Ladyboys Moving to Thailand and my first Ladyboy
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Good Boy Don't Do That free porn video
Justin Calhoun is a good boy. His mother raised him to be kind, sweet, honest and pure. Not that their family was religious, but Mrs. Calhoun made sure her little boy wasn’t going to be the type of man his father had been; lecherous, womanizing and misogynistic. Since he was their only child, Mrs. Calhoun doted on him throughout his life, being stern when needing to be to ensure her little boy became the gentleman she wanted him to be.
Now at 22 years old and on summer break from medical school, he is driving through the countryside when he sees her. She is standing on the side of the road, her right thumb in the air. It is a nice hot summer day, and the slight breeze that rustles the leaves on the trees also caresses her long, straight blonde hair, as it shines in the bright sunlight. Her little white tank top clings to her sweet breasts, and the little denim shorts cling to her upper thighs, her long legs tanned by the sun. Justin Calhoun knows he shouldn’t stop; his mother had drilled into him that you should never pick up hitchhikers. You never knew who was going to climb into the seat next to you. Even beautiful women such as this one could be dangerous. She seemed to be by herself , and the other traits Mrs. Calhoun had entrenched in her son combatted in his head, to see the good in other people….particularly this one.
Justin has never done anything adventurous in his life, he’s always been the dutiful, loving son and he has promised himself that he would do something spontaneous and adventurous (and safe) this summer. He figures this is as good an opportunity as ever.
As he slows down, he scans the trees behind the woman, not seeing anyone else lurking about who might jump him once he stops. He pulls up beside her and rolls down the passenger window.
“Need a lift?” Yes, it’s a cliché, but it’s an appropriate question.
“Yeah, if you don’t mind. I’m heading into the city, the last guy I drove with didn’t get me quite as far as I needed.” She smiles at him, her face tanned like her legs. She has a small rucksack on her back.
“Not a problem, I’m heading that way myself, hop in.” He pushes the door open and she climbs in.
“Thanks! I really appreciate it. My name’s Cindy.”
“Justin, nice to meet you. Seatbelt please.”
He reminds her as she throws her bag into the back. She smirks at him but complies. Justin puts on his turn signal, checks his blind spot, though there are no other cars on the road, and starts toward the city. It is a bit of a detour from his original plan, but he has no obligations for a few days, so this little side trip won’t hurt.
He glances at her out of the corner of his eye as he checks his rearview mirror periodically. She’s crossed her legs and undone the boots she’s been wearing.
“Do you mind if I take these off? I’ve been walking for a bit.”
“Sure, not a problem.”
Her sigh is soft and luxurious as she pulls each boot off her foot and tosses them into the back with her bag. Justin gives a small shudder he hopes she won’t see. He’s never had a serious girlfriend, and the women he had been with were like him, sweet and virginal. He’s only ever kissed a woman before. Cindy stretches her arms up and over her head and sees him glancing at her.
“Everything ok?”
" Y…Yes.” He stutters, returning his attention back to the road. She watches him for a little while, her mind lost in thought as she stares at him. He needs to break the tension.
“…So, what happened that you needed a lift?”
“I’m just exploring the state before going back to school in the fall. I’m taking photography courses at the local college.”
“You’re travelling by yourself?”
“Don’t sound so surprised, you’re by yourself too.”
“Yes, we’ll that’s different because…”
“Because you’re a man and have a car?” Justin knows this sounds condescending. His mother had raised him better than that.
“I’m sorry, it’s just hitchhiking can be really dangerous regardless of gender.”
“You’re right, but I’m a good judge of character and I don’t just get into any car. I feel the person out first.”
“Yes, I know what you mean. I’ve never picked up a hitchhiker before. But you don’t seem like an ax murderer.”
“You do seem like a good boy, Justin.” She grins at him teasingly.
“I’ve gotten that all my life, and to be honest, yes, I am good. I was raised well and apparently, that’s cause for people to comment on.” He doesn’t say this with malice, it’s just a fact.
“I’m sorry, I didn’t mean to offend you.”
“Not at all, it’s just the way it is.” She looks at him again.
“Why are you out driving the countryside?”
“I’m on summer break from medical school. I wanted to explore too. My mom was a little worried about it since I’m on my own but I wanted an adventure, to get out of my comfort zone a little.”
" I can definitely appreciate that. Say, would you mind pulling over for a minute. Just under those trees.”
Justin’s a little confused by the request but does as she asks. Once the car is in park and the engine ticks down to silence, Cindy removes her seatbelt and slides closer to Justin over the gear shift.
“You said you wanted some adventure, I think I can help with that.”
