First Times

A little background is in order. During my teen years, I became involved with a woman that helped me discover the pleasures of my female side. Sue helped me to dress and act in a very feminine manner. We were almost like sisters in the way we became so close.

She would sometimes describe how good her boyfriend would make her feel when they would make love. She seemed to think it was funny seeing me squirm when she would get a little too graphic. I know she was only giving me a playful hard time.

She did get me to admit that I was just a little curious about what it would be like to be with a man. Each time she brought up the subject, I would say "No Way". I couldn't be with a man until I felt more comfortable being a woman. After she married and moved away, I wasn't able to dress as often.

I purged myself of all my clothes and jumped into what I hoped would be manhood. Four months after she left, I joined the military.

For several years after I joined, I act like Joe Macho. I would do just about anything trying to prove my manhood. But then it happened, I was in a mall one day with some friends. The wife was in the lingerie section of the Ladies Department. Her husband and I were like all guys, in that situation, trying hard to not be there.

As I made my way past several racks of bra and pantie sets, one set in particular caught my eye. It was a pink lace baby doll set that reminded me of the first set of lingerie I had tried on.

The old urges to be a woman came flooding back. I tried to convince myself that it wasn't going to ever happen again. I even had my reason why I could never do it. I was in the military. If caught, I would be thrown out with the black mark on my discharge papers. Worst case would be if some of the guys in the barracks found out. I would be the subject of a blanket party or worse.

The more conflict I had within me, the stronger the urges got. I even tried writing to Sue about what was going on with myself. After 3 weeks and no letter from Sue, my will power caved and I devised a plan to at least try dressing.

I went back to the mall where I purchased several pairs of panties and bras that I kept stashed in my locker. I would dress and masterbate, remembering some of the fantasies I used to have after listening to Sue. I have to admit, a couple of times my mind would wonder back to her suggestion of being with a man.

Jim, my roommate at the time was a party animal that would come back to the room and pass out. After finding him several times on the floor in the morning, I would make sure Jim made it to the bed. I would help get him undressed if he couldn't do it himself and set up the trashcan next to the bed. In the mornings, I would make sure he got up, had his OJ ready after his shower and made sure he got to work on time.

The first time I did that, I laughed at him saying how easy it was for me to get a big guy like him into bed and out of his pants. He was 6'1" and 200 lbs with muscles everywhere. I was still 5'8" and 157 lbs with no real muscle mass to speak of.

One Sunday night, he came back early. When I heard the key in the door I threw on my bathrobe. My heart was pounding because I still had my bra and panties on. As was becoming the custom, Jim would attempt to tell me about his latest conquest as I helped him get undressed.

He was lying on his back and as I bent over getting his shoes off, he started running his hand over the backside of my thigh. I couldn't believe how good it felt but my mind was screaming to run before his hand reached the panties. I slapped his hand and in my best feminine voice I said "No fair getting fresh when you're drunk!"

He started talking about how much I resembled a girl and how soft and smooth my legs felt. I never really had much hair growing on my legs so I would just shave them. He started talking about how I could give him a blowjob to help him get to sleep. I jokingly said, "I would rather suck you off when you're sober so we could both enjoy it". As he drifted off to sleep he made a comment that I would make some guy a wonderful wife one day.

As I pulled his pants off, I noticed that he had a hard on poking out of his boxers. I was amazed at how big Jim was. His cock was at least 7" and at least 3 inches thick. I wanted to touch it but was afraid that if I did he would wake up. I got in my bed but I couldn't take my eyes off his cock.

I slipped my hand in my panties and slowly stroked myself to orgasm. I exploded faster and harder than I could ever remember. I had to push my face into the pillow to keep from moaning out loud. I withdrew my hand and licked the cum from my fingers. I was amazed at how it tasted.

After I was sure he was asleep, I got out of bed, cleaned myself up and got changed. I had a little trouble getting to sleep with all the thoughts that I was having. I finally drifted off thinking about his big cock and what it might be like to have Jim make love to me.

The next morning, things were not normal. It was a little easier than normal to wake him up. He jumped up and headed for the shower. Normally he would bring fresh pair of boxers with him to the shower but this morning he didn't. He came back in the room and dropped his towel with him facing me. I know he saw me glance down to his cock. He dressed and before I could give him his OJ, he left. I just shrugged it off as being a fluke.

He came back from work and took off his uniform. He was sitting in the chair with just his boxers on. We started talking and I was having trouble not taking quick peeks at his crotch. He started thanking me for taking care of him whenever he came home drunk. He also told me that he hoped that I didn't take offense to his comment about being a girl, the blowjob and being a good wife.

I laughed it off saying that I didn't mind because I knew he was drunk. It didn't dawn on me that he might not have been as drunk as I thought he was since normally he didn't remember much the next day.

