MY FIRST TRANSEXUAL EXPERIENCE
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Remembering My First Real Sexual Experience free porn video
As I recall, I had just celebrated my sixteenth birthday earlier that year. My step-mom, Joan was happy because I obtained my driver’s license and wouldn’t depend on her for transportation any more. She was a good step-mom, but her professional career kept her very busy. She was recently single after having divorced my step-dad - so it was just the two of us.
I attended an all-boy high school, maintained good grades and played sports. At five foot ten, I looked older than my schoolmates. Like other guys, I discovered how well girls looked, smelled, and dressed. Oddly, I also discovered that I was turned on by a guy’s penis, therefore considered myself bi-curious, even though I never witnessed another guy’s erect cock other than thru Internet porn.
Aside from a few near encounters with several girls in neighboring schools, I was a virgin, horny and looking forward to having sex with a girl. My exploration of the female body was strictly limited to content seen through a computer screen and occasional spying on my step-mom.
My step-mom was the classic professional. At forty-six, she was an attractive woman who stood five foot five with brown hair, small frame, and big tits. She dressed well, opting to wear skirts and heels to work. I had started spying on her when we moved into our new house several months ago. Discovering an opening in my closet wall, I could see into her private bathroom, where I could see the shower and vanity areas. I first saw her nude as she readied herself one morning.
Feeling shameful at first, I watched as she disrobed to shower – showing her big tits and luscious curves. In time, I would look forward to the morning ritual and my fingers unzipped my pants to release my enormous erection. Her positioning often revealed her shaved pussy and gorgeous labia. Time-after-time, I would quietly stroke and ejaculate cum onto the wall of my closet as I watched her.
In time, I became embarrassed by my actions, so I looked elsewhere and began stroking to the twenty-one year old neighbor across the street. A pair of binoculars quickly revealed her body through the front windows in her bedroom. After several months of spying, I made up my mind to satisfy my sexual frustration – I needed to hook up for real, but was way too shy to confront a girl or a guy.
In late May that year, my step-mom was leaving on business weekend retreat. She trusted me to take care of the house but forbade me to have any parties. I assured her everything would be OK as she departed. The first night alone, I became horny as I recalled viewing my step-mom’s body in the bathroom. With a raging hard-on, I hobbled into her room to grab a pair of undies and her bra. For two hours, I pleasured myself rubbing them on my body prior to cumming.
On Sunday, I decided to advance my sexual education by visited the nude beach an hour away. I knew that I couldn’t keep fantasizing about my step-mom forever and that seeing more people naked might make me brave. My cock was in my hands the entire ride to the beach. Upon arriving, I parked next to several cars and looked over the sand dunes down to the water. About fifty people were in the area and all appeared naked.
Nervous as hell, I stripped and grabbed my towel and bag as I walked calmly towards the beach. Several people looked up at me, but I stared straight ahead until I reached a shady grouping of trees where I sat on my towel. Through my sunglasses, my eyes shifted as I watched older guys and girls walk past me – all naked and some very hot looking. As I looked down between my legs, I noticed my erection taking form.
A few older women walked by and smiled. Their sagging tits looked really good, yet lacked the firmness of my step-mom’s tits. One by one, guys would also pass by – some walking by without glancing, while others held eye contact.
Just then, a thirty-something year old guy stopped and started talking to me.
“Are you alone?” he asked.
“Yes,” I said as he sat down a few feet away. He smiled at me and started making small talk.
“I have not seen you here before, is it your first time?”
“Yes, it’s my first time and just checking things out.”
I was a little nervous and I realized that my cock was semi-erect, so I shifted my legs trying to disguise it. Maybe it was the salt air combined with the sights surrounding me. I also noticed that he was semi-erect as well.
It was the first time I ever saw a penis somewhat aroused in person. My glance must have given me away even though I was not trying to stare. His cock was well formed.
“Do you like the scenery?” he asked. “Anything in particular you are looking for?”
I didn’t know what to say, but the thought of a nude guy beside me made me horny. I came to find women, yet was equally intrigued with the same sex. My cock stiffened a bit more as I nervously answered, “I have never been laid before and thought I might get lucky here.”
My God, I don’t believe I just blurted that out. I came here to find a woman and now this guy is turning me on!
He looked at me and smiled. I couldn’t control my excitement as he glanced between my legs to see a perfectly formed fully erect penis. My shaft was hard as a rock and my balls hung nicely below.
“Am I turning you on?” he asked. “I can’t help but notice your hard-on.”
“Well sorta,” I said, “But I really wanted to be with a girl for first time.”
“Well, I can possibly help you out with that. My girlfriend and I are swingers and have been with single guys before. Are you interested? By the way, my name is Steve. Her name is Laura and she is about ten years older than me, but I think she might be up for the idea. You game?”
