Dot s Island
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More Island Slut...Part 1 free porn video
Yet More ‘Island Slut’… Part 1
This stuff is actually a lot of fun to write. Most of these memories, for me, are very good ones. I wouldn’t have missed any of it for the world. When this happened, I was just coming into my own on St. Croix. My young body was making me a good living, my boyfriend Roger (bless his heart and deep wallet) had given me permission to slut around…as long as he had the end of the leash. Mostly, when he was out of town, I made time to improve my ‘allowance’. Yes, I was on retainer to him; I believe it was something like $500 a month. I was probably making twice that on my back.
This is about a period of time when I worked for one of the big madams there. Yes, it’s about the kinkier side of being a whore and, a young little TS one at that.
So…the girls and I were having a very lazy and late breakfast, when some nice looking black guys shows up. He undressed me as he handed me a note then, did it a few more times while he waited.
I thanked him saying, “Tell Ms. Rita I‘ll be there promptly at four.”
He blew – I wanted to…
I read the card then passed it around. There were some weird looks then a few questions. Other than a ‘meter maid’ I’d heard a song about, I didn’t have the slightest clue.
She turned out to be the biggest madam on both islands. The girls spent some time filling me in on her, why would she want to meet? I hoped that I didn’t do something to upset her.
My normal mini-moke driver was off-island. The random other I picked was very nice, handled me like a gentleman and knew exactly where to take me. He spent a lot of time trying to slyly check me out as we rode along; he also knew who and what I was. When we started up into the mountains, on a very desolate and shaded road; I reached out and put my hand on his leg then…moved up a little more. It surprised him a little, he did swallow hard and smile, “MMmmmm, you got some nice hands Ms. Bobbie.”
I don’t think he meant ‘hands’ … with my hand I could feel a very nice black cock. As I squeezed a little, it jumped a few times, as I did that and then, got bigger and harder. Not rock hard but, hard enough to do some good deeds. When we pulled into the driveway (at Ritas’) he said, “You havta get yourself out Ms. Bobbie…uh…I can’t stand up.”
It had been fun, I asked him if he could wait for me but, I didn’t know how long. He told me that it was ok, and he would, and that he wouldn’t charge me more for ‘sittin’. After what I’d felt in his pants, I was more than willing to make his waiting worthwhile.
Rita turned out to be a nice looking dark complected gal in her mid-forties. She ushered me to her patio so that we could talk and had a girl get us some drinks. When we’d gotten the small talk out of the way, Rita switched right to business. She’d heard a lot about me and, would like to have me work for her. I could pick my clients, she knew they were all ok. I could, to some extent, negotiate price, all of my tips would be mine and I’d have time off when Roger was on-island.
There was a punch line and, she approached it carefully…
Then, “You will handle some of the rougher clients dear. Not anything dangerous because, I’d never put one of my girls in trouble. These are men with a little more than a little kink.”
I kinda suspected that was it. She knew everything about me, including how I paid my drivers. In the end we exchanged numbers and I gave her a list of possible places to find me. Her man could also leave a note at my house, that would be easy, as long as there was advance notice. She assured me that everything would have enough time before; sometimes weeks. All I had to do was pay attention and be on time.
We also talked about price…she had a sort of sliding scale for kinky clients. I’d be given 35% and could keep tips and, she would pay for anything (clothing) that was ruined and…would spring for any ‘special’ clothing I might need.
I was given a nice hug in parting, she took that time to pat my ass pretty well, while she was trying to suck my lungs out through my mouth. Back at the Moke my driver asked, “Guess you be workin for Miss Rita now Ms. Bobbie”. I assured him that I would be then added, placing my hand back where it would do the most good, “Do you want to stop in some nice private shady place…for a little bit?”
What I had my fingers on was growing even quicker this time. In about five minutes, he’d pulled off onto a little road then another one. We parked in some nice cool and breezy deep shade. There was a little bit of foreplay until I freed that beautiful cock – after that, he sat back and let me make love to a very nice piece of black meat. He was all of nine inches of white bitch stretching material, pretty thick. I ended up bent over the rear end of the Moke as mine got a good workout! He’d cleaned his pipes while waiting for me – about twenty minutes into it I realized that. Over half an hour later, with my insides re-arranged and my cunt well-stretched; I found my panties, straightened myself up a little and we continued into town. He was all smiles – I was sitting in a puddle of black seed. The ride was free.
