Hypnotized

She then had me follow her to their kitchen. They had an island with tall chairs. Sara pulled out one of the chairs, turned it around so the back of the chair was facing the island, and she told me, "Sit. It will be easier for me to do your makeup this way." She returned to their bedroom for a minute and then returned holding two handfuls of makeup items and brushes. "I'll do simple for now and more elaborate for later."

Sara went to work. First, foundation and powder, then she had me close my eyes for some eye powder. "Look up," she requested and lined my lashes with mascara. She explained each step as she went along, telling me she had worked at Sephora when she was going to college, so she had done a fair number of makeovers, including a few guys. Some rouge on my cheek, pencil for my brows, and then lipstick, and in about fifteen minutes it was all done. She fluffed up the wig and placed it on my head, rearranging it with several tugs until she was satisfied.

"Cute," Sara said with a smile and then added, "want to have a look at yourself?" "Yes," I answered (trying--unsuccessfully--to keep the eagerness out of my voice) and Sara then led me to the full-length mirror in their bedroom. I had to agree; I did look cute.

"Like it?" Sara asked. I nodded and said what I was thinking, "You're right, I do look cute. You're a magician with makeup. And you're also right, it will be easier shopping looking like this."

"Ready to go?" Sara asked. I nodded yes, and then she snapped her fingers and said, "You need a purse!" and walked into their walk-in closet, and then a few seconds later walked out carrying a basic black purse and she handed it to me. "You can use this tonight and return it to me tomorrow."

"Thanks," I said, "getting a purse never crossed my mind."

Sara yelled to Eric, "Dave and I are going. Back later," and we walked out the front door.

When we were outside--and I noticed none of the other neighbors in our cul-de-sac were out--I told Sara, "Is this the part of the story where I tell you I have a pair of heels that I can wear?" Sara just told me to go to my house to get them and put them on, and she'd pick me up outside my front door--and then I would tell her why I had a pair of heels.

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Sara watched me walk out of my front door and to her car in my black two-inch pumps. I climbed in the passenger side of her van--the mom car, of course--and with a slight grin said, "You seem to walk pretty well in heels. I think you need to spill."

While driving to our first stop, Goodwill, I gave her the basics. I had made a dare with a former girlfriend Renee that she couldn't find heels in my size, and when she did, one night she dressed me up in her clothes. It was a fun night, and when we split (she started dating her eventual husband and we parted as friends) she gave me the heels.

Sara glanced at me and asked, "Are you doing this for your girlfriend or are you doing it for you?"

"Well," pausing long enough to think what I wanted to reveal "a little of both. I think she needs a bit of a laugh to reduce her stress level, but it's Halloween time and I'm curious about how I look dressed again."

"How did your prior girlfriend react to your being dressed?" Sara asked.

"Renee said I looked better in her clothes than she did," I answered.

Sara laughed. "You make a pretty decent looking woman. So did Eric. I'll have to show you the pictures."

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We made it to Goodwill and I realized I was about to walk into a store full of people dressed like a woman. I suddenly became nervous. Sara noticed and said, "C'mon, you can do this. Nobody will care. You'll be fine, and I'll be with you." With that reassurance, I managed to get out of the car and started walking to the entrance with Sara.

I went to hold the door for her--like any gentleman would--when I realized I wasn't dressed like a gentleman. Regardless, old habits die hard, and I held the door, took a deep (deep) breath and followed Sara inside.

Fortunately, nobody seemed to notice anything unusual about the two "women" who had just walked in, save a clerk who said in an uplifting tone, "Welcome to Goodwill!"

Sara led the way to an aisle of tops and blouses. I was happy to let her lead because I had little idea of what would work best. Sara looked at me and said, "I think you'll be a large or extra-large," and I just nodded, because I was pretty sure my voice didn't match my appearance. The items were arranged by size and within sizes by color, starting with white at one end and black at the other.

Sara started with the large sizes at the white end. She pushed the hangers to the right, then started looking at the tops one by one, quickly flicking through them. About every fourth or fifth she'd look at the label, take it off the rack for a closer look, and then put it back on the rack.

