So this is the story about how I got my first experience being a bottom, and why it was with a tranny
I was 18 and wanted to try being a bottom. For a long time I had experimented by myself at home with different things (hair brushes handles, screw drivers handles, ping pong paddles handles etc...) but I really wanted the real thing. I had the fantasy about sucking dick and getting fucked. I had been watching anal sex porn, gay porn and shemale porn for a long time, and always I thought the tranny porn was the best. The idea of having a beautiful woman fuck me was very exiting for me.
So this one night, I was jerking off and then i thought to myself "why not?” Went into the local gay chat room and started looking for someone to "get together with". But the idea of having a man on top of me was not what I wanted, I didn't want to have sex with a guy, I just wanted to have sex with a cock. So the idea came to mind, Why not go for a tranny? Went on Google and searched for tranny escorts on my area, and to my surprise the market was huge!!! Beautiful shemales offering sex (of course it was not for free, but who cares?). I spent a few minutes checking and decided for this brunette, long haired, girly, big breasted and with a big dick shemale.
I dialed her number on my phone, but for some reason I had a hard time pushing the "Dial" key. Until I did. The phone rang a few times until a very sweet voice answered, she sounded sexy and friendly, we spoke for a few moments and I told her that I was looking for my first time, not only with a shemale but as bottom all together. She laughed a little, and told me to come over, that she had experience with "first timers"
I jumped into the car and drove to her place. Rang the door bell, it was an intercom of a building with no doorman; she opened the door for me and told me to go in.
When I got to her apartment she was even more beautiful than the pictures. About my height (5'9"), big breasted, she was wearing a tight black and very short dress, showing all her curves. Invited me in and we sat on the living room for a little while, gave a glass of water and we started chatting. She asked what my fantasy was, and I answered "I want to be bottom... with everything that means. I want to do oral, and be bottom. I'm only afraid it may hurt a lot", she chuckled and told me "don't worry, it won't hurt. Come on, come with me" she took my hand and led me to her room. The light was dimmed, a big bed, it was quite high, on the TV was playing a porn movie, and I saw by the night stand a big bottle of lube, condoms and a roll of toilet paper. She told me to get naked and that she will be right back, and left the room. I undressed, all but my boxers.
When she came back she was no longer wearing the dress, she had on lingerie set... she looked stunning. We started kissing, very wet and passionate kisses. I started touching her boobs and butt and she also was touching me, my cock was rock hard, she started touching it gently. She went down to her knees and lowered my boxers, I knew what was about to happen and couldn't be happier, she started sucking my dick like no one had ever sucked me before, it was awesome.
She went on for a minute or so and got up, kissed me and whispered to my ear "your turn, get down to your knees". I was petrified. The moment I had dreamed about for so long it was about to become true. It was a mix of feelings; I was scared but so much exited. I went down to my knees and stared at her, She chuckled again and said "touch me trough the panties, feel me", and I started touching her cock through her underwear, and just like in a movie started licking her through the panties.
It didn't take long until she pushed very gently my head back a little and took her panties off, and then I saw it for the first time, a dick that wasn't mine own. I couldn't even move, she crouched, kissed me and took my hand. When she stand up straight she looked at me dead in the eyes and put my hand on her semi hard cock and told me "start getting comfortable with it, touch it, make me hard" and so I did, feeling it grow in my hand.
When she was hard it was a gorgeous dick, 7.5 inches, not a hair on sight, to nicely hanging and fully waxed balls, a dig head shinning because of the precum. Then she told me "look at me and open your mouth" I was eager to start doing it, so I did as told and felt how she ever so gently started slapping her cock on my face very softly, on my cheeks, closing in to the mouth until she placed the head on my tongue and told me "close your mouth, take it in, be careful with the teeth" I close my mouth around it and started moving backwards and forwards slowly. I was finally sucking dick.
A few moment went by and they told me "use your tongue too", so I did, took it out to take a breath and jerked her for a second, then she lifted it and told me "you have to take care of them too" while gently pushing my head towards her balls, I licked them and sucked them, her moaning was getting louder and hotter by the minute.
