Prelude

Sailing Date part 0 prelude

Well this is definitely the most unique second date I’ve been on I thought to myself as I turned my car onto the dirt road. I’d met the girl I was going to see on tinder. Unlike the vast majority of dates I had been on that year; the first date had been a blast. There were a couple awkward pauses, sure, but by and large Hannah had been a lot of fun and very easy to chat with. Bonus points that she didn't seem to notice, let alone mind, that I was only 5’4” and not exactly buff. Scrawny, scrawny is the word, my inner monologue reminded me.


It had been her that suggested going sailing for a second date. She had a small sailboat, kept at a dock her family owned a little ways out of town.


‘A little ways’ turned out to be more like ‘an intermediate ways’ if you asked me. It had been nearly a forty minute drive


Finally though I was turning into a driveway. It was an empty lot except for a small shed and a dock. Hannah had explained that her parents bought the lot planning to eventually build a cottage. But that was nearly ten years ago and plans were no further than that.


I pulled my car up next to hers and put it in park. I was wearing a baggy grey shirt and jeans with a bathing suit under them. Hannah had told me to bring one and I figured this way I wouldn’t have to change, just lose the pants. The bathing suit was a baggy red thing.


At first I didn't see Hannah anywhere, but the boat was in the water a short distance away. Smaller than I had expected. I don't know why but for some reason I had pictured something sort of grandiose when she said sailboat. Something you could cross the ocean in, or at least sleep on. It surprised me when she said she owned one. This made a lot more sense; it was just a little dinghy sailboat, big enough for two people, maybe three. Around fifteen long perhaps. The small boat made me a little nervous, I really wasn’t comfortable swimming, in that I didn't know how to, there was no use sugar coating it.


Just then Hannah emerged from the small shed and spotted me. Her face lit up and she waved. That was a good sign. She was gorgeous, she had a fair freckled face and dirty blond hair that was in a single long braid reaching well past her shoulders. She was wearing a pair of tight black Lycra shorts and a white tank top under a pretty slick looking black life jacket that she somehow managed to make look good. It was form fitting, hugging her body tightly unlike most of the -allways slightly too large- vests that everyone seemed to have on their power boats. The front was a solid panel, with no visible buckles or zipper.


I walked briskly over to greet her.


The fact that Hannah was wearing a lifejacket was a bit of a relief, I honestly always preferred to have one on but sometimes felt a bit awkward if I was the only one wearing one.


“Hey! Welcome!” Hannah rushed over and gave me a big, and unexpected, hug. Hannah was noticeably taller than me and her hugs were legit, she squished me into the foam of her lifejacket. I was thankful for the lack of hard plastic buckles on the front of it. It struck me that it was probably a very comfy jacket.


“Are you excited?” Hannah released me, she was beaming.


“Ya definitely, I’ve never done this before.” It was the truth, I had been out on friends' power boats once or twice but never a sailboat, although I was also more than a little nervous.


“You’ll love it. It’s a blast.”


She looked me up and down.


“You brought a bathing suit, right? You don't want to sail in jeans”


I nodded. “Ya I have it on underneath.”


“Great!” She was still looking at me then at my car.


“Wait, what about a lifejacket?”


So I guess I should have grabbed it, I thought back to when I left the house and briefly considered getting one from the basement.


“No I don’t “ I responded, I hadn’t bothered to bring one as every time I’d gone boating with friends they had plenty of them on their boats.


Hannah seemed concerned. I shared the concern as I wasn’t particularly comfortable going out on the tiny boat without one, I liked this girl but wasn’t sure I was ready to drown for her.


“Crap, that's my fault, I should have told you to bring one.” She bit her lower lip and looked back at the shed for a moment then turned to look at the boat. “We might have something in the boat, let me go check.”


I considered mentioning that I couldn’t swim but it was a bit embarrassing to bring up, and Hannah seemed determined to find me a lifejacket anyway, so for the moment I just went with the flow.


I followed her to the side of the boat as she jumped in, opening a cargo hatch and digging through it. After a few moments she closed the hatch and seemed to think.


“Ok, let me go check the shed.” She didn't sound confident.


This time I waited by the boat as she ran off to go search the shed. Her long braid bounced as she jogged lightly. I gazed out at the lake while I waited, there was already a steady breeze; it was rustling the trees and creating ripples across the surface of the lake. It was really pretty beautiful. Just my luck that something stupid like a lifejacket would ruin what clearly had potential to be an amazing date.


Hannah was only a few minutes in the shed, she was already walking back when I turned away from the water. The fact that she didn't have anything in hand was a bad sign.


“Ok, so there’s nothing there.” Hannah seemed annoyed.


I cursed myself for not bringing a jacket when it occurred to me to do so.


“I’m really sorry, but we can’t go out without a lifejacket for you. I know it's kinda dumb but if I got a ticket for you not having one I wouldn’t be able to compete in the regatta-“ I cut her off mid explanation.


