One night I went out for drinks and to find a one night stand. I had too many drinks, passed out and then woke up to a nightmare!
I woke up and saw that I was in some kind of underground room. I was scared as I saw whips, paddles, bondage equipment, torture devices and many sex toys. I tried to move but I was bent over a table with my hands secured in front and my feet tied to the table legs. I tried to get my hands free, then suddenly someone said "It's no use, you will not get free from those ropes and this room is soundproof... no one will hear you."
There she was standing in front of me, a woman in her mid 50s. She was a stunning blonde standing at least 5 ft 10 inches...of course she was wearing 5 inch black high heel boots. I continued to stare at her amazing all black latex outfit! My cock was getting hard and I could not wait to fuck this strange woman. She grabs a paddle and instantly spanks my ass "Don't get any Ideas, I see your sorry cock getting hard!" "You don't know me But I'm Donna's mom Kathleen."
I watch as she grabs another metal device. "You fucked around with my daughter and broke her heart and now I will punish you." I tell her to go fuck herself, she laughs at me and says "It's you that will fucked tonight...but not the way you want." She goes under the table, she squeezes my balls hard and I scream. Then I feel her putting something on my cock and around my balls. "There that's better, now your useless cock is locked away." Then I watch in horror as she approaches me with a penis gag, it is roughly forced into my mouth.
I struggle with the penis gag in my mouth and am forced to bite down on it and then I taste it! "Oh, did you taste the cum? Every time you bite down on the penis gag, it will squirt yummy cum into your mouth." She grabs my head roughly, "but that's the least of your worries!" She grabs another item and puts it on... A black realistic 8 inch dildo strap-on. I start to scream into my gag and a lot of cum shoots into my mouth! She then puts a blindfold on me.
I can feel Kathleen behind me, she inserts lube into my virgin asshole. She then plays with my locked cock in the chastity device; I get hard but my cock is trapped. Kathleen then explains to me that I will most likely achieve a sissy orgasm but it will not be a satisfying orgasm. I want to cum so badly but I don't want her using that strap-on on me. But I have no choice as I feel the tip enter my virgin asshole!
I scream again and shake my head as she penetrates me with that monster strap-on. I can feel my locked cock getting hard in the painful chastity device. I'm tasting cum from the penis gag as the strap-on ravages me. Then suddenly she pulls out for a moment and then a minute later I feel the raw penetration again but this time it's harder and more painful! I can feel someone stroking my hair as my blindfold is removed.
Through the mirror I can see a man behind me... a man is now fucking me with a real cock that is bigger and wider than the strap-on! Kathleen then says, "Oh by the way this is my husband." As he fucks me my sissy cock explodes and I have my first ruined orgasm. Cum is leaking out of my chastity device as I watch in horror at my own peril! Kathleen then leaves me alone with her husband and his huge cock!