Ladyboys Moving to Thailand and my first Ladyboy
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The Bad Boy Gets Sexually Schooled--Chapter 1 free porn video
My name is Ann and I am eighteen years old and in twelfth grade. I can remember the first time I met Will. He was the “new kid” in school, having just transferred to Elmore High School. He came to live with his grandmother while his parents were overseas for his father’s work. Will came at the beginning of the summer and it did not take long for him to get the reputation of being a “bad boy.” Not that he caused trouble or anything but because he wore a leather jacket and like to drag race. He was soon a member of The Dragsters race club. He was also in the twelfth grade and by the time school started in August, he had most of the females under the age of nineteen all atwitter over his good looks and sex appeal. Hell, even my best friend was hot for him and she preferred girls.
Will was about five foot seven inches, muscular although a bit on the heavy side, with soul-searching brown eyes and brown hair that just touched his shoulders. On the first day of school, Will and I literally ran into each other. My locker stuck, causing me to rush to my last class of the day. As I came around the corner of the hallway to my English class, Will ran into me, knocking me on my butt. My books and papers flew all over the hallway. My little brother, who was with Will, started to laugh but did not even offer to help me out.
“You cock sucker!” I screamed at my brother. “You could at least help me up?”
“I am going to tell Dad what you called me,” Randy said. “You know that is not right.”
“Sorry I forgot,” I said as I struggled to my feet. “You are a cunt licker want-to-be virgin boy.”
In the meantime, Will was picking up my books and papers, listening intently to the conversation between my brother and me, although at first he did not know realize we were related because we looked nothing alike. I was five foot three inches, long blond hair midway down my back and green eyes with a sprinkling of freckles across my nose. Randy was six foot even, had brown hair and green eyes.
“So Randy,” Will began, “according to your sister here you are a virgin, right?”
Randy turned three shades of red, glared at his sister, and then said, “She does not know what she is talking about. However, I do know she sucks cock and a whole lot more so if you want Will, I will hook you two up.”
If it were not for us being in school I would have knocked my brother on his ass for spreading tales about me, even if they were true. Grabbing my things from Will I muttered thanks and headed back to my locker. English was half over so I saw no sense in walking into class now. I took the books I had homework in and stuffed them in my backpack. I was determined that my brother was going to pay for his big mouth, especially to Will.
I was no virgin and had not been since I had my cherry popped by a camp counselor ten years older than I was. I always looked older so he had no idea I was only sixteen. He made the summer fun but it was just that – a summer fling. How Randy knew I was not a virgin any longer was a mystery to me because I was very careful and discreet. However, on the other hand, he might have just said it because of what I said about him. Halfway home I heard the roar of a motorcycle coming down the road. As I glanced to my left, I saw it slow down, and then pull to a stop in front of me.
“Want a ride, Ann?” Will asked as he took off his helmet
Looking down at the short skirt I was wearing I knew if I climbed on the back I would probably give him a good view of my hot red thong, but then all things considering it might not be a bad idea.
“Thanks, but only have a couple of blocks to go,” I said.
“If you do not have to be home for a while we could take a ride,” Will suggested. “I promise to be the perfect gentleman.”
I started to laugh and said, “Then why would I want to take a ride on your Harley if you are going to be a gentleman. Riding on a Harley, that vibration on my pussy, makes me horny and I don’t need a gentleman for that. I need a bad boy.”
Will started to laugh and then said, “I like your sense of humor, Ann, but you need to watch the talk of not being a virgin because some boy is going to believe you and then you are going to pay.”
“It is not just talk Will,” I began, “because I am not a virgin.”
Will was not a virgin either but he had never met such an outspoken girl that had no qualms about admitting she was not a virgin. I didn't know it at the time, but he thought I was just pulling his leg, and he decided to call me on it by stopping at his favorite spot by the lake out of town.
Before he could ask me again if I wanted a ride, I thrust my book bag at his chest. “Do you have somewhere to put these while we go for a ride?”
“Sure,” he told me as he put them in the compartment under the rider’s seat.
I hiked my skirt a little more to make it easier to get on the Harley, making sure that he caught a glimpse of my red thong. By the look in his eyes, I had succeeded in getting his attention. He got on and I wrapped my arms around his waist, letting my hand momentarily slide down to the front of his jeans and giving him a squeeze. Before he could say anything, I moved my hands back up to his waist.
I put on the helmet he had taken out of the storage area before he put my book bag there. Soon we were flying down the back roads, over the different hills, and around curves. The vibration from the motorcycle was doing a number on my pussy and I knew it would not be long before I cum. I did not want to cum from the vibrations from the motorcycle but by Will’s tongue on my clit.
