My Own Summer: Yardwork

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Shy guy seduced into first time Anal.
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Thanks to everyone who followed, left comments and feedback. I really appreciate you all. I'm getting to Vay-Cay Pt 2...promise.

Everyone is Over 18.

Trimming the top of the hedges and standing on a ladder I could see over into the neighbours yard. Their beautiful daughter Sandy, who I knew from the neighbourhood, was there sunbathing by the pool. I waved at her and seeing me she dipped her sunglasses to the edge of her nose as if to get a clearer view. Upon recognising me she eye-rolled and went back to tapping away at her phone, slowly pushing the sunglasses back into position.

I felt so stupid in these moments and they served to remind me why I kept myself to myself. In my mind I looked like Forest Gump waving to Cpt. Dan from his boat. I was the grinning idiot waving from the top of a ladder to someone who had complete disdain for me.

So I slowly shrank back behind the hedgerow and down the ladder.

"She is a little snob. Don't worry about her." I turned to see Jeff, who's yard I was working on and wobbled slightly on the ladder before deciding it was best to climb down.

"I wasn't...she...I don't think she saw me." I said waving it off.

He raised his hand. "Hey, she's real a cutie but she's also a rude little brat." He said sensing my bullshit and sitting down on the sun lounger by the pool. "And it was her dad who told me that last part so what does that tell you?"

He was kicking off his Chuck Taylor's and began rolling down his jeans to begin his after work ritual of stripping down naked and jumping in the pool.

"Works over, buddy. Time to get wet." With that he jumped in the pool and let out a loud "whooo!" when he came up for air.

"C'mon man, work is over!"

I looked at my watch and saw it was 13:23. Is work over? I kicked off my shoes and somersaulted into the pool to much cheering from Jeff. This is the best job ever?

My father got me a summer job doing some yard work around the homes of our neighbours and while it might seem strange that an 18 year old was having his employment arranged by his father; for me it was somewhat necessary.

For a while I had suffered from this crushing anxiety and it wasn't improving. I was struggling just to talk to people, to keep up with friends and even going outside was starting to feel like a big deal.

Surmising that I'd spent a chunk of my formative years reading, listening to music and doing little in the way of physical work; my father suggested that perhaps with physical confidence would come some mental confidence. While I was in decent shape, I was reedy and the weight of a man's physique had yet to come to my bones. We figured maybe some manual labor could help remedy that and I found that within a week or so I began to really feel the change.

The yard work wasn't too hard. Mostly pushing mowers picking up leaves and cleaning pool filters in the sun and I loved it. I loved being outside. I loved DOING and actually being productive. I was developing. Plus the nature of the work meant I was still on my own much of the time and only had to deal with people in a limited way.

Quickly my favorite customer was Jeff. He took me under his wing and after a few weeks I considered him more of a friend than a client or boss. His house was beautiful, near the Palisades in North Santa Monica, not too far from my family home. Jeff picked up on my shyness immediately and got it. He teased a little but mostly made a real effort to make me feel relaxed.

Jeff was in his mid forties, I think. He had this longish hair that he'd tie up in a little bun like those yoga guys you see with their little mats in Pete's Coffee. I'm pretty sure Jeff wasn't a yoga guy but he definitely took care of himself. He was about 5'10...11 and muscular but not jacked.

As for his wife I never met her. She was always away on business although Jeff joked that she'd left him but left him the house.

At home he was always strutting around the in the nude. He would just strip off like clothes made him feel comfortable, he didn't make a big deal out of it so neither did I and after a while I didn't notice so much. I mean, I noticed...I noticed he had a pretty big dick as its hard not to notice when its swinging around as he brings you a drink.

We talk about music and he'd ask me about what bands I was into and played their music on the stereo. He had a knack of hearing the bands I liked and picking out their influences then we'd listen to those. After a while it barely felt like work and just felt like we were hanging out.

It got to the point where I was at his house most days and if I had another yard to do I'd blaze through it in the morning so I could go and hang out at Jeff's in the afternoon. When Jeff wasn't there I'd swim in the pool. The garden was pretty secluded so I'd strip off my shorts and cool off. Naked swimming with some of my favorite music playing. I loved my summer.

