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John and Cindy

Category: Anal Sex
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John and Cindy were really great people to be around. We were about the same age, and they always upbeat, and Cindy had one of those faces that would light up a room when she walked in. She also exercise daily and aged very well. She was in her mid to late 40’s, but she had the body of a twenty year old. They always found something to laugh about, no matter how bad things were.

John and I worked together for the last 6 years, and I became close friends with both of them.

John and Cindy had been married for over ten years, but I just never could find the right one. So, naturally, I ended up on a lot of Double Dating with John, Cindy and what ever friend Cindy had invited for me to meet. I didn’t mind though, Cindy had great taste in friends and I ended up in bed with most of them.

Cindy would complain that I was too picky, and that I should settle down. But I’d just tell her that, “There is only one perfect woman on earth, and John had already married her. Why would I want to settle for second best?”

Last June, John and I were working on a special project that required a lot of traveling. Since I was single, and looked forward to going to new bars and checking out the local women, I volunteered for most of the travel.

John asked me to come to his office one day to discuss the project. When I got there, he told me that he wanted to start traveling more, because he loved to get ‘Strange Stuff’ every once in a while, and this was a good opportunity. This caught me totally off guard. All the years I had known John, we had joked and kidded about having orgies, or a three-way with one of my girlfriends, but I had never taken him seriously.

I told him it was not a problem, and he could go on the next trip, which was in about 10 days. As the time got closer, I began to wonder if Cindy might be looking for some free time too. So, when John ask me to check in on Cindy occasionally while he was gone, I had no objections at all. I mean, what is good for one, should be good for the other.

I went over to their house about every other day to see how she was doing. Each time, I would see if there was any indication that she might be willing to go to bed with me, but no luck.

Two days before John was due home, I went to pick her up and go to Dinner. When I got there, she was still getting ready, so I stayed in the hallway talking to her.

She came out of the room wearing a white shear blouse and a pair of slacks that gave me an instant hard-on. She looked fantastic. She passed by me and said that she had to go to the restroom before we left, but never quit talking. I noticed that she left the door open, so I walked in and leaned against the doorstop. She sat there with her slacks pulled about half way down her calve muscles and acted as if it was no big deal that I was there.

As we talked, I came up with a plan. I turned the hot water on, pick up a washrag and started soaking it in the sink.

I removed my shirt, then I walked over to her, kneeled in from of her and proceeded to remove her slacks. Her eyes got real big, and she ask, “What the hell do you think you are doing?” I simply replied, “I noticed that you do not have a B’day, so I thought I would wash you off when you are finished.”

She just sat there in disbelief, as I finished removing her slacks. Then, I started kissing her legs, especially the inside of the thigh. She said, “What are you doing now?” To which I replied, “This is all part of the service. Doesn’t John do this for you?”

She started to get up, and I ask her if she was finish? When she said yes, I got up and retrieved the washrag from the sink, and started washing her. I paid special attention to the lips around the pussy and the clitoris, then I rinsed the washrag, and slowly washed her cute little ass.

When I finished, I said that I had to check it, so I stood her up against the wall, raised her right leg over my left shoulder and started licking her pussy lips. As I was licking her lips, I used my fingers to start working her clit, and slowly started working my fingers into her pussy.

After I got a couple fingers inside, I started sucking and nibbling on her clit, while my fingers tried to find the elusive G-spot.

By now, she was really starting to get into it. She was starting to breathe faster and rocking her hips in a thrusting motions. She was rubbing my head with both hands and pushing my head deeper into her bush.

I took my other hand and started to play with her ass. Her butt was firm, and I could feel the muscles each time as she thrust her pussy into my face. I then took my fingers and started playing with her asshole.

We went hot and heavy like this for a few minutes until I heard her take in a deep breathe and hold it. Then her body started to tremble and suddenly went ridged. I was rewarded with getting my face washed as her pussy juices washed over my face.

I spent the next few minutes licking all of the juice off her while she stood there, supporting herself on the Bath-towel Ring.

I slowly stood and worked my way up her stomach, unbuttoning her blouse as I went.

