My First Cigarette & My First Man

I had been talking to man online now for 4 months; we had been sharing our fantasies and fetishes. I am a cute transsexual woman with a smooth slender body and nice full 36 C cup breasts, until now I had never been with a man, never shared my beautiful untouched body. The man online expressed meeting me, and said he would transition me into his own sexual fantasy, it sounded very exciting, so we made a date and agreed to meet.

We lived 4 hours apart and agreed to meet half way, so I booked a room for two nights at a nice hotel. He told me that I should get there the night before and he would meet me in the morning and spend the day with me. I arrived that night at the hotel and checked into my room. It was lovely, perfect for my deflowering the next morning. I spent that night bathing and shaving my silky skin, applying baby oil to my beautiful tits and full ass ensuring I would be soft and juicy for him.

I woke up to the sound of the alarm clock, it was 9 am he would be arriving at 10, so I bathed one more time, and then proceeded to dress as he requested. Sliding out of my bathrobe, I perfumed my body and began dressing, first my black satin bra with matching satin panties, the bra as requested was one size too small so my tits were mashed together spilling out of the top. Next I put on my black lace garter belt with black thigh high stockings. I ran my long nails gently across the tops of the stockings making my heart race as they did small circles along my thighs. I finished off the set with 6 inch black patent heels with ankle straps and a dark red silk dress.

I took my time with my make up, nice full red lips and slightly darker lip liner, dark seductive eyes, then a light foundation, perfect! I stood in front of the mirror and enjoyed how erotic and beautiful I looked.

It was 15 minutes after 10 when I heard a knock at my door, I opened it and he was there with flowers and a big duffel bag, I was delighted to see him but was curious what was in the bag! He introduced himself to me, his name was Steven, he was about 6'2" with a medium build, nice brown hair and a sweet smile. Steven was a few years older than me and much more experienced, so he quickly was able to take control and make me feel comfortable with him, as he knew this was my first time meeting a man from online or anywhere for that matter.

I asked him if he would like to sit and chat before we began, he agreed. We sat down next to each other on the sofa and talked for a minute, he asked if I minded if he smoked, I told him it was a non smoking room and it might not be a good idea, he laughed and said he was surprised that I didn't smoke. I told him it was a filthy habit and he responded that women who smoked were very erotic and that I should learn to smoke for him. I giggled and said I might try someday. He laughed, and said, "that might be today", took his pack of cigarettes out and proceeded to smoke. He said "it's ok they don't really care" and blew a stream of smoke in my direction. I waved my hand clearing the air, he said "get used to it baby".... I replied, "Oh I don't know about you" and smiled.

We talked for all of what was 20 minutes, getting familiar with each other, he commented on how attracted he was to me and what a good choice the outfit was perfect for my transition. He told me then that today would be a life changing experience, I said "well what did you have in mind?", you know that I am a virgin, it will take some time, and I am nervous on top of that!

Steven unzipped the bag he brought with him and removed out a bottle of pills, I said, "what's that?" He said "here take 2 of these, they are Valium it will help you get relaxed". I looked at the bottle they were indeed valium and I had taken one before, and he was right they would help me to relax, so I took two. Soon after I felt my whole body relax and I was very willing. Steven reached over and pulled me close to him and began kissing me wet and deeply, he paused and whispered in my ear, "baby, do you trust me?" I said "yes", he replied "can I make you into MY girl?" I said yes, he said you will do what I say, and pulled me tight, "Yes", "yes Steven, do as you wish".

Steven reached into his bag and removed a long silk sheet and some clear tape; he told me to standup with my hands at my sides, I did so. He began wrapping me in the sheet, pulling it tight to my body, covering me from my ankles to my neck; he then took the tape and wrapped a few bands around my legs and arms securing them snuggly. I said "this is interesting", I was so relaxed I didn't even think anything was strange. Steven quickly and with force grabbed me my ass and said firmly, "you are in training, you will not speak unless you are told so, you will let me do as I wish with you, and I promise that you are safe, you still trust me don't you?" I said "yes", he replied, "No more talking, let me finish preparing you".

I was secured in the sheet barely able to move, the pressure of the silk cocoon wrapping my body was very exciting, I felt great! My heart began beating hard with excitement and the concern of what may happen next.

