If you can remember the stories LUCK RAN OUT AND I GOT CAUGHT then good this has escalated from there if not please read it first.
It was a few weeks before my G/f college prom and said had her prom dress all prepared and hung up in the spare bedroom where i stayed. (her folks where very strict)
As you can probably guess by now i wanted to try it on, it was a gorgeous gold long dress with 7 layers of skirt from the outside it felt so good but i wanted to feel the inside, so there i was laying in bed one night wondering what i would be like.
As i was unable to get any under garments i had to wait one extra night during the next day i sneaked her strap less bra, thong and stockings with the wedges all from her bedroom and hide them in my pillow case, all that had to be done now it wait till night fall.
As we all went to bed i couldn't wait to try it on i knew i had to wait until everyone was asleep so i waited till about 1AM and got up and went to the toilet and came back up and striped off my shorts.
I got hold of the undergarments and put them on just like always and then came the time i had been waiting for i got hold of the dress unzipped the back slid it on and zipped it up now this being a prom dress the zip was going be tight to show your body off so i struggled there for a little bit but managed to get it up after 10 minutes or so.
So there i am in a gorgeous prom dress with stockings 4inch heels bra and thong i felt so good my heart was racing. I started to walk about in the dress when i heard a noise from my g/f's room.
I panicked and fell over the heels as i tried to race back into bed wearing the dress. I heard her door open and then my door open. She came into the room and walked over to me knowing i had the dress on as the hanger was on the floor, she looked at me and tried to pull the covers back i tried to resist but had to let go and she reveled me wearing her prom dress. She looked at me and shook her head and said,
"You know what's going to happen now!"
With that she walked out the room and went downstairs to the cloak room she then went to the toilet and came running back up during this time i was trying to get out of the dress but i was unable to undo the zip.
She came back into the room holding some cable ties i knew what she was going to do as she ordered me to lay on the bed with my face forward.
She got hold of my legs and zipped them together using 2 cable ties then she did the same with my hands pulling them painfully tight. With the last few cable ties she put me into a hogtie and made my hands meet my feet.
I was really excited but scared as i didn't know what she was planning.
She went out of the room and came back in and pulled the dress up to look what i was wearing seeing my under garments she said
"Looks like someone needs to be punished"
She then pulled up the bottom of the dress and moved the thong aside and inserted something into my arse i wondered what the hell it was has i had never felt anything like that before then she removed some plastic and i felt a sharp pain as my anus closed round the item inserted. She then said to me,
"That's going to be in there for a while so you better get use to it like i have said you want to be a girl you must feel what's its like"
I had found out she has inserted a tampon into my anus. I had never felt any pain like it my anus couldn't mould to it.
She then went back out of the room and came back in with a skirt hanger she then unzipped the dress and pulled it down revealing my hard awaiting nipples and slowly clicked the skirt hanger onto my nipples the pain was so bad i almost screamed with it.
She started pulling on them and giving my tampon a slight pull letting me know its there. With both of this pain i didn't know what to do then she lifted up the dress and started sucking my penis harder and faster. The faster she went the harder she pulled on my nipples.
I was about to climax when she looked at me and saw i was enjoying it as it was a dream come true yet again but as she made me climax and cum in her mouth she gave my tampon a almighty yank and pulled it straight out my arse i let out a almighty yell and with that she spat the cum in my mouth and made me eat it.
After all this she said to me good night and went back to her bedroom leaving me all tied up half in the dress with my nipples being pinched hard by the second. It must off been a good hour before she returned to release me removing my clamps first so i could not do anything then cutting me out of my hogtie and said to me to get cleaned up and get to bed.
I laid there for a few moments thinking about what i just went though and how good it felt. I then got up and got all cleaned up putting the dress back where it belonged. I laid there in bed in my under garments and fell asleep. The next think i knew it was morning and i woke up still in the under garments i quickly got up and striped before anyone came in. Once i stripped i went back to bed and 5 minutes later my girlfriend came though the door to awaken me.
God knows what would of happened if she had found me still in her undergarments.
Unfortunately we have since spilt up as we had a big argument and decided to end the relationship but i will never forget the times i had with her being bound helpless and belong forced to eat cum and endure pain i had never felt before.
Hope you enjoyed it
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<a href="https://www.lushstories.com/stories/crossdressing/caught-in-a-prom-dress.aspx">Caught in a Prom Dress</a>