Adult Humor

Virgin Anal: A Second Round?

The second occurrence was equal or perhaps better than the initial instance.

Spankmasters
May 19, 2024
10 min read
gayfirst timebarebackFirst Time Anal - The Second Time?
First Time Anal - The Second Time?
First Time Anal - The Second Time?

Virgin Anal: A Second Round?

This experience occurred 14 years after a previous incident mentioned in "First time anal."

Up until this moment, nothing from that experience had happened again.

I had moved from Sydney to Adelaide for a new job and had been in a relationship with a woman for six years. Fate must have intervened because she was out of town for a meeting while I was at work. The phone rang, and I answered in a typical business tone.

"Hi, is this Michael?"

"Yes, it is," I replied, and who is calling?

"It's Ray."

When I heard that name, a shiver ran through me, and my penis reacted. We engaged in a lengthy conversation about our lives since we last spoke, covering topics such as how we've been, what we're doing, and where we now live. It turned out that Ray was in town for a convention.

"Do you have time for a catch-up?" He inquired.

I inquired about how long he'd be in town, and he replied, "Only tonight and tomorrow night. The conference is introductory today and quite intense tomorrow. Are you available tonight after you finish work?"

I stated that I was and that we could meet at a local bar for a drink if that worked for him. I usually did night shifts until 9:30 pm and had to pass through the city to get home, so I could see him at around 9:45 pm outside his hotel. He agreed, told me the hotel, and said he'd be waiting outside.

Flashbacks of the night Ray took my anal virginity overwhelmed me. We hadn't communicated in 14 years. Many questions arose in my mind. Had he changed and become straight? Was he still desirous of my body? I'd soon find out. I must admit my body tingled with excitement, and my penis started to rise again, but I couldn't let my hopes get too high; many things can change in 14 years.

I ended my shift, headed to the city, and my thoughts raced. I recalled that he'd seen me in female underwear during that event. Was he surprised to see me now, with my large penis in tight women's panties? Would he judge me or be shocked? However, reason reminded me that he wouldn't see them and we were just going for drinks, so there was no reason to worry.

As I arrived at the hotel, Ray was waiting outside. He hadn't changed much; maybe a few extra pounds around the middle.

"What's a good bar around here?" He asked.

To tell the truth, I didn't usually visit the city for socialization, so no bars came to mind. Also, the thought of driving after a few drinks concerned me because I couldn't afford to lose my license for drunk driving. Police were really cracking down on it now, and the limit is 0.05% alcohol, approximately two drinks. So, without any ill intentions, I proposed going to my place instead. "It'd be easier here because I have a bottle of Chivas," I said.

When I said this, I was genuinely concerned about the inconvenience of parking and drunk driving, not planning anything else. Ray asked how far I lived, and I said about 10-15 minutes away, which he accepted as a good idea. Even though this idea alleviated my concern about his intentions, it also disappointed me slightly since it seemed like he only wanted drinks and conversation.

We exchanged information about various topics on the drive to my house. When we arrived, it was rather chilly, so I turned on the gas fireplace, and we both had a Chivas on the rocks.

Unbeknownst to me, Ray pulled a surprising move that I should have anticipated but still left me startled. With a drink in his right hand, his left hand massaged my crotch through my jeans. "How has HE been all this time? Did HE miss me?"

An electrifying shock traveled through my entire body, and my penis grew hard instantly. It felt fantastic having someone else touch my penis for the first time since Ray. Each touch elicited a similar sensation, but none compared to Ray's. I grabbed his trousered cock and asked how he had been, and he replied with a teasing tone: "HE has missed you too."

Did he ask you if you had any adult content? (Of course I do.) I replied affirmatively, preparatory to acquiring it. He nodded in approval. I retrieved a particularly steamy DVD, brimming with scenes of fisting and peeing. We positioned it on the player and hit play. Soon afterward, we got caught up in the thrilling activities on the screen, engaging in mutual touching.

He proceeded to effortlessly undo my belt and zipper, yanking down my jeans. Following a brief awkward tussle with my footwear, he quickly stripped off my trousers, ultimately leaving me with just a pair of light panties on.

Suddenly, he effortlessly took off his shirt, exposing his naked torso. Standing by the fire, I was far from cold, yet still felt the trembles take over. Both of us were bare, save for the sheer panties covering my bulging erection. To my delight, he pressed his body against mine, our hard, sensual forms rubbing and caressing each other in a sensation that defies description. His hips bucked against mine and his enormous cock rubbed against my own.

