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I am stunned still to this day form all of the positive feedback from my stories. I am humbled and honored.
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This material is for those 18 and older and as usual if you find the subject material offensive, that's a "you" problem.
And like my other two installments. All true and this is my all time favorite encounter.
"Oh how I miss Craigslist Part 3". The Santa Bear
I think I had to have been 39 or 40 at the time. So I must of have been using Craigslist for 5 years give or take. Now the Mrs. and I were on the road a lot, worked late into the evenings and left me many opportunities for me to fulfill my "grandpa" fantasies. This particular encounter took place in Buffalo, NY. I had to conduct an audit and I knew this would take three days and nights. I opened up my personal laptop in my hotel room and was itching to get out. So I scanned the "casual encounters" section and didn't see a lot of posters over 55. That's quite common because older men tend to be lurkers rather than posters due to their natural wariness of scammers. Now since I'm doing an audit I wasn't allowed to drink and carouse however I needed some company and a some fun.
The audit went bad from the start. The operating systems was slower than molasses, the apps were failing me and I knew I'd be here way longer than intended, which meant more mind numbing paperwork. So after ten hours of futility, I signed out, gather my belongings and headed back to my room. I cracked opened my laptop and posted this...
CL: "Hi Grandpa! This is your favorite grandson. Remember the day you and I played 'doctor' together? Even though I'm in my late 30's, I still act like a naughty nine year old. I hope you're a large man because I love to kiss, cuddle, suck, and maybe you'll breastfeed me. No pics wanted or needed. Just provide me your honest stats and tell me what you desire. I'm 6'2" 200lbs with jet black hair."
Had to discard the first batch of responses. But about a half hour later I got this response.
CL: "Hello grandson! I'm a Santa Bear. Meaning I'm jolly 70 y.o. and round in all the right places ;)), . I'm 6'5" 305 lbs but still agile and can fulfill your fantasies. I have flowing silver hair, big kitties and nipples for you to suckle on. Although I'm a bottom it's ok to keep it oral. From the zip code you have listed, I'm only ten minutes from the main drag."
Now I've seen and played with all types and sizes. "Ageplay" is my dirty talk. I can't stand in when in the throes of passion my partner says, "suck it bitch!". Total turnoff. However with the right amount of encouragement, I tend to bring my "A" game. So I replied...
CL: "Oh my god! A true Santa Bear! This is a dream come true! I've tried really, really, really hard to be a good boy. But I'll need to sit on your lap to ensure you that I'm on the naughty and nice list. If you give me a half hour to clean up and change into something more accessible, I will be at the address provided."
Now I'm sure you're wondering how I can tell the real "grandpas" from the fakes. They respond in full sentences for one. Second, the language used always gives a good indication. Third, let's say I haven't always been 100% correct and left myself room to walk away if it doesn't feel right. So hopped in the shower and made myself squeaky clean and after I toweled and dried myself off he left me the address for where to meet. I quickly replied and gave him my ETA from the maps app.
The drive was simple enough. I pulled into his driveway and marveled at this home. You see in Buffalo, NY when it expanded in the early 1900's, the richest of the rich at the time had these impressive three story, 5 to 6 bedroom mansion like houses. And when a home is designated as a NY landmark by law the exterior and parts of the interior components must stay aged preserved. So renovations cost a ton of money. I found the Lion's Head doorknocker and rapped on the door. And then I saw him.
Look I like to think I'm an above average height kinda of guy. I usually don't have to look up to people in general. He was spot on about the height and carried his weight well. He did not look morbidly obese. He was wearing a red-flanneled shirt held up by Christmas suspenders attached to his black sweatpants. His face did remind my of Kris Kringle but had no facial hair. His hair was thick, silver-grey, shoulder length but did not appear feminine. As I entered, I was so awestruck, I was dumbfounded and speechless.
"Didn't see this coming eh Grandson?" Santa Bear opened.
I laughed out loud and being a wiseass, I replied, "So where's Mrs. Clause?"
"Oh she's in the kitchen. Why don't we have a cup of coffee and chat first. She knows I play both ways, so it's all cool."
He led me through the foyer, past the main living room and swung the kitchen door open and there she was. She greeted me, had me sit down and was stuffing me with baked cookies while Santa Bear poured me a cup.
"So, I take it that you're Mrs. Clause?" I said
"Only around my hubby," she said and continued, "And if he didn't like your post you wouldn't be here. He's been bi for over 30 years. We have four kids and eleven grandchildren. So I have no issues with you having fun with him. Would you like to stay the night? We always have a bed at the ready."
"Well I'm here on assignment for three days. But the computer system was failing me miserable that I might be here longer. I must decline tonight because I have to be in the office so early in the morning. But if I can I will. By the way what an exquisite home."
"Well if you change your mind and behave, we'll welcome you like family." she said and left Santa Bear and me alone. The cup of coffee was delicious along with the freshly baked chocolate chip cookies. Once I finished he asks me, "What do you do for a living?"
"I'm a Federal Civil Servant conducting routine audits. I travel a lot in NY state and up and down the east coast. May I ask about you sir?"
