Bill Meets Jessica Ch. 01

Making my way to my car, my eyes caught sight of her, the car's bonnet open looking into the engine, I wondered if she had any clue regarding mechanics. Checked her out she had a leather dress, boots up to her knee, a slim body, and too good looking to know about engines, so I thought. Out of curiosity and more I went over and offered her my assistance. Her eyes posed on me and went through me as if she had an x-ray machine.

"Hello, there." she said, holding a second before saying, "I've got a battery issue here, have you got battery cables to make it start?"

Wow I said to myself, what a girl! "No, but I can take you in order to buy them or get a battery replacement." I said.

"Thank you, I accept you offer. Let me get my things." she said, and put her overcoat and gloves on, got her purse, closed the car and followed me to where I was parked.

"By the way I'm Jessica." and reached out her hand.

"I'm William, Bill for most, good to meet you Jessica." my hand held hers just a little too long, feeling the soft leather.

"Likewise Bill." she smiled as if picking up information about me.

"Lovely leather you have on, it makes your beauty stand out."

"Thank you." and smiled again, now in an assertive way, looking into my eyes. Started the car and although already late I still had to check, but as feared, the shop was closed, we asked a passer-by, but he did not know any other place to send us to.

"Jessica, we won't get this fixed today. How far are you from your destination?"

"Not too far." Jessica said and mentioned the address.

"Would you want me to drop you off there?"

"Would you?"

"Of course."

"Thank you so much Bill, you have gone way out in order to help me."

"Jessica, if I were in the same situation, I'd like someone to give me a hand." I drove on.

A few blocks later Jessica said, "It's there and pointed to a house."

I stopped at the driveway, "Here we are." I said.

Jessica got out of the car, thanked me, stood a second turned before closing the door and said, "Bill would you like a coffee, have you got time?"

Jessica had clicked with me, I had not even noticed yet, guess it's a female prerogative not to show or make things obvious. I would find out later about the clicking .

"Well, I'll make myself free, it's not often I get an invitation from a beautiful girl." Jessica smiled at my compliment, "I'll be with you in a second." phoned my friend and called it off. We went into the house and followed her to the kitchen, she got the coffee machine going. Now I had a better look at Jessica, she is ravishing.

"Make yourself comfortable." Jessica said.

"Thank you. Jessica, for conversation sake and curiosity also, are you married?" just could not hold back with the question.

Smiling at me, "No I'm not and doubt I will be. I'm bisexual, but more into women." Jessica looked deep into me seeking my reaction.

"Oh, I'm bisexual but more into women." I said and laughed.

Jessica burst out laughing, "Sorry, Bill it's just such a hilarious situation and add to it, that when you first came across me, the thought of you being different dangled in my mind. Well I'm right in my assumption. What information did you pick up?" Jessica asked.

"Truth?"

"If possible, yes please."

"I find you so attractive that, whatever I say might be bias in order to see you again, I would do anything with you and for you. It feels different and special being here now with you, not certain if I can put it into words." I said pouring everything out .

"I like that Bill, nice of you. Remember what you have just said. If necessary and it comes to be I'll remind you of it, in order to collect."

"I'll do, Jessica." Not giving second thoughts to what I just said.

"Since we have been quite sincere with each other, can I ask you some more intimate questions, would that be alright with you, Bill?"

"Yes you can Jessica. I think you have a way around me as no one before in my life."

"Bill, you would be surprised, not all men are so open when it comes to something different other than plane female/male sex. Anyway I'll spurt a number of questions, be kind to respond honestly." Jessica said.

"It seems you are going for all or are you fishing out of curiosity?" I asked.

"It's the second part but would want it to be the first. To know it all, and again seeing how assertive I've been in my judgement about you, do please look at it from your side as female curiosity." Jessica added.

"I guess there's no way I can ask you first?" I said.

"I could let you, but since I came up with the idea, I ask, you answer." Jessica said with a smile.

"Ok." I said and breathed out, like getting ready to lift up something heavy. Jessica took another of her long looks at me, never intimidating but reading everything about me.

"Do you want me to ask you on a black or white basis or do you prefer if I'd say what is your preference and then you correct me if there's anything to correct?" Jessica said confidently.

"The second sounds fun, go ahead with that one." I said.

"Ok Bill, here we go." Jessica put a serious face on, and then smiled.

"Right I'm all ears." and relaxed.

"Depending who you are with, you tend to be top or bottom, you have not yet had in your life a relation in which one or the other is predominant. Obviously, cross-dressing is enjoyed by you, maybe enemas, bondage and role play. Being submissive is you true nature and know it. If given a chance a woman can and will rule your life. Am I right up to now Bill?"

I blushed all colours and said nothing.

"Oh, that's a definite yes." Jessica giggled. "Oh, I was missing certain textures and materials are a plus, there's fetish in it."

"Right again." still red feeling totally exposed.

