Betty Pearl's Sissy Stories 20.1
Sissy Story Archives (older stories) => 2011-2018 Sissy Stories => Topic started by: Alana on February 04, 2017, 02:07:58 PM
-
Little Miss Retro
Stolen by Alana
Originally written by Mary Beth Sanford
Secretary day was a major event at Hark Grove Inc. Ms. Grove herself had started out as a secretary decades past, and this year the costume party was themed around those unsung heroines that are the base of most companies. Alan mentioned that, in passing, to his landlady who, years past, was herself a secretary.
Alan had asked if his landlady Ms. Baker might have something "a bit retro" for him to dress up in? She did, she noted, or thought she did. There was one dress in particular that had fond memories for her, and that was what she was thinking about when Alan mentioned it.
Back in those days, she noted as they stood out front, promising to look in her attic for something suitable for Alan to wear, girls wore dresses all the time. Colorful dresses were some of Ms. Baker's favorites. Especially in the spring, and she was sure there was an old trunk of things she hadn't had the heart to toss out.
It was a tight, colorful dress that cost her a fortune in 1972. She'd kept it because it was the first "work" dress she wore on her first day as a secretary right out of school. She had even purchased her lingerie new for that day and those too, as it happens, were in that trunk.
Alan, for obvious reasons, wasn't keen on wearing those particular items and said no until his landlady insisted, playfully, that it was all or nothing. He agreed, and his landlady promised also to get up early enough to help him with his make-up and hair. She also provided her bath salts for his bubble bath for that morning.
His new black patent pumps and thigh high silk stockings were the only two items not going back to those days. His panties, or rather the panties his landlady offered, were 100% nylon briefs with a double layer of nylon, which was before the cotton lining was popular. As was his garter for his silk stockings.
Alan's slip, as his landlady put it, was a full slip of nylon in pink with a lace bodice that he added after his satin bra. A small set of foam enhancements were put into his bra after she snapped it closed from the back. The purse was loaded with his "basics" including the eye liner, blush, and lipstick she used on him that morning. The dress was last after she set his hair in place.
Alan felt extremely feminine as the slip and dress moved sensuously over his legs and panties. A point he didn't comment on, other than his smile, when his landlady asked how it all felt. She fussed a bit more, handed him her sun glasses, and bid him a nice day as he made his way to his car.
Ms. Grove was pleasantly surprised at the pretty young man as he entered, as were the five secretaries that worked with Alan. The other guys, not nearly as adept at being girls that morning, nor as pretty, gave Alan their votes. Alan won hands down, and that afternoon, at Ms. Grove's insistence, sat pretending to take dictation for the photo she wanted.
-
Alan adjusted his glasses, and before the photographer could take the picture his steno pad slipped off his lap and onto the floor. He reached for it.
-
He smiled at Ms. Grove, who was enjoying the site of him reaching down in his sexy dress.
-
She giggled as he struggled to reach it. He was wearing a tight dress and an even tighter panty girdle, and it was with a certain degree of awkwardness and discomfort that he finally managed to retrieve the pad.
-
As he picked it up, he could sense Ms. Grove's appreciative gaze, taking in his lovely legs in nylons, his figure, his eyes, his lips. He returned her erotic glance.
-
Finally the photographer got the photo of Alan taking dictation.
-
He returned to Ms. Grove's office shortly after the office closed, and again, at her insistence, sat down to take a memo.
-
She began to dictate:
"Dear Alan,
I think you make a delightfully feminine young woman and believe you'll go far in this company, given your willingness to honor women in this way. I'd like to discuss that very thing at my place over a drink and, perhaps, dinner. In fact, I have a very pretty baby doll set that would look lovely on you while we get to know each other better.
Sign that yours truly, Helen Grove."
-
Ms. Grove said this as she moved a hand gently over Alan's silken knee. Those last words he wrote on the pad were not nearly as legible as the ones in the beginning, and Alan nodded a second before her kiss.
That following morning, driving back to his place in amazement over the night before, he mused over his new title as Little Miss Retro, given to him just before Helen slipped the baby doll top over his head. As it happens, he actually didn't wear the panties to that set for more than a few minutes.
-
Post Script:
Alan met his landlady on his way into his apartment, and wasn't sure how to explain why he was still dressed that following day. His reluctance to give up what he had on was his only thought in those minutes.
At least, he thought that until his landlady mentioned that she was fixing breakfast, and wouldn't mind him joining her if he didn't mind staying dressed for a bit longer. Alan, of course, didn't mind at all, and discovered when he entered her place that she'd been going through a number of things she had from back then.
She offered him a shower while she did the bacon, and a quilted pink robe to wear over his nightgown if he didn't mind. She had said that last part while moving in close enough to offer him a kiss before he could answer no.
He was drying himself off while looking at the outfit he was going to put on, wondering over that night's and this day's events. His smile formed, once again, as he powdered himself before gathering the light pink nightgown into his hands.
The Seventies and those ladies growing up in those times were certainly different from the girls he knew of now. He was glad of that, he mused, as the nightgown fell to his knees.
THE END
This story was written by Mary Beth Sanford, based on a dress of mine. It was gone from online until now, and I am restoring it from a printed copy. I was unable to contact Mary Beth Sanford to get permission.