pleasing-paul
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Pleasing Paul

Pleasing Paul

by Merrylevov
18 min read
4.02 (28300 views)
older manrimmingwatersportsyounger manmature
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As I walked through the baggage claim area of Rome's Fiumicino airport I wondered if I should really be doing this right now. I had booked this vacation months ago after my breakup with Janet, but now I had been laid off and wasn't sure if a one-week walking trip through Lazio, Italy was the best life decision at this particular moment.

I could have easily cancelled and only forfeited a small deposit, but it was far too late for that now. I had to go with it, my bank account be damned. With nervous anticipation I approached the two guides waiting for me at the assigned meeting spot and promised myself to just enjoy it.

The two Italian guides, Anna and Martina, greeted me with a handshake and a smile. In perfect English they explained that we were just waiting for a few more from our group to arrive and we would be on our way.

I introduced myself to the other three women who were waiting with the guides. Sue, Kate and Mary were all British women in their 50s and 60s. Given that this touring company was based in London, I figured the majority of the group would be from England. I wasn't sure, however, of the age and gender makeup for this type of tour. It was rated as one of the more rigorous trips offered by this company, so I assumed there would be some younger people signing up.

I was wrong. At 35 years old I was easily the youngest in the group by 20 years. The three women I met already seemed physically fit so I was sure they wouldn't slow us down. I was a bit worried I would be the one lagging behind, especially since I had put on entirely too much weight since the break up and wasn't quite sure if I could walk the 10-12 miles a day we would be trekking.

I made chit-chat with the women as we waited for our final members to arrive. Eventually a man and woman approached the group excitedly.

"I think we've found them!" exclaimed the man with a cheerful London accent. "Hello there! My name is Paul is and this is my daughter Sara."

"Welcome!" said our tour leader Anna. "The whole group is here. Let's make our way to the van so we can get going. If you need help with any bags Martina will be happy to help."

We made our way out of the terminal and walked to the short-term parking lot where two vans with the tour company's name and logo were parked. Anna gave a brief welcome to the group and explained that we would be having a quick drink and snack before leaving for our first destination.

Drinks in hand, the members of the group introduced themselves and made small talk. We would be spending a week together, so I thought it best not to make too many pre-judgments of anyone there. I did briefly worry that being so much younger than the rest of the group may alienate me, especially considering I was also the only American on the trip. I was grateful, however, that there was at least one other man on the trip in Paul.

I learned that Paul was 78 years old and had done a number of these trips before with his daughter. He was in terrific shape, standing about 6'1" and very trim. He wasn't traditionally handsome; with somewhat exaggerated facial features: a large nose, large ears and goofy grin filled with ever-so-slightly crooked teeth. But he projected a kind happy confidence that made me feel insecure and even a tad jealous.

"So tell me Alexander," he asked as we made our way to the first hotel. "What is it that you do in the States?"

I tactfully explained that I was "between jobs" and tried to steer the conversation elsewhere, still feeling the sting of having been laid off weeks prior.

"I'm sure you'll find your way," replied Paul. "Perhaps this trip is exactly what you need for a proper fresh start."

For the first time in months I felt a sense of warmth and kindness that had been absent from my life. Holding back tears I thanked Paul for his sentiments and told him how much I was looking forward to this trip and getting to know everyone. With a large, toothy grin and a laugh, he replied, "as the only men here we'll have to stick together!"

The first two days of the tour were delightful. Our guides took us through the Italian countryside, stopping periodically in villages that looked like they were from a different era. I got along with the group as I got to know them, sharing stories as we made our way from town to town each day.

Paul was an absolute marvel physically. On each walk he would charge ahead, sometimes leading the crew ahead of our tour guide. Even at 78 years he old he never seemed to tire, and was so sure-footed that he was the only member of the tour who didn't carry hiking poles, which I found necessary on some of the trickier sections of terrain.

