Caleb Woke Up Ch 01
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Caleb And Samantha Part 1 free porn video
I couldn’t help but stare at Caleb, my best friend’s son, as he helped my husband with some yard work. He was nineteen and I was old enough to be his mom, but I didn’t have any maternal thoughts towards him, I was glad he was legal.
“Hun, I need to go into work, there’s a problem with a transformer, Caleb is going to stay and finish up; I left money for him on my dresser.” My husband ran into the house to quickly change and he was gone.
I continued watching as Caleb pulled weeds, edged the yard and picked up twigs before he went into the shed to get the lawnmower. He paused for a moment took off his shirt and stretched. They’d already been working for a couple of hours and I thought he might need a break.
“Caleb, why don’t you come in and take a short break, I have some lemonade.” I walked out clad in black knit shorts and a tank top.
His head snapped up and his chocolate colored eyes bulged slightly. He quickly looked away; his face went red and mumbled consent as he followed me into the house. Looking over my shoulder I noticed he was staring at my ass, well maybe this will be easier than I thought, I said to myself.
He sat at the kitchen table and I handed him a glass of lemonade and slide a plate of sugar cookies to him.
“How’s school going Caleb?”
“Fine Mrs. Martin,” his eyes looking anywhere but at me.
“Your mom tells me that you’re on the Dean’s List again this semester, top of your class.”
His cheeks reddened again and he nodded.
“Do you have a girlfriend yet?”
“No,” he said quietly, still avoiding my gaze.
“Well then do you have a boyfriend?”
His head snapped up then and he looked into my eyes.
“I’m straight.” He said quietly.
I laughed softly, “I know Caleb, just trying to get you to look at me, why are you so nervous all of the sudden, we’ve always been able to chat without any problems,” the truth was I knew why he was nervous, I’d seen him watching me each time I was over having coffee with his mom since he was thirteen.
“Just tired I guess.”
I stood and moved to stand next to him.
“I don’t buy it,” I said as I ran my fingers through his wavy black hair pulling his head back to look up at me, “how long have you wanted to fuck me?”
“I don’t know what you’re talking about,” he stammered.
“I think you do,” I bent my head and kissed the side of his neck, biting just below his ear, “you’ve had your eyes on me each time I’ve had coffee with your mom since you were thirteen, and yet you’ve been avoiding looking at me since you got here.”
He moaned as my nails raked down his chest.
“Mrs. Martin, what are you doing?”
“Should be obvious darlin’,” I said taking one of his hands and placing it on my hip.
His hand slid up slightly and his thumb stroked the small of my back under my shirt.
“But what about my mom, your husband,” he whispered.
“I won’t say anything if you don’t,” I moved and straddled his hips, “kiss me.”
“No, Mrs. Martin, I can’t,”
“Ok, then I’ll kiss you.”
I pressed my lips against his, and slowly stroked his lower lip with my tongue, when his lips parted I gently ran my tongue along his. He groaned as I rocked my hips against his, he was already thick and hard.
I deepened the kiss and it wasn’t long before he was kissing me back, his hands moved to lace themselves in my hair and held me against him.
His lips left mine and he kissed his way down to my tits, I shrugged out of my tank top and he chuckled slightly as he noticed the titanium barbell that ran through each nipple.
“Does my mom know about these?” he said as his fingers tugged at the barbells gently.
“Yes,” I hissed as his head dipped and he sucked on one nipple before transferring his attention to the other, “Caleb, come with me.”
I stood and grabbed his hand.
“But, we can’t.”
“We can’t, or we shouldn’t?” I said as I slid my hand down to the bulge in his shorts, smiling as his face contorted slightly.
“Christ,” he cursed softly as he stood and let me lead him from the room, “where to?”
“Your choice,” I said stopping briefly to grind my hips against his.
“Your room,” he whispered softly, dipping his head to kiss my neck before biting it gently.
“Dirty little boy,” I teased as we walked into the master bedroom.
“You’re sure about this?” he said as he picked me up and tossed me on the bed
“Mmmhmm, very sure,”
Without warning he pounced, tearing my shorts from my hips and sliding two fingers deep into my center. His mouth hovered close to mine, his brown eyes staring intently into my green ones.
