I have a thing for older women, more specifically, older married women. It started when I was sixteen and it continues to this day, some twenty odd years later. I guess it’s fair to say that I got an early start sexually. I was playing “doctor” with the girl next door when I was eleven and just before my twelfth birthday I accidentally got to see my parents making love. It was only natural that the next time Kay and I played doctor that I had to show her what I’d seen and even though I didn’t get penetration, I did get off and it felt so damn good that I had to keep on trying. Kay must have liked it too because she kept trying with me and the day finally came that we both lost our virginity. Unfortunately Kay moved away shortly thereafter, but I still think of her and I’d like to think that she still thinks of me.
By the time I was sixteen I had managed to get myself laid a dozen or so times, almost always by a girl a year or two older than me, but getting laid as a teenager, as I’m sure most of you know, is very hard work. The success rate is like one out of fifty tries unless you are lucky enough to have a Carol Meade (school slut), but the Carol Meade’s of the world are few and far between and they are always found on the arms of the older guys, guys who already have cars.
It was the summer of my sixteenth year and my best friend Tom, who lived just across the alley from me, and I were going to hop on the DSR and ride down to Briggs Stadium to watch the Tigers play the Orioles in a double header. I went across the alley and into Tom’s back door (we did things like that back then - go into each others house unannounced) and called for him. He didn’t answer, probably couldn’t hear me over the shower that was running, and so I headed back toward his room. He wasn’t there so I figured that it must be him in the shower and so I headed for the bathroom. The shower stopped just as I got to the open bathroom door and I saw Tom’s mother stepping out of the tub and onto the bathroom floor.
I’d seen several naked girls in the last couple of years, but I’d never seen tits like those on Mrs. Rose. She noticed me standing in the doorway and I expected her to scream and grab the shower curtain to cover herself, but instead she just looked at me and said:
“What’s the matter Dan? Never seen a naked woman before?”
The look on my face said it all.
“You haven’t, have you? Well, I don’t mind if you look at me. There is nothing wrong with nudity and I think that if you are comfortable with your body and with yourself you don’t need to be ashamed. Why are you here?”
I stammered out about the ball game and she said:
“I thought Tom told you. He is spending a week with his grandparents. While you’re here” and she tossed me a towel, “dry my back for me please.”
I caught the towel and with trembling hands I began to rub the water droplets off of her back. “Thank you,” she said when I had finished drying her entire back and she turned around to take the towel from me and her breasts brushed against my arm. She either didn’t notice or didn’t care and she took the towel from me and walked back to throw it over the shower curtain rod. I watched that magnificent ass walk away from me and my dick was harder than I could ever remember and I knew that I had to hurry home so I could jack off. I started to turn and go but she said:
“Don’t run off, I need you to do something for me” and she asked me to follow her. She led me to her bedroom and said, “Just wait a minute for me to throw a few things on. I’m going to need help with the zipper on my dress.”
She sat down on the edge of the bed and rolled on her nylons, stood up and put on a garterbelt and then stepped into a pair of high heels. She walked over to the dresser and bent over, digging through the drawer and leaving me to stare at that ass and her hanging tits. Her legs were slightly apart and I could see her hairy mound between them and I was hurting bad. I was torn between running for home and taking care of my self and staying to see as much as I could.
She stood up and turned, panties and bra in her hands, and walked toward me. Handing me the bra she said, “Here, hold this” and then she stepped into her panties. She took the bra from me and turned her back, “Hook me up” she said and as I stepped forward to do it my hard cock touched the cheek of her ass. She spun around, bra dropping to the floor.
“Oh Danny, how stupid of me. I’m sorry baby, I should have known better. It’s all my fault. Here! Let me make it better.”
She went to her knees in front of me and before it even registered on me what she was going to do she had my cock out and in her hands.
“Oh it’s a nice one! Much better than Tommy’s and almost as nice as my husbands” and then she took it in her mouth.
I’m ashamed to say that I came almost immediately, but Mrs. Rose had more surprises in store for me. She kept my dick in her mouth and swallowed every bit of my cum and she kept her mouth on me until I was hard again. She stood up and undressed me, led me over to her bed and for the next two hours Mrs. Rose rocked my world. Finally she said:
“You have to go now Danny. Mr. Rose will be home soon and I have to clean up. This is our little secret, right? You won’t tell any one about this, will you?”
“No Mrs. Rose” I stammered, “I’ll never tell any one, honest.”
She gave me a smile, “Good, you keep quiet about this baby, and maybe we can do it again.”
