Bill Meets Jessica Ch 03

Following Friday night, Jess gets demanding on Alexa. Alexa (bill) still in a way trying to get back to her/his senses.

After last night we woke up sleepy. Jess got off the bed pulling the blanket to the floor and disappeared, later she came back looked at me and said, "Alexa you look a mess, come dear one, it's time to get up and have a shower."

"Ok." I said in a drowsy voice.

Jess looked fresh and radiant, already showered, just wearing panty and bra, her body nice by nature, well her parents had a lot to do with, I thought. My body dragged itself to the shower my mind somewhere else, it took time to get them together again. Watching the water bounce off my skin and enjoying it as a kid was most relaxing to me, when finished I found a set of underwear for me in black. Oh no, loving Jess is going to be quite something for me, but then again she does possess that sex-appeal and once drawn to it, I have found it impossible to let go. I have to see the bright side to her and get accustomed to the underwear which covers more parts of my body than I'm normally use to, convincing myself.

Jess´s head popped in, "Remember Alexa, you have a pussy."

"Beautiful Jess, do you always have to remind me?" I said, not quite wanting to carry on with this, but nevertheless I put my penis back to conceal it and wondering if I'll get through the weekend, knowing that once spent all kink tends to disappear from existence for me. I do know I like her, maybe that will make the difference.

"Come on be a sport dear." Jess said guessing my mood and not adding anything else.

I felt the bathroom and looked for Jess, could not find her at first, so I called her, "Jess."

"Here in the bedroom." I went there and I saw her deciding what she was going to wear. She had pantyhose on and asked me if I would to put on the pair she had set aside for me.

"Yes." I said, in a more pleasant manner and put them on. She came over and gave me a short soft kiss I accompanied her in the move. Jess looked at me as if in love, relaxed.

"Alexa, when we are here at home, I'd like if you would wear a dress, skirt or similar for me, I´ll get some for you and here get your boobs on" Jess said and she helped me with them by getting the bra unhooked and hooked up again, "Choose a dress Alexa". I did, the first I saw, it was beige or brown, so Jess got a pair of brown boots for me.

"Jess, I´m astonished at the amount of clothes and foot wear you have for the partner you have decided to share your sex life with."

"Alexa, I have a good number of items for my sex life to be fulfilled as I like, and admit my income is excellent which allows me to cover my eccentricities. It also happens that most of my male partners have had nearly always the same size, I find it incredible that every time I have come across an interesting partner they have the same size, excepting once, but he did not get past a coffee with me."

"That is strange." I said. I slid the boots on, and Jess passed over a wig for me.

"In time you´ll do all this by yourself and enjoy dressing up for me." Jess said.

Jess got a pair of jeans on, shirt and short ankle boots. The jeans had the right fit on her, the sexy look.

Jess looked at me, "Let´s have breakfast even if it's almost midday."

"Yes, I´m famished." I said.

Jess looked at me again, "Remember your female manners, please."

"All I said is I'm famished, don't nag at me when I haven't committed a crime to your standards."I said.

"Are you moody? "

"No, at least I don't think so, maybe you are pushy."

"No, I'm not pushy, or at least, not what I call pushy."

"Can we slow down and leave these comments, please." I said trying to forget and pass onto breakfast.

"You are moody."

"Ok, I am, does that make you happy, good, can we have breakfast?" looking at the toast.

"I'll let it go now, in the future we are to find a better way to communicate."

"Ok with me." Meanwhile the coffee was making itself, Jess went to apply some makeup and soon was back with me. Jess looked at me again. I could not hold myself back, and the former comments which alerted and prepped me up to say, "Jess, my male features cannot change, are you sure you don´t prefer a girl with you?"

"Alexa, I´ll let you know when we do not get along. Your male features are nothing to worry about, I take you whole, including your traits which are the ones I like. As for your physical side, with the right makeup you look good to me. Baby if I'm in the mood I´ll fuck you as you are dressed now or even with less on, you don´t know me yet, just wait and see."

"Ok I give up with the issue at least for today." I said now enjoying the toast, jam and smell of coffee freshly made.

"Last but not least, I was wondering if to put some makeup on you now, but was not sure because if we do go out, your every day face has to be available, so I decided otherwise, if we stay at home the makeup will come on, so don´t get fuzzed up. Of course your boobs and maybe the footwear have to stay at home also."

"That's good to know."

"We could in a moonless night, go out somewhere with you in your feminine attire, would you, Alexa?" Jess asked.

I went blank and white, Jess watched my face in amusement. "Even my voice is deep and thick would you like to be in such a situation with me?" I said.

