Never Judge a Boo by Its Cover

Matt rolled off of Brenda after having a great hour-long sex session. They laid their naked side by side. Brenda rolled over placing her arm across Matt's chest and her head on his shoulder.

They had met only three weeks earlier through an on-line dating site. Brenda is a 55-year-old grandmother, very conservative demeaner and a widow for about 8 years now. Matt is 58 still working for a manufacturing company that produces semi-truck parts and also a widow for about 3 years. They started chatting at first thru the site and eventually agreed to dinner. Both have been widowed for several years and were lonely so they clicked very quickly. Matt was aging well and had an older man distinguish look to him with a gray-haired mustache and still a full head of salt and pepper hair. Brenda at 55 took very good care of herself with proper food and exercise and looked much younger than her actual age. This was there first time in bed together and even though the actual session was only about an hour long they had been flirting about it for a couple of days. Brenda finally sent Matt a picture of her topless but of her back to a mirror and her waist just slightly turned to where Matt could only see a very little bit of the side of her boob.

"You tease, I can't see anything but your back and a little side boob."

"Well, perhaps you need to come over here if you want to see the rest."

They ended up in bed after a lengthy foreplay. Matt was somewhat surprised how passionate Brenda was in the foreplay and also, she seemed to like to be told what he wanted her to do.

"Why don't you unbutton my pants and take my cock out and suck it."

"Is that what you want me to do?"

"Yes"

Brenda wasted no time in complying with Matt's order. After sucking on his cock for about ten minutes he gave her a new order. Matt quickly realized she liked to be ordered when it came to sex. What little he has learned about Brenda to this point, this is not at all on how he thought she would act. He saw her as a softspoken grandmother type person. Sex, he expected would be fun but somewhat conservative and straightforward nothing to beyond what was considered by most normal.

Trying to be assertive Matt ordered. "Stand up and take your clothes off.

Brenda instantly stopped sucking his cock, stood up, pulled her top off, slid the straps of her bra off her shoulder and slid the bra off her still perfect C cup breast. She followed up by pulling her pants down along with her underwear and tossing all on a chair behind her. She stood there naked in front of Matt. My god she looks good Matt thought to himself. Brenda stood there looking at Matt like she was waiting for the next order.

With authority in his voice. "Go in the bedroom and get on the bed."

Brenda turned and headed down the hall with Matt following watching her ass wiggle as she walked. Once in the room Matt quickly took his clothes off and joined her on the bed. They embraced, kissed passionately and it wasn't long before Matt was fucking her. She was not quite about it either, she had multiple orgasms.

With her arm still across Matt's chest. "That was really good, I liked it."

Matt looked at her face. "I enjoyed it too, and you had a couple of orgasms so I figured you liked it."

"I get very turned on being ordered to perform sex acts, strip as well as other things. It sounds to me you have done that before."

In reality Matt had not done anything like that before but sensed that it seems to be what she was looking for in their foreplay and so he tried to sound authoritative.

"No, I haven't. I just felt by things you were saying you were waiting for me to tell you what I wanted. That is new to me.

"Really, well you did a good job, I like to be told what to do when it comes to sex, I love it."

"Do you have past experience with this, being ordered to perform sex acts?"

"Yes"

"I am surprised, I just didn't see you as having a, I guess you can call it somewhat of a kinky side when it comes to sex."

Brenda sat up with her back to the headboard. "I think we need to talk then."

Matt also sat up against the headboard with somewhat of a puzzled look on his face.

"I need to tell you about some things about me I am not sure you are into and may not be interested in before we go too far. I love sex! I am very open about sex and like lots of things associated with it, always have."

Matt interrupted. "Okay, like what?"

"I like to be watched having sex. I like sex clubs. I also like girls just as well as men. I have tried many things over the years since I was about 22 years old. Are you okay, should I continue?"

"I'm okay, just surprised. I guess the phrase-Never judge a book by its cover- applies here. I would not have guessed any of that in a million years about you."

"Surprise! I apologize for none of it, I have lived a fun life. I miss my Husband a lot, he was very supportive and encouraged me to try new things. And I guess I am looking for someone with the same qualities."

