Anal Deflowering Pt 4

The barman reached for my hand and wrapped it around his greasy penis. His fucking motion created a similar effect on his cock. Here we were, the barman’s arsehole jacking my cock to the rhythm of me jacking his cock.

Part 1 | Part 2 | Part 3


When Ken, my piano teacher, shaved my legs and groin before dressing me up as his ‘Barbara’, I struggled with extreme itching when my hair grew back. I failed to keep on top of my grooming regimen and had no idea what I was doing. My lack of accuracy tested Ken’s patience because we wasted precious time grooming instead of fucking. A minor issue in an otherwise fulfilling relationship.

My firm was pressuring me to take some vacation time as my leave balance had accumulated well above the annual requirement. With a sweltering summer, I decided to take a week and head to the coast for a recharge. It was also an opportunity to check out the gay scene in a new place.

Brief internet research indicated a highly rated gay massage parlor a couple of miles down the coast from the town I planned to visit. It was not a cheap place but being cashed up; I planned to pamper myself and, hopefully, score some action.

After arriving at my Airbnb, I showered and took an Uber into the entertainment district. Sampling several bars, my ‘gaydar’ did not pick any targets. As the alcohol was taking its toll, I began to despair at my lack of success. However, with the witching hour approaching, I decided on one more drink at a quaint little bar in a narrow lane on the district’s fringe.

Scanning the darkened surroundings, there were several couples, isolated groups of women huddled together interspersed with pockets of men drinking alone like I was. None of the men initially appealed, but at this point, because I was horny, I was the beggar without much of a choice.

“What are you looking for?” Asked the amused barman, who must have sensed my frustration.

Initially, I hesitated to answer, shocked at the sudden intrusion but impressed that he picked up on my sexual desperation.

“That obvious, huh?”

“Well, you’re the only one sitting at the bar,” The Barman replied with a smile, “And the only one looking around constantly.”

“It’s been a dry night,” I said with apparent resignation.

“I can change that.”

“How?” I asked, my interest — and cock — aroused.

“Ten minutes to closing time,” He said suggestively, “You can attend my personal lock-in.”

“Oh?” I answered, “Who with?”

“Just me.”

Assessing the barman, he was older than me, a little podgy, with a long black beard and a jet black ponytail. Despite purchasing several drinks, I had not noticed him in any meaningful way; as I scanned the bar for possibilities, I almost missed what was under my nose.

“Invite accepted!” I smiled and had my glass refilled on the house.

Those ten minutes crawled by, and my nerves were fizzing with anticipation. I speculated about the barman’s cock and how his seed might taste. My cock grew hard about the possibilities that my mind offered.

When the last drinker departed into the balmy evening air, the barman bolted the doors and extinguished the external lights. Pouring himself a large whiskey and refilling my glass, he joined me at the bar.


We clinked glasses and hissed as the spirits burned our throats but warmed our stomachs.

“I sussed you out the moment you walked in,” Chuckled the barman.

“I have the subtlety of a runaway train,” I admitted, “Especially when I’m running out of time.”

“Well, if you hadn’t have walked in,” Said the barman, “I would have lucked out too.”

“So, not many men of our persuasion frequent this lovely bar?”

“Not as many as I’d like,” He laughed before draining his glass.

“Guess it’s our lucky night?”

“Looks that way,” Confirmed the barman as he reached across the bar and grabbed the bottle of whiskey.

“What are you into?” I asked after thanking him for the free refill.

“I love blowing cock and receiving anal.”

His answer caught me off guard because I am not usually the receiver, and I have not given anal before. To be fair, sticking my cock inside another man’s anus was not an experience that was high up on my bucket list since I could not get enough of getting butt fucked.


“Same,” I said, tentatively, “I also cross-dress occasionally and am curious about latex and leather.”

“That’s not for me,” Said the barman, “I’m a hardcore bottom.”

So was I. This potential forthcoming session might be problematic. How do two bottoms please each other, I wondered, internally? My inexperience began to unnerve me, but I was so horny that I was passed caring. Going with the flow was my modus operandi.

“You want to get started,” He asked after we emptied the bottle.

“Sure,” I replied, slurring my words slightly.

The barman led me to a small office at the rear of the bar. Inside, the was a table with a ton of unactioned paperwork. At the back was a tattered, green Chesterfield lounge which had seen a lot of action.

