Hypnotized

Again, thanks to those who read, voted, and commented on my first two stories.

Like the first two, this one has kernels of real life. Geri, a/k/a Mary Geraldine, was my girlfriend back in the day. Unfortunately, I have lost track of her and haven't heard from her in thirty years, although I would like to know what she is doing these days.

Some of this was real, most of it not. You decide, and hopefully enjoy.

I met Geri, short for Mary Geraldine (she had a twin, Mary Katherine, who went by Kathy) at a slow pitch softball game. She was watching either someone on our team or one of our opponents, I can't remember which. We talked after the game, went out for drinks, and started dating.

Our dating history was pretty checkered. She married young and divorced a few years later. I never knew her ex's name; she just referred to him as "The Asshole." We dated a bit the first summer, nothing serious. I was in the middle of an eighteen month "sabbatical" (as my mom called it) between jobs, traveling throughout the US in a Volkswagen Campervan, and also flying overseas to New Zealand and Australia. Sometime during the eighteen months of my travels we had a fight and stopped dating and lost contact.

Three years later, back working again, I'm doing a Christmas run with some co-workers in downtown St. Louis. Stopped cars allowed us to pass at an intersection. Lo and behold, the first car that stopped was Geri's car. I recognized it, stopped to briefly talk to her (told my co-workers to go ahead) and we agreed to meet after the race. I finished the race, we met at the designated spot, let bygones be bygones, and began dating again.

It was a few months later and April Fool's. Geri's at my house and she tells me she loves me. I was honest and told her I didn't love her. She's not too happy so I start driving her home. After about ten minutes she blurts out what she meant is that she wanted to sleep with me (up until then, we hadn't had sex). I said the equivalent of "I'm down with that," turned the car around, and we proceeded to figure out we should have decided to have sex a lot sooner.

Over time I discovered the Asshole had done a number on Geri's self-esteem. She had some body issues and didn't enjoy being naked. One time I suggested we have sex "doggy style" and she told me the Asshole had said to her that he only wanted to have sex with her doggy style so he didn't have to look at her face. Needless to say, we didn't do "it" that way and I never asked again. I may be a lot of things, but asshole isn't one of them.

We also did some traveling together. I still had my VW Campervan, and we were somewhere in Southwest Colorado in the midst of a three week trip to the Southwest United States. We were at some historic hotel in a former mining town and Geri starts looking around and she says she's been here before. I asked when and the surprising answer was on her honeymoon. I had no idea. She then added the Asshole had brought drugs on the honeymoon and that was her first sign of the trouble ahead. We changed the subject and that was probably the last time we ever talked about her marriage.

Body issues aside, she did enjoy sex and especially enjoyed going down on me. She was enthusiastic and creative when giving blow jobs and I certainly enjoyed my end of the bargain. I tried to reciprocate orally but she was generally uncomfortable with me going down on her; I was never sure whether the cause was the ex or maybe her Catholic upbringing. A couple of times I did convince her to 69, and we both managed to get off, but never did it very often.

Geri once told me I was a patient and considerate lover. I didn't have a lot of ways to measure either, but we did have fun in bed, or in my campervan, and even once in the front yard of my house (it was dark, and there were trees to hide us from the neighbors, and I can't remember whose idea it was). It was mostly fairly vanilla sex which is ok with me too.

She lived with her parents for a while, then moved to a couple of different apartments in St. Louis. She was taking classes to pass the CPA exam while also working full-time at a company doing bookkeeping work. She was stressed with both, being relatively poor, living on her own, and trying to rebuild her life post-divorce. The combination of all these stresses lead to the events described below.

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It was the last Saturday in October, which meant it was a few days before Halloween, but more importantly from Geri's perspective, the last few days before the CPA exam began on Wednesday. The test had four sections over three days, Wednesday to Friday. As I had taken (and fortunately passed) the exam ten years before I knew what a PITA (pain in the ass) the exam was, so I was sympathetic to her, because I had been there, done that.

It was Saturday morning. I had spent the night, and Geri was up early to hit the library and study. We had agreed I would come back that evening and we would have something like a quick dinner, if nothing else to help her decompress after a day of studying.

