tagTranssexuals & CrossdressersCh. 02 More First Times

Ch. 02 More First Times


After Jim left, he would phone at least once a week and I would get little love notes several times during the week. We talked about how much we missed each other. Soon his letters and phone calls became fewer and further between. I knew deep down that we were not destined to be together but a girl could always hope. He would remain my first real true love.

After Jim left, I never did get another roommate. I had some suspicions why but could never confirm them. I knew that Jim had been friends with Robert, the Dorm Manager. They would occasionally go drinking together.

Robert would stop by, every once in a while, to see if I had heard from Jim. I never knew if Jim told him anything. I started wondering if he was trying to see if I would be interested in him. At times, I would catch him taking quick peeks at my crotch and chest.

He almost treated me like a military wife with a husband overseas. At times, he was a perfect gentleman just checking in on me and other times he just seemed like a perv looking to get into my panties. When I said something to Jim about Robert s actions, he just seemed to blow it off.

I know he was looking to see if I was more than just a roommate with Jim. Several times, Robert sounded almost too inquisitive about my relationship with Jim. Since I was not sure which way Robert swung, I maintained that we were just good friends. You had to be careful back then because the military had people planted in the ranks looking for offenders. That was the era prior to don t ask, don t tell.

When the letters and calls stopped, I was heartbroken. I had tried several times to call but the number was shut off. Even my letters went unanswered. This is when Robert seemed to show up more often. I still was not sure if he was trying to bed me or was looking for dirt so he could out Jim and me. In the beginning, Robert always stayed a respectable distance when talking to me. The more he came over to talk the less the distance became. At times he would get real close and run his hand softly over my upper and mid back. It was like he was looking for something. Several times his hand would just stop in the small of my back just at the crack of my butt.

He would sometimes show up on Saturday night, appearing half looped. It was those times, when I got the impression that he was looking for more than just information about Jim.

A couple of times when he came in from the bar, he would get real close, put his arm around my waist and softly whisper in my ear about how drunk he was. He once mentioned that he knew how I took care of Jim when he was drunk and wished that he had someone to take care of him.

Little did he know, Jim may have gone out with his friends but he was not getting drunk like he used to.

Back then, the shower rooms were just stalls with a shower curtain. Several times I could have sworn that he was checking me out in the shower. The more he did that, the less I dared dressing in my lingerie. I even stopped shaving in the shower and had to do it in my room.

It really started to creep me out. I was becoming paranoid that if he continued making advances and I kept turning him down, he would out me to the higher ups. I also had my suspicions that Robert was using his master key to search my room. I made sure that my lockers always stayed locked.

I was so happy when I got orders out of there. The orders were short notice and I only had 45 days till I needed to report to my new assignment. I quietly and quickly cleared the base and took leave for the remaining time. I was heading overseas.

I felt I needed to do something to make sure that Robert would never say anything to hurt Jim or myself. I devised a plan that I hoped would work. I was not going to be mean but I wanted to make sure that he understood he could not hurt me.

Robert did not know I was leaving till it was too late. I had scrubbed the room clean, turned in my linens and key to the bay orderly when Robert was out of his office. I had spent several days prior, shipping some of my stuff home. The few things that I needed for my trip, I had packed in the car. I planned on staying at a motel for my last night there.

I cleared the base early in the morning and went back to the motel room to change before getting on the road. I put on my pink lace pushup bra and matching panties under a white tank top and pink short shorts. I put a sweat suit over this to make sure I made it through the gate with no problems.

I stopped in an area on base that was somewhat secluded and put on a wig and some makeup. I pulled off the sweat pants and went by the barracks to wait for Robert outside in the parking lot.

When I saw him, I pulled up next to his car. I had opened my jacket and made sure that my tank top showed off enough cleavage and my bra. His eyes nearly popped out of his head. At first, it seemed like he did not recognize me. Maybe it was because he was too busy looking at my tits.

When he finally looked at my face, you could see the recognition start to dawn on him. After saying Hello in my most feminine voice he started to stammer about how sexy I looked. I got out of my car so he could see the full effect.

I noticed that several people saw him with me. One guy pointed towards me and made some comment to the guy he was with. I imagine it was something about Robert talking to me.

I confronted him with my suspicions that he was doing nothing more than trying to cause me trouble after Jim left. He attempted to get closer but I stopped him holding my hand out. He tried to tell me that he was only trying to show interest in me because he thought I was sexy. He also told me that he had problems talking to beautiful girls. The way he said it made me kind of believe him. I kissed him on the cheek and gave him a big hug. I think he creamed his shorts when I did that.

I got back in my car and started the engine. I told him that I hoped that he would never reveal what had seen today. He told me that he wanted to keep in touch and that he was sorry for the way he acted. He wished that he had just come right out and said how he felt. In a way I wish he had also. I know just how small the world is so I had a feeling that I would see him again.

While I was at home, I packed most of my things into a box and asked my Mom if she would ship them to me after I got to the new base. I was not sure if I would have to clear Customs during the trip. That was all I would needed, to have Customs officer ask me to open my suitcase and find my lingerie, makeup or a toy.

