DISCLAIMER: The following story is completely fictional in nature and does not describe any real people or situations although set in New York in at the end of the 19th Century.
The following content is sexually explicit in nature, and if such material offends you or is illegal for you to view, please discontinue reading and destroy now.
This is my first foray into Bisexual writing and was not my intent when I started this idea, I hope you enjoy and any feedback would be welcome.
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Washed and barbered, James was escorted through the streets to a nicer part of the neighbourhood controlled by the Three Leaf's (Leafs for short). The man walking with him was one of Jimmy Crow's men. James knew he had been selected for a special liaison. Madame Paul, who ran the Stick it Inn, had summoned him from where he was lifting and ordered him cleaned up. Jimmy had told one of his men to take him to the address, and James did as he was told neither Madame nor Mr Crow was worth crossing, and he had been paid a dollar for the effort and told to do as he was told and put on a good show. James hugged his coat close to him a biting cold ripped off the river and down the streets. James, only in New York this past half-year had only enjoyed the summer up to now.
His escort stood before a simple two-up house, and James moved to the door as a woman opened it, clearly the housemaid in a pined apron. "Aye 'alf," she said in a thick Irish accent, looking at the escort called 'Half ear' which the woman had shortened to 'alf in his thick accent. "Aye, Mary," he said, stepping in, and James followed, grateful to get out to the biting cold. Half took off his coat, and James followed suit. "he's a pretty one," she said, looking James up and down. "up the stairs door at the top," she said to James, and Half looked at him and nodded James moved up the stairs, and Half followed Mary to the back of the house. James walked hesitantly up the stairs to the landing. The door in front was slightly ajar; the other two doors were closed. James knocked on the door, and a soft American accent invited him in. James moved into the warm room; a blast of heat and perfume washed over him as he saw half sat half laying on a chaise lounge a beautiful woman with auburn red hair flowing down. Dressed only in a silk robe, she placed the book she had been reading down. "Hello," she said with a pleasant smile. "Do close the door", she spoke in that warm, inviting voice. James closed the door trapping the heat in. the robe was not tied nor closed. Her slightly darker face contrasted with the silky white flesh of his body. One petit tit was visible, and the nipple was erect despite the warmth. "I feel at a disadvantage, young man," she said as she rolled over to face him, the other tit being exposed as the robe slipped from it. James looked at her bewildered. "Take your clothes off," she said in a soft command. James did as he was told, stripping off quickly as he pulled the Suspendered from his shoulders. Unbuttoning his fly, he pulled down his trousers and exposed his cock, already filling with blood. "Why Madame Paul was right about you" She spoke softly, one hand moving between her legs. "Did she, Ma'am?" James said. "What she say?" he asked in his thick Irish voice. It took a moment for the woman to grasp what he was saying. "That he had a good looking Fresh in town and that you would buck me as hard as I want," she said, her face changing expression as a finger slipped inside. "You are very fresh. How long since you arrived?" she asked "Half a year, Ma'am", James replied. she giggled at the thought of being called Ma'am. "How old?" she pressed as James pulled his shirt off, throwing it on the pile of clothes. "One and twenty, I'm told," he said. "You don't know?" "Uncle, the man of the family I live with most of the time, says I was born in '72, but my papers say 1876." "He is not your Uncle?" she pressed. "Nah, just someone the gang in Derry knew, but it's all family," he said as he rose to full height and stood in the room naked. His cock swelling from half-mast from a thick thatch of pubic hair. He moved towards her, but she moved out her free hand to stop him. With a finger making a circular motion, James spun on the spot, allowing her to take him in. His white-skinned body spun with tanned face and hands. James had a thick chest of strong hairy arms that showed muscle definition. Black hairs covered his butt and formed a patch at the bottom of his spine. His legs, strong from being on them all day and running, were equally defined as he came back around. She looked at the hair from his chest that ran down over his belly; a mixture of muscle and lack of good nutrition left him with a trim waist. "Definitely not sixteen." She said admiring James let out a shiver even with the firelight and crackling. "Nervous?" she asked. "Cold Ma'am", James replied. "Well, let's get you warm." She smiled and sat up. Opening her legs, James took a pace forward. "Uh," she said, "Crawl", came the command. James got on his knees and crawled between her legs.
James was between the legs working on the woman for much time. She rested one thigh over his shoulder and held him in place. He did not stop and carried on as she moaned, groaned and profaned to God and the saints. James was rock hard as he worked on her. He was enjoying it, the first bit of pussy he had not had to chat up and convince he was no queer.
