A story of summer, of sun, and of skinny dipping. Or: The longest tease of [m]y life

I had known Anne for a long time. We had been roommates back when we were students. We lived in a smallish city of a few hundred thousand, somewhere in Europe. Not a very special city, but nice to live in. Not a lot of traffic, you could bike and walk everywhere, and the city is located directly on a body of water, so you have a nice little coastline promenade and a few boats in the city.

We used to have this nice little flat in a city house that we shared. We, that was me as the only guy, Anne, and another girl. Once, maybe a year after we had both moved out, when we had been drinking, Anne had mentioned to me that she would have loved to get me into bed even while we shared the flat, but I had joked it off. Explaining how we had been roommates and it would have ended up causing all sorts of drama.
By the time this story took place I had moved away for work. I was in town for my summer holidays to visit friends and family.
She knew this and called me one day. I liked the idea of re-uniting. Her confessions to me never stood between us and I looked forward to seeing her again. She is this whirlwind kind of girl, always up to mischief, and of course her suggestion for me to come around for breakfast and then hang around in town got escalated to a champagne breakfast pretty quickly.
Even the night before our date I had this feeling that this time might be more than just friends. In the morning the feeling stayed. I made sure that I would look presentable even from close up. You know how sometimes you are going to meet someone and your instincts tell you there is more going on than usual? I had this feeling all morning.

When it was time to go I hopped on my bike and got on the way.

It was a beautiful summer morning with not a single cloud in the sky, and cycling through town was a joy. I stopped on the way to pick up the bottle I had promised to bring and arrived at her house just at the agreed time.
I just wore a nice pair of shorts and a light blue shirt so I think I did look presentable but still casual, but she trumped me big time. She wore this stunning, off-white knit dress that hugged her slim body and matched her tan beautifully.
We said our hellos and hugged and she showed me around in the place that I had never been to. She lived on the fourth floor of this roughly 100 year old town house, overlooking the city’s nicest market square, with balconies both to the street and to the rear, looking out over the gardens on the inside of the block.

She had a great breakfast prepared, complete with pancakes and fresh bread from the bakery around the corner. She smiled when I presented the bottle, glad about the fact that we were both still silly enough after having started working. We agreed to save the champagne for later and put it in the freezer now.

We had a long breakfast with a lot of joking and laughter and old memories. She then kicked off the day.
“What about we take the champagne with us and go down to the water front and have it there”, she asked.
“Sure, it would be stupid to spend such a beautiful day indoors.”

We packed a little basket with some fruit and glasses and went down the stairs to our bikes. The sun had really warmed the city up, and the wind and warmth felt great. We rode down to the promenade where we found a nice spot to people-watch. It was a weekday, but because it was summer many people were on holiday so there were lots of passers-by.
We opened the bottle. We sat there in the sun, watching people stroll by, laughing about old stories and new, and about the people walking by. It was great fun. We spent probably an hour sitting there, getting slightly tipsy but not drunk.
Then Anne had a great idea.

“It’s such a beautiful day, we should actually be sailing.”

I don’t have a boat of my own, and neither does she, but she knew I could call a friend. I sent a short text, asking him if it was OK for me to take the boat for a spin.
“Sure enough”, he texted back, “I’m in the office anyway. Have fun.”
“We can go, it’s cool with him”, I said.
“Great. Sounds like a plan.”
“Yeah”, I said as we started pushing our bikes towards the marina, “probably the best thing we can do on a day like this.”
“Well, actually we should be going for a swim.”
I looked at her while we walked the few hundred metres to the dock.
“Unfortunately I didn’t bring my swimming trunks. And you haven’t as well.” She laughed and said “Well, I don’t know about you, but I guess I could just hop in in this dress.”
I laughed back. “Well, tell you what, that thing will be see-through like nothing else. That would look so funny. Honestly, if you jump in in that, I’ll jump in wrapped in a spinnaker.” She didn’t sail as much as I did, but she knew what that meant. The spinnaker, this thin, white nylon sail, would look hilarious to be wrapped in, and it would be absolutely transparent as well if it was wet and clinging to a body.
She looked back at me. She grinned slightly.
“Well, we could be going skinny dipping.”

The atmosphere changed in an instant. I ignored the mischief in her voice and half-mockingly said “Oh behave!”
We got to the boat, I picked up the keys from the harbour master and we started preparing everything.
My friend’s boat is this small, 24ft (8m) sailing boat. Small, light and very easy to sail, and a lot of fun. It does not even have an engine so it takes a minute of prep-work before you can go.
While I did the preparations I had a quick look into the storage down below. The anchor was on board.

