The Shopping Trip Series

By Roberta Ashford

Published on Apr 19, 2013

Transgender

The Shopping trip Pt.2

By Roberta

Arriving at the shopping centre Roberta parked her car and walked into the nearest entrance, finding herself in the women's dept of a large chain. Roberta started looking through the skirts and dresses, picking a number of items she walked over to the changing rooms. As she walked in she was surprised to find that the room had one open plan area with a number of benches dotted around the walls and a number of cubicles at one end.

Looking around Roberta spotted a very striking woman and walking over to the nearest bench to her, hung her items on the hooks provided. As Roberta undressed she noticed the woman sneaking furtive glances at her and wondered. Roberta quickly glanced around the room and noted that only a couple of teenage girls remained in the open area.

Taking a chance Roberta reached out and stroked the woman's arm allowing her fingers to brush against her bra, and commented on her beautiful lingerie, as she did so the woman let out a low mew and swayed slightly. Seizing the opportunity Roberta grabbed the woman and pushed her into one of the cubicles leaving their clothes behind. Expecting the woman to cry out in alarm Roberta was quite surprised when the woman stood facing the wall and said in a submissive whisper "please use me as you wish! Mistress". Roberta stood behind the woman and ran her hands over the woman's stockings, slowly bringing her hands up to the woman's ass cheeks. Sliding her hands round the front of her French knickers Roberta found them wet to the touch. "MMM. You are a horny little minx, aren't you" Roberta whispered and with that slipped two fingers straight into the woman's dripping pussy. Roberta slowly masturbated the woman as she stood there and could feel more than one area growing moist.

Bend over and touch the wall Roberta commanded, and was pleased when the woman assumed the angled position without a murmur, her ass sticking out somewhat. Roberta stood behind her and with one swift movement whipped off the woman's knickers, balling them up she stuffed them into the woman's mouth. "We can't have you crying out can we" whispered Roberta

Roberta slipped her hand up the leg of her knickers and with one quick movement released her throbbing cock and deftly slid it straight into the woman's dripping slit. The look of shock on the woman's face as Roberta pounded her 7 inch clit up the woman's pussy remained for only a couple of minutes, and Roberta soon realised that she had nothing to fear as she felt the woman bucking against her. Roberta fucked her firmly and soon felt the unmistakeable spasms from the woman's cunt as she started to orgasm. As she fucked her through her orgasm, Roberta became aware that her legs were getting very wet. Looking in the mirror Roberta could see that the woman was gushing a torrent of juice down both her and Roberta's legs and Roberta soon realised this woman was a squirter.

Roberta felt the surge in her balls building up as they slapped against the wet sticky inner thighs of the woman, pumping hard into her Roberta knew she had reached the point of no return and felt her cum spewed into the woman's pussy causing her to gasp with pleasure. Again and again Roberta felt her cock spasm as another thick wad of semen shot into the woman, finally Roberta held her as her cock started to soften and as it slipped out of the woman a mixture of cum and the woman's juices trickled out and ran down her legs.

Roberta reach down and ran her fingers through the mixture, collecting some in her finger tips she raised them and licked them clean. Wow did she taste good

Roberta reached round and took the panties from the woman's mouth. Shaking them out and giving them back to her, Roberta instructed her to clean herself up. As the woman wiped her legs and pussy Roberta slipped her now limp cockette back inside her panties and walked over to her clothes, as she dressed, the woman walked over and taking Roberta's wrist she slipped the panties into her hand saying "Thank You". Roberta dropped the panties into her bag with a rye smile, and walked out leaving the semi naked woman standing there. As she passed the two teenage girls, both of whom looked dumb struck she leaned over handed each of them a card and said "Call me". As the girls both giggled sexily Roberta turned and walked out.

Roberta wandered around the various stores buying the usual bits and pieces; she picked up a new lipstick and some mascara from the Dior counter, a pair of gold earrings with matching necklace and some new silk stockings. Next Roberta walked into La Boudoir, the most exclusive Lingerie shop around and was immediately met by the manageress whom hugged Roberta in a friendly manner. "Madam Roberta, how nice to see you again, how are you" the manageress enquired. They sat talking over a cup of coffee discussing the latest fashions and trends, after they had finished their coffee the manageress showed Roberta a new range of lingerie that had just arrived from Paris. They discussed the various aspects of the underwear, and then Roberta was offered a fitting as they had her size in stock.

Roberta followed the manageress into the fitting room and started to undress, once down to her underwear Roberta removed her girdle and stockings turned and allowed the manageress access to undo the clasp on her bra, as the garment released it fell away revealing her firm breasts and pert nipples. Next the woman bent down and slipped her fingers into the elastic of her French cut panties and slid them down her legs, allowing Roberta to lift first on leg then the other out of the briefs.

Roberta turned round to face the woman whom was still crouched down and smiled at her, "I see the cache is working, are they comfortable to wear" the manageress asked. "Yes, very" replied Roberta "you made them very well". The manageress helped Roberta try on various sizes and styles till they had been exhausted, finally agreeing on what she wanted.

