• Tag Archives Sissification
  • Story – Omegle sissification

    Story – Omegle sissification originally posted on Reddit’s sissy board.

    You’re now chatting with a random stranger. Say hi! You both like crossdressing, and panties. You
    well hello
    Stranger: Hello
    You: asl?
    Stranger: 19 M USA
    You: 22 m canada
    You: are you wearing right now?
    Stranger: Yes! My mistress laid an outfit out
    You: mmmm are you a sissy slut?
    Stranger: Yes i am
    You: then put that shit in your interests! I love it
    You: I’m looking all cute in my silk and lace panties
    You: and you?
    Stranger: French maid outfit(;
    You: ooh the best
    You: my favourite
    Stranger: With a black thong
    You: <3
    You: I wish…
    You: any tights?
    You: stockings?
    Stranger: Yes of course! White thigh high tights!
    You: oooh baby
    You: wig or no wig?
    Stranger: Blonde wig
    You: you are just perfect
    Stranger: My "mistress" likes it that way
    You: do you happen to have a plug or other toys?
    You: ^
    Stranger: Yeah she has plugs dildos rings you name it!
    You: mmm sounds like my girlfriend's collection lol
    You: tell me about your mistress, what does she make you do?
    Stranger: Lol well it's not really a mistress, it's my mom's friend, she's blackmailing
    You: oh shit, story time!
    Stranger: Me*
    You: please please do tell
    You: in excrutiating detail
    Stranger: Okay, well one day i was at her house swimming and my mom was working but she didn't care that
    Stranger: I came down and jumped in the pool so when i was done i went to change in her bathroom
    You: mhmm
    Stranger: Well i found a pair of her panties and a bra, a gorgeous black bra with a pair of red briefs and i slipped them on thinking the door was locked
    You: ooh, I have a secret love for briefs
    You: so hot
    Stranger: So as i'm checking myself out in the mirror the door opens and there she is just staring me down
    You: here's where it gets good/horrifying I'm sure
    Stranger: She's divorced so she has the house to herself and her two daughters but they weren't home for whatever reason
    Stranger: So before i could even say a word i got a swift kick to my balls and next thing i know i'm on ground in pain
    You: oh god! not where I thought that was going
    You: I hope you were ok?
    Stranger: Yeah i was, she started screaming at me and i started
    Stranger: To take off her clothes but she stopped me and told me to wait there and she came back with her phone and started taking pictures
    You: oh jeez!
    Stranger: She was threatening to send them to my mom if i didn't do what she said
    You: which was…?
    Stranger: Where i am at today, her bitch
    You: do you have a sissy name?
    Stranger: I have to come over and become a girl and do chores and stuff around the house as well as serve her needs
    Stranger: And yes i do, it's Leanne
    You: Does some part of you enjoy it Leanne?
    You: you get to wear this gorgeous stuff!
    Stranger: At first no, but now yes<333
    You: I'd love to be in your position!
    You: Have she ever made a move?
    Stranger: Are you straight?!
    You: I'm a little both
    You: girlfriend though
    Stranger: I see i see!
    Stranger: I was straight until Heather, now i'm bi
    You: oh you're too good
    You: tell me about heather!
    You: I'm sitting here only in panties with a big long vibe running up and down my shaft, your storytelling skills are great ^
    Stranger: She's awesome! She's 42, a little heavier set, nice breasts 38DDD, amazing pussy, is every caring, only punishes when needed
    You: as an aside, I almost came the moment my vibe went in me, sorry I was scared
    You: please go on
    Stranger: She forced me bi
    You: how so? toys?
    Stranger: Started with her strapon, i'd suck it and she'd fuck me with it, made
    Stranger: I had to ride it and such
    You: mmm, when was the last time you played around with a strap-on?
