Wife's First Anal Sex - Cindy

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Cindy - Wife's First Anal Sex

A Night With The Boys

By: MiamiMark

I have skipped a few stories between ‘Fiancee for Three’ and this one but it is one of the more memorable recent moments between Cindy and myself and felt you might enjoy it. I am sure I will share the other stories at a later time but I wanted to write this one down before I completely forget the details. I know there are some details that I couldn't remember (so much going on) so I left them out. Anyways, sorry it is so long but the setup is as important as what happened between us. I always appreciate any comments.

After Cindy and I were married, she made it clear to me that she did not want to have any other swinging adventures with Rick or Dr. Greer. I was quite disappointed but I had always made it a point that we would only do this if we both were willing. I would have to be content with the VCR in my brain.

We had recently moved into our new house and everything was looking great. The furniture was delivered, the boxes all unpacked and put away, and the cleaning was all done. After weeks of working at home, I took a night off to join the guys at my office to hang out and maybe catch up on the newest network game. It was four of us and we were just waiting for Rick to show up when I realized that I forgot to bring some files from home . Thinking quickly, I called Rick on the cell phone to ask if he could stop by the house and pick them up on the way here. He said that it was fine but he might be running a little late at work so he would stop by right after.

Meanwhile the four of us were talking the time away as we shared stories about marriage and honeymoons. None of the guys knew that my wife and I had dabbled a bit into swinging and least of all that Rick was one of the only two guys she had done it with. If they ever found out about us, they would all hit the floor in disbelief … especially since they have always seen my wife as a very, very, very wholesome good girl and slightly prude to boot.


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Finally, Rick showed up with the files and we asked him why it took so long to leave work and he had mentioned that they had to transfer some prisoners from one prison to another and he had to supervise. (Rick is a corrections officer at a federal prison). He went on to tell us the details since his prison stories are always entertaining. After 3 or 4 hours of goofing off and playing games, three of the guys had to leave on account they had to work early the next day.

Rick, Leo and I decided to play one more game and call it a night. I took advantage of the break to call Cindy and make sure everything was ok and to wish her a goodnight. I knew it was getting late and she would be asleep soon. When no one answered the house line I decided to try her cell phone thinking she might be asleep and her cell is always next to her. She answered the phone and told me she had decided to take advantage of the free night and visit her friend Gloria. Now she was heading back home and decided to take a small detour to my office on the way home from her friend’s house. She just wanted to just stop by, say hi to everyone, and give me a goodnight kiss. Can't say no to that!

My office has several individual rooms with computers. Rick was in the one closest to the entrance (secretary's area), Leo was in the next one, and I was at the last office down the hall. A few minutes into our game, Cindy came in and I could hear her saying hi to Rick and then walking past Leo’s office and asking him how he was doing with his new job. Then she strolled into my office, walked around my desk and wrapped her arms around around me. I looked up and she gave me a passionate kiss running her hand down my chest.

By the looks of her, I’d say her and Gloria probably went out to the clubs and she ended up getting horny from dancing with all the local Casanovas. She was wearing a sheer black blouse, soft to the touch, a little black silky skirt, and black high heels. The contrast of her black shoes, creamy white legs, and black skirt was incredible. Her blouse slightly form fitting and her nipples protruded through the fabric … that told me she was not wearing a bra. Her hair was long and wavy, clipped to drop below her shoulders on her back.

She was in a very good mood but seemed a little distracted. I thought she might have had a few drinks and so I asked her what Gloria and she did that night. “Not much. Just talk.”, was her only response. I made comment about her outfit not looking like a stay-at-home dress and she said they were going to go out but ended up watching a movie at her house because Gloria was trying to save money.

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She hung out with me for about 15 minutes and said she was taking off. Thinking I could take advantage of her sexy outfit when she got into the car, I decided to walk her out. On the way out, she waved goodbye to Leo and then told Rick not to work too hard. As I reached to open the outside door, Rick called me over to find out why the game had frozen on his computer. At the same time, Leo was cursing saying, “Who paused the game.” Rick said he thought Leo had mistakenly hit the pause key so I told Cindy I would be right back and ran to Leo’s office.

I looked at Leo’s computer screen and noticed the words ‘GAME PAUSED’ and in the top corner, it listed the person who paused the game … Rick. I was already calling him an idiot in my mind as I walked back to the front office. Cindy was in front of Rick’s desk and he was asking what she thought was the best way to impress a female co-worker of his that he liked. Walking up next to him, I slapped the back of his head and hit the pause button on the keyboard.

