Annabelle's Lockdown Ch. 04

Authors note:

You should probably read the earlier chapters. However, these chapters might be okay as stand alones. In short, Annabelle, aka 'Tink', her heart freshly broken by a cheating boyfriend, encounters a friend (Timmy) from her distant childhood who has turned to her for help. He's been abused in foster homes, fed breast forming hormones and seeks comfort and safety in Annabelle's presence. He's decided to commit to staying with her during the covid-19 pandemic lockdown, and consented to some of her demands, including wearing her clothes. Their relationship has turned sexual, with bouts of masturbation occurring over recent days.

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I woke up feeling amazing. Last night's mutual masturbation video call left me satiated and the eight hour sleep had me energized. After a light yoghurt and muesli breakfast at one of the mining camp's food centers, and a quick spin session in the gym, I hit a shower.

It was only then that I picked up my phone and called Timmy. He answered quickly and was sitting out on the balcony overlooking Scarborough Beach. He panned his phone and showed me the scene. The sand gleamed in the mid morning light and a two foot swell had small dumping waves breaking on the sandbank. Due to the lockdown, very few people were on the beach and only a dozen or so cars were in the usually packed car park.

"Tink, that call last night," he began, "was amazing. I'm still buzzing from that."

"I enjoyed it too."

"How did you know I had a pair of your undies in the hamper?"

"Timmy, it was a fair bet that an 18 year old boy, left alone in a 23 year old girl's apartment, would take a pair of her undies and do unspeakable things to them." He blushed at that comment. "It's okay though. I kind of expected you'd do something like that. I mean, you have been wearing my clothes since I threw yours out, and we do have something happening here between us. I'm not exactly sure what it is but I'm enjoying it and wanting to see where it goes."

He smiled at me through the phone. "Same. I'm just so grateful that you took me in. I'm not sure what I would have done if you hadn't come through for me. I owe you. I haven't felt this safe, or alive, since my parents died."

"Timmy, you don't owe me anything. I asked you to help out with a few things but you aren't in debt to me. Plus, you've helped me though a rough patch. He broke my heart... you've stepped in and helped me to pick up the pieces."

"What exactly happened?" He realized as soon as he said it that it was not the right time to ask. "Sorry, don't worry, I don't need to know."

Silence hung in the air for some time. I wasn't ready to really share this with him now. Only a handful of people knew we had broken up. I decided that I needed to let Timmy know a bit, despite the rawness of it still. "I found him fondling a skank in a foodhall. He'd been fucking her behind my back and whilst I was over east at Grandma's funeral."

Silence again filled the call. I felt a tear run down a cheek.

"Fuck..."

I wiped the tear trail and tried a smile. "But that's in the past. I don't live there now. But I will never speak his name again." We sat there in silence for a good thirty seconds. I hadn't expected to be deep and meaningful with Timmy so soon, but it was not really surprising, he'd been in and out of my life for, well, a large chunk of at least half my life, but mainly as a childhood friend. "With your help I'm moving on. So it is win win for both us, which is not bad in the middle of a lockdown in a global pandemic."

We then talked small talk for a while. He listened whilst I offloaded about work and the issues up here at the mining camp. He spoke about starting to become bored in the apartment. He'd watch a huge amount of netflix, had done the job's I'd left him, and was going a bit stir crazy under the lockdown orders in place. I also gained a bit more of an understanding of what he'd been through with his abuse in foster care, the bullying he'd endured in homes and at school and how resilient he'd been in the face of some downright inhumane treatment.

"So why turquoise?"

"What?"

He hadn't followed that I'd gone full circle with our conversation and we were now back at the pair of low rise thong underwear he'd used and left in the hamper. He finally caught up and went as crimson as could be.

He looked at me directly down the phone. "They looked feminine and sexy."

"That they are. They look so good on me. They hide just enough to keep things from being x-rated but they show enough to be very revealing. They also looked fantastic on you Timmy..." The image of him standing there, showing himself to me whilst wearing them caused my insides to flutter. With his slight frame, pert breasts and a tucked penis, he did look feminine and sexy. With an untucked dick, well, my insides had heated and our call had gone nuclear. The insides of my legs still ached from where I'd ground and humped myself on the mattress.

