It all started when boys teased me about having “tits” like a girl. I was a chubby boy, and my breasts had budded like a young girl’s breasts. Before too long, boys were embarrassing me by telling me I needed to wear a bra!
True, my breasts were still quite small compared to all but the tiniest of girls’ breasts–but they would have fit quite nicely into a small-cupped bra for girls whose breasts were just beginning to grow. Secretly I wished I could wear a bra, and let a boy see me wearing it, and even let the boy take it off–but I never had a chance, until I was 16 years old and Rich Royalton entered Seaview Grove High School.
Rich had gone to a private school, which he called “snob school,” until his parents decided Seaview Grove High was good enough. He was a really handsome boy, and he soon found me attractive. I had let my hair grow like a girl’s hair, and I dared to imagine that my face looked like a pretty girl’s face, but I still wore boys’ clothes, for lack of anything more feminine.
That soon changed when Rich and I became friends. We were in the same gym class, so he saw me nude in the shower room, and he sometimes got erections when he did. His penis was a masterpiece of manly beauty, and almost twice as long as mine.
He seized opportunities to be friendly with me and I responded warmly. Soon he found a chance to ask me if I’d ever worn girls’ clothes.
*No,” I said, my heart beating hard, “but I’d like to, if I had some.”
“I think that could be arranged,” Rich said. “Just give me your measurements, and I’ll buy you some.”
“Wow! Would you really?” I cried. “But–uh–how could I get a chance to let you see me wearing them in private?”
“My parents go away for weekends pretty often,” said Rich, “and my older brother and sister don’t live at home any more, so I’m home alone.”
That was all I needed to know. I took my measurements and gave them to Rich as soon as I could. Before long he told me he had the clothes and his parents were going away this weekend.
On Saturday morning Rich drove me to his house. I was impressed. My family’s house was nice, but just an ordinary suburban house. Rich’s house was a hilltop mansion overlooking the ocean.
After we entered, he wasted no time giving me the clothes, which fit perfectly: a skimpy, flimsy bra, a pair of lacy panties, a white see-through blouse with buttons down the front, and a light blue miniskirt.
“Wow, Jack, you’re a totally cute girl!” Rich exclaimed when he saw me wearing them. “I’ve got to call you Jackie!”
“Ooh, I’d love that!” I said, growing more girlish by the second.
“Come here and look at yourself in the mirror,” said Rich, leading me to a big full-length mirror. He put both his hands on my waist and stood beside me. Sure enough, I had to agree, I did look like a totally cute girl–except that my miniskirt was bulging a bit in front because of my throbbing erection.
“Thank you so much, Rich!” I exclaimed, feeling his hands move down to my hips. Then he encircled me with his arms and started to unbutton my blouse.
“Let’s just see what you look like with your blouse off,” he said, slipping my blouse off as he spoke. I did look rather nice with only my bra on above the waist, I thought. My breasts, though still small for a girl’s breasts, had grown rather bigger since the boys had started teasing me, and my erect nipples were showing through my flimsy bra cups.
Then I felt Rich unhooking my bra. “Please, Jackie, would you let me take your bra off?” he politely asked. “Or–uh–are you the kind of girl who won’t let a guy take her bra off?”
I giggled like a girl. “Well, I certainly wouldn’t let any other guy take my bra off!” I said, “But as for you–well, try taking it off, and see if I stop you.” He slipped my bra straps off my shoulders and removed my bra. I didn’t stop him.
“Wow, Jackie, you’re the greatest!” Rich moaned, standing behind me and caressing my bare breasts. I could feel his erection pressing against my butt through my skirt and panties.
“Now let’s just have your skirt and panties down,” Rich said, breathing heavily. He slipped my skirt and panties down over my hips and let them fall to the floor. Right after that, with both of us still watching ourselves in the mirror, Rich opened his pants and pressed his big penis between my plump thighs.
“Oh!” I cried, trembling with delight and clutching his penis tightly with my thighs. “Oh, Rich! Thank you! That feels so good!”
“It will feel even better soon,” Rich assured me. He gripped my bare breasts and started to thrust between my thighs. My own short penis was so excited from Rich’s thigh-plunging and breast-caressing that I could feel myself rapidly mounting toward orgasm.
“Oh, Rich!” I moaned. “This is so wonderful!” I’m so glad you invited me!”
“So am I, Jackie, honey,” Rich said. “Hold on–I’m about to come! Are you ready?”
“Yes!” I exclaimed. “I’m totally ready!”
I reached between my thighs, gripped Rich’s penis, and pressed it against the underside of my own. “Oh!” I cried. “Rich, you’re so manly! I love it! I’m coming! I’M COMING!!”
I had masturbated many times before now, but now I gushed more powerfully than I had ever done while masturbating, while Rich frantically plunged me between my thighs and spurted a huge amount of semen into my hand.
“Jackie, you’re incredible,” Rich said. “I’ve done it with other girls, but you top them all. Please come here again soon!”
“I will,” I assured him, “and again and again! I’d love to be your girlfriend!”
“You’re my girlfriend, all right,” Rich said, “and don’t be surprised if I let everyone know about it!” He thought a minute, then added “Except my parents. I don’t think they’d be too pleased to find out I’ve got a shemale girlfriend!”
“My parents wouldn’t like it if they found out I’m a shemale, either,” I said. “But they’ll never need to know!” I grinned. “Everyone who does need to know will know–and I’m so glad they will!”
