Sharing Cindy Chapter 23 “Cindy & Sandy: Two of a Kind”

“Cindy and Sandy: Two of a Kind”

This chapter will be centered on a particular friend of Cindy’s. Her name is Sandy and the two of them managed to get into a lot of situations through the years. We met Sandy right out of high school and she has continued to be a part of our lives.

As I told you about in an earlier story, a couple of friends of mine were in a band. They played drums and guitar while a cousin of theirs played lead guitar. This meant they needed a bass player. After going through several guys who really didn’t quite fit well, the happened upon Don. Don was a big bear of a guy, probably 6’2” with long dark hair and a full beard. I met him a couple of times alone and thought nothing of it until one night he showed up with a petite blonde in tow.

He introduced us all to Sandy and we all commented on how tiny she was compared to Don. She was actually only about 4’-11” and couldn’t have weighed more than 85 pounds. She did have long blonde hair and was very cute, with a little turned up nose and a sexy mouth. Over time she and Cindy became very tight and actually best friends. It was Sandy who had gotten Cindy the job at the Furniture store where Cindy ended up sleeping with her boss. (see Chapter 7 for that story)

Sandy was a very open and outgoing girl. She also liked to dress the part of a girlfriend of a rock star, even if her boyfriend was just in a local band. Being so tiny, she loved to wear tall heels and I was amazed at the many different ones she owned. Cindy of course loved to dress provocatively as well so it was always fun to see the two of them together. It made band practices a little more tolerable having those two around.

Cindy and Sandy would often go out together and it didn’t take long for them to share all sorts of intimate secrets about their relationships. Cindy let Sandy in on the fact that I enjoyed her flirting and teasing other men and even sleeping with them. They often would go out together and Cindy would end up having a little fun with a guy, but Sandy never batted an eye. She became a sort of wingman for her during her quest for other cocks.

Cindy would talk to me about Sandy and she seemed to believe Sandy was open to having fun herself. She also thought that many times when they were changing clothes to go out that Sandy was more than interested in checking out her body. We would even talk about the possibility of getting her into bed with us.

The first time anything happened with Sandy, actually involved both her and her boyfriend Don. In a small town north of where we lived, there was a drive in theater that actually showed xxx rated movies. Cindy and I had been to it a few times, and she had told Sandy all about it. One day she told me that Sandy and Don wanted to check it out and wanted us to go with them.

Now, every time that the two of us would go there, we always ended up having sex in the car during the show. I wondered what would happen with the four of us in the car. It could be an interesting night. I know I couldn’t wait.

Don picked us up in his car. He loved old classic cars and had a 1965 Chevy Impala. The great thing about these old cars is they had lots of room inside. His car had big bench seats in both the front and rear. I know I was impressed as my ’68 Camaro had bucket seats and a smaller seat in the back. We took the long drive to the drive in with few cold beers and a couple of joints. By the time we got there all of us were feeling pretty loose and ready for the movies to begin.

Of course it wasn’t too far into the movie that both couples were getting intimate. I watched as Sandy’s head disappeared in to Don’s lap. That was enough set the tone of the rest of the night. When Sandy sat back up licking her lips she looked back at us and winked. Then she reached down and puller her top up and over her head. She definitely was nowhere near as large as Cindy on top, but seeing her cute little tits with pink nipples was still great. Cindy followed suit and before long neither girl had anything on.

One memorable moment was as Cindy had lowered herself down onto my dick facing the front of the car. I was watching her sexy ass bounce up and down on me. I looked up and over her shoulder and saw Sandy riding Don’s dick as she faced the backseat. Both girls were keeping time with each other and staring at each other over Don’s shoulder. Don seemed to have his head on a permanent swivel.

Then something very special happened…..Cindy leaned forward as Sandy leaned towards the back. Both of then met over the seat and their lips met. Seeing her kissing Sandy like that was unbelievable. Don kept saying over and over “This is great!” I watched as Cindy snaked her arm over the seat and began to play with Sandy’s nipples. I heard Sandy moan and soon she was gasping out that she was cumming.

For such a little girl she was making a lot of noise as she came. I looked around and saw that several others from other cars were looking over. They all had smiles on their faces. I know I definitely did. Unfortunately not a whole lot more happened that night, other than both Don and I getting to fuck our respective girlfriends one more time. We headed home from the movies and I was wondering if this was the only time I would see Sandy naked or her and Cindy together. I shouldn’t have worried.

