A Vacation to Remember

Every winter my wife and I enjoy vacationing at all-inclusive resorts in warm climates. We generally take one or two trips a year and each stay is usually for ten days.

We are both retired. I am in my mid-sixties and my wife is eleven years younger. She has a very outgoing personality while I'm more reserved and laid back.

During our vacations, it usually only takes a day or two before my wife makes friends with other women staying at the same resort. Once she breaks the ice, I generally open up with the women's husbands. It seems to be pretty much that same routine every time.

Everything was pretty status quo on our most recent vacation to a Caribbean resort. By the second day of our stay, my wife had become friendly with three women who were vacationing together. Their group had arrived a few days before us and were staying for fourteen days.

After my wife started talking with the three women, it didn't take long before I was coming out of my shell and began to communicate with the husbands. John, Bill, and Frank were all in their mid to late sixties. We had much in common to talk about and had fun playing water volleyball together.

Once we had all gotten to know one another, my wife and I hung out with the three couples at the pool during the day. On the fourth night we also had dinner together.

I really enjoyed being with the guys as we shared many of the same interests and seemed to have the same kind of perverted sense of humor. The vacation was turning into one of the best ever.

It was our sixth day at the resort when my wife was invited to join her new friends for a shopping trip into the nearby town. I've never been thrilled to go on the shopping excursions my wife enjoyed and was more than happy to not have to participate during this vacation.

My wife was feeling bad about leaving me behind at the resort but I assured her I would be fine just hanging out with the guys for the afternoon.

After our group had lunch together the ladies went back to the rooms to get ready for shopping and the four of us men went to the pool swim up bar. With no wives nearby we were all enjoying the sights of the many boobs and butts around us. The comments we were making amongst ourselves were more crass and sexual than they had been at any other time.

The booze was flowing and the four of us were having a great time when the women returned to let us know they were leaving on their shopping trip. It was apparent by their comments that the fun we were having was obvious.

"My god, you guys looked trashed already."

"Yep, I suspect they'll all be passed out by the time we get back."

We let them make their comments and told them to have a good time as we ordered another round of drinks.

For the next thirty minutes after the wives had left the four of us guys continued drinking and checking out the hot fleshy delights around the pool. As I returned from a trip to the restroom my three friends were in the midst of a conversation amongst themselves. Bill gave me a look as if he had something on his mind.

"Hey, I'm not sure exactly what you're into but the three of us always look forward to our wives going on these shopping trips. It gives us time to enjoy our own fun."

"That's cool. So what do you guys like to do?"

"Well let me put it this way, it's something all guys like to do although most do it alone. We found out it's also fun to do with friends."

I wasn't exactly sure I knew what he meant although I thought I did. I was hesitant to say anything because it would be embarrassing if I was wrong but Bill seemed to sense my confusion.

"Ummm, in simple terms it's referred to as a circle jerk. If you're interested that's great and if not that's alright too. Don't feel pressured."

I was immediately intrigued. Although I had always been straight, in recent years I had occasionally jerked off while watching videos of other older guys masturbating. At times I had even fantasized about jerking with other men but never pursued it.

It may have been due to the lack of inhibition caused by the alcohol but I didn't take much time to think about it.

"Well I've never done it but yea, I'm interested."

Each of the three guys made reassuring comments and all seemed happy to have me join in their "what the guys do while the women shop" club.

John suggested we do a shot of tequila then get a few drinks to take up to his room.

As we rode the elevator up to the fifth floor, our conversation was pretty much the usual and nothing was mentioned of the activity we were about to enjoy. It was all I could think about however and I could feel my penis pressing tight against my swim trunks.

When we got in the room, John hung the "Do Not Disturb" sign on the door handle. Almost immediately each of the men removed their t-shirt's and I did the same. I watched as each of my three friends without hesitation took down their swim trunks.

Bill and Frank both had a similar physique as myself. We were all in the five foot ten or eleven height range, weighing two hundred twenty to two hundred thirty pounds, and all having a sizeable belly. John was about the same height but heavier. He weighed in at around two hundred fifty with the bulk of his additional poundage also in his stomach.

