Filipina Fun!

Story Info
I meet Sheila in my hotel.
2.1k words
4.36
13.7k
7

Part 1 of the 3 part series

Updated 06/11/2023
Created 01/29/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Many years ago I was chatting to someone on-line and she was from the North of The Philippines.

For those who are not familiar there are so many trans women simply walking around, working in salons or call centres and are easy to find.

At home i am a profession suit wearing man whose live in wife is vanilla and rarely enjoys sex as she says it is too painful- so we have a brother / sister type relationship and i do what i want and she is happy enough with out sex.

We have had 3 daughters so maybe she feels she has done her part. For me i love anal sex and i have alway loved the third gender-and i even love wearing lingerie sometimes and on very special times i have met other men with the same interests.

Back to the story.... This girl was sweet and looked pretty unspoiled by excess make up and botox and i decided to meet her. She lived in the north of the islands so i sent her coach fare by Western Union and she turned up at my hotel in Makati.

I went down to meet her, recognising her straight away from the countless pictures we had exchanged and we chatted enjoyed some snacks and green tea in the downstairs lobby before she suggested she wanted to change after her long journey.

I gave her the key, quietly popped a blue pill and gave her 30 minutes- I was more than 40 years older but when i went into the room and she was wearing the lingerie i had bought for her and she was laying on the bed-so i immediately put the do not disturb light on and went to kiss her for the first time.

We kissed long and deeply and i was getting very very hard. I am nearly 8 inches and thick when fully turned on and as i kissed her flat chest and tiny nipples through the peep hole bra i had asked her to purchase i was very very hard indeed!

I could sense she was also getting excited and i kissed her deeply as she brushed her hand down over my grey marl joggers. I rarely wear underwear and she gasped as she felt my girth and size. She lay on the bed and told me she had never met a foreigner and her two lovers were an Uncle who used to abuse her anally and orally when her parents were out farming their land when she at college and she was seen to be a 'soft boy ' and she had dated a boy in her salon, but he was under five inches and with a very slim shaft.

She also messed around with a gay in college who wanted to play and explore with her.

At college the trans girls invariably had to conform so she had the appearance of a boy and she said this boy and her used to suck each other off until he fucked her one day and she returned the favour but the got caught in the toilets and the boy left as his family were ashamed.

Now she looked soft and beautiful with long hair, light make up and tiny shorts and white peasant top and to me she looked 100% female.

During the course of the week we went out many times and i was proud to be seen with her in public as she was just like a regular girl, confident and smiley, stylishly dressed and always perfectly manicured and groomed.

Now i gazed at her body framed with lace and felt like i had died and gone to heaven- or wherever!

I wanted her to keep the stockings on- but on this occasion she didn't. I looked at my cock and it was so thick and throbbing with excitement and I wondered how we would do this as she was desperate to feel me fuck her as the woman she is and always has been but she looked so slight in build and i didn't want to hurt her..

I undressed rapidly and started kissing her tiny nipples. I don't normally suck cock but her tiny hairless balls looked so cute through her see through panties and now so delicate in the flesh that i rolled my tongue around them till the fabric was wet and I could see she was aroused now also so i released her cute cock from the lacy confines along with the rest of her lingerie set.

She begged me to use lots of lube and go slowly as she raised her thighs and presented her sweet hole to me. I thought this would be too painful until she got used to me so i told her to lay face down and slowly draw her knees up with her face on the pillow. That sight which was presented to me was awesome.

It takes me some time to cum but i felt so turned on i thought i would orgasm the second i probed her so I squeezed the end of my cock to calm myself down as i slowly licked her from her asshole downwards then between her legs and rolled her balls in my mouth, relaxing her as my fingers started to open her up.

After about ten minutes of this she said she was ready and those magic words were said.

"Fuck me daddy, make me your woman please please fuck me right now!"

Always a gentleman i obliged and slowly inserted the tip of my cock into her ass. She flinched and i pulled back then she said OK and she slowly backed up on to me and i found myself two or three inches in as she turned round, looked at me over her shoulder she was smiling a little grimly and gasping (clearly in pain) and I saw she was sporting a tattoo of a flamingo. Don't ask me why i remember that but i do remember all the tiny nuances from every occasion then she said...

"Go for it Daddy fuck my like your little whore."

and backed up swallowing all my nearly 8 inches of hot turgid flesh.

This was a shock as she swallowed all of me inside her hole and I was astonished as she moaned loudly with pain and pleasure and i looked down and i was really stretching her, it looked such a tight seal I stupidly wondered if i would ever be able to escape from there but we had used lots of lube so slowly she started to enjoy it.

Because of the wondrous effects of that blue pill I fucked her for a long time, more than ten minutes then she asked me to stop as she needed a break.

I slowly withdrew and her anus gaped at me it was all red and shiny, slick with my pre-cum and lube, before slowly closing and returning to its normal size. How she took me in i have no idea, but i am mighty glad she did as remembering these years later is making me hard all over again.