“It's fine, I honestly wouldn’t be comfortable without one, I’m not really comfortable swimming. I actually almost brought one but didn't want to seem weird and figured you’d have them on the boat.”


“Ow” She was surprised but didn't seem off-put. “That’s fine, ya we always wear them on the boat. I just don't have extras because I use the boat for racing, so I don't keep anything on it. You don't need to be embarrassed about that though, that’s dumb”


It was a remarkably easy exchange, I was really enjoying spending time with Hannah. I felt comfortable with her. We stood around for a moment looking at the boat and the lake. I looked up at her standing next to me and marvelled again at how out of my league she was. I couldn’t believe we were going to have to just head back to town. It surprised me how disappointed I was considering the idea of sailing was well outside my comfort zone.


Hannah seemed to sense my gloom at the turn of events. She frowned as she looked over at the boat and lake.


Then she turned and looked down at me, and her face became almost calculating, like she was sizing me up. She cocked her head to the side a little and seemed to be scanning my torso.


“Well,” she paused. “This is probably dumb but there might actually be an option here.”


I didn’t say anything, waiting for her to continue.


“This is a bit of a weird idea… my little sister's life jacket is out here. It’s a kids life jacket. But… you’re pretty small, I mean you’re small enough that you might fit into it… technically.”


She was as gentle as she could be regarding my stature but it still stung a bit, given that this was the first time she’d mentioned it in any way. She continued when I didn’t immediately respond.


“Only if you want to try it, I mean. I don’t expect you to.”


Comments about my size aside, the news was good. I really didn't see what the big deal was with a kids jacket.


“No, that's great!” More enthusiasm than I meant to show. “I mean I’m fine with that if it means we’re still on.”


She seemed less sure but brightened up and smiled at my enthusiasm. She started walking back towards the cabin, gesturing for me to follow.


“It MIGHT fit, it really is meant for kids.” Turning to me “And also it’s juvenile, like really juvenile. But honestly there’s never anyone else out here so it’s not like anyone will see you.”


“I mean if it fits me I don’t really care”


She seemed to like that comment.


“That’s honestly, really refreshing. I like that you don't seem to care that much what people think.”


She gave me a smile and the combination of smile and compliment made my knees weak.

The Lifejacket

Sailing date - part 1

Hannah opened the door to the shed revealing the interior.  It was pretty run down, containing mostly old junk it seemed.  The life jacket was immediately obvious.  It was a vibrant yellow that seemed bright even in the dim shed.  It had reflective strips which caught the sunlight coming through the open door.  My eyes were drawn to them immediately.  It was hanging on a hook on the wall next to some old ropes and shovels. 

Hannah walked over and retrieved it, I stepped back outside, making room for her as she exited with it. 

The lifejacket that Hannah was holding was very different from what I had expected.  I was picturing something with unicorns on it or something.  The lifejacket was your typical shade of neon yellow but its shape was very unusual.  

As Hannah shook it out the first thing I noticed was the collar. I had seen kids' life jackets with a sort of hood behind the head before, but this one was different.  It was thick. Like easily three inches thick. And it looked like it would sit flat across the shoulders with a cutout in the middle for your neck.  The foam panels in the front were also really thick looking. And it had a burly mess of straps hanging off of it. I was frankly more than a little turned off.  

Hannah seemed unsurprised by my reaction “Ya, I know.  It’s a bit much.  It’s from years ago, before we moved here, when we used to sail on the ocean.  It’s literally called the ‘super safe’”.

She hesitated. “I totally understand if you want to go back into town.  But honestly there’s NEVER anyone out here.  So it’s not like people will see you.  And it’s SUCH a nice day…” She held the jacket out and opened it up, giving me puppy dog eyes. “…I’ll oweeeee you?…”

It was enough for me to try it. Feeling very uncertain, I turned around and started to slide my arms through the holes. I was reasonably confident this crazy life jacket was not going to fit me anyway.  

“Ow my god! Really? You’re the best.”  Hannah’s excitement made it immediately clear she didn’t actually think I would go for it. She started to move forward with the lifejacket but then stopped.  “Do you have an extra shirt? If not, you might want to lose that one now so it doesn’t get wet.”

I did not have an extra shirt, I was also not that confident in my body and had not been shirtless in front of this attractive female yet.  But I did not want to drive home with a wet shirt, or appear to be uncomfortable being shirtless. 

I quickly and clumsily pulled my shirt off over my head. Hanna held out a hand for it and I gave it to her.  

She tossed it over her shoulder and held the lifejacket back up. 

Now even less comfortable without my shirt. I put my right hand through the first hole in the jacket.  It felt a tiny bit weird to have her hold it as I slid my arm through.  But Hannah continued to stand there holding the life jacket open. So I slid my arm the rest of the way through and rotated my back to her, looking over my shoulder for the other hole. I was struck by how soft the material was against my arm, it wasn’t the typical cheap nylon you got on every life jacket I’d seen previously. It felt almost like a velvet on my exposed skin. It felt expensive. 

