"Terry my angel, I'm thrilled that you and your stepmother agreed to meet up with me like this. You can't imagine how pleased I am with you."
A warm frisson ran down Terry's back, even though they'd long since stopped going together. He felt all the better since Amelia was praising him in front of Nancy. His stepmother looked at him, lifted her eyebrows and actually smiled at him. "Okay," he said, with his elbow on the table and his chin on his fist, "but hey, what's it all about?"
"This is what it's all about," went on Amelia, moving her patisserie to one side, the better to focus on Terry Vernon. "You know I'm getting married - I'm sorry Terry but - well I don't want there to be any bad vibes between us, honey, not with me being such a close friend with Roxy."
Terry froze at the mention of his stepsister, but yes, her and Amelia were like twin sisters.
"And she's going to be my bridesmaid, Roxy and my own sister Phoebe. I'm over the moon that they've both agreed to play such a major part in my wedding." She paused, reached her hand across the table and took Terry's fist from his chin - so that she could draw it closer to her and hold his hand on the table. He could hardly believe she did it, but it was nice. "The thing is, darling, I want you to play a major part too."
Terry's head started zinging. Why was Amelia making such a fuss of him when they weren't going any more? When she was even getting married! He suddenly felt the awful mistake he had made in passing up such a gorgeously cute blond sweetheart. She wanted to make him close again, and - well - he wanted to do anything for her.
"Well sure, Hugs." Huh, 'Hugs'. It slipped out, his special name for her when they were sweethearts. "You name it, I'll lend a hand. DEF-initely no hard feelings between you and me, girl. Like we agreed when we split up."
He found his hand being held in both of Amelia's and squeezed so tight. "I loved it when you call me Hugs," she cried and grinned at him like a perfect pussy-cat. "But now you've made me feel so happy, and Jack will be glad too, hon. He'll think you're a straight-up guy. So your sister will be my bridesmaid and you will be my pageboy. I feel like I've won the danged lottery!"
Terry was still in a half-drunk stupor as Nancy drove him home from their special fix-up at the Diamond Grill. "Well congratulations on making everything work out for the best between both our families," she said. "I'm impressed. We'll talk more about it when she tells us what role she wants you to do."
Nancy Vernon was well practised at thinking one thing and looking like she felt quite another. She sniggered to herself as her hated stepson turned up his music, and recalled the discussion she and Roxy had been in with Amelia. Her sister Phoebe was there too, hating Terry Vernon to his guts for the pangs of unhappiness he had brought on her beloved sister when he walked out on her. They'd pored over a magazine called "Female Revenge" and squealed with laughter at their little plan. There'd have been no "Sure Hugs" from him if he'd known any of that. He'd have told Amelia to F-Off like now!
It was the following day that Nancy spoke to her stepson again, still giving him the smiling stepmother treatment. "Amelia was talking to me on the phone, Terry," she said, "about the wedding plans. So her sister Phoebe and your stepsister Roxy will be her bridesmaids, but instead of pageboys she wants dressboys. You'll be superb."
"Er, what does that mean?"
"She calls it a dressboy: it's what the main men do at weddings these days. You'll be ever so smart, Terry, and hey, you are NOT to steal the show!"
As the wedding date came nearer Terry Vernon suffered a maelstrom of mixed feelings: made up that Amelia Winchester was counting on him to make her big day really happy, while a niggle of worry surrounded the whole thing: this 'dress' boy business. But if lots of guys did it, what the hell, he'd be okay. As the day itself came he was to get dressed in the hotel venue itself where the wedding would take place, and Nancy told him she had everything under control. As she led him into the room set aside for getting him ready a call came through from Amelia, who was apparently on her way in the car with her bridesmaids.
"Hon," she asked, sounding very serious, "you don't mind me getting married, do you? I know you want me to be happy."
"Course I do," came his reply without him being able to stop it. There was a heavy lump in his throat.
"Oh thank you, you wonderful man! I am so looking forward to seeing you." It was the signal for Nancy to get him ready, starting with taking everything off and starting from naked.
To begin with she put him into a white suspender belt, nicely decorated with lacy embroidery and with four delicate garters hanging, two to each leg, looking for all the world like bridal underwear. Then she rolled a pair of gossamer nylons up his legs and clipped them up with tightly stretched suspenders. Her stepson winced at it, but could tell himself that they wouldn't be seen under his pants.