“Do you do this for all of your girlfriends that go to the restroom?”, she asked.

“Only the ones that leave the Bathroom Door open. I have a B’day for the others”, I replied.

“I’ll have to remember that”, she said, more to herself than to me.

I pulled off her blouse and bra, and started kissing around her neck. “Is this also included in the service?”, she asked. “But of course.” was my only response.

I sucked on her nipples, and slowly kissed my way to her back. I undid my pants and dropped them to the floor. Then I slowly pushed her forward until I was able to part her pussy lips with my dick.

As I started to slowly work it in, she suddenly pulled forward, and said, “No, I can’t. You are much bigger than John, and I am afraid he will notice that I am stretched out of shape.”

“Let me try something else then?” With what I had of my dick still in her pussy, I open her medicine cabinet, and found some baby oil. I pushed her forward until I could see her cute little star shaped asshole. Then I put a liberal amount of Baby Oil on my fingers, and slowly worked one of them in.

“Oh my god,” she said, “I have never had it in there before.”

“That’s Ok,” I said, ” if you don’t like it, I’ll stop.” Then I slowly worked in a second finger. Cindy jumped a little, then slowly pushed her butt back onto my fingers until they were all the way in.

I started spreading my fingers apart to make the opening larger. Once got then about 1/4 of an inch apart, I squirted in the Baby Oil. I put quite a bit on my dick, then slowly started to work the nipple of my dick in the opening.

I carefully pushed until I felt the head suddenly break thru. Cindy said, “Stop! Hold it there for a second, until I get used to it.” After what seemed like 5 minutes, she started pushing her butt down on my dick until it too was all the way in. I started to move it out so I could push it in again, but she said, “Wait, I’ll let you know when.”

After another short wait, she started moving her butt back and forth. I said, “Now?” And all she said was, “Yeah.” Then she said, “John has been trying to get me to do this for years. If I had known it would feel like this, I would not have fought it so hard.”

I started to pump he butt slow and easy, but she said, “Don’t play with me, if you are going to give it to me, let me have it!” So, I did. I was ramming it in so hard that I could feel my nuts hitting her bush every time I went in.

But, I found out that the Bathroom is not the place to do it. Some of the Baby Oil got on the floor, and we started to Slip and Slide.

I picked up a large towel, and ask her to come to the guest room with me. I put a pillow on the bed, and covered it with the towel doubled over.

She started to lie down on her stomach, but I said, “No, on your back.” “I can’t,” she said, “As much as I want to, I can’t let you into my pussy.”

I pulled her close to me, and gave her a deep kiss. Then I whispered, “Trust me.” and I smiled. She returned my smile, and after thinking for a minute, she said, “Yeah, right, I’ve never heard that one before.”

She walked to her side table, and removed a vibrator from the drawer and said, “This is how big John is. Please don’t stretch me any larger.” To which I replied, “I promise.”

Once she lied on her back, I placed the pillows under her butt. I had her raise her legs toward her chest until I had access to her asshole. Then, I put more baby Oil on my dick and started working it in again.

It seemed to go in a lot easier this time. “This way I can see your beautiful body while I make love to you.” I said.

I picked up her vibrator from the bed, and carefully entered it into her pussy. “God, I’ve never felt so full in my life,” she remarked.

I twisted the end of the vibrator to turn it on, and started working it in and out of her pussy, while I worked my dick in and out of her ass.

She reached down with both hands and started working the vibrator herself, so I started playing with her nipples and kissing her legs, that were now on my shoulders.

“I can’t believe I’m doing this.” She cried while breathing very heavily.

By now, both of us were covered with sweat and breathing very heavy and almost panting.

My dick felt as though it was going to burst, and I was doing everything I could not to come before she did. Suddenly, she clinched her butt cheeks together and thrust her butt up so high, it lifted me up from the bed. I could not hold it any longer and I felt a hot stream of cum shoot out of my dick so hard it felt like I was pissing. This put her over the edge, and I felt both of our bodies explode in a mass of heat that should have set off the Fire Alarms.

