Better Late Than Never

After getting writer's block on a fiction piece that wasn't going anywhere, I take up something more autobiographical. There are some artistic embellishments (that I hope work for you) and a few less than erotic details left out (e.g. getting kicked in the head, muscle cramps, etc.). I still can't believe how lucky I turned out to be.

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I don't suppose it would be exactly accurate to refer to Tom as my new friend since we'd exchanged a lot during the past month and a half. When he first responded to my profile message that I'd supplemented with what I hoped were some artistic nudes that I'd struggled to take of myself, it was difficult for me to gauge just how interested he was. As we messaged back and forth, we revealed more and more about ourselves while our descriptions of our sexual desires became more explicit, more worthy of multiple masturbation sessions.

I was both thrilled and a little anxious when Tom suggested we move to Zoom sessions. The first few were more CrotchTime than FaceTime as our cameras focused on the cocks each of us was hungering for. I was relieved that he found my average six inch but thick uncut cock to be intriguing. I'd feared that he might have a seven and a half or larger monster, but his cock was only a bit longer than mine though not as thick. He was cut and had one of those gorgeous helmets that I'd always envied and drooled over.

I kept a great shot of his erect cock on my phone and found myself compelled to stare at it often, imagining in detail how my lips and tongue would slowly, lingeringly, fiercely bring him to maximum hardest and length. It was reassuring that staring at the photo would get me hard. Maybe I didn't have to worry that fantasy was one thing, but if he and I ever met, I'd end up with an embarrassingly limp dick.

I knew there would be times when I'd want nothing more than to feel him cum in my mouth and savor his taste. Since we were both older guys, I knew that there wouldn't be jets and jets of cum, but that was okay. Still, as older guys with extended recovery times, I knew I'd want to keep that cock hard for as long as possible. I'd imagine breaking off from sucking him, getting him on his back, and slowly lowering myself, taking each hard inch up my ass. Play with butt plugs and dildos made me confident that wouldn't be a problem.

One night he moved his camera up and moved his chair back, so I could take him all in. The lighting wasn't great, but I did like what I saw. I hastily rearranged my lights and lifted my camera up to give him a similar view. We didn't say anything; I mirrored his actions, slowly stroking my cock and tugging on a nipple.

I guess my appearance at least wasn't a turn off because he increased the pace of his strokes and I turned up the volume to hear his moans. When he stood up and moved forward to fill my screen with his hand gliding up and down his stiff shaft, I did the same. I almost lost it when his deep groan was a prelude to his cock spasming and his milky white cum spurted from his beautiful cock head. I was pretty sure that he must have splattered some cum on his screen because I did when I came about 30 seconds later.

I was mesmerized as I watched his cum slide down his shaft and reach his balls. I hoped he was as entranced watching my cum slide off my head. I loaded a finger with part of my load, moved the camera up, and slipped it into my mouth.

I wanted him to do the same, but he disconnected.

I had a few moments of anxiety. Was he done with me?

Then I my phone chimed to announce a text message.

"Fuck, yeah. We must meet."

I responded, "Fuck, yeah," but I wondered if that would really be possible.

The next night, we video chatted again. We were both nude but set back in our chairs, the lighting giving only a basic idea of our faces. Hey, he looked okay, and I was more focused on his hand lightly stroking his cock.

"So why now?" he asked. "Why not before?"

Good questions. I hesitated. Should I be honest? Why had I never moved from bicurious to bisexual? Or, I suppose, Gay. As a lifelong procrastinator, it was a step that I been putting off for nearly 40 years. What the hell, I thought. I let it all out.

Back in my 20s, I had a lover who, probably inspired by Penthouse letters, wanted to try anal. The sensation of pushing past the sphincter muscles and entering the smooth, tight warm rectum blew my mind. When she reciprocated by finger-fucking my ass, I was left with two thoughts: 1. Plunging my cock into a puckered anus was totally awesome; 2. I couldn't stop imagining how it would feel to take a cock up my ass.

Of course, there was no internet back then, but there were local tabloids with explicit personal ads. I responded to one that seemed perfect, wrote a letter, and got a response. I probably sounded like a nervous idiot when we talked on the phone and set up a meeting at a motel. Of course, my negative imagination conjured up all sorts of dire scenarios, and I called back to break it off. Lost opportunity.

