Answered an Ad

I am a young looking 40 year old single professional and well respected businessman known locally and very publicly. After years of hiding my true identity, sneaking around seedy adult stores, erasing browser history, contemplating visiting gay bars in out of state locals, I finally hit a “local” web site that intrigued me, it advertised everything from general contractors, help wanted, to services rendered, kind of like a locally sourced multi county Craig’s listing. As I browsed all topics and categories I ran into a series of personal ads that sent my heart and dick a fluttering. While I never ever considered ever answering an ad especially locally, the ads became more suggestive and discrete, I found myself getting off and horny as I read on. Each day I found myself slipping into the personals to see what were the new listings amongst all the old ones.

 One repeat ad in particular caught my attention almost every day, it was extremely descriptive as well as sensual with a suggestive tease, every few days they made slight wording changes which categorized it as “New” and therefore sorted toward the top of the list. Over the course of a few weeks, I had a very good visual, as well as a sincere temptation. Now, I would never jeopardize my status by making contact, but surely I could tease back, so called “bait the hook” and just have some fun. 

The guy….. He sounded young, could be a problem, might even be jail bait, and could be a plant, so I was very cautious, especially at first. The subject had a privately held, supposedly untraceable, commercial web email mailbox. I was Leary of trying to contact it, especially with my own personal or web email, for fear of getting caught, or exposed, so I avoided it. As the days wore on, the descriptions became more intriguing, the tag line read - Young Guy looking for fun with another, prefer 20 and older, can meet your place or I have some suggested spots, contact me with details at [email protected] anytime, Friday thru Sundays preferred, but willing to consider alternatives. Then each week additional details were added and deleted.

Week 1 - 18, closeted young gay boy, 

Week 2 - a senior in high school, has own car, discrete, 

Week 3 - 5’11”, 125 lbs, thin, smooth all over, 

Week 4 - nice 6 pack, works out, 

Week 5 - wrestler, track team, swim team,

Week 6 - blonde, long flowing, stringy, currently shoulder length hair

Week 7 - clean shaven, face and all over, bubble smooth butt

Week 8 - 7 1/2 inches, cut

Week 9 - love to suck and finger, I’m told I’m quite good, and I swallow

Week 10 - I deep throat, your wish is my command 

Each day he kept adding more and more revealing details, I even got rock hard anticipating the new add each time. One day I found myself stroking through my pants as I sat in my office searching the ads for my regulars.

 That did it, I finally got the courage to look up the 3rd party email mailbox site that he was using, I joined it, and got my own private, supposedly non traceable, discrete email and decided to try it out on my prey, that I’ve become obsessed with stalking. It was innocent at first, “Hi there, you sound cute” the response was quick and somewhat suggestive, “You ought to find out”. We merely sent each other one line teasers each day, if I skipped a day unintentionally, he sent me one before I could reply. They became more suggestive and lead me to reveal more of myself, my age, my height, weight, hair, build, and eventually some sketchy details of my work. It was odd I found the back and forth banter exciting, and looked forward to each message each day.

 One day there was an attachment, petrified to open it or not, I finally clicked it, after hovering my mouse over it for what seemed an eternity. It was a photo, a chest down to knees photo, slender in shape, body clad in a red Speedo, it was a straight on shot, a slight package bulge visible but somewhat hidden because of the angle. It was hotter than hot, it became more evident, as I found myself leaking on my fingers. Oh crap I was jerking off in my office chair to a Speedo clad photo. I simply replied “I really liked your photo” which brought me another teaser the next day. A side angle from chest down to knees, this time accentuating his protruding bulge, obviously tucked into and disappearing behind his thighs, I couldn’t see the nipples but I could just imagine. My reply this day was “Nipples Please”.

 The next day the photo was a close-up, full, pink, plump, and seemingly firm nipple, every multiple encircling bump, rising to a perfect peak, slightly larger and lighter in color as it reached the peak, the photo seemed of professional quality, and clear as day, the nipple filling the screen, full sized on my work monitor, had me leaking once again. I admit I’ve never studied the shape and texture of the nipple before, I could only imagine touching and tasting it, flicking it back and forth with my tongue and wanting to pinch the nipple between my teeth, oh my god, I came again today. I took a chance and snapped off a poor quality phone photo of my open pants and hardened dick, hidden under my grey briefs and sent it along, no words.

 The next morning I quickly opened his note, with a close up red Speedo clad crotch shot, I swear I could count the threads, I could see the distinct outline of his shaft and balls almost being able to identify veins through the material, but wait, a small darker red wet spot, just in front of where I imagine the head to be, his thighs were white against the red and smooth as silk. I wanted to run my hands over the entire photo as my hands trembled around my own member, and I closed my eyes imagining I was massaging the images in my small but growing photo collection. I got daring in my reply today by taking my shirt and tie off and photographed my naked chest from my neck down to my belt using a mirror in my private office bathroom.

  His reply the next day was merely a wide eyed, juicy dripping tongue out emoji, followed by another email a few hours later with a gorgeous close up of his exposed dick head, I mean it filled my screen, a giant slit perfectly proportioned as I followed the seam with plump mounds on each side, the skin a deep pinkish purple in color, with millions of tiny lines, almost like a finger print in perfect focus, as my eyes approached the edges of the rim of the head the focus softly faded, my god I stroked my fingers across it on my screen. His typed a note this day saying simply “I think it’s time.”

