Love the site. Great stories. They always make me horny beyond belief and add to my store of masturbation fantasies inside my head. The following story is true (believe it or not if you may). It's one of the few good sexual experiences I've had in my life.
I'm a 45 yr old married guy, very good income, great wife and no kids. My sex life is blasé to say the least. Intercourse once a month (at the most...) and a hand job every now and again. Suffice it to say I am the polar opposite to my wife when it comes to sex, and masturbation is an important outlet for me.
My wife comes from a large family and she it quite close to her little sister. When Molly (34 yrs old) split from her jerk-off husband three years ago and had nowhere to go, we offered to let her stay with us for a few months until she got back on her feet. Molly is a great gal, very outgoing and normally very happy, but the divorce really had her down in the dumps. She also put on a lot of weight, and she ballooned from a very pretty and buxom 140 lb, brown hair and green-eyed looker into a 200+ pound depressed divorcee over about a six-month period. She and I always got along very well, and shared a lot of interests. We would tease each other and flirt innocently on occasion, but nothing overtly sexual was ever said or done.
After Molly had been with us for about 3 weeks, my wife went out of town to attend a conference (she's in the marketing field). Not a big deal; I would be working all day and so would Molly, and we would be left to fend for ourselves for dinner for a few weeknights. Us staying alone wasn't an issue for me, or my wife, as there was no inkling there could possibly be any shenanigans.
The first night my wife was gone was very mundane. Molly & I both got home late, wolfed down some frozen dinners and fell asleep watching TV at 10:00. The next night I got home earlier, and Molly was already there. When I walked in I expected to find her in the kitchen or watching TV, but she was nowhere to be found. I wandered downstairs to my office and found her behind my computer. She was a bit startled when I walked in, and she stammered something about checking her email. She had told me she left work early because she wasn't feeling well, and I noticed she was already in her pajamas (flannel pajama bottoms and a tshirt). I noticed she was a bit red in the face, but didn't think anything of it. She quickly powered down the PC and walked upstairs with me, telling me she would fix dinner for us. I told her that wasn't necessary if she wasn't feeling well, but she insisted.
I went into my bedroom to change, and then told Molly I was going to check MY email on the computer and would be up in a few minutes. After I powered up and logged-on I checked my messages and was about to go upstairs when I decided to check the web browser history. I was just a tad curious as to what Molly had been doing, and was extremely surprised to find that the history showed she had been browsing a bunch of different pornographic websites (I knew they weren't mine because whenever I sign-off I always make sure I clear my web history - I've been caught by my wife before...). I put two and two together and figured that it had probably been quite some time since Molly had been with a man and had been home early and decided to have some fun. I had no problem with it, and immediately began to get aroused thinking about her masturbating in my office chair.
I quickly tried to put it out of my mind and went upstairs for dinner, but when I saw Molly standing in the kitchen the raunchiest thoughts began to race through my mind. I began to think about the best way to bring up the fact that she had been browsing porn on my computer to see where it might lead. I figured out a way that seemed to me would be non-threatening and would allow me to steer the conversation based on her response.
As we made small talk over dinner, I asked Molly if she was feeling better and she told me she was. Eventually I brought up the fact that I had run a program downstairs to scan and clean my hard drive and it had popped up some information about adult websites being accessed that I didn't know anything about. I smiled and told her that I knew which of 'those types of sites' I personally had visited before, but none of these looked familiar. I was letting her know I liked to look at porn on-line and gave her an opportunity to fess up. And she did. She blurted out that she was sorry but it 'had been so long, and I was just, you know. I wanted to...' And she started to cry.
I placed my napkin on the table and walked over to put my hands on her shoulders. I consoled her and told her not to worry, I'm not upset about it and that it's OK. I told her I thought it was actually cool that those types of images turned her on. She began to calm down and we walked into the living room and I flipped on the stereo. She freely began to pour out her feelings, about how much she hated her ex, how much she missed being with a man, and how crappy her life had become. She told me the only time she felt good was when she was satisfying herself, and that she had begun to do it several times a day over the past couple of months. To make her feel more comfortable I shared with her the fact that I also had lackluster love life (without bashing her sister...!) and that I too masturbated at least 2 times every day. She told me she knew about me and Terry (my wife) and that Terry felt awful that I didn't 'get more' from her.
My disclosure about masturbating really seemed to catch her off guard, and I saw the sadness begin to melt away and a slight glimmer appear in her eyes to replace it. After a few seconds of silence she began to pepper me with questions about where I did it, how I did it, what I fantasized about, etc. I told her that I did it wherever I could (mostly in the shower, sometimes surfing porn) and that I normally did it without lubrication. I told her my favorite time had been when I was 16 and had done it one night in the middle of the winter peeking inside my neighbor's window, watching the girl who was a few years younger than me getting undressed. I told her my fantasies ranged from tame to perverted, and she begged me to tell her more. She had become very animated, and I could tell she was more 'alive' then any time I had seen her over the past 3 weeks. I was concerned, however, about where this discussion might lead. Concerned - and curious. Hey, I'm a red-blooded guy with a penis - it wouldn't be normal if I wasn't curious when discussing my fantasies and masturbation habits with a woman (even if it was my sister in law).