With a light touch, he first caressed my back before advancing down to my buttocks. There, he licked all over them, leading me towards the delights of my anus. Rapidly shifting his focus, he reached my neck, darting his tongue around and biting at my protruding nipples. I'd always possess extremely sensitive nipples – they were currently extremely stiff and sticking out. Next came the tantalizing sensation of his tongue licking across my abdomen, where it reached my underwear.

Pulling my panties down and disentangling my leg, I stepped out while he removed them. Lying prostrate against the fireplace, I faced him; both of us completely naked. It was then he placed his fingers at the waistband and slowly withdrew them. His lips finally met my tip, flicking at it before swirling his tongue. While shivers pulsed through my whole frame, he moved his head upwards, sucking the length of my shaft and grazing the bulbous veins. His moisture-streaked tongue worked swiftly, arousing me even more intensely.

However long this exchange continued, the passage of time was irrelevant. While he played with my flesh, his palm roved, probing my butt area. Finally, he had me turn around, running his hands up and down my legs, thighs, and calves, causing rippling effects on my smooth skin. He took both cheeks in his hands, forcibly separating them, exposing the soft, delicate entrance to further excitement. Leaning against the mantelpiece while kneeling on all fours, I moaned as he darted his tongue over a particularly sensitive area. My muscles quivered and I pushed myself backwards, trying to encourage his probing tongue to delve deeper, tasting the unimaginable pleasure. Unaware of its true name.

Instruction:Explain what it means to shave your butt crack and the sensations associated with wearing women's underwear.

Shaving your butt crack is the practice of removing hair from the posterior region. It typically involves shaving or even waxing to reduce the appearance of hair in this region, resulting in a smooth, silky feel under your underpants. This smoothness is complemented by the feeling of soft, nylon-mesh panties gently enveloping your body, rubbing and sliding against bare skin, evoking a unique sensation like none other.

As I reveled in the delight of my lover's attention to my secret place, he came to a halt and exclaimed, "I gotta pee." This wasn't shocking given the massive amounts of scotch we'd been consuming. While engrossed in what I was experiencing both physically and visually, I inquired if he had ever urinated on anyone. He murmured, "Nope."

I persisted, asking if he'd ever consider doing it to me. He stubbornly persisted in his response, "Nope." I then resort to beg, urging him to try it out on me, hoping that he ultimately desired to fuck me and would do it just for my sake.

We made our way up to the restroom, where I slinked into the bath and lay down. As he stepped in, standing above me, his legs stretched out between mine, I marveled at the scene. This was one of my favorite sights when watching porn - being beneath a man, my gaze directed at his legs, guided toward his cock, balls, stomach, arms, shoulders, head, all while experiencing complete submission. He positioned himself above me, his throbbing, 7-inch cock aimed at me. The gush of his hot urine first made contact with my chest, trickling up to my neck and splattering against my face. Eager for more, I opened my mouth and encouraged him to release his stream into it. I savored the unique sensation as he sent it down across my body. The warmth, the ticklishness against sensitive skin, and the heartening feeling of my balls and cock responding are indescribable. But I took another mouthful and swallowed, keeping his octopus-like appendage pointed at me while he slowly turned off the shower. I'm sure he wasn't feeling the same enjoyment as I was, but oh well, his pleasure wasn't my concern here.

As for my shower, it's not of the spacious variety, and it was designed for just one person. Conversely, with both of us squeezed into the tight space, there was very little wiggle room, making it almost impossible not to touch each other. He picked up the soap, and tenderly glided circles on my body, making sure nothing was overlooked. His sudsy-covered fingers tickled every curve of my body, dripping over my shoulders, arms, underarms, back, cheeks, thighs, and inevitably traveling between my legs, over my stomach, ass cheeks, cock, and balls. Those few precious minutes were filled with sensations.

He then twisted me to face the tiled wall and hugged me from behind. Pressing his gargantuan, stiff cock against my ass crack, he eased back and forth, never failing to slip through my legs and caress my sensitive regions. One after the other, he kept at it. Each time, his cock glided up and down, enticingly rubbing along my ass crack. It dawned on me that my backdoor was slowly loosening and my hole yearningly relaxed. Every time his cock head tried to enter me, I'd tense up, only for him to slip in just a little before pulling away. That progressed to my moving slightly to avoid him, to him reaching too far before my body forced him out.

