Chapter 1

Caution: This Western Sex Story contains strong sexual content, including Ma/Fa, Consensual, Romantic, Historical, Humor, Oral Sex, Slow, Violent, .

Desc: Western Sex Story: Chapter 1 - Ann Olson was a school teacher who decided to go West in 1868. She had no prospects, and she hated Philadelphia, so she went looking for greener pastures. Join her on her great adventure.

Ann Olson was a good school teacher, she was just bored with life in Philadelphia. She had always been something of a tomboy and felt closed in by the limitations put on women. She couldn't do anything interesting with her life; her only choices were to get married, run a shop selling some sort of women's clothes, be a school teacher, or be a prostitute. She had no immediate prospects for the first, neither money or interest in the second, and too much of a fear of disease for the fourth, so that left the third option as the only one open to her.

She had attended Philadelphia Normal School for Young Ladies and graduated at the top of her class. This had gotten her a job teaching school, but the pay was so meager that she was living in near poverty. Ann decided that there was no place for her to be happy in the East, her only real chance for happiness was to go West. Therefore, Ann scrimped and saved her money until she had enough for a train ticket to take her somewhere west of the Mississippi River.

It was 1867, and the great war was over, so she was not too worried about her personal safety, though she had read of how uncouth ruffians were to be found in all parts of the west. Therefore, she realized that she would need some sort of personal protection, just in case. She did not know how to use a gun, but she figured that she could learn, so she went to a reputable gunsmith and asked for advice. At first, it was difficult to get the man to take her seriously, but she persisted. Finally, he recommended that she choose a Colt Pocket revolver in .31 caliber. He happened to have a used one in good condition that he would sell to her for $4.50, along with a bullet mold and 4 slugs of lead.

He recommended that she carry the weapon in a shoulder holster under her left bosom, since she was right handed; he just happened to have a suitable holster he could sell her for 75 cents. He taught her how to load the weapon, and she learned to shoot at his range. Actually, she got to be quite accurate with it, even though the gun had no sights. She spent about a month learning to shoot the gun, practicing every day; she even could draw quite rapidly, though she practiced this as a lark, never expecting this skill to be of any real use.

Ann finished out the school year, and, when spring came, gave up her one-room apartment and bought a train ticked for Kansas City, Missouri. She had only a vague idea of what she would do when she got there, but, whatever it was, at least, it would be done out West. The trip west was miserable, but it was finally over one hot day in late June, 1868. She picked up her carpet bag and headed for the hotel.

That evening after supper, she just couldn't bear to stay in her room. It was hot, and she was out West. There were no two better reasons to take a short walk outside the hotel. Since she was out West, she decided that it was appropriate that she wear her pistol. She went out the front door, never hearing the desk clerk's warning about the dangers of a woman walking alone at night on the streets of Kansas City.

She walked around for about 30 minutes, reveling in her new-found freedom, away from the restrictions of life in the staid East. Not paying too much attention to the fact, she had wandered a bit too far from the hotel and had wound up in a disreputable part of town. She walked past the mouth of a dark alley when she was grabbed by the arm and jerked into the Stygian gloom.

Ann was so startled at first that she just went along the way she was pulled, not knowing what else to do. However, she soon came to her senses and began to fight against the man who was pulling her into the depths of the alley. The man continued to pull her and another man grabbed her other arm and also pulled her toward a partially open door.

Ann was dragged into a room, possibly more properly called a shed, and thrown to the floor. When she hit the floor, her gun fell out of the holster and lay on the floor at her side. In their excitement, her two captors ignored the gun lying there and proceeded to pull at her clothes. She was wearing a skirt and a blouse, so the two men had no trouble ripping them to pieces as they pulled her clothes off. The weather was so warm that her only underclothes were a petticoat and light shift, which were also destroyed as the men pulled them from her.

Once she was virtually naked, the men stopped pulling at her and turned to removing their own clothes. She saw her chance when they both were struggling to remove their boots. Ann had regained command of her mind and body and knew what she had to do. Her pistol was there right beside her, so she calmly picked up the pistol and shot both the men in the head. At a range of less than 10 feet, there was no way that she was going to miss, and she quickly put an end to the struggles with the boots.

