Straight Man's First Time
Anyone who has browsed my profile, would know that I am also a crossdresser, though that was dependent on work trips out of town and I'm retired now so I can't get out of town overnight by myself. Having said that, I don't dress in drag any more.
Back around 2016, I was working a job where I would be out of state for 2 weeks, home for 1 week, then back to work for 2 weeks. Did this for 6 months. While on this job, I was spamming CL, Xhamster, Fetlife, if it was free and offered a way to meet people for sex, I was spamming it! I had a lot of success, probably met with 25 different men and one of them brought their girlfriend to watch.
One particular guy, I'll call Tom, had never been with another man before, not even in a 3 some. He watched a lot of tranny/sissy/cd porn, and fantasized about it constantly until he finally worked up the nerve to contact me through Fetlife. He was in his 40's and married. When he messaged me, he only said "Hey". Normally I ignore those and go on to the next message, but this night I didn't have any more messages, so I messaged back "Hey Daddy, are you looking for some fun tonight". I got no reply for 3 days.
Finally he messages back and says "Yes". We work out details on when he would come over, what he would like me to wear, and what kind of fun he's looking for. He then lays out his whole life story about his sexual desires and confides that he's never done this before and he's kind of nervous. I give him the whole speech about how since I'm the girl, he's not the gay one, I am. I guess it worked because he didn't dip out like all the other virgins do.
It's Saturday evening and he shows up at hotel room like he said he would. I'm wearing a Rock-a-Billy 50's style June Cleaver dress with black nylons, black high heels, a brunette medium length wig, and all the make up and jewelry I can put on. He comes in and sits down on the bed, I sit in a chair across from him and ask him if he's ready to do this? He says "Yes". I get down on my knees, he stands up with his bulge inches from my face and I start do undo his pants. I pull his pants down and sniff his cock through his underwear. I then gently put my teeth on his cock through his underwear and I can feel how hard his cock is. He can't deny how much he's enjoying this!
I finally pull his underwear down, remove his pants and underwear completely, then I cup his balls and massage them. He lets out a long deep groan. His cock is kind of on the slender side, but it's a nice 8 inches, and it's standing straight up! I grab his cock with my other hand and start softly stroking him, and I get another long deep moan! At this point, I'm trying to decide what I want because I don't think he'll make it though a Blowjob AND anal! I take his cock and bring it to my lips, gently breath on it then I lick the sensitive area under the head. He lets out a quick quiver. I finally decide I want to taste his cum more than I want to feel his cock inside of me, it was a tough decision to make, but there it is.
I take his cock and go all the way down on it until my nose is pressed up against his stomach. I hold for a few seconds, then come back up and look him in the eyes as a bob up and down on his cock. He's moaning, gyrating his hips and puts his hands on the back of my head. Not even a minute into the bobbing, he lets out a loud "Oh God"! and shoots a nice warm load in my mouth. I showed him his cum, which was a lot, then swallowed it all.
It got a little awkward after that, not in a bad way. He laid on the bed for a minute, talking about how great that was and how his wife never did anything like that. I wanted to cuddle with him and kiss him, but I didn't know if he was ready for that, so I didn't, I just sat on the bed and watched for clues so I would know what to do next. He eventually got up, got dressed, thanked me, then left. No kissing. Fortunately that wasn't the last time I saw him. A couple days later he messaged me wanting to meet again. This time he fucked me and I got that kiss!
Back around 2016, I was working a job where I would be out of state for 2 weeks, home for 1 week, then back to work for 2 weeks. Did this for 6 months. While on this job, I was spamming CL, Xhamster, Fetlife, if it was free and offered a way to meet people for sex, I was spamming it! I had a lot of success, probably met with 25 different men and one of them brought their girlfriend to watch.
One particular guy, I'll call Tom, had never been with another man before, not even in a 3 some. He watched a lot of tranny/sissy/cd porn, and fantasized about it constantly until he finally worked up the nerve to contact me through Fetlife. He was in his 40's and married. When he messaged me, he only said "Hey". Normally I ignore those and go on to the next message, but this night I didn't have any more messages, so I messaged back "Hey Daddy, are you looking for some fun tonight". I got no reply for 3 days.
Finally he messages back and says "Yes". We work out details on when he would come over, what he would like me to wear, and what kind of fun he's looking for. He then lays out his whole life story about his sexual desires and confides that he's never done this before and he's kind of nervous. I give him the whole speech about how since I'm the girl, he's not the gay one, I am. I guess it worked because he didn't dip out like all the other virgins do.
It's Saturday evening and he shows up at hotel room like he said he would. I'm wearing a Rock-a-Billy 50's style June Cleaver dress with black nylons, black high heels, a brunette medium length wig, and all the make up and jewelry I can put on. He comes in and sits down on the bed, I sit in a chair across from him and ask him if he's ready to do this? He says "Yes". I get down on my knees, he stands up with his bulge inches from my face and I start do undo his pants. I pull his pants down and sniff his cock through his underwear. I then gently put my teeth on his cock through his underwear and I can feel how hard his cock is. He can't deny how much he's enjoying this!
I finally pull his underwear down, remove his pants and underwear completely, then I cup his balls and massage them. He lets out a long deep groan. His cock is kind of on the slender side, but it's a nice 8 inches, and it's standing straight up! I grab his cock with my other hand and start softly stroking him, and I get another long deep moan! At this point, I'm trying to decide what I want because I don't think he'll make it though a Blowjob AND anal! I take his cock and bring it to my lips, gently breath on it then I lick the sensitive area under the head. He lets out a quick quiver. I finally decide I want to taste his cum more than I want to feel his cock inside of me, it was a tough decision to make, but there it is.
I take his cock and go all the way down on it until my nose is pressed up against his stomach. I hold for a few seconds, then come back up and look him in the eyes as a bob up and down on his cock. He's moaning, gyrating his hips and puts his hands on the back of my head. Not even a minute into the bobbing, he lets out a loud "Oh God"! and shoots a nice warm load in my mouth. I showed him his cum, which was a lot, then swallowed it all.
It got a little awkward after that, not in a bad way. He laid on the bed for a minute, talking about how great that was and how his wife never did anything like that. I wanted to cuddle with him and kiss him, but I didn't know if he was ready for that, so I didn't, I just sat on the bed and watched for clues so I would know what to do next. He eventually got up, got dressed, thanked me, then left. No kissing. Fortunately that wasn't the last time I saw him. A couple days later he messaged me wanting to meet again. This time he fucked me and I got that kiss!
1年前