We kissed, and the taste of whiskey was pungent on his tongue. There was a manliness to the barman that turned me on, especially with his beard tickling my clean-cut face. Being of similar height, our bulges pressed against each other, with each of us pressing against the other hard.

Being unable to restrain myself, I was about to drop to my knees when the barman beat me to it. He deftly undid my jeans and pulled them down to my ankles. After complimenting my cock, the barman gently eased me onto the couch and relieved me of my shoes and socks, discarding my clothes in the corner of the office.

The barman’s skill and technique were impressive, and he efficiently brought me to boiling point. He sensed this, of course, and just as I was about to pass the point of no return, he ceased his oral attention and pulled me to my feet.

“I need you to fuck me,” He said after kissing me hard.

I was so nervous, dreading this request, but also somewhat curious about how it would feel.

“But I’ve never done this before,” I stammered.

“I know,” His confidence disarmed my fear, “I’ll do the work.”

Reaching into his desk, the barman retrieved an often-used tube of personal lubricant and liberally applied it to his anus, his dick and my cock. After wiping his hands, the barman leant over the Chesterfield’s arm, spread his hairy cheeks with one hand before taking hold of my cock and guiding me to his twitching pucker.

“Push!” He hissed, and I applied pressure.

Initially, nothing happened. It seemed that my cock was pushing against an immovable object. I felt the barman work his O-ring, and suddenly, pop, I breached his shit hole.

And what a sensation it was. In an instant, my fear had been replaced with a newfound sense of eroticism as the tight confines of the barman’s anus strangled my pole.

“Fuck me hard, lover boy!”

I started slowly, but this only frustrated him. I sped up my thrusts, but nothing I did satisfied him. The excessive application of lubrication did not help because I frequently slid out.

“You can’t hurt me,” Hissed the barman, the anger in him growing, “Fuck me as hard as you can!”

I did the best I could, and, as the sound of flesh on flesh impact grew intensely, the barman, at last, felt satisfied.

After several minutes of doggy style anal sex, the barman suddenly announced that he wanted to ride me. I sat down on the Chesterfield, and the barman took hold of my legs and pulled me down so that my cock reached vertically in the air. He straddled my legs and reversed-cowboy’d me. Now that he was in charge, the barman fucked my cock with crushing violence, slamming into my groin with increasing intensity.

“You like that lover?” Asked the barman, panting hard, “You like my arse jacking your fuck stick?”

To be honest, I was enjoying fucking my first arse despite my pelvic bone taking a savage punishment. The barman reached for my hand and wrapped it around his greasy penis. His fucking motion created a similar effect on his cock. Here we were, the barman’s arsehole jacking my cock to the rhythm of me jacking his cock.

The ceaseless violence, the heat and tightness of the barman’s dirty hole inevitably took their toll on me, and there was no way I could postpone my orgasm.

“I’m going to come,” I said meekly.

“Me too,” Answered the barman breathlessly, and he wrapped his hand around mine and sped up the motion on his cock.

We both came together, loudly and passionately, with me filling his hairy hole with the entire contents of my balls. He exploded with ribbons of boiling sperm coasting our hands.

When my orgasm subsided, I had to get his hairy man off me; my groin could not take his weight any longer. We sat next to each other, chests heaving and regaining our senses.

“Did you enjoy your first arse?” The barman asked.

“It was great,” I said earnestly, “I had a strong orgasm.

“So I felt,” Laughed the barman, “How long are you in town for?”

“Till next Sunday.”

“Great, same time tomorrow?”


I met the barman the next day, and he had me fuck him again, this time in different positions. We both came simultaneously, and, again, I enjoyed fucking his arse.

The night following was a disaster. I think that I consumed too much of the barman’s free drinks, and I failed to maintain an erection, and no amount of the barman’s considerable oral skills could change the situation.

Facing a fight or flight moment, the barman calmed me down and told me that I could throat his cock and he would fuck me. His alternative placed me back into my natural element, and I readily agreed.

The barman straddled the arm of the Chesterfield and offered me his cock, which I devoured with a renewed enthusiasm. I figured that the barman was versatile enough to occasionally switch from bottom to top when the situation demanded it. In any case, the barman made the right noises as I sucked on his cock and nuzzled his hairy ball sack. His gorilla-like physique reminded me of Ken’s frustration at my lack of personal grooming.

“I’m going to fuck you now,” Growled the barman.

