Losing my Cherry, So to Speak

Susan has been encouraging me (well, actually pushing me) to share my thoughts about our entry into the world of strap-on play. I resisted at first, but am now willing to share some more details, as well as my reaction to it.

For quite some time I have been very intrigued and arroused by photos of women wearing a strap-on, especially those in which the woman appears curious, kind, and funloving about it. I am not drawn to those that are more harsh, domineering, or cruel. So, I was quite excited when Susan told me about her plans for my special treat. I can't say I liked the idea of being in my cage and wearing lingerie all day at work. I am still afraid of someone discovering that little secret in the office. But, I obviously complied with her directions and they had the effect she desired on me - keeping my attention focused on what would happen that evening. I am constantly aware of my cage when I am in it. I am also constantly aware of the different feel of my trousers when they are worn over panties and stockings. They slide over my legs and my legs feel much more confined. So, I was constantly reminded all day of what would happen that night.

On the way home from work, I stopped at a Rite Aid to pick up a few things. At the risk of earning a spanking, I will share that Susan doesn't usually think of all the details for some of her little plans. I wanted to make sure that the details were provided for, so I purchased a Fleet enema, some condoms, and a large tube of KY jelly. I was sure that making sure my lower part was fully evacuated and the use of a condom would make things much more pleasant and easier to clean up for both of us. I also wanted to be sure she had plenty of lube!

When I arrived home, she saw the bag and asked what I had bought. She was a little upset with me for not relying on her. She acknowledged that she hadn't thought about the enema or the condoms. But she also told me that I had earned a spanking for my actions. It was not a punishment level spanking, but it was also not quite the erotic spanking she alluded to in her post.

After using the Fleet and showering, I arrived in the bedroom and dressed the was she directed. I was then required to lay over a pillow on the bed, so she could sit on the small of my back and spank me in a manner you see in this photo. I love to be spanked like that (except when it is true punishment). She worked all areas of my bottom quite well and I knew I had been spanked when she was done. But, I was also pretty erect throughout the whole process. When she was done she made me kneel in front of her and use my mouth on the strap-on. I resisted at first. But, when I realized I could hold her beautiful bottom in my hands while doing so, it became a very erotic experience for me.

She then decided it was time to take my cherry, so to speak. She was kind and asked how I wanted it. I asked her to take me from behind. But, I found I didn't like that very much. I didn't like not being able to see her. She then had me lie on my back at the edge of the bed and raise my legs. She stood and was at a perfect level. I confess that I loved it! I could watch her and she could watch me. She also had easy access to stimulate and tease me. Of course I loved that.

The entire experience is puzzling to me. It was different than I expected. But, very pleasant and erotic. Susan asked me if I have any "bi" thoughts, and I don't. If I was asked to do those things with a man, I would be completely repulsed. But, watching Susan's face and smile as she lubed up and gently pentetrated me was very erotic. I know I'm not doing a very good job of explaining. But, it is the best I can offer at this time.

Barry