"Don't worry Bill, I'm in public relations and part of my job is reading people, it's not my business to judge sexual preferences and that includes you also."

"Thank you for that Jessica, do you mind if I call you Jess?"

"No not at all Bill. Can you read me?"

"It would be stupid of me to say that I can get a reading of you, Jess."

"Could you just try the exercise and see what you come up with? "

"I'll try." and started out, "You are independent, you like control, tend to be a leader when the gap is there, you may even try to make that gap in order to get what you want."

"Wow, that was good Bill, is there more?"

"You are not very obedient, but yet you want the others to obey you." This time Jessica flushed red, "In sex, I guess at least in your mind, everything goes your way?"

"Again quite right Bill, so then who said you could not read people?"

"Most of this information I shared with you, is picking on how you read me and the things you said as well as you posture Jess."

Jessica was feeling very comfortable with me now, "Bill, would you like to take it up a notch?"

"It sounds interesting, anyway not much to hide from you."

"No, it's true. Let me tell you I rarely like being penetrated, I'm mostly active and use the toys if I need them for the occasion, and have a number of them." Jess looked at me deeply. "I like dressing up for it, and having my partner being dressed by me, as part of a game." Jessica said keeping her eyes fixed on my face.

"Yes, it sounds interesting." I said and nodded nervously, as if about to be caught with my hand in a candy jar.

"Good, I like you submissiveness it makes it easier to develop a fantasy."

I was getting horny as hell, and made slow move to kiss Jessica, she slid me away,

"Sorry." I said, feeling fully exposed with desire for her.

"Are you willing to be my submissive?"

"I think so, yes I would."

"Bill, I'll have to teach you how to move and behave, at least until you are truly start acting somewhat as a fem, which if acted properly does turn me on. That means, in the first place taking a slow move, you are the receiver with me, never forget this, no more moves as you just tried." Jess said already taking over.

"Yes Jess understood."

"Having opened up this door, are your genitals hairless?"

"Wow, you are blunt. No they are not."

"Yes Bill, I am. You are not in any current relationship, are you?"

"No." I said.

"Just wanted to confirm. Is it ok removing bodily hair, the part already mentioned to you?"

"It's ok, Jessica."

"Ok then, Bill are you ready to start now?"

That blew my mind, what determination this woman has, she does not lose a second, I said to myself. "Let go for it." I answered.

Jessica led me to the bathroom. "You can shower after the process." The shaving kit was made available to me. "Do you mind if I do it for you?"

"I guess not Jess." And I removed my clothes. The lather came into action, Jess picked up a pair of latex gloves and put them on, then she stared removing everything, as soon as she touched my cock to shave around, my erection came to full attention.

Jess laughed. "I'll make it go down in a while don't worry, Bill."

"Counting on it."

"Turn around Bill, please." I did and the lather covered my butt and before I said what, the razor made it's pass, so I let it go on, what the heck, let's have fun for one night, I thought.

"Ok then, have a shower, sweetie." Jess said.

Showered and I heard Jess telling me to wait, and did as asked.

When Jess came over she had a latex cat suit on with a latex panty over the suit and high heel boots, all her body was covered from her neck downwards. Again my erection came to full attention and out of words to describe how exciting this was getting.

"No touching, until I let you." She said, knowing I wanted to, desperately.

"Come off it Jess, please let me." Jess smiled.

"I'll touch you instead." And she did, her hands touch my penis and then my shaved parts which tickled me, she turned around and with her butt moved up and down sensually.

"Oh god Jess, that is even worse."

"I know Bill that's why I do it."

"Here are some items I'm going to help you with. First please put a condom on, I want to collect whatever comes from there in a while."

"Ok."I said, all for it. Once fitted, a panty was handed to me.

"Up it goes, here give me one foot, now the other." Jess pulled it up until it covered what it was meant for. excepting for a hole in line with my hole. I felt her hand go into my butt pulled my cock backwards and settled the panty further.

"It's a tight fit." I said, Jessica ignored my comment.

"For your information, I've done it with a couple of men before, one of them did even dated me for a while." Jessica said.

"Have you ever had a steady couple, for a good length of time, Jess?"

"If a good length of time means up to four months, yes. Are you going to ask for us to become a couple? Before an answer is given, let's try this out, if it works maybe the answer is there." Jess said.

"Ok with me." Jess not bothering to ask about my relationships.

A pair of latex stockings were fitted on me, by Jess, followed by small boobs with its bra, I felt a certain sensitivity on my nipples. Jess went over my bra and touched the latex nipple boob and I felt it pinch mine. "Oh yes, they are boobs that make you feel as the real thing. Now long latex gloves a choker and sandals. Come over and sit over here, it's time for makeup." Jess said.

"Ok." I said.

She worked a good deal of time, "I enjoy this, it relaxes me when I paint you up to become fem, now the wig. Oh, yes babe, look at yourself and tell me if you can recognize who you are." Jess said.

"Wow, not for first looks at least."

