So, here's how it went down.
I was 17, in the last year of HS and VERY horny. I wanted to fuck but wanted it to be something special and memorable, since I was the last virgin in my friend group and most of the guys had bad first times.
This led me to downloading the dating app Badoo and registering as 20.
After swiping for some weeks I matched with a seemingly catfish but she was verified so I messaged her.
She was a tan, busty, Brazilian girl. 10/10. She had "TS" in her profile but I wasn't into trans and didn't know. I looked it up and got a bit weirded out. But also turned on. I quickly realized I didn't mind fucking a Trans as a top.
We messaged through kik and she immediately told me she was a top and bareback only. This threw me off for a second but I was horny, she was hot and I have had some anal play (to spice up all the masturbating I was doing). She asked me if I like to "party" and not knowing she meant drugs I said yes and agreed to be her bottom.
We decided to meet at her city center apartment in the next few days.
On the day, I got a haircut, a workout, used my mom's hair cream to clear all body hair and got an enema (since I have used sharpies and toothbrushes for anal play that turned out dirty).
I told my parents I'm going training, stole a bottle of wine and took the bus to her. When I got to her apartments I rang her and heard her voice for the first time. She sounded like pure sex with a Brazilian accent. I was super turned on but also jittery.
I got to her apartment and she opened the door in nothing but a set of red thigh stockings, panties and bra.
She was big. I mean tall, busty, big booty. A real amazon. She kissed me on the cheek and welcomed me in. We went to her dimly lit living room sat down, talked for a bit and drank some wine. She brought out a small blue bottle and asked "G?", not knowing it was GHB I said yes. She poured a capful into a half glass cola for herself and me. We drank more wine and she took out a small bag and took out a little powder that she snorted off a coin. I had never done cocaine but didn't want to seem like a loser so I took a bump. We drank a little more, smoked a cigarette ( which I also didn't do) and did more coke.
My heart was beating, I lost all hesitation and got extremely turned.
She asked what I like sexually and I replied "you". She said "oh, show me" with a grin and opened her legs. Like instinct, I got on my knees and started kissing around her panties. She pulled out her soft but plump cock. She was uncut, darker than her bronze tan, almost black with a pink head and curved slightly.
At this point I knew that this was a turning point in my life and I was about to suck cock, like a fag that my friends make fun of and call each other jokingly. But in a heartbeat I put her whole soft and floppy brown penis in my mouth. I crossed the line but I didn't mind. I actually liked it.
I started sucking her cock the way I seen girls suck boys in porn and how I wanted mine sucked. She grew quickly and got more dominant. I was overwhelmed and had to pull back a few times not to gag or tear up. But she kept going and didn't mind me getting covered in saliva, gagging and tearing up. She actually got more turned on and got almost fully hard. She pulled my head down and forced her whole semi hard cock down my throat.
She grabbed my shirt and took it off and I stood up quick and took everything else off too. I got back to sucking her cock and she was fully hard and glistening, so was I. She was so much bigger than me and it looked like one of those dildos I seen in sex shop windows and thought no one had.
I just wanted to keep sucking and trying to impress her I chipmunked on her cock and slapped my face with it. Holding her cock I saw her balls and decided to suck on them. I put my mouth on them but her sack was tight. I had to suck hard to get one and the other into my mouth. Her balls were not very large and the sack had stubble. But I didn't mind.
She lifted her legs up and her butthole was an inch from my face. Having always fantasized about eating a girls ass and pussy I dived right in. It was clean, didn't taste much like anything. After about a couple of minutes of tonguing her smooth tan hole I got back to sucking her.
The drugs were in my system fully and I felt so slutty. I tried to throat her, licked it up and down and sucked her quickly bobbing my head. I began moaning in pleasure instinctively.
She told me "let's go bedroom-y" and with her cock still in my mouth I nodded and said "hmpf-kay".
We stood up. She leaned over me and we kissed. I held her hand and she led me to her bedroom.
In that brief moment I felt shame, for being a "fag" and doing hard drugs. But I knew what I got into and the line was crossed already. Turning back now seemed like an even gayer, cowardly move.
