Annabelle's Lockdown Ch. 05

Timmy, now going by the name Timandra, or 'Timi' for short, and the pronoun of she/her, had come into my life only two weeks ago, just as I had discovered my boyfriend had been cheating on me.

In that short amount of time, Timi, whom I used to babysit when we were much much younger, and I had reconnected. With no where else to stay during the covid-19 lock down, and no clothing of his own, but sporting a pair of hormone induced A cup breasts that were his, Timi had accepted my offer to 'stay and play' and dress in my clothes. And that's when things had started to get funky.

After being called to an accident at a mine and trapped on site for several days by a tropical storm, I'd been happy to return to the apartment. Whilst I was looking forward to some more escapades with my new flat mate, I'd needed some time to recharge and revitalize, so I'd had to tell him to just give me some space.

That didn't stop Timi acting suggestively when I had entered the apartment, and I'd had to put her in her place. She'd obviously enjoyed our video call masturbation sessions, and was a typical hormone filled 18 year old teenager, wanting more of the orgasmic rush that she'd experienced. But I was in charge and she'd need to play by my rules. So I'd strung her out and made her promise not to get herself off.

We'd shared a few interesting make out moments, and had some nice 'close time', where we'd talked about 'her', my life, and a thousand other things, but I had wanted to push her out a bit and make sure she was really wanting to go as far as she looked like she did. I mean, it was one thing for a 'guy' to spend a week in a young woman's apartment by himself, dressing in her clothes, with only one adventure out into the world beyond in a skirt, and another thing to be dressing full time in a relationship. And this did seem to have become a relationship.

Some of those deep and meaningful conversations had been a bit revealing and went beyond our early discussions. I'd admitted to literally getting off to the sight of her butt that one morning, that her dressing up was more than just a turn on, and that I knew I had some controlling tendencies. She'd admitted that she had always felt a thrill dressing as a girl, even when I used to baby sit her, and that she'd fantasized about being me more than once in the past.

Our next week in lock down had been spent working during the day and watching tv at night. I'd been going out getting my mandated hour of exercise each day, usually walking along the mainly deserted beach pathways outside our apartment. I'd dashed to the nearby supermarket for food supplies when needed, but otherwise we just stayed in, as we were supposed to during this lock down. Timi had stayed inside.

My human resources job was keeping me busy and Timi's new job working for my firm, mainly in a support role for me, as an administrative assistant, was keeping her busier by the day. She worked with my old laptop from the end of the kitchen table, about eight feet or so from my work station. It was a good setup and we could get productive without being too much on top of each other. Occasionally, I'd hear her in the guest room working with one of the online voice tutorials I'd organized for her, although given the way the small changes she had made from the get go to her vocals, it wasn't like she needed to be doing much to pass off as a she. Her voice had become more and more passable with every passing day.

She'd been choosing clothes from my wardrobe each day and had been, at my suggestion, dressing very casually. It was late summer, still damn hot, and we were in lock down, so there was no need, despite her apparent occasional desires, to dress up. So she'd worked her way through a number of matching short and shirt sets, a pleated skirt and tank top that really accentuated her shapely legs and flat tummy and some simple running shorts and sports bras, although these had been a bit loose fitting, as her cup size was smaller than mine. More often than not she'd tuck her package back around into the underwear she had on. Sometimes she'd let it bulge 'man style' in front. Her hair was getting longer, and more often than not was found pulled back on her head with one of my scrunchies.

Some days she'd disappear for a while and come back with a wicked smile. I'd learnt that usually meant she'd gone and inserted the butt plug, which was mine, but she now seemed to claim as hers. That would often see her rocking on her chair slightly as she worked, which seemed to give her enough prostate stimulation to keep her buzzing with excitement. She did seem to be living up to my demand to not get herself totally off though.

As that week progressed, a number of packages arrived for both of us. Some were obviously the clothes she'd ordered after I had asked her to order some online, and the others were things I'd thought about during my time away at the mine. She'd been getting excited as the pile of boxes and post packs grew, but I'd forbidden her from touching any just yet. She didn't complain, but I could tell she wasn't really happy with me for it. But behind the pouty looks, and odd foot stamp, she followed my suggestions and never challenged me. She'd regularly glance at the growing pile, smile and then look at me, happy as can be.

