First Time Vacationing Without Family

My last year in highschool I took the last week of the summer off from my job and went away on my own for the first time. I went to this lodge for three days because it was familiar.

The owners knew us and Mrs. 'W' gave me a special price. At meals I sat with her and her husband at the 'staff' table. This particular week Mrs. W had a lady friend staying there. I met her at the first meal and she hardly looked at me, this 'Carol Wood' was not introduced as a 'missus' although she was older, and she wore no rings. I figured she was what my grandmother called a 'maiden lady'. After dessert I went for a walk on the beach. As the sun got lower to the horizon it began to get cool. I turned around and started walking back, finding it quite chilly walking into the stiff breeze. I was surprised to find Carol Wood sitting wrapped in a blanket on the beach.

Carol was maybe my mom's age, in her early 40s, with a sweet face. She carried a few more pounds than mom, but her cleavage was very generous and she had an attractive rounder shape. At 18 I found older women extremely attractive, as I had already lost my virginity to one of mom's friends.

Carol said I looked cold, and would I like to warm up with her under the blanket? We sat in the sand with the blanket wrapped round our backs and held together in front of us, watching the sun go down. We talked about all sorts of things. I decided that I really liked her a lot, but I was too shy to tell her how much I was attracted to her.

Then she asked me if I masturbated a lot. At first I couldn't decide how to answer, the truth ('yes! a lot!'), or just play stupid like I didn't know what she meant. That was when I felt her hand seeking out my maleness. I wasn't wearing any underwear under my shorts, so she found 'Willie' quite easily, and I started to get erect right away.

'Yes, I do,' I said. 'How often?' she asked. 'Coupla times a day' I admitted, not looking at her. 'Oh! That's interesting,' she said. I was really hard by now, feeling like I might ejaculate soon. 'Do women masturbate too?' I asked. 'Yes,' she replied. I never talked with anyone about sex and I found it was stimulating to be talking so openly about sex. I said that I didn't know women masturbated. She explained that women like it a lot. 'Well, I do,' she said, with a warm smile.

I didn't know what to do next. Was I supposed to reach over and touch her cunt? She was still stroking my cock, and looking at my eyes. 'You're shy, aren't you?' she said. At that moment I suddenly felt myself cumming. I got really embarrassed, but she said I shouldn't be, that it was very natural.

Then she asked me if I would do something for her, she wanted me to sneak up to her room in the lodge and sleep with her. I knew she was in the room next to mine, so there wouldn't be much sneaking to do. I said that yes, I'd like that. I had never had the chance to be in the same bed as a woman.

We walked back up to the lodge. I lay there in the darkness in my room until I heard Carol knock softly on my door, then I followed her silently into her room. With the door closed she took a deep breath and said, 'Can I see your cock?' I could see her blush in the dim light as she said 'cock', as if she had never said it before (maybe she hadn't!??). Her voice had a breathlessness now, I could tell she was excited just like me.

I dropped my shorts. My cock sprung to attention. For a minute I felt embarrassed. Then Carol turned to close the curtains and I heard her undressing in the dark. I moved toward the sounds and she hugged me, then she kissed me on the lips. As I lifted my arms to hug her, my hand brushed across the inside of her thigh and I felt her wetness on the inside of her legs. I didn't know what to do.

She led me to the bed through the darkness, and we crawled in under the covers. I lay beside her, then put my hand between her legs, probing her. In a very quiet, breathless voice she said, 'Oh! that's nice. That's very nice.' Well, that was all the encouragement I needed, and I knew that I was on my way with her now.

I had had some practice fingering my girlfriend in Grade 12. I continued to probe Carol's vagina, first with one finger, then two, then three. She reached down and moved my hand further forward, 'gently,' she whispered. She started to really enjoy my triple fingering and probing and took her right hand and started to stroke my hard cock. Several minutes later I could feel my cum beginning to put pressure on the base of my cock, 'I'm going to cum!' I said, 'I just don't want to finish...too soon.' 'Oh, come, Roddy, come for Carol!' she urged.

I could feel my climax building. She was stroking me furiously now. 'Ummh, ummh,' I began to moan. 'That's it, come for Carol! Oh, please, Roddy, come for me now!'

In the darkness I couldn't see her face. Oh! I wanted so much to look at her tits as I came. I placed my hand over hers and stroking myself just a couple of times I came, squirting four or five thick jets of cum across the space between our bodies. 'Oh, my, so much!' she said, sounding surprised.

'I'll be back,' she said, and moved quietly off the bed to the bathroom.

I was quite sleepy by the time she returned, and she had me turn my back to her as we snuggled under the covers. As I drifted off to sleep I could feel her rocking slowly in the bed, a faint 'squish-squish' noise emanating from her hand in her pussy. 'Thank you,' she said. 'We'll do it again in the morning!'

That's another story!