So I followed her down a dark corridor to an led light room. There were sex toys, lube, condoms and paper towels beside the bed on the nightstand.
She got naked and we lay on the bed kissing and caressing each other. And I will never forget how hard and huge her breasts and ass felt. One cheek was like five handfuls and her tits were bigger than anything I ever saw.
She out down a towel, laid me down on the bed, got down on her knees and started sucking me. She took me whole and hard all the way down without a problem.
The whole time she was sucking me she was putting a condom and lube on a vibrator that I felt press up against my ass. It slid in and she twisted the knob so it stared vibrating while sucking my cock.
She then jerked me off a little bit with a silicone pocket pussy with one hand while fucking me with the vibrator with the other one.
She put them away, threw out the condom and squirted a little lube on her hand which she stroked herself with. She got down again, put my knees to my ears and ate my ass. Which at this point was the least favorite part up to this point since it felt wet and weird.
But nothing could prepare me for what was to come.
She grabbed my hands and put them on the back of my knees which I just knew was to keep my legs up. She stood up and put the head of her hard cock up against my closed hole. With some effort of mashing it in she got it.
It felt like fire and I lost my erection fully. She knew I was hurt and wanted to back off but she went slow and said "stay, staaay" without thrusting. At this point I was about ready to quit but she leaned over kissed me and started moving her hips slightly. She leaned back applied another squirt of cold lube while staying in me and began fucking me.
It hurt a lot but after a little while the pain began to become bearable and even felt a little good.
She scratched my chest, but my nipple and kissed me. But she stayed close to my face and started talking to me. Calling me her "bitch", saying "delicia" and other Brazilian phrases and told me to open my mouth, in which she spit and missed but didn't wipe off the spit from my face.
She began fucking me faster and a little deeper and now I mostly liked it. She slipped out and stroked her cock over my fully soft one. She asked "why so small? why you no hard?" To which I didn't know what to say.
She grabbed my hips and put me in doggy. She entered quicker this time. The pain I thought was over was back but even more so. I wanted to back off. I wanted her to stop. But I stayed and focused on not crying.
Without knowing I was positioning myself into a more comfortable arched back position which she would push back down. The sex started feeling okay again and she thrust harder. This time I started to slowly back off of her but she stayed in and on me.
I was pinned face down in her faux fur blanket with her huge hard tits on my back and hands on my shoulders.
The pain quickly stopped and I felt something warm and wet on my back. I heard her moan and felt her body twitch on top of me.
She pulled out and painted my back with the biggest load I have ever seen.
I got wiped down with a paper towel, flipped over and saw a small wet pet where my soft cock was pressed down into the towel on her bed.
I realized I came. It was only a little and mostly clear. But I had cum.
That's when it hit me. I forever lost my virginity to a transexual and came from being fucked. Not how I had imagined my first time but the mix of emotions and drugs felt like nothing ever before.
I loved it.
We lay there and kissed a little, talked some.
We got a shower together where she peed and I got fully hard rubbing our cocks together. We got out and I got on the bathroom mat to suck her while masturbating and came all over the floor super hard.
We put on bathrobes and went into the balcony overlooking the city to smoke and chill.
That's when she told me she needed a visa and would pay me, take me to a holiday in Campinas and set up wild orgies for us if I married her. I told her I had just turned 17 not 20.
I got dressed and we kissed goodbye. Without realizing I had spent several hours in her apartment and the last bus was gone. I looked at my phone and had about 20 missed calls.
I called my dad to pick me up, which he did.
I felt ashamed the whole trip and wouldn't talk to him. When we got to the house mother was waiting. We went into the kitchen and Dad said "next time you're going out to a girl, tell us" which caught me off guard and I spat out "wuht". He told me I smelled of perfume and knew I was with someone. I could see the pride in his face. He thought his son had finally become a man.
Little did he know his son got drugged, fucked and his virginity taken by a big black Brazilian tranny cock. And that his son liked it too. And would go on to do it a lot more over the next years in secrecy.
