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A lighthearted story of discovery, teenage boys, and some sexual situations

Unintended Consequences - 2. Chapter 2

Fessing up, and taking those next steps!

Stewie let me sleep in that morning and woke me after the guys went home. When I woke and did the bathroom thing freshly showered and a mouth full of clean teeth, I felt ready to face the consequences of last night. I walked out of the bathroom to see Stewie sipping a cold can of coke and eyeing me from the basement breakfast/card table.

In front of him was the pile of money we wagered last night, he pushed it towards me saying the guys, including him, wanted me to have it. He asked one other question, one that cut deep into the part I needed to keep hidden. He wanted to know why I held out, he knew he was going to lose the bet, why did I hold back he demanded to know.

Looking into his eyes, I saw something I hadn’t seen before. A glimpse, a fleeting thought that he may be just like me, curious or possibly bi. Lying to him wasn’t going to work, he’d sus me out in a New York minute.

He deserved the truth; we had known each other for most of our lives. That we had his place to play in on Saturdays and all the other things we had done demanded no less than a forthright explanation from me. I thought all I could tell him, was that I liked yogurt.

A wan smile crossed his face as he nodded his head, as he waited for my answer. All I could figure was that we were finished. We had gone from simple groping, skinny dipping and circle jerks’ phase and blown right past it to a gay phase, ruining whatever it was we had. I simply knew once that door was opened, it couldn’t be closed. A thought struck me instantly, forever can be such a harsh word.

I took a deep breath and told him I liked yogurt, and waited for the words that would hurt so frigging much. There was a pregnant pause and I forced myself to look up into his eyes as he spoke back to me, that I wasn’t the only one that liked yogurt, that he liked it once in a while.

Both Stewie and I would turn sixteen shortly after that weekend. The whole sum of my oral experience, both giving and receiving was zilch as of that morning. By the time I left to go home, I had done both.

Stewie stood up and walked over to me, his erection plainly obvious as it tented the front of his boxers. Before I knew it, I was releasing it through the opening and marveled as it pointed skyward. Wrapping my fingers around I began to slowly stroke him, uncovering and then covering the shiny head of his dick. I could tell by Stewie’s breathing how much he was enjoying my ministrations.

Stewie closed his eyes and tilted his head back and the cool of the basement contrasted with the warmth enaminating from his groin. Little hitches became apparent in his breathing and it was time to move over to the couch.

I settled on my knees in front of Stewie and leaning forward took him into my mouth. Stewie moaned and reflexively thrust hips forward. The soft noises Stewie would make as I took him deeper convinced me I was on the right track.

Stewie dropped his hands to the sides of my head, gently running his fingers through my hair and outlining the contours. His touch was electric as he lightly encouraged me, setting my mind at ease as to what we were doing. Time passed slowly, minutes seemed like hours, the pace of Stewie’s breathing slowly quickened matching my own desire.

Stewie drew a deep breath and I knew the moment was arriving, his impending release imminent. Stewie gurgled as his hips pushed further forward, his body tightened and then I felt the initial warm release of Stewie’s essence as it coated my tongue. I continued to milk Stewie as he pumped into my mouth, only stopping when his body fully relaxed with a final exaltation of breath. I could feel Stewie soften in my mouth. As I pulled off, I milked him from the base of his cock where I could gather the last of his cum with the tip of my tongue.

I’d like to say how long I lasted once Stewie took me into his mouth. Thank God he licked, probed, and explored my groin before commencing to suckle on me. The warmth and wetness of his mouth fired off all the right nerve endings and all too soon I was thrusting my hips upwards spraying cum deep within his mouth. Stewie to his credit kept nursing on me till I had to beg him to stop as I was too sensitive.


