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Tag Archives: Boy

A vacation to remember

04 Sunday Mar 2018

Posted by BNG in Adult Fantasy, Anal Sex, College Sex, Erotic Fansasy, Erotic Fiction, Erotic Romance, Erotica, Gay, Masturbation, Oral Sex, Sex Stories

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Tags

anal, Boy, Fiction, First Time, Gay, masturbation

 Introduction:

A married man is surprised to be sexually aroused by a young man while on vacation.

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I was on a bench on the promenade at Playa Las Americas with my coffee and the latest English language newspaper. Looking out over the beach and the clear blue Atlantic. Enjoying the warm morning sun. A vacation in Tenerife was just what I needed. A week away from a stressful few months at work. We’d intended for my wife to be there, but at the last minute she’d had to cancel because of her job. But she told me I should go on my own, anyway. Knowing how much I needed a break.

As I sat there, I was people watching. Vacationers walked up and down in front of me in a continuous stream. Some families, some groups of young guys, some groups of young girls. The warm weather, even so early in the day, prompting some very skimpy clothing.

Girls in tiny swimsuits were attracting my attention. I had on my sunglasses to disguise where I was looking. Then a strange thing happened. A young man about 20 passed in front of me. He was wearing speedos and nothing else. Just carrying a bag and a drink.

His slim, smooth body somehow distracted me. I turned my head as he passed and watched him. From the rear, I watched his bottom as he walked away. It moved like a girl’s and I found myself staring. He turned his head and looked at me. There was nobody near him. It was obvious I was looking only at him. He had caught me checking him out.

He smiled a sly smile, turned and continued on his way. Wow, what was that all about? I thought to myself. I’m not gay. I don’t get turned on by guys.
But I realized that I had been turned on by this youth. His smooth, suntanned skin and his feminine ass in those tight speedos had had an effect.

Too much of an effect, in fact. I had an erection. Oh god! I’d had got an erection from looking at a boy! What was going on? But one thing was going on. I was horny as hell.

I wanted to go back to my hotel but I couldn’t get up because my hard cock would be making a big tent in my shorts. I could hide it behind my paper, I guessed, but it would be so obvious. I decided I should just sit tight for a little while and let it subside. I opened up my paper and started to catch up on the sports.

My head was buried in the paper so I didn’t notice immediately that he was approaching. Only when a shadow covered me, I looked up and there he was! The same young man who had had such a curious effect on me a little while ago.
“Hello” he said. “Can I join you”?

I lowered my paper. He stood there, in front of me. The first thing I saw was the bulge of his penis wrapped up in his tiny swimming costume. It took an effort to look up to his face.
“Uh, hi. Yes, I guess” I was stammering.
He sat down next to me. Close. I felt his leg touching mine.
“I caught you” he said.
“Caught me?”
“Yes, you were looking at my ass”
“No, no, not me” I denied it, but I could feel the blood rushing to my face.
“It’s OK. I know you were. I think you liked it.”
“I wasn’t. Honestly.”
“Don’t be shy. You can admit it.”
I was silent.
Then: “No you’re mistaken” I told him, firmly.

“OK, if you say so” he said, although his tone of voice was saying ‘you are lying and we both know it’.
He went on his way. I sat for a few more minutes and headed back to my room.
My hotel was designed in such a way that every room had a balcony overlooking the ocean and each was private.
I enjoyed the opportunity to strip off my shorts and lie naked in the sun. There is no feeling like it.
As I lay there, my thoughts went back to the alluring young man I had encountered and I felt my cock stirring.
My hand slipped down my body and I idly started stroking myself. The sun lotion I had liberally spread all over made it easy for me to run my hand up and down my stiffening shaft and soon I was masturbating. My fist gripped my hard shaft and slid up and down its length as I released my inhibitions and allowed myself to think about the boy.

This was MY fantasy, no need to be ashamed while I jerked off. Jerked off thinking about…
In my mind I thought of his ass in those speedos. Recalled how his cheeks moved as he walked away from me.
I thought about the bulge I had seen as he stood in front of me.
I fantasized about what might have happened if I’d admitted to him that I had been looking at his ass and hips and body as he passed me.
The image of his ass in my mind.
Imagining how it would feel to touch him. To run my palm over the curve of his sweet behind.