Later, when the girls and I were having drinks, we talked about what happened with Rita; my friends knew some of the guys and agreed, “Good luck honey, better you than me. Money is one thing, gettin my ass beat by (client) or getting stretched out of shape (client) is another one. We’ll let you have all the rough ones you want!”
That evening I was picked-up at the Kings Alley Bar, by a decent looking guy, taken to his room and, had my brains fucked out for almost three hours straight. Between him and the moke driver, I’d had a cock filled day.
Something like a week later, I found the first note shoved into my door jam. It read simply ‘Call Me’…I did.
Rita had a client coming down from the states for a few days. I was to be his twenty-four hour escort and, I was going to (apparently) earn every dollar he was paying for me. She filled me in on his likes and kinks – I still could turn the client down but – as the first one, from her, I didn’t want to let her down.
He was arriving in two days, staying at the King Christian Hotel and, we would meet for an early dinner that evening. I had a small list of things to buy and was told how to dress for dinner. This guy wanted 100% slut; I had to pick up a few things.
I did have a little case of nerves, when I started to get ready, that’s only normal with a new trick. I knew that he was dominant, which didn’t help relax me a lot.
When my driver picked me up, I was ogled very well, “Oh Ms. Bobbi was a date tonight…you lookin like a girl who want to get fucked bad!”
“Not my idea honey…it’s what the client wants.”
Four inch heels, bare legs, a mini; a see-thru white blouse, lacy bra and the skimpiest panties I had just bought. Yep, I looked like a slut, even down to some cheap jewelry. I met him at a little place up on the hill, just outside of town. He looked me over as I was seated and, seemed to approve. That was always a good start. He was drinking wine; after one glass I asked if I could have a gin and tonic…he ordered one immediately! Although he was dressed casually; it was rich casual – this guy was loaded. We talked a lot, had a good meal then it was time to go. The driver had waited so we had a way back without waiting too long.
I stood off to the side as he got the key for the room, both the bellman and the desk clerk approved of my ‘catch’. Once in the room, with the lights out and the curtains wide open, he took control. I was mauled pretty well, kissed a lot and, given a major feeling-up for a while. As we both shed clothes (I had worked at getting him good and hard) I was told to sit on the bed and show him what a good cocksucker I was. Within ten minutes I was on my back, the skirt was up around my waist and my panties were gone. The first fucking was short hard and bordered on ****! I’d lubed myself a little and was REALLY glad of that! He almost fucked both of us off the bed!
We took a break and talked before he ordered another bottle of wine.
When it arrived, I used the toilet. I’d left everything on, on top (the blouse was almost completely unbuttoned) but, I got out of the mini and slipped back into my panties. We got back into bed and I was groped pretty well while we sipped wine. I took breaks and worked at getting him hard again, it didn’t happen too fast.
During this, while I sucked and stroked, he moved me around so that he could play with my backside. The first hard slap took me by surprise. The next few lit a little fire back there. Yes…I knew that he was a spanker and more. By the time his cock was coming to attention, again, I was beginning to sting pretty well. He pulled me off his cock then up to his head so that he could kiss me as his hand explored my crotch.
“Bobbie dear…I think you know what comes next, don’t you?”
I nodded in the dim light. He dragged-out the waiting – the part that really sucks – with talking and more foreplay. By the time he got out of bed and, positioned an armless chair in the center of the floor, that eight inch cock was rock hard…spanking did turn him on. I was to supply the rest of it…a struggle to ‘not’ be spanked…like a girlfriend or wife that didn’t want spanked.
He came over to the bed, took me by the wrist and started to pull me out of bed. I whined, struggled a little and started to beg…
“Honey, please no…please…PLEASE, don’t spank me!” I begged. “I promise to be good…I’ll do anything…PLEASE don’t spank me…I’ll be good.”
It turned into a tug of war and a little wrestling match, as I was almost dragged to the waiting chair. I didn’t have to fake much of it; I didn’t want to be spanked! The bad news was that it was part of this trick; I was going to get a sore backside; the only question was, how sore?
I didn’t get real loud but did continue to beg and whine; once I was over his lap, I struggled more and started to kick and twist around. I wasn’t going to make it easy for him.