I didn’t know what to say, but after about thirty seconds, I nodded my head and said, “Yea that might work out for me.”
Steve picked up his cell phone to call her. As he spoke, I noticed his erection had grown. His cock was bigger than mine with an enormous head. After a few minutes, he hung up the phone and sat next to me. He placed his hand on my cock and started fondling it. I nearly came right there.
“Laura is fine with this. We can drive over to her house around noon if that’s ok.”
Unsure of what to do or say, I nodded and started touching his cock. It was thick and now noticeably veiny. The head was incredibly big and helmet shaped and his pee slit was long and wide. He let out a sigh and spread his legs apart to reveal his precious tool.
“I’m not really gay,” I said.
He replied with a smile, “Neither am I, but being bi is the best of both worlds as you will find out.”
He threw his head back as my hand nervously stroked his meaty cock. After a few minutes of mutual masturbation, he suggested we pack up to leave.
He grabbed a beach bag and motioned, “Why don’t you follow me in your own car.”
I stood up and gathered my belongings while trying to hide my very conspicuous hard-on. We walked into the sun and I dressed near my car. Steve got in his car and drove off with me not far behind. Nervous by what was happening, my sexual curiosity kept me going. We arrived at his place about twenty minutes later.
“Please come in,” he said. I followed him to the door and his girlfriend appeared.
“Tim, this is Laura.”
I looked up to see a tall brunette smiling at me. “Hi Tim.”
Laura was tall and pretty. She looked older than my step-mom, but had a nice face and smile. Her one-piece bathing suit revealed some nice cleavage.
“Hello,” I replied.
She took my hand and walked me into their bedroom. Steve followed as I sat on their bed. My heart was pumping a mile a minute as she spoke to me.
“So you would like a first time with us, huh?”
Before I could answer, she loosened my bathing suit and dropped it to the floor. My cock sprung out hard and high. Laura immediately lowered her bathing suit to reveal her older body. Her tits were medium-sized and hung low on her chest. Her stomach was flabby and several rolls of fat jiggled as she moved. Her pussy was shaved and the dark lips resembled those of my step mom’s.
Laura reached over to me and we kissed. Her tongue searched for mine and we rolled on the bed completely naked. Had it not been for the fact that I jerked off the night before, I would have cum already.
“Suck on my tits, baby.”
I fumbled my mouth onto her nipples and tasted the perfume on her body. My cock was erect and feeling the moistness on her crotch. Her pussy was not shaved at all and the mound of hair surprised me. As we played, Steve sat on the edge of the bed and quickly undressed. His large thick cock sprang out as he stroked himself.
Laura guided my cock into her pussy. Here, for the first time, I entered a woman’s pussy and felt the warm, wet sensation as it swallowed my cock.
My God, this is awesome!
She gyrated her hips as her pussy pumped my cock. Steve got up and stood in front of me.
Steve asked, “Are you ready to take me in your mouth Tim?”
I was in ecstasy as I humped her and Steve’s cock appeared in front of me. I was never this close to an erection other than my own! From only inches away, his thickness and length were bigger than life. His huge head revealed the very long slit in great detail, which opened and closed as he stroked himself. Precum was flowing just as I took him into my mouth.
The next few moments confirmed my consciousness and sexual gratification. With Steve’s cock now sliding in and out of my mouth, I tasted his precum and felt the warmth of his manhood in me. His hips thrust his enormous cock in and out of my mouth and I took my free hand and surrounded his shaft as I guided him deeper in my mouth. His moans filled the room in passionate tones.
“Suck my cock,” he moaned.
Laura was watching and then took his cock from me and proceeded to suck him off.
“Watch me,” she whispered as she deep-throated his magnificent tool.
Her mouth massaged his hot cock and we both took turns taking him into our mouth. I continued to fuck her throughout this exchange and was nearing the point of no return when Steve’s moans broke the silence, “I am going to cum, oh I am going to cum.”
Just then Laura released his cock from her wet mouth and Steve’s cock pulsed producing several ropes of thick cum onto her face. His jizz rolled down her face as she manually pumped his hard cock. At that instant, my cock started to spasm and I pushed deep into her pussy.
“I am going to cum…Oh my God.”
My cock was buried in her pussy as she wrapped her legs around my torso. I was in an inescapable hold as she thrust her hips forward to deepen the penetration. My jizz shot deep into her as she moaned loudly.
“Fuck me baby, fuck me with your young cock! Shoot your cum deep into my cunt. Oh, I feel you pulsing inside me. Cum for me.”
My ejaculation lasted for almost thirty seconds as rope upon rope of my jizz filled her. Instead of stopping, I kept thrusting wildly and felt the pleasure of my wet cum mixing in her soaking wet pussy.
