Halloween Party 2026

It was the usual crowd at my boating club's Halloween party. They're a fun group of people though many are getting on in years. I'm usually one of the youngest men at these gatherings. Yesterday was no different. As the afternoon darkened to dusk, the outdoor festivities were in full swing. The winner of this year's costume contest was a new member, Ashley, a blond in her mid-forties, wearing a Supergirl outfit. Beneath a flowing cape, the shiny blue and red spandex of her outfit clung to her shapely body, leaving very little to the imagination. What was especially noticeable was, she wasn't wearing a bra. This observation was not lost on any of the men, young or old. The cool Florida breeze blowing off the water caused her nipples to stand at attention.

The club had recently made a push to invite and recruit new members, a younger crowd so the club could live on for years to come. This was Ashley's first event. Her husband, Charlie, is twenty-five years older. I thought to myself, 'Why would this hot woman be with a man old enough to be her father?'. After mingling with a few members, I overheard some of the women gossiping. Apparently, everyone seems to know Charlie was worth a fortune. They all believed that Ashley was just after his wealth. It amazed me how they just assumed it was about money. I spoke up.

"You're all just jealous because she looks so seductive in her costume. Has anyone spoken to her? I have. She seems to be a very intelligent and interesting person. You should all be ashamed of yourselves." Mouths opened, no one responded as I walked away. I guess they were intimidated by her youth and beauty.

As I mingled around the patio, I made my way over to Charlie. I hadn't had an opportunity to speak with him before. He seemed like a nice-enough guy, a retired New York City firefighter. His past profession seemed to have affected his health as he got older. Being native New Yorkers, we had much in common. He was at the World Trade Center on 9/11. I'm sure he had hundreds of fascinating stories, but I didn't press him. I could tell it was too emotional for him. After several minutes, I excused myself and walked away. Charlie was too depressing for me.

I went to the bar and ordered a bourbon and Ashley stepped up to the bar next to me. She was still in her costume and I noticed a hint of her vanilla scent. That aroma drives me crazy- I love it. I could feel my cock thicken. With drink in hand, I walked toward the dock where my boat is moored. I was going to light a cigar and enjoy the night air. She followed me.

Pointing to my boat she said, "Is this yours?"

"Sure is. She's my baby. I bought her when I sold my company."

"It is big. Do you live aboard or is it just your fun place?"

"I spend as much time as I can aboard. Just my fun place I guess. It's a lot of work keeping her in tip-top shape. It has a comfortable living area, a full galley and two staterooms."

"I'm impressed. How about a tour?"

I hardly knew this woman but didn't want to come across as rude. I motioned yes and held her by the arm to help her step aboard. The cabin lights were off. Only the deck lights were dimly lit. She walked slowly into the cabin letting her eyes adjust to the darkness.

As I walked toward the light switch, she grabbed my arm. "No, don't turn on the lights."

I was puzzled. "What, why?"

"I don't want anyone to see us through the windows here alone."

She stepped closer to me and her body rubbed against mine. Now my cock was straining against my shorts. Her hand reached down and held my erection. I grabbed her arms and brought her close to me, grinding against her as our lips met. They were soft and tasted sweet. Our tongues danced for what seemed like an hour. I released one arm and ran my hand across the silky costume restraining her breasts. As I touched her right nipple it became rock hard and she sighed. Our lips unlocked from the passionate hold we were both enjoying.

We were still embracing one another when she whispered, "Show me where you sleep."

I reached out for her hand and led her to the captain's stateroom. No words were spoken. Ashley sat on the edge of the bed and I stood in front of her as I removed my shirt. Her hands reached out and she pulled my shorts to the floor. My dick was like steel. Her hand cupped my balls and she guided me to her lips. She sucked the head then she devoured the entire length in a continuous motion. The way she was able to engulf my member made me start to lose control. The only sound I could hear was her softly slurping. I could tell she was enjoying this. But I stopped her, short of exploding into her mouth.

It was a clear night with a full moon. The only light in my stateroom was the moonlight shining through the small portholes. It was enough to see her strip out of her silky costume and cape. Her tits were firm and skin bronze with no tan lines. It was apparent that she spent much time in the sun. This just made her more alluring. She removed her red silk Supergirl panties exposing a perfectly shaved pussy. My suspicions were confirmed. Her entire body was evenly tanned.

She noticed I was admiring her and playfully broke the silence. "What are you staring at?"

I grinned. "I was just taking in the beauty of your perfect tan. It is very sexy."

"Thanks. I'm glad someone notices it. Most mornings Charlie leaves early to go fishing. He thinks I go to the gym. And I do, in a sense. I am a member at a nudist resort close by. I have my routine. First, I spend time in the steam room. Next, I do laps in the pool to stay fit. There's a group of regulars at the club, we all swim together. On Wednesdays, I play volleyball in the pool. It's kind of an informal league. When I'm done, I sun myself dry. It's very liberating. It makes me feel so incredible. Charlie would never do anything like that. I make excuses and blame his health, but mostly he's kind of a prude."