He held onto me at the waist, snugged my panties up good and tight (they weren’t any protection anyway – they were hip-huggers) then, gave my exposed lower cheeks a couple of pretty good smacks.
“Calm down young lady; one way or the other you’re going to get a good sound spanking.”
I knew that and, the word ‘good’ had little to do with it – I was held in position, his rigid cock trapped between my side and his stomach. I was given a few more hard smacks. He kept the spanking going and I did my part by begging, kicking and wiggling. Once everything back there was on fire, I was released and told to get on my knees, between his legs (which he spread).
“Now, you little slut, suck that cock and, show me how good you are at it for ‘daddy’. “
While I gave him the sloppiest blow job I could work up; he explained what was going to happen…
“I’ve given you a ‘warm-up’ my dear, the rest of the spanking will come after you’re finished down there.” He had a good grip on my hair; he pulled me off of his cock, gave me a long wet kiss then pushed me back down to continue. My little ass tingled, it also burned…I concentrated on sucking that cock.
He had a double handful of my hair and forced me to take as much as I could; to the point of choking and gagging on it. Between his pre-cum and my saliva, it got very messy, quickly.
There was no warning when he came; he just exploded in my mouth with one big moan of pleasure. I did my best to swallow as much as I could but, for a guy who’d cum about an hour before, he still had a big load! I choked, I gagged, I tried to breathe; until he pulled me off of his cock, gave me another big kiss then ordered, “Now, get that naughty little ass back over my knee!” I didn’t let it happen easily – if he wanted to really spank me, he’d have to work at it – he did. In about a minute I was back in position and getting the real thing, no more warm-up!
The first few smacks were right across the lower part of my (bare) cheeks and stung like hell. He spanked his way up across the flimsy panties, back down then, went to work on the center of my cheeks. It didn’t take long until my little ass was on fire again; this time a lot worse.
I kept up the wiggling and kicking, the begging and pleading, the twisting around on his lap. This time, it was for real. He knew what he was doing and the pain became worse and worse. I did begin to tear-up after a little while but, I didn’t get to the point of actually crying. Making a lot of noise but, no real tears.
He stopped long enough to pull my panties down, just below my stinging cheeks, tuck me into his lap securely then…continued the spanking all over my ass.
Rita had coached me that; tears and begging really turned him on. In another few minutes – when my backside REALLY started to feel like it was on fire – I gave him that. I was wearing down with all of the kicking and wiggling, I had started to drool a little (from my yelps of pain) and, was breathing hard and fast. When he went back to spanking my lower cheeks, it didn’t take much – a few minutes and I exploded in tears. I simply let go and let my feelings take over; it wasn’t exactly sobbing but there were tears (I’d helped it a little too ;)). Satisfied, he stopped, rubbed a little then, helped me stand up. The panties slipped down to my ankles in a little puddle as I reached back and started to ‘gently’ rub my stinging cheeks.
He was rock hard all over again!
He watched me do my little dance for a few minutes then, got to his feet and gave me a nice warm hug and a kiss, before taking me to bed. I shuffled slowly – panties still around my ankles – he tried to speed things up by giving me a few well placed swats. I wound up face down across the bed, still clutching and rubbing my sore ass. When he joined me, for more foreplay and groping, he also finished stripping me before starting to give me a good finger fucking. In the slippery mess, inside of my cunt, he found my ‘G’ spot and started to massage it; he was rock hard and I started to get a little erection; along with some small dribbles of cum.
Shortly, I was ordered to my tummy, my legs were pushed together and he mounted me. After pushing the head of his cock firmly between my glowing cheeks…he pushed hard! Not only did the quick hard penetration get a yelp of pain (from me) but, when he slammed against my tender backside…it hurt like hell. My job was to lay there and take it; his job was to make me as uncomfortable as possible…he did a very good job of it. Something like an hour later, I was on my back as he pounded away then, finally, unloaded deep inside of my tingling cunt.
I was lying in a wet spot on the bed and had to pee very bad!
