Lost Beach Ch. 01

Three weeks prior to being dumped by my girlfriend, Cindy, I had purchased anon-refundable package for two at the Lost Beach resort on St. Thomas in the US Virgin Islands. I was really looking forward to going on this trip with her – she was a "big boned" girl with lots of soft curves, and she really got me hot, but she was somewhat hesitant in the bedroom. I noticed that she loved to sunbathe, and showed quite a bit of skin when she did – not so shy then. I hoped that the warm, Caribbean sun would bring her out of her shell a little bit. That is, I had hoped that spending most of the day on the beach nearly naked, in a string bikini, would make her warmed up at night. Or in the morning. Lunch time. Anytime.

I think I may have been hoping too hard, and may have pushed just a bit, because she said when we broke up that she couldn't handle my "wilder side," by which she meant my kinky side. I occasionally liked to end our love-making by masturbating on her breasts, or face. I had developed a fondness for light spanking play. And God, did she have an ass for it.

Anyway, there I was, with two tickets, and no partner.

I thought about other women I knew who I could call, but it's awkward to call someone like an ex and ask them to go away to a resort for ten days. It's also awkward to ask someone with whom you don't have that close of a relationship, so that knocked out the women at work, and the red-head with whom I flirt at the grocery store.

My problem was solved for me by a phone call I received, from my mother.

"I can't believe I'm over the hill!" she wailed. Her dramatics were only partly exaggerated. She was turning 43 and not taking it well. Every year since 40 had been more and more trying.

"Relax," I said, "you're not 'over the hill.' You don't even look your age." Which was true – mom had had me at a very young age. I was now 22.

"You're just saying that, Jack," my mom – Brenda – said. But I wasn't. Mom was what I call a 'compact' woman – short, but very curvaceous. Large, round breasts (36D, I checked once while doing her laundry when she was sick), a rounded ass – but not too round – and her skin was very silky and smooth. Green eyes and blonde hair – she was a knockout. My father had left her before I was borne, and she'd raised me as a single parent. She'd had boyfriends, usually some fellow teacher at the community college where she taught art - but never anyone permanent in her life. Since it was 'just the two of us' usually, we'd gotten pretty comfortable around the house together. We had a pool in the back, and when I was a young teen I'd checked her out many times.

Mom went on to say that she was spending another birthday alone, nothing to do, no one to do it with...dinner with me just didn't cut it, I guess....so I made the offer.

"Actually, you've been great to me, mom, and I wanted to thank you somehow. What would you say to ten days at a resort in the Virgin Islands, all expenses paid?" "Oh, I couldn't accept that," she replied.

"You don't have a choice. I already have the tickets. Spring break is coming up, and the dates of the trip fall almost perfectly into that. You deserve this trip, and that's final."

"Oh, I can't believe it," mom gushed. Honestly, I thought she was taken surprised by the offer. I started to feel pretty good about myself, Class Act Son that I am. I told her about the beaches, the restaurants, the amenities like the tennis courts, hot tubs, jet skis, kayaks, and all the rest of it.

"But we will have to share a bedroom, mom – is that OK? Actually, it's what they call a 'semi-suite,' there's a bedroom and a separate living room, and the coach folds out into a bed. I'll sleep there, and you can take the bedroom."

We went back and forth over who would take the bedroom and who would get the couch, and she finally agreed, saying, "You are just the best son ever. This break is exactly what I need. And maybe while we're there you can find a nice island girl. Don't worry, I don't need you to be with me every minute."

I realized mom didn't know Cindy had dumped me because she didn't even know about Cindy. I told her, "I'm not really in the market for meeting someone right now, mom."

"Well, never say never," mom said. "But on the other hand, I am over the hill...." We were back to that again. I distracted her from that subject by reminding her that she had to pack, which reminded her that she had to shop. "I can't go down there with out a new swimsuit, some new beach clothes...some fancy dresses for the evening.."

Shopping....an instant cure-all for many women, I thought to myself. Do they meet secretly at night and take lessons?

That evening I poured a scotch, put on a DVD, and thought about what a good son I was. I also thought about how hot mom had looked when I was a teenager, in her swim suit. (especially her "sun bathing only" two piece). I drained my glass, opened my jeans, unbuttoned my shirt, and wrapped my hand around my warm cock...getting harder by the second. My cock is seven inches, not a monster, but nice...a little thick, cut. I like to start masturbating by squeezing, caressing the head, trailing my fingers up the underside, and back to squeezing....tickling my balls...only when I am really sensitive – the head of my cock gets almost ticklish – do I begin stroking...slowly at first...lying back on the couch, eyes closed...picturing mom's breasts jiggling as she walked around the pool...tan skin against the bright yellow triangle of cloth...stroking fast now...I knew I would come soon...was that a glimpse of a hard nipple under mom's top?...yes...just before I came I gripped myself very tightly at the base of my cock...squeezed...cupped my balls lightly with my other hand, barely touching them but feeling my hand....felt a pin-prick rush to the head of my cock, let go and spurted my cum up... and down, splashing onto my chest and stomach...if I couldn't splash Cindy at least I could splash myself...as I caught my breath I caressed a drop of cum around a nipple...I could feel my nipple respond....aw, well, Cindy...your loss.

Somewhere out there, I thought to myself as I headed for the shower, is a woman who will like it when I stroke my cock for her...