“Some people are computer handicapped.” I laughed. “Ok honey, we can go now.”

Rick jumped in and said, “Hold on a second, she is giving me some female advice.” He pulled out his wallet and as I moved out of the way, Cindy walked up next to his chair to look at a picture of the girl he was trying to impress.

“Wow, she is pretty”, Cindy said. “Have you guys gone out yet?”

Rick replied, “Yeah … a couple of times. But I don't think she wants to go out anymore.”, and smiled devlish grin.

I had to ask the obvious question that his smile demanded. “Did you hook-up? And what did you do to warrant that?”

He simply nodded his head and turned red as a tomato as he looked at Cindy. She giggled. Out of nowhere, Rick asked if I wanted to hear the details and I looked at Cindy not knowing how to answer. I knew Rick's stories of women were usually graphic and, at times, abusive. I was about to tell him 'some other time', but Cindy must have been curious becuse said, “Why not?!” Cindy obviously never heard his stories before and I was preparing for the worst. Having grown up in very religious and repressed family, she had come along way in experimenting sexually but Rick's fantasies and activities were more that I felt she was ready for.




Rick started to talk about a few of the highlights with this girl and with each story he was getting a little more graphic and adding detail. His aggressive nature in the bedroom and desire for rough sex was becoming clear to Cindy, who stood stunned. Meanwhile, I was getting a hard on just watching Cindy as she stood next to him, listening to his every word. I couldn't tell if she was being turned on at all but I knew Rick was enjoying himself. This was Rick's way of getting off; He loved to have people listen to his adventures.

I don't think Cindy ever noticed the bulge growing in his shorts. Not that he was trying to hide it, but even sitting down, his erect cock was too impossible to conceal. Cindy actually never looked down … her eyes were fixed on him with a look I can only describe as awestruck.

Cindy nodded as if to say she had heard enough and interrupted Rick to say, “Gee, I wonder why she doesn’t want to go out with you anymore. I’m not quite sure any woman wants to be treated like that. What the hell were you thinking! Asshole is the only word to describe you. You really gotta grow up.”

I took that as my cue that she was ready to leave and started to head towards the door again. She looked at me nodding and said, "These are your friends and not mine", and started to turn and walk away from Rick. He gently grabbed her arm to stop her and turned her around. Cindy just looked at him and said, “Don’t try to justify yourself … I really don’t care. I can’t believe I ever ...” and with that Rick, his chair facing Cindy as she stood right in front of him, with one hand on her arm, firmly placed his other hand on her thigh and moved up, under her skirt.

“Why don’t I just show you before you say anything”, Rick said.

“In your dreams. Just stop!” and was starting to pull away when, with a faint whimper, stood motionless as Rick’s fingers slid inside of her. I could now see her ass as his hand moved from her arm down, lifting her skirt, and grabbing one cheek with a tight squeeze. His other hand was slowly thrusting up and down. She reached out and put one hand on the desk to help her keep balance and briefly closed her eyes. I also noticed that her legs were parting, giving Rick easier access.




I suddenly remembered that she was the one to say she didn't want to do this anymore but I wasn’t going to say a word. After all, she was not making any visible effort to stop him, and that said it all. I quietly closed the door to the back offices so Leo wouldn't hear anything and sat in the guest chair besides it. My pants were off in 10 seconds and I started to stroke myself. 30 seconds later I was done … that is how badly I missed these adventures … and it did not take long to get hard again.

Rick pulled her onto his lap and started to make out with her. Her legs were slightly raised on the armrests and her ass was on the edge of his lap. One hand found its way under her blouse and began caressing her breasts while the other hand was still reaching around and grabbing her ass. Then I could hear her say, ‘mmm mmm (NO)’ and pull his hand off her ass. I could not figure out why but then he tried it again. He was playing with her ass and trying to put his finger on her asshole. She stopped him again.

On his third attempt, she pulled his hand back around and Rick seemed to snap. He stood up holding her in his arms, her legs wrapped around his hips. Cindy seemed confused in the whirlwind of what was happening and, without anytime to react, he pushed her off him, turned her to face the chair, and with a forceful push, bent her over. Her head and hands landed the chair with her ass up in the air. With her legs straight and her skirt above her waist, Rick knelt down behind her and spread her ass apart. Rick started to lick her ass as if it was the forbidden fruit of the gods. Then he reached in, around her leg, and put his fingers in her mouth, making thrusting movements with his hand. She was dripping wet and Rick was drinking every drop as his tongue went back and forth between her ass and pussy.

