March 2nd 1954,
My older sister Betsy, has just been convicted of bank robbery for the third time, and she's only 22, the first time she was underage, so she got a probationary term, her boyfriend Jack, took the blame, while he was in prison, my sister visited him most weekends.
The second time was when she turned 20, I'm pretty sure Jack put her up to it, of course she went to a women's prison, they gave her a 5 yr sentence, she got out in 2 yrs for good behaviour, what a joke, within 6 months she was at it again, that's where we find ourselves today.
The prisons in the Fifties weren't like the prisons of today, especially for women, they were allowed to wear their own clothes, they had a spa and salon for the girls to learn about health and beauty while they trained for their release
Betsy has been in jail for 2 yrs,
Me - ''Hi Betsy, how you doing?'' I asked
Betsy - ''I'm doing ok, how are you?''
Me - ''Janet and I have broken up,''
Betsy - ''Oh no what happened?''
Me - ''She said I'm boring, and plain,''
Betsy went quiet,
Me - ''Betsy? do you think I'm boring and plain?''
Betsy - "Well you do always wear the same clothes and your hair is a bit lame."
Me - "Gee thanks for nothing, at least I'm not in jail. I'm sorry Betsy that was uncalled for."
Betsy - "See what I mean you cant even stand up for yourself without saying sorry all the time, you need to toughen up, are you still a virgin?"
Me - "Betsy, please you know Ive tried but nothing seems to work for me."
Betsy - "Oh Mike, you've only ever had one girlfriend, no wonder she said your boring and plain. You have to do something to change how you look, grow a beard, let your hair grow, do something different". She was right I had fallen into a rut, but that was all going to change.
Six months later,
Betsy - "Wow Bro, your hair is almost as long as mine and you look great, you been working out?"
Me - "Ok Sis, thanks for the compliment on the hair, but I'm still working on the bod, still feel skinny"
Betsy - "I think you may be ready"
Me - "Ready? Ready for what?"
Betsy - "Not yet, Drink your tea"
I started getting groggy within minutes of drinking the tea, she had drugged me, luckily I was sat in a chair or I would have fallen face first, I heard Betsy scream, then saw her fall to the floor, I only have a vague memory of what happened next, the guards rushed in and took us both to the infirmary, the guards left and I remember seeing Betsy get off the stretcher and walk over to the bed I was on,
Betsy - "Get him stripped we don't have much time" the two "nurses" wasted no time, I was stripped naked, they shaved me head to toe, beard, arms, legs, everything, The "nurses" started work on my face, powder, eyebrows plucked into a feminine arch, my eyelashes became curled and lengthened with mascara, next was eyeshadow and black eyeliner traced my eyelids, lastly bright red lipstick was applied to my lips.
I tried to move, or at least shout to get someone's attention, but the drug, whatever it was, was working better than even Betsy had hoped for, they sat me up, Betsy must have been planning this for weeks, a curtain was pulled back and revealed all sorts of women's underthings, a full length girdle was pulled up my legs, and the girls looped the straps over my arms and a large zip was pulled up the back, it was tight as it took two of the girls to get the damn zip up, I felt my stomach being pulled in giving me an hour glass shape, Betsy had sewn fake boobs into the girdle, next was the nude stockings, Betsy looked me in the eye as she rolled the stockings up my now smooth legs,and said
"Don't worry the guards will find out what has happened, but by that time I will be well away from here, Jack is waiting for me outside."
While Betsy was gluing a fake beard on her face and making her eyebrows look more manly it was then I realised she was going to leave me here while she sneaked out as me, 15 minutes later she was dressed in my clothes, she came over to help the other girls get me into her over the top feminine dress, it was bright red with white polka dots, three petticoats later a large white scarf was tied around my neck covering my adams apple, white gloves and two white cuffs on the sleeves, a large black belt was tightened around my now 26" waist, I was shocked to see Betsy take off a black curly wig to reveal straight hair just like mine, she placed the wig on my head and asked one of the other girls, "How long will the glue take to wear off?"
"Only a few hours, just enough for you to get away with Jack" said the taller of the two as she winked at the other girl.
The plan worked perfectly, the real Betsy dressed as me strolled out of the prison after getting the okay from the nurses for her to leave as me, little attention was given to her leaving, they had what they thought was their "Betsy" in the infirmary, until the nurses said it was ok for her to return to her cell. A couple of hours later the guards came to see how "Betsy" was doing and asked if "she" could return to her cell?
Finally I was to be released from this nightmare, the nurses would allow me to go back to my cell and then the guards would figure out what had happened, and the hunt would be on for my sister, I lay there waiting for them to notice I wasn't Betsy, I was shocked when the nurses told the guards "Betsy" needs to stay in the infirmary overnight," as the guards left the infirmary I saw a wry smile come over both girls, one of them pulled up my dress and tucked it under the belt around my waist, the second girl pulled down the panties Betsy had put on me, It didn't take long for Mr. Johnson to make an entrance, the first girl straddled me and began pleasuring herself, I exploded, she climbed off me only for other girl to take her place, it didn't take the second girl long before she had him to attention again.
Taller girl - "I'm sorry Mike, but you may have to stay here longer than Betsy had planned, there are a lot of girls in here that would appreciate male companionship, and look on the bright side, your not a virgin anymore, get Mike some more tea, "