Working for Madame Paul, he was touched, pinched, played with. Some men liked to just run their hands over his body and wank over him. Some wanted to suck his cock, but many wanted him to fuck them. Madame Paul, a master of his trade knew which clients he could hold off and make them pay for more and more of James. He knew that Madame Paul sent the young men in her employ to some women of the city. It was the man's knack. All allowed by the Leaf's whose territory the Stick It Inn operated from. He heard the horror stories from other lads of what they often found when they arrived. It had been with this sinking feeling he walked up to this house, but this woman was divine, a heavenly beauty no doubt in it for a bit of as she called it freshness.
She pulled James out from between her legs and had him sit back on his knees; she traced down his torso toes moving through the hair and pubes up the stiff cock and then down the underside. James's body reacted to the touch and stimulation as her foot went under his balls. 'Thwack" came the kick, and James lurched back and tried to stand "Back down", she commanded, and James did as he was told 'Thwack' came the little kick again. It was not a siring pain like being kicked in the gut, which he had experienced. It was uncomfortable but also a little erotic. His cock bounced as she applied a few more kicks, and James knelt there, taking what she gave.
Rising from her seat, she let the gown glide from her skin to the floor and moved to the bed. James followed, and as she laid down, he moved between her legs. Lining his cock up, he shoved all seven and a half inches in one forceful thrust. Her eyes popped open, and she smiled as he gripped her leg. "Buck away," she said, and James did as he was told. He moved forcefully in here back and forth, and she let out a string of words. "Fuck me. Yes. Like that. Hard. By the Saints. Mary of God fuck me." The profanities and sacrileges words combined as she got louder and louder. James just moved back and forth in her as she shouted. He was worried about the noise, but it not being where he lived, realised it was not his problem. She pulled herself up, and he slowed down. 'Slap' she struck him across the face, and James grunted and shoved deep and hard. "By Mary and Joseph, Come in", she declared loudly.
James did not hear the feet at first, but then there was a noise outside the room before he had time to react, the door swung open, and there stood a tall, stocky man, thick moustache and beard. He looked at the scene. "What do you think you are doing?" he bellowed, and James froze half in the woman who clutched her hands to her mouth and exclaimed. "Joseph!" "I asked," the man said, advancing, "what do you think you are doing with my woman?" his accent was diluted as James stammered, withdrawing from the woman and stepping back. "I..I..I" he said as the man came closer, he could see him and the face he knew that of John (Shame) O'Connor, Captain of the Three Leaf's. James retreated, begging mercy he did not know and how sorry he was. The woman started laughing, and O'Connor stopped and looked at the young man. "Didn't mean to scare you that much, lad?" he said, the tone of his voice changing. James huddled on the floor back against the windowed wall, looked up at the bigger man. O'Connor, over six feet, looked down at him, a twinkle in his eye. James took in the man; his shirt was half undone, his suspender hung about his waist, feet were bare and holding a riding crop. "Sorry, Sir" "Ya kind of ruined the story, lad" James looked confused. "We like to play," said the woman who now sat on the edge of the bed. "My big strong man bursts in catching me with a young lover," she said as she nonchalantly played with a nipple. "I get turned on by the scene and have the young man whipped into a frenzy." With that, he moved the crop for emphasis. James took it in the fear diminishing the butterflies in his stomach retreated, and O'Connor extended a hand and hauled the naked James up. "That's disappointing", the woman spoke, looking between James' legs. "Can you blame me I thought Mr O'Conor just caught me with his..." James paused "Mistress," O'Connor said as he moved over and kissed her. "I thought you were going to..." James said before being cut off "Enough", O'Connor spoke, "You can get that hard again." pointing with the riding crop at James flaccid penis. "Yes, Mr O'Connor," James said as he took his hand to his cock. "I know what got him hard." The woman said, sitting forward and opening her legs. James looked at Mr O'Connor, and with a gesture of his head, James got on his knees and back between her thighs.
It felt different knowing that her lover was standing next to them; the heat in the room rose as James went back to work. She moaned and groaned, and James felt a strong hand on the back of his head pushing him in deeper, his nose buried in her pubic area. He felt the leather of the crop slide up his back, his shoulders locking back as it slid up and down the spin. 'tap' came the crop on James butt, and he jolted forward, and she moaned. 'tap' it came again, and James moved forward, pushing his tongue deeper, she moaned again. Her hand-mixed with his O'Connor's on James' head ruffled through his thick hair. She brought both thighs up and over James' shoulders as she moaned; one large hand left his head as another came and pushed him deeper in. James could hear muffled sounds as he was held in place. It was sometimes hard to breathe. He moved to take the occasional breath before being pushed back into position, his tongue getting tired from work, beads of sweat rolled down his forehead, and his hair became damp. The two were speaking when the larger hand took a grip of his hair and pulled him back with a jank. There was the splitting pain of hair being pulled as he fell back onto his knees, taking a deep and grasping breath looking forward, he could see the lady in full glory and out the corner of his left eye the red-purple cock head of Mr O'Connor. James's head was rotated towards it, and he tried to resit ut the hand was forceful, and he saw the other picking up the crop. James had only sucked two other men's cocks, the sailor who smuggled him aboard the ship that brought him and one client of Madame Paul. James opened his mouth, knowing he could not resist, and the cock sank into his mouth and pushed to his throat.