Even though I was finished, the thrill of my first fuck kept me hard and I pushed in her for another ten minutes. As I pulled out, Steve took my cock in his mouth and I came again shortly thereafter.
This was a great first time!
I attended an all-boy high school, maintained good grades and played sports. At five foot ten, I looked older than my schoolmates. Like other guys, I discovered how well girls looked, smelled, and dressed. Oddly, I also discovered that I was turned on by a guy’s penis, therefore considered myself bi-curious, even though I never witnessed another guy’s erect cock other than thru Internet porn.
Aside from a few near encounters with several girls in neighboring schools, I was a virgin, horny and looking forward to having sex with a girl. My exploration of the female body was strictly limited to content seen through a computer screen and occasional spying on my step-mom.
My step-mom was the classic professional. At forty-six, she was an attractive woman who stood five foot five with brown hair, small frame, and big tits. She dressed well, opting to wear skirts and heels to work. I had started spying on her when we moved into our new house several months ago. Discovering an opening in my closet wall, I could see into her private bathroom, where I could see the shower and vanity areas. I first saw her nude as she readied herself one morning.
Feeling shameful at first, I watched as she disrobed to shower – showing her big tits and luscious curves. In time, I would look forward to the morning ritual and my fingers unzipped my pants to release my enormous erection. Her positioning often revealed her shaved pussy and gorgeous labia. Time-after-time, I would quietly stroke and ejaculate cum onto the wall of my closet as I watched her.
In time, I became embarrassed by my actions, so I looked elsewhere and began stroking to the twenty-one year old neighbor across the street. A pair of binoculars quickly revealed her body through the front windows in her bedroom. After several months of spying, I made up my mind to satisfy my sexual frustration – I needed to hook up for real, but was way too shy to confront a girl or a guy.
In late May that year, my step-mom was leaving on business weekend retreat. She trusted me to take care of the house but forbade me to have any parties. I assured her everything would be OK as she departed. The first night alone, I became horny as I recalled viewing my step-mom’s body in the bathroom. With a raging hard-on, I hobbled into her room to grab a pair of undies and her bra. For two hours, I pleasured myself rubbing them on my body prior to cumming.
On Sunday, I decided to advance my sexual education by visited the nude beach an hour away. I knew that I couldn’t keep fantasizing about my step-mom forever and that seeing more people naked might make me brave. My cock was in my hands the entire ride to the beach. Upon arriving, I parked next to several cars and looked over the sand dunes down to the water. About fifty people were in the area and all appeared naked.
Nervous as hell, I stripped and grabbed my towel and bag as I walked calmly towards the beach. Several people looked up at me, but I stared straight ahead until I reached a shady grouping of trees where I sat on my towel. Through my sunglasses, my eyes shifted as I watched older guys and girls walk past me – all naked and some very hot looking. As I looked down between my legs, I noticed my erection taking form.
A few older women walked by and smiled. Their sagging tits looked really good, yet lacked the firmness of my step-mom’s tits. One by one, guys would also pass by – some walking by without glancing, while others held eye contact.
Just then, a thirty-something year old guy stopped and started talking to me.
“Are you alone?” he asked.
“Yes,” I said as he sat down a few feet away. He smiled at me and started making small talk.
“I have not seen you here before, is it your first time?”
“Yes, it’s my first time and just checking things out.”
I was a little nervous and I realized that my cock was semi-erect, so I shifted my legs trying to disguise it. Maybe it was the salt air combined with the sights surrounding me. I also noticed that he was semi-erect as well.
It was the first time I ever saw a penis somewhat aroused in person. My glance must have given me away even though I was not trying to stare. His cock was well formed.
“Do you like the scenery?” he asked. “Anything in particular you are looking for?”
I didn’t know what to say, but the thought of a nude guy beside me made me horny. I came to find women, yet was equally intrigued with the same sex. My cock stiffened a bit more as I nervously answered, “I have never been laid before and thought I might get lucky here.”
My God, I don’t believe I just blurted that out. I came here to find a woman and now this guy is turning me on!
He looked at me and smiled. I couldn’t control my excitement as he glanced between my legs to see a perfectly formed fully erect penis. My shaft was hard as a rock and my balls hung nicely below.
“Am I turning you on?” he asked. “I can’t help but notice your hard-on.”
“Well sorta,” I said, “But I really wanted to be with a girl for first time.”
“Well, I can possibly help you out with that. My girlfriend and I are swingers and have been with single guys before. Are you interested? By the way, my name is Steve. Her name is Laura and she is about ten years older than me, but I think she might be up for the idea. You game?”
I didn’t know what to say, but after about thirty seconds, I nodded my head and said, “Yea that might work out for me.”