That was the first of many times over the next year or so that Stewie and I would pleasure each other. He took great delight in the fact that I received such pleasure in his body, so much more that he in mine. That he knew I was gay remained unspoken and I knew I had his acceptance and approval. Some days he’d instigate the action just as he did that first time, most other times it was me needing to safely satiate my cravings. We never kissed and his finger never went back to press inside me. He would allow me from time to time, to play with his ass, to probe that wrinkled opening, run my tongue over it and to taste and sample the delights I found within.

About six months before our eighteenth birthdays Stewie met a fine young lady and I was ecstatic for him. We messed around a little bit on the weekends we hung out. Marcus and Todd also started dating a bit more seriously. I think we all knew this would be our last summer, we had graduated high school and were off to college in the fall.

I was still seeing Mary Beth when the occasions demanded it but had yet to find another like me. I think it was Stewie saved me so to speak. Stewie was an important outlet for me as we lived in a very conservative community and state. I was looking forward to going to Boston College, it was the only way my parents would let me go to school in a liberal state.


That Saturday night we celebrated my eighteenth birthday was pretty much the same, we drank, smoked, looked at porn and did all the usual things. Towards the end of the evening, we were all pretty wrecked when Todd had the crazy idea to place a classified ad in the gay personal section of Doublelist.

He grabbed a pack of cards and shuffled them several times and had each of us pick one, the one with the low card had to be the person placing the post. We’d set up a junk e mail account for the replies to go to and a picture would have to accompany the advert. The only rules were, we had to reply to at least five of the responses one time only, and the pic had to be of one of us and be from the shoulders down. It would be up to the poster as to what would be shown, nude or otherwise.

Once we all had our cards, we were instructed to lay them face down on the table until we all had one. Once done Todd flipped his card over and had the three of clubs. Marcus flipped his over and had the eight of diamonds, Stewie flipped his over and had the three of hearts, this could be interesting, I thought as I went to flip mine over, there could be a tie breaker between those two, and I was feeling pretty good about my chances.

As I turned my card over, I grunted as I had the two of spades…what were the frigging chances! Everyone got a good laugh as I groaned good naturedly. We argued a bit about the contents of the ad and what picture of me to use. We finally settled on the language and use a pic taken one Sunday morning when we were outside cleaning up the pool area.

I am standing looking at Stewie who’s holding the camera. All I have on is a pair blue boxers and sneakers. The boxers, while covering me don’t leave anything to the imagination. I’m a bit tumescent as I know I will be fooling around with Stewie, swapping bj’s in about fifteen minutes. The head of my cock is clearly outlined, there’s no doubt as to what it looks like, the length or the shape of it. We’ve cropped the picture so all that shows is my smooth, hairless body from my shoulders to my knees.

We attach it to the posting and send it off, within fifteen minutes the fake e mail box starts to get replies. I’ve linked my phone to the account so I can peruse the ads later.


Younger Shy Boy Seeks Older Man

I’m 18 6’1’’ 165lbs white ddf blonde buzzcut/blue eyes 6” uncut/trimmed no facial hair. I’m new to this only have done mutual hand jobs and oral a couple of times but am interested in meeting an older man for some fun.

++actual dad types, married/single, suit and tie/ business casual, s+p hair, uncut++ but not necessary, in-shape dad bod, hung++ move to the front of the line.

I’m interested in talking first and taking for the first time, so if this catches your eye please respond! Must live and host in the Tampa area.

Details: 18 years old
Looking for 30 - 45 yrs. old.
Full body pic required, all others will be deleted


We all had a blast that Sunday morning. Changing the rules, a bit after going through the responses we all picked two to reply to before we “closed’ the junk e mail account. We all made short work cleaning the basement and pool area and the three of us made our goodbye’s and left for home. I had my own chores to do and told Stewie I would see later that afternoon.

Once my chores were done, I took a quick shower and fired up my desktop. Opening a link to the account there were another sixteen responses. Five of those didn’t have any pic’s and I deleted them. Another six of those responses just didn’t fit any of the criteria in the posting, it was obvious that they were much older or clearly not in shape.

