Years ago I was caught by the daughter of a friend.
Several years ago a woman who has been a friend for a vey long time offered to take care of my dog while I was out of town. She came to my house to get keys and get a bit of a rundown on the dog's needs, and she brought with her her daughter, who was at that time a high school senior. The daughter, Shari, surprised me: I had met her only a couple of times when she was very small. J. gave custody of her back to her father because he was very well to do and could better provide for her when she was about 7. I saw J only sporadically and never, it seemed on the weekends when Shari was with her. On this occasion I was confronted with a drop dead gorgeous young woman in tight faded jeans and a loose sweater. She was tall, athletic, with long blonde hair and the sweater was not so loose as to conceal the fact that she had large, full breasts. At first I honestly didn't know who she was and thought that my friend J had simply brought along a friend.
Confusion over, we arranged for the dog's care, and they left.
Before continuing, a little background is in order. I met J a little more than a decade earlier when she was 17 and I was about 25. We were good friends, but but never more than that, although not for lack of trying. For a number of reason I never managed to get in her pants, but a the time of this story I thought I might have a shot. About 2 years after I had been her I had been in the hospital for some tests, and J was to drive me home the day I was discharged. Very much on purpose I waited to change into street clothes until she arrived. I was excited by the idea of stripping in front of someone not expecting it, and this seemed like an opportunity. She wasn't going to fuck me, but I figured I could at least generate some jack off memories. When she arrived, she saw that I wasn't changed and said she would wait out in the hall. I told her to wait in the room: "No just close the door and have a seat while I get my clothes on."
She sat down about 4 feet away from the bed where I laid my clothes, and I proceeded to take off the hospital gown. My cock was rock hard and pointing at the ceiling. I looked at her and said, "Sorry about that, but I can' help it." She just kind of kept talking but she also didn’t look away or embarrassed. She didn’t say a word about it then or in the intervening years, until a couple of months before I asked her to look after the dog.
I received a phone call from her one evening, and it was very clear that she was drunk. After a bit of the nonsensical conversation that one has with someone drunk, she asked, “You remember when I drove you home from the hospital?” I told her I did, and mentioned that at the time she had a 280Z that was her pride and joy. She said, “I just want you to know that that was one of the top ten hardons I’ve ever seen. You’ve got a beautiful cock.” I remember what she said as though I were listening to it all over again, but I really don’t remember my reply. I know I was a little bit stunned by the comment since it was well outside the character of our relationship, and l believe I commented that it was a long time ago. I do remember that she said to me that she just want to tell me that and had to go. And I remember that I jacked of thinking about it without having moved from the desk chair where I had been talking to her.
There was no mention of the conversation and no repeat of anything like it. We simply went on being talking to each other occasionally and helping each other out now and then with one thing and another. And it was in that vein that she wound up taking care of my dog.
I came home a few days early. I unpacked and took a shower, and realized that I had not called J to tell her I was back and that she didn’t need to drive over for the dog. I went around the corner to use the phone in the den and as often when I was alone in the house, I wasn’t yet dressed. I sat down and called, but got no answer. In those days before cell phones, and automated voice mail, no answer was no answer, and I figured I’d try again later.
Sitting there naked at my desk I had fired up my IBM XT and was looking at pictures of a model named Jenny that I had downloaded from the Giffy BBS (and just because we can, this is her:
https://forum.oneclickchicks.com/show...0&postcount=48 ) I was naked in the chair, cock hard, and lightly stroking, when I heard the back door close.
I assumed that it was J, having come over to take care of the dog and thinking of that not too far in the past phone call, -thinking, as it turns out, with my little head- I called out, “Hey, I’m back here. I just got out of the shower and I’ve got to get dressed. You caught me in the middle of something but you can come back if you want.” I was thinking to myself that she couldn’t say I hadn’t warned her, and since she clearly hadn’t forgotten about my previous exposure those may years before and just as clearly apparently had enjoyed it, I would up the ante and take the opportunity to let her “catch me” jacking off in front of her.
I had stood up to grab some hand lotion off the shelf and was stroking it onto a very hard cock, when suddenly tall, blonde, gorgeous Shari walked into the room! All in the same moment I stopped jacking, dove for my towel and told Shari, “I had no idea it was you. I’m sorry. I had no idea.” At the same time she was saying, I’m sorry, I heard something and . . .Oh, my God, I’m sorry. I hope you’re not mad. Really, I didn’t know.
I had wrapped the towel around myself and said to her, “Shari, I’m terribly sorry. Let me go get dressed.” She hesitated for a second -one of those little pauses or interruptions that you sense as much as hear, and then said, “I’ve never seen a man do that before.”, and I replied, “Well, believe me I didn’t mean to be your first!”
She said, “Oh I’ve seen penises, but boys, not men. Yours is different.” I was actually VERY nervous, and told her so, “First of all, your mother will kill me, even though I didn’t mean for you to catch me, and secondly I am not having this conversation with J’s daughter, OK? This should not be happening.” I couldn’t help but think of all the possible ways I could wind up in trouble. But she was still there, and I point out once again that she was essentially a walking wet dream. As a result, I was also thinking of what I would LIKE to have happen.
She just said, “It’s not that big a deal. It’s not like I’ve never seen guys or had sex.” And then that hesitation again, and she pointed to my cock and said, “Well, THAT’s a big deal. I’ve never seen a guy doing himself before.” And again a slightly longer pause, and: “Will you finish and let me watch?”
Shari watched. AS I sat in my chair leaning back and holding my balls, she sat by the side of the chair and watched. The only words in the room were me saying, “Oh, fuck this feels so good.”
It was a little awkward when I finished, and was sitting there nearly passed out, slumped back in the chair, slid halfway to the door with my legs spread and hand lotion and come all over the place. I told her I needed to grab another shower to clean up and then we should talk. I asked her to stick around until I got dressed.
She said that she’d stay and then added, “Don’t worry so much. I’m not a virgin and I’m not going to fall in love or start following you around. I just think that was fun. We really don’t need to talk about it. I’m fine. Are you having sex with my mom?”
Well, out of the clear bleu, that got my attention! I answered that I was not, and she said, “Then why don’t we? I promise I won’t tell anyone, bit I REALLY want that in me.”
(I pretty much fucked Shari through most of her senior year. She went away to college, but when she was home, we often got together for sex. And these may years later we still do, although she is now married and has two kids, so it’s sporadic. Oh, and I finally got in her mom’s pants several years back and fuck her regularly. I think Shari might know that her mom and I fuck from time to time, but J has no idea that Shari and I do.)