I wish to God I'd never done it. It was a spur of the moment kind of thing and now my life is an absolute mess.
Lily's favorite sexual position is doggie style and her favorite place to do it is right on the edge of our bed so I can stand on the floor and drive into her. We found that if I stand on my toes the angle is such that I touch her someplace inside her that drives her wild; a place I never seemed to touch any other way. I tried a little stool but that apparently put me a little too high. I made a little box about half as high as the stool, but that didn't work either. I tried standing on pillows, on a pile of various sizes of rugs, but the only way I could seem to hit that spot was by standing on my tiptoes. But that was too hard to do, especially for bouts of sex that could sometimes last twenty minutes to half an hour. I was in the mall shopping one day and as I was passing by a shoe store something caught my eye and I stopped to take a look. It was a black high heeled shoe with a very high heel (turned out they were five inch) and what looked like a two or three inch platform sole and it had ankle straps. I wondered if... , nah, no way. What could I have been thinking? But I came back to that store and looked in the window at those shoes three times before I went home. The next day I was standing at the door of the store when it opened for business and I told the lady what I wanted.
"What size sir?"
"I don't know. Do women's sizes correspond to men's?"
"No sir, they don't."
"I guess we will just have to measure my foot then."
She gave me a funny look and said, "There for you? The high heels are for you?" and then gave me a look that said "What kind of pervert are you?" Her look made me feel uncomfortable and so I made up a story, "My wife and I are going to a Halloween party and she wants me to dress up as a woman."
The saleswoman gave me a dubious look and said, "Halloween is five months away."
"I know, but I'm going to need some time to learn to walk in them."
Lily could not stop laughing as I tottered out of the bathroom in my new shoes, at least not until she started moaning and screaming for me to fuck her harder and never stop. The shoes were perfect and I was able to hit Lily's spot with both feet planted on the ground. Oh I wobbled a bit, but I figured that would go away as I got used to wearing the shoes. The shoes became a regular part of our sex life and a couple of months went by and then one night I came into the bedroom and found that Lily had set up the video camera on a tripod and had pointed it straight at the bed. I asked what was going on and she told me that she wanted to see what it looked like when I fucked her wearing my heels. When we played back the tape I could see that it had some effect on her, but I had no idea how strong that effect would become.
I came home two weeks later and found her sitting on the living room couch and masturbating while she watched the tape play on the TV set. As soon as I walked in she pulled down my zipper and pulled me down onto the living room floor. With my cock sticking up out of my zipper she mounted me and fucked me right then and there while watching the tape. Two nights later I came home from work and Lily hollered out, "I'm upstairs in the bedroom." I walked into the bedroom and found her in only thigh high nylons and her Come Fuck Me pumps and she had the camera set up again. There was a package on the bed and Lily pointed at it and told me to open it. I opened it, looked at what was inside and then looked at her like she was nuts.
"Please" she said, "Please do it for me?"
Inside the box were a garter belt and a couple of pair of nylons. I stood there, staring down into the box and she said again, "Please baby, please. Do it for me?"
What the hell I thought, it won't hurt and it isn't as if anybody else will ever see the tape. I could not believe how turned on Lily was that night and on the following nights as she watched that tape and the garter belt and nylons became part of our routine.
Next came the fulfilling of a prophecy that I hadn't realized I'd made.
"Honey, Halloween is coming and I want you to do me a big favor."
Not being a mind-reader I gave my stock answer, "You know I'll do anything for you sweetheart."
She beamed, "Promise?"
"Yes I promise."
"I want you to come to my company's Halloween party as my girl friend from out of town."
I looked at her in absolute horror, "You can't be serious!"
"Honey it will be a kick. No one there has ever met you and we have almost two months to work it out."
"No Lily, absolutely not!"
"But you promised."
I can deny Lily nothing so in the end I caved in and agreed to do it. The coming weeks were spent teaching me how to behave as a woman; how to walk in heels, how to put on makeup and things like that. Every night Lily would come home with something new for me to wear. A pair of classic black CFM's with four-inch heels replaced the platforms and I had to spend a half-hour every night walking around the house in them. Then there were the bra and dresses that I had to get used to wearing. I went whole weekends walking around the house dressed as a woman with Lily constantly giving me pointers. Next came the wigs; Lily bought four different ones before she settled on the one that she thought framed my face the best. It was a soft reddish brown one that was shoulder length and I had to wear it whenever we were home alone so that I could get used to it. The thing I fought Lily the hardest on was shaving my legs, but after a couple of days of watching her pout I gave in on that also. The thing that was the hardest was trying to learn to sit like a woman. It sounds like something simple, but sitting with one leg across the other for an extended period of time is just something very unnatural for a man. I got lessons in putting on makeup. I didn't think I needed them and I told Lily so, "You can put it on me before we leave the house."
