Bi-Sexual Male / 27
I had met a gorgeous woman at a fairly new bar in New York about a year or so ago. She was hott stuff. Dark hair, dark eyes, white skin, etc. I was seated at a bar stool, to her right, and her friends had gathered various stools in order to form a small group. That's actually a huge pet peeve of mine and I'm surprised the tenders/managers didn't seem to care. Must be a rule they ignore.
At first, I simply saw her as plastered and complaining to her friends about how her husband didn't take enough photos of her as well as a few other things. I don't know why she was so insecure. This girl didn't need to prove anything. Then again, given the generous intake of Stella Artois (she must not be much of a drinker), I think I knew exactly why she was feeling insecure.
At any rate, her friends were talking about going to another friend's place. She wasn't interested. That's when I realized that she acknowledged my existence. She punched my shoulder and said I was a great listener. I thought she just wanted an excuse to keep venting. Her friends left, and unless they had a limo or something, I wasn't sure how far they'd get, considering not a single one of them was sober. That brought me to another thought: How the hell was this girl going to get home?? I mean, I sure wasn't about to become someone else's DD, especially not someone I didn't even know. Doesn't matter how much they rate on the attractiveness scale, I've been burned too many times.
She just kept going on and on about shit I didn't care about. I found it peculiar, however, that every time I glanced over at her, she seemed a little closer. Must have been the hooch. Even a seasoned vet like myself has limits.
Talking of which, I realized that her hand was on my leg. Just how long was for anyone to surmise, but I didn't care at this point. I liked her. Her hand started moving other places until she started outright fondling me. Then, without warning, she whispered into my ear in what was quite possibly the most sober voice I've heard from someone so hammered: "Let's go to my place." Fuck, what a seductress.
But there was still that problem of us both being drunk as skunks and not being able to drive anywhere. Oh...how...convenient. She lives a few blocks away. Having impaired judgment by now, I was only mildly suspicious.
On the way I vomited behind a newspaper box. Or maybe it was a fire hydrant...or a woman in a red skirt. Still not quite sure at this point.
Once at her place (it's a miracle we didn't break our necks stumbling up those stairs), I realized with horror that her husband could very well have been home. Turned out he wasn't, thankfully.
We sat on the couch for a few hours. We were laughing continuously about who knows what, but one thing was for sure, if we had moved much, we would have blown chunks again, and this was a nice penthouse. Her husband must have been very successful.
We must have started feeling better, because she started feeling my dick again and told me she liked me. She made her way inside my jeans and started grabbing my balls. She eventually swung her leg over me (nearly giving me a bloody nose in the process, which was also quite hilarious to her) and started unbuttoning my shirt. She started removing her own clothing, with difficulty, but was eventually bare. That's when I noticed it.
She had a dick.
Ho-lee shit. She was a shemale.
I stared at it for what felt like a couple of minutes. She was hot, and very well endowed in both the tit and shaved dick departments. Keep in mind that I was completely sober the first time I saw her. I did not think it was possible for a guy to look that gorgeous.
She was hard. Very hard. I decided that we were going to have fun that night whether or not we were both guys, girls, squirrels, etc.
She went first.
She sat on the couch and I knelt in front of her and started jerking her off. She had such a nice dick. I rubbed my hands and fingers all over it, making sure to get her glans and frenulum just right. She started breathing heavily and moving with almost every jerk. I figured I'd lay it on even more. I ran my lips all along that hard spear of hers and stuck it right in my mouth after it was positively glistening. I could feel her on my tongue and in my throat. The sucking was loud, and so was she. Time passed, and she eventually grabbed it and started jerking very quickly giving me a fierce gaze. Oh yes, I knew what this meant. I sucked on her balls a little just to add some pleasure to it, then, while running my fingers all over her perineum and lightly touching the tip of her anus, I closed my eyes and puckered up.
It took a little longer than I expected, but soon she sprayed her cum all over my face, rubbing her dick on my lips while moaning, "Fuuuuuuuck yeah..." She shot it out for longer than I expected as well. How long had she been saving all that????
She was tired. That load must have took a lot out of her. I quickly washed my face before taking my turn.
We started making out. She had such sweet lips. I made sure to lick every inch of the inside of her mouth. She was tasty.
She reached down and returned my favor by tickling my balls and perineum. I pushed her down onto the couch. She looked up at me, those lustful eyes squinting with desire. "Fuck me, now." I slipped my cock right into her anus with no trouble at all.
We copulated for at least 20 minutes. She pulled me down onto her, biting my ear and licking my neck, not quite knowing what to do with herself. Apparently, she was really enjoying herself.
"Fuck my little fuckin' tranny ass!" she commanded. Way ahead of you, baby.
The orgasm came gradually. I could feel my cum muscles slowly tensing up. I looked at her, she looked at me. We were both enjoying this with the same level of intensity.
Breathing softly now, she whispered into my ear, "Give it to me, big boy." She moaned quietly as my throbbing dick pulsed for at least 30 seconds squirting my cum and filling her rectum, the goosebumps intensifying at this moment of pure ecstasy.
We remained there, sweaty, and panting. The couch actually felt a tiny bit moist when we finally got up. She thanked me, telling me that she hadn't had a free amateur fuck like that in several months. Her husband was traveling the East Coast doing shoots with popular local models.
