Prison Dolls Ch. 01

It looked like a perfect Vee between Allie's legs. The same Vee that you would expect to see on a woman.

"You saw me tuck. You are going to have to do the same. This might be a little uncomfortable at first but it should not be painful," Allie reached for Bobbie's groin and she stepped away.

"Bobbie. You have to learn to trust me. Put everything out of your mind and learn from me," Allie said sternly and Bobbie nodded reluctantly.

Allie used two fingers to tuck each testicle up into Bobbie's corresponding inguinal canals. It felt weird but not painful. Allie had Bobbie do it herself a few times until she was comfortable. Then she pulled Bobbie's penis and scrotum backwards between her legs.

"This will help keep your testicles tucked up in your inguinal canals. At this stage we can either use tucking tape or your underwear to keep everything in place. I'll show you both methods," Allie said quite clinically.

"Now, let's look at your wardrobe," Allie said gleefully.

Allie had approximated Bobbie's sizes based on prison records which weren't much help but they did have Robert Valentine's waist and chest measurements and importantly his shoe size which Allie was able to convert into a female size chart. She had guessed the rest by carefully but unobtrusively observing Robert on the wing.

"But first I need to get you into this," Allie said holding up what appeared to be a band of flesh-toned spandex.

She had Bobbie step into it and pulled it up so that the top of the cincher fitted just below Bobbie's ribcage and the top of her the hips. Bobbie now had an hourglass figure.

"You can ditch this in a few weeks when you lose the weight," Allie commented flippantly.

"Now comes the fun part," Allie grinned.

None of this had seemed fun to Bobbie. It was confusing and daunting but she went along with it because the alternative was not worth considering.

Allie laid out a selection of pantyhose, stockings, panties, brassieres, slips and lingerie.

"I want you to tuck and then sit down and put on these pantyhose," Allie held out a pair of fifteen denier sheer-to-the-waist pantyhose and Bobbie took them from her.

Robert had always had a thing for women wearing nylons and he often implored Mandy to wear them for him and to occasionally wear them for him during sex. Mandy thought it strange but if it kept her man happy she was happy to comply to appease him.

Robert would never admit this to anyone, but like a lot of men, he tried on his wife's pantyhose and panties once in while so putting the pantyhose on was not alien to Bobbie.

Bobbie sat on the bed and gathered one leg of the pantyhose to the toe and then she pointed her toe and slipped her foot inside. Gently pulling the smooth fabric up her leg, easing it carefully and slowly, making sure the fabric didn't pull or rip, she kept the hose leg centred and pulled it up until she reached her thigh. She did the same with other leg and then she stood up and pulled up the pantyhose so that the elastic at the top sat around her waist.

Bobbie had worn pantyhose a few times before but the feeling of these luxurious hose on her freshly shaved legs was amazing. She risked losing her tuck as her penis began to engorge but she remained stoic and pulled the gusset of the hose snug to keep her tuck tight. Putting on the full-cut black satin panties helped keep the tuck in place too but she shivered with delight as the sleek lacy garment slid along her gossamer pantyhose. Bobbie felt a single droplet of precum leak from the eye of her cock.

"I think you did that little too well and liked it a little too much. Have you been hiding something from me Bobbie?" Allie sniggered and gave Bobbie a knowing wink.

Bobbie blushed but said nothing.

Allie helped her put on a brassiere that matched her panties and showed her how to adjust it and placed two 'chicken-fillet' breast prosthesis in the cups to give them some shape.

"I'll let you play with the slips, petticoats and lingerie later. For now I want you dressed and walking so the lessons can continue," Allie said handing Bobbie a white satin blouse.

"Why would I want to play with the slips and lingerie and when are we breaking for dinner?" Bobbie was becoming agitated again.

"You won't be eating dinner again for a while. You may have a light breakfast in the morning and a single lean quinine before you go to bed until you lose that belly. Also, you will soon discover that your eating habits will be dictated by things more important than hunger," Allie snapped.

"Now put that blouse on and keep it away from your makeup and button it carefully because it buttons on the other side to a man's shirt

The next hour or so was taken up with Bobbie trying on shoes, skirts, blouses and dresses, discarding those that didn't fit and keeping those that did. Allie paired skirts with blouses and shoes with ensembles. When they had finished Bobbie and Allie had a small wardrobe collection laid out on the bed.

"This will do for now. You will need to add to your wardrobe anyway when you lose that gut and your size changes," she tapped Bobbie in the stomach playfully.

"Tomorrow will be fingernails, followed by poise, walking in heels, mannerisms and speech. Get undressed, take off your makeup and wig and take the clothes, wigs shoes and this makeup case with you. Go back to your room and practice your makeup skills and tucking. If you're up to it, try walking in those heels for a while. See you tomorrow," Allie dismissed Bobbie.

When Robert went back to his room Allie made her way to Seg and brought Tig up to speed. It looked like Bobbie was the perfect candidate to take Allie's place. Allie had sex with a couple of the Siceresso men as usual and returned back to her dorm and had a good night's sleep.

Robert lay on his back unable to sleep, staring at the crack in the ceiling snaking its way towards the light fitting wondering why his life had been turned upside down. All he ever wanted was to just do his time and then go home and pick up the pieces of his life.

To be continued