It seemed like I might be getting my wish when he pulled down a dirt road that led to a summer hangout for the kids of town. At the end of the lane, there was a huge grassy lot and a big lake we all used as a swimming hole. Stopping under a tree, Will got off and offered me his hand. He put our helmets on the handlebars and pulled out a blanket from another saddlebag. We walked over to the tree holding hands, and while he spread it on the ground, I pulled off my t-shirt and shimmied out of my skirt. When Will turned around, I was standing there in my skimpy lacy red bra and matching thong.
Seeing him watching me, I slowly slipped the straps of my bra down each arm, one at a time, then reached behind me, unfastening it. I took it in my hands and threw it at Will, but he did not even attempt to catch it, leaving it to fall to the blanket.
“What the hell do you think you are doing?” he asked as he stared at me.
“Well, I thought we would fuck,” I said, “unless you are like my brother and a virgin boy. If that is the case I will be glad to take your cherry,” as I walked over to him, playing with my nipples. “I have plenty of experience taking boy’s cherries.”
Wrapping my arms around his neck, I pulled his head down and kissed him hard. Will figured I was playing at being grown up and acting like I was a sex symbol so he decided to give me a little scare. He scooped me up in his arms and lay down on the blanket with me in his arms, his mouth seeking my nipple. As he latched on to my nipple and began to suck and pull on it, I felt my thong getting wetter. I grabbed his hand and pushed it toward my pussy since he apparently did not know what to do. However, I was wrong; Will pushed my thong to the side and inserted a finger into my pussy, seeking my clit.
Finding his target, he began to rub my clit hard while sucking and pulling on my nipples, alternating from one to the other. I was horny from the vibration of the Harley and soon I was wiggling all over the blanket, my pussy clenching his finger so tight he had trouble moving it. Within minutes, my juices began to flow as my orgasm ripped through my body.
Will quickly pulled his finger out and stood up. I looked up at him, wondering if he was going to remove his jeans so I could give him pleasure. To my surprise, he gathered up my clothes and tossed them to me.
“Get dressed, Ann, before I do something I will regret later,” as he went over to stand by the motorcycle with his back to me.
I gave an un-ladylike snort as redressed, trying to figure out what was going through his mind. I wadded up the blanket and threw it at him asking. “Are you bi or gay?”
“Hell no!” Will yelled. “Whatever gave you that idea Ann?”
“You had a chance to fuck me and you didn’t.”
“Just because I did not fuck you does not make me bi or gay, little lady.” Will told me. “Now get your ass on my motorcycle so I can take you home before your dad comes looking for me with a shotgun.”
I laughed and climbed into the passenger seat, putting on my helmet. When I put my arms around his waist this time, I kept them away from his crotch. When we got back to my place, he gave me my book bag, put the helmet away, and roared off, leaving me standing at the end of the sidewalk. As I walked up to the front door, lost in thoughts, I did not notice my brother sitting on the steps.
“Well, sis, did you fuck him?” he asked. “You were gone long enough to.”
I had enough of my brother’s mouth so I swung my book bag at him, catching him on the side of the head. “I am a fucking virgin,”
“Not according to Fred Wilson.”
I knew exactly whom he was talking about and he was the one fuck I regretted but I pretended I did not know whom my brother was talking about. “I do not even know who you are talking about,” I said as I went in the house after kicking Randy in the hip.
For the next month, I did not see Will except in passing at school but he said nothing to me except "hi", but only if I spoke first. I was not used to a boy ignoring me so I decided I would have to seduce him if I wanted him to fuck me. In October, the school has a dance and this year the tenth graders were in charge of picking the theme. The theme they picked was a Sadie Hawkins dance based on the Little Abner comic and movie where the girls chased the boys. For this dance, the girls asked the boys and the boys could not refuse.
As soon as I heard this, I cornered Will before he even got off his motorcycle the next morning.
“Morning Will,” I said. “You are going to be my date to the Sadie Hawkins dance. It is Halloween night. Casual dress and I already have tickets. You can pick me up at six o’clock,” and with that I walked away, leaving him staring open-mouthed at me.
For the next two weeks, Will once again avoided me so I was unsure if he would take me to the dance or not. On that Saturday evening, I was dressed in a pair of tight blue jeans, a button-down red-checkered shirt, tied at the bottom, tennis shoes, and I had my hair divided into two pigtails. My brother was out with some of his friends for the weekend. Mom and dad were also gone for the weekend so I had the house to myself. I had plans to have Will in my bed that night, come hell or high water – unless he did not take me to the dance. A few minutes after six I heard the sound of a vehicle pulling in the drive. Looking out the window, I saw Will climbing out of a dark grey pickup truck.
Hurrying out the front door, I met Will halfway, throwing my arms around his neck, kissing him hard on the lips. He gently pushed me back, took my hand, and led me to his truck. After making sure I was in, he shut the door and went around getting in.
