First Time Fantasy

Fantasy - The Dom, the sub and the bi-virgin

After all these years of being in the closet, I finally believed that it was time to move from fantasy to reality. Years have gone by of me wanting more but not being ready to step out and experience things for myself. My stockings ran and my lingerie started to collect and time and time again, I purged and replaced more than one collection of heels, stockings, lingerie and sexy clothes. But now, yes now, it was time to take another step ahead.

The anal douche, the butt plug, the leather ties and online chats all added to the excitement and the pleasures I gave myself. All of the times that I came on my legs, my feet, belly, chest and face, could not fully represent what reality would be like. The thoughts of expressing my sexual freedom with other girls and at the same time feeling comfortable and yet somewhat empowered became too much to stay in the closet. It was hard for me to get through a day and not think of being dressed and having some play time with a couple of others like me.

One of the online contacts I was lucky to get in touch with was a nice girl going by the name of Nicole. She is very kind, sexy, horny and loves to have fun. Our chat sessions grew hotter and hotter each time we were online and I often fantasized about her and me. During our chats, I had divulged a lot about my fantasies and turn ons and I also learned a lot about what Nicole liked sexually but most important, that she was a beautiful person inside. I had to make a move soon as my urge to play with others grew stronger and stronger as time passed by.

During our last chat, I took up an offer to go to Nicole's cottage for a weekend play session. Wow! My heart was just pounding after that chat session. The pictures of Nicole in crotchless panties and fully fashioned stockings were such a turn on, not to mention her hot text messages. This time my load exploded and was running down my leg and before it ran into my heels. I rubbed it into my nylons and fantasized that it was Nicole's cum that I was rubbing on my legs. I'm such a perv.

I made my way upstairs and had a shower while I was still wearing my lingerie and again I thought about things that could be. In no time I was hard again and I worked up plenty of bubbles and covered my body with them. Rubbing myself all over, I washed my cum soaked stockings while still wearing them. Even the feeling of soapy wet lingerie was a thrilling feeling that I had come to enjoy . What else was I to do? So I stroked myself and inserted a finger up my ass while I continued fantasizing about my first visit with Nicole, my first cock to suck and how much fun it would be. I came quickly and it seemed to last for minutes and minutes. I slowly removed my lingerie and washed out the soap, still shaking from my second orgasm in less than an hour.

The day of facing up to my urges and stepping out finally came. I managed to get away from the house for a couple of days with my sexy things in hand and I made my way to the 'great out doors'. Well, that was the story anyways. I wasn't really sure how 'outdoors' the cottage was going to be but it didn't matter because I wasn't interested as much in the cottage but what I would be doing at the cottage.

The excitement in my mind during the drive became too much to take. I had looked forward to such an outing for years and it was getting closer and closer the further I drove. I had to pull over and put on some silky undergarments for the drive because I was so excited. I went into the back of the car and pulled out some of my favorite items. Black was the theme. Black stockings and black garter belt, black panties and some old black opaque nylons that I encased my arms with. I put back on my regular clothes on top and had to fight the urge to masturbate. After all, I had to save myself for the afternoon to cum and after what seemed like an eternity, I soon arrived at my destination. I took the stockings off of my arms and tucked them into my suitcase as I grabbed my things out of the car and headed towards the front door.

It was a very nice here out in the woods and in such a secluded place, far from cities and towns; it became easy to forget about the rest of the world and just enjoy being in this wonderful place surrounded by nature. I walked up to the cottage and Nicole was at the door with a smile and she wore a lovely red teddy. Her seamed stockings and heels accented the teddy she was wearing and she passed a glass of white wine to me. I gave her a hug and kisses and thanked her for inviting me to her place and supporting me in my quest to step out and experience things. She smiled and offered a toast to a relaxed and fun time. I entered into the cottage and was greeted by Jasmine, a stunning girl with legs to die for and a smile that made me feel welcome and most of all, comfortable. Both Jasmine and Nicole had already been relaxing and they told me they were happy that the bi-virgin had arrived.

I was shaking and very nervous and I guess it was obvious but they both calmed me down and told me to take my time to relax and not to rush. The cottage was lovely. It was an open concept and the only walls were ones that were more like space dividers that separated the rooms from each other. Nicole showed me around and let me know that I could use the purple bedroom. It was beautiful and very comfortable and the ceiling was completely open so no matter what room you were in, you would see the beautiful wooden beams that stretched across the whole cottage. Even the bathroom was fantastic. The shower was large, tile and all glass and immediately nasty thoughts crossed my mind. There was enough room in the shower for a dinner party. I'm such a perv.