The moment that I got my first glimpse of the three men naked, it was only natural that I also checked out their manhood..

Bill was uncut and thick. His limp penis hung down about five inches in front of a huge scrotum and had noticeably big balls hanging in his sack. John and Frank were similar in size to Bill but both were circumcised.

What I knew for certain by looking at them was they each had much bigger more manly looking cocks and ball sacks than I did. I was taking my time as I felt slightly embarrassed to display my little one with a small scrotum.

"Come on Dan. Take your trunks down and join the party."

As I pulled my swim trunks down my erect five inch boner popped out.

"I guess I'm a little anxious to join your club."

"Hey that's not a problem. Any guy who likes to play with his cock and watch us play with ours is a welcome member."

As I stood there with an erect penis sipping my beer I continued to discreetly check out the cocks of the other three men. I was infatuated by their size and aroused by the thought of watching them masturbate.

"I've never jerked with other guys so I'm not sure of the procedure or what you guys do?"

John got a deck of cards as Bill and Frank moved a table from along the wall to the middle of the room.

"To get everyone aroused we play a little card game we call draw and stroke. We take turns drawing from the deck and stroke our cock the number showing on the card. Ten strokes for all face cards and twenty for aces. Jokers are wild. If you draw one you immediately draw a second card and everyone has to stroke double the number shown. An ace would be forty."

"Okay, that sounds easy enough. I assume you lose the game if you cum?"

"It would be disappointing if you cum as the intent of the game is more of a warm-up for the circle jerk. When we get through the deck we determine everyone's level of arousal and decide whether we need to go through the deck a second time. Two times is usually enough foreplay and by then we're generally ready to fully enjoy ourselves."

"Alright. Anything else I need to know?"

"Nope, not really. We're just all here to watch each other get off. To start we each draw cards in turn until a jack comes up. That player strokes ten times and the game is on with the guy on his left drawing the next card."

John placed the cards on the table. We each took a few more sips of beer as we gathered around.

"Alright Dan, since you're the new member we'll let you draw the first card."

I drew a seven. Bill followed me with a five, Frank a nine, and John a two. We made it one and a half more times around the table. When Frank drew the first jack Bill got things rolling.

"Alright Frankie, show us how you stroke that cock. Give it ten good ones."

Frank wrapped his fingers around his thick penis. As he began to stroke himself he also began to count.

As I watched Frank's hand moving on his cock and looked at the expression on his face a feeling of excitement came over me. The feelings of nervousness I had a moment before were suddenly gone. I was watching another man masturbate and was truly enjoying it.

John was next and drew a queen.

"Oh yea, that's the kind of card i like to start off with."

After watching John stroke his cock while counting to ten it was my turn. I was relieved when I drew a four. With my cock already fully aroused I knew that having less stimulation was for the better at the moment.

Bill drew an ace to end the first round. I found it to be incredibly arousing watching him give twenty slow strokes to his fat uncut cock. By the final five I was getting a glimpse of his penis head peeking out from under his foreskin.

After three more rounds went by I drew the first joker. My follow up card was an eight and all of us got the pleasure of sixteen strokes.

By then, the cocks of the other three had perked up and were about semi-erect. Seeing that their cocks were getting hard was making me more aroused.

We only got through one more round before Bill drew the second joker with an ace to follow. We weren't even halfway through the forty strokes when I started thinking I wasn't going to make it through all of them. At thirty I thought for certain I was going to shoot my load but somehow managed to control myself.

When we finished the forty strokes, pre-cum was visible in the slit of my aroused penis. The other three men were now fully erect and I was getting my first look at them with boners.

Bill had about seven and a half inches of thick meat. The fully exposed head of his uncut penis was pink and shiny.

Frank was also thick and looked to be about eight inches. His erect cock had a noticeable curve to it.

John was around seven inches and appeared to have the thickest cock of the three. He also had one of the biggest mushroom shaped cock heads that I had ever seen.

