CATHLEEN Diary of a lesbian hooker of the 1930s
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CATHLEEN. Part 3 free porn video
CATHLEEN. Diary of a lesbian hooker of the 1930s. PART 3
Most of the bosses, underbosses and capos in the mob in Boston were married. Many of them had a mistress or two on the side. Most of the time, the wife was aware of it and said nothing. Most of the mob wives I met were in their late 40s to early 60s. Pretty well all of them had married for the money and some actually preferred it when their husband had a mistress. They could then lead their own life, as long as they were discreet.
I met some of them simply because they were lesbians or bisexuals. It’s not because you were married to a mobster that you liked men. Their husband actually preferred to know his wife was with another woman than another man.
The one I knew best was Vera. She was nearly 60 and had been licking twat for decades and decades. She loved her grey hair which she had down to her shoulders and kept a nice figure by walking, cycling and horse riding. She had a dramatic and kinky side to her. At one time, she was picking up regular hookers on the street, but that got dangerous and the girls didn’t always cooperate. She built a team of three girls she used for roleplaying and also had one chauffeur she could trust to keep quiet. Everything was set up beforehand of course, but we went along with it. One such encounter happened just before Christmas. Alanis had given me the particulars which changed a little each time.
I was to meet Vera in the harbour area which was quite deserted at night. I was not fond of that setup but I knew she wouldn’t let me wait long. I was dressed in typical street hooker clothes: white blouse tied in a knot over my free bouncing breasts, a very short skirt with an even smaller pair of panties, and long red leather boots. I kept in the shadow of a large warehouse not to be noticed. Then I heard the familiar sound of a large car. Vera’s limo drove towards me all lights turned off.
The side door opened and a silhouette wearing a fedora and holding a cigar stepped out.
“Come here sweetie”, the voice said
I walked over and recognized Vera dressed as a man, complete with trousers, white shirt, suspenders, and even a stuck-on moustache. I knew better than to laugh. She blew smoke in my face, but I liked the smell of a good cigar. During all this, the driver always stayed in the car which had a solid partition between the front seat and the wide back seat. Communication between Vera and her driver was only by phone.
“How much ?”, she asked
“It depends what you want”, I answered
“All the way”, she said, making her voice sound harsh, “Will this do ?”.
She showed me a $50 bill.
“That’s more than enough”, I answered as I put it into my handbag
“Get in”, she said
It was dark in there. The seat was black, Vera was dressed in black and on top of that in was pitch black in that part of the harbour. Vera had put her cigar in the ashtray sticking out of the partition. She kissed my neck, and then the top of my tits. I could really smell that cigar. Her hand went up my thigh and pushed against my panties. I opened my legs and she groped at my mound which was getting wet. She undid the knot of my blouse and began to suck on my nipples and my tits. Her hand took mine and put it between her legs. I could feel a hard smooth cylinder. I unzipped her fly and pushed my hand in.
“Suck it”, she ordered
I flipped the black rubber cock out of her fly. I bent over her lap and took the cock in my mouth. It tasted like cherry but a little salty. It was too long to get in all the way into my mouth so I concentrated on the knob. While one hand was pumping the cock, my other hand unbuttoned the trousers and slipped into her pants. She slapped my wrist.
“Don’t touch me there”, she cried
I could smell her cunt. She wanted to be the lead and I had to follow her orders.
Vera took me by the shoulders and lifted my upper body. She moved so I could lie down on the seat length wise. She took off her jacket and hung it on a hook on the partition. I was lying down on the leather seat with my legs open but my boots still on. I made a move to take them off.
“Leave them”, Vera snapped
She reached with both hands under my skirt and pulled off my panties as I lifted my ass off the seat. Vera then pushed her suspenders off her shoulders, pulled down her trousers half way down her thighs, and stretched herself on top of me. I could smell her cigar breath as she tried to kiss me. I could feel her hand searching for her cock and pushing it against my thigh by accident.
“Sorry”, she mumbled in my face.