Out of the final five, two were intriguing. The first was pushing the envelope at the top end for the age range but, clearly was in shape, if the picture was genuine. The final one came in about an hour ago and the respondent was thirty-five years old. Like the other, if the pic was genuine, then I wanted to meet this man.

‘Mark’, was height/weight proportional, had well defined body with a nice tan. His ‘goods’ were prominently displayed, a four inch or so soft uncut cock and a hefty set of balls. He was manscaped and for the most part was smooth. He was definitely in shape; you could tell he worked out.

Unlike the other respondent’s, his reply seemed to be sincere. He offered to meet me in a public place first, that he wasn’t in a rush on his part, that we would move at my pace, he wanted me to be comfortable.

I decided to fire off my own reply to his e mail telling him I was interested in meeting and we would need to work out details. I needed to make sure his pic was genuine so I asked him to take a pic standing next to his car wearing only his shorts.

From the pic in his first response, I noticed a mole just above his belly button. In his second reply I could see the mole, the guy was the same guy as the pics. I had to pause for a second and take a deep breath before composing my reply. He asked me to send him a pic of me wearing the same shorts with my dick showing through the fly.

I had to ask myself, did I really want to go through with this. I had offered Stewie several times to be the one to take me that way. He’d shake his head and simply tell me it just wasn’t his thing. It left me with a need that was unfulfilled and here was possibly the answer to that need.

I found the blue boxers and quickly put them on slipping myself out the fly. I set my camera up, pressed the timer and let the camera take the pic and sent it from the fake account. I had nothing to lose and could stop this at any time I told myself as I composed my reply and hit send.


We had established a rapport through our e mails over the previous week and were at the point where we exchanged phone numbers for texting. We decided to meet at the Cheesecake factory at the International Plaza mall that following Sunday from our initial contact. My need for someone to show me the ropes as it were, was clearly understood.

Stewie was involved in all the back and forth. I showed him all the e mails and pictures when I went back to his house that Sunday afternoon. I once again offered him first dibs on my backside and he strongly considered it. I had dropped my shorts and turned so my behind was facing him. He lightly stroked my bum, slipping his fingers downward, barely grazing my offering.

Sighing, he withdrew his hand and expressed his regret once again, it simply wasn’t his thing. He didn’t refuse a bj and was more than willing to return the favor.

The week flew by, it was one Saturday night that I managed to behave myself. I woke up at Stewie’s Sunday morning with a clear head. We were going to take my car over to the mall and get there about an hour earlier than I was expected. Stewie was going to hang around in the background in case I decided not to go through with it. Getting their early gave us a chance to pull the plug if needed.

Stewie gave me the bag from the drugstore with the two enemas, I was to use them both, one at a time so that the second got what the first didn’t get. We both knew it was important to be clean back there. When I finished my shower, I went out into the basement and relieved some of Stewie’s pressure before he pulled his cargo shorts up. I told him that if things didn’t work out later it was his turn to take care of my need, I wasn’t going to let him say no if it came down to it.

I had agreed to text when we were on the way. My ‘date’ Mark, only lived about a half hour away. I was going to wear my TB 12 Patriots shirt. Stewie could never understand why I rooted for the Pats, he being a Tampa Bay fan. Stewie was going to wear a floral print and Mark was going to wear a Seattle Mariners jersey. It was Stewie’s idea that I go to the mall commando, he gave me a pair of shorts when wearing them left little to the imagination.

We left for the mall and found convenient parking. The Cheesecake Factory was easy enough to get to and once we parked the car, I texted Mark, once there, that we were on our way and should be there shortly after him. It was interesting watching all the folks walk by all wrapped up in their own little worlds. There were a few people who noticed my tumescence. It was difficult for me to keep things under ‘control’ down there. It was never far from the back and for that matter, the front of my mind, exactly why I was at the mall today.

I figured I had about a seventy-five percent chance of finally having someone enter me in the most intimate of manner and in doing so become a part of me. I concluded, that for whatever reason, I was wired that way. It was part of who I was, that the need that manifested in me, needed to receive and to give the same pleasure to my partner.

