There is another wrinkle to my obsession that I haven't really touched on: I prefer older women. Why? Well, a few basic reasons are that they're more approachable, they know what they like and they aren't as worried about what people think of them. But the real reason is because they generally see oral sex much differently than younger women.
I grew up in a world where people learn about safe sex at an early age. It's no surprise that many of us saw oral sex as a less risky alternative to intercourse. Because of that, oral sex has taken on a status of something more casual than intercourse. It's somewhere between heavy petting and screwing. However, for many women who grew up years before me, putting a cock in their mouth is something far more intimate than taking it into their pussy.
So naturally when I get a blow job from a woman from this older generation, it means more to me because it's a bigger deal in her mind to do that. I know there are exceptions, older women who aren't uptight about it, and for them it may be no different than for a girl my age. It's just a generalization, but it gives me an incentive to seek out women fifteen and twenty years older than me. My next entry is one of my favorites in this particular twist of my blow job obsession.
I have a friend who lives in a rather pricey neighborhood and travels a lot for business. His wife is a freelance writer and usually travels with him. They're often gone for a week or two at a time and need someone to take care of their dog and keep an eye on the house. The last year or so I've been helping them out this way on a regular basis.
Their house, aside from being big, well-furnished and, compared to my apartment, luxurious, is also a bit closer to where I work. So I would stay the week, take care of the dog and live the good life. If that was all there was to it, it would still be a great deal for me. But as I was to find out, house sitting had benefits I never anticipated.
Part of taking care of the dog, AJ, included taking him for walks around the neighborhood. I usually threw on a tank top and some ratty old gym shorts and off we went. I admit, I consciously wear clothes that attract attention and this is a careful calculation on my part. I want to show myself off, since I do keep myself in good shape, but with clothes that would make it easy to deny I was. Who wears ratty clothes to get attention, right? In other words, I want to get noticed without being obvious that I'm trying.
So I would take AJ around this ritzy neighborhood in a tank top and shorts. I made sure to smile and say hi to everyone I passed. On rare occasions I would actually have a brief conversation, usually revolving around AJ. Like I said, I had a pretty good deal just doing the house sitting. I really wasn't actively pursuing my obsession; I just wasn't ruling anything out either.
There was one woman who was often out working in her flower gardens when I went by and I always said hi to her. I house sat in late April, again in the middle of May and again at the end of May. She joked once that she saw more of me than she did of my friends. By the time I was house sitting in late May, we had introduced ourselves and had had several brief conversations.
Her name was Eileen. She was married, no children and her husband traveled frequently. She was in her mid-to-late forties and hadn't worked in some time. I gathered from her comments that giving up her job hadn't been her idea. She was petite, pretty and always well-groomed despite the fact that she was usually gardening when I saw her. She had dark brown hair cut short in a very businesslike fashion. She had brown eyes, a delicate, slightly upturned nose and a crooked smile. Her body was nice, although she was probably carrying a little extra weight. Her legs were smooth and shapely, her ass round and full and her breasts were small, but perky.
Eileen wasn't a woman who ever really turned men's heads, but she was very attractive in her way. It certainly didn't hurt my opinion of her that half the times I saw her she was on her knees in her garden. Still, I wasn't going to be too forward with my friend's neighbors. Especially not the married ones. But I had given it some thought, so I can't claim what happened was totally accidental.
I was talking to Eileen during one of AJ's walks--she had made herself more and more available for conversations--when I let a casual joke slip out. We had been discussing my friends' house and Eileen said she had never been inside. So I started telling her about the huge sectional sofa, the big screen TV and all of the things that make it a real treat for me to stay there.
"Pop your head in sometime and take a look," I offered.
"Thanks, but no," she said. At first I thought she just meant she didn't want to seem nosey, but then she said, "The way this neighborhood gossips, I wouldn't want to be seen going into the house with you. They'll be saying I'm cheating." She smiled wanly.
"Just tell them that oral sex isn't considered cheating." I meant it as a joke. In fact, it just came out of my mouth before I thought about it. It's something I would have said to someone I knew much better without hesitation, but I didn't really know Eileen. She looked at me with a slightly stunned expression, her jaw slack, her eyebrows arched. I quickly apologized and made an excuse to get out of there.
I hadn't planned any of that, but I probably couldn't have played it better if I had. While I don't deny I had thought about Eileen, I certainly wasn't making any moves on her. What I wound up doing was planting a seed in her mind. It was inadvertent. At least in as much as I wasn't really trying to. But I have to say, I was glad that I did.