"What had you done when you went through my underwear drawer?"

He chuckled. "I was nervous. There were some amazing...things...in there. I saw that colour and grabbed them. I stripped off, put them on and felt great."

"Did you fantasize whilst wearing them?"

He paused, then nodded. "And then I played with myself for a while."

"Did you cum?"

He shifted in his seat. "Yes."

"In them or on them?"

"Both." He looked guilty saying it. Geez the kid, he was only just 18, must be full of jizz.

"What did you fantasize about Timmy?" Now he hesitated.

"It's ok. You are safe with me."

"I thought about you wearing these. About you getting fucked in them. About you getting cummed on whilst wearing them..."

"And?" I could read him like I could read him when we were younger, when I used to baby sit him. He put his head down, I couldn't see his eyes anymore.

"I thought about being you."

I pushed a little further, seeing where this would lead. "About being me, or about being cummed on as me?"

He nodded slightly. "Both." He took a few breaths.

"It's ok Timmy. You are safe with me." He looked up. A tear ran down a cheek. "Now we've both cried."

"And that's why I want to spend more time with you," I added. "I want to see where we can go with this." I emphasized the 'we' as I said it. "I have to go now. Go get a drink of water. I'll call you back in 20." I needed some time to process this. Unfortunately that's when my phone rang.

Two hours later, I called him.

"Is everything ok, Tink? You said you'd call in 20."

"There looks to be some issues with my return to Perth. Cyclone Charlotte has taken an unexpected turn towards us and sped up in the process. We are going to blue alert and then pretty quickly to yellow. They are giving priority returns to Perth to the 'four week on, two week off' shift that is just finishing. It looks like I won't get out till after it all blows over."

"Shit. You okay?"

"Yeah, these camps are built to withstand some heavy shit. It looks like category 3 only so we should be fine, and we are inland from it's landfall. It looks like we'll just get a huge amount of rain and a bit of wind. But my return is delayed. So listen, have you explored other parts of my room?"

"No, I put your clothes away in your wardrobe as instructed. I changed the towels in your en-suite shower but left your room untouched."

That was good. It was my personal space still. "There is something you might enjoy in the bottom drawer of my bedside. Don't go looking at anything else. Understood?"

"Understood." He looked like a child who had just been scolded. I did want to reassert this the apartment was still primarily my domain.

"There is an old laptop in a blue box on the top shelf in the cupboard in the hall. Fire it up and make yourself a user account. It should have been factory reset as it had some issues and I had it repaired but I ended up getting a new one through work."

I then went on to tell him that I had approval from work to contract out some administrative work and report typing, and that he could start earning some money by working from home. If he contacted his bank and tried to set up a new account, one unknown to any of his former foster parents, and using his first initials only, rather than a first name, and it could be paid into that. I gave him the number of one of the in house legal team to help him if she had any trouble. When he asked why, I think I shocked him with the news that I had informed my boss and the legal team that he was a 'she' and my best female friend, a friend who was looking for work, and who could help me with my workload.

I said if he set up an email address and sent me the details, I send him some links I'd found to help him with some voice coaching to make his voice a little more feminine. I also let him know I'd also transferred another $500 into his account so he could get more food or other necessities. He quizzed me about the voice thing and I just reminded him that we were on some crazy adventure here. All he had to do was say our safe word and I would stop. But the safe word was never invoked.

It was night time when we spoke again. He listened, god he was such a good listener, as I offloaded some stress from the working day. My phone buzzed.

"I've sent you a pic." he said.

It was a selfie of him in his bedroom mirror. He was wearing a short sleeve denim bodycon dress. It came to mid thigh on him and looked casually chic on him.

"Nice, casual look there Timmy."

"Wait a tic," he responded and moved from the tv area to his room. Panning the phone around he showed off the long sleeve, long white skinny shirt, dress he was wearing. The slight curve from his hips was just visible with the body fitting style. His small but pert breasts swelled the fabric just enough to hint at some shape there too.

"Tussle your hair for me sport." I requested.

