Curiosity Satisfied

This is my second submission to LitErotica. It does not involve a real-life story of mine but it's more of a fantasy that has started to crawl into my mind in the last few years since my second divorce. I am very likely to act on it soon. Constructive criticism is expected. BTW, English is not my first language. All characters are 18 or older.

If this rises enough interest, I might continue the story of these two characters. I already have a few ideas swirling in my head. Please let me know if you want more on Bert and Alex.

ONE WEEK BEFORE

I am a mature man, overweight, bald, quite hairy, with an average sized cock that still to this day hasn't failed to rise to attention when needed. I also hold a university degree with a PHD, am moderately wealthy but not rich. I have been resolutely straight since my initiation well before the accepted age and, after my second divorce, I have been living la vida loca. I was regularly getting laid with women of all ages who are not in short supply where I live and were equally casual about their sexual affairs. But, a certain type of curiosity had started to creep on, and I really wanted to try with another man; but not a man like me. No. I wanted to have a young guy, preferably a twink and who was willing to allow me to be active. Being bottom didn't hold too much appeal to me.

I wouldn't dare to indulge where I live. It's a small country and my line of work is fairly public so I couldn't take risks. Luckily enough, I live just a short flight away from a country known for its great tourism, culture and first-rate facilities, but also, well known for its catering to the sex-tourism industry. So, I signed up in a web site listing escorts and started to browse.

I found several candidates, all between 19 and 24 years of age (well below half my age) and all having the requisite characteristics I had limited myself to. They were all thin, you could even say skinny, they all had hairless or nearly hairless bodies, they were versatile but preferably passive, and willing and accommodating. They were also well educated, some being even university students and were squeaky clean.

Nevertheless, one of the guys was clearly shining above the rest. Bert (not his real name) was a 20-year-old guy, 5.3 feet tall, 99 pounds, dark haired, dark skin, nearly hairless body, full lips, green eyes and an infectious smile. He was a university student pursuing a degree in art and offered a boyfriend experience. He said in his ad that he could be top or bottom as the client preferred. As said before, I was interested in being top to his bottom and I felt sure I wouldn't think of going bottom with him even though his cock, while nice, didn't seem to be that big and intimidating.

I contacted him online. During the interchange he showed himself as a very professional guy, with intelligent conversation, nice personality and very knowledgeable and familiar with the situation I was in. Even being so young he already had been building a reputation as a good initiator to straight but curious men.

He requested photos of me which I obliged. I sent him a photo of my face; one dressed in business suit and one in my yellow speedos. When I took my selfie in my speedos, I was already feeling very horny and was almost completely hard. The photo showed off my bulge nicely. I then asked him for the same and he reciprocated. He sent me one of him dressed in yoga pants and a sleeveless t-shirt, one in a tight bathing suit (which showed an interesting bulge) and the best photo was a nude full-frontal shot showing his nicely erect cock and his hairy bush. His cock looked not bigger than 5 or 6 inches long, with a nice, red head and a respectable girth. I was already smitten and was decided to see this through.

We finished the chat and agreed to meet at the airport in his city in a weeks time. I was planning to spend a weekend there, so I booked a plane, rented an apartment and reserved a car. I preferred an apartment as it was more adequate for privacy than a hotel. I was full of trepidation waiting for the trip.

FRIDAY AFTERNOON

The week passed in a rush and suddenly I was deplaning at his city in the late afternoon after a two-hour hop. I didn't check luggage and was travelling with my old and trusty carry-on suitcase. After passing through immigration and customs, I entered the terminal area looking for him and rapidly found him. He was dressed discretely in a pair of brown slacks, light brown moccasins and a white turtleneck. He had a small backpack bag hanging in one of his shoulders. His dark hair was combed to the back in a wavy fashion. A gold ring decorated his right ear lobe, a gold chain was in his left wrist. His hands were elegant, with long fingers and perfectly manicured nails. His face was clean shaved, his lips were thick and luscious and he parted them with that infectious and seductive smile, showing the white of his teeth the moment he saw me.

"Uncle! Welcome!" he said, discretely.

We hugged like uncle and nephew, complete with manly back slaps. The top of his head only reached up to my chin. His hair smelled clean and fresh with a mix of shampoo and a cologne I couldn't indetify. His frame was thin and light. I was sure he would be easy to manhandle.

He then picked up my carry-on and we started to walk towards the rental car counter. In a spontaneous gesture, I decided to change the reservation I had for a subcompact and took instead a 4x4 jeep which we picked up in the parking lot. Who knows? maybe there were possibilites of going off-road around here.

I put my carry-on in the back seat, and he threw his small backpack there as well. He then sat shotgun, and I took the wheel. During all this time there was not a hint of anything different between us besides an uncle visiting his nephew for a few days. I dare anyone who saw us to suspect something lewd going on even though I was feeling pretty turned on already. When we left the airport, he put a hand on my groin and felt my cock already hard. A naughty smile parted his lips while he gazed at me and slowly rubbing my dick. I couldn't reciprocate as I was driving and the 4x4 was stick shift.

"I think you'd prefer to have another stick shift in your hands right now, don't you daddy?" he said with that naughty smile. This boy could read me so easily.

After a short drive of about 40 minutes, we arrived at the building where the apartment I rented was located. The check-in office would be open for one or two more hours, so I received the keys while Bert said, for the benefit of the attendant:

"You should have stayed with me, uncle. My roommate is out for the weekend."

To which I replied that I didn't want to cause any inconvenience. We went up to the apartment, a nicely appointed penthouse in the 15th floor, and I put my bag in the master bedroom. He dropped his back bag next to my carry-on and we took a look at the place where most of this weekend's activities would probably take place.

The master bedroom was huge. A large, double-king bed was against one of the walls, and the opposite wall had floor-to ceiling windows with black-out curtains that were now open. The bed was covered with a comforter, black and thick. Several cushions adorned the head. We pulled the comforter, a little curious, to discover a set of silk-imitation bedsheets, black as sin, and smooth and shiny. Above the bed there was a large mirror perfectly centered. There was a dresser, a small walk-in closet and two easy chairs with a coffee table between. A very posh bedroom, indeed.

After exploring the bedroom, we came back to the living room. I gave him an envelope with the money we agreed for this weekend, in cash, which he took without counting and returned to the bedroom, probably to stow it in his bag. When he returned, he pulled an envelope from his back pocket and gave it to me. It was a PrP HIV test done a few days before and showing negative results. I quizzically looked at him and he just said:

"Just in case, daddy. Just in case."

I assured him I was also clean but did not have a test with me and he seemed ok with that. I then asked him if he could accompany me to buy some supplies like food and booze and off we went.

Before reaching the supermarket, we stopped at a pub nearby where we had a few bears and a late, light lunch. We talked a lot about art, photography and surprisingly for me, he was very knowledgeable on movies in general and Sci-fi in particular. We discussed everything, from the classic Star Trek series and movies to the wreck of the recent Star Wars productions from Disney. Just like me, he thought that the only good things live action they had done recently were Andor and The Skeleton Crew. He loved The Mandalorian but we agreed that the third season lost much of the brightness it showed before. We also agreed to hate The Acolyte and spend a nice moment berating that abysmal show. It was a very nice and nerdy chat and reminded me a lot of the conversations about cinema I use to have with my daughter.

Then we went to a small supermarket where I got a couple of bottles of wine, a six pack of beer, a bottle of vodka which he said he loved to drink, some groceries, and several different snacks, cheeses and cold cuts. With this, we went back to the apartment.

FRIDAY EVENING

I opened the door, put the groceries in the kitchen and sat in the sofa. Bert sat next to me, faced me and asked.

"Ok, here we are. How do you want to start?"

I stared at those smiling and luscious lips and couldn't hold myself. I leaned and started to kiss him. He immediately parted his lips, and our tongues started a duel of strength and contortionism. The kiss rapidly became steamy and hot and, either he was acting or he was really enjoying it because I heard some soft moans coming out of his mouth which emboldened me. The kid really knew how to kiss. My hand went to his crotch and rested there. The sheer fabric of his slacks couldn't hide his hardon. I grasped his rod and rubbed it up and down while moaning, as he bucked his hips trying to fuck my hand. After a short time, we let go, locking eyes and he smiled again. It was a sweet smile, not patronizing, but also naughty. He licked his lips and said.

"Wow, I didn't expect that," said Bert, and added, "that was pretty bold!"

"I didn't think I would start that way but you're so tempting, and you're a fantastic kisser," I answered, and couldn't resist adding. "That cock of yours felt hard as iron as well."

"You also kiss fantastically, daddy. And I already know how your cock feels in my hand. Can't wait to see it in the flesh, so to speak. Let's get more comfortable. Come with me to the bathroom."

