Chapter 9: Jessica's Night

At this point I have to say that Melinda had a lot of class for an almost eighteen year old. Her taste in dress, environment, or situations is impeccable!

The restaurant she had chosen for Jessica's special night was a million percent appropriate. It was not inexpensive, but it certainly wasn't the most expensive dinner I had ever hosted, and she understood that price was no object.

Even with those instructions, she asked for approval if something was outside of what she would consider "her limits". I tried to impress on both her and Hailey that I trusted their judgment and I had purposely put no limits on either of them.

Responsibility is part of adulthood, well it's supposed to be, and since in my mind they were adults, they were considered in my mind to be responsible. Though it's jumping ahead in the story, neither ever violated that trust! Mel had also expressed the feeling that asking was part of her being responsible. I didn't argue. I thanked her for her consideration and approved her expenditure.

Jessica had chosen a very dark purple dress, which with her eyes, skin and hair color was perfect. It was fairly low cut in the front displaying her healthy breasts quite adequately but not ostentatiously. The back plunged down almost too low, but it was appropriate as well.

Holy shit. What an ass. Whew!

No bra or panty lines, so I assumed that she had chosen to dress in the same manner as the other two girls had on our other two formal nights.

The four of us made our way through the lobby, turning heads as we moved, and climbed into the waiting limo that was going to take us to the chosen location. I didn't even have to call the limo service this time. Mel had taken care of everything. She had even requested the same driver little realizing at this point that Sandy was always my driver. I guess I had better clue her in, but in such a way that it doesn't generate further questioning. I didn't like keeping "secrets" from either Mel or Hailey, but this was one that needed to be, at least for now.

When we arrived she opened the door for us and as we crawled out for our next adventure, I did my usual pay for what we've received and given her a healthy tip for her troubles and just shrugged my shoulders.

She laughed and observed, "Sir, you certainly know how to pick 'em. One of these days you'll have to invite me to join you."

I looked at her with a grin, "I'll do that Sandy. I think that would be a lot of fun and appropriate seeing as how you seem to draw the short straw every time we call."

"I'm at your service, may I call you Bobby?" She was playing it to the hilt.

"Absolutely. I insist!" Then with a big smile, "Calling me 'sir' makes me feel as old as I am."

"Same time frame as usual?" I asked.

She nodded her head and began to move around to drive away. I couldn't help but notice, as if I hadn't before, what a nice looking young woman she is. I knew what a nice looking young woman she was in more ways than one!

Jessica was tugging on my arm impatiently as we made our way through the front door to begin her "momentous evening".

As we were seated in a fairly dark corner of the club, the waitress took drink orders and gave us some menus. I looked at Mel and she shrugged her shoulders.

"You mean you don't know anyone here?" I asked with a laugh.

"Nope. Figured I'd choose a place that I haven't been before. It's not blind though, I called Jon and asked him to recommend a five star and this was one he suggested."

I smiled at her resourcefulness.

Jon had been quite right as usual. This place is excellent. The food is exquisite, the service exemplary, and the prices not out of sight.

I called Sandy to come pick us up and arrived back at the hotel at about 9pm or so. Jessi was hanging on my arm nervously as I paid Sandy, and gave her another tip she would appreciate.

Sandy whispered in my ear very discreetly, "Thanks Bobby, I appreciate your generosity! Especially you knowing that I don't really need it!"

I smiled at her and nodded in keeping with our discretion.

"So it's her turn tonight?" She grinned.

I raised my eyebrow to her as she giggled, but nodded almost imperceptibly.

She smiled then turned to return to the driver's seat with a chuckle.

I knew I'd have to talk with Mel and Hailey about Sandy and see if they wanted to "play" along. We just had to be very very careful about how we made that happen.

We all made our way up the elevator to the room to continue with the evening's festivities.

Jessica was obviously very nervous as the three girls went into the "other room" to change into more comfortable attire. I did the same, though when I saw them, I guess I was kind of under dressed.