“Look at me,” he growled as my eyes started to close from the attention his fingers were paying to my snatch.
I whimpered but opened my eyes again.
“You’re right,” he hissed as his fingers stroked my core, “I’ve wanted you for a long time. I can’t even tell you the number of times I’ve jerked off thinking about you.”
Well this is a turn, I thought to myself, I had figured I’d need to convince him to fuck me, but apparently not.
“Caleb,” I moaned as he added a third finger.
“Yes Mrs. Martin, you like that don’t you,” his mouth closed over one nipple and he bit it causing my back to arch off the bed, “I wonder how you taste,” he said as he slid down my body.
I trembled as he took my hips in his hands and paused smelling my snatch before placing a soft kiss to my lips. His lips sucked on my clit until it was hard and aching. He licked from my snatch down to my tight hole, he lightly ran his tongue around it and I cursed as he slid a finger into the puckered hole.
“You like that,” he murmured as he kissed and then bit my ass cheek.
I could only groan as his tongue slid along the crease and then dipped into that hole.
“So fucking sexy,” he growled as he moved to pay attention to my aching cunt.
“How many girls have you been with Caleb?”
“Three girls, two women,” he murmurs against the folds of my snatch.
“Two women,” I manage to murmur
“Yes, my French teacher my senior year and Gretchen,”
“You slept with Gretchen?”
Gretchen was a mutual friend of his mother and mine. I never would have thought that she’d ever do something like that.
“Yeah, she ‘popped my cherry’, wish it had been you though,”
I moaned again as he continued feasting on my core.
“How old were you?”
He chuckled softly before responding
“Sixteen, I don’t think she would have if I hadn’t been legal,” he laughed again, “she taught me a lot, like if I slide my fingers in and press them up, like this,” his fingers slid into my core and pressed up finding my g-spot, “it’s possible to make a woman squirt.”
“I can’t squirt Caleb,”
“Can’t, or haven’t?” he murmured as he stroked me slow and deftly, nibbling lightly on my clit.
“Can’t,” I groaned.
“Well let’s just see about that,”
He stroked faster in what felt like a come here motion and I felt my snatch clench tight.
“That’s it Mrs. Martin,” he murmured softly continuing to stroke faster, “let yourself go baby girl.”
“Caleb, I have to,” was all I got out before I gushed all over his hand, and face and onto the bedspread.
“Good girl,” he purred as he lapped up my essence.
“What just happened,” I gasped, my body shaking involuntarily.
“Mrs. Martin, you’re a gusher, you just need to be stroked the right way.”
I moaned softly as he went back to stroking my cunt with his fingers and tongue.
“Please,”
“What do you want Mrs. Martin?” he mumbled from the folds of my snatch.
“Fuck me.”
He stood slowly and eased out of his shorts; I couldn’t help but lick my lips when I got a look at his massively thick cock.
“My god Caleb,”
“You like my cock Mrs. Martin?” his hand ran the length of it, sliding down under his balls, cupping them, “Come show me.”
“Caleb,”
“Come show me,” he ran his thumb over the head of his cock capturing a bead of precum and he lapped it off, “I’m delicious Mrs. Martin, I don’t smoke, or drink, I don’t eat a lot of junk, come taste me,” he continued stroking his length teasing me, another bead of precum formed and he captured it and brought his fingers to his mouth lapped it up
I moved to the edge of the bed and lying on my side pressed a kiss to the head of his cock, my tongue flicking against the head. His fingers laced into my hair and he pressed me down his shaft. I couldn’t help but moan softly as his fingers found my snatch again and he started stroking me again.
“Hang on a second Mrs. Martin, I want to taste you at the same time,” he popped out of my mouth and positioned himself on the bed pulling me onto him.
As his tongue slid into my core I couldn’t help but moan I could barely focus on sucking his gorgeous cock.