The night at the movies seemed to bond Cindy and Sandy and they became much closer. I know that Sandy actually began to have her own extracurricular activities without Don. Cindy told me that once Don found out about how I encourage Cindy to have fun with other guys, he thought about it and found that it turned him on as well.

A few months later, Don and Sandy had a small get together at their apartment with probably about a dozen people or so. We had the drinks going strong and while some people started up a card game, Don thought it would be fun to put on some porn. We sat around joking about the movies but I could see that Cindy and Sandy were squirming a little. I figured they must be a little embarrassed about watching this sort of thing in a group of other people.

A little while later I noticed that Cindy had not come back after going to the bathroom. Looking around I also noticed that Don and Sandy were missing. Just as I was trying to decide whether to get up and go find her, she walked back into the front room with a blanket wrapped around her. It was obvious that she was naked underneath. Everyone stopped what they were doing and looked at her. She walked over to me and took my hand, leading me back to one of the bedrooms.

We entered the bedroom and I saw Sandy and Don in there, both also naked. Cindy said that when she came out of the bathroom and was passing the bedroom door, Sandy reached out and pulled her in. I watched as Cindy dropped the blanket and crawled back onto the bed. She scooted up next to Sandy and the two of them proceeded to make out hot and heavy. Don, true to form looked up at me and said “This is great!”

I felt a little funny being the only one wearing clothes, so I stripped down and sat on the edge of the bed. Both girls were really into each other and it wasn’t long before they were locked in a sixty nine, licking each other’s wet pussies. Both Don and I were sporting some serious hard ons and I know I needed some relief. I did notice that Don wasn’t very big down there. That may explain why he chose such a petite girlfriend. I told Cindy to roll over so they were on their sides and then I scooted up to spoon against her ass. I then rubbed my cock all around her hole to get it wet. In the process I bumped it into Sandy a few times and even felt her lick the head once or twice. I sank deep inside of Cindy and began to pump. Don meanwhile, was getting behind Sandy and it looked like we were going to make this a four way.

We both continued to pump our girlfriends and he even stuck out his hand for a high five. I know that once or twice I pulled out of Cindy and before I knew it, Sandy had her lips wrapped around me and I felt the heat of her mouth engulf me. I wondered if Don had gotten the same treatment from Cindy. I switched off and on from that hot mouth to Cindy’s warm pussy and just as I was beginning to fill her with my load, some asshole began pounding on the door and telling Don to get his ass back out to the party.

Needless to say that broke the mood and we all untangled ourselves and got dressed. Cindy and I left shortly after that as she was a little embarrassed because a couple of Don’s friends were making crude comments.

Cindy and Sandy continued their escapades whenever they would go out. One night she came home and wanted to talk to me. S he said that one of the bars they go to was owned by a guy named Jaime. He loved having sexy girls in the bar as it brought in more guys, so they would always drink for free while there. Sometimes when it was a little slower, Jaime would sit and talk to the girls. Apparently he became infatuated with Cindy and Sandy and made them a proposition.

Jaime said that he had always wanted to see two girls together. Hearing this, Cindy grabbed Sandy and planted a big kiss on her. They made out with each other for his benefit, not to mention all the other guys in the bar. He said that while that was great, however he meant he wanted to see two women have sex with each other. He then told them that he would be willing to pay to see it. Cindy asked him how much and he said he would pay two hundred dollars to see it. She called his bluff and said make it two hundred apiece and he had a deal. She told me he couldn’t get to the cash register fast enough.

He told them to follow him and he took them to a door that led up a flight of stairs to what turned out to be his apartment over the bar. He pulled out the money and handed it to them. They took it and put it in their purses and then proceeded to put on a show for him. Each one licked the other to orgasm and then they got into a sixty-nine and did it again. I asked her if he had fucked either of them and she said no, but he made them another offer when they were done. He offered them each another two hundred if they would come back next week and have a threesome with him. They told him to make it three hundred apiece and they would think about it.

I asked Cindy if she wanted to do it and officially become a paid whore. She laughed and said she had already been paid to perform for him so why not make more money to have some fun. I agreed with her and took her to bed and had her tell me all about her night while we pleasured each other.

The next week she got ready to go out to meet Sandy and head over to see Jaime. She looked incredible wearing a sexy little jean mini and a purple low cut top. I knew that she would return to me in a few hours with another great story to tell. Of course its hard for a guy to get his mind on other things when he knows at that minute his woman could have another guy’s cock buried balls deep inside of her. I did my best to kill the time without jacking off too many times.

