01-01-2019, 03:14 PM
After reading Aden's story, I was inspired to tell mine about my first encounter. It happened earlier this year. It was early August of this past year of 2018. I had been corresponding a lot with "Renee" whom I had met on the Fetlife website. As we got to know each other more and more through our emails, I became more and more excited at the thought of meeting with Renee. Our messages had become more and more erotic so we decided to meet at a motel in Chicago.
Those who have read some of my "particular" posts, know that I identify with being a woman. So the thought of meeting a man at a motel was thrilling to me. So often I had practiced fellatio on a dildo...so often I had jerked off into my hand and then licking my own cum off of my hand, imagining it was the result of my pleasuring another man.
I drove part of the way to Chicago, stopping at a rest area. I glued my breastforms onto my chest. In the back seat of my car, I undressed from my male clothes. I then pulled up my girdle with pads in them to get that womanly look with hips and butt. On with the panty and my Vera Wang jeans. Next my socks and ankle boots, then a blouse. I moved to the front seat and used the rearview mirror to apply my makeup. Then my tomboy wig. I thought I looked pretty good and then drove on to Chicago for my destiny with Renee's cock at a motel.
Renee made arrangements for the room and had arrived in advance of me. Renee said he was going to surprise me when I entered the door. I wasn't sure what to expect and for a moment I got crazy thoughts of a stalker attacking me from behind. After all of our correspondence, I knew that was silly so I entered through the door and called out "Renee".
Renee approached me from behind the door and softly called out "hello lover" and reached around me to cup my breasts in his hands. I turned in his arms and for a moment looked at him. Renee is a crossdresser and was wearing a dress and a wig but no makeup but to me, as Anne, I saw a man before me, maybe ever so slightly shorter than me as I am 5'8". We embraced, our mouths meeting each other, our tongues probing each others mouth, our tongues performing some exotic dance like two wet snakes twirling around each other. I pulled back as I had one thing on my mind. I dropped to my knees as Renee lifted his dress for me to gaze on his semi-hard cock. It was so surreal. I had many times fantasized and dreamed of this moment and here it was finally happening.
I took his cock in my hand and guided his cockhead to my mouth. As his tip slid into my mouth, I reveled at the sensations I felt as my lips smoothly glided over the ridge of his cockhead. How many times had I felt a synthetic dildo in my mouth and now I was ecstatic as a I felt a living cock entering my mouth. My head moved forward and could swear I felt my lips riding over the veins of his shaft. My desire took me forward as far as I could go until, for the first time, my face was buried into a man's pubic hairs. Oh the feel of his bristly pubic hairs rubbing my face. I loved the feeling of his cock tip, rubbing the back of my throat as I bobbed my head in short strokes. His stiffness was complete as I backed off him, my lips gliding backwards...oh the sensation again as my lips rose across the ridge of his cock until he was completely out of me.
I looked at his cock and it was glistening with saliva. Renee said "oh Anne you bitch suck it some more". That was such a turnon to hear him speak to me like that. I took Renee's cock into my mouth again, feeling all those sensations all over again. My hands reached around his hips for support and this time I took him in long fast strokes. His cock moved back and forth in my mouth as I sucked hard each time his tip passed between my lips. My head thrust forward and back with urgency and then, for the first time, I could taste another man's precum. Here was another new sensation as his saltiness coated my tongue as his precum was seeping out of his cock.
This was all happening too fast, I thought. We had several hours to spend together and I did not want him to cum so soon although I was looking so forward to that moment. I backed off and stood up before him and we embraced again. I asked him to undress me and he helped pull off my blouse and jeans. I sat down and sexily rolled a pair of thigh high nylons onto my legs. He helped me into my red cocktail dress and I put on my red pumps. Those pictures I posted of me in my red cocktail dress were taken of me by Renee at the motel.
After doing some sexy posing and strutting for Renee, we layed together on the bed. We embraced more and moved into a 69 position. Renee was sucking me while I was sucking Renee. Even though I was getting pleasure from Renee sucking me, my true pleasure came from the pleasure I was giving him. I got a condom out of my purse and fit it into my mouth. Using my mouth, I rolled the condom onto Renee's cock. I squirted KY all over Renee's cock, spreading it all over the length and tip, feeling its slipperiness in my grip. I then squeezed Ky onto my fingers and rubbed it over my anus, my thoughts thinking about the sensation of a cock entering my ass. I positioned myself doggy style onto the edge of the bed and begged Renee to enter. This is where I was disappointed. Renee is about the same age as me and had trouble staying hard while wearing a condom. I eagerly got on my elbows and perched my butt in the air. I felt Renee's cock rubbing against my anus and I was prepared for that initial push into me but he softened. I tried to use my hands to stroke him hard again but it wasn't happening. At that point, I removed the condom from Renee and took him in my mouth again.