Life took a small change at the end of that week when the authorities announced that there would be some slight easing of restrictions over the next few days, as case numbers had been dropping back to very small numbers. The most immediate change for us was that the pool in our apartment complex could now be used by owners, although subject to restrictions on how many people could use it at any one time. We could also go outdoors and not wear masks anymore.

After an early night, spent shared with Timi in the guest room, with some gentle kisses and warm spooning, we arose to the breaking light of dawn and discussed heading out together to enjoy our less restrictive world. I'd gone to sleep in my underwear, which consisted of a plain blue push up bra and hipster undies, which had been worn for comfort, not sexiness. Timi had slept in the women's tshirt and shorts she'd worn on her first night in the apartment. We were dressed for comfort but would need to change it up if we were going to turn heads on the pavement outside. After changing into some skin tight vivid pink running shorts and a matching sports bra, with Timi similarly dressed, but in black, we prepared to head out into the world. She'd smiled at herself in the dressing room mirror when she'd finished putting the gear on, reveling in the tight fit of the shorts and the feel of the bra across her breasts.

After checking whether she really felt ok with going out in public for only the second time as Timi, and getting an excited nod, but also a bite on her bottom lip, which sent my heart fluttering, we hit the pathway along Scarborough Beach for a serious running session. With her penis carefully tucked and secured inside a pink cotton thong, in turn held within tight running shorts, and her smallish breasts held within the confines of the bra, her 32-22-31 figure easily passed as that of a young fit woman. Of the few other local runners and walkers we encountered, none would have picked her as having been a 'he' just two weeks ago. She seemed to gain in confidence each time we passed others and seem to revel in the smiles and soft encouragement that I gave her. We returned sweaty, sore and happy.

After sculling a couple of glasses of water and sharing a carrot stick or two, I grabbed Timi by the hand and headed over to the side table where the packages were. Her eyes widened. I kissed her gently, her eyes still questioning the moment. "Lets have some fun before work!"

She visibly exhaled, squealed in delight and grabbed me in a sweaty hug as I hunted for the right package and then a particular box.

She tore at the package, finding two swim suits. A white one piece o-ring halter top with cut outs down the right hand side and across the tummy, for her, an almost the same style, but with spaghetti straps, version in black for me. The box held matching coloured open toe wedge sandals in matching colour for both of us. The one inch front and two and a half inch heel giving us both a nice boost in height.

Grabbing at the waistband of her running shorts, she pulled them down, taking the pink thong with them, leaving her six inch boner pointing outward and upward, bobbing in ever increasing erectness as her excitement heightened. She looked at it, then me, and shrugged, blushing.

I giggled. Grabbing her by the shaft, I tugged twice, feeling her harden further under my touch. Pulling, rather than tugging, I then led her to the breakfast bar and picked up the glass of water I had poured earlier, sculling it and handing it to her.

"Refill?" She looked toward the tap.

"I think fill would be better." Looking at her boner, then the glass, I tugged a few more times and stopped. Timi looked at me somewhat quizzically, somewhat expectantly. I dropped to a crouch and took the head of her penis in my mouth. She smelled of cinnamon scented sweat and tasted slightly salty. Pausing to make eye contact, I then bobbed in and out a few times, coating her length with my saliva. "Lubed up, ready for you to finish". I took the glass, stood back up and held it in front of her dick.

Getting my drift, she spread her legs slightly, smiled. Grabbing her shaft with one hand and her balls with the other, she proceeded to jack off in front of me. "Come on Timi, we haven't got all day!" Her brow furrowed and she quickened her pace. "Do it in 5 more seconds and I'll let you fuck me tonight!"

She smiled determinedly and worked harder at the task at hand whilst I counted down from five. When I hit zero she had done amazingly well to get close, but, much to her dismay, needed more time. Fairly soon thereafter, she nutted into the glass. Once the gushing had stopped, leaving an impressive amount pooling in the makeshift cum capture device, I bent down and cleaned her off. She shimmied as my oral activity pressed on and around tender nerves. "No fuck for you, but we might still have some fun." I said as she came down from her high.

"I never know what to expect when I'm with you Tink."

"And that's why you've always loved being my side kick." I added, turning her around and leading her by the hand back to the swimsuit.

