Kissing A Tranny
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Kissing A Tranny
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When I was in high school I was a bit socially awkward and especially around girls. I’d been with a number of girls, sure, but many of them left a lot to be desired. One year, a new family moved into my parent’s building and my life changed. That was because within that family, there was a very effeminate young male that I found on the back porch in total drag.
I was just coming upstairs from track practice when I noticed him. I was immediately struck by how beautiful he was in girls clothes and makeup. He was Puerto Rican descent and had full sensual lips that were even more enticing by the matte cranberry red lipstick.
I was frozen when I saw him. When he saw me, he looked horrified and backed into a corner thinking that I was going to wail on him. I assured him that he was safe and contrary to his fears, I actually thought he was really cute. The words just came out of nowhere because I was so smitten.
We wound up sitting on the back porch steps talking well into the night. And it was obvious that we had a mutual attraction for one another. We decided to slip into the basement stairwell of a vacant apartment in the building so that we could talk more freely which led to hand holding, which then led to the moment where I leaned in to kiss him. That led to another kiss, then another, then another, then more prolonged kissing and caressing. The next thing I knew, he was sitting on my lap while we continued kissing.
Knowing that our families would wonder where we were, we reluctantly decided to part and head back to our apartments. But this felt too good to abandon so we would meet regularly at the basement stairwell where we would kiss for hours. The level of intimacy was unmatchable and no girl in the neighborhood could even come close to what I experienced with this cross dresser. Every night I would rush from the dinner table just to meet up so that we could share those sensual kisses.
Unfortunately, I went away to college and when I returned that fall, I was told that this family had moved to California after the father of the family found a job there. This was before email and social media, so we never got a chance to reconnect.
I did find some consolation in the fact that one of our neighbors talked about how the son in the family cried the whole time he was leaving. I could have been wrong, but I was hoping that those tears were because we would not be together again.
Sorry if this story does not end in this cross dresser and I fully making love, but our kissing sessions were filled with the most sensuality that I’d ever experienced and something that will always hold a special place in my heart.
No “happy ending,” but a beautiful memory nonetheless.
No “happy ending,” sadly. But it’s a beautiful memory.
What a beautiful story and sad 😢, I had the same sort of thing happen to myself when I lived in Exmouth Australia and John went back to the United States. I have kicked myself ever since for not being truthful to my feelings.
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I slept with a tranny the other night
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MKS82
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By no means am I gay I never think about other dudes etc. But I was curious about trannys for the longest time. Never thought I would even consider hooking up with one. Ive slept with girls my whole life so this was new.
I was on vacay with my friend. I ended up hooking up with a tranny. It was very weird to me I was kind of drunk and felt weird. She was a dime piece though. You would never be able to tell. She was asking if I had a friend on vacay with me and if she could meet him after we were done messing around I was like hell no my life would be over.She then said he would never know which was true if he was just looking at her but I could tell by her voice even though it was pretty feminine.
Messing around was different but it was new which made it exciting I guess. I was just so curious and we did everything she was the only catcher though. i took a pic of her just to have it. I go back early in the morning to meet my friend. He was like whered you go. I said I hooked up. He asked if she was hot I was like yea. He was like did you take a pic. I was hesitante but I ended up showing him. He was like geez dude she is a dime I was like yep. He was like wow how did you pull that I want a girl like that...then I said I dont think you do. I showed her pic to multiple people i knew and they were all like holy sh!t that is a dime piece etc. Its pretty funny.
That night she texted me and asked if i got to my hotel ok and said it was nice meeting me. I said "yes im ok ..it was nice meeting you too i might stay another day so give me a call tommorrow or something".
The next day Im debating about staying because I wanted to hook up with her again. My friend is like lets just go. I was on the fence. So I said fine lets just fly back. Well Im sitting on the plane before we start going on the runway and low and behold I get a text right then saying "whats up cutie?" I was like fvvvccckkkkkkkk. I texted back and said I had to leave tonight I might be back next week and i will call you..i had fun last night.
Nobody knows what I did except for people on this board. I will never tell a soul I know what I did. I was kind of fvcked up for the next couple of days but i am getting over it.