We went to the bathroom that boasted a jacuzzi, a shower, a WC, a bidet and a large sink. There was also a futon, a couple of nice rugs, crude ceramic floors and indirect lighting coming from the roof above two Ficus plants. He stood there in front of me, I think checking me up, and then he pulled off his turtleneck. His skin was smooth, with barely a hint of muscle showing, and with two rosy nipples that appeared to be standing. There was a faint shade of hair starting at his navel and traveling below before disappearing under his pants. I started to unbutton my shirt, but he held me.

"Wait. Let me. That way you'll familiarize easily with me and the situation," murmured Bert.

I felt his manicured hands undoing my buttons, his nails barely touching my skin and then he peeled my shirt out. His hand then roamed my very hairy chest and quite large belly. He got closer and planted a kiss in the center of my slightly sweaty chest. I felt him inhaling deeply and his tongue started to lick my hairs as his mouth planted feather like kisses all over my skin ending with his lips latching in one of my nipples. His hand went to my other nipple and his fingers started caressing it. I was already rock hard. My hands went around him and I slid them over his smooth skin which felt very hot, almost febrile. His nipples were also inviting, and I started to rub them with my palm while my other hand went down and cupped his nice ass grabbing a handful of flesh under the cloth. Again, I heard that cute moan, almost a whimper that felt like a plead of desire.

He separated from me and slowly kneeled in front of my groin and started undoing my belt and zipper. Once done, I let my pants slid down and I stepped out of them. My briefs were straining with the pressure from inside, barely able to hide my hard meat. I was sporting a tent that honestly I couldn't remember when the last time was that it looked so hard. A slight dampness marked the spot where my cock head was, already leaking precum. He pressed his face there and once again, inhaled deeply. It seems he was very into body odors. Just like me, which held nice promises for the rest of our time together.

He then stood up and started to unbutton his slacks, but it was now my turn to stop him. I kneeled in front of him and in a short time had his pants in his ankles and he promptly also stepped out of them. He was wearing a white jockstrap that held his cock tightly but left his buttocks and asshole uncovered, surrounded by two taut elastic bands. His bubble-but seemed almost feminine in its firmness and roundness. A quarter could easily bounce there. This was an incredibly sexy sight. I remained kneeling and pressed my face in his bulge. I felt the flaming hot, rock-hard cock and the musky, manly smell filled my nostrils and turned my brain into mush. There was already a wet spot on his brief where the tip of his cock was, and I licked the cloth which surprised even me. It was salty, slick and slimy, and oh, so jummy.

I then stood up and planted myself in front of him. Soon I was embracing this tempting young twink. I pulled him to me and pressed his body against mine and drank on his youthful musky smell and body heat. I rose his arms above my head and sunk my nose there, deeply inhaling his armpit odor which was intoxicating and we ended in another lip lockdown and tongue wrestling that lasted a couple of minutes more. We then separated, my hands in his biceps and his on my forearms.

He said, "I knew you were hairy from the photo you sent me, but it looks amazing in person. I am such into bear daddies!"

"I can say that I knew you were the perfect twink, but you look so much hotter in person. And you smell so good, and I mean your unadulterated body odor."

I then asked, "should we go to the shower, or should we take this to the next step? I don't mind if you don't shower. I love the way you smell but I've been on the road for a few hours, and I know I am all sweaty," I inquired.

"I don't mind your smell, daddy. It's actually very hot but let's shower together," he said. "That way we can get to know each other better. I assure you, we will both be sweaty very soon."

With this he again kneeled in front of me and pulled down my brief. My cock sprang hard as a rock in all its 5.5 inches glory and with a glob of precum in the tip already. He put his index finger there and rubbed it all over my cockhead and the first inch of length. It sent shivers of pleasure through my entire body. Not wanting to be left behind, I kneeled also, pulling down his jockstrap and staring at his cock. It was a little longer and thicker than mine, inviting and tempting. An intense heat irradiated from his crotch, feverish and kind of brutal. His shaft and balls were completely shaved but he had a lush bush of hair at the root of his organ that connected with the faint hair track coming from his navel.

His cock sported a large glob of precum and without thinking, I leaned forward intending only to plant a kiss on his cockhead, but I ended opening my mouth and engulfing it with my lips. For the very first time on my life I was sucking another man's cock. It was hard, oh so hard! and the skin so soft. The smell was intoxicating and I had to push my head down and give him several deep sucks. It was salty with a hint of sweetness and citric flavor. I remained there, sucking and licking his manhood, enjoying giving my first blowjob for a few more minutes. Then I stood up again and we kissed deeply, his tongue tasting his precum on mine.

We stepped into the shower and turned it on. Warm water blasted on us from all directions while we soaked in it and in the intimacy of the moment. His hands continued to wander over my hairy chest and belly while mine were grazing his back and cupping his ass. He had a perfect bubble butt, firm and soft, and the hot water was giving his dark skin a hint of pink, specially where the sun hadn't marked it. At the same time our cocks were happily making acquaintance, rubbing each other, sending electric shock from my groin all the way to my toes and my head. Out of nowhere there was body soap in both our hands, and we luxuriously rubbed each other, spreading the suds over our bodies and giving special attention to our chests and our groins.

He grabbed my cock and peeled back my foreskin letting water and soap clean it thoroughly which I repeated on him. I was raging hard, and I still couldn't understand why my erection had lasted for that long. We rinsed the soap and fell in an embrace again while clumsily trying to dry each other up. We managed and then I took him in my arms and carried him to the bed where I laid him down gently. I then laid next to him and started to kiss and grope him like there was no tomorrow. In a short time, he turned around and began to kiss my balls, my shaft and licked my glans as if it were a lollipop. I was beside myself, turning my head side to side in bliss when I realized his cock was right next to my face.

I turned and eagerly put him in my mouth. I went deep and tried to gobble him whole, but I couldn't. His cock reached my throat, and my gag reflex kicked in. I had to withdraw with my eyes tearing but soon went back a little more carefully, giving him the strongest suction I could manage while jerking the part of his cock that I couldn't put in my mouth.

He gasped and took me in as well. It was obvious that his technique and his command of his gag reflex was clearly several grades above mine, but I couldn't care less. His mouth was incredibly warm, and he was giving me a very messy, slobbery blowjob, saliva bathing my balls and the base of my cock. A lot of women I knew could benefit a lot taking a page or two from his technique. He was masterfully keeping me on the edge but never pushing me over.

I started to suck him in earnest, licking his shaft, caressing his balls and occasionally kissing and licking them. I occasionally nibbed softly on his sac an he rewarded me with a groan that vibrated deliciously on my cock. His prick was swelling and twitching as I began to lick the part where his head joined his veiny shaft. It swelled more and was leaking a lot of precum. He was moaning and began to jerk his hips, fucking my mouth with such gusto that I had to keep my hand wrapped on his shaft to prevent him from going too deep.

He was sucking me with abandon, getting my cock to the depth of his throat. I hadn't asked if he wanted a condom before sucking me off, but it seemed the time to find out was past. I renewed my efforts and focused on the rim of his glans. I decided to lick his pee-hole and his cock responded by swelling and twitched and right then I there I knew. I was going to taste a cumshot fired directly on my mouth for the very first time.

I kept sucking with trepidation, waiting for his shot and he didn't disappoint. Gosh, the kid could cum. The first shot hit the back of my palate with incredible force while his moans became more intense. This was followed by 5 or 6 more jets that rapidly filled my mouth making it unavoidable for me to swallow. His cum was thick, salty and pungent, with a hint of fruity flavor. The smell mingled with his cologne. I could see how his ass was pulsating as rope of rope of cum filled my mouth to the brim. This kid could really cum. I gulped down his load but not before some leaked out from my lips and landed in my chin and chest. During this time, he had left my cock out of his mouth but was still stroking me. The moment I felt him ejaculating in my mouth I a wave of pleasure rose inside my groins and in no time I jumped the edge and began shooting my load all over his face, his hand and his chest.

We laid down to catch our breaths and I turned to see his face. He was lying there, eyes closed, a vague smile in his incredible mouth, and my cum dripping from his cheeks, his chin and his forehead, a very lewd image I was burning it in my mind so I would never forget it. He then rose his hands. The right one was also smeared with my cum. I didn't know I came that much. He then smeared my cum all over his face and ended by putting his fingers in his mouth and sucking them clean. Then he opened his eyes and saw me watching him.

"Alex, be honest with me," he asked. "That can't have been the first time you sucked cock."

"It was, Bert, I swear," I answered sincerely. "But I have been on the receiving end for most of my life and I know what I like to be done to me. I just did to you what I like."

"It was amazing, Alex. I usually don't lose control and cum like that with a client. Specially on the first time. It is not good practice to orgasm before the client, but I just couldn't stop myself. It was all I could do not to scream like a girl. You're good, man. You really are."