He can smell her sweat, it’s sweet and her body radiates the sun’s warmth. She gazes into his eyes as her hand trails down his chest and over his crotch. She gently rubs him through the fabric of his jeans, waiting to see if he’ll protest. She can see his mind grappling with itself, his good breeding fighting his animal instinct. He finally comes to a decision and leans back into the seat with a sigh. Her grin is wide as she strokes harder, undoing the zipper and button.
“Now look who’s being bad.”
She teases as she removes his cock from his pants. She murmurs her approval and with her other hand removes each strap of her tank top letting it slide down her shoulders until the shirt falls past her breasts. Justin stares at them as she starts to slowly massage his cock.
“Like what you see?” Justin can only nod in response.
Cindy dips her head down and starts to suck his cock. Justin inhales sharply at the initial shock but quickly surrenders to her talented tongue. He braces one hand on the ceiling above his head, his other hand shaking on her back from the sensations he’s feeling. His hand moves to her head, gliding through her hair and resting on the top. He doesn’t push, just keeps his hand there as his hips jerk against her mouth. She tightens the seal over his shaft and sucks harder on each up stroke, increasing the sucks until he cums in her mouth with a long groan. She slowly slides up his shaft and then looks at him as he continues to pant , trying to regain his breath. She opens her mouth to show him the white pearliness inside. He gulps at the sight. She keeps her eyes on him as she audibly swallows his cum. She replaces the straps on her shoulders and sits back into her seat smiling at him. He can’t believe what they’ve just done. He quickly looks around as he comes back to reality, realizing that they’re on the side of the road. But of course, no one’s around and no one’s seen what’s happened. Justin feels excited about having gotten away with this public sex act, but the tiny voice in the back of his head chides him; good boys don’t do this . He replies to the chiding voice; well, I guess I’m not such a good boy after all .
With that, he restarts the car and he and Cindy continue their drive into the city.
It’s late when they finally enter the city limits, and they are both hungry. They’ve spent the rest of the day talking about family and school, their dreams and aspirations for when they graduate. They decide to stop at a cheap motel for the night and have dinner at the small diner next door. After dinner, they go to the motel to check in.
“How many rooms do you need?”
“Just one, please.” Cindy is the first to respond. Justin looks at her surprised. “It’ll be cheaper if we share a room.”
Justin can’t deny this logic, his gentlemanly ways have surfaced again but he quickly tamps them down and doesn’t protest.
“Not a problem, here are your room keys; it’s just down the hall on the left. Room 118.”
“Thank you.”
A s Justin and Cindy walk down the hall to the room, Justin figures he’ll sleep on the couch that night and let Cindy have the bed. They enter the room and see that it’s so small that there is no couch, just a small desk, and a single bed.
“Looks like we’re sharing a bed tonight, ” Cindy observes happily.
“I can take the floor if you’re more comfortable with that.”
“Not at all, I’m not worried, are you?” Justin thinks for a minute before responding.
“No, I’m fine with it if you are.”
“Great!” Cindy heads towards the bathroom. “I’m tired, do you want to go to bed?”
“Yeah, that’s fine with me.”
“Ok, see you soon.”
Justin gets into his striped pajamas as he waits for Cindy to come out. He turns off the lights and climbs into the small bed under the covers. A minute later the door opens and Cindy is silhouetted by the light from the bathroom. She’s wearing a tiny red camisole that seems to barely contain her breasts and small matching shorts. Her hair is freshly brushed and cascades over her shoulders. Justin closes his mouth quickly.
“Sorry, this is all I have for pjs,” she apologizes as she turns off the lights and heads towards the bed. It takes a second for Justin to respond.
“That’s ok, they’re really pretty.”
“Have you ever slept beside a woman, Justin?"
“No.”
“I can sleep under the blanket if you want so we don’t touch.”
“No, I wouldn’t want you to get cold.”
“Don’t worry, I’m naturally warm blooded.” Cindy slides under the blanket and notices Justin’s pajamas.
“Cute pjs, I haven’t seen ones like those in a long time.” Justin is suddenly self-conscious, he tugs at the shirt.
“Yeah, well…”
“No! They’re nice, very retro. I like that. You don’t see guys our age wearing them anymore. It’s refreshing.”
“Thanks.”
Justin realizes he’s blushing and hopes Cindy’s doesn’t notice it in the gloom. She lays down facing him, one arm cushioning her head.
“Say, I hope you don’t mind about what I did in the car earlier today. I know it was very forward of me.”
“No, it’s ok. I really enjoyed it…a lot.” Justin gazes at her, hoping to convey how much he’d liked the blow job.
She smiles and slowly moves her hand over the covers towards his crotch, a questioning gesture. This time, Justin doesn’t need to think. He wraps Cindy in his arms and kisses her passionately. The clothes and blankets fly off of each other in seconds as Cindy throws one leg over Justin’s side, straddling him.