Then she pushed her cock back in my mouth, but no so gently anymore, she was getting into it and I loved it. At some point she turned around, bend over spreading her ass cheeks and told me "lick my hole, eat me from behind"... I didn't even questioned her or myself, just started licking that asshole as hard and wet as I could, her moaning was driving me crazy. She turned around again, sat on the edge of the bed and enjoyed the blow job I was providing.
Then she stands up and says "ok honey, it's time, get on the bed", suddenly I got very scared and was starting to second guess myself, told her "I think I just took a huge step forwards, I sucked your dick, balls and asshole... I think is enough for the first time, I rather keep doing this until you cum". She came to me, kissed me and said to my ear "you told me you want to get fucked and you're not leaving here until I have my way with your virgin ass, so climb up the bed and get on all fours" I was scared, but also fulfilling my fantasy, to be the "girl", the bottom.
I go on the bed and down on all fours and waited. Looked back and saw her putting on a rubber and taking the bottle of lube, she said "you'll feel cold, I'm lubing you up" and felt how she started touching my butthole. I was just waiting for it, on my knees and elbows. And then felt how she got on the bed, graved my by side hip on the felt and started passing her cock head through my crack, up and down, until she found the hole.
She didn't penetrated me right away, she started playing with my ass, just pushing slightly and I was getting hornier by the second, until she said "ok, I'm going in" and I felt how she started going in and hurt a lot. I jumped out and told her that it was too much for me, and I didn't want to go through with it. She told me "ok, let me try one more thing, it will help you, you'll enjoy it, trust me", I agreed.
She told me to turn around and lay on my back, raise and spread my legs, she placed a pillow on my lower back to raise my asshole a little and they went to look for something on her night stand, she grabbed a normal size bottle of lube and said "I'm going to lube you also from the inside, I'll put in only the tip of the bottle and squirt lube inside, ok?" I said yes. I felt the cold lube in my rectum, and how she started fingering me, I was getting more and more relaxed.
After a few moments she came to me, kissed me and said "let's try again" as I felt her cock's head looking for my hole again. Suddenly I realized that I was spreading my legs and had a gorgeous shemale about to fuck me, so I relaxed as much as I could, closed my eyes and "took it like a man".. or woman hahaha.
I felt how the head went in, and she started to push deeper and deeper until it was in completely, then came and whispered to my ear "there it is, your ass is not virgin anymore" and started moving in and out slowly. Then I felt how she started going faster, but carefully.
She lifted her body from mine, to hold my legs from the ankles and kept giving it to me that way, that's when I started hearing the "fucking" sound, that clapping. it went on for a few minutes and she told me "ok, let's try again doggy style, I just have to fuck you like that", I agreed by nodding and assumed the position, I was again on my knees and elbows and she said "no, put your chest down and spread you cheeks you both hands" so I did and felt her hand on my left hip and her dick head again pushing on my asshole.
Then she jammed it all the way in and I released a strong moan, I didn't hurt or maybe I was just to exited to feel the pain. At that point she went crazy fucking me, strong and hard, I could hear the clapping strong I was enjoying it, then she slapped my ass and I moaned in pleasure, and she said "ohh, so you like being spanked? I'm going to spank you, you dirty slut", jammed her cock as deep and hard as she could and spanked me strong, I was in bliss and answered "yes, keep doing it". I cummed but didn't told her, I wanted her to cum too, so I kept taking it.
Then she stops ramming me, gets off of the bed and says "I'm about to cum, get to your knees and make me cum". Quickly I got down and started sucking her cock, until she took it from my mouth.
I started jerking it hard and said "keep your mouth open, I want to cum in your mouth" so I did, I look at what was going on and saw a beautiful big breasted woman jerking her gorgeous cock and about to cum in my mouth, and I started cumming again, then she moaned hard and said "I'm cumming" and I felt the hot cum on my tongue and mouth and her cumming face...
I was in heaven. Then she said "Don't swallow, I want to see you first. Show me", I started showing her the cum on my tongue like in the movies and she said "you look hot, now you can swallow", so I did.
She told me to go clean myself in the bathroom and get dressed. Gave me a kiss goodbye, I paid her and left.
