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Anything Goes
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Straight Male / 49
I Tried It
Ok so I thought I'd make my own confession here.
About 20 years ago, give or take a few years, my girlfriend and I broke you for the last time. We had basically been together for over a year but we seemed to break up every other month. She was pretty crazy to say the least but she had the nicest ass I have ever seen and was up for anything sexually. I loved fucking her ass and she loved me fucking it.
When w I had finally had enough I told her this would be our last breakup. Her last words to me was I should find myself a boyfriend and fuck him all the time since I liked anal so much.
I had never thought about fucking guys. Yuck. Hairy asses are gross and men do nothing for me sexually at all. But it stuck in the back of my mind. I dated for a couple of years and had pretty good luck. Mostly younger girls, many of which were pretty hot, but not one would give up the ass. Pussy, sure, and I love eating pussy and did it many times. I'd even lick their assholes hoping that would open that door. But no, not one for two years or so.
So one day I'm bored and was reading the personal ads on craigslist. I keep seeing att these ads for trans women and answered a few. Most were just pros looking to get paid. Some were just bots trying to get you to join their pay sites etc... After a bit I just gave up on the notion of butt fucking some trans girl. I didn't want a CD. I wanted someone who looked like a girl and had nice tits. If she had a dick, I didn't care, I just wanted some anal!
In all I probably replied to 20 ads or more.
One out of all of them wasn't a prostitute or a fake, or a bit looking for my credit card number.
We exchanged a lot of emails over the next couple of days. She was looking for a relationship where she could be a real girlfriend to a straight man. I was honest and said I wasn't sure about a relationship but that I did enjoy our conversations and that she was pretty and seemed to be really cool. After a few more days and dozens of emails we exchanged numbers and talked on the phone for hours. I really liked talking to her. She was smart funny, a d soundedime a girl to me so we made arrangements to meet for dinner.
It was a Friday night, we met at Buffalo Wild Wings (classy, I know) but back then it was my favorite place to eat and hers too. So we meet and let me tell you, if I didn't know she was trans I never could have known until we got naked. She was prettier than her pictures even. She had pretty eyes, beautiful blonde hair and was tall and thin. Not much of a butt or tits to be honest but not bad at all either. She hadn't had implants but had been on hormones for years and had real boobs of her own. Not very big at all, maybe small B cups. But nice nipples I found out later. We eat and have a couple of beers and I realized I really liked this girl. I said I'll be willing to date her and see how it goes if she's interested. But told her I had zero experience with men. She said, honey I'm no man. If you can't see that, there's no point in going any further. I apologized over and over just trying to explain that man parts don't turn me on. She laughed and said she was just teasing and loved making me turn red. We left the restaurant and I kissed her goodbye. We went out on two more dates before we ended up at my place after our third date. We had a couple of drinks as we were making out on my couch. I was hard as a rock just from all the kissing. She started rubbing it and said, someone likes me. I said of course we do. You're so pretty, why wouldn't we? We get up and go to the bedroom and I syrup naked. She takes off her clothes but leaves her bra and panties on. We kiss more and she starts kissing down lower and lower until she reaches my throbbing hard on. Yes all 12 inches!!! Just kidding. I had to put that in here since EVERYONE is hung like a horse these days.
Anyhow it took probably two minutes of her sucking me before I came. I apologized again but it had been a while since I had cum and I was so turned on etc... She said so it wasn't just that it was the best ever?? Umm yes, yes it was great! Definitely the best I can remember at least right now.
We laid there kissing and fondling and I took her bra off and sucked on her nice titties for a bit and I was raging hard again. She said do you want to fuck me now? Hell yes I do! She asked if I had condoms and lube, which I did. She said ok baby but you have to lick it if you want to stick it! We both laughed out asses off. Then I pulled off her panties. I expected her to get on her knees so I could lick her back there but I stead she laid on her back and pulled her legs up exposing her pretty little brown eye. It was really nice! Her penis was hard too, not real big but probably 5 inches and kinda thick. Her balls were ti y though and shrunk up inside her almost. So I started licking her little butthole and loved it. She loved it too and was rubbing the head of her dick that was leaking precum. She was moaning and moaning. I licked her for about 5 minutes and was ready to fuck her and said I need that ass now. She said it's all your baby if you give my clit a quickuck or two. So I did. I licked her dick up and down and even sucked on it. It wasn't bad. I actually liked it because she seemed to really like it.
I only did it for a minute or two though. She then said ok you can fuck me now baby. I put on a condom, put some lube in her ass and on my covered cock and fucked her missionary. I was gentle at first but then started fucking her in earnest as she begged .e to fuck her harder and harder. She started shooting cum out of her dick and her ass started squeezing my cocj and releasing with every spurt. I erupted. The condom burst even and there was cum all over both of us.
I dated her for 2 years. I even think I was in love with her. I sucked her dick every day and fucked her ass every day and loved doing both. She was the first and last trans girl I ever was with. I have never sucked another dick since. I've never been with another man. But I'd love to have her back. But I fucked that all up when she caught me fucking another girl. I just missed eating pussy too much I guess. But I still think about her often and miss her.