When she came home she had a huge smile on her face and a fist full of twenties. She took my hand and led me to bed, then stripped off her clothes and climbed in with me. She proceeded to tell me all about her night. She said that Jaime must have been way too excited and he came in about ten strokes. So Cindy and Sandy put on another girl/girl show for him and eventually he was hard enough to have Sandy give him head.

Over the next couple of years, Jaime managed to set up about four or five other threesome with the two of them. Each time Cindy would come home very happy and she had some extra spending money for clothes.

The final thing I want to tell you about is when I finally got to fuck Sandy myself. The band had broken up as most of them had moved on to bigger and better things. Don unfortunately decided to focus more on his job and stopped playing. I am not sure what happened between he and Sandy, but after a short marriage, they got divorced and we didn’t see Don after that. Sandy of course, was constantly around and looking better than ever.

One night she showed up at our place with a new guy, Mark in tow. Mark seemed like a nice guy and we enjoyed hanging out with them. It was apparent that Sandy and him were at that stage of their relationship where they couldn’t keep their hands off each other. At one point during the night, I accidentally bumped into Cindy and spilled my drink all over the front of her sweater. She was bummed out about it but I said I would go get her another top. I went back to the bedroom and began going through her drawers looking for a top. I found just the right one.

Cindy has many sheer tops and usually she wears a lacy bra underneath. I knew she didn’t have one on under her sweater that night, so I grabbed a sheer blue top and headed back out to the living room. She saw what I had and started to protest. With a little convincing from me and both Sandy and Mark, we talked her into putting it on. Thank god for alcohol.

Once she had the top on, all of us could see her tits as plain as day. Mark really began to stare at them and Sandy got a little bit upset that he was focusing his attention on Cindy and not her. With that she said, “Here, let me give you something to stare at.” The next thing I know she is pulling her shirt off and standing there topless! Now it was me who was staring.

That seemed to break the ice, so to speak, and after that a lot of touching and grabbing was going on. Some how it ended up with the four of us naked and sprawled out on the floor. At one point during the fun, Sandy ended up in my arms and Cindy was across the room with Mark. I had been watching Sandy strut her cute little butt around me for years, and while we had had the chance to play and be naked around each other, I had never had the opportunity to actually fuck her. That was about to change.

I looked across the room and saw that Mark had actually positioned himself over Cindy and she was reaching between them to help guide him inside of her. I took that as the OK to do the same thing to Sandy. She looked up at me and asked if I was ready to feel her tight pussy wrapped around me. I told her I was. But first I wanted to taste her. I went down on her and licked her to a couple of really intense orgasms. She would make this cute little squeal whenever she came.

The time had finally come for me to actually fuck Sandy. I had her spread her legs and moved up between them. I couldn’t believe just how small of a girl she really was. As I began to push the head of my cock into her, it was apparent that not only was she a tiny girl outside, but inside as well. I do not have a monstrously huge cock, it is a couple inches above normal though, and right then I doubted it would even fit inside of her.

With a little patience and perseverance, I managed to finally sink deep inside of her. I swear that to this day, I have never felt anything quite as tight around my dick. He pussy was tighter than any other girls I had been in and even tighter than Cindy’s ass. She looked up at me and asked if I liked feeling that tight pussy? Oh hell yeah. It was incredible.

I would like to say I lasted for hours, but that would be a lie. A few minutes of stroking in and out of her were more than I could handle. It wasn’t long before I was ready to cum and asked where she wanted it. She told me to pull out and come on her tits. I waited until the last second and then pulled out and began to stroke it. Well, I at least tried to hit her boobs, but the force of my cum hit her square on the chin and covered her neck. What could I say? It was her tightness that had me so worked up.

I came down from my orgasm just as Cindy was hitting hers. We looked over and saw that she had climbed on top of Mark at some point and had him pinned down while she bounced on him. She really began to grind her clit hard against his pubic bone and in short order she was screaming out she was cumming. Sandy and I began clapping for the show.

We sat around naked with then for a while and were talking about some of our experiences when Sandy told Mark that she and Cindy had previously had sex together. He was super turned on by this and begged to see them together. The girls then fell into a comfortable embrace as Mark and I sat back and watched the show. Of course we both got hard again and we each were rewarded with a couple of fine blowjobs.

Sandy dated several different guys for a couple of years and finally found a great guy, Jimmy who she became serious with. Unfortunately her new guy was not into anything fun, so our sex fun came to an end with her. But up until she met Jimmy, I had the pleasure of having her share our bed on several different occasions. And on one weekend that Cindy was out of town, she sent Sandy over to keep me company for three days. I really miss that tight pussy and hope that someday I will get to experience it again.