Before she left, somewhat bowing to the stress, and almost being serious, she picked up a small silver colored ceremonial coin and waved it in front of my eyes, saying "You are getting sleepy" and then pretending to hypnotize me. Geri then said "You will take the CPA exam for me." I laughed and said I didn't think I could convince the proctors that I was actually her. I knew from experience they did have procedures in place to prevent cheating like this.

I also knew that trying anything like this, and getting caught (likely), would significantly screw up my career. Geri knew it too, but she was pretty desperate. I told her she just better go study, and I would see her later that night. She headed out and left me her second key to let myself out, and to let myself back in that night if I got to her apartment before she did (this was back in the prehistoric days before cell phones).

I was getting ready to leave when I had a crazy thought. What if I pretended to be hypnotized so I could dress like her?

Geri knew I was interested in cross dressing, but she made it clear she wasn't interested in helping me dress, so I didn't. I also didn't have any women's clothes, except for a pair of black heels a previous girlfriend Renee had given me on a dare. If I did it, would she be royally pissed off that I got dressed up, or would it be possible that it would allow her a laugh and blow off some of the pressure that had been building?

Plus, it was almost Halloween, so I could use that as an excuse, both to explain to Geri and to buy some things I would need. At least that was my rationalization.

I was mentally flipping a coin. This could be fun, or could be a relationship ending move; dressing up, wearing her clothes, etc., etc. Mushroom clouds on the horizon.

The coin landed and the answer--this was too good of an opportunity to pass up.

The first hurdle. If Geri wanted me to dress up like her, would I fit into her clothes? Only one way to find out. I walked to her closet and looked through her work business suits (again, the days before casual dress). She had four or five choices and I tried to figure out which was the largest and most likely to fit me. I picked the one that seemed to have the largest size, took it off the clothes rack and laid it on the bed. It seemed to be a basic black suit, a jacket and a skirt.

I took off my jeans and tried on the skirt first. I tried to figure out if it zipped in the back or on the side, but eventually just stepped into it, pulled it up, and managed to button it and zip up the zipper. It was a bit of a tight fit, but I pulled and tugged and got it in the right place where I could still breathe. I walked to the full-length mirror, and although it didn't go with the black socks I was wearing, it fit me decently. A small victory.

Next was the jacket. It was tight in the arms, and I couldn't button it, but a look in the mirror told me it fit ok.

Back to the closet to find a blouse to wear with the suit. Again, I checked the tags for sizes and pulled what seemed to be the largest. I tried it on--and several of the others--but they were all too small. That meant if I was doing this, I would have at least one item on my list, and a general idea of what size I needed.

Next, I started looking through her dresser drawers for her bras. I decided pretty quickly that borrowing one of hers was NOT a good idea but trying one on to figure out what size I needed was ok. I found the right drawer, put it on in reverse and tried fastening it, but like the blouse it was too small. As Geri's was a 36, I decided I needed at least a 38. Second item on my (mental) list. And as long as I was wearing a bra, panties would be in order too. Plus pantyhose, because I loved the look and feel (plus pantyhose was standard professional attire for women at that time).

With Halloween around the corner, I figured I could find a wig at one of the pop-up Halloween stores littered around town. Brunette of course, as Geri was a brunette.

All these were doable. It was Halloween, and I was willing to screw up my courage and buy girl stuff as part of my Halloween "costume." The big challenge was makeup, because I didn't have any, and I had no clue how to apply it. I wasn't ready to look like a clown, and if I was dressing, I was wearing makeup.

The thought of being a clown gave me an idea. I lived on a cul-de-sac and one of my neighbors was a husband and wife, Eric and Sara, who had a seven-year-old son Nick. Nick would often come wandering over to my house and we would throw a ball or kick a soccer ball, or just talk, and he was a fun kid.

The prior year for Halloween Nick had gone trick-or-treating as a clown, and I had complimented Sara on her makeup job on Nick. She said she enjoyed doing the makeup--and then added that one time when they were dating she had made up Eric and he had gone to a Halloween party dressed as Snow White. I decided that before I did any shopping, I would approach Sara and see if, given the situation, she would do my makeup.