"I am not sure if I fit that bill. I have no experience with any of that. If you don't mind telling me, what sort of things have you done? If you don't want to tell me, I understand."

"I am quiet and softspoken but not shy talking about sex at all. If you are interested, I would love to tell you. After I tell you about some things and a few stories hopefully it will get you excited. If you want to fuck me again by all means take control and do."

"Um, okay"

I guess I will tell you about more recent adventures. About two months ago I met up with a couple here locally that I found out was trying to find another female to join them for a threesome. I was not sure they would be interested in since I am in my mid 50's and they were mid 30's. It turned out age didn't matter to them as long as the chemistry was there. Cindy was instantly attracted to me as I was to her. Her Husband is a good-looking guy."

"So, did you guys get together?"

"I will just say that Cindy smelled and tasted delicious and her husband's cock had no problem satisfying me as well as Cindy's tongue on my pussy."

"Um, okay, wow. I have never done a threesome. It kind of sounds interesting, I am not sure."

"Oh, I have had threesomes, foursomes and more. My husband and I would often go to sex clubs where one of my favorite things was to be tied up (I Volunteered) and I was gangbanged for couple hours while my husband watched. I loved every second of it. Having multiple different size cocks in me was fun. Most were of average size and always felt good, some were smaller and I still tried to enjoy them as well. But some were a bit larger and well wow I could really feel the difference. Speaking of well-endowed that reminds me I once was fucked by a black guy who was very, very well hung. I don't know how big 9, 10 inches. I actually didn't much like it, it hurt going in and was uncomfortable."

"Wow, you have lived an interesting life it sounds like. I don't think I can match any of that in experience. You said your husband watched you get gangbanged and he was ok with that?"

"Sure, he loved to watch me have sex with other people. He sometimes arranged for me to have a friend or co-worker come over just so he could watch. Afterwards he often tied me to the bed and used me as a sex slave for a couple of hours. He would love it when I would beg him to fuck me. I love the idea of being someone's sex slave. He loved to tease me, get me worked up and horny and then walk away. That's when I would usually start to beg him for it. I have been tied to the bed many times and my husband would arranged for guys to come over and use me as a cum dump. They would show up usually one at a time, come in, take their pants off climb between my spread legs, fuck me, cum in me and leave."

Matt by now was getting aroused listening to her stories and it was showing, his cock was getting hard. This did not go unnoticed by Brenda. Matt noticed her looking at his cock.

Matt slid down from sitting up. "Get on top and ride my cock, right now."

Brenda didn't hesitate for a second. "Yes sir"

Brenda began to ride his cock while Matt squeezed her tits hard causing her to yelp a little. Matt stopped.

"Don't stop squeezing my tits. I like them being squeezed hard, I love it, I also like my nipples pulled and pinched."

Brenda began to bounce harder on his swollen cock, and Matt continued to squeezed her tits even harder. Brenda began to moan loudly.

"Yes, squeeze them harder, I going cum, OH GOD YEEEEEEES I like being your slut OH FUCK."

Brenda had an intense orgasm and shuttered to a stop with her eyes closed. Matt immediately pushed her off of him demand she turn her ass over. He got behind her and quickly shoved his cock in her pussy. After a minute he pulled it out and pushed it in her asshole.

"Ohhhhhh' Yay fuck my ass whatever you want take it. Cum in me, fill me up."

Matt was so worked up he started to fuck her ass hard, pounding against her ass cheeks. Breanda's ass was in the air, head down, her arms stretched out above her head, hands gripping the bedspread hard.

Matt pumping as hard he could. "Oh geez, AAAAAAWWWWW."

Matt's cock and balls pumped cum in her hole. After the sensation subsided he stopped and rested for a moment still breathing hard. Brenda just laid there enjoying the feeling of his cock in her ass. Matt pulled out of her ass, watched his cum ooze out. Brenda flattened out on the bed.

"Oh my god Brenda that felt so incredibly good."

Brenda laid there on her stomach and smiled and was proud of herself for providing a hole for Matt to satisfy himself in like a good little slut should.

