The Sissy Street Whore Uploaded by ALilBroken Profile | Galleries | Videos | Favorites | Fanbase | Clubs | Comments | Blog | Chat Add a description of the contents of your gallery, so it will be more visible for other users. Remember that you can also add descriptions to each image. This one is a little darker than my other stories. I often wonder what becomes of some of the young men in my scenarios, say a few years down the road. With that in mind, here we find Mark, who was once a nice and very normal guy until a few young ladies at his school feminized and humiliated him for their own amusement. After that, Mark spiraled. Mortified to show his face amongst his old friends, and discovering he had a strong and unexpected draw to sexual humiliation, Mark left town and continued crossdressing and seeking out sexually submissive scenarios on his own. He soon found other like minded people in the larger city and through a local club, he met Carla and Mauricio. Mark needed money desperately and they saw an opportunity to use Mark’s unique situation to make some money of their own. So now we join Mark today, working for Carla and Mauricio at night as a Sissy Street Whore. I hope you enjoy this little story from my broken mind. As usual, this one has a strong dominant femdom woman, a submissive sissy boi, crossdressing men, humiliation, feminization. But also forced bi, gay sex, and prostitution. Oh my! There is a lot to unpack here. And of course, our hero is wearing pantyhose. Happy fapping my friends, I hope this helps someone cum today.     Saving...     Description saved This one is a little darker than my other stories. I often wonder what becomes of some of the young men in my scenarios, say a few years down the road. With that in mind, here we find Mark, who was once a nice and very normal guy until a few young ladies at his school feminized and humiliated him for their own amusement. After that, Mark spiraled. Mortified to show his face amongst his old friends, and discovering he had a strong and unexpected draw to sexual humiliation, Mark left town and continued crossdressing and seeking out sexually submissive scenarios on his own. He soon found other like minded people in the larger city and through a local club, he met Carla and Mauricio. Mark needed money desperately and they saw an opportunity to use Mark’s unique situation to make some money of their own. So now we join Mark today, working for Carla and Mauricio at night as a Sissy Street Whore. I hope you enjoy this little story from my broken mind. As usual, this one has a strong dominant femdom woman, a submissive sissy boi, crossdressing men, humiliation, feminization. But also forced bi, gay sex, and prostitution. Oh my! There is a lot to unpack here. And of course, our hero is wearing pantyhose. Happy fapping my friends, I hope this helps someone cum today. Gallery Categories: AI Generated Gallery Tags: sissy, femdom, feminization, humiliation, crossdressing, pantyhose, gay, forced bi 6,0 (40 votes) Detailed View  /  One page Mark made his way up the dirty old alley to the rusty metal door. He was late. “Carla going to be pissed.” He thought to himself. It seemed she was always pissed about something these days.     Saving...     Description saved Mark made his way up the dirty old alley to the rusty metal door. He was late. “Carla going to be pissed.” He thought to himself. It seemed she was always pissed about something these days. img-3690.png 1254 x 1254 < 73 Views > Sure enough, Carla lit into him as soon as he walked through the apartment door. “Are you fucking kidding me!?” She scowled. “Do you want me to tell Mauricio you were late again!? Go get ready.”     Saving...     Description saved Sure enough, Carla lit into him as soon as he walked through the apartment door. “Are you fucking kidding me!?” She scowled. “Do you want me to tell Mauricio you were late again!? Go get ready.” img-3691.png 1254 x 1254 < 34 Views > Mark walked past Carla to the dingy bedroom without saying a word. He took off his jeans and t shirt, and began to get dressed.     Saving...     Description saved Mark walked past Carla to the dingy bedroom without saying a word. He took off his jeans and t shirt, and began to get dressed. img-3699.png 1254 x 1254 < 30 Views > The pantyhose always made him feel a little better. Most women hated them, but for Mark they were the turning point in the whole process, and he loved how they felt against his skin.     Saving...     Description saved The pantyhose always made him feel a little better. Most women hated them, but for Mark they were the turning point in the whole process, and he loved how they felt against his skin. img-3701.png 1254 x 1254 < 25 Views > Little by little Mark disappeared, both visually as well as in his own mind, and his counter identity Gypsy Rose emerged in Mark’s place.     Saving...     Description saved Little by little Mark disappeared, both visually as well as in his own mind, and his counter identity Gypsy Rose emerged in Mark’s place. img-3702.png 1254 x 1254 < 7 Views > Mark walked across the hall to Carla’s room and slipped on the last piece of his costume. His transformation into Gypsy was complete, and none too soon for Carla’s liking.     Saving...     Description saved Mark walked across the hall to Carla’s room and slipped on the last piece of his costume. His transformation into Gypsy was complete, and none too soon for Carla’s liking. img-3703.png 1254 x 1254 < 14 Views > Carla drove Gypsy to the nice part of town, where the men spent more money on such adventures.     Saving...     Description saved Carla drove Gypsy to the nice part of town, where the men spent more money on such adventures. img-3704.png 1254 x 1254 < 17 Views > It didn’t take long before Alan pulled up in his nice car. Gypsy remembered Alan from last month. He was a nice enough guy, had plenty of money, and some very peculiar kinks that were right up Gypsy’s aisle.     Saving...     