I’ve been questioning if I should write this, or even how, after this weekend’s events…but figured I might as well.
For a bit of a backstory, I went through a breakup earlier this year, unrelated to the events that (eventually) transpired in this story and I still maintain a friendship with my ex-girlfriend, we just wanted different things out of life. But, that’s not this story.
(I apologize for the length, skip to —— for fun)
I’ve always had a bit of an interest in crossdressing, and after the breakup, it felt like the perfect opportunity to experiment, and see if I enjoyed it. Fortunately, I have a fantastic girl friend (not my ex), that really enjoyed me helping transform myself.
As October approached, I mentioned to her that I didn’t have a costume picked out for the party, and she off-handedly suggested picking out a woman costume, and that sounded like a fantastic idea. With the new idea, her and I proceeded to put together a pretty good Velma (from Scooby Doo) costume for myself, while adding some subtle sexiness – namely lace underwear and taller heels and she went as Daphne.
The party was Friday night, so on Thursday night she came over for the preparations to begin – I won’t bore those details. By, mid-Friday afternoon, I was looking good and excited for the party.
(As a sidenote, my friend knows I’m bi-curious, so encouraged me to have fun).
After the party gets into full swing, I notice a particular guy that keeps eyeing me wherever I go, finally chatting me up as I was getting a water. I won’t bore you with the details of the conversation, but soon enough, we were dancing with each other, and his hands were roaming over my body, paying special attention to my ass. My friend caught my eye while this was going on and grinned at me.
Soon enough, my (costumed) Hulk was suggesting we leave the party and find someplace quieter, namely his place. I excused myself, told my friend, and she said to keep in contact with her, be safe, and have fun. I went back to Hulk and told him “let’s go”
———————————————————
The short drive to his place, he kept his hand caressing my thigh. After arriving, he led me into his beautiful house and into the kitchen, offering me a drink. Before I could even take a sip, he had me pinned against his island aggressively kissing me, his tongue probing my mouth and his hands squeezing my ass. We came up for air just long enough to suggest going to the bedroom.
Once in the bedroom, he suggested I do a little striptease for him, so I (tried to) sexily remove my sweater leaving my lace bra and breast forms on, then turned around shimmying the skirt down, leaving my thong, stockings, and heels on. Now, I’m standing before this man as an all sexed up Velma, and there’s no turning back.
After admiring me, he told me to undress him (which was really just removing his torn up jean shorts), and in doing so his magnificently hard cock sprang free and rock hard.
I proceeded to give him the sloppiest blowjob ever (my first) and even swallowed his cum! That was only a warmup for the main event though.
After a few minutes, his cock started to show signs of life again, so I started stroking him back to full hardness. At which point, he told me to get on all 4s, and he positioned himself behind me. He pulled my thong down, and my own cock flopped out, kinda soft. He chuckled and said that he loved ‘gurls’ like me and we would have fun.
He treated my tight, little hole to a glorious tongue fucking before grasping my cheeks and spreading me wide and positioning his much larger cock at my entrance and began pushing. Eventually, my hole relented and felt him sliding inch by inch into me, splitting me in half, until I felt his groin press against my butt.
He started sawing in and out of me, increasing speed and intensity, my moans and gasps and whimpers echoing off his bedroom walls, his balls slapping against me.
After what felt like an eternity, but was probably 15-20 minutes, he pushed deep into me one final time, and I felt his cock pulse 4-5 times, filling me with his cum. As his cock softened, he slid out of me, and some of his cum trickled out as well.
I spent the night, before having an encore performance on Saturday morning before he took me back to my friend’s place, and I’ve spent the rest of the weekend recovering.
TLDR: breakup earlier in the year, started crossdressing, went to Halloween costume party crossdressed, got my brains fucked out by a guy
Source: reddit.com/r/gonewildstories/comments/qexkqs/how_this_weekends_halloween_party_changed