I was having trouble finding the other hole, partly because the jacket was so small that the hole was more in the small of my back, partly because Hannah was holding it a little too high, causing me to have to bend forward slightly.

“Here”. Hannah seemed to have decided I needed help.  She pulled the lifejacket back down my right arm to around my elbow.  Then let go of the jacket with one hand, grabbing my left wrist, and manoeuvring it, gently but pretty firmly,  through the other hole. 

For a brief moment I was kinda stuck, with both my arms part way through the jacket and a little too close together at the elbow.  I was emotionally a bit torn here, on one hand I was being manhandled into a kids life jacket, on the other I was getting some very close and personal attention from an attractive female who I was very fond of.  

“Haha- sorry- you look kinda funny.  Ok sorry let me help.” She had laughed but it was in a kind- not a teasing way.  Hannah had moved around in front of me.  She reached around me under my left arm and over my right shoulder.  Taking hold of the lifejacket and pulling it up my arms. It got tighter as it moved up them. I was sure it was not going to fit and nearly said so, but Hannah gave it a good wriggle and all of a sudden she managed to get it around me.  The jacket practically popped up onto my shoulders, my arms were suddenly free and the jacket was around my torso instead of tied up on my arms.  

With the lifejacket now ‘on’ I was struck by a few things very quickly. 

The first was the softness of the material. I had noticed it already on my arms but with the jacket now resting on my bare shoulders, chest and upper back I was really struck by it.  It was almost fuzzy in how soft it was.  It was really comfortable, and unlike anything I had worn before.  

The next most notable thing though was definitely the collar.  Again I had noticed earlier that it was unusually thick and seemed designed to wrap around the sides of your head.  I could now confirm this observation.  The collar was thick enough, and wrapped around the sides of my head enough, that I could feel it on the bottom of my jaw bones and back of my scalp.  It frankly felt pretty restrictive. 

I was brought back to my senses by Hannah, she had never let go of the life jacket after pulling it up over my shoulders.  Now she was holding the two front panels and gave them a shake as though to line them up.  The feeling of the soft liner rubbing over my skin as she did this gave me tingles.  The jackets straps and buckles banged around, sounding heavy duty and metallic. 

Hannah had the zipper lined up.  A moment later she had it connected and with one fluid motion pulled the slider up.  Sealing the lifejacket around my torso. Even the zipper made a more heavy duty sound than a traditional jacket. As she did up the front of the vest I felt it pulled in more tightly around me.  The collar, in particular, was pulled up tight against the back of my neck when the two halves were pulled together.  And I felt contact with the jacket more fully across my upper back. 

“Wow! You actually fit.” She caught herself. “Sorry, I just didn't really think you would.”  She took a couple steps back. “Ow man this is great, we can actually go out after all.”

For my part I was busy taking stock of the jacket around me.  The back was a firm, almost rigid, panel.  I twisted left and right a little and noticed how I really did so at the waist only, my torso felt a bit like a plank. I tried moving my head around and was really limited on that front, I could look left and right if I really wanted to but only a little without angling my chin up to clear the thick foam collar.  

Looking down at the jacket I could see the chest strap hanging loose.  It also looked more premium than what you found on typical life vests.  Again the material surprised me, it wasn’t the normal sort of stiff webbing you expect, it was smoother and more flexible, like seatbelt webbing. Both sides of the chest strap ended in metal rectangles. 

I pulled the two halves of the chest strap toward each other but they were, unsurprisingly, too short. I figured it was probably ok, the jacket was zipped up, it would work even without the chest strap.

Hannah walked back up to me. “I can let some slack out for you, I know it’s kinda hard to reach things when you're wearing that haha.”

“Have you worn this?” I was surprised.  I could feel but not see her tugging on something on my right hand side, under my armpit, as she answered.

“Ow ya! It was my lifejacket before it was my sisters, I actually wore it until I was like 14 I think. It does actually fit pretty large.”

I flustered at the reminder that I was wearing a children's lifejacket.

“I think the only reason I got out of it was honestly because my sister outgrew her baby one. I still had lots of room in it.”

She stopped messing with the jacket and stepped back 

“Do those straps reach now?”

I turned my attention back to the chest straps, they reached each other easily now.  But I had no idea how to connect them.

“Ahh, how do they-”

“Here” Hannah seemed to read my mind and stepped back up, taking the two straps from my hands. She passed one rectangle sideways though the other. It made a dinging sound at the metal on metal contact.  That was obvious enough that I should have figured it out, I thought.  

Hannah then reached around me and pulled on the same out of sight fastener on my right hand side.  I was pulled forward by the unexpectedly hard tug and bumped into her.  

“Sorry!” She apologised putting a hand on my right shoulder to steady me before pulling again.

I felt the strap around my chest pull in tight.  Squishing the foam inward around my torso.

Hannah took a step back “There ya go. Cosy?”

The lifejacket was bizarre, it wasn’t at all uncomfortable despite being really pretty restrictive.  I twisted around trying to get used to it. Taking hold of the shoulders I was struck by how dense yet squishy the foam felt.