Stroking myself. Oh god I was so hard.
Wondering what his cock looked like.
Stroking myself. Up and down. Harder. Faster. The boy in my mind’s eye.
It was only a minute or two before I came. Strong as I can remember cumming since I was a teen.

The cum shot out and up my chest. Most of it slithered down off my oiled body and onto the towel that was under me. A little pool formed in the hollow of my sternum.
On a whim I dipped my fingers into it and brought it to my mouth.
Again with the new stuff! I had never in my life been with a guy or thought about it. Yet here I was, having an orgasm thinking about a guy and now I was tasting my cum for the first time.
I sucked my finger tips and then pushed my fingers deep into my mouth. Something else new.
And, as I lay there with two fingers going down into my mouth, I thought about sucking that boy’s cock.

That night, I masturbated again to the same fantasies. It was suddenly becoming an obsession and I was regretting my denials to the boy that morning. I decided that I would definitely not do so again. And I went to sleep hoping that the young man took a regular walk along the promenade each morning, because I was definitely going to be there tomorrow, in case he passed by.

I was down there again early the next day. Eager. On the same bench, same coffee, same paper. Pretending to read behind my shades, but really keeping a watchful eye for the youthful adonis who had approached me the morning before.
My mind was made up that I would take him to my room if he stopped again. I had chosen not to wear boxers under my shorts today; it added to the frisson I was feeling.

And then…. there he was. Still in those tiny speedos, sauntering along the boardwalk. A beach-bag dangling from his shoulder.
He swayed his hips as he walked. Even from the front I could see the sensual movement of his hips and recalled the appeal of his tight little bum.
He turned his head towards me and made a wry little smile.
I lifted my sunglasses to my forehead and looked at him. Today I wasn’t going to pretend a lack of interest. In fact, today I wanted him to know that I was very interested.

He changed course and slowed to a stop, standing next to where I was sitting.
We both faced out to sea. His sweet ass barely covered in the silky fabric of his swimming costume was a foot from my face.
“So, Mr “I wasn’t looking”, how are you today?”
“Very well thank you.”
“Today you are looking at me.”
“Yes, and I was yesterday. I am sorry I denied it. It was rude.”
“Rude to stare at boys half your age, or rude to deny it?”
Hmmm which? What was the right answer?
“Both, I suppose.”
“Well, perhaps I will forgive you two times.”
“What’s your name?”
“Luke, what’s yours?”
“Michael”, I told him.

“Hello Michael, I am pleased to meet you.”
“I’m pleased to meet you too, Luke. I’m glad to see you today.”
“I think I can make you more pleased, Michael” he murmured. Still looking away from me. Still teasing me with the proximity of his youthful body.
“Would you like to sit?” I asked. I was intensely aware of his sexy bum so close to me and was fighting an urge to either lean my face towards it or to raise a hand and start fondling him.
He turned and looked down at me.
“No I think you must buy me breakfast.”
“Where?” I asked.

“Room service” he replied “which is you hotel?”
I told him the name. It was half-mile to the South.
“Come on!” he told me and walked off in that direction.
I stood to follow. I realized that I had another erection. Pulled my shirt down as well as I could and tried to hide it but it was too obvious.
He turned and saw my situation. Laughed, and then walked on more quickly.
I had to hustle to keep up and it made hiding the bulge in my shorts impossible.
The fast walking pace had my cock bouncing up and down inside the loose shorts, rubbing against the material and making me even further aroused.
Passers-by were noticing…. an older man chasing after a young fem-boy and with a hard-on.

But these were all strangers to me, I decided. I ceased caring and caught up with my new friend.
I reached out and put a hand on his forearm.
He checked his pace. We walked on together.
People coming towards us could still plainly see that I was sexually aroused. I saw many people young, old, male and female staring at the lump in my shorts, looking at this mismatched couple and I saw several different reactions.
There was shock on many faces as they jumped to the right conclusion.
I saw two men look at me with envy. We walked past one guy, around Luke’s age, sitting on a wall. I saw him looking at us and he moved his hand and quickly grabbed his package, giving himself a squeeze. I heard him “tut tut” quietly, bit the smile on his face was one of approval.

