The Older Woman

When I was in college, I worked the night shift at a group home helping handicapped people.  

There were two women (Kristin and Wendy) that came in to work in the morning at 6.  Since none of the clients were awake until 6:30 or 7, I would chat with the ladies until the guys woke up. Needless to say, I got to know Wendy and Kristin pretty well.

Kristin was a around 30 years old.  Married, divorced, and with a bum boyfriend.  She also had 2 children from a couple of different fathers.  Let's just say she wasn't great at picking men.  She had a great personality, and was fairly attractive- but still a mom.  When people were around, she was the center of attention.

Wendy was around 36.  Married with 6 children.  She wasn't quite the center of attention that Kristin was, but there was something about her that I found her very sexy.  While she was not heavy, you could tell that having 6 kids put some extra weight on her.

As I got to know these women, I learned a lot about both of them.  Both of them loved to talk about sex.  Neither of them were getting enough from their men, and would tell me stories about the sex they liked.  

Kristin loved to talk about her favorite thing in the world - being eaten out.  After time spent with her man, she would go on about if he did it for her or not.  Everything in great details.  Man, I would have eaten her out with glee.  Many times, she talked about when she was younger and drunk - 5 guys took her one after the other.  She laughed when she told us about the nickname they gave the last guy, because he decided to take her in the butt.  "The rear admiral". She talked about the "crotch crickets" that she caught, and every other sordid detail that she had.  I learned a lot about sex from all of Kristin's stories, and I never had sex with her.

Wendy would also talk about sex quite often.  Her husband was only giving it to her a few times a year, and she was horny all of the time.  She said that when they were younger, the sex was non-stop.  Which is probably how they ended up getting 6 kids.  She also talked about a subscription that she and her husband had that gave detailed instructions on how to do different types of sex (These were pre-internet days).  At the time, I had a friend that wanted to try anal sex very badly - and I told Kristin and Wendy about him.  The next day, Wendy appeared with an article about how to properly prepare for anal sex.  I remember scrutinizing every detail of that article, and it really got me thinking about Wendy in that way.  Very much turned me on to the thought of anal sex with her.  I remember part of the article talked about spending time licking the woman's anus for a very long time to get them relaxed and prepared - which really turned me on to the thought of it with Wendy.

Even though I was quite shy at the time, the conversations with Kristin and Wendy were quite erotic for me, and made me really think about them sexually. I started thinking about their sex stories and imagined placing myself as the man in their stories.  I also really started paying attention to their bodies when I would see them.  Kristin would frequently come to work with her bra in her bag, and would put it on after her shift was over.  I remember many times sneaking a glance into her bag - 34b. I also remember how my eyes would be glued on the curves of her breasts when she would wear tighter shirts and no bra.  Her nipples would poke out, and it was quite a turn on.  Many times I wanted to rip off her shirt and play with those nipples.  I always wondered if she knew, and if she did this on purpose.

Kristin loved to talk and joke with me about sex.  I remember one point when I helped her move.  She had placed her vibrator on top of her underwear in the underwear drawer, and handed the drawer to me to carry out to the truck... and she laughed and joked about it the entire time I carried it out.  Man, I would have loved to put my cock in her pussy in place of that vibrator.

There were times when Wendy would talk about her husband sucking on her breasts.  She said he used to call them casaba melons - before they had kids.  She would go on about how they were not quite the same after kids, but she still loved having her breasts sucked. Man I wanted to suck on those breasts.  I also remember with fondness the shape of her ass.  There was a few extra pounds giving it a nice round shape- I loved her ass.  And there was this pair of black jeans that she would wear that really accentuated it.  One time she was standing behind me in those jeans, and she bent over to look in the fridge just as I turned around to face her.  Wow.  Here she was, nice ass, bent over, less than a foot away.  I started to reach out to touch it, but I pulled away at the last minute.  Man, I wanted her ass.

I remember at one point, Wendy telling a story that she had shaved her pussy the night before (pubic shaving was not as common in the early 90's)- that she was hoping to catch her husbands attention.  It started a long conversation about pubic hair shaving with me, Wendy and Kristin.  They both joked about engaging my help in shaving their pussies.  While I am not sure if Wendy got her husband's attention, she sure got mine. I would have happily shave both of their pussies.

As time went on, I started to find myself having feelings for Wendy, and I loved hearing more and more about her.  Many times, she would share details of her sex thoughts and life when Kristin was not there.  I learned that she was having a relationship with another man. She said they were not having sex, but she loved the attention she got from him.  She talked about the skimpy underwear and stockings that she would wear with him. How she would lay on her stomach and he would rub her ass and try to pry open her legs.  She said she would never let him put his cock in her (she was afraid to get pregnant), but I get the impression he probably rubbed it on her.  I was quite jealous.

I started to fall more and more for Wendy - one might say I was in love with her.  I was totally crushed when she told me one day - out of the blue - that she and I could never have sex.  She didn't want to ruin our great friendship.

Not too long after, both Wendy and Kristin took new jobs, but I would still hear from them from time to time.

I had learned that horniness had gotten the best of Wendy, and she was having sex with multiple men.  She mentioned that one day she had sex with three different men on the same day (one in the morning, one in the afternoon, and one at night).  Needless to say, I was kind of mad.  I was in love with her, and would have given her any kind of sex she ever could have wanted, and she was giving it away to these men that did not care about her.  One of them actually wanted to charge her for it.

Needless to say, Wendy became pregnant by one of these guys, and they all disappeared.  And her husband divorced her.

I subsequently stopped hearing from Wendy.

It is now more than 25 years later, and I still think about Wendy.  I have masturbated thinking about Wendy more than I have all other masturbation and sex with women combined.

While I never had sex with.... or got to see Kristin or Wendy naked... My memories of Wendy are quite vivid.  I still think about her casaba melons and sucking on them.  I imagine the look, feel and taste of her pussy - both hairy and shaved.  I also think most frequently about her ass and the anal sex prep guide she gave me.  One of my favorite masturbation thoughts is taking down her black jeans and rubbing her ass, taking down (and keeping) her panties, and endlessly licking her anus until she moans.  By this time in my masturbation thoughts my orgasm comes in torrents.... but sometimes, my thoughts take me to putting my cock in her anus.  At other times, I think about fucking her pussy, tits or mouth until I explode.  I never get tired of thinking about Wendy.

In hindsight, I am sure I could have had either Kristin or Wendy, but I was too shy or did not know what to do.  I think the both of them were really hoping I would have acted on my thoughts.  Why else would the both of them have shared such deeply secret sex stories with me. If I knew then what I know now, I would have taken them both... but I would not have had a lifetime of Wendy masturbation.