Are you horny or just happy to see me?

Dearest Tennessee,

I arrived home Saturday evening after enjoying a week’s respite at my family’s vacation home on the head named after Captain William Hilton who discovered the island in 1663. ‘Tis a charming place of natural wonder imbued with the spirit of the Gullah people, ex-slaves who flocked to and settled there during the Civil War when Union troops occupied the island. It is as intoxicating as it is beautiful and each time I am there I am transfixed by both its literal and figurative warmth.

Week before last as I was packing for my journey south I made the rather dubious decision to not include any of my various possessions related to sex play in those I gathered to take with me. A decision my dear sir, I assure you I will not make again as nary had I been on the island a day and I was itching to post on Craigslist to see what kind of fun I might get myself into. However, that day being Sunday (and not having any toys, lube, or protective gear with me), I resisted the temptation and instead spent the day and evening relaxing and occupying my mind and person with other activities.

Monday however was different story. I had planned a trip to Walmart to pick up a few provisions and decided if I was able to find lube and finger cots there I would purchase them. Much to my delight as I perused the Health and Beauty section, I found Astroglide (original formula) in the area reserved for products related to birth control. And in the first aid department, I found the finger cots I often use in lieu of wearing a full exam glove. Booty in hand, I made my way back to my parent’s vacation villa post haste and posted the following on Hilton Head’s Craigslist server.

Anyone up for a nice long prostate massage? Nothing gets me going like having a guy with a sweet rump on all fours, butt in the air and working it over ’til he’s moaning and begging for sweet release.

SWM, 46, 6’1″, brn/brn, 180, naturally smooth, average looks, average shape and average endowment. DDF, low-key and drama free. Generally looking for the same (-10/+5). Particularly love to pleasure the posterior of a hot daddy who doesn’t typically get such a thing at home and needs a little now and then.

Staying near the Crowne Plaza on Shipyard ’til Friday evening. So open to a little fun between now and then whenever it works.

Hit me up if interested and let’s see if we can make it happen.

While I initially received quite a few responses to the post that evening and traded quite a few emails. I was not able to line someone up for the evening. However, the next evening I received the most curious response to the ad.

Wow. You must have the best ad that I have ever read. You are offering exactly to a tee what I am looking for. I know you put the ad up yesterday (today is tues), but I am hoping you are still checking your email. My story is that I am married, 35, and str8. However, I love being touched, especially like that, and I do not care who is doing it. I just love being taken to that level. I am home alone for a couple of days and live mid island, right by the hh diner. Would love to be moaning and begging for release by you. What’s your story? Are you visiting? Do you use toys to do this or your hands? Does not matter to me. Your ad simply has me going nuts already. By the way, I am very clean. I hope this message finds you.

I was intrigued to say the least.

Three emails, several phone calls and two hours later I picked up a curiously attractive gentleman standing in front of his car in the parking lot of Hilton Head Diner and returned with him to the vacation villa. After a few moments of small talk, we found our way to the master bedroom. As he began to remove his shoes, I excused myself to relieve the call of nature. When I return to the room he was laying buck naked and prostrate on the king sized bed.,

“Wow you got out of those clothes fast!’ I laughed. “I wasn’t wearing much.” he replied as he slightly squirmed on the bed, “How do you want me?” he inquired.

“You’re good for the most part.” I said as I grabbed his ankles and spread his legs slightly which revealed the largest set of man-balls I’ve witnessed in quite a long while. This will prove to be interesting, I thought to myself.

“Let’s get you closer to the center and diagonal.” I grunted as I pulled him slightly downward and across the bed. All the while marveling at the huge globes of flesh nestled ever so deliciously between his massive hairy thighs.

I jumped on the bed, mounted his back so my rump rested ever so slightly against his, leaned over and whispered ever so softly in his ear, “Are you ready? Do you think you can handle it?” He once again squirmed, though now under my weight, and murmured, “I think I’m ready and I believe I can handle it.”

After loosening him up a bit with a long back rub, I lubed up a finger placed it on his sweet little rose bud and began to slowly work round and round to relax it. He shifted slightly back and fourth and let out a very faint moan.

“Everything okay?” I asked, “Yesssss.” he sighed, “It feels so good.”

“Oh, I’m just getting started.” I laughed.

I rolled a finger cot onto my thumb, applied a liberal amount of lube and pressed against the back gate with the slightest bit of pressure. Finally resistance gave way and I slowly began to work the digit further into the chamber. Startled by this intrusion his sphincter tightened against my thumb, l slowed my advance, it relaxed and when at last I entered the garden and brushed every so slightly against his prostate.  A guttural moan rumbled to the surface from deep from within him.

“You okay?” I asked. “Oh, yeah…” he moaned as he shifted and wriggled against the bed sheets.

After a few moments of tickling his prostate with my thumb, I pulled it out slowly, place a finger cot on my middle finger and slowly inserted it as I had my thumb. As I made my way slightly deeper in and began to massage with a slight bit more pressure he let out an ever deeper moan and sighed, “Oh fuck, that feels amazing.”

“Good.” I chuckled that’s the whole idea.

I worked him over for a good 20 minutes on his stomach alternating the stimulation between his posterior and his throbbing member. As his balls began to tighten, he managed through sighs and moans, “I’m gettin’ pretty close. I don’t think I can hold it much longer.”

“Okay then, let’s flip you over.”

On his back and with my finger once again in place, I could tell he was very close to release so increased the rhythm of the strokes along his shaft. He shifted his hips and slightly trembled.

“I’m going to cum.” he gasped, then moaned and began tremble uncontrollably with orgasm and at its conclusion laughed and said, “Man that was fucking amazing!”

“My pleasure.” I chuckled. “Let’s get you cleaned up.” I said as I jumped off the bed and headed toward the bathroom. Fifteen minutes later I was dropping him back at his vehicle in the parking lot of the Hilton Head Diner.

“Take it easy.” I said as he opened the passenger side door. “Man you gotta come down here more often.” he grinned.

“I will.” I smiled. “When you do, definitely hit me up. I’d so be down for that again.” he said with a glint of earnestness and eagerness in his eyes.

I’m seriously considering a return trip to the horny south in the fall.