My First Time With A Cross Dresser free porn video

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Growing up, like many children I went through phases. I would climb trees and play football, then as I reached my mid-teens I continued these phases but also became a lot more sexually aware, thanks to the porn magazines and porn films usually belonging to my mates dads or older brothers.

Now I am in my late teens and at college.

One day my Dad made a pot of tea and breakfast.“Did you sleep well, son?” he asked as I entered the kitchen.

“Not bad thanks, Dad, how about you?” I replied.

“Pretty good thanks, son.”

When I had finished breakfast I rose from the table and grabbed my college bag when the zip opened and the contents fell out. “Fuck it!” I snapped.

“I beg your pardon, Tim!” Dad growled. He hated foul language from teenagers.

“Sorry Dad, but I’m going to be late,” I said going red.

Dad got down on the floor and helped me pick everything up, even the porn mags that I was taking back to my mate.

“Mmm I saw these on your bed last night, very tame and boring aren't they?” He laughed.

Blushing I replied, “Compared to what? This is all me and my mates can get.”

“This is a chat for another time, go on you're running late, you said.”

Later that afternoon when I got home Dad said he had left something on my bed for me.

I ran upstairs into my room and there on my bed was a large selection of porn mags and DVDs.The mags covered every type of porn going, straight, bi, group, gay, transgendered, cross dressers and shemale; the DVDs covered pretty much the same stuff.

Flicking through a transgender mag I felt my cock stir when I heard from the door way behind me,“Well, what do you think of those then?” Dad said as he stood in my room.

“Er...erm, look great thanks, Dad,” I said blushing again.

“Seems to have the right effect on you by the look of your jeans.” He laughed."Well, if you wanna watch the DVDs we can later."

“We?” I said.

“Yeah, your old man likes porn too, you know,” he said laughing as he left my room.

As we sat down later that evening dad told me to choose a DVD. Thinking about the magazine that excited me I gave him a bi/crossdressers one.

“Good choice, son,” he said as he put it into the machine.

Straight away on screen was a long blonde haired woman and a brunette cross dresser, both in sexy outfits dancing in front of a guy.My cock began to grow in my jeans, I looked slightly across at Dad to see if he noticed, when I saw he had his cock out and was wanking. He looked across at me and said, "Don’t be shy, it’s natural to get turned on, son."

I sat a few minutes before pushing my jeans down to my ankles and began wanking my cock as on the screen the three bodies were enjoying each other orally.

“That better, son?”

“Yeah.” I quivered.

“So do you like this porn better than what your mates have?”

“It’s very good yeah, but the crossdresser thing seems strange to watch.” I chuckled.

“You never seen one before?” he asked.

I said, "No."

“Would you like to see a real one?”

“I guess so,” I said now blushing more than ever.

Dad grabbed his mobile and sent a text message. Soon after he got a reply,

“Well that takes care of that,” he said.

He got up, removed his trousers altogether and walked into the kitchen, returning with two glasses of wine and an empty glass.

“Thanks, Dad. Who’s that one for?”

“You’ll see soon enough.”

Half an hour later Dad's phone beeped. He read his message, got up and walked out the room, his cock hard as anything standing out like a perch, I couldn't take my eyes from it nor could I believe I was excited by another person's cock, let alone my own dad's.

I heard voices and he walked in with not one but two people; both looked stunning.“This is my son, Tim. Tim this is Gina and Carla.”

I grabbed a cushion and placed it over my hard cock. “H...h...hi,” I stuttered.

“Hello, Tim, pleased to meet you at last,” Gina said.

“I better get another glass. Sorry, Carla, did not know Gina was bringing you.” He smiled as he kissed her on the cheek.

“That’s okay, I was with Gina when you texted earlier,” replied Carla.

As Dad walked past them still with a hard on, the two women both stroked his cock. Well, that made mine stiffen more.

“So I see you're watching some quality TV with your dad then, Tim?” Gina said through ruby red lipstick.

I began to blush. “Err...Yeah I guess.”

“No need to blush, honey, we are all adults here,” she said. “And what's that you're hiding under that cushion?” She giggled.

Dad came back into the room. “He's got a hard on but his shyness has him hiding it.” He laughed.

“Don’t be shy, Tim, if it will help we’ll undress as well. It will make you feel better.” Gina smiled.

This they did down to a basque stockings, heels and frilly little knickers that showed the bulge of their cocks.

