I am 57 and I have a close lady friend in her early 60s. She told me that she had a very strong sex drive and that she often masturbated several times a day; she wasn't too upset about her widowhood but she really missed the sex. We had already had two masturbation sessions together.
As the fall colours turned, and more leaves fell, she became once again more flirtacious. She met me at the door, took my jacket, then gave me a long comfortable hug. We chatted for a few minutes.
We had learned that we enjoyed this pause when we knew something would happen, but what this time? I leaned toward her and we kissed, taking our time. Then I told her 'I would like to masturbate with you!'. She smiled. I unbuttoned her blouse and undid the front clasp of her bra, exposing her ample breasts. She slipped her clothes off her shoulders.
With her large nipples and D-cup breasts in view I felt a surge in my loins and I began to stiffen. She had this wonderful thing that she did, touching her breasts; she slid her palms upward from her belly, cupping a breast in each palm, lifting it slightly, then her thumbs brushing over the nipple, leaving them instantly erect and firm.
I pulled my turtleneck sweater over my head, exposing my hirsute chest. I stood up, unbuttoned and unzipped my pants, letting them fall in a pile on my loafers. I slipped off my underpants, my hand moved down to my shaft and I slowly pulled my foreskin back, revealing my dark red cock head. The sensation of that first stroke was exquisite. I told her how much it was turning me on to be naked and masturbating for her. Her neck, then her chest and shoulders became quite flushed. I could tell that she was becoming aroused.
I bent down, meeting her eager lips with my own. I cupped her breast, her hand cupped my balls, and the kiss lingered. As I broke off, I never lost eye contact with her. She broke the silence; 'It's cool today, let's slip into bed together.' I stepped out of my loafers and walked away from my pile of clothes as she took my hand to lead me into her guest bedroom.
Once there she pulled down the bedcovers, then shed her skirt. Very slowly she slipped off her matronly panties. This time she revealed a perfectly trimmed bush and shaven vulva. I told her how much I appreciated her doing this for me, as I knew 'our generation' was not one to shave pubic areas. She sat down on the edge of the bed, her labia were slightly parted, revealing the pink, moist clitoris. She smiled at me and licked her upper lip. Her hand moved to her bush. Slowly her finger ran lightly over her pussy lips, teasing us both. She repeated this stroking a few times. I was captivated, instinctively stroking myself, stretching my foreskin all the way back. The sight made my cock throb. She slipped under the covers and motioned for me to join her on the bed.
On prior occasions she had touched my member only briefly, sometimes giving it an encouraging stroke or a squeeze, or wiping off my cum at the end. Today she asked if she could stroke my 'maleness' she called it. I answered that I would enjoy her attentions very much. She pulled back my foreskin to reveal the deep purple head, clear drops of pre-cum leaking from me as I became more aroused.
She was fascinated that I was not circumcized. She slid the foreskin forward and back, I don't remember ever being so hard and aroused. In spite of the covers I could tell when she placed her other hand in the space between her legs, cupping her vulva. Then she spread her legs open, I could tell that she was rubbing her clitoris and sliding her fingers inside herself.
She said that feeling me hard and thick in her hand brought her pleasure on. These words increased my urgency. I told her I was close to cumming, and she quickened the pace, her hand fairly flying up and down my throbbing shaft. She pulled my foreskin back hard all the way as I creamed, spewing a thick rope of cum to splash on her belly. For six or seven strokes cum flowed out of my one-eyed snake.
By now she was frantically rubbing her clit, her breath coming in quick gasps and her eyes closed. She came within a minute, gasping, shaking, then finally stilled, her breathing slowed. She asked me to roll away from her, then she snuggled against my back as if we were two spoons in a drawer. We drifted off to sleep.