    Stranger: But one night when her daughters were gone and i had to stay and do stuff she went out and came home with a man so i was going to give her alone time and finish my chores when she called me to her bedroom
    Stranger: And a few hours ago
    You: Leanne! you're driving me crazy here
    Stranger: When i got to her bedroom she told me that the man wasn't for her that it was for me, i started to object when she pulled out the photos of me from the first time in her panties and said if i didn't start sucking the man's cock she would send the pictures out in a mass text
    You: and what do you do in that situation, sissy?
    Stranger: I opened my mouth
    You: was it your first time?
    You: just a few hours ago?
    Stranger: No this was a while ago
    You: ok
    Stranger: And it was my first time
    You: tell me all about it Leanne
    Stranger: She fucked me before with her strapon
    Stranger: I put my lips around his dick and started sucking with my eyes closed until i got a hard slap on my balls and was told to look my man in his eyes
    Stranger: I blew him for 7 minutes and Heather had the man pull out and blow cum all over my sissy face
    You: now there's some discipline
    You: and did you clean yourself up?
    Stranger: She did it for me because she said i did good and then she rewarded me
    You: how so, leanne?
    Stranger: She gave me a handjob and had me cum into her hand and then she fed it to me
    You: more cum, yay
    You: Leanne I'm about to burst, should I cum?
    Stranger: Yes, but eat it
    You: of course
    You: I'd like to slide that thong to the side and slip into you, well-lubed
    Stranger: Yes<3333 she had me gang banged
    Stranger: And it was a constant rotation of cock in my ass
    You: well you were just the right person to talk to
    You: that was the biggest load I've blown in a long time
    You: god I'm jealous!
    You: so hot
    Stranger: Did you lick it up!
    You: thank you for everything
    You: mostly, but just finished the job
    Stranger: My favorite thing she makes me do is service her
    You: like a maid or orally?
    Stranger: Both
    You: mmm
    You: oral is my favourite thing to do honestly
    You: most people don't understand lol
    Stranger: I love it, she
    Stranger: She makes me eat her ass and i love it more and more everytime
    You: I'm sorry gotta go and wash my hands
    You: thank you, bye
    You: stay good leanne
    You have disconnected.

    You both like crossdressing, and panties.
    You: well hello
    Stranger: Hello
    You: asl?
    Stranger: 19 M USA
    You: 22 m canada
    You: are you wearing right now?
    Stranger: Yes! My mistress laid an outfit out
    You: mmmm are you a sissy slut?
    Stranger: Yes i am
    You: then put that shit in your interests! I love it
    You: I’m looking all cute in my silk and lace panties
    You: and you?
    Stranger: French maid outfit(;
    You: ooh the best
    You: my favourite
    Stranger: With a black thong
    You: <3
    You: I wish…
    You: any tights?
    You: stockings?
    Stranger: Yes of course! White thigh high tights!
    You: oooh baby
    You: wig or no wig?
    Stranger: Blonde wig
    You: you are just perfect
    Stranger: My "mistress" likes it that way
    You: do you happen to have a plug or other toys?
    You: ^
    Stranger: Yeah she has plugs dildos rings you name it!
    You: mmm sounds like my girlfriend's collection lol
    You: tell me about your mistress, what does she make you do?
    Stranger: Lol well it's not really a mistress, it's my mom's friend, she's blackmailing
    You: oh shit, story time!
    Stranger: Me*
    You: please please do tell
    You: in excrutiating detail
    Stranger: Okay, well one day i was at her house swimming and my mom was working but she didn't care that
    Stranger: I came down and jumped in the pool so when i was done i went to change in her bathroom
    You: mhmm
    Stranger: Well i found a pair of her panties and a bra, a gorgeous black bra with a pair of red briefs and i slipped them on thinking the door was locked
    You: ooh, I have a secret love for briefs
    You: so hot
    Stranger: So as i'm checking myself out in the mirror the door opens and there she is just staring me down
    You: here's where it gets good/horrifying I'm sure
    Stranger: She's divorced so she has the house to herself and her two daughters but they weren't home for whatever reason
    Stranger: So before i could even say a word i got a swift kick to my balls and next thing i know i'm on ground in pain
    You: oh god! not where I thought that was going
    You: I hope you were ok?
