About four years ago, I was coming out of a (somewhat boring) long term relationship, and realized that I’d been working too hard and not really enjoying life to its fullest. I was an attractive woman, in my mid-30’s, with long, dark hair and green eyes. I was in excellent shape, with big, natural 35E tits, so I got plenty of attention, but lately it hadn’t been from the ‘right’ type of people. I decided to attend a local charity gala at which I was hoping to meet someone “interesting” who would also be financially sound….two characteristics I was now requiring in dating candidates.
I dressed for the event in a sexy silk gown, with slits up both sides all the way to my hips, which would show anyone who looked closely enough that I wasn’t wearing panties. It was chic and provocative, but I thought it would work at this type of event, and with this type of crowd. The top of my gown was very loose fitting, and I purposely didn’t wear a bra, so that my large breasts would sway underneath the gown as I walked around the gala grounds. With no bra on, my nipples were making obvious bumps in the fabric, which caught plenty of eyes throughout the evening, exactly as I had hoped.
One hour into the evening, I noticed a handsome man….probably early 40’s….who was dressed nicely and chatting with a pretty young lady with a beautiful figure, both of them drinking wine as they talked. He glanced around the room as they chatted, and I saw his eyes land on me. He stopped talking for a moment, then pointed me out to his companion, who smiled and nodded at the man, as if in response to a question. Then she left their conversation, with another glance in my direction, and he walked over to me and introduced himself as Warren. I told him my name was Penny. We politely shook hands, and then he suggested we go to the bar to refill our wine glasses.
I found him interesting and attractive, which I’m sure he sensed, and I noticed he would casually touch my arm or shoulder, bump my breast or hip…even my butt…as we walked around the gala laughing and observing the crowd. His casual touches were having an effect on my, and I noticed that my nipples were now much more prominent through the sheer fabric of my gown. Warren noticed, too, and I caught his eyes glancing toward my boobs on several occasions as the evening wore on.
Finally, as we were walking past a hallway off of the main floor, he pulled me into the dark corridor and planted a tongue-filled kiss on my lips. I returned the kiss, which seemed to give him a green light, as he immediately began squeezing and massaging my heavy tits, gently pulling on my nipples, which were already stiff from anticipation throughout the evening. I reached down between his legs and felt the shaft of his prick through his slacks.….it felt wonderful. Maybe 8” or 9” long, and not yet fully hard. I could feel it getting stiffer as I rubbed along its length through his pants.
Warren found one of the slits in my gown, and slipped his hand inside and around to the front, so that he was fingering my already wet pussy. Without breaking our kiss, I spread my legs so he had better access, and he slipped two fingers deep into my cunt, moving them in and out of me gently, but firmly. I could barely stand up, as he finger-blasted my vagina with one hand and squeezed and pinched my tits with the other. I pulled his zipper down and fished out his now fully erect dick. It was about 10” long now, and thick enough that my hand barely fit around the shaft. I stroked it eagerly with my right hand, while using my left hand to reach inside his pants so I could cup and fondle his ball sack.
While we were still standing in the dark hallway, leaning against the wall, he used the slit in my gown to move it completely to the side, then lined up the head of his shaft with my pussy, and shoved his rock hard cock deep into my dripping wet cunt. I wrapped my arms around his neck and pressed my face into his chest. He grabbed my ass cheeks to help hold me up as he pounded his stiff prick into me over and over. In this position the shaft of his dick was stimulating my clit like crazy, and in no time I erupted into an electrifying orgasm that washed across my entire body. As I reveled in the throes of my climax, Warren suddenly caught his breath, grunted, and slammed his cock deep into my pussy, emptying a huge load of cum inside me. He kept pounding his prick in and out of my vagina as he came over and over, finally slowing down and releasing my ass cheeks as we both leaned against the wall to catch our breath.
After settling down a bit, I used some tissue from my purse to clean my pussy, then wiped off his shaft before stuffing it back in his pants and zipping him up.
“That was amazing”, he said. “Totally unexpected.”
I laughed and agreed, “Definitely not what I planned for tonight.”
“Well, listen, Penny….I need to leave the party now, but I’m taking my yacht out this weekend, if you’d like to come aboard”, he said.
I thought to myself, ‘I like the sound of that’, so replied, “I’d love to, Warren! Just tell me where and when.”
“Meet me at the marina at 9 am on Saturday. I’ll provide food, towels, sunscreen…..everything you need, so just bring yourself and a bathing suit, and you’ll be good to go.”
“I’ll be there….what fun that’ll be!” I said.
Warren said, “Excellent. I’ll see you then.” He bent down and gave me a lingering kiss, squeezing both of my tits one last time, with a little pinch to each nipple, then patted my butt as he turned and left the gala.
As I continued enjoying myself at the gala, I kept thinking about Warren and taking a ride on his yacht on the upcoming weekend. I smiled to myself and thought…”that sounds really interesting. I can’t wait for Saturday.”