After a while, he stood up and quickly dropped his shorts. Pressed against her, he reached out and took a handful of her long black hair, and gently pulled on it asking Cindy if this was ok. She said, “Yes" and sighed. Then he pulled harder as his cock slipped right into her tight, wet pussy. She moaned and nodded yes. Again he he pulled even harder and started to fuck her with the same force. “Now?” he said, and she did not respond. He let go of her hair and gripped both sides of her waist to help leverage his thrusts but pulling her into him as he pushed. With each thrust she held in her squeals trying to not let him get too turned on, hoping he would just get it over with. Nevertheless, I knew she was turned on because, for being a very tight girl and Rick having a cock almost twice as thick as mine, he was having no trouble getting in.

Rick then started to slap her ass fairly hard. In fact so hard, it was leaving a small welt of his hand on her white skin. Cindy looked back at him and, in a hushed voice, said, “Fuck, yeah”. I could not believe that my wife, the woman who did not like to use that language in bed, just said those words to him. That almost fueled Rick because his slaps only got harder and her screams a little louder as she muffled them into the chair cushion.


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He reached over and grabbed her hair once more. Pulling it, he got her to lift herself from the chair and had her lean over the desk. She pushed some of the folders to the floor and then took off her blouse exposing her perfect breasts (biased opinion). Rick … never missed a stroke.

Now I was facing Cindy from my chair as Rick stood behind her and smiled at me. He pulled her hair and asked her if she wanted to be fucked harder. She did not answer. He yanked hard and her head snapped up and asked the same question. She shook her head no and I could see that she was getting a little concerned where this was heading.

Rick took his other hand, grabbed one breast underneath her, and squeezed. Then he let go of her hair giving her head a slight push and reached around the opposite side to grab her other breast. He was taking turns squeezing them, pulling them, and pinching her nipples. I had the best seat in the house. Her face flinched every time he squeezed her supple C-cup breasts and her pink nipples were getting some color but I knew from previous times that having her tits gripped tight was a turn on for her and him.

At one point, he had apparently squeezed so hard that she let out a yelp. Rick slowly pulled his cock out of her and started to move it around slowly, rubbing back and forth, as he kept her motionless by leaning on her. With his hands firmly grasping her tits, he stopped moving and Cindy started to wiggle under his weight. She yelled at him, “No … stop it … I can’t”, when she realized what he wanted to do. Rick’s cock was right on her asshole and he was starting to put pressure. I panicked for a moment wondering that if she screams any louder, Leo would hear.

I don’t know if she was looking for an excuse but she actually said, “ come on stop it … I’m saving that for Mark (me).” Rick looked at me and I had a complete look of surprise …, which he took to mean it was ok. Cindy always refused to try anal sex in fear the pain and to hear her say that she was saving it gave me hope. For the next two minutes, Rick kept pushing in and squeezing her tits harder as she clenched her ass. His sweat was being smeared all over her back and dripping down the sides. She did not say anything else.

As he kept pushing in, her body was visible tense. Her hands gripped the edge of the desk and she breathed loudly with an occasional moan. She actually looked at me and smiled so I knew everything was ok.

Once Rick had most of his cock all the way in, he slowly pulled it out and stood up, letting go of her breasts. Cindy just laid there on the table, eyes closed and lips pressed tight anticipating what was coming next. He grabbed her hips and began to thrust back in but this time a littler faster and further. As his pace quickened, Cindy lifted herself slightly off the desk with her arms. Her moans were getting quite loud. She couldn’t get fucked in the ass and control her yells like she was doing earlier, and she didn’t really seem to care anymore. I found out later that all of this was hurting her like hell but she was more turned on than she had ever been before. She liked knowing another man was getting off by wanting to fuck her in the ass so badly. This was something he told her he was going to do to her the very first time they did anything, but she had dismissed it as sex talk.




Suddenly the door opened up and Leo stood there looking at Rick and Cindy. I jumped out of the chair and instinctively pulled my pants up. Cindy's screams had been a little too loud but I got lost in the moment and forgot Leo was down the hall. I had no idea what to say or do. Cindy pushed Rick off her in 2 seconds flat. To this day, I have no idea where she got that burst of energy but having Leo come in like that must have freaked her out. She ran behind the chair trying to hide as much of her body as she could and looked at me for answers.