I'm not sure exactly when the sexual tension began. Maybe it was there from the beginning as Jeff was always lying naked around the pool. Often he'd bring conversation around to girls, sex or porn and more than once I noticed he was getting aroused. Not that he was fully erect...just his cock would obviously thicken as we talked and when he thought I wasn't looking he would pull it a little. But I have to admit, I was always looking at it. It was big and kinda beautiful and I'd never really been around naked men before. I couldn't help it.

He'd watch me do yard work and even though I'd never had homosexual thoughts I didn't mind being the object of his attention. Being the focus of some one's sexual energy was invigorating and honestly, I enjoyed it. In fact, so much so I often went home and stroked one off as soon as I got the chance. Some times I thought about Jeff watching me as jerked off. Playing with his hard length as he watched me writhe.

We swam in the pool that afternoon. Splashing, listening to music and throwing a ball around. We'd play fight over possession and I'd feel Jeff push his naked body against mine. He could easily overpower me and I liked that feeling. I held the ball underwater and turned away from him so he'd grip me from behind. He pushed himself against me and reached both of his thick arms around my naked body as he tried to grab the ball. I felt his cock get harder and him rubbing it against me. Against my ass. So I pushed my body back in to it. I got hard too and we ground our bodies together. Eventually his hand slipped down over my cock and he masturbated me a little under the water. An awkward silence passed as we both caught our breath and I broke away.

It was Jeff who broke the quiet first. "You know this one? Sea Within A Sea?" He said regarding the song that was playing by a British band called The Horrors.

"Yeah, I love this. Its like two or three songs in one." I said as I walked through the water to the other side of the pool. I was relieved to have changed the subject after what just happened.

He tilted his head and raised an eyebrow. "Cool, what else do you like about it" He smiled.

"OK...I guess I like how long it is. It goes on and on...but not in a bad way. Hypnotic, I guess." I shrugged. Jeff encouraged me to express ideas to explain why I did or didn't like something. Always asking what I thought about things and if I didn't know yet...well, that was OK too. Just as long as I was being myself...something I felt difficult around people.

"Did you listen to their early stuff?" Jeff asked.

"Yeah, I didn't like it as much. Seemed kinda rough....a bit like punk. Not my thing."

"Right, they were more of a garage band early on. It wasn't for me either. I got to see them in about 2017, that was really cool. Next time they're in town you should come."

"What?"

"The Horrors. You should come see them with me, it'll be fun."

I smiled. "I've never been to a gig."

"Jesus Christ kid, all the more reason for us to go." He said as he hoisted himself out of the water and walked over to the sunbed.

I hesitated in the water waiting for my erection to subside. "Do you have a towel?"

"No. You are just going to have to strut your stuff up here. The sun will dry you in about 3 minutes." Jeff looked surprised as we'd gone passed the point of shyness around my naked body weeks ago. I was a walking hard-on at this age, constantly horny and I knew this wasnt going away for a while or until I jerked off.

I climbed out of the pool with my semi erect dick bouncing between my firm thighs and covered myself as I sat down with Jeff on the sun bed. There was an awkward moment of silence before he broke it by starting to laugh.

"Matthew, were you getting a hard on in my pool!" He said adopting a fake deep & stern tone he reached forward and grabbed the cushion I'd used to hide my stiffness.

"Oh Lord. I don't care, man. I get it....all those hormones raging. We were naked...being all physical. Its normal." There was a silence between us but I felt calm.

"I take it there is no girls...no boys at the moment? No-one to see you naked....besides me of course."

"No, not really. There are girls I like but I don't speak to them much. I don't know, its weird." I trailed off.

"What do you mean? You're a good looking guy, you know."

I swallowed my words like I do when I try to talk to a girl. "What do you say, what do you talk about?"

"Them! If there is anything that is true it's that people, guys and girls, love talking about themselves. You just need to ask the right questions and most importantly listen to the answers."

"I don't know, it always feels weird. I feel weird." I confessed.

"You just have to practice. Confidence is the key, Matty. Come on, Practice on me."

I shook my head. "THAT is weird". I tried to laugh him off but he was serious.

"You wanna go in cold?"

I laughed nervously.

"You're a good looking guy. Bums me out that you've got no confidence. Handsome, got a great body" He looked down at my dick. "And you got a pretty good sized cock...someone out there is going to fucking love it."