“There now, we are all in the same state of dress, well almost.” Carla chuckled. Shemoved over to me, sat down on the sofa beside me and pulled the cushion away.“There now, that’s much much better, and wow, what a lovely thing to be hiding away. That should always be on full view.” She smiled to the others.

“You okay, son?”

“Yeah, I think so.”

“Of course he is, Tom, can’t you tell by this?” At that she took my cock in her hand and stroked it up and down.Fuck it felt good, then she cupped my balls and before I could object she lowered her head and took me in her mouth.

“Don’t waste any time, will you, Carla.” Gina laughed.

Gina knelt between my dad's legs and started to do the same for him.Gina moved up my dad’s body and straddled him, then with some jiggling I guess she was now riding my dad’s cock for she was moving up and down while my dad cupped her breasts over her black and red basque.

Minutes later when Dad said he was close to cumming Gina climbed off him and back onto her knees, then Dad shot his load into her eager swallowing mouth.“Phew, that was close,” he huffed, panting. "Thought I was gonna fill your tight hole Gina.”

“Mmmmm would not have been the first time, hey Tom?” she said as she licked her lips to savour every last drop of my dad's cum.

Carla was still sucking on my cock now for all she was worth and I felt my balls erupt and my cum shoot into her mouth. She began gulping it down.“Thank you, Tim,” she said with a smile licking her lips

“Now while you boys recover, me and Carla will do a little show for you, and I promise it will be better than this porn film.”

Dad looked at me and I just smiled back at him, with that he knew I was cool with what was going on.

Gina and Carla began doing some dirty dancing with each other before getting into a 69 on the floor. I noticed dad’s cock was stiff again and he wanked it slowly.He got on his knees behind Gina and rubbed his cock around her asshole before pushing into her.

“Mmmmm yeah, Tom, that’s lovely.”

I could see Carla lick at Dad's balls as well as taking time to suck Gina’s cock, while Gina sucked hers, then Gina’s hands went up round Carla’s butt cheeks and probed a finger around her sphincter.

“Oh, yes, Gina, please,” Carla gasped.

Dad looked across at me playing with my cock and said,“Go on, Tim, fuck Carla in the ass. She’ll love it.”

“That I would, Tim darling,” Carla said.

I moved into position behind Carla and felt Gina’s hand on my shaft rubbing it against Carla’s waiting hole. I pushed in slowly then felt a little pop as my cock sunk in. I pushed forward till I was balls deep.

“Take your time, Tim baby, let me enjoy every inch of your young talented cock.”

Dad and I seemed to be in time with each other as we fucked these two crossdressing males. I could not last long and said I was cumming.

“Fill my naughty tight hole with your seed, Tim!” cried Carla.

I did not need asking twice. I shot my load as my balls tightened. Fuck that felt good.Dad continued fucking Gina and she continued sucking Carla, when Dad grunted,“Shit yeah, I'm cumming. You feel so damn tight and hot.”

Carla screamed, “I'm cumming too, swallow me Gina.”

We all collapsed on the floor, and seemed to just sit in silence watching the porn as if nothing had just happened.After about five minutes Gina turned to me and in a soft voice asked,“So how did you enjoy your first time with cross dressing bi guys, Tim?”

“It was far better than I could have imagined and such a turn on,” I replied.

“So would you be interested in trying again sometime so I can feel you too?”

“Mmm yes please.”

With that Gina leaned over to me and kissed me full on the lips. She/he even kissed the same as some of my girlfriends. What a lovely end to a great evening.

_ _

Hi everyone, I have not written anything for so long so a little rusty, More to come soon, please leave comments, hope you enjoyed it. Tim xxx

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The town of Great Cross was named for a towering monument that never existed. The founders had talked of making a bid to become the state capital, and the cross was meant to be a declaration of their ambition. The ambitious talk was more fun than the actual work of building would have been, however, and no great cross ever materialized. The town reached a stable population of about four hundred, which varied up or down by only a few dozen as decades and generations came and went. Few who...

2 years ago
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Bound to the cross

I had thought about being a helpless damsel in distress ever since I was a teen.   But, the years had passed and I had never had the opportunity to actually live out my fantasy.   I had talked to a few close friends about it and they all seemed to say the same thing.   I was sexually repressed and the thought of being under someone’s control was my way of coping with the fact that I was really afraid of sex, of voluntarily being intimate with a man.     I had been looking at articles and...

