Serious Mistake Going Sailing

I’ve been divorced for 6 years now and in my mid-thirties. I love the outdoors and taking day hikes so I am in good physical shape. I’m 5’9 and have been told that I have great tits 40D. My eyes and hair are brown; I have straight hair that goes to the bottom on my bra strap. Several years ago I got connected to the internet and started chatting because I was lonely and not into the bar scene. There were a number of men and a few women on my friends list that I chatted with on regular basics. The women gave me an outlet to laugh & vent about kids, work, ex’s etc. The men I used as a safe sexual outlet. Sometimes I would turn on my video camera wearing only a low cut little shirt and my panties. I would angle the camera perfectly so the men could only see my face and plunging cleavage.

Matthew was the only one on my chat list that actually lived in the same town as I did. We chatted a while before we decided to meet. I was attracted to his powerful large body and somewhat forceful nature online. However, there were things about him that bothered me; like how private he was about his life and especially what he did for a living. He would just simply change the subject and tell me he didn’t want talk about it right now because he had a bad day.

While chatting & drinking a bit I invited him over late one night and before I could change my mind he was knocking on my front door. I invited him in and we sat and talked a while on the couch. Several times I caught him gazing down my shirt at my cleavage and breasts and it made me slightly giggle. Over the course of an hour or so he kept scooting closer and then I would scoot away trying to maintain my comfort zone until I couldn’t scoot any more on the couch.

He stopped talking and, with his left hand he reached up and ran his fingers through my straight hair letting the strands softly glide through just staring into my eyes. He did it again and again and again. Each time he would gather up more hair than the time before. His breathing change to deep slow breaths until he pulled my hair completely back so I wasn’t able to move my head. He planted one deep and very forceful kiss on me. He moved so his knees were on the outside of my thighs squeezing them together. At that moment my heart was racing as I felt very vulnerable and quite helpless. He released my hair gently and then again he ran his hand through my hair and pulled once more this time more aggressively. My head was being supported by the back of the couch as his lips encompassed mine, harder he pushed with his lips and body. With is right hand he massaged my breasts and squeezed and pinched my nipple. I let out a moan into his mouth. I could feel his cock pressing against stomach. My body responded to his rough handling as he released me with gentle touches.

We made out like this dozens of times most of the time he got some kind of release before he went home and each time a little rougher but we never went all the way. I loved the way he took control and expected me to follow orders which I did very happily because it pleased him. We talked and found out what more we could do for each other to make our sexual encounters better. He took me out to dinner a few times always paid in cash and always the perfect gentleman. He had a sail boat and asked me to join him sometime. It sounded like something fun to do so I agreed.

He picked me up in his car in the very early predawn hours so we could get a full day of sailing in. The weather was perfect for sailing a sunny day with a brisk breeze. He asked me to bring a nice outfit and to pack in a tote my black lacy bra, panties and heels he liked me to wear for him. He told me lots of times he enjoyed the contrast of my white skin against the lacy black silk of my bra and panties. He said “he would take care of the food and drinks but I would be the entertainment”. The sailboat I thought was a little larger than he described to me but I didn’t think anything of it. The both of us boarded and with some instructions to me we were off. We sailed out of the bay and into the ocean and then to a nice private cove. He dropped the anchor and then when down to the galley. When he came back up he had two drinks of ice tea and sat down next to me. He said “you get the Ice tea when you unbutton your top” with a wink. Which I complied slowly teasingly one button at a time, we both sat back in the seats, relaxing enjoying the warmth of the sun while we drank our tea. Being in the cove we were protected from the wind so there was just a slight gentle rocking of the boat. I closed my eyes feeling totally relaxed and before I opened my eyes I could feel Matthew stroking my hair and then gently kissing my face and neck then and mouth. Like usual, his kisses started soft and gentle and then longer we kissed the more intense and rougher the kisses and touching became. I could feel wetness in my panties as my desire increased for him.

With both of his hands he lightly took my wrists then lifted my arms up and placed them above my head leaning them against the side of the boat while straddling me on the bench seat kissing me.