"Thank you, Bert. I can't believe I took you in my mouth that way," I said. "I can't believe either that I swallowed all you had. Sorry I didn't ask if you wanted me to put a condom on before you sucked me."

"No. I never do oral with a condom," he informed me. "I like it natural. I like it in my mouth. You just didn't let me enjoy yours because I was too busy cumming when you did." And then he added, "When will you be ready for round two?"

"I'm more than twice your age, kiddo, so it will take a while," I told him. "But we can snuggle, kiss, grope, fondle; and maybe I'll be up in no time."

FRIDAY NIGHT.

After a second shower we moved to the living room and sat on the couch still naked. The living room was posh. Two love seats arranged in angle around a crystal coffee table occupied the center of the room. The leather was white and spotlessly clean. There was a large flat-screen TV in the opposite wall which we turned on without selecting a channel. It started to drone on without our attention.

We were more interested in explore each other. I was laying with my ass almost hanging on the border of the sofa and my feet planted in the floor. Bert was laying in the sofa with his head in my lap, his hair tickling my now soft cock. From my position I could see his uncut organ, soft but not flaccid, half engorged, resting beautifully on his left thigh. His pubic hair was dark, curly but not very thick. He shaved his shaft and his balls but kept a nice bush on top and around the root of his organ. His foreskin barely covered half of his glans, and it was pink and moist.

The TV was ranting on about some nonsense and I was spending half my time looking at his cock, occasionally twitching softly and the other half watching the TV. My left hand was resting on his flat abdomen. It felt toned with a deliciously soft skin that responded so well to my bare touch. His faint body hair tickled my fingertips and I kept softly massaging his skin. My other hand was caressing his head. I pulled one lock of hair to uncover his ear and began to trace it with my index finger. He kind of purred and scooted a little closer, rubbing my cock with his cheek. I was already feeling it stirring a little. He glanced up and we made eye contact. His hand came up and started softly rubbing my shaft. His touch was electric, and I started to get hard pretty fast.

My hand was still in his belly, and I began to slide south reaching for his crotch with the idea to return the favor he was giving me but once I reached my destination, my hand told me he was already hard as a rock. Oh, the stamina of youth! I grabbed his rod and started to wank him slowly but deeply, uncovering his cock head completely which was getting furiously red. His breath was getting faster as well as mine and I was getting harder but of course not as fast as him. He then put my half hard cock in his mouth and started to give me a fantastic head. One of his hands was caressing my balls and the other was holding me by the base while his mouth was sucking me like a Hoover® machine. His wandering hand went lazily from my ball sack to my perineum, even going further and gently caressing my ass. There was nothing for me to do than get fully erect.

He released me, sat up and offered his mouth. We kissed deeply. His mouth tasted of toothpaste and spunk. My spunk. It was so hot. I continued to wank him without stop. He then gently pushed my hand aside and walked to the cabinet where the TV was. His back was completely bare, hairless and his small muscles rippled under his soft skin. His buttocks were round and perfect, bouncing softly as he reached the cabinet. He then leaned down, opened a drawer and got something he had put there earlier. Without stretching up he glanced back and saw my eyes fixed on his bum. He smiled and, putting whatever he had picked up on the floor, pulled his buttocks apart with his hands and let me see his brown, wrinkled ass. It looked small, tight and oh, so inviting.

"Getting any ideas?" he asked with lust in his voice.

"All kind of ideas" I answered with a husky voice.

"I know you have," he said poiting to my groin. "That hard cock is all the clue I need. I want it buried balls deep in my ass," he said. Then added, "Let me put this in you," showing me a rubber still packed. In the other hand he had a bottle of lube that he put on the side table right next to me.

"I think this is what you were looking for when you hired me," he said. "You wanted to fuck my ass. You wanted to bury your big cock in a young guy's poopchute," he said lewdly. "Well, you're about to do it. Of course, I know this will not be, by far, the first ass you fuck, daddy, but it will be the first male one, won't it?"

"I haven't fucked that many asses, kid," I answered. "Women of my age didn't usually open their back doors 40 -- 50 years ago when I was a young scoundrel and later in life, I haven't really asked for it so maybe a few, including a few times with my two wives and we didn't do a lot of anal to be honest."

"Well, then you're in for a treat. This is a well-trained ass that loves to swallow cock, but it's very tight and I can contract it pretty much at will. After the first fuck you will be hooked on this ass! That's a promise."

With this he once again kneeled between my legs and opened the rubber with his mouth.

"You are not allergic to latex, are you?" he asked, suddenly concerned. "I forgot to ask before."

"Don't worry, Bert. No allergies there to worry about"

He then placed the rubber in his mouth and lowered his head towards my groin. With expert movements of lips and tongue he put the rubber on me without touching me; something I had only gotten in my previous years with the most experienced, mature and sluttiest of my current set of friends with benefits. When I was covered, he poured a glob of lube and thoroughly smeared it on my covered rod and stood up. He then gave me the bottle of lube and told me

"Lube me up daddy. I want to have you inside right the fuck now"

I poured some lube in my hand and some in his crack. It slid down towards his balls. I began to massage his asshole and then inserted two very well lubed fingers reaching as deep as I could, which elicited another one of those cute moans. Then I put my hands down and he turned his back on me and said.

"I am going to ride you now, daddy, and I am going to enjoy it. Try not to move a lot initially"

He grabbed me with one hand, pointed me to his entrance and pulled his butt cheeks with the other hand. Then he lowered himself until his ass was touching the tip of my cock. It was hot and slimy. He then pushed down and my head plopped inside as if nothing. He was tighter than any pussy I had fucked in all my life. He lowered himself slowly until his bottom was in my lap and I was buried balls deep in his ass. He stayed there for a little while and then he started to jerk his muscles thoroughly massaging my dick. This got me harder and madder with lust.

I could barely control myself waiting for his clues. He began to come up and down on my cock. Initially slowly but later faster with what looked like an urgency in his movements. His breath was coming in gasps in rhythm with his movements. I was also groaning loudly as his hole gripped me with incredible tightness. The friction of his sphincter on my very hardened prick was maddening. Our bodies were slamming loudly and not knowing why, I gave him some slaps on his ass which he seemed to enjoy.

"Yes daddy, hit me more!"

I kept on slapping his ass as I started to move my hips in unison, and we were now crashing on each other. He suddenly changed movements and began to swing back and forth with my rod buried deep in his ass. The feeling was incredible. The tightness of his hole and the way his muscles gripped me and released me were rapidly taking me to the point of no return and I didn't want this to end too fast, so I had to stop him and asked him to turn around.

Without taking me out of his ass, he turned and faced me. His face was flushed, and rivulets of sweat were dripping down his gorgeous chest. His smile was filled with lust and his eyes were shining wildly. Once changing position, he wrapped his legs around my back and restarted his back-and-forth movements. His cock was rock hard, swinging up and down and the angry head was slapping my belly in every movement, leaving precum spots on top of my belly-hair.

HIs legs were tightly wrapped around my waist as he impaled himself on my prick. He slowly increased his tempo with a concentrated look on his face, and I had to tell him that I was about to explode. He just mumbled something unintelligible and went at it even faster. That just made it. With a guttural growl I exploded inside the condom. Contractions came one after the other and my orgasm lasted what seemed like minutes. I didn't remember ever having a longer or more intense orgasm before. At about the middle of my climax he released a youthful cry and came. And boy did he cum! He wasn't wearing a condom and the first shot flew beautifully over my head and landed in the wall behind me. The second landed squarely in the middle of my bald head, followed by a third, fourth and fifth which hit my nose, lips and chin in that order. I licked my lips to savor his cum for the second time. Several more ropes flew from the tip of his beautiful cock landing on my chest, on my belly, on my hands and even on the sofa. It was a delicious mess. I was all sweaty, covered in young spunk with my cock buried deep in this twink's pulsating ass and feeling like there was no concern in the world. His movements slowly became more relaxed until he stopped.

He laid on my chest, catching up his breath, without pulling me out, smearing his spunk on my torso and his. He rose his hands and brought them to my head where he smeared me with the semen that landed there, leaving my bald pat shiny and moisturized. His ass muscles continued to contract and massage my cock and somehow that kept me half hard which was a good point so the condom wouldn't slide from my softening cock and remain trapped in his ass. Eventually he stood up and with one hand peeled the condom from my dick and then poured the large glob of semen directly to his mouth and swallowed it while looking at me with an incredibly naughty look.

"I hope you don't think I am too dirty, daddy but I just love the taste of cum on my mouth," he chuckled.

I was out of words. That was a tremendously raunchy sight and if I were any younger, I would have been hard again right then and there. As I wasn't, I couldn't. I pulled him down after he swallowed and said

"Come here, you dirty little slut. Kiss me right now."

His mouth, once again, tasted like mouthwash but now with a more pronounced flavor of maleness. My maleness. After a long kiss I just hugged him tight and murmured.