Her question was: Now what? She was naked except for her shoes and her gunbelt, so she certainly couldn't walk back to her hotel undressed like this. Her clothes were in tatters, so she had nothing to put on. Then she realized that she was close enough in size to the men who had attacked her that she could wear their clothing until she got back to her room. She stripped the men and put on the better of the shirts and pants. She thought about it for a moment and decided: in for a penny, in for a pound, so she tried on their boots and found that one pair was a pretty good fit. She took a hat and was fully dressed.

She had not and did not feel the least qualms about killing the two men. After all, they were about to rape her and possibly murder her, so she had simply protected herself. In fact, she decided that neither man had any further use for any of his possessions, so she took everything that she could carry with her back to her room.

She sorted through what she had looted and found guns, knives, and some money, as well as a few other items which she might sell. One of the guns was a Remington .44 caliber Army revolver; she knew that it was quite valuable and considered by many to be the finest pistol in the Army's entire arsenal. It was large and heavy, but reputed to be the best gun one could carry. She tried hanging it on her hip, the way the man had worn it, but that was just not practical for her. She swapped the holster in her shoulder rig to take the Remington and found that it would be workable. As long as she was wearing trousers, she could wear her old pistol at her right hip. When she added the bowie knife, she felt like a regular desperado—oh, such delicious fun!

She looked at herself in the mirror and realized how much she looked like a man in this outfit. Ann was 5'-4"tall, and slim, without overly prominent breasts or buttocks. Her face was pleasant looking, but not beautiful. What few discrepancies there were in her resemblance to a man should be hidden by the two pistols she was wearing. Right then, she decided to become a man! She was limited by being a woman, but she would not be limited in any way if she became a man. As of this moment, she was no longer Ann Olsen, she was ... Sandy Olsen. As soon as she could find a barber shop, she would have her hair cut in a man's style. She now had money, so she would take the $12.42 she had taken from her erstwhile rapists and buy an new outfit. Sandy Olsen would start life in style!

That night, she had a hard time sleeping, she was so excited at her new prospects. Why, she could even go into a saloon without attracting attention; man, this was heady stuff! The only thing that worried her at this stage of her new adventure was how she was going to learn to piss standing up like a man does.

The next morning, Sandy went to a barbershop before she even ate breakfast. The barber never looked twice at her, he just cut Sandy's hair short the way she wanted it and only charged the usual 5 cents. Sandy asked him what he knew about job prospects, and he suggested Sandy ask some bartenders at various saloons, since they usually knew the latest gossip in things like that. Sandy thanked him and went to breakfast.

That morning, Sandy made the rounds of some of the nearby saloons to inquire about job opportunities. The word was that with so many ex-soldiers needing jobs, there just was not that much available. One suggested that Kansas City was always looking for deputy marshals, maybe she could try asking at the local jail.

The word at the jail was that their were no deputy positions open, but had Sandy ever considered bounty hunting? The deputy she talked to explained what a bounty hunter did and why there was always room for another one, especially in Missouri. Sandy thanked the deputy and left, not really wanting to become a bounty hunter, she wasn't sure that it was a respectable job.

She needed to mull over her options, so she went to the nearest saloon. This was the nearest thing to a "Gentlemen's Club" that the average man could find to socialize in, so Sandy figured that was good enough for her. She bought a beer, just to fit in, but she figured that she would never come to like the taste. She wandered around, mostly eavesdropping on conversations so that she could learn what men talked about. She had to admit her surprise that men talked about things other than women; most women she had met only wanted to talk about men or marriage, so she had expected the same kind of thing from men.

She was listening to some general talk about the cattle business when she happen to spot a small poker game going on in the back of the barroom. Sandy wandered over and saw that there was a seat available. The professional running the game invited her to join in, so she sat down and put $20 on the table. Her brother, who had died at Bull Run, had taught her all he knew about the game, and she was quite good at it, so she felt that she should be able to hold her own.

She picked up her chips and anted up. This was no penny-ante game, so she had to be careful. She folded quickly on the early hands, so, mostly, all she lost was her ante, but she realized that her $20 would not last long at the rate she was going. Sandy buckled down and started to play in earnest; this was when she started to win, slowly, but surely. After about 2 hours, she had recovered her $20 and was starting to play with other people's money.

She and the pro ordered sandwiches from the bar and continued to play, though the rest of the players moved in and out of the game as the day wore on. By supper time, she had won a total of nearly $40 from the other players and was getting very tired. The pro asked Sandy, whom he thought was a man, to eat supper with him, he had a business proposition to discuss.