Just as before, my mouth eagerly took Renee's soft cock. I sucked on him as my moist mouth glided back and forth on him. Now, I had a new sensation to experience as I felt a soft cock grow in my mouth. I was getting excited with each stroke of my lips gliding up and down along the length of his shaft. As his stiffness grew, my pace quickened as my head bobbed back and forth. I knew I didn't want to stop now and neither did he. My passion was overtaking me as I my mouth was gliding up and down, each time my lips passing back forth over the ridge of his cocktip. Now his hips were slightly bucking to meet the thrusts of my mouth as I engulfed his cock into my throat. I pulled back just to look at the string of saliva that stretched and danced in the air from his cock to my mouth, just like a porn movie, I thought. I took him back into my mouth and stroked his cock for all I could with my mouth and his hips started bucking again. I could sense he was becoming more and more excited so I used my right hand to gently cup his testicles. My hand gently stroked his testicles back and forth to further excite him. Then came that glorious moment when his cock seemed to become extra rigid, just before that first exquisite muscle contraction. I felt that extra stiffness in my mouth and he let out a groan. Suddenly, I felt and tasted a rush of his hot, salty love into my mouth. Another new sensation for me as I experienced a man in his passion, spasming into my mouth. My senses reeled and for a moment, I was somewhat confused. I then reflexively swallowed his semen as his second contraction sent another pulse of semen into my mouth. I swallowed again while I used my mouth to work short strokes back and forth over the tip of his cock. He continued groaning and I knew I had taken everything he could give. I totally engulfed his cock once again, tasting his stickiness and lovingly used my mouth to perform a couple final long strokes. I sucked one last time, as I pulled my mouth back along his shaft and sat back. I was enthralled with myself that I could give such pleasure to a man. It was with satisfaction that I thought I had someone else's semen inside my mouth and stomach.
Afterwards we chatted a bit. Renee asked me to come down to Chicago to see him again. I haven't done that yet as it is not easy for a closeted gurl like me to get away and drive down to Chicago. Someday, I might but I was disappointed in his inability to keep hard and penetrate my ass from behind. I'm looking for that special (younger?) man that can do that for and to me. And that is the story of my very first sexual encounter with a man.
Those who have read some of my "particular" posts, know that I identify with being a woman. So the thought of meeting a man at a motel was thrilling to me. So often I had practiced fellatio on a dildo...so often I had jerked off into my hand and then licking my own cum off of my hand, imagining it was the result of my pleasuring another man.
I drove part of the way to Chicago, stopping at a rest area. I glued my breastforms onto my chest. In the back seat of my car, I undressed from my male clothes. I then pulled up my girdle with pads in them to get that womanly look with hips and butt. On with the panty and my Vera Wang jeans. Next my socks and ankle boots, then a blouse. I moved to the front seat and used the rearview mirror to apply my makeup. Then my tomboy wig. I thought I looked pretty good and then drove on to Chicago for my destiny with Renee's cock at a motel.
Renee made arrangements for the room and had arrived in advance of me. Renee said he was going to surprise me when I entered the door. I wasn't sure what to expect and for a moment I got crazy thoughts of a stalker attacking me from behind. After all of our correspondence, I knew that was silly so I entered through the door and called out "Renee".
Renee approached me from behind the door and softly called out "hello lover" and reached around me to cup my breasts in his hands. I turned in his arms and for a moment looked at him. Renee is a crossdresser and was wearing a dress and a wig but no makeup but to me, as Anne, I saw a man before me, maybe ever so slightly shorter than me as I am 5'8". We embraced, our mouths meeting each other, our tongues probing each others mouth, our tongues performing some exotic dance like two wet snakes twirling around each other. I pulled back as I had one thing on my mind. I dropped to my knees as Renee lifted his dress for me to gaze on his semi-hard cock. It was so surreal. I had many times fantasized and dreamed of this moment and here it was finally happening.
I took his cock in my hand and guided his cockhead to my mouth. As his tip slid into my mouth, I reveled at the sensations I felt as my lips smoothly glided over the ridge of his cockhead. How many times had I felt a synthetic dildo in my mouth and now I was ecstatic as a I felt a living cock entering my mouth. My head moved forward and could swear I felt my lips riding over the veins of his shaft. My desire took me forward as far as I could go until, for the first time, my face was buried into a man's pubic hairs. Oh the feel of his bristly pubic hairs rubbing my face. I loved the feeling of his cock tip, rubbing the back of my throat as I bobbed my head in short strokes. His stiffness was complete as I backed off him, my lips gliding backwards...oh the sensation again as my lips rose across the ridge of his cock until he was completely out of me.
