Ladyboys Moving to Thailand and my first Ladyboy
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My 1st Lady Older Than Me free porn video
My first experience with an older woman, oh my word. I hope that you enjoy reading this as much as I enjoyed her and her me. This happened a long time ago, at least 8 years ago, she was old enough to be my mother. So sit back and enjoy.
I was working as a barman at a 40th birthday party I met this stunning lady, her name was Sandy. She had long black hair, she had curves in all the right places, the perfect perky C cup breasts and her eyes were the kind of eyes that once you look into them you just cannot look anywhere else, you get lost. I was attracted immediately and I started flirting with her, before you know it she was visiting the bar more often throughout the night and would stand and chat with me.
The conversation started with the usual, but slowly started going like, “so, where is the most exciting place that you have ever had sex?” I would ask, she replied “well if you give me half the chance it would be on this bar counter with you while everyone watches!!” You can imagine how my cock was growing in m y pants the longer this conversation went on.
Towards the close of the evening she approached the bar and handed me her card with her address on the back and said “when you done here, give me a call and come visit”.
“I most certainly will!!”
She left and I couldn’t believe my luck, my cock was getting hard just thinking about her and what I wanted to do to her. I cleaned up as quickly as I could and was almost done when I thought I need to get rid of this tension in my pants as I don’t want to disappoint, so I went to bathroom and went into one of the cubicles. I took my cock which was already quite hard, I could feel the blood rushing through my veins my cock hard, all I had on my mind was her long black hair gently caressing her tits as I fucked her pussy, ramming my rock hard cock in and out as her pussy juices covered my shaft. I was about to come, I could feel my butt cheeks starting to tighten, next thing I heard knock at the door, “jack you in here, I want to lock up?” it’s Julie the bar manager. If she finds me like this, oh shit.
“Um…um…..yes I am, done in a sec”
“What you up to?” Julie asked
“Um……um……..nothing!” I say
Next the door bursts open and Julie is standing checking me out, my cock in my hand. Before I could say anything Julie got down on her knees and started kissing and caressing my balls while her hands started to jerk me off. Her hands were soft to the touch and I could feel myself going over the edge.
“Julie I’m going to cum!!”
“Well then let me catch it for you”, as Julie slipped my cock into her warm soft mouth, taking my cock with one swallow straight down her throat.
“Oh god…..that feels sooooo…….I’m cumming…..aarrrggggghhhh!!!”
With that I started shooting my load down Julie throat, she swallowed as quickly as she could but some of my cum dripped out over her chin. When I had finished cumming, she licked my cock clean, whipped her chin of and said, “There you go, I saw you chatting with Sandy and I know she’s into you, she is a good customer, so I couldn’t send you out of here with a loaded gun!”
“Thanks Julie, I promise I will repay the favour one day!”
I pulled up outside Sandy’s house, wow, it was nice. The garden was neat and green, it looked like she had money. I feeling rather nervous now, palms were a bit sweaty as I approached the door. Just as I was about to knock the door opened and there stood and angel, all I could do was stare!!!
She was wearing crimson red stilettos with black thigh high stocking. She had on suspenders holding the stocking up half-way up her thighs. A black see through lace pantie, which hugged her pussy oh so tight that I could make out the definition of her clean shaved pussy and lips. A black lace nightie that was also see through and all I could see were her dark hard nipples staring back at me.
“Hello there, thought you were not going to make it?!” she said with this seductive smirk on her face.
“I wouldn’t miss you/this for the world Sandy” I replied with this naughty grin.
She invited me in and as I walked I saw her glance down to my crotch region, “I see you already ready for me Jack” smirking. Which I was as my cock was bulging in my pants and was ready to burst out.
She took by the hand and led me up some stairs, all I could see was her well rounded ass moving with every step that she climbed, it was driving me mad. It must have been a reflex action as I don’t remember telling my arm but I just reached out and grabbed a handful of her ass. And before I could say anything she turned to me without stopping, “you like my ass Jack, it will all be yours shortly!!”
I have died and gone to heaven I thought to myself!!!!!!!!!!!!!!!!!
She had a mezzanine floor level with a very big puffy couch against the wall which looked out over her back yard which was lush with big green trees shrubs, kind of gave me the illusion that I was in a tropical rain forest or something.
