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.