She takes his pajama bottoms and ties his wrists to the ends of the bed posts. He doesn’t care though. He can feel how wet she is already and she takes his hand and places it over her clit, rubbing his fingers softly over that sweet pearl. She takes her hand away and moans as her pleasure builds. Justin wraps his other hand around her and rubs a little faster, staring at her all the while. She screams her orgasm and Justin feels the gush of her fluids on his hand and shudders. She rubs her dripping wet pussy over his cock, which quickly springs to life. Cindy rises up and guides him into her cunt. She grips the headboard and rides his cock, tensing her cunt as she rises up. Justin gasps, pushing his head into the hard wood as he feels his cock pulse, his hips bucking underneath him.
“Your cock feels so fucking good, Justin!” Cindy whispers as she fucks him.
He isn’t used to the language; doesn’t usually swear at all, but her dirty words just add to the sensations and he groans in pleasure.
“Cum for me, Justin. Spray your cum all over me!”
She commands, grinding onto his cock even harder and faster. He is about to protest, he isn’t even wearing a condom but his body won’t listen. The head of his cock feels like it’s going to explode and just as he’s about to cum, Cindy slides off of him and leans over his cock, grabbing it between her breasts. His eyes widen as he orgasms, his cum shooting up onto her neck and breasts in a clear sheen.
“So….fucking…hot…”
She dips her head down over the head of his cock and sucks, causing Justin to gasp out loud. His cock is so sensitive. She nips the head and plays with it until she’s sucked the rest of the cum out of him. She plays with it, smearing it over her neck and breasts, rubbing her chest over his transferring it from her skin to his. She shoves one of her breasts into his mouth, holding it as she moves it around. His tongue licks it, sliding over her nipple.
“Nip it.”
He complies and bites down gently. She moans her pleasure and he slowly increases the pressure on her nipple.
“Yes, just like that. You’re a natural!”
If only my mother could see me now.
Justin thinks, then realizing what an absurd notion it is, he quickly banishes it from his mind as Cindy replaces one nipple, now peaked and red from his mouth and gives him the other one. Again he bites softly, then increases it until Cindy howls in pleasure, smothering him in her breasts, her other hand between her legs pumping her clit furiously.
“You better be ready for round two, mister.”
“I….I don’t know if I am…”
Justin panics slightly, he doesn't know how long it will take for his cock to recover. He knows he certainly wasn’t done but his cock is still limp, satisfied for the moment.
“Ok, I’ll let your cock off the hook for a few more minutes, but your tongue could use some more exercise.”
She stands up and grabs the top of the headboard , shoving her cunt into his face. He can smell their cum and the scent of her vagina and the smells combined are intoxicating. He tentatively reaches out his tongue to lick her and liking what he tastes, dives in. Cindy mashes her pelvis into his face as his tongue reaches her clit and digs in. She rides his face up and down, Justin can hardly keep up, but it doesn’t seem to matter. Cindy’s eyes are closed (from what he can glimpse) and her screams are getting louder and louder.
I hope no one calls hotel management if they send someone up to complain they’ll see me strapped to this bed with this woman I hardly know!
Justin is a little afraid but he also feels daring. He hopes no one comes up, but a very tiny part of him hopes someone does. To see him with this beautiful woman fucking him. What a story he’d have to tell the other guys in his dorm. Of course, his mother would never hear a word of it…he hopes. Again he pushes the thought of his mother away as Cindy violently cums on him. Her legs shake from the effort. She fully extends her arms as she leans back and gasps for air.
“Your tongue is almost as good as your cock!”
“That’s nice to hear since the most strenuous activity it’s ever had is when I brush my teeth every day.”
Cindy’s laugh is short and shocked.
“That’s right, I forgot. You’re a good boy, you don’t do these sorts of things.”
“No, not usually, but I must say making an exception has been very rewarding so far.”
“Oh, don’t worry, it’s about to get even more rewarding.” Cindy’s eyes twinkle mischievously as she looks behind her.
“Looks like someone’s ready to play again.” She turns back knowingly.
Justin can feel that his cock is hard again. It bumps against Cindy’s ass, and she rises up and softly bounces on it with the outside of her cunt until Justin makes involuntary whimpers every time her skin makes contact with his.
“All right, I’ll have mercy on you now, but first…”
Cindy gets off the bed and retrieves his pajama shirt. She rolls it up and ties it behind Justin’s eyes. It’s not a perfect blindfold, but she can see it’ll suffice. As she finishes tying the blindfold, she grinds her pussy into his face, then her stomach, her breasts, and finishes by kissing him deeply, her tongue probing his mouth as she guides his cock into her slick cunt once more. Justin groans from the feeling, heightened now by the fact he can’t see much. She grabs his shoulders and rides him, bouncing on her knees up and down his shaft. Justin grips the ties around his wrists for leverage and pumps his hips up. She sees that he’s lost his rhythm.