He positioned me in the doggy position on the couch and spread my legs, leaving my limp dick dangling.

Expecting the cold, inhuman slop of lubrication on my anus, I had the shock of my life when the barman’s tongue stabbed my bung repeatedly. This was my first rim job, and I loved it. The barman knew his business and bathed my hole with copious amounts of whiskey-flavored saliva. I hissed when he digitally penetrated me then I winced in pain as two fingers roughly fingered me. However, the irritation disappeared quickly as the barman opened me up.

“You’re ready now,” Crowed the barmen, and he pressed the head of his cock against my O-ring.

Tonight was going to be my first un-lubricated penetration, and I braced myself for the inevitable pain.

“There you go, little slut,” Mocked the barman as he filled my rectum with hairy meat.

The need to express my pain was overwhelming, but I kept it internalized as I wanted not to disappoint the barman again. The stinging pain resulted from a lack of lubrication, and, as the barman seemed reluctant not to use any, I spat on my fingers and massaged it around my hole and onto the barman’s cock. The more I applied, the more the irritation receded, and soon enough, my body was engulfed in the familiar warm glow I felt when anally taken.

“Oh, fuck yes!” I sighed as the barman worked me hard.

The barman kept me pinned in position as his cock powerfully thrust in and out. While he was not the largest cock that has worked my shitter, his power was impressive. With a faulty cock, I focused on my O-ring and worked it for the barman’s pleasure.

“Oh, fuck,” He roared, “Here it comes, you slut!”

I felt his shaft jerk forcefully inside my arse as he buried himself balls deep for the climax. His hold on me was absolute, and I could not move even if I wanted to. While I tried to time my orgasm to coincide with my partner’s, tonight, I felt an unusual warmth and pleasure envelop me, satisfied that I gave the barman pleasure despite not having one of my own.

But the fun was not quite over.

Rough hands forced my arse cheeks apart to their maximum width. I gently chided the barman, but he did not let up. He blew on my buggered anus, which sent shivers across my sweaty skin.

“Push it out,” He growled.

“What?” I asked, confused at his request.

“Push my sperm from your hole.”

I flexed my O-ring and abdomen, which resulted in a low, rumbling fart and the intense sensation of liquid dribbling and running down my taint.

The barman was there with his bearded mouth to scoop up his seed. I enjoyed his cat-like tongue dance across my erogenous zones. When he sensed that I had ejected all I could, he slurped at my hole, cleaning it up, before forcefully pulling me up and pressing my lips on his.

As we kissed, I felt a noxious mixture tongued into my mouth. The taste was undeniably the barman’s, and I felt an exhilaration flow through me. We snowballed his seed back and forth before breaking and swallowing the heady cocktail. This end was the single, filthiest act that I have experienced on my journey so far.


Given my failed performance on the third meeting, I quietly avoided the barman for the rest of the week. I had the massage parlor to look forward to, and I decided not to consume any strong liquor before attending.

The parlor was tucked away from the beachfront and seemed to go out of its way to be unobtrusive. No signs out the front advertising its existence, and the front windows were frosted, thereby maximizing its privacy. There was a buzzer out the front, and when I identified myself, the door clicked open.

Walking in, an effeminate man dressed in a white smock greeted me and took my payment. He asked me if I wanted a ‘happy ending’ when my massage was complete.

“Uh, sure,” I replied, unsure as to what ‘extra’ that was, but it cost me another fifty.

Minutes later, another effeminate man opened the door to a room and led me in. Inside, a long table dominated the room, which had a circular hole about three-quarter along its length. There was a pleasant aroma, generic music tickled my ears, and a water feature was bubbling away.

My masseuse directed me to a screen where I disrobed without some embarrassment, and I laid on the table. My cock and balls hung freely in the hole. After draping a towel across my butt, the masseuse presented me with a choice of oils and prepared to weave his magic.

And what magic it was!

The oil and his hands worked every muscle and bone, turning me to jelly in the process. I never felt so relaxed and so relieved of stress and worries as I did that day. But the massage got better when the little effeminate masseuse slipped a finger inside my butt crack and penetrated my freckle. I grew instantly hard at this welcome development.

Shortly, two delicate fingers were freely opening me up, but the technique was somehow different and infinitely more pleasurable than any previous fingering. I later found out that part of the ‘happy ending’ was a prostrate massage, and it brought an incredible level of hardness in my cock that I thought I might come without external stimulation.