Good.

We would need an anchor if we wanted to go for a swim. I was really unsure about what to do. But the option was there.
We got on our way. Once we were clear of the marina we headed along the coastline. Not far from the marina were two things. A little old fishing harbour were we could go for a snack. And the swimming bay.
Named so because it is a good anchoring spot, slightly out of the way with lots of space that made it a popular spot to stop for a swim. Since it was a weekday it would be pretty empty.

While we sailed along I racked my brains about my options.
We hadn’t spoken about the skinny-dipping thing again. Was she just kidding? Was she serious? What would she say if I brought it up again? Would she really be comfortable with getting naked in front of me? And would I want this? I felt I had the power to decide. We could go for a snack. Or we could go for a swim. Which would mean that within the next 20 minutes or so she would be standing in front of me naked. While she would look at me, naked as well. What if she only wanted to go swimming, and I would get a hard-on? Would she be offended?
I felt my dick making decisions for me. Intellectually, I didn’t know what to do. I was so excited with the prospect of being naked with her that I could not think straight. Still, I had to make a decision. Time was running out as we travelled further along the coast.
I went down below and grabbed the box with the anchor in it.

I put it on deck.

“So, should we stop for a swim?”

She looked at me and smirked.

“Sure, of course!”

I started preparing everything which kept me busy. It all felt sort of natural, but I was super excited. Excited in a semi-sexual way. In a way that did not make me have an erection, but made me extremely aware of everything. The light breeze, the colours of the water and the shore in the bright sunshine. The heat of the sunshine and the coolness of the breeze on my skin. My skin that would be exposed in just a few minutes. Anne, who was steering the boat and watching me.

We did not say a thing, only what was necessary to navigate the boat. I guided her to a good anchoring spot. The bay was almost empty. Only two other boats were there, far in, tucked away under the shore. We would have no other boat within at least a hundred metres of us.
While Anne got us to our spot, I took the anchor and line to the foredeck. Tied the line to the anchor, and the other end to the boat. When we were in shallow water, we dropped the hook and took the sails down. After the boat had drifted back a bit and settled on the anchor, we had arrived.
Without the sound of the breeze and the murmuring of water flowing by, it became silent.

“OK, let’s get the sails out of the way”, I said. They had just been dropped to the deck, and we started rolling them up to put them away.
With the sails done, she looked at me. Waiting.

I started cleaning up the rest of the boat, coiling up all the lines, putting stuff back into the little stow bags. I am sure I looked normal, but my mind was in a mess. I had never done this. I was about to be naked with a girl that I had nothing sexual going on with. In broad daylight. My dick was tingling, my mind sucked everything in while she, she just stood and watched me. I felt her gaze on me, looking at my arms and hands and body.
Finally, after maybe two minutes of busy time, I was done cleaning up. I took a short rope, tied in a loop and hung it overboard. With this done, we would be able to go back on board if we were swimming. There wasn’t anything else to do.

Well, one thing was.

No-one had said it yet, still it was so obviously going to happen.

We stood, looking at each other. The breeze flowed through her hair, the bright sun bounced off her white dress.

“Well,” I said, “I guess this is where we undress.”

She hesitated. I could see in her eyes she felt the same as I. She was not comfortable. She didn’t want it to stop, but she also didn’t want to start.
I had an idea out of nowhere. “What about we play Rock Paper Scissors? Best of three, loser takes off one item?”
She seemed relieved when she agreed. Now we would almost be forced to act. There was no way of stopping. Everything from now on would just happen.

We raised our fists.

I had not even considered the odds, but I wore a blue shirt and navy shorts, together with a white undershirt and black boxer briefs.
That gave me one more item, since she had her dress, bra and panties. But that was nothing I considered. I stood opposite her and the naughtiest game of my life was about to start.

“One, two, three”

After I said three, we opened our hands. I had lost.

We played again. I lost again.

That was my first item.

I opened the buttons of my shirt. One by one exposing the fact I wore an undershirt. She did not seem disappointed to not be seeing skin though. Anne stared at me, just like me she seemed unable to process what was going on.
My shirt ended up on the deck between us.

We raised our fists again.

“One, two, three”.

She lost.

Then I lost.

Then, she lost again.

I smiled. I was going to see her in her underwear. Right now.

But then she did this magic thing women do where they reach behind their backs and wriggle a bit and then suddenly pull their bra from underneath their dress. I was disappointed and mesmerised at the same time.