"Well I worked for Kodak and retired about 5 years ago. I was a photochromotologist. I was on the engineering team that made slide technology affordable. And for the last ten years the Mrs. and I have been restoring this place to ensure the family have a fun place to be and the location is convenient." he replied. "We will be playing in the downstairs bedroom. Do you have any questions or concerns?"
I answered, "I have one simple rule. I don't ask you to do anything you're uncomfortable with and I expect the same courtesy. And since you're the host, I'll make sure your needs and taken care of before mine. Normally I don't fuck men, partially due to that I'm allergic to latex and it's usually not my style. I test myself annually for STD's and I can only screw bareback. If that's an issue no big deal. But since you and your wife are such nice people I want to please you in every was possible."
Santa Bear chuckles. "We'll cross that bridge when we get there. And I love your whimsical nature my naughty boy. Let's adjourn to the bedroom."
So back through the kitchen door, pass the living room and on the right was the only first floor bedroom. As he opened the door I was awestruck. The four poster bed had to been at least 100 years old. Inside was antique toys from the 1930's through the 1970's. The room was Christmas themed from the sheets to an old fake tree with real silver tinsel and lights. By the window was a Santa chair like the ones used in a mall. He sits on the chair and motions me over. I sit on his lap sideways so he had easy access with his right hand.
"So tell me grandson. have you've been naughty or nice?" Santa Bear asks.
"Well Santa, I have a bad habit of not being monogamous. There are so many Grandpas that know how to take care of my urges." I quipped, winked, and finished. "But I'm nice because when Grandpa gets turned on my Candy Cane sticks up nice and straight."
"Oh ho ho!" in full Santa mode. "If I can open my presents, you can open mine." I laughed so hard tears were coming down my eyes.
So I unbuttoned my dress shirt, unbuckled my belt, opened my pants buttons, unzipped my fly and said, "You can open your present now Santa." He slides my slacks down to my ankles and I was wearing flannel boxers. He finds the front door opening and fishes out my 7" cut cock. He had me so turned on I swear it was never that engorged. He then tucks my cock back in.
"We won't be needing these things for a while." Santa said.
So I'm totally naked sitting on Santa's lap. He toyed with my nipples and for a large man he was rather gentle and nice. I was getting goosebumps to the shear anticipation of what may come. His right finger was toying with the head of my cock and I was leaking like a faucet. After about five minutes of "exploring" me, he asks me to stand up so he can strip. He still had decent muscle tone. His aerolas were the size of silver dollars, the nipples were thick and puffy. He had a large gut but it had a soft look and feel to it. He tried to breastfeed me from the chair but that wasn't possible. so we moved over to the bed. He asked me to take off his sweat pants due to his arthritic knee. As I got up and brushed my hand on his crotch my other hand undid his knot. As I slid his sweats down I noticed he had a 5" banana curved cock. I let him get on the bed and be comfortable and then he turned to his side. Once I got in the bed I started suckling on his nipple. During this time he let out a soft moan and was pawing my hair and neck.
"This feels wonderful. Can you give Santa a kiss?"
"Anything to please my Santa Bear."
So I scootched forward and we kissed and frenched for quite awhile. We'd take turns who gave and recieved. I reached down and played with his cock by gliding my hand just over the head. He squirmed with joy. He then asks my to stand up so he can blow me. I obliged and he swallowed my cock whole. Now I love sticking my cock in a pussy, but his mouth was so warm and inviting that my knees buckled. He could sense that I couldn't last much longer so he stopped. He then removed two pillows and placed them at the foot of the bed.
"You don't mind if I rim and play with your ass?"
"No problem Santa. Just don't finger or fuck me."
"Of course. Anything for my grandson."
So once I was settled in position, he massaged my tiny little butt. and the next thing I knew he licked my taint and I went dizzy. I forgot that the nerve endings there provided a sexual current and started thrashing uncontrollably. His strength keep me in place. I asked for another pillow so I could scream joys of ecstasy so the neighbors weren't disturbed. It may of only lasted 15 minutes but it felt like 5 hours. when it finally concluded he said, "Tonight I want to take care of you. If you can show up the other nights you can take care of me."
"Whatever Santa Bear wants, Santa Bear gets." I moaned.
We 69'ed for a while, and I suckled for a while longer. Neither of us wanted to cum and ruin the moment. We must of made love for three hours without coming up for air. I finally said it was time for me to explode so he pulls out this bottle of lavender lotion. We moved back to the chair. I sat on his lap and straddled his thick curved cock. He applies the lotion and starts stroking me. I didn't last more than three minutes and spurted 6 huge lobs of semen and every raw nerve told me that I've never experienced this with anyone. So when I got back to reality from cloud nine, I took some lotion and applied it to my thighs. He started pumping his cock through my legs. Ten minutes later he cuts a couple of drops. He was breathing hard but heard the "whew" and I knew he was happier than a clam.