Steven finished securing me, and then removed a blindfold from his bag; he explained that depravation and bondage would help me in my sexual transformation. He placed the blindfold over my eyes; I could no longer view what he was doing. I felt something press into my ears, then silence. Now I could not see or hear was going on in the room. I was swaying almost ready to fall from the constriction of the sheet, I felt heavy hands grab me and gently lay me on to my back upon the bed. Steven then began stroking my body over the sheet his hands hungrily groping my body and then my breasts, running his rough nails over them I could feel a faint tingling in my nipples.

This was quite unnerving not knowing what will happen next but I released myself to Steven and I allowed him total control.

I felt something poking at my side, then I felt some tugging on the sheet then a release I felt cool air start to pour in over my chest, I realized that he had cut a hole in the sheet and exposed my chest. He continued cutting through my dress and my slip, then I felt two hands reach inside my bra and pull my tits up and over, this made me release a gentle moan from pleasure! Once my breasts were exposed he began fondling them gently tugging on my nipples, once they were hard he began suckling them, the sensation made me so hot! Then suddenly he stopped, I felt him get off the bed and then I felt him return, then I smelled smoke, he was smoking in the room again! Just as I thought that I felt something at my lips, it was the butt of a cigarette, he opened my mouth and placed it between my lips, when he realized I wasn't dragging on it, he gently held my nostrils together, I inhaled!

And smoke poured down my lungs, I coughed and turned away, he slapped my face and held it back in place, forcing me to repeat this, this time he held his had over my mouth and nose so I could not exhale, when he removed them, I let the smoke out of my lungs, and became very dizzy, I had never smoked before and had no idea what it would be like, he repeated this until eventually I began dragging off the cigarette, the idea I was bound and being forced to smoke began making me very aroused. When what had seemed like the first was finished he stroked my body and kissed me passionately- getting me ready for my second cigarette. He placed the butt of a new cigarette between my full red lips, I inhaled on my own this time, he removed the cigarette from my lips and as I exhaled then gently teased my nipples by rubbing the wet butt across them, making them erect and sensitive. This was repeated until the cigarette from what I assumed was finished, forcing me to have taken many drags on the second one, I was very dizzy, and extremely aroused.

Steven rolled me over onto my belly, then, I felt him position two pillows underneath me putting my ass into the air. I could not move from this position. I felt the same sensation on my ass that I did on my chest, he was cutting into the sheet over my backside. He cut a long slit and spread it, and another trough my dress and slip. Then carefully he cut a very long slit in my panties, I felt the cold metal scissors bush by my ass he completed.

I knew now this was his plan to take my virginity, as I began to ask him, he grabbed my head and forced something into my mouth, followed by a strip of tape to secure it. It took me a minute to figure out what this was, he had used his underwear to gag me, I could smell his manhood on them! Before I knew it I felt something cold being poured between the slits and onto my ass, then I felt pressure, he inserted one finger inside of me then two, I tried to moan but was unable to from my gag. He continued to work three fingers inside of me making sure I was well lubed and a bit stretched for what was to come. He got up from the bed again, when he returned I felt him position himself onto my legs and then the heavy flop of his warm cock against my lubed entry, I was defenseless, I would have to allow him to have his way. Steven expertly pressed and guided his cock into my ass, I felt a pop and moaned loudly through the gag, he paused, and then with one action slid his cock all the way into me. He must have been huge, I felt as if I were being split in half!

My asshole shivered and quaked as he withdrew his cock, then plunged in again, he did this a few times and my insides burned from the stretching of my womanhood, now he began fucking me, and the rhythm of his cock gradually began to feel amazing! The sensations of pain now replaced with ecstasy, he fucked my ass like this, long and deep pulling out and plunging back in many times gaping my virgin asshole. As the pace quickened and I felt like I would faint, his hips grinding into my bottom with force, my moans only made his thrusting harder, and then all of a sudden I felt him bury his cock deeper than ever! And with this he began to orgasm and fill my insides with his warm wet sticky sperm, my ass was spasming around his cock as he collapsed on top of me, not withdrawing but gently humping my ass until his swollen cock became limp and he slipped out. I felt a warm trail of cum escape my ass and pour down my thighs as I faded into a deep sleep.

When I awoke I was free of my bindings, and Steven was gone, my body was limp from the drugs and the stretching, along side me were the flowers he brought, a note and a pack of cigarettes. The note read, "you have now made it through your sexual transition to womanhood, I expect you to be a sexy smoker by the next time we meet," love Steven.