I commented softly, so others couldn't hear my voice, "It looks like you've done this before." Sara laughed and said in a joking manner, "Just a few times. I enjoy going thrifting and seeing if I can find any treasures."

After about fifteen tops, after looking at the label and inspecting it closer, she held it to my chest to size it up as to whether it would fit or not, then handed it to me and said, "Hold this. We'll pull a few for you to try on. We should have brought the skirt to see how they go together."

I'm not sure I heard anything after the words, "try on." I guess that was the smart thing to do, but I hadn't thought the process through. At that point, I also realized that between Sara holding blouses to my chest, and trying on clothes, perhaps shopping dressed as a woman was less embarrassing than the alternative.

And more fun.

Sara found three large blouses, two white and one light pink, and two extra-large white blouses for me to hold. Then she said, "Let me try to find you a skirt similar to the suit skirt to better judge how the two look together." She walked to a row of skirts, with me in tow, then turned to look at me, and said, "I think you might be a twelve."

"Does that mean I'm better looking than a ten?" I joked, and Sara merely snarked, "Ha ha." There were lots of black skirts, so to be safe, she pulled one in a size ten, a size twelve, and a size fourteen, and handed all three to me. "Go find a dressing room and try the skirts on first, so I know which size you are," Sara said, then added, "once you know which size skirt, try the blouses. In the meantime, I'll keep looking for suitable items."

I walked over to an open dressing room, the first one on the left, and turned and made eye contact with Sara so she knew which one I was in. I entered, closed and locked the door, and hung the skirts and blouses on the hooks provided.

As a guy, I always hated changing rooms. I didn't like to shop, hated getting fitted for business suits, relied on ties that people gave me as gifts so I didn't have to buy them, etc. I had been a chunky kid when I was young, the sizes didn't suit me, and even though I lost some of the chunks as an adult (traveling for eighteen months helped fitten me up), I still disliked buying clothes.

This was COMPLETELY different. Now, the mirror was my friend. For the longest time, I had wanted to see how I looked in woman's clothes. Because of Geri's crazed comment, and my active imagination--and a willing partner in Sara--it was all happening.

I was the kid on Christmas morning not knowing which package to open first, but I knew for sure it wasn't going to be socks, underwear, or a tie. I took off the slacks and hung them on a separate hook from the blouses and skirts.

My vanity kicked in. I tried the size ten skirt first. Nope, it wasn't gonna zip. Back on the hangar, pull the size twelve, unzip, step into, zip, fasten button, rearrange to have the front in front. So far, so good. I checked the mirror; the length was the top of my knees. My shaved legs in the black heels looked pretty good. Even the light blue top Sara had lent me looked good with the skirt.

Now time to try the blouses. Off with the top, try the first large. I put my arms in the sleeves but quickly realized it is too small to button across the front. I remove it, put it back on the hangar, and figuring the other two larges won't fit either, I skip to the extra larges.

I tried on the first of the XL white blouses and after putting my arms through the long sleeves I decided it was likely big enough so I could button it. I first buttoned the cuffs at the end of the sleeves and began working on the buttons across the chest. I immediately realized the buttons were on the wrong side, reversed from what I was used to. It was a lot harder to use my non-dominant left hand to fasten the buttons, and progress was slow. I finally had all buttons fastened from top to bottom and turned to face the mirror.

One glance and I knew the better look was to tuck the blouse into the skirt, so I unzipped the skirt, wrapped it around and over the bottom end of the blouse, and zipped up the skirt again. Another look in the mirror. Better. Also, a look at my face: I was smiling.

I was snapped out of my reverie by two knocks on the door and Sara asking, "You decent?" I answered yes and then she said, "Let me have a look," so I cracked the door half open so Sara could judge for herself. She eyed me up and down and her face seemed to send the message that she approved, then she merely nodded and said "Nice." I then noticed she was holding two items on hangers, one appearing to be a business suit and the other a black dress.

"I found these two and thought they might fit you," Sara said. "The suit is a larger size so might fit you a bit better. It looks like the suit should go with the blouse you have on. Plus," Sara added with a pause "if your girlfriend has a problem with you wearing her clothes, then you're in the clear because you didn't."

