First Time (going All the Way)

After a few months of happily sucking Chris' cock I was in for a disappointment when he started dating a girl. Now his cock was occupied I began to feel frustrated. I wasn't jealous, I just missed having a stiff piece of meat in my mouth.

I began to think of anyone I could who might be open to laying back & getting drained &, to be honest, I was beginning to wonder how other cocks might feel & taste. It didn't take me long to decide that Jay, one our one time 3-some playmates, might be worth a try.

Jay had been the first guy that my wife, Anne, had for one of our 3-some date nights. Jay had been dating Thalia, one of our girl playmates, & she'd sent him along to satisfy Anne's craving for 2 cocks in her at the same time.

Jay had always seemed at ease with being naked in a bedroom at the same time as another guy & it made me wonder if he was open to more than just sharing a woman. He & Thalia had broken up, acrimoniously, for some unknown reason. On the other hand Thalia & Anne had become best buddies, so it made bringing Jay into the bedroom again uncomfortable for Anne. As a result I'd not seen him for a while & if anything did happen between me & Jay it was a sure thing that Anne would never find out.

I hatched a cunning plan & called him up, nonchalantly making small talk until he asked about Anne. I told him "She's doing fine, enjoying the quiet now the kids are back at college. In fact she took the opportunity to take some time off & visit her parents in Minnesota this weekend."

Step one.

Of course he wanted to come & play with us, but slowly I swung the conversation around to the subject of being naked in a bedroom with another man. "You seem to handle it pretty well, not nervous or anything."

"It doesn't bother me." He replied.

I licked my lips nervously & tried not to let my throat tighten up. "Are you ever worried that the other guy might make a move on you?"

There was a slight pause, as if his eyebrows were being raised, "That's quite the question. Why do you ask?"

As nonchalant as I could, given my stomach flutters, I responded, "Oh, just curious."

Step two.

We talked some more, then I asked him if he wanted to come & play. He did (no surprise there) & he asked when. I relied "Saturday, around 4pm?"

There was another pause, this time notably longer. "Well, alright then. See you at 4pm."

Step 3.

My plan was simple. If he showed up on Saturday & we got busy then no problem. If he showed up & was not into because Anne wasn't there then I could simply claim we'd become confused over which weekend I'd been talking about.

I set the phone down & tried to calm myself, trying to let the realization sink in that I'd quite possibly just managed to talk a guy letting me suck his cock. I tried to think about it, how it would feel, given the few, furtive glimpses I'd had of it already during our 3-somes. Suddenly Saturday seemed an age away.

I was as giddy as a teenager come Saturday. I had my snowmobile in the garage up on its stand & the garage door up, because the belt needed changing. Sure enough at 4pm up rolled Jay's car & out he stepped. I looked up, seeing that he had noticed that Anne's bright yellow sedan wasn't in the drive way & gave him a smile & a wave. I made the usual friendly greeting, handed him a cold beer & made small talk. At no stage did he mention Anne's absence, which was encouraging.

Jay was a bit older than me, taller, more muscular & very hairy across the chest & turning grey in places. He wasn't all that handsome, really I'd have to say he was pretty non descript in the looks department, bland even, but had a quick & quirky sense of humor that soon had ladies giggling. A teenage motorcycle accident had left his scarred up on his left arm & the tip of his little finger was missing too. Apart from that I knew very little about him, other than he had a nice tool, a nice nut sack that hung way low & he could shoot big loads.

I closed up the garage door, "I hope you didn't mind that question the other day." He shrugged & didn't know what I meant, "You know the one about being naked in a bedroom with another guy."

He looked at me for a moment, smiled & simply said "Oh, it don't matter. I fully understand." My heart raced. What now? I was about to just dash over there & unzip his pants when Jay leaned back against the work bench, legs slightly spread, the tight t shirt he wore showing a respectably muscular chest & biceps. He looked around, "Are you finished here?" I nodded & he shifted his stance to spread his legs a little wider, "Any tools you need to put away?"

I suddenly realized that it wasn't only myself who was engaged in this dance, Jay was feeling me out too. I nodded & said "If you don't mind...I mean I can leave it if you've got other things to do." He shrugged & said that it was up to me, he was happy either way. And so I put down my beer & took my first step toward him. At the same time Jay put his beer down on the bench & leaned back, resting his hands on the edge, inviting me.

The first thing that I was aware of was the heat from his body, as I stepped up my eyes ran down to the crotch of his jeans. I could now smell him too, with the scent of fresh laundry, the slight hint of body wash, I knew that he was all clean, squeaky clean & ready for me. Taking a deep breath I hesitantly reached out for the belt buckle & nervously undid it while Jay's hands came up to rest on my shoulders. I could see a growing bulge in his pants & wanted to free it so badly. I popped the waist band button open, giddy with excitement, then found his zip & slid it down. With hands trembling I peeled his jeans down to reveal tight, blue & white candy striped boxers that contained his straining cock. Jay was breathing deeply now but didn't say a word.

