My First Time with a cross dresser
Introduction to crossdressers
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