Then AIDs really ramped up, so I put those desires on a very back burner.

After a couple more forays into anal sex, my lover didn't seem interested any more. However, she loved to begin lovemaking by lying on her stomach with her face hidden cradled in her arms, her thighs clamped together, directing me to her shapely buttocks. I loved to massage and spread her cheeks, lapping her crack with the flat of my tongue, moving up and down with sucking kisses and bites before flicking her anal bud with the stiffened tip of my tongue. She would moan when I rimmed her and pressed my tongue against the resistance of her sphincter muscles. Then she would spread her legs a bit, drawing me to the slick wetness of her vagina and slit. When my tongue probed there, she would turn over, spread her legs wide and reach down to pull back her outer lips to expose her swollen glistening clit.

I loved giving oral, finding the variety of ways I could use to make her cum several times. Many times I would press my thumb into anus as two fingers slide in and out of her vagina. I loved the taste and smell, and I would go on and on past the time my jaw began to ache until she couldn't take anymore. Eating her was far more intense than fucking.

Granting how oral I was, whenever she sucked my cock, I couldn't help but think how much better I would be at cocksucking. That thought too went on that back burner.

"So you'd make love to my ass and rim me?"

I'd hoped he'd open up more with his history, maybe chronicle a similar past. Still, the question hung there.

"Count on it," I replied, trying to sound more confident than I felt. I wasn't quite sure how to take his smile, but I noticed that his hand stroked his cock more vigorously and his fingers tugged hard at a nipple.

"Finger-fuck my ass while you suck me?"

"That's a given." I hope my expression was convincing.

I turned back to the "why now?" Late into my 60s, I found myself widowed, living alone, and retired. Finding myself experimenting with butt plugs and a realistic 7"a dildo, sticking it to the shower wall and working past my gag reflex to take it all .... Finding myself drawn to bisexual male stories and mmf porn, then gay porn and male nudes .... I changed my eating habits to lose weight and exercised more. I started shaving my pubes, got Cialis, and went for AIDs/STI testing. I felt sexy wearing thongs. I found myself getting closer to taking the risk.

Revealing all that made me feel pretty vulnerable. I wondered if I was blushing and if it showed up on the video feed.

I tried to move off the deeply personal.

I rambled on about how disappointing responses, except his, to my profile and my attempts to reach out to others had been. I was amazed to find how many guys had particular desires and definite exclusions--suck but not be sucked, anonymous jerk off in car parks, etc. Was I being naive to want it every which way I could imagine?

"I get it," he replied. "We're on the same page, I think. Actually a lot of the same pages."

I wished he'd elaborated and given me more details, but he didn't. I really wanted to believe he was just very discreet or a little shy rather than devious.

I'd revealed a lot about myself. I felt exposed, which seemed a little ridiculous to worry about since I was naked and stroking my erection.

"I want you," he said and moved forward like the last time to give me a vivid close-up of him stroking that cock I so wanted.

"I want you," I replied, also moving forward.

Once again, I mirrored his motions, wetting the tip of a finger and spreading my pre-cum over the head of my cock until it glistened, spreading to the sensitive underside beneath the rim.

A gasp and guttural moan that escaped from me when he turned around, bent over, and spread his cheeks to reveal his puckered anus.

Was his cock throbbing as he was imagined how I would spread his cheeks, lap his crack with my tongue, spread kisses and gentle bites up and down his buttocks? Did he have any idea how my lips and tongue would lap, lick, suck, probe his anal bud? Did he know I'd be of two minds--loving going slow and deliberate, all the while hungering to slide my cock into him?

He disconnected. Damn, why I thought? Did he know the last time was so burned in my brain that I could see his cum bursting from his cock? Could he see mine, I wondered, as my fingers scooped up the delicious whiteness and brought my fingers to my mouth?

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Finally we arranged to meet. We were both within comfortable distance of a glitzy casino with great hotels and restaurants. We wanted this to be special--not just a quickie in a sleazy motel.

Getting ready turned out to be the worst part. While I'd gotten pretty adept at shaving my pubes, I hadn't figured out a way to shave the hair around my anus. It took me a while, but I finally got up the courage to call to make a waxing appointment.