She piqued my curiosity. "Is it like a sex club? I've never been to anyplace like that."

"Oh no. I wish. It is just a place where people can go and be free to enjoy their bodies without judgement. It's like any other private retreat. A hotel on the property for guests to stay and plenty of amenities. A bar, a restaurant, pools, sauna, tennis courts, all the typical things you would find in any vacation resort. The only difference is, it's clothing optional.

I was fascinated with this woman. "I'd love to try that sometime."

Here I was laying naked with this stranger and she was opening up with a very intimate part of her life as if we had been friends for years. The whole time, she was lightly stroking my cock. I guided her onto her back and started to play with her tits. Her eyes closed and she arched her back, her breathing became heavy.

"That's nice, suck them. I love that."

I didn't let up. Her nipples were like diamonds. The harder I sucked, the more responsive she became. My hand slid down her soft skin. Her legs instinctively spread open as if an invitation to pleasure her. I was still sucking and gnawing on her. First, my fingers found her clitoris, exposing her most sensitive sheath. It was like a rock as it grew on my fingertips. The light touch of the circular massaging motion made her body tense up. I gently spread her open. She let out a loud moan as I buried two fingers into her. My thumb was still applying pressure to her engorged clitoris as I found and softly scratched her G-spot.

She could hardly get the words out. "I'm ready."

I took control holding her down, positioning myself on top. I slowly guided my shaft in as we became one. She broke free of my grip and grabbed me from behind to pull me deep inside her. There was no doubt, this woman knew exactly what she wanted. In no time we found a rhythm. The buildup was gradual. We were both enjoying the intensity of our bodies connecting. Our motion increased as Ashley's body clenched. She experienced spasm after spasm, her orgasm taking her in waves. I never let up the stabbing motion of my thrusts as I continued to impale her. When her body started to quiver, I couldn't hold back. Her emotion brought me to a state of exhilaration. I unleashed a flood that was intense. I became rigid as I unleashed an intense flood, delivering a thick stream of warmth into her. Although the evening air was cool, we were both coated in a sheen of sweat. I fell off to one side. Both of us were panting as if we ran a marathon.

Several minutes passed when I broke the silence. "You are incredible," I said, reaching down to caress her between her legs.

Ashley didn't utter a word out but simply let out a deep sigh and inhaled, savoring the moment. Touching her nub and feeling it become erect started making me hard again. I wanted to take her. As if she knew my thoughts, she mounted me cowboy style. Her full weight started to ride me sliding up and down as if on a merry-go-round. I lay there enjoying her power as she started to dominate me, taking what she wanted. She started to play with her tits, kneading and tweaking. I nudged her hands aside and took over fondling and stimulating her. She leaned forward pulling the hair on my chest. As she was grinding into my shaft, she started to match how I pinched her nipples. The two of us took pleasure in the slight pain we were inflicting on one another.

"Ashley, that's amazing. No one's ever done that before. Harder!"

"Now you know why I enjoy that so much. I'm so sensitive there I could come when you twist them."

I lifted her off me and tossed her to the side. She landed on her stomach confused. "Hey! Why did you do that? What's wrong?"

"Nothing's wrong!" Taking command, I positioned myself behind her and lifted her by the hips. She knew right away that I was going to take her from behind. Her hands reached out and positioned a pillow to her face to muffle the screams she knew would come. She spread wide so I could easily enter. My cock was like granite as I guided myself into her. With each stroke she let out a yelp into the pillow. It was total euphoria as I pleasured both of us. Again, her body tensed. Now she was howling into the pillow. Her screams aroused me, driving me to pound harder. I could feel her thighs starting to shake. Our frenzy was simultaneous, both of us grunting like wild animals in heat. I couldn't hold back. For the second time, I filled her. We remained still for a moment, then our bodies fell flat in a heap.

She rolled over. I was on my back and I took her into my arms holding her as we composed ourselves.

I finally spoke. "We need to get back."

Mumbling, she said, "No rush. I'm sure no one even noticed we were missing. Certainly not Charlie."

It was the way she said it, that was the first time I sensed that she really didn't care for Charlie. I didn't press the issue. It wasn't the time or place to have that discussion. I made the first move pulling my shorts on. She made no effort to get up. In fact, she made herself very comfortable in my bed.

She watched me as I dressed. "I'll wait a while before I reappear at the party. We shouldn't show up together as if we just snuck off to screw."

While that is exactly what we did, I let it go. "Good idea. Don't fall asleep. I don't want a search party to come looking for you just to find you naked in my bed," I said half-joking.

About twenty minutes passed when I saw Ashley in her Supergirl costume sitting at a table having a conversation with a group of women. I was relieved that she was off the boat. No one seemed to notice our absence. I wondered what they were talking about. Was she bragging about how she just got laid? I doubt it. Our eyes met from across the room. She shot me a devilish grin and somehow, I knew this wouldn't be my last encounter with Ashley.