We went to the front room and sat down, chatted about the place and enjoyed the wine. I was finally starting to relax and really forgot that I had some sexy clothes on under neath my jeans and shirt. When I remembered this, all I wanted to do was to get out of my normal clothes and slip into something comfortable, as the saying goes. And soon enough, Nicole mentioned to me that at any time that I felt like it, I could go into the bathroom and freshen up. She had a little twinkle in her eyes that got my blood moving.

As I was finishing my wine, we realized that it was almost time to have a bite to eat, in about 15 minutes or so, and Nicole asked if I could help. In joke I replied, "If was knew you needed help in the kitchen, I would have gotten a maid's outfit."

Nicole just smiled, grabbed my hand and led me to her bedroom. She opened up the closet doors and I just gasped. I couldn't believe all the beautiful outfits she had and the number of sexy shoes. She reached in and pulled out a stunning maid's outfit and said, "See if this fits, honey." She smiled as she looked me up and down and left the room.

After staring at myself in a mirror for a while, telling myself that it was ok, I got dressed in the maid's outfit. The fit was perfect. I put on my 5" black patent leather heels, my favorite black, fully fashioned stockings, garter belt, wig, apron, hat and some make-up. I stepped out of the room and noticed the 2 pairs of eyes checking me out and the smiles that accompanied them. My heart was just pounding with excitement. I smiled back and said, "How can I serve you?"

Jasmine didn't miss a beat and told me to get a new bottle of olive oil from the top cabinet. I noticed a step ladder in the corner, grabbed it and went to fetch the oil. I thought that it was just so Jasmine and Nicole could look up my skirt so I made sure that they were able to get a good glance at my swollen member tucked in my lacy panties as I took my time reaching up to grab the bottle. I did more duties in the kitchen and began to really feel relaxed and comfortable. It was at this time that my nervousness went away and the evening progressed. So far the reality was better than the fantasy.

We had supper out on the patio. It was just marvelous. There were no neighbors at all, just us three girls, looking hot and enjoying the company and food. The only sound around was the sound of nature and our laughter. The evening was starting to cool down a bit so we retreated inside to continue with the evening.

Inside, the music was on and Jasmine and Nicole sat down on the couch. I decided that it was time to change into something else so I asked Jasmine if she thought that it was alright if I changed into something else for the evening. She looked at me and smiled. I started to strip out of the maid's outfit to the music for them both. I slowly peeled off my layers, not that there were many. First went my maid's hat and apron. Then the dress fell to the floor. All that was left was my undies and my bulge in my panties. Slightly embarrassed, I put my hands over the bulge. Nicole got up, grabbed my hand and led me to the bedroom.

"I told Jasmine that you like to exhibit yourself so she decided that we are going to put on a lingerie show for her."

With my eyes wide open I exclaimed, "You bet!"

We quickly closed the door behind us. Jasmine yelled out to us,"Open the door. I did not tell you that it was ok to close the door."

We opened the door but still went around the wall so she couldn't see us directly but we knew she could see some things in the mirrors reflection.

Nicole picked out a lovely pink and baby blue night gown and told me to grab something from the closet. It was like shopping without the nerves of being in a store. I then saw a beautiful see thru hot red number that was just stunning. I pulled it out of the closet and Nicole commented that Jasmine bought that for her and it was one of her favorites. "She'll love to see this on you as red is Jasmin's favorite color.”

We got dressed and slowly walked into the living room to parade ourselves to Jasmine. She sat there with her wine glass in her one hand and a flogger in the other. "Don't worry about that," Nicole said to me. "She just likes to play with that as a warm up for herself."

We modeled the lingerie, playing and rubbing ourselves to help stoke the fires of the evening. We continued to try on and model various outfits until Jasmine told us to choose one outfit and leave it on. I went to my own lingerie and pulled out a burgundy corset and had Nicole do it up properly. Until then, I had only put it on myself and having someone properly tie it up was breath taking. I put on my new stockings from secrets 'n lace, put on a pair of platform heels that Nicole picked out, a skirt, and I almost forgot to put on my favorite cock ring. One ring for my balls joined by leather to the other ring for my cock. I had to struggle to get it on as my hard-on was almost already too big. We touched up our makeup and made our way to the living room. Apparently, Jasmine had been busy too.