He complied and the look was amazing. The bruises on the side of his face were almost healed. His blue eyes shone. He looked like a young blonde who could have been on her way to a casual drink at an outdoor bar on a Sunday afternoon. He stuck some poses and we both ended up laughing. Then he pulled his hair back, holding it in place with one hand. He tilted his head slightly and smiled. I swooned.

"I'm going to have some fun with you when I eventually get back!"

"Promises, promises." He replied.

"That is, as long as there is still a dick under that cotton." He grabbed his crotch and nodded. "Good," I added, "keep it ready for me. Hey, I really need some sleep. I'll talk again in the morning okay?" He looked disappointed. "I'll send you an email challenge to keep you occupied and test out your account. Set it up and send me the details." He raised an eyebrow and his blue eyes flashed. "Just don't have too much fun without me, and don't talk to strange boys." With that I ended the call and got to work with some deviousness shenanigans.

The next morning I awoke to a phone notification. On the screen in front of me was a picture of a tight ass in a snug black thong. Just visible in the crack of the thong was a pink jeweled butt plug.

I smiled and texted back "So you found what was in the bottom of the bedside? Good. I'd only used it once. You enjoy!"

With that I got up and got into my day. Around 1. p.m. I was walking into the bathroom when my phone vibrated. I'd set it to silent during the working day and smiled at what might be coming through.

Clicking the link on the message took me to a video which showed my Timmy lying on his back on the bed in his room, his sexy, skinny, legs folded up over him and his right hand slowly pumping the butt plug in and out of his ass. I hit pause and raced into a stall, turning the media volume down on the phone so I wouldn't be heard.

He was whimpering. The scene then cut to him doggy style on the bed, his hand reaching around him and the plug being hammered in and out of him. Moans loudly emanated from the figure in action. Then a final scene. He was on the bed on his back, with this legs under him, pushing his lower half up in the air and his head and shoulders down. The camera view was from his neck, up his body towards the ceiling. He was wearing what looked to be one of my black cotton g strings, pulled to the side of his penis. He seemed to still be plunging the plug into his ass. His dick swung up and down slapping on his body. He was grunting.

The camera shook and bumped along with the unseen thrusting of his hand. Pre-cum dripped from the head of his penis, rolling down his flat abdomen towards his cute belly button.

"Oh shit this is good." He moaned. "Oh, fuck....fuck...fuck.... I can feel it every fucking time it violates me..."

I was getting wet, fast. I unbuttoned my trousers and shoved a hand down the front of my plain cotton undies.

"Is this what it feels like when you get fucked Tink? It feels sooooo good.... Oh my god..." The volume of that was louder than earlier. I was worried about being heard and, in the process of trying to turn the volume down, momentarily turned it up.

"DID YOU EVER FUCK YOURSELF WITH THIS PLUG LIKE THIS?"

That ended up being so loud it would have been heard by anyone in the bathroom. Funny thing is, even though I'd only used that plug once, it had been for a date several years ago. The date, before I met the ex, had gone badly and I went home frustrated. I pretty much had done the doggy style scene myself that night. So the unspoken answer to his question was 'yes'. I was now furiously fapping away at my clit with one hand and fumbling with the volume control in the other.

That thought must have pushed him to the edge. His torso was covered in a sheen of sweat and his legs were shaking from holding that position. "I... I... I'm going to cum. Oh Fuck!"

With that his dick fired shot after shot. The first hit over the camera somewhere. The next hit his left nipple and broke, showering his chest. The next several landed on, around and between his breasts. Still more roped out, these with less force, running down his body into his belly button, down his stomach.

Still standing, I slumped into one side wall of the stall, one hand clutching the phone. The other hand rubbing hard on my clit. I wailed when I orgasmed, seeing sparks before my eyes and smelling honey, and my attempt at stifling the noise by biting my phone arm failing miserably.

Worried by the noise I'd made, I hurriedly dressed and, despite the orgasmic high, headed out of the stall, juice covered hand held up. I was hoping to get to the sink to wash my hand and splash water on my face before anyone saw me, or came in. At the exact same time the stall next to me opened and a startled looking thirty something woman, wearing a caterer's uniform stepped out. We stopped dead in our tracks and looked at each other.

