My Second Time

by MartyA

15 May 2021 3474 readers Score 9.5 (105 votes) PDF Mobi ePub Txt


Wow, this feels good. The Florida sun warming and soothing me, I sighed with sensuous pleasure as a gentle breeze caressed my naked body. Stretching my arms over my head I flexed my toes and sunk deeper into my poolside chaise. I marveled at how wonderful the sun felt on my nude body. "It's good to get away." I thought. All my tensions were beginning to melt away.

It had been a rough couple of years. My 25 year marriage broke up, work was a bitch, my kids caused me endless worries, my stress seemed unrelenting. I had decided to treat myself to a little down time. A few days of sun and swimming, read a few good books, all alone to rest and recuperate in a clothing-optional environment. "This is just what I needed to recharge." I thought.

Over the years we'd been to a few nude beaches but I could never convince my wife to go to a nudist or clothing optional resort, so this was a first for me. I love being naked in the sun. I found the other guests friendly but not intrusive and the environment was carefree and stress-less. It was as if I had shed my worries along with my clothes.

It was really freeing not to have to worry about what to wear to the pool or spa, the restaurant or the gym. Just walking nude around the beautiful spacious grounds was a uniquely relaxing and a very sensuous experience.

That said, I didn't find the atmosphere overtly sexual. I remember thinking that while I wasn't there looking for any kind of hookup, old desires were stirring and I should be open to whatever happened. At that point, I was thinking mainly about women, but most of them seemed to be accompanied. Actually, the truth is that sex was the farthest thing from my mind; I was just there for some downtime.

"Is this spot taken?" My thoughts were interrupted by a good looking guy about my age pointing to the chaise next to mine. "No, not at all, please help yourself." I roused myself enough to sit up and rearrange my books and lotions. "Here put your stuff on the table, there's plenty of room." "Thanks," he said.

I'd seen him around for the past day or so, and he too seemed to be by himself. He had a build similar to mine, slender but athletic, a couple inches shorter and maybe a little more muscle than me. We both used the gym and I'd noticed him because unlike most of the other gym goers, he knew what he was doing.

With a firm handshake he introduced himself and we chatted as he arranged his towels and he got himself settled.

His name was Dave. He'd been coming here for years. He agreed that it was a uniquely relaxing environment and he too loved to sunbathe nude. He pointed to an area of his back between his shoulder blades that was a little burned and asked if I'd mind applying some sunscreen for him. Since this was obviously an area he couldn't reach I was happy to help.

I noticed his trapezius muscles were very tight, and knowing how bothersome that can be, I kneaded his muscles a little when putting on the sunscreen. We talked about fitness and working out and how at our age it really helped to get a massage from time to time.

Dave asked me if I needed a massage and I said something like, "Of course, but I got one yesterday. They do a really good job here. I'd love to get another, but any more than one would be financially irresponsible." At that point I yawned making it clear I was getting sleepy and just wanted to doze in the blissfully warm sunshine. A little while later I said goodbye to Dave and went back to my suite for some lunch and maybe a nap. "I hope I'll see you later," he said. Thinking nothing of it, I told him I was sure that he would.

Chest down, ass up I was kneeling and trembling on the bed. "Oooo. Go ahead, please. Please fuck me," I gasped. Panting with excitement, I was entirely aroused anticipating that unique rectal pleasure-pressure and waiting for him to enter me. 

Then I woke up covered in sweat. I had been dreaming about some faceless guy preparing to fuck me.  Slowly I realized that I was all alone and sporting a raging erection. "Wow. I haven't had a dream like that in years," I thought.

Decades ago I'd had my first and only gay encounters. (See "My First Time" and "My First Time, Part Two. and Part Three etc.") It had been a wonderful time, but I'd never repeated those experiences. 

Occasionally over the years I have enjoyed homoerotic dreams, typically when I'm sexually frustrated. Suddenly I thought of Dave. "Ah ha, so that's what this is about."

Friendly, intelligent, attractive and about my age, he had a slender athletic body and now that I thought about it, a lovely package. Could I really enjoy an erotic encounter with him? When he asked me about needing a massage...was he flirting with me? Of course he was, and I'd shut him down completely. "Oh my goodness, I really blew it," I thought. I was upset with my stupidity. I needed a cigarette.

I wandered outside and found a picnic table in the sun. Lighting up I leaned back, closed my eyes and let myself relax as the hot afternoon sunshine warmed my naked body. I let my mind wander and drift back to my dream and then I began thinking about Dave and what might have been...If only I had been a little bit more perceptive when a friendly voice interrupted my reverie.

"I was wondering where you got to." Dave stood there smiling down at me. All at once I was startled and a little embarrassed, I'd been thinking about having sex with him. "Oh hey, I was just thinking about you." I said. "Good thoughts I should think." He replied, sort of nodding at my slightly chubby penis. "Any more thoughts about having an irresponsible massage, isn't that how you termed it?" He continued, "I give a great rubdown, I'm sure you'll enjoy it." Trying not to seem too eager, I accepted and asked for a little time to shower. You can shower at my place, I've got plenty of towels. "OK. Why not." We walked slowly over to his suite.