Of course I was finished first, so I took the liberty of making drinks for all of us and set them out in appropriate locations to give Jessi and I the "main stage" and the other two flanking positions. I was rather proud of myself for my arrangement.

I heard giggles and squeals coming out of the dressing room as the three girls were changing into whatever it was they were going to wear for the evening. It was obviously a time for grab assing. Little did I know?

The door slowly opened and what I saw come into the living area of the suite took my breath away. All three had put on some of Victoria's Secret best offerings.

Instant wood.

Jessica kept in the purple theme of her evening, as her skimpy Baby Doll was a slightly darkish light violet, which barely covered her ample chest and was complimented by the identical colored silk panties, which displayed her shaved mound and parts below very nicely.

Mel was in a similar Baby Doll in a light royal blue. The top barely covered her breasts and the panties were just as sheer as the pair Jessi was dressed in.

Hailey? Oh my! Her transparent Baby Doll was in a very sexy pink and did nothing to hide any portion of her breasts. Again, Hailey knew how to display what breasts she had. I was so proud of her new found confidence. Her panties may as well have not been there at all.

Mel and Hailey were smiling at me confidently, but you could see the nervousness in Jessica's face as they all moved towards me on the couch.

Jessi walked over to me and sat gently on my lap with the other two circling the couch and settling on either side of me after picking up their drinks and moving them to the table in front of us.

All I could say was, "Wow," as I looked at all three with admiration.

Jessi took a sip of her drink and set it back down, turning to me putting her arms around my neck. I could see the nerves in her look as our eyes met, but I had confidence that the nervousness would disappear in short order to be replaced with lust, desire and a powerful demand.

She lowered her face to mine and we kissed softly and passionately for a short time.

Both Mel and Hailey moved in close nibbling and licking at my neck and shoulders.

I looked over at Mel who moved in and kissed me very tenderly then moving her face next to the ear away from Jessica, whispered quietly, "Take good care of our sister Bobby. I love you so much."

Mel pulled slightly away and I felt Hailey pulling me towards her. Our eyes locked and I could see tender lust deep inside of her as she leaned in to kiss me very tenderly as well. She also moved her face next to the ear that was away from Jessi and whispered, "Give Jessi as much love as you give to us, Bobby. I love you so much."

Mel and Hailey then put their arms around Jessica and me both kissing Jessi very sensually.

Jessica then locked eyes with me and with a nervous smile whispered, "Love me Bobby. Love me now, please."

I guess that was the "signal" the girls had worked out because at those words both Mel and Hail leaned in and kissed us both on the cheeks, picked up their drinks and walked silently to their room for the night. Just before closing the door, Mel quietly said to us, "Wake up call at 9am guys. Enjoy your evening."

I heard the door close and latch, and Jessi and I were alone.

I looked directly into her eyes and smiled at her while moving in to kiss her. She met my lips tenderly as the evening's seduction began.

When the kiss was finished, she moved her face back and looked at me. Her hands started to move over my chest and shoulders, her eyes moving furtively up and down and watching what her hands were doing. Like the others she spent some time gently feeling the scars on my chest. She'd see the ones on my back later.

I just kept my eyes on her and my hands on her hips holding her gently.

She was exploring every part of me that she could reach from her position on my lap. When she brought her hands up on either side of my face she pulled it in for a tender wanting kiss, gently moving her tongue to mine, inviting me to play.

She moved her face back, put her hands behind my head and started to run her fingers through my hair. Her nervous eyes never left mine. I could hear her breathing increase in tempo and become a little irregular as she emotionally turned herself on to the activities ahead. She was ready, I could see and feel it, but she hadn't quite accepted it emotionally yet.

"Touch me Bobby, please?" She whispered to me.

I smiled at her and gently started moving my hands around on her body. I had been waiting for her to ask for my participation. I was sure that Mel had told her that she was "in control" of everything and that I'd do nothing without her asking.

I purposely avoided any contact with her breasts for now. Below the waist I only caressed her thighs on the outside and top. As I was moving my hands up and down the tops of her thighs she moved her legs apart enough to give me access to her inner skin, but for now I avoided those tempting legs.

