Toni Ch. 03

In the previous chapters: My older sister, Lisa, found out I liked 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. Next, she taught me how a girl was supposed to satisfy another woman, starting with gentle touches, kisses, and even playing with her breasts. Then Lisa trained my man-pussy using a remote-controlled vibrator. Gradually, all my reservations about appearing and accepting the role of a female melted away.

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The evening after Lisa's exam, I asked her how it went. She grinned, caressed my hair, and said, "Toni, I think I did very well. You helped me and deserve a bonus. What would you like?"

I blushed and didn't answer.

"Oh, Toni, don't be shy."

I mumbled, "I dreamt last night that I was allowed to serve you when you shower. I soaped you thoroughly, and you liked it so much, you let me kiss you again..."

She smiled, "Lately, you were such a good girl, that I'll agree to grant you your wish. But before you join me, make sure your clitty is tucked way back. I'd like to feel a girl's gentle touch, not a guy's hand grazing my skin. When I crave intimacy with a guy, there are plenty who ask me out for dates."

The same evening, Lisa notified me about going to shower when I gave up and thought it would happen another time. I carefully tucked my smallish dick between my thighs, remembering that the shower water may loosen the tape. I entered the bathroom wearing my pretty silk panties. Lisa laughed and asked me to remind her to buy me a bikini. The silk panties were beautiful but were not intended to be used in the water. I removed them and noticed Lisa's nod of approval. My man-clitty was well hidden between my thighs. She gave me the loofa with liquid soap, faced the wall, and asked me to start with her backside. I began with her legs. I admired them. They were muscular, yet very feminine. I proceeded to her round buttocks, which looked very erotic. I slowly moved from the sides to her crack. She spread her legs for me and leaned on the wall. I couldn't resist and discarded the loofa to the side and continued with my bare hands. Lisa did not object, and my fingers fumbled around her puckered hole.

I heard her whispering, "Toni, don't forget this hole is not for you..."

I got the message and gradually went up to her back, shoulders, and neck. She turned around and glanced at me, "You did good so far. It's time to do my front. Your touch is very soothing." Lisa leaned on the wall, closed her eyes, and relaxed.

Again, I began at her legs but when I reached her upper thighs, I shifted to her upper chest. I took my time massaging... sorry, I meant soaping, her gorgeous breasts, hearing her soft moans. Needless to say, eventually, I moved to her abdomen cause it was time, not that I wanted to. A moment later, I was doing her lower tummy. I knelt in the tub and gently pushed her thighs wider apart. Lisa's moistened cunt was fully exposed to me. I caressed the labia lightly. Lisa groaned louder and her feet spread wider. I continued rubbing gently her folds, now and then tapping on her love knob. She pushed her pelvis toward me, and suddenly my face was only 2 inches from her pussy. I could smell her sex - The juices she secreted during her arousal were intoxicating!

I put aside the soap, washed her vulva with water, and began lapping her folds. I felt Lisa's hands pulling me to her, encouraging me to finish her off. Within less than a minute of flipping her clitoris from side to side and massaging her vagina with 2 fingers, my sister's torso trembled and I heard her whimper. I stood up and continued fucking her cunt with 2 fingers, and my tongue-on-clit job was replaced with thumb-on-clitty. I watched Lisa's expression. It was a mixture of grimace and utter pleasure. Her mouth was partially open. The temptation was too much. I kissed her luscious lips. Her lips opened for me and my tongue slipped into her hot mouth. She tasted sweet with a tinge of soapy flavor. I disengaged from her face a short time later, feeling my man-clit harden, trying to burst free. Knowing Lisa didn't care to see it, I rushed out and entered my room. I fell asleep sometime later.

...

I won't bore you with all the bureaucratic details of how I began on spironolactone. It's the drug that was intended to lower my testosterone levels before starting estrogens. It was tricky and involved some cheating because I didn't want my parents to know about it yet. Lisa helped me achieve our goals.

When I was alone in my room, I wondered more than once how my relationship with Lisa evolved since the day she discovered my secret obsession with her clothes. From regular brother and sister relations, it changed rapidly to Lisa dominating me, and I accepted my role as Toni, her sub, little sister. The role was embarrassing and humiliating, but it turned me on in a way I never predicted. Lately, I cherished the time she spent with me, letting me see her voluptuous body, smell it, touch it, and satisfy it. Obviously, since I was now her 'sister', I was not allowed to use what was previously known as 'my dick,' but I could use my fingers, tongue, and lips.

