We had seen each other on and off at sailing club social events. Lilly looked like a compact bundle of fun. She was on the shorter side. 5' 2" maybe. Medium length black hair in ringlets when wet from salt spray and still pretty curly when dry. Trim ass and a fairly prominent bust. Not monstrous like some of those poor shorter girls with huge busts that require engineered bras and probably give them back pain. But not slim either. Maybe C going on D? She could be bubbly and enjoyed a beer with everyone. I'm sure a lot of the younger members had fantasies about her but she didn't seem to stick with any one particular group. She crewed around the boats - had a reputation of knowing what was what and not screwing up. But that was about as far as my thinking went. I was in my late 30's while she appeared to be early 20's. I wasn't rude or dismissive - just didn't consider her as someone I would approach beyond being polite.
I kept myself in pretty good shape. Not through working out. More an active lifestyle. 5' 11" and 180lb. My work as an independent computer programmer meant I could make my own schedule. Road biking during the week and sailing during the season. It kept the fat off and I was reasonably toned. A trimmed beard and that was me. I was single. Not through any particular choice. Just hadn't met the right person yet. Dates during the week and the odd fun tumble in bed after. But nothing permanent. Then there was the sailing club. It was not the place to try and date. There was a little bit of dating among members and I'm sure a little swinging went on. But if people broke up - and still had to come to the club it could get messy with "he said/she said" and people taking sides. Better to not get involved and just sail and party a bit.
We were a pretty active sailing club. Lots of small yacht and dinghy racing by day and good natured hard partying and barbequing in the clubhouse in the evening. Many owners of smaller yachts were like me. We came to town for the weekend and just stayed aboard our boats at night. It wasn't just for the economy - but in a tourism-driven town, hotels could be hard to find during the season. I have a 36ft sloop and raced in a handicap class with others of similar size. While not luxury - my yacht had four decent berths in two cabins. A double down aft which was part under the cockpit. It was my "owner's" berth and a couple of single bunks were on either side of the saloon above the bench seats. My crew tended to be a couple of guys who lived in town so we would just meet in the morning at the dock. But some nights when the partying had been a bit hard - we would take someone's car keys and I would give them a bunk to sleep it off in.
One particular warm spring weekend the barbeque and partying was pretty intense and in addition to us taking car keys from one particular member, one approached me and asked if I had a spare bunk as they didn't think it would be wise to drive home. I was happy to offer a bunk rather than see the member drive. As we headed off down to the docks Lilly appeared and asked if I had another bunk to spare as her ride home was the person whose keys we had taken. She was not in a position to drive herself and I indicated there was another bunk as long as she didn't mind it being in the saloon with the other member already weaving his way down the dock. She didn't mind and everone slept it off. Come dawn with sore heads my "overnight crew" disappeared off to the club showers. Later everyone went racing and then everyone went home.
This happened on and off a couple more times through the early summer and I didn't think much of it. Till the midsummer "longest day" barbeque when everyone had a real good time. Not many were in a state to drive. The clubhouse bar seat benches were already full of folks asleep. Lots of members were being asked if they had bunks to spare. I had already agreed to one and Lilly wove over in my direction.
"Looking for a bunk?" I asked.
"Please" was her response.
"You know the drill" I laughed and everyone made their way to the yacht and bedded down for the night.
Perhaps a couple of hours later I was woken by Lilly tapping gently on my cabin door. She was standing there in her jeans and sweater.
"What's up?" I asked - thinking that perhaps Phil the other guest had been ill.
"Ummm... It's Phil. He has had a lot to drink and is snoring loudly enough to shake the glass out the portholes. I can't sleep. I was wondering if I could sleep in here?"
It wasn't impossible. But the bunk was a double. The foot part of it was under the cockpit to make it fit. So it was a bit snug.
"It would be a bit of a squeeze" I pointed out.
"We would just be sleeping." said Lilly.
Through the open cabin door I could hear Phil take another huge snort of breath. Even with the door shut he was still going to be a bit audible. I was tired. I eased over to the side to make space. As I did, I reached up and opened the cockpit wall porthole a bit more for some extra air.
"Thanks" said Lilly as she lay down on her side of the bunk with her back to me.
As I was drifting off to sleep I sensed her reaching under her sweater and unhooking her bra. I also sensed her unbuttoning the waistband of her jeans and easing the zip down. Lying on my back in my boxers and a T-shirt - my cock took a mild interest in her movements and I drifted off to sleep with a pleasant semi-hard on. I was a little surprised in the morning when I woke to find we were in a bit of a spoon position in the bunk. Lilly still seemed to be sleeping - which was just as well as my morning wood was gently pressed against the back of her jeans through my boxers. At least my arms were not around her, I thought. I eased back slightly in the available space - but I felt Lilly arch slightly and her butt remained close to my now very hard cock. She sighed in her sleep. I eased back some more and this time she didn't follow. As she stirred, I feigned sleep and I felt her roll out the bunk, heard her zip up and presumably do up the button and bra in the pause before she left the cabin for the clubhouse. As the door opened Phil could be heard still sawing wood in his saloon berth.
I did a little more 'presuming' as I took care of my morning wood, before also rolling out the bunk and getting coffee on and getting ready of the day's racing.
Through the rest of the summer - a similar scenario played out. Usually "Phil the chainsaw snorer" and Lilly in need of bunks. If there was one advantage to the scenario - it was that the club gossip had decided Phil and Lilly were getting it on. My name stayed out of it. Fine by me. But the reality was that Lilly didn't even ask anymore. I would get into my bunk and with Phil dead to the world - she would follow me into mine, closing the cabin door for some peace. On the third or fourth occasion as Lilly unhooked her bra and eased her waistband she asked:
"Would you mind if I took my jeans off? Be a lot more comfortable. I'll still be in my underwear."
I mumbled something about her being young enough to be my daughter. But if she was OK with it - I was OK with it.