Well, I wrote several of my encounters with Cindy when she was my fiancée and when she was my wife. Today Cindy and I are divorced but still remain close friends (irreconcilable differences, but a lot of love) and is why some of the stories had her own recollections and memories. In fact, at the time of my writing this, Nat, Cindy and I had already even shared an experience, so to say the least … we are all good friends.
A couple of years after our divorce (Cindy and I) I started dating a younger girl, Natalie. Natalie was a 22 year old with Latin blood and passion, a wild combination. In so many ways she was completely different from Cindy. She had a rich bronze tan that made men crazy, smooth long brown hair, and an amazing body. Unlike Cindy’s C-cups, Natalie had at least a D or more. Her thighs were perfect and her ass was just large enough to hold.
Believe it or not, she was actually Rick’s sister (Rick, for all those who haven’t read the earlier stories, is my best friend and the man who my x-wife and I would have swinging adventures with.) Of course, Nat knew that my x-wife had slept with other men during our relationship and that I enjoyed it tremendously, but she never knew it was her brother.
At the time we started dating; Nat was finishing college up state … about 5 hours away. For most weekends I would make the trip up there to spend it with her. To say the least, she was by far, the horniest girl I have ever dated. I’m not sure if it was the age or the hormones, but she would love to have sex several times a day and I, even at 32, could hardly keep up. I guess she had it all pent up throughout the week seeing all the college studs and the constant getting hit on.
She was a recluse for most of her college years, and even in her last year, only had a couple of friends she would hang out and study with. One of these friends was Cory. He was an average looking guy with a thin goatee, slightly built but on the scrawny side and was about an inches shorter than Nat.
A few months after Nat and I started dating, he asked her to go out to dinner telling her he needed to talk about something which had happened. At the time I didn’t think anything of it since he had a longtime girlfriend and it was just dinner. When she came home that night, she told me he was torn up because him and Cindy (not my x-wife, but his girlfriend) had broken up; something about not being 100% right for each other. Although this had actually happened 3 weeks before, they would still see each other to have sex, etc …. Ah, the college life I thought.
Nat told me how their conversation started touching on sexual topics and fantasies … and I was beginning to get a little concerned where this was heading, probably because I wasn’t sure I wanted to do the same things I had done with my ex-wife. What my ex-wife and I did was wonderful and the best that had ever happened. But I knew Nat was critical of our activities ever since I told her what we had done in the past. Although I never gave her full details, she couldn’t understand why I would want another man to be with my wife or girlfriend. She kept saying that one man or woman should be enough and I explained it had nothing to do with my love for her, it was just a choice we decided on to enhance our sexuality.
I also got concerned when she confided in Cory after he asked her if she had ever had thoughts of being with another girl. She said that it had crossed her mind since a few of her friends had done it and loved to do it from time to time. I must admit that hearing this did turn me on but I didn’t put much emphasize on it. After all, I could see her one day kiss a girl at one of her parties just to say she did it and that would be the end of it.
As the weeks passed, midterms were getting closer and she would spend most of her free time with Cory studying at the school or at one of their apartments. These sessions would sometimes go late into the night and then they would unwind by going to a bar and having a couple of beers. Sometimes, he would be too drunk to drive home and she would either have him sleep on the sofa at her place or stay with him at his (on his sofa). I knew they were flirtatious because I saw how they were with each other around me and I could only imagine it was tamed with my presence. On occasion, I would ask her if she felt this might lead to a uncomfortable moment or dangerous situation and she always said he was just a very good friend and a great study companion and he would never try anything.
One Saturday she called me in the afternoon and confessed that while doing her laundry in her building’s laundry mat, she had a fantasy about Cory coming in there and having his way with her. I just laughed and we talked about it for a while. As the conversation progressed I would ask her ‘what if’ questions like, if he kissed you what would you do. Or, If he touched you, what would you do? All her answers were expected … Nothing, Stop Him, etc.
The next night we spoke on the phone and she told me that she had the same fantasy the previous night and she was starting to get concerned because the more we talked about it the more she thought about her fantasy. I probably shouldn’t have, but I kept talking about it more and more to see how she felt. I finally got her to admit that if he made a real aggressive move, like grab her and start fondling her she would probably let it happen, but if he was slow or tried to kiss her she would stop it. And so our talks got hotter and hotter as I kept throwing out scenarios and listening to her responses.
I finally broke down two days later and asked her if she wanted to fuck him. She was silent on the phone and I just waited. Nat said that she never wanted to do what Cindy and I had done but that it was an exciting thought because she saw how much it was turning me on to talk about it. I’m sure it was more than how excited I was because she had played with herself each time I would elaborate on her fantasy with him. The more we talked that more she kept fantasizing about him.
One weekend while I was up there she got pretty drunk and we had sex the entire night. Because she had so much alcohol, she wanted more and more sex. At one point, when I didn’t have the same thrusting force as she wanted she actually said, ‘Cory would fuck me harder than that’. I exploded inside of her. Within 5 minutes I was hard as rock again and started asking her if she wished it was Cory fucking her and as I was pumping away, she kept saying, “Yes!!”.