"Fuck that sounded hot." She said. With that she stepped towards me, took my raised hand by the wrist and pulled it towards her nose. She sniffed lightly, then sensually licked a finger tip. I curled the other fingers up, offering a whole single digit. She sucked it into her mouth, smiled, turned and headed to the door. As she opened it she turned, saying, "I'm going to jill myself off to this memory for years."

Heading back to my temporary work station and my colleagues, I sent a simple message. 'OMG'.

Later that night we spoke about our respective days and about that video. He beamed when I told him of the mischief he'd caused at my end. He was wearing one of my white collared corset crop tops. The fitted white cotton was a little loose on him around his breasts, understandably so given his smaller cup size. He panned the camera and showed me the white cheese cloth miniskirt he had it paired with. The skirt was short enough to be interesting, but not so short as to be slutty. The white underwear he had on was visible. He had a pair of two inch strap sandals on. He seemed excited beyond the usual as he told me about the bank account he'd set up, his success with the computer and the beautiful day that had passed as he listened to music and chilled on the balcony overlooking the beach.

I felt under-dressed lying on the bed in my room in a bath robe, a glass of white on the bed side table. After some more small talk he startled me by standing up from the kitchen chair and announcing to me "I'm doing it. Right now!"

It took me a second to catch up. "You sent me a challenge, challenge accepted." He put the phone down on the table, keeping his torso in the frame. With that he straightened the top and skirt. He was showing plenty of mid drift. He picked up the phone and headed to the kitchen, grabbing a cup. Donning a black face mask he picked up a house key and headed out the door. I couldn't see that well, his aim was for me to listen, rather than see everything as he headed across the landing and knocked on Claire, our neighbour's, door.

After some initial 'who is there in the middle of a pandemic' questioning, he introduced himself as Timandra, but 'Timi for short', a friend of mine who was crashing with me during lockdown. Claire, who knew about my ex-boyfriend's infidelity, had helped me crush his bike as an act of revenge. Claire asked about the name and Timmy filled her in, and educated me in the process, that Timandra was a Spartan princess in Greek mythology. He'd modulated his voice slightly. It wasn't over the top girly, but certainly wouldn't give him away as a guy.

The name thing caught me off guard, I had not expected he would have had a name story. The kid was inventive. With some more small talk, he asked to borrow a cup of sugar, and then left, returning to the apartment and ripping off the mask, he laughed. He was ecstatic that he had met part one of the challenge, which was to borrow something from a neighbour whilst dressed. He seemingly pulled it off. Claire gave no indication she had picked him as a guy. We spoke about the thrill of the moment and how the sharing of it was amazing. Leaving the cup on the table, he re-masked and headed out the door again. This time he kept himself in frame and we giggled as he headed off on the next part of his challenge.

Entering the elevator he shivered with excitement. "I can't believe I'm doing this. I'm leaving the apartment and the complex, dressed in your clothes!" I was enjoying the tension of the moment with him. It wasn't too long before he was out of the foyer and into the cooler night air, walking down West Coast Highway towards the local shops. He added commentary as she went. "I feel so bare in this skirt, Tink... Hopefully no one can see my butt plug from behind, the thong is tiny. I can feel it pressing up into my crack." He nodded when I asked whether it felt good. His walking was impressive. He'd obviously been practicing throughout the afternoon for this.

As he passed by the high rise hotel on his right, he deviated into the drop off area. This was not part of the challenge! He was taking risks of his own now. A family of three were getting out of a van assisted by a porter in a bit more than the usual face mask. The guy was almost in full PPE. The family, also heavily masked and gloved, were South Africans by the sound of it. A huge barrel chested guy, a very elegantly dressed blonde trophy wife at his side and a blonde, younger women, most likely a daughter. She was almost six foot, athletic looking and had the fine facial features of the older woman. Timmy, or should I say 'Timi', was cut off before he made it to them by another porter.

He smiled, directed her to leave back the way she came, as this were some VIP family who were quarantining here after arrival. I thought that this explanation was strange as the quarantine hotels were all four star hotels in the city, not ones out here on the coast. They must be really connected.