I helped her pull it up her body and gently helped her tuck herself back behind her nuts, then pushing those lovely balls up into her body cavity space in the process. Unlike some of my previous efforts, it wasn't perfect, but she'd be able to walk past people without too much drama, although they may think she had one hell of an unusual camel toe. She adjusted again slightly, nodded her approval to me and blew me a kiss. I left her to do her shoes whilst I stripped, not surprisingly finding myself slightly moist between my legs, and readied myself for our adventure.

Grabbing some keys and towels from the linen press, we headed, hand in hand, out the door, but not before I put the glass of cum in the freezer and pausing by a full length mirror. "You ok?" I asked. She nodded to the mirror, then turned to look me in the eyes. "Better than I've ever been"

The cut out panels in the suits showed off both of our flat abdomens, my tan, her paler colour, and both our curves. The o-ring top of her suit giving her smallish breasts some extra definition. I was never one for body piercings, but her belly button was begging for some adornment, something I decided needed further pondering, and her cute backside moved sexily as she took off out the door in front of me.

With no one else in the pool area, we signed in, the current rules giving us at least 20 minutes of exclusive use. The water was cool and invigorating, causing my nipples to harden in the first moments of contact. The contrast in temperature was a nice balance to the rising heat of the day. The pool deck was on the top floor of the complex, giving us privacy from our immediate apartment neighbours with no one visible to us in the other, slightly taller apartment building just north of us. A distant solitary figure could be seen on a balcony of the high rise hotel to our south. For all intents and purposes, we were alone.

We swam some laps, splashed each other a bit and enjoyed the freedom of being outside sans masks. We were just two silly young women enjoying each others company, except for the fact that Timi looked like a model, a wet swimwear model, with wet slick backed hair and drops of water running down her face, accentuating her cheek bones. My heart was racing just looking at her, wanting her. Wanting her badly.

The next thing you know, I found myself locking lips with her, one hand cupping a butt cheek and the other groping at her right boob. Whilst it wasn't a huge handful of breast, there was enough there to be of interest. I felt her nipple harden under my touch. "How sensitive are they?" I asked, after breaking away from those lips.

"Very". I pulled up on the fabric of the cut out, exposing her right scoop of perkiness for me. I bent in and kissed it gently, watching her head tilt back and eliciting a small moan from her with a slight tongue flick in the same spot.

I felt her hands move to cup mine. "Go ahead, feel them," I said, and she began to caress my larger breasts, gently at first, but then with more vigour.

"Ohh, that feels good, Timi," I said lustily as my nipples turned to hard metal bullets under her touch. "But your mouth would be better."

At that she pulled the straps of my suit down and off my shoulders, exposing both breasts to the world and her ministrations. Moving in, she kissed one breast, then slowly kissed her way across to the other fleshy boob, smiling at me as I looked down in awe and wonder at this angel in front of me. She dropped her gaze and continued with her sweet kisses and I stayed blissfully there, watching her, feeling my body react, both physically and emotionally, to her. She pulled away slightly, causing me to groan at the halt to the heavenly contact.

"God, you're beautiful..." I whispered down at her. "Please don't stop." At that a drop of water fell from the end of my nose. Time seemed to stop as I watched it fall slowly towards my chest, where it landed on the top half of my left breast and then proceeded to ever so slowly roll its way towards the nipple. I saw her eyes widen as they tracked the drop and saw her move her lips towards it even whilst it was in mid flight. It was erotic slow motion, and my senses were in overdrive at the fact that I was the center of the action.

As she started sucked at the drop, and then on my nipple, I pulled her lower regions closer to me and ended up with one of her thin legs between mine. As she continued, I slowly ground my mound against her thigh. She would throw a tongue lick into the sucking routine every now and then, sending sparks through my nipple and into my soul. "Fuuuuuck, you are teasing me now." I whispered.

I tried unsuccessfully to get my mouth near her boob again. "Enjoy your moment," she said, breaking away from my nipple. "You can play with me later." At that she resumed sucking, and I resumed grinding. I momentarily looked around, part fearful of someone finding us, still seeing no one but the figure, possibly female, on the balcony to the south. I moved my hands to the crotch of my bathing suit, pulling it awkwardly to the side, allowing my clit to get better friction against her leg. Hoping that the tidal wash of sensations would see my orgasm come sooner, rather than later.