She still stood there, fully clothed, and grinned.

We played again. I lost. I lost my shirt and stood there, just in shorts with a naked torso. I felt the sun on my back, and her stare on my front. She checked me out, then smiled and lifted her fist again.

“One, two, three”

I lost again.

I felt more nervous now. Until now, it had been harmless. Nothing special about a topless guy in shorts, and she had seen me topless quite often, back when we were roommates.
But now I opened my belt in front of her. I opened the button and the zip.

I slid my shorts down, exposing my tight, black boxer briefs. I knew my dick was just about excited enough to be really presentable, but definitely not erect. But I had butterflies in my stomach and I could just not process what was going on. One more loss and I would be naked, while she was de facto fully clothed. Still, I loved the idea. After all, I would not do this voluntarily. I had to. If I lost the game I had to get naked. The idea was too hot. To expose myself to her. She in her dress, and I naked.

With my shorts on the deck, we raised our fists once more.

This time, I was lucky. Or not, if I wanted to expose myself. But the game was to continue, and by now I wished it would go on forever.

Her hands disappeared underneath the seam of her dress. Her dress got pushed up a bit, while her hands fished for her panties.

They came down again, and the tiny bit of fabric landed on our mutual pile of clothes.

She flushed and smiled nervously. She looked just as turned on as I was. She must have felt the breeze go through the loose fabric by now. Still, she still looked fully clothed.

I said the obvious. “Well, whoever loses now,… one of us is going to be naked after this round.”

She didn’t smile any more. She had the same super-aware look on her face that I must have had. Her eyes were wide, taking everything in. From the other boats in the background, the bright sunshine, the movement of the boat, to my almost naked body just two steps away from her.

I raised my fist and smiled at her.

She smiled back. Raised her fist, too.

“One, two, three.”

I held out my paper, she had scissors. Her smile got wider.

Again.

“One, two, three.”

She had scissors again. I had rock.

“All or nothing now. One, two, three.”

She had gone for rock.

I had paper.

She would lose her dress now. It took a second until her face changed. Now it was no longer playing. Now it was getting naked in front of me. Exposing her body. With no bedroom darkness to hide in, and no way to control the pace.

It was now. No backing out. Nakedness.

Her voice was changed when she spoke. “OK, I’m doing it, but I’ll go straight in the water after that”. I calmed her down, saying “Sure, that’s what we are here for anyway.”

Then I waited. Looked at her.

Her hand reached behind her back.

She opened the zip. I could see the dress opening up, folding away from her tits. Exposing them. They were tiny and cute and had beautiful, dark nipples. Her dress started going down. She let go. The fabric exposed her slim body, tanned skin and a cute, shaved pussy just for a second before she said “OK, I’m going in”, and she started sitting down with her feet over the side, dangling into the water, started moving towards the water.
I was dumbfounded. I stood there in my boxers, watching her. It just happened so fast.

I wanted to be naked, too.

“Hey, what about me. I want to join you.”

She stopped, looked at me. I pulled down my shorts. It was not a big gesture, but she hesitated for a second, looking at my dick. It felt good to be exposed to her. She was sat down, facing away from me, just her head turned towards me. And my penis was out in the sun for her to see. I liked it. She continued her wriggle towards the side of the deck to slide into the water. I dashed to the side deck and with one jump over the guardrail wire, dove in head first.

The water felt great, it was cool and refreshing and feeling it on my whole body was great. It washed away the sexual tension and surrounded me with deep, dark green freshness. I felt alive.
A second later I surfaced and turned around to see the boat, now rising high above me, bob on the surface of the water in the sunshine, and on the side deck, Anne was almost in. One last wriggle, one light spreading of her legs, too short for me to realise I had a plain view of her pussy, and her body slid into the water.

It was obvious that she enjoyed it, too. The tension was gone, now we were just swimming together. We started talking again, about what a great idea it was to come here, and how everyone else was sitting in the office today while we had this day to ourselves.

Anne, who had seemed very reluctant a few minutes ago, seemed to really enjoy her nakedness. She seemed comfortable and secure.
Anne laid back in the water, slightly paddling with her feet, which lifted her chest so that her tiny tits were just below the surface. She looked into my face, and I checked out her body. Without shame I looked at her, her face, her tits. I even shamelessly tried to see the shaved pussy that was just not visible in the shallow water covering it. She did not mind me watching, and I wanted to return the favour. Let her look at me, too. I also leaned back, exposing my chest. I paddled, raising my hip, then arching my back. My dick came through the surface, lying on my belly, inches from her face. She looked, smiling, at my balls, tight and shrivelled from the water, at my short, trimmed pubes and the dick lying on them, wet and glistening in the sun. It felt great to have her look. I trusted her completely, and she trusted me. It was beautiful.