I looked down at my freshly trimmed my pubic hair and smooth balls I'd attended to just that morning. I'd chopped it a little too short but it did make my dick look bigger than usual.

In that moment, as Jeff mentioned my cock I looked at his. He pulled on it gently and instinctively my hand slipped down and grabbed mine mirroring his movement. Time froze for a moment as I stared at his rod as it began growing in his hand. I felt mine was growing back to life too.

"I better be going..."

I said as I snapped out of my daze suddenly, feeling self aware and awkward. As I stood and began to grab my clothes Jeff caught my wrist with one hand as his other hand gently slid up the inside of my thigh. His fingers brushed over my sack and wrapped around the base of my semi hard dick.

Frozen again I stood still and before I could think what was happening to me he had given my stiffened dick 2, 3, then 4 gentle pumps and...It felt really good. Really fucking good...having some else play with my cock was so exciting. Waves of delight made my thighs flex and I hardened in seconds in as he slowly pumped on my dick. I giggled with a shy delight as this older man stroked my cock to a full erection.

"You like that?" He asked knowing the answer already as the evidence was hot and leaking in his palm. "How big does it get?" He asked playfully. "You know, you shouldn't be too shy about this. You got a beautiful young cock, a good size piece. Mine gets to about 8 inches I think, the girls love it."

"I...I should get going now." I mumbled but my legs stayed rigid, fixed to the spot. I was like a rabbit caught in headlights as Jeff softly wanked my fully erect cock again and again. Taking a deep breath a little moan of pleasure escaped my lips. I'd never been touched in this way by anyone before...let alone by a guy. But i liked it. I really liked it.

"Relax, doesn't this feel good? You do have such a nice cock. Don't you want to play...just a little? We can have a lot of fun. No one else is here....lets have some fun." He said as he began to bend it down towards his mouth.

"Does it go all the way back?" He enquired as he slowly pulled my foreskin all the way back revealing my very swollen purple head. My cock flexed for him as the waves of arousal flowed through me and I nodded yes. Yes!

Sitting on the edge of the sun bed he reached forward grabbing my ass and pulling me closer to him. He licked the tip and Holy shit! I thought...my first ever blow job and its with a man! An older man..and I liked it. I was so turned on as my cock passed his lips and he sucked me into his warm mouth. The sensation was incredible as he sucked my virgin cock back and forth, his tongue moving around and over the tip of my now raging hard on. He took me into his mouth over and over, this felt amazing.

I don't know why, a weird kind of hetro-normative guilt maybe but I felt I had to say something I didn't even know if it was true I was so green. "Jeff..I'm not gay." I said quietly as he slurped over my teen hard on. Overwhelmed, I felt dizzy as the blood rushed from my head to my loins.

"That's OK neither am I." He said taking my cock from his lips but continuing to gently tug on on it while he spoke. I looked at him slightly confused. "You learn a language back in school, French or Spanish?" He asked.

"French." I gulped as the warm pleasure of being masturbated filled my body.

"Does that make you French or do you think maybe you have to go live in France and eat cheese for a while?"

I laughed a little "I guess so." Still stood frozen enjoying but enjoying the masturbation.

"Just relax. I'm married remember. I like girls too. Its just some fun."He said as my cock slipped back into his experienced mouth.

"Yeah, I like girls too. Its just some fun I guess." I mindlessly repeated as his hand stroked up and down on the 6 inches of my young prick. I was in now. I'd gone all in and was going to let him do this. Im not sure his logic was 100% but in that moment I was just enjoying being this man's plaything and the object of his lust.

The music played but I heard him as he moaned as I let him take over. Pulling me down on to the sun bed, as my dick slipped from his mouth. I couldn't speak as he opened my legs wide, grabbed my young cock and continued blowing me while he explored my body with his hands.

I couldn't believe this was happening but I was loving it. I'd only ever thought of girls sucking me off but I was loving being pleasured and controlled at the same time by this stronger and older man.

Jeff's head bobbed up and down on my cock and I felt my orgasm begin to swell deep inside me. He pumped my cock over and over and it felt more powerful that any orgasm I'd felt before.

I panicked thinking...I can't cum. Not like this!

Embarrassed and breathing deeply, I pushed Jeff off my cock and shifted my hips removing myself from his mouth. He looked up with a smile.

