Well

Chapter 2

By now I was rocking along through the cornfields of Iowa with my cock in full hardness from my day dreaming. What the hell, I thought, as I steered with one hand and opened my fly with the other. My cock sprang out and stood there with its cut head resting against the steering wheel. The only people who might see it would be a freight truck driver and hell, he may be as horny as I am. Checking my watch I knew I was making good time and figured in about another hour I would stop for lunch. -------------------------------------------------------------------- I was very disappointed when, a few days later I got an email from Sammy and he was leaving town. We wouldn't even get a chance to see each other again.

Back to the internet and scanning the lists and descriptions of men wanting company. Some wanted to get together but only with the possibility of a long term relationship. Not for me. Some wanted not only one on one sex but also were or wanted to meet with a guy who was a crossdresser. This thought intrigued me and I started up some correspondence with a couple of them. One guy was about 6'2 and 245#. He said he loved to wear silky things and share it with another guy. This I couldn't quite imagine.

Another guy and I traded emails for several weeks and he described in great detail how he dressed - stockings and garter belt, bra, panties and sometimes a maids uniform. It took me a while to discover just what a 'maids uniform' was but once again the internet came through for me. Had to admit it did make me kind of shiver all over.

During this time I finally got the courage up to try on a bra and panties. One day when I was alone I went to the laundry hamper and was fortunate to find one of each. Then in my locked bedroom and naked, my shaking hands drew the panties up my legs and over my ass. They seemed like a kind of a thong type as the rear just fit into the crack of my ass and the front barely covered my cock and balls. I pirouetted in front of the mirror and was actually quite pleased with what I saw. My buns protruded nicely out back but I only wished I had bigger hips. The front was just an extension of my flat belly and covered my cock..With a hard on it would have been different.

Then - the bra. For some reason this was the item that excited me the most. Physically I was just about the same size as my mother so I thought I would leave the straps alone and proceeded to slip my arms through. Then came the challenge! I reached up behind my back with both hands and managed to grasp the ends of the bra which hooked together at the back. It took several minutes of fumbling, bumbling around there but I finally got them hooked. Looking into the mirror I determined the front had to be pulled down well past my nipples so I did so. Must have been some magic to it because the mirror portrayed 'something' trying to force its way through the front of the panties.

'Now what', I thought. I obviously had the flattest chest that a bra had ever covered. Back into the hamper I went and finally emerged with 4 more panties and a couple of pair of nylons - all very soft and silky. Wanting to surprise myself I turned away from the mirror as I gently pulled back the edge of the cup and eased in two folded up nylons. This was obviously not enough but I felt they would be softer and not show lines through the bra cup. Two pair of panties were then necessary to really fill it out. C cup - which I later learned was fairly large. I quickly did the same on the other side and held my breath and closed my eyes as I turned to face the mirror.

OHMYGOSH!!! I damn near came in my panties as my eyes bulged at the beauty of what I saw in front of me. The bra was perfect and I appreciated the time I had spent carefully folding and inserting the padding. The entire cup was soft and smooth - just inviting some caressing. It seemed to fit perfectly with my torso and I only wished my hips were just a little larger.

I turned sideways and was just as thrilled as my eyes fastened on the lovely breasts which just seemed to belong to the rest of my body. I had to avoid thinking of a garter belt and stockings right then or I would explode.

Everything- my neck, my face, my shoulders and torso-seemed in perfect proportion for a slim, slinky female (who just loved to fuck and suck cock). The only thing was that a slim, slinky female didn't have a crotch like mine.

I then realized the time and I wouldn't be alone in the house for long. Quickly I stripped and returned everything to the hamper in approximately the same area I had found them. Whew - I made it as ten minutes later the family were home.

I was somewhere in Iowa when hunger finally got the best of me so I stopped at what appeared to be a truck stop. I found a table in a corner and sat there gazing at all the men while my order was being prepared. Gazing continued as I ate. My mind visualized what it would be like to 'dress up' and spend some time with one or two of them. I finally had to get up and leave before I became too obvious. Oh, I should say I had tucked my cock into my pants before I went into the café - and then pulled it out when I was safe in my car and starting down the road again.

After my first dress-up I realized that if I was going to continue I really should get my own 'clothes'. This presented something of a problem since I was rather shy and scared as hell that someone I knew might see me.