They went to a first class restaurant and had a sumptuous supper. Sandy drank coffee while the pro drank brandy and smoked a cigar. Finally, he got down to business. He said that Sandy had a good grasp of poker and should consider turning pro. Unfortunately, there was a lot about the game she still did not know. The pro would teach her all of the nuances that he had at his command in exchange for 10% of her winnings. If they worked it right, they could make a fortune, and they would not even need to cheat.

Now, professional gambling was a respectable way to make a living at that time, so Sandy was very interested. They discussed the prospects for another hour, and Sandy agreed to take on Jim Wallace as her teacher for the agreed upon 10% of her earnings. She still had not told him that she was a woman and had no immediate intention of doing so.

They went back to the same saloon, Jim had an arrangement with the bartender, and picked up the poker game where they had left off. Now that it was night time, the heavy betters began showing up, and the action picked up with larger and larger bets being placed on slimmer and slimmer cards as the alcohol was consumed. She didn't know how much Jim had made in net profit, since she did not yet know how much he paid the bartender, but Sandy's income just since supper was over $150, even after she had paid out her 10%. Sandy left the game about midnight with a promise to meet Jim at the same saloon at 10:00 o'clock the next morning. Sandy was ecstatic; she had no idea that it was so easy to make money! Professional gambling was for her!

The next day was dismal! She couldn't get a decent card the whole day. She was beginning to hate poker by supper time. Jim and Sandy went to supper and he was properly sympathetic. He said, "Now you know the down side of professional gambling! Yesterday, you just kept getting good cards, but you've had nothing but bad hands all day so far. That's the way it goes. Some days are good and some days are bad, and you just have to ride them out. Stick with it and your luck will turn—I guarantee it!"

She had no experience to fall back on, so she agreed to take his word for it. But it was hard to sit there and lose and lose. Sandy was sure that she would scream if the cards didn't turn in her favor pretty soon! They went back to "their" table in the saloon and picked up the game. Slowly, Sandy's luck began to change, she got better cards as the evening wore on, and she finally managed to show a $2 profit at the end of the night. Jim smiled and told her to keep the 20 cents she owed him, she probably needed it more than he did. She smiled back and left for her hotel room.

She passed an alley, though not "her" alley on her way back, when she heard a soft moan of pain coming from the depths of the alley. It was totally dark back there; did she have the spunk to check out what sounded like a call for help? Her eyes were beginning to adjust to the night, so she drew her Remington and slowly moved toward the rear of the alley. When she got there, she almost vomited at the sight.

Four men were holding the arms and legs of a naked woman as she lay on her back on the ground. A fifth man was between her legs, pumping away. None of the men were wearing pants, and they all had bloody crotches. This was a gang rape that looked like it had been going on for a while. Sandy was surprised that the woman was still alive, her face and body looked so battered.

Sandy exploded in rage! She started shooting without saying a word. She had killed or wounded 3 of the men before they realized what was going on. The other 2 died before they could find where they had left their own guns. Sandy rushed to the helpless woman, who said, "Thank you," and died. Sandy realized that there was nothing more that she could do for the woman, so she quickly looted the pockets of the rapists and hurried away before she could be involved with the Marshal's office, provided anybody ever showed up.

Two days later, The Kansas City Times reported on the back page of another rape, but this time the men did not escape, all 5 were found dead by a swamper the next morning. The report was that the Marshal's office had nothing more to say on the crime, since the perpetrators had obviously all been shot by some vigilante that they had no hope of apprehending.

Sandy didn't know whether to be sad or relieved that the whole matter was being dropped. The woman had been a known prostitute, so she was bound to be victimized by a customer one day, so the Marshal was not too concerned. The prostitutes all knew the kind of risks they ran when they freelanced, instead of tying themselves to the relative safety of a brothel. Sure, they could probably make more money by freelancing, but it was a dangerous way to travel.

Meanwhile, Sandy continued her education as a professional gambler. Jim was a good teacher and she learned fast. At the end of 4 weeks, he told her that he enjoyed having her as a partner, but there was nothing more that he could teach her. He did have one last piece of advice: stay off trains and riverboats, they were good places to get killed!

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Story tagged with:
Ma/Fa / Consensual / Romantic / Historical / Humor / Oral Sex / Slow / Violent /