On the floor was a large vinyl mat and Nicole giggled when she saw it as she knew that Jasmine had a plan for us all. I sat down on a chair but then moved over to the couch to give myself a chance to sit beside one of my lovely hostesses. Nicole and Jasmine started to kiss each other and I was fascinated by just watching the two of them, at least for now. Jasmine sat down beside me and said, "Do you know how to suck cock?"

I replied, "Maybe. I haven't sucked cock but I enjoy it myself."

She motioned to Nicole, and Nicole came over. Jasmine stood up while Nicole removed her panties. This was the first live hard clitty that I saw and I could not remove my eyes from looking at that lovely cock. She sat back down and Nicole proceeded to please Jasmine, all the time showing me and pointing out to me what she likes about having her cock sucked and how. "I like it when she fondles my balls while deep throating. Such a lovely feeling."

"And it looks good too," I said.

"If you promise not to bite hard, you can help Nicole." And she winked at me. The moment of truth had come. My first cock. Gleaming with Nicole's spit and rock hard from all the teasing, I got down on my knees beside Nicole and kissed her. This was my first kiss with another cross dresser and it was hot. We moved our mouths down to Jasmine's cock and began licking it up and down the shaft while fondling her balls. I moved up and took it into my mouth. It was warm and hard and I just lost the sense of it being my first time and I just started to suck and suck it. I was really getting into this and felt a hand on my head. "Slow down girl, I'm not ready to cum just yet."

I looked around and Nicole had gotten up and brought over to the mat a weird but lovely looking device. It was two vibrators that were connected to each other by a foam-like board. Placed on the floor it was a strange sight but then I realized what it was for.

Nicole removed her panties and then she came over to me and removed mine. Three beautiful cocks all were standing at attention for the ladies in the room. Nicole put some jelly on her man pussy and slowly lowered herself onto one of the vibrators that was sticking up through the board. She motioned to me to join her. Luckily the smaller one was for me as I did not have much experience with anything like this up my butt. I lubed myself and Jasmine slowly helped lower me onto my vibrator while my legs went over Nicole's legs. It must have been quite the sight. We were so close to each other that our balls and cocks were rubbing against each other. Jasmine reached over and turned on both of the vibrators and we were filled pleasure that we couldn't control.

Jasmine was in full control and I didn't mind at all. "Kiss each other," Jasmine demanded and we both started to kiss. Nicole reached over and played with my cock so I followed suit and began to play with Nicole's. This was sooooo hot. Jasmine was telling us what to do and a vibrator was up my ass, being controlled by her, while Nicole was in the same position. I thought that I would just explode but Jasmine must have caught the signs and she stopped us from touching each other. All you could hear was our heavy panting and the buzzing of our asses being pleasured.

Jasmine walked to the kitchen, got the bottle of extra virgin olive oil and began to pour it onto both of us, covering our cocks, bodies, arms legs, everything in warm oil. She then pulled up a chair, removed her stilettos and presented her legs and feet to us.

Following Nicole's lead, we both began to suck on Jasmine's toes and worship her feet and legs. She pulled them away from us; then she lowered them to our cocks and proceeded to give us both a foot job at the same time.

I was in fucking heaven! This was awesome and it all felt totally normal as if I had done this many times before. Jasmine started to play with herself while Nicole and I enjoyed the foot job, anal buzzing, and all the oil. I could not contain myself anymore and yelled out to Jasmine, "I can't hold it. I'm cumming."

At that note she got up and the started to blow both our cocks at the same time. I came in waves, shooting my load in her mouth, on her face, and all over Nicole's cock. Nicole soon came too as if to begin cumming where I left off. She covered our cocks and Jasmine's face with his hot sperm.

Jasmine then began to kiss Nicole with our cum all over her face and Nicole began to lick it off. Watching this made me want to join in and then Jasmine allowed me to have some cum too. This was better than fantasy and I was in heaven. I am such a perv.

When we finished kissing and getting all the cum off of Jasmine's face, I looked around the cottage and saw that there were four other cross dressers now in the room, enjoying the show. I did not even hear anyone else come in but it was obvious by their expressions and actions that the show was a winner.

More on the evening in the next chapter...