I might go back and see her. She is seriously a dime though and i am debating taking her out with me in public I would be curious to see the reactions. I had to get this off my chest because I never told anyone.
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I do not care how much of a dime piece he/ she is.... If I knew that this was a dude, all bets are off the table!!! Strange story and had to respond since I have not posted here in a while..... If that is your thing and it makes you happy, go ahead on. For me, finding a women is a chore in itself, but damn if I want to hook up with a fella!!
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And another one steps out of the closet....
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To quote the words of Tone Loc :
"I threw her out...I don't fool around with no Oscar Meyer wiener!"
'Nuff said
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A woman following her heart is like a man following his penis.
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When I worked inside a jail the inmates that included themselves in that gay stuff would say it was, "situational homosexual" Homosexual is homosexual, spot on!!!
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Once you are born a man, you are forever a man.
No amount of hormones or genital alterations can make you any different.
So, congrats on sleeping with another man.
Doesent it seem like this site is full of troll posts now?
" You never take the easier way,
while the is blowing straight into your face.
You never make a compromise,
for any trouble that may cross your way.
There's no risk that you're not takin',
not a mountain that's too high,
spread your wings you gonna make it,
to the best time of your life. "
Dont stop at the top..
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Once you are born a man, you are forever a man.
No amount of hormones or genital alterations can make you any different.
So, congrats on sleeping with another man.
Doesent it seem like this site is full of troll posts now?
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This is a complete joke. A good comic relief though.
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hey i just read your post mk. i understand u complety inbox me if u can we pretty much had the same expirience and i too have never told anyone anything , somebody that doesnt judge would be cool to tell stories to
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Whatever makes you happy brah. We shouldn't actually give a fvck about this sh1t guys. His life, his choice.
Inb4 trolls attack me. No, I didn't hook up with tranny. The point is we should be busy with our sh1t, not with judging what others do.
"Just make it fast,loud, and rude."
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The only trannies you should blow on the weekends are the ones in a 68 Mustang. Jeezy Creezy Puddin & Pie!:crackup:
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You are a fag,how gross dude. Only fags try to justify sleeping with a tranny
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hey i just read your post mk. i understand u complety inbox me if u can we pretty much had the same expirience and i too have never told anyone anything , somebody that doesnt judge would be cool to tell stories to
You are a fag,how gross dude. Only fags try to justify sleeping with a tranny
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To the I am not GAY butt I butted a tranny last night
if that doesn't make you gay I don't know what does...just the simple fact you sought after a tranny says it all...its time for you to come clean with yourself and admit you are at the very least bi if not gay. There is nothing wrong with being gay, the thing I feel you are wrong about is saying you aren't but f'd another dude and still texting him.
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*smh*....homo's.
Oh hi there gaylan.
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Speaking of gays, when are you gonna hop off my jock?:crackup:
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That depends. When are you gonna stop being a whitey hating liberal faggot?
Looks like we both better bunker down (no homo)
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Youre pathetic dude. If you wanna talk smack, PM me. Im not gonna derail a thread because you want to be immature and toss insults around. Grow up dude. I like having a fan club and all, but your behavior is beyond pitiful now.
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DEAR DEIDRE: I WENT home with a woman I met in a club. When she pulled off her clothes I was staggered to see that “she” had all the male goods down below.
It was a massive surprise but I still had a great time in bed.
I’m a man of 46 and I’ve always been straight. I was married for 24 years before getting divorced but I never had any complaints, at least not about my performance in bed.
An old mate got in touch and suggested we have a night out. We started off in a pub in the town and then he suggested this gay club he knows.
I wasn’t keen but he told me that people of all kinds turned up and there’s a really great atmosphere there.
I agreed and I had to admit he was right. The whole place was buzzing, the music was great and the vibe was amazing. I started really enjoying myself.
This girl started dancing with me. She looked about 35 with a beautiful smile and huge come-to-bed eyes. Then she asked me to buy her a drink and I knew I was in with a chance.
The girl asked me back to her flat — my mate had already gone home. We jumped in a cab and as soon as we got through her door she was pulling my clothes off and pushing me down on her bed.
She pulled down her undies and that’s when I saw what she had underneath. She was hung like a donkey but made me feel
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