“Ok, Good Boy, let’s try something a little different.”
Justin feels her thrust a few more times and then feels his cock slip out of her. He groans, but then feels a difference in position. Suddenly, he feels her mouth on his cock, deep throating him and covering his cock with saliva. It feels amazing and he thrusts deep into her throat as far as he can. She does this a few more times and then stops. He’s a little confused. He feels her hands on his thighs as her body settles back over him, but now it seems like she’s facing the other way. He can’t really tell. He feels her guide his cock back into her….but something’s different…her cunt feels drier, and even tighter if that’s possible. His saliva coated dick slips into her, a little difficult at first but as she begins to ride him slowly, the movements come more easily. He thrusts up, and she gasps.
“Not too fast now, Justin. I’ve done this a few times but let’s start off slow.”
Start off slow for what? He wonders. He notices he can’t fit as much of his cock into her as he could before. Maybe it’s the new angle. The curiosity gets the better of him. He rubs his head against his arm until he’s dislodged the makeshift blindfold enough so he can see. The sight shocks him….Cindy has his cock in her ass! Good boys definitely don’t do this he knows. As he stares wide-eyed at the sight in front of him, Cindy turns around and sees his face.
“Never thought you’d do anal, eh Good Boy. Do you like what you feel?”
He nods because he’d always been taught to be honest. But this truly worries him. What kind of substances are being transferred onto his cock right now? Cindy reads his mind.
“Don’t worry, I made sure I was nice and clean before I started this. You’ve got nothing to worry about.” Justin slowly looks up at her; she seems genuine.
“Aren’t you enjoying the show? Doesn’t it look so hot to see your cock inside my tiny, perfect ass? The other bonus, you don’t have to worry about getting me pregnant if you cum inside of me. Wouldn’t you like to see that, all your cum dripping out of my ass?”
“Yes, do it, make me….” He can’t finish the sentence. His breeding just won’t let him. But Cindy understands. She laughs softly.
“I’ll make you cum so hard, don’t you worry yourself, Good Boy.”
Cindy wriggles her hips and drops her ass lower onto Justin’s cock and leans forward gripping his thighs. Justin hardly blinks as he watches, the sight almost overwhelming him. Her ass continues to pump his cock, her cunt rubbing against his shaft on the upstroke. Her ass clenches every few minutes as she cums, her pussy providing the lubrication to keep him wet. The sight of her ass bobbing up and down is amazing.
“So close, Cindy!” He warns her.
“Then let it go, cum in me, Justin!”
He doesn’t need to be told twice, his breath comes in short gasps as she slams her ass onto him and clenches her cheeks at the same time. Justin bucks multiple times as he cums deep in her ass. It’s so tight and so warm and feels so very good. Cindy’s nails dig into his thighs as she feels his cock pulse in her ass, feeling the cum pump into her. She shivers, making Justin cry out from the sensation on his cock. She slowly leans forward and Justin watches as his cock emerges from her ass, and then a couple seconds later, his cum trail out of the perfect circle that is now her ass. His cum drips down the lips of her vagina, and over her entrance, it makes him want to lick it up. He starts to lean forward but is stopped short by his bonds. It brings his mind back to him for a minute. What had he been considering? Licking his cum out of a woman’s ass??? Cindy turns and sees his face, and laughs at his expression.
“It’s ok, Justin. That was intense, it makes sense you’d want to keep it going.”
“I’m just not used to thinking this way ... I was always told this wasn’t right.”
“Does it feel right to you?”
“Yes, but my mind is trying to reject these thoughts.”
“That’s ok, as long as you had fun you don’t need to do anything else. You don’t have to do anything you don’t want.”
Cindy rolls off of his legs and goes to the bathroom for a towel. She wipes herself off and comes back to the bed and takes off the blindfold and unties his wrists. She kisses him softly after she’s done and cuddles into his ches
“Was that adventurous enough for you? Did you get out of your comfort zone?”
"Oh yes, absolutely.” Justin can feel her smile against his chest.
" Good, it’s the least I could do to repay you for giving me a ride.”
“I think I should be the one thanking you for the ride.” Cindy chuckles softly.
“I think you already have.” She kisses him once more and they settle down to sleep.
*
Justin comes out of his"o reverie as his car speeds past the beautiful woman on the side of the road. He catches his breath and looks in the rearview mirror. He figures he’ll go a few more miles until she’s out of sight and then stop to pump his cock in the safety of isolation. After all, his mother always told him not to pick up hitchhikers, and Justin Calhoun is a good boy and good boys don’t do that.
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