I winced as her cock poked at my pubic area. I opened my legs wider and lifted them in the air wrapping my booth-covered legs around her waist. She finally found my hole with her cock and pushed it in slowly, trying to apologize for her previous clumsiness. It was a big cock and I breathed hard and deep when it got completely inside me. I didn’t know if she would let me but I grabbed her ass as she fucked me. She had borrowed her husband’s shorts but I could still feel her hard round asscheeks I had played with often. She let me fondle them. Vera began her up and down movement on me.
“Ahhhhhh….”, I cried, as it got a bit painful
“Sorry…baby…I’ll be more careful”, she whispered in my ear
She was and concentrated more on rubbing the top edge of the strapon against her clit than fucking me deep. Whether she was doing it consciously or not, the cock was rubbing directly against my own clit. I was nearing an orgasm when Vera shuddered and cried “fuck” in my ear.
She pulled out of me practically immediately after her orgasm. She didn’t ask me if I had cum. I didn’t say anything but I was not pleased. She was usually more caring.
“Ok…put those back on”, she gave me my panties. I pushed my boots one at a time through the holes and pulled them up under my skirt.
“Call her a cab”, she told her driver on the phone
“You can get out the other door”, she said not looking at me
I opened the heavy door and the limo drove off. A few minutes later a cab found me.
“Are you ok ?”, the nice man asked
“Yeah…don’t worry…I’m fine”, I answered, and we drove off.
--------------------------------------------------------------------------------------------------------------------------
It was getting pretty cold out there at night so I decided to find tricks indoors. One place I could always go to without taking a car was one of the local brothels. There were of course many in Boston but one nice brothel was situated a few blocks from the Pub I hung out in. Since these establishments were also controlled by the mob, I had access to this one in particular and knew most people. As long as I told the Madame (her name was Julia) I was on the premises, there was no problem. If I made a score, I always gave her a cut.
Of course the problem with hanging around a brothel is that you get propositioned by the men. I became quite resourceful in getting out of that situation.
That evening I was told by the Madame to go to the second floor, to walk along the hallway, and to follow a woman in a fur coat coming out of a room.
“Get her out of here as soon as possible”, said Julia
“Where should I take her ?”, I asked
“To a hotel somewhere”, said Julia nervously, “Tell her it’s a set-up”.
“Who is she ?”, I asked innocently
“You’ll recognize her”, said Julia, “Now scoot upstairs”.
I walked quickly down the hallway. Coming out of a room, fully dressed in her fur coat, her black felt hat pulled down over her face so that few people could recognize her, was the lady who was the main assistant to the mayor.
“Please follow me. I was told that you were walking into a set-up”, I said quickly
She stopped in her tracks, turned around and looked at me.
“Were you the person I was supposed to meet ?”, she asked
“No. I was just told to get you out of here as soon as possible ”, I answered, surprised at my assurance.
“I …was planning on meeting someone in that room…and nobody showed up”, she stammered as she approached me.
One has to remember that Boston was a mob town and that the mayor or anyone associated with him was vulnerable to blackmail if found in a brothel.
“Do you work here ?”, she asked
“No ..I work for Alanis…I’m just visiting”, I answered
The woman was obviously quite scared and didn’t know what to do.
“Trust me. We have to leave this place and go to safer surroundings”, I suggested
“You look trustworthy…I’ll follow you”, the lady answered, relieved.
I grabbed my coat and we walked quickly out of the establishment. A few minutes later we were in a taxi heading to a hotel on the outskirts of town. I knew the address and she didn’t ask questions. We checked in and I found myself in a strange hotel room with an even stranger woman.
When she took off her expensive coat and felt hat, I finally saw more of her. I was right, she was the mayor’s assistant as I had seen her on posters and in a celebration at the factory. She was quite tall and very slim. She was dressed in a business suit which made her look older but she must have been mid-40s. Her hair was curly and hung down to her shoulders. She had a wide brow which made her look like one of the actresses I liked in the movies.
“Where do you work ?”, she asked as she lit a cigarette
“During the day I work at the factory…otherwise I get tricks around town”, I answered honestly “I don’t know Alanis but I know of her”, she said looking at me with a smile
“I’ll level with you”, she began, “I was supposed to meet a woman”.