“Well I sure feel safe” I joked trying to make light of the situation.

“Ya I actually do remember it feeling kinda safe and cosy.” 

She smiled, folding her arms over her own, much cooler, lifejacket and leaning back slightly as though to admire me. 

“You know you’re actually pretty cute in that” 

The compliment gave me tingles on the back of my neck.  I was taken aback but went with it. Making a joke pose like a superhero, I put my fists on my hips and turned at the waist, leaning back and putting my chest to the sky. As I rotated I noticed again that I couldn’t really turn my head with the collar and had to twist at the waist a bit more than planned.

Hannah laughed. I beamed. 

“Is it actually ok though?  It looks not too tight on you but I know it’s pretty restrictive to have on.”

“It really isn’t that bad.” I did feel weird but I was committed to dealing with it at this point and might as well be chill about it. 

“You’re honestly so awesome for going along with this.”  

I’d never received so many complements in so short a time. 

Hannah’s tone went back to business. “So. There’s ahhh, a couple last straps….”  She trailed off and stepped forward, reaching around both sides of me. She was close enough that her life jacket brushed up against mine and I could smell her hair.  I did my best to remain calm.  I felt her grabbing at the small of my back. She stepped back with a long thin strap in each hand.  “These ahhh, … go between your legs.” She looked down.  “You might want to take your jeans off first tho. cuz you obviously won't really be able to after...”  

This took me by surprise, I had noticed the leg straps on the thing when she first got it.  But I hadn’t thought she would imply they actually be buckled up.  The jacket was for kids after all.

“Really?” I hadn’t meant to speak but maybe my expression was enough even without my saying anything.  Hannah didn’t look angry.

“Yaaa I know. Sorry.” She sounded apologetic. “It’s honestly up to you. Like I said, you really don't have to wear it.” She was still holding the ends of the leg straps. 

The implication was that if I was wearing the jacket I apparently had to wear it with the leg straps done up...  I wasn’t going to bail or argue with her at this point so I just sighed inwardly.  Feeling very awkward, I started to undo my jeans.  Hannah smiled and blushed, dropping the crotch straps to give me some freedom of movement. 

Removing my jeans with the bulky lifejacket on was actually more difficult than you would think. The collar and bulky foam over my chest restricted my movement and visibility so I had to feel around for things.  I had to move my torso a bit like a plank as I worked the pants down off my bathing suit.  Maintaining my balance was proving a bit of a challenge.  As I started trying to get my first leg out of the pants I realised I needed to take my shoes off, while standing on one foot to accomplish this with my pants halfway down I nearly managed to tumble backwards.  

Hannah, seemingly concerned, was quick to help steady me.  But instead of offering me an arm, she grabbed what must have been a loop on the back of the lifejacket, keeping a hold of it while moving to stand behind me.  At first this seemed weird and I almost straightened up, but then I lost balance again and she took most of my weight, easily holding me up in my half bent over position. It was actually really helpful.  It occurred to me that perhaps this was just a force of habit; it was how she helped her sister when she was wearing this jacket. Or even how she was helped when she used to wear it. Either way it was remarkably easy to keep myself up with her holding the jacket, and I had the use of both arms. I managed to get both shoes off and legs out of my jeans in pretty good order with her holding the jacket steady.  Straightening up I half heartedly folded up my jeans.  

I looked for Hannah planning to hand them to her as I had my shirt.  She was still behind me holding the loop on the back of my lifejacket with one hand; but using it to keep her own balance now as she leaned around in front of me. Half hanging in front of my waist she reached with her other hand between my thighs.  I froze awkwardly as she grabbed the pair of crotch straps hanging from the back of my life jacket and pulled them through my legs.

As she straightened up back into a standing position; the ends of the straps in her hand. I suddenly felt them pulled up into me.  The straps pulled up tightly, bunching up my bathing suit and giving me a wedgie.  I let out a quick yelp at the unexpected turn but Hannah must have noticed the sudden resistance in the straps as she had already lowered her hand to relieve the pressure. 

“Sorry! I guess we need to make those a bit longer for you.”  She blushed again slightly as she let go of the straps, letting them fall and swing back though my legs. 

“All good” I managed. Pulling my bathing suit out from my but awkwardly. 

“Should have seen that coming I guess, you’re small but not as small as my kid sister” Hanna laughed as she went down onto her knees by my side, leaning around behind me.  The second comment on my stature didn't seem to bother me as much as the first for some reason.  Possibly because I was distracted. 

I could feel her tugging on the straps behind me as I stood there. I twitched suddenly as her arm brushed against the inside of my bare thigh, she was passing the straps back through my legs.  Hannah took the straps in her other hand as she shuffled around on her knees to my front.

“These are kinda a pain to adjust sorry.   My dad switched out the original buckles for these sliding ones at some point.  I remember being able to adjust them without undoing them when I was a kid”

This time when Hannah brough the first strap up to the buckle it connected easily with lots of room to spare. But to my surprise she immediately unclipped it again, letting it fall loosely back.