I started to dash toward the door to close it and push Leo out but Rick put his arm out to stop me.

“He knows all about it. This is why he stayed late tonight.” Rick looked at me and explained a little more.

“I ended up not staying late at work … but your wife kept me at the house a little bit longer than I planned tonight. I knew she would be coming to the office so I called Leo on the cell and told him to stay late.”

I looked at Cindy and then at Rick in shock. “Did you guys do something at the house?”

Rick nodded and Cindy hesitatingly said, “He came over and I gave him the files at the door but he asked to use the phone and he came in and it just happened. When he left, he told me to come by the office.”

FLASHBACK ------- I found out the details later but here they are ----------

Rick rang the doorbell and Cindy had the files ready by the door. When she opened the door, she said hi and handed him the stack of files. Rick then asked if he could use the phone for a quick minute to call the guys at the office because his cell phone battery was dead.

Not suspecing anything, Cindy led him to the kitchen where the phone was on the wall. While he talked on the phone, she continued to wash the dishes, oblivious to Rick's presence.

She was wearing a pair of Victoria’s Secret’s white shorts and white tank top PJs with spaghetti straps. You know the ones that have the word ‘ANGEL’ on the front. Rick kept eyeing her from top to bottom and he said he couldn't pass up an opportunity like this. When Cindy finished with the dishes, she walked passed him to head to the living room, and he reached around her and started to caress her breasts. Cindy fell back against his chest and began gyrating her ass into his crotch until he got hard. Her hands were shadowing his hands as they squeezed her tits. The entire meantime he kept talking on the phone.

After he got hard, she turned around to kiss him. Then he put his hands on her shoulder and guided her down to her knees. According to Rick, she never tried to stop and she could not get his cock in her mouth any faster. She gave him the best blowjob he ever had. During the blowjob, he was on the phone with Leo and never hung up. He even took her into the bedroom, ripped off her clothes, and fucked her while still talking on the phone. She laid on her back with her ass on the edge of the bed, legs up on his shoulders and a pillow on over her face so she wouldn’t moan too loudly.

As he fucked her, he pushed four fingers into her mouth and had her suck them like a cock. She told me all he kept saying while putting the phone away from his mouth was, "You like that, don't you ... you want that for real, don't you."

Cindy told me that he fucked her like the first time, good and hard and without being rough. After cumming all over her stomach, he hung up the phone and went down on her for a while until she came. The real twist was that she actually got nervous and asked him not to tell me because she thought I would be upset, especially since we had not discussed it and she told me she did not want it anymore.

Rick, always with an angle, told her that she would have to come by the office later tonight and dress very sexy for him or he would tell me. He made sure to tell her no bra, no panties. He convinced her he just wanted to see her dress up and pretend as if nothing happened with me right there … said he would get a kick out of it. Cindy believed him.

She never told him she would go, so he just told her that if by the time they left the office she was not there, he would HAVE to tell me everything. Right after he left he called Leo and told him what had happened. Leo knew something was going on while he was on the phone but figured it was the girl at work. The plan was set.

BACK TO PRESENT -----------------------

I walked around the other side of the desk, stood behind Cindy, and continued to try to figure out what was going on. She grabbed my hand and held it tight. Leo walked into the room and was now standing where I had been sitting. I must admit I was still quite hard and getting excited to think that another man was now looking at my wife. I do not know where I got the guts to ask it but I whispered to Cindy, “Do you want to finish with Rick?” She looked at me in astonishment.

Rick knelt on the chair with his chest on the backrest, facing Cindy. He leaned in to give her a kiss and she pulled back. I tilted her head slightly and started to kiss her, reassuring her that everything was ok. Rick put his hand on the back of her head and pulled her towards him to kiss. This time she did.


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As they kissed, I took a quick moment to put my hand on her ass and reach down. Holy shit, her ass was still wide open from his cock. I just pushed in a little and there was no real resistance. I just about came in my pants. Unfortunately, there was not much time to explore since Rick, now pulling her by the back of her head, took her around the desk and straight to Leo. “You are going to fuck the both of us.” Leo pulled down his loose fitting jogging pants and exposed his hard cock. It was similar in size to Rick’s cock but slightly longer and curved.