A few days later Matt was sitting on his couch thinking about what Brenda had told him about her slutty side. He was still surprised by the things she said she has done and still loves to do sexually. Looking at her she just seems so far removed from any type of activity like that. He thought about his wife, would she have done experimental sexual activity, not a chance. The kinkiest thing in the bedroom she ever wanted to try was have him fuck her in the ass and even then, they had only done that twice several years apart. She didn't find it that great and it was uncomfortable for her. The only thing outside the bedroom she did was take her top off once at an adults only/clothing optional pool area at a Las Vegas resort, but of course there was some alcohol involved in that decision.

Brenda's lifestyle was completely new to him. He had heard of sex clubs but really never gave them much thought. Does he want to really go to one? Can he stand there and watch the woman he is with get fucked by another man or multiple men since she says she likes gangbangs? He just wasn't sure, how he was supposed to act or what to do.

A couple months went by and Matt and Brenda got together many more times. They seemed get along very well and had several conversations about her lifestyle.

"I am not at all opposed to the things you have said you want to continue to do. I am nervous about going to a sex club with you, not sure what to do or how to act."

"I understand that it would be new to you but I would really like to introduce you to the lifestyle. Just be yourself, I think once you see for yourself you will realize it is just sex. I am not running off with anyone there, none of the people are. I am just there for the socializing, sex and pleasure and you should to be too."

"It is such a new Idea to me; I am nervous but I like you a lot and I think I would like to learn about this lifestyle you enjoy."

Brenda made the arrangements to attend an upcoming party at a club she was a member of.

"As they approached the door to the club. "OK listen we will just go in, have a drink or two and mingle. We don't have to take our clothes off. Some people might be naked, many won't be. This is more of a meet and greet area when we go in. Just be yourself it is going to be fine. You ready?"

"Yes, I think so."

Brenda and Matt entered the meeting area and right away went and got a drink. Matt looked around and Brenda was right most all the people there were still dressed. There was a couple of women that were topless and some were wearing see thru tops that you could clearly see their breast.

Brenda was dressed in a short black skirt, not a mini dress but short, with red nylons and high heels. Underneath she had a garter belt on, crotchless panties and a matching peek a boo bra. Back at her place Matt had told her she could not get dressed until he got there to pick her up, he was going to watch. Watch he did so he knew what she had on and struggled not to throw here on the bed and fuck her right there, she looked beautiful and certainly good enough to eat.

Matt was wearing black slacks and a white shirt, no tie. Before they left Brenda remarked on how handsome he looked and the other woman were probably going to be fighting over who gets the handsome new guy first and if it wasn't her, she was going to be jealous.

They mingled and talked to some of the other people in the room, a few couples had left to the other part of the club where Matt was told there were rooms to participate in the activities, they all were there to do, but most were still drinking and talking.

A woman walked up to them. "Brenda! You made it glad to see you. You look yummy as always."

"Matt, this is Martha. Her and her husband are the host of this party. Where's Dave?"

"Oh, you know him. He is probably off getting a blowjob already somewhere. So, this is Matt, you told me about. Nice to meet you." Martha looked at Brenda. "You are going to share him-right? He is quite handsome, if you don't, I will find a way to steal him later."

"I don't know. It is up to him; I won't pressure him. This is a new experience for him and I want him to be comfortable about it."

"Well, Matt relax I think you will enjoy it here. The people are all good, friendly people, get to know them and you will see."

With that Martha turned and walked over to another couple. As she walked away Matt looked at her nice ass covered by very tight pants and she was wearing a tight pull over shirt that Matt didn't understand why it wasn't tearing open from the pressure of her very large breast pressing against it from underneath, they were straining to get out.

"I see what you were looking at. Yes, she has huge tits. She has large areolas and nipples too. I love sucking on her tits."

Matt gave her smile on her remarks about Marth's tits. They had another drink. Matt was beginning to relax more especially after they had talked to another couple who were somewhat new to this as well. This was only their second time there and they completely understood Matt's nervousness. They asked Matt and Brenda if they would be interested in swapping. Brenda knew Matt was not quite ready yet for that and said maybe later.

Brenda took Matts's hand and began to show him around. They passed by a couple of rooms where people were already having fun with each other, They passed by a room that was made to look like a dungeon and there was a woman tied to what looked like a large X. The guy in front of her was attaching clips to her nipples and what looked like a large vibrator was inserted in her pussy.

