My experience with my mother was heating up quickly. Well, weirdly, it felt like it was quick but in actual fact, we hadn't done that much. In contrast, my experiences with Chele and Mrs. J had jumped to from nothing to full contact action in moments.
I'd seen tons of pictures of her naked and having sex, but she hadn't actually been naked in front of me, let alone having sex. I'd only heard her masturbating through a wall and a closed door. She'd heard me cum and seen me come a few times now, but she hadn't actually touched me at all. And the orgasms had been amazingly intense because she was the focus of my lust. I was dying to actually touch her and be inside her but the intensity of it seemed almost dangerous.
I cleaned up the mess I made in the kitchen, threw my wrecked clothes in the laundry and took a shower. I got cleaned up and then set my attention on a first date plan. Remembering mom's concerns about her privacy and her past, I knew it needed to be low key and nothing sexual was going to happen. That's okay, the idea was to build the tension for when we were home afterwards. So, nothing like dancing and drinking and clubbing. And nothing too romantic, either. Just something quiet, just us, and enough privacy to talk and get to know her as a woman, not my mom.
I decided that an afternoon on the water and a sunset dinner on the shore would be perfect. A friend had a nice sailboat and owed me favor so I called it in. I made reservations at a quiet, traditional seafood place near the marina, it was the kind of place a mother and son could have dinner without seeming out of place.
With plans set, I went to tell her a little about the plans so she could be prepared and dressed appropriately. I found her in her room, reading on her bed.
"Hey Mom, got things set for our first date thing. Do you want to know details, or should it be a surprise?" I asked.
"Oooh! I do like surprises. Keep it a secret, ok?" She replied happily. "Do I need to know anything about it in advance?"
"Yeah, a little. "I answered, watching my words to not reveal too much, "Dress code is activewear in the afternoon and sophisticated but conservative in the evening. Maybe bring along a bathing suit if you're feeling adventurous. There will be a place to change."
"Ok. Sounds fun, a little adventure, a little romance." She agreed. "You've put some thought into this, I'm a lucky lady to have a hot date with such a catch."
I tried not to blush. This was feeling more like an actual date than I expected.
"Ok. I'll be back to pick you up right at 3. Be ready. "I said, heading for the door.
"I'll be ready!" She said and then added, "wait a sec, got something to show you!"
I turned back to face her, and she had her shirt pulled up, her tits in her hands, her fingers pinching her nipples. My eyes popped wide open. She quickly pulled her shirt back down, gave me a wink. "I'm excited for our date, just wanted you to know how much! Now, go."
I went out the door to get things ready with my cock twitching in my boxers.
I went to the marina to ensure the sailboat was seaworthy and clean. I really didn't want to take my date on my friend's boat and find disgusting evidence of his past conquests. I brought a cooler with drinks and some snacks, fruit and cheese. Fancier stuff than you'd find at a college party, but I was anticipating what my mom would prefer. I stopped by the restaurant to secure a secluded table overlooking the harbor. I ran the car through the car wash and vacuumed the inside. I picked up a nice bottle of wine and headed home. I was tired from all of the prep work but energized by the prospect of the reaping the rewards of those efforts. I showered, shaved, put on nice clothes, put the wine in the fridge and then went outside and promptly at 3, rang the doorbell.
Mom answered the door, momentarily confused that I was outside the door but quickly caught on. She was dressed for adventure. Hair up, tight low cut crop top showing a respectable amount of cleavage and her tight abs. Tight, 3/4 length stretch pants, I could see a hint of thong arching across her cheeks and into the crack of her ass when she twirled to show off her outfit.
"You look amazing," I said, "and ready for fun."
She held up a bag, and said "Thanks, but this is my outfit for fun" and pulled out her bikini from yesterday, gave the pieces a little shake and dropped them back in the bag with a wink. "I saw how much you liked this yesterday. I figured you might like another look."
She then pulled me inside the door, swung it mostly closed, kissed me with her mouth open for a moment, pulled back, pushed me out the door, followed me out, pulled the door shut behind her and said, "I'm all yours, let's go!"
A few minutes later, we were on the boat, and headed out into the harbor for an afternoon sail. Weather was great, light breeze, water was calm. Not a lot of traffic but enough that I'd need to be attentive to our surroundings. Once we were into open waters, Mom disappeared below deck. She reappeared a few minutes later in her tiny bikini. She started with maximum coverage but then scrunched up the fabric to show even more skin. My cock came to life, and I rubbed it through my shorts. I decided to push things a little and drop the shorts. As I unbuckled, she said, "Hey captain, keep your hands on the tiller, and your dick in your pants."
I rebuckled but I adjusted for comfort and gave it a good rub.
"Thanks, hon. I know you're horny but patience." she said, "it'll be worth it."
She stretched out on the deck, looking glamorous and delicious, she rubbed some lotion on, and called over to me, "I'd ask you to do my back, but I think things might get out of hand and I'm so horny I'd let them."
We sailed for a while, enjoying the sun and breeze. Well out into the harbor, I decided to drop the sails and grab a bite to eat. We sat around the table in the cockpit and snacked.
"This is a great first date so far, Joe. Thanks for arranging it. I haven't been out on a sailboat in years. Want to know a little secret?" she asked.
"You know I do." I replied.
"I got gangbanged on a sailboat once." she whispered as if there was a chance of being overheard. "I think there are pictures in one of those magazine. Did you see them and get ideas?"
"Oh my god, no. But I'm definitely gonna go look for them." I said with delight.
"It was before I met your dad. I was traveling in Europe and had just started doing photo shoots. I think it was 6 guys, another girl and me. They were supposed to be a racing crew and we were their reward for winning a race. It was an awful shoot, a boat isn't the most comfortable place to fuck, and even harder to get the camera in the right places, but we managed. They guys were all in really good shape, I got fucked so hard I couldn't walk or sit down without feeling it for a week." she retold her memories of it, staring out over the water.
"Keep an eye out for traffic coming to close." she said quietly and leaned back, pulled the gusset of her bikini bottom to the side and began rubbing her pussy. "Just watch." she said when I started to move toward her.
She started slowly, barely touching herself, lightly along the outer edges of her labia. Her lips were bare, and there was just a small patch of closely cropped hair above her clit. Gradually, she increased pressure and speed and then pushing directly across her clit. She dipped two fingers into her pussy, they came back out glistening and she used them to lubricate her clit and then really increased the tempo. She laid down on the bench, pulling her ankles to her ears and spread her pussy with one hand and explored within with the other. I just watched, occasionally glancing around for boat traffic and then back to the sensual display unfolding in front of me. There was silence except for the ripple of wind against the rigging, the water hitting the hull, her breathing hard and her wet fingers plunging in and out of her pussy.
