"I knew a very much older woman, who I helped around her yard, who would stand behind me, press up against my back, slide her hands under my shirt up my chest, and touch my nipples until she undid my belt and pants to check my hardness. Satisfied with the result, she would go back to the nipples. And very gently bump against my ass with her pelvis. She knew what she wanted to do, if I wasn't otherwise committed. If it wasn't crossing a major line, for her generation. And she knew that I couldn't help but let her. But not a word was said of this secret."
"The first time was hard enough, when his girlfriend’s promise of a “surprise birthday treat†turned out to be a game of dress-up and hand job in front of the bedroom mirror. He wasn’t sure why he agreed to wear the maid’s uniform other than a drunken lapse of inhibition and a misplaced faith in her promises that he would like it. She pleasured him relentlessly, on and on till fatigue and frustration made him almost delirious.
She hushed him as he came, wiping away his mess and holding him till drowsiness overtook him, sending him to sleep still in costume.
They did not speak of it after he left for work the next morning, but the uniform was on her bed again that evening when she led him to her bedroom.
He resisted. She persisted, kissing and fondling as she talked about the need to broaden his mind, to accept her sense of adventure, to entrust her with his pleasure. She talked about how lucky he was and how other men would be grateful to receive such attention. She stripped him and wore him down with descriptions of how she wanted to reward her open-minded lover.
And so the routine began. While she was content for him to wear what he wished when going down on her, his orgasms were conditional on being dressed to her specifications. When the maid costume was in the wash he was presented with other exaggerated fancy dress. She stroked him to surrender in a ballet dress, a peignoir, a naughty schoolgirl costume and even a corseted wedding gown. It wasn’t a question of liking it, but a realisation that he deserved it."
"It was just a test, his girlfriend explained. Her underwear had gone missing and she wanted to believe him when he denied being a “panty thiefâ€. If he could prove that he didn’t find it arousing then she could trust him again."
"The overseas work placement was pleasant and rewarding for the first two weeks while his friends were there, but no sooner had he agreed to stay on than his supervisor began implementing new rules. Punishments for infractions were bad enough when they merely involved him wearing a dunce’s hat, but with every fresh admonishment came a new garment, each more humiliating than the last.
By the end of the third week his own clothing was banished in favour of silky underwear and a minidress. “If you act like bimbo, you dress like bimbo,†the supervisor said during one of her inspections. “You have much to learn, but don’t worry. I will teach you.â€"
"She was as good as her word. At first she guarded him jealously, but in time she began to share him with other curious women wanting a discreet strap-on appointment. Most were one-offs, content with one of the half-hour sessions, but some returned for a “boyfriend experienceâ€. She coached him on how to handle the regulars: to gaze longingly as they arrived and departed, to sigh with confected ecstasy as they pegged him, to pretend that they were the one thing that made his life worthwhile."
"She always got her way. From their first meeting, when she fogged him with vodka and escorted him home, she was able to cajole and fondle him into unexpected intimacy.
Her favourite habit was to broaden his mind, as she called it, sitting with him as they browsed through pornographic images and videos, seeking inspiration for femdom fantasies that they might reenact. If he resisted an idea she would try again and again, wearing him down with affection and alcohol till it became easier just to do as she asked.
The feminisation fantasy took the longest to achieve, but after a lively lunch party he found himself as her last remaining guest, his senses buzzing a little while she undressed him in the sitting room among the wine glasses and coffee cups. She took her time, stripping him totally before bidding him to close his eyes while she hid his clothes and brought in the frilly dress.
It was the third occasion he had seen it, but this time she showed him how soft the fabric felt against his skin as she struck bargains with him.
He would only wear it as a one-off, no one would ever see him in it, he only needed to try the jewellery to see how it looked.
The compromises became more one-sided as his embarrassment increased. She agreed to finger him gently, to use only the smaller dildo, not to demean him verbally when she strapped it on, not to tell anyone the feminine name she had given him, never to share the photographs.
“They’ll be our secret,†she said as the last of his dignity faded. “For as long as we’re together.â€
She smiled as she leaned into him. “In sickness and in health. For as long as we both shall live. Till death do us part.â€"