Toni Ch. 02

In the previous chapter: My older sister, Lisa, found out I like to wear her clothes when she was out. She decided to call me Sister Toni rather than Brother Tommy, and blackmailed me into doing everything she wanted. For starters, she made me dress as a girl, stroll on a public street, and perform an oral job on her. Initially, I was reluctant but ended up liking it.

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In the next 2 days, at least one of our parents was home all the time. Lisa and I were busy preparing for important exams, and we only met for dinner. Lisa tried to be nice to me at the table. However, she never addressed me by any name. We mostly glanced at each other momentarily before talking to our parents.

On the 3rd evening, after dinner, she caught me in the hall and whispered to me to knock on her door at 9 pm. Unfortunately, 5 minutes before 9, I got a call from David, asking me relevant questions about the upcoming exam. We ended the call at 9:10.

I knocked softly on Lisa's door.

"Toni, come on in."

I entered, closed the door behind me, and gazed at her. She had a stern look on her face, "Girl, what wasn't clear about 9 pm?"

"Sorry, I got a phone call..."

"Why do you think I care? You should have said that you had to leave and talk later! Toni, I am very disappointed in you. I heard the best way to train younger disobedient sisters is with strict discipline. Toni, I have to go to Lora for half an hour. I'll be back around quarter to 10. By then you'll be wearing girly clothes and make yourself pretty for me. As a reminder, you are to use ONLY stuff you'll find on your side of my closet!"

And then she left.

As I removed my clothes and began putting on nicer ones, I hoped Mom wouldn't be looking for me. The light blue ruffled panties were sexy. My dick began stirring. The matching soft bra was already filled with cotton balls. I fastened it on my chest and checked the new colorful cosmetic box Lisa left for me. It contained shiny red lipstick, black mascara, and makeup. Great! I wore the blonde shoulder-length wig and looked in the mirror. I may have been biased, but I thought my appearance deserved applause. I checked my watch - Lisa would be here in 10.

I put on the shoes and tried to sashay on my high heels. It wasn't easy, but after 5 minutes, I felt more comfortable walking on them.

Lisa arrived at 10 pm, carrying a small box. Her eyes explored me thoroughly, and then she smiled, "Toni, you outdid yourself. You are very pretty. As a reward, you'll get your dessert. But I didn't forget you were late to my room earlier... Toni honey, please remove your panties."

I lowered the panties and Lisa sighed, "You didn't tuck your long clitty. Bad girl! Go to the bathroom, tuck your... thingy, and come back. I have a surprise for you."

I taped my dicky and small sack backward and returned to her room. Lisa was sitting on her chair with her skirt high on her wide-open thighs. I could see she was pentyless, and her moist labia were glistening. In her hands, she held a small plastic container of KY jelly and a 5" thin pink vibrator.

She grinned at me, "Honey, it's our night together. You'll lick me nicely until I climax, and this undersized pecker will fill your man-pussy. I'll have the remote control and adjust the speed according to your performance."

I pleaded, "Lisa, be reasonable, I've never stuck anything there. It will hurt..."

She smiled sweetly, "Toni, don't be bashful. You know a pussy was created to accommodate bigger objects. Trust me, in time your sphincter will dilate and adjust to much larger things. This is a very small artificial dicky."

I stared at her with tears in my eyes.

Lisa whispered, "Oh, honey, don't cry. It's for your own good. Here, let me show you; Kneel before me with your ass facing me."

I knelt in front of her and leaned on my elbows. Lisa spread the cool jelly on my crack and slowly moved to my anus. She tapped gently on my puckered hole until she felt no resistance and inserted her forefinger in. Instinctively my sphincter contracted on her finger. She left it there and mumbled, "Don't fight it. Try to relax and then push out as if you constipate. I did it and felt a second finger penetrating my bottom. It felt tighter but the lubrication helped it slide easily. She was right; it didn't hurt. I began liking the way it felt. All of a sudden both her fingers moved out. The hole felt empty and I wanted her back in.

I didn't have time to speak and the vibrator entered my butt hole. It was slightly larger and cooler than her two fingers. The warm jelly was very pleasant. Lisa bobbed it gently in and out. The feeling was terrific. I never knew!...