 I immediately took that as he wanted to see more of me, and I was so hard, I stood completely naked and propped my camera on the desk and took several poor shots of my naked body in full profile, I picked two, and quickly sent them off to him, within hours I had another reply with several photos, none of his face, the first was, his deliberately blurred face focused on his long flowing blonde hair draped slightly over his naked shoulder, a second like his dick head close-up dripping with pre cum, a third of his non erected dick resting on his smooth balls between two white smooth thighs and a fourth profile, naked from the neck down with a hard on, he was gorgeous, what could I say? A fifth photo was another close up of his entire dick dripping with cum on his masturbating hand, oh my god those photos were hotter than hell. I jerked myself at least three times straight, right there in my office chair while I played the photos on my 27 inch computer screen on auto play loop, and on repeat, over and over again.

 I finally got around to reading his latest note, saying again “I think it’s time” this time adding “we meet in person”. I froze for a minute as thoughts ran through my mind, what if he’s not 18, what if it’s a trap, this might be dangerous, what should I do? My little head overtook my big head as I began typing. “How about the state boat launch parking lot about 7 tonight, tomorrow or Wednesday?” Within seconds a reply came back, “tonight at 7 would work, I have an old blue Honda accord” I replied “great, mines a red Mazda Miata convertible.” It was still early fall and usually got pretty chilly after sunset, I was so conflicted with my decision I couldn’t concentrate the rest of the day, I went home early showered and picked out an outfit 3 different times. I wound up with fairly tight, almost dress blue jeans, a nice button down plaid dress shirt, shoes, belt the whole works, extra deodorant some over powerful after shave, damn I cleaned up nice and was ready for action, I slid into my little car seat, ass first, popped her in gear and headed for the boat launch.

 Being early fall, there were only a few cars parked, no boats tonight, mostly couples necking as they watch the moon rise reflecting over the lake and trees. It’s a small lake and mostly used by small fishing and recreational canoes, sails, kayaks and a few very small motor boats, so the colder evenings limited the small crowd to a few nature observers. I was a least an hour early as the sky slowly turned from grey to black and a crescent yet bright moon began to be visible through the mostly bare tree limbs. The closest car was a few rows away, I couldn’t see them, they couldn’t see me, and it would be perfect if it stayed this way. 

 7pm came and went, my anticipation began to turn to disappointment, when a car finally pulled up a row behind me, it could be a blue Honda accord, I caught the emblem as it parked, it took a while for the lights to go out, but it just sat there in silence as my glued eyes watched in my side view mirror for any indication of my prize.

 After a few minutes I just waited and stared, when suddenly the interior light came on, I saw that blonde mane of hair through his windshield and my nerves immediately began shaking, as my dick hardened pressing tightly in my jeans. I watched in my mirror as his slender body closed the car door and the interior light began fading to dark, he had loose fitting sweat pants with a slight tenting bulge that bounced up and down as he began to walk toward my car. A muscle sleeveless T-shirt cut high on the midriff with those obvious abs exposed to the cool autumn air. As he approached the car he veered off to the passenger side, he stopped and stood at the door window for a moment that seemed to be an eternity. His perfect abs were exposed at the top of the window frame, his package was perfectly centered in the opening, as he reached down for the handle, opened the door and slid into the seat. His hair covering his face as he closed the door and then he flung his head back forcing his hair back over his shoulder. I don’t know why, but I asked him if he was Nick, he answered, “well about that, truth be told I’m Nate”, and it hit me, as I looked into that beautiful boyish face. I think I knew him, I’m not sure if he knew me. I think it was the Nate that his mom used to bring him to the gym that I belonged to, and he used to basically just hang out while she worked out, I remember what a little snot he could be, as he played on the equipment with disregard to other customers.

 He looked at me and smiled as I melted at those perfect teeth, he immediately lifted his shirt up over his head propping it behind his neck as he raised his arms to pull his hair free from the scrunch, that motion exposed his model type body, the abs, the pecks, the nipples the protruding collarbone, the clean shaven arm pits, my god. My hands instantly rose to stroke his strong firm chest as I ran my fingers through the crevasses and up under his hair lying across his shoulder, I slid my hand under the bunched up T-shirt on his shoulder as I felt his upper back. I wanted his entire body in both hands, but I continued to explore with just one hand. I realized his hand was sliding up and down on my thigh, I saw his dick poking straight up in those sweats, as I concentrated my hand strokes on his lower abs, slowly rotating them across his smooth skin I gradually slid lower and lower eventually allowing a finger or two to breach his waist band as I dared to get closer to my so called prize. His hands were now on my crotch, damn! I wore the wrong clothes as I tried desperately to undo my belt letting Nate slide his long slender fingers right into my briefs, as his slightly cool hands quickly made contact with my manhood as I was lifting my ass out of the seat attempting to squirm out of those tight jeans. His whole body moved closer over the console as I grabbed his side around his back and pulled his head closer to mine, I could smell the shampoo in his hair as I buried my nose into his hair inhaling deeply. 

 Meanwhile my dick is already building to a climax, I had to stop him while I pulled at his waist band, I pulled it down below his balls exposing that luscious rod of pleasure, as I leaned in closer and even in the dark I could see that dick just like the close up pictures, I pressed on the pre cum covered slit with my finger, the spongy head feeling velvety on my fingers.

 To be continued…….