On several occasions I tried to pick up my speed so I could walk with him. It was a struggle, but on day 3 I managed to spend most of the day at the front with Paul. There was something about him that I couldn't quite explain, but I just knew that I enjoyed his company. He told me about his retirement from business, and we shared a laugh when we reached a fork in the trail and I explained the quote attributed to Yogi Berra: "When you get to a fork in the road, take it."

Day 3 had been our longest hike so far, and when we finally reached our hotel I could not have been happier. The hotel was an agriturismo, a working farm with full hotel-style accommodations. As we walked up the dusty road at the end of our 14-mile trek to reach the hotel, I couldn't help but feel excitement as I realized we would be staying among these active vineyards and olive tree fields. We were told in advance that the owner of the hotel was also the head chef, and to expect an authentic home cooked "Italian grandma" style meal for dinner.

The hotel rooms were essentially duplex cabins, where one structure was split into two fairly large suite-style rooms. Each cabin had a shared deck in front with rocking chairs. Our guide handed out keys to the group, and I quickly realized that Paul and I would have rooms 3 and 4, respectively. Anna pointed out its location and Paul bellowed "looks like they want us men out the way Alexander!"

My plan was to shower and nap before dinner as I felt filthy and exhausted. After a thorough cleaning, I closed all of the blinds and hopped into bed, fiddling around with my iPad before drifting off for an hour.

Once awake, I dressed for dinner and headed out a touch early, hoping to have a glass of wine before everyone arrived for the meal. When I stepped out, I looked to my right and saw Paul sitting in one of the rocking chairs on our shared deck. He was reading a book and wearing nothing but a pair of blue running shorts. "Oh hi Alexander," he said. "I got a little warm in there and decided to come out here and relax for a bit. Did you have a nice rest?"

"Yes," I replied with a slight crack in my voice. "Very nice, thank you."

Seeing Paul shirtless was something of a shock and I couldn't understand why. His bony chest was covered in wispy white hairs, and while he was very slim he still had what I considered the "old man belly." A wrinkly paunch below his ribs that appeared more as a gathering of excess skin than any kind of fat or extra weight.

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My mouth dry, I swallowed hard and said "I'm going to see about a glass of wine before dinner. Would you like join me?"

"Sure," he said. "Let me just quickly get dressed and I'll come along."

As it turned out, we weren't the only ones with that idea. We headed down towards the hotel's restaurant only to find the rest of our group sharing wine outside in a small seating area. They invited us to join and we sipped our wine until Anna came to retrieve us for dinner.

The food was as delicious as advertised but I was even more enthralled with the wine. We were served several varieties of the hotel's own brand, produced right on site from the grape vines we saw as we entered the property. I was so in love with the wine I even got information from the owner so I could purchase cases once I was back in the states. I don't know how many glasses I ended up drinking, but I could tell the group was amused at how much I was gushing over the quality of this wine and how much I enjoyed it.

Given the nature of our trip, dinners were typically early and we were heading back to our rooms at around 8pm. I was still floating from the wine, happier than ever that I decided to still make this trip.

As Paul and I approached our cabin, I headed to the door on my side. Drunk and horny, my plan was to hop into bed and jerk off, assuming that after cumming I would likely pass out and sleep the rest of the night away. Paul had other ideas.

"Alexander," he said. "It's still early. The owner gave me a bottle of wine to take back to the room. Would you like to crack it with me?"

Without hesitation I exclaimed "Yes! I'd love to!"

He opened the door to his room and ushered me inside. Shuffling over to his luggage, he pulled out a multi-tool that included a corkscrew and began to work on the wine bottle. "I think there are some plastic cups in the cabinets by the desk," he said. "Why don't you get us a couple while I uncork the bottle."

I did as he asked and retrieved the cups, hearing the pop of the cork as I turned back towards Paul. "This really should breathe for a bit," he said. "Why don't you put the cups on the desk and have a seat while we wait." He motioned for me to sit on the bench at the foot of the bed. Agreeing with him about the wine having to breathe, I placed the cups down and plopped onto the bench.

