me. I took a deep breath, recognizing there was no going back now. I was about to get my asshole violated by a man I'd just met this afternoon. He told me to take a deep breath and relax as he placed the head of his cock at my opening. He used one hand to hold his dick and another to spread me open as far as I'd stretch. I was already focused on that tearing feeling as he began to push deep inside of me.

"How are you doing?" Randy asked.

"Doing alright," I told him. "It burns a little bit, but I'm doing fine."

"Alright, let's do this! You're handling it like a champ. A very sexy champ." He pushed in further, going slowly and leaving me feeling completely filled. Here we were, two grown men, fathers and husbands, enjoying an intimate moment. Call it fucking, call it partying, but there were no words to describe the ecstasy I was feeling. I don't remember much besides throwing my head back to scream, then looking Randy in his eyes as his cock twitched up and down inside me during the throes of ejaculation. My anus puckered and convulsed as it felt his stretching. Randy slowly slid out of me. I remember being surprised at the strand of lube and mucus that dripped out of my gaping anus as Randy withdrew. So that must be what my wife feels when we make love, I thought.

Randy left the bedroom briefly to flush his condom down the toilet, then returned to find me lying on my back, exhausted. "Looks like somebody's still not happy," he said, pointing to my floppy cock. He was right; I still hadn't got off yet. Randy was determined to fix that; he sat me on the edge of the bed and whipped his cummy cock out next to mine. Grabbing them both in his hand, he stroked furiously until I came all over his smooth public mound.

Sweaty and covered in lube, mucus and cum, we showered off together, taking turns lathering each other up and drying off. Afterwards we sat on the couch naked, enjoying some of my homebrewed beer and talking about what we'd just done.

"Randy," I said, "whatever you did to me on that bed was amazing. I loved feeling your cock deep inside of me. I just felt so stretched, so filled, and so trusting that you'll make me feel amazing. We really need to do this more often. Do you want to be closed-loop? We'll see each other exclusively for all our man-on-man needs."

"Sounds great," Randy said. "Your ass is the tightest thing my cock has ever felt." He slid his wife's black lace panties back on and repeated my tease from earlier, shaking his fine ass for me. "But next time, you're gonna get a load of me!" My cock got stiff again, and Randy could see it. I was filled with excitement thinking of returning the favor on Randy's ass!

Randy and I hooked up two more times before my wife returned, and that'll be a story for another time. I hope to hook up with him again soon!

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AnonymousAnonymousalmost 2 years ago

My fantasy exactly! I love ass play, the feeling of having a dildo, butt plug, a finger, or a cock in my ass. I'm a true bottom. During an erotic massage once, my masseuse said to me as I lay on my back taking his gorgeous, thick cock, "Look me in the eyes, I love to look at the man I'm fucking!" He was wonderful! Haven't had another massage since Covid hit over two years ago. Butt I'm ready!! I'm thinking a fuckbuddy like Randy would be good. I have a divorced male friend who I'm thinking of asking if he shares my desires. Should I? I'm married like Mr. Peterotica, and feel the same - am I ready to cheat on my wife with another man? I'm also Catholic, butt older, 66 yrs old. However, I've enjoyed anal pleasures since my 20's. Looking forward to more entries from the author!

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