I was confused “Did that not work?”

“Huh? No sorry it was super loose I let out too much.  Let me try again. Sorry, I told you it was a pain”

Not sure what to say I again stood there as she pulled at the straps behind me. This time just leaning around my leg rather than moving. I pulled at the foam over my chest with my free hands and rolled my shoulders, trying to get used to the feeling of the bulky vest.  Apparently having trouble Hannah gave up leaning around me and got briefly to her feet to move behind me. I really noticed the presence of the collar with her behind me as it completely  prevented me from looking over my shoulder to see what she was doing.  

Finally Hannah seemed to be finished as she half got up half and crawled around back in front of me. Plopping herself down on her but in front of my feet. I spread my legs as she casually reached between them and retrieved one of the straps.  As she pulled it up towards the buckle I felt it bunch up my bathing suit and press into my crotch again. She’d made it too short again, but this time hadn't pulled it up as suddenly or aggressively as so I managed not to yelp.

But then there was a click as she managed to get the strap buckled in. 

“There we go!” Hannah seemed pleased as she reached quickly through my legs again for the second strap. Without really thinking I leaned forward and reached behind me to try and pull the strap out of my but as it was giving me a very mild wedgie.  The second strap must have been slightly shorter than the first as I felt it pull up more sharply as Hannah got it buckled in. 

I straightened back up and both straps pulled up more tightly but the second one, on my right, really cut up into me, and I quickly leaned forward again.  

“Ahh that's a bit tight Hannah.” I complained without a thought. 

“Crap sorry” sounded genuine. 

She was halfway to getting to her feet and dropped back down before reaching up and uncliping both straps.

“Ow shit sorry, I got the second one twisted, was it both of them or just that one?”

“They're both pretty tight, can't you just leave them loose?”  

“No, it needs to be snug, but it shouldn’t be uncomfortable. Especially seeing as we are really pushing things already using a kid jacket for you.  You’re probably over the weight range”  Apparently she was over moving around as she was just adjusting the straps by reaching though my legs this time.

“I told you they are a pain to adjust, I should have marked where it was set for my sister before changing it.”  

“Sorry about that” I said it in a joking tone as I awkwardly tried to keep my thighs as wide apart as I could while she worked at the straps though them. 

“It will be so worth it, you’ll have a blast I promise.  Ok, here this should be good.”

She leaned back pulling both straps though with her as she moved from her but to a kneeling position in front of me

“Ok hold on let me make sure I don't twist one again. God I remember that hurting. Sorry about that, I haven’t done that in ages” She was kneeling in front of me and holding the two crotch straps in her right hand, she took a moment reach though my legs again with her left hand reaching her arm all the way   Through to grab the the far end of the straps where they connected to the jacket at the small of my back, and running her hand down the entire length of the straps back to the front.  “Ok ya were good, no twists.”

As she pulled the first strap up bunching up my bathing suit once again I felt the strap press into me at the exact moment I heard the loud click of the buckle.  Hannah pulled at the strap a couple times causing some uncomfortable rubbing.  

“OK, there finally”

She brought the other strap up, bunching up the other side of my suit and again I felt it press up against me just as the buckle clicked. 

“OK”

Hannah got to her feet brushing the dirt off her knees as she did so.

Once on her feet she stepped toward me and grabbed the shoulders of the jacket.  Unexpectedly giving me a good shake. Causing the jacket to shift around and the straps between my legs to pull up into me slightly more a couple of times. 

“You look all good. Ready to go?” 

I nodded. Trying my best to remain casual despite the mass of foam secured around my torso and the straps pressing into me between my legs. 

The straps between my legs were just tight enough to be impossible to ignore.  I had an urge to pull at them or pull away from them.  

“Here’s your shirt, want to put your stuff in your car? I can put your keys in my dry bag so they don't get wet but it’s a bit small for clothing.”

I nodded, taking the shirt and turning back to my car.

Sailing

Sailing Date - Part 2

 It’s hard to express how awkward I felt walking back to my car in nothing but my bathing suit and gawky lifejacket. The ground was soft moss and grass under my bare feet.  I rarely even wore shorts; having my legs and feet bare somehow seemed to enhance the bulk of the jacket around my torso. 

I was doing my best to ignore the thick collar and straps between my legs as I deposited my clothing in the back seat of my car.  But the straps between my legs in particular made that a losing battle. As I was walking back down toward the boat I couldn’t resist hooking a thumb under the straps where they passed under my crotch and trying to pull them down a bit.  It worked as long as I was actively pulling at them but as soon as I let go they pressed right back up into me.  Hannah was looking my way now though so I resisted the urge to pull at them some more. 

“All ready to go?” Hannah was beaming again, I nodded trying to be enthusiastic despite the awkwardness of the jacket. 

“Give me your keys, I’ll put them in here” Hannah had her small waterproof bag open. I handed over my car keys feeling a bit like I was signing my life away.  Hannah smiled.  Alright hop aboard. 