Description saved It didn’t take long before Alan pulled up in his nice car. Gypsy remembered Alan from last month. He was a nice enough guy, had plenty of money, and some very peculiar kinks that were right up Gypsy’s aisle. img-3705.png 1254 x 1254 < 15 Views > Gypsy paraded Alan through the hotel lobby to really humiliate him, and she made a small spectacle of taking the room key that Carla had reserved from Peter, the concierge. “Come up in about 20 minutes.” She winked at Peter, “And I’ll make him blow you.”     Saving...     Description saved Gypsy paraded Alan through the hotel lobby to really humiliate him, and she made a small spectacle of taking the room key that Carla had reserved from Peter, the concierge. “Come up in about 20 minutes.” She winked at Peter, “And I’ll make him blow you.” img-3736.png 1254 x 1254 < 12 Views > They entered the room together and before Alan could even say anything, Gypsy ordered him to strip. Deep in sub space, Alan just nodded and began to undress.     Saving...     Description saved They entered the room together and before Alan could even say anything, Gypsy ordered him to strip. Deep in sub space, Alan just nodded and began to undress. img-3737.png 1254 x 1254 < 8 Views > Gypsy took Alan’s brown leather belt in hand and ordered him to place both of his hands on the back of the chair. Then she violently wrenched his white underpants up his butt crack before unleashing several vicious strikes to his soft pale ass cheeks.     Saving...     Description saved Gypsy took Alan’s brown leather belt in hand and ordered him to place both of his hands on the back of the chair. Then she violently wrenched his white underpants up his butt crack before unleashing several vicious strikes to his soft pale ass cheeks. img-3738.png 1254 x 1254 < 22 Views > Gypsy sat silently in the nicely upholstered chair and watched as Alan slipped off her musky leather shoes and spent the next several minutes carefully suckling each of her damp nylon toes in his mouth.     Saving...     Description saved Gypsy sat silently in the nicely upholstered chair and watched as Alan slipped off her musky leather shoes and spent the next several minutes carefully suckling each of her damp nylon toes in his mouth. img-3739.png 1254 x 1254 < 9 Views > After licking her toes, Gypsy could see that Alan was rock hard. She told him to lean back and she began to gently caress his erection with her moist nylon feet.     Saving...     Description saved After licking her toes, Gypsy could see that Alan was rock hard. She told him to lean back and she began to gently caress his erection with her moist nylon feet. img-3740.png 1254 x 1254 < 6 Views > Gypsy stopped her footjob just before Alan could cum, leaving his breathless and desperate. “My turn sweetheart.” She smiled at him, and spread her legs as Alan reached forward and took her stiff cock into his hand.     Saving...     Description saved Gypsy stopped her footjob just before Alan could cum, leaving his breathless and desperate. “My turn sweetheart.” She smiled at him, and spread her legs as Alan reached forward and took her stiff cock into his hand. img-3741.png 1254 x 1254 < 6 Views > After a few minutes of Alan rubbing and sucking her cock, Gypsy got up from the chair and took him to the large widow. “Do you see all the people outside tonight Alan?” She asked him softly. “I’m going to show them what a little bitch you really are.”     Saving...     Description saved After a few minutes of Alan rubbing and sucking her cock, Gypsy got up from the chair and took him to the large widow. “Do you see all the people outside tonight Alan?” She asked him softly. “I’m going to show them what a little bitch you really are.” img-3742.png 1254 x 1254 < 7 Views > Gypsy took her time entering Alan. He grunted in pain as she finally thrust her considerable cock deep into his tight reluctant asshole. Gypsy fucked Alan slowly at the window for several minutes until they both came at the same time.     Saving...     Description saved Gypsy took her time entering Alan. He grunted in pain as she finally thrust her considerable cock deep into his tight reluctant asshole. Gypsy fucked Alan slowly at the window for several minutes until they both came at the same time. img-3743.png 1254 x 1254 < 9 Views > Gypsy recovered and caught her breath on the bed while Alan pulled his white cotton underpants up over his sore gaping asshole, soaking them in Gypsy’s seeping cum.     Saving...     Description saved Gypsy recovered and caught her breath on the bed while Alan pulled his white cotton underpants up over his sore gaping asshole, soaking them in Gypsy’s seeping cum. img-3764.png 1254 x 1254 < 8 Views > Alan dressed to leave, but when he reached for his pants, Gypsy snatched them from him. “Nope, not so fast.” She smiled.”I have one more little surprise for you tonight Alan.”     Saving...     Description saved Alan dressed to leave, but when he reached for his pants, Gypsy snatched them from him. “Nope, not so fast.” She smiled.”I have one more little surprise for you tonight Alan.” img-3765.png 1254 x 1254 < 8 Views > For the second time that night, Gypsy paraded Alan through the busy lobby of the hotel as she walked him to his car. This time, even more humiliating for poor Alan than the last.     Saving...     Description saved For the second time that night, Gypsy paraded Alan through the busy lobby of the hotel as she walked him to his car. This time, even more humiliating for poor Alan than the last. img-3766.png 1254 x 1254 < 11 Views > The buzz of the date already wearing off. Gypsy found Carla waiting for her out on the sidewalk. Gypsy handed over the cash without a word. “Not bad.” Said Carla evenly. ”But you were late today, so let’s go find you another client.”     Saving...     Description saved The buzz of the date already wearing off. Gypsy found Carla waiting for her out on the sidewalk. Gypsy handed over the cash without a word. “Not bad.” Said Carla evenly. ”But you were late today, so let’s go find you another client.” img-3767.png 1254 x 1254 < 19 Views > Users who added this gallery You have to login in order to favorite this gallery Send this link to a friend To link to this gallery use : https://www.imagefap.com/gallery/14438600 Or generate html/bbcode here Report this gallery