 Cindy's First Experience By: MiamiMark As I probably mentioned earlier, before we ever experimented with swinging, my fiancée would have been the last person you would imagine talking about, never the less, doing it. It all happened one night during dinner when I brought up the topic … if you want details you can read FIANCEE FOR TWO which gives the details. Well, that night after dinner we were on the phone I would ask her which of my friends she would ever want to have sex with and slowly she would confide her desires of a few … but we narrowed the list to Rick being her main attraction. When I brought up the possibility of setting something up, she wasn’t comfortable with it. Then I brought up some of her friends and acquaintances in the hopes she might feel more willing with someone on her terms. One by one we went through them all and nothing sparked an interest in her until I mentioned Dr. Greer. Now, Dr. Greer is a much older man at the hospital where she works and through the year he had made several minor yet obvious advances and flirtatious comments. He would tell her how he would be working on the weekend just in case she was too and maybe they could do lunch or she could stop by and say hi. Dr. Greer was a highly respected and prominent head of his department at the hospital. For some reason, all of these things attracted Cindy but she had never taken any of his advances seriously. Her thoughts were that he was just being friendly and enjoying the sight of a younger girl. I continued to probe about the realistic possibility that maybe he wasn’t just being friendly and that he might really want her. I could hear the excitement in her voice as she conceded to that possibility. Finally she admitted to herself that the thought of being seduced by him was one of her fantasies. Cindy was still in disbelief that we were talking about this, much less, planning this out. She would laugh and giggle with nerves as she realized I was more and more serious. But still, Rick was out of the question until she felt more comfortable so I proposed that she start with Dr. Greer. Now, I wasn’t so thrilled about this because I would not be able to be present or play an active role, but I also wanted to be fair to her. A few weeks passed and we kept talking about it more and more. It got to the point where she would come home from work and call me, telling me how nervous she was around him when he would make his rounds and stop to talk with her. She made an active effort to flirt a little more and see what he would do. One day he mentioned to her again that he would be working on Saturday (a day which is much slower at the hospital than weekdays) and asked if she was going to work that day. She told him that she wasn’t on the schedule but she did have to come in to register for some special courses and might be around there to swing by and say hello. He then told her to stop by his office if she was there and they could have lunch together and talk. For the next 3 or 4 days all we talked about was what she would do and how far she would let him go. Then she would reconsider and say “No, he isn’t going to try anything”. She was going back and forth but I knew that Dr. Greer wouldn’t pass on an opportunity like this. I even made sure the offer was too good to pass up by suggesting the outfit she would wear. Saturday came and I woke up real early with butterflies in my stomach. I spent most of the day in knots and anxiety wondering what was happening and what didn’t happen. We had decided to build the day up by not talking until after she came home. The hours felt like years and all I could do was look at the clock and count the minutes.
Finally she called me and asked me to come over her house … her parents were gone for the weekend and she wanted to spend the night with me. It was already 7 pm and I knew that the rendezvous should have taken place around lunch time. I must have traveled faster than the concord to reach her house in under 10 minutes. I rushed to ring the doorbell and when she answered I held my breath. There stood Cindy wearing the exact outfit we discussed. It was a yellow linen-like dress (mid-thigh) and her top that delicately draped over her beautiful C-cup breasts. The dress was sleevelss and had a black belt holding it tightly around her waist. As she moved in the dress, the bottom of her skirt would bounce up revealing a few more inches of her soft white thighs. She had on just the right amount of makeup and her hair was pulled back into a braided pony tail. It was a real feast and made her look a few years younger to say the least (not that 22 wasn’t young enough). As I kissed her it hit me … I could smell his scent on her neck. For the first time, I now knew how you could smell someone else on someone and my eyes flared. My excitement was killing me and I grabbed her by the arm and pulled her quickly into her parents bedroom (them having the large bed). I tossed her on the bed, jumped up next to her and started to kiss her neck. She laughed and giggled and them moaned as she whispered to me “ Do you want to know?” I nodded my head like a school kid waiting for candy. She held her hand up with three fingers and it took me a few moments to realize she was telling me how many times they had sex. Oh my God … they went all the way and she was only planning on making out with him today. For the rest of the night she recreated what happened using me as a stand in for Dr. Greer and gave me as much detail as she could. At one point she even blushed and became shy telling me she felt weird telling me these things and knowing I was actually getting turned on. Here are the events which took place that afternoon. Cindy got dressed making sure to put extra perfume on every part of her body. She was actually not anticipating anything happening but figured she rather be safe. Then she took off to the hospital and took the long way into the section with doctor’s offices because she didn’t want to run into anyone she knew … just in case. Since she had made up the excuse to him of registering, she wanted it to seem legitimate and had some random forms in her hand. She walked up to his office and he had left the door slightly ajar. He later told her it was so that she wouldn’t have to buzz in and notify security she was there. Entering the foyer, she continued to the back part of the offices and knocked on the door to his private office. “Come in”, Dr. Green said. 