Now that I had a plan, I gathered Geri's suit, my overnight bag, and headed to my car. I mentally composed what I was going to say to Sara during my half hour drive home. In the end, I just decided on (mostly) the truth; Geri had asked me to imitate her, and I thought doing this would help her cope with the pressure of the CPA exam by getting her to laugh and blow off steam. I would just omit the bits about me being a crossdresser.

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With every minute I got closer to my house my resolve to ask Sara for the makeover dropped and dropped. I could feel myself chickening out; until I parked my garage in the car, got out, and started walking towards Eric and Sara's house.

I knocked on their front door. Eric answered, "Hi Dave. What's up?"

"Is Sara available?" I asked. "I need to ask her a favor."

"Sure. Let me go get her," Eric said while turning his back and walking towards the rear of their house. I heard an exchange of voices and then a few seconds later Sara came to the door and came outside.

"Hi Dave. Eric said you wanted to ask me something," Sara said.

I hesitated for a second, and then began. "I have a bit of a strange request. My girlfriend Geri is studying for the CPA exam and in professional terms it's driving her effing crazy."

Sara laughed and I interpreted that as a good sign and continued on.

"This morning I think the stress got to her," I added. "She pretended to hypnotize me and then commanded me to take the exam for her."

Sara laughed again.

"I tried to explain to her that I didn't think I could convince anyone that I was actually her"--while talking I used my hands in an up and down motion--"and from experience I know they have procedures to prevent imposters from taking the exam. I know she wasn't being serious, but right now she's pretty desperate for any light at the end of the tunnel."

"When's the exam?" Sara asked.

"It starts Wednesday and lasts until Friday," I answered. "Including today she has four more days to study, although she has to work Monday and Tuesday, so it's max stress time right now. Thus, she might be grasping at straws, including asking me to be her."

Sara smiled and asked "What can I do to help?"

"Well......well," I was stalling while I figured out what exactly to ask and then went on "I thought she might find it amusing--or she might go ballistic, not sure which--if I showed up and her place tonight dressed up like her, as IF she had hypnotized me. I've borrowed one of her business suits, I can go shopping today for a blouse and other items like a wig, but I know zip about makeup and I'd look like a clown. Then I remembered Nick last year dressed as a clown for Halloween and thought to myself, maybe Sara would be willing to do my makeup. So, if I get everything I need to pull this off, would you be willing to do the makeup?"

Sara was laughing and nodding and said, "Sure, that would be fun, and we're not doing anything tonight, so I'm available. What time were you thinking?"

"Geri is planning to study all day and we agreed we would meet about eight to get something to eat," I answered. "She lives about a half-hour away so I would need to leave around 7:30. I have no idea of how long it would take to get made up and dressed; that's probably your area of expertise rather than mine," I said while finishing with a smile.

"If we start at 6:45 you should have plenty of time to be ready to leave by 7:30," Sara replied. "Do you have a wig? We have one from several Halloween's ago when Eric went as Snow White a couple of years ago. It might work perfectly well for you."

"No, I don't have a wig. I was going to go to one of the Halloween stores to try to buy one," I answered. "But if you have one I can use that would be one less thing to worry about."

Sara said, "Let me see if I can find it" and disappeared into her house for a few minutes, during which I realized I might actually be doing this. Sara came back out holding a brunette pageboy wig saying "found it" and handed it to me. She said "Try it on," and somewhat sheepishly, standing in view of our cul-de-sac, pulled it on my head. Sara looked and nodded and said, "That will work." I removed the wig and handed it back to her.

Sara then asked, "Can I see the suit you were planning to wear?" and I answered, "It's in my car. Let me go get it" and I walked back to my car, retrieved the jacket and skirt, and walked back to Sara's. I handed her both items, and she held them up against me.

"Does it fit?" she asked. I nodded and said, "It's a bit tight, but I can get into the skirt. I can't button the jacket, but I figured I wouldn't need to anyway."

"What else were you planning to get?" Sara asked.