"Thank you, Bert. You are a real angel"

"Nothing to thank, Alex. It was my pleasure," he interjected. "I like what I do, and I liked it a lot with you. I told you I'm very into daddy bears like you, and you are a very sweet guy. Shall we watch TV, or shall we go to bed?"

"Anything is ok," I said. "We might stay watching TV and having some wine, or beer or that vodka that you like so much."

He smiled and stood up in front of me. He turned seductively and turned his back on me. He began to twerk his ass coming down and up until stopping. He then walked to the kitchen to prepare the drinks.

Swaying that glorious bubble butt he asked without turning, "What will you drink?"

"If your cum is not available, pour me the same you'll pour for you," I retorted chucklingly.

He laughed loudly and said, "Cum is on the menu for later, daddy, that's for sure. For both of us. At this rate, I think I'll turn you into a very dirty, twink-fucker cum-drinker old daddy before the weekend is over."

"You don't know the half of it, sonny," I told almost to myself. "You don't know the half of it"

I remembered when we talked online while arranging our encounter. I wanted him to be clear that I was not planning on going passive with him. I didn't think I would be prepared to be bottom and, facing the facts, I thought I was too old to be thinking of losing my anal cherry at this age. But his sweet demeanor, his nice persona and, let's face it, his hot looks, had me thinking on this possibility for the very first time of my life. Or maybe thinking on this consciously for the very first time of my life. It would be interesting and broadening my sexual experiences, but I didn't mention anything then. Let's just roll with the tide and wait to see what happens.

STILL FRIDAY NIGHT

We sat with two glasses of vodka on the rocks, without any cum in them of course. The TV was blabbering nonsense and we just sat there holding hands, occasionally caressing our fingers. I passed one arm over his shoulders, and he rested his head on mine. I turned and softly kissed the top of his head. It smelled of shampoo and something else undefinable. He purred like a kitten. Shortly we started talking.

He told me about his life story. He was the youngest of six siblings. Three older sisters and two older brothers, and he was the unplanned one being born 8 years after the last one. His family, while not rich, were wealthy enough and they had a nice ranch about two hours away from the city.

He had a very happy childhood, riding horses in the ranch, helping with the cattle, and playing with his older siblilngs, not lacking anything in general. All his older brothers and sisters went to university to study stuff related to farming and cattle rising but he didn't feel the call for that. Since a very early age he liked the arts. Painting, writing, photography, things that wouldn't help a lot in the family business. Thankfully, his parents were understanding and allowed him to pursue his dreams.

At the beginning of puberty, he realized that he didn't feel attracted to the number of hot girls that lived around the farm, including the daughters of the families that lived in the small town close by. As most boys from a Latin-American country, he ended up losing his cherry when his brothers took him to a brothel in his teens. As he told me, he did the deed, he even orgasmed, but it didn't feel right. It was kind of mechanical. He didn't feel interested in touching and playing with the lady parts. They continued to visit the brothel for the next few years, and he even had a fling with an older girl that lasted a few weeks but then came the time he had to move to the city to get into university.

His parents put him in an apartment, and he moved there alone. It didn't take long for a postgraduate student to discover his leanings and after a few dates, Bert took him to his apartment, and he lost his cherry that night. This guy, his first male lover, was almost 10 years older, tall, dark and misterious. His rigid cock took the nectar of his innocence and left him a mount of jelly after his first intense orgasm. The older guy was versatile and that night Bert learned the delights of opening his ass to a hard cock, of sucking a hard cock to orgasm, and of plowing into a tight male ass.

This relationship was meaningful to him. He loved touching, kissing, sucking, and playing with that guy's body and he knew then that he was gay. He could be passive or active without a problem, but he relished on the sensation he got when that other guy's cock flooded him with spunk while roughly plowing his entrails. After a few months, the guy finished his studies and left to another city. Bert felt a pang of sadness but promptly rebounded. He became very liberal with his body and very insaciable regarding new experiences. The older guy introduced him to the gay-swinger scene which gave Bert plenty of oportunities to sample all kinds of cocks, asses, and ages, leaving him hooked on gay intercourse. Within just a few weeks he went from the provincial, confused, straight boy to a sophisticated, lustful, young gay man capable of all kind of techniques and lewd acts.

Returning home for school break he came clear with his family, and once again, they were very supportive. They told him that their only interest was for him to grow in his chosen professional path and that whomever he decided to share a life with they will accept it. He didn't mention what he was thinking at the time. He wanted cock and ass. A lot of cock and ass. He didn't want to settle for monogamy, feeling sure that at that juncture, it was impossible for a single guy to completely satisfy him. At least not yet. Having a keen sense of business, he realized that he could fulfill his lewd needs and make some money on the side so, he placed the add I read, and which took me to contact him. He had been doing the escort thing very discreetly for two years now, and had a large stable of clients who shared his bed regularly.

I told him about my history, how I married late to a very young and hot lady, how that marriage only lasted four years but left me with a daughter I adore. How I later remarried a woman of my age, how that marriage lasted for ten years and how it cooled down slowly until we decided to call it quits. I keep in touch with both my ex-wives and particularly with my daughter. My daughter and I have a very special relationship. I rose her with the sense that she didn't need to keep anything secret from me, that I would never be judgmental and that I would always be there with advice if she asked for it or just wanted me to listen to her if that was what she needed. We were so open with each other that when she started thinking on becoming sexually active, she discussed everything with me, asking for advice, orientation, how to control the situation and what not. Soon after she informed me that she was bi, loving to play with cocks, but also loving the softness of a female body. She was now older than Bert, still single, living in Europe, and we kept no secrets from each other. In fact, she was the only other person in the world who knew what I was doing that day.

After a long talk, we decided it was time to sleep. We went for a shower, separately now, and then we went to bed. There was no need to dress anyway. He placed his head on my chest, and I put an arm on his shoulders, and we went to sleep. I woke up in the middle of the night needing to pee. I untangled myself from Bert, very delicately trying not to wake him up, went to relieve myself and returned to the bed and laid down next to this incredible person and put my arm around him. He grunted something, and opened his eyes.

"Any problems, daddy," he asked, sleppely.

"No, sonny," I answered. "I just went to take a leak."

"Mmmmmh, would have helped you, daddy," he said dreamily, "I would have hold your cock and aim it to the WC, or better, to myself and let you relieve yourself giving me a hot, golden shower," as he slowly woke up. The lewdness of his statement got me partially hard as he easily found out when his hand went to my cock and began to rub me.

"Do you like this, daddy?" he asked with lust painting his words. "Do you like my hand rubbing your cock?"

I brought my hand to him to get him hard again but found it was not necessary. He was rock hard.

"Yes, sonny. I like to be wanked by you."

We arranged ourselves in a 69 and quickly got each other's cock in our mouths. I tried to go deeper and managed to keep his cock head at the entrance of my throat without gagging. He was moaning and sucking at me with gusto. His cock was delicious. His precum filled my nostrils as my head bobbed up and down.

We shifted positions and I was lying on my back while he straddled my face and kept at sucking my cock. He caressed my balls and his finger was decidedly pressing in my ass. I took his dick out of my mouth and glued my lips on his rosebud. It was tangy and pungent, with an undefinable flavor. I thoroughly slobbered over his asshole before returning to his cock. He took his finger away from my ass but soon was again at it, slowly pressing. It felt wet and hot and involuntarily, I relaxed a little and he slipped his finger in my ass to the knuckle.

"Do you mind daddy?" he asked with a husky voice. "I couldn't resist, sorry."

I growled and showed my approval by pressing my hips against the invading finger. He pushed deeper and quickly found my prostate. He pressed on it as he gave me a very deep suck and that was it for me.

A gigantic wave of pleasure crashed on me and made me kind of lose mi mind. A deep growl came from the darkest depths of my being as a big load spurted from my tip directly into Bert's throat.

He pushed down on my groin which had the effect of simultaneously pushing his cock deeper in my throat and then he also came. His semen pouring directly from his balls into my mouth like a power hose. We kept on sucking as if our lives depended on it and it took us a while to finally calm down.

"Jesus, sonny!" I panted. "You really know how to make a man cum! That prostate massage was out of this world!"

"Your cum WAS out of this world, daddy," he retorted. "I was dreaming of the moment you would cum directly on my mouth."

We caught our breaths and turned around. Again he was lying by my side, with his head on my chest and my arm wrapped around him. He rapidly fell asleep. I remained awake, watching his chest rise and fall and listening to his soft snores. He looked angelic, with his eyes closed, his luscious lips partly opened and his breath coming and going slowly. I could not help thinking that this kind, sweet boy would be great fucking my ass if only I could decide to. With that thought, I finally drifted on to sleep.