When she came in, he smiled at her and stood up to give her a hello kiss on the cheek. Then he sat back down behind his desk and she plopped herself on one of the chairs in front of him. He looked up from the paper he was writing and they had idle chit-chat about her courses and about his day … blah, blah, blah. Then he walked over to the counter by the sink and opened the microwave where he had warmed up some food … an apparently was waiting for Cindy. After sitting back down he asked her if she had brought any food. Cindy nodded her head and said that she hadn’t intended to stay long and was only stopping by to say hi and run her errands. Up till now was still in disbelief that anything was going to happen and was already trying to imagine some lavish story to tell me and then drop the bomb that it was all a joke and nothing happened. Dr. Greer had other plans. He told her to pull her chair around his desk and sit next to him so she could try some of the food one of his patients had made for him. She hesitated but he insisted that this was the best Latin food he had ever had. Cindy pulled her chair next to him and sat down. Now, the reason I picked this dress became obvious to her. Because of the material of the dress and the belt around her waist, the dress rode up her legs to about a hand’s width away from her panties and it draped along the sides giving a descent view up her thighs with little effort. Dr. Greer gave her some food and she would lean in to take it from the fork. He would give her occasional complements on how pretty she looked that day and how nice the dress looked. She said she could tell he was a little nervous and that is when she realized he was trying to figure out if he should or shouldn’t make a move. During his casual talking he would laugh and make hand contact with her knee or arm. Finally he actually placed his hand above her knee and started asking her if she had ever been on a boat since he had one and would love her to go on it one day. She smiled and said she would love to and then he moved in and gave her a really fast peck on the lips and pulled back. I guess he was trying to read her reaction which was nothing more than a smile. Then he moved in again and gave her longer kiss and she parted her lips to let him know he could go further. As they kissed, his hand inched up her thigh. As he did, she said that she felt his hand brush up against her other leg and she panicked thinking he would interpret her legs being closed as a stop. She had never done this and until this moment, I was the only other person she was with. She told me she didn’t want him to think that so she opened her legs pretty wide to give him access. He quickly moved up her leg and began rubbing through her panties. She was a little embarrassed because she usually gets pretty wet and was concerned about his reaction. She moved her hands on to his chest and began to play with his nipples (one of my favorite things). It didn’t take long before he took her off the chair and laid her on the floor. Cindy managed to say the only thing on her mind, “wow .. we are really going to do this?!”
He had Cindy take off her clothes as he watched. One of her favorite comments was his comparing her to a beautiful model which she ate up and wanted him even more. She climbed on top of him and began to rub her moist pussy on his semi-flaccid cock. He was an older man and it took him a while longer to get hard. Since she hadn’t experienced older men before she wasn’t sure what to do and decided to slide off him and give him head for a while. The whole time she was sucking his cock, he would hold on to her braided pony tail and moan. Then he pulled her up to lie on top of him and kiss her while his hands ran up and down every inch of her body. She says she doesn’t remember ever being rubbed so hard everywhere … but it was great to see how much he wanted her. Then he pushed her up until she was sitting on his face and with her hands helping support her on the wall, he ate her out for a good 15 minutes. Then placed her on her back, lifted one leg over the other to give him an almost side entrance into her and began to rub the tip of his cock to her pussy. Slowly using his hands to help push it in, he kept gyrating and gently pushing in. She remembers that he made a comment about her being prettier than his daughters friends which would come around the house to use the pool, and none of them had the body she did. This actually turned her on even more because she realized the fantasy this guy must be having with her. Cindy stopped him and asked if he had a condom and, as if by magic, he pulled one out of his unbuttoned shirt. Sure he wasn’t planning any of this … I told her. Although he did not have a very hard penis, it was … in her words … very, very thick, almost 3 times thicker than mine. This and the latex made it a little uncomfortable for her. He didn’t have much in length and for that she was almost grateful because she wouldn’t know where to put it. I laughed at this point and had to stop the recreation as I regained my composure. He finally pushed it in and began to use short and slow strokes. It took her a few minutes to get used to his size and began to let out little sighs and heavy breathing. She was never much into loud sounds or talking in bed … at least not until Rick. Dr. Greer would run his hands over her breast and face almost as if worshiping Cindy. She loved every minute of it. He started to quicken the pace and it lasted for about 30 seconds before he gripped her and jerked back as he came. He just stayed there catching his breath and she was thinking how surreal this all was and that by tomorrow morning they would see each other in the hall and no one would know. After about 20 minutes he asked her if he could go down on her for a while. She smiled and he took the acceptance and began to eat her out. Once she started to cum and he sensed her body tensing up, he knelt in front of her and went back in to thrust his cock into her. This time it was more flaccid then before but the condom was still on … he didn’t have any semen since she found out he was operated on. It only took like 5 strokes for him to cum again.