When the masseuse judged that the time was right, he reached under the table and, with a greased up hand, took hold of my raging boner, and several short strokes brought me to a thundering climax. Sperm shot all over the place as my balls seemed out of control. When my orgasm subsided, I was completely drained of energy.

I thanked the masseuse for his incredible skill, grabbed my clothes, deposited them in the locker room, and proceeded to the sauna. Entering with a white towel wrapped around my waist, there was only one other occupant. He was a big daddy type, and he was languidly stroking his meaty cock with his eyes closed. He acknowledged me briefly before resuming his fantasy.

Sitting opposite Big Daddy, I ran my eyes over him. While his appearance was repulsive, I admired his fat cock and how he was playing with it. I found myself imagining trying to get his meat in my mouth and became semi-hard in the process. It was only 15 minutes since my last orgasm.

Suddenly, the sauna door opened and in came this slight man, with thinning grey hair and sat close to the glass door. As he sat, his towel gaped open, and I saw the biggest cock I have ever seen on a white man. Naturally, I forgot all about the man sitting opposite and made my way across and sat next to him. I was unsure about etiquette in these places, but I was determined to experience his cock, and he seemed to anticipate my request.

“Can I touch it?” I whispered, blood boiling in my veins.

“Go ahead,” He whispered back, smiling.

I slid my hand under his towel and felt his mammoth cock. It grew hard with my touch, and he discarded the towel so I could see it. Big Daddy was lost in his dream and paid us no attention. Running a finger across this new man’s helmet, I felt a tiny drop of precum.

“I want you in me,” I whispered, my salivating and anus twitching.

His answer was to stand up, replace the towel and take my hand, leading us to another room that had swings suspended on chains.

“My name’s Terry,” The man said.

“Charles,” I replied, “Nice to meet the two of you.”

Picking a swing at random, Terry climbed into one, grabbing his cock by the base and pointing it to the ceiling.

“Go right ahead,” He said softly, and I leaned over to take the head in my mouth, savoring the taste of his magnificent cock.

Terry let me suck him for a while then instructed us to change places. As I got into the swing, he passed my wrists and ankles through the leather straps attached to the chains before leaning down to kiss me and say, “I’m going to try something different ok?”

Being so turned on, I just nodded a yes with my cock and hole spasming in anticipation. Terry went over to the lubricant dispenser and filled his palm before walking back over to me, his monster cock swaying in front of him.

“Are you clean?” He asked after leaning over and kissing me.

Thinking there was a strong possibility of having sex at this place, I made sure I was clean before leaving the Airbnb. Terry was relieved with my answer and then moved down between my legs. I felt the cold gel being gently worked into my hole.

“My, you’re relaxed today,” Exclaimed Terry as he easily penetrated my O-ring, and I explained my ‘happy ending’ earlier.

While Terry did not possess the same skill as the masseuse, his fingering was very enjoyable, and the blood flowed strongly to my rejuvenated cock.

He continued and slipped a third finger into my ever-widening hole until eventually, he worked a fourth. While I may have been opened earlier, four fingers tested my tolerance, but I figured this fingering was necessary before accepting a cock of Terry’s length and girth.

Looking up from between my legs, Terry asked me if I was ready for his thumb and then I realized he was going to fist my arsehole, another first. I have gone this far, I thought, so why not and so I winced my assent.

I had to admit that the feeling of a hand inside my pucker felt strange but arousing simultaneously. There was a slightly uncomfortable pressure before a sound resembling a pop, and we both exclaimed in glee. At that moment, I felt that same sensation as I did with the masseuse. Terry’s fist had found my prostrate, and when he twisted and rotated his wrist, I gasped in pleasure.

Through the fog of pleasure, I heard a muted voice close by and felt a hand pull my head to one side, then a cock forced into my mouth. I opened my eyes to be greeted by Big Daddy’s bulky frame, who smiled lasciviously at me as he fed me his fat length. I desperately wanted to stroke my cock as I felt precum oozing from the tip, but my hands remain bound. I sucked hard on Big Daddy’s thick pole that tasted soapy from a recent shower.

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1 thoughts on “Anal Deflowering Pt 4

  1. Jonathan says:

    This story is exhausting. Would be interesting if I want falling asleep.
    Sorry but I’ve hung out long enough – got to go.

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