I nodded in agreement but then added, "She may have a problem regardless, but I guess there's only one way I'm going to find that out. But what about the dress?"

"If the suit doesn't work, you can try the dress, because it's business appropriate," Sara answered. "Besides," she added with a smile, "every girl needs an LBD, and it goes with your heels."

As I couldn't argue with either of those, I took both from her, closed the door, and said I would try on the suit first, while Sara browsed a bit more. Off with the skirt, on with the suit skirt, and on with the jacket. The jacket fit, the skirt fit, and at a $12 price tag it was a no brainer. I opened the door and walked out of the room to get Sara's opinion (and approval, I hoped). Given my voice, I didn't really want to call Sara, but I caught her eye and she began to walk over.

"I like," she said, and I answered, "so do I." With that decided I retreated to the dressing room to try on the dress.

After spending much of my life dreaming about trying on a dress, and doing it far too rarely, I was eager, "to give it a go." The buttons on the blouse were stubborn and refused to yield easily but I finally managed to take it off. I unzipped the dress and stepped into it, pulling it over my hips. I threaded my arms through the arm holes and reached behind my back to zip it up. I zipped it up as far as I could reach, but despite my best efforts, I couldn't zip it up all the way. Once again, I stepped out of the dressing room, saw Sara, and motioned to her with a "come hither" gesture with my index finger.

Sara approached, and when she came close enough, I said softly, "Can you see if you can zip me up?" and I turned my back. I felt her straighten both sides of the dress, then grasp the zipper and pull upward. It felt tight for a second, but then I felt it moving up my back until it reached the top.

"Turn around," Sara commanded, and I did.

"I'm not sure," remarked Sara.

"You don't like it?" I asked.

"No, I'm not sure if I like you in the suit or the dress better," she said with a laugh. "Have a look," and she pointed me to the mirror in the changing room.

I looked and looked and looked and stared at my image in disbelief. It was really me in a black dress that gave me curves and showed my legs and made me look girly.

Sara was right. I didn't know which one I liked better. One was more professional, the other was sexier. Should I buy the suit and blouse or the dress?

I asked Sara, "Which should I buy? I like them both."

Sara just smiled and said, "Both. It doesn't have to be either/or. You can wear the suit tonight to imitate your girlfriend. Then"--once again a long pause--"you can borrow my witch's hat on Monday night and hand out candy in your new black dress. I'll do your makeup again. I think you'll make a cute witch. Or"--another pause--"you can leave your candy at the door and walk around the neighborhood with Nick and me. Your choice."

Then she added, "Even if you don't want to dress up on Halloween, I still think you should get both. Both look really good on you."

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Sara found a few things she wanted to try on and I got to play the girlfriend role and offer comments on what she tried on. I browsed the racks myself, getting more comfortable being out dressed, and not seeing any strange looks from the other customers. Sara didn't buy anything. I nervously managed to go to the counter with my new suit, blouse, LBD, and a pair of cute black panties, and the clerk just said, "$29," and then, "Happy Halloween. Have a nice day'".

We made one more stop at a drugstore. Sara picked a pair of "nude" pantyhose for me (explaining the sizes to me), and then a bottle of quick drying red nail polish (and a bottle of polish remover), a lipstick to match the color of the nail polish, and some makeup remover. Once again, some nerves about buying them at the counter, but having Sara there helped and we were out the door.

Sara dropped me off at my house. She kept the suit, blouse, lipstick, and nail polish, promising to iron the blouse for me. I took the dress, pantyhose, nail polish remover, makeup remover, and panties. We agreed I would come over at 6:45 with the pantyhose and undergarments on, and I would get dressed after Sara did my makeup at their place.

I had about three hours to kill, alternately being amazed at just what had happened, and worried about how badly this could all backfire.

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I tried to distract myself by watching some college football, ate some leftovers for dinner (funny, I didn't have much of an appetite), then another close shave and a shower, where I cleaned up some stray hairs. Finally it was time to dress. I carefully pulled on the pantyhose, enjoying the feel on my shaved legs, then the panties and bra. I put on a polo shirt, a pair of jeans, socks and a hoodie over the girl stuff.

