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Gay Stories
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Straight Male / 22
The Trans Woman
My friends and I went to a bar in Miami one night and for the most part stood around until 2 cute girls asked me and other friend to buy them drinks. We chatted at the bar with the girls for a little while, and noticed a woman (evidentally a trans woman) staring at the both of us and smiling
My friend and i exchanged looks and blushed at the idea at first but caught eachother staring back at her multiple times
A little while later I got up to go smoke a cigarette, and as soon as I got out the door I spotted the trans woman in the back alley smoking a cigarette herself
She smiled when she saw me and said, “too embarrassed to talk to me inside so you followed me here?”
I laughed nervously and told her it was simply a coincidence and that I was enjoying a smoke myself
She got really close to me and asked, “is there anything else you enjoy?”
“Do you have something enjoyable for me?” I replied (still thankful for my smooth reply)
She got right up on me and said it might not be what I’m used to, but I’ll certainly enjoy it
“Show me don’t tell me” I said
(I was on a fuckin roll)
“With pleasure!” She gave me a sexy kiss on the mouth before getting to her knees
She pulled my dick out and frowned, “I usually only suck cock when it’s bigger than mine but you’re too cute to not have a taste”
(This line alone was enough to make me cum, but I held it in to let her continue her work)
She then proceeded to give me the best blowjob I’ve ever gotten, saliva dripping down on her chin as she deepthroated me like a professional dick sucker
At one point I saw her jerking her own dick under her skirt while she sucked me and I told her I wanted to see her cum on the floor
I took a step back and jerked my cock while watching her rub her big dick until she came all over the ground outside
She gasped as she came and smiled and she pulled me back to her mouth, “your turn baby”
She resumed sucking my dick and eventually swallowed my entire load and kissed me one last time as a thank you
“That was fun! See you back inside sugar” she said and she fixed herself up and went back inside the bar
I took out another cigarette and contemplated about the fact that I let a trans woman blow me and ended up getting hard again before going back inside.
“Where tf were you this whole time?” my friend asked “the girls left me like 10 minutes ago dude I thought we were gonna get some action!”
“Trust me I did” I smiled and nodded towards the trans woman
He looked at me and back at her and started laughing, “you’re joking right?”
He sat there in shock as I told him everything that occurred and I saw him begin to rub his crotch. “Dude do you think she’ll blow me?” he asked
“I don’t now let me ask”
I caught the trans woman’s attention and pointed at my friend questioningly
She smiled slyly and grabbed her cigarettes to go back to the alley
“She’s all yours bro” I said to my friend, and watched him head to the back for some fun himself
My friend and i exchanged looks and blushed at the idea at first but caught eachother staring back at her multiple times
A little while later I got up to go smoke a cigarette, and as soon as I got out the door I spotted the trans woman in the back alley smoking a cigarette herself
She smiled when she saw me and said, “too embarrassed to talk to me inside so you followed me here?”
I laughed nervously and told her it was simply a coincidence and that I was enjoying a smoke myself
She got really close to me and asked, “is there anything else you enjoy?”
“Do you have something enjoyable for me?” I replied (still thankful for my smooth reply)
She got right up on me and said it might not be what I’m used to, but I’ll certainly enjoy it
“Show me don’t tell me” I said
(I was on a fuckin roll)
“With pleasure!” She gave me a sexy kiss on the mouth before getting to her knees
She pulled my dick out and frowned, “I usually only suck cock when it’s bigger than mine but you’re too cute to not have a taste”
(This line alone was enough to make me cum, but I held it in to let her continue her work)
She then proceeded to give me the best blowjob I’ve ever gotten, saliva dripping down on her chin as she deepthroated me like a professional dick sucker
At one point I saw her jerking her own dick under her skirt while she sucked me and I told her I wanted to see her cum on the floor
I took a step back and jerked my cock while watching her rub her big dick until she came all over the ground outside
She gasped as she came and smiled and she pulled me back to her mouth, “your turn baby”
She resumed sucking my dick and eventually swallowed my entire load and kissed me one last time as a thank you
“That was fun! See you back inside sugar” she said and she fixed herself up and went back inside the bar
I took out another cigarette and contemplated about the fact that I let a trans woman blow me and ended up getting hard again before going back inside.
“Where tf were you this whole time?” my friend asked “the girls left me like 10 minutes ago dude I thought we were gonna get some action!”
“Trust me I did” I smiled and nodded towards the trans woman
He looked at me and back at her and started laughing, “you’re joking right?”
He sat there in shock as I told him everything that occurred and I saw him begin to rub his crotch. “Dude do you think she’ll blow me?” he asked
“I don’t now let me ask”
I caught the trans woman’s attention and pointed at my friend questioningly
She smiled slyly and grabbed her cigarettes to go back to the alley
“She’s all yours bro” I said to my friend, and watched him head to the back for some fun himself
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