Then they came to Brenda's favorite room where woman could go to, be bent over and tied to a sawhorse looking device and they would be gangbang by multiple men over the course of an hour or longer if they agreed to stay.

They walked into a locker style area where the people could undress and leave their belongings in a locked locker.

"Well, what do think? Do you want to take me in one of these rooms and fuck me, heaven knows I need to be. I am a bad girl for bringing you here, I probably should be taught a lesson.

Matt slapped her ass hard through her skirt. "Get your clothes off!"

Brenda didn't hesitate and stripped out of her skirt and blouse. "Leave everything else on! I am going to parade you around like the slut you are for bringing me here. First take my clothes off."

Brenda knelt down and took Matt's shoes and socks off, stood up and unbuttoned his pants taking them and his underwear off and finally his shirt. She put their clothes in a locker and locked it. Matt grabbed her hand and they walked out into the hall then he told Brenda she must stay behind him as he walked. Matt found the room he was looking for. A room with several mattresses arranged on the floor. Matt stopped.

"Get your ass in there on that mattress right there, on your hands and knees."

Brenda quickly obeyed. Matt knelt down in front of her face and put his cock against her lips. "Suck it!"

Brenda began to suck on Matt's very erect cock when the couple they had talked to earlier about swapping partners came in and started to get down on one of the other mattresses.

Matt looked at the guy. "You want to fuck her?" Pointing to Brenda. "Get behind her, this pretty little slut is ready for it."

The guy walked over and knelt down along with his wife and she guided her husband cock in to Brenda's pussy. Brenda jumped a little and moaned thru her nose as she felt him slid his cock in. He began to steadily move in and out of her pussy while his wife watched. Brenda's breathing and low whimpering was getting faster. Matt looked at the man's wife and her shaved pussy. She looked at him and went over to one of other mattresses, laid a towel down on it and laid down on her back spreading her legs. Matt pulled his cock out of Brenda's mouth and walked over to her. He got down, put his face in front of her clean-shaven pussy and began to lick at her clit.

She responded instantly. "Oh god yay eat me."

Brenda looked over and saw Matts face buried in this other woman's pussy and smiled. She than focused on the guy behind her and on how good his cock felt in her. The guy picked up the pace fucking her, Brenda's legs and pelvic area began to quiver some, she was going to cum she could feel it.

Matts face and tongue was working, she was lifting her hips up and down and began to squirm. Matt was having trouble keeping his tongue in her she was moving around so much. He gripped her legs some to help hold her steady. Suddenly she let out a load moan and started to squirt out of her pussy. Matt backed away some and took his thumb and started to rub her clit which caused her to squirt and moan even more.

Brenda couldn't hold back any longer, with heavy breathing she came on the man's cock. He kept on pumping hard and with a few loud grunts he exploded in Brenda's very wet pussy.

Matt slid up on to the woman and pushed his cock in her pussy. She was staring up at Matts face, rubbing and pulling on her own nipples.

With sort of a mean look on her face. "That away you bastard, take my pussy, COME ON FUCK ME, you know you want it!"

Matt thought wow, but her pussy felt very good. It wasn't going to take him long to cum.

"That pussy feels really good, doesn't it? COME ON YOU PRICK HARDER, FUCK ME HARDER, AS DEEP AS YOU CAN. I want to feel you all the way in."

She stopped pulling her nipples and grabbed Matts ass cheeks hard and pulled him in hard with each thrust. Matt began to breath harder and grunting more, he exploded in her pussy. She held on to his ass hard and held him in her as his swollen cock pulsated pumping cream in to her.

"YES, FILL ME UP, I want all of that cum in me, every last drop."

Matt his arms stretched on both side of her holding himself up watched her face. She looked angry, but once she was satisfied, he was done Cuming she let go of his ass and her face turned to a smile.

"Thank you. That felt so good, you have a nice cock."

Matt pulled out of the woman's pussy and backed away. Her husband was standing there watching.

He looked at Matt. "I know, she is a wildcat when it comes to fucking her. I have gotten used to it."