I was 18 and wanted to try being a bottom. For a long time I had experimented by myself at home with different things (hair brushes handles, screw drivers handles, ping pong paddles handles etc...) but I really wanted the real thing. I had the fantasy about sucking dick and getting fucked. I had been watching anal sex porn, gay porn and shemale porn for a long time, and always I thought the tranny porn was the best. The idea of having a beautiful woman fuck me was very exiting for me.
So this one night, I was jerking off and then i thought to myself "why not?” Went into the local gay chat room and started looking for someone to "get together with". But the idea of having a man on top of me was not what I wanted, I didn't want to have sex with a guy, I just wanted to have sex with a cock. So the idea came to mind, Why not go for a tranny? Went on Google and searched for tranny escorts on my area, and to my surprise the market was huge!!! Beautiful shemales offering sex (of course it was not for free, but who cares?). I spent a few minutes checking and decided for this brunette, long haired, girly, big breasted and with a big dick shemale.
I dialed her number on my phone, but for some reason I had a hard time pushing the "Dial" key. Until I did. The phone rang a few times until a very sweet voice answered, she sounded sexy and friendly, we spoke for a few moments and I told her that I was looking for my first time, not only with a shemale but as bottom all together. She laughed a little, and told me to come over, that she had experience with "first timers"
I jumped into the car and drove to her place. Rang the door bell, it was an intercom of a building with no doorman; she opened the door for me and told me to go in.
When I got to her apartment she was even more beautiful than the pictures. About my height (5'9"), big breasted, she was wearing a tight black and very short dress, showing all her curves. Invited me in and we sat on the living room for a little while, gave a glass of water and we started chatting. She asked what my fantasy was, and I answered "I want to be bottom... with everything that means. I want to do oral, and be bottom. I'm only afraid it may hurt a lot", she chuckled and told me "don't worry, it won't hurt. Come on, come with me" she took my hand and led me to her room. The light was dimmed, a big bed, it was quite high, on the TV was playing a porn movie, and I saw by the night stand a big bottle of lube, condoms and a roll of toilet paper. She told me to get naked and that she will be right back, and left the room. I undressed, all but my boxers.
When she came back she was no longer wearing the dress, she had on lingerie set... she looked stunning. We started kissing, very wet and passionate kisses. I started touching her boobs and butt and she also was touching me, my cock was rock hard, she started touching it gently. She went down to her knees and lowered my boxers, I knew what was about to happen and couldn't be happier, she started sucking my dick like no one had ever sucked me before, it was awesome.
She went on for a minute or so and got up, kissed me and whispered to my ear "your turn, get down to your knees". I was petrified. The moment I had dreamed about for so long it was about to become true. It was a mix of feelings; I was scared but so much exited. I went down to my knees and stared at her, She chuckled again and said "touch me trough the panties, feel me", and I started touching her cock through her underwear, and just like in a movie started licking her through the panties.
It didn't take long until she pushed very gently my head back a little and took her panties off, and then I saw it for the first time, a dick that wasn't mine own. I couldn't even move, she crouched, kissed me and took my hand. When she stand up straight she looked at me dead in the eyes and put my hand on her semi hard cock and told me "start getting comfortable with it, touch it, make me hard" and so I did, feeling it grow in my hand.
When she was hard it was a gorgeous dick, 7.5 inches, not a hair on sight, to nicely hanging and fully waxed balls, a dig head shinning because of the precum. Then she told me "look at me and open your mouth" I was eager to start doing it, so I did as told and felt how she ever so gently started slapping her cock on my face very softly, on my cheeks, closing in to the mouth until she placed the head on my tongue and told me "close your mouth, take it in, be careful with the teeth" I close my mouth around it and started moving backwards and forwards slowly. I was finally sucking dick.
A few moment went by and they told me "use your tongue too", so I did, took it out to take a breath and jerked her for a second, then she lifted it and told me "you have to take care of them too" while gently pushing my head towards her balls, I licked them and sucked them, her moaning was getting louder and hotter by the minute.