"You look like a girl and soon will be." Jess said.

"We have to find you a name now, I choose Alexa does it feel right for you?"

I nodded, letting Jess decide as she wants.

"Let's have drinks." Jess, said, and led me to the living room. I saw Jess giving me further inspection, "Oh, dear if we do hit it off tonight, I will have to teach you female moves and manners, carrying on with that possibility, my idea is that when I feel very horny or in the need to extend my dominant side, you are available as my lez-boy."

Not knowing if we would get another night after this one and not giving further thought to it I said. "Yes, dear."

Jess smiled, and had a sip of her drink, and got a small mirror out of her purse and put gloss on her lips. She came up to me, and before starting, said. "Alexa, let me lead this relation, you just follow softly, always in the touching and kissing, ok?"

"Yes." and nodded.

"Here we go Alexa I like your nod, it's with submissiveness, once you learn to be fem it will be natural and our meetings will be very lesbian like. Let me kiss you softly Alexa."

I remained still, her lips brushed mine, she let go and came over again, softly I felt her tongue touching my lips, and again the same, and her tongue started going into my mouth, it all seemed in slow motion. Jess, gently pushed me into the sofa, she's always on top of me, deep kissing and sensually we are touching each other, this seems to go on for hours. Then Jess got off me and pulled her latex panty down and stood there, "Eat me, she commanded."

"Oh yes Jess." I said. That hairless pussy was wet and I was about to dig in as I would always do, but the Jess's bell rang in my head and took it incredibly slow, kissing her lips softly then brushing my tongue going over every fold as it was the only one. I heard Jess moan low, I knew this was going to blow her mind off.

"Let me sit down." Jess said.

She sat I looked at her in silence and made my way back to that nectar, I could see she is going overdrive now. My lips and tongue carry on working, pecking in and out and soon a convulsion sweeps Jess and another and another, I could not believe it, I slowed down and she got hold of my hand and made me go up to her mouth and kissed passionately, "Oh, Alexa, that was wonderful."

She toyed with the fake nipples that made my own ones feel lively, they erected I could feel them, oh god I said to myself, this is good, "Mm." I said

Jess told me to stand. She got hold of my hand and led me to her bedroom, turned and kissed me again, "Lie down dear."

I did. She went into the wardrobe and got a pair of leather cuffs out, put them on my wrists and tied them to the bed frame, then Jess tied my thighs with restraints also to the bed frame, pulling them up exposing me to her. A pillow went under my butt. From one of the drawers, Jess got her feel doe and inserted it into her pussy and put on a panty, which had a hole for it to get through and keep her piece in place. Next came the pair of latex gloves that went over her already latex covered hands, the lube and condoms, she opened the condom packet and rolled it down her shaft, put some lube on it and came up to me, cold lube went around and into my anus, softly fingering me, the a second finger followed, until she considered I'm ready for her. Jess positioned herself on me and looking at me hungry, she placed her tool with her hand as if it were real, it headed for the right place, her whole intention is to see my face when going into me. I felt her tool go into me slowly, my mouth opening with a moan and pain as the head went passed the resistance, Jess played going in an out until the head went in easy, then she carried on until fully in me, her lips kissing mine.

"You are so cute Alexa."

"You are so dominant Jess."

She started moving her hips, I was feeling her going deep into me, at the same time kissing me, I had never experienced this and was all excited, my prostate feeling every slide Jess made, it feels as a non-stop orgasm.

"I'm making you mine Alexa."

"Yes I know you are."

"Let go and surrender to me."

"I am, I am." I said giving into her. She dominates me, knows it, feels it and craves it.

Jess got faster and faster, me helpless before her, moaning like a girl. Jess moaned with me and gave me hard thrusts until she had a succession of orgasms, with more in-discernible noises and moans from both of us . At last she quieted down and remained in me and on me for a while. Immobilized as I was, I could only wait, Jess got off me sliding out of me in the process, I felt the immediate emptiness, she untied my thighs and I dropped them, resting from that uncomfortable position. Jess came up to me and pulled down the latex panty I had on, my penis limp, she took the condom off me and held it, then her lips and tongue went all over my penis, she came up to me and kissed me and her tongue was salty, I followed knowing what I was tasting, she unlocked from the kiss.

"Alexa please open your mouth, be my girl." I opened my mouth and Jess slid the contents of the condom into my mouth. "There you are, good girl. Swallow, it will make you more submissive towards me." Jess said, as if it were hers, I did, not much of a choice at the moment.

Jess kissed me again mixing everything with our tongues. I was untied and rested for a while, moving to my side, Jess lied down spooning.

"Jess." I said, and she put a finger on my mouth to make silence.

"Alexa let's remain this way for a while."

"Ok Jess." feeling drained.

Jess breath was on my neck, she added after a while. "Alexa, I think we can do this again, I like your femininity and role reversal is definitely a turn on."

"Jess I guess I'll learn the way with you."

"You will my love."