She sat me down on the couch and in one movement removed my shirt and started to suck on my nipples, I pulled her up and gave a gentle kiss on her cherry red lips, and she returned the kiss with her tongue in my mouth. Our tongues danced around each in a passionate seductive way that I have never ever felt before. I slid one hand onto her shoulder and slowly slid one strap of her nightie off her shoulder, then the other. The nightie fell to the ground revealing her tits, her nipples were hard and erect. I caressed both her tits with my hands as we kissed, she let out a small gasp as if she was trying to get air.
The more I played with her nipples the harder they got and more she moaned. I picked her up so that she was straddling me and I started sucking and nibbling on her nipple. She starts playing with the other nipple as I suck on her tits, her skin is soft.
“Oh Jack I’m getting so wet!!” she says with short baited breathe. I slid one hand down between us and I panties were soaked with her pussy juices, I rubbed on her slit and could feel that she was as smooth as a baby bum, eventually moving her panties to the side, I was playing with her clit and her pussy lips.
“Do you like this Sandy?” I asked.
“Fuck me Jack, if you keep this up I’m going to cum”.
I pushed a bit harder on her clit, then I slid one finger in between her lips, she let out a moan, massaging her pussy and fingering her I could feel her body starting to tighten. I inserted a 2 nd finger.
“Oh my god……don’t stop Jack”, she was getting so wet now that with every stroke it felt my hand was being covered.
Then the sexiest thing ever, she moaned out load.
“I’M CUMMINGG, I’M CUMMING DON’T STOP!!!” I could feel her squirting all over my hand and arm, it was turning me on to the point where I wasn’t sure if I could hold on anymore.
Eventually after a couple of minutes Sandy collapsed along side me breathing heavily.
“Jack that was insane……now it’s my turn!!!!”
Without warning she quickly unzipped my jeans and had them and my boxers off and was stroking my cock softly while licking and sucking my balls.
“Sandy I just want you to know that my cock is so hard right now that if you keep this up for one more sec I’m going to cum!”
With that she quickly brought her mouth up from my balls and proceeded to swallow my cock, slowly she wrapped her tongue round my bulging head and sucked on it, then while sucking her hand started to caress my balls and stroke my shaft.
Oh fuck me Sandy, that’s feels sooooooo……..oh shhhhhhit………I’m going to……”
I started shooting big creamy one cum into sandy mouth, she just swallow shot after shot.
“Yes yes yes……..keep sucking” as I grabbed her hair and pushed her down harder on my cock.
“Sandy that was fucking insane…………I want to fuck you so bad”.
“Jack you aint seen nothing yet!”
Sandy carried on sucking and jerking my cock, I reached for her pussy and it was as wet as ever. I moved Sandy up on to the couch, careful not to move her mouth off my cock and got her to lie in the 69 position with her pussy right above my face.
I gently began to tease her pussy with my tongue making her quiver, and then gently I started to suck on her clit while playing with pussy lips with one hand.
“Oh jack that is so hot” raising her head from my solid cock. I inserted 2 fingers while sucking on her wet sexy pussy finger fucking her. She started to suck on my cock harder and harder.
The next thing she surprised me a little but I did it anyway, “Jack stick your finger in my ass”
“Huh?!?!?!?!”
“Are you sure Sandy?”
“Fuck yes Jack!!!!”
I inserted one finger in her ass which was so tight, she went into euphoria, her body started to shake as her orgasm started to climax. I could taste her pussy juices starting to drip into my mouth, but I didn’t stop she tasted to good.
“Yessssssss……Yesssssss” “Fuck me jack I’m cuming again!!!!!!!!
As she said those words I could not hold on any longer, she started to suck the cum right out of my cock straight down her throught.
“AAAAHHHHHHHHHH………”
“Fuck yes……..suck my cock…….that feels so good!!
Once Sandy had sucked up every last drop of my cum and lick my cock clean, and I had lick her pussy clean she climbed off and lay next to me.
“No-one has every done that to me before Jack…….I have never climaxed by oral sex before!!”
I was surprised, who has she been with then?! I thought to myself. We just lay there in each others arms chatting about random things when I asked if she had ever smoked weed before, she said no, so I suggested she follow me.
“Come with me!”
“Where is my clothes Jack?”
“Leave those!” I said and started to feel a bit excited for what I had in mind,
“Just wrap the blanket round you and follow.”
I did the same with the blanket and led Sandy by the hand out into her back yard. I unfolded my other hand and to her surprise I had a small joint,
“Sandy one of the things I’ve always wanted to do is smoke and then fuck under the stars?!”
Sandy stood for a sec and just looked at me, then she slowly spread her blanket out over the grass and gestured for me to lay next to her, which I obliged and covered both of us with the blanket. I lit the joint, with Sandy lying with her head on my shoulder and me gazing at the stars sucking on the joint, I all of a sudden felt her hand run gently across my cock.