For the first bit her eyes never left mine, but as my hands did a little more roaming, she let out a sigh and laid her head on my shoulder turning occasionally to nibble or kiss my shoulder, neck or chest. As Mel had alluded to earlier, she was obviously a very sensual woman.

Noting that, I kept all my touching, licking, nipping and nibbling soft and tender which caused her breathing to increase and her body to begin wiggling in my lap.

I know she could feel the hard meat under her ass because she wiggled to adjust her pussy around it. She was rapidly becoming ready for the fun to come.

She moved her head next to mine and tenderly nipped and licked my ear before whispering, "Take me to bed and make love to me, Bobby." Then pulled her head back to look me straight in the eyes.

I looked back with a smile, nodded my head and placed one arm under her knees and one behind her back, stood up to carry her to her virgin bed.

As I picked her up she let out a gentle moan and whispered, "Oh my god," as she lowered her head to my shoulder.

I took the short walk to the huge round bed, knelt and gently laid her on her back, her head on a couple pillows. God she is a beautiful woman. I just can't get over how desirable she looks here on the bed, on her back, nervously looking up to me with absolute trust and anticipation in her lustful eyes.

Kneeling next to her, looking down and letting my hands continue their discovery, one of her hands moved to the lump in my shorts and started to caress lovingly.

"I know I need to tell you what I want before you'll do it Bobby, so I'll just tell you now, before we really get started."

"I want you to make love to me, Bobby. I want you to lick me. I want you to kiss me. I want you to eat me. I want everything you gave to Mel and Hailey. I want you inside me, and I want your sperm in my fertility."

I must have looked at her with a strange look, because she giggled and added, "Did I cover all the bases?"

I nodded my head slowly, then asked, "You said fertility? Are you in your fertile time Jessi?"

She smiled at me and nodded her head, and then with a look that was so sexy, so sensual, I once again melted. She whispered, "I planned it this way Bobby. I want my first time to have the added excitement of possible pregnancy. If it happens, I'll be very happy and proud to carry our baby, so please don't hold anything back from me because of that. I want it this way."

I nodded my head acknowledging, "Do Mel and Hailey know?"

She paused and slowly nodded her head. "They know I set it up purposely. I wasn't supposed to tell you though.

"Bobby, I can't do that to you. It would be less than honest and I feel like it would violate the trust you have given me. They keep telling you not to violate my trust, but what about yours? They're just trying to make it right for me, and I appreciate that, but I don't think they see it from the other side. It's not really their fault. If it happens, and I do get pregnant, it will be your baby too, so you should have a part in the decision."

I nodded to her, and whispered, "Thank you Jessica. I honestly appreciate your thoughtfulness. You're right, they were wrong."

"Don't blame them Bobby. Please, for me, don't even mention that I told you about it other than to acknowledge you know I'm in my fertile time. They were afraid that you wouldn't do it with me knowing that I was fertile because I may not be part of the "family" when it's all said and done," adding, "At least not at first. Do any of us really know what the future will bring?"

In saying that, she was leaving a big door open. I had a flash thought about how much I would like her to walk through that door at some point in time.

Again, I just nodded my understanding.

"Bobby, I know it sounds crazy, but I love you. I love you a lot, but I know me well enough to know that there's no way I can share 'my man' with any other woman. At least at this point in my life."

Then continuing with a huge grin, "You won't be rid of me though. We haven't done anything yet, but I know I'll be back for more, believe me. I just want you to know at the outset; once I find my 'prince charming' I won't share him with anyone. He may have to agree to share me once in a while, but I will not share him," then after a bit added thoughtfully, "That's all in the future though."

"I may change my mind," she finished with a promising smile.

"Jessi, I knew most of that going in. Mel and Hailey both told me that you may not join our family and why, but as you said, none of us knows what the future will bring to us. They love you very much and they know you, but have no problem sharing me with you, so you may want to consider all of that in your overall feelings. After all, you didn't expect to be making love to me did you?"