SATURDAY MORNING

The following morning, I woke up first. I went to the bathroom, took a shower, shaved and brushed my teeth. Then, not bothering to dress, I went to the kitchen and got the coffee started. I donned an apron that was hanging in a hook by the fridge and began to prepare a light breakfast. Boiled eggs, toast, butter, jelly, cereal, fruit and milk.

When I was peeling the last egg, I felt someone hugging me from behind, nuzzling my neck and mumbling. "Good morning, daddy."

I turned around, to behold Bert's visage. It's usually true that nobody looks their best right after waking up, but this didn't apply to him. Bert was in front of me with his hair tangled, his eyes puffy, a red spot in his left cheek where the pillow pressed against his skin and stiffling a yawn. He was, of course, gloriously naked. For the first time I saw his limp cock. It rested demurely against his sack, the tip barely reaching below his scrotum and his head fully covered. Once again, I wondered about letting him top me. Bert was a study of youthful beauty mixed with lewdness and I drank that image of him trying to burn it in my brain. I held his head with both my hands and planted a soft kiss on his mouth saying. "Good morning, sonny"

"What are the plans for today?" he asked between yawns.

"I would love to go sightseeing a little," I suggested. "I mean, I don't know this city and I would like you to show me around if you don't mind"

"Oh, sure," he said enthusiastically. "We can go to the park a few blocks from here, have a nice walk, then go to the mall so you can do some shopping and maybe go to the beach in the afternoon. Then we can come here and fuck like rabbits for the rest of the night"

"Mmmh, sounds like a plan," I said. "Let's have breakfast and leave."

We sat at the table and had our breakfast. We talked about all sort of things, at some point, not unexpectedly, turning into sexual things.

"So, daddy," he inquired. "What got you interested in gay sex?"

"I'm not really sure, sonny," I answered truthfully. "As I went through my routine porn-watching sessions, a trans video sneaked in my playlist and I found it intriguing but I didn't think the fact of playing with breasts and cock in the same person would really grasp my interest or satisfy my curiosity."

He giggled at the tought and pushed. "But then how did you decide?"

"The seed was planted when one of my irregular partners showed me a video of a twink getting royally screwed by a gray-haired man," I said. "I don't know why she showed me that but the curiosity was firmly set in my mind."

"And how long did it take you to act on your curiosity?" he insisted.

"Longer than I thought and probably shorter than you expect," was my criptic response but then I decided to clarify, "A couple of months later I decided to search around and signed up in the page where I found your add. Once we chatted the decision was made."

"Interesting," he said. "So, mine was the first add you saw."

"Not a chance, Bert," I said, "but yours was the one that popped as the best. And now, here we are."

He stared at me as he blushing faintly and murmuring, barely audible to me.

"Damn. 'We', the damn bear had to say 'we'..."

I pretended I didn't hear and continued with my breakfast. Soon we finished, cleared the table and we went to change.

SATURDAY NOON

Bert dressed in a pair of black boxer shorts and a white sleeveless shirt. He was wearing running shoes without socks and a baseball cap of one of the local teams. I donned a pair of white Bermudas, a yellow polo shirt, also running shoes but with socks and no cover in my bald head. We walked leisurely to the park and started to stroll aimlessly while talking about anything and nothing in particular. To other people we looked like a father and his son or an uncle and his nephew spending some nice bonding time. Bert started talking about his studies which turned into an interesting chat. He was very enthusiastic about his subjects, very proud on his grades and quite knowledgeable about new and old artists, being them photographers, painters, writers and even cinema stars. I have always been a cinema buff and talking about this made the time pass pleasantly. A couple of hours later we returned to the apartment, took the 4x4 and drove the 15 miles to the mall. We shopped around for a while, at one time passing the front of a sex shop. We looked at each other with temptation painted in our faces but decided for discretion. Maybe another time. I got him a few pieces of clothing as a present which prompted a heated discussion because he didn't think it was proper, but I insisted. I was a delight to see him trying out clothes. Anything he put on looked terrific without the need for a single stitch to adjust the clothes. I finally settled for a sport blazer, a set of black slacks, a couple of pastel colored long-sleeved shirts and a few t-shirts. A couple of speedos found their way in the bag as well and the total didn't even reach one-hundred dollars. This reminded me his fee, that at five-hundred dollars for the weekend, I already found way too low, particularly after seeing how he devoted all his attention to me and catered to my every wish.

When stepping out of the store he said, "Wait for me, uncle. I need to take a leak."

Marveling at the ease with which he switched between our role-playing games I sudddenly decided he deserved to be paid better. I went to a nearby ATM machine and withdrew another 500 dollars and hid them in my pocket. Later I would put them in an envelop and give it to him.

Then we stopped at a fast-food place to grab a quick lunch and then headed for the beach across the street.

We arrived at the beach at around two pm. It was not crowded but not empty either. There were a couple of families with loud teenage kids, some young ladies and a few lone men and women. We rented a beach umbrella and a couple of beach chairs, ordered some drinks and a case of ice and sat down to talk. We quickly disposed of our clothes and remained in our bathing suits that we wore under. Bert was boasting a black tight speedo that showed off his youthlike body and the bulge of his cock. I immediately noticed some of the girls ogling him but, being this a family beach, they limited themselves to just watch. I was wearing my yellow ones, the ones I wore in the selfie I sent him, also showing a nice bulge as I was still at half mast. Somehow, this kid was managing to keep me half hard almost all the time. Obviously, my visible bulge didn't rise too much interest in the girls sitting nearby.

After one or two hours of basking in the sun and sipping bears we decided to get into the water. It was delicious, not too cold and nicely deep. After walking just 8 or 9 meters from the shore the water was already up to our necks. It was a very quiet beach. Very small waves and the water was a little murky. Bert came close to me and naughtily started to rub my cock from afar with one of his feet while smiling and talking innocent things. Of course, I started to respond so he just came closer and pulled my speedos down. He immediately went to work on my cock and began to wank me with knowledgeable movements, rubbing his thumb over the head and in general making me lose my mind, Very soon I was releasing thick ropes of cum under the water. After a few seconds, I pulled up my speedos and glared at him.

"Do you really think I would be able to walk to our chairs with a hardon inside this suit?" I asked.

"Of course I knew you couldn't, daddy," he chuckled. "That's why I gave you that hand job. Now let's wait for you to deflate a little and go finish our drinks so we can return to the apartment. I'm feeling very honry now. I need a good buggering."

We returned to our chairs to finish our drinks and dry out. Then we dressed. I looked the girls and surprisingly, they were smiling at me. They stood up and stretched, pressing the sheer spandex of their swimsuits into ther young, nubile bodies. It was a very enticing sight but this weekend, I only needed something else and it was right next to me. When I turned around, Bert was already dressed and had the chairs in his hand. I grabbed the icebox and we returned the chairs, picked up the 4x at the mall and drove to the apartment right away. All the way Bert was fondling my dick through my Bermudas and pretty soon got me hard again.

SATURDAY EVENING

We arrived at the penthouse right after four pm and I had just barely closed the door when Bert was all over me kissing, groping my cock, smacking my ass and pulling off my polo shirt. I put my hands inside his t-shirt and started to rub his nipples as I returned kiss by kiss with our tongues battling fiercely. Soon I peeled his shirt and latched on his nipple sucking it deeply as I panted hard. I was almost out of breath with lust. I desperately pulled his boxers down. I don't know when, but it seemed he had taken off his speedos before donning the boxers at the beach because, when I pulled the boxers down, his cock sprung free, hitting me in the nose, and proudly pointing up and hard as a rock.

"You naughty boy!" I said. "When did you take off your speedos?"

"While you were ogling those slutty girls that were about ten meters from us, daddy," he said while still holding a mouthful of my tongue. "I was feeling very jealous. You're mine this weekend. You can fuck them later if you want"

"Don't worry, sonny," I assured him. "Although I don't plan to quit on pussy anytime soon, I don't plan to quit on your young cock and ass either. I wouldn't think on wasting energy in a pair of young pussies while having your whole body here, next to me."

I started wanking him. His cock was so hard, the skin so soft, and it felt so hot, it was almost burning my hand. I rubbed his cockhead with the palm of my hand to take his precum and smeared it all over his shaft. In the meantime, he had already taken off my Bermudas and Speedos and was also wanking me with fast movements.

We clumsily traipsed to the bedroom and fell unceremoniously on the bed. Somehow, we fell on a sixty-nine position, and I immediately went to work on his beautiful cock. I slapped my cheeks a few times with that hard tube, smearing precum on my face, before sinking it in my mouth. I knew now what really turned him on and started to suck powerfully while masturbating the part of his cock that remained outside my mouth. I still hadn't been able to control my gag reflex and although he wasn't that big, he was big enough to trigger it if I were not careful. Anyway I was getting better, being able to hold my gag reflex if accidentally (or not?) took him too deep. I released his cock and went to lick and suck on his asshole. It was kind of spicy, sweaty, and pungent but squeaky clean and I couldn't get enough of it. I slobbered a lot over it putting two fingers and rubbing his prostate. Then I returned my mouth to his cock without abandoning his ass.