She got a wash cloth and wiped my cock and started to suck it for the first time as it seemed clear that i wasn't going to be able to continue fucking her as she was starting to get sore so she sucked me, licked my smooth balls and put her tongue in my ass as i lay on my back - i have always wanted to try this- and this sweet innocent girl was rimming me for all she was worth! Again this was a first for me.

She then put a finger insider me and started to suck me again- slowly fingering me then with her other hand she cradling my balls- this was too much for an older guy like me and i warned her i was about to cum. She tightened her lips around me and I exploded several days worth of hot cum into her mouth until it was dribbling out of the sides and she opened her mouth, releasing me and stroked me some more until I sprayed her hair, face and tiny chest with the last few drops of cum.

As i looked at her, with no time to enjoy the aftermath of a thunderous orgasm she smiled and straddled my chest, her sweet cock was hard and staring at me. There was a little drop of pre-cum from the pounding I had given her, she looked at me, smiled,and I licked the end and took the drop of pre-cum from the tip. It didn't taste of much, a little salty but not unpleasant.

I decided to try and suck her to return the favour and to experiment further with my deep desires so I made sure I didn't nip her with my teeth and I drew her into my mouth. She had only ever been fucked and forced to suck, this was the first time anyone had ever shown her some care and tenderness.

I slowly sucked her and gently stroked her small balls and tried to replicate things I like being done to me.

I could see close up now that her boobs were not as flat as i thought, they were small hormone induced boobs and sitting up they looked like a teenage girls, not that i can remember that far back anyway.

After a couple of minutes i inserted my finger gently inside her which was like touching a mains wire as she went a little crazy, panting and seemingly getting harder in my mouth and i looked at her face, it was quite red and glowing.

All of a sudden she jerked and said

"Daddy I'm cumming"

and she spurted 8 shots into my mouth. The power of the climax spurts meant that i had swallowed some before i realised. She looked at me wondering if she had gone too far. I looked at her, we kissed and swapped her cum until she swallowed it all. I found this so erotic.

We went to the shower together- but decided instead to run a big bath where we sat opposite each other in the hot soapy water. We chatted and she told me more about her family and her siblings, how and when she became to realise that she wanted to live as a girl at a surprisingly young pre school age she had realised that she was in the wrong body. She was now almost 23 years old and had plans for her own salon and savings from her work.

I was tired as it was a long journey and there were only in-direct connections involving three flights, so i really just wanted to rest before dinner and luxuriate in the warm bath simply chatting and getting to know Sheila a little better.

However she wanted to feel me inside her once again. I didn't know if i could cum again so soon, but she slid up to me, put her arms around my neck, kissed me deeply and whispered....

"Daddy please make love to me. I am your girl, now breed your girl- give me a baby"

....as she lowered herself onto rapidly hardening cock. Those words whispered, her sweet face and the tablets did the trick. She slid all the way down and as our tongues wrestled she started to stroke herself under the suds. After maybe 5 minutes she stiffened and climaxed and I could actually see the streams of white cum ejecting from her cock into the bath water and at that awesome HOT sight somehow i climaxed again when i didn't think i was that close even, this time i emptied my balls deep inside her bowels- again and again- so many spurts.

Not bad for an old guy eh - I thought to myself!

it was so tight but this exotic Filippa was milking every last drop of cum from me. This time I stayed half erect but slowly she raised herself upwards and I started to shrink as I exited her now gaping arsehole and my cum literally poured out from her as she got up.

She used the hand shower to wash off the sudds and the evidence of our gentle lovemaking and got my hot towel from the radiator, dried me off and we went to bed- for a couple of hours, sated and in each others arms, Her long black hair framed her face and her oval brown eyes closed and she had a smile on her face- as did I and we dozed off.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
HardfordiverseHardfordiverseabout 2 years agoAuthor

Hi- part two will follow for sure and very soon

AnonymousAnonymousabout 2 years ago

Seemed to have a bit of a time-warp. Initially shevarrived and you had bought her lingerie, later you hadn't seen this. Later you are making out with her after having spent most of a week yet it became the first time fucking?

Punctuation needs a bit of tightening up.

A great talent that held my interest until you both had fallen asleep.

Despite it seeming to have been almost the end of your time there, and with her, I am hoping for more.

AnonymousAnonymousabout 2 years ago

Part two please?

Share this Story

READ MORE OF THIS SERIES

Similar Stories

My Transgender Neighbor Mike falls for his blonde transgender neighbor, Caroline.in Transgender & Crossdressers
Shemale Step-Sister Teen boy spies on his shemale step-sister and gets a treat.in Transgender & Crossdressers
The Big Mature Shemale Next Door Little guy is fed cum and seduced.in Transgender & Crossdressers
Comforting My Neighbor's Daughter I fuck my innocent neighbor when she comes to me for comfort.in Mature
My Aunt's Best Friend A man comes of age thanks to his aunt and her best friend.in Mature
More Stories