I was 17, in the last year of HS and VERY horny. I wanted to fuck but wanted it to be something special and memorable, since I was the last virgin in my friend group and most of the guys had bad first times.
This led me to downloading the dating app Badoo and registering as 20.
After swiping for some weeks I matched with a seemingly catfish but she was verified so I messaged her.
She was a tan, busty, Brazilian girl. 10/10. She had "TS" in her profile but I wasn't into trans and didn't know. I looked it up and got a bit weirded out. But also turned on. I quickly realized I didn't mind fucking a Trans as a top.
We messaged through kik and she immediately told me she was a top and bareback only. This threw me off for a second but I was horny, she was hot and I have had some anal play (to spice up all the masturbating I was doing). She asked me if I like to "party" and not knowing she meant drugs I said yes and agreed to be her bottom.
We decided to meet at her city center apartment in the next few days.
On the day, I got a haircut, a workout, used my mom's hair cream to clear all body hair and got an enema (since I have used sharpies and toothbrushes for anal play that turned out dirty).
I told my parents I'm going training, stole a bottle of wine and took the bus to her. When I got to her apartments I rang her and heard her voice for the first time. She sounded like pure sex with a Brazilian accent. I was super turned on but also jittery.
I got to her apartment and she opened the door in nothing but a set of red thigh stockings, panties and bra.
She was big. I mean tall, busty, big booty. A real amazon. She kissed me on the cheek and welcomed me in. We went to her dimly lit living room sat down, talked for a bit and drank some wine. She brought out a small blue bottle and asked "G?", not knowing it was GHB I said yes. She poured a capful into a half glass cola for herself and me. We drank more wine and she took out a small bag and took out a little powder that she snorted off a coin. I had never done cocaine but didn't want to seem like a loser so I took a bump. We drank a little more, smoked a cigarette ( which I also didn't do) and did more coke.
My heart was beating, I lost all hesitation and got extremely turned.
She asked what I like sexually and I replied "you". She said "oh, show me" with a grin and opened her legs. Like instinct, I got on my knees and started kissing around her panties. She pulled out her soft but plump cock. She was uncut, darker than her bronze tan, almost black with a pink head and curved slightly.
At this point I knew that this was a turning point in my life and I was about to suck cock, like a fag that my friends make fun of and call each other jokingly. But in a heartbeat I put her whole soft and floppy brown penis in my mouth. I crossed the line but I didn't mind. I actually liked it.
I started sucking her cock the way I seen girls suck boys in porn and how I wanted mine sucked. She grew quickly and got more dominant. I was overwhelmed and had to pull back a few times not to gag or tear up. But she kept going and didn't mind me getting covered in saliva, gagging and tearing up. She actually got more turned on and got almost fully hard. She pulled my head down and forced her whole semi hard cock down my throat.
She grabbed my shirt and took it off and I stood up quick and took everything else off too. I got back to sucking her cock and she was fully hard and glistening, so was I. She was so much bigger than me and it looked like one of those dildos I seen in sex shop windows and thought no one had.
I just wanted to keep sucking and trying to impress her I chipmunked on her cock and slapped my face with it. Holding her cock I saw her balls and decided to suck on them. I put my mouth on them but her sack was tight. I had to suck hard to get one and the other into my mouth. Her balls were not very large and the sack had stubble. But I didn't mind.
She lifted her legs up and her butthole was an inch from my face. Having always fantasized about eating a girls ass and pussy I dived right in. It was clean, didn't taste much like anything. After about a couple of minutes of tonguing her smooth tan hole I got back to sucking her.
The drugs were in my system fully and I felt so slutty. I tried to throat her, licked it up and down and sucked her quickly bobbing my head. I began moaning in pleasure instinctively.
She told me "let's go bedroom-y" and with her cock still in my mouth I nodded and said "hmpf-kay".
We stood up. She leaned over me and we kissed. I held her hand and she led me to her bedroom.
In that brief moment I felt shame, for being a "fag" and doing hard drugs. But I knew what I got into and the line was crossed already. Turning back now seemed like an even gayer, cowardly move.
