Bill Meets Jessica Ch. 02

Following chapter 1. Jessica and Bill (Alexa) meet again - Friday. Jessica wants another meeting.

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I received a message from Jess asking if I wanted to meet her for coffee up town, a week had gone by since our initial meeting. That was a pleasant surprise for me.

I texted "Ok, we meet in half an hour," knowing where we are to meet, soon after I received a text, "meet you there."

At the coffee shop waiting for her I ordered beverages for us, which had just been delivered by the waitress as Jess came in, short ankle boots, knee high leather skirt, light pink blouse, leather jacket and the unforgettable calf gloves.

I got up to in order to greet her, Jess reached me with a short cheek kiss and sat down.

"It´s good to see you, how´s business?" I said.

"Oh, business well, yours I suppose well also, are you free for the weekend as from Friday night on wards?" Jess said cutting the chase.

I had a possible date, which I would automatically cancel. I had not been sure if Jess wanted to see me again until now, even though we had had a good time, I said, "Hmm, Well.." and Jess cut me off.

"Sorry this invitation came up on short notice, I had a work meeting this upcoming Saturday and it was just cancelled so I decided to reach you, last time was good for me and decided to ask in person."

"Yes Jess, I´ll see you. "

Jess looked at me, "Am I spoiling other plans?", trying to find what was she cutting off.

"Not really, and I can cancel them off. I wondered if we were ever going to get together again, not knowing if it was a onetime event for you." I said spilling my thoughts out.

"No, no, Bill I very much enjoyed my time with Alexa." Jess said, giving me a sensual look and happy that I'd drop whatever plan I have for the weekend in order to see her.

"Interesting, I thought Alexa, was an every now and then thing."

"Bill, I have to get going, see you on Friday and we will see how deep it goes." she kissed me this time on my lips, and scooted away not answering my comment about Alexa.

It's Friday, and I'm knocking at Jessica´s door, she greeted me with a kiss and to my astonishment she was in a track suit, it was just different to the way I had seen her when I met her the other occasions. Jess said nothing but noticed my confusion, "Bill dear, would you settle drinks for us?"

"Certainly Jess." and went to the cabinet and served scotch for both of us, ice for Jess, water for me. We sat down, Jess on the sofa with her legs folded, me on the armchair and spoke about a number of current topics of our daily life.

Jess got up, and tanked both our glasses, as we loosened up Jess found the right moment to mention, "Are you up for a weekend with me, Alexa? she quickly added "If we do go out, there won´t be any visible signs of Alexa, although you might be wearing some underwear belonging to her."

I looked at Jess, and she smiled wittingly back at me.

"Oh." I said.

"Let´s see, if you still be interested in walking this path and how far." Jess said.

I looked at Jess quizzically, "What do you mean by how far will I go?"

"Alexa, as and if we do carry on in this relationship, I´ll always be eager to make you in every possible situation a little more acquainted with the feminine side, so it will all depend if you are ok with it. I guess it's a matter of trying it out." she said using her preferred name for me.

"Speaking about that and thinking out loud, if it does not interfere with my daily matters and if we get along well, we can give it a try Jess." I added, trying to understand her, " It seems you find yourself comfortable with me, but it would be much easier if you had physically a woman with you instead of a me."

"Yes and no and since you brought the issue up, I can tell you Alexa." making an emphasis of the name as she mentions it, "I could be with a woman and matter of fact I have been, and there´s nothing wrong with it and would be accepted in my business, but it makes it easier with a man, independent of what goes on behind my back, because that won't change. Maybe if women ruled the world, then matters would be different."

"I see." I said.

"Following the thread, women can get very violent if the relationship goes wrong, with men it seldom does, and I prefer a peaceful ending if it happens, so for instance it were you, I definitely know that you won´t make an issue, independent of how hurt or not we could be if we become a couple."

"Sometimes, but not all women are that way." I said.

"Let me carry on, feminizing a man has it´s twist to it and I love it, further more I can mould him as I want as a mistress does with a slave, and since he does not have a female parameter, inner feelings and dialogues, which a woman has already incorporated by nature. Men are simpler in their issues and in addition to all, I have to deal with myself, which is a lot I can tell you, and if I add another female, my emotions would in many cases explode or implode not knowing which way they head to and dealing with them could make me regret what I say or do sooner or later. In my case Alexa, when I find the man suitable enough to share sex and life with, I already know he is submissive knowingly or not by him." Jess said and looked at me certifying that fact.

"Oh." and blushed knowing I'm submissive to her.

"In the case of a woman, she would also have to be my submissive. My own experience tells me, that at some point of the relationship they switched, stopped being submissive and that made it difficult for me, so I ended them. Alexa we could carry on with this conversation maybe later, now let´s stop here. Speaking of submissive Alexa, which you are please take note that I'm the one to decide when and how we are to have sex always from here on, starting right now. Women are superior to men, so revel with this fact and enjoy being fem with me."

"Have I, a say?"

