My first fuckbuddy was a woman who was 46, 21 years older than me. We started out as friends, but then after going out to a movie with some very sexy scenes that had both of us turned on, that evening we became lovers.
She had a boyfriend who was a few years older than her. 'Irene' told me once that 'Henry' was not only dating her, but other women, who also wanted Henry to settle down. According to Henry's sister, Irene told me, Henry was enjoying all this female attention, and was in no hurry to marry anyone. Irene said that after she and I became fuckbuddies, she was not interested in trying to bed Henry anymore. Besides, he was a pretty blah lover who once he got off, turned over and went to sleep. Henry had money, and knew how to show a woman a good time, but Irene said that she had lost interest in him for the long haul. She also told me that since she had stopped trying to sleep with Henry, he kept pestering her to go to bed with him. She told him that he had his other girlfriends, but he answered that he wasn't as attracted to them as he was to Irene.
One Saturday morning, as Irene and I began to wake up after a Friday night fuck session, a car pulled into the gravel driveway of her large secluded home. She sat up, looked out the window behind the bed, and said 'It's Henry!'
'Do you have a date with him you forgot about?' I asked her, teasingly.
'No, silly. I wonder what he wants.' She reached for her robe and after tying the sash around her slim waist, went into one of the six bedrooms she used as an office, and turned on the intercom. She also had a security camera mounted outside to see visitors and anyone who might pull into her driveway.
'Henry! What are you doing here?' I got up and padded into her office. I sat next to her, still naked, and she put a hand on my thigh, stroking it. Of course, this started making me hard. I put a hand into her robe, and began rolling a nipple around, making her squirm. We kissed as Henry, looking up at the camera said he was there to invite her to breakfast, and whose car was that in the driveway behind hers?
'That's my friend X's car.' We could see him go to my car and feel the hood, no doubt noting that it was cold. 'He stayed the night while helping me with a project for my class'. Irene was a schoolteacher. At that lie, she looked at me and winked.
'Well, if he doesn't mind, can I take you to breakfast?' He sounded a little peeved that another man was there, though she had told him before that she and I were just friends. Well, we were...with privileges. He couldn't fathom that Irene, a woman close to his age, would fancy young cock.
'Go ahead, Irene. I'll come back tonight, and we can pick up where we left off. It sounds like he needs some reassurance, and if he wants to spend money on you, let him.'
Irene looked at me. 'Well...but what about you and your nice prick? I was going to have a breakfast of your cock and come.' I got hard again, almost immediately, hearing those words.
'I'll call you in a few hours, okay? I'll go do some window shopping.' This was before cellphones.
'Alright, but I feel bad that he showed up unannounced. Let me take care of you first, and have some fun.'
Irene began kissing me, her hand fondling my cock and balls. When she figured I was hard enough, she took me by the hand, and led me back to the bedroom.
'He can't see up into here from where he's at, with the sun shining in, but I can look down on him. I'm going to jack you off right in the window, and he's not going to even know.'
She led me to the window, to where I could look down and see Henry, looking up at the window, but not able to see a thing. Irene came up behind me, her hand reaching around and grasping me as it had many times before. With her other hand, she rubbed my chest, and I could feel her kiss my back and move down, and even kiss my ass cheeks as she continued stroking me. My orgasm arrived quickly, causing me to spew come onto the sill and glass.
I leaned against the window, but too quickly, my head bumping it, and making a noise that caused Henry to look up. He then looked away.
As I recovered, Irene got into the shower, cleaned up, dressed in an outfit that I liked seeing her in, walked over to me, kissed me on my lips. She said she'd be back in a few hours, and she would finish what we had started.