The next weekend was a long weekend. He was supposed to be gone till Monday. I didn't see him after work Friday so I figured he left for the weekend. Saturday morning, I went to the mall and found a very pretty lavender and lace baby doll set. I figured that with the long weekend I could wear it to bed and not have to worry about Jim being home.

On Saturday evening, I dressed in my new baby doll outfit, got in bed and jacked off thinking about Jim. I came in my hand and I licked it clean. I was starting to acquire a real taste for cum. Since I didn't think he would be back, I fell asleep in my nightie. I fell into a deep sleep dreaming about Jim and what our life would be if we were married.

At around 1 AM, I started getting the sensation of someone playing with my breasts. At first I thought it was a dream but I realized that Jim was whispering in my ear that I looked pretty in my nightie. He started kissing my neck and moving next to me in bed. He was naked and I could feel his cock again my hip.

I froze in fear but he assured me that I had nothing to worry about. I was so afraid that he would tell the Shirt and my life would be ruined. He told me how he remembered what I had said the previous weekend and was testing the waters. He told me that he found my locker unlocked and discovered my little stash of undies. He also told me that he watched me get undressed last Sunday.

He gently turned my face to his and he softly kissed me on the lips. Jim told me that he hadn't had anything to drink that day so he was fully aware of what he was doing. I looked into his eyes and saw something that told me to not to be afraid. He wanted me as his woman. I put my arms around his neck and pulled him closer. The kissing became so passionate that I felt dizzy. I held on to him so tight.

I relaxed my hold on him and slipped my arm down between us. I wrapped my fingers around his cock and started slowly stroking him. He kissed his way down my neck and slowly worked his way to my nipples. He started slowly running his tongue around the nipple. It felt like a surge of electricity pulsed through my body. He slid his hand down over my tummy and I slightly spread my legs to allow him access. He slowly started stroking me through my panties.

I pushed him on his back and slowly started kissing my way down his torso. I kissed the head of his cock and tasted his pre cum. I slowly opened my mouth and he pushed the head in. He told me to run my tongue around the head and I did. He pushed himself in further and I reached up and started playing with his sac. He started pumping in and out as he was playing with my nipples. His cock reached the back of my throat and he told me to relax when I started to gag. Soon I was able to take all of his 7 inches without gagging.

My mind was screaming this was wrong but my body convinced my mind that it was right.

His hand slipped down in my panties and started rubbing my little 4 inch clitty. I spread my legs and his hand slipped in between. He started rubbing the soft spot behind my sac. Soon his finger was rubbing the opening to my anus. I started moaning at all the sensations that I was experiencing.

He slid my panties down my legs and off. The next thing I knew, I felt his finger smearing something slippery around the opening. He slipped his finger in me and started finger fucking me. The sensation caused me to spread my legs wider. He soon had two fingers in me, moving in and out.

The more he fucked my mouth and fingered my ass the more I wanted him to cum in me. Just as I felt his sac start to tighten, he stopped and told me he wanted to fuck me. I was so worked up by then that I agreed. I wanted to feel him inside of me. He moved between my legs. I felt his cock push against my opening and he kept telling me to relax so it wouldn't hurt.

He slowly entered me and took his time pumping in and out till I felt his balls hit my ass cheeks. Then he started moving faster. I was in ecstasy. I started playing with my nipples as he fucked me. As he started shooting his load into me, it pushed me over the top and I exploded with the most powerful orgasm I had ever experienced.

After he slipped out of me, he rolled over and he pulled me close to him. He whispered in my ear that he hoped that I enjoyed it as much as he did. Jim told me that from now on, he wanted his wife in his bed every night. I was so happy I had tears in my eyes. We fell asleep with me wrapped in his arms.

The next morning around 10 am, he woke me with soft kisses on my neck and lips. He told me that I looked so cute when I was sleeping. I slipped down under the covers and took his cock in my mouth. I wanted to feel him in me, to taste his cum in my mouth and to feel it in my tummy. I sucked him till he exploded. I felt like I was his woman and he was the man that I wanted to please. We spent most of the day in bed.

Around 6:30 pm, he smacked my butt and told me to get dressed that he wanted to take me to dinner. I put on my pink lacy bra and pantie set under some loose fitting clothes. I even put on some cherry flavored lip balm.

We had a really nice and slightly romantic dinner. We talked quietly about some of my past. That night when we got home, I dressed in my baby doll and climbed into bed with my man.

He shipped out 5 months later and left me with so many wonderful memories of new experiences. He taught me that I could be a woman in love.

My bed might be empty but my secret stash had grown larger.

To be continued......maybe if I get some positive feedback about my stories.