Interestingly, I even started thinking like a girl; Rather than masturbating my 'long clitty' the way I used to before, I practiced with the new vibrator that I got from Lisa. The pleasurable feeling in my man-pussy with the device inside me turned me on the deeper it entered. The buzzing that vibrated my prostate was sending me into a fantastic orgasm...

Lisa and I continued our encounters several times a week, mostly late in the evenings, before going to sleep. One day, she notified me she was going to spend 4 days with her friend Jill at her home and be back next weekend. I was disappointed, and she could see it on my face. She hugged me, and said, "Toni, every now and then, Jill and I wish to spend quality time together. You haven't met her yet but you will. Three months from now, she'll be staying in our house for several days and I'll introduce you two."

"Will you present me as your brother or sister?"

"You'll be my underdeveloped sister Toni. By then, I expect your breasts to begin showing up, and with a padded bra, you'd look the part well. I didn't mention to you an important detail - Like me, she is bisexual. so when we are together, we sleep together. You would like her. Like you, she is the submissive type, and I tell her how to behave. So Toni, if you continue progressing on the path your brain told you to go, I'll let the two of you enjoy too. One last thing - Since I dumped Morris, I haven't had sex with a guy for almost a month. The other night, my cunt reminded me that she was interested in being filled with a rigid tool. As you know, there were a few guys who knocked on my door, trying their luck securing a date. I am still debating between Allen, the tall handsome swimmer, and Tyrone, the black tight end on our football team. He is a stud and has a reputation for being gentle with the ladies, but when in bed, he is a real bull... What do you think?"

"I'd love to help you choose between them, but I haven't met either one. Are you planning to introduce us?"

"Toni dear, of course. I plan to do it later. Once your tits reach B size, I'll let my guy meet you. If you are nice, we may even enjoy a three-way..."

I stared at her face. She was serious. I kept quiet, knowing I'd have to think about the road ahead.

On the evening before she moved to Jill, we spent time together in her bed. I was privy to touch her terrific body and suck on her nipples. She smiled at me, "Honey, tomorrow I'll be in bed with Jill, and I know she'll want to play with my tits too. I am the one who showed her the ropes, and she turned up to be a good student, like you."

Hearing Lisa talking about her escapades with Jill was like an aphrodisiac for me. I moved between her thighs and lapped her sweet pussy savagely until she climaxed.

The next day Lisa was gone.

...

I was in bed, thinking. Lisa was going for 4 days to enjoy her intimate relationship with Jill. Then she said her plan was to start a new relationship, this time with a guy. I had to find something for myself, so I did not depend on her schedule. I still wanted to serve her and enjoy the benefits, but I had to have a plan B for when she was busy.

Lisa's room was empty now and I tried several of her new clothes. Being almost her size helped. I found a dress that looked perfect on me. With the right padded bra, long stockings, a wig, and certain touches on my face, I thought I looked beautiful. I sashayed in front of the mirror and felt I was more than beautiful - I was sexy!

It was 8:30 pm. I had a sudden urge to be outside and let the world see me now. The evening weather was nice, around 70 degrees, with a minor breeze. Not wanting to be seen by my parents, I exited the house from the back door and drove to a parking structure downtown. The first 50 yards I walked in a dark alley. Then I reached the much more lighted main street. I barely strolled 20 feet and I heard the first whistle in my direction. It was a young guy riding a bike. I smiled at him. I moved on, noticing that most men, irrespective of their ages were ogling and inspecting my body. To my surprise, among the ones who I caught staring at me were also women. Some smiled at me and I thought they were lesbians. The other 3 ladies glanced at me with their faces showing disgust. Those 3 women walked with mates whose eyes explored my body openly, and I concluded the females saw me as a threat or a rival. I continued walking, proud of myself, and ignored the frequent looks.

I passed near a noisy bar, hearing my favorite pop music. After being in high heels for more than half an hour, my feet hurt, and I entered the bar. Fortunately, a small table in a dark corner was empty. I sat down. A man in uniform came in my direction and asked what I wanted to drink.