“At the brothel ?”, I asked surprised
“I know..I know…It was so stupid of me”, she said as she covered her face with her hands
“You had seen pictures ?”, I asked
“How did you know ?”, she looked at me in shock
“It’s a common trick”, I said, “Now they know something about you”
“Nobody will find me here ?”, she asked nervously
“Nobody followed us”, I said reassuringly
“But what if someone walks into the room once we are together and takes pictures ?”, she said, but not very convincingly
“Then I lose my job, my other job, and the mayor has me shot”, I answered
She got up, took off her jacket, and started to unbutton her blouse.
“My name’s is Theresa. Get undressed”, she ordered, “I had my mind set on sex tonight and I’ll have it”.
I didn’t think that was her real name but who cared. I had already taken my shoes off. I quickly got out of my blouse which was the only garment covering my breasts. I slipped out of my skirt.
“No…keep your skirt on…but take off your panties”, she said, as she lay on the bed.
She was topless and she had also taken off her panties but kept her skirt on. I learned that they all had their preferences and to just go along with it.
She had medium-size breasts which were slightly sagging. I joined her on the bed, walking on my knees until I reached her. She opened her legs and lifted her skirt up only partially up her thighs.
“Suck me”, she said in a soft voice
I slipped my head between her thighs and under her skirt as she lay on the bed with her head resting on the pillow. Her skirt smelled of wet wool and my mouth was guided by the familiar smell of wet cunt. I tongued her labia and inserted my tongue in her love crack. She was very wet.
“I’m very wet”, she confirmed, as she moved and opened her legs even wider
She was shaved, which was uncommon. As I licked her, I remembered she had a reputation in lesbian circles but I had never had any confirmation of it. People said a lot of things that weren’t true. I flicked my tongue on her large erect clit and I heard her moan loudly. I could feel her hands on my head which made a large bump under her skirt.
“I wanna rub with you”, I heard her say
I pulled my head from under her skirt and sat on the bed with my own skirt lifted around my waist. She didn’t say anything but she gave me a wicked smile when she saw I was shaved.
“Let’s fuck”, Theresa said as she opened my legs with her hands
“Yeah..fuck me”, I cried, getting her even more excited
She wanted to fuck with our skirts on. It was a common fantasy and I enjoyed it also.
She settled her hips between my thighs, and we moved so that our cunts kissed making sure to keep our skirts bunched up around our waist. When she mounted me, the pile of material made it uncomfortable since it created a large bump between our tummies. She wanted us to keep our skirt on so much that she took the time to spread the material so that there was only a thin layer between us. She must have had hookers before since she didn’t even try to kiss me. Instead she put her face next to mine against the bed and kissed my neck, just like some men do.
My hard tits were not matching her sagging pair but she pushed the top of her chest against my globes and that turned me on. She was an expert at cunt rubbing and our clams were immediately kissing, crack against crack, lips against lips. I could feel our cunt juices flowing down my cunt to my ass. She kept saying “oh fuck” in my ear and I answered “fuck me hard” every time. Theresa had manoeuvered so that her clit had not touched mine directly but after a few minutes, I moved sideways a few inches and our female pricks touched. She howled and I screamed. I grabbed her small asscheeks with both hands and pulled her against me. She began to hump harder and harder, engorged clits slapping against each other, until we both came at the same time and with a common scream.
I continued playing with her ass while she was still on top of me. She nibbled on my earlobe.
“Fuck”, she whispered in my ear, “That was some fuck”.
“You like me Theresa ?”, I said without thinking
“Yes..you’re good”, she answered stretching her left arm over my tits.
“Tell Alanis when you want me and I’ll meet you anywhere you want. My name is Cathleen”, I said
“You will of course be discreet”, she said slowly as she pulled herself up and stared at me.
“Of course…I got you here didn’t I”, I answered not wanting to be intimidated.
“Yes you did and I’m grateful”’ she said giving me a genuine smile
We both got dressed and Theresa took a cab home. I hung around the lobby for a few minutes.
“I bet she didn’t pay you”, said the white-haired woman at the desk. I had seen her every time I had turned a trick in that hotel.
“You’re right. I forgot to ask”, I answered
“She must be a good fuck”, said the woman
“Let’s say it was worth it”, I said smiling.
