Georgia Rose
Schoolboy Sex (Part One).
When I was fourteen and a half years old I was already an experienced cross dresser. I fitted my sister’s clothes perfectly, not to mention my mothers high heels, my make up skills were advanced and I knew I could look a treat. My favourite outfit was my stylish sister’s black leather skirt and jacket; it looked and felt fantastic with sheer black pantyhose and pumps. My small but noticeable breasts would show from a low cut tight lycra top.
I happened to find myself at home alone for a weekend, two days of being a girl! Once everyone had gone I was straight into my sweet hobby, putting on soft panties and sheer pantyhose, my sisters bra which I filled out nicely, and a long silky night-gown of hers to wear while I got made up. Foundation, powder, and blush was all liberally applied, along with eye shadow and lipstick; I tried to looked about twenty five years old!
Looking back now I didn’t appreciate how nubile and girlish I was, if only time could reverse! My hair was relatively long and could just be tied in a ponytail, that was enough to complete the look.
I sat around watching television for a while and playing with myself. It was a great way to spend a day I thought. Into the afternoon however things got a bit boring, I thought I would go out for a walk. I put on my sister’s leather skirt and jacket and touched up my makeup, probably wisely I did not wear the highest pair of heels I could find, as was usual, but tried something more sensible.
Once out side It felt as though the eyes of the whole world were on me, they weren’t of course, the suburban street was empty. Off I wobbled in my mid size heels towards the beach which in mid winter was deserted. Once there I was able to sit on a park bench with my legs crossed in perfect poise. I enjoyed the solitude until some one began to walk toward me; it was a teenage guy probably only a couple of years older than me. I tensed up with fear.
"Do you have the time?" He said.
"About three thirty I think." I replied.
He had absolutely no idea I was the same sex as him but dressed as a girl. My voice had not broken and my smooth face was rounded and girlish; my bright red lipstick was enough to confuse anyone. I immediately relaxed as my identity as a girl was apparently confirmed.
"I have to meet someone here in a while, you haven’t seen anyone else around have you?" He said.
As I replied not, other thoughts began to cross my mind. All the girls’ teen magazines where I got my makeup tips from seemed to say; you just needed to have a boyfriend.
"Do you have a girlfriend?" I inquired.
He was somewhat taken aback. Even more so when I shortly offered to be his.
He was very nervous by now at this girl in heavy makeup and leather offering him what most boys only dream of. He also had, I noticed, a huge erection.
His response was favourable though; probably more out of shock. I took his hand and we walked off down the beach road.
After a couple of minutes I realised neither of us had a clue what to do next.
"Lets go and sit over here." I suggested.
We made ourselves comfortable in a grassy area that was relatively private, luckily for what was about to happen.
As we sat together I suddenly kissed him. He was like a wound up spring and just about leapt on me, his tongue going down my throat and his hands rubbing my tits under my jacket. This made my jacket opened up and fall of my shoulders, pushing my new breasts forward through the tight lycra top. I was rather overwhelmed but this seemed to be the natural order of things, so I thought!
His hands then moved to rubbing my legs, his grip through my pantyhose was firm, to say the least. I realised as his hand went higher and higher up my leg that I was going to be, what I had read as, "felt up."
God! I thought, my dick! His hand was actually rubbing outside the crotch of my panties by now but luckily I had my cock folded back between my legs, he hadn’t noticed or felt anything unusual yet so I did the only thing I could think of to distract him. I went straight his huge erect penis, rubbing it through his loose jeans.
He came in his pants almost immediately, and lay back on his elbows still shell shocked. I then took the opportunity to unzip his fly and have a look inside his pants. It was extremely sticky with hot fluids when I got his still erect cock out.
"Do more" he said enthusiastically.
Obligingly I put my hand around his penis and started pulling him off. I was surprised at how hard it felt, something I didn’t notice when doing it to myself. It was now time for me to give him a blowjob, as the magazines referred to it. I put my mouth over the tip of his cock and sucked. The salty burning taste took me by surprise and I almost gagged. Fuck that, I thought.
I continued pumping his cock with my hand and that seemed to keep him happy until he ejaculated again, his cum running down my hand.
He was exhausted by this time but I was just getting fired up, I made the poor boy cum a third time with my hand before letting him go.
We both lay there after we used his handkerchief to clean ourselves.
"How old are you? He said. "Seventeen or eighteen?"
"Older, closer to twenty." I replied, getting up to leave.
"I have to go now, but I’ll see you back here again sometime? I said.
"Oh God yes." He replied.
I walked off home not really believing what I had done, but laughing to myself at how easy it was to deceive a man with sex on his mind.
While taking my panties off to have hot bath afterwards I discovered that I too had ejaculated in a sticky mess. My first taste of sex was still something I think of as unreal, but it certainly set the scene for me in my later years, and I did learn to love the taste of cum. For weeks after I saw that boy hanging around the beach, I was dressed as a boy now and my hair had just been cut, so he had no idea who I, or she, was. I imagine he is still bragging to his male friends about the older woman who gave him a hand job at the beach.
Copyright owned by me,
Georgia.
Misuse will result in severe humiliation of misuser!
Names in the story have been changed.