The nice cool toilet seat felt good, for a few seconds, and then became uncomfortable. A check in the full length mirror showed why. My little ass wasn’t too bad looking but it was bruised…right where I sat. I went back to bed; to be comforted, held and kissed then, fondled a little more. I’d left a little cum in the toilet but, was still leaking. A short time later we both drifted off to sleep…
End Part 1
This stuff is actually a lot of fun to write. Most of these memories, for me, are very good ones. I wouldn’t have missed any of it for the world. When this happened, I was just coming into my own on St. Croix. My young body was making me a good living, my boyfriend Roger (bless his heart and deep wallet) had given me permission to slut around…as long as he had the end of the leash. Mostly, when he was out of town, I made time to improve my ‘allowance’. Yes, I was on retainer to him; I believe it was something like $500 a month. I was probably making twice that on my back.
This is about a period of time when I worked for one of the big madams there. Yes, it’s about the kinkier side of being a whore and, a young little TS one at that.
So…the girls and I were having a very lazy and late breakfast, when some nice looking black guys shows up. He undressed me as he handed me a note then, did it a few more times while he waited.
I thanked him saying, “Tell Ms. Rita I‘ll be there promptly at four.”
He blew – I wanted to…
I read the card then passed it around. There were some weird looks then a few questions. Other than a ‘meter maid’ I’d heard a song about, I didn’t have the slightest clue.
She turned out to be the biggest madam on both islands. The girls spent some time filling me in on her, why would she want to meet? I hoped that I didn’t do something to upset her.
My normal mini-moke driver was off-island. The random other I picked was very nice, handled me like a gentleman and knew exactly where to take me. He spent a lot of time trying to slyly check me out as we rode along; he also knew who and what I was. When we started up into the mountains, on a very desolate and shaded road; I reached out and put my hand on his leg then…moved up a little more. It surprised him a little, he did swallow hard and smile, “MMmmmm, you got some nice hands Ms. Bobbie.”
I don’t think he meant ‘hands’ … with my hand I could feel a very nice black cock. As I squeezed a little, it jumped a few times, as I did that and then, got bigger and harder. Not rock hard but, hard enough to do some good deeds. When we pulled into the driveway (at Ritas’) he said, “You havta get yourself out Ms. Bobbie…uh…I can’t stand up.”
It had been fun, I asked him if he could wait for me but, I didn’t know how long. He told me that it was ok, and he would, and that he wouldn’t charge me more for ‘sittin’. After what I’d felt in his pants, I was more than willing to make his waiting worthwhile.
Rita turned out to be a nice looking dark complected gal in her mid-forties. She ushered me to her patio so that we could talk and had a girl get us some drinks. When we’d gotten the small talk out of the way, Rita switched right to business. She’d heard a lot about me and, would like to have me work for her. I could pick my clients, she knew they were all ok. I could, to some extent, negotiate price, all of my tips would be mine and I’d have time off when Roger was on-island.
There was a punch line and, she approached it carefully…
Then, “You will handle some of the rougher clients dear. Not anything dangerous because, I’d never put one of my girls in trouble. These are men with a little more than a little kink.”
I kinda suspected that was it. She knew everything about me, including how I paid my drivers. In the end we exchanged numbers and I gave her a list of possible places to find me. Her man could also leave a note at my house, that would be easy, as long as there was advance notice. She assured me that everything would have enough time before; sometimes weeks. All I had to do was pay attention and be on time.
We also talked about price…she had a sort of sliding scale for kinky clients. I’d be given 35% and could keep tips and, she would pay for anything (clothing) that was ruined and…would spring for any ‘special’ clothing I might need.
I was given a nice hug in parting, she took that time to pat my ass pretty well, while she was trying to suck my lungs out through my mouth. Back at the Moke my driver asked, “Guess you be workin for Miss Rita now Ms. Bobbie”. I assured him that I would be then added, placing my hand back where it would do the most good, “Do you want to stop in some nice private shady place…for a little bit?”
What I had my fingers on was growing even quicker this time. In about five minutes, he’d pulled off onto a little road then another one. We parked in some nice cool and breezy deep shade. There was a little bit of foreplay until I freed that beautiful cock – after that, he sat back and let me make love to a very nice piece of black meat. He was all of nine inches of white bitch stretching material, pretty thick. I ended up bent over the rear end of the Moke as mine got a good workout! He’d cleaned his pipes while waiting for me – about twenty minutes into it I realized that. Over half an hour later, with my insides re-arranged and my cunt well-stretched; I found my panties, straightened myself up a little and we continued into town. He was all smiles – I was sitting in a puddle of black seed. The ride was free.