"Yes, I could, but you will need to freshen it up every once in a while and you need to be able to do it yourself. What if someone were to walk in on us while I was putting makeup on you?"
That's when it dawned on me that I was going to have to use the ladies room that night and I could just see disaster coming. During this period Lily and I were fucking like two people possessed. The more she dressed me as a woman and taped me, the more she wanted to fuck. I had no idea why, but the more feminine she made me look the more insatiable she became.
The night of the party I was a nervous wreck. I didn't want to do it - I really, really did not want go, but if I didn't go Lily would never forgive me. I needn't have worried as the party went off without a hitch. Lily went as Cat Woman and told everyone that I had just flown into town and hadn't had time to get a costume. I was introduced as Roberta (every one called me Bobbie) and Lily told everyone that I was going through a rather difficult trial separation from my husband and that she hoped everyone could help cheer me up. I walked around with a drink in my hand and astoundingly got hit on by several guys. Even more astoundingly to me was the fact that Lily was pissed at me all the way home from the party. I had to badger her into telling me why and she finally got a sheepish look on her face and confessed that she was jealous of the attention I got.
"I work with those guys every day and they have never sniffed after me the way they went after you."
I was flattered - I think.
Halloween was over and I thought that the cross-dressing was a thing of the past. I was wrong. Lily kept buying bras, panties, bustiers and other feminine things for me to wear and asked me to wear them when we made love. She videotaped all of our love making sessions and when I wasn't around she maturbated to them. We started getting phone calls for Bobbie and Lily giggled and told me that some of the guys she worked with had asked her for my number. If I answered I just said that Bobbie wasn't there, but if Lily answered the phone she would say, "Just a minute, I'll get her." Then she would say, "Take the call baby, I want to suck your cock while he's trying to make a date to fuck you." I went along with the gag and a couple of weeks went by while I fended off the guys she had given my number to. The next thing she hit me with was meeting her after work some night when she was going to stop for a drink with the girls she worked with. I let her talk me into it and I do have to admit that it was a kick.
I never knew a group of women could be so potty mouthed. They talked about their husbands, boyfriends and lovers and compared cock sizes, got into arguments over whether or not size mattered and discussed who was good at eating pussy. I got a little pissed when in answer to a question on cock size Lily said that her husband was kind of small (I know that seven inches isn't huge, but it isn't small either) and that someday she might cheat on him just to see what a big cock would be like. That brought a chorus of "Oh you should try..." and the girls named off guys that Lily worked with. The Lily turned to me, "What's your opinion Bobbie? What's your husband like?" I gave her an evil grin and then held my hands apart to indicate a cock of about twelve inches. That got me, "You silly girl, why are you letting him get away?" Lily said, "The problem is that he's not using it on her, he's giving it away to other women" and that got me a bunch of "Oh you poor baby"s.
While we sat at the table a couple of guys came over and asked some of us to dance. I politely declined, but Lily danced with three guys and once came back to the table giggling, "I think I found my huge cock. At least it felt huge when he poked it into my leg."
That set the girls off, "You going to give him your phone number?" and "Are you going to see him again?" One whiskey voice slut said, "Don't let him get away honey. Go out into the parking lot and fuck him now. You never know when you might find a big one again." Lily turned to me, "What do you think Bobbie, should I go for it? Think David would know if I was freshly fucked when I get home tonight?" Talk about opening a door! About five years previous I told Lily that my most persistent fantasy was to watch her fuck another man. Lily had let me know, in no uncertain terms, that I was out of my fucking mind and as a result it had never been mentioned again.
"I think you should go for it Lil. I mean if David is as lacking as you say you owe it to yourself to see what a real man is like."
That wasn't the answer she had expected, but before she could give me a nasty look the girls jumped in, "Go for it Lily" and "You go girl." A couple of them began to chant "Show us the beef, show us the beef" and almost as if on cue the man in question showed up and asked Lily to dance. She looked around the table at everyone, her glance lingering on me for a second or two, and then she got up and went out on the dance floor with the guy.
We all watched Lily and the man dance and about halfway into the dance we all saw the man's hand slide down and cup Lily's ass and Lily laid her head on his shoulder. The girls at the table were all babbling away, "Will she do it?" "I hope she does it." "Maybe I should have said yes when he asked me to dance. I'd like to see a big cock once" and whiskey voice said, "She won't do it. She isn't slut enough." The music ended, but the two of them stayed on the floor and waited for the next song. One of the girls asked, "What do you think Bobbie? You know her better than the rest of us."
"Well, we've been close since the third grade and she has always told me her deepest, darkest secrets, but she has never mentioned cheating on David. But she is headstrong and if she took what was said at this table as a dare, who knows?"