I climbed down into the small boat rather awkwardly; in part because I was just awkward, but the bulk and restriction of the lifejacket sure didn't help. Hannah set about untying the boat, moving fluidly and with a confidence I only wished I could emulate. 

I took a seat on the far side of the boat. There wasn’t a ton of space, the boat consisted of a raised beach seat along both sides and a small foot well in the middle.  Sitting down was a relief, with my legs bent the two straps between my legs loosened off enough that they weren’t pressing into me anymore.Tho the collar and general bulk was still enough of a hindrance to prevent me feeling completely normal. 

Hannah hopped lightly into the boat like it was nothing. 

Until now the sails had been flapping about lightly in the breeze. But Hannaha pulled some rope through a sort of clamp and in moments the sail was taught and the boat was gliding over the water as if by magic. 

I almost forgot about the lifejacket for a moment as the boat started moving. It was really cool to glide over the water without an engine like all the boats I’d been on previously. 

I had assumed we would sit on opposite sides of the boat the entire time but as we pulled out and started moving more quickly my side of the boat started to rise up out of the water and Hannah moved to sit next to me, with her weight added to my side of the boat we seemed to be heavy enough to keep things balanced out. 

“Ok so, sailing lesson one.  When we go to turn; the sail will flip over to the other side, I’ll yell tacking before I turn us.  When that happens we need to duck so the sail can swing over to the other side, and we also need to switch sides to keep the weight right.” 

My face must have betrayed that I wasn’t following everything. 

“Don’t worry , just do what I tell you” She smiled and patted the back of my bulky lifejacket.

I thought the boat was moving surprisingly quickly over the water but as it turned out I hadn’t seen anything yet. 

Hannah turned the boat into the wind and the sail started to vibrate.  The boat started to lift out of the water and felt to me like it would flip, but Hannah seemed unworried.

“Ok do what I do, sit up here with me and lean back a bit.”

Hannah had already moved from the seat to the side of the boat. She had the rudder in her left hand and was leaning out backwards over the water. 

Very unsure of myself I put my hands on the side of the boat behind me and slowly lifted myself upwards. Positioning my but on the edge of the boat the way Hannah was.

As I moved up to the higher seating position my legs straightened out and the straps running between them were pulled up annoyingly into my crotch again.  Glancing down I was embarrassed to see them bunching up my bathing suit. I was too busy clutching the edge of the boat with both hands to pull at the straps but managed to loosen them a touch by leaning forward slightly. 

With my weight further out apparently Hannah felt confident pushing the boat even more into the wind. I gripped the side of the boat tightly as we sped up. The boat was at nearly a 45 degree angle to the water and I felt like I was going to fall overboard. As annoying as the thick collar and the straps between my legs were, I was very thankful for the bulky lifejacket at that moment. The boat seemed on the verge of flipping and Hannah leaned out back over the water to help off-set the weight.

“Lean back!” 

I hardly had time to process her order when I felt my lifejacket pulled firmly backwards.  Hannah had grabbed the handle on the back of it again and was using it to move me into the ‘correct’ position out over the water.  The boat levelled out slightly as my weight was shifted out over the side. But the side effect was that the straps between my legs were pulled up even more, giving me a wedgie. I wanted desperately to pull at them but I wanted even more desperately not to fall overboard. My fingers were getting sore from clutching the side of the boat. I tried briefly to lean forward again but Hannah was still holding onto the handle and resisted my half hearted tug seemingly without noticing.  

“Ok ready?”  I wasn’t sure what she was asking if I was ready for; but the answer was no. 

“Tacking!”

Hannah switched from holding me back to pushing me forwards, back into the boat. She kept her hand on the back of my life jacket, holding onto the handle there.  She guided me down into a crouched position in the middle of the boat as the boat suddenly swung round and the sail swung over our heads.  Then she was pulling me forward again towards the far side of the boat. The boat was moving again and the far side was rising up out of the water.  Hannah half pulled me up to the far side before finally releasing her hold on my jacket and practically throwing me at the far side. I did my best to get back up onto the side of the boat as quickly as I could, almost forgetting the lifejacket for a moment in the scramble. A moment earlier it had felt like the boat would flip but as we both got up on the far side it stabilised and flew forward over the lake instead.  I had to admit it felt awesome, almost like flying. 

“Lean back a bit more!”

I felt the pull on the lifejacket again as Hannah pulled me out further over the water, so that I was leaning back over the edge.  I was less scared this time but the straps tightening up and pulled into my crotch was exactly the same.  I shifted at the hips, trying to make them more comfortable without the use of my hands.

“Are you having fun?!”  Hannah was still holding the back of my jacket but more casually now. It was almost kinda like she had her arm around me. 

I smiled back at her to answer yes and was stuck by how attractive she was.  She looked so confident with the rudder, her long braid was catching the wind and her slick back life jacket hugged her body, exaggerating her curves. 