As I looked at each of them I was a little envious of their manly size. I felt certain that no woman had ever been disappointed by any of their tools.

It was incredibly arousing for me watching the three of them stroke their hard cocks as our game continued. I never imagined I could get so turned on by engaging in sexual activity with men. I hadn't ever done anything like it before but I was quickly becoming a fan.

After Bill drew the last card in the deck and finished stroking John picked up the cards. He shuffled them and put the deck back on the table.

"How about this time we do a round of give your neighbor a hand?"

With Bill and Frank both in agreement I questioned John on how the game was played.

"The rules are essentially the same as the other game except you stroke your neighbor's cock instead of your own. If the card you draw is red, you stroke the guy to your right. If it's black, you stroke your neighbor on the left. The joker still doubles but only for the guy who gets stroked. The group doesn't participate."

Just like in the first game we took turns until the first jack was drawn. Once again Frank turned over the first one. It was the jack of hearts.

Bill was standing to the right of Frank with his thick penis standing erect. He put his hands on his hips and turned towards Frank.

"Oh yea, give me a hand buddy."

I could see the pleasure on Bill's face as Frank gave him a slow hand job while counting out the ten strokes.

John drew next. I was hoping he wouldn't draw black as I was afraid I would immediately shoot my load if he stroked my excited cock. He drew a red seven meaning Frank would be the recipient of the pleasure.

It was my turn next and I turned up the ten of clubs. Bill was smiling as he put his hands on his hips and presented his thick erect cock to me.

"It looks like I'm the lucky one to get your first hand job."

As I took Bill's penis in my hand I immediately noticed how much bigger it felt than my own. Again I was feeling envious as I slowly jerked his cock ten times.

We went three times around the table and I still hadn't been stroked. It was a little disappointing but was probably for the best as it gave me some time to get myself settled down and composed.

During those three rounds I stroked John each time. The third time was after I drew a joker and a queen. He was moaning with pleasure by the time I finished jerking his cock twenty times.

It was incredibly arousing watching each of the three men getting and giving pleasure but hearing John's moans really got me turned on again.

At that moment as Bill drew a red seven he looked at me with a big grin on his face.

"Well my friend, it's about time you got into the game."

When I turned towards him he took a hold on my boner and began to slowly stroke it. For the first time in my life my penis was in the hands of another man.

It felt incredible and thinking about it being a man who was giving me the hand job made it even more arousing. I instantly moaned from the intense pleasure and I don't know how I kept from shooting my load on his hand. A few more strokes and I'm sure I would have.

Over the next three rounds I was the recipient of the stroking three more times by Bill and twice by John. I was lucky that a face card was only drawn once and none of the cards were higher than a six.

My cock was as hard as it could be but I wasn't alone. It was obvious the other three were just as aroused as I was. I really enjoyed looking at each of them standing there with a boner.

The last few rounds were intense. In addition to each of us moaning and groaning while our cocks were being stroked by our "neighbor" there was also plenty of erotic talk going on.

It was difficult to not stroke myself as I watched other men standing within feet of myself thrusting their hips and getting a hand job. Seeing the expression on their faces and hearing words like "oh fuck yea, stroke my big cock" made it even more tempting.

On the final card Bill drew a red nine which meant I would be the last hand job recipient in the round. I turned towards Bill with my hands on my hips and he gripped my excited penis one more time.

"Your cock looks like it wants a little more pleasure Dan."

I didn't know what was coming next but after making it this far without ejaculating I was determined to not cum. Bill gave me five long slow strokes then four quick ones.

It took every bit of my mental capacity to concentrate on anything but the pleasurable feelings in my penis. Somehow I managed to maintain control and was happy to move on to more fun.

John picked up the cards and placed them off to the side.

"Now that we're all sufficiently aroused let's get on with what we all like to do."

Each of the three men were already stroking or rubbing their cocks as I gave John a questioning look. He sensed my confusion and smiled.