"Can you make me a vodka with watermelon punch?"

"Sure lady, be back with your drink in 5." As he left, a tall guy about 35 years old, came toward my table with a glass in his hand. He smiled at me, "Hello pretty lady. My name is Bob. I was sitting here and just went to the barman to get a drink. Do you mind if we share the same table?"

He looked nice - Smiley, polite, and nonthreatening. Why not? We could chat.

"No sir, take a seat."

In the beginning, Bob looked around, now and then staring at me. Once I caught him, he smiled, "As I said, my name is Bob. What's yours?"

"My name is Toni."

"You are very pretty but aren't you too young to be in a bar?"

I chuckled, "I am 20 years old."

My cocktail arrived. Bob's eyes made me nervous and I chugged half the glass. His eyes moved from my face to my chest and back to my face. He smiled again, "I see some couples dancing on the floor. Would you do me the honor?"

I tried politely to refuse, "Sorry, but I am a terrible dancer. Let's skip it, or I'll step on your toes with my high heels..."

He stood up, "Toni, I am a good dancer. Let me help you. Dancing is easy once you get into the rhythm."

He grabbed my arm gently and forced me on my feet. He led us to the floor. A slow music was playing. He put my right hand on his waist and the left one on his shoulder. He began moving in slow steps, following the relaxing tune. It felt good - There were no complicated moves, and Bob held me securely in his strong arms. The first song ended and the second slow one started immediately after. Bob whispered, "Toni, I watched you during the dance and thought you were amazing. Let's have more fun."

His hands pulled me into him and my head leaned on his chest. Yes, he was even taller than I thought, I'd say about 6'3"... His body and mine touched each other while we whirled around. I could smell his musky deodorant, and even feel his pulse. As we continued, I could feel something hard growing between us. I didn't want to embarrass Bob, and frankly, I saw it as a compliment for being attractive. I continued dancing, feeling free. My initial anxiousness disappeared. Was it because Bob liked me or the alcohol? I wasn't sure, but I didn't care.

In the third slow dance, Bob started slowly grinding his pole against my pelvis. Not knowing how to react I looked at his face. He took it the wrong way and kissed me gently. It wasn't a wild attack on my lips but I shivered. It was the first time a man kissed me!

I lowered my gaze and thought about it. After all, it was my decision to become a woman. The kiss itself wasn't unpleasant... I lifted my face again. His lips descended onto mine and slowly spread them. He inserted his tongue into my mouth and searched for my trembling tongue. While his mouth sucked on mine, his bulge grew further, and his hand moved from my waist to my ass. It felt good, but the progress was too fast for me. I tried to separate us. He whispered, "Toni, don't fight it. I feel good about you and think you feel the same way about me. Don't be scared. I promise not to do anything you don't like. I think you are very sexy, here feel it." Next, he grabbed my palm and placed it on his tent, pushing it to massage the bulge up and down.

I looked around; nobody was watching us. Bob was nice to me and I hated to make him feel bad, so I bobbed his tool, noticing it was MUCH bigger than mine.

He whispered again, "You like my hard cock, don't you?"

I grinned, "It's huge!"

"Toni, usually it stays quiet in my trousers, but the sudden stiffness is because of you."

"Bob, I doubt this monster is ever normal size..."

"I can easily prove it to you."

"How?"

His hand pulled me and I followed him. He opened a door at the far end and we entered a dark store room. He closed the door, leaned his back on it, and smiled, "Toni, here you'll get the proof you wanted. Unzip me."

"Bob, I don't think it's a good idea. I'll take your word for it."

"Girl, I see on your face you don't believe me. Unzip me. Now!"

"Bob, please..."

"Toni, remember I promised not to force you to do something you didn't like? I repeat my promise. However, let me prove something."

I stared at his face. He was serious, yet not alarming. Oh, what the hell. I fumbled with his zipper and carefully opened it. A massive piece of meat jolted out of its cage toward me. He had no underwear and his uncircumcised cock was directed at my face. It was between 8" and 9", with the envelope barely covering the base. The tool was large and the veins bulged outward. The basal area was covered with thick dark hair and I could see part of his heavy ball sack.