"A white blouse, a bra, maybe a pair of panties, some pantyhose, and some heels," I answered, (not mentioning I already had heels, to avoid any embarrassing questions).

"Where were you planning to go shopping?" Sara continued.

"I figured I would just go to the mall," I answered.

"You could go to Goodwill or the Salvation Army," Sara suggested. "Between one or the other, they would likely have what you need, except maybe pantyhose. Goodwill always advertises as the original Halloween store, so you would fit in."

Then she threw me a curve.

"Want help shopping? I can go with you and help you find what you need," Sara volunteered.

"Um, you don't need to, but I guess I wouldn't mind the help," I stuttered. "You have slightly more experience than me when it comes to shopping for this stuff."

"I don't have anything planned this afternoon. Eric and Nick will be watching a college football game on TV," Sara added. "Plus, it's more fun to shop with someone else and get their opinion. You might even have fun!" she said with a teasing smile.

I said OK, we agreed to go at 1:00 after we'd both had lunch, and I walked to my house, wondering what I had just agreed to.

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Besides lunch, I did as Sara suggested and climbed into my bathtub with some bubble bath and a razor and shaved my legs--and then on my own shaved my arms and upper chest. I would be showering at home instead of the Y the next couple of weeks.

I walked over to Sara and Eric's house just before one, carrying Geri's suit. Sara had offered to drive, and I figured she knew better where to go than me. I knocked on the door, expecting to climb into her car, but she had me come inside and asked me to follow her.

"Ok, you don't have to do this, but I thought you might be more comfortable shopping for clothes dressed more appropriately," Sara said, as we walked into their bedroom. I wasn't sure what she meant, and then I saw a pair of slacks and a top--and the wig--laid out on their bed.

"Oh," I said, followed by "I'm not sure I can do that. I can't go out in public dressed like that. What if I see somebody I know?"

Sara just smiled and said, "We'll just have to make sure people don't know it's you. Plus, you WERE planning to go out in public tonight, weren't you? You have to drive to your girlfriend's place dressed, or at least wearing makeup. Why tonight and not now? At least try these on and see how they look; they weren't exactly maternity clothes, but they were what I wore before Nick got too big when I was pregnant, so I think they'll fit you," as Sara picked the top and slacks up and handed them to me. "Unless you want to wear my maternity dresses instead?" she said with a smirk.

"Not until next Halloween," I answered back with a smirk of my own, taking the clothes from her. She left the room, telling me to let her know when I had changed.

Fear aside, I was excited about trying on her clothes and seeing how they looked on me. Sara and I were about the same height, and while she was thinner than me post-pregnancy, they might fit. They appeared to be suitable for business wear--Sara worked for a mortgage company. Ironically, they had moved into our neighborhood a couple of years after me, and it took me a while to realize she had done the closing when I bought my house.

Off with my jeans, on with the slacks. Tight, but they fit. Same with the top. The top was light blue, the slacks navy blue. I was surprised, but they actually looked decent on me, as I walked over and looked in the full-length mirror on the wall. I said aloud, "I've changed; you can come in."

Sara walked in and looked me up and down and said, "Those will work". Then she snapped her fingers and said, "Of course" and went digging in a drawer in her dresser drawers. Sara pulled out a bra and said, "I figured one of my regular bras wouldn't fit you but I forgot about my maternity bras. They might. Take off the top."

I did. Sara giggled a bit and said, "Did you shave your chest?" and after turning seventeen shades of red I just nodded. "Hold out your arms in front of you," said Sara and while I did she put the arm holes of the bra around my arms then went behind me and fastened the bra. "Bingo," she said and although it was a bit tight I could still breathe; and I loved the sensation. Sara repositioned the bra on my chest, then dug into another drawer, pulling out a pair of socks. Separating the two, she said "Put one in each cup," and I did as told.

Sara rearranged how the socks fit in the bra and laughed after I said, "Hey now, I'm not the kind of girl who goes to third base on the first date!"

Sara just told me to put the top back on, so I did. She took a step back and a smile told me she liked the look. "If we can't find a blouse for the suit you can wear this tonight; it's businessy enough," she added.