She left it deep in my ass and told me to turn around. Lisa pointed to her exposed cunt, "Toni, Bon Appetit!"

I crawled toward her and sniffed her juices. I liked the odor last time and it smelled the same this time too. I licked the folds. The taste was mildly different than before. Was it due to her different meals? I wasn't sure but it didn't matter, cause I liked both tastes...

I put my hands on Lisa's butt cheeks and pulled her pelvis toward me. Now both her vagina and anus were exposed to me. I lapped lightly, moving from the midpart of her labia, down to her anus. She shivered mildly. Then I moved back up, barely touching her clitoris. She trembled again and moaned.

I did it a couple of times and then I felt the vibrator in my ass coming alive. It was a slow, zooming vibration. I jolted in the beginning, but it felt much better soon after. I continued giving her oral, gradually involving my lips and even my nose in the process.

Lisa's groans turned louder, and the buzzing in my bottom increased. My tucked penis tried to stiffen but was unsuccessful and ached. I became horny - Hearing Lisa groaning deeply, licking her soaked folds, and feeling my sphincter vibrating, brought me closer to orgasm faster than I thought. I inserted 2 fingers into her pussy and rubbed the front wall.

Lisa shook wildly and began to cry. All of a sudden, I felt my face being covered with a yellowish, mild-taste fluid. Was she squirting? I've read about it but never experienced it. However, the mere thought of it took me over the edge, and my tucked, half-hard prick erupted backward. I was dizzy with my face and fingers deep in her cunt, but still continued my manipulations, pushing Lisa to a prolonged orgasm.

I got tired 10 minutes later and slowly disengaged from her.

I stayed kneeling and waited for her to recover. Eventually, her eyes opened, and she watched my face. Lisa started laughing, "Toni, you were awesome! My climax was so powerful, that I squirted all over you! It happened to me only once before. It's not just your face; look at your blouse and upper chest..."

I said in a low tone, "Both of us came. Isn't it the most important thing?"

She caressed my wig, "Of course it is. Honey, I am impressed."

"Lisa, may I ask a favor?"

"Sure. What is it?"

"Now that we are done, will you turn off the vibrator?..."

"Oh, sorry, I forgot..."

"Toni, go shower and put everything you have on in my laundry basket."

I showered and returned naked to Lisa's room. She stared at my deflated penis with the red markings and commented, "Toni, you did good today. I like your progress. On Monday morning I'll have my math exam. I want to sleep well the night before, so Sunday night, starting at 10 pm, you'll be in my room, naked. It will be the next stage in your progress."

...

On Sunday I was out and came home in the evening. I saw Lisa during dinner. She seemed nervous. I asked, "Lisa, are you OK?"

"I just came back from Rona. We went over the material together and I realized I was not as proficient as I thought..."

"Sis, you'll be OK. I know you; Before every exam, I hear the same old story, 'I am not good enough,' and the score is never less than A-. It's a mental thing. Later we can discuss options to relieve your uneasiness before the test."

And then I winked at her. She smiled.

After dinner, I went to my room and worked on my computer until 9:30 pm. It was time to prepare for Lisa. I felt sorry for her - I was facing a critical exam soon too, but I learned to take my studies less seriously, and as a result, I ended up with some Bs.

I shaved my body, showered, tucked my dicky, wore the blonde wig, and added my red lipstick. Lisa only instructed me to be naked. She didn't mention anything about wearing a wig or lipstick, but I wanted her to be pleased with the new Toni, especially now...

Exactly at 10 o'clock, I knocked on her door. She yelled, "The door is unlocked."

I opened the door and leaned on the frame in a pose I thought was half erotic and half funny. She laughed, "Toni, you are awesome. Not a man, since no penis comes off your groin, yet not a woman either, because your chest is too flat. But a nice try."

