More Than Shopping

It's been really pleasant having my wife not only accept but also enjoy having a girlfriend around the house. I loved being able to come home a dress in sexy lingerie under anything from jeans to skirts. At 5'7" I tower over my wife when I am wearing heels so we don't stand next to each other but I do plenty of walking around for her to see my sexy body. By her own admittance I walk better in heels than most women.

Walking around the house is fine but I know with the right clothes and makeup I can go out and most people don't have a clue I am a guy. I have walked into women's clothing stores before, usually on a Halloween so I have an excuse, and those women pretty much instantly know but most are very helpful and treat me like any other woman customer. I really love being able to do this occasionally but I also have to be careful and remember not everyone is fine with that sort of thing, and I don't really care to be seen by any men when I am out. I just enjoy walking around and shopping, like any other woman!

With spring around the corner I knew my time that I was able to keep shaving my body was coming to a sad close. I love the soft feeling and rubbing up to my wife and being smooth is so erotic. I know she enjoys the feeling too. With time running out I wanted to get in a quick shopping trip then come out completely made over to my wife and a wild night of lesbian lovemaking.

My heart started racing when my wife agreed agreed to let me get a makeover. This entails traveling about an hour to a place where I would not be known. I have become good friends with a very pretty make up artist at a salon located in a small strip plaza. It's relatively private and since she has been waxing my brows and doing peels etc... on me for over year we have become good friends. We had kidded before during Halloween how she could make me look like a hot babe so I knew she would be okay with doing a makeover on me.

As the day drew closer I found myself getting very aroused at the thought of transforming. I was a little worried because even though the salon is somewhat private, I was walking in a man and out as a woman which meant I would have to pass the reception desk and whoever may be milling around it. I calmed myself down by repeatedly telling myself, "No one will care, and no one knows you anyway." I knew the pedicure station was private too so I decided to go all out and get a pedicure with color before my make up appointment. As the day finally arrived I was still wavering back and forth. My mind raced with silly thoughts of being pulled over or my car breaking down as I was driving back. I pushed those thoughts away and told myself the odds of anything like that happening were slim to none.

I knew once I was in the pedicure chair I would start to relax and I certainly did. Before I knew it was was walking back with by bag of clothes to the make up room. The make up artist, Jen, looked over a few things I had brought and we mutually decided on skinny jeans from The Limited (size 4), a black Guess top and some very sexy grey high heeled booties from Guess also. I had a feminine black blazer to hide my arms and I also borrowed one of my wife's winter jackets and a scarf as it was quite cold. I had purchased a short curly wig that was a great realistic style. One of the wigs I used to wear provided a dead giveaway as it was just too much hair. I have found if I copy real styles it is much easier to blend. (I am lucky that I am small enough to fall within a typical woman's size.) Most people are simply too busy to notice "normal" attire". I could not have chosen a more typical, but sexy and classic outfit. I really should have worn flat tall boots like every woman is wearing now but I needed a little sexiness!

I changed into my outfit and Jen went to work on me. An hour later I looked in the mirror and was quite pleased. As I put on my jacket and took a deep breath to walk out to the reception area I heard Jen let out a little "Wow".

When I asked her what that was for she said, "Standing behind you I see a sexy woman's body. I would never guess you are a guy and you should plan on getting hit on by some guys when you go out."

While that made me smile it also left me a little nervous. I informed her I was quickly stopping at one store then going home so there would not be any opportunity to be hit on.

As I walked out into the cold air I reminded myself what Jen had said and simply put on my best woman walk and went to my car. From there it was a short drive to the strip plaza. I planned on going to one store that sold upscale women's fashions. I had been in the store as a male before and one woman in particular had helped me look for a dress. When I told her I was looking for myself she was very helpful. There was no one in the store that day so she encouraged me to try on a few dresses which I gladly did. One dress fit me perfectly and I heard the saleswoman exclaim that my boyfriend would love me in the dress. She assumed I was gay and I didn't bother to try to explain I wasn't especially after she was so helpful. We talked a bit and she told me her work schedule and encouraged me to come back. I knew today was a day she should be working so I figured I would let her see the finished product and maybe buy a dress.

I pulled into the parking lot as it was getting dark and I parked in a spot where I could see inside the store. I wanted to wait until the store was empty. Knowing how long it takes to try on clothes I knew this might be awhile. Fortunately it didn't look busy so I sat and waited. As I looked into the store I could see the salesperson was working so my plan seemed to be coming together. I felt my heart start to race as I considered walking away from the safety of my car and into the store. I also noticed there was man who was behind the make up counter of the store. That almost wrecked my plan as I immediately began to be reluctant walking in knowing there was a man there.