About 20 years ago, give or take a few years, my girlfriend and I broke you for the last time. We had basically been together for over a year but we seemed to break up every other month. She was pretty crazy to say the least but she had the nicest ass I have ever seen and was up for anything sexually. I loved fucking her ass and she loved me fucking it.
When w I had finally had enough I told her this would be our last breakup. Her last words to me was I should find myself a boyfriend and fuck him all the time since I liked anal so much.
I had never thought about fucking guys. Yuck. Hairy asses are gross and men do nothing for me sexually at all. But it stuck in the back of my mind. I dated for a couple of years and had pretty good luck. Mostly younger girls, many of which were pretty hot, but not one would give up the ass. Pussy, sure, and I love eating pussy and did it many times. I'd even lick their assholes hoping that would open that door. But no, not one for two years or so.
So one day I'm bored and was reading the personal ads on craigslist. I keep seeing att these ads for trans women and answered a few. Most were just pros looking to get paid. Some were just bots trying to get you to join their pay sites etc... After a bit I just gave up on the notion of butt fucking some trans girl. I didn't want a CD. I wanted someone who looked like a girl and had nice tits. If she had a dick, I didn't care, I just wanted some anal!
In all I probably replied to 20 ads or more.
One out of all of them wasn't a prostitute or a fake, or a bit looking for my credit card number.
We exchanged a lot of emails over the next couple of days. She was looking for a relationship where she could be a real girlfriend to a straight man. I was honest and said I wasn't sure about a relationship but that I did enjoy our conversations and that she was pretty and seemed to be really cool. After a few more days and dozens of emails we exchanged numbers and talked on the phone for hours. I really liked talking to her. She was smart funny, a d soundedime a girl to me so we made arrangements to meet for dinner.
It was a Friday night, we met at Buffalo Wild Wings (classy, I know) but back then it was my favorite place to eat and hers too. So we meet and let me tell you, if I didn't know she was trans I never could have known until we got naked. She was prettier than her pictures even. She had pretty eyes, beautiful blonde hair and was tall and thin. Not much of a butt or tits to be honest but not bad at all either. She hadn't had implants but had been on hormones for years and had real boobs of her own. Not very big at all, maybe small B cups. But nice nipples I found out later. We eat and have a couple of beers and I realized I really liked this girl. I said I'll be willing to date her and see how it goes if she's interested. But told her I had zero experience with men. She said, honey I'm no man. If you can't see that, there's no point in going any further. I apologized over and over just trying to explain that man parts don't turn me on. She laughed and said she was just teasing and loved making me turn red. We left the restaurant and I kissed her goodbye. We went out on two more dates before we ended up at my place after our third date. We had a couple of drinks as we were making out on my couch. I was hard as a rock just from all the kissing. She started rubbing it and said, someone likes me. I said of course we do. You're so pretty, why wouldn't we? We get up and go to the bedroom and I syrup naked. She takes off her clothes but leaves her bra and panties on. We kiss more and she starts kissing down lower and lower until she reaches my throbbing hard on. Yes all 12 inches!!! Just kidding. I had to put that in here since EVERYONE is hung like a horse these days.
Anyhow it took probably two minutes of her sucking me before I came. I apologized again but it had been a while since I had cum and I was so turned on etc... She said so it wasn't just that it was the best ever?? Umm yes, yes it was great! Definitely the best I can remember at least right now.
We laid there kissing and fondling and I took her bra off and sucked on her nice titties for a bit and I was raging hard again. She said do you want to fuck me now? Hell yes I do! She asked if I had condoms and lube, which I did. She said ok baby but you have to lick it if you want to stick it! We both laughed out asses off. Then I pulled off her panties. I expected her to get on her knees so I could lick her back there but I stead she laid on her back and pulled her legs up exposing her pretty little brown eye. It was really nice! Her penis was hard too, not real big but probably 5 inches and kinda thick. Her balls were ti y though and shrunk up inside her almost. So I started licking her little butthole and loved it. She loved it too and was rubbing the head of her dick that was leaking precum. She was moaning and moaning. I licked her for about 5 minutes and was ready to fuck her and said I need that ass now. She said it's all your baby if you give my clit a quickuck or two. So I did. I licked her dick up and down and even sucked on it. It wasn't bad. I actually liked it because she seemed to really like it.
I only did it for a minute or two though. She then said ok you can fuck me now baby. I put on a condom, put some lube in her ass and on my covered cock and fucked her missionary. I was gentle at first but then started fucking her in earnest as she begged .e to fuck her harder and harder. She started shooting cum out of her dick and her ass started squeezing my cocj and releasing with every spurt. I erupted. The condom burst even and there was cum all over both of us.
I dated her for 2 years. I even think I was in love with her. I sucked her dick every day and fucked her ass every day and loved doing both. She was the first and last trans girl I ever was with. I have never sucked another dick since. I've never been with another man. But I'd love to have her back. But I fucked that all up when she caught me fucking another girl. I just missed eating pussy too much I guess. But I still think about her often and miss her.
- That's Juicy! 16
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