I vacillated between certainty and doubts. As the certainty would rise above the doubts my shorts would tighten in anticipation. There was no mistaking that a part of me was doing its best to override the rational part of my mind. I thought about how the next several hours would be fraught with possibilities, of a need only imagined.

My shorts were becoming restrictive as the time grew closer, my breathing a bit more ragged and the nervous anticipation was bleeding adrenalin into my bloodstream, making it difficult to converse. It was evident I needed to adjust myself, sliding my hand under the top band of my shorts I was able to free up some space for growth. When I looked up, I noticed this kid across the hall from me moving his hands deeply in his pockets. It was obvious he had been staring at me and liked what he was seeing.

I needed to bleed off a bit of nervous energy and told Stewie I was going to take a leak; I’d be right back. The caffeine in the coke I was drinking wasn’t helping me at all. No sooner had I unzipped and started to piss when the kid who was watching me came in and took the urinal next to me and pulled out a nice erect circumcised cock. Giving me a show while I finished pissing, I explained I was meeting someone in a few minutes but thanks. At the sink while washing my hands, he handed me a slip of paper with his number on it. He asked me to call him if I was interested in hooking up sometime. His name was Jarred and he was sixteen.

Stewie hit my shoulder about the time Mark was due and pointed just past the Cheesecake Factory. Sure enough, we saw someone with a Seattle Mariners jersey walking towards the entrance to the Cheesecake Factory, it was Mark, of that was no doubt. The butterflies in my mid-section were going off. It was then we recognized who Mark was.


Back in high school, our parents made us take an auto mechanic’s course as part of getting our learners permit and eventually our driver’s license. Our high school’s auto shop was run by Mark Gault, who also served as coach for the JV golf team. Mark’s parents passed away during our sophomore year in some sort of accident. He was left a considerable sum of money and his father’s auto repair shop. He left school by the end of the year to take over the business and was doing very well. My family and others we knew, took their cars there for repairs and state inspections, myself included.

My nerves calmed a bit, I knew Mark would be safe to go with, and told Stewie that I should be fine. Mark was someone who had a body I appreciated whenever I saw him or passed by in school. Stewie insisted that he walk over with me and as we approached Mark there was a sign of recognition in his eyes. Before he could say anything, I told him I was the shy boy from Doublelist.

It was a bit awkward at first, Mark offered to by us both lunch and I explained Stewie was my driver as I tossed Stewie the keys. We talked for a few minutes, catching up on school and our graduations and plans for college. Mark said he would give me a ride home after and I told Stewie I would call him later tonight.

Mark wanted to know a bit about my sexual experiences on the way to his house. I told him the basic truth that nothing more than hand jobs and some oral. That I knew I was gay, that Stewie and I fooled around orally but that was as far as he would go.



I was one happy camper on the ride home from Mark’s, my afternoon could not have gone better. The whole experience was surreal and ever so enjoyable. I knew I had made the right decision in looking for someone older for my first time if it couldn’t be Stewie.

Mark was kind, loving and patient. He took his time and let me set the pace. His goal was to make this as pleasurable for me as possible. It was all that and more. I may have been a tad sore but the warm feeling deeper inside of me made it all worthwhile. It was so much better that I ever could have imagined.

Mark let me know that he didn’t frequent Doublelist. It was more out of necessity he offered. He was looking for a bit of relief other than his hand. His former partner had an issue with credit cards. Not fully understanding that you needed to pay them off, rather than max out the balances on each one. When they broke up a couple of months ago, he was nearly thirty-three thousand dollars in debt and had managed to spend an additional thirty-eight hundred on Mark’s corporate Amex card.

They had been in a relationship for nearly ten years. In addition to the debt, Mark noticed smaller items of some value were missing from his house. It was the last straw, he booted him out, changed the locks on the house and the repair business and settled for dating his right hand.

