Cutie Pie (M/m CD Crossdressing First 1st Anal)

I always liked cutely dressed boys and teenagers but I never got to have 
a relationship with one until now. It was a year ago when I met him on a 
web page for gay people to hook up. He was hiding his age as the page 
was 18+ only. He messaged me on the dating site and I sensed something 
was wrong. He was not sounding really 18 years old (He claimed he was 18 
years old on the site).

But I didn't stop messaging him and over a mount he told me of his 
fantasies of dressing up and getting fucked up the ass like a like girl. 
He was very passionate about it and He was really hitting on the stop. I 
told me of my fantasies of dressing up a man with cute dresses and how I 
would have a nice date with him after and how I would fuck him like a 
girl. 

He was so aroused by this that he let me see him on the cam. My hunch 
was right, he was underage. He was looking like he was 15 years old high 
school kid. But I said nothing about it and He talked at the cam for 
hours. I showed him some dresses left from my last boyfriend. He really 
liked short pleated skirt that looks like a nice school skirt. He even 
asked me if I had a cotton white shirt to go over the top. I didn't but 
I said I would get him one if he comes over.He didn't said yes to my 
invitation and I didn't push it.

We kept talking over the cam for a while and one day he said he wanted 
to visit me at Sunday. I smiled and said I would buy him a nice female 
school uniform for him. He jumped up and down with happiness and he sent 
me an air kiss. I returned the kiss and he closed the connection saying 
he had to ready for our date. 

I had to ready for our date as well. I went shopping for the school 
uniform and several simple makeup materials and cream to keep his tool 
down. I didn't want his tool get into our love making and I was sure it 
would even to a simple hand holding.

At Sunday, He came over to my place all by himself and I take him in. He 
was even cuter than he looked at the cam. He had smooth hairless skin 
and a short hair. His hair was raven black and his eyes were bright 
green. He walked in wearing a tight blue jean and he had a well shaped 
put. His arms sticking out the T-Shirt was thin and feminine. 

I closed the door behind him and kissed him on the cheeks whispering, “
Welcome”. He brushed bright red and joined his hand behind over his cute 
butt. I smiled at him and I held over her shoulders and told him if he 
waned to wear something better. His green eyes lightened up and said yes 
in a low tone. 

I guided him to the bed room. Female school uniform was over the bed and 
he jumped on it right away. He was really happy to see it and he place 
it over his slim body while checking it out at the body mirror. I 
stepped behind and kissed his cheek again and whispered into his ear, “
Why don't you wear?”. He smiled and started to take off his t-shirt. I 
stepped behind and placed the cream and a wig. I said him to use the 
cream on his tool and he can wear the wig if he wants to and I left him 
to dress up.

I waited for him for half a hour while watching news on TV in the living 
room and then he stepped in. He was cute as pie. He was wearing the wig. 
His slim chest was hugged by the white cotton shirt and a green tie was 
hanging from his delicate neck. His slim white legs were sockless expect 
the up to the knee white socks. Then his well shaped butt was covered by 
the pleased skirt. He really wanted to wear all of the uniform.

His sight was enough to give me a instant hard-on. He smiled to my 
reaction and walked over to me. With a feminine movement, he sit on my 
lap and leaned to my wide chest. I wrapped my arms over his delicate 
body and kissed him on the forehead and he looked up to my face and 
asked me, “About the cream, it made my ... tool ... stiff ... Honey”. He 
was really shy about the situation but still he was on my lap. I kissed 
his cheek and said, “That's normal Honey. It won't break your female 
look”. He smiled and kissed me on my lips light.

I kissed his lips back and keeps the kiss going. Our kiss was slow and 
light but was full of passion. My tool was hard under his butt and he 
was sure feeling it under his butt. Our kiss was rather tame so I 
decided to change it. I moved my tongue out into his month. He accepted 
my tongue right away and started to suckle on my tongue. Following his 
tongue suckling, I started to move my hands over his body and caress his 
back and butt. While groping his small butt, I noticed he was not 
wearing any underwear. He was a shy slut in the end and I pulled up the 
skirt. My fingers fund his hole and starts to massage his boipussy 
softly. As my fingers working on his hole, he moaned into my mouth. 

He broke the kiss and whispered softly, “You can take my virginity and 
made me a woman”. I smiled and lied him on the couch we were sitting. He 
opened his legs wide for his man and I slipped between them right away. 
My cock leaned to his stiff cock and I started to rub my cock against 
it. His stiff cock started to wet his already wet from pre cum cock with 
my own pre cum. 

I suckled on his red lips and kissed him. He opened his mouth right away 
and My tongue entered his mouth. While rubbing our cocks to each other, 
our tongues danced with each other and I was getting impatient as I 
kissed him deeply. I raised his both legs up and I started to rub my 
cock against his tight virgin hole. As I massaged his boipussy, he 
moaned into my mouth. 

Then I raised from his lips and started to rub his hole lubricant. While 
my fingers massage and rubbed over his hole, I slowly started to 
unbutton his shirt. Then I slipped one finger into his hole as I leaned 
to suckle on his nipple. He arched with pleasure and moaned loudly. I 
placed stokes on his nipple using my tongue while my finger moves in and 
out of his boipussy. His moans got stronger and I decided it was time to 
take his virginity. 

My finger slipped out and my cockhead leaned to his lubed and relaxed 
hole. I kissed his lips when I started to push it in. Cockhead slowly 
popped in and I stopped. I felt his tight hole over my cock stretching. 
He smiled at him and he brushed back at me. He really had a man's cock 
up his ass while dressed in female school uniform. He was very aware of 
it and shy about it. I really liked his tight hole and I pushed my cock 
deeper into his boipussy. He arched as it entered and then filled his 
butt well. 

I leaned to his ear and whispered, “My cock is right up your ass, cutie”
. H brushed in bright red when I whispered and I pulled back to finish 
the first thrust. My cock exited his hole except the head and I pumped 
into his butt with a long thrust. He moaned with enjoyment and lust when 
I started to fasten my thrust but before I even got actually fast, he 
climaxed wildly under my body. He squirmed with pleasure and I went for 
hard fucking as he climaxed. He screamed loudly with pleasure with my 
hard thrusting and I came close to climax. 

As I felt I was near climax, I buried my cock deeply into his butt and 
started to shoot my hot cum into his butt, filling well. I lied on his 
small body enjoying the climax and his tight hole. I lied on his body 
for a while without taking my cock out and I kissed him softly. I 
whispered to his ear, “Now you are a true woman”. He brushed and looked 
away without saying anything. He knew he was a true woman now and it was 
me who made him a true woman. 

We lied on the bed for a while and then he had to go back to home. We 
didn't take a shower saying he wanted feel my scent longer and left for 
him with my scent over his boy and my cum inside his butt.