To be continued
Most of the bosses, underbosses and capos in the mob in Boston were married. Many of them had a mistress or two on the side. Most of the time, the wife was aware of it and said nothing. Most of the mob wives I met were in their late 40s to early 60s. Pretty well all of them had married for the money and some actually preferred it when their husband had a mistress. They could then lead their own life, as long as they were discreet.
I met some of them simply because they were lesbians or bisexuals. It’s not because you were married to a mobster that you liked men. Their husband actually preferred to know his wife was with another woman than another man.
The one I knew best was Vera. She was nearly 60 and had been licking twat for decades and decades. She loved her grey hair which she had down to her shoulders and kept a nice figure by walking, cycling and horse riding. She had a dramatic and kinky side to her. At one time, she was picking up regular hookers on the street, but that got dangerous and the girls didn’t always cooperate. She built a team of three girls she used for roleplaying and also had one chauffeur she could trust to keep quiet. Everything was set up beforehand of course, but we went along with it. One such encounter happened just before Christmas. Alanis had given me the particulars which changed a little each time.
I was to meet Vera in the harbour area which was quite deserted at night. I was not fond of that setup but I knew she wouldn’t let me wait long. I was dressed in typical street hooker clothes: white blouse tied in a knot over my free bouncing breasts, a very short skirt with an even smaller pair of panties, and long red leather boots. I kept in the shadow of a large warehouse not to be noticed. Then I heard the familiar sound of a large car. Vera’s limo drove towards me all lights turned off.
The side door opened and a silhouette wearing a fedora and holding a cigar stepped out.
“Come here sweetie”, the voice said
I walked over and recognized Vera dressed as a man, complete with trousers, white shirt, suspenders, and even a stuck-on moustache. I knew better than to laugh. She blew smoke in my face, but I liked the smell of a good cigar. During all this, the driver always stayed in the car which had a solid partition between the front seat and the wide back seat. Communication between Vera and her driver was only by phone.
“How much ?”, she asked
“It depends what you want”, I answered
“All the way”, she said, making her voice sound harsh, “Will this do ?”.
She showed me a $50 bill.
“That’s more than enough”, I answered as I put it into my handbag
“Get in”, she said
It was dark in there. The seat was black, Vera was dressed in black and on top of that in was pitch black in that part of the harbour. Vera had put her cigar in the ashtray sticking out of the partition. She kissed my neck, and then the top of my tits. I could really smell that cigar. Her hand went up my thigh and pushed against my panties. I opened my legs and she groped at my mound which was getting wet. She undid the knot of my blouse and began to suck on my nipples and my tits. Her hand took mine and put it between her legs. I could feel a hard smooth cylinder. I unzipped her fly and pushed my hand in.
“Suck it”, she ordered
I flipped the black rubber cock out of her fly. I bent over her lap and took the cock in my mouth. It tasted like cherry but a little salty. It was too long to get in all the way into my mouth so I concentrated on the knob. While one hand was pumping the cock, my other hand unbuttoned the trousers and slipped into her pants. She slapped my wrist.
“Don’t touch me there”, she cried
I could smell her cunt. She wanted to be the lead and I had to follow her orders.
Vera took me by the shoulders and lifted my upper body. She moved so I could lie down on the seat length wise. She took off her jacket and hung it on a hook on the partition. I was lying down on the leather seat with my legs open but my boots still on. I made a move to take them off.
“Leave them”, Vera snapped
She reached with both hands under my skirt and pulled off my panties as I lifted my ass off the seat. Vera then pushed her suspenders off her shoulders, pulled down her trousers half way down her thighs, and stretched herself on top of me. I could smell her cigar breath as she tried to kiss me. I could feel her hand searching for her cock and pushing it against my thigh by accident.
“Sorry”, she mumbled in my face.
I winced as her cock poked at my pubic area. I opened my legs wider and lifted them in the air wrapping my booth-covered legs around her waist. She finally found my hole with her cock and pushed it in slowly, trying to apologize for her previous clumsiness. It was a big cock and I breathed hard and deep when it got completely inside me. I didn’t know if she would let me but I grabbed her ass as she fucked me. She had borrowed her husband’s shorts but I could still feel her hard round asscheeks I had played with often. She let me fondle them. Vera began her up and down movement on me.