Foolishly, I never asked her name. I've only been to that bar a handful of times since then, and, understandably, I've never seen her. She was amazing that night.
At first, I simply saw her as plastered and complaining to her friends about how her husband didn't take enough photos of her as well as a few other things. I don't know why she was so insecure. This girl didn't need to prove anything. Then again, given the generous intake of Stella Artois (she must not be much of a drinker), I think I knew exactly why she was feeling insecure.
At any rate, her friends were talking about going to another friend's place. She wasn't interested. That's when I realized that she acknowledged my existence. She punched my shoulder and said I was a great listener. I thought she just wanted an excuse to keep venting. Her friends left, and unless they had a limo or something, I wasn't sure how far they'd get, considering not a single one of them was sober. That brought me to another thought: How the hell was this girl going to get home?? I mean, I sure wasn't about to become someone else's DD, especially not someone I didn't even know. Doesn't matter how much they rate on the attractiveness scale, I've been burned too many times.
She just kept going on and on about shit I didn't care about. I found it peculiar, however, that every time I glanced over at her, she seemed a little closer. Must have been the hooch. Even a seasoned vet like myself has limits.
Talking of which, I realized that her hand was on my leg. Just how long was for anyone to surmise, but I didn't care at this point. I liked her. Her hand started moving other places until she started outright fondling me. Then, without warning, she whispered into my ear in what was quite possibly the most sober voice I've heard from someone so hammered: "Let's go to my place." Fuck, what a seductress.
But there was still that problem of us both being drunk as skunks and not being able to drive anywhere. Oh...how...convenient. She lives a few blocks away. Having impaired judgment by now, I was only mildly suspicious.
On the way I vomited behind a newspaper box. Or maybe it was a fire hydrant...or a woman in a red skirt. Still not quite sure at this point.
Once at her place (it's a miracle we didn't break our necks stumbling up those stairs), I realized with horror that her husband could very well have been home. Turned out he wasn't, thankfully.
We sat on the couch for a few hours. We were laughing continuously about who knows what, but one thing was for sure, if we had moved much, we would have blown chunks again, and this was a nice penthouse. Her husband must have been very successful.
We must have started feeling better, because she started feeling my dick again and told me she liked me. She made her way inside my jeans and started grabbing my balls. She eventually swung her leg over me (nearly giving me a bloody nose in the process, which was also quite hilarious to her) and started unbuttoning my shirt. She started removing her own clothing, with difficulty, but was eventually bare. That's when I noticed it.
She had a dick.
Ho-lee shit. She was a shemale.
I stared at it for what felt like a couple of minutes. She was hot, and very well endowed in both the tit and shaved dick departments. Keep in mind that I was completely sober the first time I saw her. I did not think it was possible for a guy to look that gorgeous.
She was hard. Very hard. I decided that we were going to have fun that night whether or not we were both guys, girls, squirrels, etc.
She went first.
She sat on the couch and I knelt in front of her and started jerking her off. She had such a nice dick. I rubbed my hands and fingers all over it, making sure to get her glans and frenulum just right. She started breathing heavily and moving with almost every jerk. I figured I'd lay it on even more. I ran my lips all along that hard spear of hers and stuck it right in my mouth after it was positively glistening. I could feel her on my tongue and in my throat. The sucking was loud, and so was she. Time passed, and she eventually grabbed it and started jerking very quickly giving me a fierce gaze. Oh yes, I knew what this meant. I sucked on her balls a little just to add some pleasure to it, then, while running my fingers all over her perineum and lightly touching the tip of her anus, I closed my eyes and puckered up.
It took a little longer than I expected, but soon she sprayed her cum all over my face, rubbing her dick on my lips while moaning, "Fuuuuuuuck yeah..." She shot it out for longer than I expected as well. How long had she been saving all that????
She was tired. That load must have took a lot out of her. I quickly washed my face before taking my turn.
We started making out. She had such sweet lips. I made sure to lick every inch of the inside of her mouth. She was tasty.
She reached down and returned my favor by tickling my balls and perineum. I pushed her down onto the couch. She looked up at me, those lustful eyes squinting with desire. "Fuck me, now." I slipped my cock right into her anus with no trouble at all.
We copulated for at least 20 minutes. She pulled me down onto her, biting my ear and licking my neck, not quite knowing what to do with herself. Apparently, she was really enjoying herself.
"Fuck my little fuckin' tranny ass!" she commanded. Way ahead of you, baby.
The orgasm came gradually. I could feel my cum muscles slowly tensing up. I looked at her, she looked at me. We were both enjoying this with the same level of intensity.
Breathing softly now, she whispered into my ear, "Give it to me, big boy." She moaned quietly as my throbbing dick pulsed for at least 30 seconds squirting my cum and filling her rectum, the goosebumps intensifying at this moment of pure ecstasy.
We remained there, sweaty, and panting. The couch actually felt a tiny bit moist when we finally got up. She thanked me, telling me that she hadn't had a free amateur fuck like that in several months. Her husband was traveling the East Coast doing shoots with popular local models.
Foolishly, I never asked her name. I've only been to that bar a handful of times since then, and, understandably, I've never seen her. She was amazing that night.