A couple days later I was walking AJ again and Eileen was outside. We just said hi to each other as I passed and I assumed that I had alienated her with my inappropriate joke.
The following day, the last one of the current house sitting stint, I saw her outside again and decided I should apologize again. Eileen seemed like a nice person and if she was offended by what I said, she had a right to be. I never like to offend people or hurt their feelings. When I do, which happens despite best intentions, I do try to make amends.
"Hi," I said to her as AJ and I came up to her. Eileen smiled slightly and said hi. "I just wanted to apologize for the other day," I said. "I shouldn't have said anything so crass."
Eileen dismissed my apology with a wave of her hand. "No need," she said. "It just caught me off guard. I do have a sense of humor. You just surprised me is all."
"Well, I didn't mean to offend you," I told her. "Anyway, Mike and Carol will be back tomorrow, so you won't have to worry about their ill-mannered house sitter anymore. Not until their next trip anyway."
I saw a funny look cross her face. I wasn't really sure what it meant and it vanished in an instant. I pretended I hadn't noticed and continued making small talk with her for a few more minutes before continuing on my way. By the time I was a couple houses away, I had completely forgotten about it. It wasn't until after the fact that I realized what that expression was about.
That night I was making myself comfortable as usual in my borrowed accommodations. I had grabbed a beer out of the fridge and was using the high speed internet connection to do some on-line dating. (More on that in another entry.) It was a work night, so I was pretty much settled in for the night. I was startled when the doorbell rang.
I was even more surprised when I looked through the peep hole and saw Eileen standing there.
"Hi," I said as I opened the door. "Wasn't expecting company."
"I just thought I'd take you up on the offer to see the house," Eileen said. The way she said it made me think of a bad high school play performer reciting a memorized line. But I'm not one to leave a lady standing on the doorstep. I invited her in and offered her a drink.
"Wine would be nice," she said as she looked around. I brought her a glass, noticing that she wasn't really showing more than perfunctory interest in the decor. I led her around room to room. She acknowledged the nicer items and made a few comments, but her distraction was becoming more and more evident. By the time I hade guided her around the whole house, her glass was empty.
"Could you freshen this for me?" she asked. Now I'm no fool and I knew something was up. But I like to play it cool until I see what the game is. So I brought Eileen another glass of wine and waited to see what she would do or say.
I should mention that I noticed what she was wearing, as I was doubtlessly supposed to. I was used to seeing her in baggy shorts and cotton blouses in which she did her gardening. Tonight she was wearing a thin, pastel sundress, low cut and fairly short. At least, considering how modest I thought Eileen would be it seemed short. And I could see no panty lines, and I'm a guy who notices a thing like that.
When I handed her the glass of wine, I said and did nothing to indicate I'd noticed anything unusual about her clothes or behavior. I smiled as she took a sip, more of a gulp actually, of her wine and waited. I should point out that I was making lots of eye contact with her. For her part, she was trying to meet my eyes, and would for a moment, but then would look away. There was definitely a charge when our gazes met. But I wasn't sure where things were going yet.
"Okay," Eileen said suddenly, putting her wine glass down. "We both know I didn't come over to see the house. And we both know that little comment of yours the other day was no accident." She paused, perhaps waiting for me to say or do something, but I was content to let her do the talking. She picked up her glass and took another gulp. She looked at me and I knew she wanted me to agree or at least encourage her to continue. I know she must have been feeling incredibly vulnerable at that moment, so I didn't leave her hanging too long.
"What do you mean?" I asked.
"What you said the other day," Eileen replied, gesturing with her hand. She said it as if it explained everything. Still I waited. "It is cheating, you know" she continued. I nodded in agreement. I was starting to get turned on. She was dancing around subjects like oral sex and cheating. She was dressed to be noticed. I almost couldn't wait any longer, but I managed to remain outwardly calm.
"Would you like to sit down?" I gestured to the sofa. We sat down and a long moment passed where neither of us said anything. We just looked at each other.
"My husband always hated doing that," she blurted out. "I always wanted it more. But he wouldn't." Eileen wasn't looking at me now. Her gaze was on the floor in front of her. She shrugged.
It dawned on me finally why she was here. It wasn't to have sex (intercourse, that is) with me or give me head. No, she was here to get oral sex. I know what you're thinking. What a disappointment to a blow job fiend like me, right? Hardly. Pleasing a woman is a wonderful thing and I have, if I may be slightly immodest, some pretty successful techniques. Besides, one thing I've always found is you've got to give a little to get a little.
"I, uh... this was a mistake," Eileen said, getting to her feet. I didn't panic, but I knew I needed to say something. She started toward the door.
