He’s at it again (Part II)
Sometimes Sargent Shameless surprises me by revealing he really does have a soft and sentimental side. Not often, I have to admit. Here he relates how, during his recent debauchery in Pattaya, he was convinced he had rediscovered his high-school crush. She did however prove to have something he would never have guessed at during his misbegotten schooldays.
I never thought I would be writing about my high-school crush for no venue called third-sex.org. The fact is that Shana (not her real name, but close) was in every way a girlie girl and, although I never actually saw, I am sure there was nothing but sweet, pinky, soft-hairy teenie pussy where a ladyboy dick need not be. Like all high-school queens, she had that perky-sassy beauty that pubescent boys cannot resist: deliciously petite, and she dyed her brown hair blonde, which in those days made her a sophisticated teenage vixen. Her best attribute was her bubbly and tightly packed butt, which inspired many a jerk-off session from me and my testosterone-rushed schoolmates.
Let’s jump the clock to a few decades later when your Sargent Shameless was out on the sois of Pattaya for another night of ladyboy buggering. For this particular night, the plan was to take home this newly arrived hung beauty that I had been groping and fondling in her bar, and knew it was time to either barfine or forget her. So what I did was I went to her bar around 20:30, had my kick-off Chang beer, played for 10 minutes with her oversize dick to make sure everything was functioning (it was!) and then bar-fined her but told her to wait for me until later. You see, it was kinda early in the night and I wanted to do some bar-hopping by myself and get the kind of attention that you can’t if you bring your own lady into other ladies’ bars.
And then it happened! I was walking past a row of outdoor lady bars and, waving at me from one of them, I saw Shana! Like she looked like when she was 16. With her dyed long blond blow-dried hair hanging down her back over that bubbly butt to die for. Her dark eyes, pale skin and mischievous smile were just as I remembered her. But the Sargent’s ladyboy radar never shuts down and immediately I knew that the Thai version of my high school Shana came with a hard little dick as standard equipment!
As I looked mesmerised at Thai-Shana, she grabbed my arm and dragged me into her bar (which had seven or eight ladies and one other ladyboy). We hit it off really well, but I had to tell her that I was busy for the night and would come back for her the next day. She was understandably disappointed and I, uncharacteristically, felt that I would regret it dearly if for any reason I did not get to be with her.
So I went back to the previously bar-fined ladyboy, took her to my hotel room, got my money’s worth with one hour of 69ing and taking turns at unclogging each other’s dirt pipes (the Captain says: that’s the Sargent Shameless we know!) and even though we had agreed to a longtime sleep-over, I sent her off early and got on a motorbike myself and rushed back to Thai-Shana.
The rest is history! After the first lady drink, I knew I would be spending the remainder of my stay in Pattaya in the loving company of Thai-Shana. Even though she looked like my high school Shana at 16 years old, she was 22, she was from Bangkok, and, contrary to my initial impression, she was 100 percent Thai blooded, with no farang in her. But soon she had THIS farang 7 inches deep in her sweet orifices as I had so often wished I had done to Shana (or any other girl for that matter) in high school.
For my remaining four days and nights in Pattaya we lived as high school sweethearts, going together to the beach, to movies, bowling, shopping, and, after taking HIV-tests together, having wild, passionate, unprotected sex three or four times a day. At night, she would hold me in her arms as I fell asleep gently clutching her ever-erect little cock. She was kinda emotional when the time came for me to leave, and I knew that Thai-Shana is one of those rare ladyboys that I will be looking up again.
Because, for a guy, can there ever be a fantasy more enticing than his high school crush?…Only his high school crush with a penis!
Posted: May 8th, 2011 under Sergeant Shameless.
Comments
Comment from Dunce
Time May 30, 2011 at 2:39 pm
I think the headmistress of my Junior School probably had an enormous cock. She sounded like a regimental sergeant major and even had the trace of a moustache. I believe she was unmarried.
Comment from The Klingon
Time May 31, 2011 at 1:05 pm
I suppose for Thai boys going to a school that has ladyboys in the school, many of them do have a high-school sweetheart who has a penis! I would love to have had that choice when I was at school. I went to a co-ed in Manchester but never had a girlfriend when I was at school. Chance would have been a fine thing! There were a couple of lads in my class who we thought were gay, and a couple more in the other classes, and they seemed to have this little clique of admirers around them all the time. Funny though, they also seemed to attract the girls around them. Probably because the girls realised they weren’t a danger. There was no hostility towards them from the other lads though, apart from a few jokes. No one seemed to have any real prejudice. BTW, even though I would love to have had ladyboys in the school, I wasn’t at all interested in the boys.
Comment from Flashman
Time May 29, 2011 at 12:56 pm
My highschool sweetheart had a penis! He was three years younger than me, and I really had the hots for him. That’s what can happen at boarding school. But I grew up (reasonably) straight and got married. That was all thirty years ago. I still think about him a lot, though, and wonder what happened to him.