I stuffed my heels, the wig, and Sara's top and slacks, the makeup remover, and my toothbrush (realizing whether I was spending the night or not at Geri's was still going to depend on her reaction to my attire) and put my camera into my gym bag. After putting on my sneakers, I made the short walk down the cul-de-sac to Eric and Sara's house, knowing the return walk to get my car would be in heels and a woman's business suit. I was somewhat comforted that it was dark out and the neighbors likely wouldn't notice me.

Eric answered the door and said, "Hi Dave. Sara is expecting you. She's doing something with Nick right now, but she'll be with you shortly. Come on in. Sounds like you had fun shopping."

"It was definitely different. Sara made it a lot easier for me. I think she enjoyed it more than I did," I answered.

Eric walked me into the kitchen as before and told me to sit on the tall chairs again. About a minute later, Sara walked in, smiling, carrying a lot of makeup and a towel.

"Take off your hoodie and shirt and wrap this towel around you," Sara instructed. "That way you won't get makeup on them." I did as requested. "Let me do your nails first," Sara said. "They can dry while I do your makeup." I held my hands out and she did them quickly and I loved the look when she was finished.

Sara then went to work on my face, telling me what she was doing, not that I understood. "I'm going to do more of a nighttime look than professional, but I figure either way you wouldn't mind."

Nick walked in and said, "Hi Dave. Going to a Halloween party?"

"Hi Nick. Sort of. Meeting a friend and trying to make her a bit happier. But no trick-or-treating for me. What are you going to be for Halloween?" I asked.

Nick smiled and said, "A Ninja turtle. My mom made the outfit."

"Well I can't wait to see you Monday night," I added. "Are you going to get a lot of candy?"

"I hope so," Nick responded and left the room.

"I know I'm biased but he's a great kid," I told Sara. "Thanks, that's sweet," Sara answered.

Sara did my eyes, "look up, look down, close." More brushes, more makeup, finally, "pucker," while she used the lipstick we bought earlier to paint my lips. She said, "OK, done, you can go into the bedroom and change. Your blouse and suit are hanging in there, and the socks are on the dresser drawer. You can stuff your bra with them," she added with a big smile.

I changed, taking forever to button the blouse, then on with the skirt, jacket and heels. I avoided glancing at the mirror, because I didn't want to see myself without the wig. I pulled out the wig, fluffed it up with my fingers, as I saw Sara do earlier, and placed it on my head.

Finally, a look in the mirror. I saw a cute face smiling back at me. Still a male face but with a feminine twist. The suit looked good. My shaved legs in the hose and heels looked great. I turned side to side and then stuck my head out the door and called to Sara, "You can have a look now."

I went back to look in the mirror and heard Sara approaching, with Nick in tow.

Sara asked, "Do you like it?"

"Absolutely, I love it," I said. "What do you think?"

"I think you look great," Sara answered. "The wig needs a bit of combing but everything else works. What do you think Nick?"

"It looks like you're ready to go trick-or-treating!" Nick answered to the combined laughter of Sara and me.

Sara found a brush suitable for a wig and did the honors to brush it out. She also tugged on it a bit until it sat more where she wanted it. I had another look in the mirror and tried to take a mental picture to replicate the wig placement for the future. Sara handed me the brush and said, "Put it in the purse--I mean YOUR purse," and then handed me the lipstick with instructions to put it also in the purse. I did as ordered.

It was nearing 7:30 and I needed to get going. But first I gave Sara my camera and asked her to take a few pictures, and after showing her how it worked, she obliged and took a handful of pictures. If nothing else, I would have something physical to remember this night. I put my camera and my boy clothes into the gym bag and took it and the purse--my purse--and headed for the door, thanking Sara and promising her a full report when I saw her next.

Sara then said, "I know you can walk in heels but can you drive in heels?"

"I guess I'm going to find out shortly! It will take some adjusting, but women have been driving in heels for a time, so I should be able to," I answered.

"Have fun and drive safely. I hope your girlfriend is OK with this--or from what you say, she might be your ex-girlfriend. Good night," Sara said as I walked towards my house. I just waved and laughed, enjoying the sensation of walking in a skirt and heels down the street to my house and car.