The next morning she remembered having said the Cory remark but she just tossed it up to being drunk and horny and said she thought I would enjoy it. We talked about it at lunch on the way to the movies and I asked her if she had ever talked to his ex-girlfriend about our sex life. She said they had and then I asked if she talked about theirs. Apparently, Cindy (Cory’s Ex), had always bragged about his size and stamina. “Did that ever cross your mind?”, I asked. She responded, “Yeah ... that was why I said what I said last night.” I was beginning to wonder if I wasn’t lasting enough for her … did I need to order Viagra at 32. LOL.
Two weekends later I was in Miami and wasn’t going to make it up to visit her because it was my birthday. I was having a get together with friends at a local restaurant and had to be there about 2 hours early to make a reservation because it always got packed. It was 7:30pm and I still had another hour and a half before anyone showed up so I called up Nat.
We chatted for a while and she brought up the fact that everyone had gone home for the weekend and she was going to be bored studying alone. I quickly made mention that I was sure she could be studying with Cory and she just laughed. It didn’t take long to get into a really hot and sexual conversation about scenarios. Then I asked her if she would do something if I asked her to. And, without hesitation, she said yes. I asked her why she didn’t go ahead and do it now before I changed my mind and she said he was gone too. She kept saying that she would do something another day and I balked. I told her we would have to talk about at that time … I could tell she was disappointed. Then I made sure and asked her to give him a call just in case and she assured me that he had called her when he was packing.
After we hung up the possibilities and the wonderment of what she would do was driving me insane. I couldn’t take it anymore and for no other reason other than to appease my anxiety, I gave a call to Cory (I had his number in case of emergencies). To my surprise, he picked up and I started saying hello. We talked for a couple of minutes and then I built up the courage to say something and pretend it was casual.
“Cory, do me a favor. I’m not coming up this weekend and Nat is in one of her depressed moods, especially since everyone is gone for the weekend. Do you have any plans tonight?”
Cory then told me how he was going to stay with his parents but then realized how much studying was left and cancelled at the last minute.
“Why, what do you need?” Cory asked.
“Would you hang out for a while with Nat or catch a movie so she cheers up? Otherwise she is going to mope around the house all night. But don’t tell her I told you because she’ll start complaining that I am interfering in her life. Just swing by her place as if it was a casual stop over.”
Cory said, “Sure, that isn’t a problem … we might even get some studying done. I’ll go over in a few” … and then I thanked him and hung up.
About 20 minutes later I called Nat and caught her as she had finished taking a shower. I asked what her plans were and she said, “Dry up, watch TV, and go to sleep”. I made fun of her exciting evening and she kept saying how she wished I was there.
At this point I was parked in a secluded part of the parking lot without lights. I reclined my chair slightly and started to stroke myself as I brought Nat into one of her fantasies. I could hear her loud breathing and knew she was playing with herself. As if I planned the timing myself, her doorbell rang and she yelled, “Be there in a sec.”. She was getting up from her bed and told me she had to put me down she got dressed. I told her I wanted her to answer the door in her silk mini-robe.
“What if it is my neighbor or another guy?”, she quipped.
“Do it for me … It’ll turn me on just wondering what they are seeing.”
“You asked for it,” she said and giggled.
She had put the phone down and I could hear her putting on her robe and walking out of her room. A few seconds later I could hear a nervous laugh and some muffled voices. Then she picked up the phone and told me that Cory had just come over. I acted surprised and asked what happened. She said that when she opened the door, it took her by surprise and she ducked behind the door. He had laughed and then she told him to enter in about 10 seconds while she ran to her bathroom (inside her bedroom). She closed the door and ran to her bathroom, picking the phone up along the way.
I started to laugh and pretend it was all funny. While she was in the bathroom I heard Cory in her bedroom saying, “Ok, I’m in here so don’t take forever.” Her college apartment had a small living/kitchen area, and two bedrooms, each with a bathroom. Whenever she had someone over to study or watch TV it was done in the bedroom.
I asked her why he was there since she said he had left town. She started to whisper on the phone and say she didn’t expect him to be here. Jokingly, I told her this was her big chance to do what she wanted. I could hear the nervousness in her voice. Then I told her to go out there and watch TV with him … but not to change. I was controlling the situation and she was letting me. She was really hesitant but kept insisting he wasn’t going to try anything. “So why are you so nervous?”, I asked.
“Oh my God, Oh my God.” she kept repeating. “He’s going to hear you if you keep it up.”, I laughed.
“Ok, I’m going to hang up now.” and she did.
Meanwhile I was at dinner the entire time dying to find out what happened. I tried to give her a call a couple of times but the phone kept ringing. This was driving me crazy … and I was beginning to regret my own idea.
Dinner was over and I was at home just counting the minutes, imagining what was going on … when the phone rang at 2:17AM (I’ll never forget the time). She said Hi and we started talking, pretending nothing happened the last time we talked. Finally I asked and she kept saying how great it was but wouldn’t give me any details. 20 minutes of pure hell as she toyed with me. Finally she told me that nothing happened.
