He hadn't made any real effort to object this morning and part of her plan was to see his level of compliance and submission. She had checked when she came into the room before she woke him up that he had obeyed her and kept the gag in. If he had any problems with her overnight orders he would have rebelled, taken it out and not continued to obey her directives to leave the butt plug in. But he stayed quiet and let her get herself off this morning. He didn't even complain about the chastity or her rules for today.
They had played with mild bondage in their relationship over the last few years and more so once they moved in together. They had taken turns in being dominant or submissive with some roleplaying. Now that she thought back it seemed that she had been the mistress more often than not the last few times. She was annoyed that he hadn't discussed cross dressing with her and that certainly needed to be talked out. She needed to find out the extent of his dressing up as a woman. Was he a transvestite?
She moved off his chest, took his restricted penis inside the pink metal sleeve and had a close look at it. Pulling at the tube and the ring retaining his balls, it certainly seemed to be secure. She had no experience with chastity and he very little and only over the last few days since Craig's penthouse party.
His balls hung below the tube and there was only a small gap between the ring and the end of the tube, no way to squeeze his testes out through that gap. His scrotum was clamped at the top without being pinched. There appeared to be a some sort of a narrowing section around the base of his penis that fastened into the locking mechanism at the top. He didn't appear to be in pain wearing it. He was erecting inside it as the end of his penis could be seen pressing against the end. It was a high quality, well made device that fitted him well and that there was no escape from. How did he get it? Custom made to measure perhaps? But then again she hadn't yet given him any opportunity to speak or ask to be released. She was absolutely enjoying his compliance. Her plan seemed to be working so far. How far could she take it? How far would she let him? She made a mental note to do some research today at work. Seeing him flushed, obedient and remaining silent she was getting aroused again. She definitely still loved him she thought and wanted to get married. She was ecstatic this morning but tried not to let it show to him.
Brad grimaced in discomfort as she pulled and played with his locked up cock and balls. He had certainly seemed to be submissive over the last few days. Otherwise why would he have stolen the chastity and butt plug from the party and bought the clothing, bondage gear and hair removal device yesterday?
He was extremely aroused playing with everything even before Erin arrived home last evening and after being caught was still feeling submissive, obedient and aroused. Having been in chastity for not even 12 hours he was aching for release. But Erin had the key and after being caught in such a compromising position when she came home he wanted to ensure her belief that he would do everything she asked. Would she really blackmail him? Unlikely but... He couldn't even imagine the epic disaster that would happen to his life if any of the pictures she took last night got out. Even thinking about any impending doom and humiliation, notched up his arousal even more. He was anticipating being dressed up after training and being even more feminine this time. He imagined it all, smooth & hairless, being in stockings, garter, panties, chastity, corset, bra and wearing makeup. His locked up cock tried fruitlessly to expand.
Erin looked up from the cage and saw his face bright red and sweating. Humiliation, arousal, frustration - all of them? He was lying on the bed taking it all. She couldn't wait for tonight and today at work would be a drag.
The sun was now up and light was leaking around the edges of the curtains in this guest room, brightening the room.
She was still in boss mode. "Ok girly, up and make me breakfast. Muesli and a coffee. And whatever you want. Then off to the club. Remember what I said - inspection sometime today and buy some matching bras and a corset. Taco's tonight I think."
Even without the gag in, he stayed silent. Getting up he started to walk out the room. She slapped him on the bum. "Cute cheeks baby!"
She watched him walk out naked except for chastity and butt plug. She loved the look of him smooth. She wondered what it felt like to have a plug in overnight? She had only played with one in for an hour or so at the longest. She loved being fucked and the feeling of fullness with a cock in her vagina and a plug in her ass, separated only by a few mm but had only done it twice. She had never been dp'd although she had vague fantasies of being gang banged but would never act on them. Sure she had watched porn. Thinking about Brad being all dolled up tonight kept her feeling wet. I might buy him some shoes with heels and a wig too if I can get some time today. That would make him feminine from head to toe.
Shower time. She checked his shoe size and compared it to hers before she left the shower and master bedroom for the kitchen. She had applied almost zero makeup as she had no time this morning to dally. She was fortunate to be beautiful with an almost perfect complexion apart from a few freckles. Even at 25 she retained a youthful wholesome girl next door look. High cheeks with full sensual lips and full minimally shaped eyebrows. Bright grey blue eyes that sparkled with intelligence. She had a slightly messed up blond page boy style hair that she thought suited her professional look. Sometimes she wished she looked more mature and older. Of course with her customary light grey knee length pencil skirt, white blouse and matching jacket.
Muesli and coffee were on the table as she ordered. As she entered the kitchen Brad poured the milk so it didn't go soggy. Brad had eggs on toast with 2 fruit muffins and a protein shake. He surprised her by waiting to sit only after she sat down. He was really getting in to the whole mistress thing.
She held her finger up to her mouth indicating that he was to stay silent while they ate. His face went red again but he remained quiet even though he was obviously bursting to talk. She was dressed and he was still naked. Emphasising the new power dynamic.
She had to leave earlier than Brad to get into work in time, park and walk to the office. She drove a Mercedes A45 AMG hatch paid for by Brad's income and she loved the performance and prestige of such a car. It suited her image of an up and coming successful attorney.
"Bye dear, see you tonight...", she waved goodbye and blew him a kiss as she left.