She shook her head slowly.

I continued, "They are truly, loving, caring, remarkable young women."

Jessica nodded vigorously, "They sure are. You are very lucky, Bobby."

"I know, Jessi. I know, and I pinch myself every day hoping that I don't wake up to find it's all a dream."

During this whole conversation neither of our hands had been idle. We were both caressing each other softly pushing that state of arousal higher.

I finally moved my hands to her ample breasts and started gently massaging the orbs being presented to me. Jessica let out a loud moan as I finally got to a place that she was waiting for.

"Yeeessssss," she gasped.

I gently manipulated all around the tits waiting for the nipples, but she wasn't waiting. She moved her body so that my hands couldn't help but include the nipples in my grasp. Taking that as a hint, I pinched both gently in my hands causing each to stiffen dramatically. At the same time she locked in on my eyes, looking like a cornered animal, and immediately started to wiggle, twitch and arch her stiffening body upward.

"OoohhhhGoddddd! Bobbbbbbeeeee."

Hmm, incredibly sensitive boobies "Give it to me Jessi honey, let it out. Let it happen. Come for me, Baby."

Her breathing was choking as her body released with multiple spasms. Her muscles contracted and she screamed loudly in orgasm.

Just as it had started in an instant, her body collapsed and relaxed in an instant.

The muscles in her abdomen continued to ripple and her whole body quivered but you could tell it was coming down from the peak.

Holy shit, I hadn't even gotten her clothes off, nor touched her anywhere near her sex and she exploded. The anticipation was overwhelming her.

I held her tenderly in my arms, kissing her face, neck and shoulders gently whispering loving things into her ears so that she would know it was all ok and I was still here for her.

After two or three minutes that seemed like an hour, her eyes fluttered open and lustfully stared at me. No nervous left in there. There was only hot, smoky, lustful desire.

"Oh my god, I never knew I could come like that, and you haven't even really touched me yet. I may not survive the night!

"That's only the first Hon, you'll survive. Trust me, if anyone wasn't going to survive the night it was Hailey, you'll do just fine."

"Holy shit," she said again. "I've never felt this good in all my life. And you say it gets better? I don't know how!"

I smiled at her and nodded, "Shall I remove those things that are in the way of our interesting continuance?"

She bit the inside of her lower lip and got a shy look but nodded her head, "Would you like some help?"

I chuckled, and asked, "Do you think I need some?"

Her laugh was priceless and I did notice her tits jiggling nicely.

I reached over and pulled the bottom of the miniscule baby doll up over her head releasing her incredible chest to the open air. I couldn't help myself. I leaned over and took a nipple in my mouth and sucked, licked and nibbled on it.

"Oooohhhhhh ... Bobbbbbbbeeeeeee"

I lifted my head and looked at her, "You rang?"

"Gawd, I don't believe how sensitive my tities are. That felt soooooo goooood."

"It's supposed to my love." I whispered to her as I put my thumbs into the elastic that was holding up the panties of the set and started to push them down. She raised her butt off the bed to help me remove them, so I guess I did need some help I smiled to myself.

Gazing down at Jessica I just gasped when I took in her body. She had a concerned look on her face, but when she saw my grin, her face relaxed and returned the smile.

"Like what you see, big boy?" She quietly giggled at her imitation of Mae West.

"I love what I see Jess. You have an incredible body Jessica; I can only imagine what you're going to look like when you're nineteen or twenty. I know it's less than a year away, but you look incredible."

"Thank you Bobby. You don't know what that means to me."

I looked at her tenderly, "I think I do Jessi. I'm very aware of a young woman being unsure of her body and how a man will view her, especially for the first time. I could see the nervousness in your eyes."

She smiled at me shyly.

"You have nothing to be nervous about my dear. Not a worry."

I leaned over and kissed her gently as my hands started to move about her body again. This one needed the timing of the main event to be accelerated just a bit, but there was still no rush.

The kiss migrated into licking her neck, and her ears, down her neck to the middle of her chest, stopping for a bit at each breast to lick and nibble. I decided to monitor her arousal a bit closer this time so that I could be in a little more control of her orgasms.

