First time with a crossdresser.
I received a message asking for a meet up from Tracy, a 40 year old transvestite, a bit risky but after a bit of searching I decided to give it a go. This was going to be my first time with a crossdresser so I was anxious how it was going to go, every hook up now I've been at I've been the bottom, so with a fellow cd I wasn't sure how this was going to go, if it was even going to lead to sex (I sure hoped it would though).
I was given a location, which was in a park behind a building, it was very private. I am getting more brave now and wearing what I feel comfortable in out and about. For this meet I knew it was going to lead to some sort of sexy fun, much more than I'd have worn out before, so I wore a sexy Basque, see through panties and a large plug, black stockings and heels, a halter neck short dress. I arrived at the spot but my date wasn't there. I started to think it was a set up. Then I started to hear the distinctive sound of high heels coming down the path, just that sound alone started to get me going. The steps got closer and my cock started to twitch with anticipation. This long legged stunning cd walked round the building. She was wearing super high heels, nude stockings a mini skirt, a huge set of fake breasts that a her top was trying ever so hard to keep them in, it wasn't working lol.
She said hi and confidently came straight up to me and kissed me, I was taking a back slightly but as she started to passionately kiss me there wasn't much I could do, so I just kissed her back. Her tongue soon came out to play and forced it's way deep into my now very open mouth, her tongue was so long it was touching the back of my mouth, it was so sexy, we kissed like that for ages, thoroughly enjoying this new experience. My hands started to explore down her back and eventually her sexy tight bum. I pulled her tight to me and that's when I felt her massive hard cock. I started to rub myself up against her huge length. She obviously liked it as her tongue went into over drive, this was turning into a good night.
I was now so Egor to see and taste her cock I pulled away from the kissing, she stopped me and quickly got to her knees. Her hands went under my dress and exposed my panties and could see my cock, she said "oh wow that's a sexy big prick" She kissed and licked my cock through my knickers and eventually released it from the shearer material. This was going to be my first ever blowjob not from a woman. Tracey held the base of my cock and pulled it towards her out stretched tongue and started to lick the tip and then the head. With her tongue being so long she was able to lick right around the head and then with her mouth open she took my shaft inside. It was amazing, she sucked and licked the head for ages and then moved herself slightly, she told me to hold her head and fuck her mouth. I didn't need asking twice, I slowly pushed the head in then half of my shaft, I pulled out and in to halfway for a time and then I felt her push herself further down, so I couldn't resist, wiith my hands on her head I push my cock deeper and deeper until my balls were on her chin, she was moaning with joy at this, I can certainly relate to this joy she was feeling in the position she was in. I fucked her mouth until I was close to coming and had to stop before I blew my load.
I said to her "it's my turn to have your balls slapping my chin" she said "good luck with that, it's never been done before" I quivered with anticipation to see how big her cock really was now. I pushed her against the wall, kissed her but my tongue explored her mouth this time. I slowly went down her body feeling and kissing her. I felt her huge swollen shaft and kissed it through her skirt. I was now crouched down, I decided this was going to go all the way so I slid her skirt down and she stepped out of it. OMG what a sight. She had on the most beautiful lingerie set, deep purple Basque and matching panties. Her cock was far too big to stay in the knickers . I have sucked quite a few cocks now but nothing like this one, it was daunting. I started to lick her balls through the shearer kickers, and then worked my way up her shaft, kissing and tonguing every inch. I soon go to the exposed part of her cock and the got to the head, she was dripping with pre cum. I licked it up so quickly, it was delicious. I then took her head in my mouth, I could soon see why she said nobody had taken her balls deep before, but I was certainly going to give it my best shot.
I started to take more and more of her down to the back of my mouth, her hands held my head and I moved to get my head in a better position and then she took over just like I did. She fucked ⅔ of her shaft in and out my mouth and then she slowed down and pushed in further, she pushed past my mouth and into my throat now, I was so turned on now I thought I might cum. She pulled out and little then pushed in but this time she didn't stop, she must of been encouraged by my moans of pleasure and she pushed her huge cock until her ball were touching my chin. I moved my hand from her balls to her hole, and started to rub it, with all the juices coming out of my mouth rubbed them all around her twitching hole and then pushed 2 fingers in. She started to shake and pulled her cock out but just left the head in, I explored her hole and found her P spot, I rubbed it with a bit of pressure and a huge spert of cum hit the back of my throat, with that she held my head and forced herself balls deep again and then started to fuck my head so violently she couldn't stop herself and shouted out " oh I can't stop, your going to taste my cum you filthy slut" I started to wank myself off and finger her arseat the same time as she skull fucked me. Then with a massive thrust she injected me with so much cum, I started to gag now but all of this was far too much for me and I came so hard. I cleaned and licked her cock and got back to my feet. She kissed me deeply tasting herself. We sorted our self's out and she said I'll message you again and winked. And then she was gone.