“What’s wrong Mrs. Martin? Having a hard time focusing? I wonder why that could be,” his hand cracked against my ass as he tongued from my snatch to my tight rosebud, “Does Mr. M ever fuck your ass?” a single digit slid into my tight hole and my hips twitched
“Not often,” I managed to gasp as he added a second finger.
“Ride me Mrs. Martin,” he gently slapped my left ass cheek.
I slowly turned and he guided his thick member into me. I slowly rocked my hips against his, he brought his hands to my ass and he squeezed it gently, his fingers grazing the crease. I leaned forward and braced my hands on either side of his head bringing my forehead to his.
“God damn Mrs. Martin, how in the fuck can you be so damned tight?” he hissed as he started to thrust his hips into mine.
“It’s been a while since I’ve had sex,” I managed to moan.
“Well pardon me for saying so, but Mr. M is crazy. If I lived in the same house as you, I wouldn’t be able to keep my hands off of you.”
He rolled quickly then pinning me beneath him. His hands went to my hips stilling them keeping me from rocking them up into mine. When I whimpered at the preventative measure he chuckled softly.
“So eager,” he murmured slowly sliding in and out of my cunt.
“Caleb, please,”
“You want me to fuck you hard and fast?”
“Yes, please.”
“I think you can beg better than that,” he hissed as he started to pick up the pace slightly, his work worn fingers rubbing my clit.
I whimpered softly and dug my nails into his ass making him grunt.
He backed off and pulled me to a standing position. His eyes blazed as he backed me up against a nearby wall. I moaned softly as he kissed his way down my body stopping briefly at each of my tits sucking lightly on the nipple. He moved lower and slid my legs over his shoulders he stood slowly and feasted on my core.
“Fuck, I can’t believe I waited this long to do this,” he murmured, “I can taste both of us, are you on birth control Mrs. Martin?”
“No,” I managed to gasp, “had to stop for health reasons.”
“Mmmmm I’d like to put a baby in your belly. Do you think Mr. M would be suspicious if you got pregnant?”
“I don’t know,” I managed to gasp as my hands went to the back of his head and I pinned him against me.
“Well we’ll find out won’t we?” he slowly lowered me until he could rock his hips forward and slide into me, he kissed my neck and gently bit my ear lobe before hissing, “I’m going to fuck you every time I’m over here, or every time you’re over at my house and see if I can put a baby in your belly.”
“Caleb,” I moaned, trying in vain to push away from him before he came in me.
He started moving faster and it wasn’t long until all I could do was moan as he drove into me faster and faster; all I could do was hang on.
I couldn’t stop myself from wrapping my legs around his waist, my hands went to either side of his head and I kissed him hard on the mouth, gently biting his lower lip.
“Where do you want me to cum?” he hissed staring intently into my eyes, “I’ll let you choose this time,”
I responded by clenching the walls of my pussy around his shaft and wrapping my legs tighter around his hips.
“Are you sure? I’m pretty potent, Gretchen’s youngest is mine.”
I could only moan as he continued sliding in and out of my cunt. It was risky that was for sure, but I couldn’t stop.
“Last chance Mrs. Martin,” he hissed
I kissed him hard on the mouth before moving to his ear.
“Cum for me Caleb.” I murmured into his ear, “Put a baby in my belly.”
He growled as he shot his spunk deep into my snatch.
We showered and fucked again before we quickly cleaned up the bedroom and made our way back downstairs.
“Shit, you mom called me a couple of times,”
He laughed and held up his phone showing several missed calls.
“I’ll handle this,” he said as he kissed my neck and slid his hand back between my legs.
“Hey mom, no I’m fine, I was upstairs with Samantha helping her with a computer issue,” he said as he slowly fingered me making me stifle a moan, “Matt left to deal with an issue at work and I need to finish up mowing the lawn. I’ll be home later than I thought,” he groaned softly as I slipped out of his grip and tugged his shorts down, my tongue lazily flicked against the head of his cock, “no I’m fine I just banged my elbow,” his hand went to the back of my head, his fingers lacing into my hair, “ok, I’ll see you tonight, I’ll have her call you.”
He dragged me to my feet and kissed me hard on the mouth.