My head was still buzzing from the wine and I wondered if it was a good idea to drink more. After sitting on the bench, I drooped my head and my eyes closed for a moment. I knew I was drunk but I was feeling so warm and happy that I didn't want to lose control. Snapping myself out of it, I whipped my head back up and opened my eyes, determined to power through. I didn't want Paul to think I was some kind of lightweight, as he had matched me glass for glass and seemed totally together.

To my surprise, after opening my eyes I was met with the sight of Paul's belt buckle. Startled, I peered up to find him looking down directly at me with a mischievous grin I hadn't seen from him before.

"Feeling okay?" he asked.

"Yes, I'm fine," I replied. "Just feeling a bit buzzed but I'm good."

"Good," he said. "So now I can ask you why you were staring at my chest when we spoke before dinner. Did you not think I noticed?"

I didn't know what to say. Had I been that obvious? "Well, I, uh..." I stammered.

"Save it," he said. "I know all about boys like you. When was the last time you got your little dick wet? Was it with your ex? I bet you were going to play with yourself when you got into your room tonight. Am I right?"

I was stunned. This previously polite 78 year-old man was standing above me and it felt like he knew every thought and instinct I had. I tried to regain my composure and started to speak when he shut me down again.

"Stop right now," he hissed. "I don't need to hear anything from you. What were you going to think about tonight when you pleasured your puny pud? Were you going to imagine yourself as a big, tough man with a thick cock plowing some pretty young thing? I bet not. I bet you were planning to think about your ex, begging and pleading with her to take you back. Offering to please her in any way she wants. I'm right, aren't I?"

He was right. Ever since the break-up all I could think about was how pathetic I was and how I wanted Janet back. The only thing that turned me on since that moment was imagining myself submitting to Janet in every degrading way imaginable.

"Today is your lucky day son," he said. "I'm going to give you what you need."

With that, he grabbed the hair on back of my head with his right hand and used his left to drop the front zipper on his trousers. "Ever suck a dick before?" he asked. Before I could shake my head no or respond he said, "You will tonight," as he fished his cock out of his pants and let it hang there.

It wasn't long at all. A pale, slender tube that hung down about 2" soft from his fly hole. I could see a few white hairs poking through as well and was surprised to see that he was circumcised. He was still gripping the back of my head and I could feel tears welling in my eyes as he brought me closer to him.

"Get acquainted with it Alexander," he growled. "Smell it, see it. Open your eyes and get your face in there." He pulled my face into his crotch and rubbed his flaccid penis all over me. Now gripping my head with both hands he pulled me back and looked directly down at me. I stared back up at him with more fear than I had ever felt before when he said "Open your fucking mouth."

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I complied. It almost felt like an out-of-body experience. I felt compelled to follow his every word. He lifted his soft cock with one hand and lurched forward, placing it directly on my tongue. "Close your lips around it and get sucking boy," he said. "And do it well."

My previous girlfriends would never suck me, so I had no real frame of reference for what I should do other than what I'd seen in porn and what I thought would feel good on me. I began sucking softly and slowly, imagining that I shouldn't go too fast or hard. I concentrated on keeping my teeth out of the way and making sure that Paul was going to be satisfied with my efforts. I could feel his cock growing in my mouth as I continued sucking, and decided to try to use my tongue a bit, swirling around the head of his dick as I bobbed up and down on it.

I could hear Paul moaning as he gripped the back of my head and started taking a more active approach, thrusting forward periodically as his once 2" flaccid dangler was now a 5" diamond cutter poking the back of my throat. His cock was harder than mine had ever been, sticking straight out from his unzipped fly. I just tried to keep breathing and sucking as he furiously fucked my mouth.

Eventually he pulled out and gave me a chance to catch my breath, but I soon realized that wouldn't last. He removed his shirt and trousers until he was standing completely naked before me. "Like what you see?" he said with that toothy grin. He gave my face a little slap with his still rock hard cock and said "Get up on the bed and lay flat on your back."

