Please leave comments
The alarm woke him. It was a work day but rather than get up he lay there thinking for a while. Had Jane really kissed him when they were in the taxi? Had really they done all those things when they got back to Jane's house? He got up and looked in the wardrobe. Yes, everything was there, even that accursed butt plug which had caused so many problems yesterday. Had Jane really needed to see how easily it slid in and out of his bottom when they got back to her place? And had she needed to keep on doing it? He supposed he only had himself to blame. It was his fault and his fault alone for getting an erection when she undid and took off his cache sex. When they'd got indoors Aunt Jane had said he could take off his new clothes. Andy had eagerly complied although Jane had insisted on removing his cache-sex herself. Maybe it was her touch or just having her near him but his cock had sprung to life when released: having a hard-on in front Auntie was so embarrassing. He tried crossing his legs to hide it but Jane didn't seem to mind. She was still wearing her latex jacket and trousers: the way she shimmied and squirmed, she was clearly loving them and the effect they seemed to have on him ... and her. And then she'd kissed him again: that didn't help his erection at all.
When he was naked except for his high heels and the plug in his bottom, she held his face in her hands. She kissed him again, long and slowly, her lips hard against his and her tongue probing into his mouth. His cock become more eager and pressed stiffly against her latex clad belly. Jane could feel the sensuous rub against her wondering if her nephew would try to frot against her. "I do hope you aren't leaving marks on my new trousers or jacket, Andrew," she said. And, seizing the opportunity, she continued "I'd like to see whether the collar and cuffs fit you so could you try them on, please?"
Although he loved being kissed by Aunt Jane, Andrew saw putting on the cuffs as a way of distracting himself and readily agreed even though he knew the cuffs and collar were adjustable so fitting was hardly going to be a problem. The steel bands slipped easily into place and Jane snapped each padlock shut. It was Jane's idea though to fasten and padlock his wrists to his steel collar. andy could hardly move his arms and when she asked him to kneel down on all fours, all he could do was rest on his elbows. He thought she was going to put him on the dog lead but instead she tried to remove his plug. Andy felt relieved. "Thank goodness," he sighed. At last that thing was coming out. At least it would be one less embarrassment: only gay boys or sissies wore butt plugs, he thought.
Unfortunately after a couple of hours of having the plug inside him, Andy's arsehole had closed firmly around its neck. Jane tried to extract the rubber plug but he was gripping it too tightly. "Do you really want this out? You seem desperate to hold on to it. You need to relax, honey" said Jane "if I'm going to get it out." This didn't seem to help. If anything his ring closed even more as Jane attempted to pull on the base of the plug. "It's not releasing darling," sniggered Jane as she tugged some more. "Let me try pushing and see if you loosen," she suggested. Jane pushed the plug forward. Already fully inserted, it couldn't go any deeper, but Andy felt it slide and bang against the walls of his rectum.
Jane alternated between pushing and pulling. Andy's cock began to sway in time with the movement in his bottom. His erection, which had earlier managed to subside, started to grow again. Andy concentrated on his cock hoping to avoid it getting hard. As he did so, the wide bulb of the plug slipped out of his sphincter. "Oh sweetie, that seemed to do the trick. Let's see if it works again." To Andy's dismay, his Aunt pushed the plug back in. To his shame, his arsehole stretched to receive the plug. "Well that went in easy enough." Jane didn't let it go all the way in this time though so his ring couldn't close around the narrow neck.
"No, please Auntie," Andy requested. "Stop, please," he pleaded. "Those ladies at the shop have given you all the wrong ideas."
"Oh but they haven't, Andy. It's clear you like seeing me in latex. Just let me indulge one of my fantasies for a while," replied Jane, "after all you seem to be enjoying it." Andy couldn't deny that he still had an erection. "You look so sweet with something in your bottom. And it's really not that big." She pulled out the plug and held it in front of Andy's eyes. Andy stared at the plug in her latex gloved hand. Up close, it looked enormous.
"But it's huge, Auntie. Those ladies should never have put that in me."
"If you're going to complain, I can fix that." Jane fetched her ball gag, thrust it into Andy's open mouth and locked it behind his head. "Now you're quiet we can properly get down to play." She greased the plug, particularly around the neck and base of the bulb, and inserted it again. This time she gave him the full length. It slipped in easily as if welcoming a familiar visitor and his anus closed again around the slippery neck.
Andy gave a muffled moan through the gag. He didn't want anything in his bottom but he was in no position to resist. "That wasn't so bad, was it honey. Now let's see how this works." Steadily Jane began to slide the plug in and out or his arsehole till. All the way in to totally out. Each time his anus opened and closed and with each stroke it became easier. Andy started to sob. He was taking the full length without difficulty and his cock had become rock hard. "Are you sure you're not enjoying this, sweetie?" Jane asked. It was impossible to answer but he could feel that his cock was dripping. "Don't cry honey, your little friend already seems to be weeping. After all that complaining too," she said with a wry smile. "Let's see if you like this too."
Jane pushed the butt plug in fully and got the leather crop from the bag. She gave Andy a light tap on his buttocks. Andy flinched. "Don't be nervous, that was nothing." She gave Andy three rather harder flicks with the crop. Tears welled up in Andy's eyes. As red welts started to appear on Andy's buttocks, she came round to the front, took off his gag and kissed him once more. "You're a good boy Andrew. I can see we're going to have fun together. Now let's get you home."
Andy found his member stiffening at the thought of yesterday and leapt out of bed before he went too far. On the chair in his bedroom, Andy found a note and some clothes that Jane must have left last night. The note said that this was his outfit to wear to work today. He knew now why Aunt Jane had insisted on shaving his legs before he left her house. At least it wasn't another dress and there were no high heels, but he did wonder how staff at the store would react given the design.
However Jane's note also presented rather more of a problem than the somewhat effeminate shorts. It stated that Andy should wear lipstick and the wig from yesterday. The first was easy, Andy didn't have any lipstick; the second was simply an impossibility at least during his journey to the shop where he worked. What would people think? Then he encountered another problem. Where was he going to put his wallet, phone and keys .... and, of course, that damned wig? The shorts had no pockets. He was going to need a bag. Also sitting on the chair was a pretty black leather clutch bag. Well, he wasn't going to use that. He'd always thought man bags rather silly and this was even worse. He found a practical shopping bag and popped his effects and the wig into it. Then he hurried downstairs to catch the bus to the station hoping to avoid anyone in the house seeing him. But his mother was already up and caught him just before he reached the front door. "Good morning, Andrew. You haven't had any breakfast."
"Hello Mum, I'm late and need to go. Don't worry I'll get some coffee at the station."
"OK. Darling you do look lovely. Is that the outfit Jane left last night? I don't know why you had to run straight up to bed without seeing us. Fortunately Jane came in and we had a long chat. She said she'd enjoyed her day out with you yesterday. She's such a dear friend. I'm glad the two of you have hit it off so well." She gave Andy a long look. Andy couldn't help blushing slightly. What had Aunt Jane said? What did his mother know? "She popped back later with those clothes. Those shorts do suit you. And you can borrow my lipstick. Sit down and I'll show you how to use it. And where's the wig you're meant to be wearing? Let's get that on before you go out. You don't want to disappoint Jane, do you?"
Andy shrank. "No Mum." All hope he had of keeping yesterday secret had vanished. His mother knew something but he didn't know how much. She didn't seem worried though. He relaxed: Jane must've said he was doing it for a bet or something like that he felt sure. At least he could choose the shade of lipstick he wanted. A nice coral red, perhaps. He'd tried that once before when his mother had been out.