It was there, but not coming here, fast enough. The visuals were driving me crazy. Those kissable lips, my breasts, a sexy ringlet of her hair that had come into focus, the ripples on the water, her small breasts lurking just below the surface. It was ringing my bells but not fast enough.

Frantic to gain maximum clit on leg pressure, I started hopping and grinding, causing us to spin around the pool, traversing most of its area. She had both hands on my hips, helping to push my cunt harder onto her leg. It was like a glorious erotic water ballet, with the added excitement of possibly getting caught. The coolness of the water made my clit a little less sensitive so I was having to work hard, yet the thrill of the moment, the angle of slide of my lips and clit against her muscles made it so hot. My urgency did not abate and became so real that I was worried I would take a layer of skin from either my privates or her leg. My actions eventually, with some relief, began to pay dividends and soon I could feel the wash of an orgasm surging towards me.

She sensed it too, smirked, and started counting down. "And five...four..." She never got to two before I bucked, swore and saw stars. Despite the chlorine water, I was sure I could smell frangipani again. My body reacted of its own accord as I floated there above it detached, watching myself and the angel who brought me such heaven.

I slowly came down from the insanity. She looked at me and smiled. "Wow"

"Wow." I replied. "That was intense." I slowly adjusted my suit as she did the same.

"You're welcome."

It took me several more minutes to fully regain composure and clarity of mind. She cuddled me from behind, whispered sweet nothings in my ear and slowly dragged us both around the pool in a more soothing manner than we had experienced just moments ago. It was intimate and something I will remember for the rest of my life.

After a final cooling dunk, we towelled off, and headed inside. I cast a final look around and still saw no one to the north. To the south, the figure on the balcony had gone. When we made it back down to the apartment, I motioned us over to the collection of packages and selected the one that seemed to be some clothes she'd ordered, handing it to her and adding "Strip spunky girl'.

She beamed, then frowned, "Don't we have to be working?"

"Look, I've earned some really browny points recently and I've let the powers that be know that you've done well too, and you have, so it won't matter if we push things a little this morning ok?"

Extracting the goods, she laid them out on the kitchen table. It was quite a haul. There were; two pairs of shorts, the same number of plain tshirts, two short sleeved round necked dresses (one in white, the other classic black), a short sleeve v-neck lightweight black jumpsuit, a white maxi dress with a red hibiscus print and a knee high slit. A 1950's style 'polka dot on maize', lapel collar, dress rounded out the major items. A package within the package contained half a dozen cotton thong undies, two gray lightweight night dresses, two simple tshirt bras and a more impressive black push up one. From the tags I could tell they were from a mass produced online store and wouldn't be amazing quality, but for a first wardrobe, they'd be more than sufficient.

The aim I'd left 'him', as at the time I'd still referred to him as such, was to buy four days' worth of 'around the apartment' clothing and one formal outfit. "Excuse me Timi, but this is not the amount I told you to purchase!"

"But at these prices, it was so cheap..."

"I'll need to teach you about quality v quantity. Now get moving, I want a fashion show."

At that she pulled the straps of the bathers off her shoulders, peeling the rest of it down from her body. Her penis swung into view and engorged instantly. She looked at me sheepishly. I smiled, went to the kitchen and came back with the glass. "Anyone might think you are a bit excited there. Heck that thing doesn't quit!"

I walked up behind her, reaching around to put the glass of frozen spunk as a target. Then I moved her to face away from the haul of clothes. Spitting into the other hand, I began jacking her off whilst nibbling on an ear, biting a shoulder and kissing her slender neck. "The sooner you cum, the sooner we play dress ups... Cum for me spunky... spurt your hot cum." She was getting there but needed more. Applying more spit, I increased my speed and force. "Close your eyes, picture my tits... cum on them... glaze them for me..." She was closer. I could feel it. "Coat them...". She started to tense. "Cum for me..." I whispered, then stuck my tongue in her ear. She spasmed in that very fashion that only is common to men, groaned and unloaded. The first shot went rogue and high, splattering on the kitchen bench top, the others hammering the insides of the glass, adding to its contents.