She was sitting on the edge of her bed and signaled to me to come closer. Her eyes explored my body and then she grinned, "Toni darling, your body is hairless, just as I like it. Period. New paragraph. Did you know we girls like to watch and touch each other's tits just like boys do? So now I'll teach you to treat girl's breasts as we prefer to be touched. From experience, boys are always in a hurry and squeeze a girl's boob as if it was dough, being prepared to make a cake. It's too rough and guys see this part as a necessary step toward their ultimate goal. Most women prefer delicate touches, at least in the beginning. It takes us more time to become horny, but once we are, all bets are off, and every girl behaves differently. Toni, it's time to learn how to undress a woman. You saw my pussy and ate it - I'd say, for a beginner, your score was a solid A. The next step is removing my top, and pleasuring me in the process."

I stood there, trying to think logically, but I felt lightheaded. I have never seen Lisa's breasts and now I was told to undress her...

Fortunately, her blouse had front buttons. I fumbled with the top button for a long time. It may have been only 10 seconds, but it felt like a full hour. Lisa leaned back on her bed and closed her eyes, which made it easier. I unbuttoned the next ones much faster to reveal her soft pink bra. Again, I was lucky, unless Lisa wore that one on purpose - The clasp was in the front. I released it, gingerly lifted the cups, and placed them by her side.

Lisa's tits were beautiful! Creamy twin peaks with dark pink nipples. Lisa opened her eyes and grinned, "Toni, you like what you see?"

I stuttered, "They are faaantastic. I loove them... I juuust doon't know if I am Tommy or tooni."

She chortled, "I can't see your clitty, but I think I know what you mean. Forget about Tommy. Toni, I want you to make love to my breasts, and don't forget you are a girl!"

I placed my palm under her areola and gently trailed along the edge of her smooth skin. I continued moving circularly, barely touching her.

Lisa closed her eyes again. I moved gradually upward, bypassing her rubbery nub to the top of her tit, feeling it lightly. As I was doing it, I felt my penis aching. It began hardening the first moment I saw her breast, but now it was wrestling against the tape.

I tried hard to distract myself, ogling the perfect boob before me. I caressed it, lightly brushing the nipple. Lisa moaned, and arched her back mildly, lifting her tit into my fingers. Next, I caught the nipple between my thumb and forefinger and rolled it gently. Lisa's moans increased. I used my other hand to massage her upper chest and move up to her long neck. Her neck artery pulsed fast. Lisa opened her lips and groaned louder. I noticed her hand crept down toward her groin.

She looked so pretty and desired... I had no idea what went through my mind at the moment, but I found myself kissing her lips softly. She opened her eyes and stared at mine for a short time. I thought I screwed up and prepared myself to be punished. However, she smiled and shut her eyes again.

God, did it mean I could kiss her again? I felt the urge to do it, but was scared. My fingers were rolling her nipple somewhat harder, and it hardened. I bent and kissed it. Lisa's right hand was now playing with her covered cunt, and the other she placed on my wig, encouraging my face to make love to her tit. I sucked on it. Lisa's torso jerked and her whimpers turned noisier. She was aroused!

I raised my head and tweaked her other breast. Her hand followed mine on her chest. With one hand on her glorious mammary, my face and the other hand were free.

I hesitated for a few seconds and decided - It was now or never. My hand slid under her skirt, found the waistband of her panties, lifted it slightly, and moved toward her snatch. Her labia were well lubricated. I rubbed her clitoris extremely gently.

It took her 2 seconds - Her body jolted as if hit by lightning, and I heard a loud scream. It was a good reason/excuse, as I leaned down and French kissed her.

Initially, she continued screaming into my mouth, while my tongue explored her oral cavity, caressing hers. Slowly, the sounds diminished, her lips wrapped mine, and her tongue caved to my demands. I wasn't sure if this was her half-conscious status during her climax or if she was aware and agreed to become more active.

I continued kissing her sweet mouth as my hand gradually moved up from her cunt toward her other breast. Once both my palms were kneading her firm tits, I raised my face from hers and watched her.

Next, my left palm caressed her hair and my right moved slowly along her body, admiring her perfect curves.

Her eyes remained closed for a couple of minutes before opening them and grinning, "Toni, you were very good! A+! I am relaxed but very tired. I think I'll sleep well tonight..."