“Ahhhhhh….”, I cried, as it got a bit painful
“Sorry…baby…I’ll be more careful”, she whispered in my ear
She was and concentrated more on rubbing the top edge of the strapon against her clit than fucking me deep. Whether she was doing it consciously or not, the cock was rubbing directly against my own clit. I was nearing an orgasm when Vera shuddered and cried “fuck” in my ear.
She pulled out of me practically immediately after her orgasm. She didn’t ask me if I had cum. I didn’t say anything but I was not pleased. She was usually more caring.
“Ok…put those back on”, she gave me my panties. I pushed my boots one at a time through the holes and pulled them up under my skirt.
“Call her a cab”, she told her driver on the phone
“You can get out the other door”, she said not looking at me
I opened the heavy door and the limo drove off. A few minutes later a cab found me.
“Are you ok ?”, the nice man asked
“Yeah…don’t worry…I’m fine”, I answered, and we drove off.
--------------------------------------------------------------------------------------------------------------------------
It was getting pretty cold out there at night so I decided to find tricks indoors. One place I could always go to without taking a car was one of the local brothels. There were of course many in Boston but one nice brothel was situated a few blocks from the Pub I hung out in. Since these establishments were also controlled by the mob, I had access to this one in particular and knew most people. As long as I told the Madame (her name was Julia) I was on the premises, there was no problem. If I made a score, I always gave her a cut.
Of course the problem with hanging around a brothel is that you get propositioned by the men. I became quite resourceful in getting out of that situation.
That evening I was told by the Madame to go to the second floor, to walk along the hallway, and to follow a woman in a fur coat coming out of a room.
“Get her out of here as soon as possible”, said Julia
“Where should I take her ?”, I asked
“To a hotel somewhere”, said Julia nervously, “Tell her it’s a set-up”.
“Who is she ?”, I asked innocently
“You’ll recognize her”, said Julia, “Now scoot upstairs”.
I walked quickly down the hallway. Coming out of a room, fully dressed in her fur coat, her black felt hat pulled down over her face so that few people could recognize her, was the lady who was the main assistant to the mayor.
“Please follow me. I was told that you were walking into a set-up”, I said quickly
She stopped in her tracks, turned around and looked at me.
“Were you the person I was supposed to meet ?”, she asked
“No. I was just told to get you out of here as soon as possible ”, I answered, surprised at my assurance.
“I …was planning on meeting someone in that room…and nobody showed up”, she stammered as she approached me.
One has to remember that Boston was a mob town and that the mayor or anyone associated with him was vulnerable to blackmail if found in a brothel.
“Do you work here ?”, she asked
“No ..I work for Alanis…I’m just visiting”, I answered
The woman was obviously quite scared and didn’t know what to do.
“Trust me. We have to leave this place and go to safer surroundings”, I suggested
“You look trustworthy…I’ll follow you”, the lady answered, relieved.
I grabbed my coat and we walked quickly out of the establishment. A few minutes later we were in a taxi heading to a hotel on the outskirts of town. I knew the address and she didn’t ask questions. We checked in and I found myself in a strange hotel room with an even stranger woman.
When she took off her expensive coat and felt hat, I finally saw more of her. I was right, she was the mayor’s assistant as I had seen her on posters and in a celebration at the factory. She was quite tall and very slim. She was dressed in a business suit which made her look older but she must have been mid-40s. Her hair was curly and hung down to her shoulders. She had a wide brow which made her look like one of the actresses I liked in the movies.
“Where do you work ?”, she asked as she lit a cigarette
“During the day I work at the factory…otherwise I get tricks around town”, I answered honestly “I don’t know Alanis but I know of her”, she said looking at me with a smile
“I’ll level with you”, she began, “I was supposed to meet a woman”.
