Ch. 01: Several Firsts with a Friend - Sex Stories

Ch. 01: Several Firsts with a Friend

... gather my thoughts and figure out where I'd go with this. I'd never really thought of her that way. It's not that I didn't find her attractive or was afraid of an older woman. In fact, most of the porn I was watching at that time was of older women and younger guys. I just hadn't considered such a possibility; that even though girls weren't interested in me, a woman would be. Plus she was married with kids my age. I actually knew them well.

So I gathered myself and explained that I too felt some connection but I knew she was married with a family. She went on to explain how loveless (and sexless) her life was and that she needed a companion the way I did. I knew what I was considering with this 51/52 year old woman was wrong but I was 21 and had never had a kiss. How many guys would say no in that situation?

She went on to explain that we were friends and truly cared about each other, and that there was nothing wrong with two friends who care for one another, taking care of each other's needs. With that, I willingly took the bait. I asked how it would work and she said we could get a room somewhere. I asked when. Her reply, "right now."

All I could say was "ok, let's go."

We walked outside and stood between our cars. She came in to hug me and with that, we somewhat awkwardly but sweetly shared our first kiss... my first kiss.

I said I thought I knew a place and told her where it was. She knew exactly where I meant. We drove separately, me as fast as I ...

... could.

When we arrived, we walked into the office together. I asked for a room with two beds as if that was going to fool anyone. We went into the room, sat down on the beds and began holding and kissing each other. My hands went to the curves of her hips and her arms wrapped around me.

Still with our tongues entwined, we slowly laid back onto the bed, she on her back, I on my side. One of my hands worked upward until I reached one of those soft peaks. They were big and for the first time, I held a tit in the palm of my hand. I massaged her slowly as our tongues flicked and danced; mine trying to mimic the movements of hers. I wondered what more I should do with my hand.

She began to pull off my shirt and so I slid out from it and did the same to her. Next I anxiously went to the rear of her bra. Having seen plenty of scenes in comedies that started this way, I filled with nerves as I reached back behind her, but I had no trouble unclasping each of the four hooks one by one.

Her tits were amazing. They were big and they were mine for at least the next few minutes (hopefully more). We quickly got out of our pants and laid backed together, me staring at the fullness of her chest, and the dark Ariel as crown by large but feminine pink nipples. We continued kissing as I didn't want to rush. I'd heard women don't like to rush. Then I heard it, "I want you."

That's when I rolled over and nothing. I went limp. Here I was ready to lose my v-card with a curvaceous cougar who was ...