1 year ago
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Bound to the cross

I had thought about being a helpless damsel in distress ever since I was a teen.   But, the years had passed and I had never had the opportunity to actually live out my fantasy.   I had talked to a few close friends about it and they all seemed to say the same thing.   I was sexually repressed and the thought of being under someone’s control was my way of coping with the fact that I was really afraid of sex, of voluntarily being intimate with a man.     I had been looking...

BDSM
4 years ago
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Judith on the Cross

Judith is one of those lapsed Catholic girls who always wants to get back at her upbringing. She hates the self-righteousness, the paternalism, the hypocrisy. Before she could even spell those words or deconstruct the messages, she was a fervent non-believer. But the hidden messages of The Church still have a powerful resonance to her. A religion built around death. One that had dispensed it in quantity, too, through most of its history. It had an undertone of eroticism, a fascination for her...

2 years ago
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Fall Cross Country Fall of a Marriage

My name is Mike Cosby. I'm about 5'9" 170lbs relatively fit and trim and my sandy blond hair and green eyes kind of stand out. When I was in college and in high school, I was never the biggest guy around so I went into some of the peripheral sports. Instead of basketball or football I ran track and cross country. Running cross got me respect in school if not star status. Even for cross country and track, I was never the star on the team, but also never the dog. I was a solid middle of the...

3 years ago
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Beastly Isekai Tales of the CrossBreeding SlutPrincess 1

The Guildmistress eventually calmed down, a few deep breaths away from lucidity. She eyed the cursed woman, making absolutely sure no apparent disgust appeared on her face, otherwise the poor thing would lose it. She knew Livia would break the second she hear it, just like she herself had so long ago; it had taken her nearly two decades to fully accept it. But this was different - it was too much to bear for a poor soul. Her life, their lives were in danger; she had a job to do. "Livia,...

1 year ago
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Aunt Convinced me for a cross dresser romance session Free Sex Stories and Adult Erotica Stories

Hi, my name is Sam and I am a 26-year-old, slim physic cross dresser. I am a fashion designer and have a thing for female clothing. Not only I love designing female clothes but I also enjoy dressing as a girl. Coming to my story, this incident took place some years back when I was around 20 years old and had cross dresser romance session with my real Aunt. With fair and curvy physic, I can look more girly than a girl with my cross dressed attire. On one weekend, I went to my aunt’s place...

Cross Dresser
3 years ago
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CrossFeed

Cross-Feed --------------- This is the first story I've written in a while. I have started several stories, but put them on the back burner because I just can't find a good ending for them. I always want to get a story 'just right'. Anyway, here's my latest installment. There is really no TG or cross dressing in it, but I feel it belongs in the genre in a weird sort of way. I hope you like it. --------------- He was a stallion, and she rode him hard. He did not...

4 years ago
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Me Mom and the Hair Dresser

Growing up as a only c***d I was smothered by my Mother, I don't know if it was normal ,but at 14 she was still breast feeding me,bathing me, and sharing one bed . I was a very shy boy, we moved every year so I was always getting beat up at the new school. I had no thoughts until my 14th birthday. It's funny how these things change so fast,I had received my first computer, I was looking up and typed in the words "Mother and Son" I was directed to a porn site one of the pictures was of a mature...

4 years ago
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Beastly Isekai Tales of the CrossBreeding SlutPrincess 2

Rhea did not often break character, her usual stony expression being the best wall against unruly employees or annoying customers; but upon see this beautiful woman reduced to such a miserable state she could not prevent old memories from resurfacing, dire times when she had no Guild that relied on her, free as the wind but as feeble as a leaf. Her responsibilities gave her weight to stand on: who cared if she was a [Sex Worker] when she led the most successful organization of the city? "As...

1 year ago
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Passing the Baton 2 Lilas StoryChapter 18 The cross

Lila woke up, the following day, to find the dungeon empty. She could barely walk, her breasts, swollen and in pain, seemed to have gotten infected from the nail wounds. She looked at them, detachedly. "It will not matter anyway, in one or two days," she said to herself. She made it to the bathroom and then, still nude, sat on an armchair to wait for her torturer to arrive. Manu, with his de-facto assistant Aisha found her sitting up in the chair, drinking juice. "Is it time?" Her...