Steve picked up his cell phone to call her. As he spoke, I noticed his erection had grown. His cock was bigger than mine with an enormous head. After a few minutes, he hung up the phone and sat next to me. He placed his hand on my cock and started fondling it. I nearly came right there.
“Laura is fine with this. We can drive over to her house around noon if that’s ok.”
Unsure of what to do or say, I nodded and started touching his cock. It was thick and now noticeably veiny. The head was incredibly big and helmet shaped and his pee slit was long and wide. He let out a sigh and spread his legs apart to reveal his precious tool.
“I’m not really gay,” I said.
He replied with a smile, “Neither am I, but being bi is the best of both worlds as you will find out.”
He threw his head back as my hand nervously stroked his meaty cock. After a few minutes of mutual masturbation, he suggested we pack up to leave.
He grabbed a beach bag and motioned, “Why don’t you follow me in your own car.”
I stood up and gathered my belongings while trying to hide my very conspicuous hard-on. We walked into the sun and I dressed near my car. Steve got in his car and drove off with me not far behind. Nervous by what was happening, my sexual curiosity kept me going. We arrived at his place about twenty minutes later.
“Please come in,” he said. I followed him to the door and his girlfriend appeared.
“Tim, this is Laura.”
I looked up to see a tall brunette smiling at me. “Hi Tim.”
Laura was tall and pretty. She looked older than my step-mom, but had a nice face and smile. Her one-piece bathing suit revealed some nice cleavage.
“Hello,” I replied.
She took my hand and walked me into their bedroom. Steve followed as I sat on their bed. My heart was pumping a mile a minute as she spoke to me.
“So you would like a first time with us, huh?”
Before I could answer, she loosened my bathing suit and dropped it to the floor. My cock sprung out hard and high. Laura immediately lowered her bathing suit to reveal her older body. Her tits were medium-sized and hung low on her chest. Her stomach was flabby and several rolls of fat jiggled as she moved. Her pussy was shaved and the dark lips resembled those of my step mom’s.
Laura reached over to me and we kissed. Her tongue searched for mine and we rolled on the bed completely naked. Had it not been for the fact that I jerked off the night before, I would have cum already.
“Suck on my tits, baby.”
I fumbled my mouth onto her nipples and tasted the perfume on her body. My cock was erect and feeling the moistness on her crotch. Her pussy was not shaved at all and the mound of hair surprised me. As we played, Steve sat on the edge of the bed and quickly undressed. His large thick cock sprang out as he stroked himself.
Laura guided my cock into her pussy. Here, for the first time, I entered a woman’s pussy and felt the warm, wet sensation as it swallowed my cock.
My God, this is awesome!
She gyrated her hips as her pussy pumped my cock. Steve got up and stood in front of me.
Steve asked, “Are you ready to take me in your mouth Tim?”
I was in ecstasy as I humped her and Steve’s cock appeared in front of me. I was never this close to an erection other than my own! From only inches away, his thickness and length were bigger than life. His huge head revealed the very long slit in great detail, which opened and closed as he stroked himself. Precum was flowing just as I took him into my mouth.
The next few moments confirmed my consciousness and sexual gratification. With Steve’s cock now sliding in and out of my mouth, I tasted his precum and felt the warmth of his manhood in me. His hips thrust his enormous cock in and out of my mouth and I took my free hand and surrounded his shaft as I guided him deeper in my mouth. His moans filled the room in passionate tones.
“Suck my cock,” he moaned.
Laura was watching and then took his cock from me and proceeded to suck him off.
“Watch me,” she whispered as she deep-throated his magnificent tool.
Her mouth massaged his hot cock and we both took turns taking him into our mouth. I continued to fuck her throughout this exchange and was nearing the point of no return when Steve’s moans broke the silence, “I am going to cum, oh I am going to cum.”
Just then Laura released his cock from her wet mouth and Steve’s cock pulsed producing several ropes of thick cum onto her face. His jizz rolled down her face as she manually pumped his hard cock. At that instant, my cock started to spasm and I pushed deep into her pussy.
“I am going to cum…Oh my God.”
My cock was buried in her pussy as she wrapped her legs around my torso. I was in an inescapable hold as she thrust her hips forward to deepen the penetration. My jizz shot deep into her as she moaned loudly.
“Fuck me baby, fuck me with your young cock! Shoot your cum deep into my cunt. Oh, I feel you pulsing inside me. Cum for me.”
My ejaculation lasted for almost thirty seconds as rope upon rope of my jizz filled her. Instead of stopping, I kept thrusting wildly and felt the pleasure of my wet cum mixing in her soaking wet pussy.
Even though I was finished, the thrill of my first fuck kept me hard and I pushed in her for another ten minutes. As I pulled out, Steve took my cock in his mouth and I came again shortly thereafter.
This was a great first time!
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