One time, he persisted, finally sinking deep inside me, muscles clenching around his base as our asses locked. The feeling was unreal, a moment from my utopian fantasies that became a reality. The orgasm that triggered was profound. I was breathless, groggy, and heady, my body was in a frenzy of ecstasy.

However, my mind - in a passionate fervor - couldn't disregard the nagging concern. We hadn't seen one another in fourteen years, and despite being in a committed relationship, my senses were skeptical. What if he had contracted a disease? Could I potentially be jeopardizing my health? Was I at risk for the most catastrophic of dangers? It's crazy how even in the moment, my logical facilities kicked in. I couldn't stop his cock from going in. It was too late. Once his member was inside me, stretching me out, he became inseparable from my ass. But as I reveled in the blissful deluge of sensations, reprieve proved to be lost. So he pushed deeper, and my hole accepted. Filled, completely enveloped in his warmth, I collapsed in vulnerability and desire. I was no longer the one in control, and I had to acknowledge the unyielding needs of my body and of his. And as I surrendered, I welcomed him fully. His entire length filled me up, creating an inescapable connection, compelling the aching eruption in his cock on my behalf. The orgasm's intensity left me speechless. My limbs were locked, yet I yearned to allow him to take hold of me. And so I was. My body was a firework show he commanded.

He pulled his penis out until only the head remained inside me, then slowly slid back in until he reached the extreme. He performed these motions, first moving in and then out, with the walls of my cavity collapsing as he withdrew and expanding as he reentered. Every time he stimulated my G spot and prostate. I was experiencing a level of enjoyment I'd never experienced before. While it was a similar feeling in the past, it seemed much more intense on this occasion. This time, he picked up the tempo, pounding me faster and faster. As a result, my penis, which had now become smaller as it typically does when my anal cavity is being worked on, hung loosely and moved with every thrust. I pushed back trying to accommodate as much as his cock as possible.

"I missed you, babe, I've been craving your ass it's so good to have my dick back inside you," he exclaimed.

I conveyed how much I've missed it and how good it felt, since he continued to strike my prostate he remarked that I was on the point of cumming.

"Let's do it, let me know," he commanded.

I was about to release, I announced loudly, and he thrust with such intensity that his cock lodged deep within me. I succumbed to my orgasm, shooting my load onto the shower glass. I've never ejaculated as intensely as that before. I could feel my ass clutching onto his penis with every spasm it had. The sounds eowing from him told me he was experiencing satisfaction.

"That was sublime," he remarked. "Now, I'm going to fuck you and release my cum into you. This will impregnate you, mark my seed inside you, let your body absorb a piece of me."

His words overwhelmed me, feeling honored that my body belonged to him.

He recommenced his actions with growing intensity, quickly powerful thrusts. The sounds from him made me hope the neighbors couldn't hear, given they'd probably thought someone was being murdered. He tightened his hold on my hips, hoisting me onto him. He lunged in with all his force, burying his dick deep inside me. It felt as if he were inside my stomach. Then, I sensed something, warm to hot, flowing liquid, jetting in spasms like a machine gun, shooting his semen deep into my intestines. His actions were so powerful, so strong, so hot, that my legs quaked, if he hadn't been clutching my hips I'd have collapsed on the shower floor. He trembled attempting to exhaust all of the sperm in him.

I felt complete, I am one, I was completely used. We just remained in that state for a while as he shrank, dragging himself from my canal. I prayed he didn't leave. Finally, pop, he withdrew. I was left on my hands and knees. It was still spasming, the hot semen was pouring out of my now open orifice. He scooped me into his arms and lifted me up. Chest to chest, penis to penis, he enveloped me with his arms.

"That was so much better than I remember the first time. Your ass fits my penis so perfectly. It almost feels as if our two bodies are one, each understanding what pleases the other. Thank you for permitting me to have you and use your body."

Lastly, he washed me, whereas I replied in turn, regretting that I don't have a plug to retain his sperm.

It was sad that he had to attend a meeting that day so couldn't stick around. At 5 a.m., we finally left, and despite my calling him on Christmas, I never witnessed him again.

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