My tongue licked the rim of his cockhead and then the inside of his foreskin while my other hand tickled his scrotum. He started doing the same, but he took me completely on his mouth and I felt the head of my cock hitting his throat repeatedly. He didn't gag at all, just continued slobbering me and then he moved his head a little and swallowed my head.

When I felt his throat muscles massaging my head I was pushed over the edge and with a wild growl I exploded and sent thick ropes of cum down his gullet directly to his stomach. It seemed that I came gallons but of course that was not the case. I had to relinquish his cock as my skin was tingling all over and I needed to breath. I started to rise my hips directly fucking his throat while my climax lasted. Afterwards I just laid on the bed panting. He was next to me with his cock still raging and a beautiful smile in his face.

"Did you like it, daddy?" he asked. "Was I any good? Am I a good cock-sucker?"

My mind was in a whirlwind of emotions I didn't know what I was saying, and I answered.

"I want you to fuck my ass, sonny," I said surprising myself. "I want you to ravage it like you mean it."

His eyes turned to plates and he said, suddenly serious. "No daddy, I will not ravage you. If you want me to fuck you, I will, with immense pleasure, but I'll be very gentle.: he continued saying "I want you to enjoy it," and then added, "But if you're sure, let's first go to the bathroom."

Intrigued, I followed him there. He brought his carry-on and pulled a plastic bag, some hoses and a cannula and said.

"Let me give you an enema before, so you're squeaky clean, OK?" he said.

I stared at the equipment and had to ask, "were you expecting I would change my mind about doing bottom?"

"Not really, Alex," he said abandoning the role-playing for a while, "but I had to be prepared just in case, don't you think?"

"OK, Bert. Then, why is it necessary?" I asked quizzically, my ignorance on gay sex evident in my question.

"It will be very intense for you, Alex," he informed me knowledgeably. "I think you are a highly sensual person very uninhibited when it comes to sex. I have seen you tend to come very hard and your muscles contract with enormous strength. If I manage to make you cum while I fuck you, I am sure you don't want any accidents to occur. Your rectum could leak and I'm sure you wouldn't want that to happen, not that I would mind though. It wouldn't be the first time I fuck the shit out of someone, but never on a first time. So, let's clean up that rectum and take that worry out of our minds."

The kid had a point so I just followed his directions.

"Step into the shower, daddy," he asked me returning to the role-playing.

He stepped in behind me and thoroughly soaped my body paying special attention to my ass. He then filled the bag with warm water and lubed the cannula.

"Come here, daddy," he said pointing to the bidet. "Sit here and relax."

He tenderly inserted the cannula in my ass. Even though this was really a medical procedure it felt incredibly sensual, and I became aroused again, with my cock unashamedly pointing up while he manipulated the cannula and started to pour the warm liquid in my rectum. The naughty boy was even making tiny in-and-out movements with the cannula which although not enough to bring me to orgasm, did wonders to keep me rock hard.

"Do you like that, daddy," he asked with a dirty smile. "Do you like the canula fucking your tight ass?"

I grunted my approval, not able to speak clearly. I guess it was some kind of training, or whatever. I didn't really care.

Soon the bag had emptied completely inside my rectum and Bert asked. "Sit in the WC, daddy, but hold it as long as you can. I'll be back shortly."

I felt horribly full and was desperate to void but held myself without knowing how. My pelvic muscles were contracted strongly and at the same time, I remained hard as a log. Soon Bert was back and asked

"Have you already voided, daddy?"

I hadn't so he encouraged me. He started to caress and massage my hairy belly with one hand while the other grabbed my ass cheek and started to pull it to a side. As expected, I released all the liquid and all the material that remained in my rectum in a single swoop down the toilette. During all this procedure both of us remained with cocks hard as steel.

We flushed the WC and returned to the shower, and he lathered me once again in soap. His hands went between my ass cheeks, and he generously spread a generous amount of soap and began to clean me up. His hands were all over the place, his fingers knew no limits as to where to touch me and even entering a few times in my chute. After the clean-up, we went back to the bedroom, and I laid on my belly. On my own volition I flexed my knees to rise my ass, exposing it completely to Bert's gaze. He kneeled behind me and started rimming me.

"Unghhh!" I uttered. "That feels sooooooo good."

The sensation of his tongue on my ass was indescribable. With every lick he sent electric shocks that made my cock twitch wildly, precum dropping in large globs and goosebumps erupting all over my skin. He seemed to enjoy a lot to be on the giving end and I decided to enjoy being on the receiving one and let myself in the hands of this knowledgeable young man.

He took the lube bottle and poured a large glob on my ass crack and started to massage my rosebud and gently introduced a finger. He began to push it in and out softly and soon was massaging my prostate. My cock was twitching involuntarily while even more precum was leaking out. Seeing this he promptly inserted a second finger and began to massage my sphincter with expert movements making it relax. At this time, I was thoroughly dominated and completely on his hands.

Then he removed his fingers, and I could see between my spread legs that he was lubing something in his hand. I couldn't see it, but I already trusted him to a fault. I buried my face on the pillows and then I felt something cool and very hard pressing my rosebud. He asked me to relax and continued relentlessly pushing whatever that was up my ass. Suddenly it kind of plopped in and I again felt very full. Whatever it was, it sent shivers of pleasure up my spine, and he was moving that thing in circular motions and pulling it a little then pushing it again. I kept my face buried on the pillows as I felt blood flush both in my cock and my face.

"What the hell is that?" I asked somewhat alarmed, my voice muffled by the pillow.

"It's a butt plug, daddy," he retorted calmly. "It's meant to show you how it feels to have something hard up your ass. The idea is to relax you and train your sphincter to allow, let's say bigger things get in. Does it hurt?" he then asked with some concern in his voice.

"Not at all," I said, and it was remarkably, true. "It feels weird but doesn't hurt," I clarified. "It feels surprisingly good," I assured him, and I could sense his smile as he started pushing it more.

After a few minutes during which he continued to slowly press and move the buttplug in my ass and kiss my perineum and my balls, I felt him pulling out the toy. My ass released it with a plop, and I felt a weird emptiness. Immediately I felt something else pushing against my rosebud. It was kind of supple and warm. I tried to relax my muscles, thinking "this is it" and then I felt it invading my rectum and going way deeper than the butt plug. It was warm, supple, and quite rigid. Bert pushed it forward and I felt it fucking my ass slowly but deliciously and I said.

"Your cock feels wonderful, sonny. Keep going."

"It's not yet my cock, daddy," he laughed. "I'm fucking you with my favorite dildo. I cannot tell you how obscene your ass looks dilated and wrapped around this rubber cock. I love the sight" said the naughty boy and then added, ". It's getting me soooo hard!. I can't wait to switch it for my cock."

"Good, sonny, glad to be of assistance but don't you dare make me cum with a rubber dildo up my ass," I told half seriously. "If I manage to come while being sodomized, I want it to be with YOUR cock buried in me and not some plastic and latex contraption, are we clear?"

He laughed again and said

"OK, daddy. Sure. I think you're ready. This is it then. Brace for fucking!"

I peeked through my legs and saw him wanking his cock that was as hard as ever, with an angry red head glistening with my saliva and his juices. He then put on a condom and lubed it thoroughly. I thought "this is it. I asked for it and its coming. He's really going to fuck me and not only I'm letting him. I actually asked for it"

He positioned himself with his cock resting between my buttocks and stopping with the role-play, he turned dead serious, and said:

"Alex, I need to make myself very clear on this. I want you to tell me honestly if you want to stop. I won't force anything, but you must know that this will be uncomfortable to begin with and although I will go slow and gentle it may hurt. How much, I can't tell. If you manage to relax it probably won't hurt much. I you don't relax it certainly will hurt more. Just let me know if it is too much and I'll gladly stop."

"Just go ahead, Bert." I assured him. "I promise I'll make you stop if I can't handle it"

He then began to push slowly but firmly. In a moment his head plopped through my already relaxed sphincter, and started to fill my ass with something it never had inside. It felt the reverse of voiding a large one. It made me want to push and I did, which funnily enough, relaxed my sphincter and made it easier for Bert to keep on plowing my chute. My sphincter was being dilated slowly but relentlessly. He hadn't moved any further. My breath was coming in short gasps when he asked:

"Are you OK, Alex?" he asked, "does it hurt too much? I just put the head in."

"UNGHHHHH!. IT FEELS SO GOOD!. YOU CAN CONTINUE, SONNY, I'M READY!" I said with more courage that I was really feeling but returning to the role-playing to signal him that everything was all right.