So I followed her down a dark corridor to an led light room. There were sex toys, lube, condoms and paper towels beside the bed on the nightstand.
She got naked and we lay on the bed kissing and caressing each other. And I will never forget how hard and huge her breasts and ass felt. One cheek was like five handfuls and her tits were bigger than anything I ever saw.
She out down a towel, laid me down on the bed, got down on her knees and started sucking me. She took me whole and hard all the way down without a problem.
The whole time she was sucking me she was putting a condom and lube on a vibrator that I felt press up against my ass. It slid in and she twisted the knob so it stared vibrating while sucking my cock.
She then jerked me off a little bit with a silicone pocket pussy with one hand while fucking me with the vibrator with the other one.
She put them away, threw out the condom and squirted a little lube on her hand which she stroked herself with. She got down again, put my knees to my ears and ate my ass. Which at this point was the least favorite part up to this point since it felt wet and weird.
But nothing could prepare me for what was to come.
She grabbed my hands and put them on the back of my knees which I just knew was to keep my legs up. She stood up and put the head of her hard cock up against my closed hole. With some effort of mashing it in she got it.
It felt like fire and I lost my erection fully. She knew I was hurt and wanted to back off but she went slow and said "stay, staaay" without thrusting. At this point I was about ready to quit but she leaned over kissed me and started moving her hips slightly. She leaned back applied another squirt of cold lube while staying in me and began fucking me.
It hurt a lot but after a little while the pain began to become bearable and even felt a little good.
She scratched my chest, but my nipple and kissed me. But she stayed close to my face and started talking to me. Calling me her "bitch", saying "delicia" and other Brazilian phrases and told me to open my mouth, in which she spit and missed but didn't wipe off the spit from my face.
She began fucking me faster and a little deeper and now I mostly liked it. She slipped out and stroked her cock over my fully soft one. She asked "why so small? why you no hard?" To which I didn't know what to say.
She grabbed my hips and put me in doggy. She entered quicker this time. The pain I thought was over was back but even more so. I wanted to back off. I wanted her to stop. But I stayed and focused on not crying.
Without knowing I was positioning myself into a more comfortable arched back position which she would push back down. The sex started feeling okay again and she thrust harder. This time I started to slowly back off of her but she stayed in and on me.
I was pinned face down in her faux fur blanket with her huge hard tits on my back and hands on my shoulders.
The pain quickly stopped and I felt something warm and wet on my back. I heard her moan and felt her body twitch on top of me.
She pulled out and painted my back with the biggest load I have ever seen.
I got wiped down with a paper towel, flipped over and saw a small wet pet where my soft cock was pressed down into the towel on her bed.
I realized I came. It was only a little and mostly clear. But I had cum.
That's when it hit me. I forever lost my virginity to a transexual and came from being fucked. Not how I had imagined my first time but the mix of emotions and drugs felt like nothing ever before.
I loved it.
We lay there and kissed a little, talked some.
We got a shower together where she peed and I got fully hard rubbing our cocks together. We got out and I got on the bathroom mat to suck her while masturbating and came all over the floor super hard.
We put on bathrobes and went into the balcony overlooking the city to smoke and chill.
That's when she told me she needed a visa and would pay me, take me to a holiday in Campinas and set up wild orgies for us if I married her. I told her I had just turned 17 not 20.
I got dressed and we kissed goodbye. Without realizing I had spent several hours in her apartment and the last bus was gone. I looked at my phone and had about 20 missed calls.
I called my dad to pick me up, which he did.
I felt ashamed the whole trip and wouldn't talk to him. When we got to the house mother was waiting. We went into the kitchen and Dad said "next time you're going out to a girl, tell us" which caught me off guard and I spat out "wuht". He told me I smelled of perfume and knew I was with someone. I could see the pride in his face. He thought his son had finally become a man.
Little did he know his son got drugged, fucked and his virginity taken by a big black Brazilian tranny cock. And that his son liked it too. And would go on to do it a lot more over the next years in secrecy.