“Thank you,” I told him
"Well, it is not like I had much choice,” Will said laughing. “But I should warn you I have two left feet.”
“Then we will just dance the slow dances and I will lead,” I told him, reaching over and patting his thigh.
When we walked into the gym the DJ was playing Creedence Clearwater Revival’s Bad Moon Rising. To my surprise, Will grabbed my hand and led me to the dance floor, doing his own version of the jitterbug. Within a couple of minutes, I was able to follow his steps. When the DJ put on another song by them entitled Down on the Corner. I then decided to show Will one of my dances, The Bump, and at first he was a little hesitant but he soon got into. Suddenly, my girlfriend, Kylie appeared on the other side of Will and was doing The Bump with Will from that side. When the DJ decided to play Proud Mary, Will bowed out and moved to the edge of the dance floor to watch Kylie and me dance. When the song ended we decided we need a cup of punch so we started off the dance floor.
“This is for all those who want to hold their honey really tight,” said the DJ as he put on Animals House of the Rising Sun.
Will grabbed me and said, “Now that is my type of song,” as he pulled me into his arms,
My arm went around his waist and I laid my head against his chest. He held my right hand in his left one, his other arm around my waist, making sure he kept a discrete distance between our bodies. After the song ended, we got ourselves something to drink and mingled with our friends. We danced a couple of more slow songs, then I suggested we leave, to which he readily agreed.
“How about coming in for a few minutes?” I asked when we pulled into the driveway and got out of the truck, walking hand and hand up to the front door.
He looked at his watch and asked, “It is almost nine o’clock. When is your curfew? Will your parents mind me coming in?”
“They are gone for the weekend,” I whispered. “We have the house to ourselves and I have a comfortable twin bed that has never been fucked in so it needs to be broke in.”
“Ah… I think it is best that I not come in.” Will told me. “I don’t want to get you in trouble if your parents should come home. And there is your brother.”
“He is gone for the weekend too. Any other excuses Will?” I asked
“No, but I am not coming in,”
I shot him a dirty look and then said angrily, “You have to be gay since you do not want to fuck me.”
Grabbing the house key out of my hand, Will unlocked the door, motioning for me to go on in. Once inside, Will shut the door, locked it and then shoved me against the door. Pressing his body against mine, he held my arms to the side, kissing me hard,
“Ann, if you are a virgin, you had better tell me now,” Will told me as he ground his pelvis against me.
“I am not a virgin,” I told him, kissing him back, my tongue delving into his mouth.
“In that case,” Will said as he slung me over his shoulder, smacking my ass hard, “where is your bedroom? I am about to show you I am all man.”
“Down the hallway, last door on the right,” I said as my body began to tingle.
Once in my bedroom, he stood me on my feet and proceeded to get undressed, leaving his clothes where they dropped. I quickly followed suit. For a few minutes, we just stood there staring at each other’s naked body. Will turned and shut the bedroom door as I turned down the covers on my bed. I crawled in and Will soon joined me. Pushing me against the wall, he started to suckle and tweak my nipples. Then he grabbed my one pigtail and pulled my head toward him, his lips ravishing mine as our tongues frantically mated. I just knew my lips would be bruised tomorrow.
Will looked at me and asked, “You suck cock?”
I nodded yes and he turned around lying at the foot of the bed, pulling me on top of him. Spreading my pussy lips, he started to lick and nip at my lips while his fingers started to explore my insides. I slowly lowered my mouth onto his cock, licking and sucking while playing with his balls. I heard Will moan as I licked the shaft and around the head. Suddenly I gave a little squeal as his tongue licked my clit.
“Someone has a very sensitive clit,” Will muttered as he licked and tugged on it, while finger fucking me with three fingers.
I continued to administer to his cock, tasting his precum. Suddenly I felt a finger probing my anus and I automatically clenched my cheeks together. He then pulled his fingers from my pussy, spread my ass cheeks and proceeded to lick my little hole, tongue fucking it, I moaned as he slipped his fingers back in my pussy, rubbing my clit. This time when his finger probed my anus, I let him insert his finger as deep as he could.
I decided to do the same to Will, so I sucked on my index finger and slowly inserted it into his anus, finger fucking him as he was doing to me while sucking his cock. I could feel him throbbing and enlarging in my mouth, precum oozing out. Will decided to increase the pressure on my clit, sending me over the edge into a mind-blowing orgasm unlike any I had ever felt before. I automatically rubbed my pussy against his face, covering it with my juices.
“On your knees,” Will demanded, “I want to blow my load into your pussy. Oh, fuck.”
“Yes, Will, fuck me,” I told him getting into a position that I had never tried before.