Later, when the girls and I were having drinks, we talked about what happened with Rita; my friends knew some of the guys and agreed, “Good luck honey, better you than me. Money is one thing, gettin my ass beat by (client) or getting stretched out of shape (client) is another one. We’ll let you have all the rough ones you want!”
That evening I was picked-up at the Kings Alley Bar, by a decent looking guy, taken to his room and, had my brains fucked out for almost three hours straight. Between him and the moke driver, I’d had a cock filled day.
Something like a week later, I found the first note shoved into my door jam. It read simply ‘Call Me’…I did.
Rita had a client coming down from the states for a few days. I was to be his twenty-four hour escort and, I was going to (apparently) earn every dollar he was paying for me. She filled me in on his likes and kinks – I still could turn the client down but – as the first one, from her, I didn’t want to let her down.
He was arriving in two days, staying at the King Christian Hotel and, we would meet for an early dinner that evening. I had a small list of things to buy and was told how to dress for dinner. This guy wanted 100% slut; I had to pick up a few things.
I did have a little case of nerves, when I started to get ready, that’s only normal with a new trick. I knew that he was dominant, which didn’t help relax me a lot.
When my driver picked me up, I was ogled very well, “Oh Ms. Bobbi was a date tonight…you lookin like a girl who want to get fucked bad!”
“Not my idea honey…it’s what the client wants.”
Four inch heels, bare legs, a mini; a see-thru white blouse, lacy bra and the skimpiest panties I had just bought. Yep, I looked like a slut, even down to some cheap jewelry. I met him at a little place up on the hill, just outside of town. He looked me over as I was seated and, seemed to approve. That was always a good start. He was drinking wine; after one glass I asked if I could have a gin and tonic…he ordered one immediately! Although he was dressed casually; it was rich casual – this guy was loaded. We talked a lot, had a good meal then it was time to go. The driver had waited so we had a way back without waiting too long.
I stood off to the side as he got the key for the room, both the bellman and the desk clerk approved of my ‘catch’. Once in the room, with the lights out and the curtains wide open, he took control. I was mauled pretty well, kissed a lot and, given a major feeling-up for a while. As we both shed clothes (I had worked at getting him good and hard) I was told to sit on the bed and show him what a good cocksucker I was. Within ten minutes I was on my back, the skirt was up around my waist and my panties were gone. The first fucking was short hard and bordered on ****! I’d lubed myself a little and was REALLY glad of that! He almost fucked both of us off the bed!
We took a break and talked before he ordered another bottle of wine.
When it arrived, I used the toilet. I’d left everything on, on top (the blouse was almost completely unbuttoned) but, I got out of the mini and slipped back into my panties. We got back into bed and I was groped pretty well while we sipped wine. I took breaks and worked at getting him hard again, it didn’t happen too fast.
During this, while I sucked and stroked, he moved me around so that he could play with my backside. The first hard slap took me by surprise. The next few lit a little fire back there. Yes…I knew that he was a spanker and more. By the time his cock was coming to attention, again, I was beginning to sting pretty well. He pulled me off his cock then up to his head so that he could kiss me as his hand explored my crotch.
“Bobbie dear…I think you know what comes next, don’t you?”
I nodded in the dim light. He dragged-out the waiting – the part that really sucks – with talking and more foreplay. By the time he got out of bed and, positioned an armless chair in the center of the floor, that eight inch cock was rock hard…spanking did turn him on. I was to supply the rest of it…a struggle to ‘not’ be spanked…like a girlfriend or wife that didn’t want spanked.
He came over to the bed, took me by the wrist and started to pull me out of bed. I whined, struggled a little and started to beg…
“Honey, please no…please…PLEASE, don’t spank me!” I begged. “I promise to be good…I’ll do anything…PLEASE don’t spank me…I’ll be good.”
It turned into a tug of war and a little wrestling match, as I was almost dragged to the waiting chair. I didn’t have to fake much of it; I didn’t want to be spanked! The bad news was that it was part of this trick; I was going to get a sore backside; the only question was, how sore?
I didn’t get real loud but did continue to beg and whine; once I was over his lap, I struggled more and started to kick and twist around. I wasn’t going to make it easy for him.
He held onto me at the waist, snugged my panties up good and tight (they weren’t any protection anyway – they were hip-huggers) then, gave my exposed lower cheeks a couple of pretty good smacks.