Mark’s house was set back in a private sub-division and judging by the outside it was well maintained and cared for. It was set back from the street and when he parked the car in the garage, I was amazed at just how organized spotless it was. If the garage was clean, the house was immaculate. The first room we came to was the kitchen, offering me a bottle of water he asked me if I wanted anything else as he drew closer to me.

I think the tent I was wearing gave me away. My erection was straining mightily against the fabric of my shorts. Mark had a growing problem as well. The house had central air I noticed as we walked in and was comfortably cool, now it seemed as if it wasn’t working. I could feel the nervous perspiration on my arms and my need to wipe the damp off my palms.

Mark, bringing his hand to my chin, lifted it up placing a soft kiss on my lips then drew back as if seeking permission. Smiling as I exhaled most of the air, I had been breathing all day, I nodded my head and leaned forward to meet his lips.

I not sure how it happened, but Mark’s lips somehow walked me to his bedroom and managed to take my clothes off. I feel the solidness of him as he presses against me, his lips and tongue caressing my adam’s apple. My sides are gently grasped as his fingers play my ribcage. A wedge of coolness forms as our bodies separate, I gasp as he’s found a nipple and suckles. His lips gently brushing over my breastbone as he seeks the other.

I am paralyzed in his embrace, his hands cupping my bottom as he sinks to his knees, his tongue leaving evidence of its passage as he descends, my navel its next destination. His fingers kneading my backside, manipulating the muscles, pulling, stretching, prying apart. I am tantalizingly exposed; I feel the effect of the cool air of the bedroom as it wafts across my rosette. Fingers tenderly dart over the wrinkled surface as I shudder in reaction.

I am being played like a fine musical instrument as he further explores me. Involuntary, the gap between my legs increases as his nose nudges my testicles aside in seeking further olfactory delights. My length is nuzzled tenderly, pulsing in reaction, yearning for more.

I am guided to turn around; I feel Mark’s arms wrap around me as he plants gentle pecks upwards along the ridge of my spine. His hands proffer security as they cup my breasts. I feel safe in his arms, I know what is to come and my desire inflames the rational part of me.

He’s nested firmly against the vale. His warmth telegraphing his desire as he presses lengthwise against me. He leans against me as my hands reach to the bed for support. I shudder as his breath slowly finds its way down the length of my back. I’m missing the warmth of him as he pulls away and sinks to his knees. My legs voluntarily move apart as he returns upwards to cup each globe as he prizes them further from one another. His mouth lands at my tailbone, his tongue traversing down the newly formed crevasse.

I am fully exposed, his fingers cajole a further opening, a separation revealing the tautness of the aperture, he seeks to pass through. Faintly his fingers pass over and create a mild tension as his tongue begins to probe. I am momentarily startled as the moist tip darts and swirls seeking further passageway.

I hear a snap of the container top, and a lubed finger replaces his tongue. Easily it slides in, working its way deeper. Soon it is joined by another as they work inside of me. All too soon I find myself on Mark’s bed on my back.

He’s hovering over me as he applies lube to himself, he glistens in the soft, diffused light that streams in from his bedroom windows. I marvel at the shape, the contours of what is soon to be inside of me. I am trying to catalogue each, and every new thing, to do my homework for this lesson.

I can’t help but admire Mark’s body, to tell the truth I am enthralled, lost in a sense of wonderment. This brief moment, when we have separated to do what’s necessary, for the next step, gives me pause. Above me was a specimen of near physical perfection. Years honing his body through hard work and exercise had culminated in what appeared before me.

Don’t get me wrong, I appreciate those bodies of my peers, Stewie excites me no end, it’s what I kept offering to him that he would not take. I even found that boy at the mall Jarred, intriguing and could see some time with him. But, at our age, we were young men just not fully grown into what nature intended.

Mark had filled out, there’s a solidity when he holds me, his feet are planted and he has deep roots. His age shows well on him, just a touch of gray at his temples. Like me he’s smooth with a minimum of body hair, it’s easy to see how toned he is, buffed is a word that comes to mind.

