Ever since I learned what masturbation was, my stepmom Pammy became my #1 jerk off subject. After every weekend I spent with my dad and stepmom I would come home and my dick would be so sore from jerking it off all weekend. I was in high school when I really started to notice Pammy; she was 37 at the time. I don't know if she would qualify as hot to most kids in my school, but she drove me wild. Pammy is average height with a slender body. Tits were 34B, I knew from always looking at her bras, and also a fantastic pair of legs on her too. I always thought she had the body of Stephanie Seymour, a famous model. Pammy's face was average though and she would always keep her hair cut very short.
So many things about Pammy turned me on. She would always wear very simple, yet sexy clothing. Maybe it would be a tight sweater or tank top, very short pair of shorts, or a nice short skirt to show off her legs. She usually wore loose tops around the house and I would always find a way to see her boobs when she would bend over to do something, I'd even catch a glimpse of her nipples now and then. If she and my dad needed to go somewhere and I didn't care to go, I'd stay behind so I could go check out her panties and bras. Pammy always did laundry so it was a rare to find a soiled pair, but there were some magnificent clean ones in her drawers. My favorite was the sheer black thong. I don't know if she ever wore it, but I used it countless times to beat off, even tried it on a few times. Her ass must have looked so good in that pair. Out of all the time I spent at their house, I can only remember hearing Pammy and my dad have sex a couple of times, and my dad was the one making all the noise.
I only saw Pammy completely naked once, I was 18 and a senior in high school. It was very late at night and I couldn't sleep. The door to their bedroom opened and I just barely opened my eyes and saw Pammy walk out to go to the kitchen. She had absolutely nothing on, not only did I see her perfect tits, but I saw her full bush too. I waited for her to walk back to get another view and then went right to work beating off. Whenever I masturbated in bed I would make sure to get my cum everywhere, I really didn't care if she found it on my sheets, I actually wanted her to. Of course, I would do other things in hopes of her getting her to fuck me, but I knew it would never happen. I'd sleep nude and hope that maybe she would come in and see my morning wood when she needed to wake me up or. I'd always look a little too long at her breasts when she was bending over. If I gave her a hug, I'd hold it a little longer than usual.
I spent a lot of time at their house during the summer before I left for college, I was 19 at the time. I couldn't even tell you how many times I beat off while thinking about Pammy. I had every fantasy too: She would catch me beating off and then take over for me first by stroking me then by sucking my dick, or I would show up when my dad wasn't home and she would be extra lonely and we would fuck all night long, or my favorite...my dad would tell me to go fuck her because he was too tired to do it.
I moved away to college and saw less and less of her, but would still beat off to Pammy occasionally. Even during the few times I would get laid or get a blow job from some college chick, my mind would drift off to Pammy and I would picture her with my 6" dick in her mouth getting ready to swallow all of my cum or jerk it all over her tits and let me lick it off of them.
My fascination with my stepmom almost went away when I got married at 24. I knew there was no way I could fuck her now. Although she looked so damn good at my wedding. She had a very nice dress on showing just a little cleavage. I gave her a nice tight hug and while I was, I started to get an erection. However Pammy gave no indication of noticing, although I knew she had to of noticed it through my slacks.
Soon after I got married I learned some terrible news from my dad, he and Pammy were getting a divorce. It took awhile to calm my dad down as he was heartbroken and I started to believe everything he said about her, I began to think she was a total bitch. I didn't think about her sexually for at least a few months, and then I realized that she was single now. Unfortunately I wasn't. I started to fantasize about her just like I was 18 again, mostly picturing her get fucked by different dudes now that she was divorced. I thought that she might even be hooking up with guys my own age; I'm now 27, which makes Pammy 49. I was beating off 3 times per day thinking about her. Even when my wife and I would have sex, I would be pretending it was Pammy. But never in my wildest dreams would I imagine that I would actually fuck her.
One night I went out with a married friend of mine, Rob. He and I have been friends forever and we both like to still have a little fun with women on the side. Rob also shares my love for older women. We stopped in at a sports bar close to his house to have a drink, watch a little sports, and check out any ladies that might be there. The women in the place were ok; we were having more fun reminiscing about the old times when we were kids. And then something caught my eye. My fucking stepmom Pammy walked in with another woman. Pammy was looking real good, she looked tanner than I remember, and was wearing a sleeveless tight black top, nice pair of jeans, and some black high heels. Her friend was not quite as hot, but I would still fuck her too. She had on a white blouse and black pants. Her blouse was pretty clingy showing off a nice pair of tits. Rob and I watched them both take a seat at the bar and order a drink. He asked me what I thought of them. I said that we she keep an eye on them and maybe make a move later. I wasn't sure if Rob recognized Pammy, he didn't act like it. They probably only met each other once or twice when I was younger.
I couldn't believe my luck, Pammy was here getting drunk and I was already drunk, I had so much liquid courage in me I knew I had to at least try to get in her pants tonight. Rob and I watched them drink a few glasses of wine and then I told Rob I was going to make my move on the one in black. He is more a breast man than me so he was fine with that. I carefully walked up behind Pammy and whispered in her ear.
You are the hottest woman in here, can I buy you a drink?
While we were watching the ladies, the bar had turned into a dance club, and there were a few couples out getting their groove on, and I was hoping that I could get dance and grind a little with Pammy before moving on to bigger and better things.
Pammy turned around not knowing what to think and was very surprised to see me. She threw her arms around me and gave me a huge hug. I could feel her breasts smash into my chest and I assume she felt my semi hardon press against her. I forgot how good she smelled. I sat down and was introduced to her friend just as Rob made his way over.