“I need to mow the lawn so your husband doesn’t suspect something happened, but I am going to fuck you again before I leave.”
And thus began my relationship with my best friend’s oldest.
“Hun, I need to go into work, there’s a problem with a transformer, Caleb is going to stay and finish up; I left money for him on my dresser.” My husband ran into the house to quickly change and he was gone.
I continued watching as Caleb pulled weeds, edged the yard and picked up twigs before he went into the shed to get the lawnmower. He paused for a moment took off his shirt and stretched. They’d already been working for a couple of hours and I thought he might need a break.
“Caleb, why don’t you come in and take a short break, I have some lemonade.” I walked out clad in black knit shorts and a tank top.
His head snapped up and his chocolate colored eyes bulged slightly. He quickly looked away; his face went red and mumbled consent as he followed me into the house. Looking over my shoulder I noticed he was staring at my ass, well maybe this will be easier than I thought, I said to myself.
He sat at the kitchen table and I handed him a glass of lemonade and slide a plate of sugar cookies to him.
“How’s school going Caleb?”
“Fine Mrs. Martin,” his eyes looking anywhere but at me.
“Your mom tells me that you’re on the Dean’s List again this semester, top of your class.”
His cheeks reddened again and he nodded.
“Do you have a girlfriend yet?”
“No,” he said quietly, still avoiding my gaze.
“Well then do you have a boyfriend?”
His head snapped up then and he looked into my eyes.
“I’m straight.” He said quietly.
I laughed softly, “I know Caleb, just trying to get you to look at me, why are you so nervous all of the sudden, we’ve always been able to chat without any problems,” the truth was I knew why he was nervous, I’d seen him watching me each time I was over having coffee with his mom since he was thirteen.
“Just tired I guess.”
I stood and moved to stand next to him.
“I don’t buy it,” I said as I ran my fingers through his wavy black hair pulling his head back to look up at me, “how long have you wanted to fuck me?”
“I don’t know what you’re talking about,” he stammered.
“I think you do,” I bent my head and kissed the side of his neck, biting just below his ear, “you’ve had your eyes on me each time I’ve had coffee with your mom since you were thirteen, and yet you’ve been avoiding looking at me since you got here.”
He moaned as my nails raked down his chest.
“Mrs. Martin, what are you doing?”
“Should be obvious darlin’,” I said taking one of his hands and placing it on my hip.
His hand slid up slightly and his thumb stroked the small of my back under my shirt.
“But what about my mom, your husband,” he whispered.
“I won’t say anything if you don’t,” I moved and straddled his hips, “kiss me.”
“No, Mrs. Martin, I can’t,”
“Ok, then I’ll kiss you.”
I pressed my lips against his, and slowly stroked his lower lip with my tongue, when his lips parted I gently ran my tongue along his. He groaned as I rocked my hips against his, he was already thick and hard.
I deepened the kiss and it wasn’t long before he was kissing me back, his hands moved to lace themselves in my hair and held me against him.
His lips left mine and he kissed his way down to my tits, I shrugged out of my tank top and he chuckled slightly as he noticed the titanium barbell that ran through each nipple.
“Does my mom know about these?” he said as his fingers tugged at the barbells gently.
“Yes,” I hissed as his head dipped and he sucked on one nipple before transferring his attention to the other, “Caleb, come with me.”
I stood and grabbed his hand.
“But, we can’t.”
“We can’t, or we shouldn’t?” I said as I slid my hand down to the bulge in his shorts, smiling as his face contorted slightly.
“Christ,” he cursed softly as he stood and let me lead him from the room, “where to?”
“Your choice,” I said stopping briefly to grind my hips against his.
“Your room,” he whispered softly, dipping his head to kiss my neck before biting it gently.
“Dirty little boy,” I teased as we walked into the master bedroom.
“You’re sure about this?” he said as he picked me up and tossed me on the bed
“Mmmhmm, very sure,”
Without warning he pounced, tearing my shorts from my hips and sliding two fingers deep into my center. His mouth hovered close to mine, his brown eyes staring intently into my green ones.
“Look at me,” he growled as my eyes started to close from the attention his fingers were paying to my snatch.