Another man was walking with his family. His wife was oblivious as her husband stared at my friend, looked to my lumpy shorts, looked back over Luke’s smooth, tanned body and finally into my eyes. The corners of his mouth came up in an almost imperceptible smile, his eyebrows raised and lowered in a flicker and he nodded ever so slightly as we passed. He knew. He was probably into it. A married man, with homosexual fantasies. Like me.
I should be ashamed…. It actually made me more aroused.

We headed into the hotel grounds, past the pool area and through the lobby to the elevators. Most people were coming down from their rooms and we had a car to ourselves. I hit 6 and the doors closed. I wanted to touch him. I wanted to feel his smooth skin under my hands. But I didn’t want to be seen on the security cameras, molesting a boy half my age, so we stood in silence. He moved closer to me. It took all my will power to keep my hands to myself. We got to my floor and I couldn’t resist. I put my hand on his sweet ass and steered him to the right, towards my room.
The maid had already been, so the place was tidy. But I hung the Do Not Disturb sign, anyway, and closed the door.

Luke dropped his beach-bag, turned to me and asked “what do you want to do?”
“Did you want breakfast?”
“No, that was just a joke. I want something else.”
I stammered…. now I had to confess something to him…
“I…. I, um, I never did anything like this before.”
“Oh I know, Michael. I know. But you want to don’t you?”
I did. I wanted to.
“Yes”. My voice was quiet.
“Shall I tell you what I think you want?”
“Yes, Luke”

“I think you want to suck my cock.”
His hand went down inside the front of his swimming trunks and he started rubbing himself. I watched his knuckles through the sheer fabric.
“You can touch yourself, if you like” he told me. I moved my hand to the front of my shorts and rubbed my hard cock.
As I touched, I noticed that precum had made a wet spot there. Had that been there as we walked past all those people? Oh no! How embarrassing!
But now it didn’t matter. I rubbed myself as I watched Luke playing with his cock and balls.

“And I think you might like to fuck me, Michael” Luke said, and turned around again.
He bent at the waist and, with one hand on each hip, started slowly slipping out of his speedos.
The top of the crack of his ass came into view. He looked behind himself at me and grinned.
“You like my ass, Michael?”
“Yes…. yes I do”
I was entranced. Even if I’d wanted to I couldn’t have taken my eyes off his bottom as he slowly revealed it to me.

“I know it’s sexy. I knew you were looking at me yesterday.”
“I was. I was. It is so sexy. I never looked at a boy before you.”
“I know. I know. It’s OK, though. Just enjoy looking at me now. Don’t feel guilty.”
I was so hard. My cock felt like iron and I traced its outline with my fingers through the material of my shorts.
The speedos came down to the tops of his thighs and he straightened up.
I watched as he flexed the muscles of his ass, first one cheek then the other, making it dance for me.

His hand went back to the front and I watched him from behind as he stroked his cock.
I reached out and tugged his speedos down to his ankles. He stepped out of them and spread his legs.
“You can touch me if you want”
I moved to my knees behind him. My nose was inches from his naked bottom. Starting at his calves, I moved my hands gradually up. Hi skin felt as smooth as it looked. What little hair he had on his legs was fine and soft.
I moved my hands around to the front of his thighs and I pulled him towards me. On my knees, hugging him from behind. Placing my cheek against his ass. Feeling the skin of his body on my face.
“Yes, Michael. That’s right. Love my body. You know you want me. You want to suck me. You want to fuck me.”

He reached down and took my hand from his thigh and raised it so that I could touch his hard penis.
It was erect and I could feel that there was no hair anywhere. But it was smooth. This youth had waxed.
His cock felt wonderful in my hand and I stroked him from behind, still kneeling.
His beautiful ass was there and I couldn’t stop myself… I kissed the cheeks of his ass all over while I stroked his hard cock from behind.
But, I wanted to see it. His penis. Wanted to watch myself stroking him.
With my other hand I gently pressed on his leg… wordlessly asking him to turn around.