Then I figured, "How bad could a make up guy be? He will probably want to touch up my make up for me!"

As I waited for a costumer to leave I noticed the store next to the clothing store sold olive oils and vinegars, etc... It was a relatively new store and there was a blonde woman working there. The store was empty and it didn't look like many other people were going to brave the weather so I told myself I was going for it.

I got out of the car and strolled up to the door, loving the sound of my heels, and right past a bundled up woman who didn't even give me a second look. I walked in the store and was warmly greeted by a very friendly woman. She asked how she could help and I said I was on my way to a party and needed a gift. She helped me pick out a nice flavored oil. I of course had to ask her at what point did she realize I was a guy. I was hoping to see a surprised look but she just smiled and said she could tell and that she had friends who dressed and that she always looked at people closely so she was able to spot me. However, she assured me from a distance no one would would think anything but "female" if they looked at me.

While I was a little sad about being spotted I took it in stride and decided to walk over to the clothing store. I walked in and started looking at some things in the front of the store, purposely turning my back so the saleswoman's first look would not be of my face. I heard a pleasant, "Hello" echo through the store. I turned and politely waved. The woman who had helped me before was standing next to another associate. I turned back to look at the jeans I was standing next to, hoping the woman would walk over. She did and said that I was brave to come out in this cold. I smiled at her and she did not appear to recognize me. I quietly reminded her how she had helped me with dress about a month ago and her eyes lit up.

She said, "Oh my god! You look great!"

She immediately grabbed my hand and insisted that I try on the same dress and a few more! She walked me back to the dresses and past the other associate who simply smiled and said, "Hi". As she was quickly grabbing the dress and a couple others, so quick that I could not say no, the male make up guy walked over to see the commotion. I was introduced to Tom as Portia. Tom was very nice and complimented me on my hair and make up. I politely thanked him and said I did not do it myself. To which he replied he could teach me. I smiled and said, "That would be great."

The saleswoman, Lisa, Walked me back to the dressing room and said she would grab some shoes for me. Truth is I was dying to see how the dress looked on me now that I was in Portia mode. Lisa came in and helped me zip up the dress. She gave me an awesome pair a strappy black heels to try on. Lisa stood behind me and said I looked stunning. She told me to wait a second as she had some great jewelry to go with the dress. She asked me to come out so her associate could she and without thinking I walked out. The associate said the dress looked great on me. I was feeling pretty comfortable at that point so instead of going back to the dressing room I stayed and waited for Lisa to return, hoping that a woman customer would walk in so I could see her reaction. While I was standing there the door to the store opened and in walked a tall thin man! All I could say to myself was, "Shit." Before I knew it Lisa was greeting the man in a way that told me they were friends. The man walked into the store toward Tom's area which was right where I was standing! Lisa quickly grabbed the jewelry and walked over to introduce us! He took my hand the way a man takes a woman's hand and I continued to shake his hand as a woman typically does. The man, James, then walked over and started talking to Tom. Lisa walked me back to the dressing room and placed a beautiful necklace, earrings, and bracelets on me. She sensed my tension and said not to worry as James was a great guy, and she said, It will all work out". Work out? What the hell did that mean?

I stood there a few minutes admiring myself not even noticing that Lisa had left to converse with Tom and James. She then came back and complimented me on the dress again, telling me I had to have the shoes too! I knew as much as I loved this I was not going to be able to afford any of it. It was then I heard Lisa tell James, who had moved closer to the dressing room as they conversed, that she would ask.

She then reiterated, "It can't hurt to ask." Lisa walked over to me and said, Portia, "I know you just met James but he is in a bit of a fix. He is a really great guy that needs some help."

I had no idea what was about to come next but I assumed it had to do with me. Lisa explained that James was supposed to go to a couple's cocktail party at a friend's house but his date had canceled at the last minute. She explained that it was a party where the men would all end up talking in one group and the women in another. His female friend's were expecting him to bring a female so they could sit and chat with her. Lisa paused for a moment and it was then I realized what she was about to ask of me! My brain was screaming, no way! However, the girl in me was thinking it would be fun to relax and hang out with some other women if they were okay with it.

Lisa then came out and asked, "Can you help him out"?

