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"Oh how I miss Craigslist Part 4" - On the road in Baltimore
This event happened prior to meeting that wonderful Santa Bear. I just wasn't able to put into story format. But luck would have it, I was able to. So without further ado...
It's about an 8 hour road trip to make it to my hotel right in the harbor of Baltimore, MD. Once again I drew the short straw and here I am conducting yet another tedious audit. However since I earned enough points at a certain hotel chain, I've decided to add the weekend as well instead of schlepping back to the snarls of Friday night traffic.
I was on the 8th floor with a stunning view of the harbor which deflated my motivation to what I was suppose to do. It was a clear crisp Friday night in November. I finished day one of the audits and for once everything worked. After a small dinner, I went back up to my room and cracked opened my personal laptop and scanned for what's out there in Craigslist land. Didn't find my usual suspects out there so once again I posted my own ad.
CL: Hi grandpa! I'm away from home and all on my own. I'm bored watching cartoons and like for some fun times. Just be over 60 and have something to offer more than your smiling face and perky attitude. Love to kiss, cuddle, and suck. No pic needed. Just give me your true stats and what you're into.
The first few responses didn't do it for me. But as the ever patient horny guy, I struck gold again.
CL" Hey Grandson! Grandpa's here and ready to go. I'm a short plump man 5'7" 195 lbs. I love what you're into and maybe if I can convince you, I'd love you to fuck me as well. No hair on top but hair all over the rest of my body as well as you should know. My 5" uncut cock is ready and primed for your pleasure.
Ding! Ding! Ding! We have a winner.
Come to find out he was staying at the same hotel as I was. This has never happened to me before so I took it as a good omen. So we agreed to meet at the lobby bar for a few drinks and get to know each other. I told him what I was wearing and was heading down. He told me he'd be there shortly.
So I'm at the bar enjoying one of the local craft brews. I'm in a simple dress shirt and slacks. I managed to grab a small table for two. It was close enough to the bar to order drinks, but far enough away to have a private and hopefully raunchy conversation. I also had prime view to see who comes and goes. Then I saw him.
Short, bowling pin type of appearance. Bald as a cue ball, but was dressed to the nines. He scans around the bar. I stood up and smiled and he headed my way. He put his suit jacket on the chair and ordered a Jack Daniels. Once he got settled we said our "hello's" and exchanged our names.
"So grandson? What brings you here?" Grandpa asked.
"Well I'm conducting audits until Friday, but decided to stay on my own dime until Sunday." I replied.
"I'm on business as well. It sure is a lot different from where I come from." He said
"Well I'm from NY, how about you?"
"East Tennessee"
"I must say, this is the first time I didn't have to drive anywhere." I said. We both chuckled.
So after three drinks, we felt comfortable enough to come to his room. It was bigger than mine, had a full service bar, and a hot tub. I already had a feeling I was in for a treat.
He pours two Jameson on the rocks and set the drinks on the table next to the bed. He walks right up to me and I bent down so he could plant me a big ole kiss on the lips. I felt his hunger and my blood rushing. He then pulls up my dress shirt over the belt line and unbuttons it from the bottom to the top. I disrobe the shirt and he pulls up my T-shirt and attacks my nips. Meanwhile, I'm unbuckling my belt and half of me was moaning, and the other half felt a twinge of pain. He then licks it, swirls his tongue around it and if you saw my eyes the old "Tilt" sign was in full force.
He finally stops suckling me and asks my to strip in front of him. I slid down my pants and slowly slid down my Scooby-Doo boxers. He got his first look at my 7" cut cock. I didn't shave at the time so I was sporting a full bush to his full delight. He starts rubbing my thighs and slowly works his way to my cock. After a minute or so of light petting, he strips naked himself. He was a full on hair bear! His tummy protruded out so much I didn't see his cock right away. We went back to kissing and touch for a little while longer and then he grabbed my cock and led me to the hot tub.
I let him get comfortable first in this four seater. I then stepped in and walked right towards him. He was sucking my cock like it was a long neck bottle of beer. I was slowly thrusting into his warm wet mouth. I was in pure heaven. This went on for another ten minutes. When he gently pushed me away, he reaches over the side and pulls out a tube of lubricant.
"Grandson I need you to do Grandpa a favor?" he asked.
"I have the feeling I know what it is." I replied.
He stood up, turned around and showed me his pear shaped ass. I probed with my index finger to find his hole. Once I had it mapped out in my mind, I took the lube and applied it to my finger. I slowly massaged my finger through his pucker and was making circles to ensure it was done right. Now I didn't apply any to my cock. It has a bad habit of making go from hero to zero. I slowly eased my head in and waiting for him to get comfortable. Well it didn't take long because he backed himself all the way with minimal effort coming from me. My lord! I don't fuck a guy often, but his ass was mighty sweet. We moved as a tandem to the seat behind me, and as one, he sat right on my cock and started fucking himself on my rod.
He would do these two "mini-bounces" and then a long one. I'm just laying back and had no conscious and just let him steer the wheel. I don't think I've ever see kids have that much fun in the water. We must of went at it for a good half hour before the surge in my balls told my I was gonna erupt. I couldn't tell you how many times I shot my load into him. But it felt like molten lava since it was so neatly trapped inside of him. We he finally came down, we showered and cleaned him and the chlorine off of our bodies. We then walked to the bed. His ass was on the edge and opened his legs up so I could see his 5" uncut. I gently pull back the foreskin and start licking his cock. I then proceeded to take him whole and fondle his very large balls. His moaning told me I was doing all the right things. After fifteen or so minutes I got two shots of semen down my gullet. We both laid in bed for a good half hour to recover. He then asks my if I could sleep with him tonight. I said no problem and called the front desk for a wake up call. We spooned and slept soundly.
Tuesday we couldn't play because he had to have dinner with his co-workers. Wednesday and Thursday was a carbon copy of Monday night.
Now Friday night things changed up a quite a bit. He joked how sore his ass was so the focus was my pleasure for the evening. He rimmed me, blew me, and tongued me all over. He then took out the lube again and jacked me so well cum hit my face and neck and I was utterly spent. This was our last night together and we slept like babies for the last time.
The following morning, he bought me breakfast and had small talk before the cab came to take him to the airport. And as I saw him leave, I knew I'd never forget this week. But you can only have these encounters like that once. And that's why I miss Craigslist so much.
The End