Lindsey had recently gotten divorced. Her husband had been mentally and physically abusive and in the last several years of the marriage, things had gotten even worse. She and her husband slept in separate bedrooms and barely even talked anymore, let alone touch. She later found out he had had several affairs. After such a long time without sex, she went a little crazy, just looking for anything with a cock to fuck. Lindsey had also recently started a new job and there was a group of girls who went out every Friday night. She was soon invited to join them one Friday and quickly became a regular with them.
They frequented several local clubs and knew many of the other regular patrons. After a while, some of the men became friendlier with her, and she began flirting with them. She hooked up with a few of them and went out on a couple of dates, but nothing came of any of them. That was ok with Lindsey, as she really was not looking for anything serious right now. She had married young and had not really dated much before she met her husband to be. So at this time, she was kind of looking to “sow some wild oats”.
As girls will do sometimes when they get together, they got to talking about men and their fantasies about them. They talked about how men often exaggerated the size of their cocks, their lasting power, and just their prowess with women in general. They all got laughs about these discussions since they found them to rarely be completely true. There was the occasional truth shared about the one guy who’s cock was almost too big to take and the one who had an amazing tongue (enough said). And one of the girls told of the time she spent naked with this one guy for an entire weekend. She said he made her cum sooo many times, she had lost count. He had had a nice size cock, and was very skilled in using it, along with his tongue and fingers.
Lindsey joked around with the others putting in her share of stories about her experiences. But her husband had been a poor lover who had only rarely given her orgasms. He did not want to have children and refused to use a condom. Although she had been on birth control pills, he did not believe her, and so pulled out before he came. Then Lindsey either sucked him off or gave him a hand job. Since he really never concerned himself much with Lindsey’s needs, she usually went into the bathroom afterwards and masturbated. Due to this, she tried to make up some stories so she would fit in with the others.
Over the first few months after her divorce, she had slept with about a dozen different guys, mostly just one night stands with men she barely knew. She kind of settled down after she started going out with her new friends from work, though she also did sleep with a few of the guys she dated from the bar. Also, at this time, Lindsey wanted a child badly and did not care if she got pregnant, so she would have unprotected sex with any guy she could find. And she discovered that most men were very easy to seduce. If she had gotten pregnant, she would have been overjoyed and would have raised the baby on her own.
One night while she was out with the other girls, she saw these two guys talking to a girl at the other end of the bar. One was sitting next to her and the other was standing behind her. They were both very close to her, touching her shoulder or her arm and whispering in her ear. She was obviously enjoying the attention, flirting back, leaning into the guy behind her and twirling her hair as she talked and laughed with them. The man sitting next to her began rubbing her back and slowly worked his hand inside the back of her blouse. She tilted her head towards the guy standing behind her and began kissing him. Then one of them whispered something to her, they finished their drinks and left the bar together.
Lindsey watched this interaction with a great deal of interest. She felt a pang of jealousy at the same time felt a twitching in her pussy. She began to wonder what being with two guys would be like and just what would happen. She remembered one time when her husband had made her watch a porn film. In it were a number of scenes where several guys took turns fucking one girl. At one point, two of the guys had both their cocks in her pussy. Lindsey doubted that she could ever do that. There was another scene where the girl was riding one of the cocks and a second guy came up behind her and pushed his cock into her ass.
Lindsey was not totally naïve, but she had never had anal sex and could not imagine how it felt. She only remembered that it looked rather painful as the girl in the movie winced when she was penetrated and as she was being fucked. Her husband had suggested it to her once, but she had refused him and he never asked again. But watching the two guys in the bar and imagining what they might have done really got her to thinking about what it would be like to have two men as sexual partners at the same time.
Shortly after moving out of her home when she divorced, a friend had given her a vibrator as a joke. It had several covers that went over the head of the vibrator. One was a long, relatively thin cover that looked like a long finger. When she got home that night, she pulled out the vibrator and some KY. She took off her clothes and laid down on her side on her bed. She reached around and put some of the lube around her hole and more on the cover. She turned on the vibrator and put the tip of the cover against her hole. She tried pushing it in but felt herself tensing against it. It was also a bit painful.
Lindsey tried to relax her muscles and push it in her again. This time she was able to get it in an inch or so before she felt herself push and expel the vibrator. She waited a minute, added a little more lube around her ass, trying to work it in a bit with her finger. She took a few deep breaths then relaxed and tried again. This time, she felt the vibrator go all the way in, popping a bit as it got past the inner muscles. She just left it there, not moving it and just feeling the vibes. After a minute, she started slowly moving it in and out. Lindsey was surprised when after about five or six minutes, she felt that familiar wave over come her and she had an orgasm. But it was just a little different than those she had had in the past.
Her curiosity piqued, Lindsey got up the courage to go to an adult book store and find a couple of other toys, which she paid for with cash and brought home. One of the toys was a small butt plug. The widest part was about half again as wide as the finger cover she had used on herself already. The other was a rubber replica of a cock. It was flesh colored and shaped just like a cock, complete with balls. It had a suction cup on the bottom of it so it could be attached to a flat surface like a chair and she could climb on and ride it. It was soft, yet firm, and had veins and texture to look and feel like skin. The store had bigger dildos, but she felt some of them were just too large. The one she selected was just a bit larger in size then any of the men she had been with.
When she got home, she could barely wait to try everything out. Lindsey experimented with several surfaces to see which worked best with the suction cup on the dildo. She decided it needed to be something she could straddle easily, so she could move up and down. She found that using the corner of one of the wooden chairs to her dining room table gave her sufficient room to move around. Also, she could face the back of the chair and use it to help her move up and down on the dildo. Once she had everything in place, Lindsey stripped naked and lubed up the butt plug. It took a bit of doing, but she finally got it inside her ass. It was a bit uncomfortable at first, so she just decided to let it sit there.
Next, she applied a liberal amount of the KY to the entire length of the dildo. She straddled the chair and tried to lower herself onto it. She was having some trouble as she expected she might, and added a bit more lube to the dildo and her pussy, but still was unable to get it in very far. Finally, she began to play with her clit and was getting aroused. While still playing with herself, she tried lowering herself on to the dildo again. This time she was successful in lowering herself all the way down.