“It feels like flying!”

Her face lit up.

“Do you want to try??” She gestured at the rudder with her head.

I didn’t think it was a good idea but also didn't want to disappoint her.  So, I am very unsure of myself.

“Ahh, sure..”

“Don't worry there’s nothing to hit out here.”  She turned the boat directly into the wind and suddenly the sail went dead, flapping lifeless.  The boat smoothly slowed to a gentle glide.  As it did so it also levelled off our side of the boat falling back down to level with the far side.  We both straightened up into a normal sitting position.  The straps between my legs finally loosening off as I bent at the waist.  I managed a quick tug at them when Hannah was looking the other way, getting them untangled from my bathing suite. 

“Ok here.”

Hannah placed the handle for the rudder on the floor and started to get to her feet.  Apparently she was still holding onto my lifejacket as I was suddenly pulled upwards. Hanna released me just as I got to my feet, and moved around in front of me.

“Ok, so sit right here.” She put a hand on each of my shoulders.  Pressing me backwards and down.  Into the spot she had been sitting. 

“So, right now we are in ‘irons’ which means pointing right up wind. This is how you make the boat stop. The closer to irons you are the faster we go until you are pointed right up wind, so when you turn, turn at least 30 degrees and we won't be going too fast”

She scooped up the rudder handle and put it in my hand.  I was overall pretty unsure, but also a bit excited to try. 

Hannah sat right next to me and leaned around my back grabbing my right forearm in her hand to guide my movement, her lifejacket squishing up against my own.  I did my best to try and focus on what she was saying.

“Ok this way to go right, this way to turn left. Turn right tho so we are on the right side.”

Our life jackets rubbed on each other making a loud swishing sound on each movement.

I nodded trying to ignore the smell of her perfume and pulled the handle towards me turning the boat right.  Right away the sail filled up again and we started moving, the boat rising up under us.  

“Good.  Now lean back a bit”. Hannah let go of my arm and moved her hand back to the handle on the back of my jacket, pulling gently and guiding me out over the boat.  I noticed the now familiar feeling of the crotch straps pulling up between my legs but I was having enough fun to more or less ignore them for the moment. 

“So turn more to the right and we’ll slow down.” I did as she said and as the boat slowed down Hannah pressed on on my back, moving us into more of a sitting position.

“The faster we go the more we have to lean out to keep the boat from flipping.  We are basically just offsetting the force in the sail.  Turn us back up wind a bit” 

I turned us left again towards the wind and felt the boat rise up.  Hannah pulled on my lifejacket, leaning us back out over the water. The lesson continued like this a few more times. Hannah had me slowly turn into and out of the wind, guiding me from sitting to leaning and sitting to leaning.  I was having fun but the constant sitting up and leaning back was causing the straps between my legs to pull and rub and brush in ways that were starting to become distracting.  Having them pulled up tight was one thing but the constant on and off was another.  I was trying to follow Hannahas instructions but one of the two straps was caught up under me in a particularly awkward  way. I was getting desperate to adjust it but didn't have a free hand.  

“You're doing great! Let’s try tacking. Get up a little speed first”

Hannah pulled me back out over the water, pulling the straps up between my legs.  I squirmed a bit as the need to adjust it was really driving me mad.

“Hold on, sorry.” I couldn’t stand it any longer. I leaned forward and let go of the boat to pull at the strap, it didn't matter that it was right in front of her I had to adjust it. But I forgot about the rudder and absentmindedly turned us upwind.  The boat sped up suddenly just as I hooked my left thumb under the crotch strap to pull at it. As the boat shot forward it also shot upward under us obviously on the route to flipping.  Hannah yanked backwards on my lifejacket but was too late.  My thumb got briefly stuck between the crotch strap and my crotch, just long enough to prevent me grabbing the boat as I toppled over backwards. Hannah, to her credit, held onto my jacket far longer than you would think.  With my weight gone the boat flipped instantly and she must have splashed into the water on the far side.  I crashed into the water upside down.

 Terror is the word to use when you fall into the water and can’t swim.  My mouth and nose full of water I immediately started to twist and flail around; trying to grab hold of something solid. Trying to find the surface. I had no idea which way was up. Everything was liquid and everything was a sinking spinning panic. Then my whole body was suddenly twisting and spinning around like some alien force had me in a tractor beam. Pulling my torso backwards past my legs and spinning me around. The surface spun into view a split second before I crashed through it. Coughing and still splashing around. I failed around on the surface for a moment or two.  Getting a few gulps of air I started to calm down a bit, and suddenly my surroundings came flooding back into my awareness.  The lifejacket was suddenly there; tightly wrapped around my torso, it was holding me like King Kong held Anna. Like the hand of a giant had come out of the sky to save me.  For a few moments it was all I was aware of.  The thick bulky foam strapped tightly around my torso, the collar cradling and supporting my head, and the crotch straps snug between my legs. I kinda sank into it, feeling viscerally that it was the only reason I wasn’t downing. It was so bulky and tight and I was immensely grateful for every ounce of it. Trance like, still blinking and coughing, I reached up grabbing the shoulders with both hands.  Clutching it like a comfort toy.  The collar was like a pillow, I relaxed and just allowed it to hold my head.  No longer kicking; my legs dangled down below me in nothingness. I absently felt around with them; hoping for something solid but knowing that there was nothing firm for them to find.  Aware of my legs hanging down into the abyss I was suddenly grateful for the tight straps between my legs.  The crotch straps were as tight as they had ever been, but now the pressure was reassuring me that my torso was staying where it was; nice and snug inside the jacket, with no danger of slipping out the bottom.  