Still clothed I asked if I should get undressed. "I'll tell you what I want and when I want it," Paul replied.

Face up on the bed, Paul climbed up and straddled my chest, his cock pointing directly at my face. As he shuffled forward, he lifted his cock and leaned slightly backwards, exposing his small, wrinkled and hairy balls to my face. "Lick them," he said.

I extended my tongue and started to lather up his furry orbs as he grabbed my hand brought it to his cock. I stroked his cock as I licked his balls, eliciting moans from Paul as I realized my own cock was straining against my pants. "Suck them," he ordered. I took each ball in my mouth and rolled them with my tongue as I continued stroking his erection.

Suddenly Paul pulled back and started to move. He swung his right leg over my body and straddled me in reverse. I thought that maybe he was positioning himself into a 69 position and that he would be going for my cock as well. I was wrong.

Paul scooted backwards until I was staring directly at his bony behind. His ass was smooth and white and well defined with a pronounced crack. "Do you know what you're going to do next?" he asked.

Unaware of his plans, I said, "No sir, I don't. Are we going to 69?"

Paul cackled loudly at my suggestion and replied "Absolutely not, m'boy. What you're going to do is stick your tongue in my asshole. You're going to lick it, suck it and eat my ass until I'm satisfied with your performance. Let's get you acquainted with it, because you're going to be in there quite a while."

This was beyond anything I had ever dreamed about, but I had no choice as he spread his cheeks and lowered himself onto my face. My lips and nose were right in his crack as he settled himself onto me.

"Now stick your tongue out and get licking. You can start slow and lick around the rim of my hole, but eventually you're going to be in there and working it. You can stroke me off while you go."

I lost all sense of who I am and what I was doing. The only thought racing through my head was to suck Paul's asshole and make sure he was happy with it. I licked and sucked like I was being given the tastiest treat of my life, darting my tongue in and out of his asshole as I stroked his cock.

It felt like Paul sat on my face for hours, though I imagine it wasn't longer than 20 minutes or so. He finally leaned forward and pulled his ass off my face and let me breathe.

"Time for dessert son," he said as he whipped back around and pointed his cock at me again. "Open wide and stick out that tongue."

As soon as my tongue was out the first glob of cum landed on it. Three more spurts shot directly into my mouth, hitting the back of my throat and landing on my tongue. I tried to speak but my mouth was wide open and he quickly said "Don't say a word. Keep my cum in there for a moment. I like to see my work before you swallow it down."

I laid there, mouth open and full of his spunk, for about 30 seconds when he sighed and said, "Okay, eat it." With one gulp I swallowed Paul's funky seed and felt relieved that this was finally over. And then Paul spoke again: "Okay, take all of your clothes off."

I stood from the bed and removed my shirt and pants. My little cock was sticking straight out from my briefs, which were soaked from the massive amounts of precum I had leaked during the ordeal. "Panties off too," Paul said. "And come with me."

He grabbed me by the ear and dragged me into the bathroom, motioning me towards the shower. I thought perhaps he'd want me to clean up a bit or perhaps shower together, but I had the wrong idea.

He pushed me into the stall shower and said, "Sit down." I was confused and must have given him a strange look, because he frowned and said sternly, "Park your ass on the floor of the shower. Sit the fuck down."

Once again I complied and found myself sitting on the cold shower floor staring up at Paul above me.

He leaned forward, cock in hand and aimed. The first splash of piss hit me square in the face. After a few warm bursts to the face, Paul unleashed a volley of urine all over me, covering my face, hair, and chest. He even pointed down and pissed all over my cock, which was now harder than I had ever felt before.

As the last few drops trickled from his piss slit, he looked down at me and said "Okay, shoot your little load now."

I reached down to grip my cock and shot instantly, covering my hand with my cum as I howled in pleasure from finally relieving the pent-up pressure.

He said, "Eat your spunk," which I did without hesitation. "Then turn the shower on, clean yourself up and see yourself out. I'll see you tomorrow."

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