EroticStories.com: The Craigslist Whore by Boyscout (infidelity)

The Craigslist Whore (bi:infidelity, 4008 words)
Author: Boyscout	Added: Jan 15 2012	Views/Reads: 9637/6004 [62%]	Story vote: 9.42 (19 votes)
I was curious how many guys thought I was attractive while dressed up in a skirt and after placing a personals ad on Craigslist I soon found out.

I don't know why or how I ended up browsing in the womens clothing section of the store but there I was browsing through some stuff they had on a clearance rack. I was there with my female friend Kristina so I didn't stick out too much but I still felt like people were gawking at me as I took a white tennis skirt from the rack and showed it to Kristina. "What do you think of this one?" I asked her as I held it up for her to see. "That would look great with your tan" she said. She was right. It was summer and I had been outside a lot this season and I definately had a rich tan going on especially on my legs since I was in shorts all the time. "You think it will fit?" I asked. She took it from me and held it to my waist. After a moment she pulled it away and replied "It will be snug but it will fit. You want it to be snug so you can show off your ass". I agreed with what she said and as I glanced back over to the rack I found the matching white top that went with the skirt. "Perfect" I said. We were done shopping for now. Kristina and I had become friends not too long ago and I felt comfortable enough around her to trust her with some deep secrets of mine, mainly my very secret bisexual tendancies. She thought it was great that I could be so sexually open minded. So ever since I told her about it she had suggested taking things a step further and seeing what I'd look like in a skirt. "You have amazingly sexy legs for a guy" she said, "I bet if we put a skirt on you it would make them even sexier." I had to admit that the thought had crossed my mind a time or two. "Heck I bet once you wear the skirt and take some pics you won't be able to tell the difference between your legs and a real females" she said. The fact that I had been shaving my legs for many years now did help the fact that I had some feminine loking legs so I had to agree with her. After we left the store we headed straight to my house to try on the outfit. It was s porty looking outfit which was something I liked, mostly because of my sneakers fetish I had developed since the beginning of puberty. I couldn't and wouldn't find anything sexually appealing or arousing unless there were some white socks and sneakers involved which was probably why I always tended to wear them and all previous girlfiends did too, mostly at my request of course. I kept the tags on the skirt and top in case we needed to return them but as it turned out they fit just fine. Snug around the ass and hips which really made them look good. The top was snug also but not bad at all. The bright white color made my tan really stand out. I stood in front of the mirrow in my new outfit complete with nearly new white Sketchers sneakers and white socks. I looked so good I started to give myself a stiffie. "Ready to take some pictures?" Kristina asked as she took the camera from the desk and turned it on. I posed in every conceivable pose we could come up with especially poses that would show off my ass and my shapely legs. After taking nearly 100 pictures we uploaded them on the computer and took a look. I was amazed that from the neck down I was a very convincing looking girl in a tennis skirt. The only thing missing was my lack of breasts but that was no big deal. My legs looked amazing and so did my ass. I thanked Kristina for helping me out and for taking the pictures and she told me it was her pleasure. Weeks went by and my new secret outfit remained in its secret storage location in my room. I would put it on every now and then just to feel it on me again but put it away soon afterwards. I didn't want it to get dirty plus I was always paranoid someone would see me in it even though all my shades were drawn and there was no way anyone could see inside. I had been trying unsuccessfully for many months now to get back into the dating scene since my wife and I had seperated. I went out on dates but nothing seemed to work. Women in my area seemed far too interested in how much you made and how hot you were rather than seeking anything meaningful from nice guys so as a result I remained single and lonely not to mention increasingly horny. I masturbated 2-3 times a day sometimes but it wasn't the same of course. It took care of the immediate need but I wanted something real. Another warm body to be with. Someone who wanted to make love to me and vice versa. A guy can only look at porn for so long before he becomes bored. It was one of those rare evenings when I was home alone when a thought popped into my head. My 3 year old son was off visiting his grandparents for a few days and I had some time alone. I decided to take advantage of the situation and see if I could get some company. I logged on to my computer and went on Craigslist. I had been a user on this site for many years now and had learned how to use it safely and

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