"Are you going to cum?" He asked.

I nodded yes with a panicked look on my face.

"That's good, so cum." He said nonchalantly and with a wry smile as he went back to sucking and pumping my throbbing cock even harder than before.

It felt like my cock had grown to twice its usual size and my balls pulled high. I threw my head back and groaned as I began to jet my cum into his mouth as he sucked and swallowed it down. I felt my pulse in my cock and Jeff brought me to a delicious orgasm and the waves of pleasure washed over me. My body convulsed and he continued to milk my dick and swallowed all of my hot young cum.

As my cock began to soften Jeff kneeled up, his pole at a half mast but glistening pre cum as he took hold of it at the root and wagged it playfully in my direction.

"Now...it's your turn" he said with a raised I eyebrow. "Have you ever?" He already knew the answer but enjoyed asking the question anyway.

I shook my head still shocked and a little dazed from the most powerful release of my young life.

Most guys lose interest in sex after they cum and just want to sleep. Me, I can go again after a short period. They call it a refractory period and at this point I didn't want to stop. I wanted to please him too. I was so horny and Jeff had been so very good to me it seemed only fair to take care of him.

"You have to try it, you are going to love it. I promise." Jeff moved closer to me and began his instructions. "First just play with it a little.

"OK" I replied and reached out mesmerized by his dick as it looked so big and I was eager to play with it. It was bigger than mine, about 8 inches or so compared to my 6 inches. Reaching out to touch it for the first time it felt really hot and hard in my hand as I tugged it up and down and smiled. I explored feeling that moment of resistance where I was pulling it too far then sliding my hand back up the length and could feel it grow harder in my hand. After I had done this a few times I worked up some speed. Tugging his cock faster.

"That's it, not too fast. You have to build up to it...slowly." He began guiding the motion of my hand mentoring me, the willing student, as I pulled on his beautiful prick. I was admiring it, staring at it. Enjoying how thick and powerful it looked it my hand. The skin tone and thick veins, it was spectacular.

"Are you ready to try tasting it?"

I nodded looking up at my friend.

"Just start by licking it. Lick the base and work up to the tip."

I began doing exactly what he said. Following his instruction dutifully as he pointed where I should focus my attention.

"That's it, now kiss it like you would a girl. Gently, start to make out with it. Kiss it up and down. Up and down the length of my cock." This instruction sent a jolt through my body. I began to grow hard again.

I wondered if someone might see us together. The girl next door. She might see me about to lick and suck this older man's big cock. My head turned, looking around and making sure we were alone away from prying eyes.

As if reading my mind he said "Don't worry, we're alone. No one can see. Now...start licking it."

I followed his instructions opening my mouth and letting my tongue taste the length of his cock for the first time. I licked and gave it tiny kisses and it pulsed in my hand as I did. This was so wild I thought, I was licking a cock for the first time!

"Like this?" I said quietly, wanting to please. Wanting to do it how he liked it as I planted more little kisses along his measure.

"Just. Like. That. That's really good. OK now, slowly lick the tip. Don't rush it, savour it. Taste it, you wanna taste the pre cum?"

"MmmHmmm" Acknowledging him timidly as I continued to kiss the length.

He passed the tip of his finger over the end of his cock scooping up a drip of hot pre cum as I watched, my eyes wide open. I opened my mouth and let him trace it over my lips. I licked it up and nodded approval, sucking his finger with a little embarrassed moan. I liked the salty sweet taste. I fucking loved the taste and looking up at him wide eyed I wondered if it will all taste so good.

Tracing the measure of his rod with my tongue from the base until I reached his swollen head. I began to circle my tongue around it and kissed it gently.

"Are you ready to try giving me a blow job? Sucking it? You'll love it." Jeff ran his hands over my head willing me to start sucking his cock for him as my making out with it was becoming more keen and excited.

He was so turned on at this point. A young man, a virgin, on his sun bed. Naked and licking his cock and balls. So eager to please him.

I opened my mouth and let his dick slide in over my tongue and a moan escaped me as I let him inside. Slowly, I began sucking his cock, giving him my very first blow job. He moaned as he gently fucked my lips. I think I was doing a good job as his hips began to thrust his cock in and out of my mouth while he while he told me what to do.