I arrived at the base and found that I was not expected. Apparently no one notified the outfit that I was coming. It was a small outfit that was assigned to a major training base. I had to room with another guy, Tom, till someone left. I found that most everyone had single rooms, which made me feel a lot better. I would have privacy all the time.

It was only 2 weeks after my arrival that a single room opened up and I moved in. A week later my package arrived from home. I dressed almost every night after that. It was like living in a fantasy come true. I even started wearing panties under my uniform and when I knew I could get away with it, a bra or camisole.

Almost every night, I wore one of the baby doll outfits or nightgowns that Jim had bought me. I also found some enjoyment using the toys that he got me. I especially enjoyed a dildo that reminded me so much of him. I would go to sleep dreaming of the times we spent together.

The first couple of months were a bit of a blur. I spent most of the time learning about what the outfit did, new types of equipment and the general layout of the areas we were in. Most of the towns near us were very small and the big ones were at least a 45 minute drive. I started venturing out into the smaller towns and villages by foot or by bus. I would catch rides, from some of the people in the outfit, to the bigger towns.

Tom would take me to some of the bars in the bigger towns on the weekends. He had a girlfriend in one town that he would occasionally stay over night with. When that happened I would either catch a ride back with someone else or I would find a room for the night and ride back with him.

One Saturday, Tom and his girlfriend took me to a new bar that just opened. It was a lot bigger than the ones that we normally frequented. I met a girl there that would become my best friend for a long time. Her name was Leona.

The first couple of times that I went there, I noticed that Leona never seemed to have a date. We talked several times but she never stayed for very long. At first I thought the lack of dates was because of her size. She was a rather big woman like so many of the other farm girls in that area. Leona stood 5 ft 10 and I guessed her weight to be a bit over 200 lbs. She had small breasts that just did not seem to be proportional to her size. I later learned that she only came in for a few drinks before meeting her boyfriend.

I was outside of the bar, one night, getting a breath of fresh air when Leona came out and looked like she had just been stabbed in the back. She was crying and looked like she needed a shoulder to cry on. I offered to talk but the language barrier was rather strong that night. Where she could normally carry on a half way decent conversation in English, she was having problems that night.

I offered to buy her a cup of coffee at the near by outdoor restaurant and she accepted. We tried to talk for over an hour but because of her emotional state, we had real problems communicating. From what I gathered during our talk, she had been dating a guy for almost a year. He was a GI and left without telling her. She found out that night, through some of his buddies. I knew that he had to have known for almost 3 months before this, because she said that he was being discharged.

She was devastated. She also learned that he was going back to marry his high school sweetheart.

I think the only reason she started talking to me was because she was looking for someone that could explain why he would do something like that to her. She later told me it was because I seemed to have a kind heart, a warm smile and did not seem to be judgmental. Over the next few weeks I made sure to find a ride back to town to see her at the bar. i would also call her during the week to see how she was doing.

One Friday, about a month after we talked, I got a message that she wanted to pick me up just outside of the gate that evening. When I called her, she asked if I would like to spend the weekend with her. I agreed without reservation. When I got back to the room I packed an overnight bag and headed for the gate. She was waiting at a small restaurant down the street.

I hugged her and gave her a quick peck on the cheek. She told me that she wanted to take me to a place that she found about 3 hours away. It was a shopping trip for her but that we would not be back till Sunday. She asked me along because she found that I had a fashion sense about me. Leona told me that in just a short amount of time, she found that I seemed to know more about women fashions than most girls did.

I told her how I grew up in a house full of women. I also started telling her a little about my relationship with Sue and how we used to look at fashion magazines all the time. I even told her about how I would help Sue pick out sexy lingerie to entice her boyfriend. I was not about to tell her, at that time, that I also wore at least panties almost every day.

She did hit me with one question that seemed to come out of the blue. She asked if I dated women. It took me a minute but I stammered that I had but was not involved with any at the time.

We arrived at the city, found a hotel and got a room with two beds. We unpacked and went to the restaurant. During dinner I started asking her to tell me more about herself. She seemed a little hesitant to tell all but she did tell me about her family and a couple of her friends.

Leona told me about the dairy farm that she grew up on. I found out that she had two brothers and an older sister. She turned 20 just 6 months ago. I learned that she had a strained relationship with her Father and her older brother. She did not say why but did say that her relationship with her sister, younger brother and Mother was fantastic.

She told me that she took turns with her sister doing some of the farm work as well as helping their Mom around the house. She laughed about how she was able to a lot more strenuous work than her smaller sized sister. Leona was going to school to learn computers. Not to date myself but that was back when you really needed a college degree to run one.

I asked her if she had many boyfriends before the asshole that dumped her. She told me about one that she dated before him but said that she never found anyone else who would accept her. I sensed that she wasn t telling me everything. I got the impression that she was afraid to talk more about dating so I let the subject drop. We started talking about her schoolwork.

After dinner we had a couple of drinks at the bar in the hotel. We even danced to a couple of slow songs. After several dances, we called it a night and headed for the room. When we got to the room, she gathered up her nightclothes and headed into the bathroom to change. I pulled a pair of shorts and a tank top out of my bag and changed. When she came out of the bathroom she was wearing, what I called, a granny style nightgown. It was a long flannel type, which covered every thing, from the neck to the ankles.