After kissing her again, he pushed her down on her knees and knelt himself down behind her. Cindy’s head was right on Leo’s lap and she started to lick the top of his cock. Leo’s hands were both on her head and pushing her lips down further on his cock. Rick was now fucking her from behind. This went on for sometime and Leo ended up coming in her mouth without telling her. She spit it out and almost gagged. Rick pulled her head back and slapped her face. “Swallow bitch”.

I’m not sure I was too thrilled with another man telling this to my wife but I figured it was the moment and didn’t bring it up later. In either case, this was a fantasy, which Cindy was apparently enjoying, and she never complained about it.

Rick kept pumping her while she stroked Leo’s cock until it was hard again. Then she got up and straddled Rick on the chair. With a slow rythm, she started to ride him with a renewed energy. She leaned into him so he could suck and bite her tits. Leo took the hint and embraced her, pulling her even closer so he could put more of them into his mouth. His hands slid down her back until they ended up on her ass where he pulled her into him with wild thrusts.

The chair had no armrests and was on wheels so as the fucking got harder, she put her hands on the wall behind Leo to stabilize the chair and planted the balls of her feet on the floor as much as she could. Rick was playing with himself right behind her and then moved in. It looked as if he was about to explode his load on her back but I was surprised once again. Placing one hand on her back as she fucked Leo, Rick pressed against her and was looking for her ass. Cindy leaned a bit more into Leo to raise her ass and give Rick better access. She reached back with one hand on the side of his ass and took hold of what she could to help him push in.

I could not figure out how someone who was having anal sex for the first time was semi ok with it and actually went from resisting to requesting it. I had always heard first time anal was the most painful thing and many women even cry. I found out later that this was not the first time Rick had fucked her in the ass but Cindy never knew I found out … but that is another story.

Rick’s hand was firmly on her back as he leaned back to get a better angle. I knew he found the hole when Cindy screamed out, "FUCK!" Now that there was no need to be quiet, she was letting it all out. Leo was having a feast biting and teething her nipples and Rick was thrusting as hard as I had ever seen anyone fuck and giving her an occasional slap on the ass every time she screamed. She even sat up and leaned back as much as she could without him pulling out to have him reach around and squeeze her tits. Leo’s hands were grabbing her waist and roaming all over her stomach and chest.




Rick whispered something into her ear and she nodded yes. Rick and Leo changed places and Cindy got on her knees again. This time Leo was behind her and in no time at all was on his knees fucking her full thrust, hands on her hips. Cindy wrapped her hands around Rick’s cock as she was being pushed back and forth by Leo, was trying to wipe Rick's cock after being in her ass. Rick grabbed her head and pushed her down giving her no time to finish.

There she was sucking one guy and being fucked from behind with her skirt bouncing up and down on Leo’s cock and her high heel shoes around his legs. The same woman who would never do this a few years ago; who ended up trying it a few times with Rick and Dr. Greer and wanted to stop after marriage; the same woman was now with two different men at once … and it wasn’t even my suggestion.

In a sudden thrust, Rick lifted his hips up to meet her lips and pushed his cock as far down her throat as he could. Holding her head against him, he jerked a couple times cumming in her mouth. He pulled his cock out and cum dripped off her lips. Without saying a word, she swallowed it all and went back to licking his head dry. *He had whispered earlier that he wanted her to swallow his cum … and she said yes.

Finally, Leo also pulled out and came on her ass as he collapsed back onto the floor exhausted. He definitely didn't have the same stamina as Rick. Rick picked her head up and kissed her passionately. He reached down with one hand and started to play with her clit and she clearly wanted more. Rick sat her on the chair and started to finger her and eat her out for almost 15 minutes. I walked up to her and started to kiss her as he did this, feeling her excitement by the movement of her tongue. As I caressed her breasts, I could feel some cum that had dripped from Rick but I did not care now … after all, her mouth was full of it a minute ago and my tongue was deep in.

As she writhed with joy, she suddenly pushed his head away. She could not take it anymore and just laid back, occasionally jolted by the orgasm.

Rick and Leo left soon after and Cindy went to the bathroom to get cleaned up. Walking to the car, she looked at me and smiled. “Did you enjoy it?”, she asked me. “More than you can imagine”, I answered.

She wanted me to drive home so we decided to take my car home and leave hers at the office. On the way home Cindy did another first … she unbuckled my pants and gave me a blowjob all the way home. That night we went straight too bed because it was 4am and she was exhausted. I on the other hand (quite literally), came three times in bed as I replayed what had happened that night. My wife obviously enjoyed other men desiring her and that was ok with me … it was her fantasy.

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