I rise off my elbows, to come closer to him. I reach out and cup the orbs that produce that which will reside deep inside me. I think it’s a phenomenon, a wonder of nature this construction that intrigues, entices me so much. It speaks to the deepest, base need of what I am…and desire. I can’t explain the attraction, it just is. I can’t deny the necessity that drives that part of me. I reach for the lube squirting some on my hand and apply it to that which will be parsing me. It will break down the barriers that stand between me and my virginity, forever changing me. I nod that I am ready and lay back down.

I’ve have seen more videos and read too many stories, not to know what’s imminent, as Mark lifts my legs, his knees move closer to me, placing himself against me as my legs now drape over his thighs. I feel the cool wetness and wince as he seeks entrance, then presses forward a bit and retreats. He does this several times weakening my internal opposition. Pausing, planted firmly against me, he leans over me seeking my lips as he holds his position, I lift my head, rising to meet him as he pushes past the barrier as I gasp.

A searing bolt of pain blazes through me as I am fully opened. I know it will pass but the thought is no help against the reality. I feel as if I am stretched wide open as Mark slowly comes to rest against me. He’s imbedding his flag so to speak; I want this and I know the pain will diminish as my body adapts. He’s kissing my neck and face, whispering to breath, relax and push out, encouraging me to move past the discomfort.

Gently he thrusts, rolling his hips as I get a bit more comfortable. Several minutes, a lifetime it seems, pass and the initial discomfort is diminishing as Mark’s pace slowly increases. My feet rest on his shoulders now, his arms pinned to the mattress beside my head, holding me in position. I shudder as the pace picks up as inexorably a threshold is crossed. I’ve gone from pain and discomfort to something quite different. He’s grazing a spot inside me that sends waves of pleasure coursing through me. I can feel the contours of his length as it transcribes my passageway. There was no discomfort now, only an increasingly pathway to pleasure.

I encourage Mark, verbally cajole him, my ardor insists. There’s a torridness to our coupling now, the mattress quakes while tremors are setting off my nerve endings. My utterances are becoming incoherent as his thrust become longer deeper if possible. Just when I think I’ve reached the pinnacle he slows; moderates his pace and I ride several waves of pleasure this way. I’m but a touch away from ejaculation.

I’ve lost focus, I can’t concentrate to catalogue my feelings, to sear the means and manner, in which I’ve been taken. I am reduced to simple animalistic pleasure. Somehow the urgency rises and the pace quickens again, I can’t stop what’s happening to me this time, as the assault hastens. Mark is battering against me now, driving me deeply against the mattress. I can’t last any longer as I groan out my release, my internal muscles clamping down, as I spray my seed all over my chest Mark stiffens and I sense the warmth of his milt fill me.


We’ve showered, dressed, and are sitting in the kitchen finishing a quick lunch of sandwiches and chips. Conversation was a bit awkward at first but we’ve passed that hurdle now. Nearly at the same time we ask each other if we would like to meet again. Once we’ve done chuckling, we agree to meet the same time next week. I’ve got a lot to talk over with Stewie, and I hope some convincing to do, the summer is young and I think I just may text Jarred as well.

I think this just may be the best summer yet!!

We'll be coming back to check in on the boys as the summer moves on, thanks for reading...your thoughts and comments are welcomed!

Copyright © 2021 drsawzall; All Rights Reserved.
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Thanks for the comment, it is appreciated, one had to realize, when you place or respond to a classified add, it's like a box of chocolates ya never know just what you're gonna get!!

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Wow that was a very hot session!

Man 18 with raging hormones, its going to be a hot and steamy story

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18 minutes ago, long1jo said:

Wow that was a very hot session!

Man 18 with raging hormones, its going to be a hot and steamy story

Thanks, Chapter 3 will be out soon, your comments are greatly appreciated!

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