He began to twitch his cock which sent soft jolts of pleasure through me and made my cock twitch in kind. Then he pushed in slowly and I felt like a train was getting inside me but remarkably, it was not painful at all. It felt strange but without even an iota of discomfort. I tried contracting my muscles the way you do when you want to stop peeing to see what happened and he grunted

"Daddy, don't do too much of that if you can avoid it or you'll make me lose control, and believe me. You don't want me losing control while taking your ass cherry."

He pushed until about half his cock was buried in me and then began to slowly withdraw. The sensation was hot. Very hot. He then started to fuck me with half his cock, every push in inching just a tiny little bit more and every pull out leaving just the head inside. I was getting more and more aroused and in the next push-in I suddenly pushed back with my hips and managed to impale his whole rod inside my ass in a single motion.

"GOD, DADDY! YOU'RE SO TIGHT!" he mumbled to which I answered.

""GO AHEAD, STUD. FUCK ME LIKE YOU MEAN IT!" I begged.

I could felt the heat of his belly resting on my buttocks. I had taken him completely in. I felt so full it was a wonder it didn't actually hurt. I felt electric shocks coming from my ass directly to my cock which was as hard as I had even seen it and once again, large globs of precum were pouring from me into the bed.

"I'll stay here for a while until you feel ready, ok?" he said.

"Don't," I said as I moved my hips back and forth, fucking myself. "Just don't sonny. Go ahead and FFFFFFFUUUCK!" I yelled as he suddenly started to fuck me.

My cock was ragingly hard as I felt my insides turning to mush with the invasion that was taking place. The heat irradiating from his cock seemed to burn my entrails and from there extended to all my body. It was feeling something I never felt. I wanted this youth to fuck me as hard as he could. As he began to move in earnest, I could identify every single vein, every single bump of his cock rubbing deliciously on my ass. His tube rubbed hard on my prostate sending flashes of lust all over my body.

Bert was grunting and moving with gusto, seesawing his cock in and out of me with progressively faster movements. At this time all kind of dirty thoughts began entering my mind. I began to wonder how it would feel if he fucked me raw and I could feel his hot cum blasting inside me. I began to wonder how his cock would taste right now, fresh out of my ass. I began to wonder how it would feel if I had another twink in front of me and I was also fucking him while Bert fucked me. I began to wonder how I would feel if Bert and another twink would spit-roast me. I was a mess of lust and lewd thoughts,. Suddenly I felt a hand grabbing my cock and starting to wank me which brought me back to reality. His attentions felt way too good, and I continued to move back and forth literally fucking myself with his pole.

"I see you're enjoying yourself, daddy. Leave it to me," he offered.

And with that he started to move hard in and out, raising the tempo relentlessly as our lust and needs increased. He released my prick and grasped my hips for balance. In no time he was smacking my back with his belly and his balls were colliding with mine giving me a weird, intensely pleasurable sensation as his cock reached the unexplored depths of my ass. I accommodated to his girth, and I began to really enjoy this. The feeling of his hard cock filling my bowels was exhilarating. The friction was maddening. The pressure applied on my prostate made me see stars and my cock was leaking furiously over the sheets. I felt a strange warmth basking me and it seemed to irradiate from my very full ass and the fire his cock was lighting up my entrails.

"YES, SONNY," I panted. "FUCK THAT OLD ASS!"

"I WILL, DADDY!. I WILL FUCK YOU SO YOU'LL NEVER FORGET ME!," he said lustily.

"GO AHEAD, FUCK AWAY. LESS WORDS MORE FUCKING!" I said as I started to contract my muscles once again.

He grunted and increased his tempo. Now he was fucking me really hard. With every movement his cock would press against my prostate and that made me gush out large globs of precum but having ejaculated so recently I was certain I wouldn't be able to cum again so soon. He kept his marvelous pace, and I could feel he was really pounding me. My movements met his in perfect sincronization, making this fuck something lewd, and marvelous. His hands were grabbing my hips as he pushed and pulled me in perfec synchronization with his fucking. Suddenly, he slowed down a little and unsheathed himself. I felt an emptiness when he pulled out with a *plop* and I turned around questioningly to see him lying down with that beautiful dick sticking in the air and he asked me.

"Wanna try riding?"

I obliged. Positioning myself over his pole, I came down on it while he guided it. Being so excited, I took him in completely and then started to wriggle on top of him. Soon I was twerking, moving back and forth and rising my ass only to slam down fiercely. my dick hitting his marvelously flat abdomen and dripping precum all over his skin. I continued contracting my muscles and could see his eyes were bright with lust. A few minutes went by and soon I felt, incredibly, how my own orgasm started to build in the depths of my being, like the threat of a tsunami after a large earthquake. I increased my own tempo pushing back every time he pushed in and contracting my muscles every time he pulled out. My cock was swinging wildly dropping my precum all over the place and over his beautiful, almost hairless torso. He started to grunt unintelligible words as I felt my orgasm swelling over me.

"I'M CUMMING!, SONNY GOD HELP ME, I'M GONNA CUM SO HARD. YEEEEEES!" I screamed.

I exploded and long, thick ropes of cum flew out of my cock and splashed over his chest, reaching his face, decorating those luscious lips, painting his cheeks until a small dripple continued to fall from my cock to his lower abdomen and his bush. In the same moment Bert pushed himself to the limit and I felt how his cock swelled and started powerful contractions, and I knew he was filling his condom with a large load.

"YESSSSS, DADDY! I'M CUMMING INSIDE YOUR ASS!" he yelled. "I'M FILLING THAT CONDOM! I WANT TO PAINT YOUR ASS WHITE! I'M CUMMING!"

I could feel every last vein and contraction of his cock which only prolonged my orgasm until I fell exhausted on his body smearing my cum all over ourselves just like we did on our first fuck. His cock still hard, twitching deeply buried in my ass. I don't know for how long we remained not moving. A short while later I shakily unmounted him and turned around to grab his cock that had barely deflated. I peeled the condom that was completely full and, imitating him, I took it on my mouth and poured his load all over my mouth and face. I swallowed most of it but I let quite a lot drip over my lips and chin. I then smeared the remaining cum in my face I lowered my head offering him my mouth. He kissed me hungrily mixing his cum in my mouth with what had landed of mine in his lips. We lustily exchanged our juices and ended in a tight embrace.

"WOW, daddy," he murmured in my ear. "That was soooo hot. You'll leave this city as a new man. A twink-fucker, cum-drinking, ass-gaping old man!"

SATURDAY NIGHT

I don't have a very clear recollection of the following minutes. I only know that later we were lying in bed, entwined in a tight embrace over the soaked and reeking sheets until we fell asleep even when it wasn't 6:00 pm yet. We laid sleeping over the mess of cum, sweat and lube and we didn't care at all. About two hours later I woke up to find him asleep in my arms, with his lusty smile decorating his face. I didn't care if I woke him up which of course I did by starting to rub his half-mast cock. When he opened his eyes, I kissed him deeply while still groping his hardening cock and thanked him for a fantastic initiation. He just hugged me back and said.

"It was my pleasure, daddy. It's always kind of magical when someone offers me his ass cherry like you did." And pensively, he added, "And it's even better when that someone is such a sweet person and such a naughty bear-daddy."

He stared deeply in my eyes. In that moment he looked very vulnerable, and I realized just how young he really was. He then said.

"I am being completely honest here and I hope you value my sincerity, daddy, but I think I could easily fall for you."

I couldn't believe how vulnerable he looked then. How whole and sincere those words sounded. It was probably part of his act with his clients, but I chose to believe he was sincere. I kissed him deeply, gently caressing his face and the back of his neck.

He purred and pressed himself to me and held my hand on his chest, softly caressing each of my fingers separately. Soon after he stood up in a sudden whirlwind of energy and said.

"We need some food, daddy." He said looking in my eyes. "Let me cook up something."

"With or without cum?" I asked to which he laughed.

"Without, of course! We'll leave that for dessert."

With that, we went to the kitchen and he donned the apron I used that morning. He then started to make some pasta while I watched him from the door of the kitchen. He looked deliciously naughty with those buttocks in the air and the strips of the apron tied on his waist. When he turned around, the apron was distinctly tenting over his cock which again was at full mast. God, the blessings of youth! Seeing my glance, he blushed and busied himself with cutting some veggies and making a sauce for the pasta which was ready in no time. He then served two plates, opened a bottle of wine and set the table.

"Let's eat, daddy," he said looking me straight in my eyes. He poured two glasses of chianti and said seriously.

"I rarely cook for my clients, but I think you deserve it. You have given me a lot and I only hope I at least managed to come close to fulfill your expectations."

Wordlessly I came close to him, hugged him from behind and sunk my head in his mane of hair. It smelled of shampoo, sea water and sweat and I swear I could remain there smelling that for hours.