We did, many, many times over the next two years and after Mrs. Rose there was no going back to girls of my own age. Mrs. Rose taught me a lot during those two years and I was a pretty accomplished lover when I went off to college. I was also a whole lot wiser about a few things. Remember her comment “….yours is much better than Tommy’s”? It turns out that she and Tom had been getting it on long before I came on the scene. I found that out one day when I was busy pounding her pussy and we heard:
“Mom, I’m home!”
Mrs. Rose pushed me off her and rushed me into the closet and warned me to keep quiet. Tom came into the room and said:
“Waiting for me I see.”
Mrs. Rose said, “I’m always ready for you baby, you know that” and then I got to watch the two of them bounce around on the bed and surprisingly enough I got a charge out of watching. When she made Tom quit, “Daddy will be home pretty soon and I have to get cleaned up” and he was out of the room she came and got me out of the closet. As she led me to the bed she said:
“We have just enough time to finish what we started before I have to get you out of here” and I got my very first sloppy seconds. “You won’t say anything about this, will you?”
I laughed and said, “And ruin what I’ve got going here? Not a chance.”
She patted my cheek and said, “You are a sweet boy. We can talk about this tomorrow.”
I stood in the closet and watched Mrs. Rose and Tom a couple of more times and Mrs. Rose always timed it so I could screw her one more time after Tom was done and before her husband got home. I always wondered if Tom ever stood in the closet and watched me, but if he did he never gave any indication.
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I owe Mrs. Rose a lot. I got three things from her that I carried forward into my life, a thing for older women, a desire to stand in a closet and watch, and the confidence and self-assurance that I needed to go after older women. In college instead of chasing after the girls my own age I haunted the malls and shopping centers looking for older women and I had surprisingly good luck in finding them. There are a lot of dissatisfied housewives out there if you know where to look and have the balls to approach them. Of course you do occasionally have to put up with a crying baby, but to me it was always worth it.
I went all the way through college without ever screwing a girl my own age and my senior year was spent almost entirely in the company of a thirty-eight year old divorcee. But I never got to watch from the closet while in school though I think I may have been watched a time or two. I was surprised at how much I missed it.
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It wasn’t until I graduated that I got to watch from the closet again and it happened in a most surprising way. It was my mother’s birthday and she and my dad had several people over for a party. I was talking to Brenda, an old and dear friend of my mom’s, they had been sorority sisters in college, and she made the remark, “I never see you with a girl Danny” and I replied “That’s because young girls don’t turn me on Aunt Brenda.”
She wasn’t really my aunt, but I’d always called her that. She asked, “What does turn you on?” and I said, “I’m into older women.” “How old?” she wanted to know and I said, “About your age.”
She gave me an odd look and we parted. About an hour later I was coming out of the upstairs bathroom and I found Brenda standing in the hallway. I thought she was waiting to use the bathroom, but she grabbed me by the arm and pulled me across the hall and into the bedroom.
“Hurry” she said, “I can’t be gone too long or Harry (her husband) will come looking for me.”
She pulled me to the bed, stepped out of her panties and knelt on the bed. Being no fool I unzipped, stepped forward and buried my bone in her waiting pussy.
“Oh god” she groaned, “That feels so good. Fuck me Danny, fuck me.”
It had been some time since my last piece of ass so I went at Brenda hard and fast. It took me about five minutes and I shot my wad and as she pulled on her panties she said:
“Thanks. I needed that. We will do it again some time - soon!”
We had just started for the door and we heard someone coming, “It’s Harry” she said, “He’s looking for me” and she grabbed me and pulled me into the closet. We left the door open just enough so that we could see and the bedroom door opened, but it wasn’t Harry who came in, it was my mother and she was followed by an old friend of the family.
“Hurry” she said as she closed the door behind them, “We don’t have much time” and then Brenda and I watched as my mother repeated the same scenario that Brenda and I had just done. Brenda had my cock out and was stroking it as she whispered in my ear, “She always was such a slut.”
I watched in fascination as the woman who gave me life showed me how I had been conceived. God, but it was one major turn on. When mom and her lover were gone Brenda pushed open the closet door and moved in front of me and wrapped her lips around my cock. I came almost immediately. Brenda looked at me when she was done and said:
“Watching her really turned you on, didn’t it?” I nodded a yes and Brenda said, “Want to watch her again?” I looked at her and wondered why she was asking and then I nodded my head yes. “Good, we can kill two birds with one stone. Call me in the morning” and then she left me there with my limp dick hanging out of my fly.
The next morning I called Brenda and she asked me if I could come over and spend a good part of the day. Since I hadn’t started job hunting yet I told her that I could.
“Good” she said, “Try and get here between twelve and twelve-thirty.”
I was there at eleven forty-five and Brenda let me in and took me straight to her bedroom. “You and I are going to have so much fun together baby. I’m sure glad that you told me that you like older women.”
