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 yenibosna escort 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 zeytinburnu escort 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.
“So you took what I said as an invitation?” I asked. She stopped and shrugged.
“Wasn’t it?” Eileen asked, without turning to look at me. “I mean, come on. You’re obviously a player. Why else would you say that?” She turned to face me.
I started to protest, but she held her hand out and shook her head, making any denial useless. I could see that the next move was up to me or she was going to turn tail and run. I stood and guided her back to the sofa. She went willingly, but she seemed brittle, suddenly very tense.
I sat down beside her, laying a hand on her shoulder. I could almost feel the tension radiating from her. I aimed to change that. I leaned toward her and gave her lips a soft kiss. I heard her breath catch and then release at this slight trespass. I knew if I moved too quickly, she would lose her nerve and go home.
I kissed her again, a little longer and deeper this time then I backed away, looking at her eyes to gauge her response. At first her eyes remained closed, expecting another kiss. When the opened, I looked into them intently with what I hoped was a warm, reassuring expression on my face. She started to say something, but I laid my index finger gently on her lips.
“Shhhhh,” I breathed and kissed her again, laying my hand on her thigh as I did. It took several more kisses and some gentle caressing of her shoulder and thigh, but slowly I felt Eileen’s muscles relax. Her breaths became deeper, almost a sighing. She was almost ready.
“Are you sure you want this?” I whispered in her ear. A slight cry escaped her as she nodded her head. That was all I needed to hear. My hand that had been massaging her lower thigh began to work its way under the hem of her dress. I felt a shiver run through her as my hand glided along the inside of her thigh. A low moan broke from her lips as my fingers reached her mound.
As I suspected, she was wearing nothing under her dress. When I reached the top of her leg, I felt her soft pubic hair. I tickled her gently with a finger for a moment before getting between her legs. Eileen lay back on the sofa, one leg on the floor, the other hiked up beside her, exposing her pussy to me. I ran my tongue along her thighs as my fingers continued to lightly brush the outside of her box.
Eileen’s mound was covered with thick black hair. It was a neatly trimmed full triangle, which I like better than the “landing strip” or shaved look. I brushed my nose through her pubes as I jumped my tongue from one thigh to the other.
“Ahhhh!” Eileen moaned, her hips bucking. “Oh, God. Lick me. Lick me, please.” I took my time working up first one thigh, then the other. By the time I actually put my tongue to her clit, she was practically ready to cum. I gave her some slow, light licks just to get her started, but it was enough to send her into a frenzy. I felt like a rodeo cowboy trying to stay on her as her hips gyrated and bucked.
“Oh! Oh, God!” she screamed after only a minute or two of my attentions. Her back arched and her body quivered as she climaxed. As she settled back onto the sofa, I began a slow steady licking of her clit, running my tongue lazily over and around it. Within five minutes, her body was twitching and thrashing as another orgasm built up. When she came the second time, she threw her head back to scream, but no sound escaped, just voiceless air rushing out of her as she exploded again.
I continued to lick her for at least another fifteen or twenty minutes. I’m not sure if she came again, but most of the time she was bucking, squirming and crying out. I could see the sweat acıbadem escort glistening on her face as she panted and moaned and gyrated her hips in ecstasy. Finally, she pushed me away.
“No more,” she sighed. “Can’t take any more.” I gave her one last lick, sucking her clit up between my lips and running my tongue across it. Then I pulled back and sat up. I suspected what would happen next and had already decided how I would play it.
Sure enough, once Eileen had caught her breath, she sat forward on the sofa and reached forward and reached for my pants.
“Oh God that was good,” she whispered as she put her hand on my crotch and started to rub me through my shorts. “Put it in me,” she said.
“Can’t do that,” I told her, gently (if reluctantly) pulling her hand away. “You’re married.”
“Little late to worry about that, isn’t it?” she asked, with a bemused smile.
“Not really. I can still honestly say I haven’t slept with a married woman.”