As she started to moan more loudly and wiggle more intensely, I moved my mouth off of her breasts to a frustrated moan, but began the journey south that would culminate at the center of her sex.

Before I even got to her belly button her legs came apart in anticipation of my need for space between them. I smiled knowing that she was thinking ahead of me just a bit. Obviously the briefing she had received from Mel and Hailey was very detailed.

Using my tongue to titillate her abdominal skin, I spent a little time licking and nipping that area that was covering her ovaries and those internal sex organs. Some would be accepting my deposit in a very short time. I made sure to spend extra time over that area where our baby could be growing soon.

Licking down her hips over her thighs and up the other thigh I circled her mound, moving the spiral ever closer basing position on her moans, gasps and motion.

I moved my face into the center of her love, stuck out my tongue, gently started at the bottom of her vulva, and slowly licked up to the top where I barely touched the little button peeking out from its cover. When my tongue came into contact with her clitoris she came unglued.

She moaned very loudly then gasped just as loudly as her body contracted. Her legs slammed into my head joining her hands to strain the muscles in my neck to their maximum.

Not to be deterred, when her body arched up, all the muscles in her tummy froze then started to twitch, and ripple, I reached up with my hands and took each breast firmly. I manipulated her nipples with some force this time and as I did that, she literally screamed out as her orgasm intensified.

I heard the click to the side of me and sensed that the door to the girl's suite had opened. I couldn't see it yet, but I was sure the two were checking on their sister wondering what the hell was going on to cause her to scream that way.

I didn't mind, and I'm pretty sure Jessi didn't detect the intrusion as she was in the throes of her most powerful orgasm to date.

Only number 2 sweets is what ran through my head as I waited patiently for her legs to release me so I could continue providing air to my system.

She grunted a couple times, and her lungs finally started allowing intake. Her body just collapsed and as it did I quickly slid up to take her in my arms and against my body to assure her that everything was okay. Her breathing was rasping in and out and I could tell that her body was still quivering in spasm. I just held her tight, kissed her tenderly and whispered love into her ears.

It was at that point that I notice there were two very concerned faces next to the bed. I looked up, smiled at Mel and Hailey, and lipped to them that everything was fine.

After looking at their friend, they could tell that she was just recovering from a powerful orgasm and that she was doing okay. They both smiled at me widely and blew me a little kiss and quietly retreated before Jessica detected them being there.

She had, but was too internalized to acknowledge their presence.

It took over five minutes for her to recover to a level where she could talk to me or look at me with anything but totally dilated eyes.

As she was coming down a bit more, she began to purr. Now that made all three of them. I'd never really experienced a woman purring like this before Mel, Hailey and now Jessica. Just like a cat. As she purred, she moved her face gently over my chest. She began to kiss my chest slowly, and then licked me tenderly.

She lowered her hand and began to stroke my hard penis very lovingly. She looked up into my eyes so that I could only see how she felt about those feelings that I had given to her and the love she was feeling.

She moved slightly and let out a heavy sigh then slowly moved down to where her face was looking directly at my cock and her hands moving up and down over it.

She seemed to study it carefully, looking at all sides and blowing her breath on it gently.

Watching her was almost amusing as she went through all kinds of facial emotions.

She wasn't quite sure what she was going to do or say at this point.

Then one hand squeezed my penis a bit harder and I could see a little of the lubricant escape at the tip. She looked at it with extreme curiosity, and then looked up at me, with question in her eyes. I raised my eyebrows in a little surprise. Keeping her eyes fully engaged with mine, she just lowered her face and licked the drop off the tip of my cock.

She drew it into her mouth and I could see the curiosity as she worked at tasting her first bit of man juice.

She laid me back on the bed so that my back was against the headboard on the pillows, more or less sitting. She raised herself to her knees and brought her face up to mine and kissed me passionately for a few moments, then pulled back with a look of surprise, and licked her lips a couple times then smiled at me with that priceless smile.