Chicago is a big city so I finally determined that I would go to a distant part of the city for my shopping. I wasn't going for spendy, high fashion stuff so I went to a Kohls store first. The plan was to act ignorant and need help to buy some lingerie for my girlfriend. I thought the sizes I needed would not be excessive or bring attention to me.

I approached the lingerie department and slowly wandered around until I found bra/panty sets in all different colors and there I stopped. Sure enough along came a middle aged lady with a nice warm smile and asked if she could help. I told her I was very nervous since I'd never done this before and I even managed to work up a blush. Then I told her what I was shopping for and why and she smiled and said she encountered guys like me every day.

Soon I found myself standing there holding a black, lace trimmed 32c bra and matching small panties. Things went so well I figured I may as well go all the way and we picked out a black garter belt and black, sheer stockings.

The worst part of it all was I had to carry this unwrapped stuff as I waited in line at the cashier. I know I got a few sideways glances but I finally got through and was greatly relieved as I got back into my car.

One thing remained to be obtained. I had seen false breasts on the net but they were very expensive - like 3 or $400 per pair. Besides the only way to get them was thru the mail and that just wouldn't work at home. A possible substitute would be just plain 'falsies' which again I saw on the net for a lot less money and likely attainable right here in town. As I understand these falsies were soft and used to present a larger breast for women. They were just inserted into the bra over the breast and were soft, smooth and even had a nipple on them. Victoria Secret web site was where I had seen them and they only amounted to about $20. There were several Victoria Secret shops in town.

Now I had to find a way to buy them. After I returned to home I sat at my desk and pondered just how to do that. I left my newly purchased things untouched until I got the falsies. I thought about a party I had been at where each person had been given a list of things to go out and get - the first one who did it and got back to the house was the winner.

This would work! I sat there and made up a list of strange, unrelated items including 'pair of falsies'. I then crinkled up the paper to make it look used and stroked out all the items except falsies. Excited as hell now I headed right out to the nearest store and went right in with my list in my hand. It turned out to be just simple as hell as I was shown a selection of sizes etc. I chose C, paid my $11.95, stroked that last item on my list out and left the store.

While I didn't worry about the privacy of my room I nonetheless stored my goodies in a suitcase in my closet for which I carried around the only key. All of my items were then removed from the shopping bags and fondled lovingly as I removed all the tags. Just to make sure I then stashed them in the suitcase and went out for a drive where I disposed of these bags, receipts etc. in a big dumpster a couple of miles away.

It was a couple of afternoons later that I took a nice, hot shower during which I endlessly massaged my cock and crack with a soft sponge. I finally got out when my cock just couldn't stand any more.

Before leaving the bathroom I looked into the mirror and just loved what I saw - except - my pubic hair. While it was blond it still just seemed to not be what I wanted. Out with shaving gear and I lathered up the entire area around my cock and also completely covered my balls. Needless to say I was very careful as I skimmed all around my cock and my balls.

The mirror quickly illustrated that this was a good move. My genitals took on a soft and clean appearance which was really neat. A little aftershave and that was that.

I reentered my bedroom and was ready to go when - a knock on my door. I was tempted to remain perfectly quiet and hopefully whoever it was would go away.

No such luck as I heard my sister call "I know you're in there. I'd really like for you and I to go out and have something to eat. I need to talk to you. It's important".

My sister, Jan, was a couple of years older than me. We were rather similar in appearance - height, build, blond hair - except for the chest. Jan was blessed with a GREAT set of tits (along with an equally great ass). We were not true brother and sister since Jan was born of a previous marriage of my father. We were, however, very close and shared many things.

For this reason I felt I had to go along with her. "Ok, I'll be out in a minute" I said and proceeded to stash my newly acquired belongings in their intended safe place. It took me another couple of minutes to get dressed and then out the door I went.

Jan was standing in the hall and quickly scanned me all over as I came out. "Don't you look all cleansed and pretty" she commented with a rather knowing look on her face. I cringed inwardly and tried not to show any outward recognition of the accuracy of her remark.

Rather than stand there I said "let's go", and I started down the stairs and out of the house. I did this on purpose as I had to get a little time to think since I was really concerned as to what Jan meant by 'important'.

I had to keep in mind that Jan and I had shared our thinking, fantasies and experiences on a very personal basis all our lives. Like the time I did get laid with a girl and her first - with several to follow - experience in fucking a guy. These things were strictly between her and I and couldn't help but make us very close.