“You’ve got me there,” she laughed. “I guess I should at least offer to return the favor, but…”
“But what?” I asked.
“Well, I don’t… I haven’t, well, you know…” Eileen’s face grew slightly red. “I told you, my husband and I, we just don’t…”
“That’s okay,” I told her. “You don’t have to do anything for me.”
“But after that,” Eileen replied, sighing, “I really want to. I just, you know…” If she was inexperienced, it could still be good. After all, it isn’t that difficult for a woman to please a man with her mouth. If she was just reluctant though, I would rather pass. First, as I’ve said before, I don’t want a woman to do anything for me that she doesn’t want to. Second, about the only way a woman can ruin a blow job is to not want to give one. The willingness of a woman to take a cock in her mouth is a big part of the turn on.
“Another time,” I said and got up off the sofa. I offered her a hand up. She took my hand, stood and straightened her dress.
“I thought tonight was your last night here,” Eileen said.
“Yeah, but I’m sure I’ll be back again the way those two travel.” She looked at me, her eyes narrowing slightly.
“And you think I’d ever do this again? This is a one-shot deal,” she said, holding up her hand to show her wedding band. “I can’t take a chance like this again.”
“Then I’m glad we made the most of it,” I said and gave her a peck of a kiss. “It really was my pleasure.”
“Yes, but I’m not sure I want it to be over yet.” Eileen reached out for my pants again. “I don’t know if I’m any good at this, but I want to try.” She pulled me back to the sofa and I sat down obediently.
Eileen sat on the sofa beside me and undid my pants. My cock was hard and getting harder at the thought of her lips around it. She looked up at me with a bashful crooked smile and then lowered her head into my lap.
She held my cock gingerly between her thumb and first two fingers and began kissing it all over. I gave her a sigh of encouragement and settled back into the cushions of the sofa. She continued kissing it for several minutes. I wasn’t sure if she just didn’t know what to do next, how soon to go on, or if she was just not ready to have me in her mouth. I started to fidget a little bit and was getting ready to stand up and forget the whole thing when I finally felt her tongue on my shaft.
Again, she seemed to spend a lot, perhaps too much, time licking me. I enjoy being licked, don’t get me wrong. But usually it’s not all I’m getting. Women with more experience will alternate licks and sucks and kisses to keep me stimulated. Again, I wasn’t sure what was holding her back, but I was thinking that maybe this wasn’t such a great idea and I should stop her.
I pushed her back and she looked up in surprise.
“It’s okay,” I reassured her. “You don’t have to.” She just stared at me for a moment. I thought for sure she would jump up and run out, telling me what a jerk I was on the way. But then she took a deep breath and lowered her head back over my cock. This time her lips parted and my head slipped into her mouth. I could feel her tongue flicking frantically at it, almost like she was licking a clit.
It was the first time Eileen’s tongue had touched the head of my cock and I felt myself throb with anticipation. She slid her mouth slowly down my shaft, taking in more than half of it before she stopped. I still felt her tongue working like crazy and I wanted to tell her she was trying to hard, but I didn’t want to discourage her. I waited until her mouth bobbed up and down on my shaft a couple of times and then gave a low moan, “Oh, yeah. That’s it.” Taking her cue from me, she continued to bob, going a little bit faster, gaining confidence with each pass of her lips.
Eileen was half sitting, half kneeling on the sofa, bent over in my lap, so that all I could see was the short brown hair on the back of her head. I wanted to see more, so I stopped her and guided her to the floor between my legs.
“You may find it easier from this position,” I suggested. “Besides, I want to see you.” She hesitated for a second, then knelt between my legs. Then I watched as my straining member disappear into her mouth. Eileen looked so good at that moment, on her knees in her little sun dress, eyes closed as her lips encircled my cock. “Ah, yeah,” I sighed, as much from the sight of her as from the warmth and wetness of her mouth. My words seemed encourage her and her pace quickened.