I looked at his cock and it was glistening with saliva. Renee said "oh Anne you bitch suck it some more". That was such a turnon to hear him speak to me like that. I took Renee's cock into my mouth again, feeling all those sensations all over again. My hands reached around his hips for support and this time I took him in long fast strokes. His cock moved back and forth in my mouth as I sucked hard each time his tip passed between my lips. My head thrust forward and back with urgency and then, for the first time, I could taste another man's precum. Here was another new sensation as his saltiness coated my tongue as his precum was seeping out of his cock.
This was all happening too fast, I thought. We had several hours to spend together and I did not want him to cum so soon although I was looking so forward to that moment. I backed off and stood up before him and we embraced again. I asked him to undress me and he helped pull off my blouse and jeans. I sat down and sexily rolled a pair of thigh high nylons onto my legs. He helped me into my red cocktail dress and I put on my red pumps. Those pictures I posted of me in my red cocktail dress were taken of me by Renee at the motel.
After doing some sexy posing and strutting for Renee, we layed together on the bed. We embraced more and moved into a 69 position. Renee was sucking me while I was sucking Renee. Even though I was getting pleasure from Renee sucking me, my true pleasure came from the pleasure I was giving him. I got a condom out of my purse and fit it into my mouth. Using my mouth, I rolled the condom onto Renee's cock. I squirted KY all over Renee's cock, spreading it all over the length and tip, feeling its slipperiness in my grip. I then squeezed Ky onto my fingers and rubbed it over my anus, my thoughts thinking about the sensation of a cock entering my ass. I positioned myself doggy style onto the edge of the bed and begged Renee to enter. This is where I was disappointed. Renee is about the same age as me and had trouble staying hard while wearing a condom. I eagerly got on my elbows and perched my butt in the air. I felt Renee's cock rubbing against my anus and I was prepared for that initial push into me but he softened. I tried to use my hands to stroke him hard again but it wasn't happening. At that point, I removed the condom from Renee and took him in my mouth again.
Just as before, my mouth eagerly took Renee's soft cock. I sucked on him as my moist mouth glided back and forth on him. Now, I had a new sensation to experience as I felt a soft cock grow in my mouth. I was getting excited with each stroke of my lips gliding up and down along the length of his shaft. As his stiffness grew, my pace quickened as my head bobbed back and forth. I knew I didn't want to stop now and neither did he. My passion was overtaking me as I my mouth was gliding up and down, each time my lips passing back forth over the ridge of his cocktip. Now his hips were slightly bucking to meet the thrusts of my mouth as I engulfed his cock into my throat. I pulled back just to look at the string of saliva that stretched and danced in the air from his cock to my mouth, just like a porn movie, I thought. I took him back into my mouth and stroked his cock for all I could with my mouth and his hips started bucking again. I could sense he was becoming more and more excited so I used my right hand to gently cup his testicles. My hand gently stroked his testicles back and forth to further excite him. Then came that glorious moment when his cock seemed to become extra rigid, just before that first exquisite muscle contraction. I felt that extra stiffness in my mouth and he let out a groan. Suddenly, I felt and tasted a rush of his hot, salty love into my mouth. Another new sensation for me as I experienced a man in his passion, spasming into my mouth. My senses reeled and for a moment, I was somewhat confused. I then reflexively swallowed his semen as his second contraction sent another pulse of semen into my mouth. I swallowed again while I used my mouth to work short strokes back and forth over the tip of his cock. He continued groaning and I knew I had taken everything he could give. I totally engulfed his cock once again, tasting his stickiness and lovingly used my mouth to perform a couple final long strokes. I sucked one last time, as I pulled my mouth back along his shaft and sat back. I was enthralled with myself that I could give such pleasure to a man. It was with satisfaction that I thought I had someone else's semen inside my mouth and stomach.
Afterwards we chatted a bit. Renee asked me to come down to Chicago to see him again. I haven't done that yet as it is not easy for a closeted gurl like me to get away and drive down to Chicago. Someday, I might but I was disappointed in his inability to keep hard and penetrate my ass from behind. I'm looking for that special (younger?) man that can do that for and to me. And that is the story of my very first sexual encounter with a man.
Anne
But I guess that makes me a 'whore in waiting'. I read Anne's story and can only dream of the pleasure I would give a man. His pleasure would be all that mattered to me. To be 'owned' by a big alpha bull, and have him use my body for his pleasure would truly make me the complete woman I must become. Oh Anne, I need a man...