Dennis Meets my Female Side, Janice

Back when I was 25, I was renting a room from a slightly older friend, Dennis. We both worked security jobs so our hours and days were odd. He mostly worked days. I mostly work nights. It was a good situation for me as he had no idea that I was an avid crossdresser.

I am five foot seven and about 130 pounds. Thin with a little pug here and there. Since I worked for a small security company, they had very lax dress codes. So I was able to grow my reddish blond hair to my shoulders. It was very curly and took a lot of care to keep under control. I shaved my body every other day. So even nude, I made an almost passible girl. I bit on the ugly side, but there is makeup for that.

I have been crossdressing since I was little. Growing up with two sisters and no father or brothers, I tended to be a bit girly from the start. I fell in love with the feel of satin, silk, and nylons almost from birth. I even inherited the occasional clothes from my sisters.

So, by this time, I was dressing as often as possible and even started to go to a local gay nightclub. So far I would just stay in the corner, drinking and fantasizing. But then events happened that changed all of that.

First, I was caught dressed up by my roommate/landlord.

It happened one day when he was at work and I took the time available to get fully dressed and just sat in the living room watching TV. All of a sudden the front door opened and Dennis came walking in. We both just froze at first. He stared kind of squinting while staring at me. I jumped up, mumbled something awkward and ran for the bathroom. I sat on the toilet and started to cry. I figured our friendship was ruined and I would need a new place to stay.

Dennis came to the door and knocked gently. He asked if he could come in and talk. I had no where to go and no way to change so I unlocked the door. "let me look at you." He stared me up and down several times.

"why didn't you tell me about this?"

"I have never told anyone about this before." I said.

"You obviously have been doing it a long time. You look kinda sexy as a girl."

I was wearing a white silky stretch top over my D size falsies, a black leather skirt, stockings and 3 inch black heels. I had a pink bra, panties, and garter set on underneath it all. I thought I looked kinda cute too.

"Thank you, that is sweet of you." I said "Does this mean you want to still be friends and such?"

He chuckled. "Of course. I do not care if you like to dress up as a girl. How does that harm me?"

"Well, it doesn't. But I will try to keep it away from you."

"Don't bother." He said. "Feel free to dress any way you like at home. After all it is your home. "

We talked most of the day away and I went to bed filling exhilarated. Not only had I been outed, but Dennis was completely OK with it. I could dress at home and not hide it any more.

So after that fateful day, I started dressing more often. I became much better at makeup and began to spend most of my money on lingerie, clothes, and shoes. I eventually threw out all of my male underwear and only wore panties from then on. I had more female clothing then male clothing.

Then two things happened in quick succession.

First the company I worked for went out of business. Times were rough and I was having a hard time finding work. Dennis was more that understanding and let my rent slide until I could find a new job.

Second, Dennis' girlfriend (whom I never liked) dumped him in a quite harsh and embarrassing way.

This all led up to "the night".

I was at home, dressed, wearing very little makeup, bra, panties, and a short negligee. All in my favorite color, pale pink with white lace trim. While I was watching TV, again the door opened and Dennis walked in. I did not look closely at first and asked why his date ended early.

Dennis broke out in tears.

"She dumped me, Janice (my fem name). Right there in the restaurant. In from of all of our friends!"

I got up and went over and hugged him. Obviously Dennis needed some consoling. I did notice the smell of alcohol on him.

"Have you been drinking?" I asked.

"I was hurting and could not bear it any longer so I stopped at McMinns and had a couple of shots."

I hugged him harder and started to rub his back.

"I am so sorry Dennis. You are a wonderful man and she is a stupid bitch to lose you."

Dennis was hugging me back and then started to rub my back.

"God, you are so soft when dressed like this. Can I hold you just a bit longer?"

"Of course. Let us sit down on the couch so we could be more comfortable."

We sat down together. He on my left, resting his head on my shoulder, while holding my hands.

He continue to cry for about a half an hour, but eventually started to nod off. I eased his head into my lap, so he would be more comfortable. I did notice some stirring in my loins as his head was in my lap, but I just tried to ignore him and watch the TV.

After an hour or so, I felt him begin to still. He woke up, looked me in the eyes, his head still in my lap.

"Are you feeling any better?" I asked.

"God you are pretty." He blurted out. "Did I ever tell you how sexy you look when you are all "dolled up"?"

"Why no, you never have. You think I am pretty as a girl? Really?" I was blushing.

Dennis suddenly sat up, grabbed me by the back of the head and locked his lips around mine. Before I know what has happening, his tongue was exploring my throat. That stirring from before came back with a vengeance. I was overcome with a rush of sexual energy.

I started kissing him back.

Dennis' hands started to rub me all over. I felt an electric thrill every time he rubbed a silk covered part of my body. I was starting to get an erection. Still kissing like crazed teenagers, Dennis pulled us both to our feet and we walked, lips still locked, tongues still dancing, to his room.

I pulled away and for a brief moment thought we should not do this. Then the thought was gone. I just had to suck Dennis' cock or I would just die. Nothing else mattered to me at that moment.

I pushed him down on the bed and attacked his belt and pants. Quickly I had his semi erect penis out in my hands. I started to slowly jack him off and his penis became a bit harder. I noticed his penis was not small, but neither was it giant. This was good because, while I have fantasized about having sex with a man for years, I had never done so. I have had a few dildos and anal plugs up my boipussy in the past, but never the real thing.

I went for it and placed the throbbing head of his cock in my mouth. It was warm and soft and felt absolutely wonderful in my mouth. It went partially down my throat, but it did not cause a gag reflex. I started lightly sucking while moving my head up and down his cock. Saliva was starting to leak out of my mouth and my nose, but it just made things sexier.

Dennis was moaning with pleasure. Oh my god! I was making a man moan with pleasure. I would have broken out into a smile, but my mouth was a bit busy sucking on his cock.

After a bit, my mouth started to get tired. I was not used to this type of "exercise". I swore to my self that I could push past this and that I was not only going to give Dennis an orgasm to remember, I was going to suck and swallow his cum. That is what any good woman would do.

By now Dennis was thrusting his hips up to meet my face and I started to get a rhythm going with his body. I occasionally hit a short gag, but mostly it was the wonderful feeling of a man's cock gliding in and out of my lips that I experienced. My body was so alive. My nipples were hard. My cock was harder that it had ever been. I was so horny I would have sucked off anyone with a dick if they had joined in.

I felt completely feminine.

After about ten minutes of this, I could tell Dennis was on the verge. His body started tensing up. He grabbed by head by both sides and started "guiding" me over his cock. I sucked harder and was soon rewarded when he suddenly tensed up and stopped moving. All of a sudden the were a gush of salty seamen in the back of my mouth. The taste was more wonderful than I could have hoped. My mind rushed with the fact that I had just sucked a guy off and he came in my mouth. I was so alive with sexual energy at that point. I was unaware of what was happening for a good minute.

I lay down next to Dennis and in a soft whisper asked "Are you feeling better now?"

"yes" was all he could get out. I lay there next to him, stroking his hair and chest. Still savoring the salty taste of seamen in my mouth.

"Well, Dennis, we might have to make this a regular thing." I said softly. "You turned me on no end. May I sleep here cuddled up with you tonight?"

He just grabbed me and pulled me close, placing my head on his chest.

"We can do this any time you like. Maybe next time I might fuck you in the ass? With that he reached down and started rubbing my panty clad behind. I wiggled and squirmed and said "I will do anything your heart desires. You bring out the real woman in me."

With that he stuck his finger slightly into my anus. I wiggled and shuddered with delight.

I moved into his room the next morning.