"Is that what I taste like?" She asked hesitantly.

I nodded to her without making any sound but smiling at her hoping to provide some assurance that all was well with the world.

She was seemingly in a dream world and hadn't returned to me quite yet, but then commented, "I know Mel and Hailey do it all the time, but not me. Now I will! I don't taste that bad, do I."

I shook my head and whispered to her, "No, Baby. You're delicious, and I want to taste you more."

She smiled at me and with her eyes becoming sparklers once again, kissed me tenderly, and then moved her face down until it was right at my cock again.

She stuck out her tongue and started to lick the sensitive head of my cock gently, and when she did I let out a loud moan causing her to stop and look up to see if something was wrong, but seeing that I was smiling with my eyes closed, she dipped her head back down and continued.

After licking up and down the entire shaft and all around my balls for a time, she opened her mouth, took the head of my cock into her mouth, and began sucking. Her tongue didn't take a break during this, and between the suction and the flicking of her tongue; I was close to blasting in to her mouth. I think Mel and Hailey have given Miss Jessi some instruction in the finer points of blowjobs. It's undoubtedly one of those "gross" things that Mel was chiding her about. She didn't seem to have any hesitation in her performance.

I held off for a little more time and allowed her to start bobbing her head up and down while continuing the tongue movement and the suction. She looked up at me with eyes that were smiling and sparkling telling me that she was very much enjoying what she was doing.

It wasn't going to be long now before I was going to blow my load at her, so I placed my hands on either side of her head gently and whispered to her, "Jess, I'm going to come in a moment."

She looked up with her grinning eyes, and slid my cock up so that only the head was still in her mouth. She continued to lick and suck in earnest.

I couldn't hold out any longer, and just gave her a quick warning, "Here it comes baby. OoohhhhhhhGgaawwwwddddJessssssiiiiiiieeeeee"!

She kept her eyes attached to mine as she took my load and didn't slop a drop. It was apparent she was swishing it around in her mouth to get the full taste of me, and then swallowed it down with a huge grin on her face.

As the last spurts were entering her mouth and she was licking them up with her tongue, she began to lick up and down and clean my now mostly flaccid penis, never once losing her connection with my eyes.

Her eyes sparkled with joy as she finished me up and still bent over on her knees, kissed the head of my tool and whispered lovingly, "Be gentle with me. I want you so badly in me, and I want to feel those squirts you just did in my mouth way deep inside, but you'll be the first to enter there. I'm pretty sure there is going to be something in the way. Please break it gently, but don't hesitate, break it. I know it will hurt some, but I want the hurt. I love you and I know you'll love me. Thanks."

Then with a shy grin, she began to move herself up to me and put her face right in front of mine.

I couldn't help myself. I just leaned in and intensely kissed her and with my hands pulled her hard to my face. It felt as though she wanted to pull away so I loosened my grip just a bit and she moved her face back from me.

"You're kissing me? After I did that with you," she sounded incredulous.

"Yes of course, Honey. I love you and I love what you just did. It made me feel incredible, why wouldn't I want to kiss you after that?" knowing full well what her response was going to be.

"I've got your cum on my breath and in my mouth..."

"Jessi, after what you did and the way it made me feel, why would I object? It's only some bodily fluid. You tasted you on me, why shouldn't I taste me on you?"

"It's just that I've heard that..."

"What you've heard is what you've heard. You know both Mel and Hailey said the same exact thing to me after they did the same thing," which brought a look of surprise to her face, "What? You're surprised they did that with me just like you did, or that I kissed them afterward." I guess I was wrong about the briefing.

With a look of surprise, she nodded to me.

"Jess, if you feel enough caring for a man to give him a blowjob like that and he won't kiss you afterward, find another man! He really doesn't care about you, only what you are able to do for him. It's the same thing I told both Mel and Hailey, and that's the way I feel!"

I leaned in and kissed her hard and passionately again nearly forcing my tongue into her mouth as if to prove my point to her. She gently played tongue tag with me while I began to move my hands over her body again.