He turned towards the direction of the hand on his cock and I saw my hand on another man’s cock for the first time.
“You like doing this, don’t you Michael?”
“Yes Luke. I didn’t know. I didn’t know it would be so good to touch a hard cock.”
He moved his hips gently in time with the rhythm of my hand.
“Do you want to put it in your mouth, Michael?”
My hands went to his ass and I pulled him to me. I opened my mouth and took him inside.

His cock felt great in my mouth. He placed his hands on the back of my head and held me. I sucked and licked him.
“Yes, Michael. Yes, you like my cock, don’t you? You like sucking cock.”
With his cock deep in my mouth, I could only nod. “Mmmm Hmmm” was all I could manage. I didn’t want to take his dick out of my mouth.
“You might make me cum, Michael. Do you want me to cum in your mouth?”
Yesterday I masturbated, thinking about this youth shooting his cum into my mouth. And, to add to my fantasy, I had tasted my own cum for the first time. While I thought about Luke.

Thought about his sweet bum, thought about sucking him off.
Having him cum in my mouth for real was fantasy turned into reality. I gripped his ass tighter and sucked harder. Bobbed my head back and forth on his cock. Sucked him until I felt his buttocks clench.
“I will cum in your mouth, Michael”
“Mmmmmmm” I held on. My lips tight round the base of his cock. Kneading his ass with my fingers.

“”Now, Michael!”
His sperm spurted from his cock. I opened up and some cum escaped, trickled down my chin, but I kept most if it in my mouth. He withdrew his cock and I closed my lips.
Then I was able to swirl his cum around in my mouth and was able to taste it properly. And then I swallowed. It was great. Tasted nicer than my own. Or maybe I was getting to like the taste more.
Before yesterday I had never tasted cum at all, and now I was able to make comparisons!
I stayed there on my knees for a moment, savoring the lingering taste in my mouth.

He reached down and grasped my hand. Lifted me to my feet. I stood in front of his naked body. His glistening cock was beginning to lose its hardness. As I looked down, I realized how petite Luke was. I stand at 6′ and he must have been a full foot shorter than me. But he was perfectly formed!
His fingers found the button of my shorts and the zipper and he quickly had them down. His hands worked their way up under my t-shirt and he ran his hands over my pecs and then his fingertips played with my nipples. It was such a fine sensation. I tugged the shirt off and then we stood facing each other. Two naked males. My hardon poking him.

“That was so nice. You gave me a fantastic cum, Michael”
I was pleased and told him so.
“Did you like it? Did you like sucking me? Did you like having a cock in your mouth? Did you like a boy cumming in your mouth?”
“Yes, yes, yes and yes”
“You made me feel special, Michael.” I smiled down at him. “Can we kiss now?” he asked.

He strained upwards toward me and I leaned down. I placed my lips on his. They were as soft and smooth as the rest of his skin. It was like kissing a girl. He opened his mouth, inviting me to put my tongue into it.
My hands roamed all over his tight smooth body as we continued for several minutes.
Then I put my arms under the cheeks of his ass as we kissed and lifted his slim body. He climbed up onto me. His legs wrapped around my waist. My erect penis was rubbing against the crack of his ass.

Luke broke away, still in my arms, still lifted off the floor and looked into my eyes.
“Do you want to fuck me, Michael?”
Oh jeez. Do I want to fuck this sexy boy?
“There’s nothing in the world I want to do more, Luke”
“I want you to. I want to feel your cock in my ass.”
“I want to fuck you Luke. Your ass is so sexy.”
He unwrapped his legs and slipped down to the floor. He went to his beach-bag and grabbed a bottle. Turned to me and winked.

“I like to be prepared when I meet horny older men.”
He squirted some lubrication onto my cock and rubbed it up and down.
“Oh Michael… look how big and hard you are!” I nearly shot my cum just from his touch. But he finished covering me with lubricant just in time.
Then I might have cum again just from the sight of Luke bending over and pushing slippery fingers into himself.
He watched my reaction over his shoulder.
“You like that?” he asked. I had no voice to reply. But he knew the answer and took his time, fingers going in and out of his ass while I stared at the show he was giving me.