"I have no problem with it. I want to see how you sway with all your emotions and I might be pushing you with that" Jess said.

"Jess, let´s not go deep into this, we are just starting and it is freaking me out."

"Alexa, I thought you were more audacious, nevertheless I like it and it does make you even more vulnerable. I am recollecting that you are moody, vulnerable, down to earth, sexy not in a feminine way yet, we have to work on that it will require time, taming and training. Guess what, I like taming and training my girl!" Jess added and giggled.

I went red and said, "I don't know if I can go that far." and Jess liked it even more.

We had a long conversation throughout the afternoon.

"Alexa." looking at me seriously and said, "Would you like to grab a bite at a very nice quiet restaurant I know?" Jess asked.

"Today I know you are teasing me, so I decline the invitation, but thank you anyway." I said.

"Ok, but we do need to shop something for tonight, so I suggest Alexa, this time get your wig, boots, dress and boobs off, but do please leave the rest on, I find it kinky when we both know that there´s something else going on. Is it alright with you Alexa?" Jess waited for my answer.

"Ok, I´ll go to the bedroom and get ready." I said not very convinced and she knew it. I walked there, sat on a chair, got the boots off, then the dress, wig and boobs. I got my pair of jeans on as well as a T shirt and sweater, Jess popped in.

"Oh, good Alexa, you left the rest on?"

"You had asked me to, you are so controlling." I said in a way that seemed she was hustling me.

Jess laughed, "You have no idea."

So looking more of a standard guy we went off to shop. We arrived there and got out of Jessica´s car. Walked into the supermarket and felt weird, knowing all I had under my clothing. Jess, knew that I had that feeling, and came up behind me and touched my butt, and said, "Hello sexy."

I went red again, "Have you got to?"

"I´m truly enjoying this." she added.

"You are mean Jess." I said.

"Yes I am and it's a way of training you." Jess said.

"What do you mean?" I asked.

"The more exposed you are the quicker you'll get accustomed to it and the less worries you'll have." Jess said.

"The problem here is that I'm a guy, if you have not yet noticed Jess." I said trying to get her to reason.

"I know dear and guess what, every step we go down this road will make us bond deeper." Jess said.

"I do not agree with you." I said,

"Let's see if we break it down and say that we are attracted to each other, would you agree?" Jess asked.

"Yes."

"Next, I like your skin, you like mine? Jess said and asked.

"Yes very much so, the truth, I have not ever felt in a woman a skin as yours." I said and this time Jess blushed. I took her a moment to get her words flowing again.

"Do you want me to go on?" Jess asked

"Since you are at it, yes." I said.

"This might get me very turned on if it goes on as it is, I may lose my head, I might not call you Bill, but you know who, do you really want to go on now?" Jess said looking at me in a sexy way.

"No I would not like it to happen and would not know how handle myself if anyone heard you calling me different than Bill."

"Could we leave this conversation for another place and moment?" Jess asked.

"Yes I agree, it could get out of hand and we don't want that to happen." I said.

"Scared of feeling or losing control?" Jess asked very interested.

"Hmm, well maybe both. I would have to see if it's infatuation or far more."

"Would you tell me once you know or feel that you have an answer to that?"

"Yes I will, even if it is not what you would like to hear?"

"Definitely, same I'll do with you, although I have a clearer look of it than you do now."

"Ok, I understand it's not the place or the moment right now, but I'd love to know what you really feel."

"You will Bill, I promise."

We bought everything and made our way back to her place. I helped her carry the packets.

"So how did you feel Alexa, you know, using the clothing?"

"Strange because of the clothing, including the role to play you have given me in this relationship. I do not quite know how to behave, my mind flips." I said.

"I saw you well having been the first time out, independent of the thoughts and feelings we've started sharing."

"If you say so, although I´m not that sure."

"As I mentioned before, as we go along matters will find their way. We could even marry, who knows." Jess, added.

I laughed out loud, but Jess looked at me seriously. Ohh, I said to myself I must have truly fucked up in something I said to Jess. I tried to make it easier on myself, "Did I fuck up?" I asked.

"Yes and no, but that's maybe for another moment." Jess said adding, "I need to fuck you now, you turn me on and gather that you have the innocence of not knowing how much. We have to get to know each other better."

"Ok... that means, now, now?"

"Yes, enough explaining, please go and get ready as I want you, condom, boobs, latex gloves, stockings, latex bra, do get out of the pantyhose set you have on now, and wait for me. Alexa, you will find two latex panties one that you know and the other to go on top of the first mentioned. There´s an additional request to you Alexa, you will find a small dildo there use it to lubricate yourself so that when I get the panty off you, I can be in you without any delays."