I was standing by the bed as she moved towards her bed. I put my arms around her to give her a hug and a quick kiss goodnight on the cheek. At first she seemed to pull away but soon loosened up. Leona looked me in the eyes with a questioning look. I told her that I felt we had become almost as close as Sue and I. I also said that nothing would happen between us unless she wanted it to happen.

I saw a tear run down her cheek and asked if it was sadness or happiness. She told me that she was happy to find someone that wanted to be friends with her. Leona said that she hoped that we would become closer before getting intimate. She mentioned that there were things about her that she wasn't ready to talk about just yet. I went to bed wondering if it had anything to do with her family situation or maybe about a past boyfriend.

I also had a deep down feeling that there was more to her than just her outward appearance.

We got up the next morning and after a quick breakfast, headed out. Leona showed me some of the sights of the city. It was a wondrous place, filled with sights, sounds and smells that drove the senses crazy. We made our way to the dress shop that she wanted to go to. It specialized in big ladies clothes and lingerie.

An older woman, who owned the shop, greeted us. She invited us to look around and if we had any questions just ask. Leona found several dresses and pants suits that she liked. She took several into the dressing room to try them on. I wondered around the lingerie section and looked at all the pretty things there.

At one point the owner came up to me and said that the smaller sizes were towards the back. I must have given her a funny look because she looked me straight in the eye and said that she had a few military type that were shopping for their girlfriends and wives. When she said the words girlfriends and wives she motioned with her fingers the quotation gesture.

When I asked her what she meant, she winked and told me it was the way I looked at the clothes that gave her the impression I did more than just look. She also told me that I had a great figure and would look good in some of the things. I stammered again no thank you but thank you for the comment. I felt my face blush as she went back to the counter.

I went over and sat down next to the dressing room. Leona came out several times wearing the different outfits. She would ask my opinion about each. She even asked what type of lingerie would look good with the clothes. I gave her my honest opinion about all that she asked.

I went over and sat down next to the dressing room. Leona came out several times wearing the different outfits. She would ask my opinion about each. She even asked what type of lingerie would look good with the clothes. I gave her my honest opinion about all that she asked.

After changing back into her own clothes, she took my advice about the lingerie. As we looked thought the racks, I asked if she would model some for me when we got back to the room. At first she hesitated but then with a nervous giggle she said maybe. We picked out several bustier and panty sets as well as several matching bra, panty and waist nippers. She also picked up several pairs of nylons in different shades and colors.

As we went to pay for her things, the woman asked if I was sure that I did not want to look though the things in the back of the store. Leona looked at me as I laughed and said no thanks. As we left the store Leona asked what that was all about. I told her that she told me the smaller sizes were in the back. She looked at me and I just shrugged it off.

When we finally got back to the room, Leona started pulling the clothes out of the bag. She took one outfit into the bathroom to change. It was a pretty knee length skirt, silk blouse and a bustier and panty set. She looked fantastic in the new outfit. The cups of the bustier were slightly padded so her breasts looked somewhat bigger under her blouse.

I teased her and asked to see what she looked like in just her lingerie. She told me to be patient and maybe if I were good she would model them for me. I lay on the bed as she tried on all her new clothes. She came out of the bathroom in just her black lace waist nipper set with dark hose. I moved to the end of the bed and started running my hand across her tummy.

At first she seemed to want to back away but as I told how sexy she looked, she relaxed. She asked me if I felt repulsed looking at her. I asked her why I would feel repulsed by her. That s when she broke down in tears. I told her that she was very sexy and I would be honored to make love to her. Her eyes welled up with tears. I stood up and took her in my arms and started kissing her softly and passionately.

She broke away and she sat down on the bed. She told me that she was different from other girls that I knew.

My female instincts stared screaming that she was like me.

I told her that she was a beautiful woman and nothing could be farther from that truth. She took my hand and placed it on her groin. At first I didn't notice anything out of the ordinary till I slipped a finger down between her legs. That s when I felt the gaffe that held her in place.

I looked her in the eye and told her that I would be right back. She looked at me with a questioning look as I grabbed my bag and ran into the bathroom. I have a habit of carrying panties, bras and sleepwear with me whenever I went anywhere. I quickly stripped off my street clothes and put on my bra that matched my panties.

When I came out she had a look on her faced that was indescribable. It was a look of fear, passion, sadness and happiness all in one. I told her that I could never be repulsed with someone that was just like me. The tears flowed from both of us as we clutched each other tightly. We held each other for what felt like hours.

I finally pushed her back on the bed and started to slowly and passionately kiss her lips and neck. I slowly worked my way down to her nipples that were rock hard. I pulled the bra down so that I could suck and take little love bites on her nipples. My hand slowly worked its way down her tummy caressing her.

She held my head to her tits as I longingly savored her nipples. Her hand moved down and she started to caress my tits through my bra. I got so hard that I couldn t keep myself tucked any longer. My clit started poking up again the waistband of my panties.

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byMichelleWhoIs© 5 comments/ 31543 views/ 7 favorites

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