"Just do whatever you like to do when you're enjoying yourself in the privacy of your home. Part of the excitement is seeing how we each like to pleasure ourselves. Don't be shy or embarrassed. Do whatever gets you off."

"Alright bit it's probably not going to take much."

It seemed a little strange but since I had never jerked off with other guys I was open to doing most anything. As I watched the other three, I placed the flat of my hand against the underside of my erect penis and started rubbing it with my palm.

Almost instantly I noticed Frank watching me.

"Oh yea that's it Dan. Palm your excited pee-pee. I really like that method too and call it the rosy palmer."

Frank placed his palm against his thick eight inch cock and began massaging it. It was exciting to see him playing with his big cock in the same manner as I was.

"I do like that term rosy palmer Frank. I refer to it as my paddy palm rub. It was the technique I used laying in bed when I first started masturbating. It's still one of my favorites and it's also a good easy one to use when you're wearing clothing."

"Yea, you got that right. I can discreetly do the rosy palmer nearly any place at any time. But if you're like me you've probably made a mess in your pants a few times too."

Despite being extremely aroused I couldn't help but chuckle at his comment.

"Yep, I've cum in my pants more times than I can count but I'm not complaining. It's part of the fun and I kind of enjoy it."

As Frank and I were palming our excited cocks the other two guys were enjoying themselves in their preferred manner.

John had his hand wrapped around his thick cock and was rocking his hips as he stroked himself. His big mushroom head became visible under his fat belly each time he thrust his hips forward.

Bill had been stroking also but after a short time he stopped. With his hand still gripping his cock he began to slap the head of his penis against his belly.

"Oh yea, I do love to beat my meat. I challenge each of you to do it and keep up with me."

Each of us took the challenge and suddenly there were four old men watching each other beat their meat. The entire scenario seemed surreal to me but also incredibly erotic.

I saw the same expressions of pleasure on each of their faces as I was feeling. Within seconds I felt my cock stiffen and throb. I looked down at the pre-cum on my belly and watched the shiny head of my penis slapping against it. I knew I wasn't going to last much longer.

At that moment I heard Frank moan loudly. I looked towards him and saw a thick glob of white semen appear on the tip of his cock.

"Oh fuck yea!"

As Frank stood there slapping his thick hard penis a stream of cum shot several inches up on his belly. Three more streams followed in rapid succession before cum began to ooze from his cock and run down over his hand.

I was already near my point of no return and seeing Frank ejaculate put me over the edge. My cock tingled with intense pleasure and as I shot a stream of cum on my belly I couldn't keep from expressing my enjoyment.

"Oh my god I can't take it any longer. I love beating my meat!"

For the next few seconds I was moaning and whimpering as semen squirted from my excited cock. When I finished, my belly and hand were both covered with a large amount of cum. I felt spent as it seemed like I had ejaculated harder and more than I ever had.

As I stood there catching my breath and trying to regain some composure, I started feeling that weird sense of guilt I sometimes have after masturbating. It quickly disappeared when I looked towards Bill and John who were still enjoying themselves.

The two men were making moaning sounds as they looked at each others cock while slapping their own against their bellies. Both suddenly groaned loudly and streams of cum erupted from their excited meat as they simultaneously began to ejaculate.

I couldn't resist from rubbing my little limp one again as I watched the intense pleasure unfold. When Bill and John finished, there was cum on their bellies, their hands, and the floor. Both had shot massive loads.

The entire room reeked with the sweet aroma of cum. I couldn't help but think of It as being the smell of pleasure and hoped that someday I would have the opportunity to again masturbate with a group of men.

A short time later, the four of us were back at the pool bar enjoying drinks and the sights. Neither Bill, Frank, or John said a word about our circle jerk. It appeared that it was just another day of fun to them. For me it was something I would not forget.

When the women returned a few hours later, they found us right where they had left us. We were all a little drunker but none of the ladies had any idea of the masturbation fun their husbands had while they were shopping.

On our last night at the resort, my wife and I joined the three couples for dinner. Afterwards the entire group went to the lounge for drinks.