BUT - I hadn't mentioned a word about my fantasizing and experiences of the last few months. Even though I knew her so well I just wasn't sure as to how she would handle this 'reversal' of mine.

I managed to keep our conversation as small talk as we walked the couple of blocks to a restaurant we often went to. We managed to get a corner table and due to the hour there was not a crowd so we were quite private.

I figured it had to happen sometime so I looked at her and said "ok, what is it that's so important"?

She fumbled with her fingers on the table as she looked intently at them for a good minute. Then, finally ready, she looked directly into my eyes and said " I don't know exactly how to approach this but since we are so close and have shared so many experiences I guess I'll get right to the point. Correct me if I'm wrong but I don't believe you are going out with a girl right now".

Knowing exactly what was coming I just said "that's right" and followed this with "please just go ahead - sharing privacy with you is about the most valued possession I have and I know you feel the same".

I could tell she felt quite relieved as she went on. "Thanks. I needed that and I do feel the same. You see my friend Stacy - you've met her - and I were just talking the other day and she mentioned that she had seen you the other day at Kohls where she works".

I took a deep breath, closed my eyes momentarily and asked her to proceed. I think by then she already had an idea as to what was going on.

"She was going to come over and say hello until she saw that you were talking with a sales lady in the lingerie department. After you left there she just didn't know what to say considering the purchases you were carrying to the check-out counter so she just returned to her own work. I know it's none of my business but I just thought I'd let you know - of course if you'd like to share with me that would be ok too", she added with a cute little smile.

Another deep breath and I just figured 'what the hell'. "I guess, considering all of our past sharing of secrets, I may as well 'fess up. You know very well I've fucked only one girl in my life and that was a so-so experience. I really just don't feel comfortable talking to girls in a way that would lead to a real relationship - you know, like steady company and fucking."

It was such a relief finally letting this out and especially to Jan whose facial expression told me she understood where I was coming from. She kept her eyes on mine and obviously was waiting for more.

"I found myself become obsessed with the internet and all the porno girl/guy stuff that was so available. You know - fucking and sucking." She nodded her head so I continued on. "For some reason I began to wonder who was having the best time - the girl or the guy." Another deep breath. " With this question on my mind I went back to the net and it didn't take long to find gay stuff galore. Pretty soon I was corresponding with a couple of guys".

From there I told her about Sammy and just how great it was. She nodded her head as if she had been there with me. "I'm sorry I haven't confided everything with you Gene", she finally said from under downcast eyes. "I had a try with girl/girl stuff and found I did enjoy it but I do like guys. I go with a girl once in a while but only if I get approached. I guess my penchant for sucking cock gets the best of me".

Another wave of relief swept over me and I guess it showed as she also seemed relieved now that she had it on the table and I had obviously accepted it.

It was easy then to go on to my experimenting with 'dressing up' and my visits to the stores.

Interspersed with all this we had managed to have something to eat and now found ourselves strolling towards home. "You know it's really coincidental that right now I'm getting together with a guy - nothing serious but he really is a great fuck. We talk about everything and he was mentioning just the other night about how he wondered what it would be like to make out with a crossdresser - even as a threesome".

I damn near fell over and turned to stare at her. "Are you saying what I think your saying"?

Her eyes lit up and with a sly grin and she said "What is it you think I'm saying"?

"Um-er-well is that an invitation"? I knew there was poorly veiled hope in my voice. I waited on pins and needles for an answer.

She wore a broad grin as she said "I'd have to clear it with him first but I'd give it a try if you'd like". I felt kind of dizzy as I turned this over and over in my mind. Jan and I had shared a lot but never physically.

Her hand found mine as we continued our stroll. "I would have to know what I'm talking about before I spoke with him though". She gently squeezed my hand as she said it.

I looked up at her and saw she was staring right at me. I realized immediately that she wasn't just messing around.

"What I could do is to help you get dressed for the first time - you know - getting the right things in the right place, make-up and maybe some additional clothes and a wig. I have a couple of wigs that I think might look great on you". Her smile told me she was wanting to do this very much. I felt I just couldn't turn her down,

Returning her hand squeeze I said "I know I just couldn't turn down such an offer, especially from you. Can we go ahead as soon as we get home? We do have the house to ourselves for the next two days".

"Let's do it", she exclaimed and it was obvious she was excited as her pace quickened and we damn near ran the rest of the way home.

More to cum...