“At the brothel ?”, I asked surprised
“I know..I know…It was so stupid of me”, she said as she covered her face with her hands
“You had seen pictures ?”, I asked
“How did you know ?”, she looked at me in shock
“It’s a common trick”, I said, “Now they know something about you”
“Nobody will find me here ?”, she asked nervously
“Nobody followed us”, I said reassuringly
“But what if someone walks into the room once we are together and takes pictures ?”, she said, but not very convincingly
“Then I lose my job, my other job, and the mayor has me shot”, I answered
She got up, took off her jacket, and started to unbutton her blouse.
“My name’s is Theresa. Get undressed”, she ordered, “I had my mind set on sex tonight and I’ll have it”.
I didn’t think that was her real name but who cared. I had already taken my shoes off. I quickly got out of my blouse which was the only garment covering my breasts. I slipped out of my skirt.
“No…keep your skirt on…but take off your panties”, she said, as she lay on the bed.
She was topless and she had also taken off her panties but kept her skirt on. I learned that they all had their preferences and to just go along with it.
She had medium-size breasts which were slightly sagging. I joined her on the bed, walking on my knees until I reached her. She opened her legs and lifted her skirt up only partially up her thighs.
“Suck me”, she said in a soft voice
I slipped my head between her thighs and under her skirt as she lay on the bed with her head resting on the pillow. Her skirt smelled of wet wool and my mouth was guided by the familiar smell of wet cunt. I tongued her labia and inserted my tongue in her love crack. She was very wet.
“I’m very wet”, she confirmed, as she moved and opened her legs even wider
She was shaved, which was uncommon. As I licked her, I remembered she had a reputation in lesbian circles but I had never had any confirmation of it. People said a lot of things that weren’t true. I flicked my tongue on her large erect clit and I heard her moan loudly. I could feel her hands on my head which made a large bump under her skirt.
“I wanna rub with you”, I heard her say
I pulled my head from under her skirt and sat on the bed with my own skirt lifted around my waist. She didn’t say anything but she gave me a wicked smile when she saw I was shaved.
“Let’s fuck”, Theresa said as she opened my legs with her hands
“Yeah..fuck me”, I cried, getting her even more excited
She wanted to fuck with our skirts on. It was a common fantasy and I enjoyed it also.
She settled her hips between my thighs, and we moved so that our cunts kissed making sure to keep our skirts bunched up around our waist. When she mounted me, the pile of material made it uncomfortable since it created a large bump between our tummies. She wanted us to keep our skirt on so much that she took the time to spread the material so that there was only a thin layer between us. She must have had hookers before since she didn’t even try to kiss me. Instead she put her face next to mine against the bed and kissed my neck, just like some men do.
My hard tits were not matching her sagging pair but she pushed the top of her chest against my globes and that turned me on. She was an expert at cunt rubbing and our clams were immediately kissing, crack against crack, lips against lips. I could feel our cunt juices flowing down my cunt to my ass. She kept saying “oh fuck” in my ear and I answered “fuck me hard” every time. Theresa had manoeuvered so that her clit had not touched mine directly but after a few minutes, I moved sideways a few inches and our female pricks touched. She howled and I screamed. I grabbed her small asscheeks with both hands and pulled her against me. She began to hump harder and harder, engorged clits slapping against each other, until we both came at the same time and with a common scream.
I continued playing with her ass while she was still on top of me. She nibbled on my earlobe.
“Fuck”, she whispered in my ear, “That was some fuck”.
“You like me Theresa ?”, I said without thinking
“Yes..you’re good”, she answered stretching her left arm over my tits.
“Tell Alanis when you want me and I’ll meet you anywhere you want. My name is Cathleen”, I said
“You will of course be discreet”, she said slowly as she pulled herself up and stared at me.
“Of course…I got you here didn’t I”, I answered not wanting to be intimidated.
“Yes you did and I’m grateful”’ she said giving me a genuine smile
We both got dressed and Theresa took a cab home. I hung around the lobby for a few minutes.
“I bet she didn’t pay you”, said the white-haired woman at the desk. I had seen her every time I had turned a trick in that hotel.
“You’re right. I forgot to ask”, I answered
“She must be a good fuck”, said the woman
“Let’s say it was worth it”, I said smiling.
To be continued
Gert
- 18.11.2022
- 12
- 0