My eyes were mesmerized by the amazing rod. I've never seen something like it, and I still remembered some friends who were proud of their organs. Compared to theirs, his was awesome!

I felt my lips drying, and I licked them, not thinking much about it. Bob smiled, "Toni, I knew you'd like my present. Go ahead, touch it, and feel its warmth."

I had to admit I was curious to touch it and feel the texture, but hesitated.

"Toni, I can see it in your eyes. You are interested but frightened. You don't have to."

His palm took mine very gently and placed it around his shaft. My hand could not encircle the large organ. I trailed gingerly along his prick. It felt velvety and very pleasant. I focused on the mushroomed head. It was somewhat larger than the shaft. I touched it with my fingers. It jerked a little. Bob grinned, "My buddy is saying hello. I think he likes you already."

I continued staring at his magic wand and mumbled, "It is very impressive, and touching it is nice."

"Toni, both you and him like each other, how about an introduction kiss?"

I guess deep down, when he closed the door, I suspected it might lead this way but refused to think logically. The gentle seduction, being curious about his giant organ, and the alcohol lowered my resistance threshold. I glanced at his face. His eyes pointed to his erect cock.

I sighed, knelt down, and took the raging thing in both my hands. I massaged it slowly, watching it grow further. A drop of precum appeared on top. I squeezed his tool from base to head and the drop increased in size.

Bob caressed my wig, "Toni, don't fight it. You know you want to taste it."

He was so right... But everything was so new. I hesitated.

His hand slowly shoved my head down onto the spongy head. I licked the drop. The taste was very mild. I raised my face and gazed into Bob's eyes. He smiled at me and whispered, "You have beautiful full lips. They know what to do now."

Of course, I knew. Now my concern was more technical than mental - How do I accommodate such a huge meat in my mouth without choking?!...

Bob kept his promise and didn't push me. And then, I decided to give it a try. If I wasn't able to take it. I'd quit.

My lips wrapped around the soft head, barely able to insert it in. If any of the readers ever tried to swallow a whole Termitomyces Titanicus, well, that's the feeling I was having. The difference was that the biggest edible mushroom can be cut using tools or teeth, yet Bob's cock was a treasure to be kept in one piece...

To my credit, I tried hard. On my third attempt, my lips enveloped the distal part of his wide girth. The organ liked it, gifting my mouth with additional precum. I swallowed it and moved at a snail's pace to accept more of his member into my mouth. When half his pole was in my oral cavity, I felt I was about to choke. I did not dare to take more of him inside. My tongue began licking his underside and I tried to bob his penis the best I could.

He laughed, "Toni, you are fantastic! The blow job queen. You make me so horny with your sexy mouth. Here, let me help you."

Subsequently, he put his hands behind my neck, and gradually began to fuck my face. He was as gentle as he could, but a moment later his body shook, and his pounding turned wilder. I tried to free my head but to no avail. Seconds later he flooded my mouth with his slimy spunk. I gagged and felt nauseated but he kept his seed pouring. I made a valiant effort to swallow it all, but it was way too much and some spilled on the floor from the sides of my mouth. I was so consumed by trying to take it all, that only later I heard his growls. It felt like an hour had passed, although I doubted his climax lasted more than a minute. The massive organ began shriveling in my mouth and I let go. I stayed in my position trying to better assess the taste. To my surprise, it wasn't bad at all! Yes, it was slimy, but unlike some of the people I talked to, who compared it to snot, to me, it felt more like raw oysters, and it was one of my favorite foods...

I stood up and smiled shyly at Bob. His palm caressed my cheek, "Toni, your mouth is a gift from heaven. I need to go now, but here is my card. Anytime you feel the urge to use my pacifier again, call me. Again, your lips are amazing. Take care, girl."

He left, and I stayed in the small room trying to understand what just happened. From a young man who liked to cross-dress, I turned into a girl serving sexually my older sister, and now becoming a cocksucker... More worrisome was the fact that I didn't suffer. At every step, my initial reaction was resistance, but later on, the overall impression was positive, and I was less reluctant to try it again... I kept Bob's card in my pocket and did not discard it. I doubted I'd call him again, but I knew for sure I'd return to the bar another time.