I was rinsing my face and hair when I felt the shower door open. "Want me to wash your back?" What a luxury I thought. "Sure." He scrubbed my back and my legs and spent plenty of time on my bottom, and it felt great. "Turn around, I might as well scrub your front." A little embarrassed, I did as I was told and he gently washed my chest and belly and then my penis and testicles, and I could feel myself starting to respond. "Calm down." I told myself, "You don't really know where this is going." I got out and he toweled me off.

Spreading a few towels out on the bed, he had me lie face down and began to oil my skin. Sitting astride my legs he massaged my back with practiced expertise. Taking time with each major muscle group he probed and squeezed and I felt myself relaxing as my back and neck loosened up. Next he worked on my legs, again squeezing, massaging and stroking as I slowly turned into jelly. I felt like I was melting into the bed. "You're so good at this," I mumbled. He even rubbed my feet, something I love. It felt so good I sighed with pleasure. Squatting on the backs of my thighs again, he returned his careful attention to my back.

By now I was feeling much more relaxed. He changed to light fluttering touches which felt wonderful on my sensitized skin. It felt like every nerve he touched was tingling. Running his hands up and down my oiled back he paused each time, lingering an extra moment over my buttocks. His hands felt so good. With each stroke I began to push my ass up slightly, trying to meet his fingers. Next he switched back to firm strokes concentrating his massage there, kneading and squeezing my gluteus muscles. I sighed audibly as the light stroking continued much closer to my opening. By now my back was extremely arched, my bottom straining upwards, and I was sighing every time his fingers brushed against that wonderfully sensitive area.

He drizzled some oil in my crack and lightly dragged his fingers up and down, right over my rosebud. It felt so good my breath caught. "Ahhh." "Now, tell me how this feels," he said. He took a finger and gently inserted it, probing inside me.  Reflexively I drew my right knee up toward my head, giving him better access. "Oooo," I replied. He responded by inserting two fingers, probing deeper and massaging my prostate. "Oh, oh oooo," quietly moaning as my toes splayed widely apart then tightly curled, responding to the pleasure.

My penis had been tucked down under me and by now I could feel my erection poking out. He noticed this also and as he continued to gently massage inside me he took his other hand and began rhythmically rubbing my member. The feeling was blissful. "Oooo. Nice." Digging my elbows into the bed, I pushed my bottom up against his hand. He asked if I would like to roll over. "Oh yes, please."

Rolling over my erection was standing tall as my breath quickened. Highly excited, I was quivering and shaking all over. I gasped again when he took me in his hands and stroked. What he did next shocked me. Unbelievably, he bent down and took my penis in his mouth. It had been decades since a man had taken my member into his mouth.  I was astounded by how good it felt.

The pleasure was very intense. He sucked on me with just the right amount of pressure, and I thrilled to feel his tongue swirling around and around my sensitive swollen head. This was far and away the best blow job ever. When he took his hand and began rubbing the base of my cock in time with his sucking, I could feel myself getting close. I cried out in utter delight: "Oooo. Oooo. My penis, my penis!"

Just when I thought I was approaching the point of no return he stopped and squeezing me hard, interrupted my rush to orgasm saying, "Oh no. You don't get to come yet. I've got plans for you."

Propping my ass up on a thick pillow, he knelt between my quivering thighs slowly stroking my trembling belly and my throbbing erection. Feeling his firm penis repeatedly slapping against my thighs, thrills of anticipation ran through me. 

Flinging my arms up over my head I surrendered completely to the moment. My breath caught again as he guided himself to my tightly clenched anus. Patiently pushing his manhood against my hole, he held himself there gently pressing, waiting for me to relax.

I focused only on that one spot as the pressure built, slowly becoming overpowering. Ever so gradually he began to enter me. "Oooo." I cried again as the head of his penis overcame the resistance of my sphincter, slipping just inside me. The pleasure was amazing. "Go slow." I panted. Grabbing my ankles he threw my feet up over his shoulders and pushed himself in a tiny bit more. 

The sensations were powerful, pleasurable and overwhelming; I was afraid it might start to hurt. "Oooo. Please, go slow," I begged. "Don't worry, I have to. You're so tight," he answered. The slow intimate intrusion continued.

His penis felt wonderful entering me. Taking his time he pushed relentlessly until it was buried to the hilt. Warm and smooth and alive, he was not overly thick but so delightfully long that it felt like he was probing into the middle of my abdomen. I thought it might split me in two.

Impaled on his man-root I was gasping for breath and writhing with pleasure. I watched fascinated as my toes fanned apart, wriggled and then curled repeatedly, grasping at the ceiling as if to pull him in deeper. "Oooo. So big, so good," I gasped.