"I'm touched, sonny," I whispered to his ear while my cock rested on the crack of his ass. Then licked the earlobe slowly and wetly and repeated. "I'm very touched."

He remained motionless and shivered as a leaf on the wind. He looked really vulnerable and young at that time.

"Daddy..." was his only word.

I softly shushed him and we sat silently to eat the pasta. It was delicious. The veggies were cooked to perfection and the pasta was al dente. I couldn't have had a better meal in an upscale restaurant.

We talked little during the meal. We kept glancing at each other and by the end, we were eating each other with hot glances and hands that couldn't find a place to rest. Trembling myself, I helped to clear the tables and silently, Bert grabbed my hand and took me to the bathroom.

We filled the jacuzzi and turned it on. He added a little bottle of bubble bath and the water turned into a decadent mass of bubbles and enticing aromas. He went to the bedroom and returned soon enough with some candles which he put around the bathroom and lit. He then turned off the lights and, dropping the apron, got into the jacuzzi silently beckoning me with a twirl of his finger. I was again rock hard and followed him inside.

We sat next to each other in a surprisingly modest position, but this, of course, would not last. He leaned to me, and we started making up heavily. I kissed his mouth and let my lips wander all over his face while my hands couldn't get enough of his fantastically soft skin. I caressed his chest, lingered in the faint shadow of hair in his lower belly, cupped his ass below water and grabbed his meat while caressing his balls. I sucked on his lips and moved to softly kiss his nose and then his chin. My lips then traced each ear with very soft kisses and licks all while murmuring tender and dirty words. His mouth was not idle either. He was planting feather kisses all over my cheeks and chin resting on my ears and softly nibling and kissing it, while his hands lingered on my chest, entwining my hairs before moving down to my large belly and repeating the action. His other hand grabbed my ass and insinuated a finger in my crack which soon found my ass and began caressing it. Leaving my belly, he grabbed my cock and began to jerk me with rapid and sensuous movements. This was more romantic than most of the intercourses I had had since my divorce.

He then sunk below the water and took me in his mouth, sucking me. He could really hold his breath, and he started by sucking me, deep throating me with ease. I felt how his throat muscles pressed against my glans, and I had to pull out to avoid cumming to soon. He came up with flushed face and swollen lips. He then turned around pulling his cheeks apart offering me his tight ass once again.

"Daddy, please, give it to me..." he begged.

"Aren't we going to put on some rubbers, sonny?" I asked.

"No, daddy," he said softly. "I want to feel your cock raw and direct if you don't mind. I want to feel your jets of cum shot deep inside my ass."

"I certainly don't mind if you don't," I said. "Somehow, I trust you to a fault." Then I came closer to him. My cock was as hard as ever and the head was a furious red glistening with precum.

Bert was leaning forward with both hands pressed on the border of the jacuzzi and turning his head.

"Please, daddy..." he repeated.

I pressed my cock to his ass and immediately buried my cock deep inside his asshole. I remained motionless but he would have none of this. With a deep grunt, he started to fuck himself while moaning loudly every time he pressed my cock deeper inside him. I reached for his dick which was harder than steel and very slimy with his precum. I rubbed a little and took it to my mouth savoring his flavor while still pounding his ass as if there was no tomorrow. This couldn't last. He moved back and forth rubbing my cock all over his chute and in no time, he made me cum very hard. I painted his entrails with thick ropes of cum while moaning loudly in a way that must have been heard in the apartment below.

After that intense orgasm, and feeling him as hard as ever, I thought I couldn't leave him like that. I turned around and opened my ass cheeks. With no preamble and with an animal grunt, he pressed his cock on my ass and pushed himself inside balls deep in a single push. The sudden invasion almost knocked me out of my senses and made me grunt in pleasure but somehow, I held out. He immediately started to plow my insides and I had to hold for dear life on the border of the jacuzzi as he ravaged my ass with youthful energy, splashing water over us and on the floor. This couldn't last either and soon his cock swelled and jerked as I felt his delicious, hot jism pouring deeply inside me. After coming, he pulled out of me and some globs of cum leaked out of my gaping ass, but he grabbed my cheeks and fastened his mouth and gave me a thorough rimming that got me at half-mast once again.

He then turned me around and kissed me deeply sharing his cum with me while our tongues intertwined. Slowly we calmed down and had our breaths bak.

He looked me in the eyes and pleaed, "Daddy... I'm... I'm..." He didn't finish the sentence, and I was hoping he wasn't going to say what I thought he was going to say.

"Sonny, I'm here," I murmured, sealing his mouth with my lips. "We'll keep on seeing each other. I'm very much into you right now."

Then we went to the bed hand in hand. We spooned with me pressing my back against his youthful chest and we both fell asleep. Not an hour passed when I felt a hand furiously wanking my very hard cock and something very hard decidedly trying to enter my chute again. I pulled my cheeks with one hand, and he pushed his delicious cock again inside me and began to fuck me in earnest.

"Daddy! Daddy!" he moaned. "Daddy, I'm fucking you! I want to cum inside you."

"Go on, stud. Fill my ass with your cum," I said lustily. "I'm ready for you."

In no time I again felt his cock twitching deep inside me and rope after rope of cum filled me up to the brim. He unmounted me rapidly and took my cock in his mouth in a single motion making me cum deep in his throat. His cock was right in front of my face, glistening with his juices and I couldn't avoid it. I put it in my mouth and sucked his cock clean as if my life depended on it. His cock reeked of my ass, and tasted like cum with nothing hiding the fact a few seconds ago it was buried balls deep in my rectum.

After we calmed down, we cuddled and kissed deeply. His mouth tasted of pasta and cum. Tasted of sweat and soap. I kissed him deeply again and then, unbelievably, went back to sleep, this time it was I who spooned against Bert, feeling his youthful body and ass snugly fitting my body. I fell asleep with my cock nested between his legs and my hand holding his dick.

SUNDAY MORNING

At around 5 am I woke up holding his raging hard on.

"Are you awake, daddy?" he asked

I didn't answer and just laid on my back and parted my legs opening my ass with my hands. He kneeled in front of me, and he pushed his cock in a single push and fucked me silly missionary-style. I felt his cock twitching inside of me and as I thought I couldn't be more aroused he increased his tempo and grabbed my cock and started to wank me as he chanted.

"Fuck, fuck, fuck. You have such a wonderful ass, daddy"

"Keep plowing my ass, sonny," I panted. "I want to feel all your spunk poured in my ass!"

He came deep in my bowels for what seemed to be hours but surely were just a few minutes. Somehow, I managed to hold my orgasm, so he rapidly turned tables, straddled me and began to ride me wildly, facing me. I would not be able to hold for much longer and in less than five minutes I was spasming inside that incredibly tight ass and pouring another load up his entrails. He unmounted me and laid next to me. Both our asses were gaping and leaking obscene amounts of cum over the sheets. Eventually we had to call it quits. We walked to the bathroom and took a caste shower. My flight was leaving in a few hours, and I needed to be at the airport very soon.

When we were ready to leave, I handed him an envelope where I had put the money I withdrew from the ATM the previous afternoon

"But daddy," he said inquiringly. "You already paid me when you arrived"

"I know," I said. "There's not enough money in the world to pay you for what you did for me this weekend, sonny. This is only a tip and a heartfelt thank you for being such a wonderful person, such a lovely boyfriend and such a professional escort. You gave me a lot of pleasure. You showed me there was nothing to lose and all to gain by doing this. You showed me and taught me more than I ever expected and you made me feel worthwhile, sure of myself and more confident. That cannot be paid. Use this money for whatever you need; school expenses, clothes, toys, whatever. And you can be sure I will return soon enough. There are a couple of things left for us to do, don't you think? I just hope you'll remember me..."

He hugged me tightly and murmured in my ear. "I would never forget you, daddy," he said very seriously. "You showed me something I didn't know. You showed me a kindness I didn't expect. You respected me as a person. You showed interest in me beyond my fantastic sexual skills," this was said with a wink. "And you showed me what it meant to really connect with someone and give with a capital G, the way you give. I will treasure this weekend as no other weekend before, and I hope we meet again."

We packed and left the apartment dropping the keys in the mailbox of the front desk. Then we drove in silence to his home to where he directed me. I parked in front of his flat without uttering a single word as we stared in each other's moist eyes as lovers saying a final goodbye. I felt at that time that if I were younger, I would easily fall for this kid and I wasn't completely sure if he was acting or if he was actually expressing his feelings sincerely. If he was acting, he was one hell of an actor. Like before, I chose to believe he was being sincere. With wrenching heart, I pulled myself apart and he alighted from the car. We looked at each other through the window once more and as I drove off, he blew me a kiss and turned around. I arrived at the airport and flew home a changed man with broader horizons. When I got home and opened my carry-on, I found the second envelope I had given Bert with a note scrawled:

"Please, save this for our next time. XOXO. B."