To say the procedure was an ordeal is an understatement. I was probably beet red with embarrassment from the time I walked in the place to the time I left. It didn't help that the young woman who did it could have been my granddaughter. Fortunately she was business oriented and didn't make any comments, but heaven knows what she had to say afterward to her co-workers. Embarrassment and the fact that she wasn't particularly attractive kept me from getting hard during the procedure that was mercifully brief though painful.

Though I knew it wasn't essential, especially because we had decided to use condoms for anal sex, I gave myself an enema early on the morning of the big day. While not fun, it was a lot less excruciating than the waxing. He hadn't really talked about taking my anal cherry, but I had my fingers crossed. Which was basically unnecessary since I knew I could take the initiative and lower myself on his gorgeous shaft. Of course, the question was whether I'd be coordinated and flexible enough to handle that. I was painfully aware that fantasy can break on the hard wall of reality.

On the drive to the casino, I turned up the radio and sang along to keep me from being overwhelmed with nervous doubts and worries. For the most part it worked. For the most part .... I set an alarm on my phone, so I could down my Cialis with a gulp of water about forty-five minutes before my expected arrival.

I checked in at 2:00, the earliest time. I went to the room with my overnight bag, turned down the bed, and placed anal lube and condoms on one of the nightstands. Once I hung up my dinner clothes, I went to take a last piss and was thrilled to see a spacious walk-in shower in the bathroom.

I headed out to meet Tom in the bar that he'd suggested. I took it as a good sign that I was semi-hard. A limp dick would be a real Hindenburg--a humiliating disaster that would send all my hyped-up fantasies crashing to earth.

The plan was fairly simple. We'd met in the bar in the afternoon and share a drink before heading to the room to get it on. We'd head out for a relaxing dinner around 7:00 to give our aged libidos time to recover before Round Two. Before an indulgent breakfast feast in the morning, there would be a Round Three.

If it didn't go well, I'd still enjoy that dinner, sleep alone, and head out early, grabbing some breakfast at a drive-thru. I'd have to resign myself to Woody Allen's maxim--"Masturbation is sex with someone I love."

Still I was more excited than anxious. My semi-hard cock had to be a good sign, right? As I headed to the elevator and my meeting with Tom, I decided to put any trepidations I had aside and let my cock do the thinking. It seemed to have the right idea.

Two obviously senior ladies were coming down the hall toward. Their low cut tops would have been more attractive on younger women, but they obviously kept themselves in shape, so they were kind of sexy. At my age, I suppose my standards had been lowered.

They were a little giddy and probably a bit tipsy, having taking advantage of the free drinks offered by casino staff. The shorter brunette, whose tight yoga pants gave her a pronounced camel toe, had her eyes riveted to my crotch, probably imagining that bulge promised that an eight inch monster lurked inside.

Sorry, ladies, my average six incher is just a little excited by the prospect of all it would do and be done to when Tom and I got naked.

The taller one with dyed red hair did a very poor acting job of dropping her key card in my direction. We both bent down to pick it up, giving her the opportunity to give me a close-up view of her ample tanned boobs that threatened to escape from her low cut blouse.

"Oh, thanks," she said when I handed her the card. 'Why don't you come in. We've got some champagne being delivered to celebrate our big winnings."

"Thanks, but I've got a friend to meet. Congratulations on your winnings."

As I waited for the elevator, I wondered if six months ago if I would have jumped at the opportunity, hoping it would lead to a kinky threesome. I had supposed I was bisexual, and I guess in theory I was, but it hit me that from this point forward it was sex with men was what I hungered for. Perhaps I'd changed. Maybe I'd always been gay. Stupid me for not figuring that out sooner. I knew that from this point forward I just wanted to be with men.

If I passed "the test" with Tom, I'd change my profile to "Gay."

When I stepped into the bar, I immediately picked out Tom at a bar height table. Much to my surprise a woman, a blonde in a green dress was seated across from him. When he saw me and raised his hand. The woman turned in my direction and smiled.

I wondered, or should I say worried, about what she was up to, but there was one positive about her presence. I climbed up on the chair right next to Tom. If she hadn't been there, I probably would have sat directly across from him.

She was definitely a young one, twenties maybe.