Once in the bedroom she stripped me and started sucking my cock. She was doing a simply marvelous job of it when the doorbell rang and she stopped sucking me and said:
“Oh good. That’s them. Pick up your clothes and get in the closet. Be quiet now, we don’t want them to know you are here.”
I guess I must have looked confused because she said, “You’ll like it, trust me on this.”
Brenda’s closet had louvers in the door so I was able to lean back against the wall and look out. It was only a minute or two before two men came into the room and started undressing. A minute later my mother walked into the room and I suddenly understood what Brenda had meant the night before when she said kill two birds with one stone.
I suppose I should be ashamed to admit that watching my mother (with Brenda’s help) fuck those two guys damn near to death turned me on something fierce, but I won’t because I’m not - ashamed that is. It turned me on to watch her, but I had no desire to fuck her, even though Brenda did eventually get around to trying to talk me into it. When my mother and Brenda had milked those two guys of all they had to offer and they, along with my mother, had dressed and gone Brenda came and got me out of the closet:
“I never asked your position on sloppy seconds” she said, and I gave her my answer by pushing her back on the bed and mounting her. Brenda and I began an affair that lasted almost three years. She got a big kick out of setting me up to watch my mother and occasionally herself bounce around on her bed with an assortment of different men and I got a kick out of it too.
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My affair with Brenda ended when she introduced me to Megan. Megan was a divorcee about ten years older than I was and she was by far the sexiest woman I had ever laid eyes on. I asked her out, she accepted and we started dating. Even though Brenda is the one who put us together for some reason it pissed her off that we were spending so much time together, maybe because it cut down on the time I was spending with Brenda. About three weeks after I started dating (and fucking) Megan, Brenda called me on the phone and told me that I needed to be in her closet by one the next afternoon.
“You are finally going to get to see a gangbang.”
She had been telling me since we started having sex together how big a slut my mother was, “And I’m not saying it in a mean way lover, I’m as big a slut as she is,” but one of the stories she told me about my mother I just refused to believe. She said my mother loved gangbangs, “The more the merrier. I watched her take on seventeen men one night. Of course I was taking care of the other nine, but I couldn’t hold a candle to your mom. God, but that woman sure does love cock.”
Like I said, I didn’t believe a word of it so I guess Brenda decided that she had to prove it to me. I was in her closet at the appointed time and I watched as the room started to fill up with guys. I counted twelve of them before the bedroom door opened and Megan walked in. Brenda had set me up! I was supposed to watch Megan get totally fucked out and then never want to see her again. Well, it backfired on Brenda. I watched as Megan fucked those guys into the ground and my cock stayed rock hard the whole time. She sucked them, she fucked them, she did double and triple penetrations and when they all left she looked like she wanted more. I pushed open the door and walked into the room and she said:
“What are you doing here?”
“Long story” I said, “What’s more important is what I’m going to do now” as I stripped off my clothes. I was going for the gold when Brenda opened the door and saw what was going on. The sudden realization that she had lost her gamble didn’t stop her from coming in and joining us and it was a good thing that it was so late in the afternoon and Megan and I had to get out of there before Harry got home. There was no way in hell that I could have done those two women justice. Over dinner that night I told Megan what I was doing in the closet and she knew right away what Brenda had tried.
“The bitch” she said as she laughed. “She wanted to keep you for herself. So tell me, did you enjoy watching me?”
I smiled and said; “I think the way I acted when I came out of the closet answers that question.”
She gave me a contemplative look and said, “Do you think you could stand doing it two or three times a week?”
Without hesitation I said, “I would much rather participate, but yeah, I could watch.”
That was eleven years ago. Megan and I are married now and I get to watch her from the closet several times a week, usually only one or two guys, occasionally three, and sometimes I get to join in. It depends a lot on who it is she is fucking. If it is one of her clients (she sells Real Estate) I don’t get to, but if it is just somebody she picks up I get to join in. She does one gangbang a month and I’m not allowed in on that. For some reason the guys invited to play have to think I’m out of town. Once or twice a month I get to go and see Brenda and she still sets my mother up for me to watch. She has never stopped trying to get me to have sex with her, “I’ll make her wear a blindfold - she’ll never know!” but I’m satisfied just watching.
I did get to see her do a gangbang - eleven guys - and it was awesome, a real turn on. I sometimes wonder if my dad knows what is going on. If he does it doesn’t seem to bother him and he and my mother seem very happy with each other. It just could be that he knows about my mother what I know about Megan; there is just no way that one man will ever be able to satisfy her. I don’t know about my dad, but I’m getting all I can handle and I don’t mind in the least watching Megan give the rest away.