Credit: https://www.nifty.org/nifty/transgender/she-male/halloween-outing by Amanda Sutton
This is a story involving transgender sex. It is not meant for those under
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I double checked my makeup and applied more lip gloss. Jenna says I should
always reapply that because a guy loves lipstick marks on his dick,I know
they do it's not
like this is the first time I have a fuck date. I wore a black lace teddy,
similar to the one that I wore the first time I did a guy.
it was such a fucking hot night I figured why not? Jenna had helped me with
my hair which has grown over the last six months. I put on a black dress
and my heels.
Jenna my wife, was on the couch. She got up and did an inspection. "Yeah
sweetie, you have it down. Going to get some hot dick tonight".
"How about you, you have someone lined up?"
"No" she said. "Unlike you I get bad cramps and I'm staying in. You're
lucky sometimes to be a gay sissy. No period cramps."
Six months ago, it was Halloween. We were invited to a party. We were
trying to decide on costumes when Jenna suggested we slut it up for
She would go as Elvira and I would go as, well a slutty girl. I of course
said no, even though the idea kind of excited me. She pushed as I knew she
and I relented. She even took me to a cross dresser boutique. I left there
with a wig, slutty lingerie, and slutty dress. She worked hard on making me
like a woman and when she finished, I did not make a bad looking woman,
albeit a slutty looking one. Black Teddy with garters,Fishnet stockings
(with a small tear to look extra slutty), heels (not easy but I actually
managed it). We went to the party.
I was a little nervous. I headed to the bar and quickly downed a drink and
then a second. Jenna was dancing with some guy, a little close for comfort.
I was about to cut in when a guy grabbed me and asked me to dance. I was a
little drunk, so I said yes and next thing I know I'm dancing with
including the one that was getting close to Jenna. He brought me another
Cut to the following morning.
I woke up in the guys bed. I realized I didn't have any guy clothes, so I
cleaned myself up, called an Uber and headed home as a woman. Jesus I look
like a slut.
I walked through the door.
"So, you finally got home "said Jenna, sitting on the couch. "That was one
hell of a party. You were dancing with guys, I guess a few drinks in you
and you were the life of the party."
I stayed silent. "So, here's what I know you went home with one of them,
the one I was dancing with. I was a little annoyed about that but let's
break down the
action. You went home with him, right?" I nodded my head.
"So what else, did you make out with him?" I nodded
as I thought back on
what happened and yeah, we made out, his hand were squeezing my fake tits,
our lips were
together, I can't believe I'm kissing a guy and liking it I thought and
then my hand landed on......
Did you at least jerk him off? I nodded as I remember him undoing his pants
and reaching my hand grabbing ahold of his cock.
I was jerking him off! "Cool, you were gone almost all night so what
else...did you blow him"? I nodded as I thought back on his pants off,
me down to my lingerie and I was on my knees and took his cock in my mouth
and started to suck on it. It was ,I don't know, I'd like to blame it on
but damn, I liked his cock in my mouth. Sucking his cock, licking his pole,
tonguing his balls, and then taking it all the way into my mouth while
It felt so good. I knew I liked sucking cock from the moment I started.
"Oh, that is so cool. I hope it was a nice wet one, guys love when there's
a lot of moisture. You know if you deep throat him it makes it
really...,you did deep
throat him? Honey, that is fantastic, you just naturally deep throated a
guys cock like you were born to do it. That must have been such a great
you gave Yeah, you liked doing that didn't you? So, did he come in your
mouth?" I shook my head, I couldn't speak. So where, your lingerie looks
your face? No, your makeup looks like it did when I did it up. Hmm ,where
did he.....holy shit did he fuck you in the ass?." I didn't answer.
"Yeah he did fuck you in the ass. That is unbelievable. I figured you might
blow him but I never expected you would take a cock in your ass."
I fucking loved being fucked, the pushing in my ass, the rubbing against
my prostate, everything about being fucked I loved.God, I may have been
dressed as a
slut but what made me want cock so badly?
She started laughing. So you made out with a guy, gave him a blow job and
you asked him to fuck you? Yeah, it was your idea. Wasn't it?
You wanted that cock, didn't you?" I smiled and nodded. I thought back,he
got some lube, put a finger in my ass with the lube, then lubed up my ass
cock. It hurt a little bit but then as he picked up the pace....fuck that's
I got a text.
"Let me see that. Oh, that's so sweet, he texted you with a heart and wants
to see you again. Do you want to see him again. I can make you up as slutty
as you want".
I texted him back right away.
"So, you're seeing him tonight again.? Looks like my husband has a fuck
date. That's okay, I kind of figured after a while that you were kind of
so I made sure you were so slutty looking the guys would fall all over you
and you loved it. Being dressed as a sissy slut made you come out. I
mean look at me and you stole a guy I was going to fuck. I had to settle
for second place after you left. Yeah, I fucked a guy from the party,
don't get so high and mighty, so did you."
:Let's face it, you're gay. You loved cock in your mouth and your ass. We
don't have to break up, we can be like two girls who tell each other about
they fucked because I'm sure this may have been the first but not the
last. So what do you say?"
That was six months ago, and I have blown guys and let them fuck my ass. I
love the taste of cum in my mouth and the feel of being fucked and havng
them cum in my ass.. It's been the best sex ever.
I'm even thinking about getting breast implants so guys can come between my
tits. As I was ready to leave, I saw Jenna getting ready to go out.
"I thought you said you had cramps?"
"Yeah, I do but my mouth isn't bleeding and there's the guy I told you
"With the 10 inch dick? I said excitedly. "You have to tell me everything.
Wow, I hope this guy I'm doing is hung. Wow, I bet he shoots a ream.
I would love to swallow that."
"I bet you would you little cum bucket. So tomorrow we get dressed, go out
in the afternoon, and have brunch and talk about the guys.
Jenna reapplied her lip gloss." She gave me a kiss on the cheek. "My gay
sissy husband. I love you more this way."
"I love myself more this way also" I replied.