"Not at this moment, understand dear Alexa, I will be taking you were I want and enjoying ourselves in the process. I gather that for the time being you are in for the ride also, yes?"

"Yes, Jess." I said.

Jess came up to me gave me a kiss, "You are wonderful, now why don´t you start getting ready, I've got the guests bedroom ready for you with the items for tonight, run along and get ready Alexa, it´s time to get you feminine for me."

"Ok let's see what is there." I said and started my way to the bedroom.

"If help is needed just let me know. Ah, remember you are a pussy, no penis is allowed to be seen." Jess said.

"Yes Jess." I remembered how it was last time and made a note of it. On the bed I saw condoms, the other night´s black latex panty, stockings and opera gloves, a necklace, pantyhose, corset and a long dress. Also there a different wig for this occasion. I called Jess, she came over, and I mentioned there are things I cannot put on by myself or even know how to.

"Alexa, put whatever you can by yourself and then call me over."

"Ok" I said. I started with the latex panty and just before getting it right up I got the condom out of its pack and rolled it on, with a huge hard on, which I could not get down to get dressed as she wants. In the meantime I passed onto the latex stockings and found them a little complicated to put on, which made my penis get back to normal, so I did put it into the requested position for the evening and pantie concealing it. Up came the gloves and guessed that the pantyhose is to go over the latex stockings, so I did it without consulting. Did not find the boobs that I had used the other night, I carried on with the boots. Having finished I summoned Jess. She had just finished her shower and came over with in dressing gown and the boobs, my boobs. I pointed to the corset.

"Oh yes, let me help you Alexa, but before let me put your boobs and holder on so that they fit correctly on you." Jess said.

Jess bit my nipple slightly and felt it, "Ah." I said.

"Ok they are ready, sweetie." Jess said, now getting the corset fitted it on me and tightening it, once finished, she pointed at the dress and the rest of what was on the bed, "Alexa do you need a hand with that also?"

"I don´t know, let me try by myself and see."

"Good girl Alexa." Jess said, and left for the bathroom. I noticed that every time she had a chance the Alexa name came up, in a sort of get used to it manner. I thought to myself, if this goes on a long time, when I hear Alexa in any place I´ll be turning around, that could become a problem for me. I got into the dress which had a zip at the side, once on, it looked ok on me, the material was somewhat stretchable, with the corset on it seemed to give a better waste shape, at least compared to my normal look. The necklace and wig were added and then waited. Jess came over with the same outfit she had on last time, latex cat suit only revealing her neck upwards, latex panty covering her crotch with the feel doe opening which I knew it had, which in turn was covered by a pvc short with zips at its sides, high heel boots, makeup and the same necklace as me.

"Alexa, let me fix that wig a little." she did, "You are nicer now, but better after makeup." Her latex hand got mine and we headed to the bathroom. Jess finished with the makeup, which she enjoyed applying.

I saw she had the feel doe in place and ready, " You have a hard on." I said.

Jess laughed, "God you are hot" she said to me.

"So are you in latex Jess." I said.

"Come Alexa, come with me let´s have a bite, us girls eat but not too much in occasions as these, ready for what might happen next." Jess said.

"Just as well I'm not hungry Jess." I said and got a disapproving look. I accompanied Jess to the kitchen got sandwiches and took them to the living room.

Jess asked if I preferred wine or to carry on with whisky, I said the later. So she came over with the fix. Jess asked me to sit with her on the sofa, she folded her legs and asked me to do the same, which with difficulty was able to finally do, but not quite the same way.

"Oh, Alexa there´s a lot I have to teach you." Jess said and reached out to me and deep kissed me. I knew I had to be soft and girlish for her, so I let her do the move on me.

"You look so sexy Jess." I said. There´s soft music playing in the background.

ess kissed me again, "Alexa it´s lovely being with you, and you are learning well." Jess looked at me in a way as if to tell me of some facts or a serious matter that had to be said.

"What's on your mind?" I said.

"Alexa, as you have noticed, I enjoy leather, latex and some other textures, but the first ones mentioned mostly. Last time we were together I dressed the same as now, because it makes me feel sexy and with authority over you, and that turns me on. I do have other clothing and different combinations to enjoy ourselves with, with this I'm t letting you know, that in the future if we get along when we meet and you see me dressed this way, I want you to remain in silence and let me lead you in every way, you are only to speak to me when spoken to." Jess said seriously.

"Wow, that´s a load of authority towards me Jess." I said. The last bit came out from my voice, sort of feminine. Jess kissed me again.

"You´ll get accustomed to me Alexa, as we progress and if you do not obey me, there could be some bondage and or discipline, by now I guess you already understand where we are slowly heading to? Sometimes I'll want you to behave badly so that we can play the bondage games and other ones."

Now I understand why most of the relationships did not reach a long period of time, I said to myself, then answering to her, "Ok Jess, but I prefer games in which we both consent, and not you overruling me when you do not like or agree to something."