The contrast between my torso and legs was interesting.  My upper torso was tightly wrapped, even my arms were held in close with the jacket.  My whole upper body felt safe; held and supported.  But my legs felt heavy and loose, hanging out in space by themselves, like explorers. I twisted in the jacket absentmindedly.  Suddenly aware of, and surprised by, the fact that I felt cosy and safe. 

I understood now what the crotch straps were for.  I briefly imagined what it would be like without them; my torso sliding down, slipping out the bottom of the jacket, following my heavy legs down deeper into the water. Clutching the jacket as gravity tried to suck my torso out of its protection. But the straps were there and they held me tightly in it. I was twisting and turning in the jacket, like I was in bed, cosy under the covers on a sunday morning.

A huge splash startled me. I twisted in the water, moving into a more vertical position and rotating to look.  The boat was back upright and Hannah was standing on it, dripping wet.  For a moment I was terrified she would be furious but then she turned, she was laughing and smiling. 

“Your first flip!” She laughed. “Did your hand get stuck on the crotch strap?!?” 

Now it was my turn to go pink. How on earth did she catch that?

Hannah was still laughing “No, no I’m sorry it’s fine, come on back up here” She was gesturing me to swim over. 

I did understand in principle how to move around in water; you’re supported to kick and move your arms, so that’s what I did, trying to crawl through the water toward her.  Hannah looked confused for a moment watching me then shook herself out of it.

“Ow, shoot, ok hold on.” Hannah looked around the boat for a moment before ducking down out of sight.  A moment later she popped up with a long yellow strap in hand. 

“Here, grab this.” Skillfully, she tossed it out. Landing it in the water just within arms reach. I managed to grab hold of it and a moment later Hannah was pulling me in much more effectively than my splashing was managing. I was pretty tuckered and happy to be pulled in, well past any inhibitions or pretence of ego by this point. 

As I reached the boat I grabbed the side and made an effort to pull myself up. Before I had gotten more than my torso out of the water Hannah was already leaning down and grabbing hold of my jacket.  Hauling me up out of the water with surprising strength. The jacket pulled up sharply around me; I felt the collar press up into my head but I was lifted by the waist and crotch straps.  While tight it was surprisingly not uncomfortable, though I did have one serious wedgie as she pulled me in over the side. I lay on my stomach dripping wet in the bottom of the boat, my legs splayed out behind me.  With some effort I rolled onto my back and bent my knees, reaching down to undo my wedgie as Hannah fought a giggle fit above me. I was generally past being embarrassed by this point, surprisingly easy with Hannah, despite her laughing I never once felt she was not laughing with me at the absurdity of the situation. 

“Ow man that was really funny, I'm sorry, here let me help.” Hannah leaned down grabbing the shoulders of my life jacket and pulled down on it. I hadn’t realised the jacket had ridden up on me but as she pulled it down I felt it against the top of shoulders again and the straps between my legs loosed up a bit.  Hannah grabbed my arms and helped me get into a sitting position. 

I twisted a bit in the jacket and managed to get up onto the seat wiping water from my face “Sorry about flipping it…”

“Ow man no not at all, it’s made for that. That’s the first time I’ve seen someone bail because they got stuck on their own crotch strap tho.” She was still giggling.  I went pink again.  “Don't worry I’m sworn to secrecy.” She looked more serious. “For real tho by not comfortable swimming you meant you can't swim at all. I didn't realise.  Thank god that jacket was buoyant enough for you, I would never have gone for it if I realised.  That could have ended…” she didn't finish. “Are you ok tho? Actually? You got really thrown there.” 

I nodded, eager to assure her I was ok  “Ya, It was totally fine. — I mean ya scary for a minute.  But this lifejacket was really good, like it was more than enough. I felt really safe in it once I calmed down.”

Hannah smiled at that.  “Ok good. — Ya it is super comfy in the water.  Not good for swimming in, even if you know how to swim, that’s probably the worst thing about it, but ya I definitely do remember it was super comfy cosy to just float in. — And hey it being no good for swimming doesnt matter for you anyway so it actually kinda suits you in that way!”

She was joking around but the comment made me feel a bit weird. I just nodded agreement.

“Ok that said tho seeing as you really can’t swim, maybe we should up your safety just a touch.” Hannah leaned down and picked up the yellow strap she had tossed me to pull me in.