I whimpered but opened my eyes again.
“You’re right,” he hissed as his fingers stroked my core, “I’ve wanted you for a long time. I can’t even tell you the number of times I’ve jerked off thinking about you.”
Well this is a turn, I thought to myself, I had figured I’d need to convince him to fuck me, but apparently not.
“Caleb,” I moaned as he added a third finger.
“Yes Mrs. Martin, you like that don’t you,” his mouth closed over one nipple and he bit it causing my back to arch off the bed, “I wonder how you taste,” he said as he slid down my body.
I trembled as he took my hips in his hands and paused smelling my snatch before placing a soft kiss to my lips. His lips sucked on my clit until it was hard and aching. He licked from my snatch down to my tight hole, he lightly ran his tongue around it and I cursed as he slid a finger into the puckered hole.
“You like that,” he murmured as he kissed and then bit my ass cheek.
I could only groan as his tongue slid along the crease and then dipped into that hole.
“So fucking sexy,” he growled as he moved to pay attention to my aching cunt.
“How many girls have you been with Caleb?”
“Three girls, two women,” he murmurs against the folds of my snatch.
“Two women,” I manage to murmur
“Yes, my French teacher my senior year and Gretchen,”
“You slept with Gretchen?”
Gretchen was a mutual friend of his mother and mine. I never would have thought that she’d ever do something like that.
“Yeah, she ‘popped my cherry’, wish it had been you though,”
I moaned again as he continued feasting on my core.
“How old were you?”
He chuckled softly before responding
“Sixteen, I don’t think she would have if I hadn’t been legal,” he laughed again, “she taught me a lot, like if I slide my fingers in and press them up, like this,” his fingers slid into my core and pressed up finding my g-spot, “it’s possible to make a woman squirt.”
“I can’t squirt Caleb,”
“Can’t, or haven’t?” he murmured as he stroked me slow and deftly, nibbling lightly on my clit.
“Can’t,” I groaned.
“Well let’s just see about that,”
He stroked faster in what felt like a come here motion and I felt my snatch clench tight.
“That’s it Mrs. Martin,” he murmured softly continuing to stroke faster, “let yourself go baby girl.”
“Caleb, I have to,” was all I got out before I gushed all over his hand, and face and onto the bedspread.
“Good girl,” he purred as he lapped up my essence.
“What just happened,” I gasped, my body shaking involuntarily.
“Mrs. Martin, you’re a gusher, you just need to be stroked the right way.”
I moaned softly as he went back to stroking my cunt with his fingers and tongue.
“Please,”
“What do you want Mrs. Martin?” he mumbled from the folds of my snatch.
“Fuck me.”
He stood slowly and eased out of his shorts; I couldn’t help but lick my lips when I got a look at his massively thick cock.
“My god Caleb,”
“You like my cock Mrs. Martin?” his hand ran the length of it, sliding down under his balls, cupping them, “Come show me.”
“Caleb,”
“Come show me,” he ran his thumb over the head of his cock capturing a bead of precum and he lapped it off, “I’m delicious Mrs. Martin, I don’t smoke, or drink, I don’t eat a lot of junk, come taste me,” he continued stroking his length teasing me, another bead of precum formed and he captured it and brought his fingers to his mouth lapped it up
I moved to the edge of the bed and lying on my side pressed a kiss to the head of his cock, my tongue flicking against the head. His fingers laced into my hair and he pressed me down his shaft. I couldn’t help but moan softly as his fingers found my snatch again and he started stroking me again.
“Hang on a second Mrs. Martin, I want to taste you at the same time,” he popped out of my mouth and positioned himself on the bed pulling me onto him.
As his tongue slid into my core I couldn’t help but moan I could barely focus on sucking his gorgeous cock.
“What’s wrong Mrs. Martin? Having a hard time focusing? I wonder why that could be,” his hand cracked against my ass as he tongued from my snatch to my tight rosebud, “Does Mr. M ever fuck your ass?” a single digit slid into my tight hole and my hips twitched
“Not often,” I managed to gasp as he added a second finger.
