It had been an unusually long and hard week at the workplace. The week started on the wrong foot when a major project was likely to be delayed by a month because of a supplier issue. Stress was adding up through the week as my manager kept demanding that I get the project back on course by week’s end. Come Thursday, there wasn't an end in sight. I was thinking my job will be on the line. I was near the breaking point and I knew I had to do something, but what?

Soon I found my thoughts drifting away from the issues at hand. It had to happen. I needed to relieve some of the stress temporarily. My mind shifted from work, to my comfort zone, and then my pleasure. Soon I was lost in thoughts of the coming weekend where I could wear panties, thigh high nylons, five inch heels, and my Little Red Riding Hood costume that I had recently acquired as a Halloween trick or treat for myself. I started thinking how much stress relief I’ll do in the confines of my bedroom. I subconsciously started rubbing my crotch through my work pants when…

“Ahem… Jesse.”

Reality struck with my co-worker Dan at my office door peering in.

“Sorry to interrupt you,” he said with a sly smile.

Dan continued, “I think we have a path to get the project back on track, and it was due to your earlier work when we bid this whole program out.”

It dawned on me. I had talked to two different suppliers with this part as I had a feeling something would happen. “That’s right! I forgot about that! Let me make a call, maybe we can get the program going again!”

I had a big smile on my face when I said, “Thanks Dan for the reminder. This will save me big time! I owe you!”

With that same sly smile, Dan said, “You owe me big time for this.”

Little did I know how much of a pay-back I would have to give to him.

Friday came and went, and with Dan’s help I successfully got the program back on track. I went home and decided a nice hot shower was in order and I would start relaxing. I turned the shower on and steam was quickly filling the bathroom. Once I hopped in the shower, I applied shaving cream to my legs and started shaving my leg hairs off. Yes, it was time to go from Jesse to Jessie, my alter-ego.

Soon I had removed all of my hair from my legs, crotch, rear, underarms, and chest. I felt really relaxed, and was ready to continue on to be Jessie. I painted my toe nails a bright read, put on a pair of red bikini panties, and my Red Riding Hood costume. Next I placed my wig cap over my head and then put on my red haired wig. I had to admit, even though at this point I wasn't passable, I felt feminine. Finally I put on my white thigh high nylons with a little red bow at the top, and my black five inch platform high heels. I looked in the mirror and thought I was really looking hot.

I sat down and watched a little TV. After my favorite show was over, I thought I would self-pleasure myself, pretending and wishing I was a total woman. These sessions always ended well. In the middle of my show, the door-bell rang. I ignored it as I was not expecting anyone. It kept ringing, so I took my heels and wig off. I quickly put on sweat pants and a robe over myself so no one could tell I was wearing woman’s clothing. I answered the door and Dan was there.

“Hi Jesse! I thought we deserved to celebrate getting that program back on track this week.”

“Dan, I’m really tired, I don’t think it really is a good idea,” I replied.

“Well, you owe me. For payment, it is celebrating our success,” he said as he barged in.

I shut the door as he sat down on the recliner with a beer. I sat on the couch.

“So Jesse, what did George say once you let him know how we were going to fix the project?”

I answered his questions, not realizing that my five inch heels and wig that I took off were visible to Dan. He got up and sat next to me on the couch. I thought it was odd, but didn't really move. He continued his conversation, and over time, his hand went on my knee to emphasize a point. His hand stayed on my knee. I was starting to get uncomfortable.

Dan suddenly said, “Model those high heels and wig for me.”

I blurted out unconvincingly, “Those aren't mine. My sister left them here.”

“We both know that isn't true, they are way bigger than what your sister would wear. Don’t you remember? I met her? There is no way those are hers. Now put them on!”

I reluctantly put them on. As I bent over to strap my heels up, my robe separated and gave away another secret.

“Wow Jesse! What have we here? You’re wearing a pretty hot looking outfit.”

I started turning red with embarrassment.

“What else is going on?” as Dan removed my robe and started pulling down my sweat pants.

“Well, well. Looks like Jesse, or should I say Jessie, likes woman’s clothes. I wonder what else Jessie likes?”

“I don’t know what you are talking about Dan.”

“I think you look really hot all dressed up like that. It would be a shame for that to go to waste. Remember, you owe me.” He leaned forward and softly caressed my left cheek just before our lips made contact.

It was a brief soft kiss. Even brief, I was amazed at the fireworks that were going off in my head.

I wanted more. I leaned back toward him and kissed him. Next thing I knew, his soft tongue slowly parted my lips, and we were locked in a very passionate kiss. This went on for minutes before we released.