Then Luke went into the bathroom and came out with a towel. Pulled back the covers on the bed so that there was just the bottom sheet, laid out the towel and, at last, lay down on his tummy.
His slim, smooth, sexy bottom lifted just off the bed.
“Fuck me Michael. You want my ass. I want your cock.”
I was on him in an instant. The sexy ass under me was quickly impaled by my hard cock. He was ready for me and I slipped my entire length into him in one thrust.
His ass gripped my cock gently and firmly at the same time. It was the most amazing sensation.

“Oh Luke, you sexy boy” I whispered into his ear. Beginning to fuck in and out of his sweet, tight ass.
Bouncy, bouncy ass. Smooth, soft, receptive.
He lifted himself up to meet me as I drove my cock into him again and again.
“You like fucking me, Michael” he said.
“Yes, Luke. I like fucking you” I nuzzled the nape of his neck as my cock went deeper and deeper into his bum.
“Boy’s asses, Michael. Now you know what you like”
“Now I know”

“Kiss me Michael”
He twisted under me and I lowered myself to reach his lips. Thrusting my hips over and over, pushing my tongue into his mouth; pushing my cock into his ass.
He wanted more intimacy and moved so that he was on his back and I was between his legs. His arms came up around my neck and his ankles on my shoulders. My cock drove deeper still into his lithe, slim body.
I gripped the sweet cheeks of his ass as I fucked him and, with his arms still clinging onto me, I raised myself. I was standing now, with this man-boy impaled on my cock. His ankles on my shoulders and my hands supporting his ass.
I walked out onto the balcony.

The sun warmed our naked bodies as I fucked Luke’s ass.
I laid him on the sunlounger and fucked him there.
I leaned him against the balcony railing and fucked him from behind as we looked out over the ocean.
I bent him over the table. Fucked him some more.
Then I took him back into my arms and he climbed back onto me.
Again I was holding him in the air by the cheeks of his ass and I lowered him down onto my erect cock.

His ass slipped over my meat and I lowered him down as far as he could take it.
He clung on to me. It was spectacular.
His lips were locked on mine and I was lifting his entire body up and down on my cock.
Soon, too soon – I wanted to fuck his ass all day, feel his ass enveloping my cock – I knew I was close to cumming.
With my cock still inside him, I carried Luke from the balcony back into the room and laid him down on the bed.

He flipped back onto his belly and lifted his ass up for me…
I climbed up behind him and started fucking him doggy-style, but soon we were flatter on the bed and my weight was supported on my forearms on either side of him. I liked feeling his bare skin against mine. I lowered myself again and he took my weight as I shoved my cock into his ass time after time after time.
The ecstasy was building. This lad, this femboi, this temptation, this unbelievably sexy ass that my cock was buried in….. was bringing me to my peak.
“I’m going to cum, Luke”

“Mmm yes. Cum up my bum. You know you want to. You’re going to have an orgasm from fucking a boy up the ass, Michael. Naughty man. Do you feel good? Does my ass feel good on your cock?”
“Fucking excellent!” and I came.
Like never before in my life.
More than that first shady hand-job behind the bicycle sheds.
More than that first ever blowie from the girl who’s name I never remembered but who’s mouth I will never forget….
More than my first ever fuck.

This was more. This was unreal. My cum filled his little asshole and with each thrust of my spurting cock some leaked out onto the towel he had put down.
I fucked in and in and into him. Cumming and cumming and cumming until I was empty. Until I felt like all my bodily fluids were inside this sexy kid’s ass.
I was spent. I collapsed onto him for a moment and then we rolled as one onto our sides. My cock stayed in his ass.

“Oh Luke, you were amazing” I breathed into his ear.
“You were as well, Michael”
He moved away and my cock slipped out. He got up and went to the bathroom. I heard the shower.
I lay there catching my breath and then I must have drifted off in the warm air coming in through the balcony doorway.
The sound of the room door closing brought me awake. Luke was gone.
But the memories he had provided would sustain me for years.

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Working ‘Girl’

01 Thursday Mar 2018

Posted by BNG in Adult Fantasy, Affairs, Anal Sex, College Sex, Erotic Fansasy, Erotic Fiction, Erotic Romance, Erotica, Masturbation, Oral Sex, Passion & Pleasure, Sex Stories

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Tags

Blowjob, Boy, fantasy, Gay, Prostitution, Transvestite, young

This idea has been in my head for a long time. If you’re not into young, crossdressing, or older man/younger boy, then turn back now. I do not condone anything in this story, it is simply a fantasy. I hope you enjoy it!