After that, both of us collapsed in a heap on the bed and fell asleep.

We had been asleep about 30 minutes when she woke me up.

She kissed me and said, “I think I changed my mind about going out to dinner. For some reason, I seem tired and I think I’ll go to bed early tonight. Thank you for coming over, I needed that, but you do realized one thing don’t you?”

“What is that?” I ask.

She smiled and said, “You do realize that anytime you come over, I’m leaving the bathroom door open.”

I laughed and said, “You can do that even if I am not here. Just give me a call.” With that, I kissed her again, got dressed and headed home.

John came back to work around 1:00 the next day. He came into my office, shut the door, and said, “Now I know why you like to travel so much. I had a blast. I was there four night and slept with a different woman every night. It was fantastic!”

“Congratulations”, I said, “does that mean you want to go back to L.A again?”

“Damn straight I do!” he said. “I’m taking Cindy out to dinner tonight, and I’d like you to come along and convince her that the project requires me to do more traveling than I have in the past.”

I said, “Sounds good to me. In fact, we have about six months left on this project, and I wouldn’t mind if you did all of the travel. That is, if you want to.”

“Do I want to?” he said, “If you let me do that, I will owe you a big one.”

I told John that I would pick them up, so about 7, I picked them up at their house, and drove to one of our favorite restaurants.

When I pulled up in front to let them out, Cindy said, “John, why don’t you go in and get us a table. I have a favor to ask Matt about.” John said, “Ok.” and I went to park the car.

As soon as we stopped, Cindy got out of the back seat, and got in the front with me. She then gave me a very long kiss, and said, “I am so glad to se you. I didn’t know how the other night effected you, but I thought it was great.” Then before I could reply, she continued, “Is there any way that John can make more of these business trips? I know he is probably screwing anything with a skirt, but this time, it doesn’t bother me, as long as you come around to check on me while he is gone.”

When she said that, my dick jumped to attention so fast it hurt. The problem with not wearing underwear, is, it is kind of hard to hide a hard-on. It jumped so hard, that, Cindy had her hand on my lap, and it knocked her hand in the air. She reached down and started rubbing it, “I take it this means yes?”

I tried to keep my composer and said, “Cindy, if I thought John would allow it, I’d rent your guest room and stay there all the time.”

We kissed again, and squeezed my dick. she said, “You had better do something about that before we get inside.”

After a few more minutes, we walked inside. Cindy said that she was going to the restroom and once she was gone, John ask me, “What was all that about.”

“John,” I said, “Cindy and I are having an affair.” John looked at me for a minute, the started laughing so hard, he almost choked on his drink. He said, “Yeah, right, and I just fucked the Pope.” and started laughing again. “Good luck on that dried up fish,” he said. “Tell you what. If you can pry her drawers off, you can have all you want.”

“You fucking Cindy, that’s a good one.”

Cindy arrived shortly, and as soon as she sat down, John says, “Matt told me about you and him having an affair.” Then he started laughing all over again. Cindy looked at me with a puzzled look on her face. “See her face, she doesn’t believe it either. Matt old boy, I think you are getting delusions of grandeur. Maybe you should stay home more often and let me go to L.A. instead..” He did not notice that he was the only one laughing.

“That’s fine with me,” I said, “I’m getting tired of a different girl every night. Cindy, Would you have any problems with him doing all of the travel for the next six months?”

Cindy was finally catching on and said, “No, not at all,” as she squeezed my leg under the table, “Not as long as he leaves you here to check on me once in a while.”

“That’s right Matt,” laughed John, “you just stay here and Baby Sit.” Cindy and I just smiled back.

After dinner, I took them home, and as Cindy was walking to the door, John stayed behind and said, “You’re a genius, I didn’t know what you had planned in the restaurant, but it worked perfectly. What were you talking about after I went inside?”

I said, “Your Christmas Gift, what else.”

“I thought that might be it,” John said. “I can tell you one thing buddy, your getting something special this year.” Then he shut the door, and waved ‘Bye’.

As I drove away, I thought to myself, “You don’t know the half of it.”

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