Fully inside me now he sighed with satisfaction and muttered, "Here we go, here we go." 

And so the gradual thrusting began. Gently and deliberately he withdrew then slowly impaled me again. I felt waves of pure sexual pleasure radiating outward from someplace very deep within me, that place he was touching with his long firm penis. The warmth of sensuous delight enveloped my body. "Oooo. Ahhh! Oh my God!" I cried. 

I was shocked by the intensity of the pure pleasure he was giving me. I was vibrating with excitement. He continued his slow long strokes, our bodies working together to find our perfect fuck rhythm.

Taking my rock hard cock in his hand and slowly, in time with the slow thrusts he began stroking me. "Oooo. Ahhh. Oooo." I cooed. Each thrust and every stroke was perfect pleasure, sending waves of bliss throughout my entire body. I couldn't believe the overwhelming power of the sensations he gave me. This was one of the most intensely erotic encounter I'd had in years. Feeling my belly tighten, I knew my orgasm was close.

His slow steady rhythm never changed: thrust in, stroke, pull out, stroke, in again. Each movement performed with an exquisitely sweet, aching slowness. On the other hand, impaled on his long penis I was constantly writhing, trembling, gasping and moaning. Arms over my head, my hands found the headboard and I began pushing myself into him. My cries became bolder, louder and more insistent. "Oooo. Fuck me. Oooo. Ooooo!"

My heels were gently bouncing off his shoulders, my toes straining toward the ceiling curling rhythmically then clutching with delight. Like a giant wave my orgasm broke over me slowly, sending me into perfect ecstasy as I called out my bliss. "Oh my God. I'm coming. I'm coming! Ooooo. Ahhhh. Ooooooo!" Long slow heavy ropes of cum exploded repeatedly out of me, splashing on my sweaty chest and heaving belly. 

When my senses returned he was standing there holding a warm washcloth for me to wipe the giant puddles of cum off my chest and belly. He had washed himself and I was very surprised to see his lovely penis sticking straight out, still quite hard. "Didn't you come?" I asked. "Almost, that was so hot." "Well sit down and let's see what I can do to cool you off." I replied. I had an idea, but I wasn't so sure I could do it.

 Shaking again, this time from nervousness I was about to try something I thought I'd never do. He sat on the edge of the bed while I got up and knelt before him. Taking his penis in my hands I took a moment to admire it.

His penis was long and circumcised and not too thick, perfectly proportioned and nicely tanned from the naked sunbathing we'd been enjoying. The head was dark purple and engorged with blood, seemingly more excited that the rest of him. His skin was soft and perfectly smooth. He smelled clean, like soap faintly mixed chlorine from the pool.

"Be patient with me, I'm new at this." I warned. "Do your best," he said, "I'm sure you'll do just fine." And so I took him in my mouth.

Surprising myself I didn't gag and I found it very enjoyable. He felt firm yet soft, warm and alive. It was like I had the core of his sexual being in my mouth. I found I liked it immediately. I tried to suck him exactly like he had done me. Not too hard, not too soft. His penis felt good in my mouth and I thrilled to feel him swell and stiffen as I ran my tongue over that lovely smooth head and up and down his swollen shaft.

My head bobbing up and down, it didn't take long for me to settle into my rhythm. As I became more comfortable I began to note how his excitement was building. His erection was rock hard by now yet at the same time the skin still felt soft and smooth on my lips and tongue. He was sighing and I could feel his abdominal muscles contracting. Letting some saliva run out of my mouth, I took my right hand and stroked his lower shaft in time with my mouth. "Mmmmm, that's nice," he said.

Encouraged by his responses I continued steadily sucking and rubbing him. Pausing occasionally to swirl my tongue round and round his gorgeous cock head, his breathing became more erratic as his belly tightened even more. A couple of times I paused to admire his gorgeous organ. It really is a marvelous thing of beauty, like an erotic sculpture only better, I thought.

His breathing deepened and he was sighing audibly with every breath, almost gasping by now. I began to notice some wetness coming from the tip of his cock, so I knew he was getting close. I redoubled my efforts. "Oh God, here it comes," he cried. Suddenly my mouth flooded with warm and thick, slightly tangy goo. By letting his cum run out I was able to keep my mouth on him and I kept sucking steadily as he bucked repeatedly, crying out again and again, pouring every drop of his seed into my hot eager mouth. I felt thrilled and gratified, like his cum was a gift to me. Collapsing backwards onto the bed he was gasping for breath. "Wow, I can't believe you've never done that before," he said.

I got up and rinsed out my mouth, returning with a warm washcloth which I used to tenderly wipe down his spent member. His eyes were closed and I wasn't sure what to do next. Suddenly exhausted, I asked if I could lie down. "Please, be my guest." He mumbled. Laying down next to him, but not touching, I was soon fast asleep...