Next came a white satin, full cut pair of panties, trimmed round each leg with an inch of white lace. A hot shock of fright swept the dressboy over the top of his scalp. Oh my God, he told himself, I'm erecting. He hoped Nancy wouldn't see as she got the next item ready for him. But she did.
"Hmm, so that's the way it is with women's underwear is it?" she observed as she let drop a long cluster of lacy, silky lingerie and opened the top of it in her fingers. "Step in for me, Terry. If you like women's panties, you're going to love these."
It was a full length pair of frilly leggings, which she pulled up all the way until they covered his white panties. Nancy took a moment out of his dressing to stroke his pointed panty front, showing him her ironic amusement as she did so with a curl on her smiling lips. We haven't finished this most important area yet," she said, with a chuckle, and over his feet she threaded another pair of satin panties, this time much wider in the leg: a pair of French knickers, with two more inches of white lace. As they slid sweetly up his leg frills his cock was telling him what he daren't admit to himself: he was loving this pretty feminine stuff, and his stepmother knew it.
Next came a petticoat flaring from the shoulders. It swept round him in layers of soft, white organza with an added frill round the hem edged with excruciatingly feminine lace. He decided his best plan was to keep quiet and hide his arousal. Oh my God, he couldn't believe the dress. Yes, he thought: he may be a dressboy - in name - but he was dressed as a girl, and Amelia would see that he was. In fact the idea sprang into his mind that if this was her wedding, and he was 'her dressboy', she must have decided what he would wear as his uniform!
The dress swished and sizzled round him as she dropped it over his head and pulled it down his petticoat. It slid so smoothly, with full satin lining, and was all hot pink satin with white lacy frills. It had a lacy collar which cupped his chin and the back of his hair, fastening at the back of his neck as far as his shoulder blades. Then there were pink high heeled shoes to go with it, a ribboned hair band, a little purse and a Lolita parasol for him to carry.
Just moments before going into the chapel Nancy turned him with his back to her, told him to put his hands in, and pulled onto the front of his dress a women's brassiere. It was filled out with all-in breast forms, in white satin to match his panties, but it was ridiculously big with massive sized cups. If he felt frightened before, now he was close to collapse.
"Don't say we have to undo my dress, my petticoat - we'll never do it in time!" he whimpered.
"No. We don't," declared his stepmother, busy behind him. "It has to go over - that's the way you're meant to have it." There was a sort of snapping sound behind him. "There we are," she said: "let me click the rest of these clasping locks through the interlocking hooks - two, three, four." The key was on a necklace round her neck, which she slotted down between her breasts. "That won't be coming out until MUCH later this evening." She turned him so that he faced the mirror and looked over his shoulder to make sure he was ready. "It's time for your grand entry, Terry my dressboy. Time to meet everyone at the wedding."
She led him by the hand, in a very matter of fact way, opened the door, and swept him through on his clicking high heels. In front of him, open mouthed and very wide-eyed, were the bride and her bridesmaids, and behind them, the full chapel of wedding guests. Amelia was ready to walk down the aisle to where Jack Cole was awaiting his bride and her party.
Click! - Snap! The bewildered male found himself cuffed by the wrists with the sweetest little pair of hand-cuffs between Phoebe and Roxy, the two of them wearing figure hugging dresses in colours to match the 'dressboy'. With laughter on all sides, they began their slow, very public walk down the aisle with Terry holding his bouquet in one hand and his pink parasol open and over his shoulder in the other, with tears streaming down his cheeks.
The roaring laugh from Jack Cole could be heard all the way from the altar, while the whole congregation split their sides with roars of amusement. It lasted every step of the way until Terry and his bridesmaid escorts stood behind Amelia as she calmed her giggles enough to get married. The girls who flanked him tittered the whole way through, hugging their dressboy's arms in both hands - or were they hanging on to him to prevent any escape?
As for poor Terry he had lost all control. He stood pressing his knees together in their lacy frills. Was he wetting himself or was he spurting his newfound pleasure inside his exciting pairs of panties, so there was no saying what mixture was making his legs warm and wet or what was in the puddle that grew rapidly on the floor between his heels.
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