I turned the tables momentarily and asked her the same questions she asked me. She told me she prefers lighting candles and taking her time, usually in her living room. She had a vibrator that a friend had given her a year before that she loved to use and described as a silver 'pocket rocket'. She told me she only watched adult movies occasionally and actually preferred using her imagination. She said when she was 15 she had masturbated with a friend at a sleepover and she still thinks about it sometimes. Molly said she fantasized about everything from being with another woman to participating in an orgy. She also confessed she had dreamed about being caught masturbating by a delivery man and had just a few weeks before stripped completely naked after she had ordered a pizza delivery but chickened out and got dressed when the doorbell rang.
This five-minute exchange had done its job on me, and Molly as well. I was rock hard and was having a difficult time hiding it through the shorts I was wearing. Molly was flushed red (she is very fair skinned) and her nipples were noticeably erect through her bra and tshirt. I desperately wanted this to continue, but was ping-ponging the ramifications back and forth in my mind. After several seconds of awkward silence, Molly broke the ice. Boy, did she ever!
She asked if I wanted to see her vibrator. At first I thought she was kidding, and then after making sure I wasn't dreaming I told her sure, if she wanted to show me. I told her I didn't know she had it with her, and she said she never goes anywhere without it. She giggled and got up, went to her bedroom and was back 20 seconds later. She sat on the couch next to me and handed it to me, and told me not to worry, that she always cleans it after she uses it. I told her that her sister could use a toy like that; it would probably help her loosen up. She made a surprisingly biting comment that her sister was 'a prude' and should learn to have a little fun. She leaned over and found the black button on the base of 'the rocket' and turned it on low speed (her breasts rubbing against my upper arm...), and explained to me how it had 3 speeds, and she liked starting it slow and then eventually turn it up high. I was truly interested, and then shocked when she told me that if I didn't mind she was going to go in her room and use it because she was so horny from what we were talking about. I laughed and said that was fine because I was horny too and 'needed to take care of business'. She burst out laughing and then simply said, 'Let's do it together'.
There. It was out in the open. It was obviously what we both wanted to do, and she said it. 'Fine' was all I said in reply, and began to remove my shirt. I was in my underwear before she had a chance to change her mind or say she was just kidding. I smiled at her and told her it was her turn, and she very nonchalantly slipped her flannel bottoms down to reveal her tan panties (girdle was more like it) I removed my underpants and immediately began to stroke my erection. Her eyes were glued to it and her mouth hung open in disbelief, and then she quickly removed her tshirt. She didn't hesitate as she then deftly reached around behind her back and unsnapped her bra, revealing just absolutely gorgeous breasts (large, 36D - I've seen her bra tag) capped with wide, brown and erect nipples. I told her she was gorgeous (I was stretching the truth - quite a bit - because she had a very large midsection). Despite her girth I was incredibly turned on, and she lowered her panties down to just above her knees, revealing a very thick patch of dark pubic hair. She picked the vibrator up and switched it on, and immediately began to slide it up and down between her legs (not inserting it inside her vagina). With her free hand she played with her breasts, tweaking her nipples and letting out soft moans of delight. She was only a few feet directly in front of me, and she smiled as she looked between my eyes and my hand working my erection. In less than three minutes I was close to cumming, and stood up so we were eye to eye. She was working the vibrator faster and faster up and down her slit, and would stop to press it against her clitoris. Just as I was about to erupt I scooted around behind her and pressed my cock up against her hip. This sent both of us over the edge; Molly pressed back against me, bucking her ass as I shot a large amount of semen all over her hip and ass (I distinctly recall a river of fluid running the length of the side of her leg to her ankle...). She let out a deep, almost animalistic moan as she squeezed her legs tight around her hand and the vibrator, shaking as she climaxed. I held her from behind, my softening cock enveloped in the folds of her ample butt.
It was of course very awkward when we were finished, and we both grabbed our clothes and left the room in silence. After we were both cleaned up (I showered, as did Molly) we both sat in the living room and talked about what had happened. We agreed it was a one-time thing, never to be discussed or disclosed again. Molly thanked me profusely and told me how wonderful I was, and I told her that I only cared about how things would work out for her. Since that time we have actually gotten closer and Molly just recently announced her engagement to a great guy. She is back to her normal weight and looks absolutely incredible (god, how I would love to masturbate with her now...!).