Not prepared for the deep invasion, James coughed as the fat head hit the back of his throat; his gag reflex kicked in, and he pulled back. The hand took a tight grip and pushed James back onto the cock, and he gagged and coughed again, trying to get air into his lungs. Allowed to pull back, the cock popped out of his mouth, and he took a deep breath in. The hand came back onto his head, but it was the woman's, and she guided James forward, and he closed his eyes and took the cock into his mouth. "Gently, honey," she said.
James Sucked on the cock now it was not being shoved into his throat. He could taste the man; it had a musk to it in both smell and taste, which James did not like but tolerated because he had no choice. The Leaf's had been good to him. They got him out of Ireland once on the boat he had been supplied with papers, and they marshalled him through immigration. He had lifted in Ireland but had been caught more than once here they taught him how to do things. It was when he got a kicking once discovered by some dockers letting a gentleman suck his cock at the docks that things changed that is when the gang moved him to Madame Paul's. A fresh was something that many of the gentlemen of New York liked. He had only fucked guys, and as he slurped and sucked on Mr O'Connor's cock he wondered if this was when it would happen and he would have to bend over. He knew it was coming as much as Madame Paul said he never forced anyone to do anything they did not want to. He knew that lads who did not bend when told to were out, and the city could become a very hostile place.
James was pulled up the blow Job finished, his jaw now sore and aching. "Back to fucking", O'Connor said as he guided James cock with his own hand into his mistress. She moaned as it slid in. "Back to the pace before," O'Connor said and, using the riding crop, whacked James ass. James kicked into gear like a racehorse and started moving back and forth. O'Connor stood next to him, his pants on the ground and his own cock head touching James as he moved back and forth. The crop in one hand he gave James encouraging but hard whacks on his butt. She encouraged him, asking for it hard. O'Connor's other hand was mauling her small breasts as he would squeeze them; a tear appeared in her eyes. "By the saints harder" O'Connor brought the crop down on James ass hard, and he let out an involuntary scream as he gripped the mistress by the hips and rammed back and forth, sweat trickled down his body. O'Connor moved close to James' ear and spoke in a harsh tone, and she swore and blasphemed below them. "Don't you plant your seed in there? You tell me when you are going to explode and do as the good fathers told you and pull out." James looked at O'Connor as he blew wet hair out his face. "Yes, Mr O'Connor" before he could finish the words, O'Connor put his lips to James, and his tongue entered his mouth. James responded as he knew how to. A large hand grabbed one butt cheek with a slap and pushed James forward, then, with a vice-like grip, pulled him back. Breaking the kiss and looking down at the woman who was writhing on the bed one the other, O'Connor hand moved from one breast, slight marks appearing around it and moved to the other she bit her finger as he body became rigid and shook at the same time she let out an almightly scream, and her body held him tight. Here hole became constricted like a vice, and James felt the boiling he knew. "Mr..." was all he got out before O'Connor pulled James back and out the head exploding with cum which fell on the soft flesh beneath him, and James let out his own roar of exhilaration. O'Connor Held James up as his cum splashed on her body, and he regained his breath both he and she were breathing heavily.
"Kneel," O'Connor said, and James climbed down between the legs thinking he was going to have to lick her again. He moved forward, but O'Connor grabbed James head and moved it to one side, pushing it against her exposed parts in his hand. He had his own cock, which he thumped back and forth with. "Open your mouth," he said, and James knew what was coming and did not want to. He looked up and O'Connor, who was redding in the face. "Open!" Mr O'Connor was not a man you wanted to annoy, and James did as he was told and opened his mouth and closed his eyes. He felt the hot spurts of cum hit his face, and some landed in his mouth. When he thought O'Connor was done, he opened his eyes and closed his mouth. "Open", O'Connor said as he stood before the kneeling James. As James opened his mouth, the cock was pushed in, and James tasted the salty flavour of O'Connor cum.
Leaning against the bed, exhausted but with a satisfied feeling, James did not know O'Connor had left. He heard the lady get up and water being splashed. She came back in her robe tied this time. She knelt down in front of James and looked at him. Cum was in his damp hair, his cheek. He looked dejected. "There is warm water in the basin by the door." She said. "Clean up and come join us for a drink in the small parlour. It is on this floor, the door opposite." She moved off towards the door. "No need to dress", she said and was gone.