I did not know what to say. Before I could open my mouth she said everyone would be cool with it. Also, that it might get his women friends to stop pestering him. I politely explained that I would like to help but that I was married to a woman and was not gay. She said that was okay and that James just wanted some eye candy. I could not believe I was being called eye candy. Then, without saying a word she handed me a beautiful black shrug and a coat.

She then said, "If you help James out with this you can walk out with all of this, dress, shoes, jewelry for free".

It took me awhile to process all of this. I was loving the dress and feeling quite feminine. I started thinking how it might be nice to infiltrate a woman's world a little more.

James then came forward and said, "Portia, I would love it if you could help me out and I think it would be fun. I wanted to say, "No!" However, "Okay" came out instead.

I think Lisa was more excited than anyone and we were quickly whisked out the door, and we walked to James' car. He opened the door for me and I could not believe what I had just agreed to do! James reassured me and said he knew I must be nervous. He also insisted that everyone would be okay with it and that I would enjoy being involved in bitchy cat talk which made me laugh out loud. So I tried to relax and wondered how I was going to explain this to my wife. In my mind I was thinking this could make for one hot story later.

We entered the house and I was warmly greeted by one of the owners, Amy. She complimented my on my dress and whisked me away to a room of a few other women. I didn't even see any of the other men which was a relief. Amy and the other women accepted me as a fellow female without any question. It became fun talking and drinking vodka flavored women's drinks. In the room of women I subconsciously relaxed and I am sure if there was a video to look back on one would have seen how I gradually settled in and acted just like the other women. I found myself loving this and reveling in being womanly. The softness of my skin and the bra against my beasts that were showing some cleavage was making me quite excited. A woman named Debra who was sitting across the room peeked a glance at my chest. I guess the drinks were getting to her and she walked over and asked to meet me in the kitchen for a drink. I walked with her and noticed my heels were a little higher than hers but she was still a little taller.

She gave me a drink and said I had great legs. I thanked her and then she said, "I would love to play with your girls!" This just about put me over the top.

A second later James entered the room and said we could leave. I got the impression he wanted to go right away so I said goodbye quickly and left. As I hit the night air James grabbed my arm to steady me and I instinctively leaned into him and mumbled something about the heels being slippery.

In the car I was trying to decide how this night was going to end. I knew I had to get a hotel as I was in no condition to drive home. James insisted that I stay at his house. He said he had plenty of room, including a separate bedroom for me. He said it was the least he could do for helping him out. Truthfully I am not sure why he needed me there but it all worked out. I knew James had paid for everything I was wearing, or had some arrangement to pay with Lisa, so he had already done too much. However, I took him up on his offer.

We walked in his house and he showed me around. We sat and talked for a bit. He said he hoped I had enjoyed myself. I told him very much so but that I needed some sleep. He showed me to my room and I walked in alone. As I have said I am not gay but my wife likes to use a double ended dildo on me and I must admit I love to be fucked with it. So for a brief second I thought about what it would be like to have James' dick in me. I quickly put it out of my mind and started to unzip my dress. It was then I realized I was going to need James' help my zipper.

I walked down to his room and knocked on his door. He said, "Come in" and I walked in to find James standing in his underwear.

I couldn't help but look down and notice his growing member. Alarm bells went off in my head. I looked away and asked him if he could unzip me. I walked over and turned my back to him. When I did I saw my reflection in a mirror. He unzipped my dress and I instinctively stepped out of it, or tried to. As I stepped up I lost my balance. Out of the corned of my eye in the mirror I saw James hands wrap around a sexy woman dressed in beautiful lingerie. We fell down together on his bed and without giving me a chance to stand he started feeling my breasts and massaging my nipples. I was immediately under his control and I submitted.

The whole evening of being dressed so femininely had taken over my persona and I knew now I wanted him to fuck me. He laid me back on the bed and I could see he was rock hard. He lubed up his cock and slid down my panties. He entered me slowly and gently and I was in heaven. I leaned back and relaxed and enjoyed him pumping me. I sensed he was getting close but I was not ready for it to end so I flipped over and got on top of him and rode him up and down and fucked him better than any woman. I found myself moaning like my wife. I was having so many mini orgasms I didn't even care if I came. But as he exploded in me I came like I had never come before without even touching my dick! I collapsed on him and we quickly fell asleep. I knew the morning would bring a lot of uneasiness and questions to be answered but right now I didn't care. I was just hoping he would wake me up by climbing on my back and screwing me with some morning wood!