Jess kissed me long and deep, "Alexa if I´m right as we build this up, by the time we are a stable couple if it comes to be, you will see that in certain situations looking at each other here or anywhere no verbal language will come in handy, because you´ll know by looks or body language, what is to happen or requested by me to you. Let's see if we are both interested getting there." Jess kissed me this time passionately, I accompanied.

I noticed that Jess, simply ignored my comment on having mutual consent. I´ll see if I´m in for the ride I thought in silence, then added, "It is difficult to keep control of myself when only being allowed to follow suit, being you who leads."

"Maybe if we are lucky after this weekend you´ll slowly start finding your place with me, I have patience if you are willing to learn. Don't worry I'll control you if you want to become mine." Jess added.

"I see you are becoming more dominant with me, it seems a prelude of what is to come." I said.

"That is good because you understand and being submissive as you are will make it easy to obey me." Jess said happily.

"Will it be always that way?" I asked weary.

"Uhm, yes." Jess kissed me deeply.

"Jess did you ever get to that mentioned state of non-verbal communication with someone?"

"Yes I did Alexa, but the girl I was with then, suddenly switched and wanted to lead, it did not work out, I did try to be submissive showing the interest I had for her, but no, I'm dominant by nature. Strangely it end well in a friendly way. The process hurt us both, but we knew we would could not make it work." Jess said.

"Are you still in contact with her Jess?"

"No, let´s get back to us, Alexa." Jess, said. She kissed me, a love song was playing that she liked, got up took my hand making me stand, then her arms surrounded my waist and we started to dance. Her heels were higher than mine so she was taller than me, not knowing what to do with my hands since she was playing my role, I moved them up onto her shoulders first, then slowly surrounded her neck, this must have given her some strong feeling because I felt her arms press me in, and kissed me our tongues playing with each other sensually. We ended up dancing and kissing longer than I ever thought we would, her leg going into my crotch, and me touching hers.

At some point I let go and asked her for a drink, "Yes Alexa, let me get you one." Jess said.

"Babe let it be a water, I need to hydrate." I said.

"Yes love." she said.

It all sounded surreal as I processed it within my mind, only clear to me that Jess is dominant to me and I'm submissive to her. I´m playing my part in this, but she is very good being the top, I thought to myself. I drank down as I normally do, and Jess got hold of my hand, "Alexa, drink as a girl." she said in an imperative voice.

"Yes Jess, sorry I'm very thirsty." I said and thought, never missing a thing.

Jess got hold of my hand and gave me a tug, "Let´s go baby I want you now." I just followed her and let her do everything, it felt strange yet not uncomfortable, but I had to hold myself back many a time, having to make a shutdown in order not to try to take control, very difficult, if not stressing. At her bedroom she unzipped my dress and off it came.

"That went quick." I said.

"Alexa, would you get your boots and necklace off, this time only please, whilst I get ready for you?"

"Are you in a hurry love?" I asked.

"You bet Alexa, I want you now, now." and unzipped the shorts, the feel doe appeared already placed in her pussy, I had not even been able to get the necklace off, she put the latex gloves on, got the condom on in no time, got the lube, looked at me and said, "Alexa I want you ready for me." and this time it felt as an order. I lay down, she got a pillow, put it under my waist got the lube going, smartly and efficiently lubricated me, threw the lube away, and came up to me, next I knew her head was going into me.

"Please Jess, be gently with me." I said.

"Yes love, I´ll go in slowly." and she did, head went past slowly.

I moaned a very low, "Ahhh." and in one move she was in me, "Uhmmm." I said, my prostate already feeling her, she pumped me no more than six times and Jess was having a huge orgasm.

She yelped, "Hahmm, Aahh, AAAhh." then pumped me hard and another orgasm, "Ahmmm." she carried on wild, I was building up and in her fifth orgasm I felt I was about to have my orgasm when she was ending one of hers.

"Aahh, Mmmnn, Uhmm," I moaned, as the milking continued lasting until her seventh or at least I thought it was. After that she collapsed on me with one last thrust. Jess had previously put a latex sheet on the bed to avoid stains and leeks, so when she rolled off me she just remained there, silent, catching her breath. Me again, feeling my butt gaping the emptiness and knowing that I had my orgasm also, luckily, everything went so fast that I thought I was going to remain waiting in frustration. Then Jess got up withdrew the condom and with a gorgeous look in her face came up to me and fiddled in my panty and got the condom out, slid it on to her feel doe and then slid it off, knelt on the bed, and came towards me.

"No, please, no not that." I said knowing what was to happen.

"Open up Alexa" with her feel doe on my lips, "Eat me." Jess commanded.

"Please, I beg you." I said. I was spent and not eager to do this, but she insisted and the head was on my lips and she pushed in forcing me to open for her and in she went.

"Alexa, you are my girl and have to get accustomed to my demands, I´m your dominant and that is the way it will be with us" she said. Swiftly fucked my mouth and in the process I sucked everything off it. Jess withdrew satisfied and then deep kissed me.

Jess got her feel doe off her and lay down beside me and drifted hugging me to sleep.