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Brian sat impatiently on the park bench, fidgeting in anticipation and excitement. He quickly checked his phone for the time yet again, seeing it was just after 1AM. It was the perfect time for meeting a customer. He reached over to run his fingers along the signature red bracelet over his left wrist, which let men in the area know he was ‘working’. His ears perked up when he heard some noises off in the distance, a gentle rustling in the bushes. Brian smiled slightly, knowing someone else must be doing just what he was about to do now.

He thought about that video game he wanted, the one all the other kids at school were talking about. But at 14, he was too young to have a job, and too old to convince his parents to buy things for him anymore. More chores and the prospect of getting an actual job wasn’t exactly palatable to him, so he went browsing on the internet for a better way to make money. After finding some questionable web sites with some not-so-mainstream suggestions, he decided that this was the best way for him to make a quick buck. The fact that it excited him so much definitely helped.

Looking down and running his eyes over his smooth petite body, he double checked himself to make sure his outfit was in order. He lifted his butt and adjusted the short black pleated skirt hitched tightly to his waist, which barely concealed the small red thong that clung tightly to his smooth boy parts and wedged right between his firm butt cheeks. The fabric felt amazing against his skin, as did the light breeze across his soft, freshly-shaven legs. The black heels strapped to his feet were slightly uncomfortable and difficult to walk in, but they looked great on him.

As his eyes adjusted to the dark and moved back up above his waist, he couldn’t help but run his hands up his flat, exposed tummy. The tight pink spaghetti-strap top he had ‘borrowed’ from his sister was just small enough that it showed his midriff when he sat up or moved at all. It hugged the black padded bra underneath, carefully stuffed with tissues to give him a slight bust. Cupping his fake chest in his hands, Brian let out a soft moan. He knew the pervy men that frequented this area would like it as much as he did.

Flicking his tongue across his lips, he tasted the bright, fruity pink lip gloss smeared over his pouty lips. He went easy on the make-up, trying not to look too trashy, instead shooting for a more naturally feminine look. Brian’s own soft features, which were often the target of school bullies, tonight would work to his advantage. Just some light mascara to accent his eyes and the lip gloss was all it took to bring out those alluring features.

Just as he finished taking himself in for the third time tonight, he heard some light footsteps coming down the path toward his bench. He quickly adjusted himself, crossing his legs and trying to appear casual for fear of someone normal coming this way. His heart fluttered as an older man came into view, clearly edgy and nervous. Brian’s heart began pounding in his chest, both from nervous anticipation and strange excitement. He turned and smiled softly at the man, whose darkened silhouette was coming into view.

The man bit his lower lip and swallowed hard, his eyes clearly roaming over the young tart before him. With a final breath, he sat down next to Brian, averting his eyes. Brian followed his every move, turning slightly to his potential customer of the night to show off a little more. He waited patiently for a minute, trying to let the man calm his nerves. Finally, he glanced over and smiled at Brian, his face slightly flushed.

“Um.. hi,” he practically stammered. Brian smiled wider and scooted closer, keeping his voice low so as not to sound too boyish.

“Hiya, mister.” A soft moan escaped the older man’s lips, clearly turned on by the overall package. His eyes moved to the red bracelet around Brian’s thin wrist, reaching out tentatively to rub his thumb over it. He glanced around cautiously before leaning in and practically whispering “Are… are you.. working?”

Brian let out a soft girlish giggle, placing his smaller hand on the man’s thigh. He practically jumped from the touch, a bulge growing across the front of his pants. “I sure am,” was Brian’s simple reply.

The man visibly swallowed hard and spread his knees a little, no longer making any effort to hide his excitement. His large hand rested over Brian’s smaller girly one, and he leaned in close, his breath smelling of alcohol. “Um.. I’ve never done this before.”

Brian’s hand squeezed his customer’s thigh softly, slowly tracing small circles along it with his fingertips, trying to boost the man’s confidence in his decision. “That’s ok. I’m very discreet,” Brian cooed.