We played in the water for some time, she even pulled up to the side of the boat, grabbed the rail, pulled herself towards the bow until she hung there, her arms dangling from the pulpit. She was out of the water almost to her hip. Then, she turned around. I looked at her wet body, her tits, wet hair, and died to see more of her, all that was hidden in the waves. I still hadn’t really seen her pussy, but she just smiled and let go. We swam some more, and I did what she did. I grabbed the pulpit, dangling from the bow. Because my arms are longer, I was in the water up to my belly button. She was close to me, and I could see in her eyes that she wanted to see more.

I smiled. I turned my hands around, brought them to pull up position. I flexed my arms and back. Slowly my body rose from the water, exposing more and more skin, then my short pubes, the shaft, finally my whole package. I stared at her, but her eyes were glued to my penis. It was dangling in front of her face, slightly bigger now as she must have realised.

This was no longer being forced to strip because you lost a game. This was full on exhibitionism. I wanted her to see me naked. And I wanted to stare at her pussy. And another thought crept into my mind.

I let go and dropped into the water. I wondered what her hand would feel like on my dick.

I felt the arousal finally take over. I knew my dick was getting bigger now. Within seconds, what I had feared had happened. I had a hard-on. I was glad the water could hide that fact and started swimming. Exercise is supposed to take your mind off sex, right. Well, I guess it somewhat worked, but when she said she was getting cold and suggested to get out of the water, I had to confess “I am a tiny bit excited at the moment, I think I’ll need a minute.” She smiled, and swam towards the boat. She grabbed the loop of rope we used as a ladder, stepped in and started pushing herself up. I saw her butt rise out of the water, but she managed to not show too much, then crawled on deck and disappeared in the cockpit.
I stayed another minute and tried to calm down a bit, and managed to go from erect to chubby. Then, I joined her on board. “Now, have you contained your excitement” she laughed, looking at my dick. “Yeah, well, sort of. I’m sorry but I think we’ll have to live with how it is at the
moment” She laughed again: “Yeah, no problem, it’s ok for me!”

We both stood, waiting for the sun to dry us, since we had no towels. Again, we looked at each other’s naked bodies, laughed and talked and looked around. I was well aware that my dick was somewhat swollen, and the feeling of it risen slightly and showing my sexual tension just excited me more. Now that I had nowhere to hide I felt incredibly exposed. It didn’t take long for me to be erect again. In her plain view.

We sat down on deck, leaning against the sides of the cockpit. I on one side, she on the other. Facing each other. She had her tits exposed and her hands by her side, but her legs were kept close. There was nothing to be seen. I, on the other hand, could not do much. I pulled my legs up a bit, but I knew she knew what was behind them anyway so decided to let her see. I lowered my legs, and my full erection pointing to the sky was in her plain view. I smiled and apologized. Then I said “It is a bit unfair, there is nothing I can do. I mean, you can just close your legs and nothing can be seen. If I am excited, it will be so obvious.” She smiled, but did not react. I had hoped that maybe she would get the hint and open her legs. It was not so much that I wanted to see her pussy, it was that I wanted to see if she was just as excited. Was her pussy swollen as well? Was she wet? Or was this all non-sexual for her? Did she like the situation? But she did not move. She was an enigma. I had no idea what she thought and my mind was just too overloaded with sensory input that I couldn’t figure anything out. She just looked at me and laughed and chatted like nothing had happened. Like I was not pointing my hard-on at her.

We sat like this, enjoying how the warm wind and the sun dried us, for some time, when I looked around and realised that the boat was no longer in the same position. “Hang on a sec”, I said, “I think we are dragging the anchor.” “Are we?” “Yes, we used to be a lot closer to the shore. Let’s check, we may have to go anchor up again and sail back into shallower water.”

It was a pity we had to interrupt our naked chat, but we had to do something. I grabbed my boxers and shorts. “Do we need to get dressed again”, she asked, sounding mockingly disappointed. “Well, we can’t really sail around in someone else’s boat, wearing nothing at all.”
She stood up in all her naked glory and bent down to pick up her dress. I was so busy with the boat I missed to chance to stare. Quickly, she was covered up again, while I kept the shirt off. I walked to the bow and put a hand onto the anchor line, feeling for the typical vibration that would indicate the anchor dragging over the ground. I felt nothing. I looked around. The boat was moving again, but I realised it was just swinging around the anchor, not drifting.