She had tried to see if he would do something by asking him to put cream on her back. She even dropped the top back of her robe so he could put it on, and he never made a move. Then she felt so self conscious that she changed and they ended up going to a movie and a few drinks. Arrrggg….. But I couldn’t let her know how it killed me the entire night.
A few months had gone by and we talked about Cory less and less. I could tell she was so worried that he would reject her that she never wanted to try it again. Then she told me she wouldn’t want to do it even if she could. But I thought she was just saying it to not think about it anymore.
It was a couple of weeks before she moved back home from college and I had gone up to help her clean and pack. Cory had come over to help us on Thursday and Friday. I’d become pretty comfortable with him and, ever since the situation, figured he was pretty safe to be hanging out with Nat. Saturday he stopped by for a minute to drop off some of Nat’s CDs and we asked him if he had any plans that night or Sunday early morning. Cindy had amassed a collection of about a dozen liquor bottles, each half full and she was going to throw them away. We figured if we had someone, we could all take em down and not let them go to waste. He was in.
That night we rented a couple of movies and started drinking early. Most of the time was spent talking about their college experience and all the crazy things they had done. Half way through the night, Cory brought up Cindy and how they still see each other often. Nat jumped in laughing and asked, “Hmmm, I wonder why you two see each other.” He just laughed and said, “yeah … the sex it too good”.
By this time most of us were a little tipsy and I was a little more than that. He asked us about our sex life and Nat took the reigns to answer. I just smiled and she had great compliments. I mentioned to Cory that from what I hear, he has nothing to complain about either. He looked at Nat and asked how we both knew and she confessed Cindy would talk about them often. The guy actually blushed.
Nat then decided that we should play Truth or Dare with alcohol. I had a flashback to the last time I was in high school and played Truth or Dare … wow, I was getting old. We went around asking stupid questions and taking shots of the weirdest mixed drinks. Drunk we pretty much all were but the fun was still going on.
On one of my turns, I asked Cory, “Truth or Dare?” and he took truth. I asked him if had ever had a fantasy or sexual thoughts about Nat. Her smile disappeared and she glared at me and called me an asshole. I ignored her and asked Cory to answer. I don’t think he really cared because he didn’t hesitate and said, “oh, yeah … a few times.” Nat laughed and quickly tried to change the subject but I was determined to let her know she could’ve had him if she wanted that night a few months back.
I started talking to Cory and asking what his best sexual experience in college was and how many girls he slept with. I even asked him if he had ever had two girls. The conversations were getting hotter and Nat just stayed quiet listening to him. She would also ask questions and hypothetical situations to get his reaction … she was loving it. We finally finished the last shots and it was obvious we weren’t going to be able to stay up much longer … especially since Cory was pretty much passed out.
Nat and I left Cory on the living room floor and went to get ready for bed. Well, at our state of mind, ready was just dropping our clothes and crashing on the bed. After all that talking I was horny as ever and when she took off her clothes, I pushed her against the wall with her ass to me and started groping her all over. She was very wet as my hand reached around and between her legs. I began to fuck her from behind and wasn’t going to last 5 minutes. I began to talk to her and ask her if she was turned on by his stories. She just nodded and hummed a yes.
I turned her around and unfastened her bra to let it drop to the floor. Then I reached over behind the door and pulled her silk robe off the hanger and told her to put it on. “But I’m going to bed”, she said. I reminded her that she had a guest out there on the floor and that she should probably help him to the sofa. She looked at me puzzled and wondering why I wasn’t getting dressed to help, after all, he was too heavy for her to lift.
I told her I wanted her to leave the robe loosely tied and help him on the sofa. Her eyes seemed to almost sober up when I said those words. I grabbed her arm as she was about to say something and I pushed outside the bedroom. “Just do it and then we’ll fuck as long as you want? I just want you to get a little wetter before we do.”
She told me later she figured this was a turn on for me since she didn’t understand what it would do for her. But she went and I peaked around the corner and watched as she helped him up. She even fastened the robe tightly so it wouldn’t open up when he leaned on her. She even took his shoes off when he laid back on the sofa. He mumbled thanks and then closed his eyes again. By the time she was almost finished I had crept up right behind her put my arms around her. She jumped and yelped but Cory didn’t wake up.
“I told you to leave your robe loose!” I said and then pulled the front open. She sort of struggled to close it back up but I wasn’t going to let her win this time. My hand went down to her pussy and I stuck a couple of fingers inside. Her arms tensed and she stopped fighting me. There she was in front of Cory with her robe open and me fingering her as I whispered things into her ear.
“Look, Cory is right in front of you. Don’t you wish you could just fuck him?” “Do you want to grab his cock and put it in your mouth.” “You know he fantasizes about you.”
Her breathing kept getting faster and her sighs would get louder and she would put her hand in her mouth to muffle the sounds. I pushed her back down and she reached over Cory to put her hands on the sofa back as I stuck my cock inside of her. To this day, that will always be the most amazing sight … fucking my girl over another guy as he lay passed out.
After a few minutes she started to get nervous he would wake up and she asked me to stop and go back to the bedroom to finish up … and we did. Well, at least we tried to until we passed out ourselves from all the alcohol. Lesson to be learned kids … too much alcohol prevents you from performing.