“Here you go Sandy, take a hit?”
Sandy took a couple of drags, not letting go of my cock once. I took a few more drags then killed it. By now my cock was almost ready for round two.
I started to rub Sandy tits, her nipples were getting hard, so I quickly went down there to lick and suck on her nipples. With every movement of my tongue I made over her nipples she squirmed and moaned.
“Jack please………I want you to fuck me!!”
Slowly running my hand down her stomach onto her thigh and then up onto her pussy lips which I could feel was so wet already. This made my cock get so hard and with her stroking it was getting harder and harder with every movement.
“You want my cock now?”
“What you waiting for………FUCK ME Jack!!!!!!”
I climbed onto my knees and raised her legs so that her thighs squashed her pussy lips together and her ankles where on my shoulders, then I slowly started to insert cock into her wet slit.
“Oh Jack please I beg you stop teasing me……”
And with that I thrust the remainder of my shaft as deep as I could into her pussy as she let out a moan, “ahhhhh……….ahhhhhh”.
I was fuck her good and solid, every movement I made I could feel her pussy muscles tighten around my cock, I was going to explode at this rate. My balls were slapping her on her asshole, it felt so good.
“Harder Jack….harder Jack!!!”
I grabbed her tits with both hands and pinched her nipples. “Fuck Jack I’m going to cum…….FFFuuuuuucccccckkkkkkkk!”
I could feel her body going into spasms, her pussy tightened that I could barely move my cock, it was happening now for both of us.
“Oh shiiiiitttttt………..I’m about to cum!!”
“Fuck yes Jack I want to feel your cum inside me……Yessssss……yesssss!!”
“Arrrrgggggghhhhhhhh………..FUCK YES!!!!”
I fell over Sandy and gave her a gentle kiss on the lips and then rolled onto my back. Sandy cuddled up next to me, I could still feel her wet pussy against my thigh, which was now filled with my cum to.
“That was out of this world Sandy……..I could not have imagined that any better, Thanks!!”
“No thank you Jack that was amazing!”
Sandy and I went back inside and lay on her bed in each others arms staring outside at the stars and fell asleep in each others arms.
We saw each other a couple of time after that and the sex was amazing every time. To this day I still Jerk-off to thought of Sandy and how we would fuck each other.
I was working as a barman at a 40th birthday party I met this stunning lady, her name was Sandy. She had long black hair, she had curves in all the right places, the perfect perky C cup breasts and her eyes were the kind of eyes that once you look into them you just cannot look anywhere else, you get lost. I was attracted immediately and I started flirting with her, before you know it she was visiting the bar more often throughout the night and would stand and chat with me.
The conversation started with the usual, but slowly started going like, “so, where is the most exciting place that you have ever had sex?” I would ask, she replied “well if you give me half the chance it would be on this bar counter with you while everyone watches!!” You can imagine how my cock was growing in m y pants the longer this conversation went on.
Towards the close of the evening she approached the bar and handed me her card with her address on the back and said “when you done here, give me a call and come visit”.
“I most certainly will!!”
She left and I couldn’t believe my luck, my cock was getting hard just thinking about her and what I wanted to do to her. I cleaned up as quickly as I could and was almost done when I thought I need to get rid of this tension in my pants as I don’t want to disappoint, so I went to bathroom and went into one of the cubicles. I took my cock which was already quite hard, I could feel the blood rushing through my veins my cock hard, all I had on my mind was her long black hair gently caressing her tits as I fucked her pussy, ramming my rock hard cock in and out as her pussy juices covered my shaft. I was about to come, I could feel my butt cheeks starting to tighten, next thing I heard knock at the door, “jack you in here, I want to lock up?” it’s Julie the bar manager. If she finds me like this, oh shit.
“Um…um…..yes I am, done in a sec”
“What you up to?” Julie asked
“Um……um……..nothing!” I say
Next the door bursts open and Julie is standing checking me out, my cock in my hand. Before I could say anything Julie got down on her knees and started kissing and caressing my balls while her hands started to jerk me off. Her hands were soft to the touch and I could feel myself going over the edge.
“Julie I’m going to cum!!”
“Well then let me catch it for you”, as Julie slipped my cock into her warm soft mouth, taking my cock with one swallow straight down her throat.
“Oh god…..that feels sooooo…….I’m cumming…..aarrrggggghhhh!!!”