"Now that your friend has arrived, I leave you two to it. I'm sure you know what I mean," she giggled and gave us a wink. She got up, gave Tom a peck on the cheek. She lightly raked her nails down my cheek and whispered in my ear, "Enjoy, Honey. I'm sure you will."

She headed back to the bar on what had to be four inch heels. She swayed her hips, but she didn't have much of a butt.

"Should I be worried about competition?" I asked. Tom had an almost full martini in front of him, and there was another with a slight trace of lipstick on the rim.

"I'll explain in a minute," he said with a laugh. "She left the drink for you after taking a little sip. There's more to her story, but I'll fill you in later. Let's toast to new meetings and new adventures."

"Most definitely, I replied. I turned the glass around as I picked it up. We clicked glasses and drank.

"She saw me sitting alone and brought me another martini. You know, the usual come-on. I was, of course, polite, but she was a little miffed though that I figured out she was a cross-dresser.

"How'd you manage that?" I asked.

"Well, her make-up foundation didn't completely cover her stubble and she really had "man hands" despite the exquisite nail job. That pissed her off because that had cost a lot."

"Man, I'll have to watch myself. You're really observant."

"Well, I've seen you naked multiple times, so you don't have much to hide. And I hope it is only going to be a few minutes until I see you naked again."

"First you should wipe the lipstick off your cheek," I replied.

I really liked his laugh and the sparkle in his eyes as he did as instructed with a cocktail napkin.

The lighting in his video streams wasn't all that great, so this was the first time that I really got a good look at his face. He definitely had a nice smile. His lips were quite full. Not only could I imagine how beautiful they would look and feel sliding over the head of my cock, but I also knew I longed to caress them with my own lips. Whatever trepidation I might have had about kissing another man instantly vanished.

I took another sip of my martini. "Enough of cocktails," I said. I slipped my hand under the table, squeezed his thigh, and lightly dragged my fingers over his crotch. It was such a turn on to find that he was already semi-hard like I was. "Shall we get on with making cock tales?" I gave his shaft a firm squeeze.

"T-A-L-E-S. I hear you," he said. When I felt his hand searching for my cock, I spread my legs to give him access. "And I feel you. Ummm. Let's go."

I so hoped for an empty elevator, so we could start groping each other, but luck wasn't on my side. We had to politely listen to an elderly couple tell us about their successful slot machine strategies. The corridor to our room was also frustratingly busy.

Once I flashed my key card over the sensor and we entered, we both flung ourselves at the other. My lips tugged at his lower lip, and he opened his mouth to accept my darting tongue. He sucked hard at it and I returned the favor when his tongue penetrated my mouth. We had both instinctively reached behind the other to grasp each other's buttocks, pressing our crotches together. The wild forceful kisses had brought our cocks to full hardness, and we swayed out hips back and forth, grinding against each other, knowing that soon we would be bare smooth skin to bare smooth skin.

We each stepped back, knowing that we needed to slow down.

"At our age," he said, our passionate embrace leaving him still a little breathless, "if we don't slow down and cum in our pants, we'll be out of commission for who knows how long."

"Not quite the slow start we had planned," I replied with a smile. "But no regrets. That was so intense. I guess to slow things down, I'll make a last trip to the bathroom."

"Good luck pissing with that hard-on," he laughed.

"I'll manage. Been there, done that."

When I finished, I made sure to run some hot water and washed off my cock, which was now back at half staff. I hoped that we would now slowly undress each other and then move to the bed.

No such luck. Tom was in the process of stepping out of his teal thong as I exited the bathroom. He was on the other side of the bed from me, and he moved up on the bed, scooting to the middle on his knees. His right hand slowly stroked his cock, and he beckoned to me with his left.

I began slowly undressing, not really to tease him, but because I was so mesmerized by his beautiful cock. Its well-defined mushroom head glistened with his precum. Being uncut myself, I had always been fascinated by and envious off well-defined cock heads. I'd even gone so far as to look up adult circumcision, but decided not to go there.

By the time I shed the last of my clothes, I had marveled at the smooth taut skin of his shaft and the bulge of the blue veins on the surface.

I moved across the bed on my knees to meet him. We each put one hand on the other's shoulder and reached down with the other to caress for the first time another's penis.