Condom 101

Rachel and I had been seeing each other for a few years when the breakup occurred. She was extremely attractive and I fell in love with her face the first time I saw her in a neighborhood bar. All in all she was an amazing woman and I loved being with her except when she became "captain of the universe" and very bossy. This led to a few disagreements but nothing fatal to the relationship. What finally undid it that I wanted to have sex three or four times a week and she only wanted sex about half as many times.

Even though we were not seeing each other after the breakup we still remained trusted friends so it was not a big surprise when she called one day and rather hesitantly told me she needed a favor and I was the only one that she could trust. She explained that she had begun to date and was concerned that one of her partners and she may want to engage in sex. Her concern was that she had no knowledge of or experience with condoms. Her request was that I help her better understand their use. Specifically, she asked if I would teach her the fundamentals of using them.

I immediately agreed that I would and suggested that she come over to my apartment the following evening about 7:30. I suggested that she dress as if it were a date to make the experience as real as possible for her.

It was late fall so I knew about that time it would be dark outside and we would have an intimate setting for the class. I told her that I would get some condoms the next morning and would put a bottle of good red wine out to breathe about 6:30. Needless to say I was already highly aroused in anticipation of whatever was going to happen. The next morning, I got six Trojan Magnums (I'm not very long but I'm very thick) for our class later that day.

At exactly 7:30 I got a call from the security folks that she was heading upstairs. I opened the door in anticipation of her getting off the elevator and was struck by how totally beautiful she was. I was flooded with an overwhelming number of very pleasant memories of dinners, drinks European trips and, yes, lots of sexual intimacy that she and I had shared. She had a full skirt, black high heels, a lovely blouse and a Hermes scarf that helped frame her beautiful face. She was wearing the diamond stud earrings that I had given her for Christmas the year before. I handed her a glass of red wine that I had prepared, and we sat in my living room looking out on the channel and the various activities that were happening at dusk.

We sat and chatted for 15 or 20 minutes and both finished our first glasses of wine. I then asked if she was ready for her lesson. Hesitantly, she said she thought she was and told me how much she appreciated the fact she could trust me to help her with this situation.

I then suggested the following plan. We would go into my office which had an attached bathroom. I told her that I had placed six packages of condoms next to the sink. The plan was to go into the bathroom together with the light on and give her a few seconds to orient herself as to where the packages were. I said after she felt comfortable, she would turn off the light which would place the room in total darkness. I said I would then remove my shorts and sit on the counter next to the sink. I then went over the six elements of the lesson we would have. First of course was opening the package being incredibly careful not to scratch or otherwise damage the contents. Second was to remove the condom carefully. Third, and I pointed out this was the most important step, was to orient the condom so that it would unroll when it was put on. I pointed out that the round ridges around the condom needed to be positioned so that it would unroll after it was put on. I suggested that she could very gently put a finger into the condom and make sure that it was positioned so it would unroll but being careful not to scratch it. I then went on to say that she would have no trouble finding my penis because it was already very erect. After placing the condom on the head of my erect penis she would then unroll the condom all the way down to its base. I also suggested that once it was fully unrolled, she gently grasp the penis and move her hand slightly up and down to make sure it was tight and remained in place. I also reminded her that we would stop at any point in the process at which she felt uncomfortable. After a quick reminder that the six steps were opening the package carefully, removing the condom, orienting it so it would roll down, placing the condom on the head of the penis, rolling it down and then checking to make sure it was secure, I asked her if she was ready and she said she was.

I suggested that she tell me what she was doing each step. I could hear her find the package and she told me she was ripping it open which I could also hear. She said she was gently removing the condom and was surprised that it was slippery. I apologized for not telling her that the Trojan Magnum was pre-lubricated and that's what she was feeling. She then said that she was orienting the condom and was ready to put it on me. Unfortunately, her orientation had not worked and so when she put the condom on it would not roll down. I suggested that she throw it in the sink and open up a new package which she did. The second time she was more careful to make sure that the edges were oriented properly and so she successfully put it on the head of my penis and then rolled it down to the base. After having done so she gently put her hand around my penis and moved it slightly up and down to make sure the condom was in place. I said she had done a great job and was a quick learner and we could consider the lesson a complete success. I pointed out that under normal conditions removing the condom would be far easier than it would be right then because after successful intercourse the penis is generally smaller, so the condom comes off very easily. In this case however the condom was still very tight and we had to unroll it to get it off. We then put it in the sink with the first one. I then put my shorts on without turning the light on and told her to go ahead and switch it on.

I told her that I thought she was ready for prime time and, after a gentle hug, that the only thing left to do was her final exam. I asked her if she had ever had sex with a man wearing a condom and she said she had not.

I told her the final exam would require her to stay in the bathroom after I left and remove her pantyhose. (I knew she never wore panties with pantyhose because she had pointed out to me that it was unnecessary; that's why they were called "panty" hose.) I reminded her to grab one of the condom packages and figure out a place for it which would be handy when she wanted to retrieve it. I told her that in my opinion it was her responsibility to ensure that her sexual experiences were safe and therefore her control of the condom was important. I suggested that perhaps the waistband of her skirt would be an easily accessible place.

I went to the kitchen and poured two new glasses of wine and then sat down at my desk. When she came out of the bathroom, I got up and walked to the bathroom door and handed her a second glass of wine. We each took a couple of sips and hugged again but this time it was accompanied by a few minutes of deep kissing. She had always been the best at kissing as foreplay. I said the final exams started with her lying on her back on the heavily carpeted floor to help create an environment that was appropriately spontaneous. The only light in the study was from the outside and because it was nearly dark outside the room was also nearly dark. I said after she was on the floor, I would take my shorts off again and kneel between her legs. I would then move her skirt up.

She would then retrieve the condom package and follow the six steps she had just learned, reminding her that it was very important to get step three correct so the condom would roll down for a snug fit. I told her that making a mistake at this point could interrupt an otherwise intimate and passionate mood. We did not speak further but I heard her rip the package, remove the condom, and waited for her to orient it. Because I still had a raging hard-on she had no trouble finding me in the semi darkness. She expertly applied the condom, rolled it down to the base and gently determined that it was a tight fit. I reminded her that we would stop at any point at which she wanted to stop.

I asked her if she was ready and moved her legs a little further apart. I then positioned myself over her and gently pushed into her. I reminded her that this part of the exam was to make sure she understood how penis with the condom felt in case it felt different or uncomfortable in any way. I then moved in and out but because this was not a lesson that required consummation I pulled out and removed the condom.

I told her that she would get extra credit if I could reenter her so she could clearly compare the two feelings. Again, I said that if she ever felt uncomfortable, she just needed to tell me to stop. After nearly 36 hours of foreplay I was very ready to finalize the extra credit portion of the exam. She began to respond in a way that was familiar to both of us and when I asked her if she wanted me to stop she said, "Don't stop, don't stop" and after a few minutes we had massive shared explosions.

I stayed on top of her and in her for a few minutes and then rolled off onto my right side. I put my right arm under her head and moved her shoulder around so that we were snuggling and enjoying wonderful afterglow. I am pleased to be able to report that our breakup ended at that moment and for the next several years neither of us ever worried about condoms again.