His eyes seeming to light up, the stranger smiled and took a deep breath. He seemed to compose himself, taking one last quick look around the park before leaning in closer and muttering, “So um.. how much?”

Taking this as his cue to pour on the marketing, Brian shifted his position so he had one leg tucked under his butt and was completely facing the man. He leaned in very close, pressing his padded chest against the stranger’s arm and pushing his hand between the man’s thighs, cupping his bulge. His voice was low, but he made no effort to hide his own excitement. “I’ll suck your cock for a hundred bucks, daddy.”

The man shook at the comment, his bulge swelling and straining against Brian’s hand. He quickly reached for his wallet, but Brian laid his hand over the man’s to stop him. Glancing around, he smiled and leaned close to his ear, whispering softly “Not here, daddy. Follow me.”

Brian did his best to stand up without creating a tent under his skirt, his own excitement straining the fabric of the panties underneath it. He held his new friend’s hand as he stood, and soon felt a gentle tug as it was used to support the larger man that stood next to him. He, however, made no such attempt to hide his bulge, the thick member outlined clearly through his pants. Gripping his hand, Brian led him along like a lost dog. He pushed directly into the bushes behind the bench, leading the man a short distance to a very small, secluded spot among the foliage.

There was very little light, and the only sound was a soft breeze rustling through the branches above. Brian turned swiftly and smiled up at his new client, reaching out to cup his hand over the bulge in his pants. He watched anxiously as the stranger reached again into his wallet and extracted a single $100 bill. He held it up in his hand, appearing to contemplate for a second. His eyes ran over the short skirt around Brian’s hips, and he blushed before blurting out softly “Now.. you are a boy… aren’t you?”

A small smile crept across Brian’s lips at the question. He lifted his skirt, flashing his own package neatly tucked into the thong. The head was already peeking out, so Brian made no move to hide it. Instead, he reached down and pushed the small triangle of fabric down to let his boyhood spring out, exposing himself to the man. It was only 6″ long with a small set of freshly-shaved balls, but its fat head and smooth texture complimented the feminine look nicely. The stranger groaned in approval, quickly handing the crossdressed boy his money.

Quickly taking the bill and stuffing it into his bra, Brian calmly slipped to his knees and reached up to press his hands against the man’s pants. He wasted no time and began undoing them, not wanting to stay out any longer than he had to; his parents could notice at any moment that he was missing. As he unzipped the pants before him, a pair of blue boxers with a noticeable wet spot across the front came into view. Pulling the stranger’s pants down just enough for access, he next tugged down the blue boxers and smiled as an average-looking cock spring out. Brian estimated it to be just a bit longer than his own, but pleasantly thick and with a long vein running along its length. The circumcised head was smeared with shiny, sticky precum, with a dribble of it already flowing from the very tip.

The boy smiled up at the man and licked his lips, sliding a hand up and wrapping his fingers around the shaft. “Nice cock, daddy” Brian cooed, gently squeezing the thick manhood in his hand. The man simply grunted in response, his eyes locked on the kneeling crossdresser. Brian started to stroke it slowly, thankful that it was a manageable size; yet he secretly lusted for a larger one, thrilled at the dirty thoughts running through his own head. But this one would have to do, money was money after all.

Without hesitation, Brian leaned in and eagerly took the dick into his mouth. Clamping his lips just under the ring under the head, he then swirled his tongue over the head. The man let out a moan of pleasure, and his cock responded by swelling and releasing a steady flow of precum over the warm tongue that enveloped it. The precum was so sweet that Brian took a second to lick the tip clean before pushing down an inch, starting to bob up and down on the man’s cock. His lips wrapped tightly around the shaft, and he sucked gently each time he pulled back toward the head. In no time the man was moaning and whimpering ecstatically above him, resting a guiding hand on the boy’s head.

Taking more and more of the delicious cock into his mouth, Brian soon felt the head thumping against the back of his throat. Fingers curled in his hair and tugged gently, urging him to go deeper. He acquiesced and pushed down further, wincing and swallowing to allow the head to pop into his throat. The rest of the meaty dick slipped right into his mouth, balls now resting on his chin. He swallowed hard and resisted the urge to gag, glancing up at the owner of the cock buried in his mouth.