With that I started shooting my load down Julie throat, she swallowed as quickly as she could but some of my cum dripped out over her chin. When I had finished cumming, she licked my cock clean, whipped her chin of and said, “There you go, I saw you chatting with Sandy and I know she’s into you, she is a good customer, so I couldn’t send you out of here with a loaded gun!”
“Thanks Julie, I promise I will repay the favour one day!”
I pulled up outside Sandy’s house, wow, it was nice. The garden was neat and green, it looked like she had money. I feeling rather nervous now, palms were a bit sweaty as I approached the door. Just as I was about to knock the door opened and there stood and angel, all I could do was stare!!!
She was wearing crimson red stilettos with black thigh high stocking. She had on suspenders holding the stocking up half-way up her thighs. A black see through lace pantie, which hugged her pussy oh so tight that I could make out the definition of her clean shaved pussy and lips. A black lace nightie that was also see through and all I could see were her dark hard nipples staring back at me.
“Hello there, thought you were not going to make it?!” she said with this seductive smirk on her face.
“I wouldn’t miss you/this for the world Sandy” I replied with this naughty grin.
She invited me in and as I walked I saw her glance down to my crotch region, “I see you already ready for me Jack” smirking. Which I was as my cock was bulging in my pants and was ready to burst out.
She took by the hand and led me up some stairs, all I could see was her well rounded ass moving with every step that she climbed, it was driving me mad. It must have been a reflex action as I don’t remember telling my arm but I just reached out and grabbed a handful of her ass. And before I could say anything she turned to me without stopping, “you like my ass Jack, it will all be yours shortly!!”
I have died and gone to heaven I thought to myself!!!!!!!!!!!!!!!!!
She had a mezzanine floor level with a very big puffy couch against the wall which looked out over her back yard which was lush with big green trees shrubs, kind of gave me the illusion that I was in a tropical rain forest or something.
She sat me down on the couch and in one movement removed my shirt and started to suck on my nipples, I pulled her up and gave a gentle kiss on her cherry red lips, and she returned the kiss with her tongue in my mouth. Our tongues danced around each in a passionate seductive way that I have never ever felt before. I slid one hand onto her shoulder and slowly slid one strap of her nightie off her shoulder, then the other. The nightie fell to the ground revealing her tits, her nipples were hard and erect. I caressed both her tits with my hands as we kissed, she let out a small gasp as if she was trying to get air.
The more I played with her nipples the harder they got and more she moaned. I picked her up so that she was straddling me and I started sucking and nibbling on her nipple. She starts playing with the other nipple as I suck on her tits, her skin is soft.
“Oh Jack I’m getting so wet!!” she says with short baited breathe. I slid one hand down between us and I panties were soaked with her pussy juices, I rubbed on her slit and could feel that she was as smooth as a baby bum, eventually moving her panties to the side, I was playing with her clit and her pussy lips.
“Do you like this Sandy?” I asked.
“Fuck me Jack, if you keep this up I’m going to cum”.
I pushed a bit harder on her clit, then I slid one finger in between her lips, she let out a moan, massaging her pussy and fingering her I could feel her body starting to tighten. I inserted a 2 nd finger.
“Oh my god……don’t stop Jack”, she was getting so wet now that with every stroke it felt my hand was being covered.
Then the sexiest thing ever, she moaned out load.
“I’M CUMMINGG, I’M CUMMING DON’T STOP!!!” I could feel her squirting all over my hand and arm, it was turning me on to the point where I wasn’t sure if I could hold on anymore.
Eventually after a couple of minutes Sandy collapsed along side me breathing heavily.
“Jack that was insane……now it’s my turn!!!!”
Without warning she quickly unzipped my jeans and had them and my boxers off and was stroking my cock softly while licking and sucking my balls.
“Sandy I just want you to know that my cock is so hard right now that if you keep this up for one more sec I’m going to cum!”
With that she quickly brought her mouth up from my balls and proceeded to swallow my cock, slowly she wrapped her tongue round my bulging head and sucked on it, then while sucking her hand started to caress my balls and stroke my shaft.
Oh fuck me Sandy, that’s feels sooooooo……..oh shhhhhhit………I’m going to……”
I started shooting big creamy one cum into sandy mouth, she just swallow shot after shot.
“Yes yes yes……..keep sucking” as I grabbed her hair and pushed her down harder on my cock.
“Sandy that was fucking insane…………I want to fuck you so bad”.
“Jack you aint seen nothing yet!”