“Ride me Mrs. Martin,” he gently slapped my left ass cheek.
I slowly turned and he guided his thick member into me. I slowly rocked my hips against his, he brought his hands to my ass and he squeezed it gently, his fingers grazing the crease. I leaned forward and braced my hands on either side of his head bringing my forehead to his.
“God damn Mrs. Martin, how in the fuck can you be so damned tight?” he hissed as he started to thrust his hips into mine.
“It’s been a while since I’ve had sex,” I managed to moan.
“Well pardon me for saying so, but Mr. M is crazy. If I lived in the same house as you, I wouldn’t be able to keep my hands off of you.”
He rolled quickly then pinning me beneath him. His hands went to my hips stilling them keeping me from rocking them up into mine. When I whimpered at the preventative measure he chuckled softly.
“So eager,” he murmured slowly sliding in and out of my cunt.
“Caleb, please,”
“You want me to fuck you hard and fast?”
“Yes, please.”
“I think you can beg better than that,” he hissed as he started to pick up the pace slightly, his work worn fingers rubbing my clit.
I whimpered softly and dug my nails into his ass making him grunt.
He backed off and pulled me to a standing position. His eyes blazed as he backed me up against a nearby wall. I moaned softly as he kissed his way down my body stopping briefly at each of my tits sucking lightly on the nipple. He moved lower and slid my legs over his shoulders he stood slowly and feasted on my core.
“Fuck, I can’t believe I waited this long to do this,” he murmured, “I can taste both of us, are you on birth control Mrs. Martin?”
“No,” I managed to gasp, “had to stop for health reasons.”
“Mmmmm I’d like to put a baby in your belly. Do you think Mr. M would be suspicious if you got pregnant?”
“I don’t know,” I managed to gasp as my hands went to the back of his head and I pinned him against me.
“Well we’ll find out won’t we?” he slowly lowered me until he could rock his hips forward and slide into me, he kissed my neck and gently bit my ear lobe before hissing, “I’m going to fuck you every time I’m over here, or every time you’re over at my house and see if I can put a baby in your belly.”
“Caleb,” I moaned, trying in vain to push away from him before he came in me.
He started moving faster and it wasn’t long until all I could do was moan as he drove into me faster and faster; all I could do was hang on.
I couldn’t stop myself from wrapping my legs around his waist, my hands went to either side of his head and I kissed him hard on the mouth, gently biting his lower lip.
“Where do you want me to cum?” he hissed staring intently into my eyes, “I’ll let you choose this time,”
I responded by clenching the walls of my pussy around his shaft and wrapping my legs tighter around his hips.
“Are you sure? I’m pretty potent, Gretchen’s youngest is mine.”
I could only moan as he continued sliding in and out of my cunt. It was risky that was for sure, but I couldn’t stop.
“Last chance Mrs. Martin,” he hissed
I kissed him hard on the mouth before moving to his ear.
“Cum for me Caleb.” I murmured into his ear, “Put a baby in my belly.”
He growled as he shot his spunk deep into my snatch.
We showered and fucked again before we quickly cleaned up the bedroom and made our way back downstairs.
“Shit, you mom called me a couple of times,”
He laughed and held up his phone showing several missed calls.
“I’ll handle this,” he said as he kissed my neck and slid his hand back between my legs.
“Hey mom, no I’m fine, I was upstairs with Samantha helping her with a computer issue,” he said as he slowly fingered me making me stifle a moan, “Matt left to deal with an issue at work and I need to finish up mowing the lawn. I’ll be home later than I thought,” he groaned softly as I slipped out of his grip and tugged his shorts down, my tongue lazily flicked against the head of his cock, “no I’m fine I just banged my elbow,” his hand went to the back of my head, his fingers lacing into my hair, “ok, I’ll see you tonight, I’ll have her call you.”
He dragged me to my feet and kissed me hard on the mouth.
“I need to mow the lawn so your husband doesn’t suspect something happened, but I am going to fuck you again before I leave.”
And thus began my relationship with my best friend’s oldest.
Charlize
- 03.03.2022
- 9
- 0