“You are so sexy Jessie.”

He gave me another passionate kiss, embraced my body softly and with respect. I was melting like butter in his arms. My resistance was weakening by the minute. Next thing I knew, his hands were under the skirt of my costume, and his hands were on my butt cheeks. My hand started making its way to his crotch. When it got there, he was very hard, and big. I started rubbing his crotch through his jeans.

“Mmmmm. Yeah Jessie. That’s it. Keep doing that.”

After five minutes of rubbing his crotch, I teasingly lowered his zipper and unbuttoned his jeans. I lowered his jeans and underwear enough to free his manhood. I placed may hand on it and started rubbing it as I would like to do with myself.

Dan started moaning loudly, and his hands were starting to migrate to my crotch. Before he got there, I backed off, and he looked a disappointed. I got down on my knees so I was level with his penis. I started stroking it lovingly until a drop of clear pre-cum graced the tip. I thought to myself it was now or never. It was definitely now. My inhibitions were gone. I wanted to know what it felt to be a woman, and I wanted to know now.

I brought my tongue to the tip of his penis and slowly licked the pre-cum off of it. I looked up at him with a smile. He looked at me with amazement and lust in his eyes. As I was looking into his eyes, his soul, I opened my mouth and started taking his penis into my mouth. Even though I never gave a blow job to anyone in my life, I knew instinctively what to do. Soon Dan was moaning and thrusting his pelvis towards my mouth. I was getting my share of his manhood as pre-cum kept oozing out of him. I savored the taste as it coated the insides of my mouth. Finally he backed off.

“Damn Jessie! That was some really awesome head that you just gave. I was about ready to bust my nuts into your mouth. But now is not the time.”

He lifted me up, and took my pre-cum soaked panties off. I was still in my sexy Red Riding Hood Costume, white thigh high nylons and high heels.

“I want you to lift your skirt up Jessie, and sit on me. I want to take you tonight. I want to be the one that completes you and makes you a woman.”

I went and got some lube to place on his penis as he was big, and I wanted to enjoy it and not fight discomfort. After applying lube on him and some at my entrance, I did as he asked. I lifted up the skirt just enough so I could straddle Dan. I stroked his penis several times to get it hard again, then I slowly lowered myself onto him. There was resistance as the tip of his cock pushed up against the ring of my anus. I kept lowering myself down until there was a release followed by some pain and then finally pleasure.

After a minute of adjusting to the new sensations, I slowly started to ride Dan’s cock. I felt so full and elated that I finally knew what it was like to be a woman. I could feel the contour of his cock as it slid in and out of my backside. While I was riding him, he lowered my lips to his and we resumed our passionate kissing. Every moment felt like mini fireworks were going off inside me. I didn't want it to end as I had never experienced anything like this before. I was also hoping that this wouldn't be the only time. After fifteen minutes of riding we stopped kissing.

“Jessie, your ass is magnificent. I have never felt anything better in my life. Now it is time for me to take control.”

While still impaled on his marvel, he laid me on the couch, and pushed my nylon and high heeled clad legs toward my chest so he could deepen the penetration. Dan started at the same pace as at the beginning of our fest, but then he started to speed up. Both of us were moaning in pleasure. My penis was hard as a rock and it got harder as he thrust into me and pushed up against my prostrate. Pre-cum was oozing out of my penis and then suddenly I felt the familiar feeling of orgasmic bliss growing inside of me. After a couple more minutes, I released in pure orgasmic pleasure that I had never felt prior in my life. Finally, cum shot out of my penis, and all over the front of my Little Red Riding Hood costume. My anus was also pulsating which started to send Dan over the edge.

“Ohhh, Jessie, it’s too much. I’m going to cum!”

Dan started to pull out, but I quickly wrapped my legs around his torso so he couldn't decouple from me. I grabbed his butt and shoved him in as deep as he could go. Then suddenly Dan groaned loudly. I could feel his cock pulsating inside of me and jets of cum splashing my insides. I smiled knowing that now, I was complete, and had my reward.

Dan stayed inside of me for a couple of minutes until he got too soft to stay in. As he withdrew, some of his cum dripped out of my ass onto the couch. He gave me a final passionate kiss, put on his pants and said, “Jessie, you were amazing! I can’t wait to tell all the guys at work about this!”

I look of pure horror was on my face. I pleaded, “Oh please no. You are the only one that knows my secret.”

Dan promptly stated, “Don’t forget, you owed me big time. This is just the start.”

He then walked out the door.