2 years ago
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Lunchtime Munchtime

As was his habit at lunchtime, Hal left the building and walked through the office park for exercise. It was a partly cloudy day, and for the moment it seemed overcast. On his way to a small path through the woods, he saw her. Sandy was an attractive redhead with a sensual voice who almost always wore a tailored blouse, a roomy ankle-length skirt, and one-inch pumps. Her wardrobe varied in color, patterns, and material, depending upon the season, but always the same ensemble. Hal watched as...

2 years ago
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Military School Crosdresser

MILITARY SCHOOL CROSSDRESSER By Kresha Matay PART 1 Tim was a sensitive young boy, bright and intelligent, but lacking many of the physical characteristics of Joe, his father. The father had wanted a son who was interested in sports, hunting and fishing just like himself. Unfortunately, through no fault of his own, young Tim couldn't measure up to the desired image. Joe had expected his son to grow up to "be a chip off the old block" and when he didn't, his father felt...

2 years ago
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The Two CrossesChapter 2

The following morning, Grant arrived at the hospital, briskly making his way to Jennifer’s room. He stopped in his steps at the sudden sight of the room empty and cleaned for later use. “Oh no ... Please don’t tell me!” He muttered, his eyes beginning to grow misty. He hurried to the Nurses Station, not wanting to know but needed to know, had Jennifer died during the night? “Excuse me Nurse, the woman who was in that room,” he pointed to the open room. “Jennifer McDermott is she ... did...

4 years ago
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Hot Cross Buns

I am fed up with the girls on the beach, they show off their great tits and a thong that hardly covers anything, they have great asses. I'm Julie a late 20's girls who is overweight and never looked good, even when I go on a diet it doesn't work. Still I do have some good friends, guys I've known for a long time, of course they aren't the best looking and one of the beach girls would never look twice at them.Then last week I thought up a plan. I told the 4 guys who are my best friends, Ron,...

2 years ago
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Wife Gangbanged on St Andrews Cross Picture Stor

THE NIGHT OF MY WIFE'S GANGBANG IN A NEIGHBORS DUNGEON[/b]Spontaneity can lead to the most erotic and fun adventures that await. Leaving caution to the wind and going with what is happening at the moment are some of the times we most cherish on our sexual experience. One such night of depravity transpired at a neighbors BDSM thralldom basement gathering. On the surface, Rick and Jan were the banner couple of suburbia....

4 years ago
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Cross Dressing Led To Sexual Heaven 8211 Part 1

Addiction lets you do anything.. I addicted to cross dressing, addicted for the femininity.. Hi, I am 24 old close door part time cross dresser from Mumbai, regular reader of ISS. Narrating my own story for first time. I am good and beautiful looking, 5’3” height, perfectly slim as like every “women” wants to be and every man feels to hold, as I kept it with having exercises and yoga because I feel sexy with it.. I started cross-dressing when I was only 12. I haven’t knew it was called as a...

2 years ago
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My Dream Of Cross Dressing Came True

This is my first story so please don’t mind and few pieces are real in this story. I will start with story rather than boring you and when I was a kid, I used to love smell of woman’s bra and panties and when that smell turned me into cross dressed I did not realize. By the time I hit my puberty I was very excited about cross dressing and used to cross dress whenever I used to get any chance to cross-dress in private. Soon after and I joined an engineer college which was mostly dominated by...

Gay Male
1 year ago
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A Proud Cross Dressing Gay Male Who Enjoys Sex Free Sex Stories and Adult Erotica Stories

When I was 12, I went to shop for shoes with my mother. I would walk around the store, making my mother laugh out loud. The onlookers at the store, would often look at me in astonishment and wonder, “How is this little boy handling pencil heels so well”?. My mama knew it back then that I was born different and she fought the world to make me who I am today, a proud cross dressing gay male. It was my first prom and I was nervous. I was worried that I will be made fun of at school, but my mama...

Cross Dresser
2 years ago
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An arrogant husband gets his comeuppance on a cross country trip with his beautiful wife of twenty years and their passenger a young black man

I couldn’t help staring at it. It was not only the biggest cock I’d seen, there was an aesthetic quality to it that begged a lingering look. Veins coursed over thick black flesh ending in a perfect golfball sized half-dome. It had to be eight inches long and, Lord Almighty, it was still soft! The first word that jumped to mind was “superior” I was staring at a superior penis. The kid’s voice snapped me back to reality. “Wanna hold it for me, Prof.?” he...

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