The man was glaring down at him, his eyes starting to glaze over in lust. His voice was soft but strained. “Holy shit… suck that cock, you little slut,” he encouraged, rocking his hips forward to thrust slightly into Brian’s mouth in rhythm with the boy’s bobbing. Brian’s eyes started to water as he looked up at the man, working along his length with his mouth and throat. He slipped a hand under the balls that bounced off his chin and cupped them gently, gagging slightly as his throat was used strictly for his partner’s pleasure.

Spit began to dribble down Brian’s chin and coat the balls that smacked against them. He could hear the man standing above him panting and grunting harder, but his pace only seemed to quicken. “You like Daddy’s big cock, little boy?” The dirty talk coming from this seemingly shy man was driving the young cocksucker wild. His own erection leaked precum all the way down his shaft, making it shimmer in the dim lighting. Brian resisted the urge to touch himself and focused on pleasuring his client instead.

As the teen teased his new Daddy with his hand and mouth, he was greeted by a hard thrust into his mouth. He gagged hard, breathing hard through his nose as the head was just as quickly tugged from his throat. His fingers curled behind the man’s balls, pressing on the spot just behind his sack. He hummed softly over the head as it dragged across his tongue, more sweet precum coating it and mixing with his own spit. His tongue flicked across the very tip, causing a sharp grunt to release from the man’s lips. The cock was pulled from his mouth, leaving his painted lips with an audible ‘pop’.

“Tell daddy how old you are, little slut.” The dirty man stood over him, panting and grunting as he furiously pumped his slick shaft in his hand. Brian smiled up at him and spread his knees wider, giving the man a good look at the cock between his smooth legs, as if to confirm once again that he really was a boy.

I’m only 14, daddy,” Brian eked out in the most feminine voice he could muster. No sooner had he spoken those works and opened his mouth that Daddy began to buck and grunt. His thick cock throbbed and erupted long spurts of white gooey cum all over the boy’s face. He quickly shut his eyes, feeling the thick fluid land all over his face and stick to his skin. Some of it landed in his mouth and over his tongue, more dribbling down his chin.

Brian opened one eye and glanced up just as the man was working the last drops of cum over his perky fake chest, getting spots of cum onto his top and chest. The spent stranger panted and almost fell backwards as his knees buckled. He reached for a nearby tree to steady himself, struggling not to fall over in post-coital bliss and exhaustion. He managed a weakened smile down at the cum-covered teenager, looking over his work.

As the cum-coated sissy wiped some of the seed from his face and smeared it across his top, he watched in mild amusement as the man fumbled with his boxers and pangs. He looked slightly ashamed but managed to gather his nerves as his cock was tucked back safely into the confines of his boxers. “Wow, that was… that was amazing. Are you really 14?” he asked, looking curiously over the boy.

Brian simply nodded and tried to giggle girlishly, flicking his tongue across his lips to lick them clean. The man let out another soft moan, seeming to blush as he realized what a dirty thing he had just done. He reached for his wallet and produced a $20 bill, then quickly pushed it into Brian’s bra right next to the first, being careful not to touch the cum peppered over his skin and clothing. “You earned that, sweetie.”

Brian smiled wide to thank the generous man, watching as he turned and made his way out of the dense bushes and into the night. Just as the man was out of sight, Brian reached between his smooth thighs and furiously stroked his own throbbing cock. He cupped one of his padded breasts in his other hand, feeling drops of cum against his fingers. He whimpered softly, feeling his balls tighten as his whole body ached for release.

His knees spread wide, back arching and head tilting back as his smooth young cock released, sending thick long ropes of cum flying out. It landed in thin streams across the grass, the last of it leaking out over his fingers, panties, and skirt. The small spot was quite a mess with a mixture of his and the customer’s cum.

As the adrenaline rush of the encounter washed away, Brian began tucking himself back into the confining panties and attempting to smooth out his sticky outfit. He licked his fingers clean of his own remnants of cum before reaching into the bra and producing his hard-earned money. He giggled when he saw a streak of cum across one of the bills, wondering if anyone would suspect how he got it when he finally went to spend it.

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