Roberta dressed as the manageress went away to pack the items, and when she returned to the counter they were neatly wrapped, boxed and bagged ready for her. "I have added them to your account Madam Roberta the assistant called out as the manageress and Roberta walked to the door, Thank You Roberta called back. As the manageress opened the door for her, Roberta leaned forward and kissed the woman goodbye in a way that you don't kiss your mother. Breaking away, the manageress looking a little flushed said "see you next month" and with that watched Roberta walk away swinging her bags as her heals clicked on the tiled floor.

Roberta walked through the shopping arcade popping into a few shops, picking up a number of items she required. As she reached the shoe store, Roberta saw the most divine pair of black 4" heals. Each shoe was exquisitely finished with a wide ankle strap closed with a small silver padlock. Without even looking at the price Roberta walked into the shop and up to the assistant waiting by the counter.

"I'd like to try on a pair of the shoes you have in the window" she said with an air of dominance "the ones with the lockable ankle straps" she added. "What size, madam" the assistant asked. "Nine", Roberta replied. The assistant looked quizzically at Roberta then turned and walked off into the store room. After a few minutes the he returned carrying 2 boxes and guided Roberta to an empty seated area.

With Roberta seated the assistant sat in front of her and removed her shoe, he then opened the first box and lifted out the shoe carefully not to mark the black patent leather, he removed the small silver lock and undid the buckle. The assistant lifted Roberta's leg sliding his hand down her calf and slipped the shoe onto her foot; he then buckled the ankle strap and slipped on the lock with a distinct CLICK. Roberta lifted her leg to get a better view of the shoe, and as she did so she caught sight of the assistant furtively looking up her skirt. "I'd like to try the other shoe on" she stated and dropped her foot to the floor.

Roberta lifted her foot to allow the assistant to slip the shoe on, and as he did so he again looked up her skirt. Roberta waited until he had completed doing up the shoe, then lifted her leg up, turning her ankle this way and that, and ensuring that the assistant had an un-inhibited view of her stockings and panties, she asked him for his opinion and offered her foot to him.

The assistant held her ankle with one hand while offering his opinion, as he spoke he stroked his hand down the back of Roberta's other leg, squeezing her calf and gently running a digit over her fine stockings. Roberta lifted her foot from the man's hand and placed it onto his crotch, leaning forward and with a seductive tone whispered "do you like looking up my skirt sissy". The man, looking a little uncomfortable stammered his reply "Yes madam". Roberta pushed the heal of her shoe firmly into his crotch and smiled, "what's in the other box" she asked. The assistant reached round and opened the box, and removed the tissue paper covering a beautiful pair of ankle boots with lockable straps, "I thought you may wish to try these as well" he replied.

Roberta eyed the boots and turned to the assistant "that was rather presumptuous of you; maybe I should teach you a lesson". Roberta pushed her shoe harder into the man's crotch and watched him wince. She noticed though, he had a faint smile on his lips and a she continued the pressure he let out an audible groan...

Roberta intimated for the assistant to remove the shoes and motioned her wish to try on the boots, the assistant nodded and proceeded to first remove one shoe then the other, taking more time than needed and caressing each foot, ankle and calf. Roberta looked at him with a bemused expression as he started to insert the laces into the ankle boot, as he did so she rubbed her stocking covered toes over the front of his trousers. Along with the feeling of his firm manhood Roberta felt the unmistakable bumps on the front of his thighs of two suspender clasps. Roberta looked at the man quizzically as he finished lacing the boot, and notice he had reddened somewhat. Roberta raised her foot to allow the boot to be slipped on, as the assistant started tightening the laces Roberta asked him directly "what else are you wearing sissy".

The assistant raised his head and said in a hushed tone "Panties Madam". "What else" Roberta retorted. "Camisole and stockings". "Mmmm you little sissy, I think I should play with you" and with that Roberta pushed her ankle boot into his crotch and started firmly rubbing her foot back and forth. After a short time Roberta could feel his cock swelling and pushing against his pants.

While Roberta continued her rubbing she leaned forward and pinched the nipples poking through the assistant's shirt. Twisting them harshly Roberta watched the sissy winch while at the same time smile with enjoyment. Suddenly the assistant stiffened, his eyes glazing over and a low audible groan escaped from his lips.

Roberta knew immediately what had occurred and speaking in a demeaning tone said "Who gave you permission to CUM, slut". Removing her foot Roberta could see a very large wet patch on the front of the assistant's trousers. "That will teach you sissy ".

Roberta had the assistant fit the second boot, and as she walked up and down feeling the way the boots encased her feet and ankles and the pull on her calf muscles she looked at the sissy boy and said "I'll take both pairs and you can wrap them for your Mistress".

Roberta sat while the assistant removed the boots, and as he carefully replaced them in the box she slipped her shoes back on. "Follow me" she commanded, and with that she walked over to the counter to pay for the items. The assistant hurried after her holding the boxes in front of his stained pants. Roberta waited while the assistant added up the items and gave her the total, as she passed her credit card over she also gave the assistant her card and informed him to deliver the purchased item to the address printed on it at 8.00pm that evening and to come suitably attired. The assistant returned Roberta's credit card and receipt with the words "Thank You Mistress"

To be continued...

Next: Chapter 3: The Shopping Trip 3


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