Then she pushed her cock back in my mouth, but no so gently anymore, she was getting into it and I loved it. At some point she turned around, bend over spreading her ass cheeks and told me "lick my hole, eat me from behind"... I didn't even questioned her or myself, just started licking that asshole as hard and wet as I could, her moaning was driving me crazy. She turned around again, sat on the edge of the bed and enjoyed the blow job I was providing.
Then she stands up and says "ok honey, it's time, get on the bed", suddenly I got very scared and was starting to second guess myself, told her "I think I just took a huge step forwards, I sucked your dick, balls and asshole... I think is enough for the first time, I rather keep doing this until you cum". She came to me, kissed me and said to my ear "you told me you want to get fucked and you're not leaving here until I have my way with your virgin ass, so climb up the bed and get on all fours" I was scared, but also fulfilling my fantasy, to be the "girl", the bottom.
I go on the bed and down on all fours and waited. Looked back and saw her putting on a rubber and taking the bottle of lube, she said "you'll feel cold, I'm lubing you up" and felt how she started touching my butthole. I was just waiting for it, on my knees and elbows. And then felt how she got on the bed, graved my by side hip on the felt and started passing her cock head through my crack, up and down, until she found the hole.
She didn't penetrated me right away, she started playing with my ass, just pushing slightly and I was getting hornier by the second, until she said "ok, I'm going in" and I felt how she started going in and hurt a lot. I jumped out and told her that it was too much for me, and I didn't want to go through with it. She told me "ok, let me try one more thing, it will help you, you'll enjoy it, trust me", I agreed.
She told me to turn around and lay on my back, raise and spread my legs, she placed a pillow on my lower back to raise my asshole a little and they went to look for something on her night stand, she grabbed a normal size bottle of lube and said "I'm going to lube you also from the inside, I'll put in only the tip of the bottle and squirt lube inside, ok?" I said yes. I felt the cold lube in my rectum, and how she started fingering me, I was getting more and more relaxed.
After a few moments she came to me, kissed me and said "let's try again" as I felt her cock's head looking for my hole again. Suddenly I realized that I was spreading my legs and had a gorgeous shemale about to fuck me, so I relaxed as much as I could, closed my eyes and "took it like a man".. or woman hahaha.
I felt how the head went in, and she started to push deeper and deeper until it was in completely, then came and whispered to my ear "there it is, your ass is not virgin anymore" and started moving in and out slowly. Then I felt how she started going faster, but carefully.
She lifted her body from mine, to hold my legs from the ankles and kept giving it to me that way, that's when I started hearing the "fucking" sound, that clapping. it went on for a few minutes and she told me "ok, let's try again doggy style, I just have to fuck you like that", I agreed by nodding and assumed the position, I was again on my knees and elbows and she said "no, put your chest down and spread you cheeks you both hands" so I did and felt her hand on my left hip and her dick head again pushing on my asshole.
Then she jammed it all the way in and I released a strong moan, I didn't hurt or maybe I was just to exited to feel the pain. At that point she went crazy fucking me, strong and hard, I could hear the clapping strong I was enjoying it, then she slapped my ass and I moaned in pleasure, and she said "ohh, so you like being spanked? I'm going to spank you, you dirty slut", jammed her cock as deep and hard as she could and spanked me strong, I was in bliss and answered "yes, keep doing it". I cummed but didn't told her, I wanted her to cum too, so I kept taking it.
Then she stops ramming me, gets off of the bed and says "I'm about to cum, get to your knees and make me cum". Quickly I got down and started sucking her cock, until she took it from my mouth.
I started jerking it hard and said "keep your mouth open, I want to cum in your mouth" so I did, I look at what was going on and saw a beautiful big breasted woman jerking her gorgeous cock and about to cum in my mouth, and I started cumming again, then she moaned hard and said "I'm cumming" and I felt the hot cum on my tongue and mouth and her cumming face...
I was in heaven. Then she said "Don't swallow, I want to see you first. Show me", I started showing her the cum on my tongue like in the movies and she said "you look hot, now you can swallow", so I did.
She told me to go clean myself in the bathroom and get dressed. Gave me a kiss goodbye, I paid her and left.