I was given a location, which was in a park behind a building, it was very private. I am getting more brave now and wearing what I feel comfortable in out and about. For this meet I knew it was going to lead to some sort of sexy fun, much more than I'd have worn out before, so I wore a sexy Basque, see through panties and a large plug, black stockings and heels, a halter neck short dress. I arrived at the spot but my date wasn't there. I started to think it was a set up. Then I started to hear the distinctive sound of high heels coming down the path, just that sound alone started to get me going. The steps got closer and my cock started to twitch with anticipation. This long legged stunning cd walked round the building. She was wearing super high heels, nude stockings a mini skirt, a huge set of fake breasts that a her top was trying ever so hard to keep them in, it wasn't working lol.
She said hi and confidently came straight up to me and kissed me, I was taking a back slightly but as she started to passionately kiss me there wasn't much I could do, so I just kissed her back. Her tongue soon came out to play and forced it's way deep into my now very open mouth, her tongue was so long it was touching the back of my mouth, it was so sexy, we kissed like that for ages, thoroughly enjoying this new experience. My hands started to explore down her back and eventually her sexy tight bum. I pulled her tight to me and that's when I felt her massive hard cock. I started to rub myself up against her huge length. She obviously liked it as her tongue went into over drive, this was turning into a good night.
I was now so Egor to see and taste her cock I pulled away from the kissing, she stopped me and quickly got to her knees. Her hands went under my dress and exposed my panties and could see my cock, she said "oh wow that's a sexy big prick" She kissed and licked my cock through my knickers and eventually released it from the shearer material. This was going to be my first ever blowjob not from a woman. Tracey held the base of my cock and pulled it towards her out stretched tongue and started to lick the tip and then the head. With her tongue being so long she was able to lick right around the head and then with her mouth open she took my shaft inside. It was amazing, she sucked and licked the head for ages and then moved herself slightly, she told me to hold her head and fuck her mouth. I didn't need asking twice, I slowly pushed the head in then half of my shaft, I pulled out and in to halfway for a time and then I felt her push herself further down, so I couldn't resist, wiith my hands on her head I push my cock deeper and deeper until my balls were on her chin, she was moaning with joy at this, I can certainly relate to this joy she was feeling in the position she was in. I fucked her mouth until I was close to coming and had to stop before I blew my load.
I said to her "it's my turn to have your balls slapping my chin" she said "good luck with that, it's never been done before" I quivered with anticipation to see how big her cock really was now. I pushed her against the wall, kissed her but my tongue explored her mouth this time. I slowly went down her body feeling and kissing her. I felt her huge swollen shaft and kissed it through her skirt. I was now crouched down, I decided this was going to go all the way so I slid her skirt down and she stepped out of it. OMG what a sight. She had on the most beautiful lingerie set, deep purple Basque and matching panties. Her cock was far too big to stay in the knickers . I have sucked quite a few cocks now but nothing like this one, it was daunting. I started to lick her balls through the shearer kickers, and then worked my way up her shaft, kissing and tonguing every inch. I soon go to the exposed part of her cock and the got to the head, she was dripping with pre cum. I licked it up so quickly, it was delicious. I then took her head in my mouth, I could soon see why she said nobody had taken her balls deep before, but I was certainly going to give it my best shot.
I started to take more and more of her down to the back of my mouth, her hands held my head and I moved to get my head in a better position and then she took over just like I did. She fucked ⅔ of her shaft in and out my mouth and then she slowed down and pushed in further, she pushed past my mouth and into my throat now, I was so turned on now I thought I might cum. She pulled out and little then pushed in but this time she didn't stop, she must of been encouraged by my moans of pleasure and she pushed her huge cock until her ball were touching my chin. I moved my hand from her balls to her hole, and started to rub it, with all the juices coming out of my mouth rubbed them all around her twitching hole and then pushed 2 fingers in. She started to shake and pulled her cock out but just left the head in, I explored her hole and found her P spot, I rubbed it with a bit of pressure and a huge spert of cum hit the back of my throat, with that she held my head and forced herself balls deep again and then started to fuck my head so violently she couldn't stop herself and shouted out " oh I can't stop, your going to taste my cum you filthy slut" I started to wank myself off and finger her arseat the same time as she skull fucked me. Then with a massive thrust she injected me with so much cum, I started to gag now but all of this was far too much for me and I came so hard. I cleaned and licked her cock and got back to my feet. She kissed me deeply tasting herself. We sorted our self's out and she said I'll message you again and winked. And then she was gone.
9ヶ月前