    Stranger: Yeah i was, she started screaming at me and i started
    Stranger: To take off her clothes but she stopped me and told me to wait there and she came back with her phone and started taking pictures
    You: oh jeez!
    Stranger: She was threatening to send them to my mom if i didn't do what she said
    You: which was…?
    Stranger: Where i am at today, her bitch
    You: do you have a sissy name?
    Stranger: I have to come over and become a girl and do chores and stuff around the house as well as serve her needs
    Stranger: And yes i do, it's Leanne
    You: Does some part of you enjoy it Leanne?
    You: you get to wear this gorgeous stuff!
    Stranger: At first no, but now yes<333
    You: I'd love to be in your position!
    You: Have she ever made a move?
    Stranger: Are you straight?!
    You: I'm a little both
    You: girlfriend though
    Stranger: I see i see!
    Stranger: I was straight until Heather, now i'm bi
    You: oh you're too good
    You: tell me about heather!
    You: I'm sitting here only in panties with a big long vibe running up and down my shaft, your storytelling skills are great ^
    Stranger: She's awesome! She's 42, a little heavier set, nice breasts 38DDD, amazing pussy, is every caring, only punishes when needed
    You: as an aside, I almost came the moment my vibe went in me, sorry I was scared
    You: please go on
    Stranger: She forced me bi
    You: how so? toys?
    Stranger: Started with her strapon, i'd suck it and she'd fuck me with it, made
    Stranger: I had to ride it and such
    You: mmm, when was the last time you played around with a strap-on?
    Stranger: But one night when her daughters were gone and i had to stay and do stuff she went out and came home with a man so i was going to give her alone time and finish my chores when she called me to her bedroom
    Stranger: And a few hours ago
    You: Leanne! you're driving me crazy here
    Stranger: When i got to her bedroom she told me that the man wasn't for her that it was for me, i started to object when she pulled out the photos of me from the first time in her panties and said if i didn't start sucking the man's cock she would send the pictures out in a mass text
    You: and what do you do in that situation, sissy?
    Stranger: I opened my mouth
    You: was it your first time?
    You: just a few hours ago?
    Stranger: No this was a while ago
    You: ok
    Stranger: And it was my first time
    You: tell me all about it Leanne
    Stranger: She fucked me before with her strapon
    Stranger: I put my lips around his dick and started sucking with my eyes closed until i got a hard slap on my balls and was told to look my man in his eyes
    Stranger: I blew him for 7 minutes and Heather had the man pull out and blow cum all over my sissy face
    You: now there's some discipline
    You: and did you clean yourself up?
    Stranger: She did it for me because she said i did good and then she rewarded me
    You: how so, leanne?
    Stranger: She gave me a handjob and had me cum into her hand and then she fed it to me
    You: more cum, yay
    You: Leanne I'm about to burst, should I cum?
    Stranger: Yes, but eat it
    You: of course
    You: I'd like to slide that thong to the side and slip into you, well-lubed
    Stranger: Yes<3333 she had me gang banged
    Stranger: And it was a constant rotation of cock in my ass
    You: well you were just the right person to talk to
    You: that was the biggest load I've blown in a long time
    You: god I'm jealous!
    You: so hot
    Stranger: Did you lick it up!
    You: thank you for everything
    You: mostly, but just finished the job
    Stranger: My favorite thing she makes me do is service her
    You: like a maid or orally?
    Stranger: Both
    You: mmm
    You: oral is my favourite thing to do honestly
    You: most people don't understand lol
    Stranger: I love it, she
    Stranger: She makes me eat her ass and i love it more and more everytime
    You: I'm sorry gotta go and wash my hands
    You: thank you, bye
    You: stay good leanne
    You have disconnected.