I looked at the clock and it was past 10pm. we played around for over three hours, while it only felt like minutes. When we both came down from the sexual hi, we got dressed and headed back to the kitchen. He got me a glass of water and poured himself a cup of coffee. After 5 minutes of silence he spoke. "How do you feel grandson?"
"Spoiled rotten. I can't thank you enough. However I have a long day tomorrow and I should be getting back to my hotel. Tell Mrs. Clause thanks for the hospitality. If I'm free tomorrow, I'll send you a message."
"Of course grandson. We understand."
The following day was just as frustrating. I worked 13 hours and was about two-thirds through the audit. When I got back to the hotel, I messaged Santa Bear that I was too exhausted to play but I should have the audit done tomorrow. He replied that I should stop over for dinner and sleep in a more comfortable bed. It was an offer I couldn't refuse. The three of us had a quiet chicken dinner followed by more coffee and fresh baked cookies. The conversation was just small talk and I was dead tired by 9pm. Mrs. Clause took me to the upstairs guest bedroom. I just barely managed to set the alarm on my phone before I passed out.
The following morning I woke up, went downstairs and Mrs. Clause was already cooking in the kitchen. Mr. Clause was snoring in the downstairs bedroom. She fixed me a thermos of coffee and packed me some breakfast sandwiches. I told her not to go out of the way for me and I thanked them for their generosity. She replied, "My husband has worked so hard to provide these bounties. He couldn't stop talking about you. You have no idea how happy he is." I kissed her on the cheek and departed before I cried my eyes out. Went back to the hotel and grabbed my kit to finish the audit.
At 3pm I made the impossible, possible by completing the audit. I got back to my room and napped for a couple of hours. I messaged Santa Bear that I finished and whatever time works for him is good for me. I got the message to arrive at 7pm. That gave me time to visit this cool vintage shop nearby and I found this cool antique Christmas tree topper. I knew I overspent on it, but it did not matter to me. The purpose was beyond price. I had it gift wrapped and grabbed a quick bite to eat. Once I arrived Santa Bear let me in and we had a long kiss in the foyer. We made our way to the kitchen for tea and coffee cake. After 30 minutes of small talk Mrs. Clause retired to the upstairs bedroom.
"So what's it going to be grandson?" Santa Bear asks.
"Tonight is for you and if you let me may I spend the night with you?"
"Yes and yes." he said and led me to the bedroom.
That I did fuck him. I can't describe our lovemaking. But the warmth and masculine strength was divine. I felt safe and loved. And I kept my promise to him.
The following morning we were in cuddle mode. We finally got up after the savory smells of a full breakfast was nearly ready. We looked at each other had a soft "good morning" kiss and headed to the kitchen. The eggs was scrambled, toast and jelly, sausage and bacon. There was water, coffee and OJ at the table. I noticed I left my wallet at the table.
"Do I have two happy and healthy boys this morning?" Mrs. Clause asked.
"Fit as a fiddle and raring to go." Santa Bear growled.
"I am humbled and honored to be treated better than gold.", I started. "You have made your grandson very happy, content and most fortunate. If you will please excuse me for a moment." I got out of the chair and headed outside to my car before they protested. I grabbed the gift box and re-entered. I placed to box in front of them. Mr's Clause opened the box and had tears of joy. Santa Bear wrapped me in a big ole bear hug. After we finished breakfast, Mrs. Clause shooed us out in order to clean up. Santa Bear and I sat in the living room in silence. We both knew what transpired was never to be recreated again and was basking and reflecting about those past few nights. When Mrs. Clause reappeared I stood up. She kissed my one cheek and pinched the other.
"So back home grandson?" Mrs. Clause asked.
"Alas, yes. I have to get back home and be with the Mrs.. I have a lot to do before Monday morning." I said.
"She doesn't know?" she asked.
"No. You see we're both civil servants. Due to a cruel twist of fate we cannot have children. the sex faded away. I love her like no other. She doesn't know I'm bi."
"Will we see you again?" Santa Bear asked.
"I wish I could say yes, but I cannot ever lie to you. I'm all over the east coast and cannot guarantee when I'll be back this way. Also if we keep a correspondence, I'll bet distracted from work for fear I'll slip up." I bowed my head low.
"Honey, sweetie." said Mrs. Clause "We understand. And we love and respect you for your candor. Tell you the truth if it was 10 years ago I'd join in the fun with you guys. We only have one life to live and you have brought joy and happiness to our hearth and home. We thank you."
After some emotional hugs, kisses, and goodbyes I could barely drive back to the hotel. When I arrived all my bags we packed and put on a cart. The manager of the hotel called me by name. As I came over he whispered in my ear, "I'm Santa Bear's oldest son. Mrs. clause saw the hotel key and he'd me prep your luggage for the journey home."
I was stunned. I loaded the car for the four hour trip home. My wife must of been out shopping because I arrived before she did. When she came in, we kissed and then sat down on the couch.
"How was the assignment?" she asked.
"Somehow managed to get it done. Some hangups, but survived." I replied.
I never kept in touch. I still feel if we got together again we couldn't recreate the magic twice.
To Santa Bear and Mrs. Clause: I love you both so very much!
The End