“Calm down young lady; one way or the other you’re going to get a good sound spanking.”
I knew that and, the word ‘good’ had little to do with it – I was held in position, his rigid cock trapped between my side and his stomach. I was given a few more hard smacks. He kept the spanking going and I did my part by begging, kicking and wiggling. Once everything back there was on fire, I was released and told to get on my knees, between his legs (which he spread).
“Now, you little slut, suck that cock and, show me how good you are at it for ‘daddy’. “
While I gave him the sloppiest blow job I could work up; he explained what was going to happen…
“I’ve given you a ‘warm-up’ my dear, the rest of the spanking will come after you’re finished down there.” He had a good grip on my hair; he pulled me off of his cock, gave me a long wet kiss then pushed me back down to continue. My little ass tingled, it also burned…I concentrated on sucking that cock.
He had a double handful of my hair and forced me to take as much as I could; to the point of choking and gagging on it. Between his pre-cum and my saliva, it got very messy, quickly.
There was no warning when he came; he just exploded in my mouth with one big moan of pleasure. I did my best to swallow as much as I could but, for a guy who’d cum about an hour before, he still had a big load! I choked, I gagged, I tried to breathe; until he pulled me off of his cock, gave me another big kiss then ordered, “Now, get that naughty little ass back over my knee!” I didn’t let it happen easily – if he wanted to really spank me, he’d have to work at it – he did. In about a minute I was back in position and getting the real thing, no more warm-up!
The first few smacks were right across the lower part of my (bare) cheeks and stung like hell. He spanked his way up across the flimsy panties, back down then, went to work on the center of my cheeks. It didn’t take long until my little ass was on fire again; this time a lot worse.
I kept up the wiggling and kicking, the begging and pleading, the twisting around on his lap. This time, it was for real. He knew what he was doing and the pain became worse and worse. I did begin to tear-up after a little while but, I didn’t get to the point of actually crying. Making a lot of noise but, no real tears.
He stopped long enough to pull my panties down, just below my stinging cheeks, tuck me into his lap securely then…continued the spanking all over my ass.
Rita had coached me that; tears and begging really turned him on. In another few minutes – when my backside REALLY started to feel like it was on fire – I gave him that. I was wearing down with all of the kicking and wiggling, I had started to drool a little (from my yelps of pain) and, was breathing hard and fast. When he went back to spanking my lower cheeks, it didn’t take much – a few minutes and I exploded in tears. I simply let go and let my feelings take over; it wasn’t exactly sobbing but there were tears (I’d helped it a little too ;)). Satisfied, he stopped, rubbed a little then, helped me stand up. The panties slipped down to my ankles in a little puddle as I reached back and started to ‘gently’ rub my stinging cheeks.
He was rock hard all over again!
He watched me do my little dance for a few minutes then, got to his feet and gave me a nice warm hug and a kiss, before taking me to bed. I shuffled slowly – panties still around my ankles – he tried to speed things up by giving me a few well placed swats. I wound up face down across the bed, still clutching and rubbing my sore ass. When he joined me, for more foreplay and groping, he also finished stripping me before starting to give me a good finger fucking. In the slippery mess, inside of my cunt, he found my ‘G’ spot and started to massage it; he was rock hard and I started to get a little erection; along with some small dribbles of cum.
Shortly, I was ordered to my tummy, my legs were pushed together and he mounted me. After pushing the head of his cock firmly between my glowing cheeks…he pushed hard! Not only did the quick hard penetration get a yelp of pain (from me) but, when he slammed against my tender backside…it hurt like hell. My job was to lay there and take it; his job was to make me as uncomfortable as possible…he did a very good job of it. Something like an hour later, I was on my back as he pounded away then, finally, unloaded deep inside of my tingling cunt.
I was lying in a wet spot on the bed and had to pee very bad!
The nice cool toilet seat felt good, for a few seconds, and then became uncomfortable. A check in the full length mirror showed why. My little ass wasn’t too bad looking but it was bruised…right where I sat. I went back to bed; to be comforted, held and kissed then, fondled a little more. I’d left a little cum in the toilet but, was still leaking. A short time later we both drifted off to sleep…
End Part 1
Maddie
- 17.11.2022
- 36
- 0