“I cannot shoot my load into you Ann,” Will said. “I am not prepared. I have no condoms. I will have to shoot onto your stomach or tits.”
“Will, fuck me. I am on the pill.”
“Are you sure you are okay going bareback?” he asked, “I promise I am clean.”
“So am I, now fuck me damn it.”
Not needing a second invitation, Will kneeled behind me and positioned his cock at my opening. Very slowly he inserted his cock, not sure if I was telling the truth or not about being a virgin. When he did not reach any resistance, he knew I was telling the truth and shoved his cock in, balls deep. I reached under myself and began to rub my clit hard.
Will began to moan and fuck me harder and deeper as he got closer to shooting his load. Giving out a cry, he filled my pussy with his load of seed just as I reached my orgasm, my pussy squeezing the last drop of cum out of him. I collapsed on the bed face down with Will lying on top of me. He began to kiss my neck as his deflated cock slid out of my pussy.
Rolling off me, he said, “I would love a repeat performance but do not want the neighbors to talk about a strange truck being in your driveway for several hours.”
Just as he started to put on his pants, my cell phone chimed, indicating a text message. “Will, stay here and I will be right back,” I told him as I grabbed my robe, leaving him staring at me.
When I came back in a few minutes later, Kylie was with me. Will was putting on his shoes when we walked into the room. He looked from me to her and back with a quizzically look on his face.
“Will,” I asked, “have you ever had two women?”
“Or watched two women go down on each other?” Kylie asked as she leaned over and kissed me, tweaking my nipple.
“And you accused me of being bi or gay,” Will said. “And the answer is no to both questions.”
“Then you have a seat there on the floor and recuperate while I get Kylie in the mood,” I said as I dropped my robe.
Kylie quickly stripped and joined me on the bed. We started out side by side, playing with each other’s breast, kissing and frenching, slowly working our way into the sixty-nine position.
Looking over at Will, Kylie smiled and said, “I get a cocktail tonight of cum and pussy juice. Never had that cocktail before so hope it is good,” as she began to lick and suck my pussy.
I was returning the favor to her along with slowly inserting my finger into her anus like I had done to Will. Kylie gave a little squeal at the unexpected finger and then started to moan. Will, in the meantime, had stripped off and was stroking his cock while watching the action on the bed. Soon both of us were moaning and wiggling all over the bed as we both reached the pinnacle and tumbled over the other side into a hard orgasm.
Rolling apart, I told Kylie, “You can ride his cock and I will let him eat me out. Is that okay, Will? Kylie? Oh, and in case you are wondering Will, she is also on the pill, clean, and loves to ride bareback.”
With everyone in agreement, Will laid down on the bed and Kylie began to lick and suck his cock while I sucked on his nipples, Kylie stopped and moved to his left against the wall while I squeezed in on his right, each of us offering him a breast as we kneeled beside him. Pulling us closer Will squeezed our breasts together and started sucking on our nipples at the same time while we played with the other. Pulling back, we took turns kissing Will and then each other while tweaking his nipples and stroking his cock.
“Girls, stay still,” Will told us. I want to mark my territory,” and he proceeded to give each of us a hickey on our breast.
Kylie and I looked at each other and then we each gave Will a hickey to mark our territory.
Kylie moved back between his legs and licked his shaft up and down, then moved into position, slowly lowering her pussy onto his cock. I positioned my pussy over his face for him to enjoy. Kylie slowly started to ride his cock, while he tongued and licked my pussy, pushing three fingers deep inside of me. Will began to moan and thrust his hips upward as Kylie started to fuck him harder and faster, reaching behind him to play with his balls.
Having been lovers for the past six months, I could tell by the look on Kylie’s face she was on the edge so I reached forward and started to pinch her nipples hard. She gave out a scream as her orgasm erupted inside her, sending all her nerve endings into overdrive.
Seeing her in the throes of an orgasm sent me over the edge. My pussy juices flowed all over his face. Within seconds, Will gave a cry and emptied his load into Kylie.
“Scoot over Will,” I told him, “It is my turn for a cum pussy juice cocktail.”
Will flattened his back against the wall while I lay down on the bed. Kylie lowered her pussy over my face while she leaned over and began to lick and suck Will’s cock clean. I drove my tongue deep into Kylie’s pussy, eating her out. Soon she was wiggling around as she had a small orgasm.
“Middle,” Kylie ordered Will as she squeezed in next to the wall while I turned around and hugged the edge of the bed.
Will kissed me deeply, and then turned his head so Kylie could kiss him. After an hour of just snuggling, Will moved off the bed, leaving Kylie and me there half-asleep. He quietly got dressed and let himself out of the house. When he looked at his watch, he saw it was just after midnight. He looked once more at her bedroom window, and then started the truck and left, knowing that this was a night he would not soon forget.
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