Brad watched her leave with mixed emotions. He couldn't wait to remove the plug as it had dried up and was sticking to his internal anal membranes. It was going to be difficult to get out, maybe he could squeeze some lube in or rub some in with his finger. Definitely going to need to take some lube with him today to keep the plug slippery. Before he got into the shower, he tried sticking a well lubricated finger into his anus around the edge of the plug. Wiping it around the rim he pushed it in and rubbed it around the perimeter of the plug. Yeah that worked. Pulling it out, he sat on the toilet before getting into the shower. He washed and cleaned it prior to reinsertion. Unsure how to clean his penis inside the chastity device without the key he simply drenched it in water and rubbed along the slots in the end and along the tube. He couldn't fit a finger-tip under the ring to wash it. Shaking it under water and rinsing off the soap suds was as good as he could do under the circumstances. He filled the anal douche and filled himself up with two loads of water, which seemed to be enough this morning.
Lube up the plug, rub plenty of lube around his rim and inside and then stick it back in. His anal ring was feeling a bit sore & tender with all the stretching it had been doing lately but no real pain. Nothing he couldn't deal with and the feeling of being full with a plug was definitely enjoyable. The biggest problem he realised was how to stop the chastity cage from flopping around hanging off his privates. He does a lot of running and jumping around in training and wearing a metal tube over his dick might be a problem and potentially obvious to others. He tried to tuck it back under his legs with the pink lace panties worn over the top. Jumping up and down it certainly jiggled around a bit. Maybe he could do an AI assisted search to give him some options later. He had a late start again today at 11:30 with a speed session and some small group drills. Still only 7:45 as Erin had woken him so early this morning. Recreational training gear in club colours as supplied to all players he carried in his bag as he was going to incognito shopping for the bras and corset first. He could get changed in the club toilets so as not to expose his chastity or plug to anyone. He would shower at home.
=
Brad shopping for Lingerie #2
Tue 10/2, day 8
Driving off he went straight to the lingerie store first. He had on his hat, glasses and scarf as well as a large baggy coat. Likely the store didn't get many solo males. The same shop assistant from yesterday was on duty again. She was quite short, a few inches over 5" and curvy but slim. Busty with a C or D cup. Her black hair was severely pulled back into a braided ponytail.. She spotted him quickly as his disguise was identical to yesterday's and grinned, "Back so soon! How can I help today?"
Realising she had gleaned what he was doing yesterday he gave up the pretence of buying for his girlfriend and asked for some bras matching the panties he bought previously. For himself. Being an athlete he had some pecs but he was all skin and lean muscle. Very little fat was layered under his skin.
She advised to get some A cups to fit him now and a larger size(s) if he wanted to get some breast forms or pack them with loose material to pad out the size.
"Are you on hormones?" She brazenly asked.
"What, no, of course not!" he exclaimed loudly in surprise, turning bright red (again). Others in the shop looked over at the raised voice and surely noticed his bright red complexion, which embarrassed him even more. Lucky he was still disguised as he was attracting too much attention. The last thing he wanted to do was to be identified. Wishing he hadn't come in but he had to fulfil Erin's "orders". He started to get aroused again - from the embarrassment and humiliation - and his penis with hardly any room to expand immediately filled the chastity tube. Still pushing against the immovable object his mere flesh and blood penis failed to get erect. His soft 1.5" couldn't even get close to his full unencumbered 6"
He sighed and said softly, "Let's go with A cups at the moment. Do you sell breast forms?"
She advised. "No, but I can give you information on a good supplier you can order online. Go for better quality ones, which are more expensive but are more shapely and made from a better quality material. You will probably need some glue also to hold them on. Once you pick a size then come back here to order bras to suit. Bring the forms in and I can do a custom fitting for you."
She obviously had some experience in this area.
"Go to the fitting rooms with some bras and try them on for size to make sure they fit."
She wasn't talking loudly but people close to them in the store where they were standing in the bra section could obviously hear their conversation. One woman looked at him in disgust, another tried to ignore him (but carefully listen) and a third was smirking.
Could it get any worse he thought. Ignoring the other customers he took the bras she had given him and went into a change room. Women in the corridor leading to the change room cubicles looked at him strangely - a guy holding some bras going into a women's lingerie shop change room. He had hoped that the store would be almost empty at opening time. Not to be as they had a sale on today and early bargain hunters were trying to get the best deals.
He quickly selected the nearest empty room and locked the door behind him. He took off his shirt, picked up the first bra, a cute red pink lacy one and examined it to work out how he was supposed to put it on. He had taken quite a few off but never before put one on. He hadn't really watched Erin put hers on either.
When he had bothered to watch her get changed it had been more to ogle her sexy body. He got more aroused handling the bra and feeling its soft material with lace trim. There were some adjustable straps and given his build and male chest size he would probably need to let out. He pushed his arms through the straps and tried to fasten the bra behind his back. His arms weren't flexible enough. Not even close. How the hell did women put these things on? Erin made it look easy from what he remembered. He tried various ways, arms above and below, looking at the mirror trying to reach the hooks together. Getting frustrated he was getting nowhere. What's the point of these things if you couldn't even put them on!
A voice he recognised, outside the room, "How's it going, need any help?"
He quickly unlocked the door and almost dragged her in the room. "Yes, I can't get it on, I can't reach behind me. How do I do it?" He whispered in obvious frustration.
"I'm Joy by the way, the store manager. Let me show you, take it off first."
Brad shrugged off the bra and she took it. She reached around his back without putting his arms through the straps so the back straps which fastened together were in front of his chest. She then asked him to fasten it which he did easily. She then rotated the bra so it was the correct way around with the cups over his pecs and nipples and told him to put his arms through the straps.