In silence I went to the bedroom finding everything set out for me, she had arranged it in no time. I had all sorts of feelings in me. If I had any doubt that I´m submissive, Jess made it crystal clear to me at the same time that she is the dominant and that will not change ever as I see it.

I froze for a minute, Jess came in naked. "What´s wrong girl?"

"I´ll dress up now Jess, sorry." I said meekly. Jess left. I obligingly did as requested and once dressed as requested with only the covering panty still missing, I got a glove that was there put lube on the small dildo and pushed it up my butt, then got it out and more lube went in, having done that step, I put the panty on which pressed against my butt, feeling sticky, wet and cold.

I did not understand Jessica´s quick change of mood. She came over with her cat suit, boots, makeup the extra pair of latex gloves she uses and her condoms, but this time with her feel doe already in place. In silence she handed me the boots to wear, I slid them on. Then she got hold of my hand and took me to the bathroom there she fixed my makeup.

"You look nice now." Jess said inspecting her work.

"You are the one that chooses how I should look."

"Yes, you are right, you'll get accustomed to it."

"Will I?" I asked.

"Yes, if we become steady and everything tells me we will."

"Is there a possibility of vanilla in the future, me being a plain guy?"

Jess sort of grinned at me, "Do you think I'll let you?"

"I prefer not to answer now."

"That is a very good and sensible answer Alexa, that is another reason I like you, you take me into consideration and try to understand me and my likes, even if it's not within your interest. That is rare to find in a man."

She got me up, looked at me and then took me to her bedroom by the hand, got behind me and fondled me, I just let myself be played with by her, she has a certain sexiness as she moves, touches and plays, she then turned to my face and deep kissed me. It is a strange feeling being overpowered by her with total control on everything I do or say.

"Jess." I said.

"Come here girl, kneel your knees on the floor your body on the stool, now open up your mouth" Jess said. I felt a ball gag being placed and tightened behind me, she tied my hands and knees to the stool, she then spanked me slowly at first it got harder as she followed and it started to burn.

"Ahghgg." I tried to yell out, and a muffled sound came out of my mouth, She spanked a bit more and then stopped. Then the second panty was lowered by Jess. She positioned herself as I felt her hands on my cheeks opening me then I felt her feel doe head against my bottom, to no later start making its way inside me, she did not go too hard on me but yes in one swift drive all the way in until I felt her hips, her body now fully placed on my back.

"Ummm." I said through the gag.

She started fucking me, I felt her hips going into me, pumping constantly, fucking me harder now. Several minutes passed by, my prostate at full, my cock leaking, I was trembling, suddenly she went well deep into me, I knew her first orgasm hit her, and again and again now moaning hard. "Ahhh, yes, Mmmm, Mmmm, yesss, mnmnm." She lost control and slipped out of me, so she placed the head in and went for it. I´m feeling such a bitch, she certainly said she wanted one. After sliding into me again in the same way, which she seemed to enjoy this time, she withdrew got up and heard her leave the bedroom. I was helpless there and all I could do is wait. Time passed by, I was totally frustrated. This bitch has left me here, I was going mad. I heard her come back, she stood in front of me far enough to let me see her.

"Alexa, you will learn to be docile." Jess said, knowing I was mad and fed up. She put the latex gloves on, I could see that her feel doe was without the condom, which I guessed she was going to make me suck. She decided to get the condom I had on and got herself in front of me and slid that condom onto her feel doe. With a smirk, she moved behind me again, I felt her hands on my waist and the feel doe go into me again, it felt different and cold, she pumped for a while and made the orgasm noises, had she more I do not know, but she stayed in me. The ball gag was released from me, I stopped drooling at last.

"Please, stop." I said. She did not speak but her answer to my plea is replied fucking me more with a hard last thrust, then withdrew and came around, got the condom off and said

"Open up girl" she moved into my mouth "Clean me up." Jess ordered, something happened which was not in my books, and don´t know if in hers, Jess has a good orgasm when I was sucking her, but hardly made a sound just a slight "Ahhhh."

When Jess was satisfied she withdrew, kneeling down to untie me. I moved from my position and got up helping myself with my hands on the stool. From the floor Jess looked at me. I reached out my hand and helped her up, she held my head and kissed me, and took me towards the bed and pushed me there and carried on kissing me and touching me all over. After a while, she got the feel doe out of her, got up and headed to the bathroom.

"I truly enjoyed you." she said.

I just looked at her wasted and seconds after I fell asleep.