I brushed my fingers over the cotton that covered his erect cock, sending shivers through him & making him gasp. "Mmmm, nice!" I said, quite without meaning too. Searching for the opening I slipped my fingers inside & felt him for the first time, making me tingle all over. My fingertips found his shaft, ran up over his firm head & then down over his ball sack before swooping back up to roll his foreskin up & down. I caught a quick glimpse of his cock head, deep red & shiny, through the fly of his boxers & felt my own cock stirring.

I had to have it! I knelt down & pulled his hard cock out, a tiny, shining star glinted in the tip with the first hint of pre cum. I curled my fingers around his shaft, cupped his balls & inched my head forward, my lips parted, sliding his fresh, clean cock into my mouth. It was indeed everything I'd hoped for. Jay must have thought so too, as he let out a gasp of pleasure.

My tongue first found his slit & lapped at that sweet drip of pre cum, then went to town over his head. I bobbed & licked, stroked & squeezed, letting my hands run along the insides of his thighs before resuming their duties caressing his balls & stroking his shaft. Soon Jay was breathing hard & each time I sank my mouth down onto him I could feel a twitch in his hips that grew with each passing second. His hands left my shoulders & were suddenly firmly planted on my head, I knew he would soon come & I felt a thrill run through me.

Then he gave a heavy grunt & cum flooded my mouth. I greedily swallowed & sucked & licked his head while my fingers gave his balls a squeeze. Jay almost bent double right over me, his chest brushing against the top of my head, before he jerked up, thrusting his cock into my mouth with one last shudder before a final squirt of cum & a fit of gasping.

It felt wonderful to have taken a cock once more & I stood up, wiped the dribble of cum from my lips & helped steady Jay against the work bench.

"You OK?" I asked, proud of myself.

He slowly nodded & fumbled for his pants, "Yeah' he mumbled, "wow!"

He folded his now limp, but still semi stiff, cock away in his pants continued to gather himself. I was sad to see that cock go.

We went inside & hung out in front of the TV & had another drink. He asked about my cock sucking & I told him all about it. It was during the later stage of the conversation when I noticed that the bulge in his pants had returned & he'd noticed that I was looking at it.

Jay smiled at me, making the corner of his eyes wrinkle & said "You know I've got more for you, lots more, if you want it." I said I would take anything he could offer, which had consequences I didn't appreciate at the time, to which he replied, "Oh really?" with a knowing wink.

We adjourned to the bedroom & stripped off, this time it was easier than I'd thought being naked with him, but I was still a little nervous. Jay pulled off his t shirt & rapidly yanked off his pants, revealing his broad chest, slim waist & stiff cock. He directed me to lay on my side, propped up on one elbow, then he kneeled on the bed & guided his cock into my lips, giving him the chance to reach over & touch my cock too!

I wasn't read for that & actually swatted his hand away. Jay seemed puzzled & I muttered something about being a bit surprised, then went back to sucking on his cock. I noticed his hand make its way back down to my cock & gingerly brush against me. It felt odd, but I had to admit that it also felt good too. I began to relax & wasn't even bothered when his hands started to stroke between my legs & over the cheeks of my ass. It felt good...it felt very good, relaxing & stimulating at the same time.

Slowly Jay began to arch over me, adjusting himself on the bed so that slowly he was on top of my, legs spread over my face, his cock still in my mouth, lowering himself. I realized that he was about to go down on me too & I once more felt the butterflies in my stomach, but I was too far gone & soon this feeling was blown away by the warm, wetness that enveloped my cock.

His hands were everywhere now, rubbing my ass, squeezing my balls, stroking my cock. Likewise I let my hands roam, rubbing his ass, stroking the inside of his thigh, his hips & groin. It felt divine.

Suddenly Jay let up & rolled off me, leaving me on the bed, dizzy. He was fumbling with his clothes & I was alarmed for a moment that he might be leaving. But then he sat up & directed me to get on all 4s on the bed. I honestly didn't know what for, but I did as he asked. I expected him to slide under, maybe a repeat of the 69 we'd had only with me on top this time, but to my astonishment he pulled up behind my ass instead.

I nearly freaked. "What are you doing?" I said, rolling over to protect my ass. Sure enough my fears were well founded. His cock was now wrapped in a condom, glistening with lube.

"I thought..." he began. "I mean...well, you sucked cock so good I thought you were...." Again he trailed off. "My mistake, I'm sorry."

I made some sort of reassuring sounds, "No worries" or something like that, but I just couldn't take my eyes off his cock. He took off the condom & cleaned up in the bathroom. "You've never done that before, or is it me?" he asked. "If it's just that's it's me then OK, it's a very personal thing who you let in you ass, I'm not offended."