Sandy carried on sucking and jerking my cock, I reached for her pussy and it was as wet as ever. I moved Sandy up on to the couch, careful not to move her mouth off my cock and got her to lie in the 69 position with her pussy right above my face.
I gently began to tease her pussy with my tongue making her quiver, and then gently I started to suck on her clit while playing with pussy lips with one hand.
“Oh jack that is so hot” raising her head from my solid cock. I inserted 2 fingers while sucking on her wet sexy pussy finger fucking her. She started to suck on my cock harder and harder.
The next thing she surprised me a little but I did it anyway, “Jack stick your finger in my ass”
“Huh?!?!?!?!”
“Are you sure Sandy?”
“Fuck yes Jack!!!!”
I inserted one finger in her ass which was so tight, she went into euphoria, her body started to shake as her orgasm started to climax. I could taste her pussy juices starting to drip into my mouth, but I didn’t stop she tasted to good.
“Yessssssss……Yesssssss” “Fuck me jack I’m cuming again!!!!!!!!
As she said those words I could not hold on any longer, she started to suck the cum right out of my cock straight down her throught.
“AAAAHHHHHHHHHH………”
“Fuck yes……..suck my cock…….that feels so good!!
Once Sandy had sucked up every last drop of my cum and lick my cock clean, and I had lick her pussy clean she climbed off and lay next to me.
“No-one has every done that to me before Jack…….I have never climaxed by oral sex before!!”
I was surprised, who has she been with then?! I thought to myself. We just lay there in each others arms chatting about random things when I asked if she had ever smoked weed before, she said no, so I suggested she follow me.
“Come with me!”
“Where is my clothes Jack?”
“Leave those!” I said and started to feel a bit excited for what I had in mind,
“Just wrap the blanket round you and follow.”
I did the same with the blanket and led Sandy by the hand out into her back yard. I unfolded my other hand and to her surprise I had a small joint,
“Sandy one of the things I’ve always wanted to do is smoke and then fuck under the stars?!”
Sandy stood for a sec and just looked at me, then she slowly spread her blanket out over the grass and gestured for me to lay next to her, which I obliged and covered both of us with the blanket. I lit the joint, with Sandy lying with her head on my shoulder and me gazing at the stars sucking on the joint, I all of a sudden felt her hand run gently across my cock.
“Here you go Sandy, take a hit?”
Sandy took a couple of drags, not letting go of my cock once. I took a few more drags then killed it. By now my cock was almost ready for round two.
I started to rub Sandy tits, her nipples were getting hard, so I quickly went down there to lick and suck on her nipples. With every movement of my tongue I made over her nipples she squirmed and moaned.
“Jack please………I want you to fuck me!!”
Slowly running my hand down her stomach onto her thigh and then up onto her pussy lips which I could feel was so wet already. This made my cock get so hard and with her stroking it was getting harder and harder with every movement.
“You want my cock now?”
“What you waiting for………FUCK ME Jack!!!!!!”
I climbed onto my knees and raised her legs so that her thighs squashed her pussy lips together and her ankles where on my shoulders, then I slowly started to insert cock into her wet slit.
“Oh Jack please I beg you stop teasing me……”
And with that I thrust the remainder of my shaft as deep as I could into her pussy as she let out a moan, “ahhhhh……….ahhhhhh”.
I was fuck her good and solid, every movement I made I could feel her pussy muscles tighten around my cock, I was going to explode at this rate. My balls were slapping her on her asshole, it felt so good.
“Harder Jack….harder Jack!!!”
I grabbed her tits with both hands and pinched her nipples. “Fuck Jack I’m going to cum…….FFFuuuuuucccccckkkkkkkk!”
I could feel her body going into spasms, her pussy tightened that I could barely move my cock, it was happening now for both of us.
“Oh shiiiiitttttt………..I’m about to cum!!”
“Fuck yes Jack I want to feel your cum inside me……Yessssss……yesssss!!”
“Arrrrgggggghhhhhhhh………..FUCK YES!!!!”
I fell over Sandy and gave her a gentle kiss on the lips and then rolled onto my back. Sandy cuddled up next to me, I could still feel her wet pussy against my thigh, which was now filled with my cum to.
“That was out of this world Sandy……..I could not have imagined that any better, Thanks!!”
“No thank you Jack that was amazing!”
Sandy and I went back inside and lay on her bed in each others arms staring outside at the stars and fell asleep in each others arms.
We saw each other a couple of time after that and the sex was amazing every time. To this day I still Jerk-off to thought of Sandy and how we would fuck each other.
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- 17.06.2021
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- Straight Sex
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