Then they lay together and he kissed lips and caressed her breasts for over an hour. He would kiss her with his tongue from her stomach to her neck and focus on the nipples for minutes at a time. She just let him and was waiting for the time to go home. As they got up from the floor, Dr. Greer stood behind her with only his opened shirt on. Cindy was completely nude and he reached around to embrace her from the back. She leaned into him and felt that he still had a little chubby pushing against her ass. She wiggled around in a teasing manner and he began to push her towards his desk, never letting go of her. She couldn’t believe that his man was going to go a third time with her … made her feel like a real turn-on. When he got her to his desk, she bent over laying her stomach flat against the cold wood table top. He put his hands on her thighs and pushed them slightly apart so she reciprocated by parting her legs as far as she could go. His hands caressed her back as he rubbed up and down that her ass. Then he took one hand and began to fondle his cock … she assumed he was trying to get it hard again. A second later, he placed his condom next to her on the table and she felt his cock sliding up and down her ass again. She wasn’t sure and didn’t want to jump to conclusions so she asked him if he put another one. He said no. Since he wasn’t being forceful, she didn’t jump up but did tell him that he had to put one on before he went in. He kept sliding up and down and pushing his groin up against her every once in a while; almost as if he was trying to see how much he could get away with. He would put his hand between her legs and finger her with 3 and four fingers and then run them up her ass and back down. Then we would continue rubbing his cock against her. This went on for a few minutes until he started to put both hands from behind, putting 2-3 fingers from both hands slightly in and pulling the lips apart while his cock was around the ass. She wasn’t sure what he was doing but it all felt nice to her and she lay there enjoying the touching and fingering. As his hands were pretty much holding her ass cheeks apart and pulling her pussy open he would actually pull upwards, slightly lifting her ass off the table. Then he would get his fingers a little deeper in her and pull up again.
Sometimes the stretching would be a little too much and she would let him know by a slight sigh of pain and he would release the grip a little but then build it back up. Dr. Greer asked, “Do you like it?” She moaned her answer to him. Then he asked her if she wanted him inside of her. She moaned her answer again. Dr Greer then said, “Good because I’m inside of you.” That caught her off guard until it dawned on her that he had actually used his hands to stretch her and lift so he could push his cock into her without her really knowing. Cindy told him to get it out and put a condom. He told her he wasn’t going to get her pregnant and that he just wants to know what she feels like. He kept talking and explaining how all he kept thinking about he past few months was her body and how beautiful she was, and how much he wanted her. I think he just talked so he wouldn’t have to pull it out … and in worked. She was so taken by him that she started to push against him and he immediately took his hands off her pushy and held on to her hips to help thrust. It didn’t take long at all and after she said, “ Yeah, Dr. Greer, I like it” was all it took for him to finish. After a few minutes and getting dressed they kissed each other on the cheek and Cindy made her careful and cautious escape from the hospital … hoping no one spotted her. That is it. All that happened and I wasn’t there for any of it. As you can imagine, it sucked but I’m at least glad she shared all the details with me. The next time we experimented it was with Rick but we she did have 5 or 6 other encounters throughout the year with Dr. Greer.
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