Anne looked at me puzzled. “What’s going on?”

I told her.

“So we can sit back down and stay here?” I took another look around. “Yeah, I guess we can.” So we did sit down again, dressed this time. We continued to chat and laugh, but soon I felt the sun on my bare shoulders. I reached into the little stowage bag on the bulkhead. Yep, there was some sunscreen. “Do you want some, too?” She shook her head. “I’ve got enough of a tan, I’m good.” She did, indeed.
I started rubbing the slippery liquid onto my arms and neck, onto my nose and ears, then on my chest and belly, too. Then I held the bottle at Anne.”Would you do my back?” “Sure”

She started massaging my shoulders and my back, moving down to my hips. Her hands were soft and firm at the same time. They felt great.
She continued downwards. Then she said “Well listen, if you don’t want sunscreen on your shorts you’ll need to move them down a bit!” I wriggled a bit. “Enough?” “If you want sunscreen on them, yes”. I laughed and opened my belt and button. I pushed my shorts down. In the front they almost exposed my short, trimmed pubes, in the back I pushed the fabric down to my butt. “That’s much better”, said her joyous voice behind my back, and her hands went into these freshly exposed areas of my body. As I sat there next to her, bent over to give her better access to my back, I realised I was an idiot. If I had asked her to do my back before doing the chest and belly, maybe she would have just continued with my front? Her slippery hands could have rubbed my chest, then my belly… And with my shorts pushed down, would she have gone down there, too? Would she have demanded my shorts to go deeper again? How much deeper? Would she have rubbed me there, a mere inch from my cock? Would she have gone even further?

“Ok, done!”, her happy voice jolted me back into reality. I thanked her, and moved to sit next to her again. We continued our chat. Being still covered, I could focus on other things than my nudeness. We were both so relaxed, sitting there in the sun, watching the scenery. I didn’t bother closing my shorts button and sat next to her with my belt undone and fly slightly apart. She didn’t mind.

After some time chatting she looked at me and smirked: “So, what do you think, should we go swimming again?”

“Sure”, I said, getting up with my belt dangling down.

She stood up, too. We faced each other. I grinned at her.

“So, do we play Rock Paper Scissors again?”

She said nothing, she just grinned back and lifted her fist.

I lost the first round and just pushed my shorts down. I felt them taking my briefs with them a bit. She looked at me with a friendly smile. I looked down. I could already see a slim strip of pubic hair above my waistband. Above the bulge in the fabric that was the last thing to hide my package from her stare.

Again, it was matchball. Whoever lost would be naked, since Anne’s bra and panties were still on the deck, together with my shirt.

We raised our fists again.

After a count to three, I lost.

As we raised our fists for the second game, I felt a wave of excitement rush through my body. Her eyes had the same intense focus, too. Just as during the first time we played, we both knew what was up.

I counted to three. I lost again.

She grinned. I smiled at her. I liked this. I wanted it.

She was fully clothed, and she would look at my naked body. I hooked my thumbs into my waistband. I inched them down, ever so slowly, while our eyes remained locked. Then, just as my shorts exposed the first small bit of my penis, she broke the contact and looked down. She did not miss anything. I felt the fabric slide along the skin of my shaft, millimetre by millimetre. I felt my dick getting free. I felt the fabric falling down my legs, dropping onto my feet. I felt the gentle breeze flow between my legs, this beautiful feeling on my balls, suddenly out in the open. I felt the sunshine on my skin. I felt her stare on my cock, on my balls, on these intimate parts of my body. She touched me with her eyes.

I loved the feeling. I loved how this was entirely one-sided. I let her stare at my cock and I expected nothing in return. She remained clothed and just watched. It was the feeling of giving her this, of trusting her so much that I would let her see me like this, completely naked, that was the best thing.

She smiled a silent, happy smile. Took everything in. My whole body. I let her watch for some time, then smiled at her and said “Well it looks like you are enjoying this, but I’m afraid I will have to jump in now” I turned to the side, showing her my penis from the another angle, before I reached the guardrail and just jumped in head-first. Again, the dark green, velvety water surrounded me, flowing along my body, my whole body.

**Continued in comments**

Source: reddit.com/r/gonewildstories/comments/7ngm4b/a_story_of_summer_of_sun_and_of_skinny_dipping_or