I told him that I'd never done that before & couldn't understand why anyone would want to. Jay laughed, "Yeah, some guys hate it, some guys love it & say it's the most amazing orgasm they've ever had."

I asked him if he'd ever been ass fucked. "No, but I've had a finger up there, right on my p-spot & it is pretty fucking amazing."

"What's this 'p-spot' thing?"

He explained it to me. "I can show you if you want." he said, smiling & reached under the bed for the box of toys which, from our previous 3-some nights, he knew was there, pulling out a thin vibrating dildo. "It's amazing." He said, smiling wickedly & twiddling the dildo. "It's just a dildo."

As if in a dream I lay back, letting my legs open. Jay came alongside me & started sucking on my nipples, something I'd never had before. So many new experiences, so much unexpected pleasures, so much I'd missed out on over the years without ever even knowing it. I didn't want anything up my butt & yet I wondered if this was something else I had missed out on. After all I'd never previously thought I'd enjoy sucking cock so much. Jay assured me he knew what he was doing, I gulped & nodded my approval, then closed my eyes, hearing only the soft rustle of his body sliding over the sheets & the bouncing of the bed.

First I felt the warm wetness around my cock again, then something probing between the cheeks of my ass. I tried not to tense up, but the slim vibrator was slippery with lube & slowly it advanced, drawing a strange, tingling sensation from my ass. I began to relax & soon felt for the first time, my ass being penetrated. Further & further it went, slowly, edging back & forth. Then came the buzzing sensation & a fresh wave of pleasure rumbled through me. I felt warm all over.

And then came a sensation that I had never thought possible. It was like an avalanche, it was like an electric shock, it was like an explosion, it was an indescribable torrent that left me seeing stars & my ears ringing.

Jay pulled the vibrator out & beamed at me. "My my," he purred, "We are sensitive, aren't we." Then laughed.

"Wow!" I croaked, "That's amazing!" then groaned once more as he let the wicked vibrator have its way with my ass.

This went on for what seemed like forever, when he whispered to me, "I've got something even better, if you'd like."

In a semi conscious state it was all I could do to nod. I felt his hand on my side, gently signaling me to roll over, then both on my hips to pull them up. Again he got behind me & I could hear the ripping sound of a fresh condom packet being opened. I felt terrified, like I was about to cross a line that meant no coming back.

"Are you ready?" he asked. I shook my head, panting. I wanted to move, but somehow couldn't. "You're still here," Jay said, his hands resting on my ass, "I won't hurt you" he purred softly, "Just say no, or walk away from it, I don't mind either way."

I could feel the warmth of his groin shining like heat lamp against my ass, my exposed, open, vulnerable, unprotected ass. I felt something rising in my gut, something inescapable, that a guy's hard cock was about to be put into my asshole, that I was about to be violated & if I didn't do something right now to break this spell another man's cock would be deep inside me, fucking me like a girl.

I breathed in deeply & let the word "NO!" form, ready to let it fly loudly & clearly...but when I opened my mouth what came out was something unexpected, a tiny, shivering voice that whispered "Fuck me...." I couldn't help it, I tried to say no again, but this time, a little louder, I repeated it, "Fuck me!"

"Just relax, let me know if you want me to stop." said a calming voice from behind me. I first felt the tip of his cock bump against me, the terror running trough me like an earthquake. I grunted, groaned & squealed, gasping & sobbing, It did hurt a little at first, but Jay was careful, probing a little deeper each time then sliding back. His grip tightened on my hips & I felt something warm, dangling & rubbery, bump against me. He was all the way in.

I gripped the sheets as he took his first, full stroke. It wasn't pain, it was the wave upon wave of orgasmic pleasure that flooded out of my p-spot as the head of his cock rolled over it, again & again. Later Jay told me I was a gibbering mess, my teeth chattering, uttering a stream of sounds that were like an animal, my head rolling around. I remember none of that, except that I was somehow trying to cling on to reality as best I could.

Jay pumped away at my virgin ass slowly & carefully but soon he was grunting too. He gave a groan, "Oh fuck, I'm gonna cum!" & then shuddered, sending me into a place even further beyond where his cock had already sent me.

After we'd recovered & cleaned up I started to feel remorse, guilt & embarrassment. Jay set me right, "Naw man, you're not gay, you're no gayer than I am. You don't look at a guy & think 'Hmmm, he's yummy' or 'I'd like to date him'. You just like pleasures you can only get from a guy. Simple test, in